#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:15:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179621 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508514.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_4508514
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            'C25 H27 F O3'
_chemical_formula_weight         394.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.929(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1337(9)
_cell_length_b                   11.8820(7)
_cell_length_c                   18.8355(16)
_cell_measurement_temperature    296(2)
_cell_volume                     2191.4(3)
_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  0.0617
_diffrn_reflns_av_sigmaI/netI    0.1351
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8340
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1862
_refine_ls_R_factor_gt           0.0731
_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)+(0.0001P)²+0.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                2664
_reflns_number_total             3966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401220x_si_009.cif
_cod_data_source_block           2e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P21/n
_cod_database_code               4508514
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C10 C 0.6712(4) 0.2170(3) 0.0374(2) 0.0402(10) Uani 1 1 d .
C11 C 0.7934(5) 0.2403(4) 0.0867(3) 0.0669(15) Uani 1 1 d .
C15 C 0.6806(5) 0.1460(3) -0.0191(2) 0.0576(13) Uani 1 1 d .
H15 H 0.6010 0.1248 -0.0535 0.069 Uiso 1 1 calc R
C12 C 0.9184(5) 0.2008(4) 0.0821(3) 0.087(2) Uani 1 1 d .
H12 H 0.9977 0.2195 0.1176 0.104 Uiso 1 1 calc R
C14 C 0.8051(6) 0.1049(4) -0.0262(3) 0.0787(17) Uani 1 1 d .
H14 H 0.8081 0.0581 -0.0653 0.094 Uiso 1 1 calc R
C13 C 0.9227(5) 0.1337(4) 0.0245(4) 0.0824(18) Uani 1 1 d .
H13 H 1.0062 0.1072 0.0195 0.099 Uiso 1 1 calc R
C9 C 0.5380(4) 0.2672(3) 0.0449(2) 0.0404(11) Uani 1 1 d .
H9 H 0.5584 0.3452 0.0608 0.049 Uiso 1 1 calc R
C16 C 0.4315(4) 0.2732(3) -0.0294(2) 0.0387(10) Uani 1 1 d .
C18 C 0.3570(5) 0.3614(3) -0.1495(2) 0.0494(12) Uani 1 1 d .
C21 C 0.3194(4) 0.2031(3) -0.0486(2) 0.0429(11) Uani 1 1 d .
H21 H 0.3065 0.1500 -0.0148 0.052 Uiso 1 1 calc R
C20 C 0.2256(4) 0.2090(3) -0.1165(2) 0.0477(11) Uani 1 1 d .
C19 C 0.2458(4) 0.2890(3) -0.1663(2) 0.0522(12) Uani 1 1 d .
H19 H 0.1833 0.2943 -0.2120 0.063 Uiso 1 1 calc R
C23 C 0.1022(4) 0.1318(3) -0.1363(2) 0.0719(15) Uani 1 1 d .
H23A H 0.0321 0.1607 -0.1154 0.108 Uiso 1 1 calc R
H23B H 0.1280 0.0578 -0.1174 0.108 Uiso 1 1 calc R
H23C H 0.0683 0.1283 -0.1888 0.108 Uiso 1 1 calc R
C22 C 0.3814(5) 0.4445(3) -0.2066(2) 0.0771(16) Uani 1 1 d .
H22A H 0.3157 0.4316 -0.2527 0.116 Uiso 1 1 calc R
H22B H 0.4718 0.4342 -0.2127 0.116 Uiso 1 1 calc R
H22C H 0.3719 0.5200 -0.1905 0.116 Uiso 1 1 calc R
C17 C 0.4502(4) 0.3532(3) -0.0806(2) 0.0456(11) Uani 1 1 d .
C6 C 0.4847(4) 0.2110(3) 0.1042(2) 0.0374(10) Uani 1 1 d .
C2 C 0.3440(4) 0.2206(3) 0.1912(2) 0.0428(11) Uani 1 1 d .
C5 C 0.5213(4) 0.1015(3) 0.1286(2) 0.0405(11) Uani 1 1 d .
H5 H 0.5811 0.0615 0.1080 0.049 Uiso 1 1 calc R
C1 C 0.3960(4) 0.2679(3) 0.1370(2) 0.0433(11) Uani 1 1 d .
C4 C 0.4710(4) 0.0508(3) 0.1823(2) 0.0448(11) Uani 1 1 d .
C3 C 0.3827(4) 0.1107(3) 0.2123(2) 0.0486(12) Uani 1 1 d .
H3 H 0.3476 0.0766 0.2480 0.058 Uiso 1 1 calc R
C7 C 0.2537(4) 0.2875(3) 0.2280(2) 0.0655(14) Uani 1 1 d .
H7A H 0.3028 0.3521 0.2518 0.098 Uiso 1 1 calc R
H7B H 0.2272 0.2413 0.2638 0.098 Uiso 1 1 calc R
H7C H 0.1737 0.3118 0.1918 0.098 Uiso 1 1 calc R
C8 C 0.5149(4) -0.0681(3) 0.2086(2) 0.0632(14) Uani 1 1 d .
H8A H 0.5458 -0.0687 0.2613 0.095 Uiso 1 1 calc R
H8B H 0.5878 -0.0920 0.1882 0.095 Uiso 1 1 calc R
H8C H 0.4388 -0.1184 0.1931 0.095 Uiso 1 1 calc R
O1 O 0.3651(3) 0.3792(2) 0.11399(18) 0.0552(9) Uani 1 1 d D
O2 O 0.5648(3) 0.4186(3) -0.05955(18) 0.0603(9) Uani 1 1 d D
F1 F 0.7881(3) 0.3086(2) 0.14446(18) 0.1184(13) Uani 1 1 d .
O3 O 0.3961(3) -0.0553(3) 0.4478(2) 0.0788(11) Uani 1 1 d .
C25 C 0.4700(7) 0.0344(5) 0.4293(3) 0.131(3) Uani 1 1 d .
H25A H 0.4212 0.1040 0.4314 0.157 Uiso 1 1 calc R
H25B H 0.4770 0.0246 0.3793 0.157 Uiso 1 1 calc R
C24 C 0.3931(6) -0.0428(5) 0.5216(4) 0.132(3) Uani 1 1 d .
H24A H 0.3464 -0.1068 0.5360 0.158 Uiso 1 1 calc R
H24B H 0.3418 0.0244 0.5265 0.158 Uiso 1 1 calc R
H1 H 0.283(2) 0.387(3) 0.108(2) 0.047(14) Uiso 1 1 d D
H2 H 0.558(5) 0.478(2) -0.082(2) 0.10(2) Uiso 1 1 d 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
_geom_angle_site_symmetry_3
C11 C10 C15 114.5(4) .
C11 C10 C9 121.9(4) .
C15 C10 C9 123.5(4) .
F1 C11 C10 116.4(5) .
F1 C11 C12 118.5(5) .
C10 C11 C12 125.1(5) .
C10 C15 C14 122.2(5) .
C13 C12 C11 118.1(5) .
C13 C14 C15 119.7(5) .
C12 C13 C14 120.3(5) .
C10 C9 C6 113.0(3) .
C10 C9 C16 111.7(3) .
C6 C9 C16 113.1(3) .
C21 C16 C17 118.5(4) .
C21 C16 C9 123.4(3) .
C17 C16 C9 118.1(4) .
C19 C18 C17 119.0(4) .
C19 C18 C22 120.6(4) .
C17 C18 C22 120.4(4) .
C16 C21 C20 122.3(4) .
C21 C20 C19 118.2(4) .
C21 C20 C23 121.5(4) .
C19 C20 C23 120.2(4) .
C18 C19 C20 121.5(4) .
O2 C17 C18 123.4(4) .
O2 C17 C16 116.1(4) .
C18 C17 C16 120.5(4) .
C1 C6 C5 117.0(4) .
C1 C6 C9 120.5(3) .
C5 C6 C9 122.5(4) .
C1 C2 C3 117.3(4) .
C1 C2 C7 121.1(4) .
C3 C2 C7 121.5(4) .
C4 C5 C6 122.0(4) .
C2 C1 C6 122.9(3) .
C2 C1 O1 121.0(4) .
C6 C1 O1 116.1(4) .
C3 C4 C5 118.5(3) .
C3 C4 C8 120.8(4) .
C5 C4 C8 120.6(4) .
C4 C3 C2 122.3(4) .
C25 O3 C24 108.4(4) .
O3 C25 C24 112.2(5) 3_656
O3 C24 C25 112.0(5) 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C10 C11 1.371(6) .
C10 C15 1.380(5) .
C10 C9 1.514(5) .
C11 F1 1.370(5) .
C11 C12 1.374(6) .
C15 C14 1.390(6) .
C12 C13 1.357(6) .
C14 C13 1.365(6) .
C9 C6 1.515(5) .
C9 C16 1.533(5) .
C16 C21 1.379(5) .
C16 C17 1.402(5) .
C18 C19 1.387(5) .
C18 C17 1.397(5) .
C18 C22 1.528(5) .
C21 C20 1.385(5) .
C20 C19 1.387(5) .
C20 C23 1.518(5) .
C17 O2 1.369(5) .
C6 C1 1.390(5) .
C6 C5 1.398(4) .
C2 C1 1.384(5) .
C2 C3 1.391(5) .
C2 C7 1.509(5) .
C5 C4 1.383(5) .
C1 O1 1.401(4) .
C4 C3 1.374(5) .
C4 C8 1.525(4) .
O3 C25 1.397(5) .
O3 C24 1.407(6) .
C25 C24 1.459(7) 3_656
C24 C25 1.459(7) 3_656
