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_7125385
_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         'C52 H30 N2 O4 S, C H Cl3'
_chemical_formula_sum            'C53 H31 Cl3 N2 O4 S'
_chemical_formula_weight         898.21
_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
_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                109.732(6)
_cell_angle_beta                 92.669(5)
_cell_angle_gamma                92.147(5)
_cell_formula_units_Z            2
_cell_length_a                   11.9568(7)
_cell_length_b                   12.3682(8)
_cell_length_c                   14.6936(10)
_cell_measurement_reflns_used    6512
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1020
_cell_measurement_theta_min      3.1610
_cell_volume                     2039.9(2)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.941
_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    -65.00  30.00   1.00   10.00    --  -42.42  38.00  60.00   95
  2  \w    -69.00  28.00   1.00   10.00    --  -42.42  57.00 -90.00   97
  3  \w   -113.00 -16.00   1.00   10.00    --  -42.42 -57.00 120.00   97
  4  \w      1.00  82.00   1.00   10.00    --   42.42 -99.00  60.00   81
  5  \w     80.00 178.00   1.00   30.00    --  111.00  77.00 120.00   98
  6  \w     94.00 178.00   1.00   30.00    --  111.00 125.00   0.00   84
  7  \w     37.00 142.00   1.00   30.00    --  111.00 -77.00  30.00  105
  8  \w     40.00 135.00   1.00   30.00    --  111.00 -45.00 -30.00   95
  9  \w     83.00 178.00   1.00   30.00    --  111.00  61.00  60.00   95
 10  \w     30.00 109.00   1.00   30.00    --  111.00 -94.00 -60.00   79
 11  \w     39.00 121.00   1.00   30.00    --  111.00-125.00-120.00   82
 12  \w     87.00 178.00   1.00   30.00    --  111.00  45.00  90.00   91
 13  \w     87.00 178.00   1.00   30.00    --  111.00  45.00-180.00   91
 14  \w   -113.00 -16.00   1.00   10.00    --  -42.42 -57.00 -60.00   97
 15  \w   -113.00 -16.00   1.00   10.00    --  -42.42 -57.00-150.00   97
 16  \w    -65.00  30.00   1.00   10.00    --  -42.42  38.00-180.00   95
 17  \w   -116.00 -11.00   1.00   10.00    --  -42.42 -77.00  30.00  105
 18  \w     87.00 132.00   1.00   30.00    --  111.00  30.00 -30.00   45
;
_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      0.1106269000
_diffrn_orient_matrix_UB_12      0.0560264000
_diffrn_orient_matrix_UB_13      -0.0171333000
_diffrn_orient_matrix_UB_21      0.0276404000
_diffrn_orient_matrix_UB_22      -0.1153124000
_diffrn_orient_matrix_UB_23      -0.0754066000
_diffrn_orient_matrix_UB_31      -0.0607290000
_diffrn_orient_matrix_UB_32      0.0336305000
_diffrn_orient_matrix_UB_33      -0.0804766000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.1040
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18981
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.890
_diffrn_reflns_theta_min         3.202
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61706
_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            brown
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.623
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0885
_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^)+(0.0836P)^2^+9.6739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2358
_refine_ls_wR_factor_ref         0.2528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6012
_reflns_number_total             8001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04607k2.cif
_cod_data_source_block           Compound7
_cod_database_code               7125385
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C50H80N8O4F20Cl3
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C52(H52)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C15(H15),
 C16(H16), C20(H20), C21(H21), C26(H26), C27(H27), C28(H28), C29(H29), C35(H35),
  C36(H36), C37(H37), C38(H38), C41(H41), C42(H42), C43(H43), C44(H44),
 C45(H45), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51)
;
_shelx_res_checksum              63571
_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 1.785
_oxdiff_exptl_absorpt_empirical_full_min 0.181