Stereospecific access to α-haloalkyl esters <i>via</i> enol ester epoxides and synthesis of a C3-C21 fragment of bastimolide A.
Howell, Lucas W.; Hackbarth, Jacob N.; Abraham, Jeffrey S.; Friestad, Gregory K.; Organic & biomolecular chemistry 23 (2025) 2802–2806; doi:10.1039/d5ob00070j

data_7160374
_publ_section_title
;
 Stereospecific access to &#x3b1;-haloalkyl esters <i>via</i> enol ester
 epoxides and synthesis of a C3-C21 fragment of bastimolide A.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2802
_journal_page_last               2806
_journal_paper_doi               10.1039/d5ob00070j
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 Cl N2 O9'
_chemical_formula_sum            'C21 H21 Cl N2 O9'
_chemical_formula_weight         480.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-11-18 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.290(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8622(6)
_cell_length_b                   9.9029(8)
_cell_length_c                   18.9327(16)
_cell_measurement_reflns_used    9571
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      72.46
_cell_measurement_theta_min      4.70
_cell_volume                     1092.48(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19964
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.456
_diffrn_reflns_theta_min         4.699
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_T_max  0.7019
_exptl_absorpt_correction_T_min  0.5263
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0358 after correction.
The Ratio of minimum to maximum transmission is 0.7498.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4260
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0235
_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^)+(0.0396P)^2^+0.1889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4241
_reflns_number_total             4260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00070j2.cif
_cod_data_source_block           S6
_cod_depositor_comments          'Adding full bibliography for 7160374.cif.'
_cod_database_code               7160374
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.599
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C17(H17), C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              10992
_olex2_exptl_crystal_mounting_method 'MiTeGen 50 micron MicroMount'
_olex2_submission_special_instructions 'No special instructions were received'