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_4035465
_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, 0.25(C7 H8)'
_chemical_formula_sum            'C35.75 H20'
_chemical_formula_weight         449.52
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                79.631(3)
_cell_angle_beta                 83.640(3)
_cell_angle_gamma                89.884(3)
_cell_formula_units_Z            4
_cell_length_a                   7.3866(3)
_cell_length_b                   17.1147(6)
_cell_length_c                   17.5278(5)
_cell_measurement_reflns_used    20611
_cell_measurement_temperature    99.99(13)
_cell_measurement_theta_max      73.8660
_cell_measurement_theta_min      3.9720
_cell_volume                     2165.89(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (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      99.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -12.00 105.00   0.50    3.41    --   16.00  68.00  48.85  234
  2  \w    -61.00  50.00   0.50    3.41    --   28.00 -50.00 101.25  222
  3  \w      0.00 121.00   0.50    3.41    --   32.00  78.00-118.44  242
  4  \w     11.00 133.00   0.50    3.41    --   44.00  81.00 -96.51  244
  5  \w     15.00 137.00   0.50    3.41    --   48.00  82.00 -47.49  244
  6  \w     20.00 141.00   0.50    9.64    --   52.00  80.00-174.32  242
  7  \w     24.00 145.00   0.50    9.64    --   56.00  80.00  -0.75  242
  8  \w     23.00 145.00   0.50    9.64    --   56.00  82.00  54.97  244
  9  \w     27.00 149.00   0.50    9.64    --   60.00  82.00 100.35  244
 10  \w     39.00 161.00   0.50    9.64    --   72.00  82.00-132.01  244
 11  \w     43.00 165.00   0.50    9.64    --   76.00  82.00 149.26  244
 12  \w     43.00 165.00   0.50    9.64    --   76.00  82.00 175.63  244
 13  \w     43.00 165.00   0.50    9.64    --   76.00  81.00  56.03  244
 14  \w     43.00 165.00   0.50    9.64    --   76.00  82.00 -59.05  244
 15  \w     44.00 165.00   0.50    9.64    --   76.00  80.00-105.58  242
 16  \w     43.00 165.00   0.50    9.64    --   76.00  82.00 -89.24  244
 17  \w     43.00 165.00   0.50    9.64    --   76.00  81.00-156.90  244
 18  \w     47.00 169.00   0.50    9.64    --   80.00  81.00 -56.11  244
 19  \w     47.00 169.00   0.50    9.64    --   80.00  82.00 155.13  244
 20  \w     47.00 169.00   0.50    9.64    --   80.00  82.00 110.30  244
 21  \w     47.00 169.00   0.50    9.64    --   80.00  82.00   7.88  244
 22  \w     51.00 173.00   0.50    9.64    --   84.00  82.00 -38.69  244
 23  \w     55.00 173.00   0.50    9.64    --   84.00  71.00-160.36  236
 24  \w     60.00 181.00   0.50    9.64    --   92.00  79.00 -26.82  242
 25  \w      8.00 130.00   0.50    9.64    --   97.10 -82.00-180.00  244
 26  \w     66.00 186.00   0.50    9.64    --   97.10  77.00  30.00  240
 27  \w     71.00 186.00   0.50    9.64    --   97.10  61.00  90.00  230
 28  \w     75.00 186.00   0.50    9.64    --   97.10  45.00 -90.00  222
 29  \w     64.00 186.00   0.50    9.64    --   97.10  82.00 150.00  244
 30  \w     66.00 186.00   0.50    9.64    --   97.10  77.00  90.00  240
 31  \w     64.00 186.00   0.50    9.64    --   97.10  82.00  60.00  244
 32  \w      8.00 130.00   0.50    9.64    --   97.10 -82.00 120.00  244
 33  \w     64.00 166.00   0.50    9.64    --   97.10  82.00-120.00  204
 34  \w     43.00 129.00   0.50    9.64    --   97.10 -82.00 -60.00  172
 35  \w     65.00 116.00   0.50    9.64    --   97.10 -45.00 150.00  102
 36  \w      8.00  97.00   0.50    9.64    --   97.10 -61.00 -60.00  178
 37  \w     72.00 181.00   0.50    9.64    --   97.10  61.00  30.00  218
 38  \w     76.00 161.00   0.50    9.64    --   97.10  61.00 150.00  170
 39  \w     64.00 162.00   0.50    9.64    --   97.10  82.00-150.00  196
 40  \w     75.00 169.00   0.50    9.64    --   97.10  45.00 -60.00  188
 41  \w     11.00  62.00   0.50    9.64    --   97.10 -82.00  30.00  102
 42  \w     66.00 121.00   0.50    9.64    --   97.10 -82.00  30.00  110
 43  \w      8.00 119.00   0.50    9.64    --   97.10 -61.00  30.00  222
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058861000
_diffrn_orient_matrix_UB_12      0.0795997000
_diffrn_orient_matrix_UB_13      0.0291024000
_diffrn_orient_matrix_UB_21      0.0344734000
_diffrn_orient_matrix_UB_22      0.0444622000
_diffrn_orient_matrix_UB_23      -0.0850236000
_diffrn_orient_matrix_UB_31      -0.2069534000
_diffrn_orient_matrix_UB_32      0.0079703000
_diffrn_orient_matrix_UB_33      -0.0030997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            69420
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.001
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.12b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             938
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 5331 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1277
_refine_ls_number_reflns         14972
_refine_ls_number_restraints     2945
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0730
_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^)+(0.1101P)^2^+2.4354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.1981
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                12863
_reflns_number_total             14972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00320_si_002.cif
_cod_data_source_block           bfc_ls
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C143 H80'
_cod_original_formula_weight         1798.07
_cod_original_formula_moiety         '4(C34 H18), C7 H8'
_cod_original_formula_units_Z            1
_cod_database_code               4035465
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C34 H18'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5.a Secondary CH2 refined with riding coordinates:
 C77(H77A,H77B), C7(H7A,H7B), C98(H98A,H98B), C130(H13A,H13B), C109(H10A,H10B),
  C28(H28A,H28B), C43(H43A,H43B), C64(H64A,H64B)
5.b Aromatic/amide H refined with riding coordinates:
 C92(H92), C79(H79), C86(H86), C93(H93), C99(H99), C14(H14), C100(H100),
 C102(H102), C21(H21), C80(H80), C87(H87), C117(H117), C15(H15), C101(H101),
 C22(H22), C49(H49), C56(H56), C70(H70), C133(H133), C71(H71), C74(H74),
 C27(H27), C123(H123), C69(H69), C124(H124), C128(H128), C129(H129), C37(H37),
 C26(H26), C48(H48), C55(H55), C3(H3), C116(H116), C35(H35), C6(H6), C57(H57),
 C1(H1), C67(H67), C38(H38), C105(H105), C66(H66), C31(H31), C36(H36), C58(H58),
  C32(H32), C2(H2), C136(H136), C33(H33), C104(H104), C34(H34), C108(H108),
 C65(H65), C68(H68), C134(H134), C135(H135), C103(H103), C138(H138), C142(H142),
  C141(H141), C140(H140), C139(H139)
5.c Fitted hexagon refined as free rotating group:
 C138(C137,C142,C141,C140,C139)
5.d Idealised Me refined as rotating group:
 C143(H14A,H14B,H14C)
;
_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 1.998
_oxdiff_exptl_absorpt_empirical_full_min 0.723