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_7160534
_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 H17 Br O3'
_chemical_formula_sum            'C15 H17 Br O3'
_chemical_formula_weight         325.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-16
_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                 101.9390(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81899(16)
_cell_length_b                   9.17658(16)
_cell_length_c                   15.2660(3)
_cell_measurement_reflns_used    7196
_cell_measurement_temperature    149.97(10)
_cell_measurement_theta_max      76.9140
_cell_measurement_theta_min      4.6020
_cell_volume                     1345.78(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (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      149.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.948
_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     87.00 112.00   0.50    0.11    --  107.75  77.00   0.00   50
  2  \w    104.00 130.00   0.50    0.11    --  107.75 111.00  28.00   52
  3  \w    123.00 174.00   0.50    0.11    --  107.75  77.00   0.00  102
  4  \w    104.00 169.00   0.50    0.11    --  107.75  37.00   0.00  130
  5  \w    -22.00  38.00   0.50    0.05    --   47.57 -37.00-180.00  120
  6  \w      7.00  38.00   0.50    0.05    --   47.57-111.00 -64.00   62
  7  \w     45.00  82.00   0.50    0.05    --   47.57-111.00 -64.00   74
  8  \w    -26.00  21.00   0.50    0.05    --   47.57 -19.00  30.00   94
  9  \w    -27.00  -2.00   0.50    0.05    --   47.57 -19.00 120.00   50
 10  \w     35.00 108.00   0.50    0.11    --  107.75-111.00 -64.00  146
 11  \w     70.00 102.00   0.50    0.11    --  107.75 -77.00 -60.00   64
 12  \w     38.00  66.00   0.50    0.11    --  107.75 -77.00 -60.00   56
 13  \w     35.00  60.00   0.50    0.11    --  107.75 -57.00 -90.00   50
 14  \w     37.00  62.00   0.50    0.11    --  107.75 -57.00 -60.00   50
 15  \w     38.00  63.00   0.50    0.11    --  107.75 -57.00   0.00   50
 16  \w     35.00  60.00   0.50    0.11    --  107.75 -57.00 120.00   50
 17  \w    -20.00  27.00   0.50    0.05    --  -47.57  19.00   0.00   94
 18  \w    -43.00  23.00   0.50    0.05    --  -47.57  37.00-120.00  132
 19  \w    -57.00 -28.00   0.50    0.11    -- -100.00  57.00-150.00   58
 20  \w    -66.00 -27.00   0.50    0.11    -- -100.00  57.00-120.00   78
 21  \w    -69.00 -29.00   0.50    0.11    -- -100.00  57.00   0.00   80
 22  \w    -53.00 -27.00   0.50    0.11    -- -100.00  57.00  60.00   52
 23  \w    -51.00 -26.00   0.50    0.05    --  -47.57 111.00  28.00   50
 24  \w   -106.00 -52.00   0.50    0.11    -- -100.00 111.00  28.00  108
 25  \w   -125.00 -94.00   0.50    0.11    -- -100.00 -57.00 150.00   62
 26  \w   -146.00 -90.00   0.50    0.11    -- -100.00-111.00 -64.00  112
;
_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      0.0415621000
_diffrn_orient_matrix_UB_12      0.1564354000
_diffrn_orient_matrix_UB_13      0.0313147000
_diffrn_orient_matrix_UB_21      0.0275410000
_diffrn_orient_matrix_UB_22      -0.0510777000
_diffrn_orient_matrix_UB_23      0.0981723000
_diffrn_orient_matrix_UB_31      0.1524132000
_diffrn_orient_matrix_UB_32      -0.0333619000
_diffrn_orient_matrix_UB_33      -0.0038866000
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8763
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.451
_diffrn_reflns_theta_min         4.932
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0509P)^2^+2.5401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2555
_reflns_number_total             2711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00655d2.cif
_cod_data_source_block           zhuangzhy_1216-2_auto
_cod_depositor_comments
'Adding full bibliography for 7160532--7160534.cif.'
_cod_database_code               7160534
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.634
_shelx_estimated_absorpt_t_min   0.592
_reflns_odcompleteness_completeness 100.00
_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:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              44090
_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 5.470
_oxdiff_exptl_absorpt_empirical_full_min 0.370