#------------------------------------------------------------------------------
#$Date: 2019-03-27 05:49:30 +0200 (Wed, 27 Mar 2019) $
#$Revision: 214378 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/28/2242878.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242878
loop_
_publ_author_name
'Shikhaliyev, Namiq Q.'
'Çelikesir, Sevim Türktekin'
'Akkurt, Mehmet'
'Bagirova, Khanim N.'
'Suleymanova, Gulnar T.'
'Toze, Flavien A. A.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]diazene
;
_journal_coeditor_code           IS5510
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              465
_journal_page_last               469
_journal_paper_doi               10.1107/S2056989019003657
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H8 Cl3 F N2'
_chemical_formula_moiety         'C14 H8 Cl3 F N2'
_chemical_formula_sum            'C14 H8 Cl3 F N2'
_chemical_formula_weight         329.57
_chemical_name_systematic
;
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]\
diazene
;
_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     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.30(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8617(8)
_cell_length_b                   24.249(5)
_cell_length_c                   14.724(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.3
_cell_volume                     1374.9(5)
_computing_cell_refinement
;
iMosflm (Battye et al.,  2011)
;
_computing_data_collection
;
Marccd (Doyle, 2011)
;
_computing_data_reduction        iMosflm
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.80246
_diffrn_reflns_av_R_equivalents  0.1145
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20761
_diffrn_reflns_theta_full        28.782
_diffrn_reflns_theta_max         30.925
_diffrn_reflns_theta_min         3.248
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scala; Evans, 2006)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.723
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0528
_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)+(0.0557P)²+1.092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                2719
_reflns_number_total             2984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5510sup1.cif
_cod_data_source_block           I
_cod_database_code               2242878
_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   0.834
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           .2013
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl1 0.68912(17) 0.12097(2) 0.17209(4) 0.0265(2) Uani d 1
Cl Cl2 0.48467(18) 0.22728(2) 0.10431(4) 0.0283(2) Uani d 1
Cl Cl3 -0.18247(18) 0.50802(2) 0.35787(5) 0.0318(2) Uani d 1
F F1 0.5868(5) 0.06509(7) 0.58998(10) 0.0386(4) Uani d 1
N N1 0.3562(6) 0.25699(8) 0.28387(14) 0.0246(5) Uani d 1
N N2 0.2435(6) 0.27366(8) 0.35685(14) 0.0230(4) Uani d 1
C C1 0.4622(7) 0.20110(9) 0.28183(16) 0.0225(5) Uani d 1
C C2 0.5361(7) 0.18506(9) 0.19760(16) 0.0237(5) Uani d 1
C C3 0.4936(7) 0.16469(9) 0.36354(16) 0.0232(5) Uani d 1
C C4 0.6716(7) 0.18329(10) 0.44378(16) 0.0249(5) Uani d 1
H H4 0.7714 0.2191 0.4459 0.030 Uiso calc 1
C C5 0.7036(7) 0.14978(10) 0.52038(16) 0.0283(6) Uani d 1
H H5 0.8242 0.1622 0.5752 0.034 Uiso calc 1
C C6 0.5558(8) 0.09804(10) 0.51483(17) 0.0287(6) Uani d 1
C C7 0.3803(7) 0.07791(10) 0.43694(17) 0.0280(5) Uani d 1
H H7 0.2840 0.0418 0.4352 0.034 Uiso calc 1
C C8 0.3485(7) 0.11196(10) 0.36103(17) 0.0243(5) Uani d 1
H H8 0.2264 0.0992 0.3067 0.029 Uiso calc 1
C C9 0.1482(7) 0.33066(9) 0.35229(16) 0.0225(5) Uani d 1
C C10 0.1990(7) 0.36475(10) 0.27784(16) 0.0251(5) Uani d 1
H H10 0.3012 0.3504 0.2261 0.030 Uiso calc 1
C C11 0.1000(7) 0.41943(10) 0.27997(16) 0.0257(5) Uani d 1
H H11 0.1332 0.4430 0.2298 0.031 Uiso calc 1
C C12 -0.0490(7) 0.43956(10) 0.35640(17) 0.0246(5) Uani d 1
C C13 -0.0997(7) 0.40658(10) 0.43064(17) 0.0255(5) Uani d 1
H H13 -0.2002 0.4212 0.4824 0.031 Uiso calc 1
C C14 -0.0012(7) 0.35157(10) 0.42818(16) 0.0248(5) Uani d 1
H H14 -0.0358 0.3282 0.4784 0.030 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 '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 0.0090 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0230 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1780 0.2030 '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
N2 N1 C1 116.43(19)
N1 N2 C9 112.0(2)
C2 C1 N1 112.1(2)
C2 C1 C3 124.1(2)
N1 C1 C3 123.8(2)
C1 C2 Cl2 122.99(19)
C1 C2 Cl1 124.22(18)
Cl2 C2 Cl1 112.79(14)
C8 C3 C4 119.3(2)
C8 C3 C1 120.9(2)
C4 C3 C1 119.8(2)
C5 C4 C3 120.4(2)
C5 C4 H4 119.8
C3 C4 H4 119.8
C6 C5 C4 118.3(2)
C6 C5 H5 120.9
C4 C5 H5 120.9
F1 C6 C7 118.4(2)
F1 C6 C5 118.3(2)
C7 C6 C5 123.2(2)
C6 C7 C8 117.9(2)
C6 C7 H7 121.0
C8 C7 H7 121.0
C7 C8 C3 120.9(2)
C7 C8 H8 119.6
C3 C8 H8 119.6
C14 C9 C10 120.4(2)
C14 C9 N2 115.8(2)
C10 C9 N2 123.9(2)
C11 C10 C9 119.6(2)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 119.2(2)
C10 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C11 122.0(2)
C13 C12 Cl3 118.9(2)
C11 C12 Cl3 119.10(18)
C12 C13 C14 118.7(2)
C12 C13 H13 120.6
C14 C13 H13 120.6
C13 C14 C9 120.1(2)
C13 C14 H14 119.9
C9 C14 H14 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.714(2)
Cl2 C2 1.713(2)
Cl3 C12 1.739(2)
F1 C6 1.363(3)
N1 N2 1.256(3)
N1 C1 1.417(3)
N2 C9 1.431(3)
C1 C2 1.351(3)
C1 C3 1.490(3)
C3 C8 1.395(3)
C3 C4 1.396(3)
C4 C5 1.388(3)
C4 H4 0.9500
C5 C6 1.378(4)
C5 H5 0.9500
C6 C7 1.377(4)
C7 C8 1.388(3)
C7 H7 0.9500
C8 H8 0.9500
C9 C14 1.391(3)
C9 C10 1.399(3)
C10 C11 1.381(3)
C10 H10 0.9500
C11 C12 1.390(4)
C11 H11 0.9500
C12 C13 1.380(3)
C13 C14 1.389(3)
C13 H13 0.9500
C14 H14 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8 Cl1 1_455 0.95 2.81 3.634(3) 146 yes
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
C1 N1 N2 C9 179.2(2)
N2 N1 C1 C2 171.9(2)
N2 N1 C1 C3 -9.0(4)
N1 C1 C2 Cl2 -3.0(3)
C3 C1 C2 Cl2 177.94(19)
N1 C1 C2 Cl1 177.14(18)
C3 C1 C2 Cl1 -1.9(4)
C2 C1 C3 C8 -49.2(4)
N1 C1 C3 C8 131.8(3)
C2 C1 C3 C4 130.5(3)
N1 C1 C3 C4 -48.4(4)
C8 C3 C4 C5 -0.1(4)
C1 C3 C4 C5 -179.9(2)
C3 C4 C5 C6 0.0(4)
C4 C5 C6 F1 -180.0(2)
C4 C5 C6 C7 0.4(4)
F1 C6 C7 C8 179.6(2)
C5 C6 C7 C8 -0.8(4)
C6 C7 C8 C3 0.7(4)
C4 C3 C8 C7 -0.3(4)
C1 C3 C8 C7 179.5(2)
N1 N2 C9 C14 175.9(2)
N1 N2 C9 C10 -4.5(4)
C14 C9 C10 C11 0.0(4)
N2 C9 C10 C11 -179.6(2)
C9 C10 C11 C12 0.0(4)
C10 C11 C12 C13 0.3(4)
C10 C11 C12 Cl3 -178.57(19)
C11 C12 C13 C14 -0.6(4)
Cl3 C12 C13 C14 178.31(19)
C12 C13 C14 C9 0.5(4)
C10 C9 C14 C13 -0.2(4)
N2 C9 C14 C13 179.4(2)

_cod_database_fobs_code 2242878
