2744 Crystal Growth & Design, Vol. 10, No. 6, 2010
Carvalho et al.
Acknowledgment. We are grateful to the Academic Re-
search Program (ARP) of the Department of National De-
fence for funding. Thanks to Elena Nadezhina for elemental
analysis.
(16) Lebel, O.; Maris, T.; Wuest, J. D. Can. J. Chem. 2006, 84, 1426–
1433.
(17) Elpern, B. Ann. N. Y. Acad. Sci. 1968, 148, 577–586.
(18) Using higher-boiling solvents such as DMF and DMSO was
attempted, but since it proved impossible to remove them comple-
tely without heating at elevated temperatures, the compounds
could not be obtained in pure form this way.
Supporting Information Available: Spectroscopic data for salts
3-53, representative TGA thermograms of salts 23 and 37, addi-
tional views of the crystal structures and Hirshfeld surfaces for
compounds 1, 2, 5, 8, 23, 37, and 48, and input and output data for
DFT calculations on biguanide 1. This material is available free of
(19) Crystal data for 1: C18H23N5, M = 309.41, monoclinic, P21/c
˚
(No. 14), a = 14.3364(3), b = 7.5018(2), c = 16.4621(3) A,
o
3
˚
β=107.7160(10) , V=1686.52(6) A , Z=4, T=180(2) K, Fcalc
=
1.219 g cm-3, μ(MoκR) 0.076 mm-1, F(000)=664, Bruker SMART
APEX II diffractometer, total reflections=6638, independent reflec-
tions=3292, Rint=0.0215, 216 parameters, F2 refinement, R1=0.0464,
wR2=0.1177, GOF=1.040, residuals based on [I > 2σΔI(I)].
References
(20) Crystal data for 2: C19H28ClN5O, M=377.91, monoclinic, P21/c
˚
(No. 14), a = 12.3594(6), b = 15.7342(10), c = 11.1135(6) A,
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β=110.845(3) , V=2019.73(19) A , Z=4, T=180(2) K, Fcalc
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1.243 g cm-3, μ(MoκR) 0.207 mm-1, F(000)=808, Bruker SMART
APEX II diffractometer, total reflections=8592, independent reflec-
tions=3961, Rint=0.0342, 243 parameters, F2 refinement, R1=0.0534,
wR2=0.1384, GOF=1.026, residuals based on [I > 2σΔI(I)].
(21) Crystal data for 5: C18H24N6O3, M=372.43, monoclinic, P21/c
˚
(No. 14), a = 9.7519(13), b = 26.693(4), c = 8.1555(11) A,
o
3
˚
β=114.2770(10) , V=1928.1(4) A , Z=4, T=180(2) K, Fcalc
=
1.283 g cm-3, μ(MoκR) 0.091 mm-1, F(000)=792, Bruker SMART
APEX II diffractometer, total reflections = 19205, independent
reflections=3774, Rint=0.0296, 256 parameters, F2 refinement, R1=
0.0398, wR2=0.1016, GOF=1.040, residuals based on [I > 2σΔI(I)].
(22) Crystal data for 8: C19H25N5O2, M=355.44, monoclinic, P21/c
˚
(No. 14), a = 13.6022(9), b = 14.0171(9), c = 11.8585(8) A,
o
3
˚
β=115.6920(10) , V=2037.5(2) A , Z=4, T=180(2) K, Fcalc
=
1.159 g cm-3, μ(MoκR) 0.078 mm-1, F(000)=760, Bruker SMART
APEX II diffractometer, total reflections = 20185, independent
reflections=4004, Rint =0.0242, 239 parameters, F2 refinement,
R1=0.0373, wR2=0.0959, GOF=1.032, residuals based on [I >
2σΔI(I)].
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(24) Crystal data for 37: C29H39N5O3, M=505.65, triclinic, P1 (No. 2),
˚
o
a=9.1806(2), b=13.0902(2), c=13.2424(2) A, R=113.0640(10) , β=
o
o
3
˚
94.3590(10) , γ=91.1590(10) , V=1457.81(4) A , Z=2, T=180(2)
K, Fcalc=1.152 g cm-3, μ(MoκR) 0.076 mm-1, F(000)=544, Bruker
SMART APEX II diffractometer, total reflections=13 469, inde-
pendent reflections=5711, Rint=0.0207, 362 parameters, F2 refine-
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[I > 2σΔI(I)].
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˚
o
a = 9.7875(19), b = 10.587(2), c = 12.438(3) A, R = 93.946(3) ,
o
o
3
˚
β=109.581(2) , γ=114.975(2) , V=1066.9(4) A , Z=1, T=180(2)
K, Fcalc=1.191 g cm-3, μ(MoκR) 0.079 mm-1, F(000)=410, Bruker
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[I > 2σΔI(I)].
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˚
o
(No. 2), a=13.574(2), b=18.461(3), c=22.346(4)A, R=111.710(3) ,
o
o
3
˚
β=94.025(2) , γ=91.123(2) , V=5183.6(15) A , Z=4, T=180(2) K,
F
calc=1.131 g cm-3, μ(MoκR) 0.076 mm-1, F(000)=1893, Bruker
SMART APEX II diffractometer, total reflections=47654, inde-
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refinement, R1 = 0.1029, wR2 = 0.2697, GOF = 1.032, residuals
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