#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503106.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_1503106
loop_
_publ_author_name
'Colquhoun, Howard M.'
'Zhu, Zhixue'
'Cardin, Christine J.'
'White, Andrew J. P.'
'Drew, Michael G. B.'
'Gan, Yu'
_publ_section_title
;
 Bis(hydroxy-isoindolinone)s: synthesis, stereochemistry, polymer
 chemistry, and supramolecular assembly.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3756
_journal_page_last               3759
_journal_paper_doi               10.1021/ol101338m
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C58 H34 F2 O4'
_chemical_formula_weight         830.84
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_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_date             2010-06-07T16:07:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                108.753(3)
_cell_angle_beta                 100.834(3)
_cell_angle_gamma                98.211(3)
_cell_formula_units_Z            1
_cell_length_a                   9.1240(3)
_cell_length_b                   12.5563(5)
_cell_length_c                   15.4232(5)
_cell_measurement_temperature    150(2)
_cell_volume                     1603.59(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11766
_diffrn_reflns_theta_full        61.27
_diffrn_reflns_theta_max         61.27
_diffrn_reflns_theta_min         3.12
_exptl_crystal_density_diffrn    0.86
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             430
_platon_squeeze_details
;
;
_refine_diff_density_max         0.78
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.1104
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1796P)²+2.7301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3098
_refine_ls_wR_factor_ref         0.3192
_reflns_number_gt                3839
_reflns_number_total             4822
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol101338m_si_001.cif
_cod_data_source_block           583_2
_cod_original_cell_volume        1603.59(10)
_cod_database_code               1503106
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 0.8903(7) 0.8259(4) 0.9392(3) 0.0454(13) Uani 1 1 d .
H1 H 0.8635 0.8967 0.9489 0.054 Uiso 1 1 calc R
C010 C 0.7343(4) 0.1340(3) 0.7211(2) 0.0125(7) Uani 1 1 d .
C011 C 0.6240(4) -0.0269(3) 0.4615(3) 0.0195(8) Uani 1 1 d .
H011 H 0.706 -0.0457 0.4365 0.023 Uiso 1 1 calc R
C013 C 0.8569(5) -0.0255(3) 0.6508(3) 0.0256(9) Uani 1 1 d .
C015 C 0.6453(4) 0.0309(3) 0.5592(3) 0.0176(8) Uani 1 1 d .
C016 C 0.5159(4) 0.0540(3) 0.5938(2) 0.0167(8) Uani 1 1 d .
C017 C 0.8007(4) -0.0879(3) 0.7000(3) 0.0248(9) Uani 1 1 d .
H017 H 0.722 -0.0682 0.7283 0.03 Uiso 1 1 calc R
C018 C 1.0132(5) 0.5053(3) 0.8886(3) 0.0259(9) Uani 1 1 d .
C019 C 0.8639(6) -0.1847(4) 0.7080(3) 0.0395(11) Uani 1 1 d .
H019 H 0.8327 -0.2248 0.7451 0.047 Uiso 1 1 calc R
C020 C 0.7918(5) 0.0740(3) 0.6379(3) 0.0265(9) Uani 1 1 d .
C021 C 0.8291(4) 0.1804(3) 0.8131(2) 0.0189(8) Uani 1 1 d .
H02A H 0.8862 0.1236 0.8219 0.023 Uiso 1 1 calc R
H02B H 0.7635 0.1897 0.8566 0.023 Uiso 1 1 calc R
C022 C 0.5732(4) 0.1187(3) 0.6979(3) 0.0200(8) Uani 1 1 d .
C023 C 0.9746(4) -0.0561(3) 0.6088(3) 0.0243(9) Uani 1 1 d .
H023 H 1.0169 -0.0091 0.5799 0.029 Uiso 1 1 calc R
C024 C 0.8938(5) 0.4011(4) 0.8559(3) 0.0343(10) Uani 1 1 d .
C026 C 1.0860(5) 0.7191(4) 0.9389(3) 0.0332(10) Uani 1 1 d .
C027 C 0.7380(5) 0.4055(4) 0.8367(3) 0.0301(10) Uani 1 1 d .
H027 H 0.6635 0.3374 0.8106 0.036 Uiso 1 1 calc R
C028 C 0.9705(4) -0.2152(3) 0.6595(3) 0.0257(9) Uani 1 1 d .
C029 C 1.1013(5) 0.2932(3) 0.8579(3) 0.0282(9) Uani 1 1 d .
H029 H 1.1322 0.2234 0.8444 0.034 Uiso 1 1 calc R
C030 C 0.9410(4) 0.2923(3) 0.8427(2) 0.0193(8) Uani 1 1 d .
C031 C 0.6955(5) 0.5095(4) 0.8562(3) 0.0297(9) Uani 1 1 d .
H031 H 0.5926 0.512 0.8485 0.036 Uiso 1 1 calc R
C032 C 1.2073(5) 0.3909(4) 0.8910(3) 0.0330(10) Uani 1 1 d .
H032 H 1.31 0.3878 0.9043 0.04 Uiso 1 1 calc R
C033 C 1.0331(5) -0.1539(4) 0.6078(3) 0.0285(9) Uani 1 1 d .
H033 H 1.1068 -0.1765 0.5758 0.034 Uiso 1 1 calc R
C034 C 1.1678(6) 0.5000(4) 0.9064(3) 0.0384(11) Uani 1 1 d .
C035 C 0.9720(7) 0.6101(5) 0.9042(3) 0.0486(13) Uani 1 1 d .
C038 C 1.2776(7) 0.6050(5) 0.9397(4) 0.0485(13) Uani 1 1 d .
H038 H 1.3811 0.6042 0.9494 0.058 Uiso 1 1 calc R
C039 C 0.8119(6) 0.6164(4) 0.8891(3) 0.0370(11) Uani 1 1 d .
C041 C 1.0393(7) 0.8236(4) 0.9593(3) 0.0483(13) Uani 1 1 d .
H041 H 1.1122 0.8925 0.9871 0.058 Uiso 1 1 calc R
C042 C 1.2368(6) 0.6981(4) 0.9560(3) 0.0426(12) Uani 1 1 d .
H042 H 1.3156 0.7636 0.9832 0.051 Uiso 1 1 calc R
C043 C 0.7730(7) 0.7257(4) 0.9043(3) 0.0454(12) Uani 1 1 d .
H043 H 0.6711 0.7308 0.8911 0.055 Uiso 1 1 calc R
O004 O 0.9025(3) 0.1513(3) 0.6238(2) 0.0270(7) Uani 1 1 d .
O005 O 0.4982(3) 0.1565(2) 0.75152(17) 0.0227(7) Uani 1 1 d .
F1 F 1.0233(3) -0.3097(2) 0.66228(19) 0.0385(7) Uani 1 1 d .
H61 H 0.877(12) 0.198(9) 0.608(7) 0.11(4) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C041 C1 C043 122.9(5) .
C021 C010 C022 125.1(3) .
C021 C010 C020 121.8(3) .
C022 C010 C020 112.1(3) .
C016 C011 C015 118.3(3) 2_656
C017 C013 C023 119.4(4) .
C017 C013 C020 121.8(4) .
C023 C013 C020 118.8(4) .
C011 C015 C016 118.5(3) .
C011 C015 C020 129.5(3) .
C016 C015 C020 112.0(3) .
C011 C016 C015 123.2(3) 2_656
C011 C016 C022 130.0(3) 2_656
C015 C016 C022 106.6(3) .
C013 C017 C019 119.8(4) .
C035 C018 C034 120.3(4) .
C035 C018 C024 118.9(4) .
C034 C018 C024 120.8(4) .
C028 C019 C017 117.7(4) .
O004 C020 C010 110.4(3) .
O004 C020 C013 110.0(3) .
C010 C020 C013 111.1(3) .
O004 C020 C015 113.0(3) .
C010 C020 C015 101.2(3) .
C013 C020 C015 110.9(3) .
C010 C021 C030 119.1(3) .
O005 C022 C010 125.7(3) .
O005 C022 C016 126.5(3) .
C010 C022 C016 107.7(3) .
C013 C023 C033 123.6(4) .
C027 C024 C018 121.1(4) .
C027 C024 C030 121.3(4) .
C018 C024 C030 117.6(4) .
C041 C026 C042 129.5(4) .
C041 C026 C035 120.1(5) .
C042 C026 C035 110.1(4) .
C031 C027 C024 120.4(4) .
F1 C028 C019 117.9(4) .
F1 C028 C033 117.3(3) .
C019 C028 C033 124.8(4) .
C032 C029 C030 122.0(4) .
C029 C030 C024 118.4(3) .
C029 C030 C021 119.2(3) .
C024 C030 C021 122.4(3) .
C027 C031 C039 120.0(4) .
C029 C032 C034 121.8(4) .
C023 C033 C028 114.3(4) .
C018 C034 C038 117.6(5) .
C018 C034 C032 119.2(4) .
C038 C034 C032 123.2(5) .
C018 C035 C039 120.5(5) .
C018 C035 C026 122.1(5) .
C039 C035 C026 117.4(4) .
C042 C038 C034 120.5(6) .
C043 C039 C035 119.2(5) .
C043 C039 C031 122.1(5) .
C035 C039 C031 118.7(4) .
C1 C041 C026 120.8(5) .
C038 C042 C026 129.2(5) .
C1 C043 C039 119.4(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C041 1.343(8) .
C1 C043 1.408(8) .
C010 C021 1.401(5) .
C010 C022 1.415(5) .
C010 C020 1.495(5) .
C011 C016 1.324(5) 2_656
C011 C015 1.407(5) .
C013 C017 1.367(6) .
C013 C023 1.392(6) .
C013 C020 1.509(6) .
C015 C016 1.414(5) .
C015 C020 1.521(5) .
C016 C011 1.324(5) 2_656
C016 C022 1.495(5) .
C017 C019 1.449(6) .
C018 C035 1.380(7) .
C018 C034 1.401(7) .
C018 C024 1.454(6) .
C019 C028 1.360(7) .
C020 O004 1.396(5) .
C021 C030 1.493(5) .
C022 O005 1.197(5) .
C023 C033 1.405(6) .
C024 C027 1.410(7) .
C024 C030 1.455(6) .
C026 C041 1.396(7) .
C026 C042 1.429(8) .
C026 C035 1.468(7) .
C027 C031 1.372(6) .
C028 F1 1.353(5) .
C028 C033 1.411(6) .
C029 C032 1.332(6) .
C029 C030 1.435(6) .
C031 C039 1.463(6) .
C032 C034 1.424(7) .
C034 C038 1.413(7) .
C035 C039 1.454(8) .
C038 C042 1.241(8) .
C039 C043 1.423(7) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.009 0.498 0.498 720.3 -20.6
