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_7160533
_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         'C15 H19 Br O3'
_chemical_formula_sum            'C15 H19 Br O3'
_chemical_formula_weight         327.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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                   21.8523(12)
_cell_length_b                   5.1108(4)
_cell_length_c                   25.9585(19)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7340
_cell_measurement_theta_min      4.0600
_cell_volume                     2899.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -65.00 -39.00   0.40   12.50    --  -15.63 139.00  25.00   65
  2  \w     44.00  73.20   0.40   12.50    --   17.66-139.00 -34.00   73
  3  \w    -78.00 -36.00   0.40   12.50    --  -15.63 -57.00-120.00  105
  4  \w    -19.00   8.20   0.40   12.50    --  -15.63 -77.00  60.00   68
  5  \w    -82.00 -38.00   0.40   12.50    --  -15.63 -77.00  60.00  110
  6  \w     35.00  60.20   0.40   12.50    --   17.66 178.00 120.00   63
  7  \w      2.00  75.20   0.40   12.50    --   17.66  57.00  60.00  183
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024191000
_diffrn_orient_matrix_UB_12      -0.0043941000
_diffrn_orient_matrix_UB_13      -0.0272004000
_diffrn_orient_matrix_UB_21      -0.0323756000
_diffrn_orient_matrix_UB_22      -0.0006070000
_diffrn_orient_matrix_UB_23      0.0020215000
_diffrn_orient_matrix_UB_31      -0.0002330000
_diffrn_orient_matrix_UB_32      0.1388535000
_diffrn_orient_matrix_UB_33      -0.0008380000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14892
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.139
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0211P)^2^+1.4692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                3989
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00655d2.cif
_cod_data_source_block           220521_s1_lgg
_cod_depositor_comments
'Adding full bibliography for 7160532--7160534.cif.'
_cod_database_code               7160533
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C190
_shelx_estimated_absorpt_t_max   0.537
_shelx_estimated_absorpt_t_min   0.437
_reflns_odcompleteness_completeness 99.63
_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, All O(H) groups
2. Restrained distances
 H14A-H13A
 2.345 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C19(HA), C23(HH), C24(HI), C4(H4), C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C20(HB,HC), C21(HD,HE), C22(HF,HG), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
3.c Idealised Me refined as rotating group:
 C28(HJ,HK,HL), C29(HM,HN,HO), C30(HP,HQ,HR), C13(H13A,H13B,H13C), C14(H14A,
 H14B,H14C), C15(H15A,H15B,H15C)
3.d Idealised tetrahedral OH refined as rotating group:
 O6(H), O3(H3)
;
_shelx_res_checksum              68747
_olex2_date_sample_data_collection 2022-05-21
_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.691