Constructing chiral bicyclo[3.2.1]octanes <i>via</i> low-loading organocatalysis.
Ashok, Etikala; Lakshmi, Pandhiti R.; Sravanthi, Revoju; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 23 (2025) 5616–5628; doi:10.1039/d5ob00203f

data_7160516
_publ_section_title
;
 Constructing chiral bicyclo[3.2.1]octanes <i>via</i> low-loading
 organocatalysis.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5616
_journal_page_last               5628
_journal_paper_doi               10.1039/d5ob00203f
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H25 N O6'
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2024-06-26 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5076(6)
_cell_length_b                   12.7385(7)
_cell_length_c                   15.5696(10)
_cell_measurement_reflns_used    5387
_cell_measurement_temperature    298.23
_cell_measurement_theta_max      23.3700
_cell_measurement_theta_min      2.0700
_cell_volume                     2084.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      298.23
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_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     -7.00  86.00   0.50   11.00    --   16.22  45.00 -30.00  186
  2  \w     -7.00  76.00   0.50   11.00    --   16.22  45.00  60.00  166
  3  \w     -2.00  61.00   0.50   11.00    --   16.22-109.00   4.00  126
  4  \w     40.00  84.00   0.50   11.00    --   16.22-146.00 -61.00   88
  5  \w    -33.00   4.00   0.50   11.00    --  -14.97 -61.00  60.00   74
  6  \w    -61.00  63.00   0.50   11.00    --  -14.97  18.00 -23.00  248
  7  \w    -67.00 -20.00   0.50   11.00    --  -14.97 125.00   0.00   94
  8  \w    -83.00 -47.00   0.50   11.00    --  -14.97 -61.00  60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0541025000
_diffrn_orient_matrix_UB_12      -0.0040659000
_diffrn_orient_matrix_UB_13      -0.0270047000
_diffrn_orient_matrix_UB_21      0.0401117000
_diffrn_orient_matrix_UB_22      -0.0127474000
_diffrn_orient_matrix_UB_23      -0.0351356000
_diffrn_orient_matrix_UB_31      -0.0054308000
_diffrn_orient_matrix_UB_32      -0.0540399000
_diffrn_orient_matrix_UB_33      0.0104102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14335
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.949
_diffrn_reflns_theta_min         2.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0653
_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^)+(0.1068P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1878
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                2518
_reflns_number_total             4297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00203f4.cif
_cod_data_source_block           dbr53
_cod_depositor_comments
'Adding full bibliography for 7160515--7160517.cif.'
_cod_database_code               7160516
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15), C11(H11), C13(H13), C14(H14), C12(H12)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              18297
_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 2.790
_oxdiff_exptl_absorpt_empirical_full_min 0.385