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

data_7155948
_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         'C39 H33 N, C6 H6'
_chemical_formula_sum            'C45 H39 N'
_chemical_formula_weight         593.77
_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
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Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
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2017-10-01 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   22.2920(4)
_cell_measurement_reflns_used    8708
_cell_measurement_temperature    120.01(10)
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_cell_measurement_theta_min      2.6689
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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  1 omega  -48.00   24.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012   37.0000 -180.0000 72

  2 omega  -49.00   21.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012   37.0000  -60.0000 70

  3 omega -117.00  -67.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012 -155.0000  -63.0000 50

  4 omega   59.00   97.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9012 -125.0000 -150.0000 38

  5 omega   40.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000   90.0000 31

  6 omega   82.00  108.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000   90.0000 26

  7 omega   48.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -30.0000 -120.0000 42

  8 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000  150.0000 25

  9 omega   88.00  169.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   39.00   66.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000  150.0000 27

 11 omega   41.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -30.0000 -150.0000 42

 12 omega   24.00   59.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000    0.0000 35

 13 omega   73.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000    0.0000 36

 14 omega  137.00  165.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  119.0000   -2.0000 28

 15 omega   24.00   88.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000  -90.0000 64

 16 omega   46.00   78.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -30.0000  -30.0000 32

 17 omega -114.00  -10.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012  -57.0000  -90.0000 104

 18 omega -114.00  -10.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012  -57.0000   30.0000 104

 19 omega  -96.00   -2.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012  125.0000  -60.0000 94

 20 omega -114.00  -10.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012  -57.0000  150.0000 104
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1249013000
_diffrn_orient_matrix_UB_12      0.0441318000
_diffrn_orient_matrix_UB_13      0.0379408000
_diffrn_orient_matrix_UB_21      0.1562794000
_diffrn_orient_matrix_UB_22      -0.0432683000
_diffrn_orient_matrix_UB_23      0.0299716000
_diffrn_orient_matrix_UB_31      0.1646734000
_diffrn_orient_matrix_UB_32      0.0075961000
_diffrn_orient_matrix_UB_33      -0.0496131000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
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_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18660
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.820
_diffrn_reflns_theta_min         2.671
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87964
_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    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.653
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_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0634P)^2^+3.0337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                5731
_reflns_number_total             6468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02537h2.cif
_cod_data_source_block           5b
_cod_original_cell_volume        3279.02(11)
_cod_database_code               7155948
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C39H33N1
_reflns_odcompleteness_completeness 99.85
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C15(H15), C17(H17), C18(H18), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32), C35(H35),
  C36(H36), C38(H38), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44),
 C45(H45), C46(H46)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C33(H33A,H33B,H33C), C40(H40A,H40B,
 H40C)
;
_olex2_submission_special_instructions 'No special instructions were received'