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

data_7155945
_publ_section_title
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 Photochemical and oxidative cyclisation of tetraphenylpyrroles
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_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02537H
_journal_year                    2017
_chemical_formula_moiety         'C30 H17 Cl4 N'
_chemical_formula_sum            'C30 H17 Cl4 N'
_chemical_formula_weight         533.24
_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
_audit_creation_date             2015-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-10-01 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                64.541(2)
_cell_angle_beta                 74.712(2)
_cell_angle_gamma                75.154(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9632(3)
_cell_length_b                   11.2079(3)
_cell_length_c                   11.9471(4)
_cell_measurement_reflns_used    6857
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.65
_cell_measurement_theta_min      2.71
_cell_volume                     1146.17(6)
_computing_cell_refinement       'SAINT v7.53A (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29287
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.148
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0546 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.8812.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         6617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0475P)^2^+0.7464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4627
_reflns_number_total             6617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02537h2.cif
_cod_data_source_block           6
_cod_original_cell_volume        1146.18(6)
_cod_database_code               7155945
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.774
_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:
 C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20),
 C22(H22), C26(H26), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'