Photochemical and oxidative cyclisation of tetraphenylpyrroles
Ferguson, Jayne L.; Squire, Marie A.; Fitchett, Christopher M.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02537H

data_7155946
_publ_section_title
;
 Photochemical and oxidative cyclisation of tetraphenylpyrroles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02537H
_journal_year                    2017
_chemical_formula_moiety         'C35 H25 N'
_chemical_formula_sum            'C35 H25 N'
_chemical_formula_weight         459.56
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2017-10-01 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.158(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1062(2)
_cell_length_b                   13.1190(3)
_cell_length_c                   18.1079(4)
_cell_measurement_reflns_used    3441
_cell_measurement_temperature    287.84(10)
_cell_measurement_theta_max      73.8080
_cell_measurement_theta_min      3.3660
_cell_volume                     2382.09(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      287.84(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega   -9.00   32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.9373   37.0000  -60.0000 41

  2 omega  -45.00  -19.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.9373   37.0000   30.0000 26

  3 omega  -34.00   22.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.9373   37.0000 -180.0000 56

  4 omega -112.00  -11.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.9373  -57.0000   60.0000 101

  5 omega  -16.00   25.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.9373   37.0000   30.0000 41

  6 omega   25.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -94.0000  150.0000 80

  7 omega   50.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -30.0000  150.0000 29

  8 omega   33.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -45.0000 -150.0000 61

  9 omega   52.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -30.0000  -60.0000 39

 10 omega   46.00   85.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -30.0000   60.0000 39

 11 omega   97.00  123.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  125.0000    0.0000 26

 12 omega  140.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  125.0000    0.0000 36

 13 omega   36.00   97.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -45.0000  -90.0000 61

 14 omega   39.00   93.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -45.0000  120.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1476658000
_diffrn_orient_matrix_UB_12      -0.0286899000
_diffrn_orient_matrix_UB_13      -0.0005298000
_diffrn_orient_matrix_UB_21      -0.0086700000
_diffrn_orient_matrix_UB_22      0.0327158000
_diffrn_orient_matrix_UB_23      -0.0821317000
_diffrn_orient_matrix_UB_31      0.0413642000
_diffrn_orient_matrix_UB_32      0.1091744000
_diffrn_orient_matrix_UB_33      0.0244702000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9069
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.972
_diffrn_reflns_theta_min         4.173
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0522P)^2^+0.5055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3749
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02537h2.cif
_cod_data_source_block           5a
_cod_original_cell_volume        2382.11(10)
_cod_database_code               7155946
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C30H20N1
_reflns_odcompleteness_completeness 99.91
_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 C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
;
_olex2_submission_special_instructions 'No special instructions were received'