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_4128882
_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         'C18 H20 O2'
_chemical_formula_sum            'C18 H20 O2'
_chemical_formula_weight         268.34
_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     direct
_audit_creation_date             2019-02-01
_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                   7.43535(11)
_cell_length_b                   12.70493(17)
_cell_length_c                   15.2334(2)
_cell_measurement_reflns_used    6450
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7690
_cell_measurement_theta_min      4.5190
_cell_volume                     1439.03(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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     32.00 117.00   1.00    3.00    --  106.99-125.00 -30.00   85
  2  \w   -112.00 -14.00   1.00    1.00    --  -40.57 -57.00 120.00   98
  3  \w    -91.00 -16.00   1.00    1.00    --  -40.57 -57.00-180.00   75
  4  \w   -112.00 -13.00   1.00    1.00    --  -40.57 -57.00 -90.00   99
  5  \w    -30.00  64.00   1.00    1.00    --   40.57 -57.00-120.00   94
  6  \w     45.00 137.00   1.00    3.00    --  106.99 -30.00 120.00   92
  7  \w     35.00 132.00   1.00    3.00    --  106.99 -30.00  30.00   97
  8  \w     24.00 110.00   1.00    3.00    --  106.99 -94.00  30.00   86
  9  \w     33.00  73.00   1.00    3.00    --  106.99 -45.00 -60.00   40
 10  \w     87.00 129.00   1.00    3.00    --  106.99 -45.00 -60.00   42
 11  \w     77.00 174.00   1.00    3.00    --  106.99  30.00 120.00   97
 12  \w     43.00 138.00   1.00    3.00    --  106.99 -77.00 120.00   95
;
_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      0.1218317000
_diffrn_orient_matrix_UB_12      0.0397923000
_diffrn_orient_matrix_UB_13      -0.0748936000
_diffrn_orient_matrix_UB_21      -0.0784463000
_diffrn_orient_matrix_UB_22      0.1115598000
_diffrn_orient_matrix_UB_23      0.0108963000
_diffrn_orient_matrix_UB_31      0.1480620000
_diffrn_orient_matrix_UB_32      0.0262875000
_diffrn_orient_matrix_UB_33      0.0670106000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8090
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.488
_diffrn_reflns_theta_min         4.532
_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    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89314
_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    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1048 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0350P)^2^+0.2030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0617
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2524
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07514_si_003.cif
_cod_data_source_block           madk8cult
_cod_original_cell_volume        1439.04(3)
_cod_database_code               4128882
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.886
_reflns_odcompleteness_completeness 99.80
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              66209
_shelx_hkl_checksum              47700
_olex2_date_sample_data_collection 2019-01-29
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.844