#------------------------------------------------------------------------------
#$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $
#$Revision: 326 $
#$URL: svn://www.crystallography.net/cod/cif/2/2101394.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_2101394
loop_
_publ_author_name
'Wojtczak, A.'
'Cody, V.'
_publ_section_title
;
 Structure-activity relationships of inotropic bipyridines:
 crystallographic analysis of four milrinone analogues
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              981
_journal_page_last               986
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C11 H16 Cl1 N3 O3'
_chemical_formula_sum            'C11 H16 Cl1 N3 O3'
_chemical_formula_weight         273.72
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                77.20(2)
_cell_angle_beta                 87.94(2)
_cell_angle_gamma                83.58(2)
_cell_formula_units_Z            4
_cell_length_a                   7.200(2)
_cell_length_b                   10.695(2)
_cell_length_c                   17.556(4)
_cell_volume                     1310.0(7)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.293
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             576
_[local]_cod_data_source_file    bk0018.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C(1) .2537(4) .1539(3) .0060(2)
C(2) .2045(4) .0560(3) .0656(2)
C(21) .1366(5) .0645(3) .1462(2)
N(3) .2115(4) -.0648(2) .05000(10)
C(4) .2617(4) -.0978(3) -.0190(2)
O(4) .2653(4) -.2118(2) -.02600(10)
C(5) .3086(4) .0050(3) -.0820(2)
N(51) .3625(4) -.0277(2) -.1518(2)
C(6) .3044(5) .1257(3) -.0683(2)
C(1') .2548(4) .2874(3) .0146(2)
C(2') .2048(5) .3901(3) -.0487(2)
C(3') .2126(5) .5153(3) -.0419(2)
N(4') .2668(4) .5401(2) .0253(2)
C(5') .3174(5) .4444(3) .0868(2)
C(6') .3141(5) .3178(3) .0825(2)
C(1A) .2439(4) .8270(3) .4969(2)
C(2A) .2934(4) .9257(3) .4378(2)
C(21A) .3635(5) .9186(3) .3575(2)
N(3A) .2855(4) 1.0459(2) .45390(10)
C(4A) .2335(4) 1.0783(3) .5228(2)
O(4A) .2293(4) 1.1919(2) .53060(10)
C(5A) .1874(4) .9746(3) .5855(2)
N(51A) .1335(4) 1.0058(3) .6559(2)
C(6A) .1914(4) .8542(3) .5711(2)
C(1'A) .2444(4) .6929(3) .4887(2)
C(2'A) .1924(5) .6604(3) .4201(2)
C(3'A) .1924(5) .5329(3) .4169(2)
N(4'A) .2385(4) .4392(2) .4795(2)
C(5'A) .2861(5) .4656(3) .5467(2)
C(6'A) .2914(5) .5918(3) .5525(2)
Cl(1) .6938(2) .29990(10) .22720(10)
Cl(2) .1578(2) .68820(10) .18920(10)
O(W1) .7800(5) .7746(3) .2708(2)
O(W2) .3472(5) .2660(3) .3426(2)
O(W3) .5544(5) .5835(3) .2636(3)
O(W4) .0519(5) .4131(3) .2683(2)
H(21A) .008 .128 .142
H(21B) .110 -.031 .178
H(21C) .241 .100 .175
H(6) .339 .204 -.115
H(2') .160 .371 -.103
H(3') .175 .595 -.091
H(5') .361 .467 .140
H(6') .357 .241 .132
H(21AA) .261 .881 .328
H(21AB) .390 1.013 .326
H(21AC) .493 .854 .362
H(6A) .156 .776 .618
H(2'A) .152 .736 .369
H(3'A) .159 .508 .363
H(5'A) .321 .387 .597
H(6'A) .330 .612 .608
H(N3) .171 -.128 .090
H(N51A) .338 -.107 -.158
H(N51B) .352 .041 -.197
H(N3A) .303 1.108 .414
H(511A) .160 1.084 .661
H(512A) .148 .934 .700
H(W1A) .706 .712 .265
H(W2A) .332 .214 .299
H(W2B) .441 .281 .307
H(W3A) .568 .608 .210
H(W3B) .592 .508 .250
H(W4A) .036 .386 .222
H(W4B) -.058 .386 .254
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) C(2) 1.374(4)
C(1) C(6) 1.428(4)
C(1) C(1') 1.470(4)
C(2) N(3) 1.374(4)
C(2) C(21) 1.500(5)
N(3) C(4) 1.360(4)
C(4) C(5) 1.437(4)
C(4) O(4) 1.250(4)
C(5) C(6) 1.362(4)
C(5) N(51) 1.379(4)
C(1') C(2') 1.404(4)
C(1') C(6') 1.396(5)
C(2') C(3') 1.378(5)
C(3') N(4') 1.345(5)
N(4') C(5') 1.342(4)
C(5') C(6') 1.376(5)
C(1A) C(2A) 1.375(4)
C(1A) C(6A) 1.425(4)
C(1A) C(1'A) 1.473(4)
C(2A) N(3A) 1.370(4)
C(2A) C(21A) 1.496(5)
N(3A) C(4A) 1.361(4)
C(4A) C(5A) 1.437(4)
C(4A) O(4A) 1.249(4)
C(5A) C(6A) 1.363(4)
C(5A) N(51A) 1.382(4)
C(1'A) C(2'A) 1.400(5)
C(1'A) C(6'A) 1.396(4)
C(2'A) C(3'A) 1.377(5)
C(3'A) N(4'A) 1.336(4)
N(4'A) C(5'A) 1.337(5)
C(5'A) C(6'A) 1.381(5)
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) C(6) 118.8(3)
C(2) C(1) C(1') 123.1(3)
C(6) C(1) C(1') 118.0(3)
C(1) C(2) N(3) 117.2(3)
C(1) C(2) C(21) 128.0(3)
C(21) C(2) N(3) 114.7(3)
C(2) N(3) C(4) 126.6(3)
N(3) C(4) O(4) 121.0(3)
N(3) C(4) C(5) 116.3(3)
O(4) C(4) C(5) 122.7(3)
C(4) C(5) C(6) 118.6(3)
C(4) C(5) N(51) 116.8(3)
N(51) C(5) C(6) 124.5(3)
C(5) C(6) C(1) 122.4(3)
C(1) C(1') C(2') 119.8(3)
C(1) C(1') C(6') 122.6(3)
C(2') C(1') C(6') 117.5(3)
C(1') C(2') C(3') 120.0(3)
C(2') C(3') N(4') 120.4(3)
C(3') N(4') C(5') 121.3(3)
N(4') C(5') C(6') 120.5(3)
C(1') C(6') C(5') 120.4(3)
(2A) C(1A) C(6A) 118.7(2)
C(2A) C(1A) C(1'A) 123.8(2)
C(6A) C(1A) C(1'A) 117.5(2)
C(1A) C(2A) N(3A) 117.3(2)
C(1A) C(2A) C(21A) 128.1(3)
C(21A) C(2A) N(3A) 114.5(2)
C(2A) N(3A) C(4A) 126.6(2)
N(3A) C(4A) O(4A) 121.1(2)
N(3A) C(4A) C(5A) 116.2(2)
O(4A) C(4A) C(5A) 122.7(2)
C(4A) C(5A) C(6A) 118.6(2)
C(4A) N(5A) N(51A) 117.0(2)
N(51A) C(5A) C(6A) 124.4(2)
C(5A) C(6A) C(1A) 122.5(2)
C(1A) C(1'A) C(2'A) 123.2(3)
C(1A) C(1'A) C(6'A) 119.5(3)
C(2'A) C(1'A) C(6'A) 117.3(3)
C(1'A) C(2'A) C(3'A) 120.1(3)
C(2'A) C(3'A) N(4'A) 120.5(3)
C(3'A) N(4'A) C(5'A) 121.5(3)
N(4'A) C(5'A) C(6'A) 120.2(3)
C(1'A) C(6'A) C(5'A) 120.3(3)