Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2
Gui, Yong-Yuan; Hu, Naifu; Chen, Xiao-Wang; Liao, Li−Li; Ju, Tao; Ye, Jian-Heng; Zhang, Zhen; Li, Jing; Yu, Da-Gang; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b10149

data_4126719
_publ_section_title
;
 Highly Regio- and Enantioselective Copper-Catalyzed Reductive
 Hydroxymethylation of Styrenes and 1,3-Dienes with CO2
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b10149
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H19 N O5 S'
_chemical_formula_sum            'C21 H19 N O5 S'
_chemical_formula_weight         397.43
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.355(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1689(4)
_cell_length_b                   8.7421(4)
_cell_length_c                   13.5756(8)
_cell_measurement_reflns_used    2889
_cell_measurement_temperature    298.0(3)
_cell_measurement_theta_max      72.2850
_cell_measurement_theta_min      5.9150
_cell_volume                     956.59(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      air
_diffrn_ambient_temperature      298.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671  -38.0000   90.0000 88

  2 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671 -125.0000 -150.0000 66

  3 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671 -125.0000 -180.0000 66

  4 omega  -32.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671  -77.0000 -120.0000 94

  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671   57.0000 -150.0000 84

  6 omega  -32.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671  -57.0000  -30.0000 84

  7 omega   91.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

  8 omega   40.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

  9 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 10 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 11 omega   40.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 95

 12 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 13 omega  100.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

 14 omega   81.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 15 omega   91.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 16 omega   11.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671   74.0000  -33.0000 92

 17 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671   77.0000   90.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1277503000
_diffrn_orient_matrix_UB_12      0.0155941000
_diffrn_orient_matrix_UB_13      0.0714000000
_diffrn_orient_matrix_UB_21      0.0868668000
_diffrn_orient_matrix_UB_22      0.1473174000
_diffrn_orient_matrix_UB_23      0.0438305000
_diffrn_orient_matrix_UB_31      -0.1124034000
_diffrn_orient_matrix_UB_32      0.0952940000
_diffrn_orient_matrix_UB_33      -0.0789149000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5638
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.355
_diffrn_reflns_theta_min         5.488
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.380
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0490
_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^)+(0.1027P)^2^+0.0098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_full    0.715
_reflns_Friedel_fraction_max     0.675
_reflns_number_gt                3003
_reflns_number_total             3158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b10149_si_001.cif
_cod_data_source_block           xxx-gyy-1
_cod_database_code               4126719
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.95
_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:
 C00R(H00R)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00B,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
2.d Idealised Me refined as rotating group:
 C00S(H00F,H00I,H00J)
;
_olex2_date_sample_data_collection 2017-07-10
_olex2_submission_special_instructions 'No special instructions were received'