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#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/11/2101116.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_2101116
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            'C19 H22 Br N5 O S'
_chemical_formula_weight         448.38
_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                90.0
_cell_angle_beta                 96.91(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   36.293(7)
_cell_length_b                   4.826(2)
_cell_length_c                   11.528(3)
_cell_volume                     2004.5(11)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    3.92
_exptl_crystal_density_diffrn    1.49
_exptl_crystal_F_000             920
_cod_data_source_file            ha0121.cif
_cod_data_source_block           ha0121d
_cod_original_cell_volume        2004.27
_cod_database_code               2101116
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) .1355(3) .1490(10) .1324(6) .0623
C(2) .1047(3) .258(2) .1660(7) .0559
C(3) .0698(3) .1810(10) .1155(5) .0475
Br(4) .02784(5) .3423(3) .17010(10) .0703
C(5) .0665(3) -.0160(10) .0276(5) .0506
C(6) .0985(3) -.1280(10) -.0066(6) .0498
C(7) .0965(5) -.347(3) -.1000(10) .0706
C(8) .1327(3) -.0420(10) .0473(5) .0475
C(9) .1702(4) -.147(3) .0210(10) .0551
C(10) .1836(4) -.015(3) -.0860(10) .0586
C(11) .2194(4) -.138(3) -.1140(10) .0590
C(12) .2333(4) -.012(3) -.2190(10) .0570
N(13) .2690(2) -.139(2) -.2383(7) .0425
C(14) .2881(3) -.051(2) -.3188(8) .0399
N(15) .2777(3) .131(2) -.3987(7) .0472
S(16) .31260(9) .2037(6) -.4749(2) .0473
O(17) .3028(2) .103(2) -.5957(5) .0519
N(18) .3443(3) -.029(2) -.4087(7) .0464
C(19) .3278(3) -.142(2) -.3254(8) .0397
N(20) .3442(3) -.329(2) -.2525(7) .0458
C(21) .3840(3) -.409(2) -.2541(9) .0460
C(22) .4100(2) -.1946(9) -.2036(6) .0428
C(23) .4086(2) -.0970(10) -.0907(6) .0627
C(24) .4347(2) .0930(10) -.0418(5) .0743
C(25) .4636(2) .2003(9) -.0972(8) .0773
C(26) .46370(10) .0960(10) -.2095(8) .0641
C(27) .4384(2) -.0930(10) -.2629(5) .0587
H(1) .1075(2) .4020(10) .2290(7) .054(6)
H(2) .0412(3) -.0720(10) -.0092(5) .054(6)
H(3) .1221(4) -.405(3) -.1140(10) .080(6)
H(4) .0827(4) -.511(3) -.0740(10) .080(6)
H(5) .0831(4) -.270(3) -.1740(10) .080(6)
H(6) .1890(4) -.102(3) .0890(10) .077(3)
H(7) .1692(4) -.353(3) .0090(10) .077(3)
H(8) .1879(4) .187(3) -.0710(10) .077(3)
H(9) .1635(4) -.040(3) -.1520(10) .077(3)
H(10) .2391(4) -.117(3) -.0460(10) .077(3)
H(11) .2147(4) -.340(3) -.1300(10) .077(3)
H(12) .2360(4) .192(3) -.2070(10) .077(3)
H(13) .2150(4) -.049(3) -.2900(10) .077(3)
H(14) .2789(2) -.286(2) -.1879(7) .050(5)
H(15) .3297(2) -.421(2) -.1998(7) .050(5)
H(16) .3884(3) -.440(2) -.3371(9) .048(5)
H(17) .3894(3) -.583(2) -.2083(9) .048(5)
H(18) .3879(2) -.1610(10) -.0474(5) .066(4)
H(19) .4329(2) .1660(10) .0384(5) .066(4)
H(20) .4836(2) .3212(9) -.0575(8) .066(4)
H(21) .48240(10) .1760(10) -.2573(8) .066(4)
H(22) .4405(2) -.1620(10) -.3437(5) .066(4)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(8) N(1) C(2) 119.2(11)
C(3) C(2) N(1) 121.9(11)
C(5) C(3) C(2) 119.4(10)
Br(4) C(3) C(2) 118.9(7)
Br(4) C(3) C(5) 121.7(8)
C(6) C(5) C(3) 118.3(10)
C(5) C(6) C(8) 119.7(10)
C(7) C(6) C(8) 119.8(10)
C(7) C(6) C(5) 120.5(9)
C(6) C(8) N(1) 121.5(10)
C(9) C(8) N(1) 112.6(9)
C(9) C(8) C(6) 125.9(9)
C(8) C(9) C(10) 113.9(8)
C(9) C(10) C(11) 112.3(10)
C(10) C(11) C(12) 113.5(10)
C(11) C(12) N(13) 109.9(10)
C(12) N(13) C(14) 122.0(9)
N(13) C(14) N(15) 126.4(11)
C(19) C(14) N(15) 111.1(9)
C(19) C(14) N(13) 122.4(9)
S(16) N(15) C(14) 110.0(8)
N(15) S(16) O(17) 108.4(5)
N(18) S(16) O(17) 106.0(4)
N(18) S(16) N(15) 98.0(4)
S(16) N(18) C(19) 104.9(7)
N(20) C(19) N(18) 122.7(10)
C(14) C(19) N(18) 115.9(9)
C(14) C(19) N(20) 121.4(9)
C(21) N(20) C(19) 121.8(9)
N(20) C(21) C(22) 112.7(7)
C(27) C(22) C(23) 117.0(2)
C(21) C(22) C(23) 121.0(7)
C(21) C(22) C(27) 121.9(7)
C(22) C(23) C(24) 120.20(10)
C(25) C(24) C(23) 125.10(10)
C(24) C(25) C(26) 112.4(2)
C(27) C(26) C(25) 125.10(10)
C(22) C(27) C(26) 120.20(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(4) C(3) 1.890(10)
N(1) C(2) 1.338(5)
N(1) C(8) 1.339(5)
C(2) C(3) 1.379(5)
C(3) C(5) 1.382(5)
C(5) C(6) 1.382(5)
C(6) C(8) 1.381(5)
C(6) C(7) 1.50(2)
C(8) C(9) 1.520(10)
C(9) C(10) 1.52(2)
C(10) C(11) 1.500(10)
C(11) C(12) 1.500(10)
C(12) N(13) 1.470(10)
N(13) C(14) 1.300(10)
C(14) N(15) 1.290(10)
C(14) C(19) 1.520(10)
N(15) S(16) 1.660(10)
S(16) O(17) 1.478(7)
S(16) N(18) 1.719(9)
N(18) C(19) 1.310(10)
C(19) N(20) 1.320(10)
N(20) C(21) 1.500(10)
C(21) C(22) 1.470(10)
C(22) C(23) 1.390(4)
C(22) C(27) 1.393(4)
C(23) C(24) 1.389(4)
C(24) C(25) 1.392(5)
C(25) C(26) 1.388(5)
C(26) C(27) 1.389(4)
C(2) H(1) 1.00
C(5) H(2) 1.00
C(7) H(3) 1.00
C(7) H(4) 1.00
C(7) H(5) 1.00
C(9) H(6) 1.00
C(9) H(7) 1.00
C(10) H(8) 1.00
C(10) H(9) 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) 0.96
N(20) H(15) 0.96
C(21) H(16) 1.00
C(21) H(17) 1.00
C(23) H(18) 1.00
C(24) H(19) 1.00
C(25) H(20) 1.00
C(26) H(21) 1.00
C(27) H(22) 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) -99.8
C(8) C(9) C(10) C(11) -175.9
C(9) C(10) C(11) C(12) 179.8
C(10) C(11) C(12) N(13) 178.2
C(11) C(12) N(13) C(14) -174.8
C(12) N(13) C(14) N(15) -7.9
C(12) N(13) C(14) C(19) 168.4
N(13) C(14) N(15) S(16) 174.4
C(19) C(14) N(15) S(16) -2.3
C(14) N(15) S(16) O(17) 113.6
C(14) N(15) S(16) N(18) -3.7
C(19) N(18) S(16) O(17) -115.8
C(19) N(18) S(16) N(15) -4.0
C(14) C(19) N(18) S(16) 3.3
N(20) C(19) N(18) S(16) -178.3
N(13) C(14) C(19) N(18) -177.6
N(13) C(14) C(19) N(20) 3.9
N(15) C(14) C(19) N(18) -0.8
N(15) C(14) C(19) N(20) -179.3
C(21) N(20) C(19) N(18) 5.0
C(21) N(20) C(19) C(14) -176.7
C(19) N(20) C(21) C(22) 74.1
N(20) C(21) C(22) C(23) 56.1
N(20) C(21) C(22) C(27) -128.1
