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

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_44

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N-Adamantan-1-yl-4-methyl-benzenesulfonamide  
;
_chemical_name_common            ?
_chemical_melting_point          437.9
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 N O2 S'
_chemical_formula_weight         305.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.189(2)
_cell_length_b                   6.5360(13)
_cell_length_c                   21.527(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.41(3)
_cell_angle_gamma                90.00
_cell_volume                     1537.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3097
_diffrn_reflns_av_R_equivalents  0.0100
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3010
_reflns_number_gt                2331
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1071P)²+0.4764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.10930(5) 0.32983(9) 0.70512(3) 0.0462(2) Uani 1 1 d . . .
O1 O -0.02069(17) 0.3514(3) 0.69587(9) 0.0700(6) Uani 1 1 d . . .
O2 O 0.1823(2) 0.5071(3) 0.70080(9) 0.0672(6) Uani 1 1 d . . .
N1 N 0.15062(15) 0.2290(3) 0.77470(8) 0.0392(4) Uani 1 1 d . . .
H1 H 0.0924 0.1877 0.7920 0.047 Uiso 1 1 calc R . .
C1 C 0.27662(17) 0.1983(3) 0.81274(8) 0.0307(4) Uani 1 1 d . . .
C3 C 0.3541(2) 0.3930(3) 0.81751(11) 0.0439(5) Uani 1 1 d . . .
H3A H 0.3121 0.5046 0.8335 0.053 Uiso 1 1 calc R . .
H3B H 0.3661 0.4308 0.7757 0.053 Uiso 1 1 calc R . .
C4 C 0.25960(19) 0.1419(4) 0.87927(9) 0.0402(5) Uani 1 1 d . . .
H4A H 0.2102 0.0190 0.8770 0.048 Uiso 1 1 calc R . .
H4B H 0.2171 0.2516 0.8959 0.048 Uiso 1 1 calc R . .
C7 C 0.4781(2) 0.3555(3) 0.86239(13) 0.0479(6) Uani 1 1 d . . .
H7A H 0.5276 0.4803 0.8653 0.057 Uiso 1 1 calc R . .
C2 C 0.3436(2) 0.0236(3) 0.78685(10) 0.0416(5) Uani 1 1 d . . .
H2A H 0.2949 -0.1004 0.7835 0.050 Uiso 1 1 calc R . .
H2B H 0.3552 0.0584 0.7447 0.050 Uiso 1 1 calc R . .
C11 C 0.13213(19) 0.1565(4) 0.64600(10) 0.0401(5) Uani 1 1 d . . .
C5 C 0.3842(2) 0.1056(4) 0.92374(9) 0.0428(5) Uani 1 1 d . . .
H5A H 0.3722 0.0687 0.9661 0.051 Uiso 1 1 calc R . .
C6 C 0.4675(2) -0.0121(3) 0.83151(10) 0.0445(5) Uani 1 1 d . . .
H6A H 0.5101 -0.1238 0.8149 0.053 Uiso 1 1 calc R . .
C9 C 0.4605(2) 0.2984(4) 0.92844(11) 0.0500(6) Uani 1 1 d . . .
H9A H 0.5394 0.2760 0.9567 0.060 Uiso 1 1 calc R . .
H9B H 0.4195 0.4089 0.9456 0.060 Uiso 1 1 calc R . .
C8 C 0.4487(2) -0.0696(3) 0.89747(10) 0.0462(6) Uani 1 1 d . . .
H8A H 0.3996 -0.1929 0.8948 0.055 Uiso 1 1 calc R . .
H8B H 0.5272 -0.0961 0.9257 0.055 Uiso 1 1 calc R . .
C14 C 0.1515(2) -0.1005(5) 0.54553(11) 0.0533(6) Uani 1 1 d . . .
C12 C 0.0758(3) -0.0331(4) 0.64003(12) 0.0543(6) Uani 1 1 d . . .
H12A H 0.0317 -0.0756 0.6697 0.065 Uiso 1 1 calc R . .
C10 C 0.5446(2) 0.1816(4) 0.83623(13) 0.0522(6) Uani 1 1 d . . .
H10A H 0.5577 0.2182 0.7945 0.063 Uiso 1 1 calc R . .
H10B H 0.6237 0.1583 0.8642 0.063 Uiso 1 1 calc R . .
C13 C 0.0855(3) -0.1580(4) 0.59023(13) 0.0581(7) Uani 1 1 d . . .
H13A H 0.0467 -0.2847 0.5863 0.070 Uiso 1 1 calc R . .
C16 C 0.2002(2) 0.2161(5) 0.60258(12) 0.0562(6) Uani 1 1 d . . .
H16A H 0.2403 0.3416 0.6069 0.067 Uiso 1 1 calc R . .
C15 C 0.2081(3) 0.0883(5) 0.55307(13) 0.0653(8) Uani 1 1 d . . .
H15A H 0.2530 0.1302 0.5236 0.078 Uiso 1 1 calc R . .
C17 C 0.1580(3) -0.2379(6) 0.49038(14) 0.0777(9) Uani 1 1 d . . .
H1C H 0.2003 -0.1688 0.4621 0.117 Uiso 1 1 calc R . .
H1A H 0.0767 -0.2718 0.4680 0.117 Uiso 1 1 calc R . .
H1B H 0.2012 -0.3609 0.5058 0.117 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.432(2) . ?
S1 O2 1.432(2) . ?
S1 N1 1.6106(18) . ?
S1 C11 1.763(2) . ?
N1 C1 1.484(2) . ?
N1 H1A 0.8600 . ?
C1 C4 1.530(3) . ?
C1 C3 1.530(3) . ?
C1 C2 1.535(3) . ?
C3 C7 1.531(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.531(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 C9 1.523(4) . ?
C7 C10 1.530(3) . ?
C7 H7A 0.9800 . ?
C2 C6 1.526(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C11 C16 1.383(3) . ?
C11 C12 1.384(3) . ?
C5 C9 1.513(3) . ?
C5 C8 1.525(3) . ?
C5 H5A 0.9800 . ?
C6 C10 1.523(4) . ?
C6 C8 1.526(3) . ?
C6 H6A 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C14 C15 1.381(4) . ?
C14 C13 1.385(4) . ?
C14 C17 1.503(4) . ?
C12 C13 1.370(4) . ?
C12 H12A 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13A 0.9300 . ?
C16 C15 1.372(4) . ?
C16 H16A 0.9300 . ?
C15 H15A 0.9300 . ?
C17 H1C 0.9600 . ?
C17 H1A 0.9600 . ?
C17 H1B 0.9600 . ?

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 O2 119.19(13) . . ?
O1 S1 N1 104.46(11) . . ?
O2 S1 N1 109.74(11) . . ?
O1 S1 C11 105.26(12) . . ?
O2 S1 C11 107.44(12) . . ?
N1 S1 C11 110.56(10) . . ?
C1 N1 S1 128.11(14) . . ?
C1 N1 H1A 115.9 . . ?
S1 N1 H1A 115.9 . . ?
N1 C1 C4 104.74(15) . . ?
N1 C1 C3 112.45(16) . . ?
C4 C1 C3 108.68(16) . . ?
N1 C1 C2 112.33(16) . . ?
C4 C1 C2 109.21(16) . . ?
C3 C1 C2 109.25(17) . . ?
C1 C3 C7 109.44(17) . . ?
C1 C3 H3A 109.8 . . ?
C7 C3 H3A 109.8 . . ?
C1 C3 H3B 109.8 . . ?
C7 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C1 C4 C5 110.05(16) . . ?
C1 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C1 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C9 C7 C10 109.4(2) . . ?
C9 C7 C3 110.25(19) . . ?
C10 C7 C3 109.5(2) . . ?
C9 C7 H7A 109.2 . . ?
C10 C7 H7A 109.2 . . ?
C3 C7 H7A 109.2 . . ?
C6 C2 C1 109.46(17) . . ?
C6 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C6 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 S1 119.58(19) . . ?
C12 C11 S1 120.59(17) . . ?
C9 C5 C8 110.19(18) . . ?
C9 C5 C4 109.73(19) . . ?
C8 C5 C4 108.92(17) . . ?
C9 C5 H5A 109.3 . . ?
C8 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C10 C6 C8 109.39(19) . . ?
C10 C6 C2 109.88(18) . . ?
C8 C6 C2 109.60(19) . . ?
C10 C6 H6A 109.3 . . ?
C8 C6 H6A 109.3 . . ?
C2 C6 H6A 109.3 . . ?
C5 C9 C7 109.03(17) . . ?
C5 C9 H9A 109.9 . . ?
C7 C9 H9A 109.9 . . ?
C5 C9 H9B 109.9 . . ?
C7 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C5 C8 C6 109.32(17) . . ?
C5 C8 H8A 109.8 . . ?
C6 C8 H8A 109.8 . . ?
C5 C8 H8B 109.8 . . ?
C6 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C15 C14 C13 117.4(2) . . ?
C15 C14 C17 121.9(3) . . ?
C13 C14 C17 120.7(3) . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C6 C10 C7 109.22(17) . . ?
C6 C10 H10A 109.8 . . ?
C7 C10 H10A 109.8 . . ?
C6 C10 H10B 109.8 . . ?
C7 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C15 C16 C11 119.4(3) . . ?
C15 C16 H16A 120.3 . . ?
C11 C16 H16A 120.3 . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
C14 C17 H1C 109.5 . . ?
C14 C17 H1A 109.5 . . ?
H1C C17 H1A 109.5 . . ?
C14 C17 H1B 109.5 . . ?
H1C C17 H1B 109.5 . . ?
H1A C17 H1B 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.051
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_database_code_depnum_ccdc_archive 'CCDC 1028778'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_45

_audit_creation_method           SHELXTL
_chemical_name_systematic        'N-Adamantan-1-yl-benzenesulfonamide '
_chemical_name_common            ?
_chemical_melting_point          397.5
_chemical_formula_moiety         'C16 H21 N O2 S'
_chemical_formula_sum            'C16 H21 N O2 S'
_chemical_formula_weight         291.40

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.9770(10)
_cell_length_b                   10.5160(10)
_cell_length_c                   11.2900(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1422.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .34
_exptl_crystal_size_min          .22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1789
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1458
_reflns_number_gt                1365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.1929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0194(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_number_reflns         1458
_refine_ls_number_parameters     185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0734
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.13607(5) 0.59364(6) -0.00273(7) 0.0465(2) Uani 1 1 d . . .
O1 O 0.0802(2) 0.5192(2) 0.0857(3) 0.0762(8) Uani 1 1 d . . .
O2 O 0.07523(14) 0.69089(18) -0.0633(3) 0.0660(7) Uani 1 1 d . . .
N1 N 0.24342(18) 0.65511(19) 0.0621(2) 0.0423(5) Uani 1 1 d D . .
H1 H 0.263(2) 0.618(2) 0.1262(17) 0.051 Uiso 1 1 d D . .
C1 C 0.18368(19) 0.4852(2) -0.1114(3) 0.0386(6) Uani 1 1 d . . .
C2 C 0.2851(2) 0.4227(2) -0.0989(3) 0.0428(6) Uani 1 1 d . . .
H2 H 0.3323 0.4422 -0.0361 0.051 Uiso 1 1 calc R . .
C3 C 0.3152(2) 0.3309(3) -0.1809(3) 0.0506(7) Uani 1 1 d . . .
H3 H 0.3832 0.2891 -0.1738 0.061 Uiso 1 1 calc R . .
C4 C 0.2442(3) 0.3017(3) -0.2732(3) 0.0557(8) Uani 1 1 d . . .
H4 H 0.2645 0.2398 -0.3279 0.067 Uiso 1 1 calc R . .
C5 C 0.1434(2) 0.3637(3) -0.2849(3) 0.0517(8) Uani 1 1 d . . .
H5 H 0.0955 0.3423 -0.3466 0.062 Uiso 1 1 calc R . .
C6 C 0.1130(2) 0.4572(3) -0.2053(3) 0.0441(7) Uani 1 1 d . . .
H6 H 0.0461 0.5009 -0.2145 0.053 Uiso 1 1 calc R . .
C7 C 0.31241(19) 0.7639(2) 0.0212(2) 0.0323(5) Uani 1 1 d . . .
C8 C 0.3518(2) 0.7469(2) -0.1062(2) 0.0376(6) Uani 1 1 d . . .
H81 H 0.2879 0.7434 -0.1589 0.045 Uiso 1 1 calc R . .
H82 H 0.3928 0.6678 -0.1137 0.045 Uiso 1 1 calc R . .
C9 C 0.4271(2) 0.8586(3) -0.1408(2) 0.0454(7) Uani 1 1 d . . .
H9 H 0.4518 0.8477 -0.2230 0.055 Uiso 1 1 calc R . .
C10 C 0.5286(2) 0.8617(3) -0.0599(3) 0.0528(8) Uani 1 1 d . . .
H101 H 0.5776 0.9310 -0.0827 0.063 Uiso 1 1 calc R . .
H102 H 0.5698 0.7827 -0.0668 0.063 Uiso 1 1 calc R . .
C11 C 0.4899(2) 0.8802(3) 0.0682(3) 0.0474(7) Uani 1 1 d . . .
H11 H 0.5551 0.8826 0.1207 0.057 Uiso 1 1 calc R . .
C12 C 0.4146(2) 0.7680(3) 0.1030(3) 0.0441(7) Uani 1 1 d . . .
H121 H 0.4560 0.6891 0.0965 0.053 Uiso 1 1 calc R . .
H122 H 0.3905 0.7776 0.1846 0.053 Uiso 1 1 calc R . .
C13 C 0.2476(2) 0.8891(2) 0.0321(2) 0.0405(6) Uani 1 1 d . . .
H131 H 0.2219 0.9002 0.1129 0.049 Uiso 1 1 calc R . .
H132 H 0.1828 0.8872 -0.0195 0.049 Uiso 1 1 calc R . .
C14 C 0.3239(2) 1.0001(2) -0.0027(3) 0.0456(6) Uani 1 1 d . . .
H14 H 0.2822 1.0800 0.0040 0.055 Uiso 1 1 calc R . .
C15 C 0.4248(2) 1.0049(3) 0.0797(3) 0.0509(7) Uani 1 1 d . . .
H151 H 0.4003 1.0164 0.1608 0.061 Uiso 1 1 calc R . .
H152 H 0.4724 1.0760 0.0585 0.061 Uiso 1 1 calc R . .
C16 C 0.3630(3) 0.9835(3) -0.1299(3) 0.0528(8) Uani 1 1 d . . .
H161 H 0.4108 1.0540 -0.1522 0.063 Uiso 1 1 calc R . .
H162 H 0.2991 0.9826 -0.1827 0.063 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.430(2) . ?
S1 O1 1.434(3) . ?
S1 N1 1.615(2) . ?
S1 C1 1.770(3) . ?
N1 C7 1.484(3) . ?
N1 H1 0.856(10) . ?
C1 C6 1.388(4) . ?
C1 C2 1.388(3) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.525(4) . ?
C7 C12 1.533(4) . ?
C7 C13 1.533(3) . ?
C8 C9 1.531(3) . ?
C8 H81 0.9700 . ?
C8 H82 0.9700 . ?
C9 C10 1.521(4) . ?
C9 C16 1.527(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.531(5) . ?
C10 H101 0.9700 . ?
C10 H102 0.9700 . ?
C11 C15 1.531(4) . ?
C11 C12 1.537(4) . ?
C11 H11 0.9800 . ?
C12 H121 0.9700 . ?
C12 H122 0.9700 . ?
C13 C14 1.534(4) . ?
C13 H131 0.9700 . ?
C13 H132 0.9700 . ?
C14 C16 1.520(5) . ?
C14 C15 1.526(4) . ?
C14 H14 0.9800 . ?
C15 H151 0.9700 . ?
C15 H152 0.9700 . ?
C16 H161 0.9700 . ?
C16 H162 0.9700 . ?

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
O2 S1 O1 119.04(15) . . ?
O2 S1 N1 109.65(11) . . ?
O1 S1 N1 105.94(15) . . ?
O2 S1 C1 107.09(15) . . ?
O1 S1 C1 106.31(13) . . ?
N1 S1 C1 108.42(11) . . ?
C7 N1 S1 127.64(19) . . ?
C7 N1 H1 118(2) . . ?
S1 N1 H1 114(2) . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 S1 118.02(18) . . ?
C2 C1 S1 121.1(2) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 112.1(2) . . ?
N1 C7 C12 106.2(2) . . ?
C8 C7 C12 109.0(2) . . ?
N1 C7 C13 110.80(19) . . ?
C8 C7 C13 109.4(2) . . ?
C12 C7 C13 109.3(2) . . ?
C7 C8 C9 109.5(2) . . ?
C7 C8 H81 109.8 . . ?
C9 C8 H81 109.8 . . ?
C7 C8 H82 109.8 . . ?
C9 C8 H82 109.8 . . ?
H81 C8 H82 108.2 . . ?
C10 C9 C16 109.6(2) . . ?
C10 C9 C8 109.5(2) . . ?
C16 C9 C8 110.0(2) . . ?
C10 C9 H9 109.2 . . ?
C16 C9 H9 109.2 . . ?
C8 C9 H9 109.2 . . ?
C9 C10 C11 109.2(2) . . ?
C9 C10 H101 109.8 . . ?
C11 C10 H101 109.8 . . ?
C9 C10 H102 109.8 . . ?
C11 C10 H102 109.8 . . ?
H101 C10 H102 108.3 . . ?
C15 C11 C10 110.0(3) . . ?
C15 C11 C12 109.7(2) . . ?
C10 C11 C12 108.8(2) . . ?
C15 C11 H11 109.4 . . ?
C10 C11 H11 109.4 . . ?
C12 C11 H11 109.4 . . ?
C7 C12 C11 109.7(2) . . ?
C7 C12 H121 109.7 . . ?
C11 C12 H121 109.7 . . ?
C7 C12 H122 109.7 . . ?
C11 C12 H122 109.7 . . ?
H121 C12 H122 108.2 . . ?
C7 C13 C14 109.37(19) . . ?
C7 C13 H131 109.8 . . ?
C14 C13 H131 109.8 . . ?
C7 C13 H132 109.8 . . ?
C14 C13 H132 109.8 . . ?
H131 C13 H132 108.2 . . ?
C16 C14 C15 109.6(2) . . ?
C16 C14 C13 109.7(2) . . ?
C15 C14 C13 109.9(2) . . ?
C16 C14 H14 109.2 . . ?
C15 C14 H14 109.2 . . ?
C13 C14 H14 109.2 . . ?
C14 C15 C11 108.9(2) . . ?
C14 C15 H151 109.9 . . ?
C11 C15 H151 109.9 . . ?
C14 C15 H152 109.9 . . ?
C11 C15 H152 109.9 . . ?
H151 C15 H152 108.3 . . ?
C14 C16 C9 109.3(2) . . ?
C14 C16 H161 109.8 . . ?
C9 C16 H161 109.8 . . ?
C14 C16 H162 109.8 . . ?
C9 C16 H162 109.8 . . ?
H161 C16 H162 108.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C7 -33.6(3) . . . . ?
O1 S1 N1 C7 -163.2(2) . . . . ?
C1 S1 N1 C7 83.0(2) . . . . ?
O2 S1 C1 C6 -38.3(2) . . . . ?
O1 S1 C1 C6 90.0(2) . . . . ?
N1 S1 C1 C6 -156.5(2) . . . . ?
O2 S1 C1 C2 146.4(2) . . . . ?
O1 S1 C1 C2 -85.4(2) . . . . ?
N1 S1 C1 C2 28.1(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
S1 C1 C2 C3 174.8(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
S1 C1 C6 C5 -173.6(2) . . . . ?
S1 N1 C7 C8 -51.4(3) . . . . ?
S1 N1 C7 C12 -170.27(19) . . . . ?
S1 N1 C7 C13 71.1(3) . . . . ?
N1 C7 C8 C9 -177.2(2) . . . . ?
C12 C7 C8 C9 -60.0(3) . . . . ?
C13 C7 C8 C9 59.5(2) . . . . ?
C7 C8 C9 C10 60.8(3) . . . . ?
C7 C8 C9 C16 -59.7(3) . . . . ?
C16 C9 C10 C11 59.8(3) . . . . ?
C8 C9 C10 C11 -61.0(3) . . . . ?
C9 C10 C11 C15 -59.5(3) . . . . ?
C9 C10 C11 C12 60.7(3) . . . . ?
N1 C7 C12 C11 -178.9(2) . . . . ?
C8 C7 C12 C11 60.2(3) . . . . ?
C13 C7 C12 C11 -59.3(3) . . . . ?
C15 C11 C12 C7 59.9(3) . . . . ?
C10 C11 C12 C7 -60.5(3) . . . . ?
N1 C7 C13 C14 176.2(2) . . . . ?
C8 C7 C13 C14 -59.8(3) . . . . ?
C12 C7 C13 C14 59.4(3) . . . . ?
C7 C13 C14 C16 60.2(3) . . . . ?
C7 C13 C14 C15 -60.5(3) . . . . ?
C16 C14 C15 C11 -60.2(3) . . . . ?
C13 C14 C15 C11 60.6(3) . . . . ?
C10 C11 C15 C14 59.5(3) . . . . ?
C12 C11 C15 C14 -60.1(3) . . . . ?
C15 C14 C16 C9 60.9(3) . . . . ?
C13 C14 C16 C9 -59.9(3) . . . . ?
C10 C9 C16 C14 -60.7(3) . . . . ?
C8 C9 C16 C14 59.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_database_code_depnum_ccdc_archive 'CCDC 1028779'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_46

_audit_creation_method           SHELXTL
_chemical_name_systematic        'N-Adamantan-1-yl-4-chloro-benzenesulfonamide '
_chemical_name_common            ?
_chemical_melting_point          460
_chemical_formula_moiety         'C16 H20 Cl N O2 S'
_chemical_formula_sum            'C16 H20 Cl N O2 S'
_chemical_formula_weight         325.84

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0510(4)
_cell_length_b                   6.4458(3)
_cell_length_c                   21.4660(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.427(3)
_cell_angle_gamma                90.00
_cell_volume                     1493.24(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    3324
_cell_measurement_theta_min      2.909
_cell_measurement_theta_max      31.36

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .95643
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SCALE3

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2060
_diffrn_standards_number         8464
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7450
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         29.05
_reflns_number_total             3990
_reflns_number_gt                3442
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'bruker XSCANS'
_computing_cell_refinement       'bruker XSCANS'
_computing_data_reduction        'BRUKER SHELXTL'
_computing_structure_solution    'BRUKER SHELXTL'
_computing_structure_refinement  'BRUKER SHELXTL'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0416P)²+0.4965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3990
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.10816(3) 0.83217(6) 0.204944(15) 0.01879(9) Uani 1 1 d . . .
Cl1 Cl 0.16206(4) 0.24245(9) -0.018699(19) 0.04399(14) Uani 1 1 d . . .
O1 O -0.02446(9) 0.85134(19) 0.19611(5) 0.0289(3) Uani 1 1 d . . .
O2 O 0.18059(10) 1.01323(17) 0.20043(5) 0.0284(2) Uani 1 1 d . . .
N1 N 0.15161(10) 0.72985(19) 0.27468(5) 0.0166(2) Uani 1 1 d . . .
H1 H 0.1028 0.6249 0.2805 0.020 Uiso 1 1 d . . .
C1 C 0.13134(12) 0.6576(2) 0.14464(6) 0.0180(3) Uani 1 1 d . . .
C2 C 0.07378(15) 0.4662(2) 0.13888(7) 0.0261(3) Uani 1 1 d . . .
H2 H 0.0287 0.4242 0.1686 0.031 Uiso 1 1 calc R . .
C3 C 0.08346(15) 0.3369(3) 0.08862(7) 0.0285(3) Uani 1 1 d . . .
H3 H 0.0454 0.2075 0.0843 0.034 Uiso 1 1 calc R . .
C4 C 0.15097(13) 0.4040(3) 0.04485(6) 0.0265(3) Uani 1 1 d . . .
C5 C 0.20880(14) 0.5929(3) 0.05036(7) 0.0334(4) Uani 1 1 d . . .
H5 H 0.2539 0.6343 0.0206 0.040 Uiso 1 1 calc R . .
C6 C 0.19944(14) 0.7221(3) 0.10087(7) 0.0281(3) Uani 1 1 d . . .
H6 H 0.2385 0.8507 0.1053 0.034 Uiso 1 1 calc R . .
C7 C 0.27987(11) 0.6999(2) 0.31270(5) 0.0135(2) Uani 1 1 d . . .
C8 C 0.34746(12) 0.5232(2) 0.28651(6) 0.0163(2) Uani 1 1 d . . .
H81 H 0.3595 0.5592 0.2444 0.020 Uiso 1 1 calc R . .
H82 H 0.2981 0.3976 0.2829 0.020 Uiso 1 1 calc R . .
C9 C 0.47371(12) 0.4863(2) 0.33181(6) 0.0181(3) Uani 1 1 d . . .
H9 H 0.5173 0.3738 0.3151 0.022 Uiso 1 1 calc R . .
C10 C 0.45390(13) 0.4270(2) 0.39819(6) 0.0194(3) Uani 1 1 d . . .
H101 H 0.4046 0.3014 0.3953 0.023 Uiso 1 1 calc R . .
H102 H 0.5332 0.4006 0.4267 0.023 Uiso 1 1 calc R . .
C11 C 0.38733(12) 0.6044(2) 0.42455(6) 0.0187(3) Uani 1 1 d . . .
H11 H 0.3747 0.5666 0.4669 0.022 Uiso 1 1 calc R . .
C12 C 0.26161(12) 0.6416(2) 0.37962(6) 0.0172(3) Uani 1 1 d . . .
H121 H 0.2184 0.7527 0.3962 0.021 Uiso 1 1 calc R . .
H122 H 0.2115 0.5171 0.3770 0.021 Uiso 1 1 calc R . .
C13 C 0.35684(12) 0.8985(2) 0.31761(6) 0.0177(3) Uani 1 1 d . . .
H131 H 0.3138 1.0106 0.3338 0.021 Uiso 1 1 calc R . .
H132 H 0.3688 0.9378 0.2757 0.021 Uiso 1 1 calc R . .
C14 C 0.48312(12) 0.8608(2) 0.36284(6) 0.0195(3) Uani 1 1 d . . .
H14 H 0.5329 0.9877 0.3658 0.023 Uiso 1 1 calc R . .
C15 C 0.46466(13) 0.8026(2) 0.42952(6) 0.0209(3) Uani 1 1 d . . .
H151 H 0.5444 0.7806 0.4581 0.025 Uiso 1 1 calc R . .
H152 H 0.4226 0.9143 0.4465 0.025 Uiso 1 1 calc R . .
C16 C 0.55109(12) 0.6849(2) 0.33681(7) 0.0212(3) Uani 1 1 d . . .
H161 H 0.5646 0.7223 0.2951 0.025 Uiso 1 1 calc R . .
H162 H 0.6312 0.6620 0.3650 0.025 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4302(11) . ?
S1 O1 1.4421(10) . ?
S1 N1 1.6115(11) . ?
S1 C1 1.7748(14) . ?
Cl1 C4 1.7413(15) . ?
N1 C7 1.4881(15) . ?
N1 H1 0.8906 . ?
C1 C2 1.382(2) . ?
C1 C6 1.3878(19) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C13 1.5279(18) . ?
C7 C8 1.5339(17) . ?
C7 C12 1.5395(16) . ?
C8 C9 1.5378(17) . ?
C8 H81 0.9700 . ?
C8 H82 0.9700 . ?
C9 C16 1.530(2) . ?
C9 C10 1.5360(18) . ?
C9 H9 0.9800 . ?
C10 C11 1.5323(19) . ?
C10 H101 0.9700 . ?
C10 H102 0.9700 . ?
C11 C15 1.528(2) . ?
C11 C12 1.5302(17) . ?
C11 H11 0.9800 . ?
C12 H121 0.9700 . ?
C12 H122 0.9700 . ?
C13 C14 1.5381(18) . ?
C13 H131 0.9700 . ?
C13 H132 0.9700 . ?
C14 C16 1.531(2) . ?
C14 C15 1.5352(19) . ?
C14 H14 0.9800 . ?
C15 H151 0.9700 . ?
C15 H152 0.9700 . ?
C16 H161 0.9700 . ?
C16 H162 0.9700 . ?

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
O2 S1 O1 119.27(7) . . ?
O2 S1 N1 109.74(6) . . ?
O1 S1 N1 104.38(6) . . ?
O2 S1 C1 107.29(7) . . ?
O1 S1 C1 105.10(6) . . ?
N1 S1 C1 110.92(6) . . ?
C7 N1 S1 128.37(9) . . ?
C7 N1 H1 111.0 . . ?
S1 N1 H1 111.9 . . ?
C2 C1 C6 120.87(13) . . ?
C2 C1 S1 119.70(10) . . ?
C6 C1 S1 119.24(12) . . ?
C1 C2 C3 119.70(13) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 118.86(15) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.83(14) . . ?
C5 C4 Cl1 119.31(12) . . ?
C3 C4 Cl1 118.86(13) . . ?
C4 C5 C6 119.29(14) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.44(15) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C13 112.32(10) . . ?
N1 C7 C8 112.12(10) . . ?
C13 C7 C8 109.86(10) . . ?
N1 C7 C12 104.05(10) . . ?
C13 C7 C12 108.84(10) . . ?
C8 C7 C12 109.43(10) . . ?
C7 C8 C9 109.28(10) . . ?
C7 C8 H81 109.8 . . ?
C9 C8 H81 109.8 . . ?
C7 C8 H82 109.8 . . ?
C9 C8 H82 109.8 . . ?
H81 C8 H82 108.3 . . ?
C16 C9 C10 109.40(11) . . ?
C16 C9 C8 109.42(11) . . ?
C10 C9 C8 109.52(10) . . ?
C16 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C8 C9 H9 109.5 . . ?
C11 C10 C9 109.41(11) . . ?
C11 C10 H101 109.8 . . ?
C9 C10 H101 109.8 . . ?
C11 C10 H102 109.8 . . ?
C9 C10 H102 109.8 . . ?
H101 C10 H102 108.2 . . ?
C15 C11 C12 109.33(12) . . ?
C15 C11 C10 110.13(11) . . ?
C12 C11 C10 109.11(11) . . ?
C15 C11 H11 109.4 . . ?
C12 C11 H11 109.4 . . ?
C10 C11 H11 109.4 . . ?
C11 C12 C7 110.05(10) . . ?
C11 C12 H121 109.7 . . ?
C7 C12 H121 109.7 . . ?
C11 C12 H122 109.7 . . ?
C7 C12 H122 109.7 . . ?
H121 C12 H122 108.2 . . ?
C7 C13 C14 109.11(11) . . ?
C7 C13 H131 109.9 . . ?
C14 C13 H131 109.9 . . ?
C7 C13 H132 109.9 . . ?
C14 C13 H132 109.9 . . ?
H131 C13 H132 108.3 . . ?
C16 C14 C15 109.46(12) . . ?
C16 C14 C13 109.66(11) . . ?
C15 C14 C13 110.03(11) . . ?
C16 C14 H14 109.2 . . ?
C15 C14 H14 109.2 . . ?
C13 C14 H14 109.2 . . ?
C11 C15 C14 108.89(10) . . ?
C11 C15 H151 109.9 . . ?
C14 C15 H151 109.9 . . ?
C11 C15 H152 109.9 . . ?
C14 C15 H152 109.9 . . ?
H151 C15 H152 108.3 . . ?
C9 C16 C14 109.55(10) . . ?
C9 C16 H161 109.8 . . ?
C14 C16 H161 109.8 . . ?
C9 C16 H162 109.8 . . ?
C14 C16 H162 109.8 . . ?
H161 C16 H162 108.2 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C7 -42.08(13) . . . . ?
O1 S1 N1 C7 -171.01(11) . . . . ?
C1 S1 N1 C7 76.29(13) . . . . ?
O2 S1 C1 C2 178.67(11) . . . . ?
O1 S1 C1 C2 -53.43(13) . . . . ?
N1 S1 C1 C2 58.82(12) . . . . ?
O2 S1 C1 C6 -6.27(13) . . . . ?
O1 S1 C1 C6 121.64(12) . . . . ?
N1 S1 C1 C6 -126.11(11) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
S1 C1 C2 C3 174.64(12) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 Cl1 -179.47(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
Cl1 C4 C5 C6 179.69(12) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
S1 C1 C6 C5 -174.44(12) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
S1 N1 C7 C13 50.19(15) . . . . ?
S1 N1 C7 C8 -74.10(14) . . . . ?
S1 N1 C7 C12 167.74(10) . . . . ?
N1 C7 C8 C9 -174.23(10) . . . . ?
C13 C7 C8 C9 60.13(13) . . . . ?
C12 C7 C8 C9 -59.31(13) . . . . ?
C7 C8 C9 C16 -59.80(13) . . . . ?
C7 C8 C9 C10 60.11(14) . . . . ?
C16 C9 C10 C11 59.24(13) . . . . ?
C8 C9 C10 C11 -60.68(14) . . . . ?
C9 C10 C11 C15 -59.69(13) . . . . ?
C9 C10 C11 C12 60.32(14) . . . . ?
C15 C11 C12 C7 60.53(14) . . . . ?
C10 C11 C12 C7 -59.96(14) . . . . ?
N1 C7 C12 C11 179.67(11) . . . . ?
C13 C7 C12 C11 -60.39(14) . . . . ?
C8 C7 C12 C11 59.67(14) . . . . ?
N1 C7 C13 C14 174.47(10) . . . . ?
C8 C7 C13 C14 -60.00(13) . . . . ?
C12 C7 C13 C14 59.80(13) . . . . ?
C7 C13 C14 C16 59.89(14) . . . . ?
C7 C13 C14 C15 -60.57(14) . . . . ?
C12 C11 C15 C14 -59.85(14) . . . . ?
C10 C11 C15 C14 60.02(14) . . . . ?
C16 C14 C15 C11 -60.30(14) . . . . ?
C13 C14 C15 C11 60.28(15) . . . . ?
C10 C9 C16 C14 -60.00(14) . . . . ?
C8 C9 C16 C14 59.98(13) . . . . ?
C15 C14 C16 C9 60.69(13) . . . . ?
C13 C14 C16 C9 -60.10(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropyl'
_database_code_depnum_ccdc_archive 'CCDC 1028780'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_48

_audit_creation_method           SHELXTL
_chemical_name_systematic        
'N-(3,5-Dimethyl-adamantan-1-yl)-4-methyl-benzenesulfonamide '
_chemical_name_common            ?
_chemical_melting_point          435.6
_chemical_formula_moiety         'C19 H27 N O2 S'
_chemical_formula_sum            'C19 H27 N O2 S'
_chemical_formula_weight         333.48

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8028(3)
_cell_length_b                   11.6083(3)
_cell_length_c                   14.0725(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.824(3)
_cell_angle_gamma                90.00
_cell_volume                     1755.61(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(18)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .25
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SCALE3

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      100.01(18)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2060
_diffrn_standards_number         10170
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            9233
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         29.07
_reflns_number_total             4679
_reflns_number_gt                4098
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'bruker XSCANS'
_computing_cell_refinement       'bruker XSCANS'
_computing_data_reduction        'BRUKER SHELXTL'
_computing_structure_solution    'BRUKER SHELXTL'
_computing_structure_refinement  'BRUKER SHELXTL'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.6840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4679
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S S 0.04004(3) 0.18446(2) 0.047223(19) 0.01151(8) Uani 1 1 d . . .
N1 N 0.14046(9) 0.12157(9) -0.01155(7) 0.01300(19) Uani 1 1 d . . .
H1 H 0.1136(14) 0.0603(14) -0.0371(10) 0.016 Uiso 1 1 d . . .
O2 O 0.10235(8) 0.26600(7) 0.11258(6) 0.01448(18) Uani 1 1 d . . .
O1 O -0.03132(8) 0.09284(7) 0.08512(6) 0.01527(18) Uani 1 1 d . . .
C1 C -0.06288(11) 0.26447(10) -0.03323(8) 0.0129(2) Uani 1 1 d . . .
C2 C -0.11383(12) 0.21444(11) -0.11838(9) 0.0169(2) Uani 1 1 d . . .
H2 H -0.0958 0.1384 -0.1325 0.020 Uiso 1 1 calc R . .
C3 C -0.19189(12) 0.27957(11) -0.18191(9) 0.0181(2) Uani 1 1 d . . .
H3 H -0.2265 0.2464 -0.2387 0.022 Uiso 1 1 calc R . .
C4 C -0.21928(11) 0.39420(10) -0.16186(8) 0.0159(2) Uani 1 1 d . . .
C5 C -0.16882(12) 0.44124(10) -0.07535(9) 0.0178(2) Uani 1 1 d . . .
H5 H -0.1878 0.5169 -0.0605 0.021 Uiso 1 1 calc R . .
C6 C -0.09083(11) 0.37733(10) -0.01092(8) 0.0159(2) Uani 1 1 d . . .
H6 H -0.0577 0.4098 0.0465 0.019 Uiso 1 1 calc R . .
C7 C 0.24759(11) 0.17647(10) -0.05251(8) 0.0124(2) Uani 1 1 d . . .
C8 C 0.21199(11) 0.28654(10) -0.10985(9) 0.0156(2) Uani 1 1 d . . .
H8A H 0.1471 0.2694 -0.1607 0.019 Uiso 1 1 calc R . .
H8B H 0.1805 0.3440 -0.0684 0.019 Uiso 1 1 calc R . .
C9 C 0.32727(12) 0.33330(11) -0.15237(9) 0.0184(2) Uani 1 1 d . . .
H9 H 0.3050 0.4037 -0.1885 0.022 Uiso 1 1 calc R . .
C10 C 0.42931(12) 0.36072(11) -0.07184(10) 0.0208(3) Uani 1 1 d . . .
H10A H 0.3993 0.4181 -0.0296 0.025 Uiso 1 1 calc R . .
H10B H 0.5013 0.3921 -0.0987 0.025 Uiso 1 1 calc R . .
C11 C 0.46686(11) 0.25110(11) -0.01472(9) 0.0182(2) Uani 1 1 d . . .
C12 C 0.35090(11) 0.20395(11) 0.02735(8) 0.0157(2) Uani 1 1 d . . .
H12A H 0.3727 0.1346 0.0638 0.019 Uiso 1 1 calc R . .
H12B H 0.3210 0.2605 0.0703 0.019 Uiso 1 1 calc R . .
C13 C 0.29509(11) 0.08643(10) -0.11979(8) 0.0145(2) Uani 1 1 d . . .
H13A H 0.2299 0.0685 -0.1702 0.017 Uiso 1 1 calc R . .
H13B H 0.3163 0.0162 -0.0845 0.017 Uiso 1 1 calc R . .
C14 C 0.41019(11) 0.13140(11) -0.16410(9) 0.0167(2) Uani 1 1 d . . .
C15 C 0.51168(11) 0.16051(11) -0.08317(9) 0.0186(2) Uani 1 1 d . . .
H15A H 0.5846 0.1894 -0.1104 0.022 Uiso 1 1 calc R . .
H15B H 0.5355 0.0910 -0.0477 0.022 Uiso 1 1 calc R . .
C16 C 0.37450(12) 0.24293(11) -0.21933(9) 0.0193(3) Uani 1 1 d . . .
H16A H 0.4465 0.2728 -0.2473 0.023 Uiso 1 1 calc R . .
H16B H 0.3102 0.2265 -0.2707 0.023 Uiso 1 1 calc R . .
C17 C 0.56906(13) 0.27822(14) 0.06563(10) 0.0280(3) Uani 1 1 d . . .
H23 H 0.5399 0.3360 0.1068 0.042 Uiso 1 1 calc R . .
H24 H 0.6415 0.3061 0.0387 0.042 Uiso 1 1 calc R . .
H25 H 0.5899 0.2096 0.1018 0.042 Uiso 1 1 calc R . .
C18 C 0.45692(13) 0.04122(12) -0.23100(10) 0.0233(3) Uani 1 1 d . . .
H15 H 0.5291 0.0702 -0.2577 0.035 Uiso 1 1 calc R . .
H16 H 0.3928 0.0248 -0.2815 0.035 Uiso 1 1 calc R . .
H22 H 0.4783 -0.0280 -0.1958 0.035 Uiso 1 1 calc R . .
C19 C -0.30014(13) 0.46624(11) -0.23230(9) 0.0213(3) Uani 1 1 d . . .
H26 H -0.3155 0.5395 -0.2042 0.032 Uiso 1 1 calc R . .
H27 H -0.3778 0.4274 -0.2489 0.032 Uiso 1 1 calc R . .
H21 H -0.2587 0.4777 -0.2888 0.032 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O2 1.4386(8) . ?
S O1 1.4467(8) . ?
S N1 1.6049(10) . ?
S C1 1.7678(12) . ?
N1 C7 1.4877(14) . ?
N1 H1 0.836(16) . ?
C1 C6 1.3875(16) . ?
C1 C2 1.3937(16) . ?
C2 C3 1.3889(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.3981(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3938(16) . ?
C4 C19 1.5065(16) . ?
C5 C6 1.3883(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C13 1.5332(16) . ?
C7 C12 1.5348(16) . ?
C7 C8 1.5390(16) . ?
C8 C9 1.5345(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C16 1.5317(18) . ?
C9 C10 1.5321(18) . ?
C9 H9 0.9800 . ?
C10 C11 1.5374(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C17 1.5307(18) . ?
C11 C15 1.5372(18) . ?
C11 C12 1.5394(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.5377(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C18 1.5276(17) . ?
C14 C15 1.5361(17) . ?
C14 C16 1.5389(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H23 0.9600 . ?
C17 H24 0.9600 . ?
C17 H25 0.9600 . ?
C18 H15 0.9600 . ?
C18 H16 0.9600 . ?
C18 H22 0.9600 . ?
C19 H26 0.9600 . ?
C19 H27 0.9600 . ?
C19 H21 0.9600 . ?

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
O2 S O1 118.71(5) . . ?
O2 S N1 109.38(5) . . ?
O1 S N1 105.60(5) . . ?
O2 S C1 106.66(5) . . ?
O1 S C1 107.36(5) . . ?
N1 S C1 108.84(5) . . ?
C7 N1 S 126.72(8) . . ?
C7 N1 H1 116.6(10) . . ?
S N1 H1 112.7(11) . . ?
C6 C1 C2 120.79(11) . . ?
C6 C1 S 119.23(9) . . ?
C2 C1 S 119.97(9) . . ?
C3 C2 C1 119.19(11) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.01(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.50(11) . . ?
C5 C4 C19 120.43(11) . . ?
C3 C4 C19 121.06(11) . . ?
C6 C5 C4 121.24(11) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.24(11) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C13 105.63(9) . . ?
N1 C7 C12 109.98(9) . . ?
C13 C7 C12 109.26(10) . . ?
N1 C7 C8 113.33(9) . . ?
C13 C7 C8 108.89(9) . . ?
C12 C7 C8 109.62(9) . . ?
C9 C8 C7 109.19(10) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C16 C9 C10 109.74(10) . . ?
C16 C9 C8 109.38(10) . . ?
C10 C9 C8 109.67(10) . . ?
C16 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
C9 C10 C11 110.28(10) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C17 C11 C15 110.74(11) . . ?
C17 C11 C10 110.38(11) . . ?
C15 C11 C10 108.77(10) . . ?
C17 C11 C12 110.07(10) . . ?
C15 C11 C12 108.55(10) . . ?
C10 C11 C12 108.27(10) . . ?
C7 C12 C11 110.60(9) . . ?
C7 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C7 C13 C14 110.73(9) . . ?
C7 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C18 C14 C15 110.61(10) . . ?
C18 C14 C13 110.40(10) . . ?
C15 C14 C13 108.65(9) . . ?
C18 C14 C16 110.29(10) . . ?
C15 C14 C16 108.23(10) . . ?
C13 C14 C16 108.60(10) . . ?
C14 C15 C11 111.63(10) . . ?
C14 C15 H15A 109.3 . . ?
C11 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C11 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C9 C16 C14 110.33(10) . . ?
C9 C16 H16A 109.6 . . ?
C14 C16 H16A 109.6 . . ?
C9 C16 H16B 109.6 . . ?
C14 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C11 C17 H23 109.5 . . ?
C11 C17 H24 109.5 . . ?
H23 C17 H24 109.5 . . ?
C11 C17 H25 109.5 . . ?
H23 C17 H25 109.5 . . ?
H24 C17 H25 109.5 . . ?
C14 C18 H15 109.5 . . ?
C14 C18 H16 109.5 . . ?
H15 C18 H16 109.5 . . ?
C14 C18 H22 109.5 . . ?
H15 C18 H22 109.5 . . ?
H16 C18 H22 109.5 . . ?
C4 C19 H26 109.5 . . ?
C4 C19 H27 109.5 . . ?
H26 C19 H27 109.5 . . ?
C4 C19 H21 109.5 . . ?
H26 C19 H21 109.5 . . ?
H27 C19 H21 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S N1 C7 -41.70(11) . . . . ?
O1 S N1 C7 -170.52(9) . . . . ?
C1 S N1 C7 74.48(10) . . . . ?
O2 S C1 C6 -14.99(11) . . . . ?
O1 S C1 C6 113.24(10) . . . . ?
N1 S C1 C6 -132.91(10) . . . . ?
O2 S C1 C2 164.32(10) . . . . ?
O1 S C1 C2 -67.45(11) . . . . ?
N1 S C1 C2 46.40(11) . . . . ?
C6 C1 C2 C3 1.00(19) . . . . ?
S C1 C2 C3 -178.30(10) . . . . ?
C1 C2 C3 C4 0.36(19) . . . . ?
C2 C3 C4 C5 -1.53(19) . . . . ?
C2 C3 C4 C19 177.73(12) . . . . ?
C3 C4 C5 C6 1.39(19) . . . . ?
C19 C4 C5 C6 -177.88(12) . . . . ?
C2 C1 C6 C5 -1.14(18) . . . . ?
S C1 C6 C5 178.17(9) . . . . ?
C4 C5 C6 C1 -0.08(19) . . . . ?
S N1 C7 C13 -167.37(8) . . . . ?
S N1 C7 C12 74.85(12) . . . . ?
S N1 C7 C8 -48.24(13) . . . . ?
N1 C7 C8 C9 -177.62(9) . . . . ?
C13 C7 C8 C9 -60.38(12) . . . . ?
C12 C7 C8 C9 59.10(12) . . . . ?
C7 C8 C9 C16 60.69(12) . . . . ?
C7 C8 C9 C10 -59.70(13) . . . . ?
C16 C9 C10 C11 -59.44(13) . . . . ?
C8 C9 C10 C11 60.73(13) . . . . ?
C9 C10 C11 C17 179.85(11) . . . . ?
C9 C10 C11 C15 58.17(13) . . . . ?
C9 C10 C11 C12 -59.61(13) . . . . ?
N1 C7 C12 C11 175.09(9) . . . . ?
C13 C7 C12 C11 59.57(12) . . . . ?
C8 C7 C12 C11 -59.67(13) . . . . ?
C17 C11 C12 C7 179.95(11) . . . . ?
C15 C11 C12 C7 -58.69(13) . . . . ?
C10 C11 C12 C7 59.22(13) . . . . ?
N1 C7 C13 C14 -177.77(9) . . . . ?
C12 C7 C13 C14 -59.50(12) . . . . ?
C8 C7 C13 C14 60.20(12) . . . . ?
C7 C13 C14 C18 179.99(10) . . . . ?
C7 C13 C14 C15 58.54(12) . . . . ?
C7 C13 C14 C16 -58.97(12) . . . . ?
C18 C14 C15 C11 -179.94(10) . . . . ?
C13 C14 C15 C11 -58.61(13) . . . . ?
C16 C14 C15 C11 59.13(12) . . . . ?
C17 C11 C15 C14 179.64(11) . . . . ?
C10 C11 C15 C14 -58.89(13) . . . . ?
C12 C11 C15 C14 58.70(13) . . . . ?
C10 C9 C16 C14 60.04(13) . . . . ?
C8 C9 C16 C14 -60.31(13) . . . . ?
C18 C14 C16 C9 179.84(10) . . . . ?
C15 C14 C16 C9 -59.04(13) . . . . ?
C13 C14 C16 C9 58.73(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.07
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropyl '
_database_code_depnum_ccdc_archive 'CCDC 1028781'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_49

_audit_creation_method           SHELXTL
_chemical_name_systematic        
'N-(3,5-Dimethyl-adamantan-1-yl)-4-fluoro-benzenesulfonamide '
_chemical_name_common            ?
_chemical_melting_point          410.5
_chemical_formula_moiety         'C18 H24 F N O2 S'
_chemical_formula_sum            'C18 H24 F N O2 S'
_chemical_formula_weight         337.44

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5261(3)
_cell_length_b                   11.5499(3)
_cell_length_c                   14.1017(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.386(2)
_cell_angle_gamma                90.00
_cell_volume                     1700.19(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    3703
_cell_measurement_theta_min      2.9073
_cell_measurement_theta_max      31.5276

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .35
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SCALE3

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2060
_diffrn_standards_number         9777
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8870
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         29.06
_reflns_number_total             4527
_reflns_number_gt                3840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'bruker XSCANS'
_computing_cell_refinement       'bruker XSCANS'
_computing_data_reduction        'BRUKER SHELXTL'
_computing_structure_solution    'BRUKER SHELXTL'
_computing_structure_refinement  'BRUKER SHELXTL'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.4148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4527
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S S 0.01809(3) 0.30275(2) 0.026898(19) 0.01870(8) Uani 1 1 d . . .
F F -0.32469(10) 0.04746(9) -0.25825(7) 0.0551(3) Uani 1 1 d . . .
O1 O -0.05679(9) 0.39264(8) 0.06397(6) 0.0259(2) Uani 1 1 d . . .
O2 O 0.07853(8) 0.21710(8) 0.09147(6) 0.02346(19) Uani 1 1 d . . .
N1 N 0.12227(9) 0.36696(9) -0.02761(7) 0.0214(2) Uani 1 1 d . . .
H1 H 0.1064 0.4369 -0.0431 0.026 Uiso 1 1 d . . .
C1 C -0.08576(11) 0.22577(11) -0.05965(8) 0.0200(2) Uani 1 1 d . . .
C2 C -0.13676(12) 0.28085(12) -0.14395(9) 0.0267(3) Uani 1 1 d . . .
H2 H -0.1160 0.3575 -0.1549 0.032 Uiso 1 1 calc R . .
C3 C -0.21839(13) 0.22085(14) -0.21124(9) 0.0324(3) Uani 1 1 d . . .
H3 H -0.2538 0.2562 -0.2678 0.039 Uiso 1 1 calc R . .
C4 C -0.24584(13) 0.10701(14) -0.19219(10) 0.0335(3) Uani 1 1 d . . .
C5 C -0.19780(13) 0.05098(12) -0.10924(10) 0.0329(3) Uani 1 1 d . . .
H5 H -0.2192 -0.0257 -0.0987 0.040 Uiso 1 1 calc R . .
C6 C -0.11655(12) 0.11188(11) -0.04175(9) 0.0252(3) Uani 1 1 d . . .
H6 H -0.0829 0.0765 0.0152 0.030 Uiso 1 1 calc R . .
C7 C 0.23755(11) 0.31478(10) -0.06132(8) 0.0175(2) Uani 1 1 d . . .
C8 C 0.20690(11) 0.20252(10) -0.11778(9) 0.0212(2) Uani 1 1 d . . .
H81 H 0.1416 0.2171 -0.1715 0.025 Uiso 1 1 calc R . .
H82 H 0.1744 0.1449 -0.0771 0.025 Uiso 1 1 calc R . .
C9 C 0.32951(12) 0.15754(11) -0.15400(9) 0.0240(3) Uani 1 1 d . . .
H9 H 0.3104 0.0855 -0.1897 0.029 Uiso 1 1 calc R . .
C10 C 0.43147(12) 0.13420(11) -0.06870(9) 0.0262(3) Uani 1 1 d . . .
H101 H 0.5081 0.1040 -0.0913 0.031 Uiso 1 1 calc R . .
H102 H 0.4002 0.0765 -0.0274 0.031 Uiso 1 1 calc R . .
C11 C 0.46405(11) 0.24575(12) -0.01187(8) 0.0249(3) Uani 1 1 d . . .
C12 C 0.34105(11) 0.29140(11) 0.02334(8) 0.0223(2) Uani 1 1 d . . .
H121 H 0.3098 0.2349 0.0657 0.027 Uiso 1 1 calc R . .
H123 H 0.3599 0.3624 0.0592 0.027 Uiso 1 1 calc R . .
C13 C 0.28751(12) 0.40472(11) -0.12743(9) 0.0228(2) Uani 1 1 d . . .
H131 H 0.3053 0.4767 -0.0928 0.027 Uiso 1 1 calc R . .
H132 H 0.2223 0.4199 -0.1811 0.027 Uiso 1 1 calc R . .
C14 C 0.41024(12) 0.36154(11) -0.16467(9) 0.0239(2) Uani 1 1 d . . .
C15 C 0.51118(12) 0.33656(12) -0.07880(9) 0.0264(3) Uani 1 1 d . . .
H151 H 0.5315 0.4077 -0.0435 0.032 Uiso 1 1 calc R . .
H152 H 0.5889 0.3089 -0.1014 0.032 Uiso 1 1 calc R . .
C16 C 0.37936(12) 0.24779(12) -0.21945(8) 0.0255(3) Uani 1 1 d . . .
H162 H 0.3152 0.2619 -0.2740 0.031 Uiso 1 1 calc R . .
H161 H 0.4559 0.2188 -0.2430 0.031 Uiso 1 1 calc R . .
C17 C 0.56614(14) 0.22226(17) 0.07335(11) 0.0427(4) Uani 1 1 d . . .
H171 H 0.5349 0.1654 0.1143 0.064 Uiso 1 1 calc R . .
H172 H 0.5851 0.2927 0.1085 0.064 Uiso 1 1 calc R . .
H173 H 0.6426 0.1939 0.0507 0.064 Uiso 1 1 calc R . .
C18 C 0.45973(15) 0.45187(13) -0.23009(11) 0.0379(3) Uani 1 1 d . . .
H181 H 0.3955 0.4665 -0.2835 0.057 Uiso 1 1 calc R . .
H182 H 0.5360 0.4235 -0.2528 0.057 Uiso 1 1 calc R . .
H183 H 0.4788 0.5224 -0.1951 0.057 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O2 1.4365(9) . ?
S O1 1.4416(9) . ?
S N1 1.6000(10) . ?
S C1 1.7698(12) . ?
F C4 1.3531(16) . ?
N1 C7 1.4866(14) . ?
N1 H1 0.8478 . ?
C1 C6 1.3856(17) . ?
C1 C2 1.3935(16) . ?
C2 C3 1.3819(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C5 C6 1.3867(19) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.5332(16) . ?
C7 C13 1.5332(16) . ?
C7 C8 1.5340(16) . ?
C8 C9 1.5382(16) . ?
C8 H81 0.9700 . ?
C8 H82 0.9700 . ?
C9 C16 1.5291(18) . ?
C9 C10 1.5295(18) . ?
C9 H9 0.9800 . ?
C10 C11 1.5327(18) . ?
C10 H101 0.9700 . ?
C10 H102 0.9700 . ?
C11 C17 1.5299(18) . ?
C11 C15 1.5353(19) . ?
C11 C12 1.5382(16) . ?
C12 H121 0.9700 . ?
C12 H123 0.9700 . ?
C13 C14 1.5388(16) . ?
C13 H131 0.9700 . ?
C13 H132 0.9700 . ?
C14 C18 1.5279(17) . ?
C14 C15 1.5322(18) . ?
C14 C16 1.5376(18) . ?
C15 H151 0.9700 . ?
C15 H152 0.9700 . ?
C16 H162 0.9700 . ?
C16 H161 0.9700 . ?
C17 H171 0.9600 . ?
C17 H172 0.9600 . ?
C17 H173 0.9600 . ?
C18 H181 0.9600 . ?
C18 H182 0.9600 . ?
C18 H183 0.9600 . ?

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
O2 S O1 118.97(5) . . ?
O2 S N1 110.41(5) . . ?
O1 S N1 106.31(5) . . ?
O2 S C1 105.97(6) . . ?
O1 S C1 107.09(5) . . ?
N1 S C1 107.59(5) . . ?
C7 N1 S 127.14(8) . . ?
C7 N1 H1 116.5 . . ?
S N1 H1 116.2 . . ?
C6 C1 C2 121.02(12) . . ?
C6 C1 S 119.31(9) . . ?
C2 C1 S 119.67(10) . . ?
C3 C2 C1 119.62(13) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 118.13(12) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
F C4 C5 118.19(14) . . ?
F C4 C3 118.39(13) . . ?
C5 C4 C3 123.42(13) . . ?
C4 C5 C6 118.17(13) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 119.64(12) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N1 C7 C12 110.49(9) . . ?
N1 C7 C13 106.12(9) . . ?
C12 C7 C13 109.14(10) . . ?
N1 C7 C8 112.50(9) . . ?
C12 C7 C8 109.65(10) . . ?
C13 C7 C8 108.82(9) . . ?
C7 C8 C9 109.17(9) . . ?
C7 C8 H81 109.8 . . ?
C9 C8 H81 109.8 . . ?
C7 C8 H82 109.8 . . ?
C9 C8 H82 109.8 . . ?
H81 C8 H82 108.3 . . ?
C16 C9 C10 109.53(10) . . ?
C16 C9 C8 109.74(10) . . ?
C10 C9 C8 109.41(10) . . ?
C16 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C9 C10 C11 110.50(10) . . ?
C9 C10 H101 109.5 . . ?
C11 C10 H101 109.5 . . ?
C9 C10 H102 109.5 . . ?
C11 C10 H102 109.5 . . ?
H101 C10 H102 108.1 . . ?
C17 C11 C10 110.43(12) . . ?
C17 C11 C15 110.74(11) . . ?
C10 C11 C15 108.73(10) . . ?
C17 C11 C12 110.03(10) . . ?
C10 C11 C12 108.41(10) . . ?
C15 C11 C12 108.43(10) . . ?
C7 C12 C11 110.63(9) . . ?
C7 C12 H121 109.5 . . ?
C11 C12 H121 109.5 . . ?
C7 C12 H123 109.5 . . ?
C11 C12 H123 109.5 . . ?
H121 C12 H123 108.1 . . ?
C7 C13 C14 110.89(10) . . ?
C7 C13 H131 109.5 . . ?
C14 C13 H131 109.5 . . ?
C7 C13 H132 109.5 . . ?
C14 C13 H132 109.5 . . ?
H131 C13 H132 108.0 . . ?
C18 C14 C15 110.50(11) . . ?
C18 C14 C16 110.28(10) . . ?
C15 C14 C16 108.45(10) . . ?
C18 C14 C13 110.56(11) . . ?
C15 C14 C13 108.58(10) . . ?
C16 C14 C13 108.41(10) . . ?
C14 C15 C11 111.62(10) . . ?
C14 C15 H151 109.3 . . ?
C11 C15 H151 109.3 . . ?
C14 C15 H152 109.3 . . ?
C11 C15 H152 109.3 . . ?
H151 C15 H152 108.0 . . ?
C9 C16 C14 110.24(9) . . ?
C9 C16 H162 109.6 . . ?
C14 C16 H162 109.6 . . ?
C9 C16 H161 109.6 . . ?
C14 C16 H161 109.6 . . ?
H162 C16 H161 108.1 . . ?
C11 C17 H171 109.5 . . ?
C11 C17 H172 109.5 . . ?
H171 C17 H172 109.5 . . ?
C11 C17 H173 109.5 . . ?
H171 C17 H173 109.5 . . ?
H172 C17 H173 109.5 . . ?
C14 C18 H181 109.5 . . ?
C14 C18 H182 109.5 . . ?
H181 C18 H182 109.5 . . ?
C14 C18 H183 109.5 . . ?
H181 C18 H183 109.5 . . ?
H182 C18 H183 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S N1 C7 36.55(11) . . . . ?
O1 S N1 C7 166.89(10) . . . . ?
C1 S N1 C7 -78.66(11) . . . . ?
O2 S C1 C6 15.21(11) . . . . ?
O1 S C1 C6 -112.73(10) . . . . ?
N1 S C1 C6 133.33(9) . . . . ?
O2 S C1 C2 -165.73(9) . . . . ?
O1 S C1 C2 66.32(10) . . . . ?
N1 S C1 C2 -47.62(11) . . . . ?
C6 C1 C2 C3 -0.60(18) . . . . ?
S C1 C2 C3 -179.64(10) . . . . ?
C1 C2 C3 C4 -0.39(19) . . . . ?
C2 C3 C4 F -179.34(12) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
F C4 C5 C6 179.71(12) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C2 C1 C6 C5 0.99(18) . . . . ?
S C1 C6 C5 -179.97(9) . . . . ?
C4 C5 C6 C1 -0.36(19) . . . . ?
S N1 C7 C12 -74.09(13) . . . . ?
S N1 C7 C13 167.73(9) . . . . ?
S N1 C7 C8 48.82(13) . . . . ?
N1 C7 C8 C9 177.31(9) . . . . ?
C12 C7 C8 C9 -59.31(12) . . . . ?
C13 C7 C8 C9 60.00(12) . . . . ?
C7 C8 C9 C16 -60.38(12) . . . . ?
C7 C8 C9 C10 59.82(13) . . . . ?
C16 C9 C10 C11 59.68(12) . . . . ?
C8 C9 C10 C11 -60.65(13) . . . . ?
C9 C10 C11 C17 -179.94(10) . . . . ?
C9 C10 C11 C15 -58.25(12) . . . . ?
C9 C10 C11 C12 59.44(13) . . . . ?
N1 C7 C12 C11 -175.86(10) . . . . ?
C13 C7 C12 C11 -59.53(13) . . . . ?
C8 C7 C12 C11 59.58(13) . . . . ?
C17 C11 C12 C7 -179.72(12) . . . . ?
C10 C11 C12 C7 -58.86(13) . . . . ?
C15 C11 C12 C7 59.03(13) . . . . ?
N1 C7 C13 C14 178.27(10) . . . . ?
C12 C7 C13 C14 59.20(12) . . . . ?
C8 C7 C13 C14 -60.44(12) . . . . ?
C7 C13 C14 C18 -179.73(11) . . . . ?
C7 C13 C14 C15 -58.36(13) . . . . ?
C7 C13 C14 C16 59.27(13) . . . . ?
C18 C14 C15 C11 -179.87(10) . . . . ?
C16 C14 C15 C11 -58.89(12) . . . . ?
C13 C14 C15 C11 58.71(13) . . . . ?
C17 C11 C15 C14 -179.93(11) . . . . ?
C10 C11 C15 C14 58.57(13) . . . . ?
C12 C11 C15 C14 -59.11(13) . . . . ?
C10 C9 C16 C14 -60.02(13) . . . . ?
C8 C9 C16 C14 60.11(13) . . . . ?
C18 C14 C16 C9 -179.85(11) . . . . ?
C15 C14 C16 C9 59.02(12) . . . . ?
C13 C14 C16 C9 -58.69(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.06
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropyl '
_database_code_depnum_ccdc_archive 'CCDC 1028782'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_51

_audit_creation_method           SHELXTL
_chemical_name_systematic        
'N-(3,5-Dimethyl-adamantan-1-yl)-benzenesulfonamide '
_chemical_name_common            ?
_chemical_melting_point          416.4
_chemical_formula_moiety         'C18 H25 N O2 S'
_chemical_formula_sum            'C18 H25 N O2 S'
_chemical_formula_weight         319.45

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.33501(18)
_cell_length_b                   11.5770(2)
_cell_length_c                   15.7703(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5871(18)
_cell_angle_gamma                90.00
_cell_volume                     1675.31(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    3556
_cell_measurement_theta_min      2.9400
_cell_measurement_theta_max      31.3228

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .37
_exptl_crystal_size_min          .30
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SCALE3

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2060
_diffrn_standards_number         9486
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8683
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         29.06
_reflns_number_total             4475
_reflns_number_gt                3753
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'bruker XSCANS'
_computing_cell_refinement       'bruker XSCANS'
_computing_data_reduction        'BRUKER SHELXTL'
_computing_structure_solution    'BRUKER SHELXTL'
_computing_structure_refinement  'BRUKER SHELXTL'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.4537P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4475
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S S 0.98645(3) 0.82159(3) 0.059799(19) 0.01722(9) Uani 1 1 d . . .
O1 O 1.10159(10) 0.87854(8) 0.02609(6) 0.0248(2) Uani 1 1 d . . .
O2 O 1.02416(10) 0.74151(8) 0.12985(6) 0.0226(2) Uani 1 1 d . . .
N1 N 0.88845(12) 0.92401(9) 0.08770(7) 0.0199(2) Uani 1 1 d . . .
H1 H 0.8844 0.9897 0.0532 0.050 Uiso 1 1 d . . .
C1 C 0.88198(13) 0.74488(12) -0.02729(8) 0.0210(3) Uani 1 1 d . . .
C2 C 0.81599(16) 0.80541(15) -0.10056(9) 0.0302(3) Uani 1 1 d . . .
H2 H 0.8250 0.8852 -0.1034 0.036 Uiso 1 1 calc R . .
C3 C 0.73640(17) 0.74409(19) -0.16927(10) 0.0431(5) Uani 1 1 d . . .
H3 H 0.6907 0.7832 -0.2183 0.052 Uiso 1 1 calc R . .
C4 C 0.72487(17) 0.6253(2) -0.16507(12) 0.0485(5) Uani 1 1 d . . .
H4 H 0.6723 0.5850 -0.2116 0.058 Uiso 1 1 calc R . .
C5 C 0.79096(13) 0.56615(10) -0.09228(8) 0.0454(4) Uani 1 1 d . . .
H5 H 0.7826 0.4862 -0.0900 0.054 Uiso 1 1 calc R . .
C6 C 0.86998(13) 0.62553(10) -0.02234(8) 0.0310(3) Uani 1 1 d R . .
H6A H 0.9141 0.5860 0.0269 0.037 Uiso 1 1 calc R . .
C7 C 0.76767(13) 0.91330(10) 0.13705(8) 0.0169(2) Uani 1 1 d . . .
C8 C 0.65913(14) 0.81701(11) 0.10402(8) 0.0188(2) Uani 1 1 d . . .
H8A H 0.7088 0.7431 0.1099 0.023 Uiso 1 1 calc R . .
H8B H 0.6198 0.8293 0.0434 0.023 Uiso 1 1 calc R . .
C9 C 0.53378(14) 0.81541(11) 0.15552(8) 0.0211(3) Uani 1 1 d . . .
C10 C 0.59919(14) 0.79806(11) 0.25115(8) 0.0206(3) Uani 1 1 d . . .
H10A H 0.6491 0.7243 0.2585 0.025 Uiso 1 1 calc R . .
H10B H 0.5212 0.7961 0.2842 0.025 Uiso 1 1 calc R . .
C11 C 0.70675(14) 0.89435(11) 0.28626(8) 0.0202(3) Uani 1 1 d . . .
C12 C 0.82944(14) 0.89523(11) 0.23316(8) 0.0189(2) Uani 1 1 d . . .
H12A H 0.8977 0.9567 0.2536 0.023 Uiso 1 1 calc R . .
H12B H 0.8818 0.8225 0.2410 0.023 Uiso 1 1 calc R . .
C13 C 0.68701(15) 1.02938(11) 0.12539(9) 0.0230(3) Uani 1 1 d . . .
H13A H 0.7546 1.0917 0.1447 0.028 Uiso 1 1 calc R . .
H13B H 0.6468 1.0415 0.0648 0.028 Uiso 1 1 calc R . .
C14 C 0.56382(16) 1.02989(12) 0.17778(9) 0.0257(3) Uani 1 1 d . . .
H14 H 0.5151 1.1039 0.1717 0.031 Uiso 1 1 d . . .
C15 C 0.62598(16) 1.01050(12) 0.27345(9) 0.0249(3) Uani 1 1 d . . .
H15A H 0.5475 1.0110 0.3061 0.030 Uiso 1 1 calc R . .
H15B H 0.6926 1.0727 0.2948 0.030 Uiso 1 1 calc R . .
C16 C 0.45588(15) 0.93309(13) 0.14536(9) 0.0273(3) Uani 1 1 d . . .
H16A H 0.4141 0.9460 0.0851 0.033 Uiso 1 1 calc R . .
H16B H 0.3773 0.9333 0.1780 0.033 Uiso 1 1 calc R . .
C17 C 0.77046(17) 0.87424(14) 0.38159(9) 0.0308(3) Uani 1 1 d . . .
H17A H 0.8205 0.8014 0.3882 0.046 Uiso 1 1 calc R . .
H17B H 0.6932 0.8735 0.4142 0.046 Uiso 1 1 calc R . .
H17C H 0.8377 0.9351 0.4022 0.046 Uiso 1 1 calc R . .
C18 C 0.42773(17) 0.71779(14) 0.12269(10) 0.0342(4) Uani 1 1 d . . .
H18A H 0.4784 0.6453 0.1296 0.051 Uiso 1 1 calc R . .
H18B H 0.3880 0.7300 0.0628 0.051 Uiso 1 1 calc R . .
H18C H 0.3502 0.7168 0.1551 0.051 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O2 1.4356(9) . ?
S O1 1.4431(9) . ?
S N1 1.6076(11) . ?
S C1 1.7702(13) . ?
N1 C7 1.4882(15) . ?
N1 H1 0.9318 . ?
C1 C6 1.3896(18) . ?
C1 C2 1.3943(19) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3908 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.5319(17) . ?
C7 C12 1.5337(17) . ?
C7 C13 1.5349(17) . ?
C8 C9 1.5422(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C18 1.5287(19) . ?
C9 C10 1.5328(18) . ?
C9 C16 1.5388(19) . ?
C10 C11 1.5340(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C17 1.5296(18) . ?
C11 C15 1.5367(19) . ?
C11 C12 1.5379(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.5345(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.5302(19) . ?
C14 C16 1.531(2) . ?
C14 H14 0.9666 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
O2 S O1 118.98(6) . . ?
O2 S N1 109.70(6) . . ?
O1 S N1 105.28(6) . . ?
O2 S C1 107.18(6) . . ?
O1 S C1 106.55(6) . . ?
N1 S C1 108.80(6) . . ?
C7 N1 S 127.27(8) . . ?
C7 N1 H1 114.8 . . ?
S N1 H1 114.0 . . ?
C6 C1 C2 121.22(13) . . ?
C6 C1 S 119.60(10) . . ?
C2 C1 S 119.17(11) . . ?
C3 C2 C1 118.73(16) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.38(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.44(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.32(9) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.91(8) . . ?
C1 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
N1 C7 C8 113.59(10) . . ?
N1 C7 C12 110.17(10) . . ?
C8 C7 C12 110.00(10) . . ?
N1 C7 C13 105.45(10) . . ?
C8 C7 C13 108.49(10) . . ?
C12 C7 C13 108.96(10) . . ?
C7 C8 C9 110.37(10) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C18 C9 C10 110.64(11) . . ?
C18 C9 C16 110.79(12) . . ?
C10 C9 C16 108.28(11) . . ?
C18 C9 C8 109.72(11) . . ?
C10 C9 C8 108.43(10) . . ?
C16 C9 C8 108.92(11) . . ?
C9 C10 C11 112.08(10) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C17 C11 C10 110.77(11) . . ?
C17 C11 C15 110.80(11) . . ?
C10 C11 C15 108.40(11) . . ?
C17 C11 C12 110.01(11) . . ?
C10 C11 C12 108.17(10) . . ?
C15 C11 C12 108.61(10) . . ?
C7 C12 C11 110.89(10) . . ?
C7 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C7 109.78(10) . . ?
C14 C13 H13A 109.7 . . ?
C7 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C7 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C16 109.21(11) . . ?
C15 C14 C13 110.15(12) . . ?
C16 C14 C13 109.25(11) . . ?
C15 C14 H14 108.3 . . ?
C16 C14 H14 110.3 . . ?
C13 C14 H14 109.6 . . ?
C14 C15 C11 110.24(10) . . ?
C14 C15 H15A 109.6 . . ?
C11 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C11 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C14 C16 C9 110.12(11) . . ?
C14 C16 H16A 109.6 . . ?
C9 C16 H16A 109.6 . . ?
C14 C16 H16B 109.6 . . ?
C9 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S N1 C7 -41.84(12) . . . . ?
O1 S N1 C7 -170.99(10) . . . . ?
C1 S N1 C7 75.12(12) . . . . ?
O2 S C1 C6 -9.12(11) . . . . ?
O1 S C1 C6 119.27(10) . . . . ?
N1 S C1 C6 -127.67(10) . . . . ?
O2 S C1 C2 172.38(10) . . . . ?
O1 S C1 C2 -59.24(11) . . . . ?
N1 S C1 C2 53.82(12) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
S C1 C2 C3 178.81(10) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -0.02(17) . . . . ?
C2 C1 C6 C5 0.28(14) . . . . ?
S C1 C6 C5 -178.19(5) . . . . ?
C4 C5 C6 C1 -0.45(9) . . . . ?
S N1 C7 C8 -46.94(15) . . . . ?
S N1 C7 C12 76.97(13) . . . . ?
S N1 C7 C13 -165.60(10) . . . . ?
N1 C7 C8 C9 -177.27(10) . . . . ?
C12 C7 C8 C9 58.73(13) . . . . ?
C13 C7 C8 C9 -60.36(13) . . . . ?
C7 C8 C9 C18 -179.16(11) . . . . ?
C7 C8 C9 C10 -58.22(13) . . . . ?
C7 C8 C9 C16 59.41(13) . . . . ?
C18 C9 C10 C11 179.79(11) . . . . ?
C16 C9 C10 C11 -58.61(13) . . . . ?
C8 C9 C10 C11 59.43(13) . . . . ?
C9 C10 C11 C17 -179.76(11) . . . . ?
C9 C10 C11 C15 58.47(13) . . . . ?
C9 C10 C11 C12 -59.12(13) . . . . ?
N1 C7 C12 C11 175.16(10) . . . . ?
C8 C7 C12 C11 -58.88(13) . . . . ?
C13 C7 C12 C11 59.93(13) . . . . ?
C17 C11 C12 C7 179.06(11) . . . . ?
C10 C11 C12 C7 57.95(13) . . . . ?
C15 C11 C12 C7 -59.51(13) . . . . ?
N1 C7 C13 C14 -177.21(11) . . . . ?
C8 C7 C13 C14 60.77(13) . . . . ?
C12 C7 C13 C14 -58.97(14) . . . . ?
C7 C13 C14 C15 59.23(14) . . . . ?
C7 C13 C14 C16 -60.74(14) . . . . ?
C16 C14 C15 C11 60.70(14) . . . . ?
C13 C14 C15 C11 -59.29(14) . . . . ?
C17 C11 C15 C14 179.59(11) . . . . ?
C10 C11 C15 C14 -58.67(14) . . . . ?
C12 C11 C15 C14 58.64(14) . . . . ?
C15 C14 C16 C9 -60.84(14) . . . . ?
C13 C14 C16 C9 59.70(14) . . . . ?
C18 C9 C16 C14 -179.51(11) . . . . ?
C10 C9 C16 C14 58.98(13) . . . . ?
C8 C9 C16 C14 -58.74(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.06
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.055
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropyl '
_database_code_depnum_ccdc_archive 'CCDC 1028783'
