#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:32:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180477 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/46/7214691.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7214691
loop_
_publ_author_name
'Iwase, Noriaki'
'Kobayashi, Yuhei'
'Kinuta, Takafumi'
'Sato, Tomohiro'
'Tajima, Nobuo'
'Kuroda, Reiko'
'Matsubara, Yoshio'
'Imai, Yoshitane'
_publ_section_title
;
 Solid-state visible molecular recognition system of bisphenol A and its
 derivatives by solid co-grinding crystallization with benzoquinone
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              8599
_journal_paper_doi               10.1039/c2ce26148k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C22 H15 Cl F6 O4'
_chemical_formula_weight         492.79
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            4
_cell_length_a                   11.2984(10)
_cell_length_b                   7.2275(6)
_cell_length_c                   24.573(2)
_cell_measurement_reflns_used    2127
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      1.66
_cell_volume                     2006.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       ω-scans
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11472
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.9344
_exptl_absorpt_correction_T_min  0.8863
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+1.5228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2127
_reflns_number_total             2349
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ce26148k.txt
_cod_data_source_block           imai023_4
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7214691
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.03621(14) 0.0539(2) 0.20070(6) 0.0205(3) Uani 1 1 d .
C2 C -0.02978(14) 0.2114(2) 0.18852(7) 0.0230(3) Uani 1 1 d .
H2 H -0.0926 0.2467 0.2120 0.028 Uiso 1 1 calc R
C3 C -0.00585(15) 0.3178(2) 0.14293(7) 0.0247(3) Uani 1 1 d .
H3 H -0.0523 0.4242 0.1353 0.030 Uiso 1 1 calc R
C4 C 0.08590(15) 0.2687(2) 0.10856(6) 0.0227(3) Uani 1 1 d .
C5 C 0.15288(15) 0.1128(2) 0.11995(7) 0.0254(3) Uani 1 1 d .
H5 H 0.2162 0.0789 0.0965 0.030 Uiso 1 1 calc R
C6 C 0.12778(15) 0.0062(2) 0.16538(7) 0.0244(3) Uani 1 1 d .
H6 H 0.1737 -0.1011 0.1726 0.029 Uiso 1 1 calc R
C7 C 0.0000 -0.0647(3) 0.2500 0.0210(4) Uani 1 2 d S
C8 C -0.10210(16) -0.1909(2) 0.23062(7) 0.0284(4) Uani 1 1 d .
F9 F -0.07849(10) -0.27025(15) 0.18271(4) 0.0377(3) Uani 1 1 d .
F10 F -0.12655(11) -0.32895(15) 0.26523(5) 0.0400(3) Uani 1 1 d .
F11 F -0.20163(9) -0.09348(16) 0.22387(4) 0.0346(3) Uani 1 1 d .
O21 O -0.01208(13) -0.29814(17) 0.06257(5) 0.0335(3) Uani 1 1 d .
C21 C -0.00483(16) -0.1585(2) 0.03485(7) 0.0262(4) Uani 1 1 d .
C22 C -0.10136(15) -0.0180(2) 0.03499(7) 0.0264(4) Uani 1 1 d .
C23 C -0.09684(16) 0.1255(2) 0.00083(7) 0.0285(4) Uani 1 1 d .
H23 H -0.1617 0.2090 -0.0004 0.034 Uiso 1 1 calc R
O4 O 0.11302(12) 0.36664(18) 0.06239(5) 0.0295(3) Uani 1 1 d .
H4 H 0.0738 0.4654 0.0619 0.044 Uiso 1 1 calc R
Cl22 Cl -0.21408(12) -0.0540(2) 0.07591(6) 0.0349(4) Uiso 0.50 1 d P
C22M C -0.1969(4) -0.0499(6) 0.08368(19) 0.0166(12) Uiso 0.50 1 d P
H22A H -0.1654 0.0010 0.1177 0.025 Uiso 0.50 1 calc PR
H22B H -0.2115 -0.1827 0.0882 0.025 Uiso 0.50 1 calc PR
H22C H -0.2712 0.0127 0.0745 0.025 Uiso 0.50 1 calc PR
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 117.75(14) . .
C2 C1 C7 118.80(14) . .
C6 C1 C7 123.34(14) . .
C3 C2 C1 121.51(15) . .
C4 C3 C2 119.83(15) . .
O4 C4 C3 122.66(15) . .
O4 C4 C5 117.69(15) . .
C3 C4 C5 119.64(15) . .
C4 C5 C6 120.19(15) . .
C5 C6 C1 121.07(15) . .
C1 C7 C1 112.34(18) 4 .
C1 C7 C8 111.88(9) 4 .
C1 C7 C8 106.52(9) . .
C1 C7 C8 106.52(9) 4 4
C1 C7 C8 111.88(9) . 4
C8 C7 C8 107.66(19) . 4
F9 C8 F11 106.52(14) . .
F9 C8 F10 106.30(14) . .
F11 C8 F10 107.31(14) . .
F9 C8 C7 112.07(13) . .
F11 C8 C7 110.80(14) . .
F10 C8 C7 113.45(14) . .
O21 C21 C23 121.42(16) . 5
O21 C21 C22 120.86(17) . .
C23 C21 C22 117.69(15) 5 .
C23 C22 C21 119.98(16) . .
C23 C22 C22M 126.7(2) . .
C21 C22 C22M 113.0(2) . .
C23 C22 Cl22 122.49(15) . .
C21 C22 Cl22 117.45(14) . .
C22M C22 Cl22 9.60(18) . .
C22 C23 C21 122.19(16) . 5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.393(2) .
C1 C6 1.394(2) .
C1 C7 1.5392(19) .
C2 C3 1.385(2) .
C3 C4 1.383(2) .
C4 O4 1.3720(19) .
C4 C5 1.386(2) .
C5 C6 1.386(2) .
C7 C1 1.5392(19) 4
C7 C8 1.546(2) .
C7 C8 1.546(2) 4
C8 F9 1.3366(19) .
C8 F11 1.337(2) .
C8 F10 1.340(2) .
O21 C21 1.221(2) .
C21 C23 1.465(2) 5
C21 C22 1.490(2) .
C22 C23 1.335(2) .
C22 C22M 1.628(4) .
C22 Cl22 1.643(2) .
C23 C21 1.465(2) 5
