Cu(i)-Catalyzed stereoselective synthesis of trisubstituted Z-enol esters via interrupting the 1,3-O-transposition reaction
Zhang, Changyuan; Chen, Lianfen; Chen, Kai; Wang, Chuntao; Xu, Zurong; Jiang, Huanfeng; Zhu, Shifa; Organic Chemistry Frontiers 5 (2018) 2510–; doi:10.1039/C8QO00664D

data_1554379
_publ_section_title
;
 Cu(i)-Catalyzed stereoselective synthesis of trisubstituted Z-enol esters
 via interrupting the 1,3-O-transposition reaction
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2510
_journal_paper_doi               10.1039/C8QO00664D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C32 H27 N O5 S'
_chemical_formula_sum            'C32 H27 N O5 S'
_chemical_formula_weight         537.60
_chemical_name_systematic        6o
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-04 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                66.455(10)
_cell_angle_beta                 73.203(9)
_cell_angle_gamma                66.317(11)
_cell_formula_units_Z            2
_cell_length_a                   10.2760(12)
_cell_length_b                   12.5669(14)
_cell_length_c                   13.0463(13)
_cell_measurement_reflns_used    3513
_cell_measurement_temperature    268(40)
_cell_measurement_theta_max      26.2490
_cell_measurement_theta_min      4.1570
_cell_volume                     1397.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      268(40)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.839
_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    -28.00  53.00   1.00    1.50    --   11.74  19.00  90.00   81
  2  \w     25.00  52.00   1.00    1.50    --   11.74  77.00 150.00   27
  3  \w    -12.00  57.00   1.00    1.50    --   11.74  37.00   0.00   69
  4  \w    -17.00  27.00   1.00    1.50    --  -11.59 -99.00   0.00   44
  5  \w    -17.00  53.00   1.00    1.50    --   11.74 -99.00 150.00   70
  6  \w    -40.00  12.00   1.00    1.50    --   11.74 -37.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0427713000
_diffrn_orient_matrix_UB_12      0.0163702000
_diffrn_orient_matrix_UB_13      -0.0534865000
_diffrn_orient_matrix_UB_21      0.0439201000
_diffrn_orient_matrix_UB_22      0.0112520000
_diffrn_orient_matrix_UB_23      0.0249872000
_diffrn_orient_matrix_UB_31      0.0453760000
_diffrn_orient_matrix_UB_32      -0.0620255000
_diffrn_orient_matrix_UB_33      0.0107867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12753
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.511
_diffrn_reflns_theta_min         3.312
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.031(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         6547
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0586P)^2^+0.0024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3584
_reflns_number_total             6547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00664d2.cif
_cod_data_source_block           exp_765
_cod_original_cell_volume        1397.7(3)
_cod_database_code               1554379
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Restrained distances
 C28-C29
 1.38 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C2(H2), C3(H3), C6(H6), C14(H14), C18(H18), C17(H17),
 C25(H25), C5(H5), C16(H16), C24(H24), C31(H31), C15(H15), C21(H21), C23(H23),
 C27(H27), C22(H22), C28(H28), C30(H30), C29(H29)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C32(H32A,H32B,H32C)
;
_olex2_date_sample_data_collection 2017-07-25
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.646