#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/22/2212282.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_2212282
loop_
_publ_author_name
'Yathirajan, H. S.'
'Mayekar, A. N.'
'Sarojini, B. K.'
'Narayana, B.'
'Bolte, Michael'
_publ_section_title
;
 (2E)-1-(2,4-Dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           LH2280
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o426
_journal_page_last               o427
_journal_paper_doi               10.1107/S1600536806055024
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H10 Cl2 O2'
_chemical_formula_moiety         'C15 H10 Cl2 O2'
_chemical_formula_sum            'C15 H10 Cl2 O2'
_chemical_formula_weight         293.13
_chemical_name_systematic
;
(2E)-1-(2,4-Dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.5702(5)
_cell_length_b                   8.8146(4)
_cell_length_c                   20.6699(7)
_cell_measurement_reflns_used    50392
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.9
_cell_measurement_theta_min      2.8
_cell_volume                     2654.65(18)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe IPDS-II two-circle'
_diffrn_measurement_method       ω
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47302
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.73
_diffrn_reflns_theta_min         2.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  0.8610
_exptl_absorpt_correction_T_min  0.8456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.318
_refine_ls_extinction_coef       0.0073(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0319
_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)+(0.0391P)²+1.2454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                3486
_reflns_number_total             3736
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2280.cif
_cod_data_source_block           I
_cod_database_code               2212282
_cod_database_fobs_code          2212282
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
Cl Cl1 0.74623(2) 0.29091(4) 0.223353(15) 0.03212(10) Uani d . 1
Cl Cl2 1.07277(2) 0.57695(4) 0.213640(18) 0.03754(10) Uani d . 1
O O1 0.73437(6) 0.28622(11) 0.02984(4) 0.02824(19) Uani d . 1
O O2 0.39744(6) 0.27875(10) 0.03016(5) 0.02800(19) Uani d . 1
H H2 0.3456(14) 0.261(2) 0.0129(10) 0.049(5) Uiso d . 1
C C1 0.72896(7) 0.37001(13) 0.07746(5) 0.0206(2) Uani d . 1
C C2 0.64258(7) 0.43662(13) 0.09997(5) 0.0226(2) Uani d . 1
H H2A 0.6433 0.5019 0.1365 0.027 Uiso calc R 1
C C3 0.56209(7) 0.40777(12) 0.07022(5) 0.0200(2) Uani d . 1
H H3 0.5628 0.3384 0.0351 0.024 Uiso calc R 1
C C11 0.81515(7) 0.41533(12) 0.11295(5) 0.0199(2) Uani d . 1
C C12 0.82791(7) 0.39183(12) 0.17911(5) 0.0211(2) Uani d . 1
C C13 0.90662(8) 0.44059(13) 0.21128(6) 0.0242(2) Uani d . 1
H H13 0.9143 0.4245 0.2564 0.029 Uiso calc R 1
C C14 0.97356(8) 0.51376(13) 0.17488(6) 0.0248(2) Uani d . 1
C C15 0.96494(8) 0.53649(13) 0.10865(6) 0.0264(2) Uani d . 1
H H15 1.0123 0.5849 0.0848 0.032 Uiso calc R 1
C C16 0.88531(8) 0.48685(14) 0.07805(6) 0.0244(2) Uani d . 1
H H16 0.8784 0.5017 0.0328 0.029 Uiso calc R 1
C C21 0.47392(7) 0.47499(12) 0.08784(5) 0.0197(2) Uani d . 1
C C22 0.39134(7) 0.40636(12) 0.06703(5) 0.0209(2) Uani d . 1
C C23 0.30627(8) 0.46780(13) 0.08488(6) 0.0254(2) Uani d . 1
H H23 0.2511 0.4192 0.0719 0.030 Uiso calc R 1
C C24 0.30274(8) 0.59963(15) 0.12152(6) 0.0282(2) Uani d . 1
H H24 0.2450 0.6407 0.1337 0.034 Uiso calc R 1
C C25 0.38357(8) 0.67231(14) 0.14066(6) 0.0287(2) Uani d . 1
H H25 0.3809 0.7638 0.1649 0.034 Uiso calc R 1
C C26 0.46771(8) 0.60980(13) 0.12402(6) 0.0244(2) Uani d . 1
H H26 0.5225 0.6592 0.1374 0.029 Uiso calc R 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'
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
C22 O2 H2 109.2(13)
O1 C1 C2 123.27(10)
O1 C1 C11 119.58(9)
C2 C1 C11 117.05(9)
C3 C2 C1 121.79(10)
C3 C2 H2A 119.1
C1 C2 H2A 119.1
C2 C3 C21 125.07(10)
C2 C3 H3 117.5
C21 C3 H3 117.5
C12 C11 C16 118.30(10)
C12 C11 C1 123.25(9)
C16 C11 C1 118.44(10)
C13 C12 C11 122.10(10)
C13 C12 Cl1 117.94(9)
C11 C12 Cl1 119.89(8)
C14 C13 C12 117.52(11)
C14 C13 H13 121.2
C12 C13 H13 121.2
C15 C14 C13 122.46(10)
C15 C14 Cl2 118.78(9)
C13 C14 Cl2 118.75(9)
C14 C15 C16 118.54(11)
C14 C15 H15 120.7
C16 C15 H15 120.7
C15 C16 C11 121.05(11)
C15 C16 H16 119.5
C11 C16 H16 119.5
C26 C21 C22 117.93(10)
C26 C21 C3 122.12(10)
C22 C21 C3 119.93(10)
O2 C22 C23 121.60(10)
O2 C22 C21 117.92(10)
C23 C22 C21 120.47(10)
C24 C23 C22 119.98(11)
C24 C23 H23 120.0
C22 C23 H23 120.0
C23 C24 C25 120.46(11)
C23 C24 H24 119.8
C25 C24 H24 119.8
C26 C25 C24 119.49(11)
C26 C25 H25 120.3
C24 C25 H25 120.3
C25 C26 C21 121.60(11)
C25 C26 H26 119.2
C21 C26 H26 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C12 1.7446(11)
Cl2 C14 1.7440(11)
O1 C1 1.2331(14)
O2 C22 1.3616(14)
O2 H2 0.85(2)
C1 C2 1.4646(15)
C1 C11 1.5082(14)
C2 C3 1.3484(15)
C2 H2A 0.9500
C3 C21 1.4609(14)
C3 H3 0.9500
C11 C12 1.3956(15)
C11 C16 1.4010(15)
C12 C13 1.3936(15)
C13 C14 1.3905(17)
C13 H13 0.9500
C14 C15 1.3893(18)
C15 C16 1.3920(16)
C15 H15 0.9500
C16 H16 0.9500
C21 C26 1.4069(15)
C21 C22 1.4137(14)
C22 C23 1.4021(15)
C23 C24 1.3880(17)
C23 H23 0.9500
C24 C25 1.3979(17)
C24 H24 0.9500
C25 C26 1.3874(16)
C25 H25 0.9500
C26 H26 0.9500
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
O2 H2 O1 4_455 0.85(2) 1.89(2) 2.7408(12) 176(2)
C15 H15 O2 8_765 0.95 2.43 3.3485(15) 161.6
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
O1 C1 C2 C3 1.23(18)
C11 C1 C2 C3 177.66(10)
C1 C2 C3 C21 -177.07(10)
O1 C1 C11 C12 -124.71(12)
C2 C1 C11 C12 58.72(15)
O1 C1 C11 C16 56.40(15)
C2 C1 C11 C16 -120.17(12)
C16 C11 C12 C13 1.69(16)
C1 C11 C12 C13 -177.21(10)
C16 C11 C12 Cl1 -175.29(9)
C1 C11 C12 Cl1 5.81(15)
C11 C12 C13 C14 -0.42(17)
Cl1 C12 C13 C14 176.61(9)
C12 C13 C14 C15 -1.17(17)
C12 C13 C14 Cl2 179.76(8)
C13 C14 C15 C16 1.40(18)
Cl2 C14 C15 C16 -179.52(9)
C14 C15 C16 C11 -0.06(18)
C12 C11 C16 C15 -1.43(17)
C1 C11 C16 C15 177.52(10)
C2 C3 C21 C26 20.03(17)
C2 C3 C21 C22 -161.58(11)
C26 C21 C22 O2 177.81(10)
C3 C21 C22 O2 -0.64(15)
C26 C21 C22 C23 -3.02(16)
C3 C21 C22 C23 178.53(10)
O2 C22 C23 C24 -178.82(11)
C21 C22 C23 C24 2.05(17)
C22 C23 C24 C25 0.24(19)
C23 C24 C25 C26 -1.47(19)
C24 C25 C26 C21 0.42(19)
C22 C21 C26 C25 1.80(17)
C3 C21 C26 C25 -179.79(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655162
