Facile synthesis of new N-(aminocycloalkylene)amino acid compounds using chiral triflate esters with N-Boc-aminopyrrolidines and N-Boc-aminopiperidines
Matulevičiūtė, Gita; Kleizienė, Neringa; Račkauskienė, Greta; Martynaitis, Vytas; Bieliauskas, Aurimas; Šachlevičiūtė, Urtė; Jankauskas, Rokas; Bartkus, Martynas R.; Sløk, Frank A.; Šačkus, Algirdas; RSC Advances 13 (2023) 21378–21394; doi:10.1039/D3RA03060A

data_7247062
_publ_section_title
;
 Facile synthesis of new N-(aminocycloalkylene)amino acid compounds using
 chiral triflate esters with N-Boc-aminopyrrolidines and
 N-Boc-aminopiperidines
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              21378
_journal_page_last               21394
_journal_paper_doi               10.1039/D3RA03060A
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H30 N2 O4'
_chemical_formula_sum            'C16 H30 N2 O4'
_chemical_formula_weight         324.43
_chemical_name_systematic
'tert-butyl 1-((R)-1-(methoxycarbonyl)-2-methylpropyl)piperidin-4-ylcarbamate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-17
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2023-03-07 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.4889(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.08686(12)
_cell_length_b                   12.80881(17)
_cell_length_c                   14.06927(18)
_cell_measurement_reflns_used    18339
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      77.1510
_cell_measurement_theta_min      3.1690
_cell_volume                     1802.25(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.93
_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    103.00 129.98   0.38    0.37    --  105.75  77.00  30.00   71
  2  \w     95.00 120.08   0.38    0.09    --   49.67  77.00-120.00   66
  3  \w     89.00 174.12   0.38    0.37    --  105.75  77.00-150.00  224
  4  \w     99.00 127.12   0.38    0.37    --  105.75  77.00-120.00   74
  5  \w    131.00 174.70   0.38    0.37    --  105.75  77.00-120.00  115
  6  \w    147.00 173.98   0.38    0.37    --  105.75  61.00 -60.00   71
  7  \w     93.00 171.66   0.38    0.37    --  105.75  61.00   0.00  207
  8  \w    103.00 128.08   0.38    0.37    --  105.75  30.00  60.00   66
  9  \w    111.00 159.64   0.38    0.37    --  105.75  15.00 120.00  128
 10  \w    109.00 170.18   0.38    0.37    --  105.75  30.00 -90.00  161
 11  \w    133.00 159.22   0.38    0.37    --  105.75  15.00-120.00   69
 12  \w    103.00 129.22   0.38    0.37    --  105.75   0.00-120.00   69
 13  \w    102.00 128.98   0.38    0.37    --  105.75  30.00-180.00   71
 14  \w     95.00 133.00   0.38    0.37    --  105.75 139.00 -37.00  100
 15  \w    110.00 134.70   0.38    0.37    --  105.75 131.00 147.00   65
 16  \w     96.00 136.66   0.38    0.37    --  105.75 125.00   0.00  107
 17  \w    144.00 172.50   0.38    0.37    --  105.75 125.00   0.00   75
 18  \w     39.00  66.36   0.38    0.37    --  105.75 -61.00-120.00   72
 19  \w     36.00  62.22   0.38    0.37    --  105.75 -77.00-180.00   69
 20  \w     49.00  74.08   0.38    0.37    --  105.75 -77.00 -60.00   66
 21  \w     50.00  76.22   0.38    0.37    --  105.75 -77.00  60.00   69
 22  \w     37.00  91.34   0.38    0.37    --  105.75 -77.00  90.00  143
 23  \w     39.00  66.36   0.38    0.37    --  105.75 -61.00 150.00   72
 24  \w     35.00  65.78   0.38    0.37    --  105.75 -61.00 -90.00   81
 25  \w     81.00 107.22   0.38    0.37    --  105.75 -86.00-140.87   69
 26  \w     46.00  79.82   0.38    0.37    --  105.75-125.00-180.00   89
 27  \w     87.00 120.06   0.38    0.37    --  105.75-139.00 -97.00   87
 28  \w     64.00  90.22   0.38    0.37    --  105.75-125.00 -60.00   69
 29  \w     48.00  73.08   0.38    0.09    --   49.67-139.00 -97.00   66
 30  \w     85.00 110.08   0.38    0.37    --  105.75-125.00-180.00   66
 31  \w     35.00 109.86   0.38    0.37    --  105.75-125.00  30.00  197
 32  \w     63.00 104.80   0.38    0.37    --  105.75 -94.00  90.00  110
 33  \w     73.00  99.22   0.38    0.37    --  105.75-131.00  76.00   69
 34  \w     79.00 104.08   0.38    0.37    --  105.75 -94.00 120.00   66
 35  \w     56.00  82.22   0.38    0.09    --   49.67-131.00  76.00   69
 36  \w     59.00 101.94   0.38    0.37    --  105.75 -94.00  60.00  113
 37  \w     46.00 100.34   0.38    0.37    --  105.75 -94.00  30.00  143
 38  \w     59.00  85.22   0.38    0.37    --  105.75 -94.00 -60.00   69
 39  \w     47.00  72.08   0.38    0.37    --  105.75 -86.00-140.87   66
 40  \w     72.00 103.92   0.38    0.37    --  105.75 -94.00-180.00   84
 41  \w    -89.00 -47.96   0.38    0.09    --  -49.67 131.00 147.00  108
 42  \w   -119.00 -89.36   0.38    0.09    --  -49.67 -77.00  60.00   78
 43  \w   -118.00 -89.88   0.38    0.09    --  -49.67 -77.00-150.00   74
 44  \w   -116.00 -88.64   0.38    0.09    --  -49.67 -77.00-180.00   72
 45  \w   -119.00 -93.92   0.38    0.09    --  -49.67 -77.00-120.00   66
 46  \w   -118.00 -91.78   0.38    0.09    --  -49.67 -77.00 -90.00   69
 47  \w    -46.00 -12.94   0.38    0.37    --  -84.25  15.00  30.00   87
 48  \w   -119.00 -71.12   0.38    0.09    --  -49.67-131.00  76.00  126
 49  \w   -138.00-112.92   0.38    0.37    --  -84.25-131.00  76.00   66
 50  \w   -120.00 -92.64   0.38    0.09    --  -49.67-139.00 -97.00   72
 51  \w   -135.00-109.92   0.38    0.37    --  -84.25-139.00 -97.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0422380000
_diffrn_orient_matrix_UB_12      -0.0455810000
_diffrn_orient_matrix_UB_13      0.1007553000
_diffrn_orient_matrix_UB_21      0.0127968000
_diffrn_orient_matrix_UB_22      0.1112863000
_diffrn_orient_matrix_UB_23      0.0417683000
_diffrn_orient_matrix_UB_31      -0.1474998000
_diffrn_orient_matrix_UB_32      -0.0034556000
_diffrn_orient_matrix_UB_33      0.0174858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22287
_diffrn_reflns_theta_full        75.0
_diffrn_reflns_theta_max         77.39
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.96016
_exptl_absorpt_correction_T_min  0.87241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.1587
_exptl_crystal_description       'Block '
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.1426
_refine_diff_density_min         -0.1904
_refine_diff_density_rms         0.0347
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_d_res_high            0.7900
_refine_ls_d_res_low             13.9493
_refine_ls_goodness_of_fit_ref   1.0525
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    84
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7121
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0525
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.2072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.864
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                6941
_reflns_number_total             7121
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ra03060a2.cif
_cod_data_source_block           GMP571
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H60 N4 O8'
_cod_original_formula_weight         628.86
_cod_original_formula_moiety         '2(C16 H30 N2 O4)'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7247062
_chemical_oxdiff_formula         'C64 H120 N8 O16'
_chemical_oxdiff_usercomment     'GMP-571 (from Vytas)'
_diffrn_oxdiff_digest_frames
;
010839e5a3ff80c227627bfe07fe3e23b300042b917
;
_diffrn_oxdiff_digest_hkl
;
01c4e0483fad013148f1a84b320c58a98b9b81
;
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C54(H54), C57(H57), C58(H58)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C5(H5a,H5b), C6(H6a,H6b), C52(H52a,H52b), C53(H53a,
 H53b), C55(H55a,H55b), C56(H56a,H56b)
2.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C10(H10a,H10b,H10c), C14(H14a,H14b,H14c), C20(H20a,H20b,
 H20c), C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C59(H59a,H59b,H59c), C60(H60a,
 H60b,H60c), C64(H64a,H64b,H64c), C70(H70a,H70b,H70c), C71(H71a,H71b,H71c),
 C72(H72a,H72b,H72c)
;
_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 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.679