#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102369.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102369
loop_
_publ_author_name
'Congshan Zhou'
'Tao Yang'
_publ_section_title
;
 Crystal structure of
 2-nitro-N'-(5-bromo-2-methoxybenzylidene)benzohydrazide, C15H12BrN3O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              39
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C15 H12 Br N3 O4'
_chemical_formula_sum            'C15 H12 Br N3 O4'
_chemical_formula_weight         378.19
_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                 90.1240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3077(3)
_cell_length_b                   7.4907(2)
_cell_length_c                   18.3286(5)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.6
_cell_volume                     1552.48(7)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 [10]'
_computing_structure_solution    'SHELXS-97 [9]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9004
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    2.672
_exptl_absorpt_correction_T_max  0.5217
_exptl_absorpt_correction_T_min  0.5012
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0367
_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)+(0.0484P)²+0.6581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2326
_reflns_number_total             3371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2453.cff
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8102369
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.17214(3) 0.41529(5) 0.133727(18) 0.07247(16) Uani 1 1 d . . .
O1 O 0.0572(2) 0.1179(3) -0.13528(11) 0.0671(6) Uani 1 1 d . . .
O2 O 0.56298(17) 0.1377(3) 0.07034(12) 0.0681(6) Uani 1 1 d . . .
O3 O 0.3406(3) 0.0567(3) 0.17837(15) 0.0832(7) Uani 1 1 d . . .
O4 O 0.2187(4) 0.2088(5) 0.2390(2) 0.1620(18) Uani 1 1 d . . .
N1 N 0.26533(18) 0.2213(3) 0.03262(11) 0.0458(5) Uani 1 1 d . . .
N2 N 0.37912(19) 0.1547(3) 0.02628(12) 0.0506(6) Uani 1 1 d D . .
N3 N 0.3055(3) 0.1969(4) 0.20059(15) 0.0699(7) Uani 1 1 d . . .
C1 C 0.0693(2) 0.2147(3) -0.01457(14) 0.0451(6) Uani 1 1 d . . .
C2 C -0.0009(2) 0.1870(4) -0.07677(15) 0.0510(7) Uani 1 1 d . . .
C3 C -0.1198(3) 0.2292(4) -0.07577(17) 0.0623(8) Uani 1 1 d . . .
H3 H -0.1658 0.2121 -0.1173 0.075 Uiso 1 1 calc R . .
C4 C -0.1706(3) 0.2969(4) -0.01314(17) 0.0619(8) Uani 1 1 d . . .
H4 H -0.2507 0.3247 -0.0124 0.074 Uiso 1 1 calc R . .
C5 C -0.1024(2) 0.3230(4) 0.04807(15) 0.0514(7) Uani 1 1 d . . .
C6 C 0.0160(2) 0.2837(4) 0.04758(14) 0.0468(6) Uani 1 1 d . . .
H6 H 0.0612 0.3034 0.0893 0.056 Uiso 1 1 calc R . .
C7 C 0.1938(2) 0.1659(4) -0.01603(14) 0.0468(6) Uani 1 1 d . . .
H7 H 0.2217 0.0929 -0.0533 0.056 Uiso 1 1 calc R . .
C8 C 0.4646(2) 0.2049(4) 0.07227(15) 0.0493(6) Uani 1 1 d . . .
C9 C 0.4407(2) 0.3612(4) 0.12200(14) 0.0466(6) Uani 1 1 d . . .
C10 C 0.3664(2) 0.3598(4) 0.18080(16) 0.0521(7) Uani 1 1 d . . .
C11 C 0.3496(3) 0.5084(5) 0.22564(17) 0.0630(8) Uani 1 1 d . . .
H11 H 0.2996 0.5027 0.2658 0.076 Uiso 1 1 calc R . .
C12 C 0.4077(3) 0.6602(5) 0.20919(19) 0.0723(9) Uani 1 1 d . . .
H12 H 0.3969 0.7608 0.2381 0.087 Uiso 1 1 calc R . .
C13 C 0.4830(4) 0.6689(5) 0.1501(2) 0.0782(10) Uani 1 1 d . . .
H13 H 0.5218 0.7750 0.1392 0.094 Uiso 1 1 calc R . .
C14 C 0.5005(3) 0.5208(4) 0.10728(16) 0.0594(7) Uani 1 1 d . . .
H14 H 0.5526 0.5265 0.0682 0.071 Uiso 1 1 calc R . .
C15 C -0.0077(4) 0.0892(6) -0.20066(18) 0.0893(12) Uani 1 1 d . . .
H15A H -0.0712 0.0072 -0.1914 0.134 Uiso 1 1 calc R . .
H15B H 0.0437 0.0405 -0.2372 0.134 Uiso 1 1 calc R . .
H15C H -0.0396 0.2006 -0.2175 0.134 Uiso 1 1 calc R . .
H2 H 0.395(3) 0.066(3) -0.0053(14) 0.080 Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C15 118.2(3) . . ?
C7 N1 N2 114.4(2) . . ?
C8 N2 N1 121.1(2) . . ?
C8 N2 H2 118(2) . . ?
N1 N2 H2 121(2) . . ?
O3 N3 O4 122.2(3) . . ?
O3 N3 C10 119.8(3) . . ?
O4 N3 C10 118.0(3) . . ?
C6 C1 C2 118.4(2) . . ?
C6 C1 C7 122.0(2) . . ?
C2 C1 C7 119.6(2) . . ?
O1 C2 C3 124.7(3) . . ?
O1 C2 C1 115.1(2) . . ?
C3 C2 C1 120.3(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 Br1 119.6(2) . . ?
C4 C5 Br1 119.8(2) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C1 121.3(2) . . ?
N1 C7 H7 119.4 . . ?
C1 C7 H7 119.4 . . ?
O2 C8 N2 121.6(3) . . ?
O2 C8 C9 120.1(2) . . ?
N2 C8 C9 118.0(2) . . ?
C10 C9 C14 117.1(3) . . ?
C10 C9 C8 125.5(3) . . ?
C14 C9 C8 117.3(2) . . ?
C9 C10 C11 122.8(3) . . ?
C9 C10 N3 119.8(3) . . ?
C11 C10 N3 117.3(3) . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 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
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.889(3) . ?
O1 C2 1.361(3) . ?
O1 C15 1.421(4) . ?
O2 C8 1.222(3) . ?
O3 N3 1.195(4) . ?
O4 N3 1.213(4) . ?
N1 C7 1.272(3) . ?
N1 N2 1.385(3) . ?
N2 C8 1.335(3) . ?
N2 H2 0.900(10) . ?
N3 C10 1.448(4) . ?
C1 C6 1.389(4) . ?
C1 C2 1.403(4) . ?
C1 C7 1.455(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.509(4) . ?
C9 C10 1.368(4) . ?
C9 C14 1.400(4) . ?
C10 C11 1.397(4) . ?
C11 C12 1.348(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.900(10) 1.994(11) 2.893(3) 177(3) 3_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7913776
