Crystal structures of intermediates in a new synthesis of antitumor drug cabozantinib

Article abstract of DOI:10.3987/COM-15-S(T)45

The heterocyclic antitumor drug cabozantinib was synthesized by condensation of 4-(6,7-dimethoxyquinolin-4-yloxy)aniline and methyl 1-(4-fluorophenylcarbamoyl)cyclopropanecarboxylate in the presence of two equivalents of sodium methoxide and azeotropic re

Full text of DOI:10.3987/COM-15-S(T)45

#\#CIF_1.1
#
#
#
CIF produced by WinGX routine CIF_UPDATE
Created on 2013-07-31 at 15:57:18
Using CIFtbx version 2.6.2 16 Jun 1998
#
#
#
#
Dictionary name : cif_core.dic
Dictionary vers : 2.4
Request file
: c:\wingx\files\archive.reqdat
CIF files read : gl567_2 gl567_2_od
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#
data_global
#------------------ AUDIT DETAILS -------------------------------------------#
_
_
_
_
_
_
audit_creation_date
2013-07-31
'WinGX routine CIF_UPDATE'
cif_core.dic
2.4
ftp://ftp.iucr.org/pub/cif_core.dic
?
audit_creation_method
audit_conform_dict_name
audit_conform_dict_version
audit_conform_dict_location
audit_update_record
#------------------ AUTHOR DETAILS -------------------------------------------#
#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#
data_gl567_2
_
_
_
_
_
;
audit_creation_date
audit_creation_method
audit_author_name
audit_contact_author
audit_contact_author_address
2013-07-31T15:57:18-00:00
'WinGX routine CIF_UPDATE'
'V. Kahlenberg'
'V. Kahlenberg'
Institut f\"ur Mineralogie und Petrographie
Leopold-Franzens-Universit\"at Innsbruck
Innrain 52
A-6020 Innsbruck
Austria
;
_
_
_
audit_contact_author_email Volker.Kahlenberg@uibk.ac.at
audit_contact_author_fax '+43 512 507 2926'
audit_contact_author_phone '+43 512 507 5503'
_audit_conform_dict_name
_audit_conform_dict_version
_audit_conform_dict_location
_publ_requested_category
cif_core.dic
2.4
ftp://ftp.iucr.org/pub/cif_core.dic
FO
#
#
#
----------------------------------------------------------------------------#
CHEMICAL INFORMATION
#
----------------------------------------------------------------------------#
_
;
chemical_name_systematic
?
;
_
_
_
_
chemical_formula_sum
'C11 H13 N O4'
'C11 H11 N O3, H2 O'
223.22
chemical_formula_moiety
chemical_formula_weight
chemical_absolute_configuration
unk

#
#
#
----------------------------------------------------------------------------#
UNIT CELL INFORMATION
----------------------------------------------------------------------------#
#
_
_
_
symmetry_cell_setting
symmetry_space_group_name_H-M
symmetry_space_group_name_Hall
monoclinic
'C 1 c 1'
'C -2yc'
loop_
_
symmetry_equiv_pos_as_xyz
'
'
'
'
x, y, z'
x, -y, z+1/2'
x+1/2, y+1/2, z'
x+1/2, -y+1/2, z+1/2'
_
_
_
_
_
_
_
_
_
_
_
_
cell_length_a
cell_length_b
cell_length_c
cell_angle_alpha
cell_angle_beta
cell_angle_gamma
cell_volume
cell_formula_units_Z
cell_measurement_temperature
cell_measurement_reflns_used
cell_measurement_theta_min
cell_measurement_theta_max
4.7469(3)
16.5037(11)
13.1660(9)
90
95.426(7)
90
1026.82(12)
4
173(2)
1783
3.3702
67.2878
#
#
#
----------------------------------------------------------------------------#
CRYSTAL INFORMATION
----------------------------------------------------------------------------#
#
_
_
_
_
_
_
_
_
_
;
exptl_crystal_description
exptl_crystal_colour
'platy fragment'
colourless
0.18
0.16
0.04
1.444
'not measured'
472
exptl_crystal_size_max
exptl_crystal_size_mid
exptl_crystal_size_min
exptl_crystal_density_diffrn
exptl_crystal_density_method
exptl_crystal_F_000
exptl_special_details
?
;
#
#
#
----------------------------------------------------------------------------#
ABSORPTION CORRECTION
----------------------------------------------------------------------------#
#
_
_
_
;
exptl_absorpt_coefficient_mu
exptl_absorpt_correction_type
exptl_absorpt_process_details
0.93
multi-scan
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_
_
exptl_absorpt_correction_T_min
exptl_absorpt_correction_T_max
0.94873
1
#
#
----------------------------------------------------------------------------#
DATA COLLECTION
#

#----------------------------------------------------------------------------#
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
diffrn_ambient_temperature
diffrn_radiation_wavelength
diffrn_radiation_type
173(2)
1.5418
CuK\a
mirror
10.3575
0.2317761
0.0560854
0.0506406
0.1180111
-0.0707372
0.067624
0.1970399
-0.0236084
-0.0816786
'Xcalibur, Ruby, Gemini ultra'
'\w scans'
0.0301
0.0244
4219
-5
5
-19
19
-15
diffrn_radiation_monochromator
diffrn_detector_area_resol_mean
diffrn_orient_matrix_ub_11
diffrn_orient_matrix_ub_12
diffrn_orient_matrix_ub_13
diffrn_orient_matrix_ub_21
diffrn_orient_matrix_ub_22
diffrn_orient_matrix_ub_23
diffrn_orient_matrix_ub_31
diffrn_orient_matrix_ub_32
diffrn_orient_matrix_ub_33
diffrn_measurement_device_type
diffrn_measurement_method
diffrn_reflns_av_R_equivalents
diffrn_reflns_av_unetI/netI
diffrn_reflns_number
diffrn_reflns_limit_h_min
diffrn_reflns_limit_h_max
diffrn_reflns_limit_k_min
diffrn_reflns_limit_k_max
diffrn_reflns_limit_l_min
diffrn_reflns_limit_l_max
diffrn_reflns_theta_min
9
5.36
67.36
67.36
diffrn_reflns_theta_max
diffrn_reflns_theta_full
diffrn_measured_fraction_theta_full
0
.995
.995
_diffrn_measured_fraction_theta_max
0
_
_
_
reflns_number_total
reflns_number_gt
reflns_threshold_expression
1221
1161
>2\s(I)
#
#
#
----------------------------------------------------------------------------#
COMPUTER PROGRAMS USED
#
----------------------------------------------------------------------------#
_
;
computing_data_collection
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(
compiled Jul 11 2012,15:38:31)
;
_
;
computing_cell_refinement
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
compiled Jul 11 2012,15:38:31)
(
;
_
;
computing_data_reduction
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
compiled Jul 11 2012,15:38:31)
(
;
_
_
computing_structure_solution
computing_structure_refinement
'SIR2002 (Burla et al., 2003)'
'SHELXL-97 (Sheldrick, 2008)'
#----------------------------------------------------------------------------#

#
#
STRUCTURE SOLUTION
----------------------------------------------------------------------------#
_atom_sites_solution_primary
_atom_sites_solution_secondary
_atom_sites_solution_hydrogens
direct
difmap
geom
#
#
#
----------------------------------------------------------------------------#
REFINEMENT INFORMATION
#
----------------------------------------------------------------------------#
_
;
refine_special_details
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_
_
_
_
refine_ls_structure_factor_coef
refine_ls_matrix_type
refine_ls_weighting_scheme
refine_ls_weighting_details
Fsqd
full
calc
'calc w=1/[\s^2^(Fo^2^)+(0.1673P)^2^+0.2782P] where P=(Fo^2^+2Fc^2^)/3'
_
_
_
_
_
_
_
_
_
_
_
_
_
_
refine_ls_hydrogen_treatment
refine_ls_extinction_method
refine_ls_number_reflns
refine_ls_number_parameters
refine_ls_number_restraints
refine_ls_R_factor_all
refine_ls_R_factor_gt
refine_ls_wR_factor_ref
refine_ls_wR_factor_gt
refine_ls_goodness_of_fit_ref
refine_ls_restrained_S_all
refine_ls_shift/su_max
refine_ls_shift/su_mean
refine_ls_abs_structure_details
mixed
none
1221
150
6
0.0541
0.0524
0.1582
0.154
1.07
1.069
0
0
'
Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack
_refine_diff_density_max
_refine_diff_density_min
_refine_diff_density_rms
0.7(4)
0.454
-0.526
0.093
#
#
#
----------------------------------------------------------------------------#
ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS
----------------------------------------------------------------------------#
#
loop_
_
_
_
_
_
atom_type_symbol
atom_type_description
atom_type_scat_dispersion_real
atom_type_scat_dispersion_imag
atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_atom_site_label
_atom_site_type_symbol

_
_
_
_
_
_
_
_
_
_
_
atom_site_fract_x
atom_site_fract_y
atom_site_fract_z
atom_site_U_iso_or_equiv
atom_site_adp_type
atom_site_occupancy
atom_site_symmetry_multiplicity
atom_site_calc_flag
atom_site_refinement_flags
atom_site_disorder_assembly
atom_site_disorder_group
O1 O 0.5135(6) 0.17149(15) 0.5050(2) 0.0351(8) Uani 1 1 d . . .
O2 O 0.4725(7) 0.32503(15) 0.4818(3) 0.0377(8) Uani 1 1 d . . .
O3 O -0.2784(7) 0.04966(17) 0.2538(3) 0.0417(8) Uani 1 1 d . . .
N1 N -0.2942(7) 0.29530(19) 0.2244(3) 0.0308(8) Uani 1 1 d D . .
H1 H -0.274(12) 0.3454(15) 0.211(4) 0.037 Uiso 1 1 d D . .
C10 C 0.4427(13) 0.4112(3) 0.4771(4) 0.0492(13) Uani 1 1 d . . .
H10A H 0.4658 0.4299 0.4077 0.074 Uiso 1 1 calc R . .
H10B H 0.5875 0.4364 0.525 0.074 Uiso 1 1 calc R . .
H10C H 0.2545 0.4265 0.4955 0.074 Uiso 1 1 calc R . .
C9 C 0.2905(9) 0.2813(3) 0.4236(3) 0.0300(9) Uani 1 1 d . . .
C7 C -0.0964(8) 0.2614(2) 0.2937(3) 0.0296(9) Uani 1 1 d . . .
C6 C -0.4773(9) 0.2502(3) 0.1662(3) 0.0314(9) Uani 1 1 d . . .
H6 H -0.6098 0.2763 0.1183 0.038 Uiso 1 1 calc R . .
C5 C -0.4807(9) 0.1673(3) 0.1732(4) 0.0351(10) Uani 1 1 d . . .
H5 H -0.615 0.137 0.1307 0.042 Uiso 1 1 calc R . .
C3 C -0.0847(8) 0.1775(2) 0.3053(3) 0.0298(10) Uani 1 1 d . . .
C1 C 0.3127(8) 0.1954(3) 0.4365(3) 0.0315(10) Uani 1 1 d . . .
C4 C -0.2830(8) 0.1264(2) 0.2441(4) 0.0334(10) Uani 1 1 d . . .
C2 C 0.1263(9) 0.1461(2) 0.3785(3) 0.0336(10) Uani 1 1 d . . .
H2 H 0.1394 0.0891 0.3877 0.04 Uiso 1 1 calc R . .
C11 C 0.5586(11) 0.0860(2) 0.5137(4) 0.0437(11) Uani 1 1 d . . .
H11A H 0.3924 0.0604 0.5389 0.065 Uiso 1 1 calc R . .
H11B H 0.7255 0.0754 0.5615 0.065 Uiso 1 1 calc R . .
H11C H 0.5887 0.0636 0.4466 0.065 Uiso 1 1 calc R . .
C8 C 0.0896(10) 0.3135(2) 0.3536(4) 0.0354(10) Uani 1 1 d . . .
H8 H 0.0749 0.3706 0.3452 0.042 Uiso 1 1 calc R . .
O4 O 0.7055(7) 0.46611(17) 0.2208(3) 0.0449(9) Uani 1 1 d D . .
H41 H 0.5693 0.4907 0.2464 0.067 Uiso 1 1 d RD . .
H42 H 0.8531 0.4959 0.2272 0.067 Uiso 1 1 d RD . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0423(17) 0.0214(14) 0.0406(16) -0.0005(11) -0.0012(14) 0.0034(11)
O2 0.0461(18) 0.0222(14) 0.0437(17) -0.0049(11) -0.0008(15) -0.0038(11)
O3 0.0338(14) 0.0289(13) 0.061(2) -0.0069(14) -0.0008(13) -0.0015(12)
N1 0.0272(15) 0.0317(15) 0.0333(17) 0.0047(14) 0.0027(13) 0.0028(14)
C10 0.072(3) 0.0182(19) 0.055(3) -0.0012(18) -0.006(3) -0.0014(18)
C9 0.0288(18) 0.0291(18) 0.032(2) -0.0022(17) 0.0003(16) 0.0009(16)
C7 0.0228(17) 0.036(2) 0.0301(19) 0.0040(18) 0.0031(15) 0.0018(16)
C6 0.0265(19) 0.040(2) 0.0275(19) 0.0014(17) -0.0001(15) 0.0021(16)
C5 0.030(2) 0.036(2) 0.039(2) -0.0105(19) 0.0013(17) -0.0059(17)
C3 0.0194(17) 0.038(2) 0.032(2) 0.0030(17) 0.0017(16) 0.0024(16)
C1 0.024(2) 0.035(2) 0.035(2) -0.0072(18) 0.0008(17) 0.0002(16)
C4 0.0228(17) 0.0320(19) 0.046(3) -0.0051(17) 0.0051(18) 0.0015(16)
C2 0.0327(19) 0.0284(18) 0.039(2) -0.0024(17) 0.0020(18) 0.0035(17)
C11 0.054(3) 0.0211(18) 0.054(3) 0.0069(18) -0.005(2) 0.0041(17)
C8 0.034(2) 0.0278(18) 0.045(3) -0.0004(17) 0.0046(19) 0.0018(16)

O4 0.0363(16) 0.0292(12) 0.069(2) -0.0049(13) 0.0055(15) 0.0004(12)
#
#
#
----------------------------------------------------------------------------#
MOLECULAR GEOMETRY
#
----------------------------------------------------------------------------#
_
;
geom_special_details
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_
_
_
_
_
geom_bond_atom_site_label_1
geom_bond_atom_site_label_2
geom_bond_distance
geom_bond_site_symmetry_2
geom_bond_publ_flag
O1 C1 1.309(6) . ?
O1 C11 1.430(5) . ?
O2 C9 1.315(5) . ?
O2 C10 1.431(5) . ?
O3 C4 1.273(5) . ?
N1 C6 1.331(6) . ?
N1 C7 1.366(5) . ?
N1 H1 0.85(2) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C9 C8 1.370(7) . ?
C9 C1 1.431(6) . ?
C7 C3 1.392(5) . ?
C7 C8 1.418(6) . ?
C6 C5 1.371(6) . ?
C6 H6 0.95 . ?
C5 C4 1.430(6) . ?
C5 H5 0.95 . ?
C3 C2 1.421(6) . ?
C3 C4 1.451(6) . ?
C1 C2 1.378(6) . ?
C2 H2 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C8 H8 0.95 . ?
O4 H41 0.8588 . ?
O4 H42 0.8538 . ?
loop_
_
_
_
_
_
_
_
geom_angle_atom_site_label_1
geom_angle_atom_site_label_2
geom_angle_atom_site_label_3
geom_angle
geom_angle_site_symmetry_1
geom_angle_site_symmetry_3
geom_angle_publ_flag
C1 O1 C11 116.5(3) . . ?
C9 O2 C10 117.6(4) . . ?
C6 N1 C7 121.7(3) . . ?
C6 N1 H1 120(4) . . ?

C7 N1 H1 117(4) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C9 C8 123.8(4) . . ?
O2 C9 C1 115.9(4) . . ?
C8 C9 C1 120.2(4) . . ?
N1 C7 C3 119.9(4) . . ?
N1 C7 C8 118.3(4) . . ?
C3 C7 C8 121.8(4) . . ?
N1 C6 C5 122.0(4) . . ?
N1 C6 H6 119 . . ?
C5 C6 H6 119 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C3 C2 117.1(4) . . ?
C7 C3 C4 120.0(4) . . ?
C2 C3 C4 122.9(3) . . ?
O1 C1 C2 126.3(4) . . ?
O1 C1 C9 114.9(3) . . ?
C2 C1 C9 118.9(4) . . ?
O3 C4 C5 122.7(4) . . ?
O3 C4 C3 121.3(4) . . ?
C5 C4 C3 116.1(3) . . ?
C1 C2 C3 122.4(3) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
H41 O4 H42 109.3 . . ?
loop_
_
_
_
_
_
_
_
_
_
_
geom_torsion_atom_site_label_1
geom_torsion_atom_site_label_2
geom_torsion_atom_site_label_3
geom_torsion_atom_site_label_4
geom_torsion
geom_torsion_site_symmetry_1
geom_torsion_site_symmetry_2
geom_torsion_site_symmetry_3
geom_torsion_site_symmetry_4
geom_torsion_publ_flag
C10 O2 C9 C8 5.3(7) . . . . ?
C10 O2 C9 C1 -175.1(4) . . . . ?
C6 N1 C7 C3 -0.5(6) . . . . ?
C6 N1 C7 C8 -179.4(4) . . . . ?
C7 N1 C6 C5 0.8(7) . . . . ?
N1 C6 C5 C4 -0.3(7) . . . . ?
N1 C7 C3 C2 179.8(4) . . . . ?
C8 C7 C3 C2 -1.3(5) . . . . ?
N1 C7 C3 C4 -0.3(5) . . . . ?
C8 C7 C3 C4 178.6(4) . . . . ?
C11 O1 C1 C2 5.9(6) . . . . ?

C11 O1 C1 C9 -174.7(3) . . . . ?
O2 C9 C1 O1 -0.1(5) . . . . ?
C8 C9 C1 O1 179.5(4) . . . . ?
O2 C9 C1 C2 179.4(3) . . . . ?
C8 C9 C1 C2 -1.0(6) . . . . ?
C6 C5 C4 O3 179.7(4) . . . . ?
C6 C5 C4 C3 -0.4(6) . . . . ?
C7 C3 C4 O3 -179.4(4) . . . . ?
C2 C3 C4 O3 0.5(6) . . . . ?
C7 C3 C4 C5 0.7(6) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
O1 C1 C2 C3 -179.7(4) . . . . ?
C9 C1 C2 C3 0.9(6) . . . . ?
C7 C3 C2 C1 0.2(6) . . . . ?
C4 C3 C2 C1 -179.7(4) . . . . ?
O2 C9 C8 C7 179.6(4) . . . . ?
C1 C9 C8 C7 -0.1(6) . . . . ?
N1 C7 C8 C9 -179.9(4) . . . . ?
C3 C7 C8 C9 1.2(6) . . . . ?
loop_
_
_
_
_
_
_
_
_
geom_hbond_atom_site_label_D
geom_hbond_atom_site_label_H
geom_hbond_atom_site_label_A
geom_hbond_distance_DH
geom_hbond_distance_HA
geom_hbond_distance_DA
geom_hbond_angle_DHA
geom_hbond_site_symmetry_A
O4 H41 O3 0.86 1.93 2.749(4) 160 3
O4 H42 O3 0.85 1.96 2.809(4) 170.8 3_655
N1 H1 O4 0.85(2) 2.00(3) 2.819(4) 161(5) 1_455
#
END of CIF

#\#CIF_1.1
#
#
#
CIF produced by WinGX routine CIF_UPDATE
Created on 2013-07-29 at 13:18:49
Using CIFtbx version 2.6.2 16 Jun 1998
#
#
#
#
Dictionary name : cif_core.dic
Dictionary vers : 2.4
Request file
: c:\wingx\files\archive.reqdat
CIF files read : gl576_1 gl576_1_od
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#
data_global
#------------------ AUDIT DETAILS -------------------------------------------#
_
_
_
_
_
_
audit_creation_date
2013-07-29
'WinGX routine CIF_UPDATE'
cif_core.dic
2.4
ftp://ftp.iucr.org/pub/cif_core.dic
?
audit_creation_method
audit_conform_dict_name
audit_conform_dict_version
audit_conform_dict_location
audit_update_record
#------------------ AUTHOR DETAILS -------------------------------------------#
#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#
data_gl576_1
_
_
_
_
_
;
audit_creation_date
audit_creation_method
audit_author_name
audit_contact_author
audit_contact_author_address
2013-07-29T13:18:49-00:00
'WinGX routine CIF_UPDATE'
'V. Kahlenberg'
'V. Kahlenberg'
Institut f\"ur Mineralogie und Petrographie
Leopold-Franzens-Universit\"at Innsbruck
Innrain 52
A-6020 Innsbruck
Austria
;
_
_
_
audit_contact_author_email Volker.Kahlenberg@uibk.ac.at
audit_contact_author_fax '+43 512 507 2926'
audit_contact_author_phone '+43 512 507 5503'
_audit_conform_dict_name
_audit_conform_dict_version
_audit_conform_dict_location
_publ_requested_category
cif_core.dic
2.4
ftp://ftp.iucr.org/pub/cif_core.dic
FO
#
#
#
----------------------------------------------------------------------------#
CHEMICAL INFORMATION
#
----------------------------------------------------------------------------#
_
;
chemical_name_systematic
?
;
_
_
_
chemical_formula_sum
chemical_formula_moiety
chemical_formula_weight
'C12 H12 F N O3'
'C12 H12 F N O3'
237.23

#
#
#
----------------------------------------------------------------------------#
UNIT CELL INFORMATION
----------------------------------------------------------------------------#
#
_
_
_
symmetry_cell_setting
symmetry_space_group_name_H-M
symmetry_space_group_name_Hall
orthorhombic
'P n m a'
'-P 2ac 2n'
loop_
_
symmetry_equiv_pos_as_xyz
'
'
'
'
'
'
'
'
x, y, z'
-x+1/2, -y, z+1/2'
x+1/2, -y+1/2, -z+1/2'
-x, y+1/2, -z'
-x, -y, -z'
x-1/2, y, -z-1/2'
-x-1/2, y-1/2, z-1/2'
x, -y-1/2, z'
_
_
_
_
_
_
_
_
_
_
_
_
cell_length_a
cell_length_b
cell_length_c
cell_angle_alpha
cell_angle_beta
cell_angle_gamma
cell_volume
cell_formula_units_Z
cell_measurement_temperature
cell_measurement_reflns_used
cell_measurement_theta_min
cell_measurement_theta_max
13.0264(6)
6.9982(5)
12.1392(6)
90
90
90
1106.63(11)
4
173(2)
1224
3.3899
67.3217
#
#
#
----------------------------------------------------------------------------#
CRYSTAL INFORMATION
----------------------------------------------------------------------------#
#
_
_
_
_
_
_
_
_
_
;
exptl_crystal_description
exptl_crystal_colour
'platy fragment'
colourless
0.4
0.32
0.16
1.424
'not measured'
496
exptl_crystal_size_max
exptl_crystal_size_mid
exptl_crystal_size_min
exptl_crystal_density_diffrn
exptl_crystal_density_method
exptl_crystal_F_000
exptl_special_details
?
;
#
#
#
----------------------------------------------------------------------------#
ABSORPTION CORRECTION
----------------------------------------------------------------------------#
#
_
_
_
;
exptl_absorpt_coefficient_mu
exptl_absorpt_correction_type
exptl_absorpt_process_details
0.965
multi-scan
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_
_
exptl_absorpt_correction_T_min
exptl_absorpt_correction_T_max
0.72469
1
#
#
#
----------------------------------------------------------------------------#
DATA COLLECTION
----------------------------------------------------------------------------#
#
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
diffrn_ambient_temperature
diffrn_radiation_wavelength
diffrn_radiation_type
173(2)
1.5418
CuK\a
mirror
10.3575
0.0282368
-0.0032562
-0.1230591
0.0035884
-0.2199795
0.002761
-0.1148223
-0.0079857
-0.0307244
'Xcalibur, Ruby, Gemini ultra'
'\w scans'
0.0256
0.0197
3313
-15
10
-8
5
-14
diffrn_radiation_monochromator
diffrn_detector_area_resol_mean
diffrn_orient_matrix_ub_11
diffrn_orient_matrix_ub_12
diffrn_orient_matrix_ub_13
diffrn_orient_matrix_ub_21
diffrn_orient_matrix_ub_22
diffrn_orient_matrix_ub_23
diffrn_orient_matrix_ub_31
diffrn_orient_matrix_ub_32
diffrn_orient_matrix_ub_33
diffrn_measurement_device_type
diffrn_measurement_method
diffrn_reflns_av_R_equivalents
diffrn_reflns_av_unetI/netI
diffrn_reflns_number
diffrn_reflns_limit_h_min
diffrn_reflns_limit_h_max
diffrn_reflns_limit_k_min
diffrn_reflns_limit_k_max
diffrn_reflns_limit_l_min
diffrn_reflns_limit_l_max
diffrn_reflns_theta_min
13
4.98
67.43
67.43
diffrn_reflns_theta_max
diffrn_reflns_theta_full
diffrn_measured_fraction_theta_full
0
.99
.99
_diffrn_measured_fraction_theta_max
0
_
_
_
reflns_number_total
reflns_number_gt
reflns_threshold_expression
1077
903
>2\s(I)
#
#
#
----------------------------------------------------------------------------#
COMPUTER PROGRAMS USED
#
----------------------------------------------------------------------------#
_
;
computing_data_collection
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(
compiled Jul 11 2012,15:38:31)
;
_
;
computing_cell_refinement
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
compiled Jul 11 2012,15:38:31)
(
;
_
;
computing_data_reduction
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
compiled Jul 11 2012,15:38:31)
(

;
_
_
computing_structure_solution
computing_structure_refinement
'SIR2002 (Burla et al., 2003)'
'SHELXL-97 (Sheldrick, 2008)'
#
#
#
----------------------------------------------------------------------------#
STRUCTURE SOLUTION
----------------------------------------------------------------------------#
_atom_sites_solution_primary
_atom_sites_solution_secondary
_atom_sites_solution_hydrogens
direct
difmap
geom
#
#
#
----------------------------------------------------------------------------#
REFINEMENT INFORMATION
#
----------------------------------------------------------------------------#
_
;
refine_special_details
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_
_
_
_
refine_ls_structure_factor_coef
refine_ls_matrix_type
refine_ls_weighting_scheme
refine_ls_weighting_details
Fsqd
full
calc
'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.1085P] where P=(Fo^2^+2Fc^2^)/3'
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
refine_ls_hydrogen_treatment
refine_ls_extinction_method
refine_ls_number_reflns
refine_ls_number_parameters
refine_ls_number_restraints
refine_ls_R_factor_all
refine_ls_R_factor_gt
refine_ls_wR_factor_ref
refine_ls_wR_factor_gt
refine_ls_goodness_of_fit_ref
refine_ls_restrained_S_all
refine_ls_shift/su_max
refine_ls_shift/su_mean
refine_diff_density_max
refine_diff_density_min
refine_diff_density_rms
mixed
none
1077
107
4
0.0426
0.0356
0.108
0.1019
1.061
1.059
0
0
0.185
-0.177
0.036
#
#
#
----------------------------------------------------------------------------#
ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS
----------------------------------------------------------------------------#
#
loop_
_
_
_
_
_
atom_type_symbol
atom_type_description
atom_type_scat_dispersion_real
atom_type_scat_dispersion_imag
atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_
_
_
_
_
_
_
_
_
_
_
_
_
atom_site_label
atom_site_type_symbol
atom_site_fract_x
atom_site_fract_y
atom_site_fract_z
atom_site_U_iso_or_equiv
atom_site_adp_type
atom_site_occupancy
atom_site_symmetry_multiplicity
atom_site_calc_flag
atom_site_refinement_flags
atom_site_disorder_assembly
atom_site_disorder_group
F1 F 0.44603(10) 0.25 -0.11234(9) 0.0579(4) Uani 1 2 d S . .
O2 O 0.60000(9) 0.25 0.50245(11) 0.0447(4) Uani 1 2 d S . .
O3 O 0.29204(10) 0.25 0.39722(11) 0.0545(5) Uani 1 2 d S . .
O1 O 0.54330(10) 0.25 0.67486(11) 0.0479(4) Uani 1 2 d S . .
N1 N 0.45845(11) 0.25 0.34212(13) 0.0358(4) Uani 1 2 d SD . .
H1 H 0.5196(13) 0.25 0.3678(17) 0.043 Uiso 1 2 d SD . .
C11 C 0.35694(14) 0.25 0.16956(16) 0.0391(5) Uani 1 2 d S . .
H11 H 0.2941 0.25 0.2093 0.047 Uiso 1 2 calc SR . .
C15 C 0.54138(14) 0.25 0.16649(16) 0.0377(5) Uani 1 2 d S . .
H15 H 0.605 0.25 0.2048 0.045 Uiso 1 2 calc SR . .
C2 C 0.34546(10) 0.3553(2) 0.61550(11) 0.0410(4) Uani 1 1 d . . .
H2A H 0.376 0.4209 0.6799 0.049 Uiso 1 1 calc R . .
H2B H 0.2854 0.4209 0.5828 0.049 Uiso 1 1 calc R . .
C12 C 0.35622(15) 0.25 0.05493(16) 0.0416(5) Uani 1 2 d S . .
H12 H 0.2931 0.25 0.0156 0.05 Uiso 1 2 calc SR . .
C1 C 0.41843(14) 0.25 0.53719(14) 0.0338(4) Uani 1 2 d S . .
C10 C 0.45007(13) 0.25 0.22575(15) 0.0340(4) Uani 1 2 d S . .
C14 C 0.54102(15) 0.25 0.05260(16) 0.0424(5) Uani 1 2 d S . .
H14 H 0.6034 0.25 0.0121 0.051 Uiso 1 2 calc SR . .
C3 C 0.52947(14) 0.25 0.56715(15) 0.0328(4) Uani 1 2 d S . .
C13 C 0.44788(15) 0.25 -0.00040(16) 0.0411(5) Uani 1 2 d S . .
C6 C 0.38376(14) 0.25 0.41861(15) 0.0362(4) Uani 1 2 d S . .
C5 C 0.64857(16) 0.25 0.71298(17) 0.0504(6) Uani 1 2 d SD . .
H5B H 0.6833(13) 0.3664(14) 0.6881(8) 0.076 Uiso 1 1 d D . .
H5A H 0.6444(17) 0.25 0.7936(2) 0.076 Uiso 1 2 d SD . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0626(9) 0.0836(10) 0.0274(6) 0 0.0003(5) 0
O2 0.0318(7) 0.0692(10) 0.0329(7) 0 0.0010(6) 0
O3 0.0283(7) 0.0985(13) 0.0368(8) 0 -0.0002(6) 0
O1 0.0377(7) 0.0773(11) 0.0287(7) 0 -0.0031(5) 0
N1 0.0267(7) 0.0527(10) 0.0281(8) 0 0.0001(6) 0
C11 0.0318(9) 0.0514(12) 0.0342(10) 0 -0.0002(7) 0
C15 0.0323(9) 0.0465(11) 0.0344(10) 0 -0.0002(7) 0
C2 0.0378(7) 0.0488(9) 0.0364(7) -0.0033(6) 0.0074(5) 0.0056(6)
C12 0.0371(10) 0.0525(12) 0.0352(10) 0 -0.0069(8) 0
C1 0.0314(9) 0.0408(10) 0.0290(9) 0 0.0041(7) 0
C10 0.0339(9) 0.0376(10) 0.0305(10) 0 -0.0006(7) 0
C14 0.0382(10) 0.0538(12) 0.0352(10) 0 0.0059(8) 0
C3 0.0343(9) 0.0347(9) 0.0293(9) 0 -0.0010(7) 0
C13 0.0502(11) 0.0455(11) 0.0275(9) 0 -0.0004(8) 0
C6 0.0314(9) 0.0445(10) 0.0327(9) 0 0.0016(8) 0
C5 0.0416(11) 0.0745(15) 0.0352(10) 0 -0.0104(9) 0

#
#
#
----------------------------------------------------------------------------#
MOLECULAR GEOMETRY
#
----------------------------------------------------------------------------#
_
;
geom_special_details
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_
_
_
_
_
geom_bond_atom_site_label_1
geom_bond_atom_site_label_2
geom_bond_distance
geom_bond_site_symmetry_2
geom_bond_publ_flag
F1 C13 1.359(2) . ?
O2 C3 1.209(2) . ?
O3 C6 1.223(2) . ?
O1 C3 1.320(2) . ?
O1 C5 1.447(2) . ?
N1 C6 1.345(2) . ?
N1 C10 1.417(2) . ?
N1 H1 0.855(16) . ?
C11 C12 1.392(3) . ?
C11 C10 1.392(3) . ?
C11 H11 0.95 . ?
C15 C14 1.383(3) . ?
C15 C10 1.390(3) . ?
C15 H15 0.95 . ?
C2 C2 1.473(3) 8_565 ?
C2 C1 1.5329(19) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C12 C13 1.370(3) . ?
C12 H12 0.95 . ?
C1 C3 1.491(2) . ?
C1 C6 1.509(3) . ?
C1 C2 1.5329(19) 8_565 ?
C14 C13 1.373(3) . ?
C14 H14 0.95 . ?
C5 H5B 0.9799(11) . ?
C5 H5A 0.9799(10) . ?
loop_
_
_
_
_
_
_
_
geom_angle_atom_site_label_1
geom_angle_atom_site_label_2
geom_angle_atom_site_label_3
geom_angle
geom_angle_site_symmetry_1
geom_angle_site_symmetry_3
geom_angle_publ_flag
C3 O1 C5 116.49(15) . . ?
C6 N1 C10 129.24(16) . . ?
C6 N1 H1 115.0(15) . . ?
C10 N1 H1 115.8(15) . . ?
C12 C11 C10 119.74(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?

C14 C15 C10 120.97(17) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C2 C2 C1 61.28(6) 8_565 . ?
C2 C2 H2A 117.6 8_565 . ?
C1 C2 H2A 117.6 . . ?
C2 C2 H2B 117.6 8_565 . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.7 . . ?
C13 C12 C11 118.97(18) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C3 C1 C6 121.53(15) . . ?
C3 C1 C2 116.75(13) . 8_565 ?
C6 C1 C2 113.96(13) . 8_565 ?
C3 C1 C2 116.75(13) . . ?
C6 C1 C2 113.96(13) . . ?
C2 C1 C2 57.44(13) 8_565 . ?
C15 C10 C11 119.49(16) . . ?
C15 C10 N1 116.74(16) . . ?
C11 C10 N1 123.77(16) . . ?
C13 C14 C15 118.13(18) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
O2 C3 O1 122.68(16) . . ?
O2 C3 C1 125.37(16) . . ?
O1 C3 C1 111.96(15) . . ?
F1 C13 C12 118.34(17) . . ?
F1 C13 C14 118.95(17) . . ?
C12 C13 C14 122.70(18) . . ?
O3 C6 N1 124.07(17) . . ?
O3 C6 C1 119.68(16) . . ?
N1 C6 C1 116.25(16) . . ?
O1 C5 H5B 109.8(10) . . ?
O1 C5 H5A 105.5(13) . . ?
H5B C5 H5A 109.47(16) . . ?
loop_
_
_
_
_
_
_
_
_
_
_
geom_torsion_atom_site_label_1
geom_torsion_atom_site_label_2
geom_torsion_atom_site_label_3
geom_torsion_atom_site_label_4
geom_torsion
geom_torsion_site_symmetry_1
geom_torsion_site_symmetry_2
geom_torsion_site_symmetry_3
geom_torsion_site_symmetry_4
geom_torsion_publ_flag
C10 C11 C12 C13 0 . . . . ?
C2 C2 C1 C3 -106.03(10) 8_565 . . . ?
C2 C2 C1 C6 104.09(10) 8_565 . . . ?
C14 C15 C10 C11 0 . . . . ?
C14 C15 C10 N1 180 . . . . ?
C12 C11 C10 C15 0 . . . . ?
C12 C11 C10 N1 180 . . . . ?
C6 N1 C10 C15 180 . . . . ?
C6 N1 C10 C11 0 . . . . ?
C10 C15 C14 C13 0 . . . . ?
C5 O1 C3 O2 0 . . . . ?
C5 O1 C3 C1 180 . . . . ?
C6 C1 C3 O2 0 . . . . ?
C2 C1 C3 O2 147.45(8) 8_565 . . . ?
C2 C1 C3 O2 -147.45(8) . . . . ?
C6 C1 C3 O1 180 . . . . ?

C2 C1 C3 O1 -32.55(8) 8_565 . . . ?
C2 C1 C3 O1 32.55(8) . . . . ?
C11 C12 C13 F1 180 . . . . ?
C11 C12 C13 C14 0 . . . . ?
C15 C14 C13 F1 180 . . . . ?
C15 C14 C13 C12 0 . . . . ?
C10 N1 C6 O3 0 . . . . ?
C10 N1 C6 C1 180 . . . . ?
C3 C1 C6 O3 180 . . . . ?
C2 C1 C6 O3 31.72(8) 8_565 . . . ?
C2 C1 C6 O3 -31.72(8) . . . . ?
C3 C1 C6 N1 0 . . . . ?
C2 C1 C6 N1 -148.28(8) 8_565 . . . ?
C2 C1 C6 N1 148.28(8) . . . . ?
loop_
_
_
_
_
_
_
_
_
geom_hbond_atom_site_label_D
geom_hbond_atom_site_label_H
geom_hbond_atom_site_label_A
geom_hbond_distance_DH
geom_hbond_distance_HA
geom_hbond_distance_DA
geom_hbond_angle_DHA
geom_hbond_site_symmetry_A
N1 H1 O2 0.855(16) 1.942(18) 2.6811(19) 144(2) .
#
END of CIF

#\#CIF_1.1
#
#
#
CIF produced by WinGX routine CIF_UPDATE
Created on 2014-01-19 at 22:05:51
Using CIFtbx version 2.6.2 16 Jun 1998
#
#
#
#
Dictionary name : cif_core.dic
Dictionary vers : 2.4
Request file
: c:\wingx\files\archive.reqdat
CIF files read : gl579_1 gl579_1_od
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#
data_global
#------------------ AUDIT DETAILS -------------------------------------------#
_
_
_
_
;
audit_creation_date
2014-01-19
'WinGX routine CIF_UPDATE'
'V. Kahlenberg'
audit_creation_method
audit_contact_author
audit_contact_author_address
Institut f\"ur Mineralogie und Petrographie
Leopold-Franzens-Universit\"at Innsbruck
Innrain 52
A-6020 Innsbruck
Austria
;
_
_
audit_contact_author_email Volker.Kahlenberg@uibk.ac.at
audit_contact_author_phone '+43 512 507 5503'
_audit_conform_dict_name
_audit_conform_dict_version
_audit_conform_dict_location
_audit_update_record
cif_core.dic
2.4
ftp://ftp.iucr.org/pub/cif_core.dic
?
#
------------------ AUTHOR DETAILS -------------------------------------------#
------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#
#
data_gl579_1
_
_
_
_
_
_
audit_creation_date
audit_creation_method
audit_conform_dict_name
audit_conform_dict_version
audit_conform_dict_location
publ_requested_category
2014-01-19T22:05:51-00:00
'WinGX routine CIF_UPDATE'
cif_core.dic
2.4
ftp://ftp.iucr.org/pub/cif_core.dic
FO
#
#
#
----------------------------------------------------------------------------#
CHEMICAL INFORMATION
#
----------------------------------------------------------------------------#
_chemical_name_systematic
;
?
;
_
_
_
chemical_formula_sum
chemical_formula_moiety
chemical_formula_weight
'C17 H14 F2 N2 O2'
'C17 H14 F2 N2 O2'
316.3
#
#
----------------------------------------------------------------------------#
UNIT CELL INFORMATION
#

#----------------------------------------------------------------------------#
_
_
_
symmetry_cell_setting
symmetry_space_group_name_H-M
symmetry_space_group_name_Hall
triclinic
'P -1'
'-P 1'
loop_
_
symmetry_equiv_pos_as_xyz
'
x, y, z'
'-x, -y, -z'
_
_
_
_
_
_
_
_
_
_
_
_
cell_length_a
cell_length_b
cell_length_c
cell_angle_alpha
cell_angle_beta
cell_angle_gamma
cell_volume
cell_formula_units_Z
cell_measurement_temperature
cell_measurement_reflns_used
cell_measurement_theta_min
cell_measurement_theta_max
8.6443(4)
11.2465(5)
15.7852(8)
100.013(4)
94.434(4)
93.114(4)
1503.12(12)
4
173(2)
4586
2.8038
28.8114
#
#
#
----------------------------------------------------------------------------#
CRYSTAL INFORMATION
----------------------------------------------------------------------------#
#
_
_
_
_
_
_
_
_
_
;
exptl_crystal_description
exptl_crystal_colour
'prismatic fragment'
colourless
0.52
0.2
0.2
1.398
'not measured'
656
exptl_crystal_size_max
exptl_crystal_size_mid
exptl_crystal_size_min
exptl_crystal_density_diffrn
exptl_crystal_density_method
exptl_crystal_F_000
exptl_special_details
?
;
#
#
#
----------------------------------------------------------------------------#
ABSORPTION CORRECTION
----------------------------------------------------------------------------#
#
_
_
_
;
exptl_absorpt_coefficient_mu
exptl_absorpt_correction_type
exptl_absorpt_process_details
0.109
multi-scan
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_
_
exptl_absorpt_correction_T_min
exptl_absorpt_correction_T_max
0.91558
1
#
#
#
----------------------------------------------------------------------------#
DATA COLLECTION
----------------------------------------------------------------------------#
#
_diffrn_ambient_temperature
_diffrn_radiation_wavelength
_diffrn_radiation_type
173(2)
0.71073
MoK\a

_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
diffrn_radiation_monochromator
diffrn_detector_area_resol_mean
diffrn_orient_matrix_ub_11
diffrn_orient_matrix_ub_12
diffrn_orient_matrix_ub_13
diffrn_orient_matrix_ub_21
diffrn_orient_matrix_ub_22
diffrn_orient_matrix_ub_23
diffrn_orient_matrix_ub_31
diffrn_orient_matrix_ub_32
diffrn_orient_matrix_ub_33
diffrn_measurement_device_type
diffrn_measurement_method
diffrn_reflns_av_R_equivalents
diffrn_reflns_av_unetI/netI
diffrn_reflns_number
diffrn_reflns_limit_h_min
diffrn_reflns_limit_h_max
diffrn_reflns_limit_k_min
diffrn_reflns_limit_k_max
diffrn_reflns_limit_l_min
diffrn_reflns_limit_l_max
diffrn_reflns_theta_min
graphite
10.3575
0.0579333
0.0404344
0.0258365
-0.0560603
0.0431
0.0092966
-0.0175152
-0.0250742
0.0366664
'Xcalibur, Ruby, Gemini ultra'
'\w scans'
0.0196
0.0322
9200
-10
10
-12
13
-18
19
2.81
25.35
25.35
diffrn_reflns_theta_max
diffrn_reflns_theta_full
diffrn_measured_fraction_theta_full
0
.988
.988
_diffrn_measured_fraction_theta_max
0
_
_
_
reflns_number_total
reflns_number_gt
reflns_threshold_expression
5455
4585
>2sigma(I)
#
#
#
----------------------------------------------------------------------------#
COMPUTER PROGRAMS USED
#
----------------------------------------------------------------------------#
_
;
computing_data_collection
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(
compiled Jul 11 2012,15:38:31)
;
_
;
computing_cell_refinement
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
compiled Jul 11 2012,15:38:31)
(
;
_
;
computing_data_reduction
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
compiled Jul 11 2012,15:38:31)
(
;
_
_
computing_structure_solution
computing_structure_refinement
'SIR2002 (Burla et al., 2003)'
'SHELXL-97 (Sheldrick, 1997)'
#
#
#
----------------------------------------------------------------------------#
STRUCTURE SOLUTION
----------------------------------------------------------------------------#
_
_
atom_sites_solution_primary
atom_sites_solution_secondary
direct
difmap

_atom_sites_solution_hydrogens
geom
#
#
#
----------------------------------------------------------------------------#
REFINEMENT INFORMATION
#
----------------------------------------------------------------------------#
_
;
refine_special_details
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_
_
_
_
refine_ls_structure_factor_coef
refine_ls_matrix_type
refine_ls_weighting_scheme
refine_ls_weighting_details
Fsqd
full
calc
'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.3963P] where P=(Fo^2^+2Fc^2^)/3'
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
refine_ls_hydrogen_treatment
refine_ls_extinction_method
refine_ls_number_reflns
refine_ls_number_parameters
refine_ls_number_restraints
refine_ls_R_factor_all
refine_ls_R_factor_gt
refine_ls_wR_factor_ref
refine_ls_wR_factor_gt
refine_ls_goodness_of_fit_ref
refine_ls_restrained_S_all
refine_ls_shift/su_max
refine_ls_shift/su_mean
refine_diff_density_max
refine_diff_density_min
refine_diff_density_rms
mixed
none
5455
431
4
0.0461
0.0364
0.091
0.0845
1.029
1.029
0
0
0.223
-0.221
0.04
#
#
#
----------------------------------------------------------------------------#
ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS
----------------------------------------------------------------------------#
#
loop_
_
_
_
_
_
atom_type_symbol
atom_type_description
atom_type_scat_dispersion_real
atom_type_scat_dispersion_imag
atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_
_
_
_
_
_
_
_
_
atom_site_label
atom_site_type_symbol
atom_site_fract_x
atom_site_fract_y
atom_site_fract_z
atom_site_U_iso_or_equiv
atom_site_adp_type
atom_site_occupancy
atom_site_symmetry_multiplicity

_
_
_
_
atom_site_calc_flag
atom_site_refinement_flags
atom_site_disorder_assembly
atom_site_disorder_group
O1B O 0.99620(11) 0.49382(10) 0.60707(7) 0.0290(2) Uani 1 1 d . . .
F1B F 1.05955(12) 1.08212(8) 0.64373(6) 0.0448(3) Uani 1 1 d . . .
O1A O 1.01091(11) 1.06762(9) 0.10434(6) 0.0270(2) Uani 1 1 d . . .
F1A F 1.05353(12) 0.51634(9) 0.14778(8) 0.0537(3) Uani 1 1 d . . .
N2A N 0.69018(14) 1.05106(11) -0.08893(8) 0.0232(3) Uani 1 1 d D . .
N1B N 0.81171(13) 0.61012(11) 0.56090(8) 0.0237(3) Uani 1 1 d D . .
F2A F 0.38825(13) 1.00250(11) -0.41567(6) 0.0548(3) Uani 1 1 d . . .
N1A N 0.80353(13) 0.92956(11) 0.07086(8) 0.0229(3) Uani 1 1 d D . .
F2B F 0.38837(12) 0.52230(11) 0.09616(6) 0.0545(3) Uani 1 1 d . . .
O2B O 0.50203(10) 0.34733(9) 0.46644(6) 0.0274(2) Uani 1 1 d . . .
O2A O 0.51370(11) 1.14986(9) -0.00909(7) 0.0280(2) Uani 1 1 d . . .
N2B N 0.68763(13) 0.43676(11) 0.39943(8) 0.0243(3) Uani 1 1 d D . .
C6B C 0.63489(15) 0.39205(12) 0.46612(9) 0.0215(3) Uani 1 1 d . . .
C6A C 0.64340(15) 1.11078(12) -0.01490(9) 0.0207(3) Uani 1 1 d . . .
C9B C 0.88352(15) 0.72880(13) 0.58403(9) 0.0225(3) Uani 1 1 d . . .
C10A C 0.82355(17) 0.71423(14) 0.04103(10) 0.0281(3) Uani 1 1 d . . .
H10A H 0.7478 0.7097 -0.0048 0.034 Uiso 1 1 calc R . .
C1A C 0.76512(16) 1.13611(13) 0.06031(9) 0.0222(3) Uani 1 1 d . . .
C1B C 0.75396(15) 0.39599(13) 0.54188(9) 0.0221(3) Uani 1 1 d . . .
C16A C 0.60643(16) 1.03838(13) -0.17152(9) 0.0233(3) Uani 1 1 d . . .
C21B C 0.67588(17) 0.53224(15) 0.27548(10) 0.0304(3) Uani 1 1 d . . .
H21B H 0.7737 0.5694 0.2956 0.036 Uiso 1 1 calc R . .
C9A C 0.87503(15) 0.82548(13) 0.08990(9) 0.0222(3) Uani 1 1 d . . .
C12B C 1.00043(18) 0.96492(14) 0.62403(10) 0.0312(4) Uani 1 1 d . . .
C17A C 0.51699(19) 1.12898(15) -0.19376(10) 0.0343(4) Uani 1 1 d . . .
H17A H 0.507 1.1983 -0.1533 0.041 Uiso 1 1 calc R . .
C14B C 1.00411(18) 0.76226(14) 0.64834(10) 0.0300(3) Uani 1 1 d . . .
H14B H 1.0446 0.7051 0.6783 0.036 Uiso 1 1 calc R . .
C11A C 0.88405(18) 0.60945(14) 0.05989(11) 0.0330(4) Uani 1 1 d . . .
H11A H 0.8499 0.5343 0.0273 0.04 Uiso 1 1 calc R . .
C10B C 0.82237(17) 0.81548(14) 0.54089(10) 0.0279(3) Uani 1 1 d . . .
H10B H 0.7416 0.7928 0.4977 0.034 Uiso 1 1 calc R . .
C11B C 0.87964(18) 0.93455(15) 0.56120(10) 0.0318(4) Uani 1 1 d . . .
H11B H 0.8373 0.9929 0.533 0.038 Uiso 1 1 calc R . .
C12A C 0.99560(18) 0.61922(15) 0.12783(11) 0.0343(4) Uani 1 1 d . . .
C4A C 0.87315(15) 1.04158(13) 0.07945(8) 0.0205(3) Uani 1 1 d . . .
C2B C 0.70298(18) 0.33391(14) 0.61410(10) 0.0309(4) Uani 1 1 d . . .
H2B1 H 0.746 0.3673 0.6725 0.037 Uiso 1 1 calc R . .
H2B2 H 0.5962 0.3005 0.6093 0.037 Uiso 1 1 calc R . .
C19A C 0.46061(19) 1.01452(16) -0.33441(10) 0.0354(4) Uani 1 1 d . . .
C16B C 0.60447(15) 0.45424(13) 0.32193(9) 0.0229(3) Uani 1 1 d . . .
C4B C 0.86658(15) 0.50395(13) 0.57194(8) 0.0215(3) Uani 1 1 d . . .
C14A C 0.98856(18) 0.83276(14) 0.15809(10) 0.0300(3) Uani 1 1 d . . .
H14A H 1.0235 0.9075 0.1911 0.036 Uiso 1 1 calc R . .
C13B C 1.06417(19) 0.88206(15) 0.66772(10) 0.0349(4) Uani 1 1 d . . .
H13B H 1.1466 0.9055 0.7098 0.042 Uiso 1 1 calc R . .
C21A C 0.62209(19) 0.93680(15) -0.23245(10) 0.0347(4) Uani 1 1 d . . .
H21A H 0.6827 0.8762 -0.218 0.042 Uiso 1 1 calc R . .
C19B C 0.45951(19) 0.49907(16) 0.17086(10) 0.0348(4) Uani 1 1 d . . .
C17B C 0.45913(16) 0.39745(14) 0.29077(9) 0.0268(3) Uani 1 1 d . . .
H17B H 0.4109 0.3441 0.321 0.032 Uiso 1 1 calc R . .
C3B C 0.80858(18) 0.27362(14) 0.55377(10) 0.0319(4) Uani 1 1 d . . .
H3B1 H 0.7663 0.2033 0.5122 0.038 Uiso 1 1 calc R . .
H3B2 H 0.9161 0.2702 0.5753 0.038 Uiso 1 1 calc R . .
C20A C 0.5483(2) 0.92420(16) -0.31500(10) 0.0392(4) Uani 1 1 d . . .
H20A H 0.5585 0.8557 -0.3561 0.047 Uiso 1 1 calc R . .
C18B C 0.38624(18) 0.42061(15) 0.21430(10) 0.0328(4) Uani 1 1 d . . .
H18B H 0.289 0.3832 0.193 0.039 Uiso 1 1 calc R . .
C18A C 0.4427(2) 1.11625(16) -0.27600(11) 0.0403(4) Uani 1 1 d . . .
H18A H 0.3816 1.1761 -0.2912 0.048 Uiso 1 1 calc R . .

C20B C 0.60327(18) 0.55530(16) 0.19971(10) 0.0362(4) Uani 1 1 d . . .
H20B H 0.6509 0.608 0.1688 0.043 Uiso 1 1 calc R . .
C13A C 1.04953(19) 0.72786(16) 0.17671(11) 0.0376(4) Uani 1 1 d . . .
H13A H 1.1262 0.7315 0.222 0.045 Uiso 1 1 calc R . .
C2A C 0.7238(2) 1.22269(16) 0.13825(10) 0.0392(4) Uani 1 1 d . . .
H2A1 H 0.6195 1.2505 0.1372 0.047 Uiso 1 1 calc R . .
H2A2 H 0.7678 1.2118 0.1946 0.047 Uiso 1 1 calc R . .
C3A C 0.8304(2) 1.26612(14) 0.07976(12) 0.0399(4) Uani 1 1 d . . .
H3A1 H 0.9395 1.2818 0.1004 0.048 Uiso 1 1 calc R . .
H3A2 H 0.7912 1.3204 0.043 0.048 Uiso 1 1 calc R . .
H8A H 0.7044(16) 0.9172(15) 0.0500(10) 0.036(5) Uiso 1 1 d D . .
H15A H 0.7814(17) 1.0219(15) -0.0862(11) 0.033(4) Uiso 1 1 d D . .
H15B H 0.7870(16) 0.4628(15) 0.4047(10) 0.033(4) Uiso 1 1 d D . .
H8B H 0.7161(17) 0.6085(15) 0.5390(10) 0.035(5) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1B 0.0161(5) 0.0375(6) 0.0345(6) 0.0126(5) -0.0045(4) 0.0016(4)
F1B 0.0608(6) 0.0295(5) 0.0408(6) 0.0057(4) -0.0050(5) -0.0109(5)
O1A 0.0176(5) 0.0283(6) 0.0336(6) 0.0039(5) -0.0043(4) 0.0025(4)
F1A 0.0504(6) 0.0357(6) 0.0821(8) 0.0296(6) -0.0013(6) 0.0168(5)
N2A 0.0187(6) 0.0261(7) 0.0248(6) 0.0047(5) -0.0016(5) 0.0067(5)
N1B 0.0143(6) 0.0269(7) 0.0288(7) 0.0045(5) -0.0030(5) 0.0011(5)
F2A 0.0587(7) 0.0726(8) 0.0283(5) 0.0036(5) -0.0161(5) 0.0095(6)
N1A 0.0167(6) 0.0229(6) 0.0296(7) 0.0080(5) -0.0028(5) 0.0031(5)
F2B 0.0494(6) 0.0824(8) 0.0348(5) 0.0253(6) -0.0117(5) 0.0075(6)
O2B 0.0154(5) 0.0319(6) 0.0355(6) 0.0100(5) -0.0011(4) -0.0014(4)
O2A 0.0181(5) 0.0315(6) 0.0340(6) 0.0046(5) -0.0003(4) 0.0071(4)
N2B 0.0145(6) 0.0325(7) 0.0259(6) 0.0072(5) -0.0020(5) -0.0002(5)
C6B 0.0173(7) 0.0196(7) 0.0269(7) 0.0022(6) 0.0011(6) 0.0043(6)
C6A 0.0179(7) 0.0172(7) 0.0279(8) 0.0072(6) -0.0001(6) 0.0013(5)
C9B 0.0182(7) 0.0281(8) 0.0215(7) 0.0043(6) 0.0036(6) 0.0005(6)
C10A 0.0261(8) 0.0277(8) 0.0310(8) 0.0083(7) -0.0010(6) 0.0024(6)
C1A 0.0207(7) 0.0202(7) 0.0256(7) 0.0050(6) -0.0008(6) 0.0027(6)
C1B 0.0167(7) 0.0251(8) 0.0254(7) 0.0065(6) 0.0009(6) 0.0037(6)
C16A 0.0200(7) 0.0260(8) 0.0243(7) 0.0067(6) -0.0011(6) 0.0012(6)
C21B 0.0219(7) 0.0366(9) 0.0337(8) 0.0105(7) -0.0009(6) 0.0015(6)
C9A 0.0191(7) 0.0255(8) 0.0242(7) 0.0086(6) 0.0044(6) 0.0056(6)
C12B 0.0383(9) 0.0264(8) 0.0277(8) 0.0037(7) 0.0035(7) -0.0049(7)
C17A 0.0418(9) 0.0294(9) 0.0298(8) 0.0022(7) -0.0065(7) 0.0088(7)
C14B 0.0317(8) 0.0310(9) 0.0265(8) 0.0067(7) -0.0041(6) 0.0007(7)
C11A 0.0351(9) 0.0231(8) 0.0417(9) 0.0067(7) 0.0057(7) 0.0040(7)
C10B 0.0221(7) 0.0350(9) 0.0272(8) 0.0095(7) -0.0015(6) -0.0009(6)
C11B 0.0329(8) 0.0326(9) 0.0324(8) 0.0137(7) 0.0008(7) 0.0013(7)
C12A 0.0310(8) 0.0286(9) 0.0498(10) 0.0206(8) 0.0061(8) 0.0124(7)
C4A 0.0198(7) 0.0247(8) 0.0170(7) 0.0031(6) 0.0003(5) 0.0045(6)
C2B 0.0281(8) 0.0352(9) 0.0322(8) 0.0161(7) 0.0001(7) -0.0007(7)
C19A 0.0321(8) 0.0491(11) 0.0234(8) 0.0068(7) -0.0077(7) 0.0005(8)
C16B 0.0191(7) 0.0262(8) 0.0233(7) 0.0028(6) 0.0007(6) 0.0073(6)
C4B 0.0160(7) 0.0306(8) 0.0187(7) 0.0060(6) 0.0027(6) 0.0026(6)
C14A 0.0335(8) 0.0268(8) 0.0293(8) 0.0065(7) -0.0038(7) 0.0043(7)
C13B 0.0377(9) 0.0364(9) 0.0274(8) 0.0038(7) -0.0086(7) -0.0044(7)
C21A 0.0368(9) 0.0335(9) 0.0334(9) 0.0037(7) -0.0017(7) 0.0129(7)
C19B 0.0329(9) 0.0469(10) 0.0257(8) 0.0092(7) -0.0041(7) 0.0128(8)
C17B 0.0219(7) 0.0296(8) 0.0280(8) 0.0034(6) -0.0005(6) 0.0022(6)
C3B 0.0301(8) 0.0266(8) 0.0394(9) 0.0095(7) -0.0059(7) 0.0065(7)
C20A 0.0447(10) 0.0397(10) 0.0289(9) -0.0046(7) -0.0021(7) 0.0067(8)
C18B 0.0254(8) 0.0411(10) 0.0288(8) 0.0011(7) -0.0061(7) 0.0026(7)

C18A 0.0461(10) 0.0395(10) 0.0352(9) 0.0091(8) -0.0099(8) 0.0138(8)
C20B 0.0326(9) 0.0448(10) 0.0354(9) 0.0172(8) 0.0046(7) 0.0067(8)
C13A 0.0344(9) 0.0406(10) 0.0399(9) 0.0170(8) -0.0090(7) 0.0071(8)
C2A 0.0437(10) 0.0403(10) 0.0300(9) -0.0051(7) -0.0076(7) 0.0212(8)
C3A 0.0386(9) 0.0210(8) 0.0565(11) 0.0067(8) -0.0170(8) -0.0005(7)
#
#
#
----------------------------------------------------------------------------#
MOLECULAR GEOMETRY
#
----------------------------------------------------------------------------#
_
;
geom_special_details
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_
_
_
_
_
geom_bond_atom_site_label_1
geom_bond_atom_site_label_2
geom_bond_distance
geom_bond_site_symmetry_2
geom_bond_publ_flag
O1B C4B 1.2311(15) . ?
F1B C12B 1.3619(18) . ?
O1A C4A 1.2280(16) . ?
F1A C12A 1.3616(17) . ?
N2A C6A 1.3453(18) . ?
N2A C16A 1.4221(18) . ?
N2A H15A 0.871(13) . ?
N1B C4B 1.3425(18) . ?
N1B C9B 1.4162(19) . ?
N1B H8B 0.869(13) . ?
F2A C19A 1.3642(17) . ?
N1A C4A 1.3466(19) . ?
N1A C9A 1.4194(17) . ?
N1A H8A 0.888(13) . ?
F2B C19B 1.3599(17) . ?
O2B C6B 1.2292(17) . ?
O2A C6A 1.2304(16) . ?
N2B C6B 1.3425(19) . ?
N2B C16B 1.4195(17) . ?
N2B H15B 0.886(14) . ?
C6B C1B 1.5093(18) . ?
C6A C1A 1.5014(19) . ?
C9B C14B 1.386(2) . ?
C9B C10B 1.387(2) . ?
C10A C9A 1.382(2) . ?
C10A C11A 1.384(2) . ?
C10A H10A 0.93 . ?
C1A C4A 1.5065(18) . ?
C1A C3A 1.509(2) . ?
C1A C2A 1.509(2) . ?
C1B C4B 1.499(2) . ?
C1B C3B 1.5162(19) . ?
C1B C2B 1.517(2) . ?
C16A C21A 1.380(2) . ?
C16A C17A 1.388(2) . ?
C21B C20B 1.379(2) . ?
C21B C16B 1.387(2) . ?
C21B H21B 0.93 . ?

C9A C14A 1.388(2) . ?
C12B C13B 1.367(2) . ?
C12B C11B 1.369(2) . ?
C17A C18A 1.384(2) . ?
C17A H17A 0.93 . ?
C14B C13B 1.391(2) . ?
C14B H14B 0.93 . ?
C11A C12A 1.371(2) . ?
C11A H11A 0.93 . ?
C10B C11B 1.377(2) . ?
C10B H10B 0.93 . ?
C11B H11B 0.93 . ?
C12A C13A 1.364(2) . ?
C2B C3B 1.476(2) . ?
C2B H2B1 0.97 . ?
C2B H2B2 0.97 . ?
C19A C20A 1.363(2) . ?
C19A C18A 1.363(2) . ?
C16B C17B 1.392(2) . ?
C14A C13A 1.386(2) . ?
C14A H14A 0.93 . ?
C13B H13B 0.93 . ?
C21A C20A 1.386(2) . ?
C21A H21A 0.93 . ?
C19B C18B 1.366(2) . ?
C19B C20B 1.371(2) . ?
C17B C18B 1.390(2) . ?
C17B H17B 0.93 . ?
C3B H3B1 0.97 . ?
C3B H3B2 0.97 . ?
C20A H20A 0.93 . ?
C18B H18B 0.93 . ?
C18A H18A 0.93 . ?
C20B H20B 0.93 . ?
C13A H13A 0.93 . ?
C2A C3A 1.476(3) . ?
C2A H2A1 0.97 . ?
C2A H2A2 0.97 . ?
C3A H3A1 0.97 . ?
C3A H3A2 0.97 . ?
loop_
_
_
_
_
_
_
_
geom_angle_atom_site_label_1
geom_angle_atom_site_label_2
geom_angle_atom_site_label_3
geom_angle
geom_angle_site_symmetry_1
geom_angle_site_symmetry_3
geom_angle_publ_flag
C6A N2A C16A 125.00(11) . . ?
C6A N2A H15A 117.1(11) . . ?
C16A N2A H15A 117.8(11) . . ?
C4B N1B C9B 129.77(12) . . ?
C4B N1B H8B 117.1(12) . . ?
C9B N1B H8B 113.0(11) . . ?
C4A N1A C9A 126.05(12) . . ?
C4A N1A H8A 118.6(11) . . ?
C9A N1A H8A 115.4(11) . . ?
C6B N2B C16B 129.08(12) . . ?
C6B N2B H15B 116.7(11) . . ?
C16B N2B H15B 114.1(11) . . ?
O2B C6B N2B 124.06(13) . . ?
O2B C6B C1B 121.05(13) . . ?
N2B C6B C1B 114.85(12) . . ?

O2A C6A N2A 123.37(12) . . ?
O2A C6A C1A 121.06(13) . . ?
N2A C6A C1A 115.40(11) . . ?
C14B C9B C10B 119.65(14) . . ?
C14B C9B N1B 123.89(13) . . ?
C10B C9B N1B 116.40(12) . . ?
C9A C10A C11A 120.38(14) . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A H10A 119.8 . . ?
C6A C1A C4A 121.42(12) . . ?
C6A C1A C3A 113.08(11) . . ?
C4A C1A C3A 116.99(12) . . ?
C6A C1A C2A 115.70(11) . . ?
C4A C1A C2A 115.28(12) . . ?
C3A C1A C2A 58.55(11) . . ?
C4B C1B C6B 121.12(11) . . ?
C4B C1B C3B 117.18(11) . . ?
C6B C1B C3B 114.56(12) . . ?
C4B C1B C2B 113.93(12) . . ?
C6B C1B C2B 116.04(12) . . ?
C3B C1B C2B 58.21(10) . . ?
C21A C16A C17A 119.38(13) . . ?
C21A C16A N2A 119.03(12) . . ?
C17A C16A N2A 121.48(13) . . ?
C20B C21B C16B 120.66(14) . . ?
C20B C21B H21B 119.7 . . ?
C16B C21B H21B 119.7 . . ?
C10A C9A C14A 120.05(13) . . ?
C10A C9A N1A 118.20(12) . . ?
C14A C9A N1A 121.68(13) . . ?
F1B C12B C13B 118.70(14) . . ?
F1B C12B C11B 118.79(13) . . ?
C13B C12B C11B 122.51(15) . . ?
C18A C17A C16A 120.05(15) . . ?
C18A C17A H17A 120 . . ?
C16A C17A H17A 120 . . ?
C9B C14B C13B 119.49(14) . . ?
C9B C14B H14B 120.3 . . ?
C13B C14B H14B 120.3 . . ?
C12A C11A C10A 118.35(15) . . ?
C12A C11A H11A 120.8 . . ?
C10A C11A H11A 120.8 . . ?
C11B C10B C9B 120.91(14) . . ?
C11B C10B H10B 119.5 . . ?
C9B C10B H10B 119.5 . . ?
C12B C11B C10B 118.29(14) . . ?
C12B C11B H11B 120.9 . . ?
C10B C11B H11B 120.9 . . ?
F1A C12A C13A 118.78(14) . . ?
F1A C12A C11A 118.68(15) . . ?
C13A C12A C11A 122.54(13) . . ?
O1A C4A N1A 123.97(12) . . ?
O1A C4A C1A 121.78(13) . . ?
N1A C4A C1A 114.17(12) . . ?
C3B C2B C1B 60.86(10) . . ?
C3B C2B H2B1 117.7 . . ?
C1B C2B H2B1 117.7 . . ?
C3B C2B H2B2 117.7 . . ?
C1B C2B H2B2 117.7 . . ?
H2B1 C2B H2B2 114.8 . . ?
C20A C19A C18A 122.61(14) . . ?
C20A C19A F2A 118.55(15) . . ?
C18A C19A F2A 118.84(14) . . ?
C21B C16B C17B 119.43(13) . . ?

C21B C16B N2B 116.64(13) . . ?
C17B C16B N2B 123.93(13) . . ?
O1B C4B N1B 123.94(13) . . ?
O1B C4B C1B 121.25(12) . . ?
N1B C4B C1B 114.75(11) . . ?
C13A C14A C9A 119.54(15) . . ?
C13A C14A H14A 120.2 . . ?
C9A C14A H14A 120.2 . . ?
C12B C13B C14B 119.13(14) . . ?
C12B C13B H13B 120.4 . . ?
C14B C13B H13B 120.4 . . ?
C16A C21A C20A 120.61(14) . . ?
C16A C21A H21A 119.7 . . ?
C20A C21A H21A 119.7 . . ?
F2B C19B C18B 119.23(15) . . ?
F2B C19B C20B 118.47(15) . . ?
C18B C19B C20B 122.31(14) . . ?
C18B C17B C16B 119.83(15) . . ?
C18B C17B H17B 120.1 . . ?
C16B C17B H17B 120.1 . . ?
C2B C3B C1B 60.93(9) . . ?
C2B C3B H3B1 117.7 . . ?
C1B C3B H3B1 117.7 . . ?
C2B C3B H3B2 117.7 . . ?
C1B C3B H3B2 117.7 . . ?
H3B1 C3B H3B2 114.8 . . ?
C19A C20A C21A 118.43(15) . . ?
C19A C20A H20A 120.8 . . ?
C21A C20A H20A 120.8 . . ?
C19B C18B C17B 119.03(15) . . ?
C19B C18B H18B 120.5 . . ?
C17B C18B H18B 120.5 . . ?
C19A C18A C17A 118.91(14) . . ?
C19A C18A H18A 120.5 . . ?
C17A C18A H18A 120.5 . . ?
C19B C20B C21B 118.73(16) . . ?
C19B C20B H20B 120.6 . . ?
C21B C20B H20B 120.6 . . ?
C12A C13A C14A 119.14(14) . . ?
C12A C13A H13A 120.4 . . ?
C14A C13A H13A 120.4 . . ?
C3A C2A C1A 60.72(11) . . ?
C3A C2A H2A1 117.7 . . ?
C1A C2A H2A1 117.7 . . ?
C3A C2A H2A2 117.7 . . ?
C1A C2A H2A2 117.7 . . ?
H2A1 C2A H2A2 114.8 . . ?
C2A C3A C1A 60.73(11) . . ?
C2A C3A H3A1 117.7 . . ?
C1A C3A H3A1 117.7 . . ?
C2A C3A H3A2 117.7 . . ?
C1A C3A H3A2 117.7 . . ?
H3A1 C3A H3A2 114.8 . . ?
loop_
_
_
_
_
_
_
_
_
_
geom_torsion_atom_site_label_1
geom_torsion_atom_site_label_2
geom_torsion_atom_site_label_3
geom_torsion_atom_site_label_4
geom_torsion
geom_torsion_site_symmetry_1
geom_torsion_site_symmetry_2
geom_torsion_site_symmetry_3
geom_torsion_site_symmetry_4

_geom_torsion_publ_flag
C16B N2B C6B O2B 7.1(2) . . . . ?
C16B N2B C6B C1B -175.07(13) . . . . ?
C16A N2A C6A O2A 8.4(2) . . . . ?
C16A N2A C6A C1A -166.92(12) . . . . ?
C4B N1B C9B C14B -23.1(2) . . . . ?
C4B N1B C9B C10B 159.61(14) . . . . ?
O2A C6A C1A C4A 141.57(14) . . . . ?
N2A C6A C1A C4A -42.96(18) . . . . ?
O2A C6A C1A C3A -71.45(18) . . . . ?
N2A C6A C1A C3A 104.02(15) . . . . ?
O2A C6A C1A C2A -6.6(2) . . . . ?
N2A C6A C1A C2A 168.90(13) . . . . ?
O2B C6B C1B C4B -141.02(14) . . . . ?
N2B C6B C1B C4B 41.07(17) . . . . ?
O2B C6B C1B C3B 69.37(17) . . . . ?
N2B C6B C1B C3B -108.54(14) . . . . ?
O2B C6B C1B C2B 4.29(19) . . . . ?
N2B C6B C1B C2B -173.62(12) . . . . ?
C6A N2A C16A C21A -150.53(15) . . . . ?
C6A N2A C16A C17A 33.4(2) . . . . ?
C11A C10A C9A C14A 0.3(2) . . . . ?
C11A C10A C9A N1A -176.73(13) . . . . ?
C4A N1A C9A C10A -147.71(14) . . . . ?
C4A N1A C9A C14A 35.3(2) . . . . ?
C21A C16A C17A C18A 0.9(2) . . . . ?
N2A C16A C17A C18A 176.99(15) . . . . ?
C10B C9B C14B C13B -1.2(2) . . . . ?
N1B C9B C14B C13B -178.34(14) . . . . ?
C9A C10A C11A C12A 0.0(2) . . . . ?
C14B C9B C10B C11B -0.1(2) . . . . ?
N1B C9B C10B C11B 177.26(13) . . . . ?
F1B C12B C11B C10B 179.02(14) . . . . ?
C13B C12B C11B C10B -0.9(2) . . . . ?
C9B C10B C11B C12B 1.2(2) . . . . ?
C10A C11A C12A F1A 178.78(14) . . . . ?
C10A C11A C12A C13A -0.5(2) . . . . ?
C9A N1A C4A O1A 1.0(2) . . . . ?
C9A N1A C4A C1A -175.85(12) . . . . ?
C6A C1A C4A O1A 141.06(14) . . . . ?
C3A C1A C4A O1A -4.7(2) . . . . ?
C2A C1A C4A O1A -70.68(18) . . . . ?
C6A C1A C4A N1A -41.98(18) . . . . ?
C3A C1A C4A N1A 172.26(13) . . . . ?
C2A C1A C4A N1A 106.28(15) . . . . ?
C4B C1B C2B C3B -108.24(13) . . . . ?
C6B C1B C2B C3B 103.97(14) . . . . ?
C20B C21B C16B C17B 1.0(2) . . . . ?
C20B C21B C16B N2B -179.56(14) . . . . ?
C6B N2B C16B C21B 162.26(14) . . . . ?
C6B N2B C16B C17B -18.3(2) . . . . ?
C9B N1B C4B O1B 0.8(2) . . . . ?
C9B N1B C4B C1B 177.81(13) . . . . ?
C6B C1B C4B O1B -150.93(13) . . . . ?
C3B C1B C4B O1B -2.07(19) . . . . ?
C2B C1B C4B O1B 63.09(17) . . . . ?
C6B C1B C4B N1B 31.94(17) . . . . ?
C3B C1B C4B N1B -179.20(12) . . . . ?
C2B C1B C4B N1B -114.04(13) . . . . ?
C10A C9A C14A C13A -0.1(2) . . . . ?
N1A C9A C14A C13A 176.88(14) . . . . ?
F1B C12B C13B C14B 179.70(14) . . . . ?
C11B C12B C13B C14B -0.4(3) . . . . ?
C9B C14B C13B C12B 1.4(2) . . . . ?

C17A C16A C21A C20A -0.6(2) . . . . ?
N2A C16A C21A C20A -176.79(15) . . . . ?
C21B C16B C17B C18B -0.9(2) . . . . ?
N2B C16B C17B C18B 179.74(13) . . . . ?
C4B C1B C3B C2B 102.60(14) . . . . ?
C6B C1B C3B C2B -106.53(14) . . . . ?
C18A C19A C20A C21A 0.0(3) . . . . ?
F2A C19A C20A C21A 179.82(15) . . . . ?
C16A C21A C20A C19A 0.2(3) . . . . ?
F2B C19B C18B C17B -179.78(14) . . . . ?
C20B C19B C18B C17B 0.5(2) . . . . ?
C16B C17B C18B C19B 0.1(2) . . . . ?
C20A C19A C18A C17A 0.3(3) . . . . ?
F2A C19A C18A C17A -179.53(16) . . . . ?
C16A C17A C18A C19A -0.8(3) . . . . ?
F2B C19B C20B C21B 179.90(14) . . . . ?
C18B C19B C20B C21B -0.4(3) . . . . ?
C16B C21B C20B C19B -0.4(2) . . . . ?
F1A C12A C13A C14A -178.51(14) . . . . ?
C11A C12A C13A C14A 0.8(3) . . . . ?
C9A C14A C13A C12A -0.5(2) . . . . ?
C6A C1A C2A C3A -102.45(14) . . . . ?
C4A C1A C2A C3A 107.43(14) . . . . ?
C6A C1A C3A C2A 106.97(13) . . . . ?
C4A C1A C3A C2A -104.49(14) . . . . ?
loop_
_
_
_
_
_
_
_
_
geom_hbond_atom_site_label_D
geom_hbond_atom_site_label_H
geom_hbond_atom_site_label_A
geom_hbond_distance_DH
geom_hbond_distance_HA
geom_hbond_distance_DA
geom_hbond_angle_DHA
geom_hbond_site_symmetry_A
N1A H8A O2A 0.888(13) 2.007(14) 2.8786(15) 166.5(16) 2_675
N2A H15A O1A 0.871(13) 2.120(14) 2.9793(15) 168.7(15) 2_775
N2B H15B O1B 0.886(14) 1.941(14) 2.8159(15) 169.0(16) 2_766
N1B H8B O2B 0.869(13) 1.975(14) 2.7933(15) 156.4(16) 2_666
#
END of CIF

data_s412
_
_
_
_
_
_
_
_
audit_creation_method
shelx_SHELXL_version_number
chemical_name_systematic
chemical_name_common
chemical_melting_point
chemical_formula_moiety
chemical_formula_sum
'SHELXL-2014/7'
'2014/7'
?
?
?
'C17 H16 N2 O3'
'C17 H16 N2 O3'
296.32
chemical_formula_weight
loop_
_
_
_
_
_
'
'
'
'
'
'
'
'
atom_type_symbol
atom_type_description
atom_type_scat_dispersion_real
atom_type_scat_dispersion_imag
atom_type_scat_source
C' 'C'
International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H' 'H' 0.0000 0.0000
International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N' 'N' 0.0061 0.0033
International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O' 'O' 0.0106 0.0060
International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
0.0033
0.0016
_space_group_crystal_system
_space_group_IT_number
_space_group_name_H-M_alt
_space_group_name_Hall
monoclinic
9
'C c'
'C -2yc'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_
'
'
'
'
space_group_symop_operation_xyz
x, y, z'
x, -y, z+1/2'
x+1/2, y+1/2, z'
x+1/2, -y+1/2, z+1/2'
_
_
_
_
_
_
_
_
_
_
_
_
cell_length_a
cell_length_b
cell_length_c
cell_angle_alpha
cell_angle_beta
cell_angle_gamma
cell_volume
cell_formula_units_Z
cell_measurement_temperature
cell_measurement_reflns_used
cell_measurement_theta_min
cell_measurement_theta_max
19.8309(4)
9.5212(4)
7.6800(6)
90
92.652(3)
90
1448.54(13)
4
233(2)
19700
1.0
25.2
_
_
_
_
exptl_crystal_description
exptl_crystal_colour
exptl_crystal_density_meas
exptl_crystal_density_method
prism
colourless
?
?

_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
exptl_crystal_density_diffrn
exptl_crystal_F_000
exptl_transmission_factor_min
exptl_transmission_factor_max
exptl_crystal_size_max
exptl_crystal_size_mid
exptl_crystal_size_min
exptl_absorpt_coefficient_mu
shelx_estimated_absorpt_T_min
shelx_estimated_absorpt_T_max
exptl_absorpt_correction_type
exptl_absorpt_correction_T_min
exptl_absorpt_correction_T_max
exptl_absorpt_process_details
exptl_absorpt_special_details
diffrn_ambient_temperature
diffrn_radiation_wavelength
diffrn_radiation_type
1.359
624
?
?
0.41
0.11
0.09
0.094
?
?
none
?
?
?
?
233(2)
0.71073
MoK\a
?
'Nonius KappaCCD'
'phi- and omega-scans'
?
4441
0.0429
0.0220
-23
23
-11
11
-9
9
diffrn_source
diffrn_measurement_device_type
diffrn_measurement_method
diffrn_detector_area_resol_mean
diffrn_reflns_number
diffrn_reflns_av_unetI/netI
diffrn_reflns_av_R_equivalents
diffrn_reflns_limit_h_min
diffrn_reflns_limit_h_max
diffrn_reflns_limit_k_min
diffrn_reflns_limit_k_max
diffrn_reflns_limit_l_min
diffrn_reflns_limit_l_max
diffrn_reflns_theta_min
diffrn_reflns_theta_max
diffrn_reflns_theta_full
diffrn_measured_fraction_theta_max
diffrn_measured_fraction_theta_full 0.991
diffrn_reflns_Laue_measured_fraction_max
diffrn_reflns_Laue_measured_fraction_full
diffrn_reflns_point_group_measured_fraction_max
diffrn_reflns_point_group_measured_fraction_full 0.978
reflns_number_total
reflns_number_gt
reflns_threshold_expression
reflns_Friedel_coverage
reflns_Friedel_fraction_max
reflns_Friedel_fraction_full
2.373
24.994
24.994
0.991
0.991
0.991
0.978
2492
2254
'I > 2\s(I)'
0.970
0.965
0.965
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_
reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_
_
_
_
_
_
computing_data_collection
computing_cell_refinement
computing_data_reduction
computing_structure_solution
computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
computing_molecular_graphics
COLLECT
?
'DENZO and SCALEPACK'
?
?