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#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240323.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_7240323
loop_
_publ_author_name
'Zhang, Zhenfeng'
_publ_section_title
;
 An X-shaped cyano-carbonyl interaction on the polar surface of
 (cyanoacetyl)hydrazones
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00359J
_journal_year                    2020
_chemical_formula_moiety         'C10 H9 N3 O'
_chemical_formula_sum            'C10 H9 N3 O'
_chemical_formula_weight         187.20
_chemical_name_common
;
benzaldehyde (cyanoacetyl)hydrazone
;
_chemical_name_systematic
;
2-cyano-N'-[(1E)-phenylmethylidene]acetohydrazide
;
_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   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-03-05 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.020(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.200(5)
_cell_length_b                   9.143(4)
_cell_length_c                   8.797(4)
_cell_measurement_reflns_used    940
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.78
_cell_measurement_theta_min      2.81
_cell_volume                     959.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4032
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.039
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_min         1.707
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       prism
_exptl_crystal_F_000             392.0
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0433
_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)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1020
_reflns_number_total             1698
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00359j10.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240323
_shelx_shelxl_version_number     2017/1
_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   0.974
_shelx_estimated_absorpt_t_max   0.983
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
N2 N 0.60660(13) 0.24310(16) 0.09739(18) 0.0495(5) Uani 1 1 d . . . . .
N1 N 0.53301(14) 0.16641(17) 0.16963(19) 0.0503(5) Uani 1 1 d . . . . .
N3 N 0.2356(2) 0.2798(2) 0.4159(3) 0.0962(8) Uani 1 1 d . . . . .
O1 O 0.44413(11) 0.37180(12) 0.22468(17) 0.0611(5) Uani 1 1 d . . . . .
C4 C 0.68141(16) 0.1641(2) 0.0552(2) 0.0510(5) Uani 1 1 d . . . . .
H4 H 0.680673 0.063715 0.072039 0.061 Uiso 1 1 calc R U . . .
C5 C 0.76756(17) 0.22490(19) -0.0180(2) 0.0479(5) Uani 1 1 d . . . . .
C6 C 0.77614(17) 0.3746(2) -0.0442(2) 0.0555(6) Uani 1 1 d . . . . .
H6 H 0.723345 0.438467 -0.018893 0.067 Uiso 1 1 calc R U . . .
C7 C 0.86218(19) 0.4282(2) -0.1070(2) 0.0675(7) Uani 1 1 d . . . . .
H7 H 0.867192 0.528246 -0.123561 0.081 Uiso 1 1 calc R U . . .
C8 C 0.9412(2) 0.3353(3) -0.1460(3) 0.0709(7) Uani 1 1 d . . . . .
H8 H 0.999487 0.372317 -0.187936 0.085 Uiso 1 1 calc R U . . .
C9 C 0.9328(2) 0.1872(3) -0.1219(3) 0.0715(7) Uani 1 1 d . . . . .
H9 H 0.985567 0.123841 -0.148136 0.086 Uiso 1 1 calc R U . . .
C10 C 0.84681(18) 0.1324(2) -0.0593(2) 0.0601(6) Uani 1 1 d . . . . .
H10 H 0.841749 0.032117 -0.044395 0.072 Uiso 1 1 calc R U . . .
C1 C 0.45758(17) 0.23891(18) 0.2312(2) 0.0465(5) Uani 1 1 d . . . . .
C2 C 0.38820(17) 0.13962(19) 0.3120(3) 0.0567(6) Uani 1 1 d . . . . .
H2B H 0.353781 0.064274 0.240031 0.068 Uiso 1 1 calc R U . . .
H2A H 0.437066 0.091895 0.398945 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3018(2) 0.2180(2) 0.3679(3) 0.0597(6) Uani 1 1 d . . . . .
H1 H 0.5437(15) 0.069(2) 0.188(2) 0.067(6) Uiso 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
_geom_angle_publ_flag
C4 N2 N1 114.53(15) . . ?
C1 N1 N2 119.93(16) . . ?
C1 N1 H1 119.7(12) . . ?
N2 N1 H1 119.6(12) . . ?
N2 C4 C5 122.60(18) . . ?
N2 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C10 C5 C6 118.3(2) . . ?
C10 C5 C4 119.35(18) . . ?
C6 C5 C4 122.31(18) . . ?
C7 C6 C5 120.39(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
O1 C1 N1 124.68(18) . . ?
O1 C1 C2 122.25(18) . . ?
N1 C1 C2 113.07(15) . . ?
C3 C2 C1 112.39(15) . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
H2B C2 H2A 107.9 . . ?
N3 C3 C2 178.1(3) . . ?
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
N2 C4 1.278(2) . ?
N2 N1 1.393(2) . ?
N1 C1 1.337(2) . ?
N1 H1 0.91(2) . ?
N3 C3 1.136(3) . ?
O1 C1 1.2259(19) . ?
C4 C5 1.453(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.389(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C1 C2 1.515(3) . ?
C2 C3 1.443(3) . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
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
N1 H1 O1 0.91(2) 1.95(2) 2.844(2) 166.2(16) 2_645 yes
N1 H1 O1 0.91(2) 1.95(2) 2.844(2) 166.2(16) 2_645 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
_geom_torsion_publ_flag
C4 N2 N1 C1 174.02(18) . . . . ?
N1 N2 C4 C5 -178.21(17) . . . . ?
N2 C4 C5 C10 179.33(19) . . . . ?
N2 C4 C5 C6 1.5(3) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C4 C5 C6 C7 176.88(19) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
C6 C5 C10 C9 1.1(3) . . . . ?
C4 C5 C10 C9 -176.81(19) . . . . ?
N2 N1 C1 O1 2.9(3) . . . . ?
N2 N1 C1 C2 -177.16(17) . . . . ?
O1 C1 C2 C3 4.2(3) . . . . ?
N1 C1 C2 C3 -175.75(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6869220
