#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:15:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179621 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508513.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_4508513
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           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.763(4)
_cell_angle_beta                 103.988(4)
_cell_angle_gamma                96.474(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0463(5)
_cell_length_b                   9.5339(6)
_cell_length_c                   13.1106(8)
_cell_measurement_temperature    296(2)
_cell_volume                     1071.13(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.990
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15773
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3850
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0448
_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)+(0.0010P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                2642
_reflns_number_total             3850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401220x_si_008.cif
_cod_data_source_block           2d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4508513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.9867(2) 0.6516(2) 0.80870(14) 0.0424(5) Uani 1 1 d .
C2 C 0.8684(2) 0.5353(2) 0.78379(15) 0.0467(5) Uani 1 1 d .
C6 C 1.0218(2) 0.7381(2) 0.90942(14) 0.0509(5) Uani 1 1 d .
H6 H 1.1002 0.8165 0.9266 0.061 Uiso 1 1 calc R
C3 C 0.7907(2) 0.5019(2) 0.85874(16) 0.0535(5) Uani 1 1 d .
C4 C 0.8315(3) 0.5926(3) 0.95844(16) 0.0593(6) Uani 1 1 d .
H4 H 0.7805 0.5718 1.0093 0.071 Uiso 1 1 calc R
C5 C 0.9440(3) 0.7117(3) 0.98483(15) 0.0572(6) Uani 1 1 d .
C8 C 0.9807(3) 0.8101(3) 1.09255(17) 0.0883(9) Uani 1 1 d .
H8A H 0.8908 0.8507 1.1006 0.133 Uiso 1 1 calc R
H8B H 1.0629 0.8859 1.0973 0.133 Uiso 1 1 calc R
H8C H 1.0116 0.7563 1.1482 0.133 Uiso 1 1 calc R
C7 C 0.6664(3) 0.3727(3) 0.8349(2) 0.0790(7) Uani 1 1 d .
H7A H 0.5690 0.3977 0.8007 0.118 Uiso 1 1 calc R
H7B H 0.6603 0.3422 0.9004 0.118 Uiso 1 1 calc R
H7C H 0.6907 0.2960 0.7883 0.118 Uiso 1 1 calc R
C9 C 1.0687(2) 0.6854(2) 0.72423(14) 0.0424(5) Uani 1 1 d .
H9 H 1.0800 0.5930 0.6848 0.051 Uiso 1 1 calc R
C10 C 1.2309(2) 0.7679(2) 0.77418(14) 0.0473(5) Uani 1 1 d .
C11 C 1.3476(3) 0.7018(3) 0.82569(18) 0.0645(6) Uani 1 1 d .
C15 C 1.2711(3) 0.9113(3) 0.77375(18) 0.0656(6) Uani 1 1 d .
H15 H 1.1966 0.9609 0.7400 0.079 Uiso 1 1 calc R
C12 C 1.4956(3) 0.7701(4) 0.8738(2) 0.0892(9) Uani 1 1 d .
H12 H 1.5704 0.7205 0.9072 0.107 Uiso 1 1 calc R
C14 C 1.4190(3) 0.9843(3) 0.8220(2) 0.0901(9) Uani 1 1 d .
H14 H 1.4425 1.0815 0.8208 0.108 Uiso 1 1 calc R
C13 C 1.5304(3) 0.9128(4) 0.8715(2) 0.0982(10) Uani 1 1 d .
H13 H 1.6299 0.9613 0.9037 0.118 Uiso 1 1 calc R
C16 C 0.9721(2) 0.75997(19) 0.64291(13) 0.0396(4) Uani 1 1 d .
C18 C 0.8931(2) 0.7996(2) 0.46027(14) 0.0458(5) Uani 1 1 d .
C17 C 0.9844(2) 0.7386(2) 0.53786(14) 0.0421(5) Uani 1 1 d .
C19 C 0.7955(2) 0.8898(2) 0.49180(15) 0.0508(5) Uani 1 1 d .
H19 H 0.7352 0.9324 0.4409 0.061 Uiso 1 1 calc R
C21 C 0.8721(2) 0.8501(2) 0.66990(14) 0.0471(5) Uani 1 1 d .
H21 H 0.8633 0.8653 0.7398 0.057 Uiso 1 1 calc R
C20 C 0.7845(2) 0.9185(2) 0.59588(15) 0.0502(5) Uani 1 1 d .
C22 C 0.8992(3) 0.7685(2) 0.34512(15) 0.0671(7) Uani 1 1 d .
H22A H 0.8189 0.8082 0.3018 0.101 Uiso 1 1 calc R
H22B H 0.8849 0.6665 0.3208 0.101 Uiso 1 1 calc R
H22C H 0.9976 0.8110 0.3395 0.101 Uiso 1 1 calc R
C23 C 0.6785(3) 1.0184(3) 0.62807(18) 0.0755(7) Uani 1 1 d .
H23A H 0.6790 1.0967 0.5899 0.113 Uiso 1 1 calc R
H23B H 0.7136 1.0554 0.7036 0.113 Uiso 1 1 calc R
H23C H 0.5756 0.9668 0.6112 0.113 Uiso 1 1 calc R
O2 O 1.09140(17) 0.65516(17) 0.51584(11) 0.0581(4) Uani 1 1 d D
F1 F 1.31281(17) 0.55938(17) 0.82847(12) 0.0934(5) Uani 1 1 d .
O1 O 0.83455(19) 0.45071(17) 0.68268(12) 0.0597(4) Uani 1 1 d D
O3 O 0.46590(19) 0.60746(19) 0.43841(14) 0.0784(5) Uani 1 1 d .
C24 C 0.4662(3) 0.6276(3) 0.5487(2) 0.0810(8) Uani 1 1 d .
H24A H 0.3918 0.6894 0.5613 0.097 Uiso 1 1 calc R
H24B H 0.5674 0.6741 0.5925 0.097 Uiso 1 1 calc R
C25 C 0.5734(3) 0.5133(3) 0.4207(2) 0.0850(8) Uani 1 1 d .
H25A H 0.6765 0.5576 0.4624 0.102 Uiso 1 1 calc R
H25B H 0.5729 0.4980 0.3457 0.102 Uiso 1 1 calc R
H1 H 0.739(2) 0.429(3) 0.653(2) 0.095(10) Uiso 1 1 d D
H2 H 1.078(3) 0.633(3) 0.4484(13) 0.087(8) 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
C6 C1 C2 118.27(18) .
C6 C1 C9 121.81(19) .
C2 C1 C9 119.85(16) .
O1 C2 C1 117.39(17) .
O1 C2 C3 121.2(2) .
C1 C2 C3 121.33(18) .
C5 C6 C1 122.2(2) .
C2 C3 C4 117.6(2) .
C2 C3 C7 122.2(2) .
C4 C3 C7 120.2(2) .
C5 C4 C3 122.80(19) .
C4 C5 C6 117.69(19) .
C4 C5 C8 121.1(2) .
C6 C5 C8 121.3(2) .
C10 C9 C16 112.46(16) .
C10 C9 C1 112.07(15) .
C16 C9 C1 111.74(15) .
C15 C10 C11 115.5(2) .
C15 C10 C9 123.47(18) .
C11 C10 C9 121.0(2) .
F1 C11 C12 118.4(2) .
F1 C11 C10 117.6(2) .
C12 C11 C10 124.1(3) .
C10 C15 C14 122.1(2) .
C13 C12 C11 118.4(3) .
C13 C14 C15 119.7(3) .
C12 C13 C14 120.1(3) .
C21 C16 C17 118.23(16) .
C21 C16 C9 122.15(15) .
C17 C16 C9 119.62(16) .
C19 C18 C17 118.03(17) .
C19 C18 C22 120.83(18) .
C17 C18 C22 121.14(18) .
O2 C17 C18 122.31(16) .
O2 C17 C16 116.42(16) .
C18 C17 C16 121.27(17) .
C20 C19 C18 122.49(18) .
C16 C21 C20 122.15(17) .
C19 C20 C21 117.69(18) .
C19 C20 C23 121.28(18) .
C21 C20 C23 121.01(18) .
C24 O3 C25 108.90(19) .
O3 C24 C25 110.3(2) 2_666
O3 C25 C24 111.1(2) 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.390(2) .
C1 C2 1.391(3) .
C1 C9 1.527(2) .
C2 O1 1.387(2) .
C2 C3 1.393(3) .
C6 C5 1.382(3) .
C3 C4 1.394(3) .
C3 C7 1.510(3) .
C4 C5 1.376(3) .
C5 C8 1.511(3) .
C9 C10 1.523(3) .
C9 C16 1.525(2) .
C10 C15 1.376(3) .
C10 C11 1.379(3) .
C11 F1 1.367(3) .
C11 C12 1.372(3) .
C15 C14 1.386(3) .
C12 C13 1.368(4) .
C14 C13 1.370(4) .
C16 C21 1.385(2) .
C16 C17 1.394(2) .
C18 C19 1.389(3) .
C18 C17 1.392(2) .
C18 C22 1.509(2) .
C17 O2 1.376(2) .
C19 C20 1.380(3) .
C21 C20 1.390(3) .
C20 C23 1.511(3) .
O3 C24 1.428(3) .
O3 C25 1.432(3) .
C24 C25 1.490(4) 2_666
C25 C24 1.490(4) 2_666
