#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:59:43 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301174 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/05/7160515.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160515
loop_
_publ_author_name
'Ashok, Etikala'
'Lakshmi, Pandhiti R.'
'Sravanthi, Revoju'
'Ramachary, Dhevalapally B.'
_publ_section_title
;
 Constructing chiral bicyclo[3.2.1]octanes via low-loading
 organocatalysis.
;
_journal_issue                   23
_journal_name_full               'Organic & 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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.1027P)²+0.1288P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.4281(2) 0.8637(2) 0.30924(14) 0.0576(6) Uani 1 1 d . . . . .
O3 O 0.6685(2) 0.77257(18) 0.37236(11) 0.0485(5) Uani 1 1 d . . . . .
O4 O 0.7273(3) 0.9194(2) 0.30993(15) 0.0686(7) Uani 1 1 d . . . . .
O2 O 0.4001(3) 0.6656(2) 0.40762(16) 0.0735(8) Uani 1 1 d . . . . .
O1 O 0.5500(4) 0.5572(3) 0.44863(17) 0.0889(10) Uani 1 1 d . . . . .
N1 N 0.5002(3) 0.6100(2) 0.40022(16) 0.0558(7) Uani 1 1 d . . . . .
C13 C 0.4689(3) 0.7791(3) 0.28979(16) 0.0467(7) Uani 1 1 d . . . . .
O5 O 0.4328(3) 0.7270(4) 0.10812(15) 0.1009(13) Uani 1 1 d . . . . .
C6 C 0.1652(3) 0.6927(3) 0.2872(2) 0.0570(8) Uani 1 1 d . . . . .
C22 C 0.7169(3) 0.8745(3) 0.36628(18) 0.0495(7) Uani 1 1 d . . . . .
C2 C 0.0544(4) 0.7503(3) 0.3976(3) 0.0726(11) Uani 1 1 d . . . . .
H2 H 0.034865 0.805390 0.429853 0.087 Uiso 1 1 calc R . . . .
C12 C 0.6053(3) 0.7278(3) 0.30946(16) 0.0470(7) Uani 1 1 d . . . . .
C5 C 0.1126(3) 0.5916(3) 0.3002(2) 0.0648(10) Uani 1 1 d . . . . .
H5 H 0.129935 0.536918 0.267338 0.078 Uiso 1 1 calc R . . . .
C11 C 0.6912(3) 0.7307(3) 0.24177(18) 0.0541(8) Uani 1 1 d . . . . .
H11 H 0.784874 0.736551 0.247233 0.065 Uiso 1 1 calc R . . . .
C7 C 0.2545(3) 0.7133(4) 0.2221(2) 0.0639(9) Uani 1 1 d . . . . .
H7A H 0.238140 0.785323 0.205086 0.077 Uiso 1 1 calc R . . . .
H7B H 0.228347 0.664871 0.183444 0.077 Uiso 1 1 calc R . . . .
C4 C 0.0351(3) 0.5713(3) 0.3612(2) 0.0660(10) Uani 1 1 d . . . . .
H4 H 0.002497 0.502631 0.368957 0.079 Uiso 1 1 calc R . . . .
C15 C 0.5660(3) 0.6105(3) 0.32453(18) 0.0501(7) Uani 1 1 d . . . . .
C10 C 0.6410(3) 0.7253(3) 0.17415(18) 0.0592(8) Uani 1 1 d . . . . .
C8 C 0.4081(3) 0.7000(3) 0.23667(18) 0.0530(8) Uani 1 1 d . . . . .
C16 C 0.6812(4) 0.5301(3) 0.3239(2) 0.0675(10) Uani 1 1 d . . . . .
H16A H 0.751065 0.552688 0.356967 0.101 Uiso 1 1 calc GR . . . .
H16B H 0.718168 0.525114 0.275636 0.101 Uiso 1 1 calc GR . . . .
H16C H 0.647397 0.461651 0.338618 0.101 Uiso 1 1 calc GR . . . .
C3 C 0.0045(3) 0.6500(4) 0.4112(2) 0.0649(9) Uani 1 1 d . . . . .
C23 C 0.7527(4) 0.9191(4) 0.4389(2) 0.0696(10) Uani 1 1 d . . . . .
H23A H 0.675918 0.956593 0.458496 0.104 Uiso 1 1 calc GR . . . .
H23B H 0.827926 0.967288 0.433943 0.104 Uiso 1 1 calc GR . . . .
H23C H 0.777402 0.862031 0.471155 0.104 Uiso 1 1 calc GR . . . .
C14 C 0.4526(3) 0.5906(3) 0.2677(2) 0.0549(8) Uani 1 1 d . . . . .
H14A H 0.375922 0.555174 0.290446 0.066 Uiso 1 1 calc R . . . .
H14B H 0.486418 0.545367 0.228867 0.066 Uiso 1 1 calc R . . . .
C1 C 0.1327(4) 0.7709(4) 0.3372(3) 0.0708(10) Uani 1 1 d . . . . .
H1 H 0.164805 0.839758 0.329712 0.085 Uiso 1 1 calc R . . . .
C9 C 0.4909(4) 0.7190(4) 0.1655(2) 0.0644(9) Uani 1 1 d . . . . .
C17 C 0.7322(4) 0.7277(4) 0.1061(2) 0.0755(12) Uani 1 1 d . . . . .
C20 C 0.7016(7) 0.6298(6) 0.0595(3) 0.116(2) Uani 1 1 d . . . . .
H20A H 0.717913 0.566394 0.087429 0.174 Uiso 1 1 calc GR . . . .
H20B H 0.759499 0.629943 0.017417 0.174 Uiso 1 1 calc GR . . . .
H20C H 0.608280 0.631502 0.044317 0.174 Uiso 1 1 calc GR . . . .
C21 C -0.0809(5) 0.6278(5) 0.4775(3) 0.0836(12) Uani 1 1 d . . . . .
H21A H -0.040683 0.661539 0.519138 0.125 Uiso 1 1 calc GR . . . .
H21B H -0.085623 0.552257 0.485448 0.125 Uiso 1 1 calc GR . . . .
H21C H -0.170863 0.655437 0.470104 0.125 Uiso 1 1 calc GR . . . .
C19 C 0.8826(5) 0.7279(7) 0.1272(3) 0.110(2) Uani 1 1 d . . . . .
H19A H 0.898768 0.782806 0.162543 0.166 Uiso 1 1 calc GR . . . .
H19B H 0.936976 0.741028 0.084777 0.166 Uiso 1 1 calc GR . . . .
H19C H 0.906382 0.659905 0.147580 0.166 Uiso 1 1 calc GR . . . .
C18 C 0.7025(7) 0.8289(5) 0.0625(3) 0.1071(18) Uani 1 1 d . . . . .
H18A H 0.608490 0.829690 0.048413 0.161 Uiso 1 1 calc GR . . . .
H18B H 0.758559 0.830238 0.019709 0.161 Uiso 1 1 calc GR . . . .
H18C H 0.721748 0.890325 0.091878 0.161 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O3 C12 116.9(2) . . ?
O2 N1 C15 116.2(3) . . ?
O1 N1 O2 124.0(3) . . ?
O1 N1 C15 119.8(3) . . ?
O6 C13 C12 126.8(3) . . ?
O6 C13 C8 130.1(3) . . ?
C8 C13 C12 102.9(3) . . ?
C5 C6 C7 120.7(3) . . ?
C1 C6 C5 116.5(3) . . ?
C1 C6 C7 122.8(4) . . ?
O3 C22 C23 111.1(3) . . ?
O4 C22 O3 123.1(3) . . ?
O4 C22 C23 125.8(3) . . ?
C3 C2 C1 121.3(4) . . ?
O3 C12 C13 114.1(3) . . ?
O3 C12 C11 114.5(2) . . ?
O3 C12 C15 109.8(3) . . ?
C13 C12 C15 102.9(2) . . ?
C11 C12 C13 106.7(2) . . ?
C11 C12 C15 108.1(3) . . ?
C4 C5 C6 121.0(3) . . ?
C10 C11 C12 124.0(3) . . ?
C6 C7 C8 114.6(3) . . ?
C5 C4 C3 121.9(4) . . ?
N1 C15 C12 105.8(2) . . ?
N1 C15 C14 107.9(2) . . ?
C12 C15 C14 102.3(3) . . ?
C16 C15 N1 108.6(3) . . ?
C16 C15 C12 116.4(3) . . ?
C16 C15 C14 115.2(3) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 C17 122.6(3) . . ?
C9 C10 C17 119.5(3) . . ?
C13 C8 C7 115.3(3) . . ?
C13 C8 C14 103.4(2) . . ?
C13 C8 C9 103.6(3) . . ?
C7 C8 C14 115.8(3) . . ?
C7 C8 C9 110.5(3) . . ?
C14 C8 C9 107.2(3) . . ?
C2 C3 C4 117.1(4) . . ?
C2 C3 C21 121.1(4) . . ?
C4 C3 C21 121.8(4) . . ?
C15 C14 C8 108.0(3) . . ?
C2 C1 C6 122.2(4) . . ?
O5 C9 C10 124.2(3) . . ?
O5 C9 C8 120.0(3) . . ?
C10 C9 C8 115.9(3) . . ?
C20 C17 C10 109.0(4) . . ?
C20 C17 C19 109.5(5) . . ?
C20 C17 C18 109.6(4) . . ?
C19 C17 C10 110.9(3) . . ?
C19 C17 C18 108.4(5) . . ?
C18 C17 C10 109.3(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C13 1.190(4) . ?
O3 C22 1.369(4) . ?
O3 C12 1.428(4) . ?
O4 C22 1.183(4) . ?
O2 N1 1.214(4) . ?
O1 N1 1.213(4) . ?
N1 C15 1.534(4) . ?
C13 C12 1.531(4) . ?
C13 C8 1.515(5) . ?
O5 C9 1.203(5) . ?
C6 C5 1.390(5) . ?
C6 C7 1.505(5) . ?
C6 C1 1.381(6) . ?
C22 C23 1.489(5) . ?
C2 C3 1.373(6) . ?
C2 C1 1.376(6) . ?
C12 C11 1.504(4) . ?
C12 C15 1.546(5) . ?
C5 C4 1.380(6) . ?
C11 C10 1.339(5) . ?
C7 C8 1.543(4) . ?
C4 C3 1.382(6) . ?
C15 C16 1.518(5) . ?
C15 C14 1.548(4) . ?
C10 C9 1.488(5) . ?
C10 C17 1.539(5) . ?
C8 C14 1.550(5) . ?
C8 C9 1.560(5) . ?
C3 C21 1.505(6) . ?
C17 C20 1.527(7) . ?
C17 C19 1.529(7) . ?
C17 C18 1.530(8) . ?
