#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/33/4033396.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_4033396
loop_
_publ_author_name
'Zhao, Meng-Yao'
'Wang, De-Xian'
'Wang, Mei-Xiang'
_publ_section_title
;
 Synthesis, Structure, and Properties of Corona[6]arenes and Their
 Assembly with Anions in the Crystalline State.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1502
_journal_page_last               1509
_journal_paper_doi               10.1021/acs.joc.7b03136
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         '2(B F4), C32 H22 N10 O6, 2(C8 H20 N)'
_chemical_formula_sum            'C48 H62 B2 F8 N12 O6'
_chemical_formula_weight         1076.71
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
????
;
_cell_angle_alpha                114.14(3)
_cell_angle_beta                 95.19(3)
_cell_angle_gamma                99.31(3)
_cell_formula_units_Z            1
_cell_length_a                   10.748(2)
_cell_length_b                   10.876(2)
_cell_length_c                   12.884(3)
_cell_measurement_reflns_used    4565
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4802
_cell_measurement_theta_min      1.9497
_cell_volume                     1335.6(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18205
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         1.759
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       Plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         6072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0501
_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)+(0.0502P)²+0.4929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5567
_reflns_number_total             6072
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b03136_si_010.cif
_cod_data_source_block           mx6158a
_cod_depositor_comments
'Adding full bibliography for 4033391--4033399.cif.'
_cod_database_code               4033396
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
F1 F 0.21958(9) 0.59875(12) 0.30258(11) 0.0567(3) Uani 1 1 d .
F2 F 0.06808(12) 0.72207(11) 0.30585(11) 0.0604(3) Uani 1 1 d .
F3 F 0.04314(11) 0.56352(11) 0.37906(9) 0.0529(3) Uani 1 1 d .
F4 F 0.02691(10) 0.49454(11) 0.18692(8) 0.0498(3) Uani 1 1 d .
B1 B 0.08962(17) 0.59516(18) 0.29356(15) 0.0327(4) Uani 1 1 d .
O1 O 0.47844(10) 0.73722(10) 0.20508(8) 0.0312(2) Uani 1 1 d .
O2 O 0.31477(11) 0.94310(11) 0.59499(9) 0.0352(3) Uani 1 1 d .
O3 O 0.13679(11) 0.83339(11) 0.98445(9) 0.0370(3) Uani 1 1 d .
N1 N 0.37771(12) 0.88705(12) 0.32337(10) 0.0282(3) Uani 1 1 d .
N2 N 0.33449(11) 0.93792(12) 0.42157(10) 0.0282(3) Uani 1 1 d .
N3 N 0.43893(11) 0.79994(12) 0.48798(10) 0.0284(3) Uani 1 1 d .
N4 N 0.48279(11) 0.74836(12) 0.38885(10) 0.0276(3) Uani 1 1 d .
N5 N 0.27087(12) 0.69895(12) 0.89993(10) 0.0272(3) Uani 1 1 d .
C1 C 0.47057(14) 0.49513(16) 0.13936(13) 0.0328(3) Uani 1 1 d .
H1 H 0.381868 0.478194 0.132303 0.039 Uiso 1 1 calc R
C2 C 0.53433(14) 0.38794(15) 0.11009(13) 0.0325(3) Uani 1 1 d .
H2 H 0.488021 0.297530 0.082556 0.039 Uiso 1 1 calc R
C3 C 0.66698(13) 0.41431(14) 0.12150(11) 0.0258(3) Uani 1 1 d .
C4 C 0.73682(14) 0.54828(15) 0.16036(13) 0.0311(3) Uani 1 1 d .
H4 H 0.825523 0.565880 0.167478 0.037 Uiso 1 1 calc R
C5 C 0.67324(14) 0.65617(15) 0.18863(13) 0.0319(3) Uani 1 1 d .
H5 H 0.718639 0.746510 0.213591 0.038 Uiso 1 1 calc R
C6 C 0.54218(14) 0.62739(14) 0.17916(11) 0.0270(3) Uani 1 1 d .
C7 C 0.44401(13) 0.78915(14) 0.30964(11) 0.0247(3) Uani 1 1 d .
C8 C 0.36267(13) 0.88636(14) 0.49689(12) 0.0261(3) Uani 1 1 d .
C9 C 0.30987(14) 0.87602(15) 0.66837(12) 0.0286(3) Uani 1 1 d .
C10 C 0.24345(14) 0.74159(16) 0.62787(12) 0.0320(3) Uani 1 1 d .
H10 H 0.207889 0.690424 0.550130 0.038 Uiso 1 1 calc R
C11 C 0.23068(14) 0.68405(15) 0.70562(12) 0.0302(3) Uani 1 1 d .
H11 H 0.186141 0.593312 0.680222 0.036 Uiso 1 1 calc R
C12 C 0.28428(13) 0.76176(14) 0.82111(12) 0.0262(3) Uani 1 1 d .
C13 C 0.35006(15) 0.89675(15) 0.86012(12) 0.0319(3) Uani 1 1 d .
H13 H 0.385103 0.948442 0.937928 0.038 Uiso 1 1 calc R
C14 C 0.36385(15) 0.95534(15) 0.78286(13) 0.0335(3) Uani 1 1 d .
H14 H 0.408475 1.045980 0.807886 0.040 Uiso 1 1 calc R
C15 C 0.19011(14) 0.74034(14) 0.97863(11) 0.0283(3) Uani 1 1 d .
C16 C 0.17205(16) 0.66901(16) 1.05567(12) 0.0340(3) Uani 1 1 d .
H16A H 0.157518 0.732771 1.128873 0.051 Uiso 1 1 calc GR
H16B H 0.247401 0.636025 1.067047 0.051 Uiso 1 1 calc GR
H16C H 0.099663 0.592491 1.020486 0.051 Uiso 1 1 calc GR
N6 N 0.16354(13) 0.18225(13) 0.30779(11) 0.0371(3) Uani 1 1 d .
C17 C 0.1140(2) 0.2511(2) 0.41911(15) 0.0576(6) Uani 1 1 d .
H17A H 0.021352 0.233316 0.401690 0.069 Uiso 1 1 calc R
H17B H 0.146087 0.350109 0.450186 0.069 Uiso 1 1 calc R
C18 C 0.1507(3) 0.2042(3) 0.51108(17) 0.0813(9) Uani 1 1 d .
H18A H 0.121602 0.105882 0.480714 0.122 Uiso 1 1 calc GR
H18B H 0.111792 0.248548 0.576864 0.122 Uiso 1 1 calc GR
H18C H 0.242146 0.228393 0.533927 0.122 Uiso 1 1 calc GR
C19 C 0.11393(15) 0.02682(16) 0.25317(13) 0.0357(3) Uani 1 1 d .
H19A H 0.146628 -0.012669 0.181638 0.043 Uiso 1 1 calc R
H19B H 0.148797 -0.009015 0.304402 0.043 Uiso 1 1 calc R
C20 C -0.03004(19) -0.0225(2) 0.2272(2) 0.0603(5) Uani 1 1 d .
H20A H -0.066411 0.014338 0.178367 0.090 Uiso 1 1 calc GR
H20B H -0.063287 0.008351 0.298079 0.090 Uiso 1 1 calc GR
H20C H -0.051841 -0.121556 0.188636 0.090 Uiso 1 1 calc GR
C21 C 0.30859(16) 0.20664(18) 0.33019(16) 0.0442(4) Uani 1 1 d .
H21A H 0.332941 0.164063 0.379726 0.053 Uiso 1 1 calc R
H21B H 0.336491 0.159863 0.257265 0.053 Uiso 1 1 calc R
C22 C 0.3800(2) 0.3564(2) 0.3854(2) 0.0739(7) Uani 1 1 d .
H22A H 0.355564 0.400717 0.338258 0.111 Uiso 1 1 calc GR
H22B H 0.470459 0.360883 0.392090 0.111 Uiso 1 1 calc GR
H22C H 0.359130 0.402370 0.460741 0.111 Uiso 1 1 calc GR
C23 C 0.11862(19) 0.24405(19) 0.22808(16) 0.0479(4) Uani 1 1 d .
H23A H 0.025754 0.223092 0.213554 0.057 Uiso 1 1 calc R
H23B H 0.147319 0.343666 0.268038 0.057 Uiso 1 1 calc R
C24 C 0.1639(2) 0.1952(2) 0.11413(18) 0.0551(5) Uani 1 1 d .
H24A H 0.127559 0.236090 0.068623 0.083 Uiso 1 1 calc GR
H24B H 0.137425 0.096486 0.073964 0.083 Uiso 1 1 calc GR
H24C H 0.255553 0.221786 0.126857 0.083 Uiso 1 1 calc GR
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'
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'
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'
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
F1 B1 F3 109.34(14) . .
F2 B1 F1 109.76(14) . .
F2 B1 F3 109.90(14) . .
F4 B1 F1 109.51(14) . .
F4 B1 F2 109.43(14) . .
F4 B1 F3 108.89(13) . .
C7 O1 C6 117.39(10) . .
C8 O2 C9 118.34(11) . .
N2 N1 C7 116.47(11) . .
N1 N2 C8 116.35(11) . .
C8 N3 N4 116.60(12) . .
C7 N4 N3 116.11(12) . .
C3 N5 C12 115.13(11) 2_666 .
C15 N5 C3 125.82(11) . 2_666
C15 N5 C12 118.61(11) . .
C2 C1 H1 121.0 . .
C6 C1 H1 121.0 . .
C6 C1 C2 118.08(14) . .
C1 C2 H2 119.7 . .
C1 C2 C3 120.56(14) . .
C3 C2 H2 119.7 . .
C2 C3 N5 118.26(12) . 2_666
C4 C3 N5 121.34(13) . 2_666
C4 C3 C2 120.25(13) . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.46(13) . .
C5 C4 H4 120.3 . .
C4 C5 H5 120.5 . .
C6 C5 C4 119.03(14) . .
C6 C5 H5 120.5 . .
C1 C6 O1 118.81(13) . .
C1 C6 C5 122.60(13) . .
C5 C6 O1 118.49(13) . .
N1 C7 O1 112.85(11) . .
N4 C7 O1 120.17(12) . .
N4 C7 N1 126.84(13) . .
N2 C8 O2 112.86(12) . .
N3 C8 O2 119.95(12) . .
N3 C8 N2 126.86(13) . .
C10 C9 O2 120.44(13) . .
C10 C9 C14 122.55(13) . .
C14 C9 O2 116.73(13) . .
C9 C10 H10 120.8 . .
C9 C10 C11 118.48(13) . .
C11 C10 H10 120.8 . .
C10 C11 H11 120.0 . .
C12 C11 C10 119.99(13) . .
C12 C11 H11 120.0 . .
C11 C12 N5 118.89(13) . .
C13 C12 N5 120.48(12) . .
C13 C12 C11 120.63(13) . .
C12 C13 H13 120.1 . .
C12 C13 C14 119.86(13) . .
C14 C13 H13 120.1 . .
C9 C14 C13 118.48(14) . .
C9 C14 H14 120.8 . .
C13 C14 H14 120.8 . .
O3 C15 N5 119.88(13) . .
O3 C15 C16 122.19(13) . .
N5 C15 C16 117.93(12) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C17 N6 C19 111.18(15) . .
C17 N6 C21 110.80(14) . .
C17 N6 C23 106.71(13) . .
C19 N6 C21 106.23(12) . .
C19 N6 C23 110.96(12) . .
C21 N6 C23 111.03(14) . .
N6 C17 H17A 108.6 . .
N6 C17 H17B 108.6 . .
N6 C17 C18 114.68(15) . .
H17A C17 H17B 107.6 . .
C18 C17 H17A 108.6 . .
C18 C17 H17B 108.6 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N6 C19 H19A 108.3 . .
N6 C19 H19B 108.3 . .
H19A C19 H19B 107.4 . .
C20 C19 N6 115.76(14) . .
C20 C19 H19A 108.3 . .
C20 C19 H19B 108.3 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N6 C21 H21A 108.3 . .
N6 C21 H21B 108.3 . .
H21A C21 H21B 107.4 . .
C22 C21 N6 115.76(15) . .
C22 C21 H21A 108.3 . .
C22 C21 H21B 108.3 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N6 C23 H23A 108.4 . .
N6 C23 H23B 108.4 . .
H23A C23 H23B 107.5 . .
C24 C23 N6 115.49(14) . .
C24 C23 H23A 108.4 . .
C24 C23 H23B 108.4 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.384(2) .
F2 B1 1.384(2) .
F3 B1 1.391(2) .
F4 B1 1.380(2) .
O1 C6 1.4099(16) .
O1 C7 1.3439(17) .
O2 C8 1.3512(17) .
O2 C9 1.4104(16) .
O3 C15 1.2213(17) .
N1 N2 1.3189(17) .
N1 C7 1.3367(18) .
N2 C8 1.3397(17) .
N3 N4 1.3328(17) .
N3 C8 1.3216(18) .
N4 C7 1.3286(17) .
N5 C3 1.4358(17) 2_666
N5 C12 1.4424(17) .
N5 C15 1.3771(18) .
C1 H1 0.9300 .
C1 C2 1.384(2) .
C1 C6 1.375(2) .
C2 H2 0.9300 .
C2 C3 1.390(2) .
C3 C4 1.385(2) .
C4 H4 0.9300 .
C4 C5 1.390(2) .
C5 H5 0.9300 .
C5 C6 1.376(2) .
C9 C10 1.375(2) .
C9 C14 1.378(2) .
C10 H10 0.9300 .
C10 C11 1.387(2) .
C11 H11 0.9300 .
C11 C12 1.385(2) .
C12 C13 1.380(2) .
C13 H13 0.9300 .
C13 C14 1.391(2) .
C14 H14 0.9300 .
C15 C16 1.497(2) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
N6 C17 1.513(2) .
N6 C19 1.518(2) .
N6 C21 1.519(2) .
N6 C23 1.523(2) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.515(3) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C19 C20 1.512(2) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C21 C22 1.515(3) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C23 C24 1.500(3) .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095926
