Mechanistic interrogation of the asymmetric lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine.
Rayner, Peter J.; Smith, Joshua C.; Denneval, Charline; O'Brien, Peter; Clarke, Paul A.; Horan, Richard A. J.; Chemical communications (Cambridge, England) 52 (2016) 1354–1357; doi:10.1039/c5cc08690f

data_7118446
_publ_section_title
;
 Mechanistic interrogation of the asymmetric lithiation-trapping of
 N-thiopivaloyl azetidine and pyrrolidine.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1354
_journal_page_last               1357
_journal_paper_doi               10.1039/c5cc08690f
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H17 N O2 S'
_chemical_formula_sum            'C10 H17 N O2 S'
_chemical_formula_weight         215.30
_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     iterative
_audit_creation_date             2015-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-05 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.51691(18)
_cell_length_b                   11.9691(3)
_cell_length_c                   29.6051(8)
_cell_measurement_reflns_used    6616
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      31.7210
_cell_measurement_theta_min      3.2270
_cell_volume                     2309.24(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -102.00  -34.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740  178.0000   60.0000 68

  2 omega   34.00  103.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802 -178.0000   90.0000 69

  3 omega  -18.00   99.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   19.0000 -120.0000 117

  4 omega    6.00   61.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   57.0000  -30.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0586619000
_diffrn_orient_matrix_UB_12      -0.0143532000
_diffrn_orient_matrix_UB_13      0.0193314000
_diffrn_orient_matrix_UB_21      0.0847316000
_diffrn_orient_matrix_UB_22      0.0132040000
_diffrn_orient_matrix_UB_23      0.0140463000
_diffrn_orient_matrix_UB_31      -0.0350241000
_diffrn_orient_matrix_UB_32      0.0559732000
_diffrn_orient_matrix_UB_33      0.0016441000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16952
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         29.990
_diffrn_reflns_theta_min         3.197
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/pentane'
_exptl_crystal_size_max          0.5506
_exptl_crystal_size_mid          0.0845
_exptl_crystal_size_min          0.0541
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0311P)^2^+0.5774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6219
_reflns_number_total             6729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc08690f2.cif
_cod_data_source_block           pac1401
_cod_original_cell_volume        2309.25(11)
_cod_database_code               7118446
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H17 N1 O2 S1'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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:
 C2(H2), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_date_sample_data_collection 2014-04-28
_olex2_submission_special_instructions 'No special instructions were received'