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#$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/10/2101095.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_2101095
loop_
_publ_author_name
'Prout, K.'
'Bannister, C.'
'Burns, K.'
'Chen, M.'
'Warrington, B. H.'
'Vinter, J. G.'
_publ_section_title
;
 Crystal and molecular structures of pyridazinone cardiovascular agents
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              71
_journal_page_last               85
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C14 H15 Br N3 O2'
_chemical_formula_weight         337.2
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2y1'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 98.544(9)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.960(2)
_cell_length_b                   9.697(6)
_cell_length_c                   13.5885(8)
_cell_volume                     1428.1(9)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    3.991
_exptl_crystal_density_diffrn    1.57
_exptl_crystal_F_000             684
_[local]_cod_data_source_file    ha0118.cif
_[local]_cod_data_source_block   ha0118i
_cod_original_cell_volume        1428.3
_cod_database_code               2101095
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1a) .5707(2) -.1187(3) .8144(2) .0373
N(2a) .6612(2) -.1019(3) .8979(2) .0392
C(3a) .7177(2) -.2014(3) .9558(2) .0397
C(4a) .6899(3) -.3458(3) .9196(3) .0443
C(5a) .5553(3) -.3592(3) .8680(2) .0379
C(6a) .5221(2) -.2384(3) .80010(10) .0323
O(7a) .7920(2) -.1735(3) 1.0306(2) .0524
C(8a) .4161(2) -.2506(3) .7177(2) .0318
C(9a) .3691(3) -.1346(3) .6643(2) .0343
C(10a) .2620(3) -.1421(3) .5949(2) .0345
C(11a) .2007(2) -.2668(3) .5780(2) .0328
C(12a) .2499(3) -.3835(3) .6272(2) .0398
C(13a) .3566(3) -.3752(3) .6964(3) .0413
N(14a) .0900(2) -.2858(2) .5108(2) .0342
C(15a) .4673(3) -.3683(5) .9435(3) .0616
C(17a) .0129(2) -.1877(3) .4660(2) .0341
C(18a) -.0921(2) -.2437(4) .3906(2) .0382
O(19a) .0259(2) -.0648(2) .4808(2) .0460
C(20a) -.0848(3) -.1841(3) .2880(2) .0402
Br(21a) .06607(3) -.23860(5) .23936(2) .0457
N(1b) 1.0237(2) -.3755(3) .8389(2) .0387
N(2b) 1.1180(2) -.3940(3) .9195(2) .0390
C(3b) 1.1507(2) -.3021(3) .9933(2) .0350
C(4b) 1.0818(3) -.1690(3) .9837(2) .0381
C(5b) 1.0427(2) -.1272(3) .8756(2) .0339
C(6b) .9875(2) -.2518(3) .8178(2) .0327
O(7b) 1.2290(2) -.3324(3) 1.06510(10) .0438
C(8b) .8868(2) -.2344(3) .7328(2) .0318
C(9b) .8456(3) -.1043(3) .6995(2) .0346
C(10b) .7489(3) -.0880(3) .6233(2) .0353
C(11b) .6887(2) -.2020(3) .5780(2) .0295
C(12b) .7306(3) -.3339(3) .6075(2) .0353
C(13b) .8290(3) -.3478(3) .6835(2) .0372
N(14b) .5891(2) -.1762(2) .5018(2) .0323
C(15b) 1.1504(3) -.0730(4) .8271(3) .0548
C(17b) .5092(2) -.2689(3) .4528(2) .0325
C(18b) .4138(3) -.2063(3) .3722(2) .0389
O(19b) .5108(2) -.3916(2) .4694(2) .0444
C(20b) .4136(2) -.2794(3) .2740(2) .0412
Br(21b) .56899(3) -.25220(5) .22204(2) .0555
H(1a) -.1571 -.2186 .2408 ?
H(2a) -.0882 -.0812 .2914 ?
H(3a) -.1727 -.2175 .4115 ?
H(4a) -.0855 -.3465 .3882 ?
H(5a) .0655 -.3834 .4945 ?
H(6a) .2291 -.0577 .5579 ?
H(7a) .4130 -.0444 .6763 ?
H(8a) .3906 -.4605 .7317 ?
H(9a) .2086 -.4748 .6132 ?
H(10a) .6848 -.0048 .9171 ?
H(11a) .7034 -.4104 .9775 ?
H(12a) .7466 -.3707 .8711 ?
H(13a) .5471 -.4441 .8257 ?
H(14a) .4911 -.4568 .9906 ?
H(15a) .3736 -.3768 .8979 ?
H(16a) .4541 -.3043 .9986 ?
H(1b) .4011 -.3803 .2838 ?
H(2b) .3442 -.2425 .2249 ?
H(3b) .4341 -.1069 .3638 ?
H(4b) .3302 -.2142 .3927 ?
H(5b) .5760 -.0775 .4816 ?
H(6b) .7210 .0066 .6010 ?
H(7b) .8872 -.0205 .7315 ?
H(8b) .8587 -.4425 .7038 ?
H(9b) .6899 -.4173 .5740 ?
H(10b) 1.1657 -.4821 .9221 ?
H(11b) 1.1362 -.0952 1.0177 ?
H(12b) 1.0063 -.1781 1.0165 ?
H(13b) .9804 -.0517 .8750 ?
H(14b) 1.1248 -.0492 .7583 ?
H(15b) 1.1885 .0102 .8591 ?
H(16b) 1.2188 -.1488 .8289 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(14a) C(11a) 1.418(3)
C(11a) C(10a) 1.386(4)
C(10a) C(9a) 1.394(4)
C(9a) C(8a) 1.395(4)
C(8a) C(13a) 1.384(4)
C(13a) C(12a) 1.398(4)
C(12a) C(11a) 1.382(4)
C(6a) C(8a) 1.493(3)
C(6a) N(1a) 1.280(4)
N(1a) N(2a) 1.401(3)
N(2a) C(3a) 1.338(4)
C(3a) O(7a) 1.234(3)
C(3a) C(4a) 1.501(4)
C(4a) C(5a) 1.541(4)
C(5a) C(6a) 1.503(4)
N(14a) C(17a) 1.355(3)
C(17a) C(18a) 1.522(4)
C(17a) O(19a) 1.213(3)
C(18a) C(20a) 1.522(4)
C(20a) Br(21a) 1.943(3)
N(2a) H(10a) 1.000(3)
C(4a) H(11a) 1.000(4)
C(4a) H(12a) 1.000(4)
C(5a) C(15a) 1.512(5)
C(5a) H(13a) 1.000(3)
C(9a) H(7a) 1.000(3)
C(10a) H(6a) 1.000(3)
C(12a) H(9a) 1.000(3)
C(13a) H(8a) 1.000(3)
N(14a) H(5a) 1.000(2)
C(15a) H(14a) 1.079(4)
C(15a) H(15a) 1.120(4)
C(15a) H(16a) 1.000(6)
C(18a) H(3a) 1.000(3)
C(18a) H(4a) 1.000(4)
C(20a) H(1a) 1.000(3)
C(20a) H(2a) 1.000(4)
N(14b) C(11b) 1.410(3)
C(11b) C(10b) 1.398(4)
C(11b) C(12b) 1.384(4)
C(8b) C(9b) 1.390(4)
C(8b) C(13b) 1.392(4)
C(12b) C(13b) 1.376(4)
C(9b) C(10b) 1.384(4)
C(6b) C(8b) 1.485(3)
C(6b) N(1b) 1.283(4)
N(1b) N(2b) 1.402(3)
N(2b) C(3b) 1.350(3)
C(3b) O(7b) 1.235(3)
C(3b) C(4b) 1.492(4)
C(4b) C(5b) 1.522(3)
C(5b) C(6b) 1.517(4)
N(14b) C(17b) 1.359(3)
C(17b) C(18b) 1.523(3)
C(17b) O(19b) 1.211(3)
C(18b) C(20b) 1.510(4)
C(20b) Br(21b) 1.956(3)
N(2b) H(10b) 1.000(3)
C(4b) H(11b) 1.000(3)
C(4b) H(12b) 1.000(3)
C(5b) C(15b) 1.528(5)
C(5b) H(13b) 1.000(3)
C(9b) H(7b) 1.000(3)
C(10b) H(6b) 1.000(3)
C(12b) H(9b) 1.000(3)
C(13b) H(8b) 1.000(3)
N(14b) H(5b) 1.000(2)
C(15b) H(14b) .964(4)
C(15b) H(15b) .980(4)
C(15b) H(16b) 1.049(5)
C(18b) H(3b) 1.000(3)
C(18b) H(4b) 1.000(3)
C(20b) H(1b) 1.000(3)
C(20b) H(2b) 1.000(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(12a) C(11a) C(10a) 119.3(2)
C(11a) C(10a) C(9a) 119.8(2)
C(10a) C(9a) C(8a) 121.2(2)
C(9a) C(8a) C(13a) 118.0(2)
C(8a) C(13a) C(12a) 121.0(3)
C(13a) C(12a) C(11a) 120.6(3)
N(1a) C(6a) C(5a) 123.8(2)
C(6a) N(1a) N(2a) 117.2(2)
N(1a) N(2a) C(3a) 127.0(2)
N(2a) C(3a) C(4a) 115.2(2)
C(3a) C(4a) C(5a) 111.2(2)
C(4a) C(5a) C(6a) 110.0(2)
N(2a) C(3a) O(7a) 121.2(3)
C(4a) C(3a) O(7a) 123.5(3)
N(1a) C(6a) C(8a) 116.5(3)
C(5a) C(6a) C(8a) 119.3(3)
C(6a) C(8a) C(9a) 120.8(3)
C(6a) C(8a) C(13a) 121.1(3)
C(10a) C(11a) N(14a) 124.5(2)
C(12a) C(11a) N(14a) 116.1(2)
C(11a) N(14a) C(17a) 128.0(2)
N(14a) C(17a) C(18a) 114.2(2)
N(14a) C(17a) O(19a) 124.4(2)
C(18a) C(17a) O(19a) 121.4(3)
C(17a) C(18a) C(20a) 110.1(2)
C(18a) C(20a) Br(21a) 111.8(2)
C(12b) C(11b) C(10b) 119.3(2)
C(11b) C(10b) C(9b) 119.3(2)
C(10b) C(9b) C(8b) 122.1(3)
C(9b) C(8b) C(13b) 117.2(2)
C(8b) C(13b) C(12b) 121.6(2)
C(13b) C(12b) C(11b) 120.4(2)
N(1b) C(6b) C(5b) 123.0(2)
C(6b) N(1b) N(2b) 117.4(2)
N(1b) N(2b) C(3b) 125.5(2)
N(2b) C(3b) C(4b) 115.5(2)
C(3b) C(4b) C(5b) 112.4(2)
C(4b) C(5b) C(6b) 108.7(2)
N(2b) C(3b) O(7b) 120.4(3)
C(4b) C(3b) O(7b) 124.0(2)
N(1b) C(6b) C(8b) 116.7(2)
C(5b) C(6b) C(8b) 120.4(2)
C(6b) C(8b) C(9b) 121.2(3)
C(6b) C(8b) C(13b) 121.6(2)
C(10b) C(11b) N(14b) 123.9(2)
C(12b) C(11b) N(14b) 116.8(2)
C(11b) N(14b) C(17b) 127.9(2)
N(14b) C(17b) C(18b) 114.4(2)
N(14b) C(17b) O(19b) 124.6(2)
C(18b) C(17b) O(19b) 121.0(2)
C(17b) C(18b) C(20b) 111.1(2)
C(18b) C(20b) Br(21b) 111.6(2)
_journal_paper_doi 10.1107/S0108768193005713