meso-Alkylidenyl dibenzihexaphyrins: synthesis and protonation studies.
Hong, Seong-Jin; Dutta, Ranjan; Kumar, Ravi; He, Qing; Lynch, Vincent M.; Sessler, Jonathan L.; Lee, Chang-Hee; Chemical communications (Cambridge, England) 55 (2019) 9693–9696; doi:10.1039/c9cc04607k

data_7125387
_publ_section_title
;
 meso-Alkylidenyl dibenzihexaphyrins: synthesis and protonation studies.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9693
_journal_page_last               9696
_journal_paper_doi               10.1039/c9cc04607k
_journal_volume                  55
_journal_year                    2019
_chemical_formula_moiety
'C41 H18 F5 N2 O4, C H Cl3, C2 F3 O2, C2 H F3 O2'
_chemical_formula_sum            'C18 H15 Cl0 F0 N4 O'
_chemical_formula_weight         303.34
_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
_audit_creation_date             2019-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-06 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                70.698(3)
_cell_angle_beta                 66.001(3)
_cell_angle_gamma                67.022(3)
_cell_formula_units_Z            2
_cell_length_a                   12.9539(16)
_cell_length_b                   14.4757(18)
_cell_length_c                   14.7250(18)
_cell_measurement_reflns_used    20264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.99
_cell_volume                     2273.4(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32004
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.993
_exptl_absorpt_coefficient_mu    0.029
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    0.443
_exptl_crystal_description       block
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     663
_refine_ls_number_reflns         8323
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0756P)^2^+2.2322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7323
_reflns_number_total             8323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04607k2.cif
_cod_data_source_block           Compound5TFA
_cod_database_code               7125387
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 O5-H5
 0.84 with sigma of 0.01
 C39-F8 \\sim C39-F8A
 with sigma of 0.02
 C39-F9 \\sim C39-F9A
 with sigma of 0.02
 C39-F10 \\sim C39-F10A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F8 \\sim F9 \\sim F10 \\sim F8A \\sim F9A \\sim F10A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F8A)
\\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(F10A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(F10A)=Sof(F9A)=Sof(F8A)=1-FVAR(1)
 Sof(F8)=Sof(F9)=Sof(F10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C40(H40)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
  C17(H17), C21(H21), C22(H22), C24(H24), C25(H25), C30(H30), C31(H31),
 C32(H32), C33(H33)
;
_shelx_res_checksum              79624
_shelx_fab_checksum              84614
_olex2_submission_special_instructions 'No special instructions were received'