Zn-ProPhenol catalyzed asymmetric inverse-electron-demand Diels-Alder reaction.
Miao, Yu-Hang; Hua, Yuan-Zhao; Jia, Shi-Kun; Xiao, Xiao; Wang, Min-Can; Mei, Guang-Jian; Chemical communications (Cambridge, England) 59 (2023) 6929–6932; doi:10.1039/d3cc01641b

data_7131643
_publ_section_title
;
 Zn-ProPhenol catalyzed asymmetric inverse-electron-demand Diels-Alder
 reaction.
;
_journal_issue                   45
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6929
_journal_page_last               6932
_journal_paper_doi               10.1039/d3cc01641b
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H28 F N O3'
_chemical_formula_sum            'C33 H28 F N O3'
_chemical_formula_weight         505.56
_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             2020-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-22 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.756(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5394(8)
_cell_length_b                   11.1681(9)
_cell_length_c                   12.3498(12)
_cell_measurement_reflns_used    3256
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9310
_cell_measurement_theta_min      3.6420
_cell_volume                     1288.1(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 0.976
_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    -88.00 -15.00   1.00    1.00    --  -33.50 -57.00-150.00   73
  2  \w    -95.00 -33.00   1.00    1.00    --  -33.50 -19.00 -60.00   62
  3  \w    -48.00  36.00   1.00    1.00    --  -33.50  37.00  30.00   84
  4  \w    -22.00  25.00   1.00    1.00    --  -33.50  57.00  90.00   47
  5  \w    -28.00   1.00   1.00    1.00    --  -33.50 -19.00 -60.00   29
  6  \w     44.00  76.00   1.00    1.00    --   36.47 -99.00-150.00   32
  7  \w     61.00 110.00   1.00    1.00    --   36.47 178.00-150.00   49
  8  \w     46.00 106.00   1.00    1.00    --   36.47  19.00 150.00   60
  9  \w     44.00  77.00   1.00    1.00    --   36.47  57.00-180.00   33
 10  \w     26.00  70.00   1.00    1.00    --   36.47  57.00  90.00   44
 11  \w     57.00 109.00   1.00    1.00    --   36.47 178.00   0.00   52
 12  \w     -4.00  21.00   1.00    1.00    --   36.47 103.00 -22.43   25
 13  \w     20.00  60.00   1.00    1.00    --   36.47  57.00 150.00   40
 14  \w      9.00  41.00   1.00    1.00    --   36.47 -99.00-150.00   32
 15  \w     16.00  85.00   1.00    1.00    --   36.47  37.00   0.00   69
 16  \w     79.00 105.00   1.00    3.00    --  108.00  77.00 150.00   26
 17  \w     82.00 108.00   1.00    3.00    --  108.00  30.00 120.00   26
 18  \w    125.00 173.00   1.00    3.00    --  108.00  77.00  90.00   48
 19  \w     45.00 104.00   1.00    3.00    --  108.00 -94.00 -60.00   59
 20  \w     79.00 105.00   1.00    3.00    --  108.00  77.00  90.00   26
 21  \w    148.00 177.00   1.00    3.00    --  108.00  45.00 150.00   29
 22  \w     88.00 114.00   1.00    3.00    --  108.00  61.00 150.00   26
 23  \w     96.00 165.00   1.00    3.00    --  108.00  61.00-180.00   69
 24  \w    131.00 175.00   1.00    3.00    --  108.00  61.00  60.00   44
 25  \w     84.00 110.00   1.00    3.00    --  108.00  30.00 150.00   26
 26  \w     88.00 114.00   1.00    3.00    --  108.00  45.00  90.00   26
 27  \w     40.00 123.00   1.00    3.00    --  108.00 -61.00 120.00   83
 28  \w    139.00 165.00   1.00    3.00    --  108.00  30.00 120.00   26
 29  \w     93.00 119.00   1.00    3.00    --  108.00  45.00-180.00   26
 30  \w     38.00  71.00   1.00    3.00    --  108.00 -94.00  30.00   33
 31  \w    128.00 172.00   1.00    3.00    --  108.00  61.00 -90.00   44
 32  \w     40.00  77.00   1.00    3.00    --  108.00-111.00 -90.00   37
 33  \w     37.00 148.00   1.00    3.00    --  108.00 -15.00  90.00  111
 34  \w     83.00 108.00   1.00    3.00    --  108.00  30.00-180.00   25
 35  \w    118.00 176.00   1.00    3.00    --  108.00  77.00 120.00   58
 36  \w     88.00 114.00   1.00    3.00    --  108.00  61.00 120.00   26
 37  \w     79.00 105.00   1.00    3.00    --  108.00  77.00 120.00   26
 38  \w     94.00 120.00   1.00    3.00    --  108.00  61.00 -90.00   26
 39  \w     88.00 114.00   1.00    3.00    --  108.00  61.00  90.00   26
 40  \w     89.00 114.00   1.00    3.00    --  108.00  61.00  60.00   25
 41  \w     95.00 121.00   1.00    3.00    --  108.00  45.00 150.00   26
 42  \w     85.00 139.00   1.00    3.00    --  108.00  30.00-150.00   54
 43  \w     88.00 126.00   1.00    3.00    --  108.00  61.00 -30.00   38
;
_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      -0.1365033000
_diffrn_orient_matrix_UB_12      -0.0687376000
_diffrn_orient_matrix_UB_13      -0.0537450000
_diffrn_orient_matrix_UB_21      -0.0809506000
_diffrn_orient_matrix_UB_22      0.0577192000
_diffrn_orient_matrix_UB_23      0.0825916000
_diffrn_orient_matrix_UB_31      -0.0449242000
_diffrn_orient_matrix_UB_32      0.1047422000
_diffrn_orient_matrix_UB_33      -0.0807993000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10480
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.675
_diffrn_reflns_theta_min         3.656
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89103
_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    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0405P)^2^+0.0314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                4182
_reflns_number_total             4794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01641b2.cif
_cod_data_source_block           202010220
_cod_depositor_comments          'Adding full bibliography for 7131643.cif.'
_cod_database_code               7131643
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N3F1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.871
_reflns_odcompleteness_completeness 100.00
_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:
 C1(H1), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.862