#------------------------------------------------------------------------------ #$Date: 2025-02-12 01:08:47 +0200 (Wed, 12 Feb 2025) $ #$Revision: 297685 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573883.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_1573883 loop_ _publ_author_name 'Luff, Martin Simon' 'Filipovic, Tin M.' 'Corsei, Celine S.' 'Oppel, Kai' 'Krummenacher, Ivo' 'Bertermann, R\"udiger' 'Finze, Maik' 'Braunschweig, Holger' 'Radius, Udo' _publ_section_title ; Azolium-2-dithiocarboxylates as redox active ligands in nickel chemistry ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC08449G _journal_year 2025 _chemical_formula_moiety 'C14 H18 N2 S2' _chemical_formula_sum 'C14 H18 N2 S2' _chemical_formula_weight 278.42 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-12-12 deposited with the CCDC. 2025-02-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.1900(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.83520(10) _cell_length_b 8.48740(10) _cell_length_c 15.0477(2) _cell_measurement_reflns_used 16265 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 76.4780 _cell_measurement_theta_min 5.6520 _cell_volume 1444.02(3) _computing_cell_refinement 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_unetI/netI 0.0206 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 25991 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 72.000 _diffrn_reflns_theta_max 76.722 _diffrn_reflns_theta_min 4.200 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 3.201 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.588 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020) 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 red _exptl_crystal_density_diffrn 1.281 _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.402 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 2991 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.139 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0350 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+1.4552P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0943 _refine_ls_wR_factor_ref 0.0950 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2823 _reflns_number_total 2991 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc08449g2.cif _cod_data_source_block Compound_1e _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1573883 _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. ; _shelx_estimated_absorpt_t_min 0.490 _shelx_estimated_absorpt_t_max 0.762 _shelx_res_file ; TITL MaLu119_filter02_a.res in P2(1)/n MaLu119_filter02_a.res created by SHELXL-2018/3 at 10:50:11 on 26-Apr-2023 REM Old TITL MaLu119_filter02 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.092, Rweak 0.046, Alpha 0.021, Orientation as input REM Formula found by SHELXT: C14 N2 S2 CELL 1.54184 11.8352 8.4874 15.0477 90.000 107.190 90.000 ZERR 4.000 0.0001 0.0001 0.0002 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N S UNIT 56 72 8 8 SIZE 0.09 0.13 0.26 L.S. 10 BOND $H LIST 4 ACTA 144 FMAP 2 PLAN 20 OMIT 3 2 0 OMIT 2 5 1 OMIT 3 1 3 WGHT 0.035300 1.455200 FVAR 0.77167 S001 4 0.538499 0.346674 0.850921 11.00000 0.02421 0.02268 = 0.01523 0.00081 0.00087 -0.00116 S002 4 0.517383 0.181969 0.666830 11.00000 0.02251 0.01612 = 0.02343 -0.00214 0.00702 0.00218 N003 3 0.486354 0.587124 0.652999 11.00000 0.01411 0.01389 = 0.01612 0.00005 0.00311 -0.00010 N004 3 0.317109 0.480514 0.653274 11.00000 0.01446 0.01448 = 0.01543 0.00081 0.00311 0.00038 C005 1 0.435134 0.465173 0.682159 11.00000 0.01476 0.01523 = 0.01457 -0.00214 0.00411 -0.00056 C006 1 0.397092 0.685639 0.599460 11.00000 0.01617 0.01600 = 0.01369 -0.00191 0.00269 0.00125 C007 1 0.234000 0.363859 0.673171 11.00000 0.01428 0.01639 = 0.01925 0.00158 0.00448 -0.00166 AFIX 13 H007 2 0.281892 0.283700 0.714341 11.00000 -1.20000 AFIX 0 C008 1 0.289668 0.618389 0.599853 11.00000 0.01871 0.01602 = 0.01333 0.00032 0.00497 0.00183 C009 1 0.616822 0.609322 0.676541 11.00000 0.01228 0.01649 = 0.02179 -0.00035 0.00334 -0.00124 AFIX 13 H009 2 0.653975 0.523490 0.718618 11.00000 -1.20000 AFIX 0 C00A 1 0.181960 0.686614 0.551942 11.00000 0.01705 0.02223 = 0.01849 0.00095 0.00456 0.00141 AFIX 43 H00A 2 0.110380 0.642381 0.552754 11.00000 -1.20000 AFIX 0 C00B 1 0.401262 0.822875 0.549937 11.00000 0.02118 0.01652 = 0.01811 0.00018 0.00710 -0.00029 AFIX 43 H00B 2 0.472821 0.867410 0.549317 11.00000 -1.20000 AFIX 0 C00C 1 0.294008 0.890285 0.501556 11.00000 0.02731 0.01795 = 0.01931 0.00391 0.00732 0.00323 AFIX 43 H00C 2 0.293552 0.981776 0.467441 11.00000 -1.20000 AFIX 0 C00D 1 0.499170 0.328290 0.735294 11.00000 0.01235 0.01518 = 0.02039 0.00234 0.00330 -0.00084 C00E 1 0.186427 0.823560 0.502975 11.00000 0.02075 0.02304 = 0.02197 0.00424 0.00339 0.00659 AFIX 43 H00E 2 0.116116 0.872398 0.470204 11.00000 -1.20000 AFIX 0 C00F 1 0.156787 0.441397 0.725613 11.00000 0.02372 0.02198 = 0.02509 0.00236 0.01179 0.00074 AFIX 137 H00D 2 0.110530 0.523448 0.688022 11.00000 -1.50000 H00F 2 0.206057 0.485588 0.782654 11.00000 -1.50000 H00G 2 0.105078 0.364055 0.739236 11.00000 -1.50000 AFIX 0 C00G 1 0.656731 0.593483 0.589842 11.00000 0.02097 0.03337 = 0.02794 -0.00202 0.01139 -0.00045 AFIX 137 H00H 2 0.636975 0.490353 0.563659 11.00000 -1.50000 H00I 2 0.740759 0.608526 0.605944 11.00000 -1.50000 H00J 2 0.617680 0.671559 0.545130 11.00000 -1.50000 AFIX 0 C00H 1 0.653285 0.763045 0.729497 11.00000 0.01843 0.02075 = 0.03036 -0.00543 0.00053 -0.00153 AFIX 137 H00K 2 0.738005 0.770075 0.750647 11.00000 -1.50000 H00L 2 0.622985 0.765628 0.782033 11.00000 -1.50000 H00M 2 0.621845 0.850314 0.689187 11.00000 -1.50000 AFIX 0 C00I 1 0.165031 0.281139 0.584229 11.00000 0.02241 0.02535 = 0.02601 -0.00443 0.00389 -0.00664 AFIX 137 H00N 2 0.115311 0.355970 0.542789 11.00000 -1.50000 H00O 2 0.117000 0.199682 0.598690 11.00000 -1.50000 H00P 2 0.219170 0.235456 0.554963 11.00000 -1.50000 AFIX 0 HKLF 4 REM MaLu119_filter02_a.res in P2(1)/n REM wR2 = 0.095046, GooF = S = 1.13853, Restrained GooF = 1.13853 for all data REM R1 = 0.035005 for 2823 Fo > 4sig(Fo) and 0.036408 for all 2991 data REM 167 parameters refined using 0 restraints END WGHT 0.0353 1.4553 REM Highest difference peak 0.402, deepest hole -0.235, 1-sigma level 0.057 Q1 1 0.3656 0.1478 0.6907 11.00000 0.05 0.40 Q2 1 0.2080 0.3474 0.5192 11.00000 0.05 0.36 Q3 1 0.3427 0.6820 0.6124 11.00000 0.05 0.28 Q4 1 0.6335 0.5979 0.6323 11.00000 0.05 0.28 Q5 1 0.4347 0.1682 0.6937 11.00000 0.05 0.28 Q6 1 0.1946 0.3968 0.7002 11.00000 0.05 0.27 Q7 1 0.1980 0.3230 0.6305 11.00000 0.05 0.26 Q8 1 0.4800 0.2338 0.7030 11.00000 0.05 0.26 Q9 1 0.4595 0.1950 0.7032 11.00000 0.05 0.26 Q10 1 0.6547 0.6778 0.5016 11.00000 0.05 0.25 Q11 1 0.6320 0.6841 0.7048 11.00000 0.05 0.24 Q12 1 0.2345 0.8220 0.4752 11.00000 0.05 0.23 Q13 1 0.4644 0.3952 0.7087 11.00000 0.05 0.23 Q14 1 0.2729 0.4200 0.6588 11.00000 0.05 0.23 Q15 1 0.4781 0.3381 0.8841 11.00000 0.05 0.22 Q16 1 0.2373 0.6482 0.5717 11.00000 0.05 0.22 Q17 1 0.4610 0.1999 0.5933 11.00000 0.05 0.22 Q18 1 0.8046 0.8188 0.6642 11.00000 0.05 0.22 Q19 1 0.4009 0.7456 0.5735 11.00000 0.05 0.21 Q20 1 0.0922 0.6470 0.6804 11.00000 0.05 0.21 ; _shelx_res_checksum 22589 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 S001 S 0.53850(4) 0.34667(5) 0.85092(3) 0.02178(13) Uani 1 1 d . . . . . S002 S 0.51738(4) 0.18197(5) 0.66683(3) 0.02063(13) Uani 1 1 d . . . . . N003 N 0.48635(12) 0.58712(17) 0.65300(10) 0.0150(3) Uani 1 1 d . . . . . N004 N 0.31711(12) 0.48051(17) 0.65327(10) 0.0151(3) Uani 1 1 d . . . . . C005 C 0.43513(15) 0.4652(2) 0.68216(11) 0.0149(3) Uani 1 1 d . . . . . C006 C 0.39709(15) 0.6856(2) 0.59946(12) 0.0157(3) Uani 1 1 d . . . . . C007 C 0.23400(15) 0.3639(2) 0.67317(12) 0.0167(3) Uani 1 1 d . . . . . H007 H 0.281892 0.283700 0.714341 0.020 Uiso 1 1 calc R U . . . C008 C 0.28967(15) 0.6184(2) 0.59985(11) 0.0160(3) Uani 1 1 d . . . . . C009 C 0.61682(14) 0.6093(2) 0.67654(12) 0.0172(3) Uani 1 1 d . . . . . H009 H 0.653975 0.523490 0.718618 0.021 Uiso 1 1 calc R U . . . C00A C 0.18196(16) 0.6866(2) 0.55194(12) 0.0194(4) Uani 1 1 d . . . . . H00A H 0.110380 0.642381 0.552754 0.023 Uiso 1 1 calc R U . . . C00B C 0.40126(16) 0.8229(2) 0.54994(12) 0.0183(4) Uani 1 1 d . . . . . H00B H 0.472821 0.867410 0.549317 0.022 Uiso 1 1 calc R U . . . C00C C 0.29401(17) 0.8903(2) 0.50156(13) 0.0214(4) Uani 1 1 d . . . . . H00C H 0.293552 0.981776 0.467441 0.026 Uiso 1 1 calc R U . . . C00D C 0.49917(14) 0.3283(2) 0.73529(12) 0.0163(3) Uani 1 1 d . . . . . C00E C 0.18643(17) 0.8236(2) 0.50297(13) 0.0226(4) Uani 1 1 d . . . . . H00E H 0.116116 0.872398 0.470204 0.027 Uiso 1 1 calc R U . . . C00F C 0.15679(17) 0.4414(2) 0.72561(13) 0.0226(4) Uani 1 1 d . . . . . H00D H 0.110530 0.523448 0.688022 0.034 Uiso 1 1 calc R U . . . H00F H 0.206057 0.485588 0.782654 0.034 Uiso 1 1 calc R U . . . H00G H 0.105078 0.364055 0.739236 0.034 Uiso 1 1 calc R U . . . C00G C 0.65673(17) 0.5935(3) 0.58984(14) 0.0265(4) Uani 1 1 d . . . . . H00H H 0.636975 0.490353 0.563659 0.040 Uiso 1 1 calc R U . . . H00I H 0.740759 0.608526 0.605944 0.040 Uiso 1 1 calc R U . . . H00J H 0.617680 0.671559 0.545130 0.040 Uiso 1 1 calc R U . . . C00H C 0.65329(17) 0.7630(2) 0.72950(14) 0.0246(4) Uani 1 1 d . . . . . H00K H 0.738005 0.770075 0.750647 0.037 Uiso 1 1 calc R U . . . H00L H 0.622985 0.765628 0.782033 0.037 Uiso 1 1 calc R U . . . H00M H 0.621845 0.850314 0.689187 0.037 Uiso 1 1 calc R U . . . C00I C 0.16503(17) 0.2811(2) 0.58423(13) 0.0253(4) Uani 1 1 d . . . . . H00N H 0.115311 0.355970 0.542789 0.038 Uiso 1 1 calc R U . . . H00O H 0.117000 0.199682 0.598690 0.038 Uiso 1 1 calc R U . . . H00P H 0.219170 0.235456 0.554963 0.038 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 S001 0.0242(2) 0.0227(2) 0.0152(2) 0.00081(16) 0.00087(17) -0.00116(17) S002 0.0225(2) 0.0161(2) 0.0234(2) -0.00214(16) 0.00702(17) 0.00218(16) N003 0.0141(7) 0.0139(7) 0.0161(7) 0.0000(5) 0.0031(5) -0.0001(5) N004 0.0145(7) 0.0145(7) 0.0154(7) 0.0008(5) 0.0031(5) 0.0004(5) C005 0.0148(8) 0.0152(8) 0.0146(8) -0.0021(6) 0.0041(6) -0.0006(6) C006 0.0162(8) 0.0160(8) 0.0137(8) -0.0019(6) 0.0027(6) 0.0013(6) C007 0.0143(8) 0.0164(8) 0.0192(8) 0.0016(6) 0.0045(6) -0.0017(6) C008 0.0187(8) 0.0160(8) 0.0133(8) 0.0003(6) 0.0050(6) 0.0018(6) C009 0.0123(8) 0.0165(8) 0.0218(8) -0.0004(7) 0.0033(6) -0.0012(6) C00A 0.0170(8) 0.0222(9) 0.0185(8) 0.0009(7) 0.0046(7) 0.0014(7) C00B 0.0212(9) 0.0165(8) 0.0181(8) 0.0002(7) 0.0071(7) -0.0003(7) C00C 0.0273(9) 0.0180(9) 0.0193(9) 0.0039(7) 0.0073(7) 0.0032(7) C00D 0.0124(7) 0.0152(8) 0.0204(8) 0.0023(6) 0.0033(6) -0.0008(6) C00E 0.0208(9) 0.0230(9) 0.0220(9) 0.0042(7) 0.0034(7) 0.0066(7) C00F 0.0237(9) 0.0220(9) 0.0251(9) 0.0024(7) 0.0118(7) 0.0007(7) C00G 0.0210(9) 0.0334(11) 0.0279(10) -0.0020(8) 0.0114(8) -0.0005(8) C00H 0.0184(9) 0.0207(9) 0.0304(10) -0.0054(8) 0.0005(7) -0.0015(7) C00I 0.0224(9) 0.0253(10) 0.0260(10) -0.0044(8) 0.0039(8) -0.0066(8) 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' S S 0.3331 0.5567 '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 C005 N003 C006 108.23(14) . . ? C005 N003 C009 123.92(14) . . ? C006 N003 C009 127.85(14) . . ? C005 N004 C008 108.02(14) . . ? C005 N004 C007 123.90(14) . . ? C008 N004 C007 128.03(14) . . ? N003 C005 N004 110.38(15) . . ? N003 C005 C00D 124.99(15) . . ? N004 C005 C00D 124.57(15) . . ? C00B C006 C008 121.42(16) . . ? C00B C006 N003 131.89(16) . . ? C008 C006 N003 106.66(15) . . ? N004 C007 C00I 110.22(14) . . ? N004 C007 C00F 110.53(14) . . ? C00I C007 C00F 114.09(15) . . ? N004 C007 H007 107.2 . . ? C00I C007 H007 107.2 . . ? C00F C007 H007 107.2 . . ? C00A C008 C006 121.59(16) . . ? C00A C008 N004 131.73(16) . . ? C006 C008 N004 106.67(14) . . ? N003 C009 C00G 110.36(14) . . ? N003 C009 C00H 110.24(14) . . ? C00G C009 C00H 114.40(16) . . ? N003 C009 H009 107.2 . . ? C00G C009 H009 107.2 . . ? C00H C009 H009 107.2 . . ? C00E C00A C008 116.84(17) . . ? C00E C00A H00A 121.6 . . ? C008 C00A H00A 121.6 . . ? C00C C00B C006 117.05(17) . . ? C00C C00B H00B 121.5 . . ? C006 C00B H00B 121.5 . . ? C00B C00C C00E 121.39(17) . . ? C00B C00C H00C 119.3 . . ? C00E C00C H00C 119.3 . . ? C005 C00D S002 112.86(13) . . ? C005 C00D S001 115.38(13) . . ? S002 C00D S001 131.76(11) . . ? C00A C00E C00C 121.70(17) . . ? C00A C00E H00E 119.1 . . ? C00C C00E H00E 119.1 . . ? C007 C00F H00D 109.5 . . ? C007 C00F H00F 109.5 . . ? H00D C00F H00F 109.5 . . ? C007 C00F H00G 109.5 . . ? H00D C00F H00G 109.5 . . ? H00F C00F H00G 109.5 . . ? C009 C00G H00H 109.5 . . ? C009 C00G H00I 109.5 . . ? H00H C00G H00I 109.5 . . ? C009 C00G H00J 109.5 . . ? H00H C00G H00J 109.5 . . ? H00I C00G H00J 109.5 . . ? C009 C00H H00K 109.5 . . ? C009 C00H H00L 109.5 . . ? H00K C00H H00L 109.5 . . ? C009 C00H H00M 109.5 . . ? H00K C00H H00M 109.5 . . ? H00L C00H H00M 109.5 . . ? C007 C00I H00N 109.5 . . ? C007 C00I H00O 109.5 . . ? H00N C00I H00O 109.5 . . ? C007 C00I H00P 109.5 . . ? H00N C00I H00P 109.5 . . ? H00O C00I H00P 109.5 . . ? 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 S001 C00D 1.6702(18) . ? S002 C00D 1.6677(18) . ? N003 C005 1.337(2) . ? N003 C006 1.400(2) . ? N003 C009 1.491(2) . ? N004 C005 1.341(2) . ? N004 C008 1.402(2) . ? N004 C007 1.487(2) . ? C005 C00D 1.485(2) . ? C006 C00B 1.391(2) . ? C006 C008 1.395(2) . ? C007 C00I 1.518(2) . ? C007 C00F 1.522(2) . ? C007 H007 0.9800 . ? C008 C00A 1.392(2) . ? C009 C00G 1.519(2) . ? C009 C00H 1.523(2) . ? C009 H009 0.9800 . ? C00A C00E 1.386(3) . ? C00A H00A 0.9300 . ? C00B C00C 1.387(3) . ? C00B H00B 0.9300 . ? C00C C00E 1.399(3) . ? C00C H00C 0.9300 . ? C00E H00E 0.9300 . ? C00F H00D 0.9600 . ? C00F H00F 0.9600 . ? C00F H00G 0.9600 . ? C00G H00H 0.9600 . ? C00G H00I 0.9600 . ? C00G H00J 0.9600 . ? C00H H00K 0.9600 . ? C00H H00L 0.9600 . ? C00H H00M 0.9600 . ? C00I H00N 0.9600 . ? C00I H00O 0.9600 . ? C00I H00P 0.9600 . ?