Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional boron difluoride arrays
Zhou, Weinan; Sarma, Tridib; Yang, Liu; Lei, Chuanhu; Sessler, Jonathan L.; Chemical Science 13 (2022) 7276–7282; doi:10.1039/D2SC01635D

data_1567077
_publ_section_title
;
 Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional
 boron difluoride arrays
;
_journal_issue                   24
_journal_name_full               'Chemical Science'
_journal_page_first              7276
_journal_page_last               7282
_journal_paper_doi               10.1039/D2SC01635D
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C104 H101 B4 F8 N11, 5(C H4 O)'
_chemical_formula_sum            'C109 H121 B4 F8 N11 O5'
_chemical_formula_weight         1860.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2251(4)
_cell_length_b                   23.1997(7)
_cell_length_c                   28.8441(8)
_cell_measurement_reflns_used    9297
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      67.68
_cell_measurement_theta_min      2.44
_cell_volume                     11526.6(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            76414
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.405
_diffrn_reflns_theta_min         2.444
_diffrn_source_current           45.0
_diffrn_source_power             2.25
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5981
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0920 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.7942.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_description       bar
_exptl_crystal_F_000             3936
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 5605 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1299
_refine_ls_number_reflns         20956
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0823
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1908P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2518
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                15514
_reflns_number_total             20956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01635d2.cif
_cod_data_source_block           t_a_sq_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1567076--1567079.cif.'
_cod_database_code               1567077
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C24A-C23 = C24-C23
 1.54 with sigma of 0.01
 C15-C14 = C15A-C14
 1.54 with sigma of 0.01
 C72A-C69 = C72-C69
 1.51 with sigma of 0.01
 C73-C72 = C73A-C72A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C24A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C15A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C72) \\sim Ueq, Uanis(C72A) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C73A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
 Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(2)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(2)
 Sof(C72A)=Sof(H72C)=Sof(H72D)=Sof(C73A)=Sof(H73D)=Sof(H73E)=Sof(H73F)=1-FVAR(3)
 Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(H73C)=FVAR(3)
5.a Riding coordinates:
 O4(H4), C108(H10U,H10V,H10W), C24A(H24D,H24E,H24F)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C14(H14C,H14D), C23(H23A,H23B), C23(H23C,
 H23D), C25(H25A,H25B), C43(H43A,H43B), C45(H45A,H45B), C52(H52A,H52B),
 C54(H54A,H54B), C72(H72A,H72B), C74(H74A,H74B), C81(H81A,H81B), C83(H83A,H83B),
  C101(H10B,H10C), C103(H10G,H10H), C72A(H72C,H72D)
5.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N10(H10), N11(H11), C5(H5A), C10(H10A), C16(H16), C28(H28), C31(H31),
 C32(H32), C34(H34), C35(H35), C37(H37), C57(H57), C58(H58), C61(H61), C62(H62),
  C64(H64), C67(H67), C76(H76), C86(H86), C87(H87), C90(H90), C91(H91),
 C93(H93), C96(H96)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C44(H44A,H44B,H44C), C46(H46A,
 H46B,H46C), C53(H53A,H53B,H53C), C55(H55A,H55B,H55C), C73(H73A,H73B,H73C),
 C75(H75A,H75B,H75C), C82(H82A,H82B,H82C), C84(H84A,H84B,H84C), C102(H10D,H10E,
 H10F), C104(H10I,H10J,H10K), C106(H10L,H10M,H10N), C105(H10O,H10P,H10Q),
 C107(H10R,H10S,H10T), C109(H10X,H10Y,H), C15A(H15D,H15E,H15F), C73A(H73D,H73E,
 H73F)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O5(H5B)
;
_shelx_res_checksum              10069
_shelx_fab_checksum              5599
_olex2_submission_special_instructions 'No special instructions were received'