# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'David Hodgson'
_publ_contact_author_address     
;
Department of Chemistry
University of Oxford
Chemistry Research Laboratory
Oxford
OX1 3TA
UNITED KINGDOM
;

_publ_contact_author_email       DAVID.HODGSON@CHEM.OX.AC.UK

_publ_section_title              
;
3-Hydroxypyrrolidines from Epoxysulfonamides and
Dimethylsulfoxonium Methylide
;
loop_
_publ_author_name
'David Hodgson'
'Matthew J. Fleming'
'Changxue Lin'
'Steven J. Stanway'
'Zhaoqing Xu.'

data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 602881'
_audit_creation_date             05-05-12
_audit_creation_method           CRYSTALS_ver_12-03-99
# arc1336
#=============================================================
# Diffractometer details
#=============================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#=============================================================
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'

_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          ?
_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_special_details          
;
The hydrxyl hydrogen atom was loacted in a difference Fourier map and its
coordinates and isotropic displacement parameter subsequently refined. Other
hydrogen atoms were positioned geometrically, the preferred orientation of
the methyl group having been previously identified by examination of a
difference Fourier map.
;
#=============================================================

_cell_length_a                   7.4856(4)
_cell_angle_alpha                95.766(2)
_cell_length_b                   9.7383(5)
_cell_angle_beta                 96.224(2)
_cell_length_c                   11.5200(6)
_cell_angle_gamma                92.306(3)
_cell_volume                     829.49(8)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'Br ' -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 International_Tables_Vol_IV_Table_2.2B
'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 International_Tables_Vol_IV_Table_2.2B

_cell_formula_units_Z            2
_chemical_formula_sum            ' C17 H18 Br1 N1 O3 S1 '
_chemical_formula_moiety         ' C17 H18 Br1 N1 O3 S1 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         396.30

_cell_measurement_reflns_used    10663
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' needle '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    2.617

_diffrn_measurement_method       \w

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.90

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            10663
_reflns_number_total             3724
_diffrn_reflns_av_R_equivalents  0.050

_diffrn_reflns_theta_min         5.178
_diffrn_reflns_theta_max         27.454
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        25.
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_refine_diff_density_min         -1.09
_refine_diff_density_max         0.57

_refine_ls_number_reflns         3008
_refine_ls_number_restraints     0
_refine_ls_number_parameters     212

#_refine_ls_R_factor_ref 0.0423
_refine_ls_wR_factor_ref         0.0507
_refine_ls_goodness_of_fit_ref   1.0388

#_reflns_number_all 3724
_refine_ls_R_factor_all          0.0531
_refine_ls_wR_factor_all         0.0597

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                3008
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_gt          0.0507

_refine_ls_shift/su_max          0.002516
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.44 0.527 1.04
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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_occupancy
_atom_site_adp_type
N1 N 0.8233(3) 0.2355(2) -0.16962(19) 0.0246 1.0000 Uani
C1 C 0.7008(3) 0.2917(3) -0.0847(2) 0.0263 1.0000 Uani
C2 C 0.5132(4) 0.2442(3) -0.1463(3) 0.0320 1.0000 Uani
C3 C 0.5460(4) 0.1092(3) -0.2177(3) 0.0351 1.0000 Uani
C4 C 0.7209(4) 0.1449(3) -0.2683(3) 0.0308 1.0000 Uani
C5 C 0.7396(3) 0.2408(3) 0.0351(2) 0.0257 1.0000 Uani
C6 C 0.8227(4) 0.1171(3) 0.0500(3) 0.0293 1.0000 Uani
C7 C 0.8578(4) 0.0725(3) 0.1615(3) 0.0293 1.0000 Uani
C8 C 0.8105(4) 0.1545(3) 0.2578(2) 0.0271 1.0000 Uani
C9 C 0.7238(4) 0.2770(3) 0.2446(3) 0.0301 1.0000 Uani
C10 C 0.6880(4) 0.3187(3) 0.1335(3) 0.0295 1.0000 Uani
Br1 Br 0.87007(4) 0.10015(3) 0.41018(2) 0.0339 1.0000 Uani
O1 O 0.4593(3) 0.3466(2) -0.2216(2) 0.0367 1.0000 Uani
S1 S 0.98594(8) 0.33867(7) -0.19877(6) 0.0245 1.0000 Uani
O2 O 1.0794(3) 0.3974(2) -0.08894(18) 0.0294 1.0000 Uani
O3 O 1.0827(3) 0.2579(2) -0.28134(18) 0.0300 1.0000 Uani
C11 C 0.8869(3) 0.4723(3) -0.2715(2) 0.0264 1.0000 Uani
C12 C 0.8406(4) 0.5912(3) -0.2072(2) 0.0281 1.0000 Uani
C13 C 0.7531(4) 0.6916(3) -0.2664(3) 0.0300 1.0000 Uani
C14 C 0.7107(4) 0.6749(3) -0.3880(3) 0.0307 1.0000 Uani
C15 C 0.7599(4) 0.5544(3) -0.4507(3) 0.0342 1.0000 Uani
C16 C 0.8469(4) 0.4528(3) -0.3939(3) 0.0309 1.0000 Uani
C17 C 0.6186(4) 0.7838(3) -0.4520(3) 0.0392 1.0000 Uani
H1 H 0.353(7) 0.316(5) -0.252(4) 0.059(13) 1.0000 Uiso
H11 H 0.7154 0.3944 -0.0665 0.0316 1.0000 Uiso
H21 H 0.4182 0.2316 -0.0930 0.0387 1.0000 Uiso
H31 H 0.4454 0.0831 -0.2816 0.0415 1.0000 Uiso
H32 H 0.5614 0.0324 -0.1667 0.0415 1.0000 Uiso
H41 H 0.6971 0.1953 -0.3394 0.0361 1.0000 Uiso
H42 H 0.7865 0.0600 -0.2887 0.0361 1.0000 Uiso
H61 H 0.8575 0.0595 -0.0201 0.0353 1.0000 Uiso
H71 H 0.9160 -0.0168 0.1716 0.0354 1.0000 Uiso
H91 H 0.6879 0.3341 0.3146 0.0359 1.0000 Uiso
H101 H 0.6243 0.4058 0.1235 0.0353 1.0000 Uiso
H121 H 0.8696 0.6046 -0.1199 0.0332 1.0000 Uiso
H131 H 0.7199 0.7778 -0.2206 0.0357 1.0000 Uiso
H151 H 0.7318 0.5414 -0.5381 0.0410 1.0000 Uiso
H161 H 0.8807 0.3668 -0.4396 0.0373 1.0000 Uiso
H171 H 0.6000 0.7527 -0.5380 0.0470 1.0000 Uiso
H172 H 0.6949 0.8718 -0.4380 0.0470 1.0000 Uiso
H173 H 0.4994 0.7996 -0.4226 0.0470 1.0000 Uiso
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0208(10) 0.0284(10) 0.0246(11) 0.0040(8) 0.0017(8) 0.0003(8)
C1 0.0197(12) 0.0298(12) 0.0295(13) 0.0058(10) 0.0007(10) 0.0025(9)
C2 0.0209(12) 0.0404(15) 0.0354(15) 0.0123(12) -0.0015(11) 0.0022(11)
C3 0.0263(14) 0.0373(15) 0.0402(16) 0.0067(12) -0.0032(12) -0.0051(11)
C4 0.0270(13) 0.0313(13) 0.0320(14) -0.0005(11) -0.0023(11) -0.0017(10)
C5 0.0179(11) 0.0312(13) 0.0278(13) 0.0042(10) 0.0018(10) 0.0010(10)
C6 0.0252(13) 0.0342(13) 0.0289(13) 0.0035(11) 0.0022(10) 0.0073(11)
C7 0.0250(13) 0.0314(13) 0.0320(14) 0.0066(11) 0.0010(11) 0.0052(10)
C8 0.0224(12) 0.0312(12) 0.0271(13) 0.0040(10) 0.0005(10) -0.0016(10)
C9 0.0257(13) 0.0323(13) 0.0318(14) 0.0020(11) 0.0031(11) -0.0002(10)
C10 0.0233(12) 0.0299(13) 0.0351(14) 0.0040(11) 0.0013(11) 0.0028(10)
Br1 0.03316(18) 0.04031(18) 0.02834(17) 0.00740(11) -0.00040(11) 0.00263(11)
O1 0.0215(10) 0.0474(12) 0.0419(12) 0.0139(10) -0.0026(9) 0.0066(9)
S1 0.0172(3) 0.0292(3) 0.0267(3) 0.0042(2) -0.0001(2) 0.0017(2)
O2 0.0213(9) 0.0364(10) 0.0285(10) 0.0021(8) -0.0039(7) -0.0006(7)
O3 0.0219(9) 0.0366(10) 0.0322(10) 0.0035(8) 0.0052(8) 0.0055(8)
C11 0.0186(11) 0.0311(13) 0.0294(13) 0.0054(10) 0.0011(10) -0.0023(10)
C12 0.0233(12) 0.0302(13) 0.0295(13) 0.0010(10) -0.0006(10) -0.0003(10)
C13 0.0248(13) 0.0294(13) 0.0350(14) 0.0024(11) 0.0015(11) -0.0003(10)
C14 0.0218(12) 0.0339(14) 0.0364(15) 0.0091(12) -0.0002(11) -0.0028(10)
C15 0.0362(15) 0.0387(15) 0.0276(13) 0.0060(11) 0.0013(11) 0.0022(12)
C16 0.0325(14) 0.0308(13) 0.0300(14) 0.0052(11) 0.0037(11) 0.0023(11)
C17 0.0338(16) 0.0400(16) 0.0438(18) 0.0132(13) -0.0048(13) 0.0036(12)
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.492(3) yes
N1 . C4 . 1.488(3) yes
N1 . S1 . 1.631(2) yes
C1 . C2 . 1.535(4) yes
C1 . C5 . 1.516(4) yes
C1 . H11 . 1.000 no
C2 . C3 . 1.522(5) yes
C2 . O1 . 1.429(3) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.530(4) yes
C3 . H31 . 1.000 no
C3 . H32 . 1.000 no
C4 . H41 . 1.000 no
C4 . H42 . 1.000 no
C5 . C6 . 1.394(4) yes
C5 . C10 . 1.399(4) yes
C6 . C7 . 1.398(4) yes
C6 . H61 . 1.000 no
C7 . C8 . 1.387(4) yes
C7 . H71 . 1.000 no
C8 . C9 . 1.395(4) yes
C8 . Br1 . 1.896(3) yes
C9 . C10 . 1.383(4) yes
C9 . H91 . 1.000 no
C10 . H101 . 1.000 no
O1 . H1 . 0.86(5) no
S1 . O2 . 1.431(2) yes
S1 . O3 . 1.447(2) yes
S1 . C11 . 1.762(3) yes
C11 . C12 . 1.388(4) yes
C11 . C16 . 1.401(4) yes
C12 . C13 . 1.392(4) yes
C12 . H121 . 1.000 no
C13 . C14 . 1.394(4) yes
C13 . H131 . 1.000 no
C14 . C15 . 1.398(4) yes
C14 . C17 . 1.501(4) yes
C15 . C16 . 1.386(4) yes
C15 . H151 . 1.000 no
C16 . H161 . 1.000 no
C17 . H171 . 1.000 no
C17 . H172 . 1.000 no
C17 . H173 . 1.000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . C4 . 110.8(2) yes
C1 . N1 . S1 . 117.61(18) yes
C4 . N1 . S1 . 118.48(18) yes
N1 . C1 . C2 . 103.0(2) yes
N1 . C1 . C5 . 112.5(2) yes
C2 . C1 . C5 . 113.3(2) yes
N1 . C1 . H11 . 113.114 no
C2 . C1 . H11 . 112.391 no
C5 . C1 . H11 . 102.856 no
C1 . C2 . C3 . 103.3(2) yes
C1 . C2 . O1 . 106.9(2) yes
C3 . C2 . O1 . 110.8(3) yes
C1 . C2 . H21 . 115.380 no
C3 . C2 . H21 . 111.771 no
O1 . C2 . H21 . 108.498 no
C2 . C3 . C4 . 102.2(2) yes
C2 . C3 . H31 . 111.250 no
C4 . C3 . H31 . 111.250 no
C2 . C3 . H32 . 111.250 no
C4 . C3 . H32 . 111.250 no
H31 . C3 . H32 . 109.467 no
N1 . C4 . C3 . 102.5(2) yes
N1 . C4 . H41 . 111.194 no
C3 . C4 . H41 . 111.195 no
N1 . C4 . H42 . 111.194 no
C3 . C4 . H42 . 111.195 no
H41 . C4 . H42 . 109.466 no
C1 . C5 . C6 . 121.9(2) yes
C1 . C5 . C10 . 119.1(2) yes
C6 . C5 . C10 . 118.9(3) yes
C5 . C6 . C7 . 120.9(3) yes
C5 . C6 . H61 . 119.557 no
C7 . C6 . H61 . 119.557 no
C6 . C7 . C8 . 118.8(2) yes
C6 . C7 . H71 . 120.599 no
C8 . C7 . H71 . 120.599 no
C7 . C8 . C9 . 121.2(3) yes
C7 . C8 . Br1 . 119.1(2) yes
C9 . C8 . Br1 . 119.7(2) yes
C8 . C9 . C10 . 119.2(3) yes
C8 . C9 . H91 . 120.392 no
C10 . C9 . H91 . 120.392 no
C5 . C10 . C9 . 120.9(3) yes
C5 . C10 . H101 . 119.545 no
C9 . C10 . H101 . 119.544 no
C2 . O1 . H1 . 103(3) no
N1 . S1 . O2 . 107.32(12) yes
N1 . S1 . O3 . 105.79(12) yes
O2 . S1 . O3 . 119.31(12) yes
N1 . S1 . C11 . 107.47(12) yes
O2 . S1 . C11 . 108.65(13) yes
O3 . S1 . C11 . 107.75(13) yes
S1 . C11 . C12 . 120.1(2) yes
S1 . C11 . C16 . 118.9(2) yes
C12 . C11 . C16 . 120.9(3) yes
C11 . C12 . C13 . 118.9(3) yes
C11 . C12 . H121 . 120.552 no
C13 . C12 . H121 . 120.552 no
C12 . C13 . C14 . 121.5(3) yes
C12 . C13 . H131 . 119.241 no
C14 . C13 . H131 . 119.241 no
C13 . C14 . C15 . 118.4(3) yes
C13 . C14 . C17 . 121.6(3) yes
C15 . C14 . C17 . 120.0(3) yes
C14 . C15 . C16 . 121.1(3) yes
C14 . C15 . H151 . 119.433 no
C16 . C15 . H151 . 119.433 no
C11 . C16 . C15 . 119.1(3) yes
C11 . C16 . H161 . 120.448 no
C15 . C16 . H161 . 120.448 no
C14 . C17 . H171 . 109.466 no
C14 . C17 . H172 . 109.466 no
H171 . C17 . H172 . 109.476 no
C14 . C17 . H173 . 109.467 no
H171 . C17 . H173 . 109.476 no
H172 . C17 . H173 . 109.476 no

loop_
_geom_hbond_atom_site_label_d
_geom_hbond_atom_site_label_h
_geom_hbond_atom_site_label_a
_geom_hbond_site_symmetry_a
_geom_hbond_distance_dh
_geom_hbond_distance_ha
_geom_hbond_distance_da
_geom_hbond_angle_dha
_geom_hbond_publ_flag
O1 H1 O3 1_455 0.86(5) 2.06(5) 2.903(3) 165(4) yes

_chemical_name_common            
(2R*,3S*)-2-(4-bromophenyl)-1-tosylpyrrolidin-3-ol