# 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
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data_px_imid_1

_audit_creation_date             2014-01-20T15:10:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C36 H36 N10 O9 S2'
_chemical_formula_moiety         '2(C15 H12 N3 O4 S), 2(C3 H5 N2), H2 O'
_chemical_formula_weight         816.87

#==============================================================================

# CRYSTAL DATA

_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                   6.8019(4)
_cell_length_b                   14.4384(8)
_cell_length_c                   19.8727(12)
_cell_angle_alpha                90.460(2)
_cell_angle_beta                 99.276(2)
_cell_angle_gamma                101.460(2)
_cell_volume                     1886.13(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_exptl_crystal_description       needles
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             852
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8647
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_number            39251
_diffrn_reflns_av_R_equivalents  0.1704
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         23.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.801
_diffrn_reflns_Laue_measured_fraction_full 0.801
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All hydrogen atoms were placed in calculated positions and refined as riding
on the atoms to which they were bonded except those involved in hydrogen
bonding.  H2A, H5A, H7A, H8A and H9A were identified using a Fourier 
difference map and the position was allowed to freely refine but the isotropic
displacement parameter was constrained to take a value of 1.2 times the atom 
to which it was bonded.  Atoms H9B and H9C are water hydrogen atoms and these
were also identified in a Fourier difference map but the isotropic 
displacement parameter constrained to be 1.5 times that of O9, the atom to 
which they are bonded.
;
_reflns_number_total             5468
_reflns_number_gt                2890
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1543
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.0996
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_number_reflns         5468
_refine_ls_number_parameters     538
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O9 0.4034(5) 0.4469(2) 0.10865(17) 0.0347(10) Uani d 1 . . O
H9A 0.248(6) 0.408(3) 0.434(2) 0.042 Uiso d 1 . . H
H5A 1.047(6) 0.414(3) 0.172(2) 0.042 Uiso d 1 . . H
H2A 0.698(6) 0.551(3) 0.419(2) 0.042 Uiso d 1 . . H
H10A 0.144(6) 0.544(3) 0.263(2) 0.042 Uiso d 1 . . H
H7A 0.585(6) 0.286(3) -0.018(2) 0.042 Uiso d 1 . . H
H8A 0.388(7) 0.304(3) -0.207(2) 0.042 Uiso d 1 . . H
H9B 0.329(7) 0.400(3) 0.134(2) 0.052 Uiso d 1 . . H
H9C 0.487(7) 0.413(3) 0.090(2) 0.052 Uiso d 1 . . H
S1 0.88639(17) 0.10538(8) 0.05152(6) 0.0183(3) Uani d 1 . . S
O8 0.6853(4) 0.35783(19) 0.05530(14) 0.0185(8) Uani d 1 . . O
O7 1.1728(4) 0.3180(2) 0.20459(14) 0.0219(8) Uani d 1 . . O
O5 0.7439(4) 0.02241(18) 0.02239(13) 0.0225(8) Uani d 1 . . O
N4 0.7600(5) 0.1798(2) 0.07801(16) 0.0149(9) Uani d 1 . . N
O6 1.0263(4) 0.15559(18) 0.01094(13) 0.0194(7) Uani d 1 . . O
N6 1.0623(5) 0.5797(2) 0.17945(17) 0.0148(9) Uani d 1 . . N
N5 0.9480(5) 0.4268(2) 0.13890(18) 0.0167(10) Uani d 1 . . N
C22 0.8894(6) 0.2611(3) 0.1174(2) 0.0148(11) Uani d 1 . . C
N7 0.5283(5) 0.2656(3) -0.06366(19) 0.0204(10) Uani d 1 . . N
N8 0.4206(6) 0.2758(3) -0.17120(19) 0.0217(10) Uani d 1 . . N
C24 0.9599(6) 0.5225(3) 0.1262(2) 0.0148(11) Uani d 1 . . C
C19 1.0988(6) 0.1532(3) 0.1775(2) 0.0159(11) Uani d 1 . . C
C23 0.8337(7) 0.3499(3) 0.1004(2) 0.0153(11) Uani d 1 . . C
C18 1.2232(6) 0.1358(3) 0.2372(2) 0.0180(11) Uani d 1 . . C
H18 1.2727 0.1836 0.2709 0.022 Uiso calc 1 . . H
C21 1.0539(7) 0.2493(3) 0.1669(2) 0.0165(11) Uani d 1 . . C
C20 1.0291(6) 0.0789(3) 0.1285(2) 0.0145(11) Uani d 1 . . C
C26 0.9156(6) 0.6527(3) 0.0573(2) 0.0185(11) Uani d 1 . . C
H26 0.8688 0.6777 0.0162 0.022 Uiso calc 1 . . H
C16 1.2016(6) -0.0248(3) 0.1979(2) 0.0205(12) Uani d 1 . . C
H16 1.2358 -0.0835 0.2051 0.025 Uiso calc 1 . . H
C27 1.0188(6) 0.7129(3) 0.1121(2) 0.0209(12) Uani d 1 . . C
H27 1.0402 0.7782 0.1085 0.025 Uiso calc 1 . . H
C25 0.8825(6) 0.5563(3) 0.0638(2) 0.0190(11) Uani d 1 . . C
H25 0.8111 0.515 0.028 0.023 Uiso calc 1 . . H
C30 0.5725(6) 0.1389(3) 0.1054(2) 0.0270(13) Uani d 1 . . C
H30A 0.4965 0.0858 0.0766 0.04 Uiso calc 1 . . H
H30B 0.4912 0.186 0.1065 0.04 Uiso calc 1 . . H
H30C 0.6086 0.1185 0.1507 0.04 Uiso calc 1 . . H
C28 1.0884(6) 0.6736(3) 0.1716(2) 0.0170(11) Uani d 1 . . C
H28 1.1571 0.7139 0.2084 0.02 Uiso calc 1 . . H
C33 0.3992(6) 0.1809(3) -0.1586(2) 0.0264(12) Uani d 1 . . C
H33 0.3481 0.1306 -0.1903 0.032 Uiso calc 1 . . H
C32 0.4672(6) 0.1751(3) -0.0909(2) 0.0224(12) Uani d 1 . . C
H32 0.4715 0.1199 -0.0674 0.027 Uiso calc 1 . . H
C31 0.4997(6) 0.3259(3) -0.1132(2) 0.0194(11) Uani d 1 . . C
H31 0.5299 0.3915 -0.1081 0.023 Uiso calc 1 . . H
C17 1.2732(6) 0.0476(3) 0.2466(2) 0.0216(12) Uani d 1 . . C
H17 1.3567 0.0373 0.2865 0.026 Uiso calc 1 . . H
C15 1.0775(6) -0.0096(3) 0.1377(2) 0.0182(11) Uani d 1 . . C
H15 1.0282 -0.0578 0.1044 0.022 Uiso calc 1 . . H
S2 0.60384(17) 0.86579(8) 0.35033(6) 0.0211(3) Uani d 1 . . S
O1 0.3907(4) 0.82213(19) 0.34041(14) 0.0256(8) Uani d 1 . . O
O4 0.6802(4) 0.61159(19) 0.27225(15) 0.0228(8) Uani d 1 . . O
O2 0.6656(4) 0.95014(19) 0.31482(14) 0.0247(8) Uani d 1 . . O
O3 0.7245(4) 0.6471(2) 0.48477(14) 0.0284(8) Uani d 1 . . O
N1 0.7290(5) 0.7869(2) 0.33154(16) 0.0156(9) Uani d 1 . . N
N2 0.6946(5) 0.5385(3) 0.37427(18) 0.0178(10) Uani d 1 . . N
C8 0.7112(6) 0.7048(3) 0.3735(2) 0.0174(11) Uani d 1 . . C
N3 0.7161(5) 0.3901(3) 0.40851(17) 0.0226(10) Uani d 1 . . N
C7 0.7275(6) 0.7160(3) 0.4444(2) 0.0198(12) Uani d 1 . . C
C9 0.6935(6) 0.6167(3) 0.3360(2) 0.0180(12) Uani d 1 . . C
C3 0.6933(6) 0.8885(3) 0.4386(2) 0.0198(12) Uani d 1 . . C
C4 0.7454(6) 0.8124(3) 0.4759(2) 0.0205(12) Uani d 1 . . C
C2 0.7090(6) 0.9771(3) 0.4682(2) 0.0255(12) Uani d 1 . . C
H2 0.674 1.026 0.4418 0.031 Uiso calc 1 . . H
C1 0.7774(6) 0.9922(3) 0.5376(2) 0.0292(13) Uani d 1 . . C
H1 0.7873 1.0514 0.5582 0.035 Uiso calc 1 . . H
C10 0.6969(6) 0.4457(3) 0.3550(2) 0.0176(11) Uani d 1 . . C
C12 0.6907(6) 0.3188(3) 0.2772(2) 0.0269(13) Uani d 1 . . C
H12 0.681 0.2946 0.233 0.032 Uiso calc 1 . . H
C5 0.8142(6) 0.8302(3) 0.5459(2) 0.0279(13) Uani d 1 . . C
H5 0.8496 0.7816 0.5726 0.033 Uiso calc 1 . . H
C13 0.7148(6) 0.2608(3) 0.3317(2) 0.0276(13) Uani d 1 . . C
H13 0.7247 0.1981 0.3255 0.033 Uiso calc 1 . . H
C11 0.6812(6) 0.4122(3) 0.2878(2) 0.0210(12) Uani d 1 . . C
H11 0.6647 0.4516 0.2515 0.025 Uiso calc 1 . . H
C6 0.8309(7) 0.9190(4) 0.5764(2) 0.0305(13) Uani d 1 . . C
H6 0.8782 0.9292 0.6229 0.037 Uiso calc 1 . . H
C14 0.7233(7) 0.3004(4) 0.3956(3) 0.0307(13) Uani d 1 . . C
H14 0.7351 0.2616 0.4325 0.037 Uiso calc 1 . . H
C29 0.9378(6) 0.8223(3) 0.3178(2) 0.0240(12) Uani d 1 . . C
H29A 0.9389 0.8761 0.2896 0.036 Uiso calc 1 . . H
H29B 0.9816 0.7734 0.2948 0.036 Uiso calc 1 . . H
H29C 1.0282 0.8406 0.3602 0.036 Uiso calc 1 . . H
N9 0.2324(5) 0.4547(3) 0.40489(19) 0.0217(10) Uani d 1 . . N
N10 0.1840(5) 0.5306(3) 0.31287(19) 0.0192(10) Uani d 1 . . N
C35 0.2068(6) 0.5940(3) 0.3670(2) 0.0223(12) Uani d 1 . . C
H35 0.2031 0.658 0.3642 0.027 Uiso calc 1 . . H
C34 0.2015(6) 0.4466(3) 0.3367(2) 0.0219(12) Uani d 1 . . C
H34 0.1937 0.3918 0.3107 0.026 Uiso calc 1 . . H
C36 0.2359(6) 0.5460(3) 0.4252(2) 0.0204(12) Uani d 1 . . C
H36 0.2544 0.5703 0.4698 0.024 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O9 H9B . 0.96(5) ?
O9 H9C . 0.94(5) ?
S1 O5 . 1.434(3) ?
S1 O6 . 1.437(3) ?
S1 N4 . 1.635(3) ?
S1 C20 . 1.763(4) ?
O8 C23 . 1.261(5) ?
O7 C21 . 1.293(5) ?
N4 C22 . 1.456(5) ?
N4 C30 . 1.483(5) ?
N6 C24 . 1.344(5) ?
N6 C28 . 1.345(5) ?
N5 C23 . 1.368(5) ?
N5 C24 . 1.395(5) ?
N5 H5A . 0.91(4) ?
C22 C21 . 1.404(5) ?
C22 C23 . 1.436(5) ?
N7 C31 . 1.336(5) ?
N7 C32 . 1.368(5) ?
N7 H7A . 0.94(4) ?
N8 C31 . 1.332(5) ?
N8 C33 . 1.378(5) ?
N8 H8A . 0.84(4) ?
C24 C25 . 1.398(5) ?
C19 C20 . 1.397(5) ?
C19 C18 . 1.398(5) ?
C19 C21 . 1.489(5) ?
C18 C17 . 1.389(5) ?
C18 H18 . 0.93 ?
C20 C15 . 1.388(5) ?
C26 C25 . 1.377(5) ?
C26 C27 . 1.389(5) ?
C26 H26 . 0.93 ?
C16 C17 . 1.377(5) ?
C16 C15 . 1.394(5) ?
C16 H16 . 0.93 ?
C27 C28 . 1.372(5) ?
C27 H27 . 0.93 ?
C25 H25 . 0.93 ?
C30 H30A . 0.96 ?
C30 H30B . 0.96 ?
C30 H30C . 0.96 ?
C28 H28 . 0.93 ?
C33 C32 . 1.361(5) ?
C33 H33 . 0.93 ?
C32 H32 . 0.93 ?
C31 H31 . 0.93 ?
C17 H17 . 0.93 ?
C15 H15 . 0.93 ?
S2 O2 . 1.437(3) ?
S2 O1 . 1.442(3) ?
S2 N1 . 1.626(3) ?
S2 C3 . 1.766(4) ?
O4 C9 . 1.256(4) ?
O3 C7 . 1.282(4) ?
N1 C8 . 1.451(5) ?
N1 C29 . 1.480(5) ?
N2 C9 . 1.366(5) ?
N2 C10 . 1.395(5) ?
N2 H2A . 0.90(4) ?
C8 C7 . 1.401(5) ?
C8 C9 . 1.443(6) ?
N3 C14 . 1.329(5) ?
N3 C10 . 1.342(5) ?
C7 C4 . 1.495(6) ?
C3 C2 . 1.381(6) ?
C3 C4 . 1.402(6) ?
C4 C5 . 1.399(5) ?
C2 C1 . 1.384(5) ?
C2 H2 . 0.93 ?
C1 C6 . 1.385(6) ?
C1 H1 . 0.93 ?
C10 C11 . 1.397(6) ?
C12 C11 . 1.379(6) ?
C12 C13 . 1.384(6) ?
C12 H12 . 0.93 ?
C5 C6 . 1.389(6) ?
C5 H5 . 0.93 ?
C13 C14 . 1.376(6) ?
C13 H13 . 0.93 ?
C11 H11 . 0.93 ?
C6 H6 . 0.93 ?
C14 H14 . 0.93 ?
C29 H29A . 0.96 ?
C29 H29B . 0.96 ?
C29 H29C . 0.96 ?
N9 C34 . 1.337(5) ?
N9 C36 . 1.370(5) ?
N9 H9A . 0.90(4) ?
N10 C34 . 1.327(5) ?
N10 C35 . 1.375(5) ?
N10 H10A . 1.01(4) ?
C35 C36 . 1.361(5) ?
C35 H35 . 0.93 ?
C34 H34 . 0.93 ?
C36 H36 . 0.93 ?

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
H9B O9 H9C 103(4) . . ?
O5 S1 O6 119.02(17) . . ?
O5 S1 N4 108.49(17) . . ?
O6 S1 N4 108.17(17) . . ?
O5 S1 C20 110.11(18) . . ?
O6 S1 C20 107.79(17) . . ?
N4 S1 C20 101.89(19) . . ?
C22 N4 C30 114.8(3) . . ?
C22 N4 S1 113.6(3) . . ?
C30 N4 S1 117.0(3) . . ?
C24 N6 C28 117.7(3) . . ?
C23 N5 C24 128.4(4) . . ?
C23 N5 H5A 115(3) . . ?
C24 N5 H5A 115(3) . . ?
C21 C22 C23 125.2(4) . . ?
C21 C22 N4 120.4(4) . . ?
C23 C22 N4 114.4(4) . . ?
C31 N7 C32 108.9(4) . . ?
C31 N7 H7A 122(3) . . ?
C32 N7 H7A 129(3) . . ?
C31 N8 C33 109.0(4) . . ?
C31 N8 H8A 119(3) . . ?
C33 N8 H8A 131(3) . . ?
N6 C24 N5 113.0(3) . . ?
N6 C24 C25 123.0(4) . . ?
N5 C24 C25 124.0(4) . . ?
C20 C19 C18 117.4(4) . . ?
C20 C19 C21 122.8(4) . . ?
C18 C19 C21 119.7(4) . . ?
O8 C23 N5 121.3(4) . . ?
O8 C23 C22 123.4(4) . . ?
N5 C23 C22 115.3(4) . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
O7 C21 C22 123.8(4) . . ?
O7 C21 C19 116.7(4) . . ?
C22 C21 C19 119.5(4) . . ?
C15 C20 C19 122.5(4) . . ?
C15 C20 S1 121.1(3) . . ?
C19 C20 S1 116.2(3) . . ?
C25 C26 C27 120.1(4) . . ?
C25 C26 H26 120 . . ?
C27 C26 H26 120 . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C28 C27 C26 118.4(4) . . ?
C28 C27 H27 120.8 . . ?
C26 C27 H27 120.8 . . ?
C26 C25 C24 117.7(4) . . ?
C26 C25 H25 121.2 . . ?
C24 C25 H25 121.2 . . ?
N4 C30 H30A 109.5 . . ?
N4 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N4 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N6 C28 C27 123.2(4) . . ?
N6 C28 H28 118.4 . . ?
C27 C28 H28 118.4 . . ?
C32 C33 N8 106.6(4) . . ?
C32 C33 H33 126.7 . . ?
N8 C33 H33 126.7 . . ?
C33 C32 N7 107.3(4) . . ?
C33 C32 H32 126.3 . . ?
N7 C32 H32 126.3 . . ?
N8 C31 N7 108.2(4) . . ?
N8 C31 H31 125.9 . . ?
N7 C31 H31 125.9 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C20 C15 C16 118.7(4) . . ?
C20 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
O2 S2 O1 118.44(17) . . ?
O2 S2 N1 108.96(17) . . ?
O1 S2 N1 108.07(17) . . ?
O2 S2 C3 108.9(2) . . ?
O1 S2 C3 108.91(18) . . ?
N1 S2 C3 102.4(2) . . ?
C8 N1 C29 113.6(3) . . ?
C8 N1 S2 114.9(3) . . ?
C29 N1 S2 116.7(3) . . ?
C9 N2 C10 130.2(4) . . ?
C9 N2 H2A 113(3) . . ?
C10 N2 H2A 116(3) . . ?
C7 C8 C9 125.7(4) . . ?
C7 C8 N1 120.2(4) . . ?
C9 C8 N1 113.8(4) . . ?
C14 N3 C10 117.3(4) . . ?
O3 C7 C8 123.5(4) . . ?
O3 C7 C4 117.1(4) . . ?
C8 C7 C4 119.5(4) . . ?
O4 C9 N2 121.6(4) . . ?
O4 C9 C8 122.5(4) . . ?
N2 C9 C8 115.9(4) . . ?
C2 C3 C4 122.7(4) . . ?
C2 C3 S2 120.8(4) . . ?
C4 C3 S2 116.5(4) . . ?
C5 C4 C3 116.5(4) . . ?
C5 C4 C7 120.4(4) . . ?
C3 C4 C7 123.1(4) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C1 C6 119.8(5) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
N3 C10 N2 112.7(4) . . ?
N3 C10 C11 122.5(4) . . ?
N2 C10 C11 124.8(4) . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C14 C13 C12 116.8(4) . . ?
C14 C13 H13 121.6 . . ?
C12 C13 H13 121.6 . . ?
C12 C11 C10 117.9(4) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N3 C14 C13 125.0(4) . . ?
N3 C14 H14 117.5 . . ?
C13 C14 H14 117.5 . . ?
N1 C29 H29A 109.5 . . ?
N1 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N1 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C34 N9 C36 109.7(4) . . ?
C34 N9 H9A 127(3) . . ?
C36 N9 H9A 124(3) . . ?
C34 N10 C35 109.0(4) . . ?
C34 N10 H10A 126(2) . . ?
C35 N10 H10A 125(2) . . ?
C36 C35 N10 107.4(4) . . ?
C36 C35 H35 126.3 . . ?
N10 C35 H35 126.3 . . ?
N10 C34 N9 107.9(4) . . ?
N10 C34 H34 126.1 . . ?
N9 C34 H34 126.1 . . ?
C35 C36 N9 106.1(4) . . ?
C35 C36 H36 126.9 . . ?
N9 C36 H36 126.9 . . ?

# The following lines are used to test the character set of files sent by
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# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 984162'
#######################################################################
#
#                 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_piroximd

_audit_creation_date             2014-01-22T11:15:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C20 H20 N6 O4 S'
_chemical_formula_moiety         'C15 H12 N3 O4 S, C3 H5 N2, C2 H3 N'
_chemical_formula_weight         440.48

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.1510(5)
_cell_length_b                   26.5997(17)
_cell_length_c                   10.1579(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.394(3)
_cell_angle_gamma                90
_cell_volume                     2021.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8629
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_number            31169
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_theta_min         1.531
_diffrn_reflns_theta_max         29.606
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.99
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All hydrogen atoms were placed on calculated positions and modelled as riding
on the atoms to which they were bonded with the exception of those involved in
hydrogen bonding. H5, H13 and H16 were identified in difference Fourier maps
and their position and isotropic displacement parameter allowed to freely
refine. 
;
_reflns_number_total             5639
_reflns_number_gt                4386
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1699
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_number_reflns         5639
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+1.7277P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N6 0.9401(3) 0.57341(9) 0.9491(3) 0.0320(6) Uani d 1 . . N
C19 0.7255(4) 0.51229(11) 1.0047(3) 0.0253(5) Uani d 1 . . C
H19A 0.7844 0.4806 1.0369 0.038 Uiso calc 1 . . H
H19B 0.6194 0.5072 0.9194 0.038 Uiso calc 1 . . H
H19C 0.6939 0.5265 1.0782 0.038 Uiso calc 1 . . H
C20 0.8457(4) 0.54656(10) 0.9733(3) 0.0238(5) Uani d 1 . . C
H5 0.756(5) 0.2615(13) 0.210(4) 0.028(9) Uiso d 1 . . H
H16 -0.017(4) 0.2773(12) 0.567(3) 0.025(8) Uiso d 1 . . H
H13 0.290(5) 0.2296(14) 0.393(4) 0.036(10) Uiso d 1 . . H
S1 0.44824(7) 0.09732(2) 0.16071(6) 0.01302(14) Uani d 1 . . S
O4 0.4470(2) 0.24431(6) 0.30044(19) 0.0175(4) Uani d 1 . . O
O3 0.8415(2) 0.20228(6) 0.1518(2) 0.0182(4) Uani d 1 . . O
O2 0.3279(2) 0.11357(7) 0.02079(19) 0.0186(4) Uani d 1 . . O
N1 0.5086(2) 0.14549(7) 0.2675(2) 0.0136(4) Uani d 1 . . N
N2 0.6742(3) 0.27104(7) 0.2385(2) 0.0152(4) Uani d 1 . . N
O1 0.3890(2) 0.05823(6) 0.2303(2) 0.0190(4) Uani d 1 . . O
N3 0.8173(3) 0.34591(8) 0.2551(2) 0.0168(4) Uani d 1 . . N
C7 0.7415(3) 0.17026(8) 0.1796(2) 0.0129(4) Uani d 1 . . C
C8 0.6069(3) 0.18342(8) 0.2263(2) 0.0126(4) Uani d 1 . . C
C9 0.5673(3) 0.23460(8) 0.2571(2) 0.0130(4) Uani d 1 . . C
C5 0.7747(3) 0.11585(8) 0.1617(2) 0.0134(4) Uani d 1 . . C
C15 0.5868(3) 0.13415(10) 0.4230(3) 0.0198(5) Uani d 1 . . C
H15A 0.7018 0.1187 0.4482 0.03 Uiso calc 1 . . H
H15B 0.5094 0.1116 0.4452 0.03 Uiso calc 1 . . H
H15C 0.6 0.1648 0.4763 0.03 Uiso calc 1 . . H
C3 0.6826(3) 0.02761(9) 0.1404(2) 0.0158(4) Uani d 1 . . C
H3 0.599 0.0035 0.1384 0.019 Uiso calc 1 . . H
C4 0.6509(3) 0.07813(8) 0.1537(2) 0.0135(4) Uani d 1 . . C
C10 0.6744(3) 0.32253(9) 0.2633(2) 0.0145(4) Uani d 1 . . C
C2 0.8419(3) 0.01350(9) 0.1299(3) 0.0183(5) Uani d 1 . . C
H2 0.8647 -0.0202 0.1194 0.022 Uiso calc 1 . . H
C1 0.9664(3) 0.04991(9) 0.1350(3) 0.0175(5) Uani d 1 . . C
H1 1.0721 0.0405 0.1274 0.021 Uiso calc 1 . . H
C11 0.5391(3) 0.34830(9) 0.2879(3) 0.0167(4) Uani d 1 . . C
H11 0.4444 0.3311 0.2963 0.02 Uiso calc 1 . . H
C12 0.5508(4) 0.40007(9) 0.2993(3) 0.0204(5) Uani d 1 . . C
H12 0.4625 0.4182 0.3145 0.024 Uiso calc 1 . . H
C14 0.8240(3) 0.39609(9) 0.2674(3) 0.0201(5) Uani d 1 . . C
H14 0.9217 0.4126 0.2619 0.024 Uiso calc 1 . . H
C13 0.6942(4) 0.42505(9) 0.2879(3) 0.0211(5) Uani d 1 . . C
H13A 0.7031 0.4599 0.2938 0.025 Uiso calc 1 . . H
C6 0.9342(3) 0.10068(9) 0.1515(3) 0.0165(4) Uani d 1 . . C
H6 1.0192 0.1246 0.1557 0.02 Uiso calc 1 . . H
N4 0.2260(3) 0.23202(8) 0.4361(2) 0.0175(4) Uani d 1 . . N
N5 0.0498(3) 0.25720(8) 0.5345(2) 0.0165(4) Uani d 1 . . N
C17 0.1635(3) 0.18949(9) 0.4797(3) 0.0195(5) Uani d 1 . . C
H17 0.1921 0.1564 0.4685 0.023 Uiso calc 1 . . H
C16 0.0527(3) 0.20525(9) 0.5417(3) 0.0185(5) Uani d 1 . . C
H16A -0.0091 0.1851 0.5814 0.022 Uiso calc 1 . . H
C18 0.1556(3) 0.27238(9) 0.4705(3) 0.0168(5) Uani d 1 . . C
H18A 0.1766 0.3056 0.4529 0.02 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N6 C20 . 1.146(4) ?
C19 C20 . 1.462(4) ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
S1 O2 . 1.4360(18) ?
S1 O1 . 1.4438(17) ?
S1 N1 . 1.624(2) ?
S1 C4 . 1.757(2) ?
O4 C9 . 1.251(3) ?
O3 C7 . 1.286(3) ?
N1 C8 . 1.449(3) ?
N1 C15 . 1.481(3) ?
N2 C9 . 1.366(3) ?
N2 C10 . 1.393(3) ?
N2 H5 . 0.86(3) ?
N3 C14 . 1.340(3) ?
N3 C10 . 1.352(3) ?
C7 C8 . 1.401(3) ?
C7 C5 . 1.497(3) ?
C8 C9 . 1.461(3) ?
C5 C4 . 1.403(3) ?
C5 C6 . 1.404(3) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C3 C4 . 1.385(3) ?
C3 C2 . 1.397(3) ?
C3 H3 . 0.93 ?
C10 C11 . 1.402(3) ?
C2 C1 . 1.388(3) ?
C2 H2 . 0.93 ?
C1 C6 . 1.398(3) ?
C1 H1 . 0.93 ?
C11 C12 . 1.382(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.388(4) ?
C12 H12 . 0.93 ?
C14 C13 . 1.390(4) ?
C14 H14 . 0.93 ?
C13 H13A . 0.93 ?
C6 H6 . 0.93 ?
N4 C18 . 1.328(3) ?
N4 C17 . 1.383(3) ?
N4 H13 . 0.81(4) ?
N5 C18 . 1.332(3) ?
N5 C16 . 1.384(3) ?
N5 H16 . 0.91(3) ?
C17 C16 . 1.357(3) ?
C17 H17 . 0.93 ?
C16 H16A . 0.93 ?
C18 H18A . 0.93 ?

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
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 C19 179.8(4) . . ?
O2 S1 O1 118.13(11) . . ?
O2 S1 N1 109.28(10) . . ?
O1 S1 N1 108.23(10) . . ?
O2 S1 C4 109.34(11) . . ?
O1 S1 C4 108.24(11) . . ?
N1 S1 C4 102.47(10) . . ?
C8 N1 C15 113.35(18) . . ?
C8 N1 S1 114.35(15) . . ?
C15 N1 S1 116.08(16) . . ?
C9 N2 C10 128.9(2) . . ?
C9 N2 H5 117(2) . . ?
C10 N2 H5 114(2) . . ?
C14 N3 C10 117.2(2) . . ?
O3 C7 C8 124.0(2) . . ?
O3 C7 C5 116.91(19) . . ?
C8 C7 C5 119.1(2) . . ?
C7 C8 N1 121.4(2) . . ?
C7 C8 C9 125.0(2) . . ?
N1 C8 C9 113.11(18) . . ?
O4 C9 N2 122.3(2) . . ?
O4 C9 C8 122.6(2) . . ?
N2 C9 C8 115.12(19) . . ?
C4 C5 C6 117.1(2) . . ?
C4 C5 C7 122.5(2) . . ?
C6 C5 C7 120.3(2) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 122.8(2) . . ?
C3 C4 S1 120.05(17) . . ?
C5 C4 S1 117.15(17) . . ?
N3 C10 N2 112.3(2) . . ?
N3 C10 C11 122.9(2) . . ?
N2 C10 C11 124.7(2) . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C12 C11 C10 118.0(2) . . ?
C12 C11 H11 121 . . ?
C10 C11 H11 121 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
N3 C14 C13 124.1(2) . . ?
N3 C14 H14 117.9 . . ?
C13 C14 H14 117.9 . . ?
C12 C13 C14 117.6(2) . . ?
C12 C13 H13A 121.2 . . ?
C14 C13 H13A 121.2 . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C18 N4 C17 109.0(2) . . ?
C18 N4 H13 130(3) . . ?
C17 N4 H13 121(3) . . ?
C18 N5 C16 109.1(2) . . ?
C18 N5 H16 126(2) . . ?
C16 N5 H16 125(2) . . ?
C16 C17 N4 107.1(2) . . ?
C16 C17 H17 126.5 . . ?
N4 C17 H17 126.5 . . ?
C17 C16 N5 106.5(2) . . ?
C17 C16 H16A 126.7 . . ?
N5 C16 H16A 126.7 . . ?
N4 C18 N5 108.3(2) . . ?
N4 C18 H18A 125.8 . . ?
N5 C18 H18A 125.8 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 984163'
#######################################################################
#
#                 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.
# 
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#  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_shelxl


# start Validation Reply Form
_vrf_PLAT201_shelxl              
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          1 Why ? 
RESPONSE: There is disorder of the pyridine ring of one of the piroxicam 
molecules.  The two positions for the atom are too close to one another to
allow anisotropic refinement.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C15 H12 N3 O4 S), 4(C3 H5 N2), C2 H3 N'
_chemical_formula_sum            'C74 H71 N21 O16 S4'
_chemical_formula_weight         1638.76

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   P21/n

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                   6.91030(10)
_cell_length_b                   22.1444(5)
_cell_length_c                   25.1813(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0680(10)
_cell_angle_gamma                90.00
_cell_volume                     3824.07(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    56462
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.10

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1708
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  KappaCCD
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            55396
_diffrn_reflns_av_R_equivalents  0.1572
_diffrn_reflns_av_sigmaI/netI    0.1152
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.08
_reflns_number_total             8406
_reflns_number_gt                4565
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo & Scalepack(Otwinowski,Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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.

There is disorder in this structure involving the pyridine ring of the 
piroxicam molecule and the acetonitrile molecule.  The acetonitrile 
molecule is 50:50 disordered over an inversion centre.  The pyridine
ring of the piroxicam molecule is not disordered by symmetry.  However, when
the acetonitrile molecule is in one position, it lies too close to the
pyridine ring if it is in the B position.  The second position for the 
pyridine ring could be identified in a difference Fourier map and the 
occupancy was allowed to freely refine with the positions of the atoms
also freely refined but constrained to take the same value for the
anisotropic displacement parameter (using EADP) as its pair atom to ensure 
a stable refinement.  Atoms C12A and C12B were located too close to one 
another to allow anisotropic refinement and so these were only refined 
isotropically also using the EADP command.  The two parts A, and B, refined
to an occupancy ratio of 60:40.  It might be expected that due to the
50:50 disorder of the acetonitrile molecule, the pyridine ring should also
be 50:50 disordered.  The 60:40 ratio can be justified as there are only
unreasonable close contacts affecting the molecule when it is in the minor
40% occupied position.  So long as this value is less than 50%, there will
be no cases where these close contacts can exist.
 
Hydrogen atoms were identified in a difference Fourier map for all 
well-behaved molecules and their positions and isotropic displacement
parameters allowed to refine freely.  For the acetonitrile molecule and
the disordered piroxicam molecule, those hydrogen atoms which could be
identified clearly in a Fourier difference map and which were well 
behaved in terms of bond length and isotropic displacement parameter were
allowed to freely refine (position and isotropic displacement parameter)
but those involved in the disordered pyridine fragment and the benzene
ring were placed in calculated positions and refined as riding on the
atoms to which they were bonded.
;

_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)+(0.0666P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8406
_refine_ls_number_parameters     592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
N11 N 1.1606(7) 0.5239(2) 0.43875(19) 0.0315(12) Uani 0.50 1 d P . .
C37 C 1.1217(8) 0.5597(3) 0.4681(2) 0.0230(13) Uani 0.50 1 d P . .
C38 C 1.0714(8) 0.6056(3) 0.5059(2) 0.0260(14) Uani 0.50 1 d P . .
H38A H 0.9751 0.5897 0.5265 0.039 Uiso 0.50 1 calc PR . .
H38B H 1.0202 0.6406 0.4865 0.039 Uiso 0.50 1 calc PR . .
H38C H 1.1860 0.6166 0.5294 0.039 Uiso 0.50 1 calc PR . .
H12 H 0.469(4) 0.8922(13) 0.1804(12) 0.037(9) Uiso 1 1 d . . .
H3 H 1.000(4) 0.4048(13) 0.1891(12) 0.030(9) Uiso 1 1 d . . .
H2 H 0.911(4) 0.3803(14) 0.1330(12) 0.034(9) Uiso 1 1 d . . .
H13 H 0.387(4) 0.9106(13) 0.1214(11) 0.020(8) Uiso 1 1 d . . .
H14 H 0.280(4) 0.7268(14) 0.2625(11) 0.032(9) Uiso 1 1 d . . .
H10 H 0.772(4) 0.5703(14) 0.2667(12) 0.038(9) Uiso 1 1 d . . .
H7 H 0.764(4) 0.6798(14) 0.2193(12) 0.036(9) Uiso 1 1 d . . .
H1 H 1.022(5) 0.4447(15) 0.1401(12) 0.046(10) Uiso 1 1 d . . .
H22 H 0.210(5) 0.9403(16) 0.2377(13) 0.055(11) Uiso 1 1 d . . .
H24 H 0.504(4) 0.8475(13) 0.1284(11) 0.024(8) Uiso 1 1 d . . .
H31 H 0.773(5) 0.8552(16) 0.2584(13) 0.054(11) Uiso 1 1 d . . .
H32 H 0.229(4) 1.1076(14) 0.2793(12) 0.036(10) Uiso 1 1 d . . .
S1 S 0.61019(10) 0.45682(3) 0.10221(3) 0.0244(2) Uani 1 1 d . . .
O3 O 0.7856(3) 0.60328(9) 0.20315(8) 0.0301(5) Uani 1 1 d . . .
N1 N 0.7461(3) 0.44500(10) 0.15937(9) 0.0227(6) Uani 1 1 d . . .
O2 O 0.4192(3) 0.47399(9) 0.11296(7) 0.0278(5) Uani 1 1 d . . .
O1 O 0.6276(3) 0.40592(9) 0.06807(7) 0.0291(5) Uani 1 1 d . . .
O4 O 0.7314(3) 0.42856(9) 0.26652(7) 0.0263(5) Uani 1 1 d . . .
C8 C 0.7556(4) 0.49682(13) 0.19456(11) 0.0226(7) Uani 1 1 d . . .
N2 N 0.7558(3) 0.53000(11) 0.28425(9) 0.0251(6) Uani 1 1 d . A .
C4 C 0.7290(4) 0.51920(13) 0.07792(11) 0.0222(7) Uani 1 1 d . . .
C10 C 0.7453(4) 0.48175(13) 0.25069(11) 0.0225(7) Uani 1 1 d . . .
C3 C 0.7997(4) 0.56216(13) 0.11637(11) 0.0239(7) Uani 1 1 d . . .
C7 C 0.7783(4) 0.55499(13) 0.17457(11) 0.0226(7) Uani 1 1 d . . .
C1 C 0.9274(4) 0.61705(14) 0.04569(12) 0.0304(8) Uani 1 1 d . . .
H1A H 0.9927 0.6506 0.0345 0.036 Uiso 1 1 calc R . .
C6 C 0.8621(4) 0.57293(14) 0.00887(12) 0.0292(7) Uani 1 1 d . . .
H6 H 0.8857 0.5766 -0.0266 0.035 Uiso 1 1 calc R . .
C9 C 0.9371(5) 0.41690(16) 0.15428(15) 0.0290(8) Uani 1 1 d . . .
C5 C 0.7615(4) 0.52332(13) 0.02479(11) 0.0259(7) Uani 1 1 d . . .
H5 H 0.7168 0.4934 0.0004 0.031 Uiso 1 1 calc R . .
C11 C 0.7377(5) 0.53224(14) 0.33869(12) 0.0316(8) Uani 1 1 d . . .
C2 C 0.8971(4) 0.61221(13) 0.09934(12) 0.0274(7) Uani 1 1 d . . .
H2A H 0.9417 0.6423 0.1236 0.033 Uiso 1 1 calc R . .
S2 S 0.09059(11) 0.82700(3) 0.09394(3) 0.0261(2) Uani 1 1 d . . .
O7 O 0.3032(3) 0.68885(9) 0.20073(7) 0.0276(5) Uani 1 1 d . . .
O8 O 0.2165(3) 0.86442(8) 0.25694(7) 0.0260(5) Uani 1 1 d . . .
N5 N 0.2614(3) 0.76491(11) 0.27844(9) 0.0235(6) Uani 1 1 d . . .
O6 O 0.0989(3) 0.87535(9) 0.05651(8) 0.0319(5) Uani 1 1 d . . .
C25 C 0.2586(4) 0.76415(13) 0.33399(11) 0.0218(7) Uani 1 1 d . . .
N4 N 0.2271(3) 0.84379(10) 0.14965(9) 0.0249(6) Uani 1 1 d . . .
O5 O -0.0966(3) 0.80829(9) 0.10663(8) 0.0311(5) Uani 1 1 d . . .
C20 C 0.2976(4) 0.72500(13) 0.11171(11) 0.0228(7) Uani 1 1 d . . .
C19 C 0.3985(4) 0.67495(13) 0.09588(11) 0.0263(7) Uani 1 1 d . . .
H19 H 0.4540 0.6477 0.1214 0.032 Uiso 1 1 calc R . .
C23 C 0.2489(4) 0.79376(12) 0.18711(11) 0.0213(6) Uani 1 1 d . . .
C24 C 0.2393(4) 0.81137(13) 0.24286(11) 0.0207(6) Uani 1 1 d . . .
C26 C 0.2158(4) 0.81400(13) 0.36413(11) 0.0244(7) Uani 1 1 d . . .
H26 H 0.1892 0.8515 0.3483 0.029 Uiso 1 1 calc R . .
C21 C 0.2153(4) 0.76439(13) 0.07223(11) 0.0224(7) Uani 1 1 d . . .
C16 C 0.2341(4) 0.75595(13) 0.01833(11) 0.0260(7) Uani 1 1 d . . .
H16 H 0.1804 0.7834 -0.0073 0.031 Uiso 1 1 calc R . .
C22 C 0.2825(4) 0.73538(13) 0.17006(11) 0.0226(7) Uani 1 1 d . . .
C30 C 0.4125(5) 0.87567(15) 0.14310(14) 0.0301(8) Uani 1 1 d . . .
N6 N 0.2973(4) 0.70953(11) 0.35486(10) 0.0315(6) Uani 1 1 d . . .
C29 C 0.2143(4) 0.80547(14) 0.41873(11) 0.0270(7) Uani 1 1 d . . .
H29 H 0.1872 0.8378 0.4403 0.032 Uiso 1 1 calc R . .
C27 C 0.2938(5) 0.70313(15) 0.40791(12) 0.0366(8) Uani 1 1 d . . .
H27 H 0.3208 0.6652 0.4230 0.044 Uiso 1 1 calc R . .
C17 C 0.3347(4) 0.70571(14) 0.00375(12) 0.0288(7) Uani 1 1 d . . .
H17 H 0.3470 0.6989 -0.0321 0.035 Uiso 1 1 calc R . .
C18 C 0.4168(4) 0.66561(14) 0.04221(12) 0.0286(7) Uani 1 1 d . . .
H18 H 0.4847 0.6321 0.0320 0.034 Uiso 1 1 calc R . .
C28 C 0.2526(4) 0.74945(14) 0.44101(12) 0.0320(8) Uani 1 1 d . . .
H28 H 0.2507 0.7431 0.4774 0.038 Uiso 1 1 calc R . .
N7 N 0.7742(3) 0.71740(12) 0.23902(10) 0.0275(6) Uani 1 1 d . . .
N8 N 0.7806(3) 0.81134(12) 0.26164(10) 0.0272(6) Uani 1 1 d . . .
C31 C 0.7832(4) 0.77361(13) 0.22055(12) 0.0260(7) Uani 1 1 d . . .
H31A H 0.7899 0.7846 0.1852 0.031 Uiso 1 1 calc R . .
C33 C 0.7676(4) 0.77825(13) 0.30717(12) 0.0274(7) Uani 1 1 d . . .
H33 H 0.7625 0.7934 0.3414 0.033 Uiso 1 1 calc R . .
C32 C 0.7634(4) 0.71952(13) 0.29281(12) 0.0278(7) Uani 1 1 d . . .
H32A H 0.7548 0.6866 0.3153 0.033 Uiso 1 1 calc R . .
N9 N 0.2199(3) 0.98377(12) 0.23377(10) 0.0263(6) Uani 1 1 d . . .
N10 N 0.2204(3) 1.07618(12) 0.26051(11) 0.0269(6) Uani 1 1 d . . .
C34 C 0.2475(5) 1.02002(14) 0.19099(12) 0.0344(8) Uani 1 1 d . . .
H34 H 0.2632 1.0069 0.1567 0.041 Uiso 1 1 calc R . .
C36 C 0.2037(4) 1.01931(13) 0.27546(12) 0.0249(7) Uani 1 1 d . . .
H36 H 0.1840 1.0064 0.3095 0.030 Uiso 1 1 calc R . .
C35 C 0.2478(4) 1.07697(14) 0.20724(13) 0.0327(8) Uani 1 1 d . . .
H35 H 0.2634 1.1110 0.1866 0.039 Uiso 1 1 calc R . .
C14A C 0.6308(8) 0.5570(2) 0.4365(2) 0.0356(12) Uani 0.597(3) 1 d P A 1
H14A H 0.5984 0.5664 0.4703 0.043 Uiso 0.597(3) 1 calc PR A 1
C13A C 0.6876(9) 0.6010(3) 0.4031(2) 0.0329(13) Uani 0.597(3) 1 d P A 1
H13A H 0.6964 0.6404 0.4158 0.039 Uiso 0.597(3) 1 calc PR A 1
C15A C 0.6239(8) 0.4980(3) 0.4178(2) 0.0290(12) Uani 0.597(3) 1 d P A 1
H15A H 0.5963 0.4662 0.4399 0.035 Uiso 0.597(3) 1 calc PR A 1
N3A N 0.7310(10) 0.5911(4) 0.3535(4) 0.0256(15) Uani 0.597(3) 1 d P A 1
C12A C 0.6584(12) 0.4874(4) 0.3663(4) 0.0258(10) Uiso 0.403(3) 1 d P A 1
H12A H 0.6282 0.4501 0.3504 0.031 Uiso 0.403(3) 1 calc PR A 1
C14B C 0.7725(13) 0.5437(4) 0.4508(3) 0.0356(12) Uani 0.403(3) 1 d P A 2
H14B H 0.7761 0.5503 0.4874 0.043 Uiso 0.403(3) 1 calc PR A 2
C13B C 0.8075(13) 0.5905(4) 0.4158(4) 0.0329(13) Uani 0.403(3) 1 d P A 2
H13B H 0.8355 0.6284 0.4306 0.039 Uiso 0.403(3) 1 calc PR A 2
C15B C 0.7329(12) 0.4882(4) 0.4290(4) 0.0290(12) Uani 0.403(3) 1 d P A 2
H15B H 0.7169 0.4553 0.4510 0.035 Uiso 0.403(3) 1 calc PR A 2
N3B N 0.8039(16) 0.5850(7) 0.3634(6) 0.0256(15) Uani 0.403(3) 1 d P A 2
C12B C 0.7162(8) 0.4806(3) 0.3724(2) 0.0258(10) Uiso 0.597(3) 1 d P A 2
H12B H 0.6915 0.4426 0.3573 0.031 Uiso 0.597(3) 1 calc PR A 2


_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
N11 C37 1.138(7) . ?
C37 C38 1.464(8) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
S1 O2 1.4307(19) . ?
S1 O1 1.4316(19) . ?
S1 N1 1.640(2) . ?
S1 C4 1.755(3) . ?
O3 C7 1.287(3) . ?
N1 C8 1.446(3) . ?
N1 C9 1.479(4) . ?
O4 C10 1.251(3) . ?
C8 C7 1.399(4) . ?
C8 C10 1.463(4) . ?
N2 C10 1.359(3) . ?
N2 C11 1.393(4) . ?
N2 H10 1.01(3) . ?
C4 C5 1.387(4) . ?
C4 C3 1.402(4) . ?
C3 C2 1.391(4) . ?
C3 C7 1.499(4) . ?
C1 C6 1.384(4) . ?
C1 C2 1.396(4) . ?
C1 H1A 0.9300 . ?
C6 C5 1.385(4) . ?
C6 H6 0.9300 . ?
C9 H3 0.97(3) . ?
C9 H2 0.98(3) . ?
C9 H1 0.95(3) . ?
C5 H5 0.9300 . ?
C11 N3A 1.358(10) . ?
C11 C12A 1.366(9) . ?
C11 N3B 1.374(16) . ?
C11 C12B 1.443(7) . ?
C2 H2A 0.9300 . ?
S2 O5 1.431(2) . ?
S2 O6 1.432(2) . ?
S2 N4 1.634(2) . ?
S2 C21 1.755(3) . ?
O7 C22 1.285(3) . ?
O8 C24 1.243(3) . ?
N5 C24 1.361(4) . ?
N5 C25 1.401(3) . ?
N5 H14 0.95(3) . ?
C25 N6 1.333(4) . ?
C25 C26 1.392(4) . ?
N4 C23 1.451(3) . ?
N4 C30 1.489(4) . ?
C20 C21 1.391(4) . ?
C20 C19 1.394(4) . ?
C20 C22 1.504(4) . ?
C19 C18 1.388(4) . ?
C19 H19 0.9300 . ?
C23 C22 1.391(4) . ?
C23 C24 1.466(4) . ?
C26 C29 1.389(4) . ?
C26 H26 0.9300 . ?
C21 C16 1.392(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C30 H12 1.04(3) . ?
C30 H13 0.95(3) . ?
C30 H24 0.99(3) . ?
N6 C27 1.346(4) . ?
C29 C28 1.374(4) . ?
C29 H29 0.9300 . ?
C27 C28 1.373(4) . ?
C27 H27 0.9300 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C28 H28 0.9300 . ?
N7 C31 1.333(4) . ?
N7 C32 1.367(4) . ?
N7 H7 0.97(3) . ?
N8 C31 1.332(4) . ?
N8 C33 1.373(4) . ?
N8 H31 0.98(3) . ?
C31 H31A 0.9300 . ?
C33 C32 1.349(4) . ?
C33 H33 0.9300 . ?
C32 H32A 0.9300 . ?
N9 C36 1.328(4) . ?
N9 C34 1.375(4) . ?
N9 H22 0.97(3) . ?
N10 C36 1.324(4) . ?
N10 C35 1.378(4) . ?
N10 H32 0.84(3) . ?
C34 C35 1.326(4) . ?
C34 H34 0.9300 . ?
C36 H36 0.9300 . ?
C35 H35 0.9300 . ?
C14A C13A 1.377(7) . ?
C14A C15A 1.388(8) . ?
C14A H14A 0.9300 . ?
C13A N3A 1.336(11) . ?
C13A H13A 0.9300 . ?
C15A C12A 1.367(10) . ?
C15A H15A 0.9300 . ?
C12A H12A 0.9300 . ?
C14B C15B 1.359(12) . ?
C14B C13B 1.400(12) . ?
C14B H14B 0.9300 . ?
C13B N3B 1.323(18) . ?
C13B H13B 0.9300 . ?
C15B C12B 1.426(11) . ?
C15B H15B 0.9300 . ?
C12B H12B 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
N11 C37 C38 179.9(7) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O2 S1 O1 118.06(12) . . ?
O2 S1 N1 108.56(11) . . ?
O1 S1 N1 108.66(12) . . ?
O2 S1 C4 109.78(12) . . ?
O1 S1 C4 109.47(12) . . ?
N1 S1 C4 100.93(13) . . ?
C8 N1 C9 114.4(2) . . ?
C8 N1 S1 112.89(18) . . ?
C9 N1 S1 114.3(2) . . ?
C7 C8 N1 120.6(2) . . ?
C7 C8 C10 125.4(3) . . ?
N1 C8 C10 114.0(2) . . ?
C10 N2 C11 129.5(3) . . ?
C10 N2 H10 115.0(17) . . ?
C11 N2 H10 115.4(17) . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 S1 121.8(2) . . ?
C3 C4 S1 115.6(2) . . ?
O4 C10 N2 122.9(3) . . ?
O4 C10 C8 122.5(3) . . ?
N2 C10 C8 114.6(3) . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 C7 119.7(3) . . ?
C4 C3 C7 122.4(2) . . ?
O3 C7 C8 124.2(3) . . ?
O3 C7 C3 117.2(2) . . ?
C8 C7 C3 118.6(3) . . ?
C6 C1 C2 121.2(3) . . ?
C6 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N1 C9 H3 110.1(16) . . ?
N1 C9 H2 107.0(17) . . ?
H3 C9 H2 107(2) . . ?
N1 C9 H1 111.0(19) . . ?
H3 C9 H1 107(3) . . ?
H2 C9 H1 114(3) . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N3A C11 C12A 121.9(6) . . ?
N3A C11 N3B 23.2(5) . . ?
C12A C11 N3B 121.3(8) . . ?
N3A C11 N2 108.4(5) . . ?
C12A C11 N2 124.5(5) . . ?
N3B C11 N2 114.2(7) . . ?
N3A C11 C12B 126.1(5) . . ?
C12A C11 C12B 17.6(4) . . ?
N3B C11 C12B 117.4(7) . . ?
N2 C11 C12B 125.4(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
O5 S2 O6 118.28(12) . . ?
O5 S2 N4 108.44(12) . . ?
O6 S2 N4 109.22(12) . . ?
O5 S2 C21 109.43(13) . . ?
O6 S2 C21 108.95(12) . . ?
N4 S2 C21 101.16(13) . . ?
C24 N5 C25 130.7(3) . . ?
C24 N5 H14 113.8(17) . . ?
C25 N5 H14 115.4(17) . . ?
N6 C25 C26 123.4(3) . . ?
N6 C25 N5 112.2(2) . . ?
C26 C25 N5 124.4(3) . . ?
C23 N4 C30 114.3(2) . . ?
C23 N4 S2 112.77(18) . . ?
C30 N4 S2 115.2(2) . . ?
C21 C20 C19 118.0(2) . . ?
C21 C20 C22 122.1(2) . . ?
C19 C20 C22 119.9(3) . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C22 C23 N4 121.1(2) . . ?
C22 C23 C24 124.9(3) . . ?
N4 C23 C24 114.0(2) . . ?
O8 C24 N5 122.3(3) . . ?
O8 C24 C23 123.2(3) . . ?
N5 C24 C23 114.5(2) . . ?
C29 C26 C25 117.4(3) . . ?
C29 C26 H26 121.3 . . ?
C25 C26 H26 121.3 . . ?
C20 C21 C16 122.3(3) . . ?
C20 C21 S2 116.5(2) . . ?
C16 C21 S2 121.2(2) . . ?
C17 C16 C21 118.4(3) . . ?
C17 C16 H16 120.8 . . ?
C21 C16 H16 120.8 . . ?
O7 C22 C23 124.8(3) . . ?
O7 C22 C20 116.7(2) . . ?
C23 C22 C20 118.6(3) . . ?
N4 C30 H12 107.5(15) . . ?
N4 C30 H13 110.6(16) . . ?
H12 C30 H13 105(2) . . ?
N4 C30 H24 109.8(16) . . ?
H12 C30 H24 112(2) . . ?
H13 C30 H24 112(2) . . ?
C25 N6 C27 117.4(3) . . ?
C28 C29 C26 120.2(3) . . ?
C28 C29 H29 119.9 . . ?
C26 C29 H29 119.9 . . ?
N6 C27 C28 123.6(3) . . ?
N6 C27 H27 118.2 . . ?
C28 C27 H27 118.2 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C27 C28 C29 118.1(3) . . ?
C27 C28 H28 121.0 . . ?
C29 C28 H28 121.0 . . ?
C31 N7 C32 108.9(3) . . ?
C31 N7 H7 129.0(18) . . ?
C32 N7 H7 121.9(17) . . ?
C31 N8 C33 108.8(3) . . ?
C31 N8 H31 124(2) . . ?
C33 N8 H31 126(2) . . ?
N8 C31 N7 108.0(3) . . ?
N8 C31 H31A 126.0 . . ?
N7 C31 H31A 126.0 . . ?
C32 C33 N8 107.0(3) . . ?
C32 C33 H33 126.5 . . ?
N8 C33 H33 126.5 . . ?
C33 C32 N7 107.3(3) . . ?
C33 C32 H32A 126.4 . . ?
N7 C32 H32A 126.4 . . ?
C36 N9 C34 107.8(3) . . ?
C36 N9 H22 119(2) . . ?
C34 N9 H22 133(2) . . ?
C36 N10 C35 108.4(3) . . ?
C36 N10 H32 129(2) . . ?
C35 N10 H32 122(2) . . ?
C35 C34 N9 108.0(3) . . ?
C35 C34 H34 126.0 . . ?
N9 C34 H34 126.0 . . ?
N10 C36 N9 108.7(3) . . ?
N10 C36 H36 125.7 . . ?
N9 C36 H36 125.7 . . ?
C34 C35 N10 107.1(3) . . ?
C34 C35 H35 126.5 . . ?
N10 C35 H35 126.5 . . ?
C13A C14A C15A 117.4(5) . . ?
C13A C14A H14A 121.3 . . ?
C15A C14A H14A 121.3 . . ?
N3A C13A C14A 124.7(7) . . ?
N3A C13A H13A 117.7 . . ?
C14A C13A H13A 117.7 . . ?
C12A C15A C14A 118.7(6) . . ?
C12A C15A H15A 120.7 . . ?
C14A C15A H15A 120.7 . . ?
C13A N3A C11 115.7(8) . . ?
C11 C12A C15A 119.1(8) . . ?
C11 C12A H12A 120.4 . . ?
C15A C12A H12A 120.4 . . ?
C15B C14B C13B 117.2(8) . . ?
C15B C14B H14B 121.4 . . ?
C13B C14B H14B 121.4 . . ?
N3B C13B C14B 125.2(11) . . ?
N3B C13B H13B 117.4 . . ?
C14B C13B H13B 117.4 . . ?
C14B C15B C12B 119.9(8) . . ?
C14B C15B H15B 120.1 . . ?
C12B C15B H15B 120.1 . . ?
C13B N3B C11 119.6(13) . . ?
C15B C12B C11 119.5(6) . . ?
C15B C12B H12B 120.2 . . ?
C11 C12B H12B 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.08
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 984164'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N3 O4 S, C4 H7 N2'
_chemical_formula_sum            'C19 H19 N5 O4 S'
_chemical_formula_weight         413.45

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   P21/n

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                   10.9928(8)
_cell_length_b                   15.3135(15)
_cell_length_c                   12.5510(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.039(4)
_cell_angle_gamma                90.00
_cell_volume                     1958.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22807
_cell_measurement_theta_min      1
_cell_measurement_theta_max      56.82

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7637
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22181
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         28.31
_reflns_number_total             4828
_reflns_number_gt                3085
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0597P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4828
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
H12 H -0.040(2) 0.1844(16) -0.2005(19) 0.017(6) Uiso 1 1 d . . .
H7 H 0.603(2) 0.0456(17) 0.283(2) 0.022(7) Uiso 1 1 d . . .
H10 H 0.443(2) 0.1701(16) 0.548(2) 0.018(6) Uiso 1 1 d . . .
H14 H 0.008(2) 0.1365(17) -0.499(2) 0.026(7) Uiso 1 1 d . . .
H11 H 0.281(3) 0.1056(19) -0.038(2) 0.043(9) Uiso 1 1 d . . .
H9 H 0.652(3) 0.1123(18) 0.608(2) 0.032(8) Uiso 1 1 d . . .
H15 H 0.211(2) 0.0721(18) -0.397(2) 0.032(7) Uiso 1 1 d . . .
H2 H 0.748(2) 0.2138(17) 0.299(2) 0.028(7) Uiso 1 1 d . . .
H8 H 0.732(2) 0.0514(16) 0.4781(19) 0.018(6) Uiso 1 1 d . . .
H13 H -0.126(3) 0.1956(18) -0.404(2) 0.030(7) Uiso 1 1 d . . .
H3 H 0.582(3) 0.144(2) 0.116(3) 0.060(10) Uiso 1 1 d . . .
H1 H 0.962(3) 0.221(2) 0.261(2) 0.041(8) Uiso 1 1 d . . .
H16 H 0.189(3) -0.0057(17) 0.277(2) 0.022(7) Uiso 1 1 d . . .
H17 H 0.063(2) 0.0047(16) 0.167(2) 0.018(6) Uiso 1 1 d . . .
H18 H 0.069(3) 0.0370(19) 0.286(2) 0.040(8) Uiso 1 1 d . . .
H4 H 0.909(3) 0.150(2) 0.056(3) 0.070(11) Uiso 1 1 d . . .
S1 S 0.23587(5) 0.18498(4) 0.32240(5) 0.01782(16) Uani 1 1 d . . .
O3 O 0.42623(14) 0.10858(11) 0.10072(13) 0.0196(4) Uani 1 1 d . . .
O1 O 0.17831(15) 0.17280(12) 0.40677(14) 0.0248(4) Uani 1 1 d . . .
O4 O 0.01457(14) 0.13016(11) -0.01435(13) 0.0204(4) Uani 1 1 d . . .
O2 O 0.23604(15) 0.27092(11) 0.27769(13) 0.0213(4) Uani 1 1 d . . .
N4 N 0.1913(2) 0.11646(14) -0.06772(16) 0.0204(5) Uani 1 1 d . . .
N3 N 0.16309(17) 0.11994(13) 0.21372(15) 0.0164(4) Uani 1 1 d . . .
C11 C 0.3629(2) 0.11188(15) 0.16892(19) 0.0163(5) Uani 1 1 d . . .
C8 C 0.3970(2) 0.14312(15) 0.37679(19) 0.0167(5) Uani 1 1 d . . .
N5 N 0.2034(2) 0.09033(15) -0.24353(17) 0.0257(5) Uani 1 1 d . . .
C12 C 0.2275(2) 0.11856(15) 0.13172(19) 0.0162(5) Uani 1 1 d . . .
C9 C 0.4432(2) 0.10870(15) 0.29609(19) 0.0167(5) Uani 1 1 d . . .
C13 C 0.1351(2) 0.12274(16) 0.0124(2) 0.0171(5) Uani 1 1 d . . .
C5 C 0.6449(2) 0.07386(17) 0.4548(2) 0.0236(6) Uani 1 1 d . . .
C15 C 0.0075(2) 0.16074(16) -0.2435(2) 0.0184(5) Uani 1 1 d . . .
C19 C 0.1195(3) 0.03384(18) 0.2394(2) 0.0216(5) Uani 1 1 d . . .
C10 C 0.5696(2) 0.07235(17) 0.3373(2) 0.0207(5) Uani 1 1 d . . .
C17 C -0.0409(2) 0.16650(17) -0.3623(2) 0.0209(5) Uani 1 1 d . . .
C7 C 0.4715(2) 0.14424(17) 0.4940(2) 0.0221(6) Uani 1 1 d . . .
C14 C 0.1297(2) 0.12210(16) -0.18867(19) 0.0178(5) Uani 1 1 d . . .
C16 C 0.1537(3) 0.09785(19) -0.3586(2) 0.0301(6) Uani 1 1 d . . .
C6 C 0.5976(2) 0.11020(18) 0.5323(2) 0.0260(6) Uani 1 1 d . . .
C18 C 0.0335(3) 0.13378(19) -0.4217(2) 0.0277(6) Uani 1 1 d . . .
N1 N 0.6717(2) 0.15563(15) 0.13315(19) 0.0262(5) Uani 1 1 d . . .
N2 N 0.8517(2) 0.16157(15) 0.10215(19) 0.0269(5) Uani 1 1 d . . .
C1 C 0.7269(2) 0.13709(16) 0.0592(2) 0.0228(6) Uani 1 1 d . . .
C2 C 0.6583(3) 0.09555(18) -0.0553(2) 0.0320(6) Uani 1 1 d . . .
H5A H 0.6139 0.0438 -0.0462 0.048 Uiso 1 1 calc R . .
H5B H 0.7213 0.0804 -0.0884 0.048 Uiso 1 1 calc R . .
H5C H 0.5955 0.1358 -0.1051 0.048 Uiso 1 1 calc R . .
C3 C 0.8766(3) 0.19803(19) 0.2099(2) 0.0307(7) Uani 1 1 d . . .
C4 C 0.7659(2) 0.19441(19) 0.2293(2) 0.0294(6) Uani 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 O2 1.4309(18) . ?
S1 O1 1.4350(17) . ?
S1 N3 1.6351(19) . ?
S1 C8 1.762(2) . ?
O3 C11 1.291(3) . ?
O4 C13 1.244(2) . ?
N4 C13 1.367(3) . ?
N4 C14 1.414(3) . ?
N4 H11 0.93(3) . ?
N3 C12 1.452(3) . ?
N3 C19 1.479(3) . ?
C11 C12 1.387(3) . ?
C11 C9 1.507(3) . ?
C8 C7 1.390(3) . ?
C8 C9 1.395(3) . ?
N5 C14 1.336(3) . ?
N5 C16 1.344(3) . ?
C12 C13 1.462(3) . ?
C9 C10 1.403(3) . ?
C5 C6 1.380(4) . ?
C5 C10 1.394(3) . ?
C5 H8 0.96(2) . ?
C15 C17 1.385(3) . ?
C15 C14 1.391(3) . ?
C15 H12 0.95(2) . ?
C19 H16 0.95(3) . ?
C19 H17 0.99(2) . ?
C19 H18 0.95(3) . ?
C10 H7 0.98(2) . ?
C17 C18 1.390(4) . ?
C17 H13 0.99(3) . ?
C7 C6 1.387(3) . ?
C7 H10 0.93(2) . ?
C16 C18 1.375(4) . ?
C16 H15 1.01(3) . ?
C6 H9 0.91(3) . ?
C18 H14 0.91(3) . ?
N1 C1 1.317(3) . ?
N1 C4 1.394(3) . ?
N1 H3 0.94(3) . ?
N2 C1 1.326(3) . ?
N2 C3 1.392(3) . ?
N2 H4 1.01(3) . ?
C1 C2 1.492(4) . ?
C2 H5A 0.9600 . ?
C2 H5B 0.9600 . ?
C2 H5C 0.9600 . ?
C3 C4 1.329(4) . ?
C3 H1 0.99(3) . ?
C4 H2 1.01(2) . ?

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 118.34(10) . . ?
O2 S1 N3 107.78(10) . . ?
O1 S1 N3 108.86(10) . . ?
O2 S1 C8 109.72(10) . . ?
O1 S1 C8 108.92(11) . . ?
N3 S1 C8 101.98(10) . . ?
C13 N4 C14 128.2(2) . . ?
C13 N4 H11 115.3(17) . . ?
C14 N4 H11 116.4(17) . . ?
C12 N3 C19 115.20(19) . . ?
C12 N3 S1 112.59(14) . . ?
C19 N3 S1 117.27(15) . . ?
O3 C11 C12 123.9(2) . . ?
O3 C11 C9 116.99(19) . . ?
C12 C11 C9 119.1(2) . . ?
C7 C8 C9 122.8(2) . . ?
C7 C8 S1 120.88(19) . . ?
C9 C8 S1 116.28(17) . . ?
C14 N5 C16 116.3(2) . . ?
C11 C12 N3 120.65(19) . . ?
C11 C12 C13 126.4(2) . . ?
N3 C12 C13 112.94(18) . . ?
C8 C9 C10 117.5(2) . . ?
C8 C9 C11 121.9(2) . . ?
C10 C9 C11 120.6(2) . . ?
O4 C13 N4 122.5(2) . . ?
O4 C13 C12 122.7(2) . . ?
N4 C13 C12 114.76(19) . . ?
C6 C5 C10 121.3(2) . . ?
C6 C5 H8 122.0(14) . . ?
C10 C5 H8 116.6(14) . . ?
C17 C15 C14 118.0(2) . . ?
C17 C15 H12 121.0(14) . . ?
C14 C15 H12 120.9(14) . . ?
N3 C19 H16 114.2(15) . . ?
N3 C19 H17 109.9(14) . . ?
H16 C19 H17 106(2) . . ?
N3 C19 H18 113.7(18) . . ?
H16 C19 H18 106(2) . . ?
H17 C19 H18 106(2) . . ?
C5 C10 C9 119.8(2) . . ?
C5 C10 H7 121.1(14) . . ?
C9 C10 H7 119.1(14) . . ?
C15 C17 C18 119.2(2) . . ?
C15 C17 H13 120.0(14) . . ?
C18 C17 H13 120.7(14) . . ?
C6 C7 C8 118.5(2) . . ?
C6 C7 H10 118.3(15) . . ?
C8 C7 H10 123.1(15) . . ?
N5 C14 C15 124.0(2) . . ?
N5 C14 N4 113.1(2) . . ?
C15 C14 N4 122.8(2) . . ?
N5 C16 C18 124.6(2) . . ?
N5 C16 H15 114.3(15) . . ?
C18 C16 H15 121.1(15) . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H9 118.2(17) . . ?
C7 C6 H9 121.8(17) . . ?
C16 C18 C17 117.9(2) . . ?
C16 C18 H14 118.8(16) . . ?
C17 C18 H14 123.3(16) . . ?
C1 N1 C4 108.2(2) . . ?
C1 N1 H3 121(2) . . ?
C4 N1 H3 131(2) . . ?
C1 N2 C3 107.7(2) . . ?
C1 N2 H4 119.0(19) . . ?
C3 N2 H4 133.3(19) . . ?
N1 C1 N2 109.5(2) . . ?
N1 C1 C2 124.8(2) . . ?
N2 C1 C2 125.7(2) . . ?
C1 C2 H5A 109.5 . . ?
C1 C2 H5B 109.5 . . ?
H5A C2 H5B 109.5 . . ?
C1 C2 H5C 109.5 . . ?
H5A C2 H5C 109.5 . . ?
H5B C2 H5C 109.5 . . ?
C4 C3 N2 107.5(2) . . ?
C4 C3 H1 127.6(16) . . ?
N2 C3 H1 124.9(16) . . ?
C3 C4 N1 107.1(2) . . ?
C3 C4 H2 129.6(14) . . ?
N1 C4 H2 123.3(14) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 984165'
#######################################################################
#
#                 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_shelx

_audit_creation_date             2014-01-21T17:40:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C22 H19 N5 O4 S'
_chemical_formula_moiety         'C15 H12 N3 O4 S, C7 H7 N2'

_chemical_formula_weight         449.48

#==============================================================================

# CRYSTAL DATA

_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                   12.005(3)
_cell_length_b                   13.789(3)
_cell_length_c                   13.810(4)
_cell_angle_alpha                72.186(7)
_cell_angle_beta                 68.682(7)
_cell_angle_gamma                80.962(7)
_cell_volume                     2024.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8275
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'


#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_number            23716
_diffrn_reflns_av_R_equivalents  0.1716
_diffrn_reflns_theta_min         1.553
_diffrn_reflns_theta_max         23.905
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.832
_diffrn_reflns_Laue_measured_fraction_full 0.832
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were placed on calculated positions with idealised geometry and
modelled as riding on the atoms to which they were bonded except those 
involved in hydrogen bonding.  Atoms H5, H24, H36, H37, H43,and H44 were
identified in Fourier difference maps, their position allowed to freely refine
but their isotropic displacement parameters constrained to take a value of 1.2
times that of the atom to which they are bonded.

Problem:
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5700
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.172
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.971      
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     --  C9      ..  5.2 su   
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ..............0.0079 Ang  

Response: 
Small, poorly diffracting needle-shaped crystals resulted in weak, poor 
resolution data.
Data presented is the best of several attempts at data collection.

;
_reflns_number_total             6114
_reflns_number_gt                2700
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1858
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.102
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_restrained_S_all      0.887
_refine_ls_number_reflns         6114
_refine_ls_number_parameters     597
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.25564(12) 0.50942(11) 0.18398(12) 0.0240(4) Uani d 1 . . S
S2 0.70300(13) 0.84871(11) 0.05735(11) 0.0221(4) Uani d 1 . . S
O1 0.2683(3) 0.4175(3) 0.2638(3) 0.0255(10) Uani d 1 . . O
O2 0.8038(3) 0.7847(2) 0.0754(2) 0.0218(9) Uani d 1 . . O
O3 0.3423(3) 0.5857(2) 0.1467(3) 0.0284(10) Uani d 1 . . O
O4 -0.0732(3) 0.5604(2) 0.4085(3) 0.0280(10) Uani d 1 . . O
O5 0.6028(3) 0.8626(2) 0.1491(2) 0.0241(10) Uani d 1 . . O
O6 -0.0475(3) 0.3697(3) 0.2134(3) 0.0251(10) Uani d 1 . . O
O7 0.9063(3) 0.8883(2) -0.2727(3) 0.0247(10) Uani d 1 . . O
N11 0.7511(3) 0.9615(3) -0.0198(3) 0.0174(11) Uani d 1 . . N
O8 0.9406(3) 1.0815(2) -0.1021(3) 0.0240(10) Uani d 1 . . O
N2 0.1219(3) 0.5616(3) 0.2293(3) 0.0187(11) Uani d 1 . . N
N3 0.0200(4) 0.6917(3) 0.4647(3) 0.0212(12) Uani d 1 . . N
H36 0.017(4) 0.637(3) 0.430(3) 0.025 Uiso d 1 . . H
N4 0.8830(4) 0.2236(3) 0.1643(3) 0.0209(12) Uani d 1 . . N
H44 0.914(4) 0.275(3) 0.180(3) 0.025 Uiso d 1 . . H
N5 1.1712(4) 1.0813(3) -0.4175(3) 0.0235(12) Uani d 1 . . N
N6 0.8508(4) 0.1142(3) 0.0922(3) 0.0217(12) Uani d 1 . . N
H43 0.869(4) 0.072(3) 0.039(3) 0.026 Uiso d 1 . . H
N7 -0.1687(4) 0.4478(3) 0.3788(3) 0.0207(12) Uani d 1 . . N
H24 -0.160(4) 0.400(3) 0.334(3) 0.025 Uiso d 1 . . H
N8 1.0181(4) 1.0315(3) -0.2576(4) 0.0227(13) Uani d 1 . . N
H5 1.010(4) 0.993(4) -0.288(4) 0.027 Uiso d 1 . . H
N9 -0.0151(4) 0.7882(3) 0.5729(3) 0.0205(12) Uani d 1 . . N
N10 -0.3432(4) 0.3681(3) 0.4700(3) 0.0255(12) Uani d 1 . . N
C1 0.8417(4) 0.9566(4) -0.1235(4) 0.0218(15) Uani d 1 . . C
C2 0.7762(4) 0.1785(4) 0.2342(4) 0.0178(14) Uani d 1 . . C
C3 0.3352(5) 0.5013(4) -0.0275(4) 0.0272(15) Uani d 1 . . C
H16 0.4067 0.5262 -0.0358 0.033 Uiso calc 1 . . H
C4 0.5731(5) 0.7603(4) -0.1717(4) 0.0247(15) Uani d 1 . . C
H1 0.5463 0.7444 -0.22 0.03 Uiso calc 1 . . H
C5 1.1154(5) 1.0939(4) -0.3176(4) 0.0188(14) Uani d 1 . . C
C6 0.6011(5) 0.1321(4) 0.3835(4) 0.0250(15) Uani d 1 . . C
H40 0.5466 0.1394 0.4492 0.03 Uiso calc 1 . . H
C7 0.6997(5) 0.1934(4) 0.3318(4) 0.0253(15) Uani d 1 . . C
H41 0.7129 0.2411 0.3612 0.03 Uiso calc 1 . . H
C8 0.1228(4) 0.4231(4) 0.0001(4) 0.0241(15) Uani d 1 . . C
H19 0.0528 0.3957 0.0087 0.029 Uiso calc 1 . . H
C9 0.1001(4) 0.6655(4) 0.1667(4) 0.0324(16) Uani d 1 . . C
H26 0.0993 0.6637 0.098 0.049 Uiso calc 1 . . H
H27 0.1626 0.7076 0.1557 0.049 Uiso calc 1 . . H
H25 0.0243 0.6932 0.2054 0.049 Uiso calc 1 . . H
C10 0.2716(5) 0.9000(4) 0.3766(4) 0.0278(16) Uani d 1 . . C
H33 0.3254 0.9494 0.3593 0.033 Uiso calc 1 . . H
C11 0.7188(5) 0.8367(4) -0.1380(4) 0.0242(15) Uani d 1 . . C
C12 1.2992(5) 1.2136(4) -0.4525(4) 0.0257(15) Uani d 1 . . C
H8 1.3609 1.2551 -0.5015 0.031 Uiso calc 1 . . H
C13 -0.3065(5) 0.4916(4) 0.5431(4) 0.0249(15) Uani d 1 . . C
H20 -0.2564 0.5392 0.5383 0.03 Uiso calc 1 . . H
C14 1.2424(4) 1.2243(4) -0.3483(4) 0.0262(15) Uani d 1 . . C
H7 1.2664 1.2724 -0.3261 0.031 Uiso calc 1 . . H
C15 -0.2749(5) 0.4382(4) 0.4670(4) 0.0206(14) Uani d 1 . . C
C16 0.6591(4) 1.0452(4) -0.0290(4) 0.0253(15) Uani d 1 . . C
H12 0.6971 1.109 -0.0636 0.038 Uiso calc 1 . . H
H11 0.6047 1.0459 0.0417 0.038 Uiso calc 1 . . H
H10 0.6159 1.0349 -0.0712 0.038 Uiso calc 1 . . H
C17 0.6797(5) 0.8090(4) -0.2082(4) 0.0230(14) Uani d 1 . . C
H4 0.7255 0.8232 -0.2811 0.028 Uiso calc 1 . . H
C18 0.8290(5) 0.8969(4) -0.1813(4) 0.0219(14) Uani d 1 . . C
C19 1.2623(5) 1.1406(4) -0.4811(4) 0.0254(15) Uani d 1 . . C
H9 1.3036 1.1317 -0.5496 0.03 Uiso calc 1 . . H
C20 0.6581(4) 0.0471(4) 0.2407(4) 0.0239(15) Uani d 1 . . C
H39 0.6445 0.0002 0.2107 0.029 Uiso calc 1 . . H
C21 0.9347(5) 1.0271(4) -0.1576(4) 0.0193(14) Uani d 1 . . C
C22 1.1503(4) 1.1626(4) -0.2788(4) 0.0209(14) Uani d 1 . . C
H6 1.1124 1.1664 -0.208 0.025 Uiso calc 1 . . H
C23 0.2458(5) 0.4813(4) 0.0712(4) 0.0213(14) Uani d 1 . . C
C24 -0.0544(5) 0.7139(4) 0.5547(4) 0.0210(14) Uani d 1 . . C
H35 -0.1247 0.6812 0.5988 0.025 Uiso calc 1 . . H
C25 -0.4875(5) 0.4019(4) 0.6333(4) 0.0319(16) Uani d 1 . . C
H22 -0.5605 0.3884 0.6888 0.038 Uiso calc 1 . . H
C26 -0.4473(5) 0.3520(4) 0.5539(4) 0.0316(16) Uani d 1 . . C
H23 -0.4955 0.3033 0.558 0.038 Uiso calc 1 . . H
C27 0.7560(5) 0.1085(4) 0.1896(4) 0.0197(14) Uani d 1 . . C
C28 0.6523(5) 0.8095(4) -0.0282(4) 0.0186(14) Uani d 1 . . C
C29 0.1692(5) 0.8936(4) 0.4680(4) 0.0284(15) Uani d 1 . . C
H34 0.1537 0.9366 0.5122 0.034 Uiso calc 1 . . H
C30 0.5073(5) 0.7359(4) -0.0626(4) 0.0273(15) Uani d 1 . . C
H2 0.4361 0.7033 -0.0379 0.033 Uiso calc 1 . . H
C31 0.9243(5) 0.1827(4) 0.0820(4) 0.0248(15) Uani d 1 . . C
H42 0.9952 0.1994 0.0247 0.03 Uiso calc 1 . . H
C32 0.0268(5) 0.4924(4) 0.2583(4) 0.0238(15) Uani d 1 . . C
C33 0.1362(5) 0.4431(4) 0.0880(4) 0.0205(14) Uani d 1 . . C
C34 0.2183(5) 0.7622(4) 0.3316(4) 0.0239(15) Uani d 1 . . C
H31 0.2346 0.7184 0.288 0.029 Uiso calc 1 . . H
C35 -0.0722(5) 0.5033(4) 0.3536(4) 0.0220(14) Uani d 1 . . C
C36 0.2123(5) 0.4434(4) -0.1001(4) 0.0255(15) Uani d 1 . . C
H18 0.2016 0.43 -0.1581 0.031 Uiso calc 1 . . H
C37 0.2961(5) 0.8359(4) 0.3113(4) 0.0293(16) Uani d 1 . . C
H32 0.3664 0.8423 0.2522 0.035 Uiso calc 1 . . H
C38 0.0918(5) 0.8187(4) 0.4887(4) 0.0206(14) Uani d 1 . . C
C39 0.5822(5) 0.0608(4) 0.3396(4) 0.0223(14) Uani d 1 . . C
H38 0.5164 0.0206 0.3777 0.027 Uiso calc 1 . . H
C40 0.1141(5) 0.7572(4) 0.4210(4) 0.0187(14) Uani d 1 . . C
C41 0.3180(5) 0.4840(4) -0.1140(4) 0.0296(16) Uani d 1 . . C
H17 0.3769 0.4993 -0.1817 0.035 Uiso calc 1 . . H
C42 -0.4139(5) 0.4734(4) 0.6269(4) 0.0296(16) Uani d 1 . . C
H21 -0.437 0.509 0.679 0.035 Uiso calc 1 . . H
C43 0.5461(5) 0.7595(4) 0.0117(4) 0.0223(15) Uani d 1 . . C
H3 0.5023 0.7422 0.0851 0.027 Uiso calc 1 . . H
C44 0.0334(5) 0.4325(4) 0.1914(4) 0.0200(14) Uani d 1 . . C
H37 -0.044(4) 0.811(3) 0.638(3) 0.024 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.432(3) ?
S1 O3 . 1.441(3) ?
S1 N2 . 1.633(4) ?
S1 C23 . 1.763(5) ?
S2 O2 . 1.433(3) ?
S2 O5 . 1.435(3) ?
S2 N11 . 1.645(4) ?
S2 C28 . 1.754(5) ?
O4 C35 . 1.245(5) ?
O6 C44 . 1.294(5) ?
O7 C18 . 1.294(5) ?
N11 C1 . 1.463(6) ?
N11 C16 . 1.476(6) ?
O8 C21 . 1.251(5) ?
N2 C32 . 1.466(6) ?
N2 C9 . 1.469(6) ?
N3 C24 . 1.333(6) ?
N3 C40 . 1.396(6) ?
N3 H36 . 1.02(4) ?
N4 C31 . 1.323(6) ?
N4 C2 . 1.396(6) ?
N4 H44 . 0.96(4) ?
N5 C19 . 1.334(5) ?
N5 C5 . 1.349(5) ?
N6 C31 . 1.334(5) ?
N6 C27 . 1.401(6) ?
N6 H43 . 1.01(4) ?
N7 C35 . 1.369(6) ?
N7 C15 . 1.396(6) ?
N7 H24 . 1.01(4) ?
N8 C21 . 1.369(6) ?
N8 C5 . 1.402(6) ?
N8 H5 . 0.80(4) ?
N9 C24 . 1.316(5) ?
N9 C38 . 1.400(6) ?
N9 H37 . 0.98(4) ?
N10 C15 . 1.345(6) ?
N10 C26 . 1.353(6) ?
C1 C18 . 1.366(6) ?
C1 C21 . 1.447(6) ?
C2 C27 . 1.384(6) ?
C2 C7 . 1.383(6) ?
C3 C23 . 1.373(6) ?
C3 C41 . 1.377(6) ?
C3 H16 . 0.93 ?
C4 C30 . 1.384(6) ?
C4 C17 . 1.392(6) ?
C4 H1 . 0.93 ?
C5 C22 . 1.401(6) ?
C6 C39 . 1.385(6) ?
C6 C7 . 1.399(6) ?
C6 H40 . 0.93 ?
C7 H41 . 0.93 ?
C8 C36 . 1.387(6) ?
C8 C33 . 1.390(6) ?
C8 H19 . 0.93 ?
C9 H26 . 0.96 ?
C9 H27 . 0.96 ?
C9 H25 . 0.96 ?
C10 C37 . 1.376(6) ?
C10 C29 . 1.396(6) ?
C10 H33 . 0.93 ?
C11 C17 . 1.386(6) ?
C11 C28 . 1.394(6) ?
C11 C18 . 1.505(6) ?
C12 C19 . 1.371(6) ?
C12 C14 . 1.393(6) ?
C12 H8 . 0.93 ?
C13 C15 . 1.373(6) ?
C13 C42 . 1.380(6) ?
C13 H20 . 0.93 ?
C14 C22 . 1.375(6) ?
C14 H7 . 0.93 ?
C16 H12 . 0.96 ?
C16 H11 . 0.96 ?
C16 H10 . 0.96 ?
C17 H4 . 0.93 ?
C19 H9 . 0.93 ?
C20 C39 . 1.389(6) ?
C20 C27 . 1.392(6) ?
C20 H39 . 0.93 ?
C22 H6 . 0.93 ?
C23 C33 . 1.409(6) ?
C24 H35 . 0.93 ?
C25 C26 . 1.372(6) ?
C25 C42 . 1.386(6) ?
C25 H22 . 0.93 ?
C26 H23 . 0.93 ?
C28 C43 . 1.393(6) ?
C29 C38 . 1.393(6) ?
C29 H34 . 0.93 ?
C30 C43 . 1.404(6) ?
C30 H2 . 0.93 ?
C31 H42 . 0.93 ?
C32 C44 . 1.391(6) ?
C32 C35 . 1.448(7) ?
C33 C44 . 1.494(6) ?
C34 C37 . 1.385(6) ?
C34 C40 . 1.395(6) ?
C34 H31 . 0.93 ?
C36 C41 . 1.393(6) ?
C36 H18 . 0.93 ?
C37 H32 . 0.93 ?
C38 C40 . 1.376(6) ?
C39 H38 . 0.93 ?
C41 H17 . 0.93 ?
C42 H21 . 0.93 ?
C43 H3 . 0.93 ?

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 O3 118.4(2) . . ?
O1 S1 N2 108.4(2) . . ?
O3 S1 N2 108.8(2) . . ?
O1 S1 C23 110.6(2) . . ?
O3 S1 C23 108.8(2) . . ?
N2 S1 C23 100.3(2) . . ?
O2 S2 O5 118.6(2) . . ?
O2 S2 N11 108.1(2) . . ?
O5 S2 N11 108.5(2) . . ?
O2 S2 C28 110.3(2) . . ?
O5 S2 C28 109.2(2) . . ?
N11 S2 C28 100.5(2) . . ?
C1 N11 C16 113.7(4) . . ?
C1 N11 S2 112.6(3) . . ?
C16 N11 S2 116.7(3) . . ?
C32 N2 C9 114.2(4) . . ?
C32 N2 S1 112.6(3) . . ?
C9 N2 S1 115.9(3) . . ?
C24 N3 C40 107.5(4) . . ?
C24 N3 H36 130(2) . . ?
C40 N3 H36 122(2) . . ?
C31 N4 C2 107.7(4) . . ?
C31 N4 H44 131(3) . . ?
C2 N4 H44 121(3) . . ?
C19 N5 C5 116.3(4) . . ?
C31 N6 C27 107.6(4) . . ?
C31 N6 H43 123(2) . . ?
C27 N6 H43 129(2) . . ?
C35 N7 C15 129.1(4) . . ?
C35 N7 H24 117(2) . . ?
C15 N7 H24 114(2) . . ?
C21 N8 C5 130.4(4) . . ?
C21 N8 H5 116(4) . . ?
C5 N8 H5 114(4) . . ?
C24 N9 C38 107.9(4) . . ?
C24 N9 H37 128(2) . . ?
C38 N9 H37 123(2) . . ?
C15 N10 C26 116.0(4) . . ?
C18 C1 C21 126.6(5) . . ?
C18 C1 N11 121.1(4) . . ?
C21 C1 N11 112.1(4) . . ?
C27 C2 C7 122.4(5) . . ?
C27 C2 N4 107.2(4) . . ?
C7 C2 N4 130.5(5) . . ?
C23 C3 C41 119.4(5) . . ?
C23 C3 H16 120.3 . . ?
C41 C3 H16 120.3 . . ?
C30 C4 C17 119.2(5) . . ?
C30 C4 H1 120.4 . . ?
C17 C4 H1 120.4 . . ?
N5 C5 C22 123.5(5) . . ?
N5 C5 N8 112.6(4) . . ?
C22 C5 N8 123.8(5) . . ?
C39 C6 C7 121.9(5) . . ?
C39 C6 H40 119 . . ?
C7 C6 H40 119 . . ?
C2 C7 C6 115.6(5) . . ?
C2 C7 H41 122.2 . . ?
C6 C7 H41 122.2 . . ?
C36 C8 C33 121.1(5) . . ?
C36 C8 H19 119.5 . . ?
C33 C8 H19 119.5 . . ?
N2 C9 H26 109.5 . . ?
N2 C9 H27 109.5 . . ?
H26 C9 H27 109.5 . . ?
N2 C9 H25 109.5 . . ?
H26 C9 H25 109.5 . . ?
H27 C9 H25 109.5 . . ?
C37 C10 C29 122.5(5) . . ?
C37 C10 H33 118.7 . . ?
C29 C10 H33 118.7 . . ?
C17 C11 C28 118.4(5) . . ?
C17 C11 C18 119.9(5) . . ?
C28 C11 C18 121.6(5) . . ?
C19 C12 C14 118.5(5) . . ?
C19 C12 H8 120.8 . . ?
C14 C12 H8 120.8 . . ?
C15 C13 C42 118.8(5) . . ?
C15 C13 H20 120.6 . . ?
C42 C13 H20 120.6 . . ?
C22 C14 C12 119.0(5) . . ?
C22 C14 H7 120.5 . . ?
C12 C14 H7 120.5 . . ?
N10 C15 C13 123.3(5) . . ?
N10 C15 N7 111.5(4) . . ?
C13 C15 N7 125.2(5) . . ?
N11 C16 H12 109.5 . . ?
N11 C16 H11 109.5 . . ?
H12 C16 H11 109.5 . . ?
N11 C16 H10 109.5 . . ?
H12 C16 H10 109.5 . . ?
H11 C16 H10 109.5 . . ?
C11 C17 C4 121.2(5) . . ?
C11 C17 H4 119.4 . . ?
C4 C17 H4 119.4 . . ?
O7 C18 C1 124.3(5) . . ?
O7 C18 C11 116.6(5) . . ?
C1 C18 C11 119.1(5) . . ?
N5 C19 C12 124.5(5) . . ?
N5 C19 H9 117.8 . . ?
C12 C19 H9 117.8 . . ?
C39 C20 C27 115.5(5) . . ?
C39 C20 H39 122.3 . . ?
C27 C20 H39 122.3 . . ?
O8 C21 N8 121.1(5) . . ?
O8 C21 C1 123.8(5) . . ?
N8 C21 C1 115.1(5) . . ?
C14 C22 C5 118.0(5) . . ?
C14 C22 H6 121 . . ?
C5 C22 H6 121 . . ?
C3 C23 C33 122.4(5) . . ?
C3 C23 S1 122.5(4) . . ?
C33 C23 S1 115.0(4) . . ?
N9 C24 N3 111.0(5) . . ?
N9 C24 H35 124.5 . . ?
N3 C24 H35 124.5 . . ?
C26 C25 C42 116.7(5) . . ?
C26 C25 H22 121.6 . . ?
C42 C25 H22 121.6 . . ?
N10 C26 C25 125.2(5) . . ?
N10 C26 H23 117.4 . . ?
C25 C26 H23 117.4 . . ?
C2 C27 C20 122.3(5) . . ?
C2 C27 N6 106.4(5) . . ?
C20 C27 N6 131.3(5) . . ?
C43 C28 C11 122.0(5) . . ?
C43 C28 S2 121.0(4) . . ?
C11 C28 S2 116.9(4) . . ?
C38 C29 C10 115.8(5) . . ?
C38 C29 H34 122.1 . . ?
C10 C29 H34 122.1 . . ?
C4 C30 C43 121.3(5) . . ?
C4 C30 H2 119.4 . . ?
C43 C30 H2 119.4 . . ?
N4 C31 N6 111.1(5) . . ?
N4 C31 H42 124.5 . . ?
N6 C31 H42 124.5 . . ?
C44 C32 C35 127.1(5) . . ?
C44 C32 N2 120.3(5) . . ?
C35 C32 N2 112.3(4) . . ?
C8 C33 C23 117.0(5) . . ?
C8 C33 C44 120.1(5) . . ?
C23 C33 C44 122.6(5) . . ?
C37 C34 C40 116.4(5) . . ?
C37 C34 H31 121.8 . . ?
C40 C34 H31 121.8 . . ?
O4 C35 N7 121.1(5) . . ?
O4 C35 C32 123.7(5) . . ?
N7 C35 C32 115.1(5) . . ?
C8 C36 C41 120.1(5) . . ?
C8 C36 H18 120 . . ?
C41 C36 H18 120 . . ?
C10 C37 C34 121.5(5) . . ?
C10 C37 H32 119.3 . . ?
C34 C37 H32 119.3 . . ?
C40 C38 C29 121.6(5) . . ?
C40 C38 N9 106.7(4) . . ?
C29 C38 N9 131.7(5) . . ?
C6 C39 C20 122.3(5) . . ?
C6 C39 H38 118.8 . . ?
C20 C39 H38 118.8 . . ?
C38 C40 C34 122.2(5) . . ?
C38 C40 N3 106.8(4) . . ?
C34 C40 N3 130.9(5) . . ?
C3 C41 C36 120.0(5) . . ?
C3 C41 H17 120 . . ?
C36 C41 H17 120 . . ?
C13 C42 C25 120.0(5) . . ?
C13 C42 H21 120 . . ?
C25 C42 H21 120 . . ?
C28 C43 C30 117.8(5) . . ?
C28 C43 H3 121.1 . . ?
C30 C43 H3 121.1 . . ?
O6 C44 C32 122.8(5) . . ?
O6 C44 C33 118.3(5) . . ?
C32 C44 C33 118.9(5) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 984166'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H13 N3 O4 S), C2 H3 N3'
_chemical_formula_sum            'C32 H29 N9 O8 S2'
_chemical_formula_weight         731.76

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.9267(2)
_cell_length_b                   8.3356(3)
_cell_length_c                   28.8177(10)
_cell_angle_alpha                86.485(2)
_cell_angle_beta                 84.209(2)
_cell_angle_gamma                76.2710(10)
_cell_volume                     1606.89(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    35311
_cell_measurement_theta_min      1
_cell_measurement_theta_max      56.60

_exptl_crystal_description       needles
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8072
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35311
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         0.71
_diffrn_reflns_theta_max         28.26
_reflns_number_total             7358
_reflns_number_gt                5437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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.

The triazole molecules are both disordered over an inversion centre.  Due to
the close proximity of the positions of N8/N9 and N11/N12, these were 
refined with only isotropic displacement parameters and the positions 
allowed to refine freely.

All H atoms were placed on calculated positions and refined as riding on the
atoms to which they are bonded except those involved in hydrogen bonding.
H9, H10, H24 and H25 were identified in a difference Fourier map and their
positions and isotropic displacement parameters allowed to refine freely.
 
;

_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)+(0.0521P)²+2.1856P] 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         7358
_refine_ls_number_parameters     503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C34 C -0.0626(9) 0.4316(7) 0.5467(2) 0.0199(12) Uani 0.50 1 d P . .
H33 H -0.1010 0.3869 0.5756 0.024 Uiso 0.50 1 calc PR . .
N12 N 0.0226(14) 0.3461(12) 0.5103(3) 0.031(3) Uiso 0.50 1 d P . .
N10 N -0.0851(11) 0.5912(9) 0.5360(3) 0.0192(14) Uani 0.50 1 d P . .
H31 H -0.1397 0.6679 0.5551 0.023 Uiso 0.50 1 calc PR . .
N11 N 0.0114(13) 0.3793(11) 0.5089(3) 0.024(3) Uiso 0.50 1 d P . .
C33 C -0.0539(15) 0.5378(12) 0.5219(3) 0.028(2) Uani 0.50 1 d P . .
H32 H -0.1169 0.5645 0.5514 0.034 Uiso 0.50 1 calc PR . .
N8 N 0.9077(12) 0.6330(10) 0.0006(3) 0.024(3) Uiso 0.50 1 d P . .
C31 C 0.8817(13) 0.5346(11) 0.0365(3) 0.0227(18) Uani 0.50 1 d P . .
H34 H 0.7970 0.5665 0.0631 0.027 Uiso 0.50 1 calc PR . .
N7 N 1.0075(9) 0.6178(9) -0.0298(2) 0.0195(13) Uani 0.50 1 d P . .
H36 H 1.0168 0.6988 -0.0492 0.023 Uiso 0.50 1 calc PR . .
N9 N 0.8991(11) 0.6245(11) 0.0116(3) 0.023(2) Uiso 0.50 1 d P . .
C32 C 0.9538(14) 0.4696(13) 0.0281(3) 0.0216(18) Uani 0.50 1 d P . .
H35 H 0.9020 0.4337 0.0568 0.026 Uiso 0.50 1 calc PR . .
H24 H 0.426(5) -0.362(4) 0.5315(11) 0.013(8) Uiso 1 1 d . . .
H10 H 1.193(5) 0.969(4) 0.0278(11) 0.018(9) Uiso 1 1 d . . .
H9 H 1.484(5) 0.656(5) -0.0231(12) 0.028(9) Uiso 1 1 d . . .
H25 H 0.301(5) -0.011(4) 0.4752(11) 0.021(9) Uiso 1 1 d . . .
S1 S 0.35122(10) -0.24081(8) 0.32362(2) 0.01544(16) Uani 1 1 d . . .
O7 O 0.4856(3) -0.3655(2) 0.46031(7) 0.0194(4) Uani 1 1 d . . .
O5 O 0.4604(3) -0.3371(2) 0.28570(7) 0.0211(4) Uani 1 1 d . . .
O8 O 0.2897(3) 0.1332(2) 0.42274(7) 0.0201(4) Uani 1 1 d . . .
N4 N 0.4948(3) -0.2612(3) 0.36653(8) 0.0154(5) Uani 1 1 d . . .
O6 O 0.1625(3) -0.2713(2) 0.34223(7) 0.0211(4) Uani 1 1 d . . .
N6 N 0.3621(4) -0.2938(3) 0.54871(8) 0.0175(5) Uani 1 1 d . . .
N5 N 0.3337(4) -0.1053(3) 0.48447(8) 0.0183(5) Uani 1 1 d . . .
C19 C 0.2939(4) 0.2490(3) 0.33014(10) 0.0188(6) Uani 1 1 d . . .
H16 H 0.2978 0.3233 0.3526 0.023 Uiso 1 1 calc R . .
C16 C 0.3176(4) -0.0283(3) 0.30759(9) 0.0147(5) Uani 1 1 d . . .
C21 C 0.3244(4) 0.0800(3) 0.34233(10) 0.0163(6) Uani 1 1 d . . .
C23 C 0.4141(4) -0.1457(3) 0.40322(9) 0.0164(6) Uani 1 1 d . . .
C25 C 0.2941(4) -0.1403(3) 0.53072(10) 0.0162(6) Uani 1 1 d . . .
C17 C 0.2800(4) 0.0287(4) 0.26226(10) 0.0187(6) Uani 1 1 d . . .
H19 H 0.2753 -0.0448 0.2396 0.022 Uiso 1 1 calc R . .
C28 C 0.2189(4) -0.2215(4) 0.62450(10) 0.0201(6) Uani 1 1 d . . .
H22 H 0.1941 -0.2495 0.6559 0.024 Uiso 1 1 calc R . .
C22 C 0.3454(4) 0.0226(3) 0.39236(10) 0.0171(6) Uani 1 1 d . . .
C18 C 0.2493(4) 0.1976(4) 0.25118(10) 0.0204(6) Uani 1 1 d . . .
H18 H 0.2229 0.2373 0.2210 0.024 Uiso 1 1 calc R . .
C24 C 0.4174(4) -0.2183(3) 0.44990(10) 0.0172(6) Uani 1 1 d . . .
C27 C 0.1434(4) -0.0606(4) 0.60672(10) 0.0198(6) Uani 1 1 d . . .
H21 H 0.0672 0.0190 0.6265 0.024 Uiso 1 1 calc R . .
C30 C 0.7110(4) -0.2828(4) 0.35309(10) 0.0211(6) Uani 1 1 d . . .
H27 H 0.7357 -0.1820 0.3385 0.032 Uiso 1 1 calc R . .
H28 H 0.7550 -0.3704 0.3316 0.032 Uiso 1 1 calc R . .
H26 H 0.7826 -0.3099 0.3804 0.032 Uiso 1 1 calc R . .
C29 C 0.3297(4) -0.3358(4) 0.59449(10) 0.0190(6) Uani 1 1 d . . .
H23 H 0.3832 -0.4427 0.6055 0.023 Uiso 1 1 calc R . .
C20 C 0.2582(4) 0.3062(4) 0.28495(10) 0.0199(6) Uani 1 1 d . . .
H17 H 0.2400 0.4185 0.2772 0.024 Uiso 1 1 calc R . .
C26 C 0.1811(4) -0.0195(3) 0.56025(10) 0.0181(6) Uani 1 1 d . . .
H20 H 0.1317 0.0874 0.5487 0.022 Uiso 1 1 calc R . .
S2 S 0.99771(10) 0.65898(9) 0.16436(3) 0.01943(17) Uani 1 1 d . . .
O4 O 1.0493(3) 1.0820(2) 0.07791(7) 0.0219(5) Uani 1 1 d . . .
O3 O 1.3856(3) 0.6135(2) 0.04181(7) 0.0226(5) Uani 1 1 d . . .
O1 O 1.0466(3) 0.5407(3) 0.20237(8) 0.0278(5) Uani 1 1 d . . .
O2 O 0.8488(3) 0.6400(2) 0.13543(8) 0.0242(5) Uani 1 1 d . . .
N3 N 1.4765(4) 0.7373(3) -0.04239(9) 0.0208(5) Uani 1 1 d . . .
N2 N 1.2659(4) 0.8836(3) 0.01787(9) 0.0206(5) Uani 1 1 d . . .
N1 N 1.2022(3) 0.6635(3) 0.13111(8) 0.0180(5) Uani 1 1 d . . .
C7 C 1.0702(4) 0.9579(4) 0.10684(10) 0.0189(6) Uani 1 1 d . . .
C13 C 1.5484(4) 0.8608(4) -0.11567(11) 0.0236(6) Uani 1 1 d . . .
H7 H 1.6120 0.8537 -0.1457 0.028 Uiso 1 1 calc R . .
C10 C 1.3582(4) 0.8794(3) -0.02620(10) 0.0183(6) Uani 1 1 d . . .
C8 C 1.1800(4) 0.7978(3) 0.09610(10) 0.0185(6) Uani 1 1 d . . .
C12 C 1.4271(4) 1.0106(4) -0.10017(11) 0.0224(6) Uani 1 1 d . . .
H6 H 1.4097 1.1038 -0.1202 0.027 Uiso 1 1 calc R . .
C3 C 0.9273(4) 0.8614(4) 0.18540(11) 0.0203(6) Uani 1 1 d . . .
C15 C 1.3883(4) 0.6297(4) 0.15492(11) 0.0247(7) Uani 1 1 d . . .
H12 H 1.5013 0.6115 0.1320 0.037 Uiso 1 1 calc R . .
H13 H 1.3951 0.5330 0.1752 0.037 Uiso 1 1 calc R . .
H11 H 1.3892 0.7225 0.1730 0.037 Uiso 1 1 calc R . .
C11 C 1.3337(4) 1.0213(3) -0.05576(10) 0.0190(6) Uani 1 1 d . . .
H5 H 1.2551 1.1215 -0.0454 0.023 Uiso 1 1 calc R . .
C5 C 0.9032(4) 1.1504(4) 0.17005(11) 0.0226(6) Uani 1 1 d . . .
H4 H 0.9254 1.2378 0.1502 0.027 Uiso 1 1 calc R . .
C4 C 0.9683(4) 0.9889(4) 0.15528(10) 0.0195(6) Uani 1 1 d . . .
C6 C 0.8052(4) 1.1818(4) 0.21419(12) 0.0258(7) Uani 1 1 d . . .
H3 H 0.7645 1.2899 0.2240 0.031 Uiso 1 1 calc R . .
C14 C 1.5717(4) 0.7255(4) -0.08591(11) 0.0243(7) Uani 1 1 d . . .
H8 H 1.6528 0.6252 -0.0955 0.029 Uiso 1 1 calc R . .
C9 C 1.2834(4) 0.7533(4) 0.05108(10) 0.0189(6) Uani 1 1 d . . .
C2 C 0.8287(4) 0.8906(4) 0.22961(11) 0.0254(7) Uani 1 1 d . . .
H1 H 0.8040 0.8036 0.2493 0.030 Uiso 1 1 calc R . .
C1 C 0.7677(5) 1.0528(4) 0.24376(11) 0.0268(7) Uani 1 1 d . . .
H2 H 0.7015 1.0749 0.2732 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
C34 N12 1.315(12) . ?
C34 N10 1.323(9) . ?
C34 H33 0.9300 . ?
N12 C33 1.338(14) 2_566 ?
N10 N11 1.373(11) 2_566 ?
N10 H31 0.8600 . ?
N11 C33 1.149(14) 2_566 ?
N11 C33 1.353(12) . ?
N11 N10 1.373(11) 2_566 ?
C33 N12 1.338(14) 2_566 ?
C33 H32 0.9300 . ?
N8 N7 1.055(9) . ?
N8 C31 1.304(11) . ?
N8 C32 1.368(12) 2_765 ?
C31 N7 1.333(9) 2_765 ?
C31 H34 0.9300 . ?
N7 C31 1.333(9) 2_765 ?
N7 H36 0.8600 . ?
N9 C32 1.329(12) . ?
N9 C32 1.566(12) 2_765 ?
C32 N8 1.368(12) 2_765 ?
C32 H35 0.9300 . ?
S1 O6 1.436(2) . ?
S1 O5 1.437(2) . ?
S1 N4 1.640(2) . ?
S1 C16 1.769(3) . ?
O7 C24 1.236(3) . ?
O8 C22 1.276(3) . ?
N4 C23 1.451(3) . ?
N4 C30 1.480(3) . ?
N6 C25 1.345(4) . ?
N6 C29 1.354(4) . ?
N6 H24 0.80(3) . ?
N5 C25 1.361(4) . ?
N5 C24 1.398(4) . ?
N5 H25 0.80(3) . ?
C19 C20 1.385(4) . ?
C19 C21 1.402(4) . ?
C19 H16 0.9300 . ?
C16 C17 1.391(4) . ?
C16 C21 1.400(4) . ?
C21 C22 1.501(4) . ?
C23 C22 1.397(4) . ?
C23 C24 1.441(4) . ?
C25 C26 1.395(4) . ?
C17 C18 1.395(4) . ?
C17 H19 0.9300 . ?
C28 C29 1.366(4) . ?
C28 C27 1.404(4) . ?
C28 H22 0.9300 . ?
C18 C20 1.385(4) . ?
C18 H18 0.9300 . ?
C27 C26 1.377(4) . ?
C27 H21 0.9300 . ?
C30 H27 0.9600 . ?
C30 H28 0.9600 . ?
C30 H26 0.9600 . ?
C29 H23 0.9300 . ?
C20 H17 0.9300 . ?
C26 H20 0.9300 . ?
S2 O2 1.432(2) . ?
S2 O1 1.439(2) . ?
S2 N1 1.635(2) . ?
S2 C3 1.769(3) . ?
O4 C7 1.278(3) . ?
O3 C9 1.240(3) . ?
N3 C10 1.350(4) . ?
N3 C14 1.354(4) . ?
N3 H9 0.85(4) . ?
N2 C10 1.362(4) . ?
N2 C9 1.394(4) . ?
N2 H10 0.82(3) . ?
N1 C8 1.451(3) . ?
N1 C15 1.481(4) . ?
C7 C8 1.406(4) . ?
C7 C4 1.507(4) . ?
C13 C14 1.363(4) . ?
C13 C12 1.399(4) . ?
C13 H7 0.9300 . ?
C10 C11 1.401(4) . ?
C8 C9 1.442(4) . ?
C12 C11 1.373(4) . ?
C12 H6 0.9300 . ?
C3 C2 1.390(4) . ?
C3 C4 1.394(4) . ?
C15 H12 0.9600 . ?
C15 H13 0.9600 . ?
C15 H11 0.9600 . ?
C11 H5 0.9300 . ?
C5 C6 1.389(4) . ?
C5 C4 1.393(4) . ?
C5 H4 0.9300 . ?
C6 C1 1.388(4) . ?
C6 H3 0.9300 . ?
C14 H8 0.9300 . ?
C2 C1 1.391(4) . ?
C2 H1 0.9300 . ?
C1 H2 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


N12 C34 N10 109.4(7) . . ?
N12 C34 H33 125.3 . . ?
N10 C34 H33 125.3 . . ?
C34 N12 C33 103.5(8) . 2_566 ?
C34 N10 N11 112.4(7) . 2_566 ?
C34 N10 H31 123.8 . . ?
N11 N10 H31 123.8 2_566 . ?
C33 N11 C33 72.7(9) 2_566 . ?
C33 N11 N10 98.6(9) . 2_566 ?
N12 C33 N11 116.1(11) 2_566 . ?
N12 C33 H32 122.0 2_566 . ?
N11 C33 H32 122.0 . . ?
N7 N8 C31 132.6(9) . . ?
C31 N8 C32 102.1(7) . 2_765 ?
N8 C31 N7 111.0(7) . 2_765 ?
N8 C31 H34 124.5 . . ?
N7 C31 H34 124.5 2_765 . ?
N8 N7 C31 116.0(8) . 2_765 ?
N8 N7 H36 122.0 . . ?
C31 N7 H36 122.0 2_765 . ?
C32 N9 C32 74.8(6) . 2_765 ?
N9 C32 N8 114.7(7) . 2_765 ?
N9 C32 H35 122.7 . . ?
N8 C32 H35 122.7 2_765 . ?
O6 S1 O5 118.72(12) . . ?
O6 S1 N4 108.20(12) . . ?
O5 S1 N4 108.52(12) . . ?
O6 S1 C16 108.74(12) . . ?
O5 S1 C16 109.22(12) . . ?
N4 S1 C16 102.18(12) . . ?
C23 N4 C30 115.0(2) . . ?
C23 N4 S1 113.16(18) . . ?
C30 N4 S1 116.34(18) . . ?
C25 N6 C29 123.0(3) . . ?
C25 N6 H24 118(2) . . ?
C29 N6 H24 119(2) . . ?
C25 N5 C24 127.0(3) . . ?
C25 N5 H25 118(2) . . ?
C24 N5 H25 115(2) . . ?
C20 C19 C21 120.6(3) . . ?
C20 C19 H16 119.7 . . ?
C21 C19 H16 119.7 . . ?
C17 C16 C21 121.5(3) . . ?
C17 C16 S1 120.7(2) . . ?
C21 C16 S1 117.7(2) . . ?
C16 C21 C19 118.1(2) . . ?
C16 C21 C22 122.1(2) . . ?
C19 C21 C22 119.6(3) . . ?
C22 C23 C24 124.6(3) . . ?
C22 C23 N4 120.5(2) . . ?
C24 C23 N4 114.9(2) . . ?
N6 C25 N5 120.2(3) . . ?
N6 C25 C26 118.7(3) . . ?
N5 C25 C26 121.1(3) . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H19 120.4 . . ?
C18 C17 H19 120.4 . . ?
C29 C28 C27 118.3(3) . . ?
C29 C28 H22 120.9 . . ?
C27 C28 H22 120.9 . . ?
O8 C22 C23 124.1(3) . . ?
O8 C22 C21 116.4(2) . . ?
C23 C22 C21 119.4(3) . . ?
C20 C18 C17 120.1(3) . . ?
C20 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O7 C24 N5 120.8(3) . . ?
O7 C24 C23 125.5(3) . . ?
N5 C24 C23 113.7(2) . . ?
C26 C27 C28 120.7(3) . . ?
C26 C27 H21 119.7 . . ?
C28 C27 H21 119.7 . . ?
N4 C30 H27 109.5 . . ?
N4 C30 H28 109.5 . . ?
H27 C30 H28 109.5 . . ?
N4 C30 H26 109.5 . . ?
H27 C30 H26 109.5 . . ?
H28 C30 H26 109.5 . . ?
N6 C29 C28 120.2(3) . . ?
N6 C29 H23 119.9 . . ?
C28 C29 H23 119.9 . . ?
C18 C20 C19 120.5(3) . . ?
C18 C20 H17 119.8 . . ?
C19 C20 H17 119.8 . . ?
C27 C26 C25 119.2(3) . . ?
C27 C26 H20 120.4 . . ?
C25 C26 H20 120.4 . . ?
O2 S2 O1 118.40(13) . . ?
O2 S2 N1 108.49(13) . . ?
O1 S2 N1 108.63(12) . . ?
O2 S2 C3 107.92(13) . . ?
O1 S2 C3 110.02(14) . . ?
N1 S2 C3 102.14(13) . . ?
C10 N3 C14 123.0(3) . . ?
C10 N3 H9 114(2) . . ?
C14 N3 H9 123(2) . . ?
C10 N2 C9 126.8(3) . . ?
C10 N2 H10 121(2) . . ?
C9 N2 H10 112(2) . . ?
C8 N1 C15 115.7(2) . . ?
C8 N1 S2 114.10(18) . . ?
C15 N1 S2 116.13(19) . . ?
O4 C7 C8 124.2(3) . . ?
O4 C7 C4 116.6(3) . . ?
C8 C7 C4 119.2(2) . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H7 120.6 . . ?
C12 C13 H7 120.6 . . ?
N3 C10 N2 120.4(3) . . ?
N3 C10 C11 118.4(3) . . ?
N2 C10 C11 121.2(3) . . ?
C7 C8 C9 124.2(3) . . ?
C7 C8 N1 121.3(3) . . ?
C9 C8 N1 114.5(2) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H6 119.7 . . ?
C13 C12 H6 119.7 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 S2 120.6(2) . . ?
C4 C3 S2 117.2(2) . . ?
N1 C15 H12 109.5 . . ?
N1 C15 H13 109.5 . . ?
H12 C15 H13 109.5 . . ?
N1 C15 H11 109.5 . . ?
H12 C15 H11 109.5 . . ?
H13 C15 H11 109.5 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H5 120.4 . . ?
C10 C11 H5 120.4 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H4 119.8 . . ?
C4 C5 H4 119.8 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 119.6(3) . . ?
C3 C4 C7 122.2(3) . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H3 119.8 . . ?
C5 C6 H3 119.8 . . ?
N3 C14 C13 119.9(3) . . ?
N3 C14 H8 120.0 . . ?
C13 C14 H8 120.0 . . ?
O3 C9 N2 121.1(3) . . ?
O3 C9 C8 124.5(3) . . ?
N2 C9 C8 114.3(3) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H1 120.7 . . ?
C1 C2 H1 120.7 . . ?
C6 C1 C2 120.4(3) . . ?
C6 C1 H2 119.8 . . ?
C2 C1 H2 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 984167'
#######################################################################
#
#                 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_pxbztaz

_audit_creation_date             2014-01-23T10:07:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C21 H18 N6 O4 S'
_chemical_formula_moiety         'C15 H13 N3 O4 S, C6 H5 N3'
_chemical_formula_weight         450.47

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   11.6101(6)
_cell_length_b                   26.2908(15)
_cell_length_c                   6.7710(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.480(3)
_cell_angle_gamma                90
_cell_volume                     2009.83(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_exptl_crystal_description       needles
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8832
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'


#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_number            5992
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_theta_min         1.963
_diffrn_reflns_theta_max         25.329
_diffrn_reflns_theta_full        20
_diffrn_measured_fraction_theta_max 0.802
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.802
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       5

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
Crystals were small and weakly diffracting and the this is the best data we
were able to obtain.  All hydrogen atoms were placed on calculated positions
and refined as riding on the atoms to which they were bonded with the 
exception of those involved in hydrogen bonding.  H5, H10 and H18 were 
identified in difference Fourier maps and their positions and isotropic
displacement parameters were allowed to freely refine.
;
_reflns_number_total             2942
_reflns_number_gt                2320
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1538
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²+3.6047P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.85
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo & Scalepack(Otwinowski&Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
H10 -0.094(4) 0.5346(15) 0.391(6) 0.023(11) Uiso d 1 . . H
H5 0.015(4) 0.6507(17) 0.403(6) 0.031(12) Uiso d 1 . . H
H18 0.065(4) 0.7404(19) -0.052(7) 0.047(15) Uiso d 1 . . H
S1 0.42513(8) 0.59641(3) 0.68394(14) 0.0177(3) Uani d 1 . . S
O4 0.0816(2) 0.53896(9) 0.4515(4) 0.0191(6) Uani d 1 . . O
O1 0.5234(2) 0.56330(9) 0.6815(4) 0.0254(7) Uani d 1 . . O
O3 0.1380(2) 0.69540(9) 0.4529(4) 0.0242(7) Uani d 1 . . O
N2 -0.0024(3) 0.61846(12) 0.4084(5) 0.0181(7) Uani d 1 . . N
O2 0.3926(2) 0.60359(9) 0.8730(4) 0.0211(6) Uani d 1 . . O
N3 -0.1494(3) 0.55535(12) 0.3502(5) 0.0179(7) Uani d 1 . . N
N1 0.3088(2) 0.57605(11) 0.5189(5) 0.0176(7) Uani d 1 . . N
N4 0.0119(3) 0.71775(12) -0.0703(5) 0.0227(8) Uani d 1 . . N
C8 0.2086(3) 0.61085(13) 0.4839(5) 0.0155(8) Uani d 1 . . C
C13 -0.3523(3) 0.57329(15) 0.2269(6) 0.0234(9) Uani d 1 . . C
H13 -0.4301 0.5624 0.1802 0.028 Uiso calc 1 . . H
C18 -0.0444(4) 0.56516(14) -0.1272(6) 0.0241(9) Uani d 1 . . C
H18A -0.0624 0.5307 -0.1422 0.029 Uiso calc 1 . . H
N6 -0.1012(3) 0.73401(11) -0.0993(5) 0.0256(8) Uani d 1 . . N
C14 -0.2634(3) 0.53917(14) 0.2897(6) 0.0211(9) Uani d 1 . . C
H14 -0.2805 0.5046 0.2913 0.025 Uiso calc 1 . . H
C11 -0.2086(3) 0.64126(14) 0.2994(6) 0.0202(9) Uani d 1 . . C
H11 -0.1902 0.6757 0.3073 0.024 Uiso calc 1 . . H
N5 -0.1719(3) 0.69458(12) -0.1291(5) 0.0264(8) Uani d 1 . . N
C7 0.2245(3) 0.66363(13) 0.4798(5) 0.0168(8) Uani d 1 . . C
C2 0.5742(3) 0.72620(15) 0.5481(6) 0.0240(9) Uani d 1 . . C
H2 0.6492 0.74 0.5593 0.029 Uiso calc 1 . . H
C21 0.0160(3) 0.66638(14) -0.0810(5) 0.0192(8) Uani d 1 . . C
C4 0.4484(3) 0.65654(13) 0.5870(5) 0.0175(8) Uani d 1 . . C
C9 0.0947(3) 0.58612(13) 0.4500(5) 0.0165(8) Uani d 1 . . C
C20 -0.1023(3) 0.65163(13) -0.1202(6) 0.0195(8) Uani d 1 . . C
C5 0.3461(3) 0.68510(14) 0.5065(6) 0.0187(8) Uani d 1 . . C
C1 0.4743(3) 0.75534(15) 0.4739(6) 0.0247(9) Uani d 1 . . C
H1 0.4829 0.7891 0.4386 0.03 Uiso calc 1 . . H
C6 0.3612(3) 0.73521(14) 0.4510(6) 0.0209(8) Uani d 1 . . C
H6 0.2953 0.7553 0.3983 0.025 Uiso calc 1 . . H
C10 -0.1190(3) 0.60480(13) 0.3541(5) 0.0162(8) Uani d 1 . . C
C16 0.1093(3) 0.63086(14) -0.0632(6) 0.0225(9) Uani d 1 . . C
H16 0.1883 0.6407 -0.0369 0.027 Uiso calc 1 . . H
C15 0.3295(3) 0.55117(14) 0.3356(6) 0.0224(9) Uani d 1 . . C
H15A 0.2589 0.5338 0.2666 0.034 Uiso calc 1 . . H
H15B 0.3931 0.5271 0.3736 0.034 Uiso calc 1 . . H
H15C 0.3501 0.5764 0.2471 0.034 Uiso calc 1 . . H
C3 0.5617(3) 0.67608(14) 0.6060(6) 0.0212(9) Uani d 1 . . C
H3 0.6281 0.656 0.6565 0.025 Uiso calc 1 . . H
C19 -0.1348(3) 0.59983(14) -0.1445(6) 0.0227(9) Uani d 1 . . C
H19 -0.2137 0.5897 -0.1709 0.027 Uiso calc 1 . . H
C12 -0.3242(3) 0.62541(14) 0.2339(6) 0.0234(9) Uani d 1 . . C
H12 -0.3842 0.6493 0.1939 0.028 Uiso calc 1 . . H
C17 0.0751(3) 0.58075(14) -0.0873(6) 0.0247(9) Uani d 1 . . C
H17 0.1334 0.556 -0.0769 0.03 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.429(3) ?
S1 O1 . 1.439(3) ?
S1 N1 . 1.630(3) ?
S1 C4 . 1.757(4) ?
O4 C9 . 1.249(4) ?
O3 C7 . 1.286(4) ?
N2 C10 . 1.366(5) ?
N2 C9 . 1.388(4) ?
N2 H5 . 0.87(4) ?
N3 C10 . 1.346(5) ?
N3 C14 . 1.358(5) ?
N3 H10 . 0.84(4) ?
N1 C8 . 1.455(4) ?
N1 C15 . 1.471(5) ?
N4 N6 . 1.352(4) ?
N4 C21 . 1.354(5) ?
N4 H18 . 0.85(5) ?
C8 C7 . 1.401(5) ?
C8 C9 . 1.443(5) ?
C13 C14 . 1.359(5) ?
C13 C12 . 1.407(5) ?
C13 H13 . 0.93 ?
C18 C19 . 1.375(5) ?
C18 C17 . 1.411(5) ?
C18 H18A . 0.93 ?
N6 N5 . 1.308(4) ?
C14 H14 . 0.93 ?
C11 C12 . 1.376(5) ?
C11 C10 . 1.399(5) ?
C11 H11 . 0.93 ?
N5 C20 . 1.381(5) ?
C7 C5 . 1.492(5) ?
C2 C1 . 1.383(5) ?
C2 C3 . 1.392(5) ?
C2 H2 . 0.93 ?
C21 C20 . 1.392(5) ?
C21 C16 . 1.414(5) ?
C4 C3 . 1.390(5) ?
C4 C5 . 1.403(5) ?
C20 C19 . 1.413(5) ?
C5 C6 . 1.392(5) ?
C1 C6 . 1.390(5) ?
C1 H1 . 0.93 ?
C6 H6 . 0.93 ?
C16 C17 . 1.374(5) ?
C16 H16 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C3 H3 . 0.93 ?
C19 H19 . 0.93 ?
C12 H12 . 0.93 ?
C17 H17 . 0.93 ?

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 117.82(16) . . ?
O2 S1 N1 107.91(16) . . ?
O1 S1 N1 109.03(15) . . ?
O2 S1 C4 108.15(16) . . ?
O1 S1 C4 110.41(16) . . ?
N1 S1 C4 102.39(16) . . ?
C10 N2 C9 127.0(3) . . ?
C10 N2 H5 118(3) . . ?
C9 N2 H5 115(3) . . ?
C10 N3 C14 122.7(3) . . ?
C10 N3 H10 116(3) . . ?
C14 N3 H10 121(3) . . ?
C8 N1 C15 115.1(3) . . ?
C8 N1 S1 114.1(2) . . ?
C15 N1 S1 116.9(2) . . ?
N6 N4 C21 110.7(3) . . ?
N6 N4 H18 117(3) . . ?
C21 N4 H18 133(3) . . ?
C7 C8 C9 124.3(3) . . ?
C7 C8 N1 121.5(3) . . ?
C9 C8 N1 114.2(3) . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18A 119.3 . . ?
C17 C18 H18A 119.3 . . ?
N5 N6 N4 109.0(3) . . ?
N3 C14 C13 120.2(3) . . ?
N3 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N6 N5 C20 107.6(3) . . ?
O3 C7 C8 123.0(3) . . ?
O3 C7 C5 117.2(3) . . ?
C8 C7 C5 119.8(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N4 C21 C20 104.0(3) . . ?
N4 C21 C16 133.7(3) . . ?
C20 C21 C16 122.3(3) . . ?
C3 C4 C5 122.4(3) . . ?
C3 C4 S1 121.5(3) . . ?
C5 C4 S1 115.9(3) . . ?
O4 C9 N2 121.0(3) . . ?
O4 C9 C8 123.7(3) . . ?
N2 C9 C8 115.3(3) . . ?
N5 C20 C21 108.8(3) . . ?
N5 C20 C19 130.2(3) . . ?
C21 C20 C19 121.1(3) . . ?
C6 C5 C4 117.6(3) . . ?
C6 C5 C7 120.0(3) . . ?
C4 C5 C7 122.4(3) . . ?
C2 C1 C6 121.3(4) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N3 C10 N2 119.9(3) . . ?
N3 C10 C11 118.8(3) . . ?
N2 C10 C11 121.3(3) . . ?
C17 C16 C21 115.4(3) . . ?
C17 C16 H16 122.3 . . ?
C21 C16 H16 122.3 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C18 C19 C20 116.8(3) . . ?
C18 C19 H19 121.6 . . ?
C20 C19 H19 121.6 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C16 C17 C18 123.0(3) . . ?
C16 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 984168'
#######################################################################
#
#                 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_cw2

# start Validation Reply Form
_vrf_RFACR01_cw2                 
;
PROBLEM: The value of the weighted R factor is > 0.45
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_RFACG01_cw2                 
;
PROBLEM: The value of the R factor is > 0.15
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_RINTA01_cw2                 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_PLAT027_cw2                 
;
PROBLEM: _diffrn_reflns_theta_full (too) Low ............      20.00 Deg.  
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_PLAT084_cw2                 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.49       
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_PLAT020_cw2                 
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.211       
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_PLAT029_cw2                 
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.950       
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_PLAT082_cw2                 
;
PROBLEM: High R1 Value ..................................       0.17       
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_PLAT340_cw2                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0157 Ang.  
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron.  This does not affect
the conclusions drawn.
;
_vrf_PLAT930_cw2                 
;
PROBLEM: Check Twin Law ( 0 0  1)[ 0 1  4] Estimated BASF       0.25       
RESPONSE: Small, poorly diffracting crystals resulted in weak, poor resolution 
data, despite data being collected using the synchotron. Interpretation of a
twin law would therefore be unreliable.This does not affect the conclusions 
drawn.
;
# end Validation Reply Form



_audit_creation_date             2014-01-23T10:51:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C15 H13 N3 O4 S), C4 H4 N2'
_chemical_formula_sum            'C34 H30 N8 O8 S2'
_chemical_formula_weight         742.80

#==============================================================================

# CRYSTAL DATA

_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                   6.792(11)
_cell_length_b                   8.646(15)
_cell_length_c                   29.66(5)
_cell_angle_alpha                94.159(11)
_cell_angle_beta                 90.513(18)
_cell_angle_gamma                104.78(4)
_cell_volume                     1679(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'ABSCOR, Rigaku 20102'


#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Rigaku Saturn CCD'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            17434
_diffrn_reflns_av_R_equivalents  0.211
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         25.929
_diffrn_reflns_theta_full        20
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.95
_diffrn_reflns_Laue_measured_fraction_full 0.95
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.95
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 ?
;
_reflns_number_total             6529
_reflns_number_gt                2898
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2644
_refine_ls_R_factor_gt           0.1739
_refine_ls_wR_factor_ref         0.4876
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_restrained_S_all      1.239
_refine_ls_number_reflns         6529
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'


#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N8 0.9852(17) 0.8382(10) 0.5016(3) 0.037(2) Uani d 1 . . N
C33 1.032(2) 0.9401(13) 0.5380(4) 0.041(3) Uani d 1 . . C
H28 1.0529 0.9007 0.5655 0.049 Uiso calc 1 . . H
C34 0.9484(18) 0.8984(12) 0.4634(4) 0.037(3) Uani d 1 . . C
H27 0.9091 0.8305 0.4373 0.044 Uiso calc 1 . . H
S1 0.7098(5) 0.1461(3) 0.32912(9) 0.0373(8) Uani d 1 . . S
O8 0.7425(14) 0.5644(9) 0.4162(2) 0.042(2) Uani d 1 . . O
O7 0.5030(12) 0.1086(8) 0.4604(2) 0.0351(19) Uani d 1 . . O
O6 0.8973(12) 0.1372(9) 0.3512(2) 0.0339(18) Uani d 1 . . O
N5 0.6513(14) 0.3762(10) 0.4796(3) 0.030(2) Uani d 1 . . N
H18 0.6822 0.4696 0.4693 0.037 Uiso calc 1 . . H
C23 0.6088(18) 0.2856(13) 0.4020(3) 0.031(3) Uani d 1 . . C
N4 0.5442(15) 0.1523(10) 0.3683(3) 0.031(2) Uani d 1 . . N
N6 0.6011(15) 0.2339(10) 0.5451(3) 0.032(2) Uani d 1 . . N
H26 0.5396 0.1498 0.5283 0.038 Uiso calc 1 . . H
O5 0.6201(13) 0.0251(9) 0.2944(2) 0.043(2) Uani d 1 . . O
C22 0.6956(17) 0.4426(13) 0.3892(4) 0.032(2) Uani d 1 . . C
C24 0.5838(18) 0.2485(12) 0.4486(3) 0.031(2) Uani d 1 . . C
C20 0.7369(17) 0.4660(12) 0.3401(3) 0.030(2) Uani d 1 . . C
C29 0.6193(19) 0.2211(13) 0.5905(4) 0.037(3) Uani d 1 . . C
H22 0.5683 0.1226 0.6023 0.044 Uiso calc 1 . . H
C26 0.7749(19) 0.5086(13) 0.5526(4) 0.037(3) Uani d 1 . . C
H19 0.8268 0.606 0.5401 0.044 Uiso calc 1 . . H
C21 0.7454(18) 0.3375(14) 0.3085(4) 0.038(3) Uani d 1 . . C
C30 0.328(2) 0.1205(14) 0.3524(4) 0.046(3) Uani d 1 . . C
H25 0.2408 0.1032 0.3778 0.069 Uiso calc 1 . . H
H24 0.2951 0.0268 0.3315 0.069 Uiso calc 1 . . H
H23 0.3092 0.211 0.3376 0.069 Uiso calc 1 . . H
C28 0.711(2) 0.3502(13) 0.6181(4) 0.039(3) Uani d 1 . . C
H21 0.7177 0.3436 0.6492 0.047 Uiso calc 1 . . H
C16 0.7937(19) 0.3585(14) 0.2633(4) 0.038(3) Uani d 1 . . C
H17 0.8006 0.273 0.243 0.046 Uiso calc 1 . . H
C17 0.832(2) 0.5179(16) 0.2500(4) 0.050(3) Uani d 1 . . C
H16 0.8588 0.5372 0.22 0.06 Uiso calc 1 . . H
C27 0.795(2) 0.4958(13) 0.5988(4) 0.040(3) Uani d 1 . . C
H20 0.8653 0.5847 0.6173 0.049 Uiso calc 1 . . H
C25 0.6751(17) 0.3720(12) 0.5253(3) 0.028(2) Uani d 1 . . C
C18 0.830(2) 0.6444(16) 0.2809(4) 0.048(3) Uani d 1 . . C
H15 0.8629 0.7484 0.2718 0.057 Uiso calc 1 . . H
C19 0.779(2) 0.6186(13) 0.3249(4) 0.044(3) Uani d 1 . . C
H14 0.7728 0.7051 0.3448 0.053 Uiso calc 1 . . H
S2 0.2512(5) 0.2514(3) 0.17170(9) 0.0369(8) Uani d 1 . . S
O3 0.0181(12) 0.1304(8) 0.0386(2) 0.0333(18) Uani d 1 . . O
O4 0.2623(13) 0.6121(8) 0.0808(2) 0.0351(19) Uani d 1 . . O
O1 0.4381(12) 0.2336(9) 0.1518(2) 0.039(2) Uani d 1 . . O
O2 0.1659(13) 0.1530(9) 0.2067(2) 0.041(2) Uani d 1 . . O
C8 0.1369(17) 0.3408(11) 0.0961(3) 0.025(2) Uani d 1 . . C
N2 0.1636(14) 0.3888(10) 0.0189(3) 0.031(2) Uani d 1 . . N
H5 0.2004 0.488 0.029 0.038 Uiso calc 1 . . H
N3 0.0882(14) 0.2067(10) -0.0465(3) 0.030(2) Uani d 1 . . N
H13 0.0293 0.1334 -0.0294 0.036 Uiso calc 1 . . H
N1 0.0795(14) 0.2265(10) 0.1303(3) 0.030(2) Uani d 1 . . N
C9 0.1006(18) 0.2748(12) 0.0504(3) 0.030(2) Uani d 1 . . C
C14 0.0921(18) 0.1668(12) -0.0919(3) 0.032(3) Uani d 1 . . C
H9 0.0327 0.0626 -0.1038 0.038 Uiso calc 1 . . H
C7 0.2192(15) 0.5049(12) 0.1093(3) 0.027(2) Uani d 1 . . C
C13 0.182(2) 0.2793(13) -0.1190(4) 0.038(3) Uani d 1 . . C
H8 0.1853 0.2533 -0.15 0.045 Uiso calc 1 . . H
C10 0.1718(18) 0.3549(13) -0.0273(3) 0.033(3) Uani d 1 . . C
C6 0.265(2) 0.5618(14) 0.1577(4) 0.039(3) Uani d 1 . . C
C15 -0.1306(19) 0.1997(13) 0.1435(4) 0.038(3) Uani d 1 . . C
H11 -0.1581 0.3005 0.1528 0.057 Uiso calc 1 . . H
H12 -0.154 0.1315 0.1681 0.057 Uiso calc 1 . . H
H10 -0.219 0.1491 0.1183 0.057 Uiso calc 1 . . H
C5 0.2838(18) 0.4540(14) 0.1902(4) 0.036(3) Uani d 1 . . C
C11 0.2645(17) 0.4731(13) -0.0553(3) 0.032(2) Uani d 1 . . C
H6 0.3208 0.5773 -0.043 0.039 Uiso calc 1 . . H
C1 0.298(2) 0.7229(14) 0.1718(4) 0.044(3) Uani d 1 . . C
H1 0.2874 0.7954 0.1508 0.052 Uiso calc 1 . . H
C3 0.3674(18) 0.6741(14) 0.2486(4) 0.041(3) Uani d 1 . . C
H3 0.4001 0.713 0.2785 0.049 Uiso calc 1 . . H
C12 0.274(2) 0.4376(14) -0.1010(4) 0.042(3) Uani d 1 . . C
H7 0.3384 0.516 -0.1196 0.05 Uiso calc 1 . . H
C4 0.339(2) 0.5098(15) 0.2355(4) 0.044(3) Uani d 1 . . C
H4 0.3555 0.4391 0.2565 0.053 Uiso calc 1 . . H
C2 0.3460(19) 0.7776(14) 0.2160(3) 0.041(3) Uani d 1 . . C
H2 0.3647 0.8862 0.2244 0.049 Uiso calc 1 . . H
N7 0.4843(15) -0.1635(10) -0.0022(3) 0.037(2) Uani d 1 . . N
C32 0.4638(19) -0.0816(12) 0.0368(4) 0.037(3) Uani d 1 . . C
H30 0.4405 -0.1343 0.0633 0.044 Uiso calc 1 . . H
C31 0.5229(18) -0.0801(13) -0.0380(4) 0.037(3) Uani d 1 . . C
H29 0.5422 -0.133 -0.0653 0.044 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N8 C33 . 1.326(15) ?
N8 C34 . 1.329(14) ?
C33 C34 2_776 1.372(15) ?
C33 H28 . 0.93 ?
C34 C33 2_776 1.372(15) ?
C34 H27 . 0.93 ?
S1 O5 . 1.427(8) ?
S1 O6 . 1.449(9) ?
S1 N4 . 1.632(9) ?
S1 C21 . 1.765(13) ?
O8 C22 . 1.247(13) ?
O7 C24 . 1.269(12) ?
N5 C24 . 1.364(14) ?
N5 C25 . 1.367(13) ?
N5 H18 . 0.86 ?
C23 C22 . 1.417(14) ?
C23 C24 . 1.443(14) ?
C23 N4 . 1.446(14) ?
N4 C30 . 1.488(16) ?
N6 C25 . 1.351(12) ?
N6 C29 . 1.366(13) ?
N6 H26 . 0.86 ?
C22 C20 . 1.504(14) ?
C20 C19 . 1.387(13) ?
C20 C21 . 1.414(14) ?
C29 C28 . 1.344(16) ?
C29 H22 . 0.93 ?
C26 C27 . 1.394(15) ?
C26 C25 . 1.398(14) ?
C26 H19 . 0.93 ?
C21 C16 . 1.396(14) ?
C30 H25 . 0.96 ?
C30 H24 . 0.96 ?
C30 H23 . 0.96 ?
C28 C27 . 1.407(14) ?
C28 H21 . 0.93 ?
C16 C17 . 1.421(17) ?
C16 H17 . 0.93 ?
C17 C18 . 1.377(17) ?
C17 H16 . 0.93 ?
C27 H20 . 0.93 ?
C18 C19 . 1.372(16) ?
C18 H15 . 0.93 ?
C19 H14 . 0.93 ?
S2 O2 . 1.423(7) ?
S2 O1 . 1.443(8) ?
S2 N1 . 1.650(10) ?
S2 C5 . 1.755(13) ?
O3 C9 . 1.254(12) ?
O4 C7 . 1.280(11) ?
C8 C7 . 1.410(14) ?
C8 C9 . 1.425(14) ?
C8 N1 . 1.454(11) ?
N2 C10 . 1.384(13) ?
N2 C9 . 1.398(12) ?
N2 H5 . 0.86 ?
N3 C10 . 1.344(13) ?
N3 C14 . 1.370(12) ?
N3 H13 . 0.86 ?
N1 C15 . 1.448(14) ?
C14 C13 . 1.336(13) ?
C14 H9 . 0.93 ?
C7 C6 . 1.488(15) ?
C13 C12 . 1.414(16) ?
C13 H8 . 0.93 ?
C10 C11 . 1.393(13) ?
C6 C1 . 1.386(15) ?
C6 C5 . 1.415(16) ?
C15 H11 . 0.96 ?
C15 H12 . 0.96 ?
C15 H10 . 0.96 ?
C5 C4 . 1.408(16) ?
C11 C12 . 1.372(15) ?
C11 H6 . 0.93 ?
C1 C2 . 1.366(16) ?
C1 H1 . 0.93 ?
C3 C2 . 1.397(17) ?
C3 C4 . 1.409(16) ?
C3 H3 . 0.93 ?
C12 H7 . 0.93 ?
C4 H4 . 0.93 ?
C2 H2 . 0.93 ?
N7 C31 . 1.316(13) ?
N7 C32 . 1.341(14) ?
C32 C31 2_655 1.375(15) ?
C32 H30 . 0.93 ?
C31 C32 2_655 1.375(15) ?
C31 H29 . 0.93 ?

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
C33 N8 C34 116.8(9) . . ?
N8 C33 C34 122.5(10) . 2_776 ?
N8 C33 H28 118.8 . . ?
C34 C33 H28 118.8 2_776 . ?
N8 C34 C33 120.7(10) . 2_776 ?
N8 C34 H27 119.7 . . ?
C33 C34 H27 119.7 2_776 . ?
O5 S1 O6 118.4(5) . . ?
O5 S1 N4 109.3(5) . . ?
O6 S1 N4 107.7(5) . . ?
O5 S1 C21 109.7(5) . . ?
O6 S1 C21 108.9(5) . . ?
N4 S1 C21 101.4(5) . . ?
C24 N5 C25 127.1(8) . . ?
C24 N5 H18 116.5 . . ?
C25 N5 H18 116.5 . . ?
C22 C23 C24 122.8(10) . . ?
C22 C23 N4 120.7(9) . . ?
C24 C23 N4 116.5(9) . . ?
C23 N4 C30 114.6(9) . . ?
C23 N4 S1 114.0(7) . . ?
C30 N4 S1 116.0(7) . . ?
C25 N6 C29 123.2(9) . . ?
C25 N6 H26 118.4 . . ?
C29 N6 H26 118.4 . . ?
O8 C22 C23 124.1(10) . . ?
O8 C22 C20 117.2(9) . . ?
C23 C22 C20 118.8(9) . . ?
O7 C24 N5 121.9(9) . . ?
O7 C24 C23 123.2(10) . . ?
N5 C24 C23 114.9(9) . . ?
C19 C20 C21 117.6(10) . . ?
C19 C20 C22 120.1(10) . . ?
C21 C20 C22 122.2(9) . . ?
C28 C29 N6 120.4(9) . . ?
C28 C29 H22 119.8 . . ?
N6 C29 H22 119.8 . . ?
C27 C26 C25 118.5(10) . . ?
C27 C26 H19 120.7 . . ?
C25 C26 H19 120.7 . . ?
C16 C21 C20 122.9(11) . . ?
C16 C21 S1 119.8(9) . . ?
C20 C21 S1 117.2(8) . . ?
N4 C30 H25 109.5 . . ?
N4 C30 H24 109.5 . . ?
H25 C30 H24 109.5 . . ?
N4 C30 H23 109.5 . . ?
H25 C30 H23 109.5 . . ?
H24 C30 H23 109.5 . . ?
C29 C28 C27 118.4(10) . . ?
C29 C28 H21 120.8 . . ?
C27 C28 H21 120.8 . . ?
C21 C16 C17 116.3(11) . . ?
C21 C16 H17 121.8 . . ?
C17 C16 H17 121.8 . . ?
C18 C17 C16 121.2(11) . . ?
C18 C17 H16 119.4 . . ?
C16 C17 H16 119.4 . . ?
C26 C27 C28 121.0(11) . . ?
C26 C27 H20 119.5 . . ?
C28 C27 H20 119.5 . . ?
N6 C25 N5 120.1(9) . . ?
N6 C25 C26 118.4(9) . . ?
N5 C25 C26 121.4(8) . . ?
C19 C18 C17 120.7(12) . . ?
C19 C18 H15 119.6 . . ?
C17 C18 H15 119.6 . . ?
C18 C19 C20 121.2(11) . . ?
C18 C19 H14 119.4 . . ?
C20 C19 H14 119.4 . . ?
O2 S2 O1 119.3(5) . . ?
O2 S2 N1 108.8(5) . . ?
O1 S2 N1 107.5(5) . . ?
O2 S2 C5 109.7(5) . . ?
O1 S2 C5 108.3(5) . . ?
N1 S2 C5 102.0(5) . . ?
C7 C8 C9 124.6(8) . . ?
C7 C8 N1 119.9(8) . . ?
C9 C8 N1 115.4(9) . . ?
C10 N2 C9 125.3(8) . . ?
C10 N2 H5 117.4 . . ?
C9 N2 H5 117.4 . . ?
C10 N3 C14 123.2(8) . . ?
C10 N3 H13 118.4 . . ?
C14 N3 H13 118.4 . . ?
C15 N1 C8 114.1(8) . . ?
C15 N1 S2 116.4(7) . . ?
C8 N1 S2 113.6(7) . . ?
O3 C9 N2 122.0(9) . . ?
O3 C9 C8 124.8(9) . . ?
N2 C9 C8 113.2(9) . . ?
C13 C14 N3 119.2(10) . . ?
C13 C14 H9 120.4 . . ?
N3 C14 H9 120.4 . . ?
O4 C7 C8 122.7(9) . . ?
O4 C7 C6 116.3(9) . . ?
C8 C7 C6 121.0(8) . . ?
C14 C13 C12 120.4(10) . . ?
C14 C13 H8 119.8 . . ?
C12 C13 H8 119.8 . . ?
N3 C10 N2 120.9(8) . . ?
N3 C10 C11 117.8(9) . . ?
N2 C10 C11 121.3(9) . . ?
C1 C6 C5 118.3(11) . . ?
C1 C6 C7 120.8(10) . . ?
C5 C6 C7 120.9(10) . . ?
N1 C15 H11 109.5 . . ?
N1 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
N1 C15 H10 109.5 . . ?
H11 C15 H10 109.5 . . ?
H12 C15 H10 109.5 . . ?
C4 C5 C6 120.7(11) . . ?
C4 C5 S2 121.1(9) . . ?
C6 C5 S2 118.1(9) . . ?
C12 C11 C10 120.7(10) . . ?
C12 C11 H6 119.6 . . ?
C10 C11 H6 119.6 . . ?
C2 C1 C6 121.5(12) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C2 C3 C4 118.8(11) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C11 C12 C13 118.5(10) . . ?
C11 C12 H7 120.7 . . ?
C13 C12 H7 120.7 . . ?
C5 C4 C3 119.2(11) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C1 C2 C3 121.5(11) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C31 N7 C32 116.4(9) . . ?
N7 C32 C31 120.3(10) . 2_655 ?
N7 C32 H30 119.9 . . ?
C31 C32 H30 119.9 2_655 . ?
N7 C31 C32 123.3(10) . 2_655 ?
N7 C31 H29 118.4 . . ?
C32 C31 H29 118.4 2_655 . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 984169'
#######################################################################
#
#                 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N3 O4 S, C6 H Cl2 O4'
_chemical_formula_sum            'C21 H15 Cl2 N3 O8 S'
_chemical_formula_weight         540.32

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.1504(4)
_cell_length_b                   10.9678(4)
_cell_length_c                   11.7747(5)
_cell_angle_alpha                89.228(2)
_cell_angle_beta                 75.765(2)
_cell_angle_gamma                70.977(2)
_cell_volume                     1080.00(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30881
_cell_measurement_theta_min      1
_cell_measurement_theta_max      61.26

_exptl_crystal_description       plates
_exptl_crystal_colour            purple
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8970
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30881
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         30.56
_reflns_number_total             6607
_reflns_number_gt                4819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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.

Problem:
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C3     -   C4     .. 1.54 Ang.
PLAT335_ALERT_2_G Check Large C6 Ring    C-C Range C1     -C6   0.19 Ang.

Response:
Conjugated ring system with deprotonated oxygen. 
;

_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)+(0.0459P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6607
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_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
H5 H 0.036(2) -0.2979(16) -0.0690(15) 0.013(4) Uiso 1 1 d . . .
H4 H 0.173(2) -0.4782(17) 0.0184(15) 0.014(4) Uiso 1 1 d . . .
H1 H 0.091(2) -0.1074(17) -0.0560(15) 0.018(5) Uiso 1 1 d . . .
H2 H 0.289(2) -0.1070(17) 0.0346(15) 0.019(5) Uiso 1 1 d . . .
H12 H 0.896(3) -0.0186(19) 0.2722(17) 0.031(6) Uiso 1 1 d . . .
H10 H 1.059(3) -0.425(2) 0.4283(17) 0.031(5) Uiso 1 1 d . . .
H13 H 1.148(3) -0.2584(18) 0.4798(17) 0.029(5) Uiso 1 1 d . . .
H6 H 0.486(3) -0.371(2) 0.1683(18) 0.031(6) Uiso 1 1 d . . .
H3 H 0.347(3) -0.473(2) 0.112(2) 0.049(7) Uiso 1 1 d . . .
H15 H 0.391(3) -0.010(2) 0.430(2) 0.051(7) Uiso 1 1 d . . .
H11 H 0.673(3) -0.070(2) 0.110(2) 0.051(8) Uiso 1 1 d . . .
H7 H 0.450(3) -0.290(2) 0.3828(19) 0.044(7) Uiso 1 1 d . . .
H14 H 1.081(3) -0.057(2) 0.3909(19) 0.041(6) Uiso 1 1 d . . .
H8 H 0.569(3) -0.282(2) 0.449(2) 0.055(7) Uiso 1 1 d . . .
H9 H 0.551(3) -0.419(2) 0.424(2) 0.052(7) Uiso 1 1 d . . .
Cl1 Cl 0.69648(5) 0.29005(4) 0.33008(3) 0.01773(9) Uani 1 1 d . . .
S1 S 0.85476(5) -0.43935(4) 0.28611(4) 0.01725(9) Uani 1 1 d . . .
Cl2 Cl 0.14024(5) 0.13058(4) 0.21357(4) 0.02280(10) Uani 1 1 d . . .
O3 O 0.27460(15) 0.33276(11) 0.10990(9) 0.0187(2) Uani 1 1 d . . .
O4 O 0.47726(14) 0.42674(10) 0.18146(9) 0.0172(2) Uani 1 1 d . . .
O2 O 0.57799(15) 0.07271(11) 0.41673(9) 0.0179(2) Uani 1 1 d . . .
O1 O 0.33596(16) 0.01180(11) 0.38004(10) 0.0195(3) Uani 1 1 d . . .
O7 O 0.51479(15) -0.11907(10) 0.08703(10) 0.0196(3) Uani 1 1 d . . .
O8 O 0.74141(16) -0.07114(11) 0.14339(10) 0.0199(3) Uani 1 1 d . . .
C5 C 0.5444(2) 0.24883(14) 0.29678(13) 0.0139(3) Uani 1 1 d . . .
N3 N 0.66978(17) -0.35842(12) 0.28138(11) 0.0141(3) Uani 1 1 d . . .
N1 N 0.30042(17) -0.39727(12) 0.07172(11) 0.0140(3) Uani 1 1 d . . .
N2 N 0.46048(17) -0.30465(13) 0.13900(11) 0.0146(3) Uani 1 1 d . . .
O6 O 0.94179(16) -0.48913(11) 0.16883(11) 0.0235(3) Uani 1 1 d . . .
C2 C 0.2927(2) 0.17140(14) 0.24513(13) 0.0150(3) Uani 1 1 d . . .
C4 C 0.4587(2) 0.32456(14) 0.22357(12) 0.0138(3) Uani 1 1 d . . .
C6 C 0.5080(2) 0.14180(14) 0.34852(12) 0.0136(3) Uani 1 1 d . . .
O5 O 0.85063(17) -0.52477(11) 0.37896(11) 0.0266(3) Uani 1 1 d . . .
C13 C 0.6581(2) -0.24911(14) 0.21077(13) 0.0142(3) Uani 1 1 d . . .
C3 C 0.3344(2) 0.27800(14) 0.18657(13) 0.0141(3) Uani 1 1 d . . .
C1 C 0.3719(2) 0.10799(14) 0.32304(13) 0.0146(3) Uani 1 1 d . . .
C20 C 0.9311(2) -0.10167(16) 0.30135(14) 0.0189(3) Uani 1 1 d . . .
C15 C 0.8700(2) -0.19707(15) 0.27791(13) 0.0160(3) Uani 1 1 d . . .
C9 C 0.3423(2) -0.29084(14) 0.07993(13) 0.0143(3) Uani 1 1 d . . .
C16 C 0.9211(2) -0.31653(15) 0.32568(14) 0.0179(3) Uani 1 1 d . . .
C12 C 0.5411(2) -0.21839(14) 0.14077(13) 0.0153(3) Uani 1 1 d . . .
C10 C 0.2649(2) -0.17918(15) 0.03196(14) 0.0172(3) Uani 1 1 d . . .
C8 C 0.1895(2) -0.40019(15) 0.01619(13) 0.0160(3) Uani 1 1 d . . .
C11 C 0.1494(2) -0.18143(15) -0.02397(14) 0.0177(3) Uani 1 1 d . . .
C14 C 0.7515(2) -0.17341(14) 0.20848(13) 0.0148(3) Uani 1 1 d . . .
C7 C 0.1099(2) -0.29248(15) -0.03264(14) 0.0173(3) Uani 1 1 d . . .
C21 C 0.5463(3) -0.33659(19) 0.39372(15) 0.0232(4) Uani 1 1 d . . .
C17 C 1.0234(2) -0.33961(18) 0.39958(16) 0.0239(4) Uani 1 1 d . . .
C19 C 1.0354(2) -0.12452(17) 0.37376(15) 0.0221(4) Uani 1 1 d . . .
C18 C 1.0798(2) -0.24188(18) 0.42339(16) 0.0255(4) Uani 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
Cl1 C5 1.7254(16) . ?
S1 O6 1.4266(13) . ?
S1 O5 1.4316(12) . ?
S1 N3 1.6498(14) . ?
S1 C16 1.7573(16) . ?
Cl2 C2 1.7179(16) . ?
O3 C3 1.2204(17) . ?
O4 C4 1.2641(18) . ?
O2 C6 1.2447(17) . ?
O1 C1 1.3304(19) . ?
O1 H15 0.85(2) . ?
O7 C12 1.2371(18) . ?
O8 C14 1.3409(19) . ?
O8 H11 0.81(3) . ?
C5 C4 1.392(2) . ?
C5 C6 1.413(2) . ?
N3 C13 1.4399(19) . ?
N3 C21 1.477(2) . ?
N1 C8 1.344(2) . ?
N1 C9 1.353(2) . ?
N1 H3 0.98(2) . ?
N2 C12 1.379(2) . ?
N2 C9 1.3918(19) . ?
N2 H6 0.79(2) . ?
C2 C1 1.353(2) . ?
C2 C3 1.459(2) . ?
C4 C3 1.540(2) . ?
C6 C1 1.506(2) . ?
C13 C14 1.368(2) . ?
C13 C12 1.460(2) . ?
C20 C19 1.392(2) . ?
C20 C15 1.396(2) . ?
C20 H12 0.95(2) . ?
C15 C16 1.401(2) . ?
C15 C14 1.469(2) . ?
C9 C10 1.390(2) . ?
C16 C17 1.392(2) . ?
C10 C11 1.382(2) . ?
C10 H2 0.893(19) . ?
C8 C7 1.372(2) . ?
C8 H4 0.913(19) . ?
C11 C7 1.390(2) . ?
C11 H1 0.945(17) . ?
C7 H5 0.899(18) . ?
C21 H7 0.91(2) . ?
C21 H8 0.99(2) . ?
C21 H9 0.96(3) . ?
C17 C18 1.391(2) . ?
C17 H10 0.97(2) . ?
C19 C18 1.385(2) . ?
C19 H14 1.00(2) . ?
C18 H13 0.997(19) . ?

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
O6 S1 O5 120.23(8) . . ?
O6 S1 N3 106.70(7) . . ?
O5 S1 N3 108.85(8) . . ?
O6 S1 C16 108.55(8) . . ?
O5 S1 C16 108.65(7) . . ?
N3 S1 C16 102.40(7) . . ?
C1 O1 H15 108.4(18) . . ?
C14 O8 H11 104.3(18) . . ?
C4 C5 C6 122.47(14) . . ?
C4 C5 Cl1 118.99(12) . . ?
C6 C5 Cl1 118.49(11) . . ?
C13 N3 C21 115.85(13) . . ?
C13 N3 S1 113.18(11) . . ?
C21 N3 S1 116.12(11) . . ?
C8 N1 C9 122.44(14) . . ?
C8 N1 H3 118.7(14) . . ?
C9 N1 H3 118.7(14) . . ?
C12 N2 C9 125.20(14) . . ?
C12 N2 H6 119.8(16) . . ?
C9 N2 H6 114.7(16) . . ?
C1 C2 C3 120.28(14) . . ?
C1 C2 Cl2 121.44(13) . . ?
C3 C2 Cl2 118.28(11) . . ?
O4 C4 C5 125.67(15) . . ?
O4 C4 C3 116.72(12) . . ?
C5 C4 C3 117.57(14) . . ?
O2 C6 C5 125.22(14) . . ?
O2 C6 C1 115.99(14) . . ?
C5 C6 C1 118.78(12) . . ?
C14 C13 N3 122.16(13) . . ?
C14 C13 C12 119.54(14) . . ?
N3 C13 C12 118.29(14) . . ?
O3 C3 C2 123.02(14) . . ?
O3 C3 C4 118.31(14) . . ?
C2 C3 C4 118.67(12) . . ?
O1 C1 C2 122.32(15) . . ?
O1 C1 C6 116.29(12) . . ?
C2 C1 C6 121.39(14) . . ?
C19 C20 C15 120.26(16) . . ?
C19 C20 H12 119.7(12) . . ?
C15 C20 H12 120.0(12) . . ?
C20 C15 C16 118.14(14) . . ?
C20 C15 C14 121.76(14) . . ?
C16 C15 C14 120.07(14) . . ?
N1 C9 C10 118.92(14) . . ?
N1 C9 N2 115.12(13) . . ?
C10 C9 N2 125.95(15) . . ?
C17 C16 C15 121.95(15) . . ?
C17 C16 S1 120.59(13) . . ?
C15 C16 S1 117.44(11) . . ?
O7 C12 N2 121.99(14) . . ?
O7 C12 C13 121.36(15) . . ?
N2 C12 C13 116.65(13) . . ?
C11 C10 C9 118.75(15) . . ?
C11 C10 H2 119.2(11) . . ?
C9 C10 H2 122.0(11) . . ?
N1 C8 C7 120.79(15) . . ?
N1 C8 H4 112.5(11) . . ?
C7 C8 H4 126.7(11) . . ?
C10 C11 C7 121.27(15) . . ?
C10 C11 H1 122.1(11) . . ?
C7 C11 H1 116.6(11) . . ?
O8 C14 C13 122.71(14) . . ?
O8 C14 C15 114.64(14) . . ?
C13 C14 C15 122.65(14) . . ?
C8 C7 C11 117.80(15) . . ?
C8 C7 H5 118.4(11) . . ?
C11 C7 H5 123.8(11) . . ?
N3 C21 H7 109.7(15) . . ?
N3 C21 H8 108.5(17) . . ?
H7 C21 H8 105.2(19) . . ?
N3 C21 H9 108.6(15) . . ?
H7 C21 H9 114(2) . . ?
H8 C21 H9 110.6(19) . . ?
C18 C17 C16 118.62(16) . . ?
C18 C17 H10 121.8(12) . . ?
C16 C17 H10 119.5(12) . . ?
C18 C19 C20 120.56(16) . . ?
C18 C19 H14 118.3(12) . . ?
C20 C19 H14 121.1(12) . . ?
C19 C18 C17 120.40(16) . . ?
C19 C18 H13 122.1(12) . . ?
C17 C18 H13 117.5(12) . . ?

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
N1 H3 O4 0.98(2) 1.70(2) 2.6342(16) 158(2) 1_545
N1 H3 O3 0.98(2) 2.43(2) 3.0649(18) 121.9(17) 1_545
N2 H6 O4 0.79(2) 2.25(2) 2.9422(17) 146.9(19) 1_545
O1 H15 O2 0.85(2) 1.98(2) 2.7562(15) 152(3) 2_656
O8 H11 O7 0.81(3) 1.78(3) 2.5325(17) 153(3) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 984170'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N3 O4 S, C6 H Cl2 O4'
_chemical_formula_sum            'C21 H15 Cl2 N3 O8 S'
_chemical_formula_weight         540.32

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   P21/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                   8.5627(5)
_cell_length_b                   13.3395(7)
_cell_length_c                   19.3963(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.925(3)
_cell_angle_gamma                90.00
_cell_volume                     2175.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    39751
_cell_measurement_theta_min      1
_cell_measurement_theta_max      89.897

_exptl_crystal_description       plates
_exptl_crystal_colour            purple
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9023
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38649
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.72
_reflns_number_total             5083
_reflns_number_gt                3284
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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.

Problem:
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5     -   C6     ...1.54 Ang. 
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1     -C5     1.44 Ang. 
PLAT335_ALERT_2_G Check Large C6 Ring    C-C Range C1     -C5     0.20 Ang.

Response:
Conjugated ring system with deprotonated oxygen. 
;

_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)+(0.0289P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5083
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_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
H12 H -0.140(2) 0.5362(15) 0.3403(11) 0.019(6) Uiso 1 1 d . . .
H11 H -0.047(2) 0.6935(15) 0.3780(12) 0.019(6) Uiso 1 1 d . . .
H4 H 0.534(2) 0.7098(15) -0.1471(11) 0.017(6) Uiso 1 1 d . . .
H7 H 0.009(3) 0.7433(15) 0.0196(12) 0.026(6) Uiso 1 1 d . . .
H9 H -0.072(3) 0.7526(16) 0.0909(12) 0.031(7) Uiso 1 1 d . . .
H13 H -0.091(2) 0.4724(15) 0.2374(11) 0.017(6) Uiso 1 1 d . . .
H2 H 0.302(3) 0.4407(15) -0.0642(11) 0.022(7) Uiso 1 1 d . . .
H10 H 0.107(2) 0.7824(15) 0.3129(11) 0.014(6) Uiso 1 1 d . . .
H5 H 0.400(3) 0.7289(17) -0.0590(12) 0.033(7) Uiso 1 1 d . . .
H3 H 0.564(2) 0.5520(15) -0.1979(11) 0.020(6) Uiso 1 1 d . . .
H1 H 0.438(2) 0.4159(15) -0.1557(10) 0.018(6) Uiso 1 1 d . . .
H8 H 0.052(3) 0.8324(16) 0.0718(11) 0.023(7) Uiso 1 1 d . . .
H14 H 0.095(3) 0.4317(18) 0.0986(14) 0.054(9) Uiso 1 1 d . . .
H6 H 0.281(3) 0.6753(17) 0.0178(13) 0.037(8) Uiso 1 1 d . . .
H15 H 0.405(3) 0.5812(18) 0.2980(14) 0.043(9) Uiso 1 1 d . . .
S1 S 0.22971(7) 0.74010(4) 0.18995(3) 0.01620(13) Uani 1 1 d . . .
Cl2 Cl 0.80123(7) 0.53699(4) 0.50984(3) 0.02354(15) Uani 1 1 d . . .
Cl3 Cl 0.25249(7) 0.31402(4) 0.29987(3) 0.02535(15) Uani 1 1 d . . .
O8 O 0.17273(18) 0.45919(11) 0.02896(8) 0.0210(4) Uani 1 1 d . . .
O2 O 0.44676(18) 0.23702(11) 0.43408(8) 0.0226(4) Uani 1 1 d . . .
O4 O 0.36089(19) 0.52545(12) 0.29357(8) 0.0228(4) Uani 1 1 d . . .
O1 O 0.68962(18) 0.32443(10) 0.51973(8) 0.0214(4) Uani 1 1 d . . .
O3 O 0.58158(18) 0.61655(11) 0.38131(8) 0.0245(4) Uani 1 1 d . . .
O6 O 0.38358(17) 0.69509(10) 0.21108(7) 0.0184(3) Uani 1 1 d . . .
O7 O 0.05524(19) 0.44384(11) 0.14042(9) 0.0222(4) Uani 1 1 d . . .
N1 N 0.1603(2) 0.70533(12) 0.10841(9) 0.0165(4) Uani 1 1 d . . .
O5 O 0.21624(18) 0.84673(10) 0.19419(8) 0.0203(4) Uani 1 1 d . . .
N2 N 0.2640(2) 0.61258(14) 0.00065(9) 0.0181(4) Uani 1 1 d . . .
C5 C 0.4803(3) 0.32250(16) 0.41948(11) 0.0171(5) Uani 1 1 d . . .
N3 N 0.4097(2) 0.66434(14) -0.08028(10) 0.0189(4) Uani 1 1 d . . .
C6 C 0.6170(3) 0.37566(16) 0.46899(11) 0.0170(5) Uani 1 1 d . . .
C13 C 0.1411(3) 0.59804(15) 0.10072(11) 0.0160(5) Uani 1 1 d . . .
C4 C 0.6500(3) 0.47457(15) 0.45455(11) 0.0162(5) Uani 1 1 d . . .
C16 C 0.1918(3) 0.55017(16) 0.04111(12) 0.0184(5) Uani 1 1 d . . .
C17 C 0.3386(3) 0.58622(16) -0.05372(11) 0.0173(5) Uani 1 1 d . . .
C3 C 0.5627(3) 0.52769(16) 0.39706(12) 0.0180(5) Uani 1 1 d . . .
C22 C 0.0668(3) 0.72143(17) 0.29789(12) 0.0196(5) Uani 1 1 d . . .
C1 C 0.3982(3) 0.37582(16) 0.35784(11) 0.0176(5) Uani 1 1 d . . .
C14 C 0.0796(3) 0.54301(16) 0.14834(11) 0.0169(5) Uani 1 1 d . . .
C15 C 0.0235(3) 0.76449(19) 0.06995(13) 0.0220(5) Uani 1 1 d . . .
C10 C 0.0399(3) 0.58591(15) 0.21247(11) 0.0169(5) Uani 1 1 d . . .
C2 C 0.4349(3) 0.47176(16) 0.34804(11) 0.0173(5) Uani 1 1 d . . .
C19 C 0.4304(3) 0.48016(17) -0.13593(12) 0.0202(5) Uani 1 1 d . . .
C11 C 0.0989(2) 0.68049(15) 0.23664(11) 0.0154(5) Uani 1 1 d . . .
C18 C 0.3486(3) 0.49158(17) -0.08215(12) 0.0190(5) Uani 1 1 d . . .
C20 C 0.5028(3) 0.56153(17) -0.16175(12) 0.0217(5) Uani 1 1 d . . .
C21 C 0.4904(3) 0.65351(18) -0.13250(12) 0.0226(6) Uani 1 1 d . . .
C9 C -0.0501(3) 0.53341(17) 0.25283(12) 0.0203(5) Uani 1 1 d . . .
C8 C -0.0806(3) 0.57372(18) 0.31421(13) 0.0232(6) Uani 1 1 d . . .
C7 C -0.0234(3) 0.66742(17) 0.33683(12) 0.0235(6) Uani 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 1.4306(14) . ?
S1 O6 1.4352(15) . ?
S1 N1 1.6473(18) . ?
S1 C11 1.758(2) . ?
Cl2 C4 1.730(2) . ?
Cl3 C1 1.723(2) . ?
O8 C16 1.241(2) . ?
O2 C5 1.222(2) . ?
O4 C2 1.333(3) . ?
O4 H15 0.83(2) . ?
O1 C6 1.261(2) . ?
O3 C3 1.242(2) . ?
O7 C14 1.343(2) . ?
O7 H14 0.95(3) . ?
N1 C13 1.445(2) . ?
N1 C15 1.490(3) . ?
N2 C16 1.369(3) . ?
N2 C17 1.378(3) . ?
N2 H6 0.90(2) . ?
C5 C1 1.453(3) . ?
C5 C6 1.539(3) . ?
N3 C21 1.338(3) . ?
N3 C17 1.357(3) . ?
N3 H5 0.96(2) . ?
C6 C4 1.389(3) . ?
C13 C14 1.362(3) . ?
C13 C16 1.457(3) . ?
C4 C3 1.410(3) . ?
C17 C18 1.387(3) . ?
C3 C2 1.505(3) . ?
C22 C7 1.381(3) . ?
C22 C11 1.382(3) . ?
C22 H10 0.91(2) . ?
C1 C2 1.340(3) . ?
C14 C10 1.466(3) . ?
C15 H7 1.00(2) . ?
C15 H9 1.00(2) . ?
C15 H8 0.94(2) . ?
C10 C9 1.387(3) . ?
C10 C11 1.406(3) . ?
C19 C18 1.371(3) . ?
C19 C20 1.390(3) . ?
C19 H1 0.95(2) . ?
C18 H2 0.89(2) . ?
C20 C21 1.364(3) . ?
C20 H3 0.96(2) . ?
C21 H4 0.91(2) . ?
C9 C8 1.376(3) . ?
C9 H13 0.913(19) . ?
C8 C7 1.383(3) . ?
C8 H12 0.93(2) . ?
C7 H11 0.93(2) . ?

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 O6 118.63(9) . . ?
O5 S1 N1 108.47(9) . . ?
O6 S1 N1 107.53(9) . . ?
O5 S1 C11 110.72(9) . . ?
O6 S1 C11 107.68(9) . . ?
N1 S1 C11 102.58(10) . . ?
C2 O4 H15 105.2(19) . . ?
C14 O7 H14 101.0(15) . . ?
C13 N1 C15 114.20(18) . . ?
C13 N1 S1 113.02(14) . . ?
C15 N1 S1 115.98(14) . . ?
C16 N2 C17 127.49(19) . . ?
C16 N2 H6 114.3(15) . . ?
C17 N2 H6 117.0(15) . . ?
O2 C5 C1 123.3(2) . . ?
O2 C5 C6 118.00(19) . . ?
C1 C5 C6 118.68(18) . . ?
C21 N3 C17 122.5(2) . . ?
C21 N3 H5 121.1(14) . . ?
C17 N3 H5 116.3(14) . . ?
O1 C6 C4 125.7(2) . . ?
O1 C6 C5 116.20(18) . . ?
C4 C6 C5 118.1(2) . . ?
C14 C13 N1 120.99(19) . . ?
C14 C13 C16 120.91(19) . . ?
N1 C13 C16 118.10(18) . . ?
C6 C4 C3 122.6(2) . . ?
C6 C4 Cl2 119.29(17) . . ?
C3 C4 Cl2 118.07(16) . . ?
O8 C16 N2 122.9(2) . . ?
O8 C16 C13 122.1(2) . . ?
N2 C16 C13 115.03(19) . . ?
N3 C17 N2 113.64(19) . . ?
N3 C17 C18 118.9(2) . . ?
N2 C17 C18 127.5(2) . . ?
O3 C3 C4 126.9(2) . . ?
O3 C3 C2 115.5(2) . . ?
C4 C3 C2 117.62(19) . . ?
C7 C22 C11 119.1(2) . . ?
C7 C22 H10 120.6(13) . . ?
C11 C22 H10 120.3(13) . . ?
C2 C1 C5 119.6(2) . . ?
C2 C1 Cl3 121.64(18) . . ?
C5 C1 Cl3 118.71(16) . . ?
O7 C14 C13 121.7(2) . . ?
O7 C14 C10 115.17(19) . . ?
C13 C14 C10 123.1(2) . . ?
N1 C15 H7 106.1(12) . . ?
N1 C15 H9 110.1(13) . . ?
H7 C15 H9 113.3(18) . . ?
N1 C15 H8 108.8(14) . . ?
H7 C15 H8 107.0(18) . . ?
H9 C15 H8 111.4(18) . . ?
C9 C10 C11 117.9(2) . . ?
C9 C10 C14 121.6(2) . . ?
C11 C10 C14 120.43(19) . . ?
O4 C2 C1 122.5(2) . . ?
O4 C2 C3 114.45(19) . . ?
C1 C2 C3 123.1(2) . . ?
C18 C19 C20 121.0(2) . . ?
C18 C19 H1 119.8(12) . . ?
C20 C19 H1 119.2(12) . . ?
C22 C11 C10 121.6(2) . . ?
C22 C11 S1 120.94(17) . . ?
C10 C11 S1 117.25(16) . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H2 123.0(14) . . ?
C17 C18 H2 118.2(14) . . ?
C21 C20 C19 118.5(2) . . ?
C21 C20 H3 121.2(12) . . ?
C19 C20 H3 120.2(12) . . ?
N3 C21 C20 120.3(2) . . ?
N3 C21 H4 116.6(13) . . ?
C20 C21 H4 123.1(13) . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H13 120.6(13) . . ?
C10 C9 H13 118.8(13) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H12 118.3(13) . . ?
C7 C8 H12 120.8(13) . . ?
C22 C7 C8 119.9(2) . . ?
C22 C7 H11 120.7(13) . . ?
C8 C7 H11 119.4(13) . . ?

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
N3 H5 O1 0.96(2) 1.74(2) 2.654(2) 157(2) 2_655
N3 H5 O2 0.96(2) 2.53(2) 3.028(2) 112.2(16) 2_655
N2 H6 O1 0.90(2) 2.15(2) 2.891(2) 139(2) 2_655
N2 H6 O2 0.90(2) 2.48(2) 3.050(2) 121.4(18) 2_655
O4 H15 O6 0.83(2) 2.25(3) 2.799(2) 124(2) .
O7 H14 O8 0.95(3) 1.65(3) 2.560(2) 157(2) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.72
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 984171'
#######################################################################
#
#                 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_pirox_chlor_4b

_audit_creation_date             2014-01-22T10:01:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C20 H17 Cl N4 O6 S'
_chemical_formula_moiety         'C15 H14 N3 O4 S, 0.5(C6 Cl2 O4), C2 H3 N'
_chemical_formula_weight         476.89

#==============================================================================

# CRYSTAL DATA

_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                   7.0616(8)
_cell_length_b                   11.6031(13)
_cell_length_c                   13.2994(17)
_cell_angle_alpha                71.351(5)
_cell_angle_beta                 84.932(5)
_cell_angle_gamma                78.919(5)
_cell_volume                     1012.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_exptl_crystal_description       plates
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.34
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7148
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'


#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_number            15739
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_theta_min         1.617
_diffrn_reflns_theta_max         24.951
_diffrn_reflns_theta_full        22.5
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were placed on calculated positions and refined as riding on the
atoms to which they were bonded with the exception of those involved in 
hydrogen bonding.  H3, H6 and H10 were identified in a Fourier difference map
and their positions and isotropic displacement parameters allowed to freely
refine.
;
_reflns_number_total             2948
_reflns_number_gt                1959
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.045
_refine_ls_wR_factor_ref         0.1065
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N4 0.5437(5) 0.1540(3) 0.5704(3) 0.0476(10) Uani d 1 . . N
C20 0.5672(6) 0.2176(4) 0.6144(4) 0.0415(11) Uani d 1 . . C
C19 0.6032(6) 0.2988(4) 0.6750(4) 0.0500(12) Uani d 1 . . C
H19A 0.5228 0.2859 0.7383 0.075 Uiso calc 1 . . H
H19B 0.5736 0.3836 0.6319 0.075 Uiso calc 1 . . H
H19C 0.7363 0.2793 0.6938 0.075 Uiso calc 1 . . H
H6 0.191(5) 0.154(3) 0.816(3) 0.024(13) Uiso d 1 . . H
H10 0.299(5) -0.055(3) 1.126(3) 0.030(12) Uiso d 1 . . H
H3 0.120(6) 0.159(4) 0.663(3) 0.061(13) Uiso d 1 . . H
S 0.34146(12) 0.35562(8) 0.97037(7) 0.0206(3) Uani d 1 . . S
Cl2 0.80665(13) 0.45513(8) 0.31249(7) 0.0290(3) Uani d 1 . . Cl
O4 0.2286(3) -0.0591(2) 1.00912(19) 0.0264(6) Uani d 1 . . O
O2 0.2617(3) 0.48351(19) 0.92620(18) 0.0234(6) Uani d 1 . . O
O1 0.5348(3) 0.31080(19) 0.94063(18) 0.0238(6) Uani d 1 . . O
O3 0.3154(3) -0.0124(2) 1.1685(2) 0.0271(6) Uani d 1 . . O
O6 0.9751(3) 0.2688(2) 0.50973(18) 0.0260(6) Uani d 1 . . O
O5 0.8761(3) 0.6959(2) 0.32884(19) 0.0288(6) Uani d 1 . . O
N1 0.1996(4) 0.2727(2) 0.9433(2) 0.0192(7) Uani d 1 . . N
C4 0.3051(5) 0.1925(3) 1.1663(3) 0.0210(9) Uani d 1 . . C
N2 0.1944(4) 0.0880(3) 0.8481(3) 0.0210(8) Uani d 1 . . N
C3 0.3235(4) 0.3149(3) 1.1094(3) 0.0202(8) Uani d 1 . . C
C8 0.2360(4) 0.1438(3) 1.0047(3) 0.0177(8) Uani d 1 . . C
N3 0.1475(4) 0.0672(3) 0.6854(2) 0.0233(7) Uani d 1 . . N
C12 0.2099(4) -0.1185(3) 0.8261(3) 0.0210(9) Uani d 1 . . C
H12 0.2354 -0.1606 0.8971 0.025 Uiso calc 1 . . H
C10 0.2193(4) 0.0517(3) 0.9547(3) 0.0205(9) Uani d 1 . . C
C2 0.3388(4) 0.3984(3) 1.1614(3) 0.0233(9) Uani d 1 . . C
H2 0.3474 0.4798 1.123 0.028 Uiso calc 1 . . H
C1 0.3411(5) 0.3598(3) 1.2710(3) 0.0264(9) Uani d 1 . . C
H1 0.3514 0.4154 1.3065 0.032 Uiso calc 1 . . H
C11 0.1843(4) 0.0103(3) 0.7888(3) 0.0190(8) Uani d 1 . . C
C7 0.2832(5) 0.1068(3) 1.1091(3) 0.0212(9) Uani d 1 . . C
C14 0.1628(5) -0.1223(3) 0.6501(3) 0.0233(9) Uani d 1 . . C
H14 0.1559 -0.1659 0.6032 0.028 Uiso calc 1 . . H
C5 0.3094(5) 0.1556(3) 1.2763(3) 0.0246(9) Uani d 1 . . C
H5 0.2996 0.0746 1.3152 0.03 Uiso calc 1 . . H
C6 0.3281(5) 0.2382(3) 1.3283(3) 0.0290(9) Uani d 1 . . C
H6A 0.332 0.2123 1.402 0.035 Uiso calc 1 . . H
C17 0.9820(5) 0.3774(3) 0.5018(3) 0.0198(9) Uani d 1 . . C
C9 -0.0082(4) 0.3308(3) 0.9302(3) 0.0238(9) Uani d 1 . . C
H9A -0.0784 0.2764 0.9136 0.036 Uiso calc 1 . . H
H9B -0.0199 0.4076 0.8737 0.036 Uiso calc 1 . . H
H9C -0.06 0.3457 0.995 0.036 Uiso calc 1 . . H
C13 0.1970(5) -0.1820(3) 0.7566(3) 0.0237(9) Uani d 1 . . C
H13 0.2116 -0.2677 0.7818 0.028 Uiso calc 1 . . H
C15 0.1396(5) 0.0042(3) 0.6168(3) 0.0256(9) Uani d 1 . . C
H15 0.1179 0.0473 0.5455 0.031 Uiso calc 1 . . H
C18 0.9106(5) 0.4815(3) 0.4144(3) 0.0204(9) Uani d 1 . . C
C16 0.9283(5) 0.6004(3) 0.4066(3) 0.0210(9) Uani d 1 . . C



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N4 C20 . 1.121(5) ?
C20 C19 . 1.488(6) ?
S O2 . 1.430(2) ?
S O1 . 1.434(2) ?
S N1 . 1.648(3) ?
S C3 . 1.756(4) ?
Cl2 C18 . 1.731(3) ?
O4 C10 . 1.249(4) ?
O3 C7 . 1.342(4) ?
O6 C17 . 1.240(4) ?
O5 C16 . 1.269(4) ?
N1 C8 . 1.441(4) ?
N1 C9 . 1.493(4) ?
C4 C5 . 1.387(5) ?
C4 C3 . 1.405(5) ?
C4 C7 . 1.469(5) ?
N2 C10 . 1.361(4) ?
N2 C11 . 1.390(4) ?
C3 C2 . 1.381(5) ?
C8 C7 . 1.368(5) ?
C8 C10 . 1.453(5) ?
N3 C11 . 1.346(4) ?
N3 C15 . 1.350(4) ?
C12 C13 . 1.372(5) ?
C12 C11 . 1.396(4) ?
C2 C1 . 1.382(5) ?
C1 C6 . 1.389(5) ?
C14 C15 . 1.371(4) ?
C14 C13 . 1.382(5) ?
C5 C6 . 1.379(5) ?
C17 C18 . 1.427(5) ?
C17 C16 2_766 1.534(5) ?
C18 C16 . 1.379(4) ?
C16 C17 2_766 1.534(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
N4 C20 C19 178.1(5) . . ?
O2 S O1 119.33(14) . . ?
O2 S N1 108.67(14) . . ?
O1 S N1 107.35(14) . . ?
O2 S C3 109.06(15) . . ?
O1 S C3 108.32(15) . . ?
N1 S C3 102.86(15) . . ?
C8 N1 C9 115.4(2) . . ?
C8 N1 S 114.1(2) . . ?
C9 N1 S 115.6(2) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 C7 121.6(3) . . ?
C3 C4 C7 119.9(3) . . ?
C10 N2 C11 125.6(3) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 S 121.1(3) . . ?
C4 C3 S 117.8(3) . . ?
C7 C8 N1 121.3(3) . . ?
C7 C8 C10 119.5(3) . . ?
N1 C8 C10 119.2(3) . . ?
C11 N3 C15 122.3(3) . . ?
C13 C12 C11 119.1(3) . . ?
O4 C10 N2 120.7(3) . . ?
O4 C10 C8 120.3(3) . . ?
N2 C10 C8 119.0(3) . . ?
C3 C2 C1 119.4(3) . . ?
C2 C1 C6 120.3(3) . . ?
N3 C11 N2 115.3(3) . . ?
N3 C11 C12 118.3(3) . . ?
N2 C11 C12 126.4(3) . . ?
O3 C7 C8 122.5(3) . . ?
O3 C7 C4 113.9(3) . . ?
C8 C7 C4 123.6(3) . . ?
C15 C14 C13 117.1(3) . . ?
C6 C5 C4 120.6(3) . . ?
C5 C6 C1 120.2(4) . . ?
O6 C17 C18 124.4(3) . . ?
O6 C17 C16 117.1(3) . 2_766 ?
C18 C17 C16 118.6(3) . 2_766 ?
C12 C13 C14 121.9(3) . . ?
N3 C15 C14 121.3(3) . . ?
C16 C18 C17 122.5(3) . . ?
C16 C18 Cl2 119.4(3) . . ?
C17 C18 Cl2 118.1(2) . . ?
O5 C16 C18 125.6(3) . . ?
O5 C16 C17 115.6(3) . 2_766 ?
C18 C16 C17 118.8(3) . 2_766 ?

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
O3 H10 O4 0.89(4) 1.69(4) 2.500(3) 150(3) .
N2 H6 O5 0.74(4) 2.16(4) 2.833(4) 151(4) 2_666
N3 H3 O5 0.99(4) 1.73(4) 2.667(4) 156(4) 2_666
N3 H3 O6 0.99(4) 2.24(4) 2.885(4) 121(3) 1_455
C12 H12 O4 0.93 2.17 2.754(4) 120.1 .
C15 H15 O6 0.93 2.48 2.989(4) 114.5 1_455
C2 H2 O1 0.93 2.58 3.470(4) 160.7 2_667
N2 H6 O5 0.74(4) 2.16(4) 2.833(4) 151(4) 2_666
C14 H14 O6 0.93 2.52 3.417(4) 161.8 2_656
N3 H3 O6 0.99(4) 2.24(4) 2.885(4) 121(3) 1_455
N3 H3 O5 0.99(4) 1.73(4) 2.667(4) 156(4) 2_666
O3 H10 O4 0.89(4) 1.69(4) 2.500(3) 150(3) .
C9 H9B Cl2 0.96 2.95 3.747(4) 141.8 2_666
C9 H9C O2 0.96 2.65 3.469(4) 143.3 2_567

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 984172'
#######################################################################
#
#                 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_pirox_brom

_audit_creation_date             2014-01-20T12:12:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C21 H15 Br2 N3 O8 S'
_chemical_formula_weight         629.24

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.8422(17)
_cell_length_b                   13.437(2)
_cell_length_c                   19.242(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.518(11)
_cell_angle_gamma                90
_cell_volume                     2247.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    3.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7574
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'


#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_number            62927
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         27.827
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were placed on calculated positons and refined as riding on the
atoms to which they were bonded except those involved in hydrogen bonds, H2,
H3, H7, H22 which were identified in a difference Fourier map and freely 
refined with isotropic thermal parameters.
;
_reflns_number_total             5308
_reflns_number_gt                3937
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0785
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_number_reflns         5308
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O8 1.1700(2) 1.04258(14) 0.52587(10) 0.0197(4) Uani d 1 . . O
N2 1.2623(3) 0.88969(18) 0.50041(13) 0.0163(5) Uani d 1 . . N
C16 1.1905(3) 0.9533(2) 0.53989(15) 0.0164(6) Uani d 1 . . C
N3 1.4043(3) 0.83496(18) 0.41977(12) 0.0172(5) Uani d 1 . . N
C18 1.3513(3) 1.0078(2) 0.41690(15) 0.0176(6) Uani d 1 . . C
H18 1.3048 1.063 0.4333 0.021 Uiso calc 1 . . H
C17 1.3373(3) 0.9141(2) 0.44556(14) 0.0154(6) Uani d 1 . . C
C20 1.5049(4) 0.9341(2) 0.33878(16) 0.0223(7) Uani d 1 . . C
H20 1.5618 0.9406 0.3029 0.027 Uiso calc 1 . . H
C21 1.4359(3) 1.0172(2) 0.36351(16) 0.0200(6) Uani d 1 . . C
H21 1.4469 1.0794 0.3439 0.024 Uiso calc 1 . . H
C19 1.4874(4) 0.8433(2) 0.36822(16) 0.0217(7) Uani d 1 . . C
H19 1.533 0.7872 0.3525 0.026 Uiso calc 1 . . H
H3 1.398(4) 0.773(2) 0.4391(17) 0.030(9) Uiso d 1 . . H
H2 1.278(3) 0.836(2) 0.5153(15) 0.010(8) Uiso d 1 . . H
H7 1.074(4) 1.073(3) 0.6041(19) 0.036(12) Uiso d 1 . . H
H22 0.598(5) 0.440(3) 0.699(2) 0.057(16) Uiso d 1 . . H
Br1 0.19809(3) 0.45744(2) 0.48799(2) 0.02149(9) Uani d 1 . . Br
Br2 0.74488(3) 0.70099(2) 0.70590(2) 0.02250(9) Uani d 1 . . Br
S1 1.22578(8) 0.76846(5) 0.69250(4) 0.01456(15) Uani d 1 . . S
O7 1.0537(3) 1.06090(15) 0.63847(13) 0.0220(5) Uani d 1 . . O
O4 0.3060(2) 0.67725(14) 0.48205(10) 0.0197(4) Uani d 1 . . O
N1 1.1603(3) 0.80097(16) 0.61014(12) 0.0148(5) Uani d 1 . . N
O3 0.5362(2) 0.76877(14) 0.56674(11) 0.0220(5) Uani d 1 . . O
O2 0.6432(3) 0.48261(17) 0.70662(11) 0.0208(5) Uani d 1 . . O
O1 0.4306(2) 0.38790(14) 0.62070(11) 0.0240(5) Uani d 1 . . O
C1 0.5100(3) 0.6830(2) 0.58217(15) 0.0163(6) Uani d 1 . . C
O6 1.2122(2) 0.66299(14) 0.69800(10) 0.0198(5) Uani d 1 . . O
C3 0.3538(3) 0.5282(2) 0.54755(15) 0.0155(6) Uani d 1 . . C
C5 0.5658(3) 0.5351(2) 0.65329(15) 0.0161(6) Uani d 1 . . C
O5 1.3745(2) 0.81299(13) 0.71300(10) 0.0174(4) Uani d 1 . . O
C6 0.5933(3) 0.6319(2) 0.64365(15) 0.0153(6) Uani d 1 . . C
C8 1.0665(3) 0.7898(2) 0.80088(15) 0.0179(6) Uani d 1 . . C
H8A 1.1054 0.7279 0.8168 0.022 Uiso calc 1 . . H
C2 0.3797(3) 0.6272(2) 0.53249(14) 0.0149(6) Uani d 1 . . C
C4 0.4432(3) 0.4768(2) 0.60461(15) 0.0173(6) Uani d 1 . . C
C15 1.0296(3) 0.7405(2) 0.57157(15) 0.0191(6) Uani d 1 . . C
H15A 0.9389 0.7535 0.5909 0.029 Uiso calc 1 . . H
H15B 1.0549 0.6711 0.5766 0.029 Uiso calc 1 . . H
H15C 1.0111 0.7581 0.5224 0.029 Uiso calc 1 . . H
C9 0.9757(4) 0.8447(2) 0.83934(16) 0.0235(7) Uani d 1 . . C
H9A 0.9546 0.8198 0.8816 0.028 Uiso calc 1 . . H
C12 1.0396(3) 0.9219(2) 0.71281(15) 0.0154(6) Uani d 1 . . C
C7 1.0973(3) 0.8294(2) 0.73871(15) 0.0147(6) Uani d 1 . . C
C14 1.0785(3) 0.9632(2) 0.64762(15) 0.0158(6) Uani d 1 . . C
C11 0.9486(3) 0.9752(2) 0.75219(16) 0.0192(6) Uani d 1 . . C
H11 0.9092 1.037 0.7364 0.023 Uiso calc 1 . . H
C13 1.1404(3) 0.9070(2) 0.60071(15) 0.0151(6) Uani d 1 . . C
C10 0.9173(4) 0.9361(2) 0.81455(16) 0.0233(7) Uani d 1 . . C
H10 0.8559 0.9718 0.8402 0.028 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O8 C16 . 1.236(3) ?
N2 C16 . 1.374(4) ?
N2 C17 . 1.385(4) ?
N2 H2 . 0.77(3) ?
C16 C13 . 1.464(4) ?
N3 C19 . 1.342(4) ?
N3 C17 . 1.355(4) ?
N3 H3 . 0.92(3) ?
C18 C21 . 1.382(4) ?
C18 C17 . 1.388(4) ?
C18 H18 . 0.93 ?
C20 C19 . 1.367(4) ?
C20 C21 . 1.397(4) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
C19 H19 . 0.93 ?
Br1 C3 . 1.880(3) ?
Br2 C6 . 1.872(3) ?
S1 O6 . 1.428(2) ?
S1 O5 . 1.433(2) ?
S1 N1 . 1.644(2) ?
S1 C7 . 1.767(3) ?
O7 C14 . 1.337(3) ?
O7 H7 . 0.74(4) ?
O4 C2 . 1.260(3) ?
N1 C13 . 1.443(3) ?
N1 C15 . 1.494(3) ?
O3 C1 . 1.223(3) ?
O2 C5 . 1.327(3) ?
O2 H22 . 0.70(4) ?
O1 C4 . 1.243(3) ?
C1 C6 . 1.448(4) ?
C1 C2 . 1.550(4) ?
C3 C2 . 1.389(4) ?
C3 C4 . 1.411(4) ?
C5 C6 . 1.343(4) ?
C5 C4 . 1.515(4) ?
C5 H22 . 1.55(4) ?
C8 C7 . 1.381(4) ?
C8 C9 . 1.398(4) ?
C8 H8A . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C9 C10 . 1.383(4) ?
C9 H9A . 0.93 ?
C12 C11 . 1.398(4) ?
C12 C7 . 1.401(4) ?
C12 C14 . 1.469(4) ?
C14 C13 . 1.366(4) ?
C11 C10 . 1.384(4) ?
C11 H11 . 0.93 ?
C10 H10 . 0.93 ?

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
C16 N2 C17 127.4(2) . . ?
C16 N2 H2 116(2) . . ?
C17 N2 H2 115(2) . . ?
O8 C16 N2 123.2(3) . . ?
O8 C16 C13 122.3(3) . . ?
N2 C16 C13 114.5(2) . . ?
C19 N3 C17 122.7(2) . . ?
C19 N3 H3 117(2) . . ?
C17 N3 H3 120(2) . . ?
C21 C18 C17 118.5(3) . . ?
C21 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
N3 C17 N2 113.3(2) . . ?
N3 C17 C18 119.3(3) . . ?
N2 C17 C18 127.4(3) . . ?
C19 C20 C21 118.9(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C18 C21 C20 120.6(3) . . ?
C18 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
N3 C19 C20 119.9(3) . . ?
N3 C19 H19 120 . . ?
C20 C19 H19 120 . . ?
O6 S1 O5 118.66(12) . . ?
O6 S1 N1 108.40(12) . . ?
O5 S1 N1 107.37(12) . . ?
O6 S1 C7 110.61(12) . . ?
O5 S1 C7 108.06(12) . . ?
N1 S1 C7 102.49(13) . . ?
C14 O7 H7 106(3) . . ?
C13 N1 C15 114.1(2) . . ?
C13 N1 S1 113.39(18) . . ?
C15 N1 S1 116.02(18) . . ?
C5 O2 H22 95(4) . . ?
O3 C1 C6 123.7(3) . . ?
O3 C1 C2 117.3(3) . . ?
C6 C1 C2 119.0(2) . . ?
C2 C3 C4 122.7(3) . . ?
C2 C3 Br1 119.1(2) . . ?
C4 C3 Br1 118.1(2) . . ?
O2 C5 C6 122.7(3) . . ?
O2 C5 C4 114.4(2) . . ?
C6 C5 C4 122.9(3) . . ?
O2 C5 H22 26.7(15) . . ?
C6 C5 H22 149.2(16) . . ?
C4 C5 H22 87.8(16) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 Br2 121.2(2) . . ?
C1 C6 Br2 119.0(2) . . ?
C7 C8 C9 118.6(3) . . ?
C7 C8 H8A 120.7 . . ?
C9 C8 H8A 120.7 . . ?
O4 C2 C3 126.2(3) . . ?
O4 C2 C1 116.0(2) . . ?
C3 C2 C1 117.9(2) . . ?
O1 C4 C3 126.9(3) . . ?
O1 C4 C5 115.4(3) . . ?
C3 C4 C5 117.6(2) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9A 120 . . ?
C8 C9 H9A 120 . . ?
C11 C12 C7 118.0(3) . . ?
C11 C12 C14 121.1(3) . . ?
C7 C12 C14 120.8(2) . . ?
C8 C7 C12 122.3(3) . . ?
C8 C7 S1 120.3(2) . . ?
C12 C7 S1 117.3(2) . . ?
O7 C14 C13 122.1(3) . . ?
O7 C14 C12 115.1(2) . . ?
C13 C14 C12 122.7(3) . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C14 C13 N1 121.2(2) . . ?
C14 C13 C16 120.6(3) . . ?
N1 C13 C16 118.2(2) . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 984173'
