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

data_7155947
_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'
_chemical_formula_sum            'C39 H33 N'
_chemical_formula_weight         515.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-28
_audit_creation_method
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Olex2 1.2
(compiled Aug 10 2017 17:28:52 for OlexSys, GUI svn.r5381)
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_audit_update_record
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2017-10-01 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                109.469(4)
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_cell_angle_gamma                91.218(4)
_cell_formula_units_Z            2
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_cell_measurement_reflns_used    4917
_cell_measurement_temperature    120.00(10)
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_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
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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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_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 10.6501
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_diffrn_measured_fraction_theta_max 0.966
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;
  1 omega  -48.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063   37.0000  120.0000 83

  2 omega  -28.00   23.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063   37.0000  -90.0000 51

  3 omega  -48.00    8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063   37.0000   60.0000 56

  4 omega  -91.00   -4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063  125.0000  120.0000 87

  5 omega  -89.00  -26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063  -37.0000  -90.0000 63

  6 omega   52.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9063 -125.0000    0.0000 41

  7 omega   55.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000 -120.0000 36

  8 omega   31.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -77.0000  120.0000 105

  9 omega   34.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -125.0000  -30.0000 87

 10 omega   31.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000  -60.0000 59

 11 omega   60.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000 -120.0000 27

 12 omega   33.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -125.0000   30.0000 58

 13 omega   93.00  119.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -125.0000   30.0000 26

 14 omega   39.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000  120.0000 40

 15 omega   69.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -94.0000   90.0000 40

 16 omega   32.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000 -180.0000 44

 17 omega   79.00  154.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   30.0000   90.0000 75

 18 omega   56.00  133.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -61.0000  -30.0000 77

 19 omega  114.00  142.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -15.0000   60.0000 28

 20 omega   26.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -15.0000   60.0000 77

 21 omega -116.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063  -69.0000   19.0000 106

 22 omega -114.00  -85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063  -57.0000  120.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1415708000
_diffrn_orient_matrix_UB_12      -0.0385122000
_diffrn_orient_matrix_UB_13      0.0072389000
_diffrn_orient_matrix_UB_21      0.0048512000
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_diffrn_orient_matrix_UB_33      -0.0816377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10379
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.961
_diffrn_reflns_theta_min         3.775
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.529
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_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    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.300
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_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
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_refine_ls_number_reflns         5488
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.4486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4674
_reflns_number_total             5488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02537h2.cif
_cod_data_source_block           4b
_cod_original_cell_volume        1398.13(12)
_cod_database_code               7155947
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C39H40N1
_reflns_odcompleteness_completeness 99.98
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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:
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22),
 C24(H24), C25(H25), C28(H28), C29(H29), C31(H31), C32(H32), C36(H36), C37(H37),
  C38(H38), C39(H39), C40(H40)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C33(H33A,H33B,
 H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'