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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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data_shelxl

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N3 O4 S'
_chemical_formula_weight         334.37

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 0.0016 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.085(3)
_cell_length_b                   9.738(3)
_cell_length_c                   10.671(4)
_cell_angle_alpha                78.516(9)
_cell_angle_beta                 83.189(9)
_cell_angle_gamma                68.866(9)
_cell_volume                     766.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10043
_cell_measurement_theta_min      1.950
_cell_measurement_theta_max      26.997

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             350
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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_source                   ?
_diffrn_measurement_device_type  'Bruker AXS SMART APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10043
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.950
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3232
_reflns_number_gt                2609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX 2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'Microsoft word 2007'

_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)+(0.0910P)²+0.2955P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3232
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
C1 C 0.2878(4) 0.9782(3) 0.0932(3) 0.0612(7) Uani 1 1 d . . . . .
H1A H 0.2986 1.0738 0.0589 0.092 Uiso 1 1 calc R U . . .
H1B H 0.1678 0.9920 0.1251 0.092 Uiso 1 1 calc R U . . .
H1C H 0.3180 0.9182 0.0269 0.092 Uiso 1 1 calc R U . . .
C2 C 0.4107(3) 0.9018(3) 0.1996(2) 0.0508(6) Uani 1 1 d . . . . .
H2A H 0.5313 0.8907 0.1673 0.061 Uiso 1 1 calc R U . . .
H2B H 0.3806 0.9635 0.2657 0.061 Uiso 1 1 calc R U . . .
C3 C 0.4952(3) 0.6431(3) 0.1927(2) 0.0442(5) Uani 1 1 d . . . . .
C4 C 0.4847(3) 0.4956(2) 0.2579(2) 0.0415(5) Uani 1 1 d . . . . .
C5 C 0.5800(4) 0.3738(3) 0.1981(3) 0.0624(7) Uani 1 1 d . . . . .
H5 H 0.6441 0.3875 0.1213 0.075 Uiso 1 1 calc R U . . .
C6 C 0.5800(5) 0.2331(3) 0.2517(3) 0.0720(9) Uani 1 1 d . . . . .
H6 H 0.6447 0.1520 0.2114 0.086 Uiso 1 1 calc R U . . .
C7 C 0.4838(4) 0.2121(3) 0.3657(3) 0.0549(6) Uani 1 1 d . . . . .
H7 H 0.4845 0.1168 0.4019 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3857(3) 0.3331(2) 0.4264(2) 0.0385(5) Uani 1 1 d . . . . .
C9 C 0.3871(3) 0.4750(2) 0.3722(2) 0.0371(5) Uani 1 1 d . . . . .
H9 H 0.3228 0.5562 0.4123 0.045 Uiso 1 1 calc R U . . .
C10 C 0.0821(3) 0.3860(2) 0.7223(2) 0.0372(5) Uani 1 1 d . . . . .
C11 C -0.0959(3) 0.4463(3) 0.8921(2) 0.0472(5) Uani 1 1 d . . . . .
H11 H -0.1682 0.5100 0.9464 0.057 Uiso 1 1 calc R U . . .
C12 C -0.0661(3) 0.2984(3) 0.9150(3) 0.0533(6) Uani 1 1 d . . . . .
H12 H -0.1130 0.2487 0.9855 0.064 Uiso 1 1 calc R U . . .
C13 C 0.0107(4) 0.8144(3) 0.6074(3) 0.0546(6) Uani 1 1 d . . . . .
C14 C -0.0329(5) 0.9792(3) 0.5634(3) 0.0783(10) Uani 1 1 d . . . . .
H14A H -0.1610 1.0272 0.5678 0.094 Uiso 1 1 calc R U . . .
H14B H 0.0148 1.0175 0.6224 0.094 Uiso 1 1 calc R U . . .
C19 C 0.2834(3) 0.2962(2) 0.5476(2) 0.0396(5) Uani 1 1 d . . . . .
N1 N 0.4019(2) 0.75527(17) 0.25536(15) 0.0338(4) Uani 1 1 d . . . . .
H1 H 0.3399 0.7416 0.3249 0.041 Uiso 1 1 calc R U . . .
N2 N 0.1789(2) 0.4099(2) 0.60964(18) 0.0398(4) Uani 1 1 d . . . . .
N3 N -0.0118(3) 0.4960(2) 0.78276(19) 0.0437(4) Uani 1 1 d . . . . .
O1 O 0.5812(3) 0.6591(2) 0.09519(18) 0.0667(6) Uani 1 1 d . . . . .
O2 O 0.2932(2) 0.16761(17) 0.59036(17) 0.0537(5) Uani 1 1 d . . . . .
O3 O 0.0991(3) 0.72168(17) 0.54209(17) 0.0612(5) Uani 1 1 d . . . . .
O4 O -0.0583(3) 0.7817(2) 0.7205(2) 0.0814(8) Uani 1 1 d . . . . .
S1 S 0.07116(9) 0.21465(6) 0.79506(6) 0.0509(2) Uani 1 1 d . . . . .
H4C H -0.025(6) 0.678(5) 0.746(4) 0.125(15) Uiso 1 1 d . . . . .
H2C H 0.171(4) 0.503(3) 0.575(3) 0.055(7) 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
C1 C2 1.493(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.456(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.197(3) . ?
C3 N1 1.336(3) . ?
C3 C4 1.494(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.392(3) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(3) . ?
C8 C19 1.504(3) . ?
C9 H9 0.9300 . ?
C10 N3 1.309(3) . ?
C10 N2 1.382(3) . ?
C10 S1 1.723(2) . ?
C11 C12 1.347(4) . ?
C11 N3 1.372(3) . ?
C11 H11 0.9300 . ?
C12 S1 1.721(3) . ?
C12 H12 0.9300 . ?
C13 O3 1.216(3) . ?
C13 O4 1.298(3) . ?
C13 C14 1.501(3) . ?
C14 C14 1.429(6) 2_576 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C19 O2 1.221(3) . ?
C19 N2 1.364(3) . ?
N1 H1 0.8600 . ?
N2 H2C 0.89(3) . ?
O4 H4C 0.94(5) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 112.3(2) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 N1 123.2(2) . . ?
O1 C3 C4 123.4(2) . . ?
N1 C3 C4 113.35(19) . . ?
C5 C4 C9 119.6(2) . . ?
C5 C4 C3 116.3(2) . . ?
C9 C4 C3 124.05(19) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 C19 125.43(18) . . ?
C7 C8 C19 115.2(2) . . ?
C8 C9 C4 120.10(19) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
N3 C10 N2 121.34(19) . . ?
N3 C10 S1 114.15(17) . . ?
N2 C10 S1 124.51(16) . . ?
C12 C11 N3 115.1(2) . . ?
C12 C11 H11 122.4 . . ?
N3 C11 H11 122.4 . . ?
C11 C12 S1 110.34(19) . . ?
C11 C12 H12 124.8 . . ?
S1 C12 H12 124.8 . . ?
O3 C13 O4 123.8(2) . . ?
O3 C13 C14 123.0(2) . . ?
O4 C13 C14 113.2(2) . . ?
C14 C14 C13 115.2(3) 2_576 . ?
C14 C14 H14A 108.5 2_576 . ?
C13 C14 H14A 108.5 . . ?
C14 C14 H14B 108.5 2_576 . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O2 C19 N2 120.3(2) . . ?
O2 C19 C8 121.15(19) . . ?
N2 C19 C8 118.51(19) . . ?
C3 N1 C2 116.43(18) . . ?
C3 N1 H1 121.8 . . ?
C2 N1 H1 121.8 . . ?
C19 N2 C10 122.42(19) . . ?
C19 N2 H2C 118.8(18) . . ?
C10 N2 H2C 118.8(17) . . ?
C10 N3 C11 111.21(19) . . ?
C13 O4 H4C 110(3) . . ?
C12 S1 C10 89.17(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2C O3 0.89(3) 1.96(3) 2.825(3) 163(3) .
O4 H4C N3 0.94(5) 1.70(5) 2.625(3) 167(4) .
C9 H9 O3 0.93 2.45 3.344(3) 162.5 .
N1 H1 O3 0.86 2.87 3.724(3) 173.4 .

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1012219'
