#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2101118.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_2101118
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 H~1~-receptor antagonists derived from the
 cimetidine group of histamine H~2~-receptor antagonists
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              221
_journal_page_last               243
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C19 H23 F N6 O S'
_chemical_formula_weight         402.5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 97.83(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   6.686(2)
_cell_length_b                   14.717(3)
_cell_length_c                   20.850(5)
_cell_volume                     2032.47
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    1.641
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_F_000             848
_[local]_cod_data_source_file    ha0121.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) .3001(5) .5504(2) .2580(2) .0706
C(2) .3655(7) .6127(2) .3032(2) .0767
C(3) .2592(8) .6376(3) .3528(2) .0884
C(4) .0770(8) .5951(2) .3548(2) .0823
C(5) .0042(6) .5309(2) .3095(2) .0680
C(6) .1210(5) .5103(2) .2615(2) .0580
N(7) .0530(7) .4486(3) .2146(2) .0650
C(8) -.1419(9) .4070(4) .2118(3) .0703
C(9) -.1484(5) .3263(2) .25760(10) .0569
C(10) .0184(5) .2969(2) .29900(10) .0641
C(11) .0109(5) .2237(2) .34050(10) .0723
C(12) -.1746(5) .1816(2) .33800(10) .0738
F(13) -.1884(6) .1091(3) .3792(2) .1037
C(14) -.3481(5) .2067(2) .29810(10) .0879
C(15) -.3290(5) .2804(2) .25800(10) .0779
C(16) .1805(8) .4229(3) .1653(2) .0628
C(17) .1431(7) .4812(3) .1052(2) .0537
C(18) .2986(7) .4636(3) .0593(2) .0587
N(19) .2836(5) .3711(2) .0432(2) .0506
C(20) .4453(5) .3210(3) .0279(2) .0450
N(21) .6288(5) .3479(3) .0477(2) .0614
S(22) .7803(2) .26040(10) .03661(7) .0741
O(23) .9024(5) .2913(3) -.0138(2) .0896
N(24) .6087(5) .1899(3) -.0015(2) .0630
C(25) .4325(6) .2280(3) -.0018(2) .0473
N(26) .2622(5) .1891(3) -.0247(2) .0548
C(27) .2540(9) .0992(4) -.0545(3) .0784
C(28) .0530(10) .0763(7) -.0853(5) .1262
H(1) .4993(7) .6415(2) .3002(2) .079(3)
H(2) .3096(8) .6840(3) .3862(3) .079(3)
H(3) -.0046(8) .6117(2) .3898(2) .079(3)
H(4) -.1293(6) .5012(2) .3116(2) .079(3)
H(5) -.2412(9) .4536(4) .2224(3) .077(4)
H(6) -.1818(9) .3848(4) .1665(3) .077(4)
H(7) .1488(5) .3302(2) .29900(10) .075(3)
H(8) .1306(5) .2020(2) .37070(10) .075(3)
H(9) -.4776(5) .1728(2) .29860(10) .075(3)
H(10) -.4497(5) .3014(2) .22800(10) .075(3)
H(11) .3251(8) .4321(3) .1838(2) .069(2)
H(12) .1580(8) .3578(3) .1526(2) .069(2)
H(13) .1432(7) .5463(3) .1190(2) .069(2)
H(14) .0066(7) .4648(3) .0824(2) .069(2)
H(15) .2769(7) .5073(3) .0223(2) .069(2)
H(16) .4364(7) .4728(3) .0838(2) .069(2)
H(17) .1510(5) .3454(2) .0104(2) .062(4)
H(18) .1467(5) .2259(3) -.0363(2) .062(4)
H(19) .3551(9) .0939(4) -.0855(3) .098(4)
H(20) .2879(9) .0549(4) -.0183(3) .098(4)
H(21) -.0540(10) .1121(7) -.1126(5) .156(5)
H(22) .0390(10) .0549(7) -.0416(5) .156(5)
H(23) .0620(10) .0095(7) -.1126(5) .156(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.345(4)
N(1) C(6) 1.346(4)
C(2) C(3) 1.381(4)
C(3) C(4) 1.375(4)
C(4) C(5) 1.377(4)
C(5) C(6) 1.385(4)
C(6) N(7) 1.367(6)
N(7) C(8) 1.434(7)
N(7) C(16) 1.472(6)
C(8) C(9) 1.528(6)
C(9) C(10) 1.384(4)
C(9) C(15) 1.385(4)
C(10) C(11) 1.388(4)
C(11) C(12) 1.381(4)
C(12) F(13) 1.381(4)
C(12) C(14) 1.382(4)
C(14) C(15) 1.386(4)
C(16) C(17) 1.509(6)
C(17) C(18) 1.529(5)
C(18) N(19) 1.458(6)
N(19) C(20) 1.330(5)
C(20) N(21) 1.301(5)
C(20) C(25) 1.500(6)
S(22) O(23) 1.487(4)
S(22) N(24) 1.666(4)
S(22) N(21) 1.674(4)
N(24) C(25) 1.304(5)
C(25) N(26) 1.306(5)
N(26) C(27) 1.459(6)
C(27) C(28) 1.449(9)
C(2) H(1) 1.00
C(3) H(2) 1.00
C(4) H(3) 1.00
C(5) H(4) 1.00
C(8) H(5) 1.00
C(8) H(6) 1.00
C(10) H(7) 1.00
C(11) H(8) 1.00
C(14) H(9) 1.00
C(15) H(10) 1.00
C(16) H(11) 1.00
C(16) H(12) 1.00
C(17) H(13) 1.00
C(17) H(14) 1.00
C(18) H(15) 1.00
C(18) H(16) 1.00
N(19) H(17) 1.03
N(26) H(18) 0.95
C(27) H(19) 1.00
C(27) H(20) 1.00
C(28) H(21) 1.00
C(28) H(22) 0.98
C(28) H(23) 1.14
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(6) N(1) C(2) 117.9(4)
C(3) C(2) N(1) 123.6(5)
C(2) C(3) C(4) 116.8(5)
C(5) C(4) C(3) 121.6(5)
C(6) C(5) C(4) 117.6(5)
N(7) C(6) N(1) 117.6(4)
C(5) C(6) N(1) 122.5(4)
C(5) C(6) N(7) 119.8(4)
C(8) N(7) C(6) 121.7(4)
C(16) N(7) C(6) 120.2(4)
C(16) N(7) C(8) 118.1(4)
C(9) C(8) N(7) 114.2(4)
C(15) C(9) C(10) 118.2(2)
C(8) C(9) C(10) 123.0(3)
C(8) C(9) C(15) 118.8(3)
C(11) C(10) C(9) 122.51(9)
C(10) C(11) C(12) 115.67(9)
F(13) C(12) C(11) 117.28(9)
C(14) C(12) C(11) 125.40(10)
C(14) C(12) F(13) 117.31(9)
C(15) C(14) C(12) 115.65(9)
C(14) C(15) C(9) 122.50(10)
C(17) C(16) N(7) 112.8(4)
C(18) C(17) C(16) 111.9(4)
C(17) C(18) N(19) 111.3(4)
C(18) N(19) C(20) 122.4(3)
N(19) C(20) N(21) 122.9(4)
C(25) C(20) N(21) 114.0(4)
C(25) C(20) N(19) 123.0(3)
S(22) N(21) C(20) 106.5(3)
N(21) S(22) O(23) 105.3(2)
N(21) S(22) N(24) 98.9(2)
N(24) S(22) O(23) 105.2(2)
S(22) N(24) C(25) 107.3(3)
N(26) C(25) N(24) 123.8(4)
C(20) C(25) N(24) 112.9(4)
C(20) C(25) N(26) 123.3(4)
C(27) N(26) C(25) 122.2(4)
N(26) C(27) C(28) 112.2(6)
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
C(5) C(6) N(7) C(8) 2.6
C(5) C(6) N(7) C(16) -176.9
N(1) C(6) N(7) C(8) -175.8
N(1) C(6) N(7) C(16) 4.7
C(5) C(6) N(1) C(2) 0.0
C(6) N(7) C(8) C(9) -80.8
N(7) C(8) C(9) C(10) -0.3
N(7) C(8) C(9) C(15) -179.8
C(6) N(7) C(16) C(17) -92.4
C(9) C(8) N(7) C(16) 98.7
C(8) N(7) C(16) C(17) 88.1
N(7) C(16) C(17) C(18) 171.2
C(16) C(17) C(18) N(19) 64.5
C(17) C(18) N(19) C(20) -138.6
C(18) N(19) C(20) N(21) 4.9
C(18) N(19) C(20) C(25) -175.5
N(19) C(20) N(21) S(22) 174.6
C(20) N(21) S(22) O(23) 115.1
C(20) N(21) S(22) N(24) 6.1
N(21) S(22) N(24) C(25) -5.3
O(23) S(22) N(24) C(25) -114.2
S(22) N(24) C(25) C(20) 3.1
S(22) N(24) C(25) N(26) -175.9
N(24) C(25) C(20) N(19) -178.2
N(24) C(25) C(20) N(21) 1.4
C(25) C(20) N(21) S(22) -5.0
N(26) C(25) C(20) N(19) 0.7
N(26) C(25) C(20) N(21) -179.6
C(27) N(26) C(25) C(20) 179.3
C(27) N(26) C(25) N(24) -1.9
C(25) N(26) C(27) C(28) -169.6
_cod_database_code 2101118