#------------------------------------------------------------------------------ #$Date: 2023-11-16 01:37:55 +0200 (Thu, 16 Nov 2023) $ #$Revision: 287627 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247736.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_7247736 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 H3 N5 O4' _chemical_formula_sum 'C8 H3 N5 O4' _chemical_formula_weight 233.15 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2023-06-11 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _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 8 _cell_length_a 8.6598(2) _cell_length_b 12.7026(3) _cell_length_c 15.5750(4) _cell_measurement_reflns_used 7039 _cell_measurement_temperature 100.0(4) _cell_measurement_theta_max 77.3860 _cell_measurement_theta_min 2.7580 _cell_volume 1713.28(7) _computing_cell_refinement 'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (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 100.0(4) _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 -121.00 -53.00 0.50 1.50 -- -48.70 -36.00-102.00 136 2 \w -97.00 -53.00 0.50 1.50 -- -48.70-154.00-121.00 88 3 \w -65.00 -15.00 0.50 1.50 -- -48.70 86.00-129.00 100 4 \w 133.00 159.00 0.50 6.00 -- 107.75 36.00 53.00 52 5 \w 105.00 130.00 0.50 6.00 -- 107.75 86.00-129.00 50 6 \w 49.00 98.00 0.50 6.00 -- 107.75 -86.00 112.00 98 7 \w 61.00 106.00 0.50 6.00 -- 107.75-121.00 36.00 90 8 \w 35.00 93.00 0.50 1.50 -- 48.70-125.00 -60.00 116 9 \w 42.00 68.00 0.50 6.00 -- 107.75 -61.00 150.00 52 10 \w 36.00 69.00 0.50 6.00 -- 107.75 -61.00-120.00 66 11 \w 100.00 127.00 0.50 6.00 -- 107.75 125.00 150.00 54 12 \w 146.00 172.00 0.50 6.00 -- 107.75 125.00 150.00 52 13 \w 37.00 80.00 0.50 6.00 -- 107.75 -77.00-180.00 86 14 \w 40.00 65.00 0.50 6.00 -- 107.75 -61.00 -90.00 50 15 \w 98.00 132.00 0.50 6.00 -- 107.75 45.00 150.00 68 16 \w 143.00 178.00 0.50 6.00 -- 107.75 45.00 150.00 70 17 \w 70.00 100.00 0.50 6.00 -- 107.75 -95.00 30.00 60 18 \w 87.00 122.00 0.50 6.00 -- 107.75 77.00 60.00 70 19 \w 144.00 175.00 0.50 6.00 -- 107.75 77.00 60.00 62 20 \w 57.00 83.00 0.50 6.00 -- 107.75 -77.00 120.00 52 21 \w 44.00 70.00 0.50 6.00 -- 107.75 -77.00 90.00 52 22 \w 36.00 61.00 0.50 6.00 -- 107.75 -61.00 -30.00 50 23 \w 40.00 65.00 0.50 6.00 -- 107.75-125.00 0.00 50 24 \w 62.00 88.00 0.50 6.00 -- 107.75 -77.00 150.00 52 25 \w 72.00 102.00 0.50 6.00 -- 107.75 -95.00 -90.00 60 26 \w 99.00 150.00 0.50 6.00 -- 107.75 45.00 30.00 102 27 \w 36.00 61.00 0.50 6.00 -- 107.75 -95.00 30.00 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 -0.0753862000 _diffrn_orient_matrix_UB_12 0.1070162000 _diffrn_orient_matrix_UB_13 0.0201907000 _diffrn_orient_matrix_UB_21 0.0341470000 _diffrn_orient_matrix_UB_22 -0.0162046000 _diffrn_orient_matrix_UB_23 0.0961463000 _diffrn_orient_matrix_UB_31 0.1574432000 _diffrn_orient_matrix_UB_32 0.0547864000 _diffrn_orient_matrix_UB_33 -0.0114003000 _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 0.0636 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 10416 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.670 _diffrn_reflns_theta_min 5.681 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.308 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71733 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.485 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.098 _refine_ls_extinction_coef 0.0042(6) _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 1.059 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 1824 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0439 _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^)+(0.0858P)^2^+0.6883P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1219 _refine_ls_wR_factor_ref 0.1247 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1680 _reflns_number_total 1824 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00964e2.cif _cod_data_source_block z461201 _cod_database_code 7247736 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C8 H3 N5 O4' _chemical_oxdiff_usercomment Z461201 _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 0.869 _shelx_estimated_absorpt_t_min 0.727 _olex2_refinement_description ; ; _shelx_res_file ; TITL 23tei011r_a.res in Pbca z461201.res created by SHELXL-2018/3 at 22:10:35 on 11-Jun-2023 REM Old TITL 23TEI011R in Pbca REM SHELXT solution in Pbca REM R1 0.097, Rweak 0.003, Alpha 0.024, Orientation as input REM Formula found by SHELXT: C13 N O3 CELL 1.54184 8.6598 12.7026 15.575 90 90 90 ZERR 8 0.0002 0.0003 0.0004 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 64 24 40 32 L.S. 10 0 0 PLAN 5 SIZE 0.11 0.11 0.26 TEMP -173 CONF list 4 MORE -1 fmap 2 53 BOND $H ACTA REM REM REM WGHT 0.085800 0.688300 EXTI 0.004175 FVAR 0.38985 O1 4 0.432779 0.211094 0.687017 11.00000 0.02558 0.01934 = 0.01562 0.00220 0.00328 -0.00448 O2 4 0.891405 0.511971 0.666913 11.00000 0.01793 0.02054 = 0.02133 -0.00436 -0.00397 -0.00358 O3 4 0.497075 0.204473 0.427797 11.00000 0.02895 0.01126 = 0.02000 0.00051 -0.00200 -0.00266 O4 4 0.358066 0.331763 0.375315 11.00000 0.01541 0.02243 = 0.02400 -0.00726 -0.00429 0.00373 N1 3 0.445267 0.239889 0.601330 11.00000 0.02199 0.01580 = 0.01503 0.00173 0.00317 -0.00117 N2 3 0.536750 0.264124 0.738336 11.00000 0.02261 0.02018 = 0.01580 0.00007 0.00172 0.00030 N3 3 0.725313 0.393660 0.711276 11.00000 0.02096 0.01862 = 0.01411 -0.00094 0.00034 0.00145 N4 3 0.784710 0.449713 0.649488 11.00000 0.01492 0.01492 = 0.01609 -0.00282 -0.00015 0.00109 N5 3 0.470462 0.297758 0.414210 11.00000 0.01513 0.01536 = 0.01369 -0.00227 0.00158 -0.00103 C1 1 0.611380 0.325734 0.684986 11.00000 0.01763 0.01500 = 0.01582 -0.00136 0.00202 0.00344 C2 1 0.735814 0.444968 0.559500 11.00000 0.01297 0.01388 = 0.01505 -0.00183 -0.00014 0.00289 C3 1 0.804967 0.514988 0.502335 11.00000 0.01408 0.01315 = 0.02063 -0.00063 0.00184 0.00055 H3 2 0.879733 0.563365 0.522497 11.00000 0.02853 C4 1 0.761351 0.513574 0.417124 11.00000 0.01626 0.01393 = 0.01931 0.00097 0.00209 0.00004 H4 2 0.806275 0.562725 0.374135 11.00000 0.02472 C5 1 0.649141 0.442938 0.387644 11.00000 0.01782 0.01353 = 0.01540 0.00096 0.00090 0.00209 H5 2 0.622097 0.441716 0.327814 11.00000 0.02252 C6 1 0.583934 0.374242 0.445715 11.00000 0.01358 0.01219 = 0.01591 -0.00179 -0.00075 0.00093 C7 1 0.623097 0.372747 0.532933 11.00000 0.01375 0.01189 = 0.01590 0.00013 0.00143 0.00282 C8 1 0.555762 0.310001 0.600510 11.00000 0.01633 0.01293 = 0.01572 -0.00024 0.00124 0.00227 HKLF 4 REM 23tei011r_a.res in Pbca REM wR2 = 0.1247, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0439 for 1680 Fo > 4sig(Fo) and 0.0464 for all 1824 data REM 167 parameters refined using 0 restraints END WGHT 0.0858 0.6884 REM Highest difference peak 0.485, deepest hole -0.318, 1-sigma level 0.098 Q1 1 0.5879 0.3222 0.6423 11.00000 0.05 0.48 Q2 1 0.7609 0.4470 0.6023 11.00000 0.05 0.34 Q3 1 0.7348 0.5029 0.3355 11.00000 0.05 0.33 Q4 1 0.4475 0.2147 0.8028 11.00000 0.05 0.33 Q5 1 0.5744 0.2421 0.3644 11.00000 0.05 0.33 ; _shelx_res_checksum 75134 _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 2.773 _oxdiff_exptl_absorpt_empirical_full_min 0.327 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 0.43278(13) 0.21109(9) 0.68702(7) 0.0202(3) Uani 1 1 d . . . . . O2 O 0.89140(12) 0.51197(9) 0.66691(7) 0.0199(3) Uani 1 1 d . . . . . O3 O 0.49707(13) 0.20447(8) 0.42780(7) 0.0201(3) Uani 1 1 d . . . . . O4 O 0.35807(12) 0.33176(9) 0.37531(7) 0.0206(3) Uani 1 1 d . . . . . N1 N 0.44527(15) 0.23989(10) 0.60133(8) 0.0176(3) Uani 1 1 d . . . . . N2 N 0.53675(15) 0.26412(10) 0.73834(8) 0.0195(3) Uani 1 1 d . . . . . N3 N 0.72531(14) 0.39366(10) 0.71128(8) 0.0179(3) Uani 1 1 d . . . . . N4 N 0.78471(14) 0.44971(10) 0.64949(8) 0.0153(3) Uani 1 1 d . . . . . N5 N 0.47046(14) 0.29776(10) 0.41421(8) 0.0147(3) Uani 1 1 d . . . . . C1 C 0.61138(17) 0.32573(12) 0.68499(9) 0.0161(3) Uani 1 1 d . . . . . C2 C 0.73581(15) 0.44497(11) 0.55950(9) 0.0140(3) Uani 1 1 d . . . . . C3 C 0.80497(17) 0.51499(11) 0.50234(10) 0.0160(3) Uani 1 1 d . . . . . H3 H 0.880(3) 0.5634(19) 0.5225(15) 0.029(5) Uiso 1 1 d . . . . . C4 C 0.76135(16) 0.51357(11) 0.41712(10) 0.0165(3) Uani 1 1 d . . . . . H4 H 0.806(2) 0.5627(18) 0.3741(15) 0.025(5) Uiso 1 1 d . . . . . C5 C 0.64914(16) 0.44294(11) 0.38764(9) 0.0156(3) Uani 1 1 d . . . . . H5 H 0.622(2) 0.4417(17) 0.3278(14) 0.023(5) Uiso 1 1 d . . . . . C6 C 0.58393(15) 0.37424(11) 0.44571(9) 0.0139(3) Uani 1 1 d . . . . . C7 C 0.62310(16) 0.37275(11) 0.53293(9) 0.0138(3) Uani 1 1 d . . . . . C8 C 0.55576(16) 0.31000(11) 0.60051(9) 0.0150(3) 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 0.0256(6) 0.0193(6) 0.0156(5) 0.0022(4) 0.0033(4) -0.0045(4) O2 0.0179(5) 0.0205(6) 0.0213(6) -0.0044(4) -0.0040(4) -0.0036(4) O3 0.0290(6) 0.0113(6) 0.0200(6) 0.0005(4) -0.0020(4) -0.0027(4) O4 0.0154(5) 0.0224(6) 0.0240(6) -0.0073(4) -0.0043(4) 0.0037(4) N1 0.0220(6) 0.0158(6) 0.0150(6) 0.0017(5) 0.0032(5) -0.0012(5) N2 0.0226(6) 0.0202(6) 0.0158(7) 0.0001(5) 0.0017(5) 0.0003(5) N3 0.0210(6) 0.0186(6) 0.0141(6) -0.0009(5) 0.0003(5) 0.0014(5) N4 0.0149(6) 0.0149(6) 0.0161(6) -0.0028(4) -0.0001(4) 0.0011(4) N5 0.0151(6) 0.0154(6) 0.0137(6) -0.0023(4) 0.0016(4) -0.0010(4) C1 0.0176(7) 0.0150(7) 0.0158(7) -0.0014(5) 0.0020(5) 0.0034(5) C2 0.0130(6) 0.0139(7) 0.0150(7) -0.0018(5) -0.0001(5) 0.0029(5) C3 0.0141(6) 0.0131(7) 0.0206(7) -0.0006(5) 0.0018(5) 0.0005(5) C4 0.0163(7) 0.0139(7) 0.0193(7) 0.0010(5) 0.0021(5) 0.0000(5) C5 0.0178(7) 0.0135(6) 0.0154(7) 0.0010(5) 0.0009(5) 0.0021(5) C6 0.0136(6) 0.0122(7) 0.0159(7) -0.0018(5) -0.0008(5) 0.0009(5) C7 0.0137(6) 0.0119(6) 0.0159(7) 0.0001(5) 0.0014(5) 0.0028(5) C8 0.0163(7) 0.0129(7) 0.0157(7) -0.0002(5) 0.0012(5) 0.0023(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 1 1 -1 0.0565 0 -1 1 0.1113 0 1 -1 0.0297 1 -1 1 0.0741 -1 1 0 0.0460 1 -1 0 0.0646 0 0 -1 0.0191 0 0 1 0.0881 1 0 1 0.0658 0 1 1 0.0517 -1 -1 0 0.1771 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 N2 O1 N1 112.18(10) . . ? C8 N1 O1 104.24(11) . . ? C1 N2 O1 104.23(12) . . ? N4 N3 C1 114.00(12) . . ? O2 N4 N3 118.60(12) . . ? O2 N4 C2 116.66(12) . . ? N3 N4 C2 124.74(12) . . ? O3 N5 C6 117.18(12) . . ? O4 N5 O3 125.15(12) . . ? O4 N5 C6 117.66(12) . . ? N2 C1 N3 122.68(13) . . ? N2 C1 C8 109.69(13) . . ? N3 C1 C8 127.62(13) . . ? C3 C2 N4 117.43(13) . . ? C3 C2 C7 121.88(13) . . ? C7 C2 N4 120.69(13) . . ? C2 C3 H3 119.8(14) . . ? C4 C3 C2 119.24(13) . . ? C4 C3 H3 121.0(14) . . ? C3 C4 H4 122.1(13) . . ? C3 C4 C5 120.91(14) . . ? C5 C4 H4 116.9(13) . . ? C4 C5 H5 119.8(13) . . ? C6 C5 C4 118.36(13) . . ? C6 C5 H5 121.8(13) . . ? C5 C6 N5 118.33(13) . . ? C5 C6 C7 123.10(13) . . ? C7 C6 N5 118.55(12) . . ? C2 C7 C8 115.30(13) . . ? C6 C7 C2 116.49(13) . . ? C6 C7 C8 128.11(13) . . ? N1 C8 C1 109.65(13) . . ? N1 C8 C7 132.77(13) . . ? C1 C8 C7 117.55(13) . . ? 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 1.3880(16) . ? O1 N2 1.3796(17) . ? O2 N4 1.2461(16) . ? O3 N5 1.2256(17) . ? O4 N5 1.2251(17) . ? N1 C8 1.307(2) . ? N2 C1 1.312(2) . ? N3 N4 1.3029(18) . ? N3 C1 1.373(2) . ? N4 C2 1.4654(17) . ? N5 C6 1.4664(18) . ? C1 C8 1.415(2) . ? C2 C3 1.394(2) . ? C2 C7 1.402(2) . ? C3 H3 0.95(2) . ? C3 C4 1.380(2) . ? C4 H4 0.99(2) . ? C4 C5 1.400(2) . ? C5 H5 0.96(2) . ? C5 C6 1.378(2) . ? C6 C7 1.4002(19) . ? C7 C8 1.4433(19) . ? 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 C8 C1 -0.45(15) . . . . ? O1 N1 C8 C7 -178.17(15) . . . . ? O1 N2 C1 N3 179.09(12) . . . . ? O1 N2 C1 C8 -0.89(15) . . . . ? O2 N4 C2 C3 -4.18(18) . . . . ? O2 N4 C2 C7 176.15(12) . . . . ? O3 N5 C6 C5 123.47(14) . . . . ? O3 N5 C6 C7 -55.33(17) . . . . ? O4 N5 C6 C5 -55.41(17) . . . . ? O4 N5 C6 C7 125.79(14) . . . . ? N1 O1 N2 C1 0.63(15) . . . . ? N2 O1 N1 C8 -0.10(15) . . . . ? N2 C1 C8 N1 0.89(17) . . . . ? N2 C1 C8 C7 179.01(12) . . . . ? N3 N4 C2 C3 176.15(13) . . . . ? N3 N4 C2 C7 -3.5(2) . . . . ? N3 C1 C8 N1 -179.08(14) . . . . ? N3 C1 C8 C7 -1.0(2) . . . . ? N4 N3 C1 N2 -178.98(13) . . . . ? N4 N3 C1 C8 1.0(2) . . . . ? N4 C2 C3 C4 -179.54(12) . . . . ? N4 C2 C7 C6 179.93(11) . . . . ? N4 C2 C7 C8 3.27(19) . . . . ? N5 C6 C7 C2 177.94(11) . . . . ? N5 C6 C7 C8 -5.9(2) . . . . ? C1 N3 N4 O2 -178.43(12) . . . . ? C1 N3 N4 C2 1.24(19) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C2 C7 C8 N1 176.32(15) . . . . ? C2 C7 C8 C1 -1.26(19) . . . . ? C3 C2 C7 C6 0.3(2) . . . . ? C3 C2 C7 C8 -176.39(12) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C4 C5 C6 N5 -177.85(12) . . . . ? C4 C5 C6 C7 0.9(2) . . . . ? C5 C6 C7 C2 -0.8(2) . . . . ? C5 C6 C7 C8 175.37(13) . . . . ? C6 C7 C8 N1 0.1(3) . . . . ? C6 C7 C8 C1 -177.47(13) . . . . ? C7 C2 C3 C4 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 0.9992 0.9990 -1.0000 0.0114 -0.0782 0.2235 0.0003 -0.9995 0.9996 -0.0868 0.1123 -0.0661 -0.0003 0.9995 -0.9996 0.0868 -0.1123 0.0661 0.9998 -1.0000 0.9992 -0.1622 0.1464 0.0912 -0.9995 1.0002 0.0006 0.1824 -0.0503 -0.1026 0.9995 -1.0002 -0.0006 -0.1824 0.0503 0.1026 -0.0003 -0.0002 -0.9998 -0.0202 -0.0961 0.0113 0.0003 0.0002 0.9998 0.0202 0.0961 -0.0113 0.9997 -0.0003 0.9994 -0.0552 0.1302 0.1460 0.0002 0.9999 1.0000 0.1272 0.0800 0.0434 -0.9995 -0.9992 0.0002 -0.0316 -0.0179 -0.2121