#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024554.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024554
loop_
_publ_author_name
'David Cruz Cruz'
'Francisco Yuste'
'M. Rosario Martín'
'Amelia Tito'
'José L. García Ruano'
_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
_chemical_name_systematic
; 
 ? 
;
_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       ω-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/[σ²(Fo²)+(0.0478P)²+0.1428P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44173(7) 0.43273(4) 0.919544(19) 0.02657(12) Uani 1 1 d . . .
O1 O 0.5017(2) 0.37948(12) 0.98351(5) 0.0366(3) Uani 1 1 d . . .
O2 O 0.4168(2) 0.45647(11) 0.77924(5) 0.0336(3) Uani 1 1 d . . .
C1 C 0.5864(3) 0.33339(14) 0.86093(7) 0.0224(3) Uani 1 1 d . . .
C2 C 0.5632(3) 0.38464(15) 0.79448(7) 0.0268(4) Uani 1 1 d . . .
O3 O 0.7124(2) 0.35058(14) 0.75007(6) 0.0374(3) Uani 1 1 d . . .
C4 C 0.8870(3) 0.2584(2) 0.76338(9) 0.0375(4) Uani 1 1 d . . .
H4A H 1.0080 0.2711 0.7321 0.045 Uiso 1 1 calc R . .
H4B H 0.8288 0.1706 0.7574 0.045 Uiso 1 1 calc R . .
C5 C 0.9767(3) 0.27126(18) 0.83054(8) 0.0323(4) Uani 1 1 d . . .
H5A H 1.0839 0.2017 0.8388 0.039 Uiso 1 1 calc R . .
H5B H 1.0547 0.3541 0.8347 0.039 Uiso 1 1 calc R . .
C6 C 0.7946(3) 0.26452(16) 0.87943(8) 0.0259(4) Uani 1 1 d . . .
H6 H 0.8413 0.2749 0.9253 0.031 Uiso 1 1 calc R . .
C7 C 0.5909(3) 0.18696(15) 0.86911(8) 0.0260(4) Uani 1 1 d . . .
H7 H 0.5883 0.1380 0.8278 0.031 Uiso 1 1 calc R . .
C8 C 0.4821(3) 0.11923(16) 0.92479(9) 0.0326(4) Uani 1 1 d . . .
H8A H 0.5207 0.0281 0.9238 0.049 Uiso 1 1 calc R . .
H8B H 0.3220 0.1286 0.9214 0.049 Uiso 1 1 calc R . .
H8C H 0.5328 0.1570 0.9653 0.049 Uiso 1 1 calc R . .
C9 C 0.6063(3) 0.57457(15) 0.90991(7) 0.0241(3) Uani 1 1 d . . .
C10 C 0.5308(3) 0.67576(15) 0.87302(8) 0.0284(4) Uani 1 1 d . . .
H10 H 0.3924 0.6707 0.8519 0.034 Uiso 1 1 calc R . .
C11 C 0.6594(3) 0.78437(16) 0.86732(8) 0.0295(4) Uani 1 1 d . . .
H11 H 0.6094 0.8533 0.8413 0.035 Uiso 1 1 calc R . .
C12 C 0.8601(3) 0.79500(16) 0.89877(8) 0.0270(4) Uani 1 1 d . . .
C13 C 0.9300(3) 0.69348(16) 0.93664(8) 0.0325(4) Uani 1 1 d . . .
H13 H 1.0661 0.6994 0.9589 0.039 Uiso 1 1 calc R . .
C14 C 0.8038(3) 0.58342(16) 0.94248(8) 0.0300(4) Uani 1 1 d . . .
H14 H 0.8529 0.5146 0.9687 0.036 Uiso 1 1 calc R . .
C15 C 0.9982(3) 0.91403(16) 0.89188(9) 0.0394(5) Uani 1 1 d . . .
H15A H 1.1544 0.8908 0.8929 0.059 Uiso 1 1 calc R . .
H15B H 0.9659 0.9728 0.9274 0.059 Uiso 1 1 calc R . .
H15C H 0.9642 0.9559 0.8509 0.059 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C9 105.73(7) . . ?
O1 S1 C1 105.47(7) . . ?
C9 S1 C1 97.20(7) . . ?
C2 C1 C6 119.23(15) . . ?
C2 C1 C7 117.48(13) . . ?
C6 C1 C7 58.83(11) . . ?
C2 C1 S1 111.71(12) . . ?
C6 C1 S1 120.38(11) . . ?
C7 C1 S1 119.94(11) . . ?
O2 C2 O3 118.84(14) . . ?
O2 C2 C1 122.50(16) . . ?
O3 C2 C1 118.66(16) . . ?
C2 O3 C4 122.37(13) . . ?
O3 C4 C5 112.38(15) . . ?
C6 C5 C4 110.88(14) . . ?
C7 C6 C5 122.53(15) . . ?
C7 C6 C1 61.68(10) . . ?
C5 C6 C1 115.05(14) . . ?
C6 C7 C8 120.44(14) . . ?
C6 C7 C1 59.49(11) . . ?
C8 C7 C1 122.87(14) . . ?
C14 C9 C10 120.59(15) . . ?
C14 C9 S1 118.94(12) . . ?
C10 C9 S1 120.39(12) . . ?
C11 C10 C9 119.08(16) . . ?
C10 C11 C12 121.47(16) . . ?
C13 C12 C11 118.38(16) . . ?
C13 C12 C15 120.91(17) . . ?
C11 C12 C15 120.71(16) . . ?
C14 C13 C12 120.91(17) . . ?
C9 C14 C13 119.53(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4867(13) . ?
S1 C9 1.7978(16) . ?
S1 C1 1.8256(16) . ?
O2 C2 1.206(2) . ?
C1 C2 1.488(2) . ?
C1 C6 1.505(2) . ?
C1 C7 1.538(2) . ?
C2 O3 1.342(2) . ?
O3 C4 1.458(2) . ?
C4 C5 1.505(3) . ?
C5 C6 1.504(2) . ?
C6 C7 1.495(2) . ?
C7 C8 1.509(2) . ?
C9 C14 1.381(2) . ?
C9 C10 1.384(2) . ?
C10 C11 1.382(2) . ?
C11 C12 1.388(3) . ?
C12 C13 1.387(2) . ?
C12 C15 1.506(2) . ?
C13 C14 1.386(2) . ?
