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#$Date: 2022-05-13 10:35:53 +0300 (Fri, 13 May 2022) $
#$Revision: 275393 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105238.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_8105238
loop_
_publ_author_name
'Akintayo, Damilola Caleb'
'Zamisa, Sizwe J.'
'Omondi, Bernard'
'Jonnalagadda, Sreekantha B.'
_publ_section_title
;
 Crystal structure of (E)-4-((4-chlorophenylimino)methyl)pyridinium
 3,5-dinitrobenzoate, C19H13ClN4O6
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              621
_journal_page_last               623
_journal_paper_doi               10.1515/ncrs-2019-0860
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C12 H10 Cl N2, C7 H3 N2 O6'
_chemical_formula_sum            'C19 H13 Cl N4 O6'
_chemical_formula_weight         428.78
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.6400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.80320(10)
_cell_length_b                   19.5545(5)
_cell_length_c                   19.6915(6)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.32
_cell_volume                     1849.39(8)
_computing_cell_refinement       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23587
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_min         2.069
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0478 before and 0.0363 after correction. The Ratio of minimum to maximum transmission is 0.8855. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_recrystallization_method
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0469P)²+1.3480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4077
_reflns_number_total             4595
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0860_suppl.cif
_cod_data_source_block           Clpy4DNB
_cod_database_code               8105238
_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_max   0.941
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C3(H3A), C5(H5), C7(H7)
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.24030(7) 0.17151(2) 0.22774(2) 0.02373(10) Uani 1 1 d . . . . .
O1 O -0.6861(2) -0.15929(6) 0.88344(6) 0.0303(3) Uani 1 1 d . . . . .
O2 O -1.0191(2) -0.14248(5) 0.95467(5) 0.0266(2) Uani 1 1 d . . . . .
O3 O -1.4605(2) 0.07664(5) 0.96821(5) 0.0245(2) Uani 1 1 d . . . . .
O4 O -1.3363(2) 0.15901(5) 0.90140(6) 0.0275(2) Uani 1 1 d . . . . .
O5 O -0.6239(2) 0.11936(6) 0.72800(5) 0.0290(2) Uani 1 1 d . . . . .
O6 O -0.3923(2) 0.02022(6) 0.73132(5) 0.0276(2) Uani 1 1 d . . . . .
N1 N -0.8627(3) -0.12316(6) 0.90962(6) 0.0207(2) Uani 1 1 d . . . . .
N2 N -1.3163(2) 0.10035(6) 0.92263(6) 0.0194(2) Uani 1 1 d . . . . .
C1 C -0.5720(3) 0.05961(7) 0.75157(7) 0.0200(3) Uani 1 1 d . . . . .
C2 C -0.7529(3) 0.03677(7) 0.81005(6) 0.0185(3) Uani 1 1 d . . . . .
C3 C -0.7222(3) -0.02998(7) 0.83349(7) 0.0190(3) Uani 1 1 d . . . . .
H3A H -0.588469 -0.059708 0.814061 0.023 Uiso 1 1 calc R . . . .
C4 C -0.8907(3) -0.05222(7) 0.88575(7) 0.0183(3) Uani 1 1 d . . . . .
C5 C -1.0871(3) -0.01087(7) 0.91609(6) 0.0178(3) Uani 1 1 d . . . . .
H5 H -1.201508 -0.027042 0.951712 0.021 Uiso 1 1 calc R . . . .
C6 C -1.1080(3) 0.05523(7) 0.89178(6) 0.0175(3) Uani 1 1 d . . . . .
C7 C -0.9479(3) 0.08027(7) 0.83905(6) 0.0183(3) Uani 1 1 d . . . . .
H7 H -0.970819 0.125824 0.823184 0.022 Uiso 1 1 calc R . . . .
N3 N -0.3050(3) 0.13949(7) 0.62705(6) 0.0233(3) Uani 1 1 d . . . . .
H3 H -0.418643 0.132159 0.661030 0.028 Uiso 1 1 calc R . . . .
N4 N 0.4151(3) 0.13075(6) 0.44523(6) 0.0209(2) Uani 1 1 d . . . . .
C8 C -0.2935(3) 0.20121(7) 0.59871(7) 0.0219(3) Uani 1 1 d . . . . .
H8 H -0.411018 0.236564 0.614904 0.026 Uiso 1 1 calc R . . . .
C9 C -0.1129(3) 0.21478(7) 0.54600(7) 0.0210(3) Uani 1 1 d . . . . .
H9 H -0.105578 0.259140 0.526427 0.025 Uiso 1 1 calc R . . . .
C10 C 0.0573(3) 0.16282(7) 0.52204(7) 0.0190(3) Uani 1 1 d . . . . .
C11 C 0.0382(3) 0.09823(8) 0.55152(7) 0.0249(3) Uani 1 1 d . . . . .
H11 H 0.149314 0.061523 0.535580 0.030 Uiso 1 1 calc R . . . .
C12 C -0.1447(3) 0.08833(8) 0.60424(8) 0.0281(3) Uani 1 1 d . . . . .
H12 H -0.157379 0.044488 0.624759 0.034 Uiso 1 1 calc R . . . .
C13 C 0.2526(3) 0.17694(7) 0.46668(7) 0.0194(3) Uani 1 1 d . . . . .
H13 H 0.257027 0.221175 0.446774 0.023 Uiso 1 1 calc R . . . .
C14 C 0.6074(3) 0.14498(7) 0.39310(7) 0.0191(3) Uani 1 1 d . . . . .
C15 C 0.6740(3) 0.21052(7) 0.36949(7) 0.0228(3) Uani 1 1 d . . . . .
H15 H 0.586773 0.249484 0.388681 0.027 Uiso 1 1 calc R . . . .
C16 C 0.8670(3) 0.21873(7) 0.31817(7) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.909986 0.263031 0.301474 0.027 Uiso 1 1 calc R . . . .
C17 C 0.9961(3) 0.16144(7) 0.29162(7) 0.0193(3) Uani 1 1 d . . . . .
C18 C 0.9382(3) 0.09634(7) 0.31485(7) 0.0211(3) Uani 1 1 d . . . . .
H18 H 1.030379 0.057670 0.296454 0.025 Uiso 1 1 calc R . . . .
C19 C 0.7423(3) 0.08864(7) 0.36569(7) 0.0202(3) Uani 1 1 d . . . . .
H19 H 0.699963 0.044150 0.381974 0.024 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.1484 0.1585 '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 N3 C12 120.57(12) . .
C13 N4 C14 120.67(12) . .
N3 C8 C9 121.14(13) . .
C8 C9 C10 119.32(13) . .
C9 C10 C11 118.64(12) . .
C9 C10 C13 119.75(12) . .
C11 C10 C13 121.61(13) . .
C12 C11 C10 119.06(13) . .
N3 C12 C11 121.26(14) . .
N4 C13 C10 120.81(13) . .
C15 C14 N4 124.98(13) . .
C19 C14 N4 115.89(12) . .
C19 C14 C15 119.11(12) . .
C16 C15 C14 120.27(13) . .
C17 C16 C15 119.10(13) . .
C16 C17 Cl1 119.28(11) . .
C18 C17 Cl1 118.88(11) . .
C18 C17 C16 121.83(12) . .
C17 C18 C19 118.59(13) . .
C18 C19 C14 121.08(13) . .
O1 N1 O2 124.04(12) . .
O1 N1 C4 118.15(11) . .
O2 N1 C4 117.81(12) . .
O3 N2 C6 117.81(11) . .
O4 N2 O3 123.99(12) . .
O4 N2 C6 118.20(11) . .
O5 C1 C2 115.65(12) . .
O6 C1 O5 126.13(13) . .
O6 C1 C2 118.21(13) . .
C3 C2 C1 117.93(12) . .
C3 C2 C7 120.40(12) . .
C7 C2 C1 121.66(12) . .
C4 C3 C2 118.69(12) . .
C3 C4 N1 118.77(12) . .
C5 C4 N1 118.28(12) . .
C5 C4 C3 122.94(13) . .
C6 C5 C4 116.39(12) . .
C5 C6 N2 117.73(11) . .
C5 C6 C7 123.41(12) . .
C7 C6 N2 118.84(12) . .
C6 C7 C2 118.17(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C17 1.7407(13) .
N3 C8 1.3310(19) .
N3 C12 1.3428(19) .
N4 C13 1.2691(18) .
N4 C14 1.4161(17) .
C8 C9 1.3856(18) .
C9 C10 1.3900(19) .
C10 C11 1.394(2) .
C10 C13 1.4721(18) .
C11 C12 1.3809(19) .
C14 C15 1.4017(19) .
C14 C19 1.3905(19) .
C15 C16 1.3882(19) .
C16 C17 1.386(2) .
C17 C18 1.382(2) .
C18 C19 1.3895(19) .
O1 N1 1.2222(16) .
O2 N1 1.2284(16) .
O3 N2 1.2307(15) .
O4 N2 1.2243(16) .
O5 C1 1.2807(18) .
O6 C1 1.2269(17) .
N1 C4 1.4703(18) .
N2 C6 1.4703(17) .
C1 C2 1.5173(18) .
C2 C3 1.392(2) .
C2 C7 1.3927(19) .
C3 C4 1.3863(18) .
C4 C5 1.3834(18) .
C5 C6 1.3815(19) .
C6 C7 1.3881(18) .
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
N3 H3 O5 0.88 1.67 2.5535(15) 177.5 .
C12 H12 O6 0.95 2.44 3.0849(18) 125.0 .
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
Cl1 C17 C18 C19 -179.78(11) . . . .
N3 C8 C9 C10 0.5(2) . . . .
N4 C14 C15 C16 179.73(13) . . . .
N4 C14 C19 C18 -179.16(12) . . . .
C8 N3 C12 C11 0.7(2) . . . .
C8 C9 C10 C11 0.7(2) . . . .
C8 C9 C10 C13 -179.17(13) . . . .
C9 C10 C11 C12 -1.2(2) . . . .
C9 C10 C13 N4 178.15(13) . . . .
C10 C11 C12 N3 0.5(2) . . . .
C11 C10 C13 N4 -1.8(2) . . . .
C12 N3 C8 C9 -1.2(2) . . . .
C13 N4 C14 C15 12.1(2) . . . .
C13 N4 C14 C19 -169.79(13) . . . .
C13 C10 C11 C12 178.67(14) . . . .
C14 N4 C13 C10 -178.45(12) . . . .
C14 C15 C16 C17 -1.2(2) . . . .
C15 C14 C19 C18 -0.9(2) . . . .
C15 C16 C17 Cl1 -179.48(11) . . . .
C15 C16 C17 C18 -0.1(2) . . . .
C16 C17 C18 C19 0.8(2) . . . .
C17 C18 C19 C14 -0.3(2) . . . .
C19 C14 C15 C16 1.7(2) . . . .
O1 N1 C4 C3 1.85(19) . . . .
O1 N1 C4 C5 -178.91(13) . . . .
O2 N1 C4 C3 -178.02(12) . . . .
O2 N1 C4 C5 1.22(18) . . . .
O3 N2 C6 C5 -0.15(18) . . . .
O3 N2 C6 C7 178.31(12) . . . .
O4 N2 C6 C5 -179.98(12) . . . .
O4 N2 C6 C7 -1.52(19) . . . .
O5 C1 C2 C3 174.31(13) . . . .
O5 C1 C2 C7 -4.52(19) . . . .
O6 C1 C2 C3 -5.75(19) . . . .
O6 C1 C2 C7 175.42(13) . . . .
N1 C4 C5 C6 -179.52(12) . . . .
N2 C6 C7 C2 -179.57(12) . . . .
C1 C2 C3 C4 -178.40(12) . . . .
C1 C2 C7 C6 179.15(12) . . . .
C2 C3 C4 N1 178.74(12) . . . .
C2 C3 C4 C5 -0.5(2) . . . .
C3 C2 C7 C6 0.3(2) . . . .
C3 C4 C5 C6 -0.3(2) . . . .
C4 C5 C6 N2 179.56(11) . . . .
C4 C5 C6 C7 1.2(2) . . . .
C5 C6 C7 C2 -1.2(2) . . . .
C7 C2 C3 C4 0.5(2) . . . .
