#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/47/2234729.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_2234729
loop_
_publ_author_name
'Dai, Ling-Ling'
'Yin, Ben-Tao'
'Lv, Jing-Song'
'Cui, Sheng-Feng'
'Zhou, Cheng-He'
_publ_section_title
;
 (Z)-1,3-Bis(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one
;
_journal_coeditor_code           LH5453
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1456
_journal_paper_doi               10.1107/S1600536812016170
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H11 Cl2 N3 O'
_chemical_formula_moiety         'C17 H11 Cl2 N3 O'
_chemical_formula_sum            'C17 H11 Cl2 N3 O'
_chemical_formula_weight         344.19
_chemical_name_systematic
;
(Z)-1,3-Bis(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-
1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                74.787(10)
_cell_angle_beta                 88.884(9)
_cell_angle_gamma                86.461(9)
_cell_formula_units_Z            2
_cell_length_a                   5.588(3)
_cell_length_b                   11.850(7)
_cell_length_c                   12.653(8)
_cell_measurement_reflns_used    2086
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      3.34
_cell_volume                     806.9(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4414
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.9412
_exptl_absorpt_correction_T_min  0.9154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.1439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                2458
_reflns_number_total             3104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lh5453.cif
_cod_data_source_block           I
_cod_original_cell_volume        807.1(8)
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               2234729
_cod_database_fobs_code          2234729
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 1.58438(14) 0.60011(6) -0.17465(5) 0.1010(3) Uani d . 1 1
Cl Cl2 0.14916(9) 0.80981(5) 0.64259(4) 0.07445(19) Uani d . 1 1
C C1 1.4458(4) 0.6784(2) -0.08893(15) 0.0703(6) Uani d . 1 1
C C2 1.5551(4) 0.7730(2) -0.07247(16) 0.0719(6) Uani d . 1 1
H H2A 1.6975 0.7964 -0.1085 0.086 Uiso calc R 1 1
C C3 1.4505(4) 0.83280(18) -0.00168(16) 0.0654(5) Uani d . 1 1
H H3A 1.5235 0.8969 0.0100 0.079 Uiso calc R 1 1
C C4 1.2364(3) 0.79806(16) 0.05257(14) 0.0532(4) Uani d . 1 1
C C5 1.1286(4) 0.70284(18) 0.03344(15) 0.0637(5) Uani d . 1 1
H H5A 0.9861 0.6788 0.0691 0.076 Uiso calc R 1 1
C C6 1.2320(4) 0.6435(2) -0.03847(17) 0.0733(6) Uani d . 1 1
H H6A 1.1579 0.5808 -0.0525 0.088 Uiso calc R 1 1
C C7 1.1296(3) 0.87101(16) 0.12331(15) 0.0557(4) Uani d . 1 1
C C8 0.9716(3) 0.81969(14) 0.21872(14) 0.0487(4) Uani d . 1 1
C C9 1.1937(3) 0.63087(16) 0.31196(15) 0.0582(5) Uani d . 1 1
H H9A 1.3439 0.6594 0.3154 0.070 Uiso calc R 1 1
C C10 0.9086(4) 0.52367(17) 0.32519(19) 0.0736(6) Uani d . 1 1
H H10A 0.8222 0.4566 0.3425 0.088 Uiso calc R 1 1
C C11 0.8102(3) 0.88957(15) 0.25517(14) 0.0522(4) Uani d . 1 1
H H11A 0.7981 0.9669 0.2131 0.063 Uiso calc R 1 1
C C12 0.6506(3) 0.86366(14) 0.35025(13) 0.0475(4) Uani d . 1 1
C C13 0.6915(3) 0.77059(16) 0.44322(14) 0.0554(4) Uani d . 1 1
H H13A 0.8248 0.7190 0.4452 0.067 Uiso calc R 1 1
C C14 0.5387(3) 0.75364(16) 0.53190(15) 0.0564(4) Uani d . 1 1
H H14A 0.5684 0.6911 0.5931 0.068 Uiso calc R 1 1
C C15 0.3405(3) 0.83027(15) 0.52953(14) 0.0524(4) Uani d . 1 1
C C16 0.2943(3) 0.92271(17) 0.43910(16) 0.0637(5) Uani d . 1 1
H H16A 0.1595 0.9733 0.4373 0.076 Uiso calc R 1 1
C C17 0.4495(3) 0.93960(15) 0.35136(15) 0.0586(5) Uani d . 1 1
H H17A 0.4198 1.0033 0.2911 0.070 Uiso calc R 1 1
N N1 0.9986(2) 0.69650(11) 0.26747(11) 0.0466(3) Uani d . 1 1
N N2 0.8100(3) 0.62670(13) 0.27539(14) 0.0621(4) Uani d . 1 1
N N3 1.1434(3) 0.52092(14) 0.34991(15) 0.0737(5) Uani d . 1 1
O O1 1.1701(3) 0.97469(12) 0.10500(12) 0.0776(4) Uani d . 1 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C2 C1 C6 121.6(2)
C2 C1 Cl1 118.80(18)
C6 C1 Cl1 119.6(2)
C1 C2 C3 119.1(2)
C1 C2 H2A 120.5
C3 C2 H2A 120.5
C2 C3 C4 120.7(2)
C2 C3 H3A 119.6
C4 C3 H3A 119.6
C5 C4 C3 118.93(19)
C5 C4 C7 123.74(16)
C3 C4 C7 117.23(18)
C6 C5 C4 120.40(19)
C6 C5 H5A 119.8
C4 C5 H5A 119.8
C1 C6 C5 119.2(2)
C1 C6 H6A 120.4
C5 C6 H6A 120.4
O1 C7 C4 120.59(16)
O1 C7 C8 118.20(17)
C4 C7 C8 121.21(16)
C11 C8 N1 122.27(15)
C11 C8 C7 119.71(16)
N1 C8 C7 118.02(14)
N3 C9 N1 110.62(17)
N3 C9 H9A 124.7
N1 C9 H9A 124.7
N2 C10 N3 115.89(18)
N2 C10 H10A 122.1
N3 C10 H10A 122.1
C8 C11 C12 130.38(16)
C8 C11 H11A 114.8
C12 C11 H11A 114.8
C13 C12 C17 117.31(16)
C13 C12 C11 124.22(15)
C17 C12 C11 118.39(15)
C14 C13 C12 121.34(16)
C14 C13 H13A 119.3
C12 C13 H13A 119.3
C13 C14 C15 119.61(16)
C13 C14 H14A 120.2
C15 C14 H14A 120.2
C16 C15 C14 120.58(17)
C16 C15 Cl2 119.85(14)
C14 C15 Cl2 119.56(14)
C17 C16 C15 119.36(17)
C17 C16 H16A 120.3
C15 C16 H16A 120.3
C16 C17 C12 121.78(17)
C16 C17 H17A 119.1
C12 C17 H17A 119.1
C9 N1 N2 109.33(15)
C9 N1 C8 129.36(14)
N2 N1 C8 121.31(13)
C10 N2 N1 101.71(16)
C9 N3 C10 102.45(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.745(2)
Cl2 C15 1.743(2)
C1 C2 1.372(3)
C1 C6 1.379(3)
C2 C3 1.381(3)
C2 H2A 0.9300
C3 C4 1.398(3)
C3 H3A 0.9300
C4 C5 1.389(3)
C4 C7 1.492(3)
C5 C6 1.386(3)
C5 H5A 0.9300
C6 H6A 0.9300
C7 O1 1.224(2)
C7 C8 1.499(2)
C8 C11 1.343(2)
C8 N1 1.428(2)
C9 N3 1.311(3)
C9 N1 1.342(2)
C9 H9A 0.9300
C10 N2 1.311(3)
C10 N3 1.351(3)
C10 H10A 0.9300
C11 C12 1.461(2)
C11 H11A 0.9300
C12 C13 1.397(2)
C12 C17 1.398(2)
C13 C14 1.377(2)
C13 H13A 0.9300
C14 C15 1.384(2)
C14 H14A 0.9300
C15 C16 1.377(3)
C16 C17 1.375(3)
C16 H16A 0.9300
C17 H17A 0.9300
N1 N2 1.366(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
C6 C1 C2 C3 1.4(3)
Cl1 C1 C2 C3 -177.75(14)
C1 C2 C3 C4 0.0(3)
C2 C3 C4 C5 -0.6(3)
C2 C3 C4 C7 -177.11(17)
C3 C4 C5 C6 -0.1(3)
C7 C4 C5 C6 176.17(18)
C2 C1 C6 C5 -2.1(3)
Cl1 C1 C6 C5 177.06(15)
C4 C5 C6 C1 1.4(3)
C5 C4 C7 O1 -150.2(2)
C3 C4 C7 O1 26.1(3)
C5 C4 C7 C8 30.1(3)
C3 C4 C7 C8 -153.57(17)
O1 C7 C8 C11 25.1(3)
C4 C7 C8 C11 -155.23(17)
O1 C7 C8 N1 -155.21(17)
C4 C7 C8 N1 24.5(2)
N1 C8 C11 C12 5.7(3)
C7 C8 C11 C12 -174.66(17)
C8 C11 C12 C13 23.4(3)
C8 C11 C12 C17 -159.82(19)
C17 C12 C13 C14 0.6(3)
C11 C12 C13 C14 177.44(17)
C12 C13 C14 C15 -0.2(3)
C13 C14 C15 C16 0.4(3)
C13 C14 C15 Cl2 -179.19(14)
C14 C15 C16 C17 -1.1(3)
Cl2 C15 C16 C17 178.52(15)
C15 C16 C17 C12 1.6(3)
C13 C12 C17 C16 -1.3(3)
C11 C12 C17 C16 -178.32(18)
N3 C9 N1 N2 -0.5(2)
N3 C9 N1 C8 178.82(17)
C11 C8 N1 C9 -122.4(2)
C7 C8 N1 C9 58.0(2)
C11 C8 N1 N2 56.9(2)
C7 C8 N1 N2 -122.75(17)
N3 C10 N2 N1 0.0(2)
C9 N1 N2 C10 0.3(2)
C8 N1 N2 C10 -179.08(16)
N1 C9 N3 C10 0.5(2)
N2 C10 N3 C9 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8982668
