#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:09:07 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/32/7233268.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_7233268
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'
_chemical_formula_sum            'C24 H14 Cl4 F4 N4'
_chemical_formula_weight         576.19
_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                97.953(5)
_cell_angle_beta                 97.431(5)
_cell_angle_gamma                111.124(4)
_cell_formula_units_Z            1
_cell_length_a                   5.9278(9)
_cell_length_b                   7.2851(11)
_cell_length_c                   15.889(3)
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.64
_cell_volume                     621.86(18)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.956
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9847
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.707
_diffrn_reflns_theta_min         3.080
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       prisme
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.058
_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     164
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0390
_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)+(0.0393P)²+0.3553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1681
_reflns_number_total             2260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00956f2.cif
_cod_data_source_block           ane28_a
_cod_depositor_comments
'Adding full bibliography for 7233265--7233268.cif.'
_cod_original_cell_volume        621.87(17)
_cod_database_code               7233268
_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   0.906
_shelx_estimated_absorpt_t_max   0.935
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 -0.28932(13) 0.49254(10) 0.81322(4) 0.0308(2) Uani 1 1 d . .
Cl2 Cl -0.52823(12) 0.30038(10) 0.63751(4) 0.0318(2) Uani 1 1 d . .
F1 F -0.1042(3) 0.18063(19) 0.57871(8) 0.0243(4) Uani 1 1 d . .
F2 F 0.0427(3) 0.86342(19) 0.58454(9) 0.0253(4) Uani 1 1 d . .
N1 N 0.1514(4) 0.6843(3) 0.74435(12) 0.0211(5) Uani 1 1 d . .
N2 N 0.3427(4) 0.7621(3) 0.71402(12) 0.0200(5) Uani 1 1 d . .
C1 C -0.0317(4) 0.5234(3) 0.58726(14) 0.0170(5) Uani 1 1 d . .
C2 C -0.0545(4) 0.3411(3) 0.54062(15) 0.0182(5) Uani 1 1 d . .
C3 C 0.0230(4) 0.6818(3) 0.54384(15) 0.0174(5) Uani 1 1 d . .
C4 C -0.0526(4) 0.5536(3) 0.68005(15) 0.0191(5) Uani 1 1 d . .
C5 C -0.2626(5) 0.4600(4) 0.70690(15) 0.0220(6) Uani 1 1 d . .
C6 C 0.5499(5) 0.8981(3) 0.77711(15) 0.0205(6) Uani 1 1 d . .
C7 C 0.7650(5) 0.9776(4) 0.74612(15) 0.0225(6) Uani 1 1 d . .
H7 H 0.766513 0.940898 0.686504 0.027 Uiso 1 1 calc R U
C8 C 0.9785(5) 1.1108(4) 0.80224(16) 0.0262(6) Uani 1 1 d . .
H8 H 1.126172 1.164219 0.780777 0.031 Uiso 1 1 calc R U
C9 C 0.9792(5) 1.1670(4) 0.88897(16) 0.0287(7) Uani 1 1 d . .
C10 C 0.7609(5) 1.0857(4) 0.91892(16) 0.0334(7) Uani 1 1 d . .
H10 H 0.759457 1.122925 0.978496 0.040 Uiso 1 1 calc R U
C11 C 0.5470(5) 0.9525(4) 0.86434(16) 0.0305(7) Uani 1 1 d . .
H11 H 0.399608 0.898629 0.885918 0.037 Uiso 1 1 calc R U
C12 C 1.2078(5) 1.3192(5) 0.94953(18) 0.0425(8) Uani 1 1 d . .
H12A H 1.193183 1.308194 1.009526 0.064 Uiso 1 1 calc R U
H12B H 1.226322 1.454637 0.941675 0.064 Uiso 1 1 calc R U
H12C H 1.352403 1.293681 0.936712 0.064 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'
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 112.8(2) . .
N1 N2 C6 114.1(2) . .
C2 C1 C3 116.2(2) . .
C2 C1 C4 122.7(2) . .
C3 C1 C4 121.1(2) . .
F1 C2 C3 118.4(2) . 2_566
F1 C2 C1 119.7(2) . .
C3 C2 C1 121.9(2) 2_566 .
F2 C3 C2 118.5(2) . 2_566
F2 C3 C1 119.6(2) . .
C2 C3 C1 121.9(2) 2_566 .
C5 C4 N1 116.8(2) . .
C5 C4 C1 122.5(2) . .
N1 C4 C1 120.7(2) . .
C4 C5 Cl1 123.01(19) . .
C4 C5 Cl2 122.9(2) . .
Cl1 C5 Cl2 114.06(15) . .
C7 C6 C11 120.2(2) . .
C7 C6 N2 115.1(2) . .
C11 C6 N2 124.7(2) . .
C6 C7 C8 119.9(2) . .
C6 C7 H7 120.1 . .
C8 C7 H7 120.1 . .
C9 C8 C7 120.8(3) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 118.5(2) . .
C8 C9 C12 121.1(3) . .
C10 C9 C12 120.4(3) . .
C11 C10 C9 121.6(3) . .
C11 C10 H10 119.2 . .
C9 C10 H10 119.2 . .
C10 C11 C6 119.0(3) . .
C10 C11 H11 120.5 . .
C6 C11 H11 120.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 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 1.709(3) .
Cl2 C5 1.710(2) .
F1 C2 1.346(2) .
F2 C3 1.347(3) .
N1 N2 1.262(3) .
N1 C4 1.412(3) .
N2 C6 1.423(3) .
C1 C2 1.380(3) .
C1 C3 1.386(3) .
C1 C4 1.488(3) .
C2 C3 1.375(4) 2_566
C4 C5 1.343(4) .
C6 C7 1.383(4) .
C6 C11 1.392(4) .
C7 C8 1.386(3) .
C7 H7 0.9500 .
C8 C9 1.381(4) .
C8 H8 0.9500 .
C9 C10 1.391(4) .
C9 C12 1.509(4) .
C10 C11 1.378(4) .
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 178.68(19) .
C3 C1 C2 F1 179.12(19) .
C4 C1 C2 F1 1.8(4) .
C3 C1 C2 C3 0.5(4) 2_566
C4 C1 C2 C3 -176.8(2) 2_566
C2 C1 C3 F2 178.5(2) .
C4 C1 C3 F2 -4.1(4) .
C2 C1 C3 C2 -0.5(4) 2_566
C4 C1 C3 C2 176.9(2) 2_566
N2 N1 C4 C5 178.3(2) .
N2 N1 C4 C1 -1.8(3) .
C2 C1 C4 C5 -64.7(4) .
C3 C1 C4 C5 118.1(3) .
C2 C1 C4 N1 115.4(3) .
C3 C1 C4 N1 -61.8(3) .
N1 C4 C5 Cl1 -0.2(3) .
C1 C4 C5 Cl1 179.84(18) .
N1 C4 C5 Cl2 178.78(17) .
C1 C4 C5 Cl2 -1.1(4) .
N1 N2 C6 C7 176.9(2) .
N1 N2 C6 C11 -3.1(4) .
C11 C6 C7 C8 0.4(4) .
N2 C6 C7 C8 -179.6(2) .
C6 C7 C8 C9 -0.5(4) .
C7 C8 C9 C10 0.4(4) .
C7 C8 C9 C12 -177.2(2) .
C8 C9 C10 C11 -0.2(4) .
C12 C9 C10 C11 177.4(3) .
C9 C10 C11 C6 0.1(4) .
C7 C6 C11 C10 -0.1(4) .
N2 C6 C11 C10 179.8(2) .
