Organocatalytic Access to a <i>cis</i>-Cyclopentyl-γ-amino Acid: An Intriguing Model of Selectivity and Formation of a Stable 10/12-Helix from the Corresponding γ/α-Peptide.
Fanelli, Rossana; Berta, Dénes; Földes, Tamás; Rosta, Edina; Atkinson, Robert Andrew; Hofmann, Hans-Jörg; Shankland, Kenneth; Cobb, Alexander J. A.; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b10861

data_4133861
_publ_section_title
;
 Organocatalytic Access to a <i>cis</i>-Cyclopentyl-\g-amino Acid: An
 Intriguing Model of Selectivity and Formation of a Stable 10/12-Helix
 from the Corresponding \g/\a-Peptide.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10861
_journal_year                    2019
_chemical_formula_moiety         'C17 H25 N O6'
_chemical_formula_sum            'C17 H25 N O6'
_chemical_formula_weight         339.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.772(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4204(2)
_cell_length_b                   11.9299(4)
_cell_length_c                   11.1764(4)
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    153(5)
_cell_measurement_theta_max      59.8630
_cell_measurement_theta_min      3.9690
_cell_volume                     851.71(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      153(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2086
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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   -108.00 -57.00   1.00    5.00    --  -33.80-178.00  30.00   51
  2  \w     15.00 102.00   1.00    5.00    --   33.80  57.00-120.00   87
  3  \w     12.00 104.00   1.00    5.00    --   33.80  38.00 120.00   92
  4  \w     61.00 158.00   1.00   17.50    --   86.50  30.00 -90.00   97
  5  \w     15.00  90.00   1.00   17.50    --   86.50-112.00 -30.00   75
  6  \w     16.00  84.00   1.00   17.50    --   86.50 -95.00-150.00   68
  7  \w     66.00 156.00   1.00   17.50    --   86.50  45.00 150.00   90
  8  \w     16.00  84.00   1.00   17.50    --   86.50 -95.00 120.00   68
  9  \w     14.00  91.00   1.00   17.50    --   86.50-113.00  80.00   77
 10  \w     17.00 115.00   1.00   17.50    --   86.50 -77.00  30.00   98
 11  \w     15.00  90.00   1.00   17.50    --   86.50-112.00-180.00   75
 12  \w     58.00 156.00   1.00   17.50    --   86.50  77.00-180.00   98
 13  \w     15.00  90.00   1.00   17.50    --   86.50-112.00 -60.00   75
 14  \w     16.00 124.00   1.00   17.50    --   86.50 -93.00  29.05  108
 15  \w   -108.00 -57.00   1.00    5.00    --  -33.80-178.00-180.00   51
 16  \w      5.00 103.00   1.00    5.00    --   33.80  77.00 150.00   98
 17  \w     15.00 102.00   1.00    5.00    --   33.80  57.00   0.00   87
 18  \w     58.00 156.00   1.00   17.50    --   86.50  77.00 -60.00   98
 19  \w     41.00 159.00   1.00   17.50    --   86.50  15.00  60.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0608391000
_diffrn_orient_matrix_UB_12      -0.0746621000
_diffrn_orient_matrix_UB_13      0.1103373000
_diffrn_orient_matrix_UB_21      -0.0103025000
_diffrn_orient_matrix_UB_22      0.1025604000
_diffrn_orient_matrix_UB_23      0.0830054000
_diffrn_orient_matrix_UB_31      -0.2332140000
_diffrn_orient_matrix_UB_32      -0.0239296000
_diffrn_orient_matrix_UB_33      0.0110354000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6574
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        59.997
_diffrn_reflns_theta_max         59.997
_diffrn_reflns_theta_min         3.975
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0390P)^2^+0.0730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                2328
_reflns_number_total             2431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10861_si_001.cif
_cod_data_source_block           rf266a
_cod_database_code               4133861
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'c17 H25 N1 O6'
_chemical_oxdiff_usercomment     'Copper radiation 150K'
_reflns_odcompleteness_completeness 82.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C12(H12), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C17(H17A,H17B), C15(H15A,H15B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              43472
_shelx_hkl_checksum              15034
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.844