#------------------------------------------------------------------------------
#$Date: 2019-07-17 07:09:53 +0300 (Wed, 17 Jul 2019) $
#$Revision: 217102 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/30/2243019.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_2243019
loop_
_publ_author_name
'Akkurt, Mehmet'
'Shikhaliyev, Namiq Q.'
'Askerova, Ulviyya F.'
'Mukhtarova, Sevinc H.'
'Mammadova, Gunay Z.'
'Toze, Flavien A. A.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (E)-4-{[2,2-dichloro-1-(4-methoxyphenyl)ethenyl]diazenyl}benzonitrile
;
_journal_coeditor_code           LH5909
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1190
_journal_page_last               1194
_journal_paper_doi               10.1107/S2056989019009642
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C16 H11 Cl2 N3 O'
_chemical_formula_moiety         'C16 H11 Cl2 N3 O'
_chemical_formula_sum            'C16 H11 Cl2 N3 O'
_chemical_formula_weight         332.18
_chemical_name_systematic
;
(E)-4-{[2,2-Dichloro-1-(4-methoxyphenyl)ethenyl]diazenyl}benzonitrile
;
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 97.07(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9117(8)
_cell_length_b                   25.109(5)
_cell_length_c                   14.968(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      1.8
_cell_volume                     1459.0(5)
_computing_cell_refinement
;
iMosflm (Battye et al.,  2011)
;
_computing_data_collection
;
Marccd (Doyle, 2011)
;
_computing_data_reduction
;
iMosflm (Battye et al.,  2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXLS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_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  0.0678
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22750
_diffrn_reflns_theta_full        28.782
_diffrn_reflns_theta_max         30.862
_diffrn_reflns_theta_min         1.798
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scala; Evans, 2006)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.458
_refine_ls_extinction_coef       0.049(5)
_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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0454
_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)+(0.0660P)²+0.9448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                2978
_reflns_number_total             3144
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5909sup1.cif
_cod_data_source_block           I
_cod_database_code               2243019
_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   0.858
_shelx_estimated_absorpt_t_max   0.981
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
C C1 0.4566(5) 0.66476(7) 0.67302(12) 0.0215(4) Uani d 1
H H1 0.463381 0.687885 0.723440 0.026 Uiso calc 1
C C2 0.3294(5) 0.61359(7) 0.67752(13) 0.0221(4) Uani d 1
H H2 0.244963 0.601450 0.730780 0.026 Uiso calc 1
C C3 0.3261(5) 0.57981(7) 0.60312(13) 0.0215(4) Uani d 1
C C4 0.4409(5) 0.59720(7) 0.52351(12) 0.0228(4) Uani d 1
H H4 0.436434 0.574023 0.473208 0.027 Uiso calc 1
C C5 0.5621(5) 0.64912(7) 0.51906(12) 0.0214(4) Uani d 1
H H5 0.636172 0.661965 0.464913 0.026 Uiso calc 1
C C6 0.5748(5) 0.68213(7) 0.59378(12) 0.0197(4) Uani d 1
C C7 0.9517(5) 0.80678(7) 0.65882(12) 0.0199(4) Uani d 1
C C8 1.0851(5) 0.82299(7) 0.74254(13) 0.0218(4) Uani d 1
C C9 0.9344(5) 0.84019(7) 0.57700(12) 0.0199(4) Uani d 1
C C10 1.0545(5) 0.82125(7) 0.49838(13) 0.0210(4) Uani d 1
H H10 1.155098 0.786823 0.498109 0.025 Uiso calc 1
C C11 1.0283(5) 0.85197(7) 0.42152(12) 0.0213(4) Uani d 1
H H11 1.108147 0.838403 0.368576 0.026 Uiso calc 1
C C12 0.8849(5) 0.90295(7) 0.42105(12) 0.0198(4) Uani d 1
C C13 0.7626(5) 0.92238(7) 0.49813(13) 0.0208(4) Uani d 1
H H13 0.662374 0.956840 0.498230 0.025 Uiso calc 1
C C14 0.7886(5) 0.89082(7) 0.57518(13) 0.0210(4) Uani d 1
H H14 0.704725 0.904154 0.627752 0.025 Uiso calc 1
C C15 0.1992(5) 0.52632(8) 0.61044(13) 0.0249(4) Uani d 1
C C16 0.7123(5) 0.98149(7) 0.33590(13) 0.0246(4) Uani d 1
H H16A 0.731494 0.997143 0.276745 0.037 Uiso calc 1
H H16B 0.823240 1.005003 0.383095 0.037 Uiso calc 1
H H16C 0.468596 0.977180 0.343527 0.037 Uiso calc 1
N N1 0.7074(4) 0.73473(6) 0.58427(10) 0.0207(3) Uani d 1
N N2 0.8218(4) 0.75417(6) 0.65946(10) 0.0212(3) Uani d 1
N N3 0.1007(5) 0.48385(7) 0.61986(13) 0.0345(4) Uani d 1
O O1 0.8781(4) 0.93062(5) 0.34222(9) 0.0233(3) Uani d 1
Cl Cl1 1.07739(13) 0.78390(2) 0.83659(3) 0.02703(18) Uani d 1
Cl Cl2 1.27416(13) 0.88356(2) 0.76669(3) 0.02496(18) Uani d 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'
O O 0.0150 0.0080 '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
C2 C1 C6 119.40(17)
C2 C1 H1 120.3
C6 C1 H1 120.3
C1 C2 C3 119.55(18)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 121.20(17)
C4 C3 C15 120.48(17)
C2 C3 C15 118.32(17)
C5 C4 C3 118.80(17)
C5 C4 H4 120.6
C3 C4 H4 120.6
C6 C5 C4 119.96(17)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 121.04(17)
C5 C6 N1 116.61(16)
C1 C6 N1 122.33(16)
C8 C7 N2 111.75(16)
C8 C7 C9 124.52(17)
N2 C7 C9 123.71(15)
C7 C8 Cl2 124.62(15)
C7 C8 Cl1 122.71(15)
Cl2 C8 Cl1 112.66(11)
C14 C9 C10 118.16(17)
C14 C9 C7 120.73(17)
C10 C9 C7 121.08(16)
C11 C10 C9 120.81(17)
C11 C10 H10 119.6
C9 C10 H10 119.6
C10 C11 C12 120.36(17)
C10 C11 H11 119.8
C12 C11 H11 119.8
O1 C12 C13 124.46(17)
O1 C12 C11 115.79(16)
C13 C12 C11 119.74(17)
C12 C13 C14 119.34(17)
C12 C13 H13 120.3
C14 C13 H13 120.3
C9 C14 C13 121.59(17)
C9 C14 H14 119.2
C13 C14 H14 119.2
N3 C15 C3 177.3(2)
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N2 N1 C6 111.24(15)
N1 N2 C7 116.40(15)
C12 O1 C16 118.13(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(3)
C1 C6 1.395(3)
C1 H1 0.9500
C2 C3 1.399(3)
C2 H2 0.9500
C3 C4 1.394(3)
C3 C15 1.441(3)
C4 C5 1.392(3)
C4 H4 0.9500
C5 C6 1.388(3)
C5 H5 0.9500
C6 N1 1.433(2)
C7 C8 1.359(3)
C7 N2 1.416(2)
C7 C9 1.479(2)
C8 Cl2 1.7103(19)
C8 Cl1 1.7196(19)
C9 C14 1.392(2)
C9 C10 1.403(3)
C10 C11 1.378(3)
C10 H10 0.9500
C11 C12 1.397(3)
C11 H11 0.9500
C12 O1 1.367(2)
C12 C13 1.391(3)
C13 C14 1.393(3)
C13 H13 0.9500
C14 H14 0.9500
C15 N3 1.149(3)
C16 O1 1.430(2)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
N1 N2 1.257(2)
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
C2 H2 O1 4_476 0.95 2.47 3.391(2) 165
C16 H16C O1 1_455 0.98 2.59 3.516(3) 158
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
C6 C1 C2 C3 0.9(3)
C1 C2 C3 C4 -1.6(3)
C1 C2 C3 C15 178.65(18)
C2 C3 C4 C5 0.3(3)
C15 C3 C4 C5 -179.91(18)
C3 C4 C5 C6 1.5(3)
C4 C5 C6 C1 -2.2(3)
C4 C5 C6 N1 179.12(16)
C2 C1 C6 C5 0.9(3)
C2 C1 C6 N1 179.54(17)
N2 C7 C8 Cl2 178.27(14)
C9 C7 C8 Cl2 -3.3(3)
N2 C7 C8 Cl1 -2.2(2)
C9 C7 C8 Cl1 176.26(14)
C8 C7 C9 C14 -52.1(3)
N2 C7 C9 C14 126.2(2)
C8 C7 C9 C10 129.9(2)
N2 C7 C9 C10 -51.9(3)
C14 C9 C10 C11 0.0(3)
C7 C9 C10 C11 178.04(17)
C9 C10 C11 C12 0.8(3)
C10 C11 C12 O1 178.52(17)
C10 C11 C12 C13 -1.1(3)
O1 C12 C13 C14 -178.90(17)
C11 C12 C13 C14 0.7(3)
C10 C9 C14 C13 -0.4(3)
C7 C9 C14 C13 -178.47(17)
C12 C13 C14 C9 0.0(3)
C5 C6 N1 N2 -156.50(17)
C1 C6 N1 N2 24.8(2)
C6 N1 N2 C7 -178.37(15)
C8 C7 N2 N1 -176.77(17)
C9 C7 N2 N1 4.8(3)
C13 C12 O1 C16 -4.7(3)
C11 C12 O1 C16 175.67(16)

_cod_database_fobs_code 2243019
