#------------------------------------------------------------------------------
#$Date: 2019-11-25 16:28:21 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/10/4131000.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_4131000
loop_
_publ_author_name
'Lu, Jingzhi'
'Khetrapal, Navneet S.'
'Johnson, Jacob A.'
'Zeng, Xiao Cheng'
'Zhang, Jian'
_publ_section_title
;
 "π-Hole-π" Interaction Promoted Photocatalytic
 Hydrodefluorination via Inner-Sphere Electron Transfer.
;
_journal_issue                   49
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15805
_journal_page_last               15808
_journal_paper_doi               10.1021/jacs.6b08620
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C52 H42 F12'
_chemical_formula_weight         894.86
_chemical_name_common            Py3:HFB
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                98.279(3)
_cell_angle_beta                 91.547(3)
_cell_angle_gamma                103.011(3)
_cell_formula_units_Z            1
_cell_length_a                   6.6791(6)
_cell_length_b                   11.7780(12)
_cell_length_c                   14.4954(15)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.126
_cell_measurement_theta_min      5.646
_cell_volume                     1097.36(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24749
_diffrn_reflns_theta_full        16.21
_diffrn_reflns_theta_max         16.21
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.068
_exptl_crystal_colour            light_yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.378
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5270
_refine_ls_number_restraints     345
_refine_ls_restrained_S_all      1.334
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0910
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2848
_refine_ls_wR_factor_ref         0.3028
_reflns_number_gt                4535
_reflns_number_total             5270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b08620_si_002.cif
_cod_data_source_block           Py3:HFB
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4131000
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
F28 F 0.8258(2) 0.69897(13) 0.62625(9) 0.0421(4) Uani 1 1 d U
F27 F 0.9282(2) 0.89303(15) 0.54287(9) 0.0509(4) Uani 1 1 d U
F29 F 0.8263(3) 0.71758(15) 0.81420(10) 0.0542(4) Uani 1 1 d U
C7 C 0.4275(2) 0.91794(12) 0.72308(9) 0.0152(3) Uani 1 1 d U
H7 H 0.4085 0.8958 0.7833 0.018 Uiso 1 1 calc R
C8 C 0.4900(2) 1.03760(12) 0.71517(9) 0.0142(3) Uani 1 1 d U
C12 C 0.3924(2) 0.83042(12) 0.64483(9) 0.0146(3) Uani 1 1 d U
C11 C 0.4200(2) 0.86192(12) 0.55419(9) 0.0129(3) Uani 1 1 d U
C21 C 0.5261(2) 1.12301(13) 0.79860(10) 0.0169(3) Uani 1 1 d U
C9 C 0.5188(2) 1.07182(12) 0.62601(9) 0.0130(3) Uani 1 1 d U
C10 C 0.4843(2) 0.98331(12) 0.54530(9) 0.0120(3) Uani 1 1 d U
F32 F 1.0289(2) 1.11098(15) 0.64980(15) 0.0685(6) Uani 1 1 d U
F30 F 0.9216(3) 0.9324(2) 0.92152(10) 0.0699(6) Uani 1 1 d U
C13 C 0.3302(2) 0.70915(13) 0.65743(10) 0.0175(4) Uani 1 1 d U
C14 C 0.2796(2) 0.60731(13) 0.66830(10) 0.0186(4) Uani 1 1 d U
C19 C 0.5845(2) 1.19320(12) 0.61431(10) 0.0166(3) Uani 1 1 d U
H19 H 0.6082 1.2525 0.6678 0.020 Uiso 1 1 calc R
F31 F 1.0261(2) 1.13083(17) 0.83988(16) 0.0792(7) Uani 1 1 d U
C22 C 0.5554(2) 1.18964(13) 0.87187(10) 0.0183(4) Uani 1 1 d U
C20 C 0.6135(2) 1.22529(12) 0.52837(10) 0.0159(3) Uani 1 1 d U
H20 H 0.6565 1.3064 0.5228 0.019 Uiso 1 1 calc R
C23 C 0.5923(3) 1.26949(14) 0.96174(10) 0.0219(4) Uani 1 1 d .
C15 C 0.2192(3) 0.48241(13) 0.67987(11) 0.0225(4) Uani 1 1 d .
C25 C 0.4003(3) 1.31809(16) 0.98251(12) 0.0306(4) Uani 1 1 d .
H25B H 0.4274 1.3749 1.0404 0.046 Uiso 1 1 calc R
H25C H 0.2839 1.2530 0.9895 0.046 Uiso 1 1 calc R
H25A H 0.3672 1.3573 0.9308 0.046 Uiso 1 1 calc R
C3 C 0.8780(3) 0.80575(17) 0.67829(12) 0.0290(4) Uani 1 1 d U
C2 C 0.9285(3) 0.90477(19) 0.63623(13) 0.0319(5) Uani 1 1 d U
C4 C 0.8785(3) 0.8156(2) 0.77457(13) 0.0331(5) Uani 1 1 d U
C26 C 0.6353(4) 1.20010(18) 1.03902(12) 0.0371(5) Uani 1 1 d .
H26B H 0.6666 1.2534 1.0987 0.056 Uiso 1 1 calc R
H26C H 0.7530 1.1655 1.0238 0.056 Uiso 1 1 calc R
H26E H 0.5138 1.1372 1.0438 0.056 Uiso 1 1 calc R
C16 C 0.3872(3) 0.45386(16) 0.74106(14) 0.0364(5) Uani 1 1 d .
H16B H 0.3535 0.3694 0.7451 0.055 Uiso 1 1 calc R
H16C H 0.3950 0.4992 0.8038 0.055 Uiso 1 1 calc R
H16E H 0.5201 0.4747 0.7133 0.055 Uiso 1 1 calc R
C24 C 0.7772(3) 1.37271(17) 0.95626(13) 0.0352(5) Uani 1 1 d .
H24B H 0.8020 1.4258 1.0161 0.053 Uiso 1 1 calc R
H24C H 0.7478 1.4161 0.9066 0.053 Uiso 1 1 calc R
H24E H 0.8997 1.3420 0.9425 0.053 Uiso 1 1 calc R
C5 C 0.9280(3) 0.9250(2) 0.82867(14) 0.0408(5) Uani 1 1 d U
C17 C 0.0150(3) 0.45988(18) 0.72854(17) 0.0417(5) Uani 1 1 d .
H17B H -0.0201 0.3781 0.7405 0.063 Uiso 1 1 calc R
H17C H -0.0946 0.4736 0.6882 0.063 Uiso 1 1 calc R
H17E H 0.0298 0.5136 0.7879 0.063 Uiso 1 1 calc R
C6 C 0.9780(3) 1.0251(2) 0.78778(18) 0.0453(6) Uani 1 1 d U
C18 C 0.1949(4) 0.40514(16) 0.58411(13) 0.0338(5) Uani 1 1 d .
H18B H 0.1674 0.3219 0.5921 0.051 Uiso 1 1 calc R
H18C H 0.3218 0.4252 0.5516 0.051 Uiso 1 1 calc R
H18E H 0.0798 0.4188 0.5472 0.051 Uiso 1 1 calc R
C1 C 0.9797(3) 1.01595(19) 0.69067(19) 0.0415(5) Uani 1 1 d U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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'
F F 0.0096 0.0061 '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 C7 C8 121.66(12) . .
C12 C7 H7 119.2 . .
C8 C7 H7 119.2 . .
C7 C8 C9 119.76(12) . .
C7 C8 C21 118.80(12) . .
C9 C8 C21 121.43(13) . .
C7 C12 C11 119.97(13) . .
C7 C12 C13 119.11(12) . .
C11 C12 C13 120.92(12) . .
C12 C11 C10 118.87(12) . .
C12 C11 C20 121.89(13) . 2_676
C10 C11 C20 119.24(12) . 2_676
C22 C21 C8 176.19(15) . .
C8 C9 C10 119.25(12) . .
C8 C9 C19 121.86(12) . .
C10 C9 C19 118.88(12) . .
C11 C10 C9 120.49(12) . .
C11 C10 C10 119.70(15) . 2_676
C9 C10 C10 119.81(15) . 2_676
C14 C13 C12 179.41(17) . .
C13 C14 C15 178.95(15) . .
C20 C19 C9 121.49(13) . .
C20 C19 H19 119.3 . .
C9 C19 H19 119.3 . .
C21 C22 C23 179.15(16) . .
C19 C20 C11 120.88(13) . 2_676
C19 C20 H20 119.6 . .
C11 C20 H20 119.6 2_676 .
C22 C23 C26 108.84(13) . .
C22 C23 C24 109.48(13) . .
C26 C23 C24 110.36(16) . .
C22 C23 C25 109.31(13) . .
C26 C23 C25 109.60(15) . .
C24 C23 C25 109.23(15) . .
C14 C15 C18 109.45(13) . .
C14 C15 C16 108.91(14) . .
C18 C15 C16 109.77(15) . .
C14 C15 C17 109.42(14) . .
C18 C15 C17 110.22(16) . .
C16 C15 C17 109.04(16) . .
C23 C25 H25B 109.5 . .
C23 C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C23 C25 H25A 109.5 . .
H25B C25 H25A 109.5 . .
H25C C25 H25A 109.5 . .
F28 C3 C2 120.09(17) . .
F28 C3 C4 119.50(19) . .
C2 C3 C4 120.41(19) . .
F27 C2 C3 119.34(19) . .
F27 C2 C1 120.8(2) . .
C3 C2 C1 119.90(18) . .
F29 C4 C5 120.58(18) . .
F29 C4 C3 119.41(19) . .
C5 C4 C3 120.0(2) . .
C23 C26 H26B 109.5 . .
C23 C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C23 C26 H26E 109.5 . .
H26B C26 H26E 109.5 . .
H26C C26 H26E 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C16 H16E 109.5 . .
H16B C16 H16E 109.5 . .
H16C C16 H16E 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C23 C24 H24E 109.5 . .
H24B C24 H24E 109.5 . .
H24C C24 H24E 109.5 . .
F30 C5 C6 120.7(2) . .
F30 C5 C4 118.9(2) . .
C6 C5 C4 120.4(2) . .
C15 C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C15 C17 H17E 109.5 . .
H17B C17 H17E 109.5 . .
H17C C17 H17E 109.5 . .
F31 C6 C5 120.5(3) . .
F31 C6 C1 119.5(3) . .
C5 C6 C1 120.0(2) . .
C15 C18 H18B 109.5 . .
C15 C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C15 C18 H18E 109.5 . .
H18B C18 H18E 109.5 . .
H18C C18 H18E 109.5 . .
F32 C1 C2 119.6(2) . .
F32 C1 C6 121.1(2) . .
C2 C1 C6 119.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F28 C3 1.337(2) .
F27 C2 1.340(2) .
F29 C4 1.343(3) .
C7 C12 1.3943(18) .
C7 C8 1.3993(19) .
C7 H7 0.9500 .
C8 C9 1.4136(19) .
C8 C21 1.4344(18) .
C12 C11 1.4215(19) .
C12 C13 1.4346(19) .
C11 C10 1.4229(18) .
C11 C20 1.4371(18) 2_676
C21 C22 1.209(2) .
C9 C10 1.4264(18) .
C9 C19 1.4340(19) .
C10 C10 1.432(3) 2_676
F32 C1 1.322(3) .
F30 C5 1.339(3) .
C13 C14 1.205(2) .
C14 C15 1.470(2) .
C19 C20 1.359(2) .
C19 H19 0.9500 .
F31 C6 1.327(3) .
C22 C23 1.4724(19) .
C20 C11 1.4371(18) 2_676
C20 H20 0.9500 .
C23 C26 1.535(2) .
C23 C24 1.538(2) .
C23 C25 1.538(2) .
C15 C18 1.529(2) .
C15 C16 1.536(3) .
C15 C17 1.540(3) .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C25 H25A 0.9800 .
C3 C2 1.373(3) .
C3 C4 1.384(2) .
C2 C1 1.393(3) .
C4 C5 1.374(3) .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C26 H26E 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C16 H16E 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C24 H24E 0.9800 .
C5 C6 1.374(4) .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C17 H17E 0.9800 .
C6 C1 1.397(4) .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C18 H18E 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C12 C7 C8 C9 0.0(2) . .
C12 C7 C8 C21 -179.16(12) . .
C8 C7 C12 C11 0.0(2) . .
C8 C7 C12 C13 179.50(13) . .
C7 C12 C11 C10 0.2(2) . .
C13 C12 C11 C10 -179.26(12) . .
C7 C12 C11 C20 179.73(12) . 2_676
C13 C12 C11 C20 0.2(2) . 2_676
C7 C8 C21 C22 9(2) . .
C9 C8 C21 C22 -170(2) . .
C7 C8 C9 C10 -0.2(2) . .
C21 C8 C9 C10 178.91(12) . .
C7 C8 C9 C19 -179.42(13) . .
C21 C8 C9 C19 -0.3(2) . .
C12 C11 C10 C9 -0.5(2) . .
C20 C11 C10 C9 -179.98(11) 2_676 .
C12 C11 C10 C10 179.11(15) . 2_676
C20 C11 C10 C10 -0.4(2) 2_676 2_676
C8 C9 C10 C11 0.5(2) . .
C19 C9 C10 C11 179.68(12) . .
C8 C9 C10 C10 -179.10(15) . 2_676
C19 C9 C10 C10 0.1(2) . 2_676
C7 C12 C13 C14 -74(15) . .
C11 C12 C13 C14 106(15) . .
C12 C13 C14 C15 -87(19) . .
C8 C9 C19 C20 179.43(13) . .
C10 C9 C19 C20 0.3(2) . .
C8 C21 C22 C23 27(13) . .
C9 C19 C20 C11 -0.3(2) . 2_676
C21 C22 C23 C26 -14(12) . .
C21 C22 C23 C24 107(12) . .
C21 C22 C23 C25 -133(12) . .
C13 C14 C15 C18 -19(10) . .
C13 C14 C15 C16 101(10) . .
C13 C14 C15 C17 -140(10) . .
F28 C3 C2 F27 -1.1(2) . .
C4 C3 C2 F27 179.60(16) . .
F28 C3 C2 C1 178.97(16) . .
C4 C3 C2 C1 -0.3(3) . .
F28 C3 C4 F29 0.0(3) . .
C2 C3 C4 F29 179.23(16) . .
F28 C3 C4 C5 -178.72(17) . .
C2 C3 C4 C5 0.6(3) . .
F29 C4 C5 F30 -0.6(3) . .
C3 C4 C5 F30 178.10(17) . .
F29 C4 C5 C6 -178.91(18) . .
C3 C4 C5 C6 -0.2(3) . .
F30 C5 C6 F31 1.8(3) . .
C4 C5 C6 F31 -179.93(18) . .
F30 C5 C6 C1 -178.63(18) . .
C4 C5 C6 C1 -0.3(3) . .
F27 C2 C1 F32 -0.1(3) . .
C3 C2 C1 F32 179.76(17) . .
F27 C2 C1 C6 179.85(16) . .
C3 C2 C1 C6 -0.3(3) . .
F31 C6 C1 F32 0.2(3) . .
C5 C6 C1 F32 -179.46(18) . .
F31 C6 C1 C2 -179.81(16) . .
C5 C6 C1 C2 0.6(3) . .
