#------------------------------------------------------------------------------ #$Date: 2023-11-16 01:37:55 +0200 (Thu, 16 Nov 2023) $ #$Revision: 287627 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247734.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_7247734 loop_ _publ_author_name 'Baraboshkin, Nikita' 'Zelenov, Victor Petrovich' '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_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00964E _journal_year 2023 _chemical_formula_moiety 'C8 H4 N4 O2' _chemical_formula_sum 'C8 H4 N4 O2' _chemical_formula_weight 188.15 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2023-02-15 _audit_creation_method ; Olex2 1.3 (compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938) ; _audit_update_record ; 2023-08-15 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.3886(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.74397(15) _cell_length_b 5.37413(10) _cell_length_c 18.7390(3) _cell_measurement_reflns_used 5623 _cell_measurement_temperature 99.97(15) _cell_measurement_theta_max 76.5310 _cell_measurement_theta_min 5.7650 _cell_volume 769.42(2) _computing_cell_refinement 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _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 99.97(15) _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 0.996 _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 40.00 79.00 0.50 0.25 -- 107.75-125.00 0.00 78 2 \w 39.00 111.00 0.50 0.25 -- 107.75-125.00-120.00 144 3 \w -62.00 24.00 0.50 0.08 -- -48.68 55.00 0.00 172 4 \w -51.00 -14.00 0.50 0.25 -- -86.25 45.00-180.00 74 5 \w -63.00 -14.00 0.50 0.25 -- -86.25 55.00 0.00 98 6 \w 61.00 87.00 0.50 0.25 -- 107.75-125.00 90.00 52 7 \w 45.00 77.00 0.50 0.25 -- 107.75-125.00 120.00 64 8 \w 82.00 109.00 0.50 0.25 -- 107.75-125.00 120.00 54 9 \w 36.00 105.00 0.50 0.25 -- 107.75 -95.00 -60.00 138 10 \w 69.00 94.00 0.50 0.25 -- 107.75 -95.00-120.00 50 11 \w 42.00 67.00 0.50 0.25 -- 107.75-125.00-180.00 50 12 \w 36.00 62.00 0.50 0.25 -- 107.75 -95.00-120.00 52 13 \w 40.00 66.00 0.50 0.25 -- 107.75 -83.00 -27.90 52 14 \w 106.00 132.00 0.50 0.25 -- 107.75 -83.00 -27.90 52 15 \w 51.00 90.00 0.50 0.25 -- 107.75 -77.00 30.00 78 16 \w 38.00 64.00 0.50 0.25 -- 107.75 -61.00 150.00 52 17 \w 36.00 71.00 0.50 0.25 -- 107.75 -61.00 0.00 70 18 \w 40.00 71.00 0.50 0.25 -- 107.75 -61.00-120.00 62 19 \w 36.00 63.00 0.50 0.25 -- 107.75 -55.00-142.00 54 20 \w 36.00 166.00 0.50 0.25 -- 107.75 0.00 0.00 260 21 \w 97.00 178.00 0.50 0.25 -- 107.75 45.00 -60.00 162 22 \w 86.00 133.00 0.50 0.25 -- 107.75 77.00 0.00 94 23 \w 95.00 178.00 0.50 0.25 -- 107.75 55.00 0.00 166 24 \w 120.00 146.00 0.50 0.25 -- 107.75 30.00 -30.00 52 25 \w 110.00 136.00 0.50 0.25 -- 107.75 30.00 90.00 52 26 \w 97.00 146.00 0.50 0.25 -- 107.75 45.00 120.00 98 27 \w 36.00 120.00 0.50 0.08 -- 48.68 55.00 0.00 168 28 \w 96.00 128.00 0.50 0.25 -- 107.75 125.00-120.00 64 29 \w -22.00 62.00 0.50 0.08 -- 48.68 -55.00-142.00 168 30 \w 137.00 176.00 0.50 0.25 -- 107.75 125.00-120.00 78 31 \w -25.00 26.00 0.50 0.08 -- 48.68 -19.00 30.00 102 32 \w -120.00 -35.00 0.50 0.08 -- -48.68 -55.00-142.00 170 33 \w -158.00 -73.00 0.50 0.25 -- -86.25 -55.00-142.00 170 34 \w -118.00 -73.00 0.50 0.08 -- -48.68-125.00-180.00 90 ; _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 -0.0134039000 _diffrn_orient_matrix_UB_12 0.0603290000 _diffrn_orient_matrix_UB_13 -0.0810875000 _diffrn_orient_matrix_UB_21 0.1525398000 _diffrn_orient_matrix_UB_22 -0.1796052000 _diffrn_orient_matrix_UB_23 -0.0051457000 _diffrn_orient_matrix_UB_31 -0.1311815000 _diffrn_orient_matrix_UB_32 -0.2150304000 _diffrn_orient_matrix_UB_33 -0.0185772000 _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 0.0311 _diffrn_reflns_av_unetI/netI 0.0201 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 8675 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.623 _diffrn_reflns_theta_min 4.784 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.051 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.603 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022) 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 colorless _exptl_crystal_density_diffrn 1.624 _exptl_crystal_description prism _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.212 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.059 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1627 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0382 _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^)+(0.0603P)^2^+0.2643P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1047 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1531 _reflns_number_total 1627 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00964e2.cif _cod_data_source_block Z-458101 _cod_database_code 7247734 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C8H4N4O2 _chemical_oxdiff_usercomment Z458101 _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 0.949 _shelx_estimated_absorpt_t_min 0.655 _reflns_odcompleteness_completeness 98.64 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 78.52 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C11(H11), C8(H8), C10(H10), C9(H9) ; _shelx_res_file ; TITL 23sai_r009_g_a.res in P2(1)/c 23sai_r009_g.res created by SHELXL-2018/3 at 10:54:18 on 15-Feb-2023 REM Old TITL 23SAI_R009_G in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.120, Rweak 0.063, Alpha 0.016, Orientation as input REM Formula found by SHELXT: C12 O2 CELL 1.54184 7.74397 5.37413 18.739 90 99.3886 90 ZERR 4 0.00015 0.0001 0.0003 0 0.0018 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 32 16 16 8 L.S. 4 0 0 PLAN 5 SIZE 0.05 0.14 0.44 TEMP -173 CONF BOND $H list 4 MORE -1 fmap 2 53 acta REM REM REM WGHT 0.060300 0.264300 FVAR 0.75515 O2 4 0.261775 0.497588 0.434136 11.00000 0.02620 0.04252 = 0.03447 -0.00514 0.00986 0.00501 O6 4 0.727464 0.690642 0.247157 11.00000 0.03647 0.03096 = 0.02614 0.00697 0.00726 -0.00431 N6 3 0.652377 0.599497 0.295168 11.00000 0.02642 0.02382 = 0.02149 0.00074 0.00265 -0.00154 N5 3 0.506925 0.700339 0.306711 11.00000 0.02761 0.02369 = 0.02733 -0.00041 0.00099 0.00320 N1 3 0.392964 0.318272 0.446262 11.00000 0.02521 0.03656 = 0.02768 -0.00326 0.00782 0.00242 N3 3 0.287985 0.663395 0.380589 11.00000 0.02744 0.03390 = 0.03500 -0.00483 0.00418 0.00564 C12 1 0.660384 0.268051 0.388240 11.00000 0.02326 0.02462 = 0.01794 -0.00307 0.00277 0.00043 C7 1 0.737326 0.386378 0.334628 11.00000 0.02420 0.02196 = 0.01946 -0.00158 0.00229 0.00017 C13 1 0.497712 0.375014 0.400737 11.00000 0.02414 0.02584 = 0.02020 -0.00319 0.00387 -0.00050 C11 1 0.744734 0.065552 0.425384 11.00000 0.03001 0.02622 = 0.01975 0.00030 0.00387 0.00073 AFIX 43 H11 2 0.694269 -0.015851 0.462004 11.00000 -1.20000 AFIX 0 C4 1 0.433183 0.586414 0.359962 11.00000 0.02444 0.02551 = 0.02477 -0.00499 0.00131 0.00171 C8 1 0.896949 0.305890 0.317977 11.00000 0.02586 0.03235 = 0.02148 -0.00128 0.00618 -0.00034 AFIX 43 H8 2 0.948767 0.387563 0.281782 11.00000 -1.20000 AFIX 0 C10 1 0.902581 -0.015419 0.408331 11.00000 0.03102 0.02644 = 0.02210 -0.00169 -0.00140 0.00677 AFIX 43 H10 2 0.960033 -0.154328 0.433046 11.00000 -1.20000 AFIX 0 C9 1 0.978210 0.105339 0.355078 11.00000 0.02496 0.03485 = 0.02452 -0.00529 0.00411 0.00578 AFIX 43 H9 2 1.087195 0.048402 0.344287 11.00000 -1.20000 AFIX 0 HKLF 4 REM 23sai_r009_g_a.res in P2(1)/c REM wR2 = 0.1047, GooF = S = 1.041, Restrained GooF = 1.041 for all data REM R1 = 0.0382 for 1531 Fo > 4sig(Fo) and 0.0398 for all 1627 data REM 127 parameters refined using 0 restraints END WGHT 0.0600 0.2643 REM Highest difference peak 0.212, deepest hole -0.333, 1-sigma level 0.059 Q1 1 0.4803 0.4934 0.3810 11.00000 0.05 0.21 Q2 1 0.4500 0.8662 0.2994 11.00000 0.05 0.17 Q3 1 0.7010 0.9117 0.2544 11.00000 0.05 0.16 Q4 1 0.4975 0.8609 0.2836 11.00000 0.05 0.16 Q5 1 0.7053 0.3411 0.3608 11.00000 0.05 0.15 ; _shelx_res_checksum 3329 _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 1.199 _oxdiff_exptl_absorpt_empirical_full_min 0.871 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' 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 O2 O 0.26178(12) 0.4976(2) 0.43414(5) 0.0338(3) Uani 1 1 d . . . . . O6 O 0.72746(13) 0.69064(18) 0.24716(5) 0.0309(2) Uani 1 1 d . . . . . N6 N 0.65238(13) 0.59950(19) 0.29517(5) 0.0241(2) Uani 1 1 d . . . . . N5 N 0.50692(14) 0.70034(19) 0.30671(6) 0.0266(3) Uani 1 1 d . . . . . N1 N 0.39296(14) 0.3183(2) 0.44626(6) 0.0294(3) Uani 1 1 d . . . . . N3 N 0.28798(15) 0.6634(2) 0.38059(6) 0.0322(3) Uani 1 1 d . . . . . C12 C 0.66038(15) 0.2681(2) 0.38824(6) 0.0220(3) Uani 1 1 d . . . . . C7 C 0.73733(15) 0.3864(2) 0.33463(6) 0.0220(3) Uani 1 1 d . . . . . C13 C 0.49771(16) 0.3750(2) 0.40074(6) 0.0234(3) Uani 1 1 d . . . . . C11 C 0.74473(16) 0.0656(2) 0.42538(6) 0.0254(3) Uani 1 1 d . . . . . H11 H 0.694269 -0.015851 0.462004 0.030 Uiso 1 1 calc R U . . . C4 C 0.43318(16) 0.5864(2) 0.35996(7) 0.0252(3) Uani 1 1 d . . . . . C8 C 0.89695(16) 0.3059(2) 0.31798(6) 0.0263(3) Uani 1 1 d . . . . . H8 H 0.948767 0.387563 0.281782 0.032 Uiso 1 1 calc R U . . . C10 C 0.90258(17) -0.0154(2) 0.40833(6) 0.0272(3) Uani 1 1 d . . . . . H10 H 0.960033 -0.154328 0.433046 0.033 Uiso 1 1 calc R U . . . C9 C 0.97821(16) 0.1053(3) 0.35508(7) 0.0281(3) Uani 1 1 d . . . . . H9 H 1.087195 0.048402 0.344287 0.034 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 O2 0.0262(5) 0.0425(6) 0.0345(5) -0.0051(4) 0.0099(4) 0.0050(4) O6 0.0365(5) 0.0310(5) 0.0261(5) 0.0070(4) 0.0073(4) -0.0043(4) N6 0.0264(5) 0.0238(5) 0.0215(5) 0.0007(4) 0.0026(4) -0.0015(4) N5 0.0276(5) 0.0237(5) 0.0273(5) -0.0004(4) 0.0010(4) 0.0032(4) N1 0.0252(5) 0.0366(6) 0.0277(5) -0.0033(4) 0.0078(4) 0.0024(4) N3 0.0274(6) 0.0339(6) 0.0350(6) -0.0048(5) 0.0042(4) 0.0056(5) C12 0.0233(6) 0.0246(6) 0.0179(5) -0.0031(4) 0.0028(4) 0.0004(5) C7 0.0242(6) 0.0220(6) 0.0195(5) -0.0016(4) 0.0023(4) 0.0002(5) C13 0.0241(6) 0.0258(6) 0.0202(5) -0.0032(4) 0.0039(4) -0.0005(5) C11 0.0300(6) 0.0262(6) 0.0198(5) 0.0003(4) 0.0039(4) 0.0007(5) C4 0.0244(6) 0.0255(6) 0.0248(6) -0.0050(5) 0.0013(4) 0.0017(5) C8 0.0259(6) 0.0323(7) 0.0215(6) -0.0013(5) 0.0062(4) -0.0003(5) C10 0.0310(6) 0.0264(6) 0.0221(6) -0.0017(5) -0.0014(5) 0.0068(5) C9 0.0250(6) 0.0349(7) 0.0245(6) -0.0053(5) 0.0041(5) 0.0058(5) 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 0 0 -1 0.0701 0 0 1 0.0678 1 0 0 0.0253 -1 0 0 0.0206 0 -1 0 0.1924 0 1 0 0.2435 1 0 -1 0.0395 -1 0 1 0.0206 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 N3 O2 N1 112.05(9) . . ? O6 N6 N5 118.34(10) . . ? O6 N6 C7 116.64(10) . . ? N5 N6 C7 125.02(10) . . ? N6 N5 C4 114.20(10) . . ? C13 N1 O2 104.26(10) . . ? C4 N3 O2 104.17(10) . . ? C7 C12 C13 114.93(11) . . ? C11 C12 C7 119.49(11) . . ? C11 C12 C13 125.57(11) . . ? C12 C7 N6 120.65(11) . . ? C8 C7 N6 118.25(11) . . ? C8 C7 C12 121.10(11) . . ? N1 C13 C12 131.84(12) . . ? N1 C13 C4 109.77(11) . . ? C4 C13 C12 118.35(11) . . ? C12 C11 H11 120.3 . . ? C10 C11 C12 119.31(12) . . ? C10 C11 H11 120.3 . . ? N5 C4 C13 126.81(11) . . ? N3 C4 N5 123.44(12) . . ? N3 C4 C13 109.75(11) . . ? C7 C8 H8 120.7 . . ? C9 C8 C7 118.63(11) . . ? C9 C8 H8 120.7 . . ? C11 C10 H10 119.7 . . ? C11 C10 C9 120.55(12) . . ? C9 C10 H10 119.7 . . ? C8 C9 C10 120.92(11) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? 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 O2 N1 1.3918(15) . ? O2 N3 1.3815(15) . ? O6 N6 1.2483(13) . ? N6 N5 1.2995(15) . ? N6 C7 1.4603(15) . ? N5 C4 1.3721(17) . ? N1 C13 1.3056(16) . ? N3 C4 1.3140(17) . ? C12 C7 1.4014(16) . ? C12 C13 1.4382(17) . ? C12 C11 1.3954(17) . ? C7 C8 1.3922(17) . ? C13 C4 1.4141(17) . ? C11 H11 0.9500 . ? C11 C10 1.3831(18) . ? C8 H8 0.9500 . ? C8 C9 1.3778(18) . ? C10 H10 0.9500 . ? C10 C9 1.3967(18) . ? C9 H9 0.9500 . ? 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 N1 C13 C12 177.34(12) . . . . ? O2 N1 C13 C4 -0.39(13) . . . . ? O2 N3 C4 N5 179.80(10) . . . . ? O2 N3 C4 C13 -0.40(13) . . . . ? O6 N6 N5 C4 179.45(10) . . . . ? O6 N6 C7 C12 -178.41(10) . . . . ? O6 N6 C7 C8 2.14(16) . . . . ? N6 N5 C4 N3 178.63(11) . . . . ? N6 N5 C4 C13 -1.13(18) . . . . ? N6 C7 C8 C9 179.84(10) . . . . ? N5 N6 C7 C12 2.07(18) . . . . ? N5 N6 C7 C8 -177.38(11) . . . . ? N1 O2 N3 C4 0.17(13) . . . . ? N1 C13 C4 N5 -179.68(11) . . . . ? N1 C13 C4 N3 0.53(15) . . . . ? N3 O2 N1 C13 0.15(13) . . . . ? C12 C7 C8 C9 0.39(18) . . . . ? C12 C13 C4 N5 2.24(19) . . . . ? C12 C13 C4 N3 -177.55(10) . . . . ? C12 C11 C10 C9 0.69(19) . . . . ? C7 N6 N5 C4 -1.04(17) . . . . ? C7 C12 C13 N1 -178.63(12) . . . . ? C7 C12 C13 C4 -1.06(16) . . . . ? C7 C12 C11 C10 -0.29(18) . . . . ? C7 C8 C9 C10 0.01(18) . . . . ? C13 C12 C7 N6 -0.83(16) . . . . ? C13 C12 C7 C8 178.60(10) . . . . ? C13 C12 C11 C10 -179.01(11) . . . . ? C11 C12 C7 N6 -179.68(10) . . . . ? C11 C12 C7 C8 -0.25(18) . . . . ? C11 C12 C13 N1 0.1(2) . . . . ? C11 C12 C13 C4 177.72(11) . . . . ? C11 C10 C9 C8 -0.56(19) . . . . ? 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 0.0002 -0.0000 -0.9997 0.0811 0.0052 0.0186 -0.0002 0.0000 0.9997 -0.0811 -0.0052 -0.0186 0.9994 0.0004 0.0018 -0.0135 0.1524 -0.1312 -0.9994 -0.0004 -0.0018 0.0135 -0.1524 0.1312 -0.0005 -0.9995 0.0001 -0.0603 0.1794 0.2150 0.0005 0.9995 -0.0001 0.0603 -0.1794 -0.2150 0.9996 0.0004 -0.9979 0.0675 0.1576 -0.1127 -0.9996 -0.0004 0.9979 -0.0675 -0.1576 0.1127