#------------------------------------------------------------------------------
#$Date: 2019-11-26 02:22:03 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242387 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/75/4037593.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_4037593
loop_
_publ_author_name
'Jeong, Eunjeong'
'Takahashi, Kohtaro'
'Rajagopal, Shinaj K.'
'Koganezawa, Tomoyuki'
'Hayashi, Hironobu'
'Aratani, Naoki'
'Suzuki, Mitsuharu'
'Nguyen, Thuc-Quyen'
'Yamada, Hiroko'
_publ_section_title
;
 Orbital-Energy Modulation of Tetrabenzoporphyrin-Derived Non-Fullerene
 Acceptors for Improved Open-Circuit Voltage in Organic Solar Cells.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02386
_journal_year                    2019
_chemical_formula_moiety         'C38 H20 F6 N4'
_chemical_formula_sum            'C38 H20 F6 N4'
_chemical_formula_weight         646.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.708(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   5.02838(14)
_cell_length_b                   15.2818(5)
_cell_length_c                   17.3664(6)
_cell_measurement_reflns_used    12541
_cell_measurement_temperature    103
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      3.56
_cell_volume                     1322.42(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.335
_diffrn_reflns_theta_min         3.566
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             660.00
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0363P)²+0.9402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1931
_reflns_number_total             2400
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo9b02386_si_002.cif
_cod_data_source_block           2CF3BP
_cod_database_code               4037593
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+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
F1 F 0.8479(2) 0.74629(8) 0.73116(7) 0.0238(3) Uani 1 1 d . .
F2 F 0.9740(2) 0.80469(8) 0.63098(7) 0.0244(3) Uani 1 1 d . .
F3 F 1.2528(2) 0.72497(8) 0.70619(7) 0.0246(3) Uani 1 1 d . .
N1 N 0.5543(3) 0.53789(11) 0.61508(9) 0.0185(4) Uani 1 1 d . .
N2 N 0.1769(3) 0.40724(11) 0.50478(9) 0.0160(4) Uani 1 1 d . .
H2 H 0.2975 0.4455 0.4940 0.019 Uiso 1 1 calc R U
C1 C 0.8960(4) 0.65221(13) 0.62530(12) 0.0187(5) Uani 1 1 d . .
C2 C 0.7390(4) 0.58944(13) 0.65889(12) 0.0182(4) Uani 1 1 d . .
C3 C 0.7484(4) 0.56819(13) 0.74199(12) 0.0191(5) Uani 1 1 d . .
C4 C 0.5452(4) 0.50633(13) 0.74585(12) 0.0187(4) Uani 1 1 d . .
C5 C 0.4261(4) 0.49058(13) 0.66571(11) 0.0182(4) Uani 1 1 d . .
C6 C 0.2097(4) 0.43409(13) 0.64678(12) 0.0186(4) Uani 1 1 d . .
H6 H 0.1233 0.4171 0.6898 0.022 Uiso 1 1 calc R U
C7 C 0.0978(4) 0.39826(13) 0.57683(11) 0.0177(4) Uani 1 1 d . .
C8 C -0.1138(4) 0.33344(13) 0.56835(12) 0.0178(4) Uani 1 1 d . .
C9 C -0.1446(4) 0.30255(13) 0.49123(12) 0.0187(5) Uani 1 1 d . .
C10 C 0.0482(4) 0.35037(13) 0.45152(12) 0.0179(4) Uani 1 1 d . .
C11 C 0.9938(4) 0.73020(14) 0.67318(12) 0.0213(5) Uani 1 1 d . .
C12 C 0.9255(4) 0.58861(14) 0.80914(12) 0.0215(5) Uani 1 1 d . .
H12 H 1.0703 0.6281 0.8071 0.026 Uiso 1 1 calc R U
C13 C 0.8830(4) 0.54962(14) 0.87834(12) 0.0235(5) Uani 1 1 d . .
H13 H 1.0005 0.5631 0.9243 0.028 Uiso 1 1 calc R U
C14 C 0.6720(4) 0.49087(14) 0.88263(12) 0.0246(5) Uani 1 1 d . .
H14 H 0.6446 0.4666 0.9313 0.029 Uiso 1 1 calc R U
C15 C 0.5029(4) 0.46813(14) 0.81584(12) 0.0226(5) Uani 1 1 d . .
H15 H 0.3615 0.4274 0.8179 0.027 Uiso 1 1 calc R U
C16 C -0.2706(4) 0.30243(14) 0.62262(12) 0.0193(5) Uani 1 1 d . .
H16 H -0.2485 0.3244 0.6743 0.023 Uiso 1 1 calc R U
C17 C -0.4592(4) 0.23888(14) 0.59931(12) 0.0218(5) Uani 1 1 d . .
H17 H -0.5656 0.2156 0.6357 0.026 Uiso 1 1 calc R U
C18 C -0.4953(4) 0.20864(14) 0.52310(12) 0.0213(5) Uani 1 1 d . .
H18 H -0.6271 0.1651 0.5084 0.026 Uiso 1 1 calc R U
C19 C -0.3448(4) 0.24011(14) 0.46814(12) 0.0211(5) Uani 1 1 d . .
H19 H -0.3759 0.2200 0.4159 0.025 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(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
C5 N1 C2 106.90(16) . .
C10 N2 C7 112.65(17) . .
C10 N2 H2 123.7 . .
C7 N2 H2 123.7 . .
C10 C1 C2 124.56(19) 3_666 .
C10 C1 C11 117.29(18) 3_666 .
C2 C1 C11 118.02(18) . .
N1 C2 C1 122.34(18) . .
N1 C2 C3 110.36(17) . .
C1 C2 C3 127.29(18) . .
C4 C3 C12 119.73(19) . .
C4 C3 C2 105.53(17) . .
C12 C3 C2 134.24(19) . .
C15 C4 C3 121.55(19) . .
C15 C4 C5 132.33(19) . .
C3 C4 C5 105.93(17) . .
N1 C5 C6 126.70(18) . .
N1 C5 C4 110.98(17) . .
C6 C5 C4 122.32(18) . .
C7 C6 C5 131.76(19) . .
C7 C6 H6 114.1 . .
C5 C6 H6 114.1 . .
N2 C7 C6 129.01(19) . .
N2 C7 C8 105.99(17) . .
C6 C7 C8 124.62(18) . .
C16 C8 C9 122.01(19) . .
C16 C8 C7 129.82(19) . .
C9 C8 C7 108.17(17) . .
C19 C9 C8 118.80(19) . .
C19 C9 C10 134.51(19) . .
C8 C9 C10 106.62(18) . .
N2 C10 C1 121.69(18) . 3_666
N2 C10 C9 106.44(17) . .
C1 C10 C9 131.84(19) 3_666 .
F1 C11 F2 104.13(16) . .
F1 C11 F3 106.51(16) . .
F2 C11 F3 106.05(16) . .
F1 C11 C1 112.91(17) . .
F2 C11 C1 112.00(16) . .
F3 C11 C1 114.45(17) . .
C13 C12 C3 118.1(2) . .
C13 C12 H12 121.0 . .
C3 C12 H12 121.0 . .
C12 C13 C14 121.9(2) . .
C12 C13 H13 119.0 . .
C14 C13 H13 119.0 . .
C15 C14 C13 120.0(2) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C4 118.5(2) . .
C14 C15 H15 120.7 . .
C4 C15 H15 120.7 . .
C17 C16 C8 118.09(19) . .
C17 C16 H16 121.0 . .
C8 C16 H16 121.0 . .
C16 C17 C18 120.7(2) . .
C16 C17 H17 119.7 . .
C18 C17 H17 119.7 . .
C19 C18 C17 121.9(2) . .
C19 C18 H18 119.1 . .
C17 C18 H18 119.1 . .
C18 C19 C9 118.48(19) . .
C18 C19 H19 120.8 . .
C9 C19 H19 120.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C11 1.345(2) .
F2 C11 1.350(2) .
F3 C11 1.353(2) .
N1 C5 1.365(3) .
N1 C2 1.368(3) .
N2 C10 1.367(3) .
N2 C7 1.370(3) .
N2 H2 0.8800 .
C1 C10 1.400(3) 3_666
C1 C2 1.417(3) .
C1 C11 1.498(3) .
C2 C3 1.474(3) .
C3 C4 1.400(3) .
C3 C12 1.404(3) .
C4 C15 1.390(3) .
C4 C5 1.459(3) .
C5 C6 1.393(3) .
C6 C7 1.382(3) .
C6 H6 0.9500 .
C7 C8 1.447(3) .
C8 C16 1.391(3) .
C8 C9 1.409(3) .
C9 C19 1.406(3) .
C9 C10 1.459(3) .
C10 C1 1.400(3) 3_666
C12 C13 1.383(3) .
C12 H12 0.9500 .
C13 C14 1.399(3) .
C13 H13 0.9500 .
C14 C15 1.387(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C17 1.380(3) .
C16 H16 0.9500 .
C17 C18 1.391(3) .
C17 H17 0.9500 .
C18 C19 1.381(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 N1 3_666 2.760(2) 0.880 2.141 126.8 no
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
C5 N1 C2 C1 -175.29(18) . .
C5 N1 C2 C3 5.7(2) . .
C10 C1 C2 N1 -22.8(3) 3_666 .
C11 C1 C2 N1 152.78(19) . .
C10 C1 C2 C3 156.1(2) 3_666 .
C11 C1 C2 C3 -28.4(3) . .
N1 C2 C3 C4 -4.5(2) . .
C1 C2 C3 C4 176.51(19) . .
N1 C2 C3 C12 167.0(2) . .
C1 C2 C3 C12 -11.9(4) . .
C12 C3 C4 C15 4.0(3) . .
C2 C3 C4 C15 177.10(18) . .
C12 C3 C4 C5 -171.52(18) . .
C2 C3 C4 C5 1.5(2) . .
C2 N1 C5 C6 175.1(2) . .
C2 N1 C5 C4 -4.7(2) . .
C15 C4 C5 N1 -173.0(2) . .
C3 C4 C5 N1 1.9(2) . .
C15 C4 C5 C6 7.1(3) . .
C3 C4 C5 C6 -177.99(18) . .
N1 C5 C6 C7 13.1(4) . .
C4 C5 C6 C7 -167.1(2) . .
C10 N2 C7 C6 169.2(2) . .
C10 N2 C7 C8 -3.9(2) . .
C5 C6 C7 N2 1.9(4) . .
C5 C6 C7 C8 173.8(2) . .
N2 C7 C8 C16 -177.2(2) . .
C6 C7 C8 C16 9.4(3) . .
N2 C7 C8 C9 2.9(2) . .
C6 C7 C8 C9 -170.59(19) . .
C16 C8 C9 C19 1.7(3) . .
C7 C8 C9 C19 -178.39(18) . .
C16 C8 C9 C10 179.08(18) . .
C7 C8 C9 C10 -1.0(2) . .
C7 N2 C10 C1 -178.78(18) . 3_666
C7 N2 C10 C9 3.3(2) . .
C19 C9 C10 N2 175.5(2) . .
C8 C9 C10 N2 -1.3(2) . .
C19 C9 C10 C1 -2.1(4) . 3_666
C8 C9 C10 C1 -179.0(2) . 3_666
C10 C1 C11 F1 154.47(17) 3_666 .
C2 C1 C11 F1 -21.4(3) . .
C10 C1 C11 F2 37.3(2) 3_666 .
C2 C1 C11 F2 -138.57(18) . .
C10 C1 C11 F3 -83.4(2) 3_666 .
C2 C1 C11 F3 100.7(2) . .
C4 C3 C12 C13 -3.4(3) . .
C2 C3 C12 C13 -174.0(2) . .
C3 C12 C13 C14 0.4(3) . .
C12 C13 C14 C15 2.0(3) . .
C13 C14 C15 C4 -1.4(3) . .
C3 C4 C15 C14 -1.6(3) . .
C5 C4 C15 C14 172.6(2) . .
C9 C8 C16 C17 0.6(3) . .
C7 C8 C16 C17 -179.3(2) . .
C8 C16 C17 C18 -1.6(3) . .
C16 C17 C18 C19 0.3(3) . .
C17 C18 C19 C9 2.0(3) . .
C8 C9 C19 C18 -2.9(3) . .
C10 C9 C19 C18 -179.4(2) . .
