#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226749.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_2226749
loop_
_publ_author_name
'Chen, Rener'
'Zhou, Qizhong'
_publ_section_title
;
 1,3-Bis(4-chlorophenyl)-1-methyl-1H-benzo[f]chromene
;
_journal_coeditor_code           ZQ2041
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1760
_journal_paper_doi               10.1107/S1600536810022610
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H18 Cl2 O'
_chemical_formula_moiety         'C26 H18 Cl2 O'
_chemical_formula_sum            'C26 H18 Cl2 O'
_chemical_formula_weight         417.33
_chemical_name_systematic
;
1,3-Bis(4-chlorophenyl)-1-methyl-1H-benzo[f]chromene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                93.511(2)
_cell_angle_beta                 102.0453(15)
_cell_angle_gamma                94.287(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9554(6)
_cell_length_b                   9.4439(6)
_cell_length_c                   12.3206(7)
_cell_measurement_reflns_used    6736
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     1013.05(11)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for windows (Farrugia, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10050
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             432.00
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.33
_refine_ls_extinction_coef       0.0188(6)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4596
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0010P)²+0.9200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                2783
_reflns_number_total             4596
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            zq2041.cif
_cod_data_source_block           I
_cod_database_code               2226749
_cod_database_fobs_code          2226749
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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
Cl Cl1 0.25919(11) -0.05748(9) 0.82025(6) 0.0899(3) Uani d . 1.00 . .
Cl Cl2 0.54898(11) 0.29006(9) -0.01095(6) 0.0875(2) Uani d . 1.00 . .
O O1 0.27277(19) 0.50754(14) 0.53308(12) 0.0492(4) Uani d . 1.00 . .
C C1 0.1329(2) 0.4692(2) 0.29332(18) 0.0405(5) Uani d . 1.00 . .
C C2 0.2049(2) 0.6121(2) 0.35548(17) 0.0380(4) Uani d . 1.00 . .
C C3 0.2145(2) 0.7416(2) 0.29947(18) 0.0406(5) Uani d . 1.00 . .
C C4 0.1688(2) 0.7468(2) 0.1828(2) 0.0521(6) Uani d . 1.00 . .
C C5 0.1790(3) 0.8718(2) 0.1324(2) 0.0614(7) Uani d . 1.00 . .
C C6 0.2364(3) 0.9992(2) 0.1961(2) 0.0635(7) Uani d . 1.00 . .
C C7 0.2840(2) 0.9991(2) 0.3080(2) 0.0543(6) Uani d . 1.00 . .
C C8 0.2758(2) 0.8720(2) 0.3627(2) 0.0430(5) Uani d . 1.00 . .
C C9 0.3277(2) 0.8730(2) 0.4787(2) 0.0473(5) Uani d . 1.00 . .
C C10 0.3245(2) 0.7510(2) 0.53063(19) 0.0465(5) Uani d . 1.00 . .
C C11 0.2644(2) 0.6220(2) 0.46756(18) 0.0403(4) Uani d . 1.00 . .
C C12 0.2041(2) 0.3771(2) 0.48333(18) 0.0406(5) Uani d . 1.00 . .
C C13 0.1397(2) 0.3577(2) 0.37734(19) 0.0431(5) Uani d . 1.00 . .
C C14 0.2173(2) 0.2685(2) 0.56609(18) 0.0401(4) Uani d . 1.00 . .
C C15 0.0923(2) 0.1769(2) 0.5723(2) 0.0542(6) Uani d . 1.00 . .
C C16 0.1045(2) 0.0765(2) 0.6511(2) 0.0609(7) Uani d . 1.00 . .
C C17 0.2428(3) 0.0687(2) 0.7219(2) 0.0532(6) Uani d . 1.00 . .
C C18 0.3693(2) 0.1574(2) 0.7168(2) 0.0538(6) Uani d . 1.00 . .
C C19 0.3551(2) 0.2575(2) 0.63937(19) 0.0483(5) Uani d . 1.00 . .
C C20 0.2310(2) 0.4205(2) 0.21085(17) 0.0419(5) Uani d . 1.00 . .
C C21 0.1736(3) 0.3746(2) 0.09965(19) 0.0542(6) Uani d . 1.00 . .
C C22 0.2691(3) 0.3322(2) 0.0309(2) 0.0618(7) Uani d . 1.00 . .
C C23 0.4242(3) 0.3367(2) 0.0735(2) 0.0571(6) Uani d . 1.00 . .
C C24 0.4842(2) 0.3788(2) 0.1839(2) 0.0547(6) Uani d . 1.00 . .
C C25 0.3879(2) 0.4192(2) 0.25085(19) 0.0475(5) Uani d . 1.00 . .
C C26 -0.0378(2) 0.4756(2) 0.2390(2) 0.0551(6) Uani d . 1.00 . .
H H4 0.1309 0.6630 0.1389 0.063 Uiso c R 1.00 . .
H H5 0.1474 0.8717 0.0556 0.074 Uiso c R 1.00 . .
H H6 0.2420 1.0839 0.1619 0.076 Uiso c R 1.00 . .
H H7 0.3229 1.0842 0.3498 0.065 Uiso c R 1.00 . .
H H9 0.3648 0.9586 0.5202 0.057 Uiso c R 1.00 . .
H H10 0.3615 0.7523 0.6071 0.056 Uiso c R 1.00 . .
H H13 0.0939 0.2670 0.3510 0.052 Uiso c R 1.00 . .
H H15 -0.0010 0.1823 0.5234 0.065 Uiso c R 1.00 . .
H H16 0.0198 0.0156 0.6555 0.073 Uiso c R 1.00 . .
H H18 0.4629 0.1501 0.7649 0.065 Uiso c R 1.00 . .
H H19 0.4400 0.3190 0.6363 0.058 Uiso c R 1.00 . .
H H21 0.0688 0.3724 0.0707 0.065 Uiso c R 1.00 . .
H H22 0.2287 0.3010 -0.0432 0.074 Uiso c R 1.00 . .
H H24 0.5889 0.3798 0.2127 0.066 Uiso c R 1.00 . .
H H25 0.4289 0.4468 0.3256 0.057 Uiso c R 1.00 . .
H H261 -0.0469 0.5428 0.1831 0.066 Uiso c R 1.00 . .
H H262 -0.0806 0.3831 0.2052 0.066 Uiso c R 1.00 . .
H H263 -0.0921 0.5047 0.2948 0.066 Uiso c R 1.00 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C12 . . . 117.40(15) ?
C2 C1 C13 . . . 108.24(16) ?
C2 C1 C20 . . . 109.59(17) ?
C2 C1 C26 . . . 111.80(18) ?
C13 C1 C20 . . . 106.20(17) ?
C13 C1 C26 . . . 106.86(18) ?
C20 C1 C26 . . . 113.82(17) ?
C1 C2 C3 . . . 122.33(17) ?
C1 C2 C11 . . . 120.91(18) ?
C3 C2 C11 . . . 116.76(17) ?
C2 C3 C4 . . . 123.51(18) ?
C2 C3 C8 . . . 119.56(19) ?
C4 C3 C8 . . . 116.9(2) ?
C3 C4 C5 . . . 121.9(2) ?
C4 C5 C6 . . . 120.3(2) ?
C5 C6 C7 . . . 119.8(2) ?
C6 C7 C8 . . . 121.4(2) ?
C3 C8 C7 . . . 119.6(2) ?
C3 C8 C9 . . . 119.6(2) ?
C7 C8 C9 . . . 120.82(19) ?
C8 C9 C10 . . . 120.91(19) ?
C9 C10 C11 . . . 119.3(2) ?
O1 C11 C2 . . . 124.47(17) ?
O1 C11 C10 . . . 111.76(17) ?
C2 C11 C10 . . . 123.8(2) ?
O1 C12 C13 . . . 122.56(19) ?
O1 C12 C14 . . . 110.38(16) ?
C13 C12 C14 . . . 127.05(18) ?
C1 C13 C12 . . . 126.12(19) ?
C12 C14 C15 . . . 120.82(19) ?
C12 C14 C19 . . . 120.67(19) ?
C15 C14 C19 . . . 118.5(2) ?
C14 C15 C16 . . . 120.7(2) ?
C15 C16 C17 . . . 119.1(2) ?
Cl1 C17 C16 . . . 119.3(2) ?
Cl1 C17 C18 . . . 119.22(18) ?
C16 C17 C18 . . . 121.5(2) ?
C17 C18 C19 . . . 118.9(2) ?
C14 C19 C18 . . . 121.4(2) ?
C1 C20 C21 . . . 124.8(2) ?
C1 C20 C25 . . . 118.00(17) ?
C21 C20 C25 . . . 117.2(2) ?
C20 C21 C22 . . . 121.4(2) ?
C21 C22 C23 . . . 119.3(2) ?
Cl2 C23 C22 . . . 120.80(18) ?
Cl2 C23 C24 . . . 118.6(2) ?
C22 C23 C24 . . . 120.6(2) ?
C23 C24 C25 . . . 119.3(2) ?
C20 C25 C24 . . . 122.2(2) ?
C3 C4 H4 . . . 119.0 ?
C5 C4 H4 . . . 119.0 ?
C4 C5 H5 . . . 119.8 ?
C6 C5 H5 . . . 119.8 ?
C5 C6 H6 . . . 120.1 ?
C7 C6 H6 . . . 120.1 ?
C6 C7 H7 . . . 119.3 ?
C8 C7 H7 . . . 119.3 ?
C8 C9 H9 . . . 119.5 ?
C10 C9 H9 . . . 119.5 ?
C9 C10 H10 . . . 120.4 ?
C11 C10 H10 . . . 120.4 ?
C1 C13 H13 . . . 116.9 ?
C12 C13 H13 . . . 116.9 ?
C14 C15 H15 . . . 119.6 ?
C16 C15 H15 . . . 119.6 ?
C15 C16 H16 . . . 120.5 ?
C17 C16 H16 . . . 120.5 ?
C17 C18 H18 . . . 120.6 ?
C19 C18 H18 . . . 120.6 ?
C14 C19 H19 . . . 119.3 ?
C18 C19 H19 . . . 119.3 ?
C20 C21 H21 . . . 119.3 ?
C22 C21 H21 . . . 119.3 ?
C21 C22 H22 . . . 120.4 ?
C23 C22 H22 . . . 120.4 ?
C23 C24 H24 . . . 120.4 ?
C25 C24 H24 . . . 120.4 ?
C20 C25 H25 . . . 118.9 ?
C24 C25 H25 . . . 118.9 ?
C1 C26 H261 . . . 109.5 ?
C1 C26 H262 . . . 109.5 ?
C1 C26 H263 . . . 109.5 ?
H261 C26 H262 . . . 109.5 ?
H261 C26 H263 . . . 109.5 ?
H262 C26 H263 . . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C17 . . 1.743(2) ?
Cl2 C23 . . 1.740(3) ?
O1 C11 . . 1.385(2) ?
O1 C12 . . 1.381(2) ?
C1 C2 . . 1.536(2) ?
C1 C13 . . 1.517(3) ?
C1 C20 . . 1.547(3) ?
C1 C26 . . 1.542(3) ?
C2 C3 . . 1.446(3) ?
C2 C11 . . 1.367(2) ?
C3 C4 . . 1.415(3) ?
C3 C8 . . 1.424(2) ?
C4 C5 . . 1.373(3) ?
C5 C6 . . 1.397(3) ?
C6 C7 . . 1.356(4) ?
C7 C8 . . 1.416(3) ?
C8 C9 . . 1.407(3) ?
C9 C10 . . 1.353(3) ?
C10 C11 . . 1.411(2) ?
C12 C13 . . 1.308(2) ?
C12 C14 . . 1.484(3) ?
C14 C15 . . 1.381(3) ?
C14 C19 . . 1.383(2) ?
C15 C16 . . 1.391(3) ?
C16 C17 . . 1.368(3) ?
C17 C18 . . 1.372(3) ?
C18 C19 . . 1.378(3) ?
C20 C21 . . 1.389(2) ?
C20 C25 . . 1.389(3) ?
C21 C22 . . 1.386(4) ?
C22 C23 . . 1.375(4) ?
C23 C24 . . 1.375(3) ?
C24 C25 . . 1.371(3) ?
C4 H4 . . 0.930 ?
C5 H5 . . 0.930 ?
C6 H6 . . 0.930 ?
C7 H7 . . 0.930 ?
C9 H9 . . 0.930 ?
C10 H10 . . 0.930 ?
C13 H13 . . 0.930 ?
C15 H15 . . 0.930 ?
C16 H16 . . 0.930 ?
C18 H18 . . 0.930 ?
C19 H19 . . 0.930 ?
C21 H21 . . 0.930 ?
C22 H22 . . 0.930 ?
C24 H24 . . 0.930 ?
C25 H25 . . 0.930 ?
C26 H261 . . 0.960 ?
C26 H262 . . 0.960 ?
C26 H263 . . 0.960 ?
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
C11 O1 C12 C13 . . . . 3.5(3) ?
C11 O1 C12 C14 . . . . -177.32(19) ?
C12 O1 C11 C2 . . . . -6.0(3) ?
C12 O1 C11 C10 . . . . 173.84(19) ?
C2 C1 C13 C12 . . . . -3.8(3) ?
C13 C1 C2 C3 . . . . -179.1(2) ?
C13 C1 C2 C11 . . . . 1.3(2) ?
C2 C1 C20 C21 . . . . -131.0(2) ?
C2 C1 C20 C25 . . . . 50.4(2) ?
C20 C1 C2 C3 . . . . 65.5(2) ?
C20 C1 C2 C11 . . . . -114.1(2) ?
C26 C1 C2 C3 . . . . -61.6(2) ?
C26 C1 C2 C11 . . . . 118.8(2) ?
C13 C1 C20 C21 . . . . 112.3(2) ?
C13 C1 C20 C25 . . . . -66.3(2) ?
C20 C1 C13 C12 . . . . 113.8(2) ?
C26 C1 C13 C12 . . . . -124.4(2) ?
C26 C1 C20 C21 . . . . -5.0(3) ?
C26 C1 C20 C25 . . . . 176.4(2) ?
C1 C2 C3 C4 . . . . -4.6(3) ?
C1 C2 C3 C8 . . . . 176.9(2) ?
C1 C2 C11 O1 . . . . 3.4(3) ?
C1 C2 C11 C10 . . . . -176.4(2) ?
C3 C2 C11 O1 . . . . -176.2(2) ?
C3 C2 C11 C10 . . . . 4.0(3) ?
C11 C2 C3 C4 . . . . 175.1(2) ?
C11 C2 C3 C8 . . . . -3.4(3) ?
C2 C3 C4 C5 . . . . 179.8(2) ?
C2 C3 C8 C7 . . . . -179.5(2) ?
C2 C3 C8 C9 . . . . 0.6(3) ?
C4 C3 C8 C7 . . . . 1.9(3) ?
C4 C3 C8 C9 . . . . -178.0(2) ?
C8 C3 C4 C5 . . . . -1.7(3) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
C4 C5 C6 C7 . . . . 0.7(4) ?
C5 C6 C7 C8 . . . . -0.5(4) ?
C6 C7 C8 C3 . . . . -0.9(3) ?
C6 C7 C8 C9 . . . . 179.0(2) ?
C3 C8 C9 C10 . . . . 2.0(3) ?
C7 C8 C9 C10 . . . . -177.9(2) ?
C8 C9 C10 C11 . . . . -1.7(3) ?
C9 C10 C11 O1 . . . . 178.7(2) ?
C9 C10 C11 C2 . . . . -1.5(3) ?
O1 C12 C13 C1 . . . . 1.6(3) ?
O1 C12 C14 C15 . . . . 133.8(2) ?
O1 C12 C14 C19 . . . . -45.6(2) ?
C13 C12 C14 C15 . . . . -47.0(3) ?
C13 C12 C14 C19 . . . . 133.5(2) ?
C14 C12 C13 C1 . . . . -177.5(2) ?
C12 C14 C15 C16 . . . . -179.0(2) ?
C12 C14 C19 C18 . . . . 179.9(2) ?
C15 C14 C19 C18 . . . . 0.4(3) ?
C19 C14 C15 C16 . . . . 0.4(3) ?
C14 C15 C16 C17 . . . . -0.6(4) ?
C15 C16 C17 Cl1 . . . . -179.6(2) ?
C15 C16 C17 C18 . . . . 0.0(3) ?
Cl1 C17 C18 C19 . . . . -179.58(19) ?
C16 C17 C18 C19 . . . . 0.8(3) ?
C17 C18 C19 C14 . . . . -1.0(3) ?
C1 C20 C21 C22 . . . . -179.8(2) ?
C1 C20 C25 C24 . . . . -179.5(2) ?
C21 C20 C25 C24 . . . . 1.8(3) ?
C25 C20 C21 C22 . . . . -1.2(3) ?
C20 C21 C22 C23 . . . . -0.6(3) ?
C21 C22 C23 Cl2 . . . . -177.82(19) ?
C21 C22 C23 C24 . . . . 1.9(3) ?
Cl2 C23 C24 C25 . . . . 178.40(19) ?
C22 C23 C24 C25 . . . . -1.3(3) ?
C23 C24 C25 C20 . . . . -0.6(3) ?
