#------------------------------------------------------------------------------
#$Date: 2017-07-25 03:02:39 +0300 (Tue, 25 Jul 2017) $
#$Revision: 198965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/62/4126298.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_4126298
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 H18 F14 O4'
_chemical_formula_weight         828.54
_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                77.396(3)
_cell_angle_beta                 85.184(3)
_cell_angle_gamma                79.972(3)
_cell_formula_units_Z            1
_cell_length_a                   4.3521(7)
_cell_length_b                   11.0812(17)
_cell_length_c                   17.984(3)
_cell_measurement_reflns_used    6260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.32
_cell_volume                     832.5(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10936
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.610
_diffrn_reflns_theta_min         1.162
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_description       Prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          2.000
_exptl_crystal_size_mid          1.000
_exptl_crystal_size_min          1.000
_exptl_transmission_factor_max   0.8670
_exptl_transmission_factor_min   0.7580
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0567P)²+0.5018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2562
_reflns_number_total             3132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b00878_si_002.cif
_cod_data_source_block           CF3-F3_Blue
_cod_database_code               4126298
_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   0.742
_shelx_estimated_absorpt_t_max   0.857
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4922(3) 0.75399(11) 0.55877(7) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.6799(3) 0.76482(11) 0.43748(7) 0.0201(3) Uani 1 1 d . . . . .
F1A F 0.1387(17) 0.8203(6) 1.0542(3) 0.081(2) Uani 0.502(5) 1 d D . P A 1
F1B F -0.0457(7) 0.6701(3) 1.02705(15) 0.0582(12) Uani 0.502(5) 1 d D . P A 1
F1C F 0.4322(12) 0.6438(6) 1.0512(3) 0.0683(15) Uani 0.502(5) 1 d D . P A 1
C1AB C 0.2062(18) 0.7273(12) 1.0160(5) 0.0487(19) Uani 0.498(5) 1 d . . P A 1
C1AA C 0.2048(16) 0.7916(9) 1.0220(5) 0.0386(16) Uani 0.502(5) 1 d . . P A 2
F2A F 0.3522(10) 0.8477(3) 1.06360(15) 0.0521(11) Uani 0.498(5) 1 d D . P A 2
F2B F -0.0971(9) 0.8310(4) 1.03238(18) 0.0689(13) Uani 0.498(5) 1 d D . P A 2
F2C F 0.2574(17) 0.6719(5) 1.0550(3) 0.0630(16) Uani 0.498(5) 1 d D . P A 2
C1 C 0.3015(6) 0.7951(4) 0.93688(14) 0.0632(9) Uani 1 1 d . U . . .
C2 C 0.2576(7) 0.7197(4) 0.88877(16) 0.0697(10) Uani 1 1 d . U . . .
H2 H 0.1609 0.6478 0.9079 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3533(6) 0.7478(3) 0.81275(13) 0.0462(6) Uani 1 1 d . U . . .
H3 H 0.3208 0.6956 0.7796 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4959(5) 0.85135(19) 0.78472(11) 0.0284(4) Uani 1 1 d . . . . .
C5 C 0.5340(7) 0.9275(2) 0.83379(13) 0.0497(7) Uani 1 1 d . U . . .
H5 H 0.6292 0.9999 0.8152 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4352(8) 0.8991(3) 0.90920(14) 0.0656(9) Uani 1 1 d . U . . .
H6 H 0.4603 0.9525 0.9423 0.079 Uiso 1 1 calc R U . . .
C7 C 0.6111(4) 0.87900(17) 0.70723(10) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.7148(4) 0.90214(16) 0.64286(10) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.8555(4) 0.94720(15) 0.56974(10) 0.0173(4) Uani 1 1 d . . . . .
C10 C 0.8288(4) 0.90282(15) 0.50343(9) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.9725(4) 0.95639(15) 0.43541(10) 0.0175(4) Uani 1 1 d . . . . .
H11 H 0.9527 0.9262 0.3908 0.021 Uiso 1 1 calc R U . . .
C12 C 0.6464(4) 0.80021(15) 0.50523(10) 0.0178(4) Uani 1 1 d . . . . .
C13 C 0.5106(4) 0.66601(16) 0.43175(10) 0.0209(4) Uani 1 1 d . . . . .
H13A H 0.2856 0.6993 0.4260 0.025 Uiso 1 1 calc R U . . .
H13B H 0.5337 0.5986 0.4782 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6470(4) 0.61664(16) 0.36323(10) 0.0201(4) Uani 1 1 d . . . . .
F15 F 0.9623(3) 0.45076(10) 0.43822(6) 0.0293(3) Uani 1 1 d . . . . .
C15 C 0.8714(4) 0.51053(17) 0.36844(10) 0.0217(4) Uani 1 1 d . . . . .
C16 C 1.0085(5) 0.46264(18) 0.30717(12) 0.0318(5) Uani 1 1 d . . . . .
H16 H 1.1593 0.3885 0.3132 0.038 Uiso 1 1 calc R U . . .
F17 F 1.0464(4) 0.48528(13) 0.17508(7) 0.0610(5) Uani 1 1 d . . . . .
C17 C 0.9151(6) 0.5282(2) 0.23678(12) 0.0371(5) Uani 1 1 d . . . . .
C18 C 0.6940(6) 0.6345(2) 0.22558(11) 0.0366(5) Uani 1 1 d . . . . .
H18 H 0.6330 0.6775 0.1760 0.044 Uiso 1 1 calc R U . . .
F19 F 0.3470(3) 0.77901(12) 0.28167(7) 0.0437(4) Uani 1 1 d . . . . .
C19 C 0.5660(5) 0.67543(18) 0.28988(11) 0.0277(4) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 O2 C13 115.61(14) . .
F1C C1AB F1A 107.7(7) . .
F1C C1AB F1B 105.3(9) . .
F1A C1AB F1B 105.4(6) . .
F1C C1AB C1 114.4(6) . .
F1A C1AB C1 102.5(9) . .
F1B C1AB C1 120.6(6) . .
F2C C1AA F2B 106.9(7) . .
F2C C1AA F2A 104.7(7) . .
F2B C1AA F2A 106.5(8) . .
F2C C1AA C1 104.8(8) . .
F2B C1AA C1 112.1(6) . .
F2A C1AA C1 120.9(6) . .
C6 C1 C2 119.8(2) . .
C6 C1 C1AB 134.6(5) . .
C2 C1 C1AB 105.3(5) . .
C6 C1 C1AA 108.2(5) . .
C2 C1 C1AA 131.8(5) . .
C1 C2 C3 120.3(3) . .
C4 C3 C2 120.2(3) . .
C3 C4 C5 118.8(2) . .
C3 C4 C7 121.3(2) . .
C5 C4 C7 119.9(2) . .
C6 C5 C4 120.5(3) . .
C1 C6 C5 120.4(3) . .
C8 C7 C4 178.4(2) . .
C7 C8 C9 170.27(19) . .
C11 C9 C10 118.39(16) 2_776 .
C11 C9 C8 116.59(16) 2_776 .
C10 C9 C8 125.01(16) . .
C11 C10 C9 119.32(16) . .
C11 C10 C12 119.78(16) . .
C9 C10 C12 120.90(15) . .
C10 C11 C9 122.29(16) . 2_776
O1 C12 O2 123.99(16) . .
O1 C12 C10 125.70(16) . .
O2 C12 C10 110.31(14) . .
O2 C13 C14 106.76(14) . .
C19 C14 C15 115.07(17) . .
C19 C14 C13 122.66(17) . .
C15 C14 C13 122.25(16) . .
F15 C15 C16 117.84(17) . .
F15 C15 C14 117.61(16) . .
C16 C15 C14 124.55(18) . .
C17 C16 C15 116.0(2) . .
F17 C17 C16 118.0(2) . .
F17 C17 C18 118.2(2) . .
C16 C17 C18 123.83(19) . .
C19 C18 C17 116.44(18) . .
F19 C19 C18 118.51(18) . .
F19 C19 C14 117.43(17) . .
C18 C19 C14 124.06(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.198(2) .
O2 C12 1.349(2) .
O2 C13 1.448(2) .
F1A C1AB 1.338(10) .
F1B C1AB 1.339(10) .
F1C C1AB 1.325(11) .
C1AB C1 1.518(10) .
C1AA F2C 1.318(10) .
C1AA F2B 1.322(8) .
C1AA F2A 1.335(10) .
C1AA C1 1.547(10) .
C1 C6 1.360(5) .
C1 C2 1.372(5) .
C2 C3 1.380(4) .
C3 C4 1.378(3) .
C4 C5 1.384(3) .
C4 C7 1.427(3) .
C5 C6 1.373(3) .
C7 C8 1.197(3) .
C8 C9 1.428(2) .
C9 C11 1.391(3) 2_776
C9 C10 1.406(2) .
C10 C11 1.387(2) .
C10 C12 1.489(2) .
C11 C9 1.391(3) 2_776
C13 C14 1.493(3) .
C14 C19 1.383(3) .
C14 C15 1.383(3) .
F15 C15 1.341(2) .
C15 C16 1.373(3) .
C16 C17 1.370(3) .
F17 C17 1.346(2) .
C17 C18 1.375(3) .
C18 C19 1.373(3) .
F19 C19 1.348(2) .
