#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:15:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179621 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508507.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_4508507
loop_
_publ_author_name
'Nath, Bhaskar'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Polymorphs, Solvates, Polymorphs of Solvate and Cs+--π Interactions of
 Fluorine-Substitutedbis-Phenols
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5146
_journal_paper_doi               10.1021/cg401220x
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C23 H23 F O2'
_chemical_formula_weight         350.41
_chemical_name_systematic
; 
 ? 
;
_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                   4.9312(3)
_cell_length_b                   19.1560(13)
_cell_length_c                   41.744(2)
_cell_measurement_temperature    296(2)
_cell_volume                     3943.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            10770
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0090P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                1870
_reflns_number_total             3636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401220x_si_002.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4508507
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_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
O1 O 0.1875(6) 0.67585(16) 0.73120(6) 0.0545(8) Uani 1 1 d .
F1 F 0.6537(4) 0.43259(13) 0.65223(6) 0.0704(8) Uani 1 1 d .
O2 O 0.1797(7) 0.70554(17) 0.50492(7) 0.0552(8) Uani 1 1 d .
C21 C 0.1794(6) 0.63646(19) 0.58687(8) 0.0380(9) Uani 1 1 d .
H21 H 0.0903 0.6430 0.6063 0.046 Uiso 1 1 calc R
C20 C 0.1050(7) 0.67744(19) 0.56079(8) 0.0390(9) Uani 1 1 d .
C9 C 0.4627(7) 0.54173(19) 0.61380(8) 0.0388(9) Uani 1 1 d .
H9 H 0.6612 0.5391 0.6136 0.047 Uiso 1 1 calc R
C3 C 0.1839(6) 0.5487(2) 0.66551(8) 0.0413(10) Uani 1 1 d .
H3 H 0.0957 0.5079 0.6594 0.050 Uiso 1 1 calc R
C10 C 0.3588(6) 0.4669(2) 0.61113(8) 0.0380(9) Uani 1 1 d .
C4 C 0.3829(7) 0.5760(2) 0.64550(8) 0.0365(9) Uani 1 1 d .
C16 C 0.3804(6) 0.5865(2) 0.58500(8) 0.0388(9) Uani 1 1 d .
C2 C 0.1123(7) 0.5804(2) 0.69423(8) 0.0420(10) Uani 1 1 d .
C18 C 0.4312(7) 0.6138(2) 0.52828(8) 0.0436(10) Uani 1 1 d .
C1 C 0.2391(7) 0.6422(2) 0.70252(8) 0.0428(10) Uani 1 1 d .
C17 C 0.5015(7) 0.57528(19) 0.55528(8) 0.0436(10) Uani 1 1 d .
H17 H 0.6338 0.5409 0.5534 0.052 Uiso 1 1 calc R
C19 C 0.2335(7) 0.6650(2) 0.53182(8) 0.0416(9) Uani 1 1 d .
C5 C 0.5044(7) 0.6383(2) 0.65482(8) 0.0433(10) Uani 1 1 d .
H5 H 0.6369 0.6577 0.6417 0.052 Uiso 1 1 calc R
C23 C -0.1090(7) 0.7333(2) 0.56461(9) 0.0528(11) Uani 1 1 d .
H23A H -0.1666 0.7351 0.5866 0.079 Uiso 1 1 calc R
H23B H -0.2615 0.7225 0.5512 0.079 Uiso 1 1 calc R
H23C H -0.0350 0.7776 0.5585 0.079 Uiso 1 1 calc R
C14 C 0.0609(8) 0.3785(2) 0.58907(11) 0.0610(12) Uani 1 1 d .
H14 H -0.0719 0.3660 0.5743 0.073 Uiso 1 1 calc R
C7 C -0.0974(7) 0.5462(2) 0.71545(9) 0.0565(12) Uani 1 1 d .
H7A H -0.1383 0.5005 0.7074 0.085 Uiso 1 1 calc R
H7B H -0.2594 0.5740 0.7156 0.085 Uiso 1 1 calc R
H7C H -0.0278 0.5425 0.7369 0.085 Uiso 1 1 calc R
C6 C 0.4358(7) 0.6724(2) 0.68274(9) 0.0442(10) Uani 1 1 d .
C15 C 0.1565(7) 0.4465(2) 0.58971(9) 0.0503(11) Uani 1 1 d .
H15 H 0.0845 0.4792 0.5756 0.060 Uiso 1 1 calc R
C8 C 0.5671(8) 0.7403(2) 0.69148(9) 0.0631(12) Uani 1 1 d .
H8A H 0.6748 0.7342 0.7104 0.095 Uiso 1 1 calc R
H8B H 0.4297 0.7748 0.6954 0.095 Uiso 1 1 calc R
H8C H 0.6811 0.7555 0.6742 0.095 Uiso 1 1 calc R
C11 C 0.4557(7) 0.4154(2) 0.63134(9) 0.0492(11) Uani 1 1 d .
C13 C 0.1606(8) 0.3292(2) 0.61004(12) 0.0652(13) Uani 1 1 d .
H13 H 0.0930 0.2839 0.6099 0.078 Uiso 1 1 calc R
C22 C 0.5641(8) 0.6001(2) 0.49648(9) 0.0632(13) Uani 1 1 d .
H22A H 0.6843 0.5609 0.4984 0.095 Uiso 1 1 calc R
H22B H 0.6652 0.6406 0.4900 0.095 Uiso 1 1 calc R
H22C H 0.4275 0.5902 0.4807 0.095 Uiso 1 1 calc R
C12 C 0.3620(8) 0.3481(2) 0.63118(11) 0.0610(12) Uani 1 1 d .
H12 H 0.4339 0.3154 0.6453 0.073 Uiso 1 1 calc R
H1 H 0.020(9) 0.666(2) 0.7378(11) 0.11(2) Uiso 1 1 d .
H2 H 0.049(9) 0.728(2) 0.5055(12) 0.09(2) Uiso 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 C21 C20 122.4(3)
C19 C20 C21 117.7(3)
C19 C20 C23 122.2(3)
C21 C20 C23 120.1(3)
C10 C9 C4 112.3(3)
C10 C9 C16 112.3(3)
C4 C9 C16 111.8(3)
C2 C3 C4 122.3(4)
C11 C10 C15 116.0(4)
C11 C10 C9 120.6(3)
C15 C10 C9 123.3(3)
C3 C4 C5 117.2(3)
C3 C4 C9 122.8(3)
C5 C4 C9 120.0(3)
C21 C16 C17 117.7(3)
C21 C16 C9 122.3(3)
C17 C16 C9 119.9(3)
C1 C2 C3 118.3(3)
C1 C2 C7 122.2(3)
C3 C2 C7 119.5(4)
C17 C18 C19 117.6(3)
C17 C18 C22 121.0(4)
C19 C18 C22 121.4(3)
O1 C1 C2 122.1(3)
O1 C1 C6 116.5(4)
C2 C1 C6 121.3(3)
C18 C17 C16 122.2(4)
C20 C19 O2 121.4(4)
C20 C19 C18 122.3(3)
O2 C19 C18 116.2(3)
C6 C5 C4 122.5(3)
C13 C14 C15 120.7(4)
C5 C6 C1 118.3(4)
C5 C6 C8 120.8(4)
C1 C6 C8 121.0(4)
C14 C15 C10 121.2(4)
F1 C11 C12 118.5(4)
F1 C11 C10 118.0(4)
C12 C11 C10 123.5(4)
C12 C13 C14 118.9(4)
C11 C12 C13 119.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.383(4)
F1 C11 1.350(4)
O2 C19 1.390(4)
C21 C16 1.380(4)
C21 C20 1.391(4)
C20 C19 1.386(5)
C20 C23 1.511(5)
C9 C10 1.527(5)
C9 C4 1.528(4)
C9 C16 1.531(4)
C3 C2 1.389(5)
C3 C4 1.390(4)
C10 C11 1.383(5)
C10 C15 1.395(5)
C4 C5 1.391(5)
C16 C17 1.394(5)
C2 C1 1.384(5)
C2 C7 1.510(5)
C18 C17 1.391(5)
C18 C19 1.391(5)
C18 C22 1.503(5)
C1 C6 1.399(5)
C5 C6 1.378(5)
C14 C13 1.379(5)
C14 C15 1.385(5)
C6 C8 1.498(5)
C11 C12 1.369(5)
C13 C12 1.377(6)
