Cyclophane-Sustained Ultrastable Porphyrins.
Liu, Wenqi; Lin, Chenjian; Weber, Jacob Andrew; Stern, Charlotte L.; Young, Ryan M.; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02311

data_4134789
_publ_section_title
;
 Cyclophane-Sustained Ultrastable Porphyrins.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02311
_journal_year                    2020
_chemical_formula_moiety
'C96 H76 N8, C32 H20 N4 Zn, 8(F6 P), 4(C3 H6 O)'
_chemical_formula_sum            'C140 H120 F48 N12 O4 P8 Zn'
_chemical_formula_weight         3259.60
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                108.894(8)
_cell_angle_beta                 106.654(8)
_cell_angle_gamma                102.130(8)
_cell_formula_units_Z            1
_cell_length_a                   14.6658(16)
_cell_length_b                   17.540(2)
_cell_length_c                   19.0390(19)
_cell_measurement_reflns_used    8249
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      58.915
_cell_measurement_theta_min      2.825
_cell_volume                     4184.0(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2017)'
_computing_data_collection       'APEX2 V2017.3 (Bruker, 2017)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.97
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18658
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        59.384
_diffrn_reflns_theta_max         59.384
_diffrn_reflns_theta_min         2.656
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.4206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1122 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.6972. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             1658
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.961
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1011
_refine_ls_number_reflns         11339
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0928
_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/[\s^2^(Fo^2^)+(0.1557P)^2^+4.3299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2544
_refine_ls_wR_factor_ref         0.2863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7410
_reflns_number_total             11339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02311_si_003.cif
_cod_data_source_block           cx1631
_cod_database_code               4134789
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.507
_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. Restrained distances
 F22A-F21A \\sim F22A-F23A \\sim F21A-F24A \\sim F24A-F23A
 with sigma of 0.02
 F24-F21 \\sim F24-F23 \\sim F21-F22 \\sim F23-F22
 with sigma of 0.02
 P4A-F20 \\sim P4A-F19 \\sim P4A-F22A \\sim P4A-F21A \\sim P4A-F24A \\sim
P4A-F23A
 with sigma of 0.01
 P4-F20 \\sim P4-F19 \\sim P4-F24 \\sim P4-F21 \\sim P4-F23 \\sim P4-F22
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 P4, P4A, F21, F21A, F22, F22A, F23, F23A, F24, F24A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(P4A)=Sof(F21A)=Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(1)
 Sof(P4)=Sof(F21)=Sof(F22)=Sof(F23)=Sof(F24)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C24(H24A,H24B), C41(H41A,H41B), C44(H44A,H44B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26),
  C27(H27), C29(H29), C32(H32), C36(H36), C37(H37), C38(H38), C39(H39),
 C40(H40), C42(H42), C43(H43), C45(H45), C46(H46), C47(H47), C48(H48), C50(H50),
  C51(H51), C55(H55), C56(H56), C58(H58), C60(H60), C61(H61), C62(H62),
 C63(H63), C64(H64)
5.c Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C69(H69A,H69B,H69C), C70(H70A,H70B,
 H70C)
;
_shelx_res_checksum              43194
_shelx_hkl_checksum              10113
_shelx_fab_checksum              89263
_olex2_date_sample_data_collection 2019-09-16
_olex2_date_sample_submission    2019-09-15
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with Paratone oil'
_olex2_submission_original_sample_id cx1631
_olex2_submission_special_instructions 'No special instructions were received'