1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls.
Liu, Shi; Roch, Loïc M; Allemann, Oliver; Xu, Jun; Vanthuyne, Nicolas; Baldridge, Kim K.; Siegel, Jay S.; The Journal of organic chemistry 83 (2018) 3979–3986; doi:10.1021/acs.joc.8b00320

data_4035466
_publ_section_title
;
 1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and
 Chirality of Corannulene Bowls.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3979
_journal_page_last               3986
_journal_paper_doi               10.1021/acs.joc.8b00320
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C34 H18'
_chemical_formula_sum            'C34 H18'
_chemical_formula_weight         426.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.3604(4)
_cell_length_b                   9.2591(2)
_cell_length_c                   8.11380(10)
_cell_measurement_reflns_used    5660
_cell_measurement_temperature    100.01(16)
_cell_measurement_theta_max      73.1260
_cell_measurement_theta_min      5.0380
_cell_volume                     1980.36(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(16)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -29.00  89.00   0.50    9.00    --    0.00  57.00-120.00  236
  2  \w    -29.00  89.00   0.50    9.00    --    0.00  57.00-180.00  236
  3  \w      9.00 128.00   0.50   45.00    --   98.20 -45.00 -60.00  238
  4  \w      9.00 135.00   0.50   45.00    --   98.20 -77.00 -90.00  252
  5  \w      9.00 130.00   0.50   45.00    --   98.20 -61.00 120.00  242
  6  \w      9.00 137.00   0.50   45.00    --   98.20 -82.00 120.00  256
  7  \w     69.00 188.00   0.50   45.00    --   98.20  45.00  60.00  238
  8  \w    -31.00  89.00   0.50    9.00    --    0.00  38.00   0.00  240
  9  \w    -31.00  89.00   0.50    9.00    --    0.00  38.00 120.00  240
 10  \w     28.00 188.00   0.50   45.00    --   98.20  15.00 -30.00  320
 11  \w     58.00 188.00   0.50   45.00    --   98.20  24.00  27.00  260
 12  \w     63.00 188.00   0.50   45.00    --   98.20  30.00-180.00  250
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0336328000
_diffrn_orient_matrix_UB_12      0.0310488000
_diffrn_orient_matrix_UB_13      -0.1511299000
_diffrn_orient_matrix_UB_21      0.0440707000
_diffrn_orient_matrix_UB_22      -0.0424017000
_diffrn_orient_matrix_UB_23      -0.1148743000
_diffrn_orient_matrix_UB_31      -0.0184627000
_diffrn_orient_matrix_UB_32      -0.1579278000
_diffrn_orient_matrix_UB_33      0.0011007000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9115
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.269
_diffrn_reflns_theta_min         5.063
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             888
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0478P)^2^+0.5523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                1878
_reflns_number_total             1961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00320_si_004.cif
_cod_data_source_block           20170929---tju
_cod_database_code               4035466
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C17(H17), C6(H6), C1(H1), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C18(H18C,H18B,H18A)
;
_shelx_res_checksum              13116
_shelx_hkl_checksum              76261
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.392
_oxdiff_exptl_absorpt_empirical_full_min 0.850