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_7128474
_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 H17 Br Cl N O4 S'
_chemical_formula_sum            'C14 H17 Br Cl N O4 S'
_chemical_formula_weight         410.71
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 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                 90.055(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5794(9)
_cell_length_b                   8.0509(19)
_cell_length_c                   33.122(6)
_cell_measurement_reflns_used    2068
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.6530
_cell_measurement_theta_min      3.0690
_cell_volume                     1754.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Rigaku Mercury area detector'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    8.00    --   30.00  54.00   0.00  180
  2  \w    -60.00 114.00   1.00    8.00    --   30.00  54.00 120.00  174
;
_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      -0.1055717000
_diffrn_orient_matrix_UB_12      -0.0175931000
_diffrn_orient_matrix_UB_13      0.0010955000
_diffrn_orient_matrix_UB_21      0.0078460000
_diffrn_orient_matrix_UB_22      -0.0087131000
_diffrn_orient_matrix_UB_23      0.0211500000
_diffrn_orient_matrix_UB_31      -0.0207576000
_diffrn_orient_matrix_UB_32      0.0861680000
_diffrn_orient_matrix_UB_33      0.0023866000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            9634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.604
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (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    1.555
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0857
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0884P)^2^+6.4801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2556
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02952e2.cif
_cod_data_source_block           sim_up
_cod_depositor_comments
'Adding full bibliography for 7128471--7128475.cif.'
_cod_database_code               7128474
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H18 Br Cl2 N O4 S'
_shelx_estimated_absorpt_t_max   0.353
_shelx_estimated_absorpt_t_min   0.228
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.802(3)
 0.198(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C6(H6)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              90242
_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 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.646