# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_7a
_chemical_name_systematic        ?
_chemical_name_common            
trans-Methyl-3-(phenylsulfonyl)-1-propylpyrrolidin-2-one
_chemical_formula_moiety         'C14 H19 N O3 S'
_chemical_formula_sum            'C14 H19 N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         281.36
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   7.681(3)
_cell_length_b                   12.525(5)
_cell_length_c                   14.693(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1413.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.9926
_cell_measurement_theta_max      26.3706
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            21075
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             2909
_reflns_number_gt                2814
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0634
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         2909
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+0.2827P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)

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'

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al, 2008)'
_computing_publication_material  ?


loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.19094(15) 0.52095(9) 0.95273(8) 0.0176(2) Uani d . 1 . .
C C2 0.22022(17) 0.62584(10) 0.94040(9) 0.0166(3) Uani d . 1 . .
C C3 0.05852(17) 0.67435(11) 0.89691(9) 0.0160(3) Uani d . 1 . .
H H3 0.0056 0.7284 0.9387 0.019 Uiso calc R 1 . .
C C4 -0.06967(17) 0.58118(10) 0.88120(10) 0.0184(3) Uani d . 1 . .
H H4 -0.0802 0.5684 0.8142 0.022 Uiso calc R 1 . .
C C5 0.01969(18) 0.48371(12) 0.92501(11) 0.0226(3) Uani d . 1 . .
H H5A -0.0474 0.4583 0.9783 0.027 Uiso calc R 1 . .
H H5B 0.0299 0.4246 0.8806 0.027 Uiso calc R 1 . .
C C6 0.3191(2) 0.45054(11) 0.99403(10) 0.0202(3) Uani d . 1 . .
H H6A 0.2636 0.4104 1.0443 0.024 Uiso calc R 1 . .
H H6B 0.4142 0.4941 1.0203 0.024 Uiso calc R 1 . .
C C7 0.3955(2) 0.37199(11) 0.92590(10) 0.0250(3) Uani d . 1 . .
H H7A 0.4441 0.4118 0.8735 0.03 Uiso calc R 1 . .
H H7B 0.3019 0.3249 0.9028 0.03 Uiso calc R 1 . .
C C8 0.5383(2) 0.30396(14) 0.96873(14) 0.0381(4) Uani d . 1 . .
H H8A 0.6327 0.3503 0.99 0.057 Uiso calc R 1 . .
H H8B 0.5837 0.2538 0.9234 0.057 Uiso calc R 1 . .
H H8C 0.4903 0.2641 1.0203 0.057 Uiso calc R 1 . .
O O9 0.35254(12) 0.67427(8) 0.96143(7) 0.0236(2) Uani d . 1 . .
S S10 0.10430(4) 0.73380(3) 0.78842(2) 0.01811(9) Uani d . 1 . .
O O11 0.19619(15) 0.65645(8) 0.73388(7) 0.0278(2) Uani d . 1 . .
O O12 -0.05840(13) 0.77503(8) 0.75431(7) 0.0262(2) Uani d . 1 . .
C C13 0.24413(19) 0.84334(11) 0.80781(9) 0.0204(3) Uani d . 1 . .
C C14 0.4232(2) 0.82857(13) 0.80502(10) 0.0274(3) Uani d . 1 . .
H H14 0.471 0.7594 0.7958 0.033 Uiso calc R 1 . .
C C15 0.5315(2) 0.91653(16) 0.81588(11) 0.0359(4) Uani d . 1 . .
H H15 0.6543 0.9077 0.8147 0.043 Uiso calc R 1 . .
C C16 0.4607(2) 1.01679(15) 0.82840(11) 0.0349(4) Uani d . 1 . .
H H16 0.5354 1.0768 0.8345 0.042 Uiso calc R 1 . .
C C17 0.2812(2) 1.03093(13) 0.83223(11) 0.0315(4) Uani d . 1 . .
H H17 0.2338 1.1002 0.8415 0.038 Uiso calc R 1 . .
C C18 0.1716(2) 0.94368(12) 0.82253(10) 0.0242(3) Uani d . 1 . .
H H18 0.0488 0.9523 0.8259 0.029 Uiso calc R 1 . .
C C19 -0.2494(2) 0.60252(13) 0.91944(14) 0.0333(4) Uani d . 1 . .
H H19A -0.3251 0.5413 0.907 0.05 Uiso calc R 1 . .
H H19B -0.2982 0.6665 0.8908 0.05 Uiso calc R 1 . .
H H19C -0.2412 0.6136 0.9853 0.05 Uiso calc R 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3452(18) ?
N1 C5 . 1.4537(18) ?
N1 C6 . 1.4541(18) ?
C2 O9 . 1.2233(17) ?
C2 C3 . 1.5232(19) ?
C3 C4 . 1.5442(18) ?
C3 S10 . 1.7941(14) ?
C3 H3 . 1.0 ?
C4 C19 . 1.514(2) ?
C4 C5 . 1.541(2) ?
C4 H4 . 1.0 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.521(2) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.525(2) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
S10 O11 . 1.4419(11) ?
S10 O12 . 1.4420(11) ?
S10 C13 . 1.7656(15) ?
C13 C14 . 1.389(2) ?
C13 C18 . 1.392(2) ?
C14 C15 . 1.390(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.381(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.391(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.387(2) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . 115.27(12) ?
C2 N1 C6 . . 122.37(12) ?
C5 N1 C6 . . 122.33(12) ?
O9 C2 N1 . . 126.10(13) ?
O9 C2 C3 . . 125.84(12) ?
N1 C2 C3 . . 108.05(11) ?
C2 C3 C4 . . 106.33(11) ?
C2 C3 S10 . . 112.24(9) ?
C4 C3 S10 . . 107.80(9) ?
C2 C3 H3 . . 110.1 ?
C4 C3 H3 . . 110.1 ?
S10 C3 H3 . . 110.1 ?
C19 C4 C5 . . 113.00(13) ?
C19 C4 C3 . . 113.10(12) ?
C5 C4 C3 . . 104.61(11) ?
C19 C4 H4 . . 108.7 ?
C5 C4 H4 . . 108.7 ?
C3 C4 H4 . . 108.7 ?
N1 C5 C4 . . 105.41(11) ?
N1 C5 H5A . . 110.7 ?
C4 C5 H5A . . 110.7 ?
N1 C5 H5B . . 110.7 ?
C4 C5 H5B . . 110.7 ?
H5A C5 H5B . . 108.8 ?
N1 C6 C7 . . 112.25(12) ?
N1 C6 H6A . . 109.2 ?
C7 C6 H6A . . 109.2 ?
N1 C6 H6B . . 109.2 ?
C7 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C6 C7 C8 . . 111.54(14) ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O11 S10 O12 . . 118.14(7) ?
O11 S10 C13 . . 108.31(7) ?
O12 S10 C13 . . 107.75(7) ?
O11 S10 C3 . . 108.11(7) ?
O12 S10 C3 . . 106.71(6) ?
C13 S10 C3 . . 107.36(6) ?
C14 C13 C18 . . 121.44(14) ?
C14 C13 S10 . . 119.62(12) ?
C18 C13 S10 . . 118.90(12) ?
C13 C14 C15 . . 118.94(16) ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
C16 C15 C14 . . 120.03(16) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.77(16) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C18 C17 C16 . . 119.81(17) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C13 . . 118.98(15) ?
C17 C18 H18 . . 120.5 ?
C13 C18 H18 . . 120.5 ?
C4 C19 H19A . . 109.5 ?
C4 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C4 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 O9 . . . . 177.64(13) ?
C6 N1 C2 O9 . . . . -0.1(2) ?
C5 N1 C2 C3 . . . . -1.50(16) ?
C6 N1 C2 C3 . . . . -179.28(11) ?
O9 C2 C3 C4 . . . . 178.47(13) ?
N1 C2 C3 C4 . . . . -2.40(14) ?
O9 C2 C3 S10 . . . . 60.82(16) ?
N1 C2 C3 S10 . . . . -120.04(11) ?
C2 C3 C4 C19 . . . . 128.36(13) ?
S10 C3 C4 C19 . . . . -111.09(13) ?
C2 C3 C4 C5 . . . . 4.98(14) ?
S10 C3 C4 C5 . . . . 125.53(10) ?
C2 N1 C5 C4 . . . . 4.73(16) ?
C6 N1 C5 C4 . . . . -177.48(12) ?
C19 C4 C5 N1 . . . . -129.16(13) ?
C3 C4 C5 N1 . . . . -5.71(14) ?
C2 N1 C6 C7 . . . . -110.66(15) ?
C5 N1 C6 C7 . . . . 71.71(17) ?
N1 C6 C7 C8 . . . . 176.11(12) ?
C2 C3 S10 O11 . . . . 51.16(11) ?
C4 C3 S10 O11 . . . . -65.60(10) ?
C2 C3 S10 O12 . . . . 179.21(9) ?
C4 C3 S10 O12 . . . . 62.45(10) ?
C2 C3 S10 C13 . . . . -65.48(11) ?
C4 C3 S10 C13 . . . . 177.76(9) ?
O11 S10 C13 C14 . . . . -25.30(14) ?
O12 S10 C13 C14 . . . . -154.18(12) ?
C3 S10 C13 C14 . . . . 91.21(13) ?
O11 S10 C13 C18 . . . . 152.52(11) ?
O12 S10 C13 C18 . . . . 23.65(13) ?
C3 S10 C13 C18 . . . . -90.96(12) ?
C18 C13 C14 C15 . . . . -1.0(2) ?
S10 C13 C14 C15 . . . . 176.80(11) ?
C13 C14 C15 C16 . . . . -0.6(2) ?
C14 C15 C16 C17 . . . . 1.3(3) ?
C15 C16 C17 C18 . . . . -0.6(3) ?
C16 C17 C18 C13 . . . . -0.9(2) ?
C14 C13 C18 C17 . . . . 1.7(2) ?
S10 C13 C18 C17 . . . . -176.10(11) ?

_database_code_depnum_ccdc_archive 'CCDC 1012785'
