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_7160515
_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         'C23 H27 N O6'
_chemical_formula_sum            'C23 H27 N O6'
_chemical_formula_weight         413.45
_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     iterative
_audit_creation_date             2023-05-10
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2024-06-04 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                   9.8373(7)
_cell_length_b                   12.5432(11)
_cell_length_c                   18.3743(13)
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    296(2)
_cell_volume                     2267.2(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7149
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.966
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1325 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.8478.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
 Flack x determined using 1489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0780
_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^)+(0.1027P)^2^+0.1288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1819
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                4170
_reflns_number_total             4922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00203f4.cif
_cod_data_source_block           dbr011_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160515--7160517.cif.'
_cod_database_code               7160515
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.979
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C11(H11), C4(H4), C1(H1)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              49303
_olex2_submission_special_instructions 'No special instructions were received'