#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/62/7226243.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_7226243
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 H9 Br N4'
_chemical_formula_weight         301.15
_chemical_melting_point          524.5(15)
_chemical_name_systematic        '4-CNbenzaldehyde 2-(5Br-2pyridinyl)hydrazone'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.71(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.552(5)
_cell_length_b                   3.962(3)
_cell_length_c                   25.17(2)
_cell_measurement_reflns_used    2879
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.39
_cell_measurement_theta_min      3.66
_cell_volume                     1221.1(14)
_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_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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     1.54184
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14181
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.484
_diffrn_reflns_theta_min         3.600
_diffrn_source                   'ImuS micro-focus'
_exptl_absorpt_coefficient_mu    4.478
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0411
_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)+4.7349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2163
_reflns_number_total             2480
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01519k2.cif
_cod_data_source_block           16022a4NNC
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '523-526 K' was changed to
'524.5(15)' - 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_original_cell_volume        1220.9(14)
_cod_database_code               7226243
_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   0.401
_shelx_estimated_absorpt_t_max   0.957
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br1 Br -0.13070(3) 0.65794(10) 0.28322(2) 0.02922(13) Uani 1 1 d . .
C1 C 0.2811(2) 0.2801(9) 0.56903(13) 0.0229(7) Uani 1 1 d . .
H1 H 0.2412 0.1454 0.5891 0.028 Uiso 1 1 calc R U
C2 C 0.3896(3) 0.4043(9) 0.59583(13) 0.0223(7) Uani 1 1 d . .
C3 C 0.4261(3) 0.3533(10) 0.65169(13) 0.0235(7) Uani 1 1 d . .
H3 H 0.3804 0.2399 0.6714 0.028 Uiso 1 1 calc R U
C4 C 0.5284(3) 0.4663(10) 0.67879(13) 0.0256(7) Uani 1 1 d . .
H4 H 0.5525 0.4323 0.7169 0.031 Uiso 1 1 calc R U
C5 C 0.5951(3) 0.6299(10) 0.64950(14) 0.0239(7) Uani 1 1 d . .
C6 C 0.5596(3) 0.6831(10) 0.59344(14) 0.0257(7) Uani 1 1 d . .
H6 H 0.6055 0.7956 0.5737 0.031 Uiso 1 1 calc R U
C7 C 0.4572(3) 0.5708(10) 0.56690(13) 0.0250(7) Uani 1 1 d . .
H7 H 0.4328 0.6070 0.5289 0.030 Uiso 1 1 calc R U
C8 C 0.0824(2) 0.3296(9) 0.44789(13) 0.0210(7) Uani 1 1 d . .
C9 C -0.0805(2) 0.3246(10) 0.38504(13) 0.0226(7) Uani 1 1 d . .
H9 H -0.1548 0.2565 0.3745 0.027 Uiso 1 1 calc R U
C10 C -0.0381(3) 0.5190(9) 0.34971(13) 0.0221(7) Uani 1 1 d . .
C11 C 0.0701(3) 0.6247(9) 0.36384(14) 0.0236(7) Uani 1 1 d . .
H11 H 0.1007 0.7592 0.3397 0.028 Uiso 1 1 calc R U
C12 C 0.1313(3) 0.5288(10) 0.41370(13) 0.0230(7) Uani 1 1 d . .
H12 H 0.2055 0.5960 0.4249 0.028 Uiso 1 1 calc R U
C13 C 0.7007(3) 0.7566(10) 0.67753(14) 0.0258(8) Uani 1 1 d . .
H2N H 0.101(3) 0.106(10) 0.5181(14) 0.031 Uiso 1 1 d D U
N1 N 0.2390(2) 0.3490(8) 0.51926(11) 0.0219(6) Uani 1 1 d . .
N2 N 0.1374(2) 0.2247(8) 0.49834(11) 0.0232(6) Uani 1 1 d D .
N3 N -0.0223(2) 0.2255(8) 0.43391(11) 0.0220(6) Uani 1 1 d . .
N4 N 0.7843(2) 0.8584(9) 0.69882(12) 0.0317(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'
Br Br -0.6763 1.2805 '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 121.4(3)
N1 C1 H1 119.3
C2 C1 H1 119.3
C3 C2 C7 119.4(3)
C3 C2 C1 118.7(3)
C7 C2 C1 121.8(3)
C4 C3 C2 120.8(3)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 119.3(3)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C6 120.6(3)
C4 C5 C13 119.8(3)
C6 C5 C13 119.5(3)
C7 C6 C5 119.6(3)
C7 C6 H6 120.2
C5 C6 H6 120.2
C6 C7 C2 120.4(3)
C6 C7 H7 119.8
C2 C7 H7 119.8
N3 C8 N2 114.3(3)
N3 C8 C12 123.0(3)
N2 C8 C12 122.7(3)
N3 C9 C10 123.2(3)
N3 C9 H9 118.4
C10 C9 H9 118.4
C9 C10 C11 120.1(3)
C9 C10 Br1 119.0(2)
C11 C10 Br1 120.8(3)
C12 C11 C10 118.0(3)
C12 C11 H11 121.0
C10 C11 H11 121.0
C11 C12 C8 118.9(3)
C11 C12 H12 120.5
C8 C12 H12 120.5
N4 C13 C5 178.9(4)
C1 N1 N2 116.9(3)
N1 N2 C8 119.2(3)
N1 N2 H2N 122(3)
C8 N2 H2N 118(3)
C9 N3 C8 116.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.897(3)
C1 N1 1.277(4)
C1 C2 1.466(4)
C1 H1 0.95
C2 C3 1.394(5)
C2 C7 1.399(5)
C3 C4 1.389(5)
C3 H3 0.95
C4 C5 1.391(5)
C4 H4 0.95
C5 C6 1.399(5)
C5 C13 1.448(5)
C6 C7 1.385(5)
C6 H6 0.95
C7 H7 0.95
C8 N3 1.349(4)
C8 N2 1.370(4)
C8 C12 1.404(5)
C9 N3 1.344(4)
C9 C10 1.370(5)
C9 H9 0.95
C10 C11 1.390(5)
C11 C12 1.373(5)
C11 H11 0.95
C12 H12 0.95
C13 N4 1.141(5)
N1 N2 1.361(4)
N2 H2N 0.879(10)
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 0.879(10) 2.166(12) 3.043(4) 175(4) 3_556
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 172.9(3)
N1 C1 C2 C7 -7.3(6)
C2 C1 N1 N2 -179.3(3)
C1 N1 N2 C8 170.9(3)
N3 C8 N2 N1 -172.0(3)
C12 C8 N2 N1 8.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202594
