#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/97/2229735.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_2229735
loop_
_publ_author_name
'Wang, Zong-Gui'
'Yuan, Ling'
'Zhou, Li'
'Nan, Yi'
_publ_section_title
;
 N'-(2-Bromo-5-hydroxy-4-methoxybenzylidene)-3,5-dihydroxybenzohydrazide
 methanol monosolvate
;
_journal_coeditor_code           KJ2170
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o841
_journal_paper_doi               10.1107/S1600536811008695
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H13 Br N2 O5, C H4 O'
_chemical_formula_moiety         'C15 H13 Br N2 O5, C H4 O'
_chemical_formula_sum            'C16 H17 Br N2 O6'
_chemical_formula_weight         413.23
_chemical_name_systematic
;
N'-(2-Bromo-5-hydroxy-4-methoxybenzylidene)-3,5-dihydroxybenzohydrazide
methanol monosolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.493(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4242(17)
_cell_length_b                   17.709(4)
_cell_length_c                   12.927(3)
_cell_measurement_reflns_used    2413
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.30
_cell_volume                     1688.7(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9884
_diffrn_reflns_theta_full        27.24
_diffrn_reflns_theta_max         27.24
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_T_max  0.616
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.191
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0482P)²+0.8829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2569
_reflns_number_total             3780
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2170.cif
_cod_data_source_block           I
_cod_original_cell_volume        1688.7(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229735
_cod_database_fobs_code          2229735
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.38821(6) 0.687078(19) 0.54748(3) 0.05529(16) Uani d . 1 . .
O O1 0.6149(3) 0.58020(13) 0.91725(17) 0.0527(6) Uani d . 1 . .
O O2 0.5254(4) 0.43891(13) 0.86339(18) 0.0652(8) Uani d . 1 . .
H H2A 0.6165 0.4422 0.9054 0.098 Uiso d PR 0.50 A 1
H H2B 0.4884 0.4338 0.9204 0.098 Uiso d PR 0.50 A 2
O O3 0.1127(4) 0.31210(12) 0.42579(17) 0.0541(7) Uani d . 1 . .
O O4 -0.2407(4) 0.19793(12) 0.12235(16) 0.0501(6) Uani d . 1 . .
H H4A -0.2804 0.1933 0.0609 0.075 Uiso calc R 1 . .
O O5 -0.1488(4) 0.45108(14) 0.01335(18) 0.0636(8) Uani d . 1 . .
H H5A -0.0942 0.4914 0.0180 0.095 Uiso d PR 0.50 B 1
H H5B -0.2327 0.4458 -0.0330 0.095 Uiso d PR 0.50 B 2
N N1 0.2142(3) 0.44876(14) 0.49680(17) 0.0348(6) Uani d . 1 . .
N N2 0.1270(3) 0.43712(14) 0.39748(18) 0.0354(6) Uani d . 1 . .
H H2 0.1071 0.4774 0.3608 0.059(11) Uiso d R 1 . .
C C1 0.3706(4) 0.53397(16) 0.6178(2) 0.0314(7) Uani d . 1 . .
C C2 0.4255(4) 0.60688(16) 0.6447(2) 0.0327(7) Uani d . 1 . .
C C3 0.5083(4) 0.62529(17) 0.7431(2) 0.0370(7) Uani d . 1 . .
H H3A 0.5428 0.6748 0.7590 0.044 Uiso calc R 1 . .
C C4 0.5387(4) 0.56937(17) 0.8169(2) 0.0373(7) Uani d . 1 . .
C C5 0.4914(5) 0.49492(17) 0.7916(2) 0.0394(8) Uani d . 1 . .
C C6 0.4093(4) 0.47768(17) 0.6937(2) 0.0367(7) Uani d . 1 . .
H H6A 0.3787 0.4278 0.6774 0.044 Uiso calc R 1 . .
C C7 -0.0144(4) 0.35570(16) 0.2601(2) 0.0311(7) Uani d . 1 . .
C C8 -0.0809(4) 0.28403(17) 0.2367(2) 0.0343(7) Uani d . 1 . .
H H8A -0.0643 0.2459 0.2863 0.041 Uiso calc R 1 . .
C C9 -0.1723(4) 0.26884(16) 0.1392(2) 0.0323(7) Uani d . 1 . .
C C10 -0.1920(4) 0.32480(16) 0.0639(2) 0.0326(7) Uani d . 1 . .
H H10A -0.2497 0.3146 -0.0023 0.039 Uiso calc R 1 . .
C C11 -0.1249(4) 0.39546(17) 0.0888(2) 0.0369(7) Uani d . 1 . .
C C12 -0.0367(4) 0.41262(16) 0.1864(2) 0.0345(7) Uani d . 1 . .
H H12A 0.0062 0.4611 0.2019 0.041 Uiso calc R 1 . .
C C13 0.6728(5) 0.6544(2) 0.9486(3) 0.0553(10) Uani d . 1 . .
H H13A 0.7628 0.6715 0.9062 0.083 Uiso calc R 1 . .
H H13B 0.7237 0.6536 1.0203 0.083 Uiso calc R 1 . .
H H13C 0.5710 0.6882 0.9406 0.083 Uiso calc R 1 . .
C C14 0.2758(4) 0.51463(17) 0.5154(2) 0.0350(7) Uani d . 1 . .
H H14A 0.2607 0.5512 0.4636 0.042 Uiso calc R 1 . .
C C15 0.0798(4) 0.36657(17) 0.3681(2) 0.0329(7) Uani d . 1 . .
O O6 0.0298(5) 0.58875(17) 0.3072(3) 0.0832(9) Uani d . 1 . .
H H6 -0.0533 0.6068 0.3359 0.125 Uiso calc R 1 . .
C C16 0.0995(12) 0.6427(4) 0.2480(5) 0.156(4) Uani d . 1 . .
H H16A 0.0079 0.6588 0.1942 0.234 Uiso calc R 1 . .
H H16B 0.2005 0.6222 0.2171 0.234 Uiso calc R 1 . .
H H16C 0.1391 0.6850 0.2911 0.234 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C13 . . 118.5(3) ?
C5 O2 H2A . . 118.4 ?
C5 O2 H2B . . 129.6 ?
H2A O2 H2B . . 75.4 ?
C9 O4 H4A . . 109.5 ?
C11 O5 H5A . . 123.0 ?
C11 O5 H5B . . 117.4 ?
H5A O5 H5B . . 118.8 ?
C14 N1 N2 . . 115.7(2) ?
C15 N2 N1 . . 118.7(2) ?
C15 N2 H2 . . 126.4 ?
N1 N2 H2 . . 114.8 ?
C2 C1 C6 . . 117.1(3) ?
C2 C1 C14 . . 122.7(3) ?
C6 C1 C14 . . 120.2(3) ?
C1 C2 C3 . . 122.4(3) ?
C1 C2 Br1 . . 121.0(2) ?
C3 C2 Br1 . . 116.6(2) ?
C4 C3 C2 . . 119.2(3) ?
C4 C3 H3A . . 120.4 ?
C2 C3 H3A . . 120.4 ?
O1 C4 C3 . . 125.0(3) ?
O1 C4 C5 . . 114.9(3) ?
C3 C4 C5 . . 120.0(3) ?
O2 C5 C6 . . 119.6(3) ?
O2 C5 C4 . . 120.4(3) ?
C6 C5 C4 . . 120.0(3) ?
C5 C6 C1 . . 121.3(3) ?
C5 C6 H6A . . 119.4 ?
C1 C6 H6A . . 119.4 ?
C8 C7 C12 . . 120.4(2) ?
C8 C7 C15 . . 116.0(2) ?
C12 C7 C15 . . 123.6(3) ?
C7 C8 C9 . . 120.2(3) ?
C7 C8 H8A . . 119.9 ?
C9 C8 H8A . . 119.9 ?
O4 C9 C10 . . 122.6(3) ?
O4 C9 C8 . . 117.3(2) ?
C10 C9 C8 . . 120.1(3) ?
C11 C10 C9 . . 118.8(3) ?
C11 C10 H10A . . 120.6 ?
C9 C10 H10A . . 120.6 ?
C10 C11 O5 . . 118.0(3) ?
C10 C11 C12 . . 122.3(3) ?
O5 C11 C12 . . 119.7(3) ?
C7 C12 C11 . . 118.3(3) ?
C7 C12 H12A . . 120.9 ?
C11 C12 H12A . . 120.9 ?
O1 C13 H13A . . 109.5 ?
O1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 C1 . . 120.8(3) ?
N1 C14 H14A . . 119.6 ?
C1 C14 H14A . . 119.6 ?
O3 C15 N2 . . 122.2(3) ?
O3 C15 C7 . . 120.3(3) ?
N2 C15 C7 . . 117.5(2) ?
C16 O6 H6 . . 109.5 ?
O6 C16 H16A . . 109.5 ?
O6 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O6 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.896(3) ?
O1 C4 . 1.368(3) ?
O1 C13 . 1.428(4) ?
O2 C5 . 1.362(4) ?
O2 H2A . 0.8200 ?
O2 H2B . 0.8200 ?
O3 C15 . 1.227(3) ?
O4 C9 . 1.363(3) ?
O4 H4A . 0.8200 ?
O5 C11 . 1.383(3) ?
O5 H5A . 0.8200 ?
O5 H5B . 0.8200 ?
N1 C14 . 1.266(4) ?
N1 N2 . 1.386(3) ?
N2 C15 . 1.341(4) ?
N2 H2 . 0.8600 ?
C1 C2 . 1.386(4) ?
C1 C6 . 1.405(4) ?
C1 C14 . 1.468(4) ?
C2 C3 . 1.388(4) ?
C3 C4 . 1.376(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.394(4) ?
C5 C6 . 1.375(4) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.383(4) ?
C7 C12 . 1.384(4) ?
C7 C15 . 1.501(4) ?
C8 C9 . 1.388(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.385(4) ?
C10 C11 . 1.372(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.388(4) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9300 ?
O6 C16 . 1.362(6) ?
O6 H6 . 0.8200 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2A O5 1_656 0.82 2.11 2.932(3) 180
O2 H2B O1 3_667 0.82 2.33 3.148(4) 180
O4 H4A O3 4_565 0.82 1.84 2.655(3) 175
O5 H5A O5 3_565 0.82 2.15 2.859(5) 145
O5 H5B O2 1_454 0.82 2.12 2.932(3) 171
N2 H2 O6 . 0.86 2.15 2.984(4) 164
O6 H6 O4 2_455 0.82 2.33 3.101(4) 157
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 N1 N2 C15 . . . . 171.4(3) ?
C6 C1 C2 C3 . . . . -2.7(5) ?
C14 C1 C2 C3 . . . . 177.2(3) ?
C6 C1 C2 Br1 . . . . 177.9(2) ?
C14 C1 C2 Br1 . . . . -2.2(4) ?
C1 C2 C3 C4 . . . . 0.5(5) ?
Br1 C2 C3 C4 . . . . 179.9(2) ?
C13 O1 C4 C3 . . . . -1.8(5) ?
C13 O1 C4 C5 . . . . 177.9(3) ?
C2 C3 C4 O1 . . . . -178.4(3) ?
C2 C3 C4 C5 . . . . 1.9(5) ?
O1 C4 C5 O2 . . . . -1.5(5) ?
C3 C4 C5 O2 . . . . 178.3(3) ?
O1 C4 C5 C6 . . . . 178.3(3) ?
C3 C4 C5 C6 . . . . -2.0(5) ?
O2 C5 C6 C1 . . . . 179.5(3) ?
C4 C5 C6 C1 . . . . -0.3(5) ?
C2 C1 C6 C5 . . . . 2.5(5) ?
C14 C1 C6 C5 . . . . -177.3(3) ?
C12 C7 C8 C9 . . . . -0.7(5) ?
C15 C7 C8 C9 . . . . 179.1(3) ?
C7 C8 C9 O4 . . . . -177.4(3) ?
C7 C8 C9 C10 . . . . 2.1(5) ?
O4 C9 C10 C11 . . . . 177.5(3) ?
C8 C9 C10 C11 . . . . -2.0(5) ?
C9 C10 C11 O5 . . . . -178.8(3) ?
C9 C10 C11 C12 . . . . 0.5(5) ?
C8 C7 C12 C11 . . . . -0.8(5) ?
C15 C7 C12 C11 . . . . 179.4(3) ?
C10 C11 C12 C7 . . . . 0.9(5) ?
O5 C11 C12 C7 . . . . -179.8(3) ?
N2 N1 C14 C1 . . . . 179.9(3) ?
C2 C1 C14 N1 . . . . -173.9(3) ?
C6 C1 C14 N1 . . . . 5.9(5) ?
N1 N2 C15 O3 . . . . -0.7(5) ?
N1 N2 C15 C7 . . . . -180.0(3) ?
C8 C7 C15 O3 . . . . 8.3(4) ?
C12 C7 C15 O3 . . . . -171.9(3) ?
C8 C7 C15 N2 . . . . -172.4(3) ?
C12 C7 C15 N2 . . . . 7.3(5) ?
