#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:59:50 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288796 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247735.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_7247735 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 H3 N5 O4' _chemical_formula_sum 'C8 H3 N5 O4' _chemical_formula_weight 233.15 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2023-04-11 _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.2846(2) _cell_length_b 9.99780(10) _cell_length_c 6.38630(10) _cell_measurement_reflns_used 5599 _cell_measurement_temperature 99.9(3) _cell_measurement_theta_max 76.9440 _cell_measurement_theta_min 5.3760 _cell_volume 912.06(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 99.9(3) _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 0.998 _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 -120.00 -64.00 0.50 1.00 -- -48.70-139.00 13.00 112 2 \w -122.00 -39.00 0.50 1.00 -- -48.70 -22.00 45.00 166 3 \w -28.00 26.00 0.50 1.00 -- -48.70 22.00-148.00 108 4 \w -156.00 -84.00 0.50 3.87 -- -86.25-103.00 -96.00 144 5 \w -90.00 -16.00 0.50 3.87 -- -86.25 131.00-100.00 148 6 \w 38.00 116.00 0.50 3.87 -- 107.75-131.00-171.00 156 7 \w 97.00 178.00 0.50 3.87 -- 107.75 22.00-148.00 162 8 \w 46.00 121.00 0.50 3.87 -- 107.75-139.00 13.00 150 9 \w 71.00 97.00 0.50 3.87 -- 107.75-103.00 -96.00 52 10 \w -22.00 25.00 0.50 1.00 -- 48.70 -19.00 -90.00 94 11 \w 37.00 71.00 0.50 3.87 -- 107.75 -61.00 30.00 68 12 \w 40.00 72.00 0.50 3.87 -- 107.75-125.00 -30.00 64 13 \w 49.00 75.00 0.50 3.87 -- 107.75 -95.00 30.00 52 14 \w 39.00 65.00 0.50 3.87 -- 107.75-103.00 -34.16 52 15 \w 36.00 69.00 0.50 3.87 -- 107.75 -95.00 90.00 66 16 \w 138.00 178.00 0.50 3.87 -- 107.75 45.00 -60.00 80 17 \w 83.00 109.00 0.50 3.87 -- 107.75-125.00 -30.00 52 18 \w 39.00 70.00 0.50 3.87 -- 107.75 -61.00-150.00 62 19 \w 147.00 177.00 0.50 3.87 -- 107.75 30.00 90.00 60 20 \w 41.00 69.00 0.50 3.87 -- 107.75 -61.00 -30.00 56 21 \w 69.00 106.00 0.50 3.87 -- 107.75-103.00 -34.16 74 22 \w 43.00 69.00 0.50 3.87 -- 107.75-125.00 0.00 52 23 \w 84.00 110.00 0.50 3.87 -- 107.75-125.00 90.00 52 24 \w 109.00 135.00 0.50 3.87 -- 107.75 45.00 27.49 52 25 \w 36.00 61.00 0.50 3.87 -- 107.75 -61.00 60.00 50 ; _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 -0.0776967000 _diffrn_orient_matrix_UB_12 0.1032424000 _diffrn_orient_matrix_UB_13 0.0430505000 _diffrn_orient_matrix_UB_21 -0.0747014000 _diffrn_orient_matrix_UB_22 -0.1056354000 _diffrn_orient_matrix_UB_23 -0.0537301000 _diffrn_orient_matrix_UB_31 -0.0030715000 _diffrn_orient_matrix_UB_32 -0.0438743000 _diffrn_orient_matrix_UB_33 0.2312489000 _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 0.0227 _diffrn_reflns_av_unetI/netI 0.0191 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 6846 _diffrn_reflns_point_group_measured_fraction_full 0.777 _diffrn_reflns_point_group_measured_fraction_max 0.758 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.814 _diffrn_reflns_theta_min 5.401 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.229 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.491 _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 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.129 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 396 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.10(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1472 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0238 _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^)+(0.0316P)^2^+0.2094P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.0625 _reflns_Friedel_coverage 0.389 _reflns_Friedel_fraction_full 0.507 _reflns_Friedel_fraction_max 0.468 _reflns_number_gt 1441 _reflns_number_total 1472 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00964e2.cif _cod_data_source_block Z461401 _cod_depositor_comments 'Adding full bibliography for 7247734--7247739.cif.' _cod_database_code 7247735 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C8H3N5O4 _chemical_oxdiff_usercomment Z461401 _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 0.976 _shelx_estimated_absorpt_t_min 0.551 _reflns_odcompleteness_completeness 98.40 _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: C8(H8), C10(H10), C11(H11) ; _shelx_res_file ; TITL 23ndi_r043_g_a.res in Pna2(1) 23ndi_r043_g.res created by SHELXL-2018/3 at 16:51:30 on 11-Apr-2023 REM Old TITL 23NDI_R043_g in Pna2(1) REM SHELXT solution in Pna2(1) REM R1 0.077, Rweak 0.016, Alpha 0.000, Orientation as input REM Flack x = 0.186 ( 0.109 ) from Parsons' quotients REM Formula found by SHELXT: C13 O4 CELL 1.54184 14.2846 9.9978 6.3863 90 90 90 ZERR 4 0.0002 0.0001 0.0001 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H N O UNIT 32 12 20 16 L.S. 11 PLAN 5 SIZE 0.02 0.04 0.55 TEMP -173 CONF BOND $H list 4 MORE -1 fmap 2 53 acta REM REM REM WGHT 0.031600 0.209400 FVAR 1.09745 O2 4 0.612763 0.883306 0.683328 11.00000 0.02544 0.04072 = 0.03780 -0.00596 -0.00262 -0.01171 O6 4 0.389469 0.457454 0.910548 11.00000 0.02866 0.02369 = 0.02364 0.00648 -0.00278 -0.00053 O15 4 0.169635 0.364579 0.376634 11.00000 0.02839 0.02236 = 0.02579 0.00491 -0.00289 -0.00653 O16 4 0.171779 0.478251 0.088576 11.00000 0.04113 0.03000 = 0.02520 0.00671 -0.01244 -0.00964 N1 3 0.545873 0.867650 0.525233 11.00000 0.02565 0.03103 = 0.03084 -0.00542 0.00211 -0.00740 N3 3 0.602459 0.791127 0.842003 11.00000 0.02475 0.03525 = 0.03697 -0.00494 -0.00449 -0.00508 N5 3 0.494928 0.616485 0.901202 11.00000 0.02054 0.02708 = 0.02718 -0.00197 -0.00613 0.00261 N6 3 0.424631 0.554562 0.815311 11.00000 0.01950 0.02259 = 0.02093 0.00021 -0.00217 0.00340 N14 3 0.198768 0.455958 0.265272 11.00000 0.02114 0.01919 = 0.02364 -0.00032 -0.00281 -0.00089 C4 1 0.529491 0.720537 0.783097 11.00000 0.01828 0.02582 = 0.02901 -0.00503 -0.00035 0.00185 C7 1 0.383047 0.590268 0.614582 11.00000 0.01760 0.01919 = 0.01739 -0.00046 0.00055 0.00438 C8 1 0.310142 0.510306 0.543037 11.00000 0.01831 0.01801 = 0.02111 0.00149 0.00182 0.00141 AFIX 43 H8 2 0.287360 0.436729 0.622182 11.00000 -1.20000 AFIX 0 C9 1 0.272762 0.543494 0.351387 11.00000 0.01854 0.01845 = 0.02050 -0.00169 0.00059 -0.00013 C10 1 0.301448 0.652454 0.232662 11.00000 0.02600 0.02039 = 0.02045 0.00110 -0.00221 0.00078 AFIX 43 H10 2 0.271862 0.672884 0.103332 11.00000 -1.20000 AFIX 0 C11 1 0.374097 0.730474 0.307218 11.00000 0.02803 0.01954 = 0.02005 0.00064 0.00261 -0.00221 AFIX 43 H11 2 0.395160 0.805487 0.229000 11.00000 -1.20000 AFIX 0 C12 1 0.416396 0.698557 0.498008 11.00000 0.01913 0.01859 = 0.02271 -0.00164 0.00293 0.00143 C13 1 0.495343 0.766871 0.590174 11.00000 0.02030 0.02132 = 0.02373 -0.00407 0.00493 0.00030 HKLF 4 REM 23ndi_r043_g_a.res in Pna2(1) REM wR2 = 0.0625, GooF = S = 1.075, Restrained GooF = 1.075 for all data REM R1 = 0.0238 for 1441 Fo > 4sig(Fo) and 0.0243 for all 1472 data REM 154 parameters refined using 1 restraints END WGHT 0.0316 0.2094 REM Highest difference peak 0.129, deepest hole -0.154, 1-sigma level 0.035 Q1 1 0.2406 0.5038 0.3191 11.00000 0.05 0.13 Q2 1 0.2973 0.4139 0.6426 11.00000 0.05 0.12 Q3 1 0.2841 0.5439 0.4474 11.00000 0.05 0.12 Q4 1 0.1801 0.7056 0.0635 11.00000 0.05 0.12 Q5 1 0.5029 0.6170 1.0614 11.00000 0.05 0.11 ; _shelx_res_checksum 8460 _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 1.150 _oxdiff_exptl_absorpt_empirical_full_min 0.793 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, 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 0.61276(10) 0.88331(15) 0.6833(3) 0.0347(4) Uani 1 1 d . . . . . O6 O 0.38947(9) 0.45745(13) 0.9105(2) 0.0253(3) Uani 1 1 d . . . . . O15 O 0.16963(9) 0.36458(13) 0.3766(3) 0.0255(3) Uani 1 1 d . . . . . O16 O 0.17178(10) 0.47825(14) 0.0886(3) 0.0321(4) Uani 1 1 d . . . . . N1 N 0.54587(11) 0.86765(17) 0.5252(3) 0.0292(4) Uani 1 1 d . . . . . N3 N 0.60246(11) 0.79113(18) 0.8420(3) 0.0323(4) Uani 1 1 d . . . . . N5 N 0.49493(11) 0.61649(16) 0.9012(3) 0.0249(3) Uani 1 1 d . . . . . N6 N 0.42463(10) 0.55456(15) 0.8153(3) 0.0210(3) Uani 1 1 d . . . . . N14 N 0.19877(10) 0.45596(14) 0.2653(3) 0.0213(3) Uani 1 1 d . . . . . C4 C 0.52949(12) 0.72054(18) 0.7831(3) 0.0244(4) Uani 1 1 d . . . . . C7 C 0.38305(11) 0.59027(17) 0.6146(3) 0.0181(4) Uani 1 1 d . . . . . C8 C 0.31014(11) 0.51031(17) 0.5430(3) 0.0191(4) Uani 1 1 d . . . . . H8 H 0.287360 0.436729 0.622182 0.023 Uiso 1 1 calc R U . . . C9 C 0.27276(11) 0.54349(17) 0.3514(3) 0.0192(4) Uani 1 1 d . . . . . C10 C 0.30145(13) 0.65245(18) 0.2327(3) 0.0223(4) Uani 1 1 d . . . . . H10 H 0.271862 0.672884 0.103332 0.027 Uiso 1 1 calc R U . . . C11 C 0.37410(12) 0.73047(18) 0.3072(3) 0.0225(4) Uani 1 1 d . . . . . H11 H 0.395160 0.805487 0.229000 0.027 Uiso 1 1 calc R U . . . C12 C 0.41640(12) 0.69856(17) 0.4980(3) 0.0201(4) Uani 1 1 d . . . . . C13 C 0.49534(12) 0.76687(17) 0.5902(3) 0.0218(4) 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 O2 0.0254(6) 0.0407(8) 0.0378(9) -0.0060(8) -0.0026(6) -0.0117(6) O6 0.0287(6) 0.0237(6) 0.0236(7) 0.0065(6) -0.0028(6) -0.0005(5) O15 0.0284(6) 0.0224(6) 0.0258(7) 0.0049(6) -0.0029(6) -0.0065(5) O16 0.0411(7) 0.0300(7) 0.0252(8) 0.0067(7) -0.0124(7) -0.0096(6) N1 0.0256(7) 0.0310(8) 0.0308(10) -0.0054(8) 0.0021(8) -0.0074(6) N3 0.0247(7) 0.0353(9) 0.0370(11) -0.0049(8) -0.0045(8) -0.0051(7) N5 0.0205(6) 0.0271(8) 0.0272(9) -0.0020(7) -0.0061(7) 0.0026(6) N6 0.0195(6) 0.0226(7) 0.0209(8) 0.0002(7) -0.0022(6) 0.0034(6) N14 0.0211(6) 0.0192(7) 0.0236(8) -0.0003(7) -0.0028(7) -0.0009(6) C4 0.0183(7) 0.0258(9) 0.0290(11) -0.0050(8) -0.0004(8) 0.0019(7) C7 0.0176(6) 0.0192(8) 0.0174(9) -0.0005(7) 0.0005(7) 0.0044(6) C8 0.0183(7) 0.0180(7) 0.0211(10) 0.0015(7) 0.0018(7) 0.0014(6) C9 0.0185(7) 0.0184(7) 0.0205(9) -0.0017(7) 0.0006(7) -0.0001(6) C10 0.0260(8) 0.0204(8) 0.0205(10) 0.0011(7) -0.0022(8) 0.0008(7) C11 0.0280(8) 0.0195(8) 0.0200(10) 0.0006(8) 0.0026(8) -0.0022(7) C12 0.0191(7) 0.0186(8) 0.0227(9) -0.0016(8) 0.0029(7) 0.0014(6) C13 0.0203(7) 0.0213(8) 0.0237(10) -0.0041(8) 0.0049(8) 0.0003(6) 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 0.0120 -1 -1 0 0.0120 0 0 1 0.2971 0 0 -1 0.2484 0 1 0 0.0145 0 -1 0 0.0187 -1 1 0 0.0078 1 -1 0 0.0180 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 112.52(13) . . ? C13 N1 O2 103.56(17) . . ? C4 N3 O2 103.50(17) . . ? N6 N5 C4 113.92(17) . . ? O6 N6 N5 118.31(16) . . ? O6 N6 C7 117.01(15) . . ? N5 N6 C7 124.68(16) . . ? O15 N14 C9 117.80(15) . . ? O16 N14 O15 124.52(16) . . ? O16 N14 C9 117.68(15) . . ? N3 C4 N5 122.25(19) . . ? N3 C4 C13 110.47(18) . . ? N5 C4 C13 127.28(17) . . ? C8 C7 N6 116.98(16) . . ? C8 C7 C12 121.72(17) . . ? C12 C7 N6 121.29(16) . . ? C7 C8 H8 121.8 . . ? C9 C8 C7 116.39(16) . . ? C9 C8 H8 121.8 . . ? C8 C9 N14 117.75(15) . . ? C8 C9 C10 124.07(17) . . ? C10 C9 N14 118.17(16) . . ? C9 C10 H10 120.8 . . ? C11 C10 C9 118.41(18) . . ? C11 C10 H10 120.8 . . ? C10 C11 H11 120.1 . . ? C10 C11 C12 119.74(17) . . ? C12 C11 H11 120.1 . . ? C7 C12 C13 114.55(17) . . ? C11 C12 C7 119.61(16) . . ? C11 C12 C13 125.83(17) . . ? N1 C13 C4 109.94(17) . . ? N1 C13 C12 131.81(19) . . ? C4 C13 C12 118.24(16) . . ? 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 1.399(2) . ? O2 N3 1.378(3) . ? O6 N6 1.251(2) . ? O15 N14 1.230(2) . ? O16 N14 1.213(2) . ? N1 C13 1.307(2) . ? N3 C4 1.314(2) . ? N5 N6 1.301(2) . ? N5 C4 1.377(3) . ? N6 C7 1.457(2) . ? N14 C9 1.478(2) . ? C4 C13 1.404(3) . ? C7 C8 1.390(2) . ? C7 C12 1.398(3) . ? C8 H8 0.9500 . ? C8 C9 1.376(3) . ? C9 C10 1.389(3) . ? C10 H10 0.9500 . ? C10 C11 1.383(3) . ? C11 H11 0.9500 . ? C11 C12 1.397(3) . ? C12 C13 1.444(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 N1 C13 C4 -0.05(19) . . . . ? O2 N1 C13 C12 -178.56(18) . . . . ? O2 N3 C4 N5 -179.61(17) . . . . ? O2 N3 C4 C13 0.6(2) . . . . ? O6 N6 C7 C8 -2.2(2) . . . . ? O6 N6 C7 C12 178.94(15) . . . . ? O15 N14 C9 C8 5.6(2) . . . . ? O15 N14 C9 C10 -175.60(17) . . . . ? O16 N14 C9 C8 -173.56(17) . . . . ? O16 N14 C9 C10 5.3(2) . . . . ? N1 O2 N3 C4 -0.6(2) . . . . ? N3 O2 N1 C13 0.4(2) . . . . ? N3 C4 C13 N1 -0.3(2) . . . . ? N3 C4 C13 C12 178.40(16) . . . . ? N5 N6 C7 C8 177.92(16) . . . . ? N5 N6 C7 C12 -0.9(3) . . . . ? N5 C4 C13 N1 179.84(17) . . . . ? N5 C4 C13 C12 -1.4(3) . . . . ? N6 N5 C4 N3 -177.55(17) . . . . ? N6 N5 C4 C13 2.3(3) . . . . ? N6 C7 C8 C9 -178.74(15) . . . . ? N6 C7 C12 C11 -179.37(15) . . . . ? N6 C7 C12 C13 1.7(2) . . . . ? N14 C9 C10 C11 -176.56(16) . . . . ? C4 N5 N6 O6 179.12(15) . . . . ? C4 N5 N6 C7 -1.1(2) . . . . ? C7 C8 C9 N14 176.62(15) . . . . ? C7 C8 C9 C10 -2.2(3) . . . . ? C7 C12 C13 N1 177.76(18) . . . . ? C7 C12 C13 C4 -0.6(2) . . . . ? C8 C7 C12 C11 1.9(3) . . . . ? C8 C7 C12 C13 -177.06(16) . . . . ? C8 C9 C10 C11 2.2(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C7 -1.8(3) . . . . ? C10 C11 C12 C13 176.97(17) . . . . ? C11 C12 C13 N1 -1.1(3) . . . . ? C11 C12 C13 C4 -179.50(16) . . . . ? C12 C7 C8 C9 0.1(2) . . . . ? 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 0.9984 0.9997 0.0001 0.0256 -0.1802 -0.0469 -0.9984 -0.9997 -0.0001 -0.0256 0.1802 0.0469 0.0003 -0.0007 0.9998 0.0429 -0.0537 0.2312 -0.0003 0.0007 -0.9998 -0.0429 0.0537 -0.2312 -0.0009 0.9990 -0.0002 0.1032 -0.1055 -0.0439 0.0009 -0.9990 0.0002 -0.1032 0.1055 0.0439 -1.0001 0.9983 -0.0004 0.1808 -0.0307 -0.0408 1.0001 -0.9983 0.0004 -0.1808 0.0307 0.0408