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_1567076
_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         '3(C H4 O), C104 H107 N11, C4 H8 O1'
_chemical_formula_sum            'C111 H127 N11 O4'
_chemical_formula_weight         1679.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-09-16 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                66.8150(10)
_cell_angle_beta                 72.3480(10)
_cell_angle_gamma                74.252(2)
_cell_formula_units_Z            2
_cell_length_a                   14.7293(4)
_cell_length_b                   18.9653(6)
_cell_length_c                   22.0241(6)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      65.12
_cell_measurement_theta_min      2.57
_cell_volume                     5307.4(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0676
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            50076
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        65.643
_diffrn_reflns_theta_max         65.643
_diffrn_reflns_theta_min         2.573
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1089 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.8014.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.051
_exptl_crystal_description       bar
_exptl_crystal_F_000             1804
_refine_diff_density_max         1.143
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.818
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1202
_refine_ls_number_reflns         17902
_refine_ls_number_restraints     134
_refine_ls_restrained_S_all      1.847
_refine_ls_R_factor_all          0.1788
_refine_ls_R_factor_gt           0.1249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3110
_refine_ls_wR_factor_ref         0.3375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10051
_reflns_number_total             17902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01635d2.cif
_cod_data_source_block           t_a_sq
_cod_depositor_comments
'Adding full bibliography for 1567076--1567079.cif.'
_cod_database_code               1567076
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C108-C107 = C106-C107 = C106-C105 = C1C-C1A = C1B-C1C = C1B-C1D
 1.54 with sigma of 0.01
 O4A-C1A = O4A-C1D = O4-C108 = O4-C105
 1.47 with sigma of 0.01
3. Rigid bond restraints
 C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C89, C90
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C79, C83
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C43, C44
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O4 \\sim C105 \\sim C106 \\sim C107 \\sim C108 \\sim O4A \\sim C1A \\sim C1B
\\sim C1C \\sim C1D: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
Uanis(C1C) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(C1D)
\\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(O4) \\sim Ueq,
Uanis(C105) \\sim Ueq, Uanis(C108) \\sim Ueq, Uanis(C106) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(O4A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C1C)=
 Sof(H1CA)=Sof(H1CB)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=1-FVAR(1)
 Sof(O4)=Sof(C105)=Sof(H10A)=Sof(H10B)=Sof(C106)=Sof(H10C)=Sof(H10D)=Sof(C107)=
 Sof(H10E)=Sof(H10F)=Sof(C108)=Sof(H10G)=Sof(H10H)=FVAR(1)
6.a Riding coordinates:
 O2(H2A)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C14(H14A,H14B), C16(H16A,H16B), C23(H23A,H23B),
 C25(H25A,H25B), C43(H43A,H43B), C45(H45A,H45B), C52(H52A,H52B), C54(H54A,H54B),
  C61(H61A,H61B), C63(H63A,H63B), C81(H81A,H81B), C83(H83A,H83B), C89(H89A,
 H89B), C91(H91A,H91B), C105(H10A,H10B), C106(H10C,H10D), C107(H10E,H10F),
 C108(H10G,H10H), C1A(H1AA,H1AB), C1B(H1BA,H1BB), C1C(H1CA,H1CB), C1D(H1DA,H1DB)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), N8(H8), N10(H10), C9(H9), C28(H28),
 C29(H29), C32(H32), C33(H33), C35(H35), C38(H38), C56(H56), C66(H66), C67(H67),
  C70(H70), C71(H71), C73(H73), C76(H76), C94(H94), C97(H97), C99(H99),
 C100(H100), C103(H103), C104(H104)
6.d Idealised Me refined as rotating group:
 C111(H11A,H11B,H11C), C109(H10I,H10J,H10K), C110(H11D,H11E,H11F), C6(H6A,H6B,
 H6C), C8(H8A,H8B,H8C), 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), C62(H62A,H62B,H62C), C64(H64A,H64B,H64C),
 C82(H82A,H82B,H82C), C84(H84A,H84B,H84C), C90(H90A,H90B,H90C), C92(H92A,H92B,
 H92C)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_shelx_res_checksum              49848
_shelx_fab_checksum              2347
_olex2_submission_special_instructions 'No special instructions were received'