Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes.
You, Yong; Li, Ting-Ting; Yuan, Shu-Pei; Xie, Ke-Xin; Wang, Zhen-Hua; Zhao, Jian-Qiang; Zhou, Ming-Qiang; Yuan, Wei-Cheng; Chemical communications (Cambridge, England) 56 (2020) 439–442; doi:10.1039/c9cc08316b

data_7125713
_publ_section_title
;
 Catalytic asymmetric [4+2] cycloaddition of
 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone
 methides for the synthesis of polysubstituted chromanes.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              439
_journal_page_last               442
_journal_paper_doi               10.1039/c9cc08316b
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H32 O2, C2 H6 O S'
_chemical_formula_sum            'C37 H38 O3 S'
_chemical_formula_weight         562.73
_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             2019-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-16 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.43565(16)
_cell_length_b                   16.9768(3)
_cell_length_c                   19.2055(3)
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0820
_cell_measurement_theta_min      5.1990
_cell_volume                     3076.47(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -44.00   -3.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  120.0000 82

  2 omega  -97.00  -68.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 58

  3 omega   -1.00   34.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  120.0000 70

  4 omega   33.00   76.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 86

  5 omega   -4.00   24.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 56

  6 omega   19.00  106.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 174

  7 omega   78.00  104.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -120.0000 52

  8 omega   62.00   91.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 58

  9 omega   58.00   89.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 62

 10 omega   18.00   53.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -120.0000 70

 11 omega   12.00   55.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 86

 12 omega  150.00  178.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 56

 13 omega   63.00   99.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 72

 14 omega   78.00  109.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 62

 15 omega   46.00   98.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 104

 16 omega   38.00   63.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 50

 17 omega  107.00  178.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 142

 18 omega   73.00   99.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 52

 19 omega   42.00   85.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 86

 20 omega   38.00   94.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 112

 21 omega   40.00  125.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0252629000
_diffrn_orient_matrix_UB_12      0.0440868000
_diffrn_orient_matrix_UB_13      0.0690112000
_diffrn_orient_matrix_UB_21      0.0171071000
_diffrn_orient_matrix_UB_22      0.0792937000
_diffrn_orient_matrix_UB_23      -0.0380719000
_diffrn_orient_matrix_UB_31      -0.1604069000
_diffrn_orient_matrix_UB_32      0.0015570000
_diffrn_orient_matrix_UB_33      -0.0149072000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11706
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.895
_diffrn_reflns_theta_min         3.475
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93248
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0567
_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^)+(0.0765P)^2^+0.2006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                5075
_reflns_number_total             5806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08316b2.cif
_cod_data_source_block           201906158
_cod_original_cell_volume        3076.49(10)
_cod_database_code               7125713
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O1
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.804
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C11(H11), C12(H12), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C16(H16), C17(H17), C19(H19),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'