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#$Date: 2022-11-24 10:08:35 +0200 (Thu, 24 Nov 2022) $
#$Revision: 279527 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106229.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_8106229
loop_
_publ_author_name
'Peng-Fei, Li'
'Chang-Qing, Cao'
'Xi-Shi, Tai'
_publ_section_title
;
 The crystal structure of 2-carboxybenzaldehyde-2-phenylacetohydrazone,
 C16H14N2O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              601
_journal_page_last               602
_journal_paper_doi               10.1515/ncrs-2017-0361
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                92.94(3)
_cell_angle_beta                 107.03(3)
_cell_angle_gamma                110.41(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7698(16)
_cell_length_b                   8.3020(17)
_cell_length_c                   12.197(2)
_cell_measurement_reflns_used    1848
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7455
_cell_measurement_theta_min      2.3434
_cell_volume                     694.6(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5320
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         3.139
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   0.9957
_exptl_transmission_factor_min   0.9579
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0582
_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)+(0.1180P)²+0.0177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1848
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0361_suppl.cif
_cod_data_source_block           ww
_cod_database_code               8106229
_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   0.983
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.0770(2) -0.1613(2) -0.22481(13) 0.0418(4) Uani 1 1 d . . . . .
N2 N -0.1027(2) -0.2628(2) -0.22069(14) 0.0452(4) Uani 1 1 d . . . . .
H2A H -0.1268 -0.2502 -0.1570 0.054 Uiso 1 1 calc R U . . .
C1 C 0.4035(3) 0.2771(2) 0.04399(16) 0.0420(5) Uani 1 1 d . . . . .
C2 C 0.4892(2) 0.2221(2) -0.03860(15) 0.0387(5) Uani 1 1 d . . . . .
C3 C 0.6775(3) 0.3255(3) -0.03187(18) 0.0491(5) Uani 1 1 d . . . . .
H3A H 0.7480 0.4250 0.0249 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7614(3) 0.2827(3) -0.1083(2) 0.0599(6) Uani 1 1 d . . . . .
H4A H 0.8874 0.3529 -0.1032 0.072 Uiso 1 1 calc R U . . .
C5 C 0.6571(3) 0.1351(3) -0.1922(2) 0.0625(7) Uani 1 1 d . . . . .
H5A H 0.7124 0.1067 -0.2446 0.075 Uiso 1 1 calc R U . . .
C6 C 0.4716(3) 0.0295(3) -0.19910(17) 0.0512(5) Uani 1 1 d . . . . .
H6A H 0.4048 -0.0713 -0.2549 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3818(3) 0.0703(2) -0.12436(15) 0.0394(5) Uani 1 1 d . . . . .
C8 C 0.1859(3) -0.0482(2) -0.13280(15) 0.0410(5) Uani 1 1 d . . . . .
H8A H 0.1404 -0.0413 -0.0709 0.049 Uiso 1 1 calc R U . . .
C9 C -0.2434(3) -0.3814(3) -0.31167(16) 0.0413(5) Uani 1 1 d . . . . .
C10 C -0.1956(3) -0.4234(3) -0.41802(16) 0.0429(5) Uani 1 1 d . . . . .
H10A H -0.0847 -0.3263 -0.4223 0.051 Uiso 1 1 calc R U . . .
H10B H -0.3054 -0.4418 -0.4874 0.051 Uiso 1 1 calc R U . . .
C11 C -0.1491(2) -0.5858(2) -0.41227(15) 0.0378(5) Uani 1 1 d . . . . .
C12 C 0.0233(3) -0.5814(3) -0.33352(17) 0.0476(5) Uani 1 1 d . . . . .
H12A H 0.1109 -0.4774 -0.2846 0.057 Uiso 1 1 calc R U . . .
C13 C 0.0663(3) -0.7282(3) -0.32671(19) 0.0565(6) Uani 1 1 d . . . . .
H13A H 0.1820 -0.7231 -0.2729 0.068 Uiso 1 1 calc R U . . .
C14 C -0.0608(3) -0.8830(3) -0.39907(19) 0.0578(6) Uani 1 1 d . . . . .
H14A H -0.0314 -0.9824 -0.3945 0.069 Uiso 1 1 calc R U . . .
C15 C -0.2321(3) -0.8896(3) -0.47846(19) 0.0570(6) Uani 1 1 d . . . . .
H15A H -0.3183 -0.9936 -0.5279 0.068 Uiso 1 1 calc R U . . .
C16 C -0.2760(3) -0.7420(3) -0.48466(16) 0.0468(5) Uani 1 1 d . . . . .
H16A H -0.3922 -0.7477 -0.5381 0.056 Uiso 1 1 calc R U . . .
O1 O 0.53628(18) 0.38260(19) 0.13923(12) 0.0572(5) Uani 1 1 d . . . . .
H1 H 0.4824 0.4090 0.1818 0.086 Uiso 1 1 calc R U . . .
O2 O 0.22998(18) 0.23251(19) 0.02573(12) 0.0548(4) Uani 1 1 d . . . . .
O3 O -0.40693(19) -0.45740(19) -0.30428(12) 0.0533(4) Uani 1 1 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'
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
C8 N1 N2 114.11(15) . .
C9 N2 N1 123.24(15) . .
C9 N2 H2A 118.4 . .
N1 N2 H2A 118.4 . .
O2 C1 O1 122.93(18) . .
O2 C1 C2 124.00(17) . .
O1 C1 C2 113.06(15) . .
C3 C2 C7 119.82(17) . .
C3 C2 C1 118.69(17) . .
C7 C2 C1 121.47(15) . .
C4 C3 C2 120.9(2) . .
C4 C3 H3A 119.6 . .
C2 C3 H3A 119.6 . .
C5 C4 C3 119.51(19) . .
C5 C4 H4A 120.2 . .
C3 C4 H4A 120.2 . .
C6 C5 C4 120.46(19) . .
C6 C5 H5A 119.8 . .
C4 C5 H5A 119.8 . .
C5 C6 C7 121.5(2) . .
C5 C6 H6A 119.3 . .
C7 C6 H6A 119.3 . .
C6 C7 C2 117.85(17) . .
C6 C7 C8 119.61(18) . .
C2 C7 C8 122.46(16) . .
N1 C8 C7 120.46(17) . .
N1 C8 H8A 119.8 . .
C7 C8 H8A 119.8 . .
O3 C9 N2 119.27(17) . .
O3 C9 C10 121.48(16) . .
N2 C9 C10 119.20(16) . .
C9 C10 C11 109.83(16) . .
C9 C10 H10A 109.7 . .
C11 C10 H10A 109.7 . .
C9 C10 H10B 109.7 . .
C11 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
C16 C11 C12 118.23(19) . .
C16 C11 C10 121.30(17) . .
C12 C11 C10 120.46(17) . .
C13 C12 C11 121.04(19) . .
C13 C12 H12A 119.5 . .
C11 C12 H12A 119.5 . .
C12 C13 C14 120.3(2) . .
C12 C13 H13A 119.8 . .
C14 C13 H13A 119.8 . .
C15 C14 C13 119.5(2) . .
C15 C14 H14A 120.3 . .
C13 C14 H14A 120.3 . .
C14 C15 C16 120.1(2) . .
C14 C15 H15A 119.9 . .
C16 C15 H15A 119.9 . .
C11 C16 C15 120.77(19) . .
C11 C16 H16A 119.6 . .
C15 C16 H16A 119.6 . .
C1 O1 H1 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C8 1.280(2) .
N1 N2 1.374(2) .
N2 C9 1.350(2) .
N2 H2A 0.8600 .
C1 O2 1.213(2) .
C1 O1 1.321(2) .
C1 C2 1.492(3) .
C2 C3 1.389(3) .
C2 C7 1.414(3) .
C3 C4 1.380(3) .
C3 H3A 0.9300 .
C4 C5 1.378(3) .
C4 H4A 0.9300 .
C5 C6 1.376(3) .
C5 H5A 0.9300 .
C6 C7 1.392(3) .
C6 H6A 0.9300 .
C7 C8 1.466(3) .
C8 H8A 0.9300 .
C9 O3 1.239(2) .
C9 C10 1.506(3) .
C10 C11 1.513(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C16 1.383(3) .
C11 C12 1.388(3) .
C12 C13 1.372(3) .
C12 H12A 0.9300 .
C13 C14 1.376(3) .
C13 H13A 0.9300 .
C14 C15 1.379(3) .
C14 H14A 0.9300 .
C15 C16 1.382(3) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
O1 H1 0.8200 .
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 N1 N2 C9 175.43(18) . . . .
O2 C1 C2 C3 156.5(2) . . . .
O1 C1 C2 C3 -22.4(3) . . . .
O2 C1 C2 C7 -22.1(3) . . . .
O1 C1 C2 C7 158.97(18) . . . .
C7 C2 C3 C4 0.3(3) . . . .
C1 C2 C3 C4 -178.28(19) . . . .
C2 C3 C4 C5 -0.1(3) . . . .
C3 C4 C5 C6 -0.9(4) . . . .
C4 C5 C6 C7 1.8(4) . . . .
C5 C6 C7 C2 -1.6(3) . . . .
C5 C6 C7 C8 -178.45(19) . . . .
C3 C2 C7 C6 0.5(3) . . . .
C1 C2 C7 C6 179.10(17) . . . .
C3 C2 C7 C8 177.29(17) . . . .
C1 C2 C7 C8 -4.1(3) . . . .
N2 N1 C8 C7 -179.74(16) . . . .
C6 C7 C8 N1 -18.7(3) . . . .
C2 C7 C8 N1 164.64(18) . . . .
N1 N2 C9 O3 -174.00(16) . . . .
N1 N2 C9 C10 8.4(3) . . . .
O3 C9 C10 C11 -80.9(2) . . . .
N2 C9 C10 C11 96.6(2) . . . .
C9 C10 C11 C16 108.52(18) . . . .
C9 C10 C11 C12 -71.5(2) . . . .
C16 C11 C12 C13 -0.6(3) . . . .
C10 C11 C12 C13 179.42(17) . . . .
C11 C12 C13 C14 0.6(3) . . . .
C12 C13 C14 C15 -0.1(3) . . . .
C13 C14 C15 C16 -0.4(3) . . . .
C12 C11 C16 C15 0.1(3) . . . .
C10 C11 C16 C15 -179.90(17) . . . .
C14 C15 C16 C11 0.4(3) . . . .
