# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_alpha1
_database_code_depnum_ccdc_archive 'CCDC 1050926'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2013

_chemical_name_systematic        Piroxicam
_chemical_name_common            'Piroxicam: Form Alpha1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O4 S'
_chemical_formula_sum            'C15 H13 N3 O4 S'
_chemical_formula_weight         331.34
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P b c 21'
_space_group_name_Hall           'P 2c -2b'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.3964(14)
_cell_length_b                   11.7965(10)
_cell_length_c                   6.9851(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1433.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2039
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      50.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.250
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5468
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3586
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         7.639
_diffrn_reflns_theta_max         50.437
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.485
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.485
_diffrn_reflns_point_group_measured_fraction_max 0.635
_diffrn_reflns_point_group_measured_fraction_full 0.364
_reflns_number_total             949
_reflns_number_gt                743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_max     0.389
_reflns_Friedel_fraction_full    0.219

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL-2013

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+2.1533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.11(4)
_refine_ls_abs_structure_details 
;
Flack x determined using 190 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_number_reflns         949
_refine_ls_number_parameters     208
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.067

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3032(2) 0.4456(3) -0.0072(5) 0.0394(11) Uani 1 1 d . . . . .
O1 O 0.3081(5) 0.3261(7) 0.0436(11) 0.045(3) Uani 1 1 d . . . . .
O2 O 0.2777(5) 0.4790(7) -0.1935(12) 0.051(3) Uani 1 1 d . . . . .
O3 O 0.1729(5) 0.7975(8) 0.1654(13) 0.046(3) Uani 1 1 d . . . . .
O4 O 0.3196(5) 0.7996(8) 0.1148(13) 0.048(3) Uani 1 1 d . . . . .
H1 H 0.2767 0.8272 0.1282 0.073 Uiso 1 1 calc R U . . .
N1 N 0.2457(6) 0.5073(9) 0.1502(13) 0.029(3) Uani 1 1 d . . . . .
N2 N 0.1119(8) 0.6260(10) 0.1548(16) 0.045(3) Uani 1 1 d . . . . .
H2 H 0.1202 0.5549 0.1375 0.067 Uiso 1 1 calc R U . . .
N3 N -0.0114(7) 0.5621(10) 0.1890(15) 0.044(3) Uani 1 1 d . . . . .
C1 C 0.2468(10) 0.6288(13) 0.1358(18) 0.034(4) Uani 1 1 d . U . . .
C2 C 0.3142(11) 0.6832(14) 0.1159(18) 0.038(4) Uani 1 1 d . U . . .
C3 C 0.4569(10) 0.6839(13) 0.1124(18) 0.045(5) Uani 1 1 d . U . . .
H3 H 0.4564 0.7599 0.1478 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5275(10) 0.6290(14) 0.0862(18) 0.049(5) Uani 1 1 d . U . . .
H4 H 0.5734 0.6690 0.0947 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5273(10) 0.5158(14) 0.0480(18) 0.046(5) Uani 1 1 d . U . . .
H5 H 0.5737 0.4769 0.0397 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4587(10) 0.4579(13) 0.0214(19) 0.045(4) Uani 1 1 d . U . . .
H6 H 0.4589 0.3812 -0.0093 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3916(9) 0.5147(13) 0.0407(16) 0.033(4) Uani 1 1 d . U . . .
C8 C 0.3879(11) 0.6278(14) 0.0868(16) 0.035(4) Uani 1 1 d . U . . .
C9 C 0.2501(7) 0.4623(11) 0.3476(17) 0.044(4) Uani 1 1 d . U . . .
H9A H 0.2158 0.5040 0.4288 0.067 Uiso 1 1 calc R U . . .
H9B H 0.3017 0.4698 0.3945 0.067 Uiso 1 1 calc R U . . .
H9C H 0.2358 0.3837 0.3476 0.067 Uiso 1 1 calc R U . . .
C10 C 0.1751(11) 0.6930(16) 0.153(2) 0.047(5) Uani 1 1 d . U . . .
C11 C 0.0324(10) 0.6574(13) 0.182(2) 0.038(4) Uani 1 1 d . U . . .
C12 C 0.0059(8) 0.7657(13) 0.1896(16) 0.038(4) Uani 1 1 d . U . . .
H12 H 0.0391 0.8271 0.1785 0.046 Uiso 1 1 calc R U . . .
C13 C -0.0719(9) 0.7808(13) 0.214(2) 0.051(5) Uani 1 1 d . U . . .
H13 H -0.0923 0.8533 0.2242 0.061 Uiso 1 1 calc R U . . .
C14 C -0.1192(8) 0.6871(13) 0.2239(18) 0.044(4) Uani 1 1 d . U . . .
H14 H -0.1720 0.6952 0.2393 0.053 Uiso 1 1 calc R U . . .
C15 C -0.0864(10) 0.5823(13) 0.210(2) 0.047(4) Uani 1 1 d . U . . .
H15 H -0.1189 0.5199 0.2167 0.057 Uiso 1 1 calc R U . . .


_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(9) . ?
S1 O1 1.456(8) . ?
S1 N1 1.656(10) . ?
S1 C7 1.773(14) . ?
O3 C10 1.236(15) . ?
O4 C2 1.377(14) . ?
O4 H1 0.8200 . ?
N1 C1 1.437(16) . ?
N1 C9 1.480(13) . ?
N2 C10 1.354(17) . ?
N2 C11 1.444(16) . ?
N2 H2 0.8600 . ?
N3 C15 1.334(15) . ?
N3 C11 1.358(15) . ?
C1 C2 1.344(18) . ?
C1 C10 1.46(2) . ?
C2 C8 1.452(18) . ?
C3 C8 1.383(17) . ?
C3 C4 1.400(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.354(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(17) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.359(17) . ?
C12 C13 1.376(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(16) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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 120.5(5) . . ?
O2 S1 N1 107.2(5) . . ?
O1 S1 N1 107.4(5) . . ?
O2 S1 C7 108.3(6) . . ?
O1 S1 C7 110.4(7) . . ?
N1 S1 C7 101.3(7) . . ?
C2 O4 H1 109.5 . . ?
C1 N1 C9 115.0(10) . . ?
C1 N1 S1 112.6(10) . . ?
C9 N1 S1 115.4(8) . . ?
C10 N2 C11 129.0(14) . . ?
C10 N2 H2 115.5 . . ?
C11 N2 H2 115.5 . . ?
C15 N3 C11 113.8(14) . . ?
C2 C1 N1 119.7(15) . . ?
C2 C1 C10 120.4(15) . . ?
N1 C1 C10 119.9(15) . . ?
C1 C2 O4 122.4(16) . . ?
C1 C2 C8 124.7(16) . . ?
O4 C2 C8 112.8(17) . . ?
C8 C3 C4 121.6(15) . . ?
C8 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 118.5(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 120.7(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.0(14) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 123.0(16) . . ?
C6 C7 S1 120.1(13) . . ?
C8 C7 S1 116.8(14) . . ?
C7 C8 C3 117.0(17) . . ?
C7 C8 C2 120.8(17) . . ?
C3 C8 C2 122.2(16) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N2 123.8(17) . . ?
O3 C10 C1 123.2(17) . . ?
N2 C10 C1 113.0(15) . . ?
N3 C11 C12 126.0(15) . . ?
N3 C11 N2 109.2(13) . . ?
C12 C11 N2 124.7(14) . . ?
C11 C12 C13 117.3(15) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C12 C13 C14 119.3(14) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 118.2(14) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
N3 C15 C14 125.3(15) . . ?
N3 C15 H15 117.3 . . ?
C14 C15 H15 117.3 . . ?

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_alpha2
_database_code_depnum_ccdc_archive 'CCDC 1050927'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2013

_chemical_name_systematic        Piroxicam
_chemical_name_common            'Piroxicam: Form Alpha2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O4 S'
_chemical_formula_sum            'C15 H13 N3 O4 S'
_chemical_formula_weight         331.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.577(3)
_cell_length_b                   11.745(2)
_cell_length_c                   6.8516(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.07(1)
_cell_angle_gamma                90
_cell_volume                     1400.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5298
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      49.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.303
_shelx_estimated_absorpt_T_min   0.656
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_process_details   'TWINABS (Bruker, 2014)'

_exptl_special_details           
;
Crystal is a 2-component twin with domains related by 2-fold rotation
around the c axis. Refined BASF = 0.464(5).
Diffraction was weak, and data were integrated only to 1 Å resolution.
All atoms are refined with isotropic displacement parameters.
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2092
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_av_R_equivalents  0.1265
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         7.661
_diffrn_reflns_theta_max         50.394
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.553
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.553
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.553
_reflns_number_total             2092
_reflns_number_gt                1646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

Data merging carried out in TWINABS:

 Statistics for singles of twin component  1
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   48.0  0.0498   0.729 - 0.875   0.867 - 1.269   1.497     213     135
    2   48.0  0.1041   0.232 - 0.528   0.843 - 1.270   1.695     196     126
    3   48.0  0.0455   0.989 - 1.387   0.853 - 1.274   1.459     198     135
    4   48.0  0.2954   1.034 - 1.313   0.977 - 1.247   1.976      24       6
    5   48.0  0.1230   0.232 - 0.348   0.851 - 1.101   1.745      44      17
    7   33.0  0.0296   1.150 - 1.666   0.843 - 1.116   1.533      97      69
    9   48.0  0.0543   0.806 - 0.964   0.844 - 1.164   1.716      67      31
   12   48.0  0.0449   0.778 - 0.944   0.909 - 1.274   1.468     121      83
   13   48.0  0.0902   0.796 - 1.072   0.854 - 1.165   1.620      71      35
   15   48.0  0.0556   0.146 - 0.256   0.843 - 1.243   1.428     214     154
   18   18.0  0.0245   1.143 - 1.645   0.843 - 1.157   1.474     131      99
   19   48.0  0.0995   1.024 - 2.312   0.844 - 1.279   1.355     981     573

   All scans  0.0677   0.146 - 2.312   0.843 - 1.279   0.998    2357    1463


 Statistics for singles of twin component  2
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   48.0  0.0501   0.752 - 0.847   0.877 - 1.202   1.497     198     120
    2   48.0  0.0955   0.211 - 0.472   0.863 - 1.224   1.695     217     144
    3   48.0  0.0465   1.102 - 1.607   0.886 - 1.211   1.459     201     126
    4   48.0  0.2527   1.031 - 1.150   1.001 - 1.194   1.976      23       6
    5   48.0  0.1704   0.288 - 0.324   0.862 - 1.066   1.745      46      19
    7   33.0  0.0569   1.026 - 1.422   0.887 - 1.086   1.533      96      57
    9   48.0  0.0493   0.862 - 1.063   0.854 - 1.145   1.716      66      26
   12   48.0  0.0335   0.744 - 0.869   0.944 - 1.214   1.468     116      82
   13   48.0  0.0363   0.744 - 1.021   0.888 - 1.171   1.620      78      46
   15   48.0  0.0404   0.125 - 0.218   0.856 - 1.296   1.428     215     168
   18   18.0  0.0338   0.996 - 1.415   0.887 - 1.153   1.474     120      85
   19   48.0  0.1113   1.089 - 2.168   0.857 - 1.228   1.355    1002     560

   All scans  0.0695   0.125 - 2.168   0.854 - 1.296   0.998    2378    1439


 Statistics for all composite reflections
 ----------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   48.0  0.1608   0.739 - 0.845   0.879 - 1.229   1.497     508     320
    2   48.0  0.2056   0.216 - 0.513   0.851 - 1.266   1.695    1817    1023
    3   48.0  0.1580   1.002 - 1.489   0.860 - 1.249   1.459     487     341
    4   48.0  0.2161   1.042 - 1.300   0.874 - 1.241   1.976     407     228
    5   48.0  0.2146   0.251 - 0.336   0.850 - 1.202   1.745     491     282
    7   33.0  0.1134   1.045 - 1.589   0.853 - 1.147   1.533     391     277
    9   48.0  0.2216   0.825 - 0.985   0.867 - 1.200   1.716     345     215
   12   48.0  0.1244   0.759 - 0.919   0.870 - 1.247   1.468     593     399
   13   48.0  0.1885   0.760 - 1.049   0.859 - 1.239   1.620     399     241
   15   48.0  0.0941   0.131 - 0.251   0.854 - 1.265   1.428    1530    1228
   18   18.0  0.0741   1.011 - 1.558   0.860 - 1.136   1.474     363     294
   19   48.0  0.1712   1.038 - 2.272   0.849 - 1.254   1.355    1841    1141

   All scans  0.1569   0.131 - 2.272   0.849 - 1.266   0.998    9172    5989


 Statistics for all single and composite reflections
 ---------------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   48.0  0.0975   0.729 - 0.875   0.867 - 1.269   1.497     919     575
    2   48.0  0.1856   0.211 - 0.528   0.843 - 1.270   1.695    2230    1293
    3   48.0  0.0984   0.989 - 1.607   0.853 - 1.274   1.459     886     602
    4   48.0  0.2194   1.031 - 1.313   0.874 - 1.247   1.976     454     240
    5   48.0  0.2081   0.232 - 0.348   0.850 - 1.202   1.745     581     318
    7   33.0  0.0818   1.026 - 1.666   0.843 - 1.147   1.533     584     403
    9   48.0  0.1481   0.806 - 1.063   0.844 - 1.200   1.716     478     272
   12   48.0  0.0885   0.744 - 0.944   0.870 - 1.274   1.468     830     564
   13   48.0  0.1496   0.744 - 1.072   0.854 - 1.239   1.620     548     322
   15   48.0  0.0863   0.125 - 0.256   0.843 - 1.296   1.428    1959    1550
   18   18.0  0.0540   0.996 - 1.645   0.843 - 1.157   1.474     614     478
   19   48.0  0.1423   1.024 - 2.312   0.844 - 1.279   1.355    3824    2274

   All scans  0.1265   0.125 - 2.312   0.843 - 1.296   0.998   13907    8891

 su = K * Sqrt[ sigma^2(I) + (g)^2 ]  where sigma(I) is estimated by SAINT
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL-2013

_refine_special_details          Twin

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1240P)²+12.3031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2092
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.1004
_refine_ls_wR_factor_ref         0.2586
_refine_ls_wR_factor_gt          0.2381
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.167

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70084(16) 0.9450(3) 0.3834(5) 0.0155(10) Uani 1 1 d . . . . .
O1 O 0.6959(4) 0.8263(6) 0.3357(11) 0.014(2) Uiso 1 1 d . . . . .
O2 O 0.7248(4) 0.9799(7) 0.5832(14) 0.019(2) Uiso 1 1 d . . . . .
O3 O 0.8282(4) 1.2987(7) 0.2457(13) 0.016(2) Uiso 1 1 d . . . . .
O4 O 0.6810(4) 1.2986(6) 0.2392(13) 0.019(2) Uiso 1 1 d . . . . .
H4 H 0.7239 1.3270 0.2448 0.028 Uiso 1 1 calc R U . . .
N1 N 0.7582(5) 1.0062(8) 0.2429(16) 0.013(2) Uiso 1 1 d . . . . .
N2 N 0.8923(5) 1.1289(8) 0.2814(15) 0.018(3) Uiso 1 1 d . . . . .
H2 H 0.8846 1.0576 0.2989 0.022 Uiso 1 1 calc R U . . .
N3 N 1.0140(5) 1.0676(8) 0.2887(15) 0.015(3) Uiso 1 1 d . . . . .
C1 C 0.7560(7) 1.1291(10) 0.2512(19) 0.018(3) Uiso 1 1 d . . . . .
C2 C 0.6871(7) 1.1845(10) 0.241(2) 0.015(3) Uiso 1 1 d . . . . .
C3 C 0.5438(6) 1.1797(10) 0.1804(19) 0.018(3) Uiso 1 1 d . . . . .
H3 H 0.5430 1.2548 0.1369 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4751(7) 1.1207(10) 0.185(2) 0.022(3) Uiso 1 1 d . . . . .
H4 H 0.4286 1.1586 0.1528 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4748(6) 1.0083(10) 0.2367(17) 0.012(3) Uiso 1 1 d . . . . .
H5 H 0.4284 0.9697 0.2333 0.014 Uiso 1 1 calc R U . . .
C6 C 0.5437(6) 0.9515(10) 0.2942(18) 0.013(3) Uiso 1 1 d . . . . .
H6 H 0.5438 0.8754 0.3315 0.016 Uiso 1 1 calc R U . . .
C7 C 0.6131(6) 1.0107(9) 0.2950(18) 0.011(3) Uiso 1 1 d . . . . .
C8 C 0.6137(6) 1.1253(10) 0.2412(19) 0.015(3) Uiso 1 1 d . . . . .
C9 C 0.7511(7) 0.9620(10) 0.0369(19) 0.022(4) Uiso 1 1 d . . . . .
H9A H 0.7863 1.0018 -0.0338 0.034 Uiso 1 1 calc R U . . .
H9B H 0.6996 0.9735 -0.0276 0.034 Uiso 1 1 calc R U . . .
H9C H 0.7629 0.8821 0.0395 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8280(7) 1.1937(11) 0.261(2) 0.016(3) Uiso 1 1 d . . . . .
C11 C 0.9704(6) 1.1589(9) 0.2791(18) 0.010(3) Uiso 1 1 d . . . . .
C12 C 0.9954(6) 1.2692(10) 0.2742(18) 0.015(3) Uiso 1 1 d . . . . .
H12 H 0.9614 1.3302 0.2692 0.018 Uiso 1 1 calc R U . . .
C13 C 1.0726(6) 1.2858(9) 0.2770(19) 0.019(4) Uiso 1 1 d . . . . .
H13 H 1.0922 1.3592 0.2735 0.022 Uiso 1 1 calc R U . . .
C14 C 1.1213(7) 1.1935(10) 0.2849(19) 0.019(3) Uiso 1 1 d . . . . .
H14 H 1.1739 1.2035 0.2879 0.023 Uiso 1 1 calc R U . . .
C15 C 1.0900(6) 1.0853(10) 0.2885(19) 0.017(3) Uiso 1 1 d . . . . .
H15 H 1.1225 1.0226 0.2907 0.021 Uiso 1 1 calc R U . . .


_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 1.431(8) . ?
S1 O2 1.435(9) . ?
S1 N1 1.652(10) . ?
S1 C7 1.754(11) . ?
O3 C10 1.238(11) . ?
O4 C2 1.344(12) . ?
O4 H4 0.8200 . ?
N1 C1 1.445(14) . ?
N1 C9 1.493(15) . ?
N2 C10 1.354(15) . ?
N2 C11 1.418(14) . ?
N2 H2 0.8600 . ?
N3 C11 1.314(13) . ?
N3 C15 1.353(14) . ?
C1 C2 1.368(16) . ?
C1 C10 1.468(17) . ?
C2 C8 1.467(16) . ?
C3 C8 1.394(16) . ?
C3 C4 1.398(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(16) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.370(17) . ?
C12 C13 1.369(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(15) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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 119.8(5) . . ?
O1 S1 N1 108.3(5) . . ?
O2 S1 N1 108.0(5) . . ?
O1 S1 C7 109.1(5) . . ?
O2 S1 C7 109.3(5) . . ?
N1 S1 C7 100.7(5) . . ?
C2 O4 H4 109.5 . . ?
C1 N1 C9 112.7(10) . . ?
C1 N1 S1 113.0(8) . . ?
C9 N1 S1 115.0(8) . . ?
C10 N2 C11 130.9(10) . . ?
C10 N2 H2 114.6 . . ?
C11 N2 H2 114.6 . . ?
C11 N3 C15 116.4(10) . . ?
C2 C1 N1 120.1(10) . . ?
C2 C1 C10 120.5(10) . . ?
N1 C1 C10 119.4(10) . . ?
O4 C2 C1 122.9(11) . . ?
O4 C2 C8 113.8(11) . . ?
C1 C2 C8 123.2(11) . . ?
C8 C3 C4 119.6(11) . . ?
C8 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.3(11) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.1(10) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 119.1(11) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.0(10) . . ?
C8 C7 S1 118.5(8) . . ?
C6 C7 S1 120.3(9) . . ?
C3 C8 C7 118.8(11) . . ?
C3 C8 C2 121.3(11) . . ?
C7 C8 C2 119.8(10) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N2 123.8(12) . . ?
O3 C10 C1 121.6(12) . . ?
N2 C10 C1 114.6(10) . . ?
N3 C11 C12 125.9(10) . . ?
N3 C11 N2 110.8(9) . . ?
C12 C11 N2 123.3(10) . . ?
C13 C12 C11 117.0(10) . . ?
C13 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
C12 C13 C14 119.9(11) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 118.5(11) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
N3 C15 C14 122.3(11) . . ?
N3 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?

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
O1 S1 N1 C1 169.0(8) . . . . ?
O2 S1 N1 C1 -59.9(9) . . . . ?
C7 S1 N1 C1 54.5(9) . . . . ?
O1 S1 N1 C9 37.7(9) . . . . ?
O2 S1 N1 C9 168.8(8) . . . . ?
C7 S1 N1 C9 -76.8(9) . . . . ?
C9 N1 C1 C2 87.6(14) . . . . ?
S1 N1 C1 C2 -44.8(15) . . . . ?
C9 N1 C1 C10 -89.2(14) . . . . ?
S1 N1 C1 C10 138.3(10) . . . . ?
N1 C1 C2 O4 -177.1(12) . . . . ?
C10 C1 C2 O4 0(2) . . . . ?
N1 C1 C2 C8 6(2) . . . . ?
C10 C1 C2 C8 -176.7(13) . . . . ?
C8 C3 C4 C5 -4(2) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
C4 C5 C6 C7 -1.1(18) . . . . ?
C5 C6 C7 C8 0.7(18) . . . . ?
C5 C6 C7 S1 175.4(9) . . . . ?
O1 S1 C7 C8 -150.8(9) . . . . ?
O2 S1 C7 C8 76.5(11) . . . . ?
N1 S1 C7 C8 -37.1(11) . . . . ?
O1 S1 C7 C6 34.4(12) . . . . ?
O2 S1 C7 C6 -98.3(10) . . . . ?
N1 S1 C7 C6 148.1(10) . . . . ?
C4 C3 C8 C7 3.6(18) . . . . ?
C4 C3 C8 C2 -179.3(12) . . . . ?
C6 C7 C8 C3 -2.0(18) . . . . ?
S1 C7 C8 C3 -176.7(10) . . . . ?
C6 C7 C8 C2 -179.1(12) . . . . ?
S1 C7 C8 C2 6.1(17) . . . . ?
O4 C2 C8 C3 20.0(18) . . . . ?
C1 C2 C8 C3 -163.3(12) . . . . ?
O4 C2 C8 C7 -163.0(12) . . . . ?
C1 C2 C8 C7 14(2) . . . . ?
C11 N2 C10 O3 -4(2) . . . . ?
C11 N2 C10 C1 173.9(11) . . . . ?
C2 C1 C10 O3 -5(2) . . . . ?
N1 C1 C10 O3 171.8(13) . . . . ?
C2 C1 C10 N2 176.6(12) . . . . ?
N1 C1 C10 N2 -6.5(18) . . . . ?
C15 N3 C11 C12 -1.9(19) . . . . ?
C15 N3 C11 N2 -179.7(10) . . . . ?
C10 N2 C11 N3 -174.9(12) . . . . ?
C10 N2 C11 C12 7(2) . . . . ?
N3 C11 C12 C13 1(2) . . . . ?
N2 C11 C12 C13 178.6(11) . . . . ?
C11 C12 C13 C14 -0.2(19) . . . . ?
C12 C13 C14 C15 0.5(19) . . . . ?
C11 N3 C15 C14 2.1(18) . . . . ?
C13 C14 C15 N3 -1.5(19) . . . . ?

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
