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_7132105
_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         'C20 H20 O6'
_chemical_formula_sum            'C20 H20 O6'
_chemical_formula_weight         356.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-12 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.968(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4049(3)
_cell_length_b                   8.66607(17)
_cell_length_c                   26.3242(6)
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    293.29(10)
_cell_measurement_theta_max      69.5170
_cell_measurement_theta_min      6.2770
_cell_volume                     3674.05(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.29(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_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     31.00  59.00   1.00    1.00    --   54.00 -57.00   0.00   28
  2  \w     34.00  60.00   1.00    1.00    --   54.00-125.00 -30.00   26
  3  \w     80.00 133.00   1.00    1.00    --  108.00 -91.00 -30.00   53
  4  \w     55.00 117.00   1.00    1.00    --  108.00 -50.00-180.00   62
  5  \w     35.00  88.00   1.00    1.00    --  108.00 -25.00-120.00   53
  6  \w     36.00  65.00   1.00    1.00    --  108.00 -91.00 -30.00   29
  7  \w      4.00  93.00   1.00    1.00    --   54.00 -99.00-120.00   89
  8  \w      5.00  67.00   1.00    1.00    --    0.00  38.00 -30.00   62
  9  \w     29.00 125.00   1.00    1.00    --   54.00  38.00  30.00   96
 10  \w     95.00 122.00   1.00    1.00    --   54.00  57.00 120.00   27
 11  \w     80.00 119.00   1.00    1.00    --  108.00  25.00 150.00   39
 12  \w    104.00 178.00   1.00    1.00    --  108.00  38.00  60.00   74
 13  \w    104.00 178.00   1.00    1.00    --  108.00 111.00 -60.00   74
 14  \w    145.00 176.00   1.00    1.00    --  108.00 111.00-120.00   31
 15  \w     88.00 177.00   1.00    1.00    --  108.00  50.00   0.00   89
 16  \w     32.00  61.00   1.00    1.00    --    0.00  57.00-150.00   29
 17  \w    -19.00  21.00   1.00    1.00    --    0.00  57.00-150.00   40
 18  \w     33.00  87.00   1.00    1.00    --   54.00  57.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0904016000
_diffrn_orient_matrix_UB_12      -0.0582631000
_diffrn_orient_matrix_UB_13      0.0103849000
_diffrn_orient_matrix_UB_21      0.0194590000
_diffrn_orient_matrix_UB_22      0.1068384000
_diffrn_orient_matrix_UB_23      -0.0429205000
_diffrn_orient_matrix_UB_31      0.0246170000
_diffrn_orient_matrix_UB_32      0.1294783000
_diffrn_orient_matrix_UB_33      0.0400629000
_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  0.0137
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.714
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0680P)^2^+2.1222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2932
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02988c2.cif
_cod_data_source_block           leixx_0526
_cod_original_cell_volume        3674.04(13)
_cod_database_code               7132105
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.74
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C17(H17), C19(H19), C18(H18), C3(H3), C16(H16), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              48112
_shelx_hkl_checksum              14081
_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 1.130
_oxdiff_exptl_absorpt_empirical_full_min 0.804