Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of ( E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters.
Xiong, Qian; Lin, Lili; Zhao, Xiaohu; Lang, Jiawen; Liu, Xiaohua; Feng, Xiaoming; The Journal of organic chemistry 83 (2018) 12527–12534; doi:10.1021/acs.joc.8b01771

data_4035426
_publ_section_title
;
 Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of ( E)-1-Phenyl
 Dienes with \b,\g-Unsaturated \a-Ketoesters.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12527
_journal_page_last               12534
_journal_paper_doi               10.1021/acs.joc.8b01771
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H21 F O3'
_chemical_formula_sum            'C22 H21 F O3'
_chemical_formula_weight         352.39
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5771(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.33980(13)
_cell_length_b                   10.15555(18)
_cell_length_c                   10.95054(19)
_cell_measurement_reflns_used    8580
_cell_measurement_temperature    294.6(5)
_cell_measurement_theta_max      72.3410
_cell_measurement_theta_min      4.4130
_cell_volume                     925.65(3)
_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      294.6(5)
_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 0.994
_diffrn_measurement_details
;
  1 omega    1.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   93.0000  117.4486 26

  2 omega   15.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   68.0000   82.0000 88

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

  4 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  120.0000 67

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  120.0000 84

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -120.0000 74

  7 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000    0.0000 88

  8 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

  9 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -60.0000 74

 10 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000 -120.0000 101

 11 omega    8.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   82.0000  -44.4630 37

 12 omega   11.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   84.0000   81.2356 27

 13 omega   12.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   83.0000    8.4185 28

 14 omega   11.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   84.0000  -98.2197 27

 15 omega   24.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   76.0000   88.9725 93

 16 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  153.1435 26

 17 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000 -155.1508 26

 18 omega   28.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000 -132.2124 93

 19 omega   29.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   74.0000  135.8655 92

 20 omega   28.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000    7.6748 93

 21 omega   28.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   75.0000  -66.2392 93

 22 omega   27.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -114.8607 95

 23 omega   27.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   68.7837 95

 24 omega   29.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   73.0000  -32.1142 92

 25 omega   64.00  157.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -       90.0000   76.0000  141.8550 93

 26 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 27 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

 28 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 29 omega   41.00  126.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 85

 30 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 31 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 85

 32 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

 33 omega   39.00  109.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 34 omega   39.00  109.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 35 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 36 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 85

 37 omega   38.00  116.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

 38 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 39 omega   40.00   98.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 40 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 41 omega   86.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   68.0000   82.0000 89

 42 omega   40.00   98.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 43 omega   39.00  109.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 44 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 45 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 46 omega   90.00  175.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 85

 47 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 48 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 49 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 50 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 51 omega   81.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 52 omega   91.00  130.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 39

 53 omega   81.00  107.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 54 omega   81.00  107.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26
;
_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      -0.0470217000
_diffrn_orient_matrix_UB_12      0.0890642000
_diffrn_orient_matrix_UB_13      0.1058800000
_diffrn_orient_matrix_UB_21      0.1783789000
_diffrn_orient_matrix_UB_22      0.0332824000
_diffrn_orient_matrix_UB_23      0.0297735000
_diffrn_orient_matrix_UB_31      -0.0147094000
_diffrn_orient_matrix_UB_32      0.1182874000
_diffrn_orient_matrix_UB_33      -0.0880945000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19160
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.630
_diffrn_reflns_theta_min         5.314
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49520
_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 whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details
;
 Flack x determined using 1503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3609
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1080P)^2^+0.0060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3459
_reflns_number_total             3609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01771_si_002.cif
_cod_data_source_block           fxm-xq-159
_cod_database_code               4035426
_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 Ternary CH refined with riding coordinates:
 C007(H007), C00C(H00d), C00E(H00f)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00b,H00c)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00D(H00e), C00F(H00g), C00J(H00k), C00K(H00l),
 C00L(H00m), C00N(H00N), C00O(H00O), C00Q(H00s)
2.d Idealised Me refined as rotating group:
 C00I(H00h,H00i,H00j), C00P(H00p,H00q,H00r)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-27
_olex2_submission_special_instructions 'No special instructions were received'