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#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/59/1545945.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_1545945
loop_
_publ_author_name
'Tominaga, Masahide'
'Takahashi, Eri'
'Ukai, Hiroyuki'
'Ohara, Kazuaki'
'Itoh, Tsutomu'
'Yamaguchi, Kentaro'
_publ_section_title
;
 Solvent-Dependent Self-Assembly and Crystal Structures of a Salen-Based
 Macrocycle.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1508
_journal_page_last               1511
_journal_paper_doi               10.1021/acs.orglett.7b00264
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C60 H56 N4 O4'
_chemical_formula_weight         897.08
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.101(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.5759(6)
_cell_length_b                   13.1086(5)
_cell_length_c                   12.2124(5)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3720
_cell_measurement_theta_min      2.8046
_cell_volume                     2522.27(17)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.3'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'D8 Venture Ultra'
_diffrn_measurement_method       'φ and ω, two θ position'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23606
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.852
_diffrn_reflns_theta_min         4.387
_diffrn_source                   'rotation anode'
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.847
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0425
_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)+(0.0740P)²+1.4946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4172
_reflns_number_total             4808
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00264_si_002.cif
_cod_data_source_block           p21c_sq
_cod_database_code               1545945
_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   0.859
_shelx_estimated_absorpt_t_max   0.955
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1A C 0.30958(9) -0.15760(11) -0.52329(12) 0.0300(3) Uani 1 1 d . .
C2A C 0.25822(9) -0.16865(11) -0.61676(12) 0.0311(3) Uani 1 1 d . .
C3A C 0.20311(9) -0.18551(12) -0.73217(12) 0.0308(3) Uani 1 1 d . .
C4A C 0.17532(9) -0.28360(12) -0.76812(12) 0.0320(3) Uani 1 1 d . .
H4AA H 0.1891 -0.3385 -0.7148 0.038 Uiso 1 1 calc R U
C5A C 0.12718(9) -0.30166(13) -0.88233(13) 0.0344(3) Uani 1 1 d . .
C6A C 0.10534(9) -0.21995(14) -0.96094(12) 0.0369(4) Uani 1 1 d . .
C7A C 0.13236(10) -0.12257(14) -0.92224(13) 0.0401(4) Uani 1 1 d . .
H7AA H 0.1171 -0.0670 -0.9746 0.048 Uiso 1 1 calc R U
C8A C 0.18087(10) -0.10406(13) -0.80948(13) 0.0379(4) Uani 1 1 d . .
H8AA H 0.1989 -0.0367 -0.7849 0.046 Uiso 1 1 calc R U
O9A O 0.10326(7) -0.39792(9) -0.91530(10) 0.0458(3) Uani 1 1 d . .
C10A C 0.05555(10) -0.23750(16) -1.08133(13) 0.0432(4) Uani 1 1 d . .
H10A H 0.0401 -0.1808 -1.1320 0.052 Uiso 1 1 calc R U
N11A N 0.03246(8) -0.32621(14) -1.11994(11) 0.0467(4) Uani 1 1 d . .
C12A C -0.01839(10) -0.33751(18) -1.24060(14) 0.0528(5) Uani 1 1 d . .
H12A H 0.0119 -0.3814 -1.2810 0.063 Uiso 1 1 calc R U
H12B H -0.0274 -0.2699 -1.2786 0.063 Uiso 1 1 calc R U
C1B C 0.38190(8) 0.01883(10) -0.15149(11) 0.0269(3) Uani 1 1 d . .
C2B C 0.35073(8) 0.07861(11) -0.10209(12) 0.0279(3) Uani 1 1 d . .
C3B C 0.31025(8) 0.14786(10) -0.04456(11) 0.0262(3) Uani 1 1 d . .
C4B C 0.27456(9) 0.11055(11) 0.03685(12) 0.0292(3) Uani 1 1 d . .
H4BA H 0.2785 0.0399 0.0552 0.035 Uiso 1 1 calc R U
C5B C 0.23321(9) 0.17589(11) 0.09137(12) 0.0297(3) Uani 1 1 d . .
C6B C 0.22670(8) 0.28055(11) 0.06422(12) 0.0286(3) Uani 1 1 d . .
C7B C 0.26268(9) 0.31640(11) -0.01789(12) 0.0307(3) Uani 1 1 d . .
H7BA H 0.2582 0.3868 -0.0373 0.037 Uiso 1 1 calc R U
C8B C 0.30442(9) 0.25209(11) -0.07125(12) 0.0296(3) Uani 1 1 d . .
H8BA H 0.3292 0.2783 -0.1259 0.036 Uiso 1 1 calc R U
O9B O 0.19990(8) 0.13708(9) 0.16997(10) 0.0428(3) Uani 1 1 d . .
C10B C 0.18194(8) 0.34934(12) 0.11937(12) 0.0316(3) Uani 1 1 d . .
H10B H 0.1765 0.4195 0.0987 0.038 Uiso 1 1 calc R U
N11B N 0.15000(7) 0.31621(11) 0.19517(10) 0.0349(3) Uani 1 1 d . .
C12B C 0.10381(9) 0.38536(15) 0.24775(13) 0.0435(4) Uani 1 1 d . .
H12C H 0.0948 0.4516 0.2068 0.052 Uiso 1 1 calc R U
H12D H 0.1370 0.3977 0.3293 0.052 Uiso 1 1 calc R U
C1C C 0.41255(8) -0.05782(10) -0.21679(11) 0.0247(3) Uani 1 1 d . .
C2C C 0.34654(8) -0.06672(10) -0.33768(11) 0.0256(3) Uani 1 1 d . .
H2CA H 0.2905 -0.0847 -0.3301 0.031 Uiso 1 1 calc R U
H2CB H 0.3411 -0.0002 -0.3777 0.031 Uiso 1 1 calc R U
C8C C 0.38226(8) -0.25220(10) -0.34617(11) 0.0266(3) Uani 1 1 d . .
H8CA H 0.3268 -0.2722 -0.3381 0.032 Uiso 1 1 calc R U
H8CB H 0.3998 -0.3055 -0.3916 0.032 Uiso 1 1 calc R U
C3C C 0.42126(9) -0.16202(10) -0.15554(11) 0.0273(3) Uani 1 1 d . .
H3CA H 0.4640 -0.1572 -0.0783 0.033 Uiso 1 1 calc R U
H3CB H 0.3663 -0.1814 -0.1455 0.033 Uiso 1 1 calc R U
C5C C 0.37369(8) -0.14898(10) -0.40915(11) 0.0254(3) Uani 1 1 d . .
C9C C 0.46085(9) -0.11848(11) -0.42096(12) 0.0294(3) Uani 1 1 d . .
H9CA H 0.4793 -0.1702 -0.4672 0.035 Uiso 1 1 calc R U
H9CB H 0.4560 -0.0520 -0.4610 0.035 Uiso 1 1 calc R U
C6C C 0.52653(8) -0.11066(11) -0.30097(13) 0.0308(3) Uani 1 1 d . .
H6CA H 0.5828 -0.0916 -0.3090 0.037 Uiso 1 1 calc R U
C7C C 0.44844(9) -0.24332(10) -0.22689(12) 0.0286(3) Uani 1 1 d . .
H7CA H 0.4537 -0.3105 -0.1865 0.034 Uiso 1 1 calc R U
C4C C 0.49911(9) -0.02876(11) -0.22998(12) 0.0296(3) Uani 1 1 d . .
H4CA H 0.4947 0.0381 -0.2690 0.036 Uiso 1 1 calc R U
H4CB H 0.5421 -0.0230 -0.1530 0.036 Uiso 1 1 calc R U
C10C C 0.53419(9) -0.21444(11) -0.24040(13) 0.0324(3) Uani 1 1 d . .
H10C H 0.5519 -0.2671 -0.2864 0.039 Uiso 1 1 calc R U
H10D H 0.5777 -0.2107 -0.1637 0.039 Uiso 1 1 calc R U
H9A H 0.0669(18) -0.394(2) -1.009(3) 0.103(9) Uiso 1 1 d . .
H9B H 0.1708(16) 0.201(2) 0.199(2) 0.083(7) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_3
C2A C1A C5C 177.36(15) .
C1A C2A C3A 174.64(15) .
C4A C3A C8A 120.10(13) .
C4A C3A C2A 119.92(13) .
C8A C3A C2A 119.91(14) .
C3A C4A C5A 120.21(14) .
O9A C5A C4A 118.80(14) .
O9A C5A C6A 121.30(14) .
C4A C5A C6A 119.90(15) .
C7A C6A C5A 118.72(14) .
C7A C6A C10A 120.58(16) .
C5A C6A C10A 120.70(16) .
C8A C7A C6A 121.81(15) .
C7A C8A C3A 119.24(15) .
N11A C10A C6A 121.89(17) .
C10A N11A C12A 118.75(17) .
N11A C12A C12B 109.50(14) 3_554
C2B C1B C1C 174.99(14) .
C1B C2B C3B 177.66(14) .
C4B C3B C8B 119.61(13) .
C4B C3B C2B 119.58(13) .
C8B C3B C2B 120.79(13) .
C5B C4B C3B 120.49(13) .
O9B C5B C4B 118.77(13) .
O9B C5B C6B 121.17(13) .
C4B C5B C6B 120.07(13) .
C7B C6B C5B 118.56(13) .
C7B C6B C10B 121.00(13) .
C5B C6B C10B 120.43(13) .
C8B C7B C6B 121.54(13) .
C7B C8B C3B 119.72(13) .
N11B C10B C6B 120.63(14) .
C10B N11B C12B 120.04(15) .
N11B C12B C12A 108.91(15) 3_554
C1B C1C C4C 112.23(11) .
C1B C1C C3C 109.80(11) .
C4C C1C C3C 108.65(11) .
C1B C1C C2C 108.00(10) .
C4C C1C C2C 108.96(11) .
C3C C1C C2C 109.17(11) .
C5C C2C C1C 110.47(10) .
C7C C8C C5C 109.62(11) .
C7C C3C C1C 109.90(11) .
C1A C5C C2C 109.79(11) .
C1A C5C C8C 109.44(11) .
C2C C5C C8C 109.26(10) .
C1A C5C C9C 110.60(11) .
C2C C5C C9C 108.51(11) .
C8C C5C C9C 109.22(11) .
C6C C9C C5C 109.53(11) .
C10C C6C C4C 110.02(12) .
C10C C6C C9C 109.22(11) .
C4C C6C C9C 109.85(11) .
C10C C7C C3C 109.69(11) .
C10C C7C C8C 109.36(11) .
C3C C7C C8C 110.11(11) .
C6C C4C C1C 109.57(11) .
C7C C10C C6C 109.34(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C2A 1.202(2) .
C1A C5C 1.4713(18) .
C2A C3A 1.4386(19) .
C3A C4A 1.390(2) .
C3A C8A 1.397(2) .
C4A C5A 1.395(2) .
C5A O9A 1.346(2) .
C5A C6A 1.408(2) .
C6A C7A 1.386(2) .
C6A C10A 1.463(2) .
C7A C8A 1.383(2) .
C10A N11A 1.268(2) .
N11A C12A 1.460(2) .
C12A C12B 1.526(2) 3_554
C1B C2B 1.1995(19) .
C1B C1C 1.4681(18) .
C2B C3B 1.4356(19) .
C3B C4B 1.3940(19) .
C3B C8B 1.401(2) .
C4B C5B 1.389(2) .
C5B O9B 1.3470(17) .
C5B C6B 1.408(2) .
C6B C7B 1.398(2) .
C6B C10B 1.4588(19) .
C7B C8B 1.376(2) .
C10B N11B 1.277(2) .
N11B C12B 1.4579(19) .
C12B C12A 1.526(2) 3_554
C1C C4C 1.5406(18) .
C1C C3C 1.5424(18) .
C1C C2C 1.5448(17) .
C2C C5C 1.5398(18) .
C8C C7C 1.5316(18) .
C8C C5C 1.5410(19) .
C3C C7C 1.5304(18) .
C5C C9C 1.5484(18) .
C9C C6C 1.5335(19) .
C6C C10C 1.535(2) .
C6C C4C 1.5348(19) .
C7C C10C 1.528(2) .
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_4
C8A C3A C4A C5A 1.9(2) .
C2A C3A C4A C5A -175.14(13) .
C3A C4A C5A O9A 178.13(13) .
C3A C4A C5A C6A -1.2(2) .
O9A C5A C6A C7A -179.47(14) .
C4A C5A C6A C7A -0.2(2) .
O9A C5A C6A C10A 0.2(2) .
C4A C5A C6A C10A 179.44(13) .
C5A C6A C7A C8A 0.9(2) .
C10A C6A C7A C8A -178.74(14) .
C6A C7A C8A C3A -0.2(2) .
C4A C3A C8A C7A -1.2(2) .
C2A C3A C8A C7A 175.84(13) .
C7A C6A C10A N11A 177.58(15) .
C5A C6A C10A N11A -2.0(2) .
C6A C10A N11A C12A 178.94(13) .
C10A N11A C12A C12B -119.33(18) 3_554
C8B C3B C4B C5B 0.1(2) .
C2B C3B C4B C5B -178.36(12) .
C3B C4B C5B O9B -179.67(12) .
C3B C4B C5B C6B 0.3(2) .
O9B C5B C6B C7B 179.87(13) .
C4B C5B C6B C7B -0.1(2) .
O9B C5B C6B C10B -1.2(2) .
C4B C5B C6B C10B 178.78(12) .
C5B C6B C7B C8B -0.5(2) .
C10B C6B C7B C8B -179.43(13) .
C6B C7B C8B C3B 1.0(2) .
C4B C3B C8B C7B -0.8(2) .
C2B C3B C8B C7B 177.71(12) .
C7B C6B C10B N11B -179.28(13) .
C5B C6B C10B N11B 1.9(2) .
C6B C10B N11B C12B -178.65(12) .
C10B N11B C12B C12A 129.64(15) 3_554
C1B C1C C2C C5C -178.03(11) .
C4C C1C C2C C5C 59.82(14) .
C3C C1C C2C C5C -58.69(14) .
C1B C1C C3C C7C 176.86(11) .
C4C C1C C3C C7C -60.06(14) .
C2C C1C C3C C7C 58.65(14) .
C1C C2C C5C C1A 179.14(11) .
C1C C2C C5C C8C 59.11(14) .
C1C C2C C5C C9C -59.88(14) .
C7C C8C C5C C1A -179.55(11) .
C7C C8C C5C C2C -59.30(14) .
C7C C8C C5C C9C 59.24(13) .
C1A C5C C9C C6C -179.66(11) .
C2C C5C C9C C6C 59.85(14) .
C8C C5C C9C C6C -59.16(14) .
C5C C9C C6C C10C 60.08(14) .
C5C C9C C6C C4C -60.67(15) .
C1C C3C C7C C10C 60.47(14) .
C1C C3C C7C C8C -59.92(14) .
C5C C8C C7C C10C -60.47(14) .
C5C C8C C7C C3C 60.13(14) .
C10C C6C C4C C1C -59.89(14) .
C9C C6C C4C C1C 60.37(15) .
C1B C1C C4C C6C -178.83(11) .
C3C C1C C4C C6C 59.57(14) .
C2C C1C C4C C6C -59.27(14) .
C3C C7C C10C C6C -59.62(14) .
C8C C7C C10C C6C 61.24(14) .
C4C C6C C10C C7C 59.53(14) .
C9C C6C C10C C7C -61.12(14) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 137266898
