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

_audit_creation_date '2019-01-24'
_audit_creation_method  'from SHELXTL CIF, local template and enCIFer'
_audit_update_record
;   

;

#===========================================================================
# 1. SUBMISSION DETAILS
#===========================================================================

_publ_contact_author_name       'Dr Damon A. Parrish'

_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;

_publ_contact_author_email        'damon.parrish@nrl.navy.mil'
_publ_contact_author_fax          '202-767-6874'
_publ_contact_author_phone        '202-404-2141'


_publ_requested_journal           ?
_publ_requested_category         ?
_publ_requested_coeditor_name     ?

_publ_contact_letter
;

; 

#===========================================================================
# 2. PROCESSING SUMMARY  (IUCr Office Use Only)
# Do  NOT  alter anthing in this section.
#===========================================================================
_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_techeditor_notes
; ?
;
_journal_coden_ASTM            ?
_journal_name_full             ?
_journal_year                  ?
_journal_volume                ?
_journal_issue                 ?
_journal_page_first            ?
_journal_page_last             ?
_journal_suppl_publ_number      ?
_journal_suppl_publ_pages       ?

#===========================================================================
# 3. TITLE AND AUTHOR LIST
#===========================================================================

_publ_section_title
;
title
;


loop_
 _publ_author_name
 _publ_author_address
 _publ_author_footnote
'Parrish, Damon A.'
;
CBMSE, Code 6910
Naval Research Laboratory
Washington, DC 20375
;
?
'Imler, Gregory H.'
;
CBMSE, Code 6910
Naval Research Laboratory
Washington, DC 20375
;
?
'Shreeve, Jean'ne'
;
Chemistry Department 
University of Idaho
Moscow, ID, 83843
;
?
'Tang, Yongxing'
;
Chemistry Department 
University of Idaho
Moscow, ID, 83843
;
?
#===========================================================================
# 4. TEXT
#===========================================================================

_publ_section_abstract
;

;

_publ_section_comment
;
;

_publ_section_exptl_prep
;
;

_publ_section_exptl_refinement
; 
;

_publ_section_references
;
Bruker (2015). APEX3 v2015.5-2. Bruker AXS Inc., Madison, Wisconsin, 
USA.

Bruker (2013). SAINT v8.34A. Bruker AXS Inc., Madison, Wisconsin, 
USA.

Bruker (2014). SADABS v2014/5, Bruker AXS Inc., Madison, Wisconsin, 
USA.

Bruker (2014). XPREP v2014/2. Bruker AXS Inc., Madison, Wisconsin, 
USA.

Bruker (2014). SHELXTL v2014/7. Bruker AXS Inc., Madison, Wisconsin, 
USA.

Sheldrick, G. M. (2014). SHELXL-2014/7. University of Gottingen, Germany.

Spek, A. L.  (2001) PLATON, A Multipurpose Crystallographic Tool, 
Utrecht University, Utrecht, The Netherlands. 
;

_publ_section_figure_captions
;
Fig 1.  View of 1 showing the labeling of the non-hydrogen atoms...   
Thermal ellipsoids are shown at the  ??% probability level.
;


_publ_section_table_legends
; 
;
#  E.g. Table 1.  Selected geometric parameters (\%A, \%) for compound (1)
#
#  E.g. Table 2.  Hydrogen-bond parameters (\%A, \%) for compound (1)
#  No table legends are required for Electronic-Paper submissions.


_publ_section_acknowledgements
;
Crystallographic studies were supported in part by the Office of Naval 
Research (ONR) and the Naval Research Laboratory (NRL).
;
 
data_shrv774
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C2 H N6 O4, C2 H7 N2 O'
_chemical_formula_sum
 'C4 H8 N8 O5' 
_chemical_formula_weight          248.18

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    4.9044(19)
_cell_length_b                    26.767(10)
_cell_length_c                    7.710(3)
_cell_angle_alpha                 90
_cell_angle_beta                  96.835(12)
_cell_angle_gamma                 90
_cell_volume                      1005.0(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used      1102
_cell_measurement_theta_min        2.77
_cell_measurement_theta_max       22.07
 
_exptl_crystal_description        plate
_exptl_crystal_colour             'clear colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.640          
_exptl_crystal_F_000              512
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.261
_exptl_crystal_size_mid           0.183
_exptl_crystal_size_min           0.020
_exptl_absorpt_coefficient_mu     0.147
_shelx_estimated_absorpt_T_min    0.963
_shelx_estimated_absorpt_T_max    0.997
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5251
_exptl_absorpt_correction_T_max   0.7452
_exptl_absorpt_process_details    'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(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 SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6901
_diffrn_reflns_av_unetI/netI      0.1167
_diffrn_reflns_av_R_equivalents   0.1204
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -32
_diffrn_reflns_limit_k_max        32
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          1.522
_diffrn_reflns_theta_max          25.614
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.968
_diffrn_measured_fraction_theta_full  0.986
_diffrn_reflns_Laue_measured_fraction_max    0.968
_diffrn_reflns_Laue_measured_fraction_full   0.986
_diffrn_reflns_point_group_measured_fraction_max   0.968
_diffrn_reflns_point_group_measured_fraction_full  0.986
_reflns_number_total              1830
_reflns_number_gt                 993
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement        'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction         
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution     'Bruker SHELXTL v2014/7 (Bruker, 2014)' 
_computing_structure_refinement 
'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material   'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0380P)²+8.0051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1830
_refine_ls_number_parameters      155
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1947
_refine_ls_R_factor_gt            0.1169
_refine_ls_wR_factor_ref          0.2689
_refine_ls_wR_factor_gt           0.2437
_refine_ls_goodness_of_fit_ref    1.105
_refine_ls_restrained_S_all       1.105
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 1.0825(11) 0.6515(2) 0.7717(8) 0.0495(18) Uani 1 1 d . . . . .
O2 O 0.8942(14) 0.7142(2) 0.6261(10) 0.066(2) Uani 1 1 d . . . . .
N3 N 0.8965(13) 0.6695(2) 0.6648(9) 0.0387(19) Uani 1 1 d . . . . .
C4 C 0.6969(16) 0.6362(3) 0.5934(11) 0.035(2) Uani 1 1 d . . . . .
N5 N 0.4770(14) 0.6532(2) 0.4748(9) 0.0400(19) Uani 1 1 d . . . . .
O6 O 0.4414(13) 0.6974(2) 0.4328(9) 0.058(2) Uani 1 1 d . . . . .
O7 O 0.3184(13) 0.6204(2) 0.4088(9) 0.065(2) Uani 1 1 d . . . . .
C8 C 0.7124(15) 0.5841(3) 0.6390(10) 0.031(2) Uani 1 1 d . . . . .
N9 N 0.5026(14) 0.5552(2) 0.6689(10) 0.043(2) Uani 1 1 d . . . . .
H9 H 0.3344 0.5649 0.6616 0.051 Uiso 1 1 calc R U . . .
N10 N 0.5893(15) 0.5091(3) 0.7120(11) 0.053(2) Uani 1 1 d . . . . .
N11 N 0.8526(16) 0.5099(2) 0.7071(12) 0.060(3) Uani 1 1 d . . . . .
N12 N 0.9373(14) 0.5558(3) 0.6611(10) 0.044(2) Uani 1 1 d . . . . .
N13 N 0.5475(14) 0.8012(2) 0.4874(10) 0.048(2) Uani 1 1 d . . . . .
H13A H 0.5822 0.7699 0.5007 0.057 Uiso 1 1 calc R U . . .
H13B H 0.4063 0.8109 0.4187 0.057 Uiso 1 1 calc R U . . .
N14 N 0.9244(14) 0.8211(2) 0.6766(10) 0.050(2) Uani 1 1 d . . . . .
H14A H 1.0289 0.8435 0.7298 0.061 Uiso 1 1 calc R U . . .
H14B H 0.9622 0.7900 0.6927 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7101(17) 0.8344(3) 0.5721(11) 0.040(2) Uani 1 1 d . . . . .
O16 O 0.6403(12) 0.8805(2) 0.5413(8) 0.0513(19) Uani 1 1 d . . . . .
C17 C 0.814(2) 0.9202(3) 0.6204(14) 0.055(3) Uani 1 1 d . . . . .
H17A H 0.8189 0.9187 0.7451 0.083 Uiso 1 1 calc R U . . .
H17B H 0.7421 0.9520 0.5791 0.083 Uiso 1 1 calc R U . . .
H17C H 0.9969 0.9162 0.5894 0.083 Uiso 1 1 calc R U . . .
 
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
O1 0.034(3) 0.049(4) 0.060(4) 0.000(3) -0.019(3) -0.004(3)
O2 0.059(4) 0.026(3) 0.103(6) 0.003(3) -0.035(4) -0.006(3)
N3 0.029(4) 0.040(4) 0.045(5) -0.002(3) -0.005(4) -0.002(3)
C4 0.031(4) 0.034(4) 0.037(5) -0.002(4) -0.008(4) -0.001(3)
N5 0.033(4) 0.033(4) 0.050(5) -0.001(3) -0.011(4) 0.002(3)
O6 0.050(4) 0.035(3) 0.080(5) 0.005(3) -0.028(4) 0.006(3)
O7 0.058(4) 0.033(3) 0.089(5) 0.002(3) -0.047(4) -0.007(3)
C8 0.027(4) 0.034(4) 0.029(5) -0.003(4) -0.008(4) -0.001(4)
N9 0.035(4) 0.031(4) 0.057(5) 0.007(3) -0.013(4) 0.001(3)
N10 0.041(5) 0.038(4) 0.076(6) 0.011(4) -0.007(4) 0.001(4)
N11 0.047(5) 0.029(4) 0.098(7) 0.013(4) -0.014(5) 0.006(4)
N12 0.029(4) 0.040(4) 0.061(5) 0.010(4) 0.001(4) 0.002(3)
N13 0.042(4) 0.034(4) 0.061(5) -0.001(4) -0.021(4) 0.001(3)
N14 0.047(5) 0.033(4) 0.064(5) -0.001(4) -0.022(4) 0.002(3)
C15 0.038(5) 0.037(5) 0.044(5) -0.001(4) -0.003(4) 0.002(4)
O16 0.050(4) 0.034(3) 0.065(4) -0.002(3) -0.018(3) 0.003(3)
C17 0.060(6) 0.039(5) 0.062(7) -0.004(5) -0.013(6) -0.007(5)
 
_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
O1 N3 1.250(8) . ?
O2 N3 1.234(8) . ?
N3 C4 1.388(9) . ?
C4 N5 1.404(9) . ?
C4 C8 1.440(10) . ?
N5 O6 1.233(8) . ?
N5 O7 1.240(8) . ?
C8 N9 1.329(10) . ?
C8 N12 1.331(10) . ?
N9 N10 1.336(9) . ?
N9 H9 0.8600 . ?
N10 N11 1.296(11) . ?
N11 N12 1.358(9) . ?
N13 C15 1.314(10) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
N14 C15 1.295(10) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
C15 O16 1.296(9) . ?
O16 C17 1.451(9) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
 
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 N3 O1 121.1(6) . . ?
O2 N3 C4 122.8(6) . . ?
O1 N3 C4 116.1(6) . . ?
N3 C4 N5 120.1(7) . . ?
N3 C4 C8 120.7(6) . . ?
N5 C4 C8 119.1(6) . . ?
O6 N5 O7 120.5(6) . . ?
O6 N5 C4 123.7(6) . . ?
O7 N5 C4 115.7(6) . . ?
N9 C8 N12 107.2(7) . . ?
N9 C8 C4 125.9(7) . . ?
N12 C8 C4 126.9(8) . . ?
C8 N9 N10 110.5(7) . . ?
C8 N9 H9 124.8 . . ?
N10 N9 H9 124.8 . . ?
N11 N10 N9 105.4(7) . . ?
N10 N11 N12 111.1(6) . . ?
C8 N12 N11 105.8(7) . . ?
C15 N13 H13A 120.0 . . ?
C15 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C15 N14 H14A 120.0 . . ?
C15 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N14 C15 O16 123.5(7) . . ?
N14 C15 N13 121.6(7) . . ?
O16 C15 N13 114.9(7) . . ?
C15 O16 C17 119.4(6) . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 N3 C4 N5 -1.5(14) . . . . ?
O1 N3 C4 N5 178.7(8) . . . . ?
O2 N3 C4 C8 178.3(9) . . . . ?
O1 N3 C4 C8 -1.5(12) . . . . ?
N3 C4 N5 O6 -2.9(14) . . . . ?
C8 C4 N5 O6 177.3(8) . . . . ?
N3 C4 N5 O7 175.4(8) . . . . ?
C8 C4 N5 O7 -4.4(13) . . . . ?
N3 C4 C8 N9 139.4(9) . . . . ?
N5 C4 C8 N9 -40.8(13) . . . . ?
N3 C4 C8 N12 -39.7(13) . . . . ?
N5 C4 C8 N12 140.1(9) . . . . ?
N12 C8 N9 N10 0.7(10) . . . . ?
C4 C8 N9 N10 -178.6(8) . . . . ?
C8 N9 N10 N11 -0.3(10) . . . . ?
N9 N10 N11 N12 -0.2(11) . . . . ?
N9 C8 N12 N11 -0.8(10) . . . . ?
C4 C8 N12 N11 178.5(8) . . . . ?
N10 N11 N12 C8 0.6(11) . . . . ?
N14 C15 O16 C17 2.8(15) . . . . ?
N13 C15 O16 C17 -176.6(9) . . . . ?
 
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 
N9 H9 N12  0.86 1.96 2.766(10) 155.0 1_455
N14 H14A O6  0.86 2.64 3.063(8) 111.4 4_676
N14 H14A O7  0.86 2.09 2.926(8) 162.6 4_676
N14 H14B O2  0.86 2.11 2.889(9) 150.7 .
N13 H13B O1  0.86 2.10 2.943(8) 168.6 4_475
N13 H13A O6  0.86 2.10 2.850(9) 144.6 .
N13 H13A O2  0.86 2.27 3.004(9) 143.7 .
 
_refine_diff_density_max    0.421
_refine_diff_density_min   -0.357
_refine_diff_density_rms    0.089

# start Validation Reply Form
_vrf_PLAT015_shrv774
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
# end Validation Reply Form