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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/62/7226241.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_7226241
loop_
_publ_author_name
'Beard, Lindsey E.'
'Ojala, Charles R.'
'Kassekert, Kara J.'
'Ojala, William H.'
_publ_section_title
;
 Molecular packing preferences in “bridge-flipped” isomeric
 aryl-2-pyridylhydrazones and 2-pyridinecarboxaldehyde arylhydrazones
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              7036
_journal_paper_doi               10.1039/C6CE01519K
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C13 H10 N4'
_chemical_formula_weight         222.25
_chemical_melting_point          514(3)
_chemical_name_systematic        2-pyrcarboxaldehyde-2-(4-CNphenyl)hydrazone
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.093(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0570(7)
_cell_length_b                   3.8670(2)
_cell_length_c                   18.2283(7)
_cell_measurement_reflns_used    2926
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.21
_cell_measurement_theta_min      2.86
_cell_volume                     1088.85(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'PLATON (Spek 2009) Mercury (Macrae et al. 2008)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.527
_diffrn_reflns_theta_min         2.861
_diffrn_source                   'ImuS micro-focus'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_correction_T_min  0.7525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.115
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0798
_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)+(0.1281P)²+1.7150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2227
_refine_ls_wR_factor_ref         0.2489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1677
_reflns_number_total             2216
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01519k2.cif
_cod_data_source_block           15283a3NNC
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '511-516K' was changed to '514(3)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7226237--7226244.cif.
;
_cod_database_code               7226241
_shelx_shelxl_version_number     2014/7
_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   0.847
_shelx_estimated_absorpt_t_max   0.986
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
C1 C 0.29731(17) 0.7810(8) 0.33477(15) 0.0266(7) Uani 1 1 d . .
H1 H 0.2951 0.6596 0.3792 0.032 Uiso 1 1 calc R U
C2 C 0.21642(17) 0.8901(8) 0.26819(15) 0.0252(6) Uani 1 1 d . .
C3 C 0.13851(17) 0.8166(8) 0.27213(16) 0.0261(6) Uani 1 1 d . .
H3 H 0.1388 0.6989 0.3180 0.031 Uiso 1 1 calc R U
C4 C 0.06041(18) 0.9137(8) 0.20973(16) 0.0275(7) Uani 1 1 d . .
H4 H 0.0074 0.8615 0.2127 0.033 Uiso 1 1 calc R U
C5 C 0.06009(17) 1.0891(8) 0.14237(15) 0.0270(7) Uani 1 1 d . .
C6 C 0.13790(18) 1.1631(8) 0.13767(15) 0.0276(7) Uani 1 1 d . .
H6 H 0.1377 1.2810 0.0919 0.033 Uiso 1 1 calc R U
C7 C 0.21522(18) 1.0637(8) 0.20003(15) 0.0264(6) Uani 1 1 d . .
H7 H 0.2682 1.1133 0.1968 0.032 Uiso 1 1 calc R U
C8 C 0.52375(18) 0.8119(8) 0.40735(17) 0.0295(7) Uani 1 1 d . .
C9 C 0.6705(2) 0.7950(9) 0.48342(17) 0.0348(8) Uani 1 1 d . .
H9 H 0.7182 0.7242 0.5316 0.042 Uiso 1 1 calc R U
C10 C 0.68742(18) 0.9749(8) 0.42630(16) 0.0296(7) Uani 1 1 d . .
H10 H 0.7449 1.0315 0.4349 0.036 Uiso 1 1 calc R U
C11 C 0.61644(19) 1.0693(8) 0.35563(16) 0.0302(7) Uani 1 1 d . .
H11 H 0.6251 1.1872 0.3139 0.036 Uiso 1 1 calc R U
C12 C 0.53488(19) 0.9939(9) 0.34589(17) 0.0326(7) Uani 1 1 d . .
H12 H 0.4862 1.0632 0.2983 0.039 Uiso 1 1 calc R U
C13 C -0.02194(19) 1.2001(8) 0.07951(17) 0.0310(7) Uani 1 1 d . .
H2N H 0.429(2) 0.632(9) 0.4368(15) 0.037 Uiso 1 1 d D U
N1 N 0.37111(16) 0.8443(7) 0.33496(14) 0.0327(7) Uani 1 1 d . .
N2 N 0.44183(16) 0.7308(8) 0.39955(14) 0.0352(7) Uani 1 1 d D .
N3 N 0.59027(17) 0.7139(7) 0.47502(14) 0.0319(6) Uani 1 1 d . .
N4 N -0.08716(17) 1.2947(8) 0.03243(15) 0.0403(7) 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 0.0181 0.0091 '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 0.0311 0.0180 '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
N1 C1 C2 121.9(3)
N1 C1 H1 119.1
C2 C1 H1 119.1
C3 C2 C7 119.2(2)
C3 C2 C1 119.0(2)
C7 C2 C1 121.8(3)
C4 C3 C2 120.6(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.7(3)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 120.2(2)
C6 C5 C13 121.1(3)
C4 C5 C13 118.7(3)
C7 C6 C5 119.6(2)
C7 C6 H6 120.2
C5 C6 H6 120.2
C6 C7 C2 120.8(3)
C6 C7 H7 119.6
C2 C7 H7 119.6
N3 C8 N2 117.4(3)
N3 C8 C12 122.2(3)
N2 C8 C12 120.4(3)
N3 C9 C10 124.0(3)
N3 C9 H9 118.0
C10 C9 H9 118.0
C9 C10 C11 116.9(3)
C9 C10 H10 121.6
C11 C10 H10 121.6
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C8 118.8(3)
C11 C12 H12 120.6
C8 C12 H12 120.6
N4 C13 C5 177.2(3)
C1 N1 N2 116.9(2)
N1 N2 C8 120.4(3)
N1 N2 H2N 113(2)
C8 N2 H2N 126(2)
C8 N3 C9 117.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.281(4)
C1 C2 1.461(4)
C1 H1 0.9500
C2 C3 1.390(4)
C2 C7 1.405(4)
C3 C4 1.387(4)
C3 H3 0.9500
C4 C5 1.401(4)
C4 H4 0.9500
C5 C6 1.395(4)
C5 C13 1.448(4)
C6 C7 1.381(4)
C6 H6 0.9500
C7 H7 0.9500
C8 N3 1.329(4)
C8 N2 1.379(4)
C8 C12 1.402(4)
C9 N3 1.347(4)
C9 C10 1.381(4)
C9 H9 0.9500
C10 C11 1.391(4)
C10 H10 0.9500
C11 C12 1.357(4)
C11 H11 0.9500
C12 H12 0.9500
C13 N4 1.139(4)
N1 N2 1.353(3)
N2 H2N 0.884(5)
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 H2N N3 0.884(5) 2.220(10) 3.090(4) 168(3) 3_666
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
N1 C1 C2 C3 -179.3(3)
N1 C1 C2 C7 1.4(5)
C2 C1 N1 N2 -179.8(3)
C1 N1 N2 C8 -175.0(3)
N3 C8 N2 N1 175.2(3)
C12 C8 N2 N1 -4.1(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9675733
