data_global #=========================================================================== _audit_creation_date '2015-07-13' _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 ; ? 'Mitchell, Lauren A.' ; CBMSE, Code 6910 Naval Research Laboratory Washington, DC 20375 ; ? 'Shreeve, Jean'ne' ; Chemsitry Department University of Idaho Moscow, ID, 83843 ; ? 'Tang, Yongxing' ; Chemsitry 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 (2014). APEX2 v2014.11-0. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2009). SAINT v7.68A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SADABS v2008/1, 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. Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854. Sheldrick, G. M. (2014). SHELXL-2014/7. University of Gottingen, Germany. ; _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_shrv312 _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 N6 O5, 2(H2 O), 2(H4 N)' _chemical_formula_sum 'C2 H12 N8 O7' _chemical_formula_weight 260.20 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' '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _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, -z' _cell_length_a 3.7177(2) _cell_length_b 9.6263(5) _cell_length_c 14.2216(7) _cell_angle_alpha 82.456(2) _cell_angle_beta 89.502(2) _cell_angle_gamma 86.436(2) _cell_volume 503.58(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2439 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 68.84 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_F_000 272 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.115 _exptl_crystal_size_mid 0.062 _exptl_crystal_size_min 0.025 _exptl_absorpt_coefficient_mu 1.469 _shelx_estimated_absorpt_T_min 0.849 _shelx_estimated_absorpt_T_max 0.964 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6792 _exptl_absorpt_correction_T_max 0.7532 _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device 'Bruker PLATINUM 135 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 2974 _diffrn_reflns_av_unetI/netI 0.0187 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.134 _diffrn_reflns_theta_max 68.914 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.843 _diffrn_measured_fraction_theta_full 0.856 _diffrn_reflns_Laue_measured_fraction_max 0.843 _diffrn_reflns_Laue_measured_fraction_full 0.856 _diffrn_reflns_point_group_measured_fraction_max 0.843 _diffrn_reflns_point_group_measured_fraction_full 0.856 _reflns_number_total 1588 _reflns_number_gt 1496 _reflns_threshold_expression 'I > 2\s(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 APEX2 v2014.11-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2014.11-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2014/7 (Bruker, 2008)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)' _computing_molecular_graphics 'Bruker SHELXTL v2014/7 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2014/7 (Bruker, 2008)' _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/[\s^2^(Fo^2^)+(0.0556P)^2^+0.1825P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 1588 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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_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 0.0460(3) 1.03267(11) 0.40316(7) 0.0215(3) Uani 1 1 d . . . . . O2 O 0.2284(3) 1.16080(10) 0.27571(7) 0.0200(3) Uani 1 1 d . . . . . N3 N 0.1914(3) 1.04265(12) 0.32220(9) 0.0152(3) Uani 1 1 d . . . . . N4 N 0.2951(3) 0.92297(12) 0.29185(8) 0.0155(3) Uani 1 1 d . . . . . C5 C 0.4690(3) 0.93184(14) 0.20562(10) 0.0135(3) Uani 1 1 d . . . . . N6 N 0.5980(3) 1.03811(12) 0.15167(9) 0.0160(3) Uani 1 1 d . . . . . O7 O 0.7610(3) 0.98084(10) 0.07536(7) 0.0179(3) Uani 1 1 d . . . . . N8 N 0.7229(3) 0.83749(12) 0.08249(9) 0.0165(3) Uani 1 1 d . . . . . C9 C 0.5465(3) 0.80519(14) 0.16150(10) 0.0136(3) Uani 1 1 d . . . . . N10 N 0.4348(3) 0.67836(12) 0.20545(9) 0.0157(3) Uani 1 1 d . . . . . N11 N 0.4780(3) 0.57216(12) 0.15732(9) 0.0153(3) Uani 1 1 d . . . . . O12 O 0.6073(3) 0.57884(11) 0.07526(7) 0.0217(3) Uani 1 1 d . . . . . O13 O 0.3774(3) 0.45487(10) 0.19824(7) 0.0202(3) Uani 1 1 d . . . . . N1S N -0.0360(3) 0.29681(13) 0.08172(10) 0.0163(3) Uani 1 1 d . . . . . H1S H -0.148(5) 0.225(2) 0.1160(13) 0.020 Uiso 1 1 d . U . . . H2S H 0.074(5) 0.2604(19) 0.0293(14) 0.020 Uiso 1 1 d . U . . . H3S H -0.188(5) 0.371(2) 0.0614(13) 0.020 Uiso 1 1 d . U . . . H4S H 0.111(5) 0.3285(19) 0.1163(14) 0.020 Uiso 1 1 d . U . . . N2S N 0.6281(4) 0.77780(15) 0.47672(10) 0.0194(3) Uani 1 1 d . . . . . H5S H 0.501(5) 0.818(2) 0.4340(15) 0.023 Uiso 1 1 d . U . . . H6S H 0.783(5) 0.718(2) 0.4492(13) 0.023 Uiso 1 1 d . U . . . H7S H 0.491(5) 0.729(2) 0.5251(14) 0.023 Uiso 1 1 d . U . . . H8S H 0.728(5) 0.845(2) 0.4989(14) 0.023 Uiso 1 1 d . U . . . O3S O 0.7721(3) 0.35549(12) 0.36658(8) 0.0228(3) Uani 1 1 d . . . . . H9S H 0.902(6) 0.290(2) 0.3408(15) 0.034 Uiso 1 1 d . U . . . H10S H 0.635(6) 0.389(2) 0.3205(16) 0.034 Uiso 1 1 d . U . . . O4S O 1.1137(3) 0.59857(13) 0.39482(9) 0.0252(3) Uani 1 1 d . . . . . H11S H 1.016(6) 0.526(3) 0.3876(15) 0.038 Uiso 1 1 d . U . . . H12S H 1.186(6) 0.628(2) 0.3464(17) 0.038 Uiso 1 1 d . 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 0.0303(6) 0.0207(6) 0.0147(6) -0.0053(4) 0.0082(5) -0.0057(4) O2 0.0296(5) 0.0114(5) 0.0187(6) -0.0004(4) 0.0041(5) -0.0023(4) N3 0.0169(5) 0.0147(6) 0.0144(6) -0.0024(5) 0.0002(5) -0.0034(4) N4 0.0198(6) 0.0134(7) 0.0137(6) -0.0031(5) 0.0022(5) -0.0019(4) C5 0.0129(6) 0.0155(8) 0.0122(7) -0.0016(5) -0.0017(6) -0.0019(5) N6 0.0185(6) 0.0160(7) 0.0140(6) -0.0036(5) 0.0027(5) -0.0030(4) O7 0.0238(5) 0.0130(6) 0.0176(6) -0.0029(4) 0.0066(4) -0.0045(4) N8 0.0197(6) 0.0123(7) 0.0180(7) -0.0024(5) 0.0016(5) -0.0030(4) C9 0.0132(6) 0.0147(8) 0.0132(7) -0.0018(5) -0.0010(6) -0.0015(5) N10 0.0210(6) 0.0110(6) 0.0156(6) -0.0032(4) 0.0012(5) -0.0026(4) N11 0.0178(5) 0.0137(7) 0.0144(7) -0.0016(5) -0.0016(5) -0.0011(4) O12 0.0338(6) 0.0186(6) 0.0131(5) -0.0040(4) 0.0047(5) -0.0010(4) O13 0.0299(5) 0.0116(6) 0.0194(6) -0.0005(4) 0.0002(5) -0.0062(4) N1S 0.0194(6) 0.0128(7) 0.0168(7) -0.0020(5) 0.0009(6) -0.0024(5) N2S 0.0213(6) 0.0158(7) 0.0209(7) -0.0001(5) -0.0029(6) -0.0037(5) O3S 0.0276(6) 0.0197(6) 0.0211(6) -0.0038(4) -0.0003(5) 0.0004(4) O4S 0.0299(6) 0.0269(7) 0.0207(6) -0.0064(5) 0.0059(5) -0.0101(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 1.2623(16) . ? O2 N3 1.2530(16) . ? N3 N4 1.3171(17) . ? N4 C5 1.3765(19) . ? C5 N6 1.3091(18) . ? C5 C9 1.4550(19) . ? N6 O7 1.3975(15) . ? O7 N8 1.3864(16) . ? N8 C9 1.308(2) . ? C9 N10 1.3827(18) . ? N10 N11 1.3042(17) . ? N11 O12 1.2537(16) . ? N11 O13 1.2766(16) . ? N1S H1S 0.912(19) . ? N1S H2S 0.945(19) . ? N1S H3S 0.898(19) . ? N1S H4S 0.84(2) . ? N2S H5S 0.81(2) . ? N2S H6S 0.91(2) . ? N2S H7S 0.94(2) . ? N2S H8S 0.86(2) . ? O3S H9S 0.89(2) . ? O3S H10S 0.85(2) . ? O4S H11S 0.83(3) . ? O4S H12S 0.76(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 N3 O1 120.35(11) . . ? O2 N3 N4 123.95(12) . . ? O1 N3 N4 115.70(11) . . ? N3 N4 C5 116.54(12) . . ? N6 C5 N4 131.73(12) . . ? N6 C5 C9 108.73(12) . . ? N4 C5 C9 119.52(13) . . ? C5 N6 O7 105.30(10) . . ? N8 O7 N6 111.45(10) . . ? C9 N8 O7 105.53(11) . . ? N8 C9 N10 131.53(13) . . ? N8 C9 C5 108.98(13) . . ? N10 C9 C5 119.49(13) . . ? N11 N10 C9 116.23(12) . . ? O12 N11 O13 119.29(11) . . ? O12 N11 N10 124.53(12) . . ? O13 N11 N10 116.18(12) . . ? H1S N1S H2S 107.0(16) . . ? H1S N1S H3S 113.1(16) . . ? H2S N1S H3S 109.9(15) . . ? H1S N1S H4S 109.5(16) . . ? H2S N1S H4S 112.9(16) . . ? H3S N1S H4S 104.6(16) . . ? H5S N2S H6S 105.8(17) . . ? H5S N2S H7S 111.7(17) . . ? H6S N2S H7S 111.0(16) . . ? H5S N2S H8S 104.0(19) . . ? H6S N2S H8S 114.8(17) . . ? H7S N2S H8S 109.2(17) . . ? H9S O3S H10S 100.7(19) . . ? H11S O4S H12S 107(2) . . ? 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 N4 C5 3.18(18) . . . . ? O1 N3 N4 C5 -177.12(11) . . . . ? N3 N4 C5 N6 10.7(2) . . . . ? N3 N4 C5 C9 -171.53(11) . . . . ? N4 C5 N6 O7 176.93(13) . . . . ? C9 C5 N6 O7 -1.05(13) . . . . ? C5 N6 O7 N8 1.27(13) . . . . ? N6 O7 N8 C9 -0.95(14) . . . . ? O7 N8 C9 N10 -179.37(13) . . . . ? O7 N8 C9 C5 0.27(14) . . . . ? N6 C5 C9 N8 0.52(15) . . . . ? N4 C5 C9 N8 -177.75(11) . . . . ? N6 C5 C9 N10 -179.79(11) . . . . ? N4 C5 C9 N10 1.94(19) . . . . ? N8 C9 N10 N11 -7.6(2) . . . . ? C5 C9 N10 N11 172.79(11) . . . . ? C9 N10 N11 O12 -0.93(19) . . . . ? C9 N10 N11 O13 179.48(11) . . . . ? 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 N1S H1S N6 0.912(19) 2.09(2) 2.9648(17) 161.5(16) 1_445 N1S H1S O7 0.912(19) 2.536(19) 3.1918(16) 129.2(15) 1_445 N1S H2S N8 0.945(19) 2.07(2) 3.0065(18) 173.5(16) 2_665 N1S H2S O12 0.945(19) 2.366(18) 2.9035(17) 115.7(13) 2_665 N1S H3S O12 0.898(19) 2.132(19) 2.9371(16) 148.8(15) 1_455 N1S H3S O12 0.898(19) 2.482(19) 3.1612(17) 132.8(14) 2_565 N1S H4S O13 0.84(2) 2.09(2) 2.9017(17) 164.4(17) . N2S H5S O1 0.81(2) 2.58(2) 3.2405(17) 139.0(17) . N2S H5S N4 0.81(2) 2.26(2) 3.0455(18) 163.6(18) . N2S H6S O4S 0.91(2) 1.86(2) 2.7744(18) 177.8(17) . N2S H7S O3S 0.94(2) 1.93(2) 2.8730(18) 173.2(17) 2_666 N2S H8S O1 0.86(2) 2.47(2) 3.0496(17) 125.1(16) 1_655 N2S H8S O1 0.86(2) 2.15(2) 2.9739(18) 161.3(18) 2_676 O3S H9S O1 0.89(2) 2.54(2) 3.1870(16) 130.1(17) 1_645 O3S H9S O2 0.89(2) 1.99(2) 2.8746(15) 173.0(19) 1_645 O3S H9S N3 0.89(2) 2.59(2) 3.4346(16) 158.4(17) 1_645 O3S H10S O13 0.85(2) 2.00(2) 2.8434(16) 170(2) . O4S H11S O3S 0.83(3) 1.98(3) 2.8062(17) 178(2) . O4S H12S N10 0.76(2) 2.21(3) 2.9635(18) 170(2) 1_655 _refine_diff_density_max 0.265 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.060 # start Validation Reply Form _vrf_PLAT015_shrv312 ; 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. ; _vrf_PLAT029_shrv312 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.856 Note RESPONSE: ... ; _vrf_PLAT430_shrv312 ; PROBLEM: Short Inter D...A Contact O1 .. O1 .. 2.77 Ang. RESPONSE: High density energetic materials often display close contacts. ; # end Validation Reply Form