Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines.
Panduwawala, Tharindi D.; Iqbal, Sarosh; Tirfoin, Rémi; Moloney, Mark G.; Organic & biomolecular chemistry 14 (2016) 4464–4478; doi:10.1039/c6ob00557h

data_7155073
_publ_section_title
;
 Chemoselectivity and stereoselectivity of cyclisation pathways leading to
 bicyclic tetramates controlled by ring-chain tautomerisation in
 thiazolidines.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4464
_journal_page_last               4478
_journal_paper_doi               10.1039/c6ob00557h
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H19 N1 O4 S1'
_chemical_formula_sum            'C12 H19 N O4 S'
_chemical_formula_weight         273.35
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-11
_audit_creation_method           CRYSTALS_ver_14.61_build_5555
_audit_update_record
;
2016-02-11 deposited with the CCDC.
2016-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.2930(12)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   8.7753(1)
_cell_length_b                   21.3925(2)
_cell_length_c                   12.0847(1)
_cell_measurement_reflns_used    14046
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     2166.06(4)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22837
_diffrn_reflns_theta_full        74.285
_diffrn_reflns_theta_max         75.801
_diffrn_reflns_theta_min         3.831
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.064
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack (1983), 4293 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8859
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.0007404
_refine_ls_shift/su_mean         0.0000545
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.38P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0734
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0734
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              26
_reflns_limit_k_min              -26
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                8614
_reflns_number_total             8896
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.35
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0293
_oxford_refine_ls_scale          6.49(7)
_oxford_reflns_number_all        8859
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6515
_cod_data_source_file            c6ob00557h2.cif
_cod_data_source_block           3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155073.cif.
;
_cod_original_sg_symbol_H-M      'P 21 '
_cod_original_formula_sum        'C12 H19 N1 O4 S1'
_cod_database_code               7155073