Sc(OTf)<sub>3</sub> catalyzed intramolecular single-electron transfer of 2-alkyl-1,4-benzoquinones: synthesis of 6-chromanols from donor-acceptor cyclopropanes.
Wang, Yi-Lin; Lei, Xin-Xin; Jin, Xin-Chen; Zhang, Xin-Yu; Xu, Peng-Fei; Luo, Yong-Chun; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc02988c

data_7132106
_publ_section_title
;
 Sc(OTf)<sub>3</sub> catalyzed intramolecular single-electron transfer of
 2-alkyl-1,4-benzoquinones: synthesis of 6-chromanols from donor-acceptor
 cyclopropanes.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc02988c
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 O6'
_chemical_formula_sum            'C21 H20 O6'
_chemical_formula_weight         368.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-05-14 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.6420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0449(2)
_cell_length_b                   7.77050(10)
_cell_length_c                   27.9991(3)
_cell_measurement_reflns_used    10448
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.9520
_cell_measurement_theta_min      1.6210
_cell_volume                     3666.30(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (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      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.934
_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     35.00  60.00   0.50    0.05    --  107.75 -57.00 -30.00   50
  2  \w     42.00 100.00   0.50    0.05    --  107.75 -77.00-180.00  116
  3  \w     35.00  63.00   0.50    0.05    --  107.75 -57.00-150.00   56
  4  \w     35.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   52
  5  \w    -26.00  35.00   0.50    0.05    --   47.45 -37.00  30.00  122
  6  \w     95.00 156.00   0.50    0.05    --  107.75  57.00 -90.00  122
  7  \w     85.00 167.00   0.50    0.05    --  107.75  97.00 -68.00  164
  8  \w    -40.00 -14.00   0.50    0.05    --  -47.45  97.00 -68.00   52
  9  \w    -96.00 -58.00   0.50    0.05    -- -100.00  97.00 -68.00   76
 10  \w    -93.00 -35.00   0.50    0.05    -- -100.00 125.00  60.00  116
 11  \w    -65.00 -29.00   0.50    0.05    -- -100.00  57.00 150.00   72
 12  \w    -68.00 -28.00   0.50    0.05    -- -100.00  57.00 120.00   80
 13  \w    -62.00 -35.00   0.50    0.05    -- -100.00  57.00  90.00   54
 14  \w    -68.00 -27.00   0.50    0.05    -- -100.00  57.00  60.00   82
 15  \w    -55.00 -28.00   0.50    0.05    -- -100.00  57.00 -90.00   54
 16  \w   -120.00 -33.00   0.50    0.05    --  -47.45 -77.00  30.00  174
 17  \w   -168.00 -97.00   0.50    0.05    -- -100.00 -97.00-176.00  142
 18  \w    -14.00  80.00   0.50    0.05    --   47.45 -97.00-176.00  188
 19  \w     60.00 106.00   0.50    0.05    --  107.75 -97.00-176.00   92
 20  \w     42.00  84.00   0.50    0.05    --  107.75 -99.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0725825000
_diffrn_orient_matrix_UB_12      0.0992706000
_diffrn_orient_matrix_UB_13      -0.0123373000
_diffrn_orient_matrix_UB_21      -0.0528227000
_diffrn_orient_matrix_UB_22      0.1580926000
_diffrn_orient_matrix_UB_23      -0.0144741000
_diffrn_orient_matrix_UB_31      0.0171215000
_diffrn_orient_matrix_UB_32      0.0670451000
_diffrn_orient_matrix_UB_33      0.0522977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11635
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.429
_diffrn_reflns_theta_min         5.723
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0419P)^2^+3.3998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3549
_reflns_number_total             3641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02988c2.cif
_cod_data_source_block           wangyang_0512_auto
_cod_database_code               7132106
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.888
_reflns_odcompleteness_completeness 98.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H15), C21(H31), C22(H33), C34(H40), C38(H47), C32(H39)
2.c Idealised Me refined as rotating group:
 C10(H18,H19,H20), C17(H28,H29,H30), C35(H41,H42,H43), C36(H44,H45,H46)
2.d Idealised tetrahedral OH refined as rotating group:
 O27(H37)
;
_shelx_res_checksum              8507
_shelx_hkl_checksum              45432
_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 1.810
_oxdiff_exptl_absorpt_empirical_full_min 0.702