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_7125386
_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         '0.89(C82 H38 F10 N4 O10), 1.78(O)'
_chemical_formula_sum            'C72.89 H33.78 Cl0 F8.89 N3.56 O10.67'
_chemical_formula_weight         1298.81
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-06
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            9
_cell_length_a                   20.1536(4)
_cell_length_b                   20.1536(4)
_cell_length_c                   55.493(2)
_cell_measurement_reflns_used    10257
_cell_measurement_temperature    99.97(16)
_cell_measurement_theta_max      71.3530
_cell_measurement_theta_min      3.1760
_cell_volume                     22539.5(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.959
_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    -59.00  30.00   1.00   15.00    --  -42.42  38.00 -60.00   89
  2  \w   -113.00 -25.00   1.00   15.00    --  -42.42 -57.00 150.00   88
  3  \w     64.00 111.00   1.00   15.00    --   42.42 170.00  78.00   47
  4  \w     45.00  93.00   1.00   60.00    --  111.00 -94.00 -30.00   48
  5  \w     42.00 125.00   1.00   60.00    --  111.00 -77.00  60.00   83
  6  \w     59.00 140.00   1.00   60.00    --  111.00 -77.00-180.00   81
  7  \w     49.00 132.00   1.00   60.00    --  111.00 -45.00 150.00   83
  8  \w     43.00 133.00   1.00   60.00    --  111.00 -45.00  60.00   90
  9  \w     87.00 174.00   1.00   60.00    --  111.00  30.00-120.00   87
;
_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      0.0695712000
_diffrn_orient_matrix_UB_12      -0.0193591000
_diffrn_orient_matrix_UB_13      0.0091079000
_diffrn_orient_matrix_UB_21      -0.0199357000
_diffrn_orient_matrix_UB_22      0.0203207000
_diffrn_orient_matrix_UB_23      0.0257706000
_diffrn_orient_matrix_UB_31      -0.0246531000
_diffrn_orient_matrix_UB_32      -0.0710795000
_diffrn_orient_matrix_UB_33      0.0049050000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       69
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            47049
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.128
_diffrn_reflns_theta_min         3.487
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.861
_exptl_crystal_description       block
_exptl_crystal_F_000             5952
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.33
_refine_diff_density_max         1.468
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         11321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.1311
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3318
_refine_ls_wR_factor_ref         0.3889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5696
_reflns_number_total             11321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04607k2.cif
_cod_data_source_block           Compound8
_cod_original_cell_volume        22539.3(12)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7125386
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C100H120N8O8F10Cl8
_chemical_oxdiff_usercomment     'red block'
_reflns_odcompleteness_completeness 98.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C19(H19), C28(H28), C29(H29), C30(H30), C32(H32), C36(H36), C37(H37),
  C38(H38), C39(H39)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_shelx_res_checksum              51689
_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 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.815