#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:09:07 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/32/7233265.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_7233265
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         'C24 H14 Cl4 F4 N4 O2'
_chemical_formula_sum            'C24 H14 Cl4 F4 N4 O2'
_chemical_formula_weight         608.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                76.471(5)
_cell_angle_beta                 81.089(5)
_cell_angle_gamma                64.077(5)
_cell_formula_units_Z            1
_cell_length_a                   6.9129(9)
_cell_length_b                   7.2480(9)
_cell_length_c                   14.7369(19)
_cell_measurement_reflns_used    2876
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.85
_cell_volume                     644.49(15)
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.364
_diffrn_reflns_theta_min         1.424
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       prisme
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0418
_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)+(0.0556P)²+0.2695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2088
_reflns_number_total             2908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00956f2.cif
_cod_data_source_block           N6
_cod_depositor_comments
'Adding full bibliography for 7233265--7233268.cif.'
_cod_original_cell_volume        644.50(15)
_cod_database_code               7233265
_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   0.908
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.74645(10) -0.17851(9) 0.14913(4) 0.02436(17) Uani 1 1 d . .
Cl2 Cl 0.78691(11) -0.42186(9) 0.33515(4) 0.02900(18) Uani 1 1 d . .
F1 F 0.9135(2) -0.1284(2) 0.43016(10) 0.0309(4) Uani 1 1 d . .
F2 F 0.1732(2) 0.1200(2) 0.38858(10) 0.0285(4) Uani 1 1 d . .
O1 O 0.1052(3) 1.1364(3) 0.06423(12) 0.0294(4) Uani 1 1 d . .
N1 N 0.5215(3) 0.1876(3) 0.23779(13) 0.0206(4) Uani 1 1 d . .
N2 N 0.4317(3) 0.3427(3) 0.27867(14) 0.0206(4) Uani 1 1 d . .
C1 C 0.5467(4) -0.0071(4) 0.40348(16) 0.0194(5) Uani 1 1 d . .
C2 C 0.7070(4) -0.0652(4) 0.46349(17) 0.0211(5) Uani 1 1 d . .
C3 C 0.3381(4) 0.0592(4) 0.44295(16) 0.0208(5) Uani 1 1 d . .
C4 C 0.5912(4) -0.0035(4) 0.30124(16) 0.0187(5) Uani 1 1 d . .
C5 C 0.6947(4) -0.1787(4) 0.26595(16) 0.0203(5) Uani 1 1 d . .
C6 C 0.3564(4) 0.5388(4) 0.21922(16) 0.0203(5) Uani 1 1 d . .
C7 C 0.2587(4) 0.7069(4) 0.26529(17) 0.0216(5) Uani 1 1 d . .
H7 H 0.250355 0.682132 0.331690 0.026 Uiso 1 1 calc R U
C8 C 0.1735(4) 0.9096(4) 0.21608(17) 0.0225(5) Uani 1 1 d . .
H8 H 0.106310 1.023669 0.248205 0.027 Uiso 1 1 calc R U
C9 C 0.1873(4) 0.9443(4) 0.11919(17) 0.0208(5) Uani 1 1 d . .
C10 C 0.2880(4) 0.7756(4) 0.07203(17) 0.0234(6) Uani 1 1 d . .
H10 H 0.299254 0.800255 0.005627 0.028 Uiso 1 1 calc R U
C11 C 0.3700(4) 0.5753(4) 0.12165(16) 0.0219(5) Uani 1 1 d . .
H11 H 0.436228 0.461071 0.089619 0.026 Uiso 1 1 calc R U
C12 C -0.0183(5) 1.3102(4) 0.1102(2) 0.0354(7) Uani 1 1 d . .
H12A H -0.081471 1.437189 0.063292 0.053 Uiso 1 1 calc R U
H12B H 0.075786 1.327671 0.147683 0.053 Uiso 1 1 calc R U
H12C H -0.133524 1.284460 0.151027 0.053 Uiso 1 1 calc R U
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'
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
C9 O1 C12 117.14(19) . .
N2 N1 C4 112.28(19) . .
N1 N2 C6 115.21(19) . .
C2 C1 C3 116.2(2) . .
C2 C1 C4 122.7(2) . .
C3 C1 C4 121.0(2) . .
F1 C2 C3 118.4(2) . 2_656
F1 C2 C1 119.7(2) . .
C3 C2 C1 121.9(2) 2_656 .
F2 C3 C2 118.5(2) . 2_656
F2 C3 C1 119.5(2) . .
C2 C3 C1 122.0(2) 2_656 .
C5 C4 N1 117.6(2) . .
C5 C4 C1 122.2(2) . .
N1 C4 C1 120.2(2) . .
C4 C5 Cl1 123.03(19) . .
C4 C5 Cl2 122.48(18) . .
Cl1 C5 Cl2 114.49(14) . .
C7 C6 C11 119.5(2) . .
C7 C6 N2 114.4(2) . .
C11 C6 N2 126.2(2) . .
C8 C7 C6 121.0(2) . .
C8 C7 H7 119.5 . .
C6 C7 H7 119.5 . .
C7 C8 C9 119.1(2) . .
C7 C8 H8 120.5 . .
C9 C8 H8 120.5 . .
O1 C9 C8 123.9(2) . .
O1 C9 C10 115.8(2) . .
C8 C9 C10 120.3(2) . .
C11 C10 C9 120.0(2) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C10 C11 C6 120.1(2) . .
C10 C11 H11 120.0 . .
C6 C11 H11 120.0 . .
O1 C12 H12A 109.5 . .
O1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.703(2) .
Cl2 C5 1.712(2) .
F1 C2 1.343(3) .
F2 C3 1.347(3) .
O1 C9 1.356(3) .
O1 C12 1.433(3) .
N1 N2 1.266(3) .
N1 C4 1.406(3) .
N2 C6 1.404(3) .
C1 C2 1.381(3) .
C1 C3 1.383(3) .
C1 C4 1.487(3) .
C2 C3 1.372(3) 2_656
C4 C5 1.339(3) .
C6 C7 1.388(3) .
C6 C11 1.396(3) .
C7 C8 1.382(3) .
C7 H7 0.9500 .
C8 C9 1.386(3) .
C8 H8 0.9500 .
C9 C10 1.402(3) .
C10 C11 1.370(3) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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 -179.44(19) .
C3 C1 C2 F1 -179.0(2) .
C4 C1 C2 F1 -2.3(4) .
C3 C1 C2 C3 0.5(4) 2_656
C4 C1 C2 C3 177.2(2) 2_656
C2 C1 C3 F2 179.5(2) .
C4 C1 C3 F2 2.7(3) .
C2 C1 C3 C2 -0.5(4) 2_656
C4 C1 C3 C2 -177.3(2) 2_656
N2 N1 C4 C5 -178.0(2) .
N2 N1 C4 C1 2.9(3) .
C2 C1 C4 C5 69.9(3) .
C3 C1 C4 C5 -113.5(3) .
C2 C1 C4 N1 -110.9(3) .
C3 C1 C4 N1 65.6(3) .
N1 C4 C5 Cl1 0.6(3) .
C1 C4 C5 Cl1 179.74(18) .
N1 C4 C5 Cl2 -179.64(17) .
C1 C4 C5 Cl2 -0.5(4) .
N1 N2 C6 C7 -179.9(2) .
N1 N2 C6 C11 0.8(4) .
C11 C6 C7 C8 0.4(4) .
N2 C6 C7 C8 -178.9(2) .
C6 C7 C8 C9 -0.3(4) .
C12 O1 C9 C8 -5.4(4) .
C12 O1 C9 C10 173.6(2) .
C7 C8 C9 O1 178.6(2) .
C7 C8 C9 C10 -0.5(4) .
O1 C9 C10 C11 -178.0(2) .
C8 C9 C10 C11 1.1(4) .
C9 C10 C11 C6 -0.9(4) .
C7 C6 C11 C10 0.2(4) .
N2 C6 C11 C10 179.5(2) .
