#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/88/2218861.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_2218861
loop_
_publ_author_name
'Tang, Chun-Bao'
_publ_section_title
;
 2-Chloro-N'-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide
 methanol solvate
;
_journal_coeditor_code           AT2583
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1382
_journal_paper_doi               10.1107/S160053680801965X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H9 Br2 Cl N2 O2, C1 H4 O1'
_chemical_formula_moiety         'C14 H9 Br2 Cl N2 O2, C1 H4 O1'
_chemical_formula_sum            'C15 H13 Br2 Cl N2 O3'
_chemical_formula_weight         464.54
_chemical_name_systematic
;
2-Chloro-N'-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol
solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 120.356(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.156(4)
_cell_length_b                   9.696(3)
_cell_length_c                   18.536(3)
_cell_measurement_reflns_used    2286
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.4
_cell_volume                     1730.1(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.1009
_diffrn_reflns_av_sigmaI/netI    0.1581
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9035
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.854
_exptl_absorpt_correction_T_max  0.4436
_exptl_absorpt_correction_T_min  0.4015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.709
_refine_ls_extinction_coef       0.0119(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0746P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                1895
_reflns_number_total             3627
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2583.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218861
_cod_database_fobs_code          2218861
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br Br1 -0.36755(9) 1.09036(8) 0.95218(6) 0.0603(4) Uani d . 1
Br Br2 -0.19725(9) 0.54059(7) 1.04896(6) 0.0557(3) Uani d . 1
Cl Cl1 0.3094(2) 1.28217(17) 0.81645(14) 0.0580(6) Uani d . 1
O O1 -0.1788(5) 1.0664(4) 0.8816(3) 0.0443(14) Uani d . 1
H H1 -0.1429 1.0532 0.8531 0.067 Uiso calc R 1
O O2 0.0171(5) 1.1554(5) 0.7617(4) 0.0543(15) Uani d . 1
O O3 0.2494(6) 0.7016(5) 0.8572(4) 0.0560(16) Uani d . 1
H H3A 0.1924 0.6511 0.8203 0.084 Uiso calc R 1
N N1 0.0034(6) 0.9492(5) 0.8546(4) 0.0373(16) Uani d . 1
N N2 0.0939(6) 0.9488(5) 0.8251(4) 0.0388(16) Uani d D 1
C C1 -0.0946(7) 0.8351(6) 0.9261(4) 0.0325(16) Uani d . 1
C C2 -0.1773(7) 0.9478(5) 0.9204(4) 0.0307(16) Uani d . 1
C C3 -0.2590(7) 0.9362(6) 0.9571(5) 0.0374(18) Uani d . 1
C C4 -0.2624(7) 0.8177(6) 0.9961(5) 0.0400(19) Uani d . 1
H H4 -0.3182 0.8124 1.0200 0.048 Uiso calc R 1
C C5 -0.1835(7) 0.7073(6) 0.9999(5) 0.0386(18) Uani d . 1
C C6 -0.0988(7) 0.7157(6) 0.9662(5) 0.0389(19) Uani d . 1
H H6 -0.0438 0.6407 0.9702 0.047 Uiso calc R 1
C C7 0.0008(7) 0.8415(6) 0.8926(5) 0.0415(19) Uani d . 1
H H7 0.0583 0.7672 0.8993 0.050 Uiso calc R 1
C C8 0.0941(7) 1.0545(6) 0.7797(5) 0.0353(18) Uani d . 1
C C9 0.1906(7) 1.0373(6) 0.7455(4) 0.0357(17) Uani d . 1
C C10 0.2917(8) 1.1341(6) 0.7595(5) 0.0415(19) Uani d . 1
C C11 0.3785(8) 1.1138(7) 0.7278(5) 0.049(2) Uani d . 1
H H11 0.4449 1.1799 0.7366 0.058 Uiso calc R 1
C C12 0.3676(9) 0.9973(8) 0.6836(6) 0.059(3) Uani d . 1
H H12 0.4265 0.9842 0.6624 0.071 Uiso calc R 1
C C13 0.2705(9) 0.9004(7) 0.6706(6) 0.056(2) Uani d . 1
H H13 0.2645 0.8205 0.6412 0.068 Uiso calc R 1
C C14 0.1819(8) 0.9187(7) 0.7002(5) 0.048(2) Uani d . 1
H H14 0.1152 0.8521 0.6901 0.057 Uiso calc R 1
C C15 0.3807(10) 0.6749(9) 0.8694(7) 0.092(4) Uani d . 1
H H15A 0.4377 0.7555 0.8916 0.138 Uiso calc R 1
H H15B 0.3730 0.6508 0.8170 0.138 Uiso calc R 1
H H15C 0.4221 0.5998 0.9080 0.138 Uiso calc R 1
H H2 0.149(7) 0.875(5) 0.839(5) 0.080 Uiso d D 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'
Cl Cl 0.1484 0.1585 '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
C2 O1 H1 109.5
C15 O3 H3A 109.5
C7 N1 N2 116.6(5)
C8 N2 N1 119.3(5)
C8 N2 H2 125(5)
N1 N2 H2 115(5)
C6 C1 C2 119.4(5)
C6 C1 C7 119.0(5)
C2 C1 C7 121.5(5)
O1 C2 C3 119.6(5)
O1 C2 C1 122.3(5)
C3 C2 C1 118.1(5)
C4 C3 C2 121.8(5)
C4 C3 Br1 119.9(4)
C2 C3 Br1 118.3(5)
C5 C4 C3 119.7(5)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.3(5)
C4 C5 Br2 119.0(4)
C6 C5 Br2 120.6(5)
C5 C6 C1 120.7(5)
C5 C6 H6 119.7
C1 C6 H6 119.7
N1 C7 C1 119.4(5)
N1 C7 H7 120.3
C1 C7 H7 120.3
O2 C8 N2 124.1(5)
O2 C8 C9 121.5(6)
N2 C8 C9 114.3(5)
C10 C9 C14 118.1(5)
C10 C9 C8 122.2(6)
C14 C9 C8 119.7(5)
C11 C10 C9 120.3(6)
C11 C10 Cl1 119.3(5)
C9 C10 Cl1 120.4(4)
C12 C11 C10 120.4(6)
C12 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C11 120.0(6)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 120.9(7)
C12 C13 H13 119.6
C14 C13 H13 119.6
C13 C14 C9 120.3(7)
C13 C14 H14 119.8
C9 C14 H14 119.8
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.897(6)
Br2 C5 1.899(6)
Cl1 C10 1.733(6)
O1 C2 1.352(6)
O1 H1 0.8200
O2 C8 1.232(7)
O3 C15 1.389(9)
O3 H3A 0.8200
N1 C7 1.269(7)
N1 N2 1.369(6)
N2 C8 1.327(7)
N2 H2 0.89(7)
C1 C6 1.390(8)
C1 C2 1.400(8)
C1 C7 1.480(8)
C2 C3 1.389(8)
C3 C4 1.368(8)
C4 C5 1.366(8)
C4 H4 0.9300
C5 C6 1.372(8)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.509(8)
C9 C10 1.387(9)
C9 C14 1.399(9)
C10 C11 1.377(8)
C11 C12 1.365(10)
C11 H11 0.9300
C12 C13 1.361(10)
C12 H12 0.9300
C13 C14 1.362(9)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 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
O3 H3A O2 2_546 0.82 2.05 2.697(9) 136.1
N2 H2 O3 . 0.89(7) 1.946(17) 2.840(7) 173(8)
O1 H1 N1 . 0.82 1.91 2.590(6) 140.1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655548
