#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/82/1508280.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_1508280
loop_
_publ_author_name
'Kulshrestha, Aman'
'Salehi Marzijarani, Nastaran'
'Dilip Ashtekar, Kumar'
'Staples, Richard'
'Borhan, Babak'
_publ_section_title
;
 3,4-Dihydroxypyrrolidines via modified tandem aza-Payne/hydroamination
 pathway.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3592
_journal_page_last               3595
_journal_paper_doi               10.1021/ol301204w
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C16 H19 N O5 S'
_chemical_formula_sum            'C16 H19 N O5 S'
_chemical_formula_weight         337.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                65.8500(10)
_cell_angle_beta                 86.6440(10)
_cell_angle_gamma                88.9920(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4553(7)
_cell_length_b                   10.7405(10)
_cell_length_c                   11.3712(11)
_cell_measurement_reflns_used    5614
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      2.20
_cell_volume                     829.40(14)
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13277
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         1.97
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0588
_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/[σ²(Fo²)+(0.0820P)²+1.0398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                2320
_reflns_number_total             3001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301204w_si_003.cif
_cod_data_source_block           bb85_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1508279--1508280.cif.
;
_cod_database_code               1508280
#BEGIN Tags that were not found in dictionaries:
_contact_crystallographer_name   'Richard Staples'
_contact_crystallographer_email  staples@chemistry.msu.com
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.80104(11) 0.11126(8) 0.07822(7) 0.0347(3) Uani 1 1 d . A 1
O1 O 0.7377(4) -0.3378(3) 0.3063(2) 0.0513(7) Uani 1 1 d . A 1
O2 O 0.6557(4) -0.4188(2) 0.5155(2) 0.0536(7) Uani 1 1 d . A 1
O3 O 0.8204(4) -0.5482(3) 0.4381(3) 0.0625(8) Uani 1 1 d . A 1
O4 O 0.8387(3) 0.1254(2) -0.0520(2) 0.0394(6) Uani 1 1 d . A 1
O5 O 0.6239(3) 0.1369(2) 0.1176(2) 0.0427(6) Uani 1 1 d . A 1
N1 N 0.8499(4) -0.0440(3) 0.1678(2) 0.0349(6) Uani 1 1 d . A 1
H1 H 0.9174 -0.0893 0.1328 0.042 Uiso 1 1 calc R A 1
C1 C 1.0864(5) -0.0679(4) 0.3780(4) 0.0564(10) Uani 1 1 d . A 1
H1A H 1.1410 -0.0250 0.2901 0.085 Uiso 1 1 calc R A 1
H1B H 1.1800 -0.1111 0.4386 0.085 Uiso 1 1 calc R A 1
H1C H 1.0256 0.0017 0.4006 0.085 Uiso 1 1 calc R A 1
C2 C 0.9513(5) -0.1747(4) 0.3856(3) 0.0450(9) Uani 1 1 d . A 1
H2A H 0.9079 -0.2252 0.4767 0.054 Uiso 1 1 calc R A 1
H2B H 1.0119 -0.2407 0.3565 0.054 Uiso 1 1 calc R A 1
C3 C 0.7893(4) -0.1148(3) 0.3037(3) 0.0353(7) Uani 1 1 d . A 1
H3 H 0.7323 -0.0459 0.3321 0.042 Uiso 1 1 calc R A 1
C4 C 0.6466(5) -0.2216(4) 0.3190(3) 0.0421(8) Uani 1 1 d . A 1
C5 C 0.5610(5) -0.2901(3) 0.4573(3) 0.0443(8) Uani 1 1 d . A 1
H5 H 0.4324 -0.3109 0.4517 0.053 Uiso 1 1 calc R A 1
C6 C 0.5675(5) -0.2174(4) 0.5417(3) 0.0471(9) Uani 1 1 d . A 1
C7 C 0.5617(5) -0.1634(4) 0.6131(4) 0.0478(9) Uani 1 1 d . A 1
H7 H 0.5570 -0.1197 0.6709 0.057 Uiso 1 1 calc R A 1
C8 C 0.5056(5) -0.1743(4) 0.2215(4) 0.0541(10) Uani 1 1 d . A 1
H8A H 0.5623 -0.1495 0.1349 0.081 Uiso 1 1 calc R A 1
H8B H 0.4445 -0.0946 0.2257 0.081 Uiso 1 1 calc R A 1
H8C H 0.4179 -0.2478 0.2402 0.081 Uiso 1 1 calc R A 1
C9 C 0.7451(5) -0.4440(4) 0.4209(4) 0.0521(10) Uani 1 1 d . A 1
C10 C 0.9482(5) 0.2223(3) 0.1050(3) 0.0362(7) Uani 1 1 d . A 1
C11 C 1.1243(5) 0.2364(4) 0.0549(4) 0.0490(9) Uani 1 1 d . A 1
H11 H 1.1658 0.1846 0.0084 0.059 Uiso 1 1 calc R A 1
C12 C 1.2383(6) 0.3249(4) 0.0724(4) 0.0557(10) Uani 1 1 d . A 1
H12 H 1.3589 0.3334 0.0379 0.067 Uiso 1 1 calc R A 1
C13 C 1.1815(6) 0.4025(4) 0.1394(4) 0.0504(9) Uani 1 1 d . A 1
C14 C 1.0065(6) 0.3850(4) 0.1909(4) 0.0591(11) Uani 1 1 d . A 1
H14 H 0.9657 0.4355 0.2390 0.071 Uiso 1 1 calc R A 1
C15 C 0.8894(5) 0.2961(4) 0.1743(4) 0.0505(10) Uani 1 1 d . A 1
H15 H 0.7694 0.2859 0.2102 0.061 Uiso 1 1 calc R A 1
C16 C 1.3062(7) 0.5019(4) 0.1549(5) 0.0702(13) Uani 1 1 d . A 1
H16A H 1.4198 0.4567 0.1863 0.105 Uiso 1 1 calc R A 1
H16B H 1.2512 0.5349 0.2171 0.105 Uiso 1 1 calc R A 1
H16C H 1.3290 0.5792 0.0714 0.105 Uiso 1 1 calc R A 1
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'
N N 0.0061 0.0033 '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
O5 S1 O4 119.52(14)
O5 S1 N1 107.84(14)
O4 S1 N1 105.29(13)
O5 S1 C10 107.34(15)
O4 S1 C10 107.15(15)
N1 S1 C10 109.45(15)
C9 O1 C4 111.3(3)
C9 O2 C5 108.7(3)
C3 N1 S1 124.2(2)
C3 N1 H1 117.9
S1 N1 H1 117.9
C1 C2 C3 113.4(3)
C1 C2 H2A 108.9
C3 C2 H2A 108.9
C1 C2 H2B 108.9
C3 C2 H2B 108.9
H2A C2 H2B 107.7
N1 C3 C2 109.8(3)
N1 C3 C4 110.0(3)
C2 C3 C4 113.2(3)
N1 C3 H3 107.9
C2 C3 H3 107.9
C4 C3 H3 107.9
O1 C4 C8 107.5(3)
O1 C4 C3 107.9(3)
C8 C4 C3 115.0(3)
O1 C4 C5 101.0(3)
C8 C4 C5 111.2(3)
C3 C4 C5 113.2(3)
O2 C5 C6 108.9(3)
O2 C5 C4 104.6(3)
C6 C5 C4 118.5(3)
O2 C5 H5 108.2
C6 C5 H5 108.2
C4 C5 H5 108.2
C7 C6 C5 175.4(4)
C6 C7 H7 180.0
O3 C9 O1 124.6(4)
O3 C9 O2 123.8(4)
O1 C9 O2 111.6(3)
C15 C10 C11 119.7(3)
C15 C10 S1 120.6(3)
C11 C10 S1 119.7(3)
C12 C11 C10 120.1(3)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 121.3(4)
C11 C12 H12 119.3
C13 C12 H12 119.3
C12 C13 C14 117.7(4)
C12 C13 C16 120.9(4)
C14 C13 C16 121.4(4)
C15 C14 C13 121.7(3)
C15 C14 H14 119.1
C13 C14 H14 119.1
C14 C15 C10 119.3(4)
C14 C15 H15 120.3
C10 C15 H15 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.428(2)
S1 O4 1.436(2)
S1 N1 1.607(3)
S1 C10 1.761(4)
O1 C9 1.339(5)
O1 C4 1.465(4)
O2 C9 1.350(4)
O2 C5 1.456(4)
O3 C9 1.191(4)
N1 C3 1.463(4)
N1 H1 0.8800
C1 C2 1.512(5)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.534(5)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.529(5)
C3 H3 1.0000
C4 C8 1.500(5)
C4 C5 1.541(5)
C5 C6 1.467(5)
C5 H5 1.0000
C6 C7 1.173(5)
C7 H7 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C10 C15 1.379(5)
C10 C11 1.385(5)
C11 C12 1.366(6)
C11 H11 0.9500
C12 C13 1.387(5)
C12 H12 0.9500
C13 C14 1.382(6)
C13 C16 1.498(6)
C14 C15 1.381(6)
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.88 2.09 2.899(3) 152.1 2_755
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O5 S1 N1 C3 -34.4(3)
O4 S1 N1 C3 -163.0(3)
C10 S1 N1 C3 82.1(3)
S1 N1 C3 C2 -126.5(3)
S1 N1 C3 C4 108.3(3)
C1 C2 C3 N1 60.7(4)
C1 C2 C3 C4 -175.9(3)
C9 O1 C4 C8 -129.6(3)
C9 O1 C4 C3 105.9(3)
C9 O1 C4 C5 -13.1(4)
N1 C3 C4 O1 75.4(3)
C2 C3 C4 O1 -47.9(4)
N1 C3 C4 C8 -44.5(4)
C2 C3 C4 C8 -167.8(3)
N1 C3 C4 C5 -173.8(3)
C2 C3 C4 C5 62.9(4)
C9 O2 C5 C6 -142.7(3)
C9 O2 C5 C4 -15.2(4)
O1 C4 C5 O2 16.4(3)
C8 C4 C5 O2 130.1(3)
C3 C4 C5 O2 -98.7(3)
O1 C4 C5 C6 137.8(3)
C8 C4 C5 C6 -108.4(4)
C3 C4 C5 C6 22.8(4)
O2 C5 C6 C7 -93(5)
C4 C5 C6 C7 148(5)
C4 O1 C9 O3 -175.8(4)
C4 O1 C9 O2 4.3(4)
C5 O2 C9 O3 -172.5(4)
C5 O2 C9 O1 7.4(4)
O5 S1 C10 C15 10.6(3)
O4 S1 C10 C15 140.1(3)
N1 S1 C10 C15 -106.2(3)
O5 S1 C10 C11 -168.9(3)
O4 S1 C10 C11 -39.3(3)
N1 S1 C10 C11 74.4(3)
C15 C10 C11 C12 -1.1(6)
S1 C10 C11 C12 178.4(3)
C10 C11 C12 C13 -0.3(6)
C11 C12 C13 C14 1.6(6)
C11 C12 C13 C16 -178.3(4)
C12 C13 C14 C15 -1.5(6)
C16 C13 C14 C15 178.3(4)
C13 C14 C15 C10 0.2(6)
C11 C10 C15 C14 1.1(5)
S1 C10 C15 C14 -178.4(3)
