#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/18/2201890.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_2201890
loop_
_publ_author_name
'Jose Kavitha, Savaridasson'
'Sarangarajan, Thanjavur Ramabhadran'
'Thanikasalam, Kanagasabapathy'
'Panchanatheswaran, Krishnaswamy'
'Jeyaraman, Ramasubbu'
_publ_section_title
r-2,c-6-Bis(4-chlorophenyl)-t-3,t-5-dimethyltetrahydropyran-4-one
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o463
_journal_page_last               o465
_journal_paper_doi               10.1107/S1600536803005361
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C19 H18 Cl2 O2'
_chemical_formula_moiety         'C19 H18 Cl2 O2'
_chemical_formula_sum            'C19 H18 Cl2 O2'
_chemical_formula_weight         349.23
_chemical_melting_point          463.5(5)
_chemical_name_systematic
;
r-2,c-6-di(4-chlorophenyl)-t-3,t-5-dimethyltetrahydropyran-4-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                   15.0130(10)
_cell_length_b                   9.1230(16)
_cell_length_c                   25.462(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      2
_cell_volume                     3487.4(9)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3164
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.9628
_exptl_absorpt_correction_T_min  0.9336
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.339
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0478P)²+2.3284P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                2205
_reflns_number_total             3163
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6205.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '463-464 K' was changed to '463.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '463-464 K' was changed to '463.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2201890
_cod_database_fobs_code          2201890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
Cl1 -0.23836(7) 0.02833(16) 0.01666(4) 0.0972(4) Uani d . 1 . . Cl
Cl2 -0.08127(7) 0.15480(12) 0.46889(3) 0.0824(3) Uani d . 1 . . Cl
O1 0.02534(12) 0.1605(2) 0.21639(7) 0.0458(5) Uani d . 1 . . O
O8 0.24462(15) 0.3915(3) 0.18791(9) 0.0769(7) Uani d . 1 . . O
C2 0.06250(18) 0.1593(3) 0.16462(10) 0.0443(7) Uani d . 1 . . C
H2 0.1069 0.0808 0.1622 0.053 Uiso calc R 1 . . H
C3 0.10719(19) 0.3064(3) 0.15152(11) 0.0503(7) Uani d . 1 . . C
H3 0.0599 0.3802 0.1494 0.060 Uiso calc R 1 . . H
C4 0.16895(19) 0.3520(4) 0.19549(11) 0.0512(7) Uani d . 1 . . C
C5 0.12892(19) 0.3420(3) 0.24983(11) 0.0473(7) Uani d . 1 . . C
H5 0.0795 0.4120 0.2516 0.057 Uiso calc R 1 . . H
C6 0.08960(18) 0.1865(3) 0.25631(10) 0.0437(6) Uani d . 1 . . C
H6 0.1376 0.1141 0.2533 0.052 Uiso calc R 1 . . H
C7 0.1531(2) 0.3028(5) 0.09841(12) 0.0757(11) Uani d . 1 . . C
H7A 0.1804 0.3961 0.0917 0.114 Uiso calc R 1 . . H
H7B 0.1100 0.2823 0.0715 0.114 Uiso calc R 1 . . H
H7C 0.1979 0.2277 0.0984 0.114 Uiso calc R 1 . . H
C9 0.1958(2) 0.3839(5) 0.29223(13) 0.0718(10) Uani d . 1 . . C
H9A 0.2177 0.4811 0.2857 0.108 Uiso calc R 1 . . H
H9B 0.2446 0.3160 0.2918 0.108 Uiso calc R 1 . . H
H9C 0.1673 0.3811 0.3260 0.108 Uiso calc R 1 . . H
C10 -0.01328(19) 0.1260(3) 0.12766(10) 0.0466(7) Uani d . 1 . . C
C11 -0.0038(2) 0.0220(4) 0.08873(11) 0.0569(8) Uani d . 1 . . C
H11 0.0498 -0.0283 0.0853 0.068 Uiso calc R 1 . . H
C12 -0.0732(2) -0.0083(4) 0.05471(12) 0.0654(9) Uani d . 1 . . C
H12 -0.0665 -0.0795 0.0289 0.079 Uiso calc R 1 . . H
C13 -0.1515(2) 0.0666(4) 0.05918(11) 0.0616(9) Uani d . 1 . . C
C14 -0.1623(2) 0.1733(4) 0.09694(12) 0.0625(9) Uani d . 1 . . C
H14 -0.2154 0.2256 0.0993 0.075 Uiso calc R 1 . . H
C15 -0.09288(19) 0.2017(4) 0.13140(12) 0.0538(8) Uani d . 1 . . C
H15 -0.0999 0.2724 0.1574 0.065 Uiso calc R 1 . . H
C16 0.04384(18) 0.1679(3) 0.30830(10) 0.0424(6) Uani d . 1 . . C
C17 0.08966(19) 0.1095(4) 0.35091(11) 0.0506(7) Uani d . 1 . . C
H17 0.1473 0.0745 0.3462 0.061 Uiso calc R 1 . . H
C18 0.0508(2) 0.1028(4) 0.40025(11) 0.0557(8) Uani d . 1 . . C
H18 0.0822 0.0648 0.4286 0.067 Uiso calc R 1 . . H
C19 -0.0341(2) 0.1526(3) 0.40650(11) 0.0547(8) Uani d . 1 . . C
C20 -0.0826(2) 0.2061(4) 0.36463(12) 0.0562(8) Uani d . 1 . . C
H20 -0.1412 0.2365 0.3692 0.067 Uiso calc R 1 . . H
C21 -0.04284(18) 0.2138(3) 0.31581(11) 0.0496(7) Uani d . 1 . . C
H21 -0.0750 0.2505 0.2875 0.060 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
C6 O1 C2 113.28(19) y
O1 C2 C10 106.4(2) ?
O1 C2 C3 111.3(2) y
C10 C2 C3 111.7(2) ?
O1 C2 H2 109.1 ?
C10 C2 H2 109.1 ?
C3 C2 H2 109.1 ?
C4 C3 C7 112.8(2) ?
C4 C3 C2 110.3(2) y
C7 C3 C2 111.9(3) ?
C4 C3 H3 107.2 ?
C7 C3 H3 107.2 ?
C2 C3 H3 107.2 ?
O8 C4 C5 122.6(3) ?
O8 C4 C3 122.7(3) ?
C5 C4 C3 114.7(2) y
C4 C5 C9 111.8(2) ?
C4 C5 C6 107.7(2) y
C9 C5 C6 114.0(3) ?
C4 C5 H5 107.7 ?
C9 C5 H5 107.7 ?
C6 C5 H5 107.7 ?
O1 C6 C16 107.5(2) ?
O1 C6 C5 109.6(2) y
C16 C6 C5 111.9(2) ?
O1 C6 H6 109.2 ?
C16 C6 H6 109.2 ?
C5 C6 H6 109.2 ?
C3 C7 H7A 109.5 ?
C3 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C3 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C5 C9 H9A 109.5 ?
C5 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C5 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C11 C10 C15 118.8(3) ?
C11 C10 C2 120.6(3) ?
C15 C10 C2 120.6(3) ?
C10 C11 C12 120.6(3) ?
C10 C11 H11 119.7 ?
C12 C11 H11 119.7 ?
C13 C12 C11 119.8(3) ?
C13 C12 H12 120.1 ?
C11 C12 H12 120.1 ?
C12 C13 C14 120.9(3) ?
C12 C13 Cl1 119.7(3) ?
C14 C13 Cl1 119.4(3) ?
C13 C14 C15 119.0(3) ?
C13 C14 H14 120.5 ?
C15 C14 H14 120.5 ?
C10 C15 C14 120.9(3) ?
C10 C15 H15 119.6 ?
C14 C15 H15 119.6 ?
C21 C16 C17 118.3(3) ?
C21 C16 C6 121.3(2) ?
C17 C16 C6 120.3(2) ?
C18 C17 C16 121.0(3) ?
C18 C17 H17 119.5 ?
C16 C17 H17 119.5 ?
C19 C18 C17 119.0(3) ?
C19 C18 H18 120.5 ?
C17 C18 H18 120.5 ?
C18 C19 C20 121.4(3) ?
C18 C19 Cl2 119.5(2) ?
C20 C19 Cl2 119.1(2) ?
C21 C20 C19 119.0(3) ?
C21 C20 H20 120.5 ?
C19 C20 H20 120.5 ?
C16 C21 C20 121.1(3) ?
C16 C21 H21 119.4 ?
C20 C21 H21 119.4 ?
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
Cl1 C13 . 1.731(3) ?
Cl2 C19 . 1.740(3) ?
O1 C6 . 1.421(3) y
O1 C2 . 1.431(3) y
O8 C4 . 1.207(3) y
C2 C10 . 1.507(4) ?
C2 C3 . 1.537(4) y
C2 H2 . 0.98 ?
C3 C4 . 1.512(4) y
C3 C7 . 1.518(4) y
C3 H3 . 0.98 ?
C4 C5 . 1.511(4) y
C5 C9 . 1.523(4) y
C5 C6 . 1.546(4) y
C5 H5 . 0.98 ?
C6 C16 . 1.501(4) ?
C6 H6 . 0.98 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C10 C11 . 1.380(4) ?
C10 C15 . 1.383(4) ?
C11 C12 . 1.383(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.364(5) ?
C12 H12 . 0.93 ?
C13 C14 . 1.378(5) ?
C14 C15 . 1.387(4) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 C21 . 1.380(4) ?
C16 C17 . 1.391(4) ?
C17 C18 . 1.387(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.362(4) ?
C18 H18 . 0.93 ?
C19 C20 . 1.381(4) ?
C20 C21 . 1.381(4) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
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
_geom_torsion_publ_flag
C6 O1 C2 C10 178.3(2) ?
C6 O1 C2 C3 -59.8(3) y
O1 C2 C3 C4 49.2(3) y
C10 C2 C3 C4 167.9(2) ?
O1 C2 C3 C7 175.6(2) ?
C10 C2 C3 C7 -65.6(3) ?
C7 C3 C4 O8 5.1(5) ?
C2 C3 C4 O8 131.1(3) ?
C7 C3 C4 C5 -174.0(3) ?
C2 C3 C4 C5 -48.0(3) y
O8 C4 C5 C9 -1.3(4) ?
C3 C4 C5 C9 177.8(3) ?
O8 C4 C5 C6 -127.3(3) ?
C3 C4 C5 C6 51.8(3) y
C2 O1 C6 C16 -173.7(2) ?
C2 O1 C6 C5 64.5(3) y
C4 C5 C6 O1 -57.9(3) y
C9 C5 C6 O1 177.4(2) ?
C4 C5 C6 C16 -177.1(2) ?
C9 C5 C6 C16 58.2(3) ?
O1 C2 C10 C11 -133.0(3) ?
C3 C2 C10 C11 105.3(3) ?
O1 C2 C10 C15 48.5(4) ?
C3 C2 C10 C15 -73.2(3) ?
C15 C10 C11 C12 -1.3(5) ?
C2 C10 C11 C12 -179.8(3) ?
C10 C11 C12 C13 0.8(5) ?
C11 C12 C13 C14 0.6(5) ?
C11 C12 C13 Cl1 -179.9(3) ?
C12 C13 C14 C15 -1.5(5) ?
Cl1 C13 C14 C15 179.0(2) ?
C11 C10 C15 C14 0.3(5) ?
C2 C10 C15 C14 178.9(3) ?
C13 C14 C15 C10 1.0(5) ?
O1 C6 C16 C21 -37.5(3) ?
C5 C6 C16 C21 83.0(3) ?
O1 C6 C16 C17 145.4(3) ?
C5 C6 C16 C17 -94.1(3) ?
C21 C16 C17 C18 -2.5(5) ?
C6 C16 C17 C18 174.6(3) ?
C16 C17 C18 C19 0.9(5) ?
C17 C18 C19 C20 1.6(5) ?
C17 C18 C19 Cl2 -176.2(2) ?
C18 C19 C20 C21 -2.3(5) ?
Cl2 C19 C20 C21 175.5(2) ?
C17 C16 C21 C20 1.8(4) ?
C6 C16 C21 C20 -175.3(3) ?
C19 C20 C21 C16 0.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 292878
