Rational Functionalization of a C<sub>70</sub> Buckybowl To Enable a C<sub>70</sub>:Buckybowl Cocrystal for Organic Semiconductor Applications.
Gao, Guangpeng; Chen, Meng; Roberts, Josiah; Feng, Meng; Xiao, Chengyi; Zhang, Guowei; Parkin, Sean; Risko, Chad; Zhang, Lei; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12192

data_4133951
_publ_section_title
;
 Rational Functionalization of a C<sub>70</sub> Buckybowl To Enable a
 C<sub>70</sub>:Buckybowl Cocrystal for Organic Semiconductor
 Applications.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12192
_journal_year                    2020
_chemical_formula_moiety         'C58 H56, C7 H8'
_chemical_formula_sum            'C65 H64'
_chemical_formula_weight         845.16
_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     dual
_audit_creation_date             2019-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.4750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.30070(10)
_cell_length_b                   18.60490(10)
_cell_length_c                   31.7768(2)
_cell_measurement_reflns_used    39437
_cell_measurement_temperature    219.97(15)
_cell_measurement_theta_max      75.1630
_cell_measurement_theta_min      2.3970
_cell_volume                     9986.76(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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      219.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_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    -82.00 -41.00   0.50    0.05    --  -47.20 -53.00-110.00   82
  2  \w    -61.00  25.00   0.50    0.05    --  -47.20  53.00  33.00  172
  3  \w    -24.00  31.00   0.50    0.05    --   47.20 -53.00-110.00  110
  4  \w     40.00 114.00   0.50    0.05    --   47.20  53.00  33.00  148
  5  \w   -151.00-126.00   0.50    0.50    --  -99.00 -53.00-110.00   50
  6  \w    -94.00 -69.00   0.50    0.50    --  -99.00  53.00  33.00   50
  7  \w     90.00 169.00   0.50    0.50    --  103.25  53.00  33.00  158
  8  \w     33.00 117.00   0.50    0.50    --  103.25 -53.00-110.00  168
  9  \w   -119.00 -78.00   0.50    0.05    --  -47.20-125.00   0.00   82
 10  \w   -116.00 -71.00   0.50    0.05    --  -47.20-125.00  30.00   90
 11  \w   -111.00 -24.00   0.50    0.50    --  -99.00  15.00-120.00  174
 12  \w   -166.00-101.00   0.50    0.50    --  -99.00 -15.00 -60.00  130
 13  \w   -114.00 -40.00   0.50    0.50    --  -99.00  61.00 120.00  148
 14  \w   -101.00 -75.00   0.50    0.50    --  -99.00  45.00-120.00   52
 15  \w   -162.00 -97.00   0.50    0.50    --  -99.00 -45.00   0.00  130
 16  \w     62.00 119.00   0.50    0.50    --  103.25 -61.00 150.00  114
 17  \w     38.00 125.00   0.50    0.50    --  103.25 -77.00 120.00  174
 18  \w    136.00 162.00   0.50    0.50    --  103.25  61.00  60.00   52
 19  \w     90.00 126.00   0.50    0.50    --  103.25  61.00  60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0537749000
_diffrn_orient_matrix_UB_12      -0.0417920000
_diffrn_orient_matrix_UB_13      -0.0369381000
_diffrn_orient_matrix_UB_21      -0.0736460000
_diffrn_orient_matrix_UB_22      0.0329641000
_diffrn_orient_matrix_UB_23      0.0124398000
_diffrn_orient_matrix_UB_31      0.0029805000
_diffrn_orient_matrix_UB_32      0.0634048000
_diffrn_orient_matrix_UB_33      -0.0307466000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            76891
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.594
_diffrn_reflns_theta_min         2.616
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             3632
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1382
_refine_ls_number_reflns         19781
_refine_ls_number_restraints     333
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+3.1064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16879
_reflns_number_total             19781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12192_si_004.cif
_cod_data_source_block           tx963
_cod_database_code               4133951
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CH
_chemical_oxdiff_usercomment     CH
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.788
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Restrained distances
 C66-C67 = C68-C67 = C69-C68 = C70-C69 = C70-C71 = C71-C66
 1.39 with sigma of 0.01
 C66A-C67A = C68A-C67A = C69A-C68A = C70A-C69A = C70A-C71A = C71A-C66A
 1.39 with sigma of 0.01
 C72A-C66A
 1.51 with sigma of 0.01
 C4AA-C45 = C46-C45 = C4AA-C3AA = C47-C46 = C3AA-C2AA = C48-C47 = C49-C2AA =
 C49-C48
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C66A
\\sim C67A \\sim C68A \\sim C69A \\sim C70A \\sim C71A \\sim C72A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C66) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C71)
\\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C70) \\sim Ueq,
Uanis(C68A) \\sim Ueq, Uanis(C67A) \\sim Ueq, Uanis(C69A) \\sim Ueq,
Uanis(C66A) \\sim Ueq, Uanis(C70A) \\sim Ueq, Uanis(C72A) \\sim Ueq,
Uanis(C71A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C4AA) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C2AA) \\sim Ueq, Uanis(C3AA)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C66A)=Sof(C67A)=Sof(H67A)=Sof(C68A)=Sof(H68A)=Sof(C69A)=Sof(H69A)=
 Sof(C70A)=Sof(H70A)=Sof(C71A)=Sof(H71A)=Sof(C72A)=Sof(H72D)=Sof(H72E)=
 Sof(H72F)=1-FVAR(1)
 Sof(C66)=Sof(C67)=Sof(H67)=Sof(C68)=Sof(H68)=Sof(C69)=Sof(H69)=Sof(C70)=
 Sof(H70)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=FVAR(1)
 Sof(H41C)=Sof(C42B)=Sof(H42G)=Sof(H42H)=Sof(H42I)=Sof(C43B)=Sof(H43G)=
 Sof(H43H)=Sof(H43I)=1-FVAR(2)
 Sof(H41B)=Sof(C42A)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C43A)=Sof(H43D)=
 Sof(H43E)=Sof(H43F)=FVAR(2)
 Sof(H53B)=Sof(C54B)=Sof(H54G)=Sof(H54H)=Sof(H54I)=Sof(C55B)=Sof(H55G)=
 Sof(H55H)=Sof(H55I)=1-FVAR(3)
 Sof(H53A)=Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=Sof(C55A)=Sof(H55D)=
 Sof(H55E)=Sof(H55F)=FVAR(3)
 Sof(H41A)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=Sof(C1AA)=Sof(H1AA)=
 Sof(H1AB)=Sof(H1AC)=1-FVAR(4)
 Sof(H41)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(C43)=Sof(H43A)=Sof(H43B)=
 Sof(H43C)=FVAR(4)
 Sof(C2AA)=Sof(H2AA)=Sof(C3AA)=Sof(C4AA)=Sof(H4AA)=Sof(C5AA)=Sof(H5AA)=
 Sof(C6AA)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(C7AA)=Sof(H7AA)=Sof(H7AB)=
 Sof(H7AC)=1-FVAR(5)
 Sof(C46)=Sof(H46)=Sof(C47)=Sof(C48)=Sof(H48)=Sof(C53)=Sof(H53)=Sof(C54)=
 Sof(H54A)=Sof(H54B)=Sof(H54C)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=FVAR(5)
5.a Ternary CH refined with riding coordinates:
 C35(H35), C38(H38), C41(H41), C41(H41A), C50(H50), C53(H53), C56(H56),
 C35A(H35A), C38A(H38A), C41A(H41B), C41A(H41C), C50A(H50A), C53A(H53A),
 C53A(H53B), C56A(H56A), C5AA(H5AA)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C31(H31), C33(H33), C46(H46), C48(H48), C3A(H3A), C4A(H4A),
  C5A(H5A), C8A(H8A), C9A(H9A), C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A),
 C19A(H19A), C31A(H31A), C33A(H33A), C46A(H46A), C48A(H48A), C60(H60), C61(H61),
  C62(H62), C63(H63), C64(H64), C67(H67), C68(H68), C69(H69), C70(H70),
 C71(H71), C67A(H67A), C68A(H68A), C69A(H69A), C70A(H70A), C71A(H71A),
 C2AA(H2AA), C4AA(H4AA)
5.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C51(H51A,H51B,H51C), C52(H52A,
 H52B,H52C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C),
 C58(H58A,H58B,H58C), C36A(H36D,H36E,H36F), C37A(H37D,H37E,H37F), C39A(H39D,
 H39E,H39F), C40A(H40D,H40E,H40F), C42A(H42D,H42E,H42F), C43A(H43D,H43E,H43F),
 C51A(H51D,H51E,H51F), C52A(H52D,H52E,H52F), C54A(H54D,H54E,H54F), C55A(H55D,
 H55E,H55F), C57A(H57D,H57E,H57F), C58A(H58D,H58E,H58F), C65(H65A,H65B,H65C),
 C72(H72A,H72B,H72C), C72A(H72D,H72E,H72F), C42B(H42G,H42H,H42I), C43B(H43G,
 H43H,H43I), C54B(H54G,H54H,H54I), C55B(H55G,H55H,H55I), C0AA(H0AA,H0AB,H0AC),
 C1AA(H1AA,H1AB,H1AC), C6AA(H6AA,H6AB,H6AC), C7AA(H7AA,H7AB,H7AC)
;
_shelx_res_checksum              78641
_shelx_hkl_checksum              17347
_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 1.712
_oxdiff_exptl_absorpt_empirical_full_min 0.482