1,3-Dipolar Cycloaddition of Diazoalkanes to (S)-(+)-3-[(4-Methylphenyl)sulfinyl]-5,6-dihydropyran-2-one. Synthesis of Optically Pure Cyclopropanes by Denitrogenation of Sulfinyl and Sulfonyl Pyrazolines
David Cruz Cruz; Francisco Yuste; M. Rosario Martín; Amelia Tito; José L. García Ruano; Journal of Organic Chemistry 74 (2009) 3820–3826; doi:10.1021/jo900525s

data_4024554
_publ_section_title
;
1,3-Dipolar Cycloaddition of Diazoalkanes to
(S)-(+)-3-[(4-Methylphenyl)sulfinyl]-5,6-dihydropyran-2-one. Synthesis of
Optically Pure Cyclopropanes by Denitrogenation of Sulfinyl and Sulfonyl
Pyrazolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3820
_journal_page_last               3826
_journal_paper_doi               10.1021/jo900525s
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H16 O3 S'
_chemical_formula_sum            'C14 H16 O3 S'
_chemical_formula_weight         264.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0768(7)
_cell_length_b                   10.4374(13)
_cell_length_c                   20.790(3)
_cell_measurement_reflns_used    6579
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.18
_cell_volume                     1318.6(3)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23C (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.661
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart Apex CCD diffractometer'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8198
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_correction_T_min  0.8712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.344
_exptl_crystal_size_min          0.238
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0478P)^2^+0.1428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                2362
_reflns_number_total             2419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900525s_si_003.cif
_cod_data_source_block           COMPOUND_10
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024554