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_7128471
_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 H21 Cl F3 N O4 S'
_chemical_formula_sum            'C17 H21 Cl F3 N O4 S'
_chemical_formula_weight         427.86
_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     dual
_audit_creation_date             2019-04-10
_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                90.570(10)
_cell_angle_beta                 106.868(11)
_cell_angle_gamma                100.186(9)
_cell_formula_units_Z            2
_cell_length_a                   7.3770(8)
_cell_length_b                   11.8839(13)
_cell_length_c                   12.4930(17)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      32.5380
_cell_measurement_theta_min      2.9530
_cell_volume                     1029.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (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                 'CCD plate'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.858
_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   80.00    --   30.00  54.00   0.00  180
  2  \w    -60.00 120.00   1.00   80.00    --   30.00  54.00 120.00  180
  3  \w    -60.00 120.00   1.00   80.00    --   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      0.0013122000
_diffrn_orient_matrix_UB_12      -0.0087631000
_diffrn_orient_matrix_UB_13      -0.0559933000
_diffrn_orient_matrix_UB_21      0.0752546000
_diffrn_orient_matrix_UB_22      -0.0314917000
_diffrn_orient_matrix_UB_23      0.0188665000
_diffrn_orient_matrix_UB_31      -0.0692742000
_diffrn_orient_matrix_UB_32      -0.0512301000
_diffrn_orient_matrix_UB_33      -0.0066069000
_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  0.1067
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12539
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.946
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (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    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         6632
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1380
_refine_ls_R_factor_gt           0.0922
_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^)+(0.1315P)^2^+0.7699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2428
_refine_ls_wR_factor_ref         0.2750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4112
_reflns_number_total             6632
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.2097\% 
 around [0.87 -0.25 -0.43] (reciprocal) or [1.00 0.00 -0.00] (direct)
Component 3 rotated by -179.4368\% 
 around [0.87 -0.24 -0.43] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
_cod_data_source_file            d1cc02952e2.cif
_cod_data_source_block           imai_cf3bn_me075_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7128471--7128475.cif.'
_cod_database_code               7128471
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H21ClF3NO4S
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F1 \\sim F1A \\sim F2 \\sim F2A \\sim C17 \\sim F3 \\sim F3A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 F2, F2A, F3, F3A, F1, F1A, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F2)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C15(H15), C14(H14)
5.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C5(H5A,
 H5B,H5C)
;
_shelx_res_checksum              77165
_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 2.512
_oxdiff_exptl_absorpt_empirical_full_min 0.475
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3