#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227410.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227410
loop_
_publ_author_name
'Susindran, V.'
'Athimoolam, S.'
'Bahadur, S. Asath'
'Manikannan, R.'
'Muthusubramanian, S.'
_publ_section_title
;
 (E)-3-(4-Chlorophenyl)-3-[3-(4-chlorophenyl)-1H-pyrazol-1-yl]prop-2-enal
;
_journal_coeditor_code           FB2206
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2594
_journal_page_last               o2595
_journal_paper_doi               10.1107/S1600536810035646
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H12 Cl2 N2 O'
_chemical_formula_moiety         'C18 H12 Cl2 N2 O'
_chemical_formula_sum            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20
_chemical_name_systematic
(E)-3-(4-Chlorophenyl)-3-[3-(4-chlorophenyl)-1H-pyrazol-1-yl]prop-2-enal
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                90.533(7)
_cell_angle_beta                 116.924(4)
_cell_angle_gamma                93.427(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4321(6)
_cell_length_b                   9.6081(5)
_cell_length_c                   9.9439(7)
_cell_measurement_reflns_used    4879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7
_cell_measurement_theta_min      2.4
_cell_volume                     801.38(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8950
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.8837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0640P)²+0.1138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                2982
_reflns_number_total             3464
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fb2206.cif
_cod_data_source_block           I
_cod_database_code               2227410
_cod_database_fobs_code          2227410
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_disorder_assembly
_atom_site_disorder_group
N N1 0.32051(15) 0.14597(14) 0.94391(16) 0.0637(3) Uani d . 1 . .
N N2 0.33330(15) 0.11932(14) 0.81571(16) 0.0645(3) Uani d . 1 . .
C C3 0.23105(17) 0.01018(15) 0.74769(19) 0.0609(4) Uani d . 1 . .
C C4 0.1527(2) -0.03430(17) 0.8341(2) 0.0703(4) Uani d . 1 . .
H H4 0.0765 -0.1085 0.8109 0.084 Uiso calc R 1 . .
C C5 0.2117(2) 0.05315(17) 0.9566(2) 0.0704(4) Uani d . 1 . .
H H5 0.1838 0.0510 1.0351 0.084 Uiso calc R 1 . .
C C11 0.42212(17) 0.24992(16) 1.05026(18) 0.0616(4) Uani d . 1 . .
C C12 0.36968(16) 0.29488(15) 1.16169(18) 0.0588(3) Uani d . 1 . .
C C13 0.21605(17) 0.33822(17) 1.1154(2) 0.0656(4) Uani d . 1 . .
H H13 0.1469 0.3408 1.0129 0.079 Uiso calc R 1 . .
C C14 0.16603(17) 0.37703(17) 1.2194(2) 0.0674(4) Uani d . 1 . .
H H14 0.0635 0.4053 1.1877 0.081 Uiso calc R 1 . .
C C15 0.26958(18) 0.37363(15) 1.3718(2) 0.0617(4) Uani d . 1 . .
C C16 0.42360(18) 0.33354(15) 1.42098(19) 0.0625(4) Uani d . 1 . .
H H16 0.4931 0.3333 1.5235 0.075 Uiso calc R 1 . .
C C17 0.47177(16) 0.29416(15) 1.31565(18) 0.0604(4) Uani d . 1 . .
H H17 0.5746 0.2665 1.3479 0.072 Uiso calc R 1 . .
C C31 0.21217(16) -0.04755(15) 0.60370(19) 0.0596(4) Uani d . 1 . .
C C32 0.2953(2) 0.01493(17) 0.5314(2) 0.0679(4) Uani d . 1 . .
H H32 0.3586 0.0971 0.5730 0.082 Uiso calc R 1 . .
C C33 0.28550(19) -0.04239(17) 0.4007(2) 0.0695(4) Uani d . 1 . .
H H33 0.3421 0.0002 0.3544 0.083 Uiso calc R 1 . .
C C34 0.19066(18) -0.16420(17) 0.33797(18) 0.0637(4) Uani d . 1 . .
C C35 0.10245(17) -0.22597(17) 0.4035(2) 0.0670(4) Uani d . 1 . .
H H35 0.0357 -0.3059 0.3590 0.080 Uiso calc R 1 . .
C C36 0.11458(17) -0.16782(16) 0.5355(2) 0.0651(4) Uani d . 1 . .
H H36 0.0561 -0.2099 0.5803 0.078 Uiso calc R 1 . .
C C1A 0.55695(18) 0.29870(18) 1.0452(2) 0.0694(4) Uani d . 1 . .
H H1A 0.5853 0.2553 0.9778 0.083 Uiso calc R 1 . .
C C2A 0.65832(19) 0.4138(2) 1.1383(2) 0.0739(4) Uani d . 1 . .
O O1 0.78899(15) 0.44765(18) 1.14726(18) 0.0993(5) Uani d . 1 . .
Cl Cl1 0.20652(6) 0.41935(5) 1.50378(6) 0.08373(18) Uani d . 1 . .
Cl Cl2 0.18660(6) -0.24132(5) 0.17751(5) 0.08459(18) Uani d . 1 . .
H H2A 0.612(3) 0.475(2) 1.198(3) 0.102 Uiso 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'
O O 0.0106 0.0060 '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
N2 N1 C5 . . 111.32(14) ?
N2 N1 C11 . . 120.54(13) ?
C5 N1 C11 . . 127.88(15) ?
C3 N2 N1 . . 105.24(13) ?
N2 C3 C4 . . 110.62(16) ?
N2 C3 C31 . . 120.42(14) ?
C4 C3 C31 . . 128.96(15) ?
C5 C4 C3 . . 105.75(15) ?
C5 C4 H4 . . 127.1 ?
C3 C4 H4 . . 127.1 ?
C4 C5 N1 . . 107.06(16) ?
C4 C5 H5 . . 126.5 ?
N1 C5 H5 . . 126.5 ?
C1A C11 N1 . . 119.59(16) ?
C1A C11 C12 . . 125.45(15) ?
N1 C11 C12 . . 114.95(13) ?
C17 C12 C13 . . 118.47(15) ?
C17 C12 C11 . . 120.65(13) ?
C13 C12 C11 . . 120.88(14) ?
C14 C13 C12 . . 120.84(15) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 119.37(14) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C14 C15 C16 . . 121.07(15) ?
C14 C15 Cl1 . . 119.74(12) ?
C16 C15 Cl1 . . 119.20(13) ?
C17 C16 C15 . . 118.93(15) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C16 C17 C12 . . 121.30(13) ?
C16 C17 H17 . . 119.3 ?
C12 C17 H17 . . 119.3 ?
C36 C31 C32 . . 117.70(16) ?
C36 C31 C3 . . 121.53(14) ?
C32 C31 C3 . . 120.75(14) ?
C33 C32 C31 . . 121.34(15) ?
C33 C32 H32 . . 119.3 ?
C31 C32 H32 . . 119.3 ?
C32 C33 C34 . . 119.49(15) ?
C32 C33 H33 . . 120.3 ?
C34 C33 H33 . . 120.3 ?
C35 C34 C33 . . 120.66(16) ?
C35 C34 Cl2 . . 120.04(13) ?
C33 C34 Cl2 . . 119.29(13) ?
C36 C35 C34 . . 119.15(15) ?
C36 C35 H35 . . 120.4 ?
C34 C35 H35 . . 120.4 ?
C35 C36 C31 . . 121.60(15) ?
C35 C36 H36 . . 119.2 ?
C31 C36 H36 . . 119.2 ?
C11 C1A C2A . . 123.32(17) ?
C11 C1A H1A . . 118.3 ?
C2A C1A H1A . . 118.3 ?
O1 C2A C1A . . 123.47(19) ?
O1 C2A H2A . . 119.7(13) ?
C1A C2A H2A . . 116.7(13) ?
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
N1 N2 . 1.357(2) ?
N1 C5 . 1.370(2) ?
N1 C11 . 1.408(2) ?
N2 C3 . 1.327(2) ?
C3 C4 . 1.418(2) ?
C3 C31 . 1.460(2) ?
C4 C5 . 1.346(3) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C11 C1A . 1.351(2) ?
C11 C12 . 1.474(2) ?
C12 C17 . 1.392(2) ?
C12 C13 . 1.399(2) ?
C13 C14 . 1.374(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.384(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.387(2) ?
C15 Cl1 . 1.7313(17) ?
C16 C17 . 1.375(2) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C31 C36 . 1.391(2) ?
C31 C32 . 1.398(2) ?
C32 C33 . 1.369(2) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.384(2) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.382(2) ?
C34 Cl2 . 1.7366(18) ?
C35 C36 . 1.375(2) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C1A C2A . 1.431(3) ?
C1A H1A . 0.9300 ?
C2A O1 . 1.219(2) ?
C2A H2A . 1.07(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
C13 H13 Cl2 2_556 0.93 2.93 3.6447(16) 134.3
C14 H14 O1 1_455 0.93 2.49 3.407(2) 167.4
C36 H36 Cl1 2_557 0.93 2.90 3.6334(16) 137.2
C17 H17 Cg1 2_657 0.93 2.68 3.4919(18) 147
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
C5 N1 N2 C3 . . . . 0.51(16) ?
C11 N1 N2 C3 . . . . 175.14(12) ?
N1 N2 C3 C4 . . . . -0.49(16) ?
N1 N2 C3 C31 . . . . 179.66(12) ?
N2 C3 C4 C5 . . . . 0.30(18) ?
C31 C3 C4 C5 . . . . -179.86(14) ?
C3 C4 C5 N1 . . . . 0.03(18) ?
N2 N1 C5 C4 . . . . -0.34(18) ?
C11 N1 C5 C4 . . . . -174.48(14) ?
N2 N1 C11 C1A . . . . -16.7(2) ?
C5 N1 C11 C1A . . . . 156.99(16) ?
N2 N1 C11 C12 . . . . 164.21(12) ?
C5 N1 C11 C12 . . . . -22.1(2) ?
C1A C11 C12 C17 . . . . -52.2(2) ?
N1 C11 C12 C17 . . . . 126.86(15) ?
C1A C11 C12 C13 . . . . 128.27(18) ?
N1 C11 C12 C13 . . . . -52.66(19) ?
C17 C12 C13 C14 . . . . -1.0(2) ?
C11 C12 C13 C14 . . . . 178.48(14) ?
C12 C13 C14 C15 . . . . 0.3(2) ?
C13 C14 C15 C16 . . . . 0.9(2) ?
C13 C14 C15 Cl1 . . . . -178.85(12) ?
C14 C15 C16 C17 . . . . -1.3(2) ?
Cl1 C15 C16 C17 . . . . 178.47(11) ?
C15 C16 C17 C12 . . . . 0.5(2) ?
C13 C12 C17 C16 . . . . 0.7(2) ?
C11 C12 C17 C16 . . . . -178.87(13) ?
N2 C3 C31 C36 . . . . 175.27(13) ?
C4 C3 C31 C36 . . . . -4.6(2) ?
N2 C3 C31 C32 . . . . -3.1(2) ?
C4 C3 C31 C32 . . . . 177.04(15) ?
C36 C31 C32 C33 . . . . -2.1(2) ?
C3 C31 C32 C33 . . . . 176.38(14) ?
C31 C32 C33 C34 . . . . 0.4(2) ?
C32 C33 C34 C35 . . . . 1.9(2) ?
C32 C33 C34 Cl2 . . . . -176.72(12) ?
C33 C34 C35 C36 . . . . -2.4(2) ?
Cl2 C34 C35 C36 . . . . 176.17(11) ?
C34 C35 C36 C31 . . . . 0.7(2) ?
C32 C31 C36 C35 . . . . 1.5(2) ?
C3 C31 C36 C35 . . . . -176.91(13) ?
N1 C11 C1A C2A . . . . 173.32(15) ?
C12 C11 C1A C2A . . . . -7.7(3) ?
C11 C1A C2A O1 . . . . 170.98(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656215
