Semipinacol Rearrangement of Cis-Fused β-Lactam Diols into Keto-Bridged Bicyclic Lactams.
Grainger, Richard S.; Betou, Marie; Male, Louise; Pitak, Mateusz B.; Coles, Simon J.; Organic letters 14 (2012) 2234–2237; doi:10.1021/ol300605y

data_1507614
_publ_section_title
;
 Semipinacol Rearrangement of Cis-Fused \b-Lactam Diols into Keto-Bridged
 Bicyclic Lactams.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2234
_journal_page_last               2237
_journal_paper_doi               10.1021/ol300605y
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H28 N2 O2 S2'
_chemical_formula_sum            'C20 H28 N2 O2 S2'
_chemical_formula_weight         392.56
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.759(12)
_cell_angle_beta                 89.300(18)
_cell_angle_gamma                74.762(18)
_cell_formula_units_Z            2
_cell_length_a                   6.3563(16)
_cell_length_b                   7.9604(13)
_cell_length_c                   20.414(4)
_cell_measurement_reflns_used    1264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.4
_cell_measurement_theta_min      21.9
_cell_volume                     995.8(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn944+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10836
_diffrn_reflns_theta_full        66.43
_diffrn_reflns_theta_max         66.43
_diffrn_reflns_theta_min         2.17
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    2.553
_exptl_absorpt_correction_T_max  0.8218
_exptl_absorpt_correction_T_min  0.7844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0320(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0710P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                2903
_reflns_number_total             3410
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol300605y_si_005.cif
_cod_data_source_block           2011ncs0282
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507614