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_7128473
_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         'C14 H18 Br Cl2 N O4 S'
_chemical_formula_sum            'C14 H18 Br Cl2 N O4 S'
_chemical_formula_weight         447.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-02-13
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.17(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.396(4)
_cell_length_b                   14.044(4)
_cell_length_c                   11.920(3)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.3190
_cell_measurement_theta_min      2.3260
_cell_volume                     1829.3(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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_temperature      293.15
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   70.00    --   30.00  54.00   0.00  180
  2  \w    -60.00 120.00   1.00   70.00    --   30.00  54.00 120.00  180
  3  \w    -60.00 120.00   1.00   70.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15794
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.362
_exptl_absorpt_coefficient_mu    2.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0358P)^2^+0.6943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1768
_reflns_number_total             3349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02952e2.cif
_cod_data_source_block           sim_down
_cod_depositor_comments
'Adding full bibliography for 7128471--7128475.cif.'
_cod_database_code               7128473
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C6A
 At 1.2 times of:
  H2 of C2, H6 of C6, H5 of C5, H5A of C5A, H6A of C6A, H7 of C7, H3 of C3
2. Uiso/Uaniso restraints and constraints
C5 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C5A \\sim C6A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5A, C6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=1-FVAR(1)
 Sof(C6)=Sof(H6)=Sof(C5)=Sof(H5)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C5(H5), C5A(H5A), C6A(H6A)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C)
;
_shelx_res_checksum              99091
_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
;