#------------------------------------------------------------------------------
#$Date: 2020-07-11 08:07:59 +0300 (Sat, 11 Jul 2020) $
#$Revision: 254202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243483.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_2243483
loop_
_publ_author_name
'Özkaraca, Kadriye'
'Akkurt, Mehmet'
'Shikhaliyev, Namiq Q.'
'Askerova, Ulviyya F.'
'Suleymanova, Gulnar T.'
'Mammadova, Gunay Z.'
'Shadrack, Daniel M.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (E)-4-{2,2-dichloro-1-[(3,5-dimethylphenyl)diazenyl]ethenyl}-N,N-dimethylaniline
;
_journal_coeditor_code           HB7912
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1251
_journal_page_last               1254
_journal_paper_doi               10.1107/S2056989020009202
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C18 H19 Cl2 N3'
_chemical_formula_moiety         'C18 H19 Cl2 N3'
_chemical_formula_sum            'C18 H19 Cl2 N3'
_chemical_formula_weight         348.26
_chemical_name_systematic
(E)-4-{2,2-Dichloro-1-[(3,5-dimethylphenyl)diazenyl]ethenyl}-N,N-dimethylaniline
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.421(2)
_cell_angle_beta                 95.880(2)
_cell_angle_gamma                91.105(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1035(4)
_cell_length_b                   9.1965(5)
_cell_length_c                   12.3665(7)
_cell_measurement_reflns_used    7784
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.27
_cell_volume                     894.48(8)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13675
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.747
_diffrn_reflns_theta_min         2.270
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0449
_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)+(0.0539P)²+0.3599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2786
_reflns_number_total             3339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7912sup1.cif
_cod_data_source_block           I
_cod_database_code               2243483
_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   0.905
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4932(2) 0.5319(2) 0.78212(16) 0.0507(4) Uani d 1 . .
C C2 0.3377(3) 0.5251(2) 0.72287(17) 0.0572(5) Uani d 1 . .
H H2A 0.313279 0.592879 0.678105 0.069 Uiso calc 1 . .
C C3 0.2180(2) 0.4186(2) 0.72940(19) 0.0586(5) Uani d 1 . .
C C4 0.2585(2) 0.3198(2) 0.79718(18) 0.0578(5) Uani d 1 . .
H H4A 0.179261 0.247628 0.801995 0.069 Uiso calc 1 . .
C C5 0.4136(2) 0.3245(2) 0.85843(16) 0.0528(4) Uani d 1 . .
C C6 0.5313(2) 0.4323(2) 0.85097(16) 0.0515(4) Uani d 1 . .
H H6A 0.635267 0.438287 0.891630 0.062 Uiso calc 1 . .
C C7 0.8563(2) 0.7644(2) 0.81327(15) 0.0486(4) Uani d 1 . .
C C8 0.8188(2) 0.8616(2) 0.73299(15) 0.0470(4) Uani d 1 . .
C C9 0.7799(3) 1.0079(2) 0.76813(17) 0.0624(5) Uani d 1 . .
H H9A 0.780539 1.047283 0.844019 0.075 Uiso calc 1 . .
C C10 0.7401(3) 1.0978(2) 0.69421(18) 0.0663(6) Uani d 1 . .
H H10A 0.713687 1.195886 0.721428 0.080 Uiso calc 1 . .
C C11 0.7385(2) 1.0455(2) 0.58013(16) 0.0530(4) Uani d 1 . .
C C12 0.7818(4) 0.8986(3) 0.54516(18) 0.0731(7) Uani d 1 . .
H H12A 0.785747 0.859575 0.469609 0.088 Uiso calc 1 . .
C C13 0.8188(3) 0.8099(2) 0.61981(18) 0.0705(6) Uani d 1 . .
H H13A 0.844835 0.711493 0.593078 0.085 Uiso calc 1 . .
C C14 0.0476(3) 0.4121(3) 0.6668(3) 0.0815(7) Uani d 1 . .
H H14A 0.015539 0.310513 0.631791 0.122 Uiso calc 1 . .
H H14B 0.049299 0.470111 0.610925 0.122 Uiso calc 1 . .
H H14C -0.030567 0.451581 0.717658 0.122 Uiso calc 1 . .
C C15 0.4523(3) 0.2146(3) 0.9306(2) 0.0681(6) Uani d 1 . .
H H15A 0.553126 0.246587 0.978497 0.102 Uiso calc 1 . .
H H15B 0.465759 0.118284 0.884317 0.102 Uiso calc 1 . .
H H15C 0.362933 0.208661 0.974908 0.102 Uiso calc 1 . .
C C16 0.9971(2) 0.7786(2) 0.88186(16) 0.0520(4) Uani d 1 . .
C C17 0.6238(4) 1.2751(3) 0.5403(2) 0.0806(7) Uani d 1 . .
H H17A 0.556425 1.271764 0.599308 0.121 Uiso calc 1 . .
H H17B 0.556809 1.299516 0.478616 0.121 Uiso calc 1 . .
H H17C 0.711966 1.349476 0.566573 0.121 Uiso calc 1 . .
C C18 0.6996(5) 1.0776(3) 0.3882(2) 0.0944(9) Uani d 1 . .
H H18A 0.639013 0.983527 0.364268 0.142 Uiso calc 1 . .
H H18B 0.813161 1.065188 0.373532 0.142 Uiso calc 1 . .
H H18C 0.651020 1.147779 0.348239 0.142 Uiso calc 1 . .
Cl Cl1 1.04137(8) 0.67088(7) 0.97728(5) 0.0734(2) Uani d 1 . .
Cl Cl2 1.15092(7) 0.90973(7) 0.88372(5) 0.0707(2) Uani d 1 . .
N N1 0.6056(2) 0.64606(18) 0.76759(14) 0.0552(4) Uani d 1 . .
N N2 0.7438(2) 0.64937(17) 0.82395(13) 0.0523(4) Uani d 1 . .
N N3 0.6932(3) 1.1321(2) 0.50518(15) 0.0745(6) 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.38(17) ?
C2 C1 N1 . . 115.34(17) ?
C6 C1 N1 . . 124.28(17) ?
C1 C2 C3 . . 120.85(19) ?
C1 C2 H2A . . 119.6 ?
C3 C2 H2A . . 119.6 ?
C4 C3 C2 . . 118.00(19) ?
C4 C3 C14 . . 120.8(2) ?
C2 C3 C14 . . 121.2(2) ?
C3 C4 C5 . . 122.48(18) ?
C3 C4 H4A . . 118.8 ?
C5 C4 H4A . . 118.8 ?
C6 C5 C4 . . 118.55(18) ?
C6 C5 C15 . . 120.77(19) ?
C4 C5 C15 . . 120.67(18) ?
C5 C6 C1 . . 119.72(18) ?
C5 C6 H6A . . 120.1 ?
C1 C6 H6A . . 120.1 ?
C16 C7 N2 . . 114.49(16) ?
C16 C7 C8 . . 123.12(16) ?
N2 C7 C8 . . 122.39(16) ?
C9 C8 C13 . . 116.53(18) ?
C9 C8 C7 . . 121.42(17) ?
C13 C8 C7 . . 122.04(17) ?
C8 C9 C10 . . 121.94(18) ?
C8 C9 H9A . . 119.0 ?
C10 C9 H9A . . 119.0 ?
C9 C10 C11 . . 121.60(19) ?
C9 C10 H10A . . 119.2 ?
C11 C10 H10A . . 119.2 ?
N3 C11 C10 . . 122.27(19) ?
N3 C11 C12 . . 121.46(18) ?
C10 C11 C12 . . 116.26(18) ?
C13 C12 C11 . . 121.38(19) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C12 C13 C8 . . 122.3(2) ?
C12 C13 H13A . . 118.9 ?
C8 C13 H13A . . 118.9 ?
C3 C14 H14A . . 109.5 ?
C3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C5 C15 H15A . . 109.5 ?
C5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C7 C16 Cl1 . . 124.05(14) ?
C7 C16 Cl2 . . 122.70(14) ?
Cl1 C16 Cl2 . . 113.24(11) ?
N3 C17 H17A . . 109.5 ?
N3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N3 C18 H18A . . 109.5 ?
N3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N2 N1 C1 . . 113.12(16) ?
N1 N2 C7 . . 114.22(16) ?
C11 N3 C18 . . 121.15(19) ?
C11 N3 C17 . . 121.07(19) ?
C18 N3 C17 . . 117.6(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.384(3) ?
C1 C6 . 1.397(3) ?
C1 N1 . 1.429(2) ?
C2 C3 . 1.385(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.385(3) ?
C3 C14 . 1.506(3) ?
C4 C5 . 1.394(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.387(3) ?
C5 C15 . 1.503(3) ?
C6 H6A . 0.9300 ?
C7 C16 . 1.336(3) ?
C7 N2 . 1.420(2) ?
C7 C8 . 1.485(2) ?
C8 C9 . 1.375(3) ?
C8 C13 . 1.378(3) ?
C9 C10 . 1.378(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.388(3) ?
C10 H10A . 0.9300 ?
C11 N3 . 1.374(3) ?
C11 C12 . 1.391(3) ?
C12 C13 . 1.373(3) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 Cl1 . 1.7123(19) ?
C16 Cl2 . 1.7129(18) ?
C17 N3 . 1.438(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 N3 . 1.433(3) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
N1 N2 . 1.254(2) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.9(3) ?
N1 C1 C2 C3 . . . . 179.58(18) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C1 C2 C3 C14 . . . . 178.9(2) ?
C2 C3 C4 C5 . . . . 0.2(3) ?
C14 C3 C4 C5 . . . . -178.5(2) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C3 C4 C5 C15 . . . . -179.74(19) ?
C4 C5 C6 C1 . . . . -0.6(3) ?
C15 C5 C6 C1 . . . . 179.08(18) ?
C2 C1 C6 C5 . . . . 1.1(3) ?
N1 C1 C6 C5 . . . . -179.40(17) ?
C16 C7 C8 C9 . . . . -72.4(3) ?
N2 C7 C8 C9 . . . . 107.0(2) ?
C16 C7 C8 C13 . . . . 108.5(3) ?
N2 C7 C8 C13 . . . . -72.1(3) ?
C13 C8 C9 C10 . . . . 1.1(3) ?
C7 C8 C9 C10 . . . . -178.0(2) ?
C8 C9 C10 C11 . . . . -0.5(4) ?
C9 C10 C11 N3 . . . . 177.5(2) ?
C9 C10 C11 C12 . . . . -1.0(4) ?
N3 C11 C12 C13 . . . . -176.6(2) ?
C10 C11 C12 C13 . . . . 1.9(4) ?
C11 C12 C13 C8 . . . . -1.4(4) ?
C9 C8 C13 C12 . . . . -0.2(4) ?
C7 C8 C13 C12 . . . . 179.0(2) ?
N2 C7 C16 Cl1 . . . . -0.9(3) ?
C8 C7 C16 Cl1 . . . . 178.48(14) ?
N2 C7 C16 Cl2 . . . . 179.97(14) ?
C8 C7 C16 Cl2 . . . . -0.6(3) ?
C2 C1 N1 N2 . . . . 179.06(17) ?
C6 C1 N1 N2 . . . . -0.5(3) ?
C1 N1 N2 C7 . . . . -178.40(15) ?
C16 C7 N2 N1 . . . . -173.27(17) ?
C8 C7 N2 N1 . . . . -6.1(3) ?
C10 C11 N3 C18 . . . . 177.2(3) ?
C12 C11 N3 C18 . . . . -4.4(4) ?
C10 C11 N3 C17 . . . . -8.3(4) ?
C12 C11 N3 C17 . . . . 170.1(3) ?

_cod_database_fobs_code 2243483
