Unexpected formation of [5]helicenes from hexaarylbenzenes containing pyrrole moieties
Ammon, Felix; Sauer, Stephanie Theresia; Lippert, Rainer; Lungerich, Dominik; Reger, David; Hampel, Frank; Jux, Norbert; Organic Chemistry Frontiers 4 (2017) 861–; doi:10.1039/C7QO00112F

data_1553742
_publ_section_title
;
 Unexpected formation of [5]helicenes from hexaarylbenzenes containing
 pyrrole moieties
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              861
_journal_paper_doi               10.1039/C7QO00112F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C11 H8 N O2 S'
_chemical_formula_sum            'C11 H8 N O2 S'
_chemical_formula_weight         218.24
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-01-12 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.927(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.69674(11)
_cell_length_b                   8.92923(16)
_cell_length_c                   19.6982(5)
_cell_measurement_reflns_used    2683
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      61.5490
_cell_measurement_theta_min      4.4920
_cell_volume                     998.30(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.843
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     16.00  90.00   1.00    1.00    --   82.59 -30.00 -90.00   74
  2  \w     58.00 121.00   1.00    1.00    --   82.59  45.00-180.00   63
  3  \w     58.00 115.00   1.00    1.00    --   82.59  45.00-120.00   57
  4  \w     52.00 150.00   1.00    1.00    --   82.59  77.00  30.00   98
  5  \w     19.00 132.00   1.00    1.00    --   82.59 -15.00 -30.00  113
  6  \w     30.00 117.00   1.00    1.00    --   82.59-125.00-120.00   87
  7  \w     20.00  98.00   1.00    1.00    --   82.59 -77.00 -90.00   78
  8  \w    -64.00  25.00   1.00    1.00    --    0.00 -38.00-180.00   89
  9  \w    -86.00 -34.00   1.00    1.00    --    0.00 178.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1996531000
_diffrn_orient_matrix_UB_12      0.1169307000
_diffrn_orient_matrix_UB_13      -0.0033195000
_diffrn_orient_matrix_UB_21      0.0554304000
_diffrn_orient_matrix_UB_22      0.0433720000
_diffrn_orient_matrix_UB_23      -0.0725845000
_diffrn_orient_matrix_UB_31      -0.1751819000
_diffrn_orient_matrix_UB_32      -0.1193844000
_diffrn_orient_matrix_UB_33      -0.0296444000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.843
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4209
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         61.416
_diffrn_reflns_theta_min         4.506
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_recrystallization_method 'crystallized from toluene/hexanes'
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0690P)^2^+0.5343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1376
_reflns_number_total             1524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00112f2.cif
_cod_data_source_block           16jux-fa01
_cod_database_code               1553742
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C22 H16 N2 O4 S2'
_reflns_odcompleteness_completeness 96.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.05
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C2(H2), C15(H15), C3(H3), C12(H12), C6(H6), C4(H4)
;
_olex2_date_sample_data_collection 2016-03-01
_olex2_exptl_crystal_mounting_method 'mounted on a loop'
_olex2_submission_original_sample_id FA143
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.729