#------------------------------------------------------------------------------
#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/11/2101115.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_2101115
loop_
_publ_author_name
'Bannister, C.'
'Burns, K.'
'Prout, K.'
'Watkin, D. J.'
'Cooper, D. G.'
'Durant, G. J.'
'Ganellin, C. R.'
'Ife, R. J.'
'Sach, G. S.'
_publ_section_title
;
 Structures of histamine H₁-receptor antagonists derived from the
 cimetidine group of histamine H₂-receptor antagonists
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              221
_journal_page_last               243
_journal_paper_doi               10.1107/S0108768193010407
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C12 H16 Br N5 O S'
_chemical_formula_weight         358.26
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                95.77(2)
_cell_angle_beta                 113.86(2)
_cell_angle_gamma                106.910(10)
_cell_formula_units_Z            4
_cell_length_a                   14.295(2)
_cell_length_b                   12.447(2)
_cell_length_c                   9.917(2)
_cell_volume                     1495.2(6)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    5.096
_exptl_crystal_density_diffrn    1.59
_exptl_crystal_F_000             728
_cod_data_source_file            ha0121.cif
_cod_data_source_block           ha0121c
_cod_original_cell_volume        1495.18
_cod_database_code               2101115
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) -.1057(2) .0350(3) -.2581(3) .0486
C(2) -.1603(3) .0174(4) -.1751(4) .0480
C(3) -.1146(3) .0762(3) -.0260(4) .0402
Br(4) -.19840(3) .05224(4) .08231(5) .0564
C(5) -.0069(3) .1529(3) .0445(4) .0445
C(6) .0509(3) .1717(3) -.0395(4) .0437
C(7) .1683(3) .2552(4) .0372(6) .0639
C(8) -.0026(3) .1112(3) -.1933(4) .0398
C(9) .0502(3) .1277(4) -.2981(5) .0513
C(10) -.0136(3) .1672(3) -.4349(4) .0453
C(11) -.0201(3) .2840(3) -.3904(3) .0375
C(12) -.0953(3) .3187(4) -.2540(4) .0377
N(13) -.0429(2) .3579(3) -.6185(3) .0332
C(14) -.0968(2) .3835(3) -.7445(3) .0341
S(16) -.24720(10) .36840(10) -.98750(10) .0390
S(26) -.21660(10) .4686(2) -.9136(2) .0350
N(15) -.2056(3) .3545(7) -.8102(4) .0359
N(25) -.1913(5) .3991(9) -.7765(9) .0356
O(27) -.3138(4) .3888(6) -1.0541(5) .0480
O(17) -.2971(4) .4587(4) -1.0029(6) .0431
N(18) -.1222(2) .4298(7) -.9787(5) .0352
N(28) -.1056(5) .4795(9) -.9416(9) .0362
C(19) -.0467(2) .4301(3) -.8434(3) .0343
N(20) .0573(2) .4517(3) -.8094(3) .0363
N(101) -.4169(2) -.1559(3) .5539(3) .0420
C(102) -.3832(3) -.1017(3) .4620(4) .0444
C(103) -.4569(3) -.0863(3) .3312(3) .0389
Br(104) -.40567(4) -.01079(4) .20454(5) .0591
C(105) -.5664(3) -.1237(3) .2944(4) .0415
C(106) -.6023(3) -.1796(3) .3878(3) .0397
C(107) -.7211(3) -.2230(5) .3497(5) .0564
C(108) -.5233(2) -.1937(3) .5190(3) .0342
C(109) -.5580(3) -.2542(3) .6252(3) .0402
C(110) -.4646(3) -.2483(3) .7744(3) .0372
C(111) -.5079(2) -.3023(3) .8783(3) .0357
C(112) -.4169(2) -.3060(3) 1.0237(3) .0338
N(113) -.4622(2) -.3550(3) 1.1213(3) .0326
C(114) -.4015(2) -.3626(3) 1.2570(3) .0342
S(116) -.25321(8) -.32980(10) 1.50730(10) .0411
S(126) -.2655(2) -.4293(3) 1.4355(3) .0335
N(115) -.2926(2) -.3139(4) 1.3307(3) .0401(8)
N(125) -.2997(4) -.3605(7) 1.2978(8) .0140(10)
O(127) -.1690(4) -.3493(5) 1.5754(5) .0160(10)
O(117) -.1886(3) -.4072(3) 1.5289(5) .0601(9)
N(118) -.3758(2) -.4097(3) 1.4919(3) .0359(7)
N(128) -.3803(4) -.4530(7) 1.4581(7) .0130(10)
C(119) -.4502(2) -.4179(3) 1.3535(3) .0332
N(120) -.5567(2) -.4604(3) 1.3086(3) .0370
H(1) -.2370(3) -.0409(4) -.2242(4) .080(10)
H(2) .0284(3) .1943(3) .1544(4) .080(10)
H(3) .1901(3) .3003(4) .1540(6) .130(10)
H(4) .1768(3) .3137(4) -.0232(6) .130(10)
H(5) .2186(3) .2123(4) .0429(6) .130(10)
H(6) .1253(3) .1889(4) -.2395(5) .069(4)
H(7) .0564(3) .0532(4) -.3334(5) .069(4)
H(8) .0218(3) .1719(3) -.5040(4) .069(4)
H(9) -.0901(3) .1085(3) -.4900(4) .069(4)
H(10) .0557(3) .3439(3) -.3462(3) .069(4)
H(11) -.0468(3) .2816(3) -.3114(3) .069(4)
H(12) -.1129(3) .3833(4) -.4841(4) .069(4)
H(13) -.1647(3) .2503(4) -.5872(4) .069(4)
H(14) .0271(2) .3635(3) -.5893(3) .069(4)
H(15) .0803(2) .4951(3) -.8694(3) .053(8)
H(16) .1026(2) .4488(2) -.7225(3) .053(8)
H(101) -.3033(3) -.0732(3) .4890(4) .080(10)
H(102) -.6200(3) -.1117(3) .1999(4) .080(10)
H(103) -.7515(3) -.2978(5) .3565(5) .110(10)
H(104) -.7313(3) -.1695(5) .4203(5) .110(10)
H(105) -.7634(3) -.2197(5) .2425(5) .110(10)
H(106) -.6058(3) -.2187(3) .6489(3) .068(4)
H(107) -.6013(3) -.3378(3) .5708(3) .068(4)
H(108) -.4166(3) -.1652(3) .8260(3) .068(4)
H(109) -.4207(3) -.2911(3) .7534(3) .068(4)
H(110) -.5468(2) -.2555(3) .9055(3) .068(4)
H(111) -.5607(2) -.3833(3) .8229(3) .068(4)
H(112) -.3629(2) -.2254(3) 1.0791(3) .068(4)
H(113) -.3790(2) -.3547(3) .9979(3) .068(4)
H(114) -.5357(2) -.3813(3) 1.0853(3) .068(4)
H(115) -.5819(2) -.4801(3) 1.3778(3) .070(10)
H(116) -.6098(2) -.4716(3) 1.2001(3) .070(10)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) N(1) C(8) 119.2(3)
C(3) C(2) N(10 122.2(3)
C(5) C(3) C(2) 119.5(3)
Br(4) C(3) C(2) 120.1(3)
Br(4) C(3) C(5) 120.5(3)
C(6) C(5) C(3) 119.0(3)
C(8) C(6) C(5) 118.3(3)
C(7) C(6) C(5) 119.0(3)
C(7) C(6) C(8) 122.7(3)
C(6) C(8) N(1) 121.8(3)
C(9) C(8) N(1) 115.0(3)
C(9) C(8) C(6) 123.2(3)
C(10) C(9) C(8) 112.6(3)
C(9) C(10) C(11) 112.7(3)
C(12) C(11) C(10) 113.6(3)
C(11) C(12) N(13) 111.2(2)
C(12) N(13) C(14) 120.6(2)
N(15) C(14) N(13) 123.0(3)
N(25) C(14) N(13) 122.0(3)
C(19) C(14) N(13) 123.6(2)
C(19) C(14) N(15) 112.7(2)
C(19) C(14) N(25) 112.4(3)
S(16) N(15) C(14) 108.7(2)
S(26) N(25) C(14) 108.8(3)
N(15) S(16) O(17) 108.3(3)
N(25) S(26) O(27) 108.9(5)
N(18) S(16) O(17) 106.6(3)
N(28) S(26) O(27) 106.4(5)
N(18) S(16) N(15) 97.9(2)
N(28) S(26) N(25) 98.4(2)
S(16) N(18) C(19) 107.9(2)
S(26) N(28) C(19) 107.3(3)
N(18) C(19) N(20) 123.8(3)
N(28) C(19) N(20) 121.0(3)
C(14) C(19) N(20) 123.1(2)
C(14) C(19) N(18) 112.3(2)
C(14) C(19) N(28) 113.1(3)
C(102) N(101) C(108) 119.6(3)
C(103) C(102) N(101) 121.0(3)
C(102) C(103) C(105) 120.2(3)
Br(104) C(103) C(105) 120.3(2)
Br(104) C(103) C(102) 119.5(3)
C(106) C(105) C(103) 119.4(3)
C(108) C(106) C(105) 117.8(3)
C(107) C(106) C(105) 120.7(3)
C(107) C(106) C(108) 121.5(3)
C(106) C(108) N(101) 122.1(3)
C(109) C(108) N(101) 118.0(3)
C(109) C(108) C(106) 119.9(3)
C(110) C(109) C(108) 115.1(3)
C(111) C(110) C(109) 111.1(3)
C(110) C(111) C(112) 112.4(2)
C(111) C(112) N(113) 110.2(2)
C(112) N(113) C(114) 123.1(2)
N(115) C(114) N(113) 124.7(3)
N(125) C(114) N(113) 121.3(3)
C(119) C(114) N(113) 122.2(2)
C(119) C(114) N(115) 112.7(2)
C(119) C(114) N(125) 112.6(3)
S(116) N(115) C(114) 107.5(2)
S(126) N(125) C(114) 109.6(3)
N(115) S(116) O(117) 108.1(2)
N(125) S(126) O(127) 110.5(4)
N(118) S(116) O(117) 106.2(2)
N(128) S(126) O(127) 109.6(4)
N(118) S(116) N(115) 99.30(10)
N(128) S(126) N(125) 96.4(2)
S(116) N(118) C(119) 106.7(2)
S(126) N(128) C(119) 109.8(3)
N(118) C(119) N(120) 123.5(2)
N(128) C(119) N(120) 122.4(3)
C(114) C(119) N(120) 122.7(2)
C(114) C(119) N(118) 113.5(2)
C(114) C(119) N(128) 11.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(4) C(3) 1.891(3)
N(1) C(8) 1.335(5)
N(1) C(2) 1.339(5)
C(2) C(3) 1.368(5)
C(3) C(5) 1.382(5)
C(5) C(6) 1.383(5)
C(6) C(8) 1.403(5)
C(6) C(7) 1.506(5)
C(8) C(9) 1.511(5)
C(9) C(10) 1.519(5)
C(10) C(11) 1.516(5)
C(11) C(12) 1.527(4)
C(12) N(13) 1.458(3)
N(13) C(14) 1.305(4)
C(14) N(15) 1.334(3)
C(14) N(25) 1.334(3)
C(14) C(19) 1.501(4)
S(16) O(27) 1.036(7)
S(16) S(26) 1.235(3)
S(16) O(17) 1.486(3)
S(16) N(15) 1.658(3)
S(16) N(18) 1.688(3)
S(16) N(25) 1.863(8)
S(16) N(28) 1.927(7)
S(26) O(17) 1.093(5)
S(26) O(27) 1.488(3)
S(26) N(25) 1.658(3)
S(26) N(28) 1.688(3)
S(26) N(15) 1.840(6)
S(26) N(18) 1.868(6)
N(15) N(25) 0.550(10)
O(27) O(17) 0.874(6)
N(18) N(28) 0.610(10)
N(18) C(19) 1.338(3)
N(28) C(19) 1.339(3)
C(19) N(20) 1.319(4)
Br(104) C(103) 1.891(3)
N(101) C(108) 1.333(4)
N(101) C(102) 1.345(4)
C(102) C(103) 1.375(5)
C(103) C(105) 1.372(5)
C(105) C(106) 1.383(4)
C(106) C(108) 1.405(4)
C(106) C(107) 1.492(5)
C(108) C(109) 1.512(4)
C(109) C(110) 1.517(4)
C(110) C(111) 1.520(4)
C(111) C(112) 1.518(4)
C(112) C(113) 1.457(3)
N(113) C(114) 1.305(4)
C(114) N(115) 1.328(2)
C(114) N(125) 1.334(3)
C(114) C(119) 1.506(4)
S(116) O(127) 1.228(6)
S(116) S(126) 1.291(4)
S(116) O(117) 1.492(2)
S(116) N(115) 1.661(2)
S(116) N(118) 1.680(2)
S(116) N(125) 1.865(7)
S(116) N(128) 1.845(7)
S(126) O(117) 1.045(4)
S(126) O(127) 1.481(3)
S(126) N(125) 1.666(3)
S(126) N(128) 1.691(3)
S(126) N(115) 1.895(4)
S(126) N(118) 1.941(4)
N(115) N(125) 0.595(7)
O(127) O(117) 0.722(5)
N(118) N(128) 0.578(7)
N(118) C(119) 1.324(2)
N(128) C(119) 1.332(3)
C(119) N(120) 1.316(4)
C(107) H(105) 1.00
C(109) H(106) 1.00
C(109) H(107) 1.00
C(110) H(108) 1.00
C(110) H(109) 1.00
C(111) H(110) 1.00
C(111) H(111) 1.00
C(112) H(112) 1.00
C(112) H(113) 1.00
N(113) H(114) 0.90
N(120) H(115) 0.92
N(120) H(116) 1.00
C(5) H(2) 1.00
C(7) H(3) 1.11
C(7) H(4) 1.00
C(7) H(4) 1.00
C(9) H(6) 1.00
C(9) H(7) 1.00
C(10) H(8) 1.00
C(10) H(8) 1.00
C(11) H(10) 1.00
C(11) H(11) 1.00
C(12) H(12) 1.00
C(12) H(13) 1.00
N(13) H(14) 0.90
N(20) H(15) 0.93
N(20) H(16) 0.86
C(102) H(101) 1.00
C(105) H(102) 1.00
C(107) H(103) 0.93
C(107) H(104) 1.00
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
N(1) C(8) C(9) C(10) 3.9
C(6) C(8) C(9) C(10) -177.1
C(8) C(9) C(10) C(11) -169.4
C(9) C(10) C(11) C(12) -173.0
C(10) C(11) C(12) N(13) 80.8
C(11) C(12) N(13) C(14) 83.3
C(12) N(13) C(14) N(15) 175.2
C(12) N(13) C(14) N(20) -4.1
C(14) N(15) C(16) O(17) 176.7
N(13) C(14) N(15) S(16) -164.5
N(13) C(14) N(25) S(26) 162.6
N(13) C(14) C(19) N(18) 168.6
N(13) C(14) C(19) N(28) -162.8
N(13) C(14) C(19) N(20) -1.6
C(14) N(15) S(16) O(17) -117.4
C(14) N(25) S(26) O(27) 111.9
C(14) N(15) S(16) N(18) -6.9
C(14) N(25) S(26) N(28) 1.2
C(14) C(19) N(18) S(16) -3.2
C(14) C(19) N(28) S(26) -0.2
N(15) C(14) C(19) N(18) -1.8
N(15) C(14) C(19) N(20) -172.0
N(15) S(16) N(18) C(19) 5.9
N(25) S(26) N(28) C(19) -172.0
C(19) N(18) S(16) O(17) 117.8
C(19) N(28) S(26) O(27) -113.3
C(19) N(18) S(16) O(17) 117.8
C(19) N(28) S(26) O(27) -113.3
N(20) C(19) N(18) S(16) 166.9
N(20) C(19) N(28) S(26) -161.7
N(15) C(14) C(19) N(18) -1.7
N(25) C(14) C(19) N(28) 1.0
N(15) C(14) C(19) N(20) -172.0
N(25) C(14) C(19) N(20) 162.2
N(101) C(108) C(109) C(110) 9.3
C(106) C(108) C(109) C(110) -171.1
C(108) C(109) C(110) C(111) 175.1
C(109) C(110) C(111) C(112) 175.7
C(110) C(111) C(112) N(113) 178.2
C(111) C(112) N(113) C(114) -176.2
C(112) N(113) C(114) N(115) 9.4
C(112) N(113) C(114) N(125) -21.2
C(112) N(113) C(114) C(119) -177.5
N(113) C(114) N(115) S(116) 171.5
N(113) C(114) N(125) S(126) -154.4
N(113) C(114) C(119) N(118) -175.1
N(113) C(114) C(119) N(128) 157.8
N(113) C(114) C(119) N(120) -1.1
C(114) N(115) S(116) O(117) 114.6
C(114) N(125) S(126) O(127) -118.9
C(114) N(115) S(116) N(118) 4.0
C(114) N(125) S(126) N(128) -5.2
C(114) C(119) N(118) S(116) 3.9
C(114) C(119) N(128) S(126) -3.4
N(115) C(114) C(119) N(118) -1.2
N(115) C(114) C(119) N(120) 172.8
N(115) S(116) N(118) C(119) -4.7
N(125) S(126) N(128) C(119) 172.8
C(119) N(118) S(116) O(117) -116.7
C(119) N(128) S(126) O(127) 119.7
C(119) N(118) S(116) O(117) -116.7
C(119) N(128) S(126) O(127) 119.6
N(120) C(119) N(118) S(116) -170.0
N(120) C(119) N(128) S(126) 155.5
N(115) C(114) C(119) N(118) 172.8
C(119) N(118) S(116) O(117) -116.7
C(119) N(128) S(126) O(127) 119.7
C(119) N(118) S(116) O(117) -116.7
C(119) N(128) S(126) O(127) 119.6
N(120) C(119) N(118) S(116) -170.0
N(120) C(119) N(128) S(126) 155.5
N(115) C(114) C(119) N(118) -1.3
N(125) C(114) C(119) N(128) -0.3
N(115) C(114) C(119) N(120) 172.7
N(125) C(114) C(119) N(120) -159.2
