data_global
_audit_creation_date                               2019-10-28
_audit_creation_method                            'by CrystalStructure 4.3'
_audit_update_record                               ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic                      ?
_journal_date_from_coeditor                        ?
_journal_date_accepted                             ?
_journal_coeditor_code                             ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name                         'ENTER NAME'
_publ_contact_author_email                        'ENTER EMAIL ADDRESS'
_publ_contact_author_fax                          'ENTER FAX NUMBER'
_publ_contact_author_phone                        'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                           'ENTER JOURNAL NAME HERE'
_publ_requested_category
                                               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name                      ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2018). CrystalStructure. Version 4.3. 
    Rigaku Corporation, Tokyo, Japan.

    Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., 
    Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. and Spagna R.
    (2005). J. Appl. Cryst. 38, 381-388.
    SIR2004

    Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany.

    Rigaku (1995). ABSCOR. 
    Rigaku Corporation, Tokyo, Japan.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_2018040401

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                             'C6 H9 N4 O4 P S2'
_chemical_formula_moiety                          'C6 H9 N4 O4 P S2'
_chemical_formula_weight                           296.26
_chemical_melting_point                            ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system                        monoclinic
_space_group_name_H-M_alt                         'P 1 21/c 1'
_space_group_name_Hall                            '-P 2ybc'
_space_group_IT_number                             14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1   '+X,+Y,+Z'
2   '-X,1/2+Y,1/2-Z'
3   '-X,-Y,-Z'
4   '+X,-1/2-Y,-1/2+Z'
#------------------------------------------------------------------------------
_cell_length_a                                     13.8433(4)
_cell_length_b                                     10.0451(2)
_cell_length_c                                     8.1208(3)
_cell_angle_alpha                                  90.0000
_cell_angle_beta                                   95.190(2)
_cell_angle_gamma                                  90.0000
_cell_volume                                       1124.63(5)
_cell_formula_units_Z                              4
_cell_measurement_reflns_used                      4880
_cell_measurement_theta_min                        3.21
_cell_measurement_theta_max                        68.14
_cell_measurement_temperature                      150
#------------------------------------------------------------------------------
_exptl_crystal_description                         platelet
_exptl_crystal_colour                              colorless
_exptl_crystal_size_max                            0.100
_exptl_crystal_size_mid                            0.100
_exptl_crystal_size_min                            0.100
_exptl_crystal_density_diffrn                      1.750
_exptl_crystal_density_meas                        ?
_exptl_crystal_density_method                     'not measured'
_exptl_crystal_F_000                               608.00
_exptl_absorpt_coefficient_mu                      5.789
_exptl_absorpt_correction_type                     multi-scan
_exptl_absorpt_process_details                    'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min                    0.459
_exptl_absorpt_correction_T_max                    0.561

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature                        150
_diffrn_radiation_type                            'Cu K\a'
_diffrn_radiation_wavelength                       1.54187
_diffrn_measurement_device_type                   'Rigaku R-AXIS RAPID'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   10.000
_diffrn_reflns_number                              12324
_diffrn_reflns_av_unetI/netI                       0.0372
_diffrn_reflns_av_R_equivalents                    0.0509
_diffrn_reflns_theta_max                           68.210
_diffrn_reflns_theta_min                           3.206
_diffrn_reflns_theta_full                          68.210
_diffrn_measured_fraction_theta_max                0.996
_diffrn_measured_fraction_theta_full               0.996
_diffrn_reflns_Laue_measured_fraction_max          0.000
_diffrn_reflns_Laue_measured_fraction_full         0.000
_diffrn_reflns_point_group_measured_fraction_max   0.000
_diffrn_reflns_point_group_measured_fraction_full  0.000
_diffrn_reflns_limit_h_min                        -16
_diffrn_reflns_limit_h_max                         16
_diffrn_reflns_limit_k_min                        -12
_diffrn_reflns_limit_k_max                         12
_diffrn_reflns_limit_l_min                        -9
_diffrn_reflns_limit_l_max                         9
_diffrn_standards_number                           0
_diffrn_standards_interval_count                   .
_diffrn_standards_decay_%                          ?
_reflns_number_total                               2050
_reflns_number_gt                                  1806
_reflns_threshold_expression                       F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef                   Fsqd
_refine_ls_R_factor_all                            0.0444
_refine_ls_R_factor_gt                             0.0397
_refine_ls_wR_factor_ref                           0.1130
_refine_ls_wR_factor_gt                            0.1058
_refine_ls_number_restraints                       0
_refine_ls_hydrogen_treatment                      constr
_refine_ls_number_reflns                           2050
_refine_ls_number_parameters                       154
_refine_ls_goodness_of_fit_ref                     1.090
_refine_ls_weighting_scheme                        calc
_refine_ls_weighting_details
           'w = 1/[σ²(Fo²)+(0.0635P)²+0.6957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens                     geom
_atom_sites_solution_primary                       direct
_atom_sites_solution_secondary                     difmap
_refine_ls_shift/su_max                            0.001
_refine_diff_density_max                           0.38
_refine_diff_density_min                          -0.53
_refine_ls_extinction_method                       none
_refine_ls_extinction_coef                         ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'N' 'N'  0.0311 0.0180 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'P' 'P'  0.2955 0.4335 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
  'S' 'S'  0.3331 0.5567 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0492 0.0322 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 
S1 S 0.99890(5) 0.36106(6) 0.36268(10) 0.0332(2) Uani 1 1 d . . . 
S2 S 0.61277(4) 0.12019(6) 0.65574(9) 0.0275(2) Uani 1 1 d . . . 
N1 N 0.91356(16) 0.1498(2) 0.4564(3) 0.0277(5) Uani 1 1 d . . . 
N2 N 0.70218(14) 0.3325(2) 0.5938(3) 0.0223(5) Uani 1 1 d . . . 
H5 H 0.7174 0.4171 0.5850 0.027 Uiso 1 1 calc R . . 
N3 N 1.06883(16) 0.1121(2) 0.3696(3) 0.0356(6) Uani 1 1 d . . . 
H2B H 1.0661 0.0261 0.3893 0.043 Uiso 1 1 calc R . . 
H3A H 1.1207 0.1465 0.3308 0.043 Uiso 1 1 calc R . . 
N4 N 0.55660(16) 0.3720(2) 0.7136(3) 0.0308(6) Uani 1 1 d . . . 
H6A H 0.5652 0.4588 0.7114 0.037 Uiso 1 1 calc R . . 
H7B H 0.5048 0.3388 0.7537 0.037 Uiso 1 1 calc R . . 
C1 C 0.85259(17) 0.2569(2) 0.4762(3) 0.0233(5) Uani 1 1 d . . . 
C2 C 0.88532(19) 0.3768(3) 0.4311(4) 0.0309(6) Uani 1 1 d . . . 
H1 H 0.8507 0.4581 0.4364 0.037 Uiso 1 1 calc R . . 
C3 C 0.99365(18) 0.1911(2) 0.3988(4) 0.0252(6) Uani 1 1 d . . . 
C4 C 0.76067(17) 0.2294(2) 0.5429(3) 0.0234(5) Uani 1 1 d . . . 
C5 C 0.72181(18) 0.1094(3) 0.5678(3) 0.0276(6) Uani 1 1 d . . . 
H4 H 0.7509 0.0277 0.5402 0.033 Uiso 1 1 calc R . . 
C6 C 0.62128(18) 0.2919(2) 0.6570(3) 0.0234(5) Uani 1 1 d . . . 
P1 P 0.32357(4) 0.29901(6) 0.32144(8) 0.0226(2) Uani 1 1 d . . . 
O1 O 0.28270(13) 0.38561(16) 0.4492(2) 0.0265(4) Uani 1 1 d . . . 
O2 O 0.38304(14) 0.37086(17) 0.2020(2) 0.0312(5) Uani 1 1 d . . . 
O3 O 0.39126(15) 0.18842(19) 0.4047(2) 0.0362(5) Uani 1 1 d . . . 
H9 H 0.3612 0.1460 0.4731 0.043 Uiso 1 1 calc R . . 
O4 O 0.23758(13) 0.22437(19) 0.2222(2) 0.0318(5) Uani 1 1 d . . . 
H8 H 0.2598 0.1693 0.1574 0.038 Uiso 1 1 calc R . . 


#==============================================================================
_computing_data_collection                        'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement                        'RAPID AUTO'
_computing_data_reduction                         'RAPID AUTO'
_computing_structure_solution
                                                'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement                   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material
                                          'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics                     'CrystalStructure 4.3'

#==============================================================================
# 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_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
S1 C2 1.722(3) . ? 
S1 C3 1.735(3) . ? 
S2 C6 1.729(2) . ? 
S2 C5 1.731(3) . ? 
N1 C3 1.309(3) . ? 
N1 C1 1.386(3) . ? 
N2 C6 1.337(3) . ? 
N2 C4 1.400(3) . ? 
N2 H5 0.8800 . ? 
N3 C3 1.347(3) . ? 
N3 H2B 0.8800 . ? 
N3 H3A 0.8800 . ? 
N4 C6 1.317(3) . ? 
N4 H6A 0.8800 . ? 
N4 H7B 0.8800 . ? 
C1 C2 1.349(3) . ? 
C1 C4 1.454(3) . ? 
C2 H1 0.9500 . ? 
C4 C5 1.342(3) . ? 
C5 H4 0.9500 . ? 
P1 O1 1.5033(18) . ? 
P1 O2 1.5112(18) . ? 
P1 O3 1.5666(19) . ? 
P1 O4 1.5669(19) . ? 
O3 H9 0.8400 . ? 
O4 H8 0.8400 . ? 

loop_
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 S1 C3 88.98(12) . . ? 
C6 S2 C5 90.19(12) . . ? 
C3 N1 C1 109.9(2) . . ? 
C6 N2 C4 114.5(2) . . ? 
C6 N2 H5 122.8 . . ? 
C4 N2 H5 122.8 . . ? 
C3 N3 H2B 120.0 . . ? 
C3 N3 H3A 120.0 . . ? 
H2B N3 H3A 120.0 . . ? 
C6 N4 H6A 120.0 . . ? 
C6 N4 H7B 120.0 . . ? 
H6A N4 H7B 120.0 . . ? 
C2 C1 N1 116.0(2) . . ? 
C2 C1 C4 126.7(2) . . ? 
N1 C1 C4 117.3(2) . . ? 
C1 C2 S1 110.16(19) . . ? 
C1 C2 H1 124.9 . . ? 
S1 C2 H1 124.9 . . ? 
N1 C3 N3 124.7(2) . . ? 
N1 C3 S1 114.99(19) . . ? 
N3 C3 S1 120.33(19) . . ? 
C5 C4 N2 111.7(2) . . ? 
C5 C4 C1 127.1(2) . . ? 
N2 C4 C1 121.2(2) . . ? 
C4 C5 S2 112.49(19) . . ? 
C4 C5 H4 123.8 . . ? 
S2 C5 H4 123.8 . . ? 
N4 C6 N2 124.6(2) . . ? 
N4 C6 S2 124.28(19) . . ? 
N2 C6 S2 111.15(18) . . ? 
O1 P1 O2 115.31(10) . . ? 
O1 P1 O3 111.12(10) . . ? 
O2 P1 O3 106.04(11) . . ? 
O1 P1 O4 108.42(10) . . ? 
O2 P1 O4 109.33(11) . . ? 
O3 P1 O4 106.23(11) . . ? 
P1 O3 H9 109.5 . . ? 
P1 O4 H8 109.5 . . ? 

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 
C3 N1 C1 C2 1.3(4) . . . . ? 
C3 N1 C1 C4 -178.6(2) . . . . ? 
N1 C1 C2 S1 -1.1(3) . . . . ? 
C4 C1 C2 S1 178.9(2) . . . . ? 
C3 S1 C2 C1 0.4(2) . . . . ? 
C1 N1 C3 N3 178.4(3) . . . . ? 
C1 N1 C3 S1 -0.9(3) . . . . ? 
C2 S1 C3 N1 0.3(2) . . . . ? 
C2 S1 C3 N3 -179.0(3) . . . . ? 
C6 N2 C4 C5 0.5(3) . . . . ? 
C6 N2 C4 C1 -178.1(2) . . . . ? 
C2 C1 C4 C5 170.6(3) . . . . ? 
N1 C1 C4 C5 -9.5(4) . . . . ? 
C2 C1 C4 N2 -11.1(4) . . . . ? 
N1 C1 C4 N2 168.8(2) . . . . ? 
N2 C4 C5 S2 -0.4(3) . . . . ? 
C1 C4 C5 S2 178.1(2) . . . . ? 
C6 S2 C5 C4 0.2(2) . . . . ? 
C4 N2 C6 N4 179.4(3) . . . . ? 
C4 N2 C6 S2 -0.3(3) . . . . ? 
C5 S2 C6 N4 -179.6(2) . . . . ? 
C5 S2 C6 N2 0.1(2) . . . . ? 

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_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H5 O1 . . 3_666 2.863(3) 0.880 2.001 166.0 no
N3 H2B S1 . . 2_745 3.237(2) 0.880 2.723 118.5 no
N3 H2B N1 . . 3_756 2.986(3) 0.880 2.170 154.0 no
N3 H3A O4 . . 1_655 2.944(3) 0.880 2.066 175.7 no
N4 H6A O2 . . 3_666 2.781(3) 0.880 1.961 154.5 no
N4 H7B O3 . . 4_566 2.942(3) 0.880 2.097 160.9 no
O3 H9 O2 . . 4_566 2.500(3) 0.840 1.863 131.4 no
O4 H8 O1 . . 4_565 2.603(3) 0.840 1.834 151.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
