Synthesis of α-alkylated γ-butyrolactones with concomitant anhydride kinetic resolution using a sulfamide-based catalyst.
Claveau, Romain; Twamley, Brendan; Connon, Stephen J.; Organic & biomolecular chemistry 16 (2018) 7574–7578; doi:10.1039/c8ob02248h

data_7156510
_publ_section_title
;
 Synthesis of \a-alkylated \g-butyrolactones with concomitant anhydride
 kinetic resolution using a sulfamide-based catalyst.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7574
_journal_page_last               7578
_journal_paper_doi               10.1039/c8ob02248h
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H28 F6 N4 O3 S, H2 O'
_chemical_formula_sum            'C28 H30 F6 N4 O4 S'
_chemical_formula_weight         632.62
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-09-10 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0847(3)
_cell_length_b                   12.3157(4)
_cell_length_c                   23.0056(7)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.61
_cell_volume                     2857.30(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2016) '
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            39589
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.430
_diffrn_reflns_theta_min         2.610
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0670 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.8789. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 2607 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         7137
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0543P)^2^+1.6261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                6559
_reflns_number_total             7137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02248h2.cif
_cod_data_source_block           tcd887
_cod_depositor_comments
'Adding full bibliography for 7156510--7156511.cif.'
_cod_database_code               7156510
_shelx_shelxl_version_number     2014/7
_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. Restrained distances
 N24-H24 = N28-H28
 0.89 with sigma of 0.01
 O1-H1A = O1-H1B
 0.87 with sigma of 0.01
 H1B-H24
 2.2 with sigma of 0.01
 H20B-H23A
 -2.1 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C22 \\sim C23: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C18(H18), C21(H21)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C11(H11), C12(H12), C22(H22), C30(H30), C33(H33),
 C36(H36)
4.d X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
4.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              33665
_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen holder'
_olex2_submission_original_sample_id RCL417
_olex2_submission_special_instructions 'No special instructions were received'