# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Srinivasulu Aitipamula'
_publ_contact_author_email       'SRINIVASULU AITIPAMULA@ICES.A-STAR.EDU.SG'

_publ_section_title              
;
Dimorphs of 1:1 cocrystal of ethenzamide and
saccharin: solid-state grinding methods result in metastable polymorph
;
loop_
_publ_author_name
'Srinivasulu Aitipamula'
'Pui Shan Chow'
'Reginald B H Tan'

# Attachment 'B821373A_Cif.cif'

data_EASACFI
_database_code_depnum_ccdc_archive 'CCDC 711674'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'Form I of 1:1 cocrystal of ethenzamide and saccharin'
;
_chemical_name_common            
"'Form I of 1:1 cocrystal of ethenzamide and saccharin'"
_chemical_melting_point          395.57
_chemical_formula_moiety         ' C9 H11 N O2, C7 H5 N O3 S'
_chemical_formula_sum            'C16 H16 N2 O5 S'
_chemical_formula_weight         348.37

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2141(14)
_cell_length_b                   7.4923(15)
_cell_length_c                   15.456(3)
_cell_angle_alpha                85.14(3)
_cell_angle_beta                 86.43(3)
_cell_angle_gamma                70.65(3)
_cell_volume                     784.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2460
_cell_measurement_theta_min      2.6468
_cell_measurement_theta_max      30.9526

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_T_max  0.9542
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(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  'Rigaku Saturn CCD area deterctor'

_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10878
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3823
_reflns_number_gt                3707
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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)+(0.0457P)²+0.4596P] 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         3823
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
S1 S 0.14065(5) 0.21941(4) 0.34324(2) 0.01944(9) Uani 1 1 d . . .
O3 O 0.20291(15) 0.67494(14) 0.39190(7) 0.0258(2) Uani 1 1 d . . .
O5 O -0.05627(15) 0.21497(14) 0.34012(7) 0.0259(2) Uani 1 1 d . . .
O4 O 0.28746(16) 0.09552(14) 0.28911(6) 0.0267(2) Uani 1 1 d . . .
N2 N 0.14295(18) 0.43899(16) 0.32513(8) 0.0225(2) Uani 1 1 d . . .
C16 C 0.21408(18) 0.20163(18) 0.45059(8) 0.0181(2) Uani 1 1 d . . .
C15 C 0.24222(18) 0.36914(18) 0.46880(8) 0.0187(2) Uani 1 1 d . . .
C12 C 0.30785(19) 0.0656(2) 0.59124(9) 0.0227(3) Uani 1 1 d . . .
H12 H 0.3299 -0.0347 0.6333 0.027 Uiso 1 1 calc R . .
C11 C 0.3402(2) 0.2311(2) 0.61041(9) 0.0238(3) Uani 1 1 d . . .
H11 H 0.3850 0.2384 0.6647 0.029 Uiso 1 1 calc R . .
C14 C 0.19659(19) 0.51446(18) 0.39406(8) 0.0204(2) Uani 1 1 d . . .
C13 C 0.24328(19) 0.04718(18) 0.51049(8) 0.0205(2) Uani 1 1 d . . .
H13 H 0.2210 -0.0627 0.4974 0.025 Uiso 1 1 calc R . .
C10 C 0.30669(19) 0.38602(19) 0.54972(9) 0.0219(3) Uani 1 1 d . . .
H10 H 0.3268 0.4969 0.5629 0.026 Uiso 1 1 calc R . .
O1 O 1.05749(17) -0.38247(14) 0.17163(6) 0.0290(2) Uani 1 1 d . . .
O2 O 0.71642(14) 0.18529(13) 0.13330(6) 0.0225(2) Uani 1 1 d . . .
N1 N 0.96896(18) -0.09755(17) 0.22766(7) 0.0223(2) Uani 1 1 d . . .
C7 C 0.96863(19) -0.20750(18) 0.16474(8) 0.0193(2) Uani 1 1 d . . .
C6 C 0.8966(2) -0.24455(18) 0.01591(8) 0.0216(3) Uani 1 1 d . . .
H6 H 0.9739 -0.3707 0.0260 0.026 Uiso 1 1 calc R . .
C1 C 0.86507(18) -0.12237(17) 0.08292(8) 0.0181(2) Uani 1 1 d . . .
C5 C 0.8169(2) -0.1843(2) -0.06499(9) 0.0228(3) Uani 1 1 d . . .
H5 H 0.8406 -0.2682 -0.1086 0.027 Uiso 1 1 calc R . .
C4 C 0.7008(2) 0.0041(2) -0.07960(8) 0.0224(3) Uani 1 1 d . . .
H4 H 0.6459 0.0466 -0.1335 0.027 Uiso 1 1 calc R . .
C3 C 0.66597(19) 0.12918(19) -0.01468(9) 0.0217(3) Uani 1 1 d . . .
H3 H 0.5880 0.2549 -0.0254 0.026 Uiso 1 1 calc R . .
C2 C 0.74715(18) 0.06793(18) 0.06685(8) 0.0184(2) Uani 1 1 d . . .
C8 C 0.5996(2) 0.38156(19) 0.11780(9) 0.0249(3) Uani 1 1 d . . .
H8A H 0.4678 0.3922 0.1025 0.030 Uiso 1 1 calc R . .
H8B H 0.6582 0.4407 0.0705 0.030 Uiso 1 1 calc R . .
C9 C 0.5932(2) 0.4766(2) 0.20073(11) 0.0324(3) Uani 1 1 d . . .
H9A H 0.5444 0.4106 0.2479 0.049 Uiso 1 1 calc R . .
H9B H 0.5080 0.6057 0.1944 0.049 Uiso 1 1 calc R . .
H9C H 0.7232 0.4738 0.2127 0.049 Uiso 1 1 calc R . .
H1B H 0.912(3) 0.022(3) 0.2202(13) 0.034(5) Uiso 1 1 d . . .
H2 H 0.118(3) 0.502(3) 0.2701(16) 0.053(6) Uiso 1 1 d . . .
H1A H 1.039(3) -0.153(3) 0.2759(14) 0.039(5) Uiso 1 1 d . . .


_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 O4 1.4328(12) . ?
S1 O5 1.4358(11) . ?
S1 N2 1.6507(12) . ?
S1 C16 1.7540(13) . ?
O3 C14 1.2158(17) . ?
N2 C14 1.3794(17) . ?
N2 H2 0.93(2) . ?
C16 C13 1.3863(18) . ?
C16 C15 1.3897(18) . ?
C15 C10 1.3909(18) . ?
C15 C14 1.4917(19) . ?
C12 C13 1.3922(19) . ?
C12 C11 1.394(2) . ?
C12 H12 0.9300 . ?
C11 C10 1.394(2) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
O1 C7 1.2525(16) . ?
O2 C2 1.3684(15) . ?
O2 C8 1.4402(16) . ?
N1 C7 1.3272(17) . ?
N1 H1B 0.85(2) . ?
N1 H1A 0.92(2) . ?
C7 C1 1.4932(18) . ?
C6 C5 1.3855(19) . ?
C6 C1 1.3985(17) . ?
C6 H6 0.9300 . ?
C1 C2 1.4074(18) . ?
C5 C4 1.389(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.3856(19) . ?
C4 H4 0.9300 . ?
C3 C2 1.3991(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.509(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O4 S1 O5 116.91(7) . . ?
O4 S1 N2 110.20(7) . . ?
O5 S1 N2 110.26(7) . . ?
O4 S1 C16 112.27(7) . . ?
O5 S1 C16 111.52(7) . . ?
N2 S1 C16 93.17(7) . . ?
C14 N2 S1 115.55(10) . . ?
C14 N2 H2 123.8(14) . . ?
S1 N2 H2 120.5(14) . . ?
C13 C16 C15 123.13(12) . . ?
C13 C16 S1 127.16(10) . . ?
C15 C16 S1 109.71(10) . . ?
C16 C15 C10 120.02(12) . . ?
C16 C15 C14 112.50(11) . . ?
C10 C15 C14 127.48(12) . . ?
C13 C12 C11 121.47(13) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C11 C10 121.25(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
O3 C14 N2 123.84(13) . . ?
O3 C14 C15 127.12(12) . . ?
N2 C14 C15 109.04(11) . . ?
C16 C13 C12 116.35(12) . . ?
C16 C13 H13 121.8 . . ?
C12 C13 H13 121.8 . . ?
C15 C10 C11 117.76(13) . . ?
C15 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C2 O2 C8 118.48(11) . . ?
C7 N1 H1B 119.3(13) . . ?
C7 N1 H1A 118.0(13) . . ?
H1B N1 H1A 122.5(18) . . ?
O1 C7 N1 121.26(12) . . ?
O1 C7 C1 118.73(12) . . ?
N1 C7 C1 119.99(12) . . ?
C5 C6 C1 122.32(12) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C6 C1 C2 118.21(12) . . ?
C6 C1 C7 115.62(11) . . ?
C2 C1 C7 126.12(12) . . ?
C6 C5 C4 118.62(12) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C3 C4 C5 120.68(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C3 C2 120.53(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O2 C2 C3 122.88(12) . . ?
O2 C2 C1 117.49(11) . . ?
C3 C2 C1 119.63(12) . . ?
O2 C8 C9 107.01(12) . . ?
O2 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.054

#===END

data_EASACFII
_database_code_depnum_ccdc_archive 'CCDC 711675'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'Form II of 1:1 cocrystal of ethenzamide and saccharin'
;
_chemical_name_common            
"'Form II of 1:1 cocrystal of ethenzamide and saccharin'"
_chemical_melting_point          394.34
_chemical_formula_moiety         ' C9 H11 N O2, C7 H5 N O3 S'
_chemical_formula_sum            'C16 H16 N2 O5 S'
_chemical_formula_weight         348.37

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.0000 '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)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.6125(17)
_cell_length_b                   16.607(3)
_cell_length_c                   11.183(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.45(3)
_cell_angle_gamma                90.00
_cell_volume                     1598.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5455
_cell_measurement_theta_min      2.1960
_cell_measurement_theta_max      31.0825

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9507
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(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  'CCD area deterctor'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12033
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3951
_reflns_number_gt                3526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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)+(0.0840P)²+0.6428P] 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         3951
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
S1 S 0.79388(5) 0.13461(3) 0.61302(4) 0.02297(17) Uani 1 1 d . . .
O5 O 0.89417(18) 0.13275(9) 0.71728(13) 0.0301(3) Uani 1 1 d . . .
O2 O 0.68908(16) 0.25224(8) 0.29227(13) 0.0259(3) Uani 1 1 d . . .
O1 O 0.42636(18) 0.04262(9) 0.24510(13) 0.0328(4) Uani 1 1 d . . .
O3 O 0.70884(17) -0.05839(9) 0.45456(13) 0.0304(3) Uani 1 1 d . . .
C1 C 0.6079(2) 0.13832(11) 0.17672(18) 0.0220(4) Uani 1 1 d . . .
O4 O 0.67747(17) 0.19660(9) 0.60821(14) 0.0291(3) Uani 1 1 d . . .
N1 N 0.4925(2) 0.14135(11) 0.37444(16) 0.0262(4) Uani 1 1 d . . .
C2 C 0.8983(2) 0.13074(12) 0.48024(18) 0.0230(4) Uani 1 1 d . . .
N2 N 0.71371(19) 0.04548(10) 0.58961(15) 0.0246(4) Uani 1 1 d . . .
C3 C 0.8654(2) 0.05953(12) 0.42008(17) 0.0236(4) Uani 1 1 d . . .
C4 C 0.7003(2) 0.20822(12) 0.18952(17) 0.0230(4) Uani 1 1 d . . .
C5 C 0.9995(2) 0.18761(13) 0.43699(19) 0.0265(4) Uani 1 1 d . . .
H5 H 1.0193 0.2354 0.4781 0.032 Uiso 1 1 calc R . .
C6 C 0.8000(2) 0.22955(13) 0.09824(18) 0.0263(4) Uani 1 1 d . . .
H6 H 0.8619 0.2752 0.1065 0.032 Uiso 1 1 calc R . .
C7 C 0.5021(2) 0.10528(12) 0.26893(18) 0.0246(4) Uani 1 1 d . . .
C8 C 0.7552(2) 0.00753(12) 0.48538(17) 0.0241(4) Uani 1 1 d . . .
C9 C 0.7675(2) 0.32911(12) 0.2988(2) 0.0286(4) Uani 1 1 d . . .
H9A H 0.7366 0.3625 0.2311 0.034 Uiso 1 1 calc R . .
H9B H 0.8791 0.3215 0.2977 0.034 Uiso 1 1 calc R . .
C10 C 0.7156(3) 0.11475(13) -0.0193(2) 0.0314(5) Uani 1 1 d . . .
H10 H 0.7194 0.0840 -0.0886 0.038 Uiso 1 1 calc R . .
C11 C 0.9354(2) 0.04323(13) 0.31190(18) 0.0267(4) Uani 1 1 d . . .
H11 H 0.9133 -0.0040 0.2701 0.032 Uiso 1 1 calc R . .
C12 C 0.8074(2) 0.18309(13) -0.00509(19) 0.0298(5) Uani 1 1 d . . .
H12 H 0.8744 0.1979 -0.0652 0.036 Uiso 1 1 calc R . .
C13 C 0.6188(2) 0.09366(13) 0.07197(19) 0.0273(4) Uani 1 1 d . . .
H13 H 0.5581 0.0476 0.0631 0.033 Uiso 1 1 calc R . .
C14 C 1.0708(2) 0.17064(14) 0.32932(19) 0.0297(5) Uani 1 1 d . . .
H14 H 1.1404 0.2074 0.2981 0.036 Uiso 1 1 calc R . .
C15 C 1.0390(2) 0.09936(14) 0.26798(19) 0.0298(4) Uani 1 1 d . . .
H15 H 1.0880 0.0891 0.1964 0.036 Uiso 1 1 calc R . .
C16 C 0.7221(3) 0.36851(13) 0.4137(2) 0.0345(5) Uani 1 1 d . . .
H16A H 0.6130 0.3804 0.4105 0.052 Uiso 1 1 calc R . .
H16B H 0.7798 0.4175 0.4247 0.052 Uiso 1 1 calc R . .
H16C H 0.7446 0.3328 0.4794 0.052 Uiso 1 1 calc R . .
H1 H 0.553(3) 0.1826(15) 0.386(2) 0.026(6) Uiso 1 1 d . . .
H2 H 0.433(3) 0.1216(16) 0.432(3) 0.042(8) Uiso 1 1 d . . .
H3 H 0.662(4) 0.018(2) 0.645(3) 0.068(10) Uiso 1 1 d . . .


_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 O5 1.4337(16) . ?
S1 O4 1.4370(15) . ?
S1 N2 1.6512(18) . ?
S1 C2 1.757(2) . ?
O2 C4 1.367(2) . ?
O2 C9 1.445(2) . ?
O1 C7 1.253(2) . ?
O3 C8 1.212(2) . ?
C1 C13 1.392(3) . ?
C1 C4 1.412(3) . ?
C1 C7 1.498(3) . ?
N1 C7 1.328(3) . ?
N1 H1 0.87(3) . ?
N1 H2 0.90(3) . ?
C2 C5 1.381(3) . ?
C2 C3 1.386(3) . ?
N2 C8 1.380(3) . ?
N2 H3 0.90(3) . ?
C3 C11 1.392(3) . ?
C3 C8 1.488(3) . ?
C4 C6 1.396(3) . ?
C5 C14 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C12 1.392(3) . ?
C6 H6 0.9300 . ?
C9 C16 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.380(3) . ?
C10 C12 1.390(3) . ?
C10 H10 0.9300 . ?
C11 C15 1.389(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O5 S1 O4 116.81(9) . . ?
O5 S1 N2 110.52(9) . . ?
O4 S1 N2 110.34(9) . . ?
O5 S1 C2 112.07(9) . . ?
O4 S1 C2 111.49(9) . . ?
N2 S1 C2 93.11(9) . . ?
C4 O2 C9 118.13(16) . . ?
C13 C1 C4 118.28(18) . . ?
C13 C1 C7 116.05(17) . . ?
C4 C1 C7 125.62(18) . . ?
C7 N1 H1 116.0(17) . . ?
C7 N1 H2 121.7(18) . . ?
H1 N1 H2 122(2) . . ?
C5 C2 C3 122.46(19) . . ?
C5 C2 S1 127.76(16) . . ?
C3 C2 S1 109.78(14) . . ?
C8 N2 S1 115.28(14) . . ?
C8 N2 H3 120(2) . . ?
S1 N2 H3 124(2) . . ?
C2 C3 C11 119.99(18) . . ?
C2 C3 C8 112.46(17) . . ?
C11 C3 C8 127.54(19) . . ?
O2 C4 C6 122.45(18) . . ?
O2 C4 C1 118.23(17) . . ?
C6 C4 C1 119.32(19) . . ?
C2 C5 C14 117.4(2) . . ?
C2 C5 H5 121.3 . . ?
C14 C5 H5 121.3 . . ?
C12 C6 C4 120.55(19) . . ?
C12 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
O1 C7 N1 121.33(18) . . ?
O1 C7 C1 118.71(18) . . ?
N1 C7 C1 119.95(18) . . ?
O3 C8 N2 124.21(18) . . ?
O3 C8 C3 126.43(18) . . ?
N2 C8 C3 109.36(17) . . ?
O2 C9 C16 107.22(17) . . ?
O2 C9 H9A 110.3 . . ?
C16 C9 H9A 110.3 . . ?
O2 C9 H9B 110.3 . . ?
C16 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C13 C10 C12 118.4(2) . . ?
C13 C10 H10 120.8 . . ?
C12 C10 H10 120.8 . . ?
C15 C11 C3 118.2(2) . . ?
C15 C11 H11 120.9 . . ?
C3 C11 H11 120.9 . . ?
C10 C12 C6 120.62(19) . . ?
C10 C12 H12 119.7 . . ?
C6 C12 H12 119.7 . . ?
C10 C13 C1 122.8(2) . . ?
C10 C13 H13 118.6 . . ?
C1 C13 H13 118.6 . . ?
C15 C14 C5 120.82(19) . . ?
C15 C14 H14 119.6 . . ?
C5 C14 H14 119.6 . . ?
C11 C15 C14 121.1(2) . . ?
C11 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.076

#===END


