#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/22/2222215.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_2222215
loop_
_publ_author_name
'Lin, Xue-Song'
'Sang, Ya-Li'
_publ_section_title
;
 N'-(5-Bromo-2-methoxybenzylidene)-2-methoxybenzohydrazide
;
_journal_coeditor_code           AT2816
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1649
_journal_paper_doi               10.1107/S1600536809022971
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H15 Br N2 O3'
_chemical_formula_moiety         'C16 H15 Br N2 O3'
_chemical_formula_sum            'C16 H15 Br N2 O3'
_chemical_formula_weight         363.21
_chemical_name_systematic
;
N'-(5-Bromo-2-methoxybenzylidene)-2-methoxybenzohydrazide
;
_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                 99.1280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3286(3)
_cell_length_b                   11.4816(3)
_cell_length_c                   10.1233(2)
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.35
_cell_volume                     1529.59(6)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9188
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.701
_exptl_absorpt_correction_T_max  0.6420
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.685
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+1.0409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                2281
_reflns_number_total             3323
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2816.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222215
_cod_database_fobs_code          2222215
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.36301(2) 1.06194(4) 0.08660(4) 0.07080(16) Uani d . 1 . .
O O1 0.67425(14) 1.12056(19) 0.5818(2) 0.0511(5) Uani d . 1 . .
O O2 0.80411(13) 0.73514(17) 0.15200(18) 0.0419(5) Uani d . 1 . .
O O3 1.01119(14) 0.80174(18) 0.4696(2) 0.0497(5) Uani d . 1 . .
N N1 0.72756(15) 0.88017(18) 0.3201(2) 0.0327(5) Uani d . 1 . .
N N2 0.80859(15) 0.80683(19) 0.3608(2) 0.0322(5) Uani d D 1 . .
C C1 0.61419(18) 1.0218(2) 0.3825(3) 0.0335(6) Uani d . 1 . .
C C2 0.60017(19) 1.1107(2) 0.4729(3) 0.0377(6) Uani d . 1 . .
C C3 0.5157(2) 1.1822(2) 0.4485(3) 0.0447(7) Uani d . 1 . .
H H3 0.5068 1.2409 0.5089 0.054 Uiso calc R 1 . .
C C4 0.4447(2) 1.1667(3) 0.3350(3) 0.0484(7) Uani d . 1 . .
H H4 0.3873 1.2138 0.3194 0.058 Uiso calc R 1 . .
C C5 0.4594(2) 1.0810(3) 0.2451(3) 0.0438(7) Uani d . 1 . .
C C6 0.54289(19) 1.0089(2) 0.2674(3) 0.0383(6) Uani d . 1 . .
H H6 0.5516 0.9515 0.2054 0.046 Uiso calc R 1 . .
C C7 0.6646(3) 1.2090(3) 0.6772(4) 0.0734(11) Uani d . 1 . .
H H7A 0.6630 1.2839 0.6347 0.110 Uiso calc R 1 . .
H H7B 0.7214 1.2054 0.7483 0.110 Uiso calc R 1 . .
H H7C 0.6027 1.1974 0.7129 0.110 Uiso calc R 1 . .
C C8 0.70088(18) 0.9428(2) 0.4122(3) 0.0340(6) Uani d . 1 . .
H H8 0.7366 0.9383 0.4988 0.041 Uiso calc R 1 . .
C C9 0.84257(17) 0.7374(2) 0.2700(2) 0.0300(5) Uani d . 1 . .
C C10 0.93090(18) 0.6607(2) 0.3210(2) 0.0331(6) Uani d . 1 . .
C C11 1.01527(19) 0.6938(3) 0.4138(3) 0.0376(6) Uani d . 1 . .
C C12 1.0973(2) 0.6182(3) 0.4424(3) 0.0517(8) Uani d . 1 . .
H H12 1.1548 0.6414 0.5010 0.062 Uiso calc R 1 . .
C C13 1.0941(3) 0.5100(3) 0.3852(3) 0.0588(9) Uani d . 1 . .
H H13 1.1493 0.4600 0.4056 0.071 Uiso calc R 1 . .
C C14 1.0107(3) 0.4748(3) 0.2987(3) 0.0576(9) Uani d . 1 . .
H H14 1.0080 0.4002 0.2626 0.069 Uiso calc R 1 . .
C C15 0.9304(2) 0.5502(2) 0.2649(3) 0.0447(7) Uani d . 1 . .
H H15 0.8747 0.5267 0.2034 0.054 Uiso calc R 1 . .
C C16 1.0993(2) 0.8449(4) 0.5536(4) 0.0690(10) Uani d . 1 . .
H H16A 1.1117 0.7995 0.6342 0.103 Uiso calc R 1 . .
H H16B 1.0887 0.9248 0.5757 0.103 Uiso calc R 1 . .
H H16C 1.1568 0.8395 0.5076 0.103 Uiso calc R 1 . .
H H2 0.830(3) 0.802(3) 0.4490(12) 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'
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
C2 O1 C7 . . 118.5(2) ?
C11 O3 C16 . . 118.6(2) ?
C8 N1 N2 . . 115.0(2) ?
C9 N2 N1 . . 119.2(2) ?
C9 N2 H2 . . 124(2) ?
N1 N2 H2 . . 116(2) ?
C6 C1 C2 . . 118.7(2) ?
C6 C1 C8 . . 121.3(2) ?
C2 C1 C8 . . 120.0(2) ?
O1 C2 C3 . . 124.0(3) ?
O1 C2 C1 . . 115.7(2) ?
C3 C2 C1 . . 120.3(3) ?
C4 C3 C2 . . 120.3(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 119.5(3) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C6 C5 C4 . . 121.2(3) ?
C6 C5 Br1 . . 119.3(2) ?
C4 C5 Br1 . . 119.5(2) ?
C5 C6 C1 . . 120.1(3) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C1 . . 120.2(2) ?
N1 C8 H8 . . 119.9 ?
C1 C8 H8 . . 119.9 ?
O2 C9 N2 . . 123.0(2) ?
O2 C9 C10 . . 120.7(2) ?
N2 C9 C10 . . 116.3(2) ?
C15 C10 C11 . . 118.3(2) ?
C15 C10 C9 . . 116.3(2) ?
C11 C10 C9 . . 125.3(2) ?
O3 C11 C12 . . 124.2(3) ?
O3 C11 C10 . . 116.3(2) ?
C12 C11 C10 . . 119.5(3) ?
C13 C12 C11 . . 120.5(3) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C14 C13 C12 . . 120.6(3) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 119.7(3) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C10 . . 121.3(3) ?
C14 C15 H15 . . 119.4 ?
C10 C15 H15 . . 119.4 ?
O3 C16 H16A . . 109.5 ?
O3 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O3 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 C5 . 1.902(3) ?
O1 C2 . 1.363(3) ?
O1 C7 . 1.421(4) ?
O2 C9 . 1.223(3) ?
O3 C11 . 1.367(3) ?
O3 C16 . 1.425(3) ?
N1 C8 . 1.273(3) ?
N1 N2 . 1.380(3) ?
N2 C9 . 1.348(3) ?
N2 H2 . 0.894(10) ?
C1 C6 . 1.390(4) ?
C1 C2 . 1.402(4) ?
C1 C8 . 1.462(3) ?
C2 C3 . 1.383(4) ?
C3 C4 . 1.380(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(4) ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.495(3) ?
C10 C15 . 1.390(4) ?
C10 C11 . 1.398(3) ?
C11 C12 . 1.389(4) ?
C12 C13 . 1.369(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.363(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.377(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
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
N2 H2 O2 4_576 0.894(10) 2.179(19) 2.997(3) 152(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7932383
