Enantioselective Dearomative Mizoroki–Heck Reaction of Naphthalenes
Han, Xiao-Qing; Wang, Lei; Yang, Ping; Liu, Jing-Yuan; Xu, Wei-Yan; Zheng, Chao; Liang, Ren-Xiao; You, Shu-Li; Zhang, Junliang; Jia, Yi-Xia; ACS Catalysis  (2021) 655–661; doi:10.1021/acscatal.1c05008

data_4519243
_publ_section_title
;
 Enantioselective Dearomative Mizoroki--Heck Reaction of Naphthalenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              655
_journal_page_last               661
_journal_paper_doi               10.1021/acscatal.1c05008
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H17 N O2'
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35
_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             2020-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.81977(6)
_cell_length_b                   11.79139(7)
_cell_length_c                   14.96200(9)
_cell_measurement_reflns_used    29402
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1460
_cell_measurement_theta_min      3.7500
_cell_volume                     1556.008(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_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    -80.00 -22.00   1.00    1.00    --    0.00 -57.00-120.00   58
  2  \w    -17.00  32.00   1.00    1.00    --    0.00  38.00  90.00   49
  3  \w    -89.00 -31.00   1.00    1.00    --    0.00 -38.00  30.00   58
  4  \w    -35.00  -9.00   1.00    1.00    --    0.00 -77.00  90.00   26
  5  \w    -15.00  17.00   1.00    1.00    --    0.00  38.00-120.00   32
  6  \w    -89.00 -48.00   1.00    1.00    --    0.00 -77.00  90.00   41
  7  \w     40.00  83.00   1.00    1.00    --    0.00  38.00   0.00   43
  8  \w     42.00  89.00   1.00    1.00    --    0.00  38.00-120.00   47
  9  \w     38.00  81.00   1.00    1.00    --    0.00  38.00  90.00   43
 10  \w    -23.00  50.00   1.00    1.00    --    0.00  57.00-180.00   73
 11  \w     26.00  78.00   1.00    1.00    --    0.00  57.00 -60.00   52
 12  \w    -23.00  13.00   1.00    1.00    --    0.00  57.00 -60.00   36
 13  \w    -18.00  35.00   1.00    1.00    --    0.00  38.00   0.00   53
 14  \w     75.00 114.00   1.00    1.00    --   95.80  45.00  60.00   39
 15  \w     38.00 128.00   1.00    1.00    --   95.80 -82.00  90.00   90
 16  \w    157.00 183.00   1.00    1.00    --   95.80  73.00 -61.18   26
 17  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 18  \w     63.00  90.00   1.00    1.00    --   95.80  82.00 150.00   27
 19  \w     67.00  92.00   1.00    1.00    --   95.80  73.00 -61.18   25
 20  \w    130.00 174.00   1.00    1.00    --   95.80  77.00-157.92   44
 21  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 22  \w    136.00 162.00   1.00    1.00    --   95.80  49.00 -32.42   26
 23  \w     75.00 139.00   1.00    1.00    --   95.80  45.00-150.00   64
 24  \w    130.00 179.00   1.00    1.00    --   95.80  82.00 150.00   49
 25  \w     72.00  97.00   1.00    1.00    --   95.80  61.00  30.00   25
 26  \w     75.00 185.00   1.00    1.00    --   95.80  61.00 -30.00  110
 27  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 28  \w     63.00 163.00   1.00    1.00    --   95.80  82.00-150.00  100
 29  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00-120.00  121
 30  \w     73.00  99.00   1.00    1.00    --   95.80  53.00 -94.92   26
 31  \w    114.00 179.00   1.00    1.00    --   95.80  70.00-112.06   65
 32  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 33  \w     27.00 126.00   1.00    1.00    --   95.80 -82.00 150.00   99
 34  \w     68.00  94.00   1.00    1.00    --   95.80  70.00-112.06   26
 35  \w    143.00 169.00   1.00    1.00    --   95.80  80.00  73.55   26
 36  \w     71.00 113.00   1.00    1.00    --   95.80  61.00-150.00   42
 37  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 38  \w    101.00 126.00   1.00    1.00    --   95.80 -77.00  30.00   25
 39  \w     71.00  99.00   1.00    1.00    --   95.80  61.00 -60.00   28
 40  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 41  \w    158.00 183.00   1.00    1.00    --   95.80  77.00 -60.00   25
 42  \w     74.00 112.00   1.00    1.00    --   95.80  49.00 -32.42   38
 43  \w      6.00  84.00   1.00    1.00    --   95.80 -77.00  30.00   78
 44  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 45  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 46  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 47  \w     65.00 161.00   1.00    1.00    --   95.80  78.00 -17.66   96
 48  \w     76.00 185.00   1.00    1.00    --   95.80  45.00  90.00  109
 49  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 50  \w     65.00 137.00   1.00    1.00    --   95.80  77.00  90.00   72
 51  \w     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 52  \w     77.00 108.00   1.00    1.00    --   95.80  30.00-180.00   31
 53  \w     76.00 104.00   1.00    1.00    --   95.80  45.00-180.00   28
 54  \w     76.00 184.00   1.00    1.00    --   95.80  45.00 -90.00  108
 55  \w     75.00 101.00   1.00    1.00    --   95.80  45.00 150.00   26
 56  \w    134.00 162.00   1.00    1.00    --   95.80  45.00 150.00   28
 57  \w     72.00 108.00   1.00    1.00    --   95.80  61.00 -90.00   36
 58  \w    160.00 185.00   1.00    1.00    --   95.80  61.00 -90.00   25
 59  \w      6.00 101.00   1.00    1.00    --   95.80 -61.00-120.00   95
 60  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 61  \w     72.00 178.00   1.00    1.00    --   95.80  61.00 120.00  106
 62  \w     71.00  96.00   1.00    1.00    --   95.80  61.00  76.00   25
 63  \w     64.00 101.00   1.00    1.00    --   95.80  80.00  73.55   37
 64  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-157.92   25
 65  \w     51.00 121.00   1.00    1.00    --   95.80 -82.00   0.00   70
 66  \w     66.00  92.00   1.00    1.00    --   95.80  74.00 120.99   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0851657000
_diffrn_orient_matrix_UB_12      0.0074965000
_diffrn_orient_matrix_UB_13      -0.0896847000
_diffrn_orient_matrix_UB_21      -0.0102744000
_diffrn_orient_matrix_UB_22      0.1302898000
_diffrn_orient_matrix_UB_23      0.0034282000
_diffrn_orient_matrix_UB_31      0.1522517000
_diffrn_orient_matrix_UB_32      0.0046129000
_diffrn_orient_matrix_UB_33      0.0504682000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35351
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         4.775
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1155 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_coef       0.0085(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0241
_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^)+(0.0297P)^2^+0.3735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2763
_reflns_number_total             2775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05008_si_002.cif
_cod_data_source_block           exp_1159
_cod_database_code               4519243
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.878
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.94
_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 Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C16(H16), C17(H17),
 C19(H19)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_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 2.188
_oxdiff_exptl_absorpt_empirical_full_min 0.555