n→ π* Interactions Engender Chirality in Carbonyl Groups.
Choudhary, Amit; Newberry, Robert W.; Raines, Ronald T.; Organic letters 16 (2014) 3421–3423; doi:10.1021/ol5012967

data_1516631
_publ_section_title
;
 n\\rightarrow \p* Interactions Engender Chirality in Carbonyl Groups.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3421
_journal_page_last               3423
_journal_paper_doi               10.1021/ol5012967
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H15 N O3 S'
_chemical_formula_weight         217.28
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
;
_cell_angle_alpha                90
_cell_angle_beta                 99.245(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3034(9)
_cell_length_b                   6.8102(9)
_cell_length_c                   12.5634(17)
_cell_measurement_reflns_used    3375
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5037
_cell_measurement_theta_min      3.2744
_cell_volume                     532.31(13)
_computing_cell_refinement       'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXTL Ver. 6.10'
_computing_publication_material  'SHELXTL Ver. 6.10'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTL Ver. 6.10 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker CCD-1000 area detector'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7824
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.009
_diffrn_reflns_theta_min         3.274
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.8892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.14(9)
_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     131
_refine_ls_number_reflns         2923
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0475P)^2^+0.0766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2638
_reflns_number_total             2923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5012967_si_006.cif
_cod_data_source_block           global
_cod_depositor_comments
'Adding full bibliography for 1516628--1516633.cif.'
_cod_database_code               1516631
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-4
_shelx_res_checksum              21597
_shelx_hkl_checksum              48036