#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:59:50 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288796 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247739.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7247739 loop_ _publ_author_name 'Baraboshkin, Nikita M.' 'Zelenov, Victor P.' 'Fedyanin, Ivan V.' _publ_section_title ; What are the prospects of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides, 1,5-dioxides and their nitro derivatives as high-energy-density materials? Synthesis, experimental and predicted crystal structures, and calculated explosive properties ; _journal_issue 48 _journal_name_full CrystEngComm _journal_page_first 6719 _journal_page_last 6739 _journal_paper_doi 10.1039/D3CE00964E _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C8 H2 N6 O6' _chemical_formula_sum 'C8 H2 N6 O6' _chemical_formula_weight 278.16 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2023-09-18 _audit_creation_method ; Olex2 1.3 (compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938) ; _audit_update_record ; 2023-09-19 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.53304(19) _cell_length_b 8.30693(13) _cell_length_c 9.61288(13) _cell_measurement_reflns_used 9012 _cell_measurement_temperature 99.9(5) _cell_measurement_theta_max 78.3880 _cell_measurement_theta_min 3.5270 _cell_volume 1000.81(3) _computing_cell_refinement 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.9(5) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -38.00 28.00 0.50 1.50 -- -46.94 33.00 74.00 132 2 \w -121.00 -32.00 0.50 1.50 -- -46.94 -33.00 -84.00 178 3 \w 8.00 82.00 0.50 1.50 -- 46.94-102.00 75.00 148 4 \w -166.00 -77.00 0.50 6.00 -- -91.75 -33.00 -84.00 178 5 \w -80.00 -21.00 0.50 6.00 -- -91.75 101.00 -85.00 118 6 \w -163.00 -85.00 0.50 6.00 -- -91.75-102.00 75.00 156 7 \w 42.00 106.00 0.50 6.00 -- 113.25-102.00 75.00 128 8 \w 107.00 178.00 0.50 6.00 -- 113.25 101.00 -85.00 142 9 \w 106.00 178.00 0.50 6.00 -- 113.25 102.00 178.00 144 10 \w 42.00 106.00 0.50 6.00 -- 113.25-101.00 170.00 128 11 \w 99.00 178.00 0.50 6.00 -- 113.25 33.00 74.00 158 12 \w -81.00 14.00 0.50 1.50 -- -46.94 102.00 178.00 190 13 \w -26.00 25.00 0.50 1.50 -- 46.94 -19.00 150.00 102 14 \w 137.00 163.00 0.50 6.00 -- 113.25 77.00-120.00 52 15 \w 96.00 141.00 0.50 6.00 -- 113.25 125.00-120.00 90 16 \w 43.00 79.00 0.50 6.00 -- 113.25-125.00 60.00 72 17 \w 83.00 109.00 0.50 6.00 -- 113.25-125.00 60.00 52 18 \w 81.00 106.00 0.50 6.00 -- 113.25 -95.00 90.00 50 19 \w 41.00 67.00 0.50 6.00 -- 113.25 -61.00 30.00 52 20 \w 43.00 97.00 0.50 6.00 -- 113.25 -77.00 -60.00 108 21 \w 42.00 89.00 0.50 6.00 -- 113.25 -77.00 -30.00 94 22 \w 78.00 111.00 0.50 6.00 -- 113.25-125.00-150.00 66 23 \w 140.00 166.00 0.50 6.00 -- 113.25 15.00-180.00 52 24 \w 43.00 69.00 0.50 6.00 -- 113.25 -77.00-180.00 52 25 \w 65.00 103.00 0.50 6.00 -- 113.25 -77.00-120.00 76 26 \w 41.00 69.00 0.50 6.00 -- 113.25 -95.00 90.00 56 27 \w 41.00 68.00 0.50 6.00 -- 113.25 -61.00 150.00 54 28 \w 42.00 71.00 0.50 6.00 -- 113.25 -61.00 90.00 58 29 \w 70.00 106.00 0.50 6.00 -- 113.25-125.00-120.00 72 30 \w 74.00 108.00 0.50 6.00 -- 113.25-125.00 30.00 68 31 \w 107.00 133.00 0.50 6.00 -- 113.25 45.00-150.00 52 32 \w 49.00 75.00 0.50 6.00 -- 113.25 -77.00-150.00 52 33 \w 62.00 103.00 0.50 6.00 -- 113.25 -77.00 -90.00 82 34 \w 49.00 100.00 0.50 6.00 -- 113.25 -77.00 90.00 102 35 \w 91.00 138.00 0.50 6.00 -- 113.25 0.00-180.00 94 36 \w 151.00 177.00 0.50 6.00 -- 113.25 90.00 -43.37 52 37 \w 105.00 175.00 0.50 6.00 -- 113.25 45.00-120.00 140 38 \w 104.00 174.00 0.50 6.00 -- 113.25 45.00-153.54 140 39 \w 93.00 175.00 0.50 6.00 -- 113.25 77.00 120.00 164 40 \w 68.00 111.00 0.50 6.00 -- 113.25 -82.00-162.92 86 41 \w 42.00 71.00 0.50 6.00 -- 113.25 -61.00-150.00 58 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0865604000 _diffrn_orient_matrix_UB_12 -0.1065404000 _diffrn_orient_matrix_UB_13 0.0668261000 _diffrn_orient_matrix_UB_21 -0.0794001000 _diffrn_orient_matrix_UB_22 0.1414677000 _diffrn_orient_matrix_UB_23 -0.0062789000 _diffrn_orient_matrix_UB_31 -0.0362754000 _diffrn_orient_matrix_UB_32 -0.0549599000 _diffrn_orient_matrix_UB_33 -0.1455292000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_unetI/netI 0.0184 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12518 _diffrn_reflns_point_group_measured_fraction_full 0.881 _diffrn_reflns_point_group_measured_fraction_max 0.871 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.794 _diffrn_reflns_theta_min 5.325 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.432 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.742 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.846 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.262 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details ; Flack x determined using 724 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.07(9) _refine_ls_extinction_coef 0.0032(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 1908 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0322 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.4434P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.0882 _reflns_Friedel_coverage 0.643 _reflns_Friedel_fraction_full 0.744 _reflns_Friedel_fraction_max 0.728 _reflns_number_gt 1884 _reflns_number_total 1908 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00964e2.cif _cod_data_source_block Z461504 _cod_depositor_comments 'Adding full bibliography for 7247734--7247739.cif.' _cod_database_code 7247739 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C8H2N6O6 _chemical_oxdiff_usercomment Z461504 _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. ; _shelx_estimated_absorpt_t_max 0.958 _shelx_estimated_absorpt_t_min 0.783 _reflns_odcompleteness_completeness 99.31 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 80.50 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C10(H10), C12(H12) ; _shelx_res_file ; TITL 23sai_r074_g_a.res in Pca2(1) 23sai_r074_g.res created by SHELXL-2018/3 at 14:25:43 on 18-Sep-2023 REM Old TITL 23SAI_R074_g in Pca2(1) REM SHELXT solution in Pca2(1) REM R1 0.086, Rweak 0.054, Alpha 0.017, Orientation as input REM Flack x = 0.229 ( 0.091 ) from Parsons' quotients REM Formula found by SHELXT: C14 N2 O4 CELL 1.54184 12.53304 8.30693 9.61288 90 90 90 ZERR 4 0.00019 0.00013 0.00013 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,-Y,+Z SYMM 0.5-X,+Y,0.5+Z SFAC C H N O UNIT 32 8 24 24 L.S. 11 PLAN 6 SIZE 0.03 0.05 0.18 TEMP -173 CONF BOND $H list 4 MORE -1 fmap 2 53 acta REM REM REM WGHT 0.048500 0.443400 EXTI 0.003205 FVAR 0.91989 O1 4 0.382639 0.425666 0.734309 11.00000 0.02739 0.02818 = 0.02556 -0.00065 0.00565 -0.00076 O5 4 0.716030 0.818051 0.579018 11.00000 0.03235 0.02348 = 0.05880 0.00239 -0.00652 -0.00571 O15 4 0.835457 0.422710 0.424656 11.00000 0.02937 0.03162 = 0.07136 0.00283 0.00976 -0.00284 O16 4 0.788132 0.254195 0.263971 11.00000 0.03685 0.07193 = 0.02456 0.00262 0.01068 0.00306 O18 4 0.523341 -0.133857 0.375179 11.00000 0.04034 0.02810 = 0.03037 -0.01038 0.00292 0.00426 O19 4 0.395360 -0.071848 0.517712 11.00000 0.03431 0.03140 = 0.04834 -0.00977 0.01048 -0.00798 N1 3 0.467353 0.478186 0.683403 11.00000 0.02761 0.02328 = 0.02133 -0.00125 0.00000 0.00156 N2 3 0.499442 0.621025 0.717976 11.00000 0.03504 0.02529 = 0.03090 -0.00446 -0.00155 -0.00218 N4 3 0.629156 0.814696 0.669123 11.00000 0.03507 0.02772 = 0.04491 -0.00053 -0.00452 -0.00199 N6 3 0.730326 0.674396 0.510416 11.00000 0.03038 0.02742 = 0.04356 0.00727 -0.00442 -0.00259 N14 3 0.772035 0.328564 0.370878 11.00000 0.02799 0.03193 = 0.03101 0.01114 0.00553 0.00430 N17 3 0.478725 -0.041830 0.456524 11.00000 0.02771 0.02495 = 0.03021 -0.00347 0.00087 0.00090 C3 1 0.590509 0.669271 0.651467 11.00000 0.03267 0.02312 = 0.03027 0.00164 -0.00432 -0.00034 C7 1 0.653408 0.580818 0.554962 11.00000 0.02694 0.02387 = 0.02953 0.00633 -0.00581 -0.00091 C8 1 0.620892 0.416588 0.525127 11.00000 0.02568 0.02290 = 0.02158 0.00536 -0.00080 0.00194 C9 1 0.670325 0.298622 0.442149 11.00000 0.02344 0.02807 = 0.02220 0.00696 0.00094 0.00100 C10 1 0.625734 0.149424 0.418948 11.00000 0.02867 0.02640 = 0.02096 0.00169 0.00078 0.00521 AFIX 43 H10 2 0.660006 0.072598 0.360961 11.00000 -1.20000 AFIX 0 C11 1 0.529584 0.115083 0.482698 11.00000 0.02860 0.02149 = 0.01927 0.00085 -0.00186 -0.00016 C12 1 0.477400 0.221807 0.568080 11.00000 0.02556 0.02233 = 0.02058 0.00361 0.00011 0.00150 AFIX 43 H12 2 0.411776 0.194420 0.611507 11.00000 -1.20000 AFIX 0 C13 1 0.524341 0.370997 0.588301 11.00000 0.02494 0.02216 = 0.01890 0.00245 -0.00282 0.00230 HKLF 4 REM 23sai_r074_g_a.res in Pca2(1) REM wR2 = 0.0882, GooF = S = 1.058, Restrained GooF = 1.057 for all data REM R1 = 0.0322 for 1884 Fo > 4sig(Fo) and 0.0326 for all 1908 data REM 182 parameters refined using 1 restraints END WGHT 0.0485 0.4434 REM Highest difference peak 0.262, deepest hole -0.202, 1-sigma level 0.046 Q1 1 0.7600 0.5583 0.4311 11.00000 0.05 0.26 Q2 1 0.7856 0.6883 0.4412 11.00000 0.05 0.23 Q3 1 0.6422 0.6938 0.5762 11.00000 0.05 0.22 Q4 1 0.3814 0.3206 0.7331 11.00000 0.05 0.18 Q5 1 0.6300 0.2555 0.4139 11.00000 0.05 0.17 Q6 1 0.7755 0.0783 0.2057 11.00000 0.05 0.16 ; _shelx_res_checksum 16697 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.211 _oxdiff_exptl_absorpt_empirical_full_min 0.865 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' 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 0.38264(15) 0.4257(2) 0.7343(2) 0.0270(4) Uani 1 1 d . . . . . O5 O 0.71603(16) 0.8181(2) 0.5790(3) 0.0382(5) Uani 1 1 d . . . . . O15 O 0.83546(17) 0.4227(2) 0.4247(3) 0.0441(6) Uani 1 1 d . . . . . O16 O 0.78813(18) 0.2542(3) 0.2640(3) 0.0444(6) Uani 1 1 d . . . . . O18 O 0.52334(16) -0.1339(2) 0.3752(2) 0.0329(5) Uani 1 1 d . . . . . O19 O 0.39536(17) -0.0718(2) 0.5177(3) 0.0380(5) Uani 1 1 d . . . . . N1 N 0.46735(17) 0.4782(3) 0.6834(2) 0.0241(5) Uani 1 1 d . . . . . N2 N 0.4994(2) 0.6210(3) 0.7180(3) 0.0304(5) Uani 1 1 d . . . . . N4 N 0.62916(19) 0.8147(3) 0.6691(3) 0.0359(6) Uani 1 1 d . . . . . N6 N 0.73033(19) 0.6744(3) 0.5104(3) 0.0338(6) Uani 1 1 d . . . . . N14 N 0.77204(18) 0.3286(3) 0.3709(3) 0.0303(5) Uani 1 1 d . . . . . N17 N 0.47873(17) -0.0418(3) 0.4565(3) 0.0276(5) Uani 1 1 d . . . . . C3 C 0.5905(2) 0.6693(3) 0.6515(3) 0.0287(6) Uani 1 1 d . . . . . C7 C 0.6534(2) 0.5808(3) 0.5550(3) 0.0268(6) Uani 1 1 d . . . . . C8 C 0.6209(2) 0.4166(3) 0.5251(3) 0.0234(5) Uani 1 1 d . . . . . C9 C 0.67032(19) 0.2986(3) 0.4421(3) 0.0246(5) Uani 1 1 d . . . . . C10 C 0.6257(2) 0.1494(3) 0.4189(3) 0.0253(5) Uani 1 1 d . . . . . H10 H 0.660006 0.072598 0.360961 0.030 Uiso 1 1 calc R U . . . C11 C 0.5296(2) 0.1151(3) 0.4827(3) 0.0231(5) Uani 1 1 d . . . . . C12 C 0.4774(2) 0.2218(3) 0.5681(3) 0.0228(5) Uani 1 1 d . . . . . H12 H 0.411776 0.194420 0.611507 0.027 Uiso 1 1 calc R U . . . C13 C 0.52434(19) 0.3710(3) 0.5883(3) 0.0220(5) Uani 1 1 d . . . . . 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 0.0274(9) 0.0282(9) 0.0256(10) -0.0006(8) 0.0056(7) -0.0008(7) O5 0.0324(10) 0.0235(9) 0.0588(15) 0.0024(9) -0.0065(10) -0.0057(7) O15 0.0294(9) 0.0316(10) 0.0714(18) 0.0028(11) 0.0098(11) -0.0028(8) O16 0.0368(11) 0.0719(16) 0.0246(11) 0.0026(12) 0.0107(9) 0.0031(10) O18 0.0403(11) 0.0281(9) 0.0304(12) -0.0104(8) 0.0029(9) 0.0043(8) O19 0.0343(10) 0.0314(10) 0.0483(15) -0.0098(10) 0.0105(10) -0.0080(8) N1 0.0276(10) 0.0233(10) 0.0213(11) -0.0013(9) 0.0000(9) 0.0016(8) N2 0.0350(12) 0.0253(11) 0.0309(13) -0.0045(9) -0.0015(10) -0.0022(9) N4 0.0351(12) 0.0277(11) 0.0449(16) -0.0005(11) -0.0045(12) -0.0020(9) N6 0.0304(12) 0.0274(11) 0.0436(17) 0.0073(11) -0.0044(11) -0.0026(9) N14 0.0280(11) 0.0319(11) 0.0310(14) 0.0111(10) 0.0055(10) 0.0043(9) N17 0.0277(11) 0.0250(11) 0.0302(14) -0.0035(9) 0.0009(9) 0.0009(8) C3 0.0327(13) 0.0231(11) 0.0303(16) 0.0016(11) -0.0043(12) -0.0003(10) C7 0.0269(12) 0.0239(12) 0.0295(16) 0.0063(10) -0.0058(10) -0.0009(9) C8 0.0257(11) 0.0229(11) 0.0216(13) 0.0054(9) -0.0008(10) 0.0019(9) C9 0.0234(11) 0.0281(11) 0.0222(14) 0.0070(10) 0.0009(10) 0.0010(9) C10 0.0287(12) 0.0264(11) 0.0210(14) 0.0017(10) 0.0008(11) 0.0052(9) C11 0.0286(12) 0.0215(12) 0.0193(13) 0.0008(9) -0.0019(10) -0.0002(9) C12 0.0256(11) 0.0223(11) 0.0206(13) 0.0036(10) 0.0001(9) 0.0015(9) C13 0.0249(12) 0.0222(11) 0.0189(13) 0.0024(10) -0.0028(10) 0.0023(9) 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' H H 0.0000 0.0000 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 -1 0 0.0266 -1 1 0 0.0171 -1 -1 0 0.0162 1 1 0 0.0145 0 0 -1 0.0847 0 0 1 0.0950 -1 0 0 0.0217 1 0 0 0.0235 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 N6 O5 N4 112.5(2) . . ? O1 N1 N2 118.9(2) . . ? O1 N1 C13 116.6(2) . . ? N2 N1 C13 124.5(2) . . ? N1 N2 C3 114.0(2) . . ? C3 N4 O5 103.1(2) . . ? C7 N6 O5 105.2(2) . . ? O15 N14 C9 118.2(3) . . ? O16 N14 O15 124.9(2) . . ? O16 N14 C9 116.9(2) . . ? O18 N17 C11 117.6(2) . . ? O19 N17 O18 124.6(2) . . ? O19 N17 C11 117.9(2) . . ? N2 C3 C7 128.0(2) . . ? N4 C3 N2 121.1(3) . . ? N4 C3 C7 110.8(3) . . ? N6 C7 C3 108.3(2) . . ? N6 C7 C8 134.4(3) . . ? C3 C7 C8 117.3(2) . . ? C9 C8 C7 130.0(2) . . ? C13 C8 C7 114.2(2) . . ? C13 C8 C9 115.9(2) . . ? C8 C9 N14 121.9(2) . . ? C10 C9 N14 115.4(2) . . ? C10 C9 C8 122.7(2) . . ? C9 C10 H10 121.1 . . ? C9 C10 C11 117.9(2) . . ? C11 C10 H10 121.1 . . ? C10 C11 N17 119.0(2) . . ? C12 C11 N17 117.9(2) . . ? C12 C11 C10 123.2(2) . . ? C11 C12 H12 121.3 . . ? C11 C12 C13 117.3(2) . . ? C13 C12 H12 121.3 . . ? C8 C13 N1 121.8(2) . . ? C12 C13 N1 115.1(2) . . ? C12 C13 C8 123.1(2) . . ? 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 N1 1.248(3) . ? O5 N4 1.392(4) . ? O5 N6 1.375(3) . ? O15 N14 1.229(4) . ? O16 N14 1.216(4) . ? O18 N17 1.228(3) . ? O19 N17 1.225(3) . ? N1 N2 1.296(3) . ? N1 C13 1.462(3) . ? N2 C3 1.368(4) . ? N4 C3 1.313(4) . ? N6 C7 1.310(4) . ? N14 C9 1.468(3) . ? N17 C11 1.473(3) . ? C3 C7 1.422(4) . ? C7 C8 1.452(3) . ? C8 C9 1.407(4) . ? C8 C13 1.406(3) . ? C9 C10 1.378(4) . ? C10 H10 0.9500 . ? C10 C11 1.382(4) . ? C11 C12 1.374(4) . ? C12 H12 0.9500 . ? C12 C13 1.386(3) . ? 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 O1 N1 N2 C3 -177.2(2) . . . . ? O1 N1 C13 C8 -179.7(2) . . . . ? O1 N1 C13 C12 -1.0(3) . . . . ? O5 N4 C3 N2 -176.6(3) . . . . ? O5 N4 C3 C7 1.6(3) . . . . ? O5 N6 C7 C3 0.5(3) . . . . ? O5 N6 C7 C8 179.2(3) . . . . ? O15 N14 C9 C8 30.1(4) . . . . ? O15 N14 C9 C10 -151.6(3) . . . . ? O16 N14 C9 C8 -151.7(3) . . . . ? O16 N14 C9 C10 26.6(4) . . . . ? O18 N17 C11 C10 -2.0(4) . . . . ? O18 N17 C11 C12 176.8(2) . . . . ? O19 N17 C11 C10 177.6(3) . . . . ? O19 N17 C11 C12 -3.6(4) . . . . ? N1 N2 C3 N4 175.8(3) . . . . ? N1 N2 C3 C7 -2.0(4) . . . . ? N2 N1 C13 C8 -0.2(4) . . . . ? N2 N1 C13 C12 178.5(3) . . . . ? N2 C3 C7 N6 176.6(3) . . . . ? N2 C3 C7 C8 -2.4(4) . . . . ? N4 O5 N6 C7 0.5(3) . . . . ? N4 C3 C7 N6 -1.4(3) . . . . ? N4 C3 C7 C8 179.6(2) . . . . ? N6 O5 N4 C3 -1.3(3) . . . . ? N6 C7 C8 C9 5.7(5) . . . . ? N6 C7 C8 C13 -173.4(3) . . . . ? N14 C9 C10 C11 -179.6(2) . . . . ? N17 C11 C12 C13 -178.0(2) . . . . ? C3 C7 C8 C9 -175.7(3) . . . . ? C3 C7 C8 C13 5.2(3) . . . . ? C7 C8 C9 N14 1.5(4) . . . . ? C7 C8 C9 C10 -176.7(3) . . . . ? C7 C8 C13 N1 -4.2(3) . . . . ? C7 C8 C13 C12 177.2(2) . . . . ? C8 C9 C10 C11 -1.3(4) . . . . ? C9 C8 C13 N1 176.5(2) . . . . ? C9 C8 C13 C12 -2.1(4) . . . . ? C9 C10 C11 N17 178.3(2) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? C11 C12 C13 N1 -178.2(2) . . . . ? C11 C12 C13 C8 0.5(4) . . . . ? C13 N1 N2 C3 3.3(4) . . . . ? C13 C8 C9 N14 -179.4(2) . . . . ? C13 C8 C9 C10 2.4(4) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.9988 -1.0000 -0.0012 0.0200 -0.2208 0.0189 -0.9988 1.0000 0.0012 -0.0200 0.2208 -0.0189 -1.0001 -1.0003 0.0005 0.1932 -0.0621 0.0912 1.0001 1.0003 -0.0005 -0.1932 0.0621 -0.0912 -0.0007 -0.0001 -1.0003 -0.0668 0.0063 0.1456 0.0007 0.0001 1.0003 0.0668 -0.0063 -0.1456 -0.9995 -0.0002 0.0008 0.0866 0.0793 0.0361 0.9995 0.0002 -0.0008 -0.0866 -0.0793 -0.0361