Enantioselective conjugate addition to nitroolefins catalysed by helical peptides with a single remote stereogenic centre.
Tilly, David P.; McColl, Catherine; Hu, Mingda; Vitórica-Yrezábal, Iñigo J; Webb, Simon J.; Organic & biomolecular chemistry 21 (2023) 9562–9571; doi:10.1039/d3ob01594g

data_7159687
_publ_section_title
;
 Enantioselective conjugate addition to nitroolefins catalysed by helical
 peptides with a single remote stereogenic centre.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9562
_journal_page_last               9571
_journal_paper_doi               10.1039/d3ob01594g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H44 N6 O5, H2 O'
_chemical_formula_sum            'C23 H46 N6 O6'
_chemical_formula_weight         502.66
_chemical_name_systematic        H2NAib4-L-AlaNHtBu
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-15 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.063(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6820(2)
_cell_length_b                   16.3850(3)
_cell_length_c                   15.2184(3)
_cell_measurement_reflns_used    19451
_cell_measurement_temperature    99.99(14)
_cell_measurement_theta_max      75.7350
_cell_measurement_theta_min      3.0120
_cell_volume                     2837.57(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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     13.00  42.00   1.00    3.00    --  -44.36   0.00 150.00   29
  2  \w   -129.00   7.00   1.00    3.00    --  -44.36   0.00 150.00  136
  3  \w    -73.00  -1.00   1.00    3.00    --  -44.36  38.00 -30.00   72
  4  \w    -70.00  18.00   1.00    3.00    --  -46.44  57.00-180.00   88
  5  \w    -87.00  26.00   1.00    3.00    --  -46.44  76.00  30.00  113
  6  \w   -145.00-119.00   1.00   10.00    -- -107.20  76.00-120.00   26
  7  \w   -174.00 -70.00   1.00   10.00    -- -107.20   0.00  30.00  104
  8  \w   -148.00 -19.00   1.00   10.00    -- -107.20  76.00   0.00  129
  9  \w    -83.00 -19.00   1.00   10.00    -- -107.20  76.00  60.00   64
 10  \w   -140.00 -86.00   1.00   10.00    -- -107.20  76.00  60.00   54
 11  \w   -196.00 -77.00   1.00   10.00    -- -107.20 -38.00 150.00  119
 12  \w   -110.00 -42.00   1.00   10.00    -- -107.20  76.00-180.00   68
 13  \w   -188.00 -69.00   1.00   10.00    -- -107.20 -38.00-180.00  119
 14  \w   -141.00 -24.00   1.00   10.00    -- -107.20  76.00 120.00  117
 15  \w   -112.00 -18.00   1.00   10.00    -- -107.20  76.00-120.00   94
 16  \w   -144.00-117.00   1.00   10.00    -- -107.20  76.00-180.00   27
 17  \w    -83.00 -24.00   1.00    4.00    --    5.00 -76.00  90.00   59
 18  \w    -19.00  38.00   1.00    4.00    --    5.00 -76.00  90.00   57
 19  \w   -131.00 -80.00   1.00    4.00    --  -43.99 -76.00  60.00   51
 20  \w    -29.00  -4.00   1.00    4.00    --  -43.99 -76.00  60.00   25
 21  \w   -134.00 -89.00   1.00    4.00    --  -46.21 -76.00   0.00   45
 22  \w    -87.00 -54.00   1.00    4.00    --  -46.21 -76.00-150.00   33
 23  \w    -60.00  -7.00   1.00    4.00    --  -46.21 -76.00   0.00   53
 24  \w   -134.00-108.00   1.00    4.00    --  -46.21 -76.00-150.00   26
 25  \w    -37.00  -8.00   1.00    4.00    --  -46.21 -76.00-150.00   29
 26  \w    -52.00 -22.00   1.00    4.00    --  -62.00 -76.00 -56.17   30
 27  \w    -68.00 -26.00   1.00    4.00    --  -66.00 -76.00 157.85   42
 28  \w    -55.00 -26.00   1.00    4.00    --  -66.00 -76.00  99.69   29
 29  \w    -63.00 -30.00   1.00    4.00    --  -70.00 -76.00  23.59   33
 30  \w    -56.00 -31.00   1.00    4.00    --  -70.00 -74.00-163.77   25
 31  \w    -60.00 -34.00   1.00    4.00    --  -74.00 -76.00  64.11   26
 32  \w    -60.00 -34.00   1.00    4.00    --  -74.00 -76.00  10.08   26
 33  \w    -62.00 -37.00   1.00    4.00    --  -74.00 -70.00 -84.48   25
 34  \w    -62.00 -34.00   1.00    4.00    --  -74.00 -76.00-104.75   28
 35  \w   -111.00 -43.00   1.00   10.00    --  -82.00 -75.00 111.19   68
 36  \w    -78.00 -47.00   1.00   10.00    --  -86.00 -75.00  -2.49   31
 37  \w    -79.00 -54.00   1.00   10.00    --  -90.00 -73.00-173.20   25
 38  \w   -133.00-107.00   1.00   10.00    --  -90.00 -76.00 141.67   26
 39  \w   -145.00 -99.00   1.00   10.00    --  -90.00 -71.00  87.92   46
 40  \w    -86.00 -53.00   1.00   10.00    --  -90.00 -71.00  87.92   33
 41  \w    -94.00 -50.00   1.00   10.00    --  -90.00 -76.00 141.67   44
 42  \w   -166.00 -54.00   1.00   10.00    --  -94.00 -76.00-116.48  112
 43  \w    -88.00 -54.00   1.00   10.00    --  -94.00 -76.00  52.90   34
 44  \w   -167.00 -94.00   1.00   10.00    --  -94.00 -76.00  52.90   73
 45  \w    -81.00 -54.00   1.00   10.00    --  -94.00 -76.00 -86.49   27
 46  \w   -131.00 -87.00   1.00   10.00    --  -94.00 -76.00 -86.49   44
 47  \w    -80.00 -55.00   1.00   10.00    --  -94.00 -74.00 -43.09   25
 48  \w   -138.00-111.00   1.00   10.00    --  -94.00 -74.00 -43.09   27
 49  \w   -156.00-122.00   1.00   10.00    --  -98.00 -70.00 120.16   34
 50  \w   -122.00 -59.00   1.00   10.00    --  -98.00 -76.00  79.24   63
 51  \w   -157.00 -65.00   1.00   10.00    --  -98.00 -71.00  -2.68   92
 52  \w   -104.00 -59.00   1.00   10.00    --  -98.00 -74.00 -65.19   45
 53  \w   -182.00-156.00   1.00   10.00    --  -98.00 -76.00  79.24   26
 54  \w   -164.00 -60.00   1.00   10.00    --  -98.00 -73.00 -17.07  104
 55  \w   -155.00 -64.00   1.00   10.00    --  -98.00 -69.00   4.29   91
 56  \w    -97.00 -60.00   1.00   10.00    --  -98.00 -73.00  40.75   37
 57  \w   -113.00 -62.00   1.00   10.00    --  -98.00 -73.00-135.88   51
 58  \w   -170.00-103.00   1.00   10.00    --  -98.00 -73.00  40.75   67
 59  \w   -167.00 -60.00   1.00   10.00    --  -98.00 -74.00 -48.87  107
 60  \w   -117.00 -61.00   1.00   10.00    --  -98.00 -70.00 120.16   56
 61  \w   -146.00-109.00   1.00   10.00    --  -98.00 -74.00 -65.19   37
 62  \w    -89.00 -64.00   1.00   10.00    -- -102.00 -74.00 -92.23   25
 63  \w   -191.00-123.00   1.00   10.00    -- -102.00 -74.00 -92.23   68
 64  \w    -93.00 -62.00   1.00   10.00    -- -102.00 -76.00-177.92   31
 65  \w   -189.00-161.00   1.00   10.00    -- -102.00 -76.00-177.92   28
 66  \w   -119.00 -69.00   1.00   10.00    -- -107.20 -74.00 155.91   50
 67  \w   -137.00 -71.00   1.00   10.00    -- -107.20  76.00 -60.00   66
 68  \w   -195.00-169.00   1.00   10.00    -- -107.20 -74.00 155.91   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356702000
_diffrn_orient_matrix_UB_12      -0.0071230000
_diffrn_orient_matrix_UB_13      -0.0911954000
_diffrn_orient_matrix_UB_21      -0.0280960000
_diffrn_orient_matrix_UB_22      -0.0919616000
_diffrn_orient_matrix_UB_23      -0.0027985000
_diffrn_orient_matrix_UB_31      -0.1275145000
_diffrn_orient_matrix_UB_32      0.0181907000
_diffrn_orient_matrix_UB_33      -0.0497791000
_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  0.0643
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72133
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.438
_diffrn_reflns_theta_min         2.981
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 4102 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         11450
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0497P)^2^+0.2530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                9824
_reflns_number_total             11450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01594g2.cif
_cod_data_source_block           s6125r
_cod_depositor_comments          'Adding full bibliography for 7159687.cif.'
_cod_database_code               7159687
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.927
_olex2_refinement_description
;
1.a Riding coordinates:
 N3(H3), N6(H6), N9(H9), N12(H12), N23(H23), N27(H27A,H27B), N1(H1A,H1B),
 N37(H37), N40(H40), N43(H43), N49(H49), N52(H52), O69(H69A,H69B), O70(H70A,
 H70B)
1.b Ternary CH refined with riding coordinates:
 C10(H10), C41(H41)
1.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C26(H26A,H26B,H26C), C28(H28A,
 H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C),
 C34(H34A,H34B,H34C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C47(H47A,H47B,
 H47C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C), C59(H59A,H59B,H59C), C60(H60A,
 H60B,H60C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C65(H65A,H65B,H65C),
 C67(H67A,H67B,H67C), C68(H68A,H68B,H68C)
;
_shelx_res_checksum              87163
_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 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.568