#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/33/2013316.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_2013316
loop_
_publ_author_name
'Thinagar, S.'
'Velmurugan, D.'
'Shanmuga Sundara Raj, S.'
'Fun, Hoong-Kun'
'Gupta, S. C.'
'Merazig, H.'
'Bouacida, S.'
_publ_section_title
;
 3,3'-[o-Phenylenebis(methyleneoxy)]bis(6-chloroflavone) and
 3,3'-propylenedioxybis[6-chloro-2-(2-furyl)-4H-1-benzopyran-4-one]
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o181
_journal_page_last               o183
_journal_paper_doi               10.1107/S0108270103002361
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C38 H24 Cl2 O6'
_chemical_formula_moiety         'C38 H24 Cl2 O6'
_chemical_formula_sum            'C38 H24 Cl2 O6'
_chemical_formula_weight         647.47
_chemical_name_common            Bis(6-chloroflavanone-3-yloxy)-o-xylene
_chemical_name_systematic
;
3,3'-[o-Phenylenebis(methyleneoxy)]bis(6-chloro-2-phenylflavanone)
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.393(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2360(10)
_cell_length_b                   10.799(4)
_cell_length_c                   21.775(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1.2
_cell_volume                     3111.5(13)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.467
_diffrn_measured_fraction_theta_max 0.467
_diffrn_measurement_device_type
;
Enraf-Nonius CAD-4
;
_diffrn_measurement_method       'Non-profiled w/2θ'
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4781
_diffrn_reflns_theta_full        30.41
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1929
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1073P)²+1.2599P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.2298
_reflns_number_gt                1928
_reflns_number_total             4612
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1583.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2013316
_cod_database_fobs_code          2013316
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_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 -0.00142(10) 0.19640(16) 0.02509(5) 0.1133(6) Uani d . 1 . . Cl
O1 0.31016(18) -0.0226(2) -0.08577(10) 0.0645(7) Uani d . 1 . . O
O2 0.14304(14) 0.1378(2) -0.22423(8) 0.0434(5) Uani d . 1 . . O
O3 0.37549(15) -0.03714(19) -0.20629(9) 0.0472(5) Uani d . 1 . . O
C1 0.2884(2) 0.0245(3) -0.19096(12) 0.0381(6) Uani d . 1 . . C
C2 0.2607(2) 0.0279(3) -0.12679(13) 0.0434(7) Uani d . 1 . . C
C3 0.1672(2) 0.0969(3) -0.11629(13) 0.0423(7) Uani d . 1 . . C
C4 0.1304(3) 0.1116(3) -0.05660(14) 0.0576(9) Uani d . 1 . . C
H4 0.1642 0.0759 -0.0231 0.069 Uiso calc R 1 . . H
C5 0.0444(3) 0.1791(4) -0.04859(15) 0.0622(10) Uani d . 1 . . C
C6 -0.0083(3) 0.2306(4) -0.09685(16) 0.0616(10) Uani d . 1 . . C
H6 -0.0667 0.2759 -0.0899 0.074 Uiso calc R 1 . . H
C7 0.0250(2) 0.2153(3) -0.15547(15) 0.0520(8) Uani d . 1 . . C
H7 -0.0108 0.2490 -0.1888 0.062 Uiso calc R 1 . . H
C8 0.1128(2) 0.1488(3) -0.16410(13) 0.0409(7) Uani d . 1 . . C
C9 0.2309(2) 0.0754(3) -0.23602(12) 0.0383(6) Uani d . 1 . . C
C10 0.2516(2) 0.0731(3) -0.30218(13) 0.0400(7) Uani d . 1 . . C
C11 0.2684(3) -0.0377(3) -0.33210(15) 0.0543(8) Uani d . 1 . . C
H11 0.2658 -0.1116 -0.3102 0.065 Uiso calc R 1 . . H
C12 0.2890(3) -0.0404(4) -0.39440(16) 0.0618(10) Uani d . 1 . . C
H12 0.2992 -0.1156 -0.4141 0.074 Uiso calc R 1 . . H
C13 0.2943(3) 0.0683(4) -0.42649(15) 0.0641(10) Uani d . 1 . . C
H13 0.3093 0.0670 -0.4680 0.077 Uiso calc R 1 . . H
C14 0.2776(3) 0.1794(4) -0.39761(15) 0.0605(9) Uani d . 1 . . C
H14 0.2812 0.2530 -0.4196 0.073 Uiso calc R 1 . . H
C15 0.2554(2) 0.1817(3) -0.33566(14) 0.0505(8) Uani d . 1 . . C
H15 0.2431 0.2570 -0.3165 0.061 Uiso calc R 1 . . H
C16 0.4669(2) 0.0283(4) -0.18564(14) 0.0544(9) Uani d . 1 . . C
H16A 0.5249 -0.0253 -0.1909 0.065 Uiso calc R 1 . . H
H16B 0.4623 0.0465 -0.1422 0.065 Uiso calc R 1 . . H
C17 0.4833(2) 0.1466(3) -0.21990(13) 0.0450(7) Uani d . 1 . . C
C18 0.4660(3) 0.2595(4) -0.1916(2) 0.0765(12) Uani d . 1 . . C
H18 0.4425 0.2606 -0.1517 0.092 Uiso calc R 1 . . H
C19 0.4828(3) 0.3696(4) -0.2213(3) 0.106(2) Uani d . 1 . . C
H19 0.4703 0.4442 -0.2016 0.127 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O2 C8 . . 119.0(2) y
C1 O3 C16 . . 112.5(2) ?
C9 C1 O3 . . 118.9(2) ?
C9 C1 C2 . . 122.6(2) y
O3 C1 C2 . . 118.5(2) ?
O1 C2 C1 . . 123.2(3) ?
O1 C2 C3 . . 123.4(3) ?
C1 C2 C3 . . 113.3(2) y
C8 C3 C4 . . 117.9(3) ?
C8 C3 C2 . . 121.2(2) y
C4 C3 C2 . . 120.9(3) ?
C5 C4 C3 . . 119.1(3) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
C6 C5 C4 . . 122.0(3) ?
C6 C5 Cl1 . . 118.9(3) ?
C4 C5 Cl1 . . 119.0(3) ?
C5 C6 C7 . . 119.9(3) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C6 C7 C8 . . 118.6(3) ?
C6 C7 H7 . . 120.7 ?
C8 C7 H7 . . 120.7 ?
C3 C8 C7 . . 122.4(3) y
C3 C8 O2 . . 121.7(2) y
C7 C8 O2 . . 115.9(3) ?
C1 C9 O2 . . 122.1(2) y
C1 C9 C10 . . 126.2(2) ?
O2 C9 C10 . . 111.7(2) ?
C11 C10 C15 . . 118.5(3) ?
C11 C10 C9 . . 120.7(3) ?
C15 C10 C9 . . 120.8(3) ?
C10 C11 C12 . . 121.0(3) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C13 C12 C11 . . 119.6(3) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 120.3(3) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.1(3) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C10 C15 C14 . . 120.6(3) ?
C10 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
O3 C16 C17 . . 112.8(2) ?
O3 C16 H16A . . 109.0 ?
C17 C16 H16A . . 109.0 ?
O3 C16 H16B . . 109.0 ?
C17 C16 H16B . . 109.0 ?
H16A C16 H16B . . 107.8 ?
C18 C17 C17 . 2_654 118.5(2) ?
C18 C17 C16 . . 120.0(3) ?
C17 C17 C16 2_654 . 121.43(17) ?
C19 C18 C17 . . 121.4(4) ?
C19 C18 H18 . . 119.3 ?
C17 C18 H18 . . 119.3 ?
C19 C19 C18 2_654 . 120.1(3) ?
C19 C19 H19 2_654 . 120.0 ?
C18 C19 H19 . . 120.0 ?
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 C5 . 1.739(3) ?
O1 C2 . 1.223(4) ?
O2 C9 . 1.373(3) ?
O2 C8 . 1.383(3) y
O3 C1 . 1.379(3) ?
O3 C16 . 1.463(4) ?
C1 C9 . 1.345(4) y
C1 C2 . 1.454(4) y
C2 C3 . 1.468(4) y
C3 C8 . 1.371(4) y
C3 C4 . 1.408(4) ?
C4 C5 . 1.367(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.365(5) ?
C6 C7 . 1.370(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.384(4) ?
C7 H7 . 0.9300 ?
C9 C10 . 1.473(4) ?
C10 C11 . 1.384(4) ?
C10 C15 . 1.382(4) ?
C11 C12 . 1.391(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.369(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.375(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.388(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.498(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.387(5) ?
C17 C17 2_654 1.394(6) ?
C18 C19 . 1.375(7) ?
C18 H18 . 0.9300 ?
C19 C19 2_654 1.340(11) ?
C19 H19 . 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
C16 H16B O1 1_555 0.97 2.50 3.091(4) 119 y
C18 H18 Cl1 7_555 0.93 2.88 3.676(5) 144 y
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_4
_geom_torsion
_geom_torsion_publ_flag
C16 O3 C1 C9 . . 111.1(3) ?
C16 O3 C1 C2 . . -71.0(3) ?
C9 C1 C2 O1 . . 176.8(3) ?
O3 C1 C2 O1 . . -1.0(5) ?
C9 C1 C2 C3 . . -2.7(4) ?
O3 C1 C2 C3 . . 179.5(3) ?
O1 C2 C3 C8 . . -178.1(3) ?
C1 C2 C3 C8 . . 1.4(4) ?
O1 C2 C3 C4 . . 1.8(5) ?
C1 C2 C3 C4 . . -178.7(3) ?
C8 C3 C4 C5 . . -1.7(5) ?
C2 C3 C4 C5 . . 178.4(3) ?
C3 C4 C5 C6 . . 1.4(6) ?
C3 C4 C5 Cl1 . . 179.6(3) ?
C4 C5 C6 C7 . . -0.1(6) ?
Cl1 C5 C6 C7 . . -178.3(3) ?
C5 C6 C7 C8 . . -0.9(6) ?
C4 C3 C8 C7 . . 0.7(5) ?
C2 C3 C8 C7 . . -179.4(3) ?
C4 C3 C8 O2 . . -179.4(3) ?
C2 C3 C8 O2 . . 0.5(5) ?
C6 C7 C8 C3 . . 0.6(5) ?
C6 C7 C8 O2 . . -179.3(3) ?
C9 O2 C8 C3 . . -1.4(4) ?
C9 O2 C8 C7 . . 178.5(3) ?
O3 C1 C9 O2 . . 179.8(3) ?
C2 C1 C9 O2 . . 2.0(4) ?
O3 C1 C9 C10 . . -0.3(4) ?
C2 C1 C9 C10 . . -178.1(3) ?
C8 O2 C9 C1 . . 0.2(4) ?
C8 O2 C9 C10 . . -179.7(2) ?
C1 C9 C10 C11 . . 54.1(4) y
O2 C9 C10 C11 . . -126.0(3) ?
C1 C9 C10 C15 . . -125.4(3) ?
O2 C9 C10 C15 . . 54.4(4) ?
C15 C10 C11 C12 . . 0.2(5) ?
C9 C10 C11 C12 . . -179.3(3) ?
C10 C11 C12 C13 . . 0.9(5) ?
C11 C12 C13 C14 . . -1.1(5) ?
C12 C13 C14 C15 . . 0.1(5) ?
C11 C10 C15 C14 . . -1.3(5) ?
C9 C10 C15 C14 . . 178.3(3) ?
C13 C14 C15 C10 . . 1.1(5) ?
C1 O3 C16 C17 . . -68.8(3) ?
O3 C16 C17 C18 . . 106.2(3) y
O3 C16 C17 C17 . 2_654 -74.4(4) ?
C17 C17 C18 C19 2_654 . -1.1(6) ?
C16 C17 C18 C19 . . 178.3(4) ?
C17 C18 C19 C19 . 2_654 -0.4(8) ?
