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_7128475
_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         'C17 H29 Cl N O4 S, C12 H24 N, 0.5(C6 H14)'
_chemical_formula_sum            'C32 H60 Cl N2 O4 S'
_chemical_formula_weight         604.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.248(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.1676(19)
_cell_length_b                   21.601(3)
_cell_length_c                   23.423(4)
_cell_measurement_reflns_used    4632
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.0460
_cell_measurement_theta_min      2.3540
_cell_volume                     7148.5(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_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    'SHELXT  (Sheldrick, 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      -0.0366654000
_diffrn_orient_matrix_UB_12      0.0060305000
_diffrn_orient_matrix_UB_13      0.0182798000
_diffrn_orient_matrix_UB_21      -0.0324604000
_diffrn_orient_matrix_UB_22      0.0040573000
_diffrn_orient_matrix_UB_23      -0.0242476000
_diffrn_orient_matrix_UB_31      -0.0110550000
_diffrn_orient_matrix_UB_32      -0.0320182000
_diffrn_orient_matrix_UB_33      0.0003770000
_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  0.0845
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31587
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.374
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
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    1.123
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             2648
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6551
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0861P)^2^+0.4865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3296
_reflns_number_total             6551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02952e2.cif
_cod_data_source_block           imai_20201118_2
_cod_depositor_comments
'Adding full bibliography for 7128471--7128475.cif.'
_cod_original_cell_volume        7148.8(17)
_cod_database_code               7128475
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C25H39ClN2O3S
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.29
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33-C34 \\sim C35-C34 \\sim C33-C32 \\sim C32-C31 \\sim C30-C31
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C35 \\sim C34 \\sim C33 \\sim C32 \\sim C31 \\sim C30: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C35, C31, H31A, H31B, C32, C30, C33, H32A, H32B, H30A, H30B, H30C, H33A, H33B,
  C34, H34A, H34B, H35A, H35B, H35C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C31(0.5) H31A(0.5) H31B(0.5) C33(0.5) H33A(0.5) H33B(0.5)
 H35A(0.5) H35B(0.5) H35C(0.5) C34(0.5) H34A(0.5) H34B(0.5) C32(0.5) H32A(0.5)
 H32B(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
6.a Riding coordinates:
 N1(H1)
6.b Ternary CH refined with riding coordinates:
 C2(H2), C18(H18), C24(H24), C11(H11)
6.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C10(H10A,H10B), C9(H9A,H9B), C29(H29A,H29B), C23(H23A,H23B),
 C25(H25A,H25B), C6(H6A,H6B), C19(H19A,H19B), C26(H26A,H26B), C27(H27A,H27B),
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C7(H7A,H7B), C28(H28A,H28B),
 C8(H8A,H8B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B), C32(H32A,H32B)
6.d Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C)
6.e Aromatic/amide H refined with riding coordinates:
 C3(H3)
6.f Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              98621
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.665