#------------------------------------------------------------------------------ #$Date: 2026-06-27 02:19:08 +0100 (Sat, 27 Jun 2026) $ #$Revision: 306667 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/44/7064456.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_7064456 loop_ _publ_author_name 'Dogra, Sunanda' 'Harsha, Priyasha' 'Roy Choudhury, Angshuman' _publ_section_title ; Mechanical Behaviour Modulation through Substituent Reversal in Schiff Base Molecular Crystals ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D6NJ01952H _journal_year 2026 _chemical_formula_moiety 'C14 H9 N3 O2' _chemical_formula_sum 'C14 H9 N3 O2' _chemical_formula_weight 251.24 _chemical_name_systematic E25LT _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 _audit_creation_date 2026-03-26 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2026-05-20 deposited with the CCDC. 2026-06-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.973(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 3.7943(6) _cell_length_b 22.906(3) _cell_length_c 13.931(2) _cell_measurement_reflns_used 763 _cell_measurement_temperature 100.00(1) _cell_measurement_theta_max 25.0570 _cell_measurement_theta_min 2.9550 _cell_volume 1201.8(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _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 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(1) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _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 -69.00 118.20 0.30 37.00 -- 29.89 54.00 150.00 624 2 \w -69.00 14.10 0.30 37.00 -- 29.89 54.00 -30.00 277 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0717248000 _diffrn_orient_matrix_UB_12 -0.0279046000 _diffrn_orient_matrix_UB_13 -0.0080510000 _diffrn_orient_matrix_UB_21 0.0235043000 _diffrn_orient_matrix_UB_22 -0.0052200000 _diffrn_orient_matrix_UB_23 0.0505746000 _diffrn_orient_matrix_UB_31 -0.1723904000 _diffrn_orient_matrix_UB_32 -0.0124042000 _diffrn_orient_matrix_UB_33 -0.0032770000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_unetI/netI 0.0559 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5353 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.344 _diffrn_reflns_theta_min 2.946 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.56294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear whiteish colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier whiteish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.389 _exptl_crystal_description needle _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.353 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2181 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0601 _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^)+(0.0849P)^2^+0.0233P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1429 _refine_ls_wR_factor_ref 0.1666 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1528 _reflns_number_total 2181 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj01952h2.cif _cod_data_source_block e25lt _cod_database_code 7064456 _shelx_shelxl_version_number 2018/3 _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. ; _cell_oxdiff_angle_alpha 90.035(6) _cell_oxdiff_angle_beta 96.994(11) _cell_oxdiff_angle_gamma 90.141(9) _cell_oxdiff_length_a 3.7977(7) _cell_oxdiff_length_b 22.8945(14) _cell_oxdiff_length_c 13.9264(13) _cell_oxdiff_measurement_reflns_used 759 _cell_oxdiff_volume 1201.8(2) _shelx_estimated_absorpt_t_max 0.999 _shelx_estimated_absorpt_t_min 0.998 _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), C1(H1), C14(H14), C11(H11), C4(H4), C7(H7), C3(H3), C6(H6), C13(H13) ; _shelx_res_file ; TITL e25lt_a.res in P2(1)/c e25lt.res created by SHELXL-2018/3 at 10:11:11 on 23-Feb-2026 REM Old TITL E25LT in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.150, Rweak 0.004, Alpha 0.013 REM 0.366 for 66 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N3 O CELL 0.71073 3.7943 22.9057 13.9315 90 96.973 90 ZERR 4 0.0006 0.0031 0.0022 0 0.015 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 56 36 12 8 L.S. 10 0 0 PLAN 10 SIZE 0.01 0.02 0.01 TEMP 100.00(1) CONF list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.084900 0.023300 FVAR 0.63303 O2 4 0.154168 0.580710 0.977749 11.00000 0.06264 0.03876 = 0.02683 -0.00690 0.00756 0.00506 O1 4 -0.134021 0.634561 0.866692 11.00000 0.05165 0.03091 = 0.04150 -0.00709 0.01062 0.01295 N1 3 0.315573 0.430499 0.603178 11.00000 0.02713 0.02078 = 0.02574 -0.00084 0.00804 0.00024 N3 3 0.038033 0.590352 0.893078 11.00000 0.03501 0.02734 = 0.02986 -0.00394 0.01156 0.00041 N2 3 0.826733 0.179800 0.290248 11.00000 0.03140 0.03197 = 0.03608 -0.00645 0.01057 -0.00119 C2 1 0.405060 0.333454 0.545240 11.00000 0.01974 0.02188 = 0.02315 -0.00302 0.00598 -0.00046 C10 1 0.056886 0.520207 0.652057 11.00000 0.02620 0.02181 = 0.02306 0.00190 0.00731 -0.00235 AFIX 43 H10 2 -0.016314 0.528236 0.587264 11.00000 -1.20000 AFIX 0 C1 1 0.298285 0.375269 0.616632 11.00000 0.02055 0.02336 = 0.02257 -0.00065 0.00698 0.00043 AFIX 43 H1 2 0.216656 0.361321 0.672613 11.00000 -1.20000 AFIX 0 C5 1 0.607564 0.252942 0.412617 11.00000 0.02088 0.02297 = 0.02256 -0.00305 0.00585 -0.00125 C14 1 0.347710 0.456324 0.776046 11.00000 0.02396 0.01909 = 0.02982 0.00003 0.00515 0.00033 AFIX 43 H14 2 0.467357 0.421745 0.793334 11.00000 -1.20000 AFIX 0 C12 1 0.104271 0.547337 0.818619 11.00000 0.02488 0.02073 = 0.02680 -0.00504 0.01008 -0.00046 C11 1 -0.009505 0.559927 0.722996 11.00000 0.02269 0.01808 = 0.03395 0.00192 0.00810 -0.00010 AFIX 43 H11 2 -0.129161 0.594584 0.706273 11.00000 -1.20000 AFIX 0 C4 1 0.623792 0.312823 0.392860 11.00000 0.02387 0.02465 = 0.02190 0.00028 0.00752 -0.00136 AFIX 43 H4 2 0.699668 0.325702 0.335476 11.00000 -1.20000 AFIX 0 C9 1 0.234391 0.468070 0.678556 11.00000 0.02476 0.02101 = 0.02673 -0.00232 0.01077 -0.00305 C7 1 0.386232 0.273564 0.563725 11.00000 0.02432 0.02315 = 0.02369 0.00149 0.00685 -0.00111 AFIX 43 H7 2 0.304276 0.260740 0.620351 11.00000 -1.20000 AFIX 0 C3 1 0.525894 0.352572 0.459514 11.00000 0.02565 0.01899 = 0.02548 0.00277 0.00519 0.00008 AFIX 43 H3 2 0.540443 0.392359 0.447293 11.00000 -1.20000 AFIX 0 C6 1 0.489438 0.232872 0.497883 11.00000 0.02486 0.01864 = 0.02876 0.00066 0.00589 0.00008 AFIX 43 H6 2 0.479703 0.193083 0.510578 11.00000 -1.20000 AFIX 0 C8 1 0.726705 0.211606 0.344863 11.00000 0.02328 0.02364 = 0.02672 -0.00204 0.00691 -0.00158 C13 1 0.282397 0.495996 0.846928 11.00000 0.03055 0.02483 = 0.02415 0.00016 0.00773 -0.00041 AFIX 43 H13 2 0.356021 0.488431 0.911855 11.00000 -1.20000 AFIX 0 HKLF 4 REM e25lt_a.res in P2(1)/c REM wR2 = 0.1666, GooF = S = 1.083, Restrained GooF = 1.083 for all data REM R1 = 0.0601 for 1528 Fo > 4sig(Fo) and 0.0886 for all 2181 data REM 172 parameters refined using 0 restraints END WGHT 0.0849 0.0233 REM Highest difference peak 0.353, deepest hole -0.264, 1-sigma level 0.070 Q1 1 -0.0855 0.5198 0.5800 11.00000 0.05 0.29 Q2 1 0.0253 0.4837 0.6538 11.00000 0.05 0.26 Q3 1 0.0143 0.6423 0.9474 11.00000 0.05 0.24 Q4 1 -0.2488 0.6394 0.8000 11.00000 0.05 0.23 Q5 1 -0.1000 0.5987 0.7928 11.00000 0.05 0.23 Q6 1 0.7375 0.3195 0.4626 11.00000 0.05 0.22 Q7 1 0.0339 0.1622 0.4790 11.00000 0.05 0.21 Q8 1 -0.2649 0.6003 0.6808 11.00000 0.05 0.21 Q9 1 0.4249 0.4956 0.9074 11.00000 0.05 0.21 Q10 1 0.3689 0.3583 0.3798 11.00000 0.05 0.21 ; _shelx_res_checksum 4907 _olex2_submission_original_sample_id E25LT _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 1.854 _oxdiff_exptl_absorpt_empirical_full_min 0.801 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 0.1542(6) 0.58071(8) 0.97775(13) 0.0426(6) Uani 1 1 d . . . . . O1 O -0.1340(6) 0.63456(8) 0.86669(13) 0.0409(6) Uani 1 1 d . . . . . N1 N 0.3156(5) 0.43050(8) 0.60318(14) 0.0242(5) Uani 1 1 d . . . . . N3 N 0.0380(6) 0.59035(9) 0.89308(15) 0.0301(6) Uani 1 1 d . . . . . N2 N 0.8267(6) 0.17980(9) 0.29025(16) 0.0326(6) Uani 1 1 d . . . . . C2 C 0.4051(6) 0.33345(10) 0.54524(17) 0.0213(6) Uani 1 1 d . . . . . C10 C 0.0569(7) 0.52021(10) 0.65206(17) 0.0233(6) Uani 1 1 d . . . . . H10 H -0.016314 0.528236 0.587264 0.028 Uiso 1 1 calc R U . . . C1 C 0.2983(6) 0.37527(10) 0.61663(17) 0.0218(6) Uani 1 1 d . . . . . H1 H 0.216656 0.361321 0.672613 0.026 Uiso 1 1 calc R U . . . C5 C 0.6076(6) 0.25294(10) 0.41262(16) 0.0219(6) Uani 1 1 d . . . . . C14 C 0.3477(7) 0.45632(10) 0.77605(17) 0.0241(6) Uani 1 1 d . . . . . H14 H 0.467357 0.421745 0.793334 0.029 Uiso 1 1 calc R U . . . C12 C 0.1043(7) 0.54734(10) 0.81862(17) 0.0236(6) Uani 1 1 d . . . . . C11 C -0.0095(7) 0.55993(10) 0.72300(17) 0.0245(6) Uani 1 1 d . . . . . H11 H -0.129161 0.594584 0.706273 0.029 Uiso 1 1 calc R U . . . C4 C 0.6238(6) 0.31282(10) 0.39286(16) 0.0231(6) Uani 1 1 d . . . . . H4 H 0.699668 0.325702 0.335476 0.028 Uiso 1 1 calc R U . . . C9 C 0.2344(7) 0.46807(10) 0.67856(17) 0.0235(6) Uani 1 1 d . . . . . C7 C 0.3862(6) 0.27356(10) 0.56373(17) 0.0234(6) Uani 1 1 d . . . . . H7 H 0.304276 0.260740 0.620351 0.028 Uiso 1 1 calc R U . . . C3 C 0.5259(6) 0.35257(10) 0.45951(17) 0.0232(6) Uani 1 1 d . . . . . H3 H 0.540443 0.392359 0.447293 0.028 Uiso 1 1 calc R U . . . C6 C 0.4894(7) 0.23287(10) 0.49788(17) 0.0239(6) Uani 1 1 d . . . . . H6 H 0.479703 0.193083 0.510578 0.029 Uiso 1 1 calc R U . . . C8 C 0.7267(7) 0.21161(10) 0.34486(17) 0.0242(6) Uani 1 1 d . . . . . C13 C 0.2824(7) 0.49600(10) 0.84693(18) 0.0261(6) Uani 1 1 d . . . . . H13 H 0.356021 0.488431 0.911855 0.031 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 0.0626(15) 0.0388(12) 0.0268(10) -0.0069(8) 0.0076(10) 0.0051(10) O1 0.0516(14) 0.0309(11) 0.0415(11) -0.0071(9) 0.0106(10) 0.0129(9) N1 0.0271(12) 0.0208(11) 0.0257(11) -0.0008(8) 0.0080(10) 0.0002(8) N3 0.0350(14) 0.0273(12) 0.0299(12) -0.0039(9) 0.0116(11) 0.0004(10) N2 0.0314(14) 0.0320(13) 0.0361(12) -0.0065(10) 0.0106(11) -0.0012(10) C2 0.0197(13) 0.0219(13) 0.0231(12) -0.0030(9) 0.0060(11) -0.0005(9) C10 0.0262(14) 0.0218(12) 0.0231(12) 0.0019(10) 0.0073(11) -0.0023(10) C1 0.0205(14) 0.0234(13) 0.0226(12) -0.0007(9) 0.0070(11) 0.0004(10) C5 0.0209(14) 0.0230(13) 0.0226(12) -0.0030(9) 0.0058(11) -0.0012(10) C14 0.0240(14) 0.0191(12) 0.0298(13) 0.0000(10) 0.0052(11) 0.0003(10) C12 0.0249(14) 0.0207(13) 0.0268(13) -0.0050(10) 0.0101(11) -0.0005(10) C11 0.0227(14) 0.0181(12) 0.0339(14) 0.0019(10) 0.0081(12) -0.0001(10) C4 0.0239(14) 0.0246(13) 0.0219(12) 0.0003(10) 0.0075(11) -0.0014(10) C9 0.0248(14) 0.0210(13) 0.0267(13) -0.0023(10) 0.0108(11) -0.0031(10) C7 0.0243(14) 0.0232(13) 0.0237(12) 0.0015(10) 0.0069(11) -0.0011(10) C3 0.0257(15) 0.0190(12) 0.0255(13) 0.0028(10) 0.0052(11) 0.0001(10) C6 0.0249(14) 0.0186(12) 0.0288(13) 0.0007(10) 0.0059(11) 0.0001(10) C8 0.0233(14) 0.0236(13) 0.0267(13) -0.0020(11) 0.0069(11) -0.0016(10) C13 0.0306(15) 0.0248(13) 0.0241(13) 0.0002(10) 0.0077(12) -0.0004(11) 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' 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 C1 N1 C9 118.1(2) . . ? O2 N3 O1 123.2(2) . . ? O2 N3 C12 118.9(2) . . ? O1 N3 C12 117.9(2) . . ? C7 C2 C1 119.3(2) . . ? C7 C2 C3 119.5(2) . . ? C3 C2 C1 121.2(2) . . ? C11 C10 H10 120.2 . . ? C11 C10 C9 119.7(2) . . ? C9 C10 H10 120.2 . . ? N1 C1 C2 121.3(2) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C4 C5 C8 119.2(2) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 C8 119.8(2) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C13 C14 C9 120.3(2) . . ? C11 C12 N3 118.7(2) . . ? C11 C12 C13 122.4(2) . . ? C13 C12 N3 119.0(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 C10 119.2(2) . . ? C12 C11 H11 120.4 . . ? C5 C4 H4 120.3 . . ? C3 C4 C5 119.4(2) . . ? C3 C4 H4 120.3 . . ? C10 C9 N1 117.6(2) . . ? C10 C9 C14 120.1(2) . . ? C14 C9 N1 122.2(2) . . ? C2 C7 H7 119.7 . . ? C6 C7 C2 120.6(2) . . ? C6 C7 H7 119.7 . . ? C2 C3 H3 119.7 . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3 119.7 . . ? C5 C6 H6 120.6 . . ? C7 C6 C5 118.9(2) . . ? C7 C6 H6 120.6 . . ? N2 C8 C5 178.3(3) . . ? C14 C13 C12 118.4(2) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? 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 N3 1.228(3) . ? O1 N3 1.236(3) . ? N1 C1 1.282(3) . ? N1 C9 1.420(3) . ? N3 C12 1.474(3) . ? N2 C8 1.151(3) . ? C2 C1 1.473(3) . ? C2 C7 1.399(3) . ? C2 C3 1.400(3) . ? C10 H10 0.9300 . ? C10 C11 1.389(3) . ? C10 C9 1.398(3) . ? C1 H1 0.9300 . ? C5 C4 1.402(3) . ? C5 C6 1.397(3) . ? C5 C8 1.448(3) . ? C14 H14 0.9300 . ? C14 C9 1.400(3) . ? C14 C13 1.386(3) . ? C12 C11 1.380(3) . ? C12 C13 1.389(3) . ? C11 H11 0.9300 . ? C4 H4 0.9300 . ? C4 C3 1.383(3) . ? C7 H7 0.9300 . ? C7 C6 1.397(3) . ? C3 H3 0.9300 . ? C6 H6 0.9300 . ? C13 H13 0.9300 . ? 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 C12 C11 -176.4(2) . . . . ? O2 N3 C12 C13 2.8(4) . . . . ? O1 N3 C12 C11 3.8(4) . . . . ? O1 N3 C12 C13 -177.0(2) . . . . ? N3 C12 C11 C10 178.9(2) . . . . ? N3 C12 C13 C14 -179.0(2) . . . . ? C2 C7 C6 C5 -0.8(4) . . . . ? C1 N1 C9 C10 -143.9(2) . . . . ? C1 N1 C9 C14 40.7(3) . . . . ? C1 C2 C7 C6 -179.3(2) . . . . ? C1 C2 C3 C4 -179.7(2) . . . . ? C5 C4 C3 C2 -1.2(4) . . . . ? C11 C10 C9 N1 -176.2(2) . . . . ? C11 C10 C9 C14 -0.7(4) . . . . ? C11 C12 C13 C14 0.2(4) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C9 N1 C1 C2 -175.2(2) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C9 C14 C13 C12 -0.3(4) . . . . ? C7 C2 C1 N1 179.1(2) . . . . ? C7 C2 C3 C4 0.5(4) . . . . ? C3 C2 C1 N1 -0.7(4) . . . . ? C3 C2 C7 C6 0.5(4) . . . . ? C6 C5 C4 C3 0.9(4) . . . . ? C8 C5 C4 C3 -177.0(2) . . . . ? C8 C5 C6 C7 178.0(2) . . . . ? C13 C14 C9 N1 175.8(2) . . . . ? C13 C14 C9 C10 0.5(4) . . . . ? C13 C12 C11 C10 -0.3(4) . . . . ?