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#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2101158.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2101158
loop_
_publ_author_name
'Heine, A.'
'Herbst-Irmer, R.'
'Stalke, D.'
'K\"uhnle, W.'
'Zachariasse, K. A.'
_publ_section_title
;
 Structure and crystal packing of 4-aminobenzonitriles and
 4-amino-3,5-dimethylbenzonitriles at various temperatures
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              363
_journal_page_last               373
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.2
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_beta                 98.99(2)
_cell_formula_units_Z            16
_cell_length_a                   17.100(2)
_cell_length_b                   22.385(2)
_cell_length_c                   8.747(2)
_cell_volume                     3307.1(6)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.07
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_F_000             1248
_[local]_cod_data_source_file    se0122.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) .39160(10) .31540(10) .5574(3) .0350(10)
C(1) .33420(10) .31580(10) .4307(3) .0300(10)
C(2) .30830(10) .26150(10) .3573(3) .0280(10)
C(3) .24790(10) .26270(10) .2332(3) .0290(10)
C(4) .2128(2) .31670(10) .1762(3) .0280(10)
C(5) .2409(2) .36980(10) .2485(3) .0310(10)
C(6) .29990(10) .37060(10) .3735(3) .0280(10)
C(7) .3452(2) .20380(10) .4163(3) .0350(10)
C(8) .3287(2) .42770(10) .4511(3) .0400(10)
C(9) .1517(2) .31760(10) .0476(3) .0340(10)
N(2) .1016(2) .31930(10) -.0576(3) .0430(10)
N(3) .5000 .71570(10) .7500 .0340(10)
C(10) .5000 .6548(2) .7500 .0280(10)
C(11) .45040(10) .62340(10) .6324(3) .0270(10)
C(12) .4513(2) .56210(10) .6356(3) .0300(10)
C(13) .5000 .5302(2) .7500 .0270(10)
C(14) .3979(2) .65710(10) .5098(3) .0360(10)
C(15) .5000 .4670(2) .7500 .0320(10)
N(4) .5000 .4154(2) .7500 .0430(10)
N(5) .5000 -.08110(10) .7500 .0410(10)
C(16) .5000 -.0201(2) .7500 .0310(10)
C(17) .55810(10) .01130(10) .8522(3) .0280(10)
C(18) .5562(2) .07280(10) .8504(3) .0330(10)
C(19) .5000 .1045(2) .7500 .0280(10)
C(20) .6196(2) -.02240(10) .9585(3) .0380(10)
C(21) .5000 .1679(2) .7500 .0340(10)
N(6) .5000 .2194(2) .7500 .0430(10)
H(1B) .4174(15) .2801(9) .591(3) .040(4)
H(1A) .4146(15) .3511(10) .597(3) .040(4)
H(3) .22950(10) .22620(10) .1850(3) .035
H(5) .2182(2) .40660(10) .2095(3) .037
H(7A) .3386(9) .1984(4) .5247(6) .052
H(7B) .4018(2) .2043(3) .4085(18) .052
H(7C) .3195(7) .17070(10) .3542(12) .052
H(8A) .3850(3) .4329(4) .4447(18) .060
H(8B) .3214(10) .4264(3) .5599(6) .060
H(8C) .2985(7) .46120(10) .3994(13) .060
H(3A) .5341(14) .7374(12) .824(3) .040(4)
H(12) .4178(2) .54080(10) .5574(3) .036
H(14A) .4301(2) .6829(6) .4541(13) .055
H(14B) .3608(7) .6816(6) .5576(4) .055
H(14C) .3681(8) .62880(10) .4372(11) .055
H(5A) .5365(14) -.1027(12) .819(3) .040(4)
H(18) .5945(2) .09420(10) .9198(3) .039
H(20A) .6513(7) -.0465(6) .8975(3) .057
H(20B) .5937(2) -.0486(6) 1.0251(14) .057
H(20C) .6541(7) .00590(10) 1.0228(14) .057
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(1) 1.360(4)
N(1) H(1A) 0.93(2)
C(1) C(6) 1.417(3)
C(2) C(7) 1.494(3)
C(3) H(3) 0.95
C(4) C(9) 1.410(4)
C(5) H(5) 0.95
C(7) H(7A) 0.98
C(7) H(7C) 0.98
C(8) H(8B) 0.98
C(9) N(2) 1.156(4)
N(3) H(3A) 0.93(2)
C(10) C(11)* 1.414(3)
C(11) C(14) 1.491(4)
C(12) H(12) 0.95
C(13) C(15) 1.416(6)
C(14) H(14B) 0.98
C(15) N(4) 1.154(5)
N(5) H(5A) 0.93(2)
C(16) C(17)* 1.415(3)
C(17) C(20) 1.494(4)
C(18) H(18) 0.95
C(19) C(21) 1.418(5)
C(20) H(20B) 0.98
C(21) N(6) 1.152(5)
N(1) H(1B) 0.93(2)
C(1) C(2) 1.413(3)
(2) C(3) 1.377(4)
C(3) C(4) 1.404(3)
C(4) C(5) 1.395(3)
C(5) C(6) 1.368(4)
C(6) C(8) 1.494(4)
C(7) H(7B) 0.98
C(8) H(8A) 0.98
C(8) H(8C) 0.98
N(3) C(10) 1.364(5)
C(10) C(11) 1.414(3)
C(11) C(12) 1.372(4)
C(12) C(13) 1.395(3)
C(13) C(12)* 1.395(3)
C(14) H(14A) 0.98
C(14) H(14C) 0.98
N(5) C(16) 1.367(5)
C(16) C(17) 1.415(3)
C(17) C(18) 1.378(4)
C(18) C(19) 1.392(3)
C(19) C(18)* 1.392(3)
C(20) H(20A) 0.98
C(20) H(20C) 0.98
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(18) C(19) C(21) 120.7(2)
C(17) C(20) H(20B) 109.47(14)
C(17) C(20) H(20C) 109.47(14)
H(20B) C(20) H(20C) 109.5
C(1) N(1) H(1B) 120(2)
H(1B) N(1) H(1A) 118(3)
N(1) C(1) C(6) 119.9(2)
C(3) C(2) C(1) 119.0(2)
C(1) C(2) C(7) 120.1(2)
C(2) C(3) H(3) 119.2(2)
C(5) C(4) C(3) 118.3(2)
C(3) C(4) C(9) 121.2(2)
C(6) C(5) H(5) 118.9(2)
C(5) C(6) C(1) 119.0(2)
C(1) C(6) C(8) 119.5(2)
C(2) C(7) H(7B) 109.47(13)
C(2) C(7) H(7C) 109.47(14)
H(7B) C(7) H(7C) 109.5
C(6) C(8) H(8B) 109.47(14)
C(6) C(8) H(8C) 109.47(14)
H(8B) C(8) H(8C) 109.5
C(10) N(3) H(3A) 121(2)
N(3) C(10) C(11)* 119.8(2)
(12) C(11) C(10) 118.6(2)
C(10) C(11) C(14) 119.8(2)
C(11) C(12) H(12) 119.0(2)
C(12)* C(13) C(12) 118.4(3)
C(12) C(13) C(15) 120.8(2)
C(11) C(14) H(14B) 109.47(13)
C(11) C(14) H(14C) 109.47(14)
H(14B) C(14) H(14C) 109.5
C(16) N(5) H(5A) 121(2)
N(5) C(16) C(17) 119.7(2)
C(18) C(17) C(16) 118.4(3)
C(16) C(17) C(20) 120.0(3)
C(17) C(18) H(18) 119.0(2)
C(18) C(19) C(18) 118.5(3)
C(17) C(20) H(20A) 109.47(14)
H(20A) C(20) H(20B) 109.5
H(20A) C(20) H(20C) 109.5
N(6) C(21) C(19) 180.0
C(1) N(1) H(1A) 120(2)
N(1) C(1) C(2) 120.0(2)
C(2) C(1) C(6) 120.0(2)
C(3) C(2) C(7) 120.9(2)
C(2) C(3) C(4) 121.6(2)
C(4) C(3) H(3) 119.2(2)
C(5) C(4) C(9) 120.5(2)
C(6) C(5) C(4) 122.1(2)
C(4) C(5) H(5) 118.9(2)
C(5) C(6) C(8) 121.6(2)
C(2) C(7) H(7A) 109.47(13)
H(7A) C(7) H(7B) 109.5
H(7A) C(7) H(7C) 109.5
C(6) C(8) H(8A) 109.47(14)
H(8A) C(8) H(8B) 109.5
H(8A) C(8) H(8C) 109.5
N(2) C(9) C(4) 179.0(3)
N(3) C(10) C(11) 119.8(2)
C(11) C(10) C(11)* 120.4(3)
C(12) C(11) C(14) 121.6(2)
C(11) C(12) C(13) 122.0(2)
C(13) C(12) H(12) 119.0(2)
C(12)* C(13) C(15) 120.8(2)
C(11) C(14) H(14A) 109.47(14)
H(14A) C(14) H(14B) 109.5
H(14A) C(14) H(14C) 109.5
N(4) C(15) C(13) 180.0
N(5) C(16) C(17) 119.7(2)
C(17) C(16) C(17)* 120.5(3)
C(18) C(17) C(20) 121.6(2)
C(17) C(18) C(19) 122.1(3)
C(19) C(18) H(18) 119.0(2)
C(18)* C(19) C(21) 120.7(2)
_cod_database_code 2101158