Synthesis and structural analysis of a new class of azaspiro[3.3]heptanes as building blocks for medicinal chemistry.
Burkhard, Johannes A.; Guérot, Carine; Knust, Henner; Rogers-Evans, Mark; Carreira, Erick M.; Organic letters 12 (2010) 1944–1947; doi:10.1021/ol1003302

data_1502903
_publ_section_title
;
 Synthesis and structural analysis of a new class of azaspiro[3.3]heptanes
 as building blocks for medicinal chemistry.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1944
_journal_page_last               1947
_journal_paper_doi               10.1021/ol1003302
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         'C12 H12 Br N O3 S '
_chemical_formula_sum            'C12 H12 Br N O3 S'
_chemical_formula_weight         330.205
_chemical_name_systematic
;
(4-bomophenyl)(1,1-dioxo-1-thia-6-azaspiro[3.3]heptan-6-yl)methanone
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.7240(8)
_cell_length_b                   5.8436(2)
_cell_length_c                   10.4288(4)
_cell_measurement_reflns_used    5158
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.425
_cell_volume                     1262.96(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97(Altomare et al., J. Appl. Cryst.,1999)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.11438
_diffrn_orient_matrix_UB_12      -0.11281
_diffrn_orient_matrix_UB_13      -0.05895
_diffrn_orient_matrix_UB_21      -0.03907
_diffrn_orient_matrix_UB_22      -0.06827
_diffrn_orient_matrix_UB_23      0.05484
_diffrn_orient_matrix_UB_31      -0.03003
_diffrn_orient_matrix_UB_32      -0.01167
_diffrn_orient_matrix_UB_33      -0.03592
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.086
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4954
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    3.419
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664.0
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .255
_exptl_crystal_size_min          .021
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2143
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.791
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                2044
_reflns_number_total             2143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1003302_si_003.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P n a 21      '
_cod_original_formula_sum        'C12 H12 Br N O3 S '
_cod_database_code               1502903