Unified Synthesis of Multiply Arylated Alkanes by Catalytic Deoxygenative Transformation of Diarylketones
Kurosawa, Miki B.; Kato, Kenta; Muto, Kei; Yamaguchi, Junichiro; Chemical Science  (2022) –; doi:10.1039/D2SC03720C

data_1567515
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_publ_section_title
;
 Unified Synthesis of Multiply Arylated Alkanes by Catalytic Deoxygenative
 Transformation of Diarylketones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03720C
_journal_year                    2022
_chemical_formula_moiety         'C27 H20 O'
_chemical_formula_sum            'C27 H20 O'
_chemical_formula_weight         360.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-20 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.0850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.33910(10)
_cell_length_b                   10.8689(2)
_cell_length_c                   11.7668(2)
_cell_measurement_reflns_used    7392
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8910
_cell_measurement_theta_min      3.7820
_cell_volume                     933.33(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_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     21.00  69.00   0.50    0.05    --   43.05  57.00 150.00   96
  2  \w     61.00  86.00   0.50    0.05    --   43.05  34.00  94.00   50
  3  \w     96.00 121.00   0.50    0.17    --  108.01  34.00  94.00   50
  4  \w    132.00 159.00   0.50    0.17    --  108.01  34.00  94.00   54
  5  \w     44.00  97.00   0.50    0.17    --  108.01 -77.00 -60.00  106
  6  \w     43.00  68.00   0.50    0.17    --  108.01 -61.00 120.00   50
  7  \w     42.00  67.00   0.50    0.17    --  108.01 -61.00  60.00   50
  8  \w     34.00  61.00   0.50    0.17    --  108.01 -61.00  30.00   54
  9  \w     36.00  66.00   0.50    0.17    --  108.01 -61.00   0.00   60
 10  \w     35.00  60.00   0.50    0.17    --  108.01 -61.00-180.00   50
 11  \w    -36.00  32.00   0.50    0.05    --   43.05 -19.00-180.00  136
 12  \w    -17.00  16.00   0.50    0.05    --   43.05 -34.00 -63.00   66
 13  \w     35.00  61.00   0.50    0.05    --   43.05-125.00-180.00   52
 14  \w     38.00  64.00   0.50    0.17    --  108.01-125.00-180.00   52
 15  \w     80.00 108.00   0.50    0.17    --  108.01-125.00-180.00   56
 16  \w    -50.00 -21.00   0.50    0.17    --  -96.00  45.00-180.00   58
 17  \w    -70.00 -22.00   0.50    0.17    --  -96.00  61.00-150.00   96
 18  \w    -51.00 -21.00   0.50    0.17    --  -96.00  45.00-150.00   60
 19  \w    -47.00 -21.00   0.50    0.17    --  -96.00  45.00-120.00   52
 20  \w     -5.00  34.00   0.50    0.05    --  -43.05  34.00  94.00   78
 21  \w    -42.00  -9.00   0.50    0.05    --  -43.05  34.00  94.00   66
 22  \w    -65.00 -22.00   0.50    0.17    --  -96.00  61.00 -90.00   86
 23  \w    -52.00 -27.00   0.50    0.17    --  -96.00  45.00 -90.00   50
 24  \w   -173.00-120.00   0.50    0.17    --  -96.00 -34.00 -63.00  106
 25  \w   -169.00 -67.00   0.50    0.17    --  -96.00 -77.00-120.00  204
 26  \w    -92.00 -67.00   0.50    0.17    --  -96.00 -77.00-180.00   50
 27  \w    -73.00 -19.00   0.50    0.05    --  -43.05 -77.00-150.00  108
 28  \w    -93.00 -67.00   0.50    0.17    --  -96.00 -76.00-110.84   52
 29  \w   -112.00 -69.00   0.50    0.17    --  -96.00 -75.00-149.35   86
 30  \w   -161.00-135.00   0.50    0.17    --  -96.00 -75.00-149.35   52
 31  \w   -166.00-141.00   0.50    0.17    --  -96.00 -77.00 -90.00   50
 32  \w   -139.00 -68.00   0.50    0.17    --  -96.00 -77.00 -90.00  142
 33  \w    -96.00 -70.00   0.50    0.17    --  -96.00 -69.00-149.48   52
 34  \w    -95.00 -70.00   0.50    0.17    --  -96.00 -72.00-136.72   50
 35  \w   -140.00 -73.00   0.50    0.17    --  -96.00 -61.00-120.00  134
 36  \w    -93.00 -68.00   0.50    0.17    --  -96.00 -77.00 150.00   50
 37  \w    -95.00 -70.00   0.50    0.17    --  -96.00 -69.00 178.04   50
 38  \w   -105.00 -72.00   0.50    0.17    --  -96.00 -64.00 150.92   66
 39  \w   -169.00 -74.00   0.50    0.17    --  -96.00 -61.00 150.00  190
 40  \w   -127.00-102.00   0.50    0.17    --  -96.00 -61.00 -90.00   50
 41  \w    -97.00 -72.00   0.50    0.17    --  -96.00 -61.00-157.06   50
 42  \w    -97.00 -72.00   0.50    0.17    --  -96.00 -61.00-180.00   50
 43  \w   -147.00-107.00   0.50    0.17    --  -96.00 -61.00-180.00   80
 44  \w   -145.00-120.00   0.50    0.17    --  -96.00 -61.00-157.06   50
 45  \w   -117.00 -20.00   0.50    0.05    --  -43.05 -34.00 -63.00  194
 46  \w   -114.00 -74.00   0.50    0.17    --  -96.00 -34.00 -63.00   80
 47  \w   -149.00 -75.00   0.50    0.17    --  -96.00 -45.00 150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075847000
_diffrn_orient_matrix_UB_12      -0.0593470000
_diffrn_orient_matrix_UB_13      -0.1192477000
_diffrn_orient_matrix_UB_21      -0.2086472000
_diffrn_orient_matrix_UB_22      -0.0166725000
_diffrn_orient_matrix_UB_23      -0.0015810000
_diffrn_orient_matrix_UB_31      -0.0308952000
_diffrn_orient_matrix_UB_32      0.1276980000
_diffrn_orient_matrix_UB_33      -0.0557462000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11335
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.083
_diffrn_reflns_theta_min         3.778
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
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            'clear colourless'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0357P)^2^+0.1139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.881
_reflns_number_gt                3382
_reflns_number_total             3526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03720c2.cif
_cod_data_source_block           18
_cod_database_code               1567515
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C27H20O
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.853
_diffrn_oxdiff_digest_frames
;
019297801f8be3fbb4ae3f79c9e5cab41903672ae5e
;
_diffrn_oxdiff_digest_hkl
;
016fc47879ed0db1f98fffd81eb1f3db6bb4cf
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C9(H9), C26(H26), C3(H3), C5(H5), C16(H16), C10(H10),
 C19(H19), C4(H4), C21(H21), C6(H6), C18(H18), C25(H25), C17(H17), C11(H11),
 C15(H15), C24(H24), C12(H12), C23(H23)
;
_shelx_res_checksum              88461
_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 1.722
_oxdiff_exptl_absorpt_empirical_full_min 0.729