
#=======================================================================
data_global
#=======================================================================

_audit_creation_method                   'Jana2006 Version : 23/11/2014'


# 1. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic            ?
_journal_date_to_coeditor                ?
_journal_date_from_coeditor              ?
_journal_date_accepted                   ?
_journal_date_printers_first             ?
_journal_date_printers_final             ?
_journal_date_proofs_out                 ?
_journal_date_proofs_in                  ?
_journal_coeditor_name                   ?
_journal_coeditor_code                   ?
_journal_coeditor_notes
; ?
;
_journal_techeditor_code                 ?
_journal_paper_category                  ?
_journal_techeditor_notes
; ?
;
_journal_coden_ASTM                      ?
_journal_name_full                       'Acta Crystallographica Section C'
_journal_year                            ?
_journal_volume                          ?
_journal_issue                           ?
_journal_page_first                      ?
_journal_page_last                       ?
_journal_suppl_publ_number               ?
_journal_suppl_publ_pages                ?

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

# 2. SUBMISSION DETAILS

_publ_contact_author_name                'Hamdi BEN YAHIA'
_publ_contact_author_address
; ?
;
_publ_contact_author_email               'hyahia@hbku.edu.qa'
_publ_contact_author_fax                 '+97444541528'
_publ_contact_author_phone               '+97444547762'

_publ_requested_journal                  'Acta Crystallographica Section C'
_publ_requested_category                 ?


_publ_contact_letter
; ?
;

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

# 3. TITLE AND AUTHOR LIST

_publ_section_title
; ?
;
_publ_section_title_footnote
; ?
;
loop_
 _publ_author_name
 _publ_author_footnote
 _publ_author_address
; ?      # name
;
; ?      # footnote
;
; ?      # address
;

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

# 4. TEXT

_publ_section_synopsis
; ?
;
_publ_section_abstract
; ?
;
_publ_section_comment
; ?
;
_publ_section_introduction
; ?
;
_publ_section_experimental
; ?
;
_publ_section_exptl_prep
; ?
;
_publ_section_exptl_refinement
; ?
;
_publ_section_exptl_solution
; ?
;
_publ_section_discussion
; ?
;
_publ_section_acknowledgements
; ?
;
_publ_section_references
;
Petricek, V., Dusek, M. & Palatinus L. (2014). Z. Kristallogr. 229(5), 345-352;

Palatinus L. & Chapuis G. (2007). J. Appl. Cryst. 40, 786-790.

# enable this reference if Diamond ver. 2 was used for visualization
#Brandenburg, K. (1999). DIAMOND. Version. 2.1c.
#Crystal Impact GbR, Bonn, Germany.

# enable this reference if Diamond ver. 3 was used for visualization
#Brandenburg, K. & Putz, H. (2005). DIAMOND Version 3.
#Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany.

# enable this reference if SIR97 was used for solving of the structure
#Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C.,
#Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R. (1997).
#SIR97. A Package for Crystal Structure Solution by Direct Methods
#and Refinement, Bari, Rome, Italy.

# use this reference if SIR2002 was used for solving of the structure
#Burla, M.C., Camalli, M., Carrozzini, B., Cascarano, G., Giacovazzo, C.,
#Polidori, G., Spagna, R.
#SIR2002: the program, J. Appl. Cryst, (2003). 36, 1103


# use this reference if SIR2011 was used for solving of the structure
#Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano,
#G.L., Giacovazzo, C., Mallamo. M., Mazzone, A., Polidori, G., Spagna, R.
#SIR2011: a new package for crystal structure determination and refinement,
#J.Appl.Cryst. (2012) 45, 357-361

# enable this reference if bond valences were calculated
#Brown, I. D. (1996). J. Appl. Cryst. 29, 479-480.

# enable this reference if Xshape wase used for crystal shape refinement
#Stoe & Cie (1998). X-SHAPE. Stoe & Cie, Darmstadt, Germany.


# enable this reference if Flack coefficient was refined
#Flack, H. D. (1983). Acta Cryst. A39, 876-881.
;
_publ_section_figure_captions
; ?
;
_publ_section_table_legends
; ?
;

#=======================================================================
data_(4)
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic
; ?
;
_chemical_name_common                    ?
_chemical_formula_moiety                 'C9 H5 N O5 S, H2 O, 2(H4 N)'
_chemical_formula_structural             ?
_chemical_formula_analytical             ?
_chemical_formula_iupac                  ?
_chemical_formula_sum                    'C9 H15 N3 O6 S1'
_chemical_formula_weight                 293.3
_chemical_melting_point                  ?
_chemical_compound_source                ?
_chemical_absolute_configuration         .

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

# 6. CRYSTAL DATA

_symmetry_cell_setting                   triclinic
_symmetry_space_group_name_H-M           'P -1'
_symmetry_space_group_name_Hall          '-P 1'
_symmetry_Int_Tables_number              2

loop_
 _space_group_symop_id
 _space_group_symop_operation_xyz
 1   x,y,z
 2   -x,-y,-z

_cell_length_a                           5.6564(3)
_cell_length_b                           10.7717(6)
_cell_length_c                           11.2333(6)
_cell_angle_alpha                        67.751(2)
_cell_angle_beta                         80.440(2)
_cell_angle_gamma                        83.967(2)
_cell_volume                             624.01(6)

loop_
 _twin_individual_id
 _twin_individual_mass_fraction_refined
 _twin_individual_twin_matrix_11
 _twin_individual_twin_matrix_12
 _twin_individual_twin_matrix_13
 _twin_individual_twin_matrix_21
 _twin_individual_twin_matrix_22
 _twin_individual_twin_matrix_23
 _twin_individual_twin_matrix_31
 _twin_individual_twin_matrix_32
 _twin_individual_twin_matrix_33
 ? ? ? ? ? ? ? ? ? ? ?

_cell_formula_units_Z                    2

_cell_measurement_reflns_used            9883
_cell_measurement_theta_min              2.26
_cell_measurement_theta_max              28.31
_cell_measurement_temperature            293
_cell_special_details
; ?
;

_exptl_crystal_density_diffrn            1.561
_exptl_crystal_density_meas              ?
_exptl_crystal_density_method            ?
_exptl_crystal_F_000                     308

_exptl_absorpt_coefficient_mu            0.288
_exptl_crystal_description               needle
_exptl_crystal_size_max                  0.220
_exptl_crystal_size_mid                  0.080
_exptl_crystal_size_min                  0.050
_exptl_crystal_size_rad                  ?
_exptl_crystal_colour                    colorless
_exptl_absorpt_correction_type           'multi-scan'
_exptl_absorpt_process_details           'sadabs'
_exptl_absorpt_correction_T_min          0.92
_exptl_absorpt_correction_T_max          0.98
loop_
 _exptl_crystal_face_index_h
 _exptl_crystal_face_index_k
 _exptl_crystal_face_index_l
 _exptl_crystal_face_perp_dist
 ? ? ? ?

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

# 7. EXPERIMENTAL DATA

_exptl_special_details                   ?

_diffrn_ambient_temperature              293
_diffrn_source                           ?
_diffrn_source_power                     ?
_diffrn_source_voltage                   ?
_diffrn_source_current                   ?
_diffrn_radiation_type                   'Mo K\a'
_diffrn_radiation_source                 'X-ray tube'
_diffrn_radiation_wavelength             0.71073
_diffrn_radiation_monochromator          ?
_diffrn_measurement_device               'four circle diffractometer'
_diffrn_measurement_device_type          'D8 Venture'
_diffrn_detector                         ?
_diffrn_detector_area_resol_mean         ?
_diffrn_measurement_method               'multi-scan'
_diffrn_measurement_specimen_support     ?

_diffrn_reflns_number                    9883
_diffrn_reflns_theta_min                 2.26
_diffrn_reflns_theta_max                 28.31
_diffrn_reflns_theta_full                28.31
_diffrn_measured_fraction_theta_max      1
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_av_R_equivalents          0.0334
_diffrn_reflns_av_unetI/netI             0.0418
_diffrn_reflns_limit_h_min               -7
_diffrn_reflns_limit_h_max               7
_diffrn_reflns_limit_k_min               -13
_diffrn_reflns_limit_k_max               14
_diffrn_reflns_limit_l_min               -14
_diffrn_reflns_limit_l_max               14
_diffrn_reflns_reduction_process         ?

_diffrn_standards_number                 ?
_diffrn_standards_interval_count         ?
_diffrn_standards_interval_time          ?
_diffrn_standards_decay_%                ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
  ? ? ?

_diffrn_radiation_probe                  X-ray

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

# 8. REFINEMENT DATA

_refine_special_details
; ?
;

_reflns_number_total                     3089
_reflns_number_gt                        2144
_reflns_threshold_expression             'I>3σ(I)'

_refine_ls_structure_factor_coef         Fsqd
_refine_ls_R_factor_gt                   0.0354
_refine_ls_wR_factor_gt                  0.0985
_refine_ls_R_factor_all                  0.0626
_refine_ls_wR_factor_ref                 0.1116
_refine_ls_goodness_of_fit_ref           1.12
_refine_ls_goodness_of_fit_gt            1.20
_refine_ls_restrained_S_gt               ?
_refine_ls_restrained_S_all              ?
_refine_ls_number_reflns                 3089
_refine_ls_number_parameters             185
_refine_ls_number_restraints             5
_refine_ls_number_constraints            48
_refine_ls_weighting_scheme              sigma
_refine_ls_weighting_details             'w=1/(σ²(I)+0.0035999999I²)'
_refine_ls_hydrogen_treatment            'mixed'
_refine_ls_shift/su_max                  0.0053
_refine_ls_shift/su_mean                 0.0001
_refine_diff_density_max                 0.30
_refine_diff_density_min                 -0.19
_refine_ls_extinction_method
 'B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef               5300(1000)
_refine_ls_abs_structure_details         ?
_refine_ls_abs_structure_Flack           ?
_refine_ls_abs_structure_Rogers          ?

loop_
 _atom_type_symbol
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 C    0.0033  0.0016
 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
 H    0.0000  0.0000
 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
 N    0.0061  0.0033
 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
 O    0.0106  0.0060
 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
 S    0.1246  0.1234
 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection               'Apex 3'
_computing_cell_refinement               'SAINT V8.38A (Bruker AXS Inc., 2016)'
_computing_data_reduction                'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution            'Direct method'
_computing_structure_refinement          'Jana2006'
_computing_molecular_graphics            'Diamond'
_computing_publication_material          ?

loop_
 _restr_distance_atom_site_label_1
 _restr_distance_site_symmetry_1
 _restr_distance_atom_site_label_2
 _restr_distance_site_symmetry_2
 _restr_distance_target
 _restr_distance_target_weight_param
N3 . H1n3 . 0.87 0.0015
N2 . H1n2 . 0.87 0.001
O6 . H1o6 . 0.96 0.005
O6 . H2o6 . 0.96 0.005

loop_
 _restr_angle_atom_site_label_1
 _restr_angle_site_symmetry_1
 _restr_angle_atom_site_label_2
 _restr_angle_site_symmetry_2
 _restr_angle_atom_site_label_3
 _restr_angle_site_symmetry_3
 _restr_angle_target
 _restr_angle_target_weight_param
H1o6 . O6 . H2o6 . 104.45 0.05


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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_adp_type
 _atom_site_U_iso_or_equiv
 _atom_site_site_symmetry_multiplicity
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
  S1 S 0.49810(9) 0.18604(5) 1.04691(4) Uani 0.03142(18) 2 1 d . . .
  N1 N 0.3687(2) 0.34983(13) 0.82931(12) Uani 0.0185(5) 2 1 d . . .
  O1 O 0.2313(2) 0.45441(12) 0.63444(12) Uani 0.0301(5) 2 1 d . . .
  C1 C 0.2147(3) 0.15737(18) 1.00826(17) Uani 0.0297(7) 2 1 d . . .
  O5 O 0.5478(3) 0.14917(15) 0.74543(15) Uani 0.0456(6) 2 1 d . . .
  C5 C 0.6795(3) 0.54760(16) 0.77539(16) Uani 0.0206(6) 2 1 d . . .
  O2 O 0.9981(2) 0.64499(13) 0.81862(13) Uani 0.0335(5) 2 1 d . . .
  N2 N 0.9159(3) 0.30990(15) 0.56994(15) Uani 0.0303(6) 2 1 d . . .
  C2 C 0.2221(3) 0.23365(15) 0.86175(15) Uani 0.0194(6) 2 1 d . . .
  O4 O 0.1833(2) 0.07612(13) 0.76854(14) Uani 0.0391(6) 2 1 d . . .
  O3 O 0.8151(2) 0.76459(12) 0.64639(12) Uani 0.0317(5) 2 1 d . . .
  N3 N 0.7037(3) 0.13049(15) 0.32850(15) Uani 0.0275(6) 2 1 d . . .
  C3 C 0.3694(3) 0.45441(16) 0.71194(15) Uani 0.0205(6) 2 1 d . . .
  C4 C 0.5323(3) 0.55578(16) 0.68749(16) Uani 0.0225(6) 2 1 d . . .
  C9 C 0.3270(3) 0.14634(16) 0.78282(15) Uani 0.0222(6) 2 1 d . . .
  C8 C 0.8464(3) 0.66080(17) 0.74578(17) Uani 0.0227(6) 2 1 d . . .
  C6 C 0.6770(3) 0.43624(16) 0.89294(16) Uani 0.0220(6) 2 1 d . . .
  O6 O 0.7939(3) 0.03548(13) 0.58466(12) Uani 0.0352(5) 2 1 d . . .
  C7 C 0.5220(3) 0.33834(16) 0.91607(15) Uani 0.0197(6) 2 1 d . . .
  H1c1 H 0.203253 0.063184 1.027934 Uiso 0.0356 2 1 d . . .
  H2c1 H 0.085107 0.194175 1.053619 Uiso 0.0356 2 1 d . . .
  H1c2 H 0.062702 0.260583 0.840036 Uiso 0.0233 2 1 d . . .
  H1c4 H 0.539174 0.631907 0.607254 Uiso 0.027 2 1 d . . .
  H1c6 H 0.781006 0.429426 0.954765 Uiso 0.0264 2 1 d . . .
  H1n3 H 0.7166(15) 0.0660(7) 0.2988(10) Uiso 0.0329 2 1 d . . .
  H2n3 H 0.741087 0.099131 0.406961 Uiso 0.0329 2 1 d . . .
  H3n3 H 0.800455 0.193093 0.27875 Uiso 0.0329 2 1 d . . .
  H4n3 H 0.556798 0.163785 0.32951 Uiso 0.0329 2 1 d . . .
  H1n2 H 0.9881(13) 0.2557(8) 0.5330(9) Uiso 0.0364 2 1 d . . .
  H2n2 H 0.84876 0.377805 0.512952 Uiso 0.0364 2 1 d . . .
  H3n2 H 0.806709 0.26745 0.632546 Uiso 0.0364 2 1 d . . .
  H4n2 H 1.020134 0.338631 0.601269 Uiso 0.0364 2 1 d . . .
  H1o6 H 0.816(3) -0.0598(5) 0.6158(15) Uiso 0.0423 2 1 d . . .
  H2o6 H 0.688(3) 0.0532(16) 0.6524(12) Uiso 0.0423 2 1 d . . .


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

# 10. MOLECULAR GEOMETRY


loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_1
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
  S1 C1 . . 1.814(2) ?
  S1 C7 . . 1.7391(14) ?
  N1 C2 . . 1.469(2) ?
  N1 C3 . . 1.3717(18) ?
  N1 C7 . . 1.372(2) ?
  O1 C3 . . 1.263(2) ?
  C1 C2 . . 1.531(2) ?
  C1 H1c1 . . 0.96 ?
  C1 H2c1 . . 0.96 ?
  O5 C9 . . 1.250(2) ?
  C5 C4 . . 1.367(3) ?
  C5 C8 . . 1.523(3) ?
  C5 C6 . . 1.407(2) ?
  O2 C8 . . 1.238(2) ?
  N2 H1n2 . . 0.870(10) ?
  N2 H2n2 . . 0.87 ?
  N2 H3n2 . . 0.87 ?
  N2 H4n2 . . 0.87 ?
  C2 C9 . . 1.537(3) ?
  C2 H1c2 . . 0.96 ?
  O4 C9 . . 1.234(3) ?
  O3 C8 . . 1.2676(18) ?
  N3 H1n3 . . 0.870(11) ?
  N3 H2n3 . . 0.87 ?
  N3 H3n3 . . 0.87 ?
  N3 H4n3 . . 0.87 ?
  C3 C4 . . 1.420(3) ?
  C4 H1c4 . . 0.96 ?
  C6 C7 . . 1.364(3) ?
  C6 H1c6 . . 0.96 ?
  O6 H1o6 . . 0.953(6) ?
  O6 H2o6 . . 0.953(15) ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_2
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
  C1 S1 C7 . . . 91.49(8) ?
  C2 N1 C3 . . . 120.74(15) ?
  C2 N1 C7 . . . 115.64(12) ?
  C3 N1 C7 . . . 123.18(14) ?
  S1 C1 C2 . . . 105.56(12) ?
  S1 C1 H1c1 . . . 109.47 ?
  S1 C1 H2c1 . . . 109.47 ?
  C2 C1 H1c1 . . . 109.47 ?
  C2 C1 H2c1 . . . 109.47 ?
  H1c1 C1 H2c1 . . . 113.11 ?
  C9 O5 H2o6 . . . 121.1(6) ?
  C4 C5 C8 . . . 119.47(13) ?
  C4 C5 C6 . . . 120.67(16) ?
  C8 C5 C6 . . . 119.85(17) ?
  H1n2 N2 H2n2 . . . 109.47 ?
  H1n2 N2 H3n2 . . . 109.47 ?
  H1n2 N2 H4n2 . . . 109.47 ?
  H2n2 N2 H3n2 . . . 109.47 ?
  H2n2 N2 H4n2 . . . 109.47 ?
  H3n2 N2 H4n2 . . . 109.47 ?
  N1 C2 C1 . . . 105.94(16) ?
  N1 C2 C9 . . . 111.14(12) ?
  N1 C2 H1c2 . . . 111.81 ?
  C1 C2 C9 . . . 112.49(13) ?
  C1 C2 H1c2 . . . 110.43 ?
  C9 C2 H1c2 . . . 105.16 ?
  C8 O3 H1o6 . . 1_565 132.3(6) ?
  H1n3 N3 H2n3 . . . 109.47 ?
  H1n3 N3 H3n3 . . . 109.47 ?
  H1n3 N3 H4n3 . . . 109.47 ?
  H2n3 N3 H3n3 . . . 109.47 ?
  H2n3 N3 H4n3 . . . 109.47 ?
  H3n3 N3 H4n3 . . . 109.47 ?
  N1 C3 O1 . . . 119.45(15) ?
  N1 C3 C4 . . . 115.58(16) ?
  O1 C3 C4 . . . 124.97(13) ?
  C5 C4 C3 . . . 121.60(13) ?
  C5 C4 H1c4 . . . 119.2 ?
  C3 C4 H1c4 . . . 119.2 ?
  O5 C9 C2 . . . 117.17(18) ?
  O5 C9 O4 . . . 127.13(19) ?
  C2 C9 O4 . . . 115.61(15) ?
  C5 C8 O2 . . . 118.65(13) ?
  C5 C8 O3 . . . 115.59(17) ?
  O2 C8 O3 . . . 125.77(17) ?
  C5 C6 C7 . . . 117.76(17) ?
  C5 C6 H1c6 . . . 121.12 ?
  C7 C6 H1c6 . . . 121.12 ?
  H1o6 O6 H2o6 . . . 104.5(13) ?
  S1 C7 N1 . . . 111.79(12) ?
  S1 C7 C6 . . . 127.03(14) ?
  N1 C7 C6 . . . 121.11(13) ?


loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_site_symmetry_D
 _geom_hbond_site_symmetry_H
 _geom_hbond_site_symmetry_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_publ_flag
  N3 H1n3 O4 . . 2_656   0.870(11)   1.946(10)   2.803(3)   168.1(8) ?
  N3 H2n3 O6 . . .   0.87   1.91   2.781(2)   174.69 ?
  N3 H3n3 O2 . . 2_766   0.87   2.02   2.8860(19)   170.84 ?
  N3 H4n3 O3 . . 2_666   0.87   2.17   3.039(2)   174.06 ?
  N2 H1n2 O3 . . 2_766   0.870(10)   2.210(10)   2.976(2)   146.7(7) ?
  N2 H2n2 O1 . . 2_666   0.87   2.01   2.8612(18)   167.36 ?
  N2 H3n2 O5 . . .   0.87   1.98   2.833(2)   165.90 ?
  N2 H4n2 O1 . . 1_655   0.87   1.98   2.828(2)   163.39 ?
  O6 H1o6 O3 . . 1_545   0.953(6)   1.790(7)   2.7261(19)   166.7(18) ?
  O6 H2o6 O5 . . .   0.953(15)   1.778(17)   2.680(2)   156.8(14) ?


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

# 11. STRUCTURE-FACTOR LIST



