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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/4/12/43/4124332.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_4124332
loop_
_publ_author_name
'Ono, Toshikazu'
'Sugimoto, Manabu'
'Hisaeda, Yoshio'
_publ_section_title
;
 Multicomponent Molecular Puzzles for Photofunction Design: Emission Color
 Variation in Lewis Acid-Base Pair Crystals Coupled with Guest-to-Host
 Charge Transfer Excitation.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9519
_journal_page_last               9522
_journal_paper_doi               10.1021/jacs.5b04178
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C60 H12 B2 F30 N4 O4, 2(C9 H12)'
_chemical_formula_sum            'C78 H36 B2 F30 N4 O4'
_chemical_formula_weight         1684.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2010.1-2'
_cell_angle_alpha                90
_cell_angle_beta                 99.764(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1604(11)
_cell_length_b                   21.035(2)
_cell_length_c                   14.8978(15)
_cell_measurement_temperature    100
_cell_volume                     3446.7(6)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40997
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         7108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0499P)²+1.6753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                5479
_reflns_number_total             7108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b04178_si_007.cif
_cod_data_source_block           I
_cod_database_code               4124332
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
B B1 0.19643(18) 0.82129(9) 0.06621(13) 0.0179(4) Uani d . 1
C C1 -0.02165(17) 0.90680(8) 0.33435(12) 0.0222(4) Uani d . 1
C C2 -0.02306(16) 0.92699(8) 0.42886(12) 0.0201(4) Uani d . 1
C C3 -0.04523(17) 0.88242(8) 0.49165(13) 0.0240(4) Uani d . 1
H H3 -0.0601 0.8394 0.4735 0.029 Uiso calc R 1
C C4 -0.04588(17) 0.90015(8) 0.58213(12) 0.0227(4) Uani d . 1
H H4 -0.0614 0.8692 0.6252 0.027 Uiso calc R 1
C C5 0.02557(16) 1.01955(8) 0.29519(12) 0.0197(4) Uani d . 1
C C6 0.02397(16) 1.03759(8) 0.39119(12) 0.0190(4) Uani d . 1
C C7 0.00055(15) 0.99106(8) 0.45436(11) 0.0175(3) Uani d . 1
C C8 0.08685(15) 0.89314(8) 0.16325(11) 0.0179(3) Uani d . 1
H H8 0.1459 0.8782 0.2123 0.021 Uiso calc R 1
C C9 0.00114(16) 0.93596(8) 0.18066(11) 0.0187(4) Uani d . 1
C C10 -0.08474(16) 0.95887(8) 0.11056(12) 0.0216(4) Uani d . 1
H H10 -0.143 0.9896 0.1215 0.026 Uiso calc R 1
C C11 -0.08323(16) 0.93572(9) 0.02375(12) 0.0220(4) Uani d . 1
H H11 -0.1419 0.9499 -0.026 0.026 Uiso calc R 1
C C12 0.00341(15) 0.89210(8) 0.00987(12) 0.0192(4) Uani d . 1
H H12 0.0027 0.8759 -0.0497 0.023 Uiso calc R 1
C C1A 0.32735(16) 0.85924(9) 0.07840(11) 0.0195(4) Uani d . 1
C C2A 0.42740(17) 0.82670(9) 0.05632(12) 0.0247(4) Uani d . 1
C C3A 0.53806(18) 0.85406(11) 0.05117(13) 0.0332(5) Uani d . 1
C C4A 0.55493(18) 0.91720(12) 0.07124(14) 0.0350(5) Uani d . 1
C C5A 0.46185(18) 0.95190(10) 0.09561(13) 0.0299(4) Uani d . 1
C C6A 0.35120(16) 0.92297(9) 0.09787(12) 0.0216(4) Uani d . 1
C C7A 0.17349(16) 0.79488(8) -0.03909(12) 0.0203(4) Uani d . 1
C C8A 0.15610(19) 0.73196(9) -0.06608(13) 0.0288(4) Uani d . 1
C C9A 0.1515(2) 0.71157(9) -0.15485(14) 0.0333(5) Uani d . 1
C C10A 0.16396(19) 0.75462(10) -0.22167(13) 0.0296(4) Uani d . 1
C C11A 0.18051(16) 0.81762(9) -0.19921(12) 0.0245(4) Uani d . 1
C C12A 0.18577(16) 0.83598(8) -0.11001(12) 0.0202(4) Uani d . 1
C C13A 0.18696(17) 0.76757(8) 0.14456(12) 0.0212(4) Uani d . 1
C C14A 0.27978(18) 0.74687(9) 0.21214(12) 0.0250(4) Uani d . 1
C C15A 0.2640(2) 0.70332(9) 0.27893(13) 0.0317(5) Uani d . 1
C C16A 0.1510(2) 0.67952(9) 0.28213(13) 0.0371(5) Uani d . 1
C C17A 0.0541(2) 0.69909(10) 0.21798(14) 0.0360(5) Uani d . 1
C C18A 0.07449(19) 0.74104(9) 0.15131(13) 0.0276(4) Uani d . 1
C C1S 0.29057(18) 0.89305(9) 0.45914(13) 0.0293(4) Uani d . 1
C C2S 0.29134(18) 0.91108(9) 0.54899(13) 0.0282(4) Uani d . 1
H H2S 0.2763 0.88 0.592 0.034 Uiso calc R 1
C C3S 0.31357(18) 0.97357(9) 0.57743(13) 0.0275(4) Uani d . 1
C C4S 0.33324(17) 1.01879(9) 0.51386(14) 0.0288(4) Uani d . 1
H H4S 0.3476 1.0617 0.5325 0.035 Uiso calc R 1
C C5S 0.33236(17) 1.00249(10) 0.42292(14) 0.0292(4) Uani d . 1
C C6S 0.31091(18) 0.93975(10) 0.39711(13) 0.0292(4) Uani d . 1
H H6S 0.31 0.9282 0.3354 0.035 Uiso calc R 1
C C7S 0.2701(2) 0.82481(11) 0.43038(16) 0.0447(6) Uani d . 1
H H7Z 0.2609 0.7989 0.4834 0.067 Uiso calc R 1
H H7Y 0.3398 0.8095 0.4044 0.067 Uiso calc R 1
H H7X 0.1962 0.8216 0.3845 0.067 Uiso calc R 1
C C8S 0.3183(2) 0.99179(11) 0.67613(14) 0.0384(5) Uani d . 1
H H8Z 0.3654 1.031 0.689 0.058 Uiso calc R 1
H H8X 0.3571 0.9576 0.7154 0.058 Uiso calc R 1
H H8Y 0.2355 0.9985 0.688 0.058 Uiso calc R 1
C C9S 0.3547(2) 1.05302(12) 0.35588(16) 0.0421(6) Uani d . 1
H H9Z 0.3509 1.0339 0.2955 0.063 Uiso calc R 1
H H9Y 0.4352 1.0718 0.3755 0.063 Uiso calc R 1
H H9X 0.2925 1.0862 0.3531 0.063 Uiso calc R 1
F F2A 0.41640(11) 0.76400(5) 0.03728(8) 0.0336(3) Uani d . 1
F F3A 0.62878(11) 0.81980(7) 0.02708(8) 0.0475(4) Uani d . 1
F F4A 0.66106(11) 0.94598(8) 0.06637(10) 0.0574(4) Uani d . 1
F F5A 0.47655(12) 1.01435(6) 0.11463(9) 0.0438(3) Uani d . 1
F F6A 0.26372(10) 0.96263(5) 0.11808(8) 0.0271(3) Uani d . 1
F F8A 0.14541(13) 0.68587(5) -0.00496(8) 0.0421(3) Uani d . 1
F F9A 0.13419(15) 0.64989(6) -0.17620(9) 0.0541(4) Uani d . 1
F F10A 0.15885(12) 0.73570(6) -0.30781(8) 0.0431(3) Uani d . 1
F F11A 0.19041(11) 0.86074(6) -0.26396(7) 0.0327(3) Uani d . 1
F F12A 0.20469(10) 0.89892(5) -0.09267(7) 0.0239(2) Uani d . 1
F F14A 0.39435(10) 0.76956(6) 0.21811(8) 0.0334(3) Uani d . 1
F F15A 0.35944(13) 0.68592(6) 0.34203(8) 0.0456(3) Uani d . 1
F F16A 0.13448(16) 0.63722(6) 0.34614(8) 0.0554(4) Uani d . 1
F F17A -0.05733(14) 0.67640(7) 0.22043(9) 0.0551(4) Uani d . 1
F F18A -0.02310(11) 0.75670(6) 0.08825(8) 0.0365(3) Uani d . 1
N N1 0.00152(13) 0.95504(7) 0.27331(10) 0.0190(3) Uani d . 1
N N2 0.08953(12) 0.87163(7) 0.07851(9) 0.0173(3) Uani d . 1
O O1 -0.04033(14) 0.85277(6) 0.30747(9) 0.0326(3) Uani d . 1
O O2 0.04576(12) 1.05647(6) 0.23718(9) 0.0270(3) Uani d . 1
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'
N N 0.0061 0.0033 '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'
B B 0.0013 0.0007 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N2 B1 C13A . . 103.35(13)
N2 B1 C7A . . 109.20(14)
C13A B1 C7A . . 115.34(14)
N2 B1 C1A . . 108.99(14)
C13A B1 C1A . . 114.71(15)
C7A B1 C1A . . 105.11(14)
O1 C1 N1 . . 120.01(16)
O1 C1 C2 . . 123.87(16)
N1 C1 C2 . . 116.11(15)
C3 C2 C7 . . 120.93(16)
C3 C2 C1 . . 119.05(16)
C7 C2 C1 . . 120.01(15)
C2 C3 C4 . . 120.27(16)
C2 C3 H3 . . 119.9
C4 C3 H3 . . 119.9
C6 C4 C3 3_576 . 120.07(16)
C6 C4 H4 3_576 . 120.0
C3 C4 H4 . . 120.0
O2 C5 N1 . . 120.20(16)
O2 C5 C6 . . 123.95(16)
N1 C5 C6 . . 115.85(15)
C4 C6 C7 3_576 . 120.68(16)
C4 C6 C5 3_576 . 119.37(15)
C7 C6 C5 . . 119.95(15)
C6 C7 C2 . . 121.94(16)
C6 C7 C7 . 3_576 119.30(19)
C2 C7 C7 . 3_576 118.75(19)
N2 C8 C9 . . 121.71(16)
N2 C8 H8 . . 119.1
C9 C8 H8 . . 119.1
C8 C9 C10 . . 120.28(16)
C8 C9 N1 . . 118.48(15)
C10 C9 N1 . . 121.22(15)
C9 C10 C11 . . 117.86(16)
C9 C10 H10 . . 121.1
C11 C10 H10 . . 121.1
C12 C11 C10 . . 119.73(16)
C12 C11 H11 . . 120.1
C10 C11 H11 . . 120.1
N2 C12 C11 . . 121.86(16)
N2 C12 H12 . . 119.1
C11 C12 H12 . . 119.1
C6A C1A C2A . . 112.97(16)
C6A C1A B1 . . 128.76(15)
C2A C1A B1 . . 117.80(16)
F2A C2A C3A . . 116.56(17)
F2A C2A C1A . . 118.73(17)
C3A C2A C1A . . 124.71(19)
F3A C3A C4A . . 119.90(19)
F3A C3A C2A . . 121.1(2)
C4A C3A C2A . . 119.05(18)
F4A C4A C3A . . 121.1(2)
F4A C4A C5A . . 119.4(2)
C3A C4A C5A . . 119.58(18)
F5A C5A C4A . . 120.32(18)
F5A C5A C6A . . 120.08(18)
C4A C5A C6A . . 119.56(19)
F6A C6A C5A . . 114.47(17)
F6A C6A C1A . . 121.39(15)
C5A C6A C1A . . 124.10(17)
C8A C7A C12A . . 113.59(16)
C8A C7A B1 . . 126.22(16)
C12A C7A B1 . . 119.74(15)
F8A C8A C9A . . 115.43(17)
F8A C8A C7A . . 120.93(16)
C9A C8A C7A . . 123.62(18)
F9A C9A C10A . . 119.66(17)
F9A C9A C8A . . 120.47(18)
C10A C9A C8A . . 119.86(18)
F10A C10A C9A . . 120.54(18)
F10A C10A C11A . . 120.29(18)
C9A C10A C11A . . 119.17(17)
F11A C11A C10A . . 120.11(16)
F11A C11A C12A . . 120.62(17)
C10A C11A C12A . . 119.26(17)
F12A C12A C11A . . 115.91(16)
F12A C12A C7A . . 119.60(15)
C11A C12A C7A . . 124.49(17)
C14A C13A C18A . . 113.15(17)
C14A C13A B1 . . 127.05(17)
C18A C13A B1 . . 119.66(16)
F14A C14A C15A . . 114.82(17)
F14A C14A C13A . . 121.20(16)
C15A C14A C13A . . 123.97(19)
F15A C15A C16A . . 120.14(18)
F15A C15A C14A . . 119.9(2)
C16A C15A C14A . . 119.89(19)
F16A C16A C15A . . 120.5(2)
F16A C16A C17A . . 120.4(2)
C15A C16A C17A . . 119.12(18)
F17A C17A C18A . . 121.1(2)
F17A C17A C16A . . 119.84(19)
C18A C17A C16A . . 119.1(2)
F18A C18A C17A . . 116.44(18)
F18A C18A C13A . . 118.79(17)
C17A C18A C13A . . 124.77(19)
C2S C1S C6S . . 118.12(18)
C2S C1S C7S . . 120.70(19)
C6S C1S C7S . . 121.18(19)
C1S C2S C3S . . 121.53(18)
C1S C2S H2S . . 119.2
C3S C2S H2S . . 119.2
C4S C3S C2S . . 118.78(18)
C4S C3S C8S . . 120.48(18)
C2S C3S C8S . . 120.73(18)
C3S C4S C5S . . 121.26(18)
C3S C4S H4S . . 119.4
C5S C4S H4S . . 119.4
C6S C5S C4S . . 118.43(18)
C6S C5S C9S . . 121.90(19)
C4S C5S C9S . . 119.67(19)
C5S C6S C1S . . 121.87(18)
C5S C6S H6S . . 119.1
C1S C6S H6S . . 119.1
C1S C7S H7Z . . 109.5
C1S C7S H7Y . . 109.5
H7Z C7S H7Y . . 109.5
C1S C7S H7X . . 109.5
H7Z C7S H7X . . 109.5
H7Y C7S H7X . . 109.5
C3S C8S H8Z . . 109.5
C3S C8S H8X . . 109.5
H8Z C8S H8X . . 109.5
C3S C8S H8Y . . 109.5
H8Z C8S H8Y . . 109.5
H8X C8S H8Y . . 109.5
C5S C9S H9Z . . 109.5
C5S C9S H9Y . . 109.5
H9Z C9S H9Y . . 109.5
C5S C9S H9X . . 109.5
H9Z C9S H9X . . 109.5
H9Y C9S H9X . . 109.5
C5 N1 C1 . . 126.13(14)
C5 N1 C9 . . 117.39(14)
C1 N1 C9 . . 116.48(14)
C8 N2 C12 . . 118.51(15)
C8 N2 B1 . . 117.21(14)
C12 N2 B1 . . 124.28(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 N2 . 1.629(2)
B1 C13A . 1.641(3)
B1 C7A . 1.643(2)
B1 C1A . 1.648(3)
C1 O1 . 1.211(2)
C1 N1 . 1.415(2)
C1 C2 . 1.473(2)
C2 C3 . 1.376(2)
C2 C7 . 1.413(2)
C3 C4 . 1.400(3)
C3 H3 . 0.95
C4 C6 3_576 1.378(2)
C4 H4 . 0.95
C5 O2 . 1.211(2)
C5 N1 . 1.411(2)
C5 C6 . 1.483(2)
C6 C4 3_576 1.378(2)
C6 C7 . 1.413(2)
C7 C7 3_576 1.413(3)
C8 N2 . 1.346(2)
C8 C9 . 1.370(2)
C8 H8 . 0.95
C9 C10 . 1.379(2)
C9 N1 . 1.437(2)
C10 C11 . 1.385(3)
C10 H10 . 0.95
C11 C12 . 1.374(2)
C11 H11 . 0.95
C12 N2 . 1.350(2)
C12 H12 . 0.95
C1A C6A . 1.388(3)
C1A C2A . 1.396(2)
C2A F2A . 1.350(2)
C2A C3A . 1.376(3)
C3A F3A . 1.340(2)
C3A C4A . 1.367(3)
C4A F4A . 1.343(2)
C4A C5A . 1.368(3)
C5A F5A . 1.348(2)
C5A C6A . 1.382(3)
C6A F6A . 1.356(2)
C7A C8A . 1.387(3)
C7A C12A . 1.390(2)
C8A F8A . 1.349(2)
C8A C9A . 1.383(3)
C9A F9A . 1.342(2)
C9A C10A . 1.370(3)
C10A F10A . 1.336(2)
C10A C11A . 1.372(3)
C11A F11A . 1.342(2)
C11A C12A . 1.376(2)
C12A F12A . 1.359(2)
C13A C14A . 1.387(3)
C13A C18A . 1.393(3)
C14A F14A . 1.354(2)
C14A C15A . 1.386(3)
C15A F15A . 1.346(2)
C15A C16A . 1.365(3)
C16A F16A . 1.340(2)
C16A C17A . 1.379(3)
C17A F17A . 1.338(2)
C17A C18A . 1.376(3)
C18A F18A . 1.353(2)
C1S C2S . 1.390(3)
C1S C6S . 1.393(3)
C1S C7S . 1.504(3)
C2S C3S . 1.390(3)
C2S H2S . 0.95
C3S C4S . 1.386(3)
C3S C8S . 1.512(3)
C4S C5S . 1.396(3)
C4S H4S . 0.95
C5S C6S . 1.384(3)
C5S C9S . 1.508(3)
C6S H6S . 0.95
C7S H7Z . 0.98
C7S H7Y . 0.98
C7S H7X . 0.98
C8S H8Z . 0.98
C8S H8X . 0.98
C8S H8Y . 0.98
C9S H9Z . 0.98
C9S H9Y . 0.98
C9S H9X . 0.98
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139124406
