#------------------------------------------------------------------------------
#$Date: 2020-06-20 07:54:02 +0300 (Sat, 20 Jun 2020) $
#$Revision: 253292 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243445.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_2243445
loop_
_publ_author_name
'Özkaraca, Kadriye'
'Akkurt, Mehmet'
'Shikhaliyev, Namiq Q.'
'Askerova, Ulviyya F.'
'Suleymanova, Gulnar T.'
'Mammadova, Gunay Z.'
'Mlowe, Sixberth'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-{2,2-dichloro-1-[(E)-2-(4-methylphenyl)diazen-1-yl]ethenyl}-N,N-dimethylaniline
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1122
_journal_page_last               1125
_journal_paper_doi               10.1107/S2056989020007744
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C17 H17 Cl2 N3'
_chemical_formula_moiety         'C17 H17 Cl2 N3'
_chemical_formula_sum            'C17 H17 Cl2 N3'
_chemical_formula_weight         334.23
_chemical_name_systematic
4-{2,2-Dichloro-1-[(E)-2-(4-methylphenyl)diazen-1-yl]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
_cell_angle_alpha                114.162(5)
_cell_angle_beta                 109.930(5)
_cell_angle_gamma                90.917(6)
_cell_formula_units_Z            2
_cell_length_a                   9.5967(15)
_cell_length_b                   9.6767(15)
_cell_length_c                   10.8043(17)
_cell_measurement_reflns_used    8175
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.23
_cell_volume                     846.3(2)
_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, 2015b)
;
_computing_structure_solution
;
SHELXT2016/6 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEXII PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13168
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.126
_diffrn_reflns_theta_min         2.423
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0407
_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)+(0.0413P)²+0.2744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2808
_reflns_number_total             3286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5539sup1.cif
_cod_data_source_block           I
_cod_database_code               2243445
_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   0.881
_shelx_estimated_absorpt_t_max   0.910
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 0.62327(18) 0.77347(17) 0.27963(16) 0.0430(3) Uani d 1 . .
C C2 0.55622(19) 0.69400(19) 0.12860(18) 0.0511(4) Uani d 1 . .
H H2A 0.458599 0.638289 0.084781 0.061 Uiso calc 1 . .
C C3 0.6330(2) 0.6968(2) 0.04271(18) 0.0556(4) Uani d 1 . .
H H3A 0.586196 0.643088 -0.058810 0.067 Uiso calc 1 . .
C C4 0.7787(2) 0.77812(19) 0.1045(2) 0.0524(4) Uani d 1 . .
C C5 0.8437(2) 0.8594(2) 0.2560(2) 0.0546(4) Uani d 1 . .
H H5A 0.940803 0.916211 0.299537 0.065 Uiso calc 1 . .
C C6 0.76843(19) 0.85845(19) 0.34383(18) 0.0504(4) Uani d 1 . .
H H6A 0.814274 0.914147 0.445239 0.060 Uiso calc 1 . .
C C7 0.50704(19) 0.81792(18) 0.56909(17) 0.0466(4) Uani d 1 . .
C C8 0.36451(18) 0.70537(18) 0.49547(17) 0.0459(4) Uani d 1 . .
C C9 0.3511(2) 0.58051(19) 0.52632(19) 0.0516(4) Uani d 1 . .
H H9A 0.432363 0.569863 0.597144 0.062 Uiso calc 1 . .
C C10 0.2204(2) 0.4724(2) 0.4546(2) 0.0533(4) Uani d 1 . .
H H10A 0.215848 0.390240 0.477657 0.064 Uiso calc 1 . .
C C11 0.09506(19) 0.48342(19) 0.34826(19) 0.0508(4) Uani d 1 . .
C C12 0.1089(2) 0.6101(2) 0.3183(2) 0.0553(4) Uani d 1 . .
H H12A 0.027551 0.622051 0.248519 0.066 Uiso calc 1 . .
C C13 0.2401(2) 0.7167(2) 0.39000(19) 0.0527(4) Uani d 1 . .
H H13A 0.245451 0.798834 0.366953 0.063 Uiso calc 1 . .
C C14 0.8640(3) 0.7763(3) 0.0098(3) 0.0783(6) Uani d 1 . .
H H14A 0.889625 0.879225 0.023489 0.118 Uiso calc 1 . .
H H14B 0.802118 0.712384 -0.091347 0.118 Uiso calc 1 . .
H H14C 0.954396 0.736056 0.036936 0.118 Uiso calc 1 . .
C C15 0.5678(2) 0.9067(2) 0.71430(18) 0.0517(4) Uani d 1 . .
C C16 -0.0462(3) 0.2427(2) 0.3018(3) 0.0794(6) Uani d 1 . .
H H16A 0.034913 0.189498 0.288174 0.119 Uiso calc 1 . .
H H16B -0.140759 0.175108 0.234394 0.119 Uiso calc 1 . .
H H16C -0.039713 0.274646 0.400506 0.119 Uiso calc 1 . .
C C17 -0.1688(2) 0.3981(3) 0.1783(3) 0.0790(6) Uani d 1 . .
H H17A -0.149409 0.401936 0.098146 0.118 Uiso calc 1 . .
H H17B -0.196497 0.493105 0.230865 0.118 Uiso calc 1 . .
H H17C -0.249623 0.314219 0.140945 0.118 Uiso calc 1 . .
Cl Cl1 0.73773(6) 1.03097(6) 0.80319(5) 0.07071(18) Uani d 1 . .
Cl Cl2 0.48299(7) 0.90774(6) 0.82988(5) 0.07116(18) Uani d 1 . .
N N1 0.53535(15) 0.75555(15) 0.35683(14) 0.0473(3) Uani d 1 . .
N N2 0.59263(16) 0.83959(15) 0.49225(14) 0.0477(3) Uani d 1 . .
N N3 -0.03590(19) 0.37582(19) 0.2751(2) 0.0710(5) 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 . . 119.28(14) ?
C2 C1 N1 . . 115.14(14) ?
C6 C1 N1 . . 125.54(14) ?
C3 C2 C1 . . 120.38(16) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C2 C3 C4 . . 121.27(16) ?
C2 C3 H3A . . 119.4 ?
C4 C3 H3A . . 119.4 ?
C3 C4 C5 . . 117.74(15) ?
C3 C4 C14 . . 120.93(17) ?
C5 C4 C14 . . 121.33(18) ?
C6 C5 C4 . . 121.83(16) ?
C6 C5 H5A . . 119.1 ?
C4 C5 H5A . . 119.1 ?
C5 C6 C1 . . 119.47(15) ?
C5 C6 H6A . . 120.3 ?
C1 C6 H6A . . 120.3 ?
C15 C7 N2 . . 114.01(15) ?
C15 C7 C8 . . 123.11(15) ?
N2 C7 C8 . . 122.87(14) ?
C13 C8 C9 . . 116.98(16) ?
C13 C8 C7 . . 121.61(14) ?
C9 C8 C7 . . 121.38(15) ?
C10 C9 C8 . . 121.69(16) ?
C10 C9 H9A . . 119.2 ?
C8 C9 H9A . . 119.2 ?
C9 C10 C11 . . 121.48(15) ?
C9 C10 H10A . . 119.3 ?
C11 C10 H10A . . 119.3 ?
N3 C11 C10 . . 122.12(15) ?
N3 C11 C12 . . 121.30(16) ?
C10 C11 C12 . . 116.58(16) ?
C13 C12 C11 . . 121.43(16) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C12 C13 C8 . . 121.84(15) ?
C12 C13 H13A . . 119.1 ?
C8 C13 H13A . . 119.1 ?
C4 C14 H14A . . 109.5 ?
C4 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C4 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C7 C15 Cl2 . . 123.03(14) ?
C7 C15 Cl1 . . 123.91(13) ?
Cl2 C15 Cl1 . . 113.06(10) ?
N3 C16 H16A . . 109.5 ?
N3 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N3 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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 ?
N2 N1 C1 . . 113.76(13) ?
N1 N2 C7 . . 113.53(14) ?
C11 N3 C17 . . 121.17(17) ?
C11 N3 C16 . . 120.75(18) ?
C17 N3 C16 . . 117.94(18) ?
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 . 1.382(2) ?
C1 C6 . 1.391(2) ?
C1 N1 . 1.4251(19) ?
C2 C3 . 1.375(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.385(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.386(3) ?
C4 C14 . 1.507(2) ?
C5 C6 . 1.377(2) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C15 . 1.340(2) ?
C7 N2 . 1.418(2) ?
C7 C8 . 1.480(2) ?
C8 C13 . 1.384(2) ?
C8 C9 . 1.393(2) ?
C9 C10 . 1.378(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.393(2) ?
C10 H10A . 0.9300 ?
C11 N3 . 1.377(2) ?
C11 C12 . 1.405(2) ?
C12 C13 . 1.375(3) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 Cl2 . 1.7046(17) ?
C15 Cl1 . 1.7179(19) ?
C16 N3 . 1.439(3) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 N3 . 1.432(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N1 N2 . 1.2520(18) ?
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
C15 Cl2 Cg1 2_676 1.7046(17) 3.6017(12) 4.065(2) 93.03(7) 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_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 . . . . 1.0(2) ?
N1 C1 C2 C3 . . . . -177.02(15) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
C2 C3 C4 C5 . . . . -1.3(3) ?
C2 C3 C4 C14 . . . . 177.94(17) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C14 C4 C5 C6 . . . . -178.15(17) ?
C4 C5 C6 C1 . . . . 0.2(3) ?
C2 C1 C6 C5 . . . . -1.3(2) ?
N1 C1 C6 C5 . . . . 176.59(15) ?
C15 C7 C8 C13 . . . . 119.31(18) ?
N2 C7 C8 C13 . . . . -61.7(2) ?
C15 C7 C8 C9 . . . . -62.6(2) ?
N2 C7 C8 C9 . . . . 116.43(17) ?
C13 C8 C9 C10 . . . . 0.4(2) ?
C7 C8 C9 C10 . . . . -177.74(15) ?
C8 C9 C10 C11 . . . . -0.4(3) ?
C9 C10 C11 N3 . . . . 179.61(16) ?
C9 C10 C11 C12 . . . . 0.0(2) ?
N3 C11 C12 C13 . . . . -179.23(17) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C11 C12 C13 C8 . . . . -0.4(3) ?
C9 C8 C13 C12 . . . . -0.1(2) ?
C7 C8 C13 C12 . . . . 178.13(15) ?
N2 C7 C15 Cl2 . . . . 177.33(11) ?
C8 C7 C15 Cl2 . . . . -3.6(2) ?
N2 C7 C15 Cl1 . . . . -2.5(2) ?
C8 C7 C15 Cl1 . . . . 176.56(12) ?
C2 C1 N1 N2 . . . . -173.79(14) ?
C6 C1 N1 N2 . . . . 8.3(2) ?
C1 N1 N2 C7 . . . . -178.18(12) ?
C15 C7 N2 N1 . . . . 179.64(14) ?
C8 C7 N2 N1 . . . . 0.6(2) ?
C10 C11 N3 C17 . . . . 172.96(19) ?
C12 C11 N3 C17 . . . . -7.4(3) ?
C10 C11 N3 C16 . . . . -2.6(3) ?
C12 C11 N3 C16 . . . . 177.03(18) ?

_cod_database_fobs_code 2243445
