Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
Okude, Ryo; Mori, Genki; Yagi, Akiko; Itami, Kenichiro; Chemical Science 11 (2020) 7672–7675; doi:10.1039/D0SC01909G

data_1557901
_publ_section_title
;
 Programmable synthesis of multiply arylated cubanes through C--H
 metalation and arylation
;
_journal_issue                   29
_journal_name_full               'Chemical Science'
_journal_page_first              7672
_journal_page_last               7675
_journal_paper_doi               10.1039/D0SC01909G
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C42 H34 F9 N O'
_chemical_formula_sum            'C42 H34 F9 N O'
_chemical_formula_weight         739.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-02-21
_audit_creation_method
;
Olex2 1.3
(compiled 2019.11.21 svn.r41b79517 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.6320(10)
_cell_length_b                   14.8891(4)
_cell_length_c                   13.0219(4)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.3190
_cell_measurement_theta_min      2.1160
_cell_volume                     7296.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.841
_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    -69.00 -41.00   0.50   20.36    --   11.29 -57.00-120.00   56
  2  \w    -21.00  11.00   0.50   20.36    --   11.29 -57.00-120.00   64
  3  \w    -15.00  62.00   0.50   20.36    --   11.29 -99.00   0.00  154
  4  \w      2.00  39.00   0.50   20.36    --   11.29  77.00 146.00   74
  5  \w     60.00  86.00   0.50   20.36    --   11.29  77.00 146.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0186332000
_diffrn_orient_matrix_UB_12      -0.0040060000
_diffrn_orient_matrix_UB_13      -0.0066842000
_diffrn_orient_matrix_UB_21      0.0000624000
_diffrn_orient_matrix_UB_22      -0.0399691000
_diffrn_orient_matrix_UB_23      0.0296510000
_diffrn_orient_matrix_UB_31      -0.0028047000
_diffrn_orient_matrix_UB_32      0.0256134000
_diffrn_orient_matrix_UB_33      0.0452170000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27734
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.888
_diffrn_reflns_theta_min         2.123
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       needle
_exptl_crystal_F_000             3056
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         7329
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0697
_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^)+(0.0659P)^2^+8.8591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1699
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5137
_reflns_number_total             7329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01909g2.cif
_cod_data_source_block           5a
_cod_depositor_comments
;Adding full bibliography for 1557900--1557907.cif.

 Adding full bibliography for 1557900--1557907.cif.
;
_cod_database_code               1557901
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C42 H34 F9 N O'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_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. Restrained distances
 F1-C01C = F00X-C01C = F00Y-C01C = F01H-C01C = F01I-C01C = F01G-C01C
 1.35 with sigma of 0.01
 F00Y-C01C = F01H-C01C = F00X-C01C = F1-C01C = F01G-C01C = F01I-C01C
 1.35 with sigma of 0.01
 F1-F01I
 2.2 with sigma of 0.02
 F00Y-F1
 2.2 with sigma of 0.02
 F00X-F01H
 2.2 with sigma of 0.02
 F00Y-F01I
 2.2 with sigma of 0.02
 F01H-F01G
 2.2 with sigma of 0.02
 F00X-F01G
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F00X) \\sim Ueq, Uanis(F01G) \\sim Ueq, Uanis(F01H) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F00Y) \\sim Ueq, Uanis(F01I) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
4. Others
 Sof(F1)=Sof(F00Y)=Sof(F01I)=1-FVAR(1)
 Sof(F00X)=Sof(F01G)=Sof(F01H)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00M(H00M), C00Z(H00Z), C017(H017)
5.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00H(H00H), C00J(H00J), C00L(H00L), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00Y(H00Y), C012(H012), C013(H013),
 C014(H014), C018(H018), C01B(H01J), C01D(H01K), C01F(H01O)
5.c Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C), C019(H01D,H01E,H01F), C01A(H01G,H01H,H01I), C01E(H01L,
 H01M,H01N)
;
_shelx_res_checksum              51892
_shelx_hkl_checksum              68857
_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 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.666