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#$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/13/2101393.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_2101393
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_paper_doi               10.1107/S0108768195000395
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C13 H11 N3 O1'
_chemical_formula_sum            'C13 H11 N3 O'
_chemical_formula_weight         225.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                81.31(2)
_cell_angle_beta                 85.28(2)
_cell_angle_gamma                66.02(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7040(10)
_cell_length_b                   6.8460(10)
_cell_length_c                   13.273(3)
_cell_volume                     550.06(19)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             236
_cod_data_source_file            bk0018.cif
_cod_data_source_block           bk0018b
_cod_original_cell_volume        550.0(2)
_cod_original_formula_sum        'C13 H11 N3 O1'
_cod_database_code               2101393
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C(1) .4874(3) .8758(3) .80740(10)
C(2) .7107(3) .7840(2) .81850(10)
C(21) .8741(3) .7910(3) .73650(10)
N(3) .7935(2) .6876(2) .91220(10)
C(4) .6742(3) .6698(2) .99980(10)
O(4) .7671(2) .5666(2) 1.08070(10)
C(5) .4424(3) .7755(3) .98860(10)
C(51) .3052(3) .7706(3) 1.07650(10)
N(52) .1915(3) .7678(2) 1.14590(10)
C(6) .3547(3) .8733(3) .89410(10)
C(1') .3827(3) .9779(3) .70700(10)
C(2') .3830(3) .8548(3) .63200(10)
C(21') .4964(4) .6134(3) .6440(2)
C(3') .2685(3) .9661(3) .54370(10)
N(4') .1618(3) 1.1803(2) .52530(10)
C(5') .1647(3) 1.2942(3) .59810(10)
C(6') .2701(3) 1.2013(3) .68950(10)
H(21A) .822(4) .795(3) .672(2)
H(21B) 1.015(4) .667(3) .748(2)
H(21C) .897(4) .919(3) .738(2)
H(6) .194(4) .944(3) .8870(10)
H(21'A) .658(4) .563(3) .635(2)
H(21'B) .438(4) .554(4) .596(2)
H(21'C) .484(4) .548(3) .714(2)
H(3') .261(4) .885(3) .489(2)
H(5') .086(4) 1.451(3) .584(2)
H(6') .266(4) 1.292(3) .742(2)
H(N3) .947(4) .604(3) .9160(10)
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) 118.3(2)
C(2) C(1) C(1') 122.7(2)
C(6) C(1) C(1') 119.0(2)
C(1) C(2) N(3) 119.1(2)
C(1) C(2) C(21) 125.1(2)
C(21) C(2) N(3) 115.7(2)
C(2) N(3) C(4) 126.0(2)
N(3) C(4) O(4) 120.8(2)
N(3) C(4) C(5) 114.5(2)
O(4) C(4) C(5) 124.7(2)
C(4) C(5) C(6) 120.4(2)
C(4) C(5) C(51) 118.4(2)
C(51) C(5) C(6) 121.2(2)
C(5) C(51) N(52) 178.6(2)
C(5) C(6) C(1) 121.6(2)
C(1) C(1') C(2') 121.8(2)
C(1) C(1') C(6') 119.3(2)
C(2') C(1') C(6') 118.8(2)
C(1') C(2') C(3') 117.0(2)
C(1') C(2') C(21') 122.9(2)
C(21') C(2') C(3') 120.1(2)
C(2') C(3') N(4') 125.0(2)
C(3') N(4') C(5') 116.8(2)
N(4') C(5') C(6') 123.4(2)
C(1') C(6') C(5') 119.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) C(2) 1.379(2)
C(1) C(6) 1.398(2)
C(1) C(1') 1.494(2)
C(2) N(3) 1.363(2)
C(2) C(21) 1.489(3)
N(3) C(4) 1.374(2)
C(4) C(5) 1.432(2)
C(4) O(4) 1.251(2)
C(5) C(6) 1.384(2)
C(5) C(51) 1.430(2)
C(51) N(52) 1.150(2)
C(1') C(2') 1.398(3)
C(1') C(6') 1.395(2)
C(2') C(3') 1.395(2)
C(2') C(21') 1.501(2)
C(3') N(4') 1.338(2)
N(4') C(5') 1.336(3)
C(5') C(6') 1.385(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10082379