data_global #=========================================================================== _audit_creation_date '2015-07-23' _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_shrv315 _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(H5 N2), H2 O' _chemical_formula_sum 'C2 H12 N10 O6' _chemical_formula_weight 272.22 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 orthorhombic _space_group_IT_number 33 _space_group_name_H-M_alt 'P n a 21' _space_group_name_Hall 'P 2c -2n' _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+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 19.3262(11) _cell_length_b 3.6054(2) _cell_length_c 15.2342(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1061.50(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2467 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 25.89 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.703 _exptl_crystal_F_000 568 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.164 _exptl_crystal_size_mid 0.054 _exptl_crystal_size_min 0.010 _exptl_absorpt_coefficient_mu 0.159 _shelx_estimated_absorpt_T_min 0.974 _shelx_estimated_absorpt_T_max 0.998 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6845 _exptl_absorpt_correction_T_max 0.7454 _diffrn_ambient_temperature 296(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9040 _diffrn_reflns_av_unetI/netI 0.0310 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.406 _diffrn_reflns_theta_max 26.387 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_point_group_measured_fraction_full 0.997 _reflns_number_total 2175 _reflns_number_gt 1837 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.923 _reflns_Friedel_fraction_max 0.997 _reflns_Friedel_fraction_full 0.997 _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^)+(0.0429P)^2^] 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 2175 _refine_ls_number_parameters 199 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.075 _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 0.12417(11) 0.4831(7) 0.59066(15) 0.0412(6) Uani 1 1 d . . . . . O2 O 0.18020(11) 0.4170(7) 0.46800(14) 0.0383(6) Uani 1 1 d . . . . . N3 N 0.17814(12) 0.5349(7) 0.54503(17) 0.0265(6) Uani 1 1 d . . . . . N4 N 0.22920(12) 0.7073(7) 0.58427(16) 0.0263(6) Uani 1 1 d . . . . . C5 C 0.28778(14) 0.7753(8) 0.53512(19) 0.0220(6) Uani 1 1 d . . . . . N6 N 0.30143(13) 0.7115(8) 0.45255(18) 0.0313(6) Uani 1 1 d . . . . . O7 O 0.36832(11) 0.8485(7) 0.43947(15) 0.0379(6) Uani 1 1 d . . . . . N8 N 0.39529(13) 0.9970(8) 0.51706(17) 0.0326(7) Uani 1 1 d . . . . . C9 C 0.34667(15) 0.9536(8) 0.57562(19) 0.0228(6) Uani 1 1 d . . . . . N10 N 0.34375(12) 1.0491(7) 0.66313(17) 0.0265(6) Uani 1 1 d . . . . . N11 N 0.39749(13) 1.2250(7) 0.69704(16) 0.0290(6) Uani 1 1 d . . . . . O12 O 0.44981(11) 1.3101(8) 0.65371(16) 0.0433(7) Uani 1 1 d . . . . . O13 O 0.39201(13) 1.3099(7) 0.77670(14) 0.0430(6) Uani 1 1 d . . . . . N1S N 0.30219(15) 0.5849(8) 0.25953(18) 0.0334(6) Uani 1 1 d D . . . . H1S H 0.3439(10) 0.538(9) 0.280(2) 0.040 Uiso 1 1 d D U . . . H2S H 0.2979(18) 0.541(11) 0.2043(11) 0.040 Uiso 1 1 d D U . . . N2S N 0.25346(15) 0.3237(8) 0.29509(18) 0.0316(6) Uani 1 1 d D . . . . H3S H 0.2665(17) 0.093(5) 0.288(2) 0.038 Uiso 1 1 d D U . . . H4S H 0.2498(18) 0.373(10) 0.3516(11) 0.038 Uiso 1 1 d D U . . . H5S H 0.2153(12) 0.367(11) 0.267(2) 0.038 Uiso 1 1 d D U . . . N3S N 0.02480(14) 0.1256(9) 0.48272(18) 0.0301(6) Uani 1 1 d D . . . . H6S H 0.0595(13) 0.180(10) 0.518(2) 0.036 Uiso 1 1 d D U . . . H7S H 0.0255(16) -0.102(5) 0.460(2) 0.036 Uiso 1 1 d D U . . . N4S N 0.03036(15) 0.3930(8) 0.41263(19) 0.0340(7) Uani 1 1 d D . . . . H8S H -0.0160(11) 0.164(11) 0.505(2) 0.041 Uiso 1 1 d D U . . . H9S H 0.0702(11) 0.360(11) 0.388(2) 0.041 Uiso 1 1 d D U . . . H10S H -0.0025(15) 0.330(10) 0.376(2) 0.041 Uiso 1 1 d D U . . . O5S O 0.44737(16) 1.3054(10) 0.2538(2) 0.0607(8) Uani 1 1 d D . . . . H12S H 0.475(2) 1.445(13) 0.225(3) 0.091 Uiso 1 1 d D U . . . H11S H 0.433(3) 1.156(14) 0.216(3) 0.091 Uiso 1 1 d 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 0.0246(11) 0.0612(17) 0.0378(13) -0.0099(13) 0.0084(10) -0.0129(11) O2 0.0320(12) 0.0533(16) 0.0297(13) -0.0147(11) -0.0018(10) -0.0099(11) N3 0.0225(13) 0.0312(15) 0.0258(14) -0.0019(12) -0.0030(11) -0.0020(11) N4 0.0218(13) 0.0329(16) 0.0242(13) -0.0055(11) -0.0015(11) -0.0048(11) C5 0.0229(14) 0.0218(15) 0.0212(15) -0.0005(12) -0.0002(12) 0.0004(11) N6 0.0285(12) 0.0397(16) 0.0256(13) -0.0041(12) 0.0020(11) -0.0069(12) O7 0.0344(12) 0.0525(15) 0.0267(12) -0.0084(11) 0.0063(9) -0.0126(11) N8 0.0303(14) 0.0411(18) 0.0263(13) -0.0039(12) 0.0027(12) -0.0061(12) C9 0.0232(14) 0.0241(15) 0.0210(14) 0.0004(13) 0.0003(12) 0.0001(12) N10 0.0242(13) 0.0330(16) 0.0224(12) -0.0014(11) -0.0024(11) -0.0048(11) N11 0.0286(14) 0.0308(16) 0.0276(14) 0.0025(11) -0.0054(11) -0.0023(12) O12 0.0343(14) 0.0573(17) 0.0382(14) -0.0028(12) -0.0015(12) -0.0175(11) O13 0.0537(15) 0.0528(16) 0.0227(12) -0.0051(11) -0.0111(11) -0.0106(12) N1S 0.0417(16) 0.0347(16) 0.0238(13) -0.0029(12) -0.0023(13) -0.0048(13) N2S 0.0381(15) 0.0264(14) 0.0303(14) -0.0025(12) -0.0067(13) 0.0009(13) N3S 0.0249(14) 0.0265(15) 0.0390(16) -0.0031(12) -0.0011(12) -0.0002(12) N4S 0.0339(15) 0.0362(17) 0.0319(15) -0.0009(14) 0.0035(12) 0.0013(13) O5S 0.0506(17) 0.075(2) 0.056(2) 0.0027(16) 0.0048(14) -0.0065(15) _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 1.267(3) . ? O2 N3 1.249(3) . ? N3 N4 1.310(4) . ? N4 C5 1.379(3) . ? C5 N6 1.306(4) . ? C5 C9 1.445(4) . ? N6 O7 1.398(3) . ? O7 N8 1.398(3) . ? N8 C9 1.305(4) . ? C9 N10 1.378(4) . ? N10 N11 1.322(3) . ? N11 O12 1.246(3) . ? N11 O13 1.256(3) . ? N1S N2S 1.438(4) . ? N1S H1S 0.879(14) . ? N1S H2S 0.860(14) . ? N2S H3S 0.877(14) . ? N2S H4S 0.881(14) . ? N2S H5S 0.869(14) . ? N3S N4S 1.443(4) . ? N3S H6S 0.880(14) . ? N3S H7S 0.887(14) . ? N3S H8S 0.870(14) . ? N4S H9S 0.865(14) . ? N4S H10S 0.871(14) . ? O5S H12S 0.854(15) . ? O5S H11S 0.833(15) . ? 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 119.4(2) . . ? O2 N3 N4 124.5(2) . . ? O1 N3 N4 116.1(3) . . ? N3 N4 C5 117.1(2) . . ? N6 C5 N4 131.1(3) . . ? N6 C5 C9 109.3(2) . . ? N4 C5 C9 119.6(2) . . ? C5 N6 O7 105.2(2) . . ? N6 O7 N8 111.1(2) . . ? C9 N8 O7 105.3(2) . . ? N8 C9 N10 131.4(3) . . ? N8 C9 C5 109.2(3) . . ? N10 C9 C5 119.5(3) . . ? N11 N10 C9 117.8(2) . . ? O12 N11 O13 121.3(3) . . ? O12 N11 N10 123.3(3) . . ? O13 N11 N10 115.4(3) . . ? N2S N1S H1S 110(2) . . ? N2S N1S H2S 101(3) . . ? H1S N1S H2S 113(3) . . ? N1S N2S H3S 113(2) . . ? N1S N2S H4S 107(2) . . ? H3S N2S H4S 109(4) . . ? N1S N2S H5S 104(3) . . ? H3S N2S H5S 111(4) . . ? H4S N2S H5S 113(3) . . ? N4S N3S H6S 104(2) . . ? N4S N3S H7S 110(2) . . ? H6S N3S H7S 115(3) . . ? N4S N3S H8S 105(3) . . ? H6S N3S H8S 115(4) . . ? H7S N3S H8S 108(3) . . ? N3S N4S H9S 107(3) . . ? N3S N4S H10S 104(3) . . ? H9S N4S H10S 110(4) . . ? H12S O5S H11S 104(6) . . ? 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 2.9(4) . . . . ? O1 N3 N4 C5 -178.3(2) . . . . ? N3 N4 C5 N6 3.4(5) . . . . ? N3 N4 C5 C9 -178.0(3) . . . . ? N4 C5 N6 O7 178.4(3) . . . . ? C9 C5 N6 O7 -0.3(3) . . . . ? C5 N6 O7 N8 0.3(3) . . . . ? N6 O7 N8 C9 -0.1(3) . . . . ? O7 N8 C9 N10 -179.4(3) . . . . ? O7 N8 C9 C5 0.0(3) . . . . ? N6 C5 C9 N8 0.2(3) . . . . ? N4 C5 C9 N8 -178.7(3) . . . . ? N6 C5 C9 N10 179.7(3) . . . . ? N4 C5 C9 N10 0.8(4) . . . . ? N8 C9 N10 N11 2.0(5) . . . . ? C5 C9 N10 N11 -177.4(3) . . . . ? C9 N10 N11 O12 0.6(4) . . . . ? C9 N10 N11 O13 179.2(3) . . . . ? 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 O5S 0.879(14) 2.20(2) 2.983(4) 147(3) 1_545 N1S H2S N4 0.860(14) 2.25(2) 3.058(4) 156(4) 3_544 N2S H4S O2 0.881(14) 2.23(2) 3.009(4) 147(3) . N2S H4S N6 0.881(14) 2.20(3) 2.927(4) 139(3) . N2S H5S N10 0.869(14) 2.05(2) 2.869(4) 156(3) 3_544 N3S H6S O1 0.880(14) 1.996(19) 2.838(4) 160(3) . N3S H6S O2 0.880(14) 2.60(3) 3.190(4) 125(3) . N3S H8S N8 0.870(14) 2.11(2) 2.897(4) 149(4) 4_465 N3S H8S O12 0.870(14) 2.36(3) 2.990(4) 130(3) 4_465 N4S H9S O2 0.865(14) 2.46(3) 3.017(4) 123(3) . N4S H9S O13 0.865(14) 2.46(4) 2.966(4) 118(3) 3_544 N4S H10S O5S 0.871(14) 2.16(2) 2.989(4) 159(3) 4_465 O5S H12S O12 0.854(15) 2.019(18) 2.863(4) 170(5) 2_684 O5S H11S O1 0.833(15) 2.30(3) 3.073(4) 155(6) 3_554 _refine_diff_density_max 0.168 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.039 # start Validation Reply Form _vrf_PLAT015_shrv315 ; 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