Stereoselective Synthesis of Alkyl-, Aryl-, Vinyl- and Alkynyl-Substituted Z- Enamides and Enol Ethers
Caramenti, Paola; Declas, Nina; Tessier, Romain; Wodrich, Matthew D.; Waser, Jerome; Chemical Science  (2019) –; doi:10.1039/C8SC05573D

data_1550556
_publ_section_title
;
 Stereoselective Synthesis of Alkyl-, Aryl-, Vinyl- and
 Alkynyl-Substituted Z- Enamides and Enol Ethers
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05573D
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 I N O5 S, C H4 O'
_chemical_formula_sum            'C25 H26 I N O6 S'
_chemical_formula_weight         595.43
_chemical_name_systematic        N-vBX
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-29 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.056(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0732(3)
_cell_length_b                   30.9671(9)
_cell_length_c                   10.1196(4)
_cell_measurement_reflns_used    4655
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      74.5060
_cell_measurement_theta_min      4.6460
_cell_volume                     2510.78(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_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    -55.00  32.00   1.00    2.00    --  -40.91  38.00 150.00   87
  2  \w    -65.00  30.00   1.00    2.00    --  -40.91  38.00  60.00   95
  3  \w    -38.00 -11.00   1.00    2.00    --  -40.91  57.00 -60.00   27
  4  \w     23.00  74.00   1.00    2.00    --   40.91-125.00-120.00   51
  5  \w    125.00 173.00   1.00    8.00    --  112.00 125.00  60.00   48
  6  \w    118.00 156.00   1.00    8.00    --  112.00  45.00-120.00   38
  7  \w     91.00 137.00   1.00    8.00    --  112.00 -61.00 150.00   46
  8  \w     59.00 178.00   1.00    8.00    --  112.00  15.00-180.00  119
  9  \w     40.00 111.00   1.00    8.00    --  112.00-125.00 -90.00   71
 10  \w    132.00 172.00   1.00    8.00    --  112.00  15.00-150.00   40
 11  \w     40.00  90.00   1.00    8.00    --  112.00 -61.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1484452000
_diffrn_orient_matrix_UB_12      -0.0132483000
_diffrn_orient_matrix_UB_13      -0.1023576000
_diffrn_orient_matrix_UB_21      -0.1111535000
_diffrn_orient_matrix_UB_22      -0.0041742000
_diffrn_orient_matrix_UB_23      0.1127782000
_diffrn_orient_matrix_UB_31      -0.0507584000
_diffrn_orient_matrix_UB_32      0.0477601000
_diffrn_orient_matrix_UB_33      -0.0184717000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9471
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.967
_diffrn_reflns_theta_min         2.854
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.141
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_correction_T_min  0.098
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.117
_refine_diff_density_max         1.871
_refine_diff_density_min         -1.801
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+16.1692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.1935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4499
_reflns_number_total             5052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05573d2.cif
_cod_data_source_block           pc6-068
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2510.76(15)
_cod_database_code               1550556
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H26 I N O6 S'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.281
_oxdiff_exptl_absorpt_empirical_full_min 0.635