Targeted Synthesis of Regioisomerically Pure Dodecasubstituted Type I Porphyrins through the Exploitation of Peri-interactions.
Kielmann, Marc; Flanagan, Keith J.; Senge, Mathias O.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00798

data_4038417
_publ_section_title
;
 Targeted Synthesis of Regioisomerically Pure Dodecasubstituted Type I
 Porphyrins through the Exploitation of Peri-interactions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00798
_journal_year                    2020
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22
_chemical_name_systematic        'methyl 4-phenyl-1H-pyrrole-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.743(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0408(10)
_cell_length_b                   9.2884(13)
_cell_length_c                   16.116(3)
_cell_measurement_reflns_used    3374
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.05
_cell_volume                     1046.7(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11142
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.374
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0586 before and 0.0508 after correction. The Ratio of minimum to maximum transmission is 0.9277. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0665P)^2^+0.2018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1848
_reflns_number_total             2629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00798_si_005.cif
_cod_data_source_block           kjf304
_cod_database_code               4038417
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.98 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C8(H8), C12(H12), C4(H4), C11(H11), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              41434
_shelx_hkl_checksum              67567
_olex2_submission_special_instructions 'No special instructions were received'