Catalytic Asymmetric Radical-Mediated Three-Component Piancatelli-Type Rearrangement of Furylalkenes
Xu, Lei; Zhong, Sishi; Yang, Qian; Wei, Jie; Zou, Jiaming; Li, Hongxiang; Cai, Yunfei; ACS Catalysis 11 (2021) 10198–10207; doi:10.1021/acscatal.1c03119

data_4518935
_publ_section_title
;
 Catalytic Asymmetric Radical-Mediated Three-Component Piancatelli-Type
 Rearrangement of Furylalkenes
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10198
_journal_page_last               10207
_journal_paper_doi               10.1021/acscatal.1c03119
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H24 Cl F2 N O3'
_chemical_formula_sum            'C28 H24 Cl F2 N O3'
_chemical_formula_weight         495.93
_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             2021-01-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.692(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6182(4)
_cell_length_b                   7.3866(4)
_cell_length_c                   19.3609(10)
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.4560
_cell_measurement_theta_min      4.0590
_cell_volume                     1229.94(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.889
_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    -53.00  68.00   1.00    5.77    --   18.74   0.00 -60.00  121
  2  \w    -49.00  38.00   1.00    5.77    --   18.74 -57.00-180.00   87
  3  \w    -22.00  36.00   1.00    5.77    --   18.74 -57.00 -90.00   58
  4  \w    -89.00 -64.00   1.00    5.77    --  -18.97-178.00 -90.00   25
  5  \w    -81.00   0.00   1.00    5.77    --  -18.97 -57.00 -60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0424353000
_diffrn_orient_matrix_UB_12      0.0700091000
_diffrn_orient_matrix_UB_13      -0.0177686000
_diffrn_orient_matrix_UB_21      -0.0039776000
_diffrn_orient_matrix_UB_22      -0.0528265000
_diffrn_orient_matrix_UB_23      -0.0306278000
_diffrn_orient_matrix_UB_31      -0.0706863000
_diffrn_orient_matrix_UB_32      -0.0390332000
_diffrn_orient_matrix_UB_33      0.0096207000
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9403
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.084
_diffrn_reflns_theta_min         3.472
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5582
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0612
_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^)+(0.0678P)^2^+0.4167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.794
_reflns_number_gt                3886
_reflns_number_total             5582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03119_si_003.cif
_cod_data_source_block           20210113-caiyunfei-zss-cy-01
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4518934--4518935.cif.
;
_cod_database_code               4518935
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H24 F2 O3 Cl'
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C2
 1.51 with sigma of 0.02
3. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
5.a Ternary CH refined with riding coordinates:
 C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C24(H24), C22(H22), C18(H18), C19(H19), C21(H21), C8(H8), C25(H25),
 C28(H28), C27(H27), C15(H15), C12(H12), C26(H26), C9(H9), C13(H13), C14(H14)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              97202
_shelx_hkl_checksum              88595
_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 1.934
_oxdiff_exptl_absorpt_empirical_full_min 0.490