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#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/09/2100957.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_2100957
loop_
_publ_author_name
'Prout, K.'
'Burns, K.'
'Watkin, D. J.'
'Cooper, D. G.'
'Durant, G. J.'
'Ganellin, C. R.'
'Sach, G. S.'
_publ_section_title
;
 Structures of nine histamine H₂ antagonists related to
 N-cyano-N'-methyl-N''-[4-(2-pyridyl)butyl]guanidine
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              547
_journal_page_last               559
_journal_paper_doi               10.1107/S0108768193000217
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C11 H14 Br1 N5 S1'
_chemical_formula_sum            'C11 H14 Br N5 S'
_chemical_formula_weight         328.23
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 100.4(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.928(4)
_cell_length_b                   9.183(2)
_cell_length_c                   14.229(8)
_cell_volume                     1404(4)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71069
_exptl_absorpt_coefficient_mu    3.23
_exptl_crystal_density_diffrn    1.55
_exptl_crystal_F_000             664
_cod_data_source_file            ha0114.cif
_cod_data_source_block           ha0114c
_cod_original_cell_volume        1404.42
_cod_original_formula_sum        'C11 H14 Br1 N5 S1'
_cod_database_code               2100957
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(1) .5463(4) .0675(5) .1295(3) .0348
C(2) .5871(5) -.0585(6) .1789(4) .0426
C(3) .7078(6) -.1011(6) .1804(4) .0494
C(4) .7837(5) -.01688(6) .1355(5) .0473
N(5) .7451(4) .1046(4) .0866(3) .0394
C(6) .6269(4) .1486(5) .0828(3) .0306
C(7) .5906(5) .2894(5) .0351(3) .0367
S(8) .59910(10) .43650(10) .12270(10) .0391
C(9) .7628(5) .4818(6) .1401(3) .0368
C(10) .7907(4) .5770(6) .0593(3) .0366
N(11) .9188(4) .6287(5) .0798(3) .0351
C(12) .9689(4) .6972(5) .0125(3) .0308
N(13) 1.0820(4) .7542(5) .0353(3) .0381
C(14) 1.1569(6) .7523(10) .1308(4) .0566
N(15) .9002(4) .7011(6) -.0755(3) .0400
C(16) .9437(4) .7649(6) -.1445(3) .0395
N(17) .9699(4) .8188(7) -.2107(3) .0507
Br(18) .38019(5) .13124(6) .12388(4) .0472
H(1) .535(5) -.116(6) .213(4) .040(10)
H(2) .739(6) -.196(4) .206(4) .06(2)
H(3) .873(7) -.041(9) .145(5) .09(2)
H(4) .650(5) .313(6) -.005(4) .040(10)
H(5) .504(5) .287(6) -.000(4) .040(10)
H(6) .779(5) .536(6) .198(4) .040(10)
H(7) .807(4) .387(4) .147(3) .012(9)
H(8) .730(4) .657(4) .051(4) .040(10)
H(9) .781(5) .521(5) -.001(3) .040(10)
H(10) .963(5) .626(6) .146(2) .040(10)
H(11) 1.126(6) .802(6) -.009(4) .06(2)
H(12) 1.235(7) .800(8) .127(5) .07(2)
H(13) 1.109(9) .825(9) .161(7) .14(4)
H(14) 1.175(7) .649(8) .141(5) .07(2)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) C(1) Br(18) 119.83
C(6) C(1) Br(18) 119.52
C(6) C(1) C(2) 120.7(4)
C(3) C(2) C(1) 117.8(5)
H(1) C(2) C(1) 122.92
H(1) C(2) C(3) 119.27
C(4) C(3) C(2) 119.4(5)
H(2) C(3) C(2) 121.72
H(2) C(3) C(4) 118.47
N(5) C(4) C(3) 123.4(5)
H(3) C(4) C(3) 118.35
H(3) C(4) N(5) 117.97
C(6) N(5) C(4) 118.7(4)
N(5) C(6) C(1) 120.0(6)
C(7) C(6) C(1) 122.7(4)
C(7) C(6) N(5) 117.3(4)
S(8) C(7) C(6) 110.8(3)
H(4) C(7) C(6) 108.42
H(4) C(7) S(8) 106.45
H(5) C(7) C(6) 111.27
H(5) C(7) S(8) 107.09
H(5) C(7) H(4) 112.67
C(9) S(8) C(7) 101.0(2)
C(10) C(9) S(8) 111.0(3)
H(6) C(9) S(8) 105.22
H(6) C(9) C(10) 108.96
H(7) C(9) S(8) 105.05
H(7) C(9) C(10) 114.60
H(7) C(9) H(6) 111.62
N(11) C(10) C(9) 110.7(4)
H(8) C(10) C(9) 106.89
H(8) C(10) N(11) 112.83
H(9) C(10) C(9) 110.71
H(9) C(10) N(11) 106.77
H(9) C(10) H(8) 108.99
C(12) N(11) C(10) 120.8(4)
H(10) N(11) C(10) 118.31
H(10) N(11) C(12) 120.31
N(13) C(12) N(11) 119.5(4)
N(15) C(12) N(11) 116.6(4)
N(15) C(12) N(13) 123.9(4)
C(14) N(13) C(12) 124.5(4)
H(11) N(13) C(12) 124.66
H(11) N(13) C(14) 110.89
H(12) C(14) N(13) 106.93
H(13) C(14) N(13) 98.46
H(13) C(14) H(12) 104.93
H(14) C(14) N(13) 102.33
H(14) C(14) H(12) 107.03
H(14) C(14) H(13) 134.40
C(16) N(15) C(12) 119.8(4)
N(17) C(16) N(15) 172.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(18) C(1) 1.90
C(1) C(2) 1.385(7)
C(1) C(6) 1.408(6)
C(2) C(3) 1.373(8)
C(2) H(1) 0.97
C(3) C(4) 1.373(8)
C(3) H(2) 0.98
C(4) N(5) 1.341(7)
C(4) H(3) 0.98
N(5) C(6) 1.345(6)
C(6) C(7) 1.481(7)
C(7) S(8) 1.829(5)
C(7) H(4) 0.97
C(7) H(5) 0.99
S(8) C(9) 1.809(5)
C(9) C(10) 1.518(7)
C(9) H(6) 0.95
C(9) H(7) 0.99
C(10) N(11) 1.456(6)
C(10) H(8) 0.98
C(10) H(9) 0.99
N(11) C(12) 1.343(6)
N(11) H(10) 0.98
C(12) N(13) 1.327(6)
C(12) N(15) 1.339(6)
N(13) C(14) 1.454(7)
N(13) H(11) 0.97
C(14) H(12) 0.97
C(14) H(13) 0.99
C(14) H(14) 0.97
N(15) C(16) 1.304(7)
C(16) N(17) 1.15
