#------------------------------------------------------------------------------
#$Date: 2023-05-22 10:32:51 +0300 (Mon, 22 May 2023) $
#$Revision: 283920 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107227.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_8107227
loop_
_publ_author_name
'Deng, Xin'
'Zhang, Zhijian'
_publ_section_title
;
 Crystal structure of
 (E)-N′-benzylidene-4-nitrobenzohydrazide -- methanol (1/1),
 C15H15N3O4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              825
_journal_page_last               827
_journal_paper_doi               10.1515/ncrs-2022-0242
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H15 N3 O4'
_chemical_formula_sum            'C15 H15 N3 O4'
_chemical_formula_weight         301.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.598(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5787(12)
_cell_length_b                   6.5393(5)
_cell_length_c                   16.3645(14)
_cell_measurement_reflns_used    2348
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      27.0260
_cell_measurement_theta_min      2.8350
_cell_volume                     1448.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f [1]'
_computing_data_collection       'CrysAlisPro 1.171.38.43f [1]'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [2]'
_diffrn_ambient_temperature      149.99(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6846
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.099
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.497
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.3229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2088
_reflns_number_total             2577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0242_suppl.cif
_cod_data_source_block           jwj061E_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107227
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85320(13) 0.3308(2) 0.69640(10) 0.0196(4) Uani 1 1 d . . . . .
C2 C 0.87129(13) 0.1263(3) 0.71618(11) 0.0218(4) Uani 1 1 d . . . . .
H2A H 0.834548 0.061785 0.754248 0.026 Uiso 1 1 calc R U . . .
C3 C 0.94353(13) 0.0188(3) 0.67955(11) 0.0230(4) Uani 1 1 d . . . . .
H3A H 0.956484 -0.117283 0.693011 0.028 Uiso 1 1 calc R U . . .
C4 C 0.99598(13) 0.1179(3) 0.62255(11) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.97937(13) 0.3207(3) 0.60125(11) 0.0249(4) Uani 1 1 d . . . . .
H5 H 1.015686 0.383914 0.562555 0.030 Uiso 1 1 calc R U . . .
C6 C 0.90778(13) 0.4265(3) 0.63875(11) 0.0237(4) Uani 1 1 d . . . . .
H6 H 0.895733 0.563037 0.625507 0.028 Uiso 1 1 calc R U . . .
C7 C 0.77983(13) 0.4581(2) 0.73704(10) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.55663(14) 0.3625(3) 0.81940(11) 0.0257(4) Uani 1 1 d . . . . .
H8 H 0.551512 0.226722 0.802641 0.031 Uiso 1 1 calc R U . . .
C9 C 0.47776(13) 0.4511(3) 0.86366(11) 0.0236(4) Uani 1 1 d . . . . .
C10 C 0.48136(14) 0.6511(3) 0.89301(12) 0.0289(5) Uani 1 1 d . . . . .
H10 H 0.534736 0.734593 0.883581 0.035 Uiso 1 1 calc R U . . .
C11 C 0.40562(15) 0.7255(3) 0.93613(13) 0.0352(5) Uani 1 1 d . . . . .
H11 H 0.408479 0.858892 0.955890 0.042 Uiso 1 1 calc R U . . .
C12 C 0.32539(14) 0.6030(3) 0.95020(12) 0.0323(5) Uani 1 1 d . . . . .
H12 H 0.274887 0.653378 0.979686 0.039 Uiso 1 1 calc R U . . .
C13 C 0.32096(14) 0.4060(3) 0.92023(12) 0.0316(5) Uani 1 1 d . . . . .
H13 H 0.266749 0.324070 0.928728 0.038 Uiso 1 1 calc R U . . .
C14 C 0.39665(14) 0.3299(3) 0.87766(11) 0.0281(5) Uani 1 1 d . . . . .
H14 H 0.393393 0.196332 0.858139 0.034 Uiso 1 1 calc R U . . .
C15 C 0.72124(17) 0.9465(3) 0.89505(13) 0.0414(6) Uani 1 1 d . . . . .
H15A H 0.791290 0.965599 0.894572 0.062 Uiso 1 1 calc R U . . .
H15B H 0.708300 0.818735 0.921011 0.062 Uiso 1 1 calc R U . . .
H15C H 0.693712 1.056253 0.924843 0.062 Uiso 1 1 calc R U . . .
N1 N 0.70154(11) 0.3582(2) 0.76270(9) 0.0237(4) Uani 1 1 d . . . . .
H1 H 0.694521 0.229036 0.754164 0.028 Uiso 1 1 calc R U . . .
N2 N 0.63247(11) 0.4658(2) 0.80300(9) 0.0243(4) Uani 1 1 d . . . . .
N3 N 1.07158(11) 0.0030(3) 0.58203(9) 0.0289(4) Uani 1 1 d . . . . .
O1 O 0.79181(9) 0.64431(17) 0.74479(8) 0.0297(3) Uani 1 1 d . . . . .
O2 O 1.11450(10) 0.0903(2) 0.52886(9) 0.0369(4) Uani 1 1 d . . . . .
O3 O 1.08699(11) -0.1752(2) 0.60235(9) 0.0404(4) Uani 1 1 d . . . . .
O4 O 0.67749(10) 0.94499(17) 0.81329(8) 0.0291(3) Uani 1 1 d . . . . .
H4 H 0.693270 0.839935 0.790297 0.044 Uiso 1 1 calc R U . . .
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'
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
C15 O4 H4 109.5 . .
C8 N2 N1 114.86(14) . .
C7 N1 N2 119.07(14) . .
C7 N1 H1 120.5 . .
N2 N1 H1 120.5 . .
O3 N3 O2 123.68(15) . .
O3 N3 C4 118.25(16) . .
O2 N3 C4 118.06(16) . .
C2 C1 C6 119.65(16) . .
C2 C1 C7 122.86(16) . .
C6 C1 C7 117.43(14) . .
C3 C2 C1 120.38(17) . .
C3 C2 H2A 119.8 . .
C1 C2 H2A 119.8 . .
O1 C7 N1 123.31(16) . .
O1 C7 C1 120.55(16) . .
N1 C7 C1 116.14(14) . .
C3 C4 C5 122.51(16) . .
C3 C4 N3 118.76(16) . .
C5 C4 N3 118.73(16) . .
C4 C3 C2 118.48(16) . .
C4 C3 H3A 120.8 . .
C2 C3 H3A 120.8 . .
C14 C9 C10 119.00(17) . .
C14 C9 C8 118.51(16) . .
C10 C9 C8 122.49(16) . .
C5 C6 C1 120.58(16) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
C6 C5 C4 118.39(17) . .
C6 C5 H5 120.8 . .
C4 C5 H5 120.8 . .
N2 C8 C9 121.98(16) . .
N2 C8 H8 119.0 . .
C9 C8 H8 119.0 . .
C13 C14 C9 120.61(17) . .
C13 C14 H14 119.7 . .
C9 C14 H14 119.7 . .
C11 C10 C9 119.98(18) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C13 C12 C11 119.58(18) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 120.26(18) . .
C12 C13 H13 119.9 . .
C14 C13 H13 119.9 . .
C10 C11 C12 120.56(18) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
O4 C15 H15A 109.5 . .
O4 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O4 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
O1 C7 1.234(2) .
O4 C15 1.420(2) .
O4 H4 0.8200 .
O2 N3 1.226(2) .
O3 N3 1.225(2) .
N2 C8 1.278(2) .
N2 N1 1.381(2) .
N1 C7 1.344(2) .
N1 H1 0.8600 .
N3 C4 1.472(2) .
C1 C2 1.393(2) .
C1 C6 1.394(2) .
C1 C7 1.495(2) .
C2 C3 1.382(2) .
C2 H2A 0.9300 .
C4 C3 1.380(3) .
C4 C5 1.385(2) .
C3 H3A 0.9300 .
C9 C14 1.391(3) .
C9 C10 1.393(3) .
C9 C8 1.460(3) .
C6 C5 1.377(3) .
C6 H6 0.9300 .
C5 H5 0.9300 .
C8 H8 0.9300 .
C14 C13 1.380(3) .
C14 H14 0.9300 .
C10 C11 1.381(3) .
C10 H10 0.9300 .
C12 C13 1.378(3) .
C12 C11 1.386(3) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C11 H11 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
_geom_hbond_publ_flag
O4 H4 O1 0.82 2.03 2.7949(17) 153.9 . yes
O4 H4 N2 0.82 2.60 3.1948(18) 131.0 . yes
N1 H1 O4 0.86 2.12 2.8524(18) 143.4 1_545 yes
C8 H8 O4 0.93 2.51 3.191(2) 130.2 1_545 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8 N2 N1 C7 174.67(16) . . . .
C6 C1 C2 C3 0.6(3) . . . .
C7 C1 C2 C3 -176.74(15) . . . .
N2 N1 C7 O1 -2.8(3) . . . .
N2 N1 C7 C1 178.05(14) . . . .
C2 C1 C7 O1 150.32(18) . . . .
C6 C1 C7 O1 -27.1(2) . . . .
C2 C1 C7 N1 -30.6(2) . . . .
C6 C1 C7 N1 152.06(16) . . . .
O3 N3 C4 C3 -2.1(2) . . . .
O2 N3 C4 C3 176.77(16) . . . .
O3 N3 C4 C5 178.70(16) . . . .
O2 N3 C4 C5 -2.4(2) . . . .
C5 C4 C3 C2 0.4(3) . . . .
N3 C4 C3 C2 -178.72(15) . . . .
C1 C2 C3 C4 -0.8(3) . . . .
C2 C1 C6 C5 0.0(3) . . . .
C7 C1 C6 C5 177.46(16) . . . .
C1 C6 C5 C4 -0.3(3) . . . .
C3 C4 C5 C6 0.1(3) . . . .
N3 C4 C5 C6 179.29(15) . . . .
N1 N2 C8 C9 178.37(15) . . . .
C14 C9 C8 N2 178.69(17) . . . .
C10 C9 C8 N2 -2.0(3) . . . .
C10 C9 C14 C13 -0.2(3) . . . .
C8 C9 C14 C13 179.06(17) . . . .
C14 C9 C10 C11 0.8(3) . . . .
C8 C9 C10 C11 -178.52(18) . . . .
C11 C12 C13 C14 1.1(3) . . . .
C9 C14 C13 C12 -0.7(3) . . . .
C9 C10 C11 C12 -0.4(3) . . . .
C13 C12 C11 C10 -0.6(3) . . . .
