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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/63/4126302.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_4126302
loop_
_publ_author_name
'Sharber, Seth A.'
'Baral, Rom Nath'
'Frausto, Fanny'
'Haas, Terry E.'
'Müller, Peter'
'Thomas Iii, Samuel W.'
_publ_section_title
;
 Substituent Effects That Control Conjugated Oligomer Conformation through
 Non-covalent Interactions.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b00878
_journal_year                    2017
_chemical_formula_sum            'C40 H24 F6 O6'
_chemical_formula_weight         714.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-15 # Formatted by publCIF

;
_cell_angle_alpha                105.718(2)
_cell_angle_beta                 91.546(2)
_cell_angle_gamma                99.403(2)
_cell_formula_units_Z            1
_cell_length_a                   7.6773(6)
_cell_length_b                   9.1349(7)
_cell_length_c                   12.3066(10)
_cell_measurement_reflns_used    9557
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      3.09
_cell_volume                     817.33(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17374
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.793
_diffrn_reflns_theta_min         3.090
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       Plate
_exptl_crystal_F_000             366
_exptl_crystal_size_max          2.000
_exptl_crystal_size_mid          2.000
_exptl_crystal_size_min          0.400
_exptl_transmission_factor_max   0.9540
_exptl_transmission_factor_min   0.7960
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0640P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3899
_reflns_number_total             4647
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b00878_si_013.cif
_cod_data_source_block           OMe-F3
_cod_database_code               4126302
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.954
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F001 F 0.54475(11) 1.15113(9) 0.57163(6) 0.02914(18) Uani 1 1 d . .
F002 F 0.36656(12) 1.56055(9) 0.83729(8) 0.0364(2) Uani 1 1 d . .
F003 F 0.34639(13) 1.08422(10) 0.91411(7) 0.0368(2) Uani 1 1 d . .
O004 O 0.15037(12) -0.52916(9) 0.10014(7) 0.02132(18) Uani 1 1 d . .
O005 O 0.46486(10) 0.65194(9) 0.60233(7) 0.02087(18) Uani 1 1 d . .
O006 O 0.31513(10) 0.84737(9) 0.65469(7) 0.01982(18) Uani 1 1 d . .
C007 C 0.15413(13) 0.60331(11) 0.55259(9) 0.01346(19) Uani 1 1 d . .
C008 C 0.32800(13) 0.70145(12) 0.60526(9) 0.0149(2) Uani 1 1 d . .
C009 C 0.03482(13) 0.19665(12) 0.37215(9) 0.0153(2) Uani 1 1 d . .
C00A C 0.05724(14) 0.07065(12) 0.31999(9) 0.0162(2) Uani 1 1 d . .
C00B C 0.01130(13) 0.34780(11) 0.43570(9) 0.01345(19) Uani 1 1 d . .
C00C C 0.07600(13) -0.08430(12) 0.26250(9) 0.0155(2) Uani 1 1 d . .
C00D C 0.16255(13) 0.45377(11) 0.48912(9) 0.01417(19) Uani 1 1 d . .
H00D H 0.2747 0.4224 0.4817 0.017 Uiso 1 1 calc R U
C00E C 0.12829(14) -0.12428(12) 0.15154(9) 0.0167(2) Uani 1 1 d . .
H00E H 0.1484 -0.0481 0.1117 0.020 Uiso 1 1 calc R U
C00F C 0.15080(14) -0.27385(12) 0.09959(9) 0.0172(2) Uani 1 1 d . .
H00F H 0.1863 -0.3000 0.0244 0.021 Uiso 1 1 calc R U
C00G C 0.12125(14) -0.38617(12) 0.15764(9) 0.0164(2) Uani 1 1 d . .
C00H C 0.44673(14) 1.10896(12) 0.74093(10) 0.0183(2) Uani 1 1 d . .
C00I C 0.48110(15) 1.20714(13) 0.67276(10) 0.0197(2) Uani 1 1 d . .
C00J C 0.04436(15) -0.19850(12) 0.31878(9) 0.0184(2) Uani 1 1 d . .
H00J H 0.0072 -0.1731 0.3936 0.022 Uiso 1 1 calc R U
C00K C 0.06649(15) -0.34909(12) 0.26699(9) 0.0184(2) Uani 1 1 d . .
H00K H 0.0444 -0.4260 0.3061 0.022 Uiso 1 1 calc R U
C00L C 0.38294(16) 1.17396(13) 0.84392(11) 0.0227(2) Uani 1 1 d . .
C00M C 0.48117(14) 0.94708(12) 0.70666(11) 0.0204(2) Uani 1 1 d . .
H00A H 0.5738 0.9373 0.6520 0.025 Uiso 1 1 calc R U
H00B H 0.5218 0.9179 0.7737 0.025 Uiso 1 1 calc R U
C00N C 0.45639(16) 1.35872(13) 0.70144(10) 0.0225(2) Uani 1 1 d . .
H00N H 0.4813 1.4222 0.6521 0.027 Uiso 1 1 calc R U
C00O C 0.12363(19) -0.64744(13) 0.15679(11) 0.0261(3) Uani 1 1 d . .
H00C H 0.2036 -0.6166 0.2257 0.039 Uiso 1 1 calc R U
H00G H 0.1483 -0.7440 0.1066 0.039 Uiso 1 1 calc R U
H00H H 0.0007 -0.6629 0.1770 0.039 Uiso 1 1 calc R U
C00P C 0.39336(16) 1.41250(13) 0.80589(11) 0.0241(2) Uani 1 1 d . .
C00Q C 0.35502(17) 1.32479(14) 0.87960(11) 0.0265(3) Uani 1 1 d . .
H00Q H 0.3117 1.3654 0.9511 0.032 Uiso 1 1 calc R U
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_1
_geom_angle_site_symmetry_3
C00G O004 C00O 117.49(9) . .
C008 O006 C00M 114.87(8) . .
C00D C007 C00B 119.67(9) . 2_566
C00D C007 C008 115.53(9) . .
C00B C007 C008 124.79(9) 2_566 .
O005 C008 O006 123.90(9) . .
O005 C008 C007 123.09(9) . .
O006 C008 C007 113.01(8) . .
C00A C009 C00B 178.89(11) . .
C009 C00A C00C 176.07(11) . .
C00D C00B C007 118.06(9) . 2_566
C00D C00B C009 117.75(9) . .
C007 C00B C009 124.19(9) 2_566 .
C00J C00C C00E 118.80(9) . .
C00J C00C C00A 119.30(10) . .
C00E C00C C00A 121.88(10) . .
C007 C00D C00B 122.27(9) . .
C007 C00D H00D 118.9 . .
C00B C00D H00D 118.9 . .
C00F C00E C00C 120.53(10) . .
C00F C00E H00E 119.7 . .
C00C C00E H00E 119.7 . .
C00E C00F C00G 119.96(10) . .
C00E C00F H00F 120.0 . .
C00G C00F H00F 120.0 . .
O004 C00G C00K 124.20(10) . .
O004 C00G C00F 115.55(9) . .
C00K C00G C00F 120.24(9) . .
C00L C00H C00I 114.86(10) . .
C00L C00H C00M 122.94(11) . .
C00I C00H C00M 122.18(10) . .
F001 C00I C00N 117.61(11) . .
F001 C00I C00H 117.77(10) . .
C00N C00I C00H 124.62(11) . .
C00K C00J C00C 120.94(10) . .
C00K C00J H00J 119.5 . .
C00C C00J H00J 119.5 . .
C00G C00K C00J 119.51(10) . .
C00G C00K H00K 120.2 . .
C00J C00K H00K 120.2 . .
F003 C00L C00Q 117.90(11) . .
F003 C00L C00H 117.78(10) . .
C00Q C00L C00H 124.33(11) . .
O006 C00M C00H 107.12(8) . .
O006 C00M H00A 110.3 . .
C00H C00M H00A 110.3 . .
O006 C00M H00B 110.3 . .
C00H C00M H00B 110.3 . .
H00A C00M H00B 108.5 . .
C00P C00N C00I 115.99(11) . .
C00P C00N H00N 122.0 . .
C00I C00N H00N 122.0 . .
O004 C00O H00C 109.5 . .
O004 C00O H00G 109.5 . .
H00C C00O H00G 109.5 . .
O004 C00O H00H 109.5 . .
H00C C00O H00H 109.5 . .
H00G C00O H00H 109.5 . .
F002 C00P C00Q 118.09(11) . .
F002 C00P C00N 117.95(11) . .
C00Q C00P C00N 123.95(11) . .
C00P C00Q C00L 116.25(11) . .
C00P C00Q H00Q 121.9 . .
C00L C00Q H00Q 121.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F001 C00I 1.3486(13) .
F002 C00P 1.3538(13) .
F003 C00L 1.3485(14) .
O004 C00G 1.3638(12) .
O004 C00O 1.4280(14) .
O005 C008 1.2077(13) .
O006 C008 1.3280(12) .
O006 C00M 1.4576(13) .
C007 C00D 1.3906(13) .
C007 C00B 1.4120(13) 2_566
C007 C008 1.5010(14) .
C009 C00A 1.1987(15) .
C009 C00B 1.4334(14) .
C00A C00C 1.4332(14) .
C00B C00D 1.4016(14) .
C00B C007 1.4119(13) 2_566
C00C C00J 1.3946(15) .
C00C C00E 1.4024(15) .
C00D H00D 0.9500 .
C00E C00F 1.3839(14) .
C00E H00E 0.9500 .
C00F C00G 1.3945(15) .
C00F H00F 0.9500 .
C00G C00K 1.3902(15) .
C00H C00L 1.3855(16) .
C00H C00I 1.3857(16) .
C00H C00M 1.4935(15) .
C00I C00N 1.3793(15) .
C00J C00K 1.3909(14) .
C00J H00J 0.9500 .
C00K H00K 0.9500 .
C00L C00Q 1.3824(16) .
C00M H00A 0.9900 .
C00M H00B 0.9900 .
C00N C00P 1.3772(18) .
C00N H00N 0.9500 .
C00O H00C 0.9800 .
C00O H00G 0.9800 .
C00O H00H 0.9800 .
C00P C00Q 1.3721(19) .
C00Q H00Q 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125507
