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_7125714
_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         'C39 H39 Cl O3, C2 H3 N'
_chemical_formula_sum            'C41 H42 Cl N O3'
_chemical_formula_weight         632.20
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-16 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.393(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8441(7)
_cell_length_b                   10.6009(8)
_cell_length_c                   15.1947(9)
_cell_measurement_reflns_used    4290
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8750
_cell_measurement_theta_min      4.2950
_cell_volume                     1855.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 1.000
_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    -68.00 -22.00   1.00    1.50    --  -33.50 -77.00 -60.00   46
  2  \w   -107.00 -52.00   1.00    1.50    --  -33.50 178.00  30.00   55
  3  \w      8.00  51.00   1.00    1.50    --   36.47  77.00 120.00   43
  4  \w     32.00  58.00   1.00    1.50    --   36.47  37.00-180.00   26
  5  \w     65.00  96.00   1.00    1.50    --   36.47 178.00 -30.00   31
  6  \w     11.00  49.00   1.00    1.50    --   36.47  77.00  60.00   38
  7  \w     78.00 104.00   1.00    1.50    --   36.47  57.00  30.00   26
  8  \w     43.00  69.00   1.00    1.50    --   36.47  57.00 -30.00   26
  9  \w     62.00  87.00   1.00    1.50    --   36.47  77.00 120.00   25
 10  \w      9.00  63.00   1.00    1.50    --   36.47  77.00   0.00   54
 11  \w     20.00  89.00   1.00    1.50    --   36.47  37.00-150.00   69
 12  \w    -20.00 107.00   1.00    1.50    --   36.47   0.00 150.00  127
 13  \w      3.00  33.00   1.00    1.50    --   36.47 -99.00  90.00   30
 14  \w     45.00  88.00   1.00    1.50    --   36.47  37.00  90.00   43
 15  \w     19.00  45.00   1.00    1.50    --   36.47  77.00-150.00   26
 16  \w     70.00 110.00   1.00    1.50    --   36.47 178.00 150.00   40
 17  \w     23.00  63.00   1.00    1.50    --   36.47  37.00 -30.00   40
 18  \w     53.00  80.00   1.00    1.50    --   36.47  77.00  60.00   27
 19  \w     36.00  61.00   1.00    1.50    --   36.47 -77.00   0.00   25
 20  \w    -13.00  29.00   1.00    1.50    --   36.47 -77.00   0.00   42
 21  \w     88.00 114.00   1.00    6.00    --  108.00  61.00  60.00   26
 22  \w     58.00 101.00   1.00    6.00    --  108.00 -94.00 120.00   43
 23  \w     79.00 105.00   1.00    6.00    --  108.00  77.00  60.00   26
 24  \w     79.00 104.00   1.00    6.00    --  108.00  77.00  30.00   25
 25  \w     82.00 112.00   1.00    6.00    --  108.00  30.00  60.00   30
 26  \w     79.00 104.00   1.00    6.00    --  108.00  77.00   0.00   25
 27  \w    124.00 177.00   1.00    6.00    --  108.00  30.00  90.00   53
 28  \w     84.00 119.00   1.00    6.00    --  108.00  30.00  90.00   35
 29  \w     48.00 109.00   1.00    6.00    --  108.00 -94.00  30.00   61
 30  \w     88.00 114.00   1.00    6.00    --  108.00  61.00  90.00   26
 31  \w    144.00 177.00   1.00    6.00    --  108.00  45.00  60.00   33
 32  \w     88.00 114.00   1.00    6.00    --  108.00  61.00   0.00   26
 33  \w     91.00 117.00   1.00    6.00    --  108.00  45.00 -60.00   26
 34  \w     82.00 115.00   1.00    6.00    --  108.00  30.00   0.00   33
 35  \w     44.00 110.00   1.00    6.00    --  108.00 -94.00-120.00   66
 36  \w     88.00 114.00   1.00    6.00    --  108.00  61.00 -60.00   26
 37  \w    115.00 177.00   1.00    6.00    --  108.00  77.00 -30.00   62
 38  \w     93.00 119.00   1.00    6.00    --  108.00  45.00  60.00   26
 39  \w     88.00 141.00   1.00    6.00    --  108.00  61.00 -30.00   53
 40  \w     79.00 110.00   1.00    6.00    --  108.00  77.00 -30.00   31
 41  \w     88.00 115.00   1.00    6.00    --  108.00  30.00 120.00   27
 42  \w     82.00 161.00   1.00    6.00    --  108.00  30.00 -30.00   79
 43  \w     82.00 108.00   1.00    6.00    --  108.00  30.00  30.00   26
 44  \w     90.00 117.00   1.00    6.00    --  108.00  61.00  30.00   27
 45  \w     91.00 122.00   1.00    6.00    --  108.00  45.00  30.00   31
 46  \w     79.00 118.00   1.00    6.00    --  108.00  77.00 -60.00   39
 47  \w    101.00 170.00   1.00    6.00    --  108.00 111.00  90.00   69
 48  \w     85.00 176.00   1.00    6.00    --  108.00  77.00-150.00   91
 49  \w     64.00  89.00   1.00    6.00    --  108.00  15.00 150.00   25
 50  \w    125.00 162.00   1.00    6.00    --  108.00  15.00 150.00   37
 51  \w     38.00  84.00   1.00    6.00    --  108.00 -94.00-180.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1274414000
_diffrn_orient_matrix_UB_12      0.0395223000
_diffrn_orient_matrix_UB_13      0.0363598000
_diffrn_orient_matrix_UB_21      0.0147103000
_diffrn_orient_matrix_UB_22      0.0132752000
_diffrn_orient_matrix_UB_23      -0.0977108000
_diffrn_orient_matrix_UB_31      -0.0375818000
_diffrn_orient_matrix_UB_32      0.1392111000
_diffrn_orient_matrix_UB_33      -0.0010347000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16351
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         3.836
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.131
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.052(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6064
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.0598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                5053
_reflns_number_total             6064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08316b2.cif
_cod_data_source_block           201911293
_cod_database_code               7125714
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4Cl1
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.842
_reflns_odcompleteness_completeness 99.97
_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 Riding coordinates:
 O3(H3A)
2.b Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C23(H23), C24(H24), C25(H25), C27(H27), C31(H31)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C37(H37A,H37B,
 H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C)
;
_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 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.898