Organocatalytic Asymmetric Nucleophilic Addition to o-Quinone Methides by Alcohols.
Lai, Zengwei; Wang, Zhaobin; Sun, Jianwei; Organic letters 17 (2015) 6058–6061; doi:10.1021/acs.orglett.5b03072

data_1555446
_publ_section_title
;
 Organocatalytic Asymmetric Nucleophilic Addition to o-Quinone Methides by
 Alcohols.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6058
_journal_page_last               6061
_journal_paper_doi               10.1021/acs.orglett.5b03072
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 O2'
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.35
_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             2015-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0068(2)
_cell_length_b                   10.4780(3)
_cell_length_c                   16.4734(4)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2930
_cell_measurement_theta_min      5.3700
_cell_volume                     1554.65(7)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega   33.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 57

  2 omega -117.00  -15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -37.0000   30.0000 102

  3 omega -117.00  -15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -37.0000  120.0000 102

  4 omega   33.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 57

  5 omega   33.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -90.0000 57

  6 omega   94.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000  -90.0000 84

  7 omega   36.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -120.0000 62

  8 omega   26.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000    0.0000 82

  9 omega  -52.00    0.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828   41.0000   65.0000 52
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1469274000
_diffrn_orient_matrix_UB_12      -0.0745967000
_diffrn_orient_matrix_UB_13      0.0060836000
_diffrn_orient_matrix_UB_21      0.0233981000
_diffrn_orient_matrix_UB_22      0.0153503000
_diffrn_orient_matrix_UB_23      -0.0921330000
_diffrn_orient_matrix_UB_31      0.0844159000
_diffrn_orient_matrix_UB_32      0.1257630000
_diffrn_orient_matrix_UB_33      0.0147942000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5580
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.393
_diffrn_reflns_theta_min         5.002
_diffrn_source                   '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    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89234
_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            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0490P)^2^+0.0098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2472
_reflns_number_total             2764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03072_si_002.cif
_cod_data_source_block           lai4cult
_cod_database_code               1555446
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              59138
_shelx_hkl_checksum              82534
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-03
_olex2_submission_special_instructions 'No special instructions were received'