Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation.
Goodman, C. Guy; Walker, Morgan M.; Johnson, Jeffrey S.; Journal of the American Chemical Society 137 (2015) 122–125; doi:10.1021/ja511701j

data_4123191
_publ_section_title
;
 Enantioconvergent Synthesis of Functionalized \g-Butyrolactones via (3 +
 2)-Annulation.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              122
_journal_page_last               125
_journal_paper_doi               10.1021/ja511701j
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 Cl O4 S'
_chemical_formula_sum            'C21 H23 Cl O4 S'
_chemical_formula_weight         406.90
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5681(4)
_cell_length_b                   12.5973(4)
_cell_length_c                   13.5922(5)
_cell_measurement_reflns_used    8520
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.04
_cell_measurement_theta_min      4.79
_cell_volume                     1980.75(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15433
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.083
_diffrn_reflns_theta_min         4.786
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.894
_exptl_absorpt_correction_T_max  0.8204
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0638 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.7857.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0404P)^2^+0.4215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3630
_reflns_number_total             3738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511701j_si_001.cif
_cod_data_source_block           x1409001
_cod_depositor_comments          'Adding full bibliography for 4123191.cif.'
_cod_database_code               4123191
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.535
_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:
 C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              19714
_shelx_hkl_checksum              21266
_olex2_submission_original_sample_id GG-8-47
_olex2_submission_special_instructions 'No special instructions were received'