#------------------------------------------------------------------------------
#$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $
#$Revision: 326 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100960.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2100960
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 H~2~ antagonists related to
 <i>N</i>-cyano-<i>N</i>'-methyl-<i>N</i>''-[4-(2-pyridyl)butyl]guanidine
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              547
_journal_page_last               559
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C13 H19 N5 O1'
_chemical_formula_sum            'C13 H19 N5 O1'
_chemical_formula_weight         261.33
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  ' '
_symmetry_space_group_name_H-M   'I 1 2/c 1'
_cell_angle_beta                 111.470(10)
_cell_formula_units_Z            16
_cell_length_a                   23.780(4)
_cell_length_b                   9.162(2)
_cell_length_c                   28.144(5)
_cell_volume                     5706.8
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71069
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_density_diffrn    1.22
_exptl_crystal_F_000             2240
_[local]_cod_data_source_file    ha0114.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(1A) .43860(10) .8698(2) 1.09040(10) .0486
C(2A) .48000(10) .9340(3) 1.13300(10) .0585
C(3A) .46260(10) .9648(3) 1.17320(10) .0646
C(4A) .40530(10) .9322(3) 1.16990(10) .0630
N(5A) .36390(10) .8704(2) 1.12840(10) .0524
C(6A) .38030(10) .8389(2) 1.08910(10) .0424
C(7A) .33440(10) .7690(2) 1.04300(10) .0471
C(8A) .30480(10) .8758(2) .99960(10) .0451
C(9A) .26070(10) .8023(2) .95210(10) .0446
C(10A) .23480(10) .9092(2) .90860(10) .0479
N(11A) .18730(10) .8503(2) .86360(10) .0470
C(12A) .19940(10) .7633(2) .83020(10) .0444
N(13A) .15410(10) .7214(2) .78810(10) .0502
C(14A) .09310(10) .7771(3) .77220(10) .0613
N(15A) .25670(10) .7236(2) .84160(10) .0523
C(16A) .27000(10) .6395(3) .80970(10) .0533
N(17A) .28740(10) .5643(3) .78510(10) .0693
O(18A) .44970(10) .8319(2) 1.04800(10) .0664
C(19A) .51060(10) .8413(4) 1.05070(10) .0814
C(1B) -.01490(10) .1373(2) .39440(10) .0492
C(2B) -.05180(10) .0424(3) .35810(10) .0579
C(3B) -.02570(10) -.0482(3) .33270(10) .0596
C(4B) .03480(10) -.0376(3) .34300(10) .0589
N(5B) .07120(10) .0546(2) .37780(10) .0520
C(6B) .04720(10) .1402(2) .40380(10) .0438
C(7B) .08970(10) .2328(2) .44560(10) .0473
C(8B) .11770(10) .1456(2) .49490(10) .0485
C(9B) .16080(10) .2338(2) .53910(10) .0440
C(10B) .18800(10) .1424(2) .58710(10) .0503
N(11B) .23360(10) .2180(2) .62930(10) .0473
C(12B) .21940(10) .3095(2) .66010(10) .0448
N(13B) .26330(10) .3663(2) .70010(10) .0490
C(14B) .32600(10) .3264(3) .71580(10) .0634
N(15B) .16080(10) .3412(2) .64850(10) .0539
C(16B) .14650(10) .4293(3) .67910(10) .0535
N(17B) .12920(10) .5055(3) .70340(10) .0689
O(18B) -.03380(10) .2313(2) .42290(10) .0651
C(19B) -.09720(10) .2438(3) .41110(10) .0751
H(1) .5120(10) .811(3) 1.0172(9) ?
H(2) .5370(10) .775(3) 1.0783(9) ?
H(3) .5250(10) .944(3) 1.0583(9) ?
H(4) .5220(10) .958(3) 1.1345(9) ?
H(5) .4920(10) 1.011(3) 1.2048(9) ?
H(6) .3930(10) .955(3) 1.1997(9) ?
H(7) .3020(10) .724(3) 1.0532(9) ?
H(8) .3550(10) .691(3) 1.0303(9) ?
H(9) .2820(10) .951(3) 1.0116(9) ?
H(10) .3370(10) .925(3) .9906(9) ?
H(11) .2270(10) .759(3) .9605(9) ?
H(12) .2820(10) .723(3) .9413(9) ?
H(13) .2180(10) .994(3) .9213(9) ?
H(14) .2680(10) .944(3) .8981(9) ?
H(15) .1460(10) .874(3) .8577(9) ?
H(16) .1620(10) .650(3) .7673(9) ?
H(17) .0670(10) .729(3) .7396(9) ?
H(18) .0760(10) .757(3) .7992(9) ?
H(19) .0940(10) .885(3) .7667(9) ?
H(20) -.1050(10) .316(3) .4346(9) ?
H(21) -.1170(10) .278(3) .3750(10) ?
H(22) -.1140(10) .147(3) .4153(9) ?
H(23) -.0960(10) .039(3) .3503(9) ?
H(24) -.0510(10) -.120(3) .3071(9) ?
H(25) .0530(10) -.102(3) .3238(9) ?
H(26) .0670(10) .317(3) .4520(9) ?
H(27) .1230(10) .270(3) .4347(9) ?
H(28) .0840(10) .108(3) .5052(9) ?
H(29) .1410(10) .062(3) .4881(9) ?
H(30) .1380(10) .317(3) .5465(9) ?
H(31) .1940(10) .272(3) .5291(9) ?
H(32) .1550(10) .111(3) .5985(9) ?
H(33) .2070(10) .054(3) .5784(9) ?
H(34) .2750(10) .202(3) .6352(9) ?
H(35) .2520(10) .438(3) .7197(9) ?
H(36) .3500(10) .384(3) .7468(9) ?
H(37) .3310(10) .220(3) .7239(9) ?
H(38) .3410(10) .348(3) .6875(9) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(19A) O(18A) 1.425(3)
C(19A) H(1) 1.00(2)
C(19A) H(2) 1.00(2)
C(19A) H(3) 1.00(3)
O(18A) C(1A) 1.358(2)
C(1A) C(2A) 1.375(3)
C(1A) C(6A) 1.404(3)
C(2A) C(3A) 1.369(3)
C(2A) H(4) 1.00(2)
C(3A) C(4A) 1.365(3)
C(3A) H(5) 1.00(2)
C(4A) N(5A) 1.345(3)
C(4A) H(6) 1.00(2)
N(5A) C(6A) 1.332(2)
C(6A) C(7A) 1.500(3)
C(7A) C(8A) 1.521(3)
C(7A) H(7) 1.00(2)
C(7A) H(8) 1.00(2)
C(8A) C(9A) 1.522(3)
C(8A) H(9) 1.00(2)
C(8A) H(10) 1.00(2)
C(9A) C(10A) 1.512(3)
C(9A) H(11) 1.00(2)
C(9A) H(12) 1.00(2)
C(10A) N(11A) 1.457(2)
C(10A) H(13) 1.00(2)
C(10A) H(14) 1.00(2)
N(11A) C(12A) 1.342(2)
N(11A) H(15) 0.95(2)
C(12A) N(13A) 1.332(2)
C(12A) N(15A) 1.331(2)
N(13A) C(14A) 1.446(3)
N(13A) H(16) 0.95(2)
C(14A) H(17) 1.00(2)
C(14A) H(18) 1.00(2)
C(14A) H(19) 1.00(3)
N(15A) C(16A) 1.307(3)
C(16A) N(17A) 1.155(3)
C(19B) O(18B) 1.426(3)
C(19B) H(20) 1.00(2)
C(19B) H(21) 1.00(2)
C(19B) H(22) 1.00(2)
O(18B) C(1B) 1.361(3)
C(1B) C(2B) 1.384(3)
C(1B) C(2B) 1.401(3)
C(2B) C(3B) 1.380(3)
C(2B) H(23) 1.00(2)
C(3B) C(4B) 1.364(3)
C(3B) H(24) 1.00(2)
C(4B) N(5B) 1.342(3)
C(4B) H(25) 1.00(2)
N(5B) C(6B) 1.335(3)
C(6B) C(7B) 1.501(3)
C(7B) C(8B) 1.527(3)
C(7B) H(26) 1.00(2)
C(7B) H(27) 1.00(2)
C(8B) C(9B) 1.521(3)
C(8B) H(28) 1.00(2)
C(8B) H(29) 1.00(2)
C(9B) C(10B) 1.518(3)
C(9B) H(30) 1.00(2)
C(9B) H(31) 1.00(2)
C(10B) N(11B) 1.457(2)
C(10B) H(32) 1.00(2)
C(10B) H(33) 1.00(2)
N(11B) C(12B) 1.336(2)
N(11B) H(34) 0.95(2)
C(12B) N(13B) 1.329(2)
C(12B) N(15B) 1.340(2)
N(13B) C(14B) 1.439(3)
N(13B) H(35) 0.95(2)
C(14B) H(36) 1.00(2)
C(14B) H(37) 1.00(3)
C(14B) H(38) 1.00(2)
N(15B) C(16B) 1.313(3)
C(16B) N(17B) 1.154(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H(1) C(19A) O(18A) 109.0(14)
H(2) C(19A) O(18A) 109.5(14)
H(2) C(19A) H(1) 109.5(19)
H(3) C(19A) O(18A) 109.9(14)
H(3) C(19A) H(1) 110.(2)
H(3) C(19A) H(2) 109.5(19)
C(1A) O(18A) C(19A) 117.2(2)
C(2A) C(1A) O(18A) 124.7(2)
C(6A) C(1A) O(18A) 115.7(2)
C(6A) C(1A) C(2A) 119.6(2)
C(3A) C(2A) C(1A) 118.3(2)
H(4) C(2A) C(1A) 120.8(13)
H(4) C(2A) C(3A) 120.9(13)
C(4A) C(3A) C(2A) 119.6(2)
H(5) C(3A) C(2A) 120.1(13)
H(5) C(3A) C(4A) 120.3(13)
N(5A) C(4A) C(3A) 123.2(2)
H(6) C(4A) C(3A) 118.4(13)
H(6) C(4A) N(5A) 118.4(13)
C(6A) N(5A) C(4A) 117.9(2)
N(5A) C(6A) C(1A) 121.4(2)
C(7A) C(6A) C(1A) 120.5(2)
C(7A) C(6A) N(5A) 118.1(2)
C(8A) C(7A) C(6A) 113.4(2)
H(7) C(7A) C(6A) 108.5(13)
H(7) C(7A) C(8A) 108.4(13)
H(8) C(7A) C(6A) 108.6(13)
H(8) C(7A) C(8A) 108.5(13)
H(8) C(7A) H(7) 109.5(18)
C(9A) C(8A) C(7A) 112.8(2)
H(9) C(8A) C(7A) 108.6(13)
H(9) C(8A) C(9A) 108.7(13)
H(10) C(8A) C(7A) 108.5(13)
H(10) C(8A) C(9A) 108.7(13)
H(10) C(8A) H(9) 109.5(18)
C(10A) C(9A) C(8A) 111.7(2)
H(11) C(9A) C(8A) 108.9(13)
H(11) C(9A) C(10A) 108.9(13)
H(12) C(9A) C(8A) 108.8(13)
H(12) C(9A) C(10A) 109.0(13)
H(12) C(9A) H(11A) 109.5(18)
N(11A) C(10A) C(9A) 114.8(2)
H(13) C(10A) C(9A) 108.1(13)
H(13) C(10A) N(11A) 108.2(13)
H(14) C(10A) C(9A) 108.0(13)
H(14) C(10A) N(11A) 108.1(13)
H(14) C(10A) H(13) 109.5(19)
C(12) N(11A) C(10A) 122.1(2)
H(15) N(11A) C(10A) 119.0(14)
H(15) N(11A) C(12A) 118.9(14)
N(13) C(12A) N(11A) 118.9(2)
N(15) C(12A) N(11A) 117.2(2)
N(15) C(12A) N(13A) 123.9(2)
C(14) N(13A) C(12A) 124.5(2)
H(16) N(13A) C(12A) 117.8(14)
H(16) N(13A) C(14A) 117.8(14)
H(17) C(14A) N(13A) 109.5(14)
H(18) C(14A) N(13A) 109.7(14)
H(18) C(14A) H(17) 109.5(19)
H(19) C(14A) N(13A) 109.2(13)
H(19) C(14A) H(17) 109.5(19)
H(19) C(14A) H(18) 109.5(19)
C(16A) N(15A) C(12A) 118.7(2)
N(17A) C(16A) N(15A) 173.4(2)
H(20) C(19B) O(18B) 109.2(14)
H(21) C(19B) O(18B) 109.6(14)
H(21) C(19A) H(20) 109.5(19)
H(22) C(19A) O(18B) 109.7(14)
H(22) C(19A) H(20) 109.5(19)
H(22) C(19A) H(21) 109.5(19)
C(1B) O(18B) C(19B) 117.5(2)
C(2B) C(1B) O(18B) 125.2(2)
C(6B) C(1B) O(18B) 115.4(2)
C(6B) C(1B) C(2B) 119.4(2)
C(3B) C(2B) C(1B) 118.5(2)
H(23) C(2B) C(1B) 120.8(14)
H(23) C(2B) C(3B) 120.7(14)
C(4B) C(3B) C(2B) 119.1(2)
H(24) C(3B) C(2B) 120.4(13)
H(24) C(3B) C(4B) 120.5(13)
N(5B) C(4B) C(3B) 123.2(2)
H(25) C(4B) C(3B) 118.3(13)
H(25) C(4B) N(5B) 118.4(13)
C(6B) N(5B) C(4B) 118.7(2)
N(5B) C(6B) C(1B) 121.1(2)
C(7B) C(6B) C(1B) 121.3(2)
C(7B) C(6B) N(5B) 117.5(2)
C(8B) C(7B) C(6B) 111.2(2)
H(26) C(7B) C(6B) 108.8(13)
H(26) C(7B) C(8B) 109.0(13)
H(27) C(7B) C(6B) 109.3(13)
H(27) C(7B) C(8B) 109.0(13)
H(27) C(7B) H(26) 109.5(19)
C(9B) C(8B) C(7B) 113.9(2)
H(28) C(8B) C(7B) 108.4(13)
H(28) C(8B) C(9B) 108.3(13)
H(29) C(8B) C(7B) 108.3(13)
H(29) C(8B) C(9B) 108.4(13)
H(29) C(8B) H(28) 109.5(19)
C(10B) C(9B) C(8B) 112.0(2)
H(30) C(9B) C(8B) 108.9(13)
H(30) C(9B) C(10B) 108.9(13)
H(31) C(9B) C(8B) 108.8(13)
H(31) C(9B) C(10B) 108.8(13)
H(31) C(9B) H(30) 109.5(18)
N(11B) C(10B) C(9B) 114.3(2)
H(32) C(10B) C(9B) 108.2(13)
H(32) C(10B) N(1B) 108.3(13)
H(33) C(10B) C(9B) 108.2(13)
H(33) C(10B) N(11B) 108.3(13)
H(33) C(10B) H(32) 109.5(19)
C(12B) N(11B) C(10B) 122.6(2)
H(34) N(11B) C(10B) 118.8(14)
H(34) N(11B) C(12B) 118.7(14)
N(3B) C(12B) N(11B) 119.2(2)
N(15B) C(12B) N(11B) 117.7(2)
N(15B) C(12B) N(13B) 123.1(2)
C(14B) N(13B) C(12B) 124.4(2)
H(35) N(13B) C(12B) 117.7(14)
H(35) N(13B) C(14B) 117.9(14)
H(36) C(14B) N(13B) 109.5(13)
H(37) C(14B) N(13B) 109.6(14)
H(37) C(14B) H(36) 109.5(19)
H(38) C(14B) N(13B) 109.4(13)
H(38) C(14B) H(36) 109.5(19)
H(38) C(14B) H(37) 109.5(19)
C(16B) N(15B) C(12B) 117.9(2)
N(17B) C(16B) N(15B) 174.5(2)