# Electronic Supplementary Material (ESI) for RSC Advances.
# 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.
#
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#  fide research purposes only. It may contain copyright material
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#  from this site to visualise CIF-encoded structures and 
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data_tr2

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 O3 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' 
_chemical_formula_structural     ?
_chemical_formula_sum            'C16 H15 N3 O3 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         329.38
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   7.5729(13)
_cell_length_b                   9.0487(16)
_cell_length_c                   22.692(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1555.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_special_details            
;
 
;

_exptl_crystal_description       ?
_exptl_crystal_colour            ?

_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.019
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA, 
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   ' ?'
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 18.4

# number of measured reflections (redundant set)
_diffrn_reflns_number            2511
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         64.61
_diffrn_reflns_theta_full        64.61
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.898
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2041
# number of observed reflections (> n sig(I))
_reflns_number_gt                1987
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

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

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.2000P)²]         where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall            - refined all H-atom parameters
# refxyz            - refined H-atom coordinates only
# refU              - refined H-atom U only
# noref             - no refinement of H-atom parameters
# constr            - H-atom parameters constrained
# hetero            - H-atom parameters constrained for H on C,
#                     all H-atom parameters refined for H on
#                     heteroatoms
# heteroxyz         - H-atom parameters constrained for H on C,
#                     refined H-atom coordinates only for H
#                     on heteroatoms
# heteroU           - H-atom parameters constrained for H on C,
#                     refined H-atom U's only for H on
#                     heteroatoms
# heteronoref       - H-atom parameters constrained for H on C,
#                     no refinement of H-atom parameters for
#                     H on heteroatoms
# hetero-mixed      - H-atom parameters constrained for H on C
#                     and some heteroatoms, all H-atom
#                     parameters refined for H on remaining
#                     heteroatoms.
# heteroxyz-mixed   - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     coordinates only for H on remaining
#                     heteroatoms.
# heteroU-mixed     - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     U's only for H on remaining heteroatoms
# heteronoref-mixed - H-atom parameters constrained for H on C
#                     and some heteroatoms, no refinement of
#                     H-atom parameters for H on remaining
#                     heteroatoms
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.86(6)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad' 
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration ?

_refine_ls_number_reflns         2041
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2649
_refine_ls_wR_factor_gt          0.2221
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_restrained_S_all      1.311
_refine_ls_shift/su_max          0.352
_refine_ls_shift/su_mean         0.061
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.129

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S10 S Uani 0.5649(2) 0.41106(15) 0.09916(7) 1.000 0.0603(5) d . . .
O8 O Uani 0.6412(6) 0.3366(4) 0.22087(18) 1.000 0.0593(14) d . . .
O20 O Uani 1.0092(6) 0.2916(5) 0.4785(2) 1.000 0.0653(16) d . . .
O22 O Uani 0.8935(5) 0.4617(4) 0.39492(18) 1.000 0.0563(11) d . . .
N1 N Uani 0.7144(6) -0.1479(5) 0.2110(2) 1.000 0.0517(14) d . . .
N2 N Uani 0.6741(6) -0.0340(5) 0.1791(2) 1.000 0.0467(14) d . . .
N5 N Uani 0.7793(6) -0.1179(5) 0.2637(2) 1.000 0.0490(14) d . . .
C3 C Uani 0.7131(6) 0.0831(6) 0.2115(3) 1.000 0.0463(14) d . . .
C4 C Uani 0.7806(6) 0.0310(5) 0.2657(3) 1.000 0.0467(16) d . . .
C6 C Uani 0.6832(8) -0.2989(6) 0.1915(3) 1.000 0.0600(19) d . . .
C7 C Uani 0.6730(6) 0.2333(6) 0.1884(2) 1.000 0.0437(14) d . . .
C9 C Uani 0.6644(7) 0.2534(6) 0.1234(2) 1.000 0.0460(16) d . . .
C11 C Uani 0.6154(8) 0.3719(7) 0.0287(3) 1.000 0.0613(19) d . . .
C12 C Uani 0.7047(9) 0.2429(8) 0.0215(3) 1.000 0.060(2) d . . .
C13 C Uani 0.7368(8) 0.1721(7) 0.0772(3) 1.000 0.0570(19) d . . .
C14 C Uani 0.8451(6) 0.1013(6) 0.3210(3) 1.000 0.0467(14) d . . .
C15 C Uani 0.8404(7) 0.2535(6) 0.3307(3) 1.000 0.0463(16) d . . .
C16 C Uani 0.8966(6) 0.3133(6) 0.3823(2) 1.000 0.0447(14) d . . .
C17 C Uani 0.9611(6) 0.2219(6) 0.4281(3) 1.000 0.0500(18) d . . .
C18 C Uani 0.9680(7) 0.0695(6) 0.4184(3) 1.000 0.0533(19) d . . .
C19 C Uani 0.9121(8) 0.0123(5) 0.3658(3) 1.000 0.0543(18) d . . .
C21 C Uani 1.0311(11) 0.2013(9) 0.5281(4) 1.000 0.077(3) d . . .
C23 C Uani 0.8107(11) 0.5570(7) 0.3541(3) 1.000 0.073(3) d . . .
H6A H Uiso 0.56790 -0.30580 0.17420 1.000 0.0900 c R . .
H6B H Uiso 0.69060 -0.36460 0.22460 1.000 0.0900 c R . .
H6C H Uiso 0.77060 -0.32590 0.16280 1.000 0.0900 c R . .
H11 H Uiso 0.58490 0.43310 -0.00260 1.000 0.0730 c R . .
H12 H Uiso 0.74040 0.20530 -0.01480 1.000 0.0720 c R . .
H13 H Uiso 0.79780 0.08360 0.08170 1.000 0.0680 c R . .
H15 H Uiso 0.79790 0.31530 0.30120 1.000 0.0560 c R . .
H18 H Uiso 1.01070 0.00700 0.44770 1.000 0.0640 c R . .
H19 H Uiso 0.91890 -0.08920 0.35980 1.000 0.0650 c R . .
H21A H Uiso 0.92120 0.15350 0.53710 1.000 0.1160 c R . .
H21B H Uiso 1.06750 0.26050 0.56100 1.000 0.1160 c R . .
H21C H Uiso 1.11940 0.12790 0.52000 1.000 0.1160 c R . .
H23A H Uiso 0.88110 0.56320 0.31900 1.000 0.1090 c R . .
H23B H Uiso 0.79870 0.65350 0.37120 1.000 0.1090 c R . .
H23C H Uiso 0.69600 0.51890 0.34440 1.000 0.1090 c R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S10 0.0754(9) 0.0424(8) 0.0631(11) 0.0021(6) -0.0117(7) 0.0048(6)
O8 0.095(3) 0.045(2) 0.038(2) -0.0102(16) -0.011(2) 0.019(2)
O20 0.076(3) 0.055(2) 0.065(3) -0.0072(19) -0.023(2) 0.004(2)
O22 0.079(2) 0.0348(19) 0.055(2) -0.0088(16) -0.013(2) -0.0001(18)
N1 0.054(2) 0.037(2) 0.064(3) -0.009(2) -0.002(2) 0.0012(18)
N2 0.055(2) 0.040(2) 0.045(3) 0.0012(18) 0.002(2) -0.0006(18)
N5 0.058(2) 0.033(2) 0.056(3) 0.0012(18) -0.007(2) 0.0003(18)
C3 0.047(2) 0.035(2) 0.057(3) -0.003(2) 0.000(2) 0.001(2)
C4 0.043(2) 0.028(2) 0.069(4) -0.005(2) -0.002(2) 0.0029(19)
C6 0.073(3) 0.041(3) 0.066(4) -0.015(3) 0.007(3) -0.006(3)
C7 0.053(2) 0.044(2) 0.034(3) -0.001(2) 0.001(2) -0.002(2)
C9 0.053(2) 0.043(3) 0.042(3) 0.000(2) -0.002(2) -0.007(2)
C11 0.071(3) 0.063(3) 0.050(4) 0.017(3) -0.016(3) -0.009(3)
C12 0.068(3) 0.068(4) 0.044(4) -0.001(3) -0.001(3) 0.005(3)
C13 0.057(3) 0.050(3) 0.064(4) 0.000(3) -0.001(3) 0.009(2)
C14 0.043(2) 0.036(2) 0.061(3) -0.001(2) -0.004(2) -0.003(2)
C15 0.047(2) 0.040(3) 0.052(3) -0.002(2) -0.006(2) 0.001(2)
C16 0.048(2) 0.035(2) 0.051(3) -0.006(2) -0.001(2) -0.0012(19)
C17 0.045(2) 0.042(3) 0.063(4) -0.003(2) -0.009(2) -0.003(2)
C18 0.058(3) 0.042(3) 0.060(4) 0.006(2) -0.013(2) 0.002(2)
C19 0.062(3) 0.030(2) 0.071(4) -0.005(2) -0.013(3) -0.002(2)
C21 0.089(4) 0.074(5) 0.069(5) -0.004(3) -0.031(4) 0.009(4)
C23 0.092(5) 0.041(3) 0.085(5) -0.006(3) -0.017(4) 0.000(3)

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

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S10 C9 1.705(6) . . yes
S10 C11 1.682(7) . . yes
O8 C7 1.214(6) . . yes
O20 C17 1.356(8) . . yes
O20 C21 1.401(10) . . yes
O22 C16 1.373(7) . . yes
O22 C23 1.412(8) . . yes
N1 N2 1.296(6) . . yes
N1 N5 1.321(6) . . yes
N1 C6 1.456(7) . . yes
N2 C3 1.323(7) . . yes
N5 C4 1.348(6) . . yes
C3 C4 1.413(9) . . no
C3 C7 1.488(8) . . no
C4 C14 1.489(9) . . no
C7 C9 1.488(6) . . no
C9 C13 1.393(8) . . no
C11 C12 1.359(10) . . no
C12 C13 1.438(10) . . no
C14 C15 1.395(8) . . no
C14 C19 1.393(9) . . no
C15 C16 1.358(8) . . no
C16 C17 1.415(8) . . no
C17 C18 1.398(8) . . no
C18 C19 1.368(9) . . no
C6 H6A 0.9600 . . no
C6 H6B 0.9600 . . no
C6 H6C 0.9600 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C15 H15 0.9300 . . no
C18 H18 0.9300 . . no
C19 H19 0.9300 . . no
C21 H21A 0.9600 . . no
C21 H21B 0.9600 . . no
C21 H21C 0.9600 . . no
C23 H23A 0.9600 . . no
C23 H23B 0.9600 . . no
C23 H23C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S10 C11 91.7(3) . . . yes
C17 O20 C21 116.0(5) . . . yes
C16 O22 C23 117.9(4) . . . yes
N2 N1 N5 115.5(4) . . . yes
N2 N1 C6 122.6(5) . . . yes
N5 N1 C6 121.9(5) . . . yes
N1 N2 C3 105.9(5) . . . yes
N1 N5 C4 103.8(5) . . . yes
N2 C3 C4 107.3(5) . . . yes
N2 C3 C7 119.4(5) . . . yes
C4 C3 C7 133.3(5) . . . no
N5 C4 C3 107.6(5) . . . yes
N5 C4 C14 117.2(5) . . . yes
C3 C4 C14 135.2(5) . . . no
O8 C7 C3 122.0(5) . . . yes
O8 C7 C9 119.9(5) . . . yes
C3 C7 C9 118.0(5) . . . no
S10 C9 C7 116.2(4) . . . yes
S10 C9 C13 111.9(4) . . . yes
C7 C9 C13 131.6(5) . . . no
S10 C11 C12 114.1(5) . . . yes
C11 C12 C13 111.2(6) . . . no
C9 C13 C12 111.1(5) . . . no
C4 C14 C15 123.1(5) . . . no
C4 C14 C19 119.2(5) . . . no
C15 C14 C19 117.7(6) . . . no
C14 C15 C16 121.4(6) . . . no
O22 C16 C15 124.3(5) . . . yes
O22 C16 C17 115.1(4) . . . yes
C15 C16 C17 120.6(5) . . . no
O20 C17 C16 116.1(5) . . . yes
O20 C17 C18 125.6(6) . . . yes
C16 C17 C18 118.3(6) . . . no
C17 C18 C19 120.0(6) . . . no
C14 C19 C18 122.1(5) . . . no
N1 C6 H6A 109.00 . . . no
N1 C6 H6B 110.00 . . . no
N1 C6 H6C 109.00 . . . no
H6A C6 H6B 109.00 . . . no
H6A C6 H6C 109.00 . . . no
H6B C6 H6C 109.00 . . . no
S10 C11 H11 123.00 . . . no
C12 C11 H11 123.00 . . . no
C11 C12 H12 124.00 . . . no
C13 C12 H12 124.00 . . . no
C9 C13 H13 125.00 . . . no
C12 C13 H13 124.00 . . . no
C14 C15 H15 119.00 . . . no
C16 C15 H15 119.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 120.00 . . . no
C14 C19 H19 119.00 . . . no
C18 C19 H19 119.00 . . . no
O20 C21 H21A 109.00 . . . no
O20 C21 H21B 109.00 . . . no
O20 C21 H21C 109.00 . . . no
H21A C21 H21B 110.00 . . . no
H21A C21 H21C 109.00 . . . no
H21B C21 H21C 110.00 . . . no
O22 C23 H23A 109.00 . . . no
O22 C23 H23B 109.00 . . . no
O22 C23 H23C 109.00 . . . no
H23A C23 H23B 110.00 . . . no
H23A C23 H23C 109.00 . . . no
H23B C23 H23C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 S10 C9 C13 0.4(5) . . . . no
C11 S10 C9 C7 175.3(4) . . . . no
C9 S10 C11 C12 0.4(5) . . . . no
C21 O20 C17 C16 164.8(5) . . . . no
C21 O20 C17 C18 -14.3(8) . . . . no
C23 O22 C16 C17 -172.4(5) . . . . no
C23 O22 C16 C15 6.5(8) . . . . no
C6 N1 N2 C3 177.3(5) . . . . no
N5 N1 N2 C3 -0.1(6) . . . . no
N2 N1 N5 C4 0.0(6) . . . . no
C6 N1 N5 C4 -177.3(5) . . . . no
N1 N2 C3 C7 -176.8(4) . . . . no
N1 N2 C3 C4 0.1(6) . . . . no
N1 N5 C4 C14 179.0(4) . . . . no
N1 N5 C4 C3 0.0(5) . . . . no
C7 C3 C4 C14 -2.5(10) . . . . no
N2 C3 C4 N5 -0.1(6) . . . . no
N2 C3 C4 C14 -178.8(5) . . . . no
C7 C3 C4 N5 176.2(5) . . . . no
C4 C3 C7 C9 158.4(5) . . . . no
N2 C3 C7 C9 -25.7(7) . . . . no
C4 C3 C7 O8 -24.4(8) . . . . no
N2 C3 C7 O8 151.5(5) . . . . no
C3 C4 C14 C19 -176.8(6) . . . . no
N5 C4 C14 C15 -174.8(5) . . . . no
C3 C4 C14 C15 3.8(9) . . . . no
N5 C4 C14 C19 4.6(7) . . . . no
O8 C7 C9 S10 -13.4(7) . . . . no
O8 C7 C9 C13 160.3(6) . . . . no
C3 C7 C9 S10 163.9(4) . . . . no
C3 C7 C9 C13 -22.5(8) . . . . no
S10 C9 C13 C12 -1.0(7) . . . . no
C7 C9 C13 C12 -174.9(6) . . . . no
S10 C11 C12 C13 -1.0(7) . . . . no
C11 C12 C13 C9 1.3(8) . . . . no
C19 C14 C15 C16 -1.0(8) . . . . no
C4 C14 C19 C18 -177.8(5) . . . . no
C15 C14 C19 C18 1.6(8) . . . . no
C4 C14 C15 C16 178.4(5) . . . . no
C14 C15 C16 C17 -0.3(8) . . . . no
C14 C15 C16 O22 -179.2(5) . . . . no
O22 C16 C17 O20 0.8(6) . . . . no
C15 C16 C17 C18 1.0(7) . . . . no
O22 C16 C17 C18 180.0(4) . . . . no
C15 C16 C17 O20 -178.1(5) . . . . no
O20 C17 C18 C19 178.7(5) . . . . no
C16 C17 C18 C19 -0.4(8) . . . . no
C17 C18 C19 C14 -0.9(9) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C11 H11 O22 0.9300 2.5200 3.389(8) 156.00 2_664 yes
C13 H13 N2 0.9300 2.6300 3.008(8) 105.00 . yes
C15 H15 O8 0.9300 2.1800 3.009(8) 147.00 . yes
C19 H19 N5 0.9300 2.4400 2.787(8) 102.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;

_iucr_refine_instructions_details 
;
;

#===END
_database_code_depnum_ccdc_archive 'CCDC 1009982'
