π-Extended and Curved Anti-Aromatic Polycyclic Hydrocarbons.
Liu, Junzhi; Ma, Ji; Zhang, Ke; Ravat, Prince; Machata, Peter; Avdoshenko, Stanislav M.; Hennersdorf, Felix; Komber, Hartmut; Pisula, Wojciech; Weigand, Jan J.; Popov, Alexey A.; Berger, Reinhard; Müllen, Klaus; Feng, Xinliang; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b01619

data_4126068
_publ_section_title
;
 \p-Extended and Curved Anti-Aromatic Polycyclic Hydrocarbons.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b01619
_journal_year                    2017
_chemical_formula_moiety         '2(C66 H44), C H4 O'
_chemical_formula_sum            'C133 H92 O'
_chemical_formula_weight         1706.06
_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             2016-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                94.985(3)
_cell_angle_beta                 91.707(2)
_cell_angle_gamma                116.401(3)
_cell_formula_units_Z            1
_cell_length_a                   11.3283(3)
_cell_length_b                   12.3518(3)
_cell_length_c                   17.8043(6)
_cell_measurement_reflns_used    15600
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      76.4240
_cell_measurement_theta_min      4.0150
_cell_volume                     2216.45(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -38.00 -11.00   0.50    2.00    --  -38.50  41.00  30.00   54
  2  \w    -72.00  -6.00   0.50    2.00    --  -38.50 125.00 120.00  132
  3  \w     26.00 113.00   0.50    2.00    --   42.75  41.00  30.00  174
  4  \w    103.00 150.00   0.50    8.00    --  111.00  41.00  30.00   94
  5  \w     92.00 119.00   0.50    8.00    --  111.00 -30.00  90.00   54
  6  \w     77.00 109.00   0.50    8.00    --  111.00 -94.00 150.00   64
  7  \w     68.00 120.00   0.50    8.00    --  111.00-125.00  60.00  104
  8  \w     95.00 121.00   0.50    8.00    --  111.00-125.00 -60.00   52
  9  \w     91.00 132.00   0.50    8.00    --  111.00 -41.00-122.00   82
 10  \w     67.00 172.00   0.50    8.00    --  111.00  15.00 -30.00  210
 11  \w    136.00 178.00   0.50    8.00    --  111.00  61.00-120.00   84
 12  \w    118.00 178.00   0.50    8.00    --  111.00 125.00-120.00  120
 13  \w    120.00 158.00   0.50    8.00    --  111.00 125.00 -90.00   76
 14  \w    115.00 161.00   0.50    8.00    --  111.00 125.00 -60.00   92
 15  \w     88.00 170.00   0.50    8.00    --  111.00  30.00   0.00  164
 16  \w    126.00 153.00   0.50    8.00    --  111.00 125.00 120.00   54
 17  \w     81.00 177.00   0.50    8.00    --  111.00  77.00  30.00  192
 18  \w     48.00  79.00   0.50    8.00    --  111.00 -41.00-122.00   62
 19  \w     51.00 132.00   0.50    8.00    --  111.00 -77.00 -60.00  162
 20  \w     61.00 121.00   0.50    8.00    --  111.00-125.00-180.00  120
 21  \w     39.00 101.00   0.50    8.00    --  111.00-125.00 -90.00  124
 22  \w     42.00 113.00   0.50    8.00    --  111.00 -45.00   0.00  142
 23  \w     41.00 108.00   0.50    8.00    --  111.00-125.00 120.00  134
 24  \w     41.00  66.00   0.50    8.00    --  111.00 -94.00   0.00   50
 25  \w     37.00  77.00   0.50    8.00    --  111.00 -30.00  90.00   80
 26  \w     12.00 116.00   0.50    2.00    --   42.75  77.00 -90.00  208
 27  \w     -6.00  19.00   0.50    2.00    --   42.75 -41.00-122.00   50
 28  \w     49.00  74.00   0.50    8.00    --  111.00 -94.00-150.00   50
 29  \w     33.00 105.00   0.50    8.00    --  111.00 -94.00 -90.00  144
 30  \w      2.00  52.00   0.50    2.00    --   42.75 -99.00 150.00  100
 31  \w    -44.00 -15.00   0.50    2.00    --  -38.50 -41.00-122.00   58
 32  \w   -108.00 -72.00   0.50    2.00    --  -38.50 -41.00-122.00   72
 33  \w    -94.00  -2.00   0.50    2.00    --  -38.50 125.00  30.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0224355000
_diffrn_orient_matrix_UB_12      -0.1194855000
_diffrn_orient_matrix_UB_13      0.0313892000
_diffrn_orient_matrix_UB_21      -0.1449944000
_diffrn_orient_matrix_UB_22      -0.0595646000
_diffrn_orient_matrix_UB_23      -0.0327727000
_diffrn_orient_matrix_UB_31      0.0407535000
_diffrn_orient_matrix_UB_32      -0.0425469000
_diffrn_orient_matrix_UB_33      -0.0743593000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25029
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.510
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       plate
_exptl_crystal_F_000             898
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         9224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0623P)^2^+1.0017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8799
_reflns_number_total             9224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01619_si_004.cif
_cod_data_source_block           feng018
_cod_original_cell_volume        2216.47(12)
_cod_database_code               4126068
_chemical_oxdiff_formula         'C133 H92 O1 '
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H64D)=Sof(H64E)=Sof(H64F)=1-FVAR(1)
 Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(1)
 Sof(H65D)=Sof(H65E)=Sof(H65F)=1-FVAR(2)
 Sof(H65A)=Sof(H65B)=Sof(H65C)=FVAR(2)
 Fixed Sof: O1(0.5) H1(0.5) C67(0.5) H67A(0.5) H67B(0.5) H67C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C28(H28), C29(H29), C30(H30), C31(H31), C34(H34),
  C35(H35), C36(H36), C37(H37), C41(H41), C42(H42), C43(H43), C51(H51),
 C53(H53), C60(H60), C62(H62)
3.b Disordered Me refined as rotating group:
 C64(H64A,H64B,H64C,H64D,H64E,H64F), C65(H65A,H65B,H65C,H65D,H65E,H65F)
3.c Idealised Me refined as rotating group:
 C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C66(H66A,H66B,
 H66C), C67(H67A,H67B,H67C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              52053
_shelx_hkl_checksum              8704
_shelx_shelxl_version_number     2014/7
_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 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.703