Stereoselective synthesis of highly functionalized (<i>Z</i>)-chloroalkene dipeptide isosteres containing an α,α-disubstituted amino acid.
Kodama, Yuki; Imai, Saki; Fujimoto, Junko; Sato, Kohei; Mase, Nobuyuki; Narumi, Tetsuo; Chemical communications (Cambridge, England) 57 (2021) 6915–6918; doi:10.1039/d1cc02952e

data_7128472
_publ_section_title
;
 Stereoselective synthesis of highly functionalized
 (<i>Z</i>)-chloroalkene dipeptide isosteres containing an
 \a,\a-disubstituted amino acid.
;
_journal_issue                   56
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6915
_journal_page_last               6918
_journal_paper_doi               10.1039/d1cc02952e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C15 H24 Cl N O4 S'
_chemical_formula_sum            'C15 H24 Cl N O4 S'
_chemical_formula_weight         349.86
_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     iterative
_audit_creation_date             2021-02-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2021-03-01 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                93.204(8)
_cell_angle_beta                 99.536(10)
_cell_angle_gamma                96.869(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0093(11)
_cell_length_b                   8.9932(9)
_cell_length_c                   14.7723(15)
_cell_measurement_reflns_used    2618
_cell_measurement_temperature    293
_cell_measurement_theta_max      32.4880
_cell_measurement_theta_min      2.3730
_cell_volume                     909.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku Mercury area detector'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    -60.00 120.00   1.00  120.00    --   30.00  54.00   0.00  180
  2  \w    -60.00 120.00   1.00  120.00    --   30.00  54.00 120.00  180
  3  \w    -60.00 120.00   1.00  120.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0184560000
_diffrn_orient_matrix_UB_12      0.0586344000
_diffrn_orient_matrix_UB_13      0.0357145000
_diffrn_orient_matrix_UB_21      0.0182758000
_diffrn_orient_matrix_UB_22      -0.0530817000
_diffrn_orient_matrix_UB_23      0.0330839000
_diffrn_orient_matrix_UB_31      0.1001911000
_diffrn_orient_matrix_UB_32      0.0096538000
_diffrn_orient_matrix_UB_33      -0.0038417000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7608
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         2.288
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0398P)^2^+0.7456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2464
_reflns_number_total             3211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02952e2.cif
_cod_data_source_block           kodama_20210222
_cod_depositor_comments
'Adding full bibliography for 7128471--7128475.cif.'
_cod_database_code               7128472
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H24ClNO4S
_reflns_odcompleteness_completeness 89.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C6 \\sim C12 \\sim C13A \\sim C13 \\sim C14A \\sim C14 \\sim C15: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
3. Others
 Sof(H12C)=Sof(H12D)=Sof(H15C)=Sof(H15D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=
 Sof(C13A)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(H12A)=Sof(H12B)=Sof(H15A)=Sof(H15B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12(H12C,H12D), C10(H10A,H10B), C15(H15A,H15B), C15(H15C,
 H15D), C13(H13A,H13B), C14(H14A,H14B), C14A(H14C,H14D), C13A(H13C,H13D)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C4(H4A,H4B,H4C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              33583
_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.762