#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:09:07 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/32/7233267.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_7233267
loop_
_publ_author_name
'Shikhaliyev, Namiq Q.'
'Kuznetsov, Maxim L.'
'Maharramov, Abel M.'
'Gurbanov, Atash V.'
'Ahmadova, Nigar E.'
'Nenajdenko, Valentine G.'
'Mahmudov, Kamran T.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Noncovalent interactions in the design of bis-azo dyes
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5032
_journal_paper_doi               10.1039/C9CE00956F
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C22 H10 Cl4 F4 N4'
_chemical_formula_sum            'C22 H10 Cl4 F4 N4'
_chemical_formula_weight         548.14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-06-19 deposited with the CCDC.    2019-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.0200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2519(4)
_cell_length_b                   7.2378(3)
_cell_length_c                   13.8051(5)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.01
_cell_volume                     1134.89(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17128
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         3.011
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0310
_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)+(0.0470P)²+0.3320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2283
_reflns_number_total             2607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00956f2.cif
_cod_data_source_block           N1607
_cod_depositor_comments
'Adding full bibliography for 7233265--7233268.cif.'
_cod_database_code               7233267
_shelx_shelxl_version_number     2016/6
_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   0.884
_shelx_estimated_absorpt_t_max   0.909
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
Cl1 Cl 1.02919(3) 0.64325(6) 0.77879(3) 0.04223(13) Uani 1 1 d . .
Cl2 Cl 0.80148(4) 0.76070(6) 0.76530(3) 0.05281(14) Uani 1 1 d . .
F1 F 0.81805(7) 0.29128(13) 0.50292(7) 0.0402(2) Uani 1 1 d . .
N1 N 0.72344(11) 0.67772(19) 0.54195(10) 0.0399(3) Uani 1 1 d . .
N2 N 0.68837(10) 0.64206(19) 0.44605(10) 0.0406(3) Uani 1 1 d . .
C1 C 0.92262(11) 0.57203(19) 0.54541(9) 0.0299(3) Uani 1 1 d . .
C2 C 0.90708(11) 0.3979(2) 0.50165(10) 0.0304(3) Uani 1 1 d . .
C4 C 0.84414(12) 0.6453(2) 0.59689(11) 0.0337(3) Uani 1 1 d . .
C10 C 0.37363(17) 0.7726(4) 0.3781(2) 0.0756(7) Uani 1 1 d . .
H10 H 0.324364 0.826110 0.407659 0.091 Uiso 1 1 calc R U
C9 C 0.32808(16) 0.7167(3) 0.27598(19) 0.0698(6) Uani 1 1 d . .
H9 H 0.247995 0.729748 0.237095 0.084 Uiso 1 1 calc R U
C5 C 0.88532(12) 0.6792(2) 0.70006(11) 0.0347(3) Uani 1 1 d . .
C11 C 0.49224(15) 0.7505(3) 0.43811(16) 0.0621(5) Uani 1 1 d . .
H11 H 0.522603 0.787036 0.507778 0.075 Uiso 1 1 calc R U
C8 C 0.39979(17) 0.6419(3) 0.23116(19) 0.0692(6) Uani 1 1 d . .
H8 H 0.368626 0.605236 0.161534 0.083 Uiso 1 1 calc R U
C7 C 0.51943(15) 0.6201(3) 0.28912(15) 0.0549(4) Uani 1 1 d . .
H7 H 0.568415 0.570142 0.258234 0.066 Uiso 1 1 calc R U
C6 C 0.56499(13) 0.6729(2) 0.39248(13) 0.0424(4) Uani 1 1 d . .
F2 F 1.03628(8) 0.84535(12) 0.58006(7) 0.0433(2) Uani 1 1 d . .
C3 C 1.01688(11) 0.67358(19) 0.54128(10) 0.0310(3) 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'
F F 0.0171 0.0103 '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'
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
N2 N1 C4 114.15(12) . .
N1 N2 C6 113.00(12) . .
C2 C1 C3 116.49(12) . .
C2 C1 C4 121.72(12) . .
C3 C1 C4 121.77(13) . .
F1 C2 C3 118.24(13) . 3_766
F1 C2 C1 119.95(12) . .
C3 C2 C1 121.78(12) 3_766 .
C5 C4 N1 116.25(12) . .
C5 C4 C1 121.16(12) . .
N1 C4 C1 122.57(12) . .
C9 C10 C11 120.8(2) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C8 C9 C10 120.15(18) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C4 C5 Cl2 124.20(11) . .
C4 C5 Cl1 122.30(11) . .
Cl2 C5 Cl1 113.50(8) . .
C10 C11 C6 118.9(2) . .
C10 C11 H11 120.5 . .
C6 C11 H11 120.5 . .
C9 C8 C7 120.3(2) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C6 C7 C8 119.68(18) . .
C6 C7 H7 120.2 . .
C8 C7 H7 120.2 . .
C7 C6 C11 120.17(15) . .
C7 C6 N2 115.59(14) . .
C11 C6 N2 124.24(16) . .
F2 C3 C2 118.24(12) . 3_766
F2 C3 C1 120.06(12) . .
C2 C3 C1 121.70(13) 3_766 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.7086(15) .
Cl2 C5 1.7053(14) .
F1 C2 1.3418(15) .
N1 N2 1.2560(19) .
N1 C4 1.4059(18) .
N2 C6 1.4296(18) .
C1 C2 1.379(2) .
C1 C3 1.3880(19) .
C1 C4 1.4909(17) .
C2 C3 1.3789(18) 3_766
C4 C5 1.343(2) .
C10 C9 1.369(4) .
C10 C11 1.386(3) .
C10 H10 0.9300 .
C9 C8 1.362(3) .
C9 H9 0.9300 .
C11 C6 1.388(2) .
C11 H11 0.9300 .
C8 C7 1.391(2) .
C8 H8 0.9300 .
C7 C6 1.377(3) .
C7 H7 0.9300 .
F2 C3 1.3391(16) .
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_4
C4 N1 N2 C6 178.89(13) .
C3 C1 C2 F1 179.80(11) .
C4 C1 C2 F1 1.34(19) .
C3 C1 C2 C3 1.8(2) 3_766
C4 C1 C2 C3 -176.66(12) 3_766
N2 N1 C4 C5 -179.15(14) .
N2 N1 C4 C1 -0.9(2) .
C2 C1 C4 C5 113.88(16) .
C3 C1 C4 C5 -64.50(19) .
C2 C1 C4 N1 -64.28(19) .
C3 C1 C4 N1 117.35(15) .
C11 C10 C9 C8 -1.5(4) .
N1 C4 C5 Cl2 -1.1(2) .
C1 C4 C5 Cl2 -179.33(11) .
N1 C4 C5 Cl1 178.82(11) .
C1 C4 C5 Cl1 0.6(2) .
C9 C10 C11 C6 1.0(4) .
C10 C9 C8 C7 0.7(4) .
C9 C8 C7 C6 0.6(3) .
C8 C7 C6 C11 -1.1(3) .
C8 C7 C6 N2 178.88(18) .
C10 C11 C6 C7 0.3(3) .
C10 C11 C6 N2 -179.66(19) .
N1 N2 C6 C7 -174.26(16) .
N1 N2 C6 C11 5.7(2) .
C2 C1 C3 F2 178.55(11) .
C4 C1 C3 F2 -2.99(19) .
C2 C1 C3 C2 -1.8(2) 3_766
C4 C1 C3 C2 176.66(12) 3_766
