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

data_7155944
_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         'C34 H31 N, 1(C6 H6)'
_chemical_formula_sum            'C40 H37 N'
_chemical_formula_weight         531.70
_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             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                99.880(3)
_cell_angle_beta                 95.857(3)
_cell_angle_gamma                116.117(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8521(3)
_cell_length_b                   10.1991(4)
_cell_length_c                   16.8567(6)
_cell_measurement_reflns_used    9158
_cell_measurement_temperature    290.81(10)
_cell_measurement_theta_max      73.6738
_cell_measurement_theta_min      2.7138
_cell_volume                     1467.80(10)
_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
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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_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      290.81(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega  -46.00   31.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063   37.0000  -60.0000 77

  2 omega  -42.00    3.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063   37.0000  120.0000 45

  3 omega -120.00   -3.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063  -19.0000  120.0000 117

  4 omega   38.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9063 -125.0000   30.0000 47

  5 omega    2.00   34.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9063  -99.0000   30.0000 32

  6 omega   35.00   96.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9063 -125.0000 -180.0000 61

  7 omega   42.00   87.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000  -90.0000 45

  8 omega   40.00  109.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -94.0000  120.0000 69

  9 omega   66.00   91.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000    0.0000 25

 10 omega   46.00   90.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000   90.0000 44

 11 omega   47.00  177.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   15.0000 -180.0000 130

 12 omega   36.00   62.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000 -150.0000 26

 13 omega   32.00   90.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000 -150.0000 58

 14 omega   27.00  106.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -94.0000   30.0000 79

 15 omega   94.00  128.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -77.0000  170.0000 34

 16 omega   33.00   86.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000    0.0000 53

 17 omega  120.00  176.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   45.0000 -150.0000 56

 18 omega   33.00   96.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000  150.0000 63

 19 omega   72.00  101.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -94.0000 -180.0000 29

 20 omega   67.00  121.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -125.0000    0.0000 54

 21 omega -114.00  -10.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063  -57.0000   60.0000 104

 22 omega -114.00  -10.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9063  -57.0000  -30.0000 104

 23 omega    1.00   82.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9063  -99.0000 -180.0000 81

 24 omega    6.00  119.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9063   77.0000 -180.0000 113

 25 omega    6.00  119.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9063   77.0000  -90.0000 113

 26 omega   80.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   45.0000  -90.0000 98

 27 omega   46.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   15.0000   30.0000 132

 28 omega   74.00   99.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   77.0000   60.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1636011000
_diffrn_orient_matrix_UB_12      0.1181091000
_diffrn_orient_matrix_UB_13      0.0465841000
_diffrn_orient_matrix_UB_21      -0.0105843000
_diffrn_orient_matrix_UB_22      -0.0933399000
_diffrn_orient_matrix_UB_23      0.0641024000
_diffrn_orient_matrix_UB_31      0.0687335000
_diffrn_orient_matrix_UB_32      -0.0860479000
_diffrn_orient_matrix_UB_33      -0.0518448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15594
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.837
_diffrn_reflns_theta_min         2.716
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93897
_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             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         5810
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.4176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5245
_reflns_number_total             5810
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02537h2.cif
_cod_data_source_block           3b
_cod_original_cell_volume        1467.81(10)
_cod_database_code               7155944
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C24H19N
_reflns_odcompleteness_completeness 99.98
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C37A-C36A \\sim C38A-C37A \\sim C38B-C37B \\sim C37B-C36B \\sim C41A-C36A
\\sim C41B-C36B \\sim C41B-
 C40B \\sim C41A-C40A \\sim C40B-C39B \\sim C40A-C39A \\sim C39B-C38B \\sim
C39A-C38A
 with sigma of 0.002
3. Others
 Sof(C36B)=Sof(H36B)=Sof(C41B)=Sof(H41B)=Sof(C37B)=Sof(H37B)=Sof(C38B)=
 Sof(H38B)=Sof(C39B)=Sof(H39B)=Sof(C40B)=Sof(H40B)=1-FVAR(1)
 Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=Sof(C39A)=Sof(H39A)=Sof(C40A)=
 Sof(H40A)=Sof(C41A)=Sof(H41A)=Sof(C36A)=Sof(H36A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C15(H15), C17(H17), C18(H18), C23(H23), C24(H24),
 C26(H26), C27(H27), C30(H30), C31(H31), C33(H33), C34(H34), C36B(H36B),
 C37A(H37A), C38A(H38A), C39A(H39A), C40A(H40A), C41A(H41A), C41B(H41B),
 C37B(H37B), C38B(H38B), C39B(H39B), C40B(H40B), C36A(H36A)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C28(H28A,H28B,
 H28C), C35(H35A,H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'