#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/30/2233037.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_2233037
loop_
_publ_author_name
'Singh, Shailja'
'Singh, Manavendra K.'
'Agarwal, Alka'
'Awasthi, Satish K.'
_publ_section_title
;
 2-(4-Chlorophenyl)chromen-4-one
;
_journal_coeditor_code           ZJ2023
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3163
_journal_paper_doi               10.1107/S1600536811043832
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H9 Cl O2'
_chemical_formula_moiety         'C15 H9 Cl O2'
_chemical_formula_sum            'C15 H9 Cl O2'
_chemical_formula_weight         256.67
_chemical_name_systematic
;
2-(4-Chlorophenyl)chromen-4-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.524(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.1564(16)
_cell_length_b                   3.8745(2)
_cell_length_c                   26.7728(18)
_cell_measurement_reflns_used    3949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5723
_cell_measurement_theta_min      3.0740
_cell_volume                     2287.6(3)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Xcalibur Eos'
_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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8152
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.9413
_exptl_absorpt_correction_T_min  0.9384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0483P)²+1.8360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                1910
_reflns_number_total             2249
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zj2023.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2233037
_cod_database_fobs_code          2233037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.31934(3) 0.85487(18) 0.02358(2) 0.0570(2) Uani d . 1 1
C C9 0.53822(9) 1.4266(6) 0.14239(7) 0.0337(5) Uani d . 1 1
C C6 0.64493(9) 1.7175(6) 0.18541(7) 0.0354(5) Uani d . 1 1
C C10 0.48486(9) 1.2780(6) 0.11311(7) 0.0337(5) Uani d . 1 1
C C1 0.63679(9) 1.6341(5) 0.13486(7) 0.0339(5) Uani d . 1 1
C C13 0.38335(9) 1.0144(6) 0.05827(8) 0.0397(5) Uani d . 1 1
C C15 0.48053(10) 1.2743(6) 0.06106(8) 0.0400(5) Uani d . 1 1
H H15 0.5123 1.3606 0.0445 0.048 Uiso calc R 1 1
C C8 0.54262(10) 1.5012(7) 0.19128(8) 0.0461(6) Uani d . 1 1
H H8 0.5095 1.4573 0.2092 0.055 Uiso calc R 1 1
C C5 0.70028(10) 1.8653(6) 0.20370(8) 0.0428(5) Uani d . 1 1
H H5 0.7069 1.9248 0.2374 0.051 Uiso calc R 1 1
C C2 0.68118(10) 1.6940(6) 0.10315(8) 0.0431(5) Uani d . 1 1
H H2 0.6748 1.6370 0.0693 0.052 Uiso calc R 1 1
C C14 0.42994(10) 1.1448(6) 0.03366(8) 0.0436(6) Uani d . 1 1
H H14 0.4273 1.1455 -0.0012 0.052 Uiso calc R 1 1
C C11 0.43729(10) 1.1410(6) 0.13715(8) 0.0416(5) Uani d . 1 1
H H11 0.4397 1.1385 0.1720 0.050 Uiso calc R 1 1
C C12 0.38674(10) 1.0092(6) 0.10974(8) 0.0431(5) Uani d . 1 1
H H12 0.3551 0.9172 0.1260 0.052 Uiso calc R 1 1
C C7 0.59653(11) 1.6468(6) 0.21751(8) 0.0445(6) Uani d . 1 1
O O2 0.60167(9) 1.7078(6) 0.26277(6) 0.0690(6) Uani d . 1 1
C C3 0.73488(10) 1.8388(6) 0.12232(9) 0.0472(6) Uani d . 1 1
H H3 0.7651 1.8809 0.1013 0.057 Uiso calc R 1 1
C C4 0.74463(11) 1.9233(6) 0.17286(9) 0.0475(6) Uani d . 1 1
H H4 0.7814 2.0193 0.1856 0.057 Uiso calc R 1 1
O O1 0.58414(6) 1.4868(4) 0.11337(5) 0.0382(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'
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
C8 C9 O1 122.4(2)
C8 C9 C10 125.9(2)
O1 C9 C10 111.72(17)
C1 C6 C5 117.7(2)
C1 C6 C7 119.74(19)
C5 C6 C7 122.57(19)
C15 C10 C11 118.6(2)
C15 C10 C9 120.89(19)
C11 C10 C9 120.54(18)
O1 C1 C2 116.05(18)
O1 C1 C6 122.07(18)
C2 C1 C6 121.9(2)
C14 C13 C12 121.1(2)
C14 C13 Cl1 119.24(17)
C12 C13 Cl1 119.70(17)
C14 C15 C10 120.9(2)
C14 C15 H15 119.5
C10 C15 H15 119.5
C9 C8 C7 122.8(2)
C9 C8 H8 118.6
C7 C8 H8 118.6
C4 C5 C6 121.0(2)
C4 C5 H5 119.5
C6 C5 H5 119.5
C3 C2 C1 118.9(2)
C3 C2 H2 120.5
C1 C2 H2 120.5
C13 C14 C15 119.4(2)
C13 C14 H14 120.3
C15 C14 H14 120.3
C12 C11 C10 120.5(2)
C12 C11 H11 119.7
C10 C11 H11 119.7
C13 C12 C11 119.5(2)
C13 C12 H12 120.2
C11 C12 H12 120.2
O2 C7 C8 123.3(2)
O2 C7 C6 122.7(2)
C8 C7 C6 114.01(18)
C2 C3 C4 120.6(2)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 119.9(2)
C5 C4 H4 120.1
C3 C4 H4 120.1
C9 O1 C1 118.96(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.733(2)
C9 C8 1.335(3)
C9 O1 1.358(2)
C9 C10 1.471(3)
C6 C1 1.386(3)
C6 C5 1.399(3)
C6 C7 1.463(3)
C10 C15 1.388(3)
C10 C11 1.392(3)
C1 O1 1.374(2)
C1 C2 1.379(3)
C13 C14 1.373(3)
C13 C12 1.373(3)
C15 C14 1.374(3)
C15 H15 0.9300
C8 C7 1.441(3)
C8 H8 0.9300
C5 C4 1.362(3)
C5 H5 0.9300
C2 C3 1.370(3)
C2 H2 0.9300
C14 H14 0.9300
C11 C12 1.377(3)
C11 H11 0.9300
C12 H12 0.9300
C7 O2 1.229(3)
C3 C4 1.389(3)
C3 H3 0.9300
C4 H4 0.9300
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
C11 H11 O2 2_645 0.93 2.64 3.345(3) 133.86(14) 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
C8 C9 C10 C15 167.0(2)
O1 C9 C10 C15 -12.2(3)
C8 C9 C10 C11 -12.3(4)
O1 C9 C10 C11 168.48(19)
C5 C6 C1 O1 179.74(19)
C7 C6 C1 O1 0.3(3)
C5 C6 C1 C2 -0.2(3)
C7 C6 C1 C2 -179.6(2)
C11 C10 C15 C14 1.3(4)
C9 C10 C15 C14 -178.1(2)
O1 C9 C8 C7 -0.9(4)
C10 C9 C8 C7 180.0(2)
C1 C6 C5 C4 -0.3(3)
C7 C6 C5 C4 179.1(2)
O1 C1 C2 C3 -179.7(2)
C6 C1 C2 C3 0.3(3)
C12 C13 C14 C15 -0.5(4)
Cl1 C13 C14 C15 179.43(18)
C10 C15 C14 C13 -0.6(4)
C15 C10 C11 C12 -0.9(3)
C9 C10 C11 C12 178.5(2)
C14 C13 C12 C11 0.9(4)
Cl1 C13 C12 C11 -179.02(18)
C10 C11 C12 C13 -0.2(4)
C9 C8 C7 O2 -178.0(3)
C9 C8 C7 C6 2.2(4)
C1 C6 C7 O2 178.3(2)
C5 C6 C7 O2 -1.1(4)
C1 C6 C7 C8 -1.9(3)
C5 C6 C7 C8 178.7(2)
C1 C2 C3 C4 0.2(4)
C6 C5 C4 C3 0.7(4)
C2 C3 C4 C5 -0.7(4)
C8 C9 O1 C1 -0.9(3)
C10 C9 O1 C1 178.32(17)
C2 C1 O1 C9 -178.86(19)
C6 C1 O1 C9 1.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 133537
