Catalytic Enantioselective House-Meinwald Rearrangement: Efficient Construction of All-Carbon Quaternary Stereocenters.
Ma, Dengke; Miao, Chun-Bao; Sun, Jianwei; Journal of the American Chemical Society 141 (2019) 13783–13787; doi:10.1021/jacs.9b07514

data_4128883
_publ_section_title
;
 Catalytic Enantioselective House-Meinwald Rearrangement: Efficient
 Construction of All-Carbon Quaternary Stereocenters.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13783
_journal_page_last               13787
_journal_paper_doi               10.1021/jacs.9b07514
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 F3 O2'
_chemical_formula_sum            'C19 H17 F3 O2'
_chemical_formula_weight         334.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81945(10)
_cell_length_b                   10.42071(11)
_cell_length_c                   15.41623(15)
_cell_measurement_reflns_used    6973
_cell_measurement_temperature    100.2(4)
_cell_measurement_theta_max      73.7060
_cell_measurement_theta_min      5.1050
_cell_volume                     1577.48(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.2(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     78.00 104.00   1.00    3.00    --  106.99  61.00 -60.00   26
  2  \w   -116.00 -14.00   1.00    2.00    --  -40.57 -37.00 -60.00  102
  3  \w    -67.00  32.00   1.00    2.00    --  -40.57  37.00 120.00   99
  4  \w    -92.00  -3.00   1.00    2.00    --  -40.57 125.00 150.00   89
  5  \w    104.00 176.00   1.00    3.00    --  106.99 125.00 -30.00   72
  6  \w     33.00 133.00   1.00    3.00    --  106.99 -61.00 -60.00  100
  7  \w     23.00 109.00   1.00    3.00    --  106.99 -94.00 -90.00   86
  8  \w     91.00 173.00   1.00    3.00    --  106.99  45.00  90.00   82
  9  \w    118.00 178.00   1.00    3.00    --  106.99  61.00 -60.00   60
 10  \w    107.00 172.00   1.00    3.00    --  106.99 125.00 -90.00   65
 11  \w     39.00 117.00   1.00    3.00    --  106.99-125.00 150.00   78
 12  \w     77.00 176.00   1.00    3.00    --  106.99  30.00  30.00   99
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0765885000
_diffrn_orient_matrix_UB_12      0.0680725000
_diffrn_orient_matrix_UB_13      0.0743189000
_diffrn_orient_matrix_UB_21      -0.1325737000
_diffrn_orient_matrix_UB_22      0.0682197000
_diffrn_orient_matrix_UB_23      0.0270532000
_diffrn_orient_matrix_UB_31      -0.0339130000
_diffrn_orient_matrix_UB_32      -0.1120884000
_diffrn_orient_matrix_UB_33      0.0611734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8586
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.489
_diffrn_reflns_theta_min         5.123
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0219
_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^)+(0.0330P)^2^+0.2780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0573
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2801
_reflns_number_total             2818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07514_si_002.cif
_cod_data_source_block           madk9cult
_cod_database_code               4128883
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.794
_reflns_odcompleteness_completeness 99.70
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C24(H24), C25(H25), C26(H26)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              64193
_shelx_hkl_checksum              12789
_olex2_date_sample_data_collection 2019-03-14
_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 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.774