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_7125388
_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         '2(C82 H34 F10 N4 O8), 4(C H Cl3)'
_chemical_formula_sum            'C168 H72 Cl12 F20 N8 O16'
_chemical_formula_weight         3263.73
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-06-06 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.269(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5016(3)
_cell_length_b                   35.2797(7)
_cell_length_c                   23.3317(6)
_cell_measurement_reflns_used    9272
_cell_measurement_temperature    99.95(18)
_cell_measurement_theta_max      67.4920
_cell_measurement_theta_min      2.5060
_cell_volume                     16052.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00  32.00   1.00   31.51    --  -41.34  57.00-120.00  101
  2  \w   -113.00 -13.00   1.00   31.51    --  -41.34 -57.00  90.00  100
  3  \w     23.00  97.00   1.00   31.51    --   41.34-125.00-180.00   74
  4  \w     35.00 134.00   1.00  110.00    --  108.34 -45.00  30.00   99
  5  \w     80.00 178.00   1.00  110.00    --  108.34  30.00-150.00   98
  6  \w     26.00 104.00   1.00  110.00    --  108.34 -94.00   0.00   78
  7  \w     94.00 178.00   1.00  110.00    --  108.34 125.00   0.00   84
  8  \w     94.00 178.00   1.00  110.00    --  108.34 125.00 -30.00   84
  9  \w   -113.00 -13.00   1.00   31.51    --  -41.34 -57.00 -90.00  100
 10  \w    -33.00  66.00   1.00   31.51    --   41.34 -38.00 -60.00   99
 11  \w     83.00 178.00   1.00  110.00    --  108.34  45.00  90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0176256000
_diffrn_orient_matrix_UB_12      -0.0088952000
_diffrn_orient_matrix_UB_13      -0.0630170000
_diffrn_orient_matrix_UB_21      -0.0388651000
_diffrn_orient_matrix_UB_22      -0.0358374000
_diffrn_orient_matrix_UB_23      0.0190291000
_diffrn_orient_matrix_UB_31      -0.0664702000
_diffrn_orient_matrix_UB_32      0.0233118000
_diffrn_orient_matrix_UB_33      0.0052186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.1222
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            91104
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.156
_diffrn_reflns_theta_min         2.266
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       needle
_exptl_crystal_F_000             6592
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2017
_refine_ls_number_reflns         31428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1770
_refine_ls_R_factor_gt           0.0943
_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^)+(0.1449P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2450
_refine_ls_wR_factor_ref         0.3053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14417
_reflns_number_total             31428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04607k2.cif
_cod_data_source_block           Compound5
_cod_database_code               7125388
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C100H120N8O8F12Cl10
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C168(H168), C165(H165), C166(H166), C167(H167)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), N4(H4A), C6(H6), C7(H7), C10(H10), C11(H11), C15(H15),
  C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28),
 C32(H32), C33(H33), C38(H38), C39(H39), C40(H40), C41(H41), C47(H47), C48(H48),
  C49(H49), C50(H50), C62(H62), C63(H63), C64(H64), C65(H65), C71(H71),
 C72(H72), C73(H73), C74(H74), N6(H6A), N8(H8), C85(H85), C86(H86), C88(H88),
 C89(H89), C92(H92), C93(H93), C97(H97), C98(H98), C102(H102), C103(H103),
 C105(H105), C106(H106), C109(H109), C110(H110), C114(H114), C115(H115),
 C120(H120), C121(H121), C122(H122), C123(H123), C129(H129), C130(H130),
 C131(H131), C132(H132), C144(H144), C145(H145), C146(H146), C147(H147),
 C153(H153), C154(H154), C155(H155), C156(H156)
;
_shelx_res_checksum              99416
_shelx_fab_checksum              69593
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.797
_oxdiff_exptl_absorpt_empirical_full_min 0.663