Divergent synthetic studies towards bisabosqual A and fargenone B <i>via</i> an intramolecular S<sub>N</sub>2 reaction.
Guo, Chen; Zhu, Mao-Mei; Ze Lang, Si-Ji; Wang, Ya-Wen; Xiao, Jian; Peng, Yu; Organic & biomolecular chemistry 23 (2025) 5298–5300; doi:10.1039/d5ob00655d

data_7160532
_publ_section_title
;
 Divergent synthetic studies towards bisabosqual A and fargenone B
 <i>via</i> an intramolecular S<sub>N</sub>2 reaction.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5298
_journal_page_last               5300
_journal_paper_doi               10.1039/d5ob00655d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2025-03-13 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7570(2)
_cell_length_b                   10.12180(10)
_cell_length_c                   18.1651(2)
_cell_measurement_reflns_used    8658
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.9870
_cell_measurement_theta_min      2.8230
_cell_volume                     2897.14(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.934
_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     12.00  84.00   0.50    0.05    --   47.57-116.00 174.00  144
  2  \w     37.00  75.00   0.50    0.05    --  107.75-116.00 174.00   76
  3  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00  60.00   50
  4  \w     58.00  92.00   0.50    0.05    --  107.75 -74.00  58.00   68
  5  \w     36.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   50
  6  \w     49.00  87.00   0.50    0.05    --   47.57 165.00  50.00   76
  7  \w    -29.00  23.00   0.50    0.05    --  -47.57  19.00 -60.00  104
  8  \w    -57.00 -31.00   0.50    0.05    -- -100.00  48.00  35.00   52
  9  \w   -112.00 -63.00   0.50    0.05    -- -100.00 125.00 -30.00   98
 10  \w    -59.00 -31.00   0.50    0.05    -- -100.00 125.00 -30.00   56
 11  \w   -108.00 -39.00   0.50    0.05    -- -100.00 116.00 -96.00  138
 12  \w   -164.00-117.00   0.50    0.05    -- -100.00 -74.00  58.00   94
 13  \w   -112.00 -78.00   0.50    0.05    -- -100.00 -74.00  58.00   68
 14  \w   -152.00-100.00   0.50    0.05    -- -100.00 -99.00-150.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0453242000
_diffrn_orient_matrix_UB_12      0.1170767000
_diffrn_orient_matrix_UB_13      -0.0373513000
_diffrn_orient_matrix_UB_21      0.0363035000
_diffrn_orient_matrix_UB_22      0.0943014000
_diffrn_orient_matrix_UB_23      0.0586756000
_diffrn_orient_matrix_UB_31      0.0785952000
_diffrn_orient_matrix_UB_32      0.0238553000
_diffrn_orient_matrix_UB_33      -0.0485884000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11033
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.413
_diffrn_reflns_theta_min         5.615
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+1.0798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2668
_reflns_number_total             2869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00655d2.cif
_cod_data_source_block           zhungzhy_0730_auto
_cod_depositor_comments
'Adding full bibliography for 7160532--7160534.cif.'
_cod_database_code               7160532
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.870
_reflns_odcompleteness_completeness 99.46
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_shelx_res_checksum              7284
_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 2.513
_oxdiff_exptl_absorpt_empirical_full_min 0.510