# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2lt _database_code_depnum_ccdc_archive 'CCDC 905798' #TrackingRef '2LTnew.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; R-N'-3-methylcyclopentylidene-4-hydroxy benzohydrazide ; _database_code_depnum_ccdc_archive 905798 _chemical_absolute_configuration syn _chemical_enantioexcess_crystal 1.0 _chemical_optical_rotation '[\a]^20^~D~ = +25.7 (c = 0.47, EtOH)' _chemical_melting_point 464 _chemical_formula_moiety 'C13 H16 N2 O2' _chemical_formula_sum 'C13 H16 N2 O2' _chemical_formula_weight 232.28 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.159(3) _cell_length_b 18.175(6) _cell_length_c 12.684(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.77(3) _cell_angle_gamma 90.00 _cell_volume 1186.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 2.751 _cell_measurement_theta_max 11.110 _exptl_crystal_description 'elongated plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9569 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_detector 'CCD plate' _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method ; CCD rotation images, thick slices ; loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _diffrn_reflns_number 6489 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.1023 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3426 _reflns_number_gt 2099 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement ; Dirax/lsq (Duisenberg et al., 2000) ; _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_structure_solution 'SIR97 (Altomare at al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al, 2008) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.7944P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3426 _refine_ls_number_parameters 418 _refine_ls_number_restraints 245 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.2817(14) 0.8503(5) 0.6774(6) 0.055(2) Uani 1 1 d D . . C2A C 0.0740(14) 0.8557(5) 0.7400(6) 0.059(2) Uani 1 1 d D . . H2A H -0.0288 0.8990 0.7391 0.070 Uiso 1 1 calc R . . C3A C 0.0180(13) 0.7978(4) 0.8034(7) 0.057(2) Uani 1 1 d D . . H3A H -0.1240 0.8013 0.8472 0.069 Uiso 1 1 calc R . . C4A C 0.1645(12) 0.7345(4) 0.8047(6) 0.0418(19) Uani 1 1 d D . . C5A C 0.3694(14) 0.7292(4) 0.7424(6) 0.052(2) Uani 1 1 d D . . H5A H 0.4748 0.6862 0.7450 0.062 Uiso 1 1 calc R . . C6A C 0.4232(13) 0.7866(4) 0.6755(6) 0.045(2) Uani 1 1 d D . . H6A H 0.5580 0.7819 0.6284 0.054 Uiso 1 1 calc R . . C7A C 0.0897(11) 0.6733(4) 0.8773(5) 0.0419(19) Uani 1 1 d D . . C1B C 0.2208(12) 0.1184(4) 0.8278(6) 0.044(2) Uani 1 1 d D . . C2B C 0.4236(15) 0.1106(5) 0.7608(7) 0.064(3) Uani 1 1 d D . . H2B H 0.5167 0.0657 0.7581 0.076 Uiso 1 1 calc R . . C3B C 0.4866(14) 0.1697(5) 0.6981(7) 0.060(3) Uani 1 1 d D . . H3B H 0.6315 0.1651 0.6560 0.072 Uiso 1 1 calc R . . C4B C 0.3495(14) 0.2346(5) 0.6940(7) 0.056(2) Uani 1 1 d D . . C5B C 0.1432(14) 0.2385(4) 0.7616(7) 0.058(2) Uani 1 1 d D . . H5B H 0.0443 0.2825 0.7625 0.070 Uiso 1 1 calc R . . C6B C 0.0799(14) 0.1822(4) 0.8252(7) 0.065(3) Uani 1 1 d D . . H6B H -0.0632 0.1870 0.8681 0.078 Uiso 1 1 calc R . . C7B C 0.4200(14) 0.2944(5) 0.6262(7) 0.064(3) Uani 1 1 d D . . C8D C 0.375(3) 0.5131(6) 0.9898(11) 0.041(5) Uani 0.497(10) 1 d PDU A 1 C9D C 0.569(3) 0.4911(5) 0.9153(10) 0.042(4) Uani 0.497(10) 1 d PDU A 1 H9D1 H 0.7167 0.5259 0.9177 0.050 Uiso 0.497(10) 1 calc PR A 1 H9D2 H 0.4903 0.4884 0.8421 0.050 Uiso 0.497(10) 1 calc PR A 1 C10D C 0.6548(19) 0.4154(5) 0.9553(10) 0.051(4) Uani 0.497(10) 1 d PDU A 1 H10D H 0.8077 0.4218 1.0072 0.061 Uiso 0.497(10) 1 calc PR A 1 C11D C 0.428(2) 0.3867(5) 1.0144(10) 0.036(3) Uani 0.497(10) 1 d PDU A 1 H11A H 0.4864 0.3483 1.0660 0.043 Uiso 0.497(10) 1 calc PR A 1 H11B H 0.2909 0.3660 0.9648 0.043 Uiso 0.497(10) 1 calc PR A 1 C12D C 0.331(3) 0.4547(5) 1.0702(10) 0.052(4) Uani 0.497(10) 1 d PDU A 1 H12A H 0.1449 0.4503 1.0840 0.063 Uiso 0.497(10) 1 calc PR A 1 H12B H 0.4336 0.4642 1.1376 0.063 Uiso 0.497(10) 1 calc PR A 1 C13D C 0.731(4) 0.3626(9) 0.8693(14) 0.107(8) Uani 0.497(10) 1 d PDU A 1 H13A H 0.8715 0.3844 0.8312 0.160 Uiso 0.497(10) 1 calc PR A 1 H13B H 0.5806 0.3535 0.8198 0.160 Uiso 0.497(10) 1 calc PR A 1 H13C H 0.7905 0.3161 0.9015 0.160 Uiso 0.497(10) 1 calc PR A 1 C8C C 0.141(2) 0.4569(4) 0.5485(10) 0.042(3) Uani 0.702(11) 1 d PDU B 2 C9C C 0.152(2) 0.5258(6) 0.4853(10) 0.076(4) Uani 0.702(11) 1 d PDU B 2 H9C1 H 0.1248 0.5149 0.4089 0.091 Uiso 0.702(11) 1 calc PR B 2 H9C2 H 0.3229 0.5501 0.4983 0.091 Uiso 0.702(11) 1 calc PR B 2 C10C C -0.064(2) 0.5747(4) 0.5213(8) 0.056(3) Uani 0.702(11) 1 d PDU B 2 H10C H -0.2290 0.5627 0.4789 0.068 Uiso 0.702(11) 1 calc PR B 2 C11C C -0.090(2) 0.5507(5) 0.6355(8) 0.070(4) Uani 0.702(11) 1 d PDU B 2 H11C H -0.2634 0.5634 0.6592 0.084 Uiso 0.702(11) 1 calc PR B 2 H11D H 0.0448 0.5743 0.6834 0.084 Uiso 0.702(11) 1 calc PR B 2 C12C C -0.052(3) 0.4673(5) 0.6327(10) 0.060(4) Uani 0.702(11) 1 d PDU B 2 H12C H 0.0192 0.4486 0.7020 0.072 Uiso 0.702(11) 1 calc PR B 2 H12D H -0.2177 0.4418 0.6131 0.072 Uiso 0.702(11) 1 calc PR B 2 C13C C -0.015(3) 0.6576(4) 0.5150(11) 0.083(5) Uani 0.702(11) 1 d PDU B 2 H13D H -0.0058 0.6721 0.4410 0.125 Uiso 0.702(11) 1 calc PR B 2 H13E H 0.1489 0.6697 0.5545 0.125 Uiso 0.702(11) 1 calc PR B 2 H13F H -0.1577 0.6842 0.5456 0.125 Uiso 0.702(11) 1 calc PR B 2 C8A C 0.372(3) 0.5119(5) 0.9489(12) 0.036(5) Uani 0.503(10) 1 d PDU A 3 C9A C 0.361(2) 0.4416(5) 1.0094(8) 0.026(3) Uani 0.503(10) 1 d PDU A 3 H9A1 H 0.1841 0.4327 1.0326 0.032 Uiso 0.503(10) 1 calc PR A 3 H9A2 H 0.4853 0.4424 1.0723 0.032 Uiso 0.503(10) 1 calc PR A 3 C10A C 0.4360(17) 0.3828(4) 0.9309(8) 0.033(3) Uani 0.503(10) 1 d PDU A 3 H10A H 0.2846 0.3744 0.8789 0.039 Uiso 0.503(10) 1 calc PR A 3 C11A C 0.650(2) 0.4207(5) 0.8740(10) 0.042(4) Uani 0.503(10) 1 d PDU A 3 H11E H 0.6666 0.3988 0.8033 0.050 Uiso 0.503(10) 1 calc PR A 3 H11F H 0.8190 0.4166 0.9154 0.050 Uiso 0.503(10) 1 calc PR A 3 C12A C 0.565(2) 0.5009(5) 0.8645(11) 0.038(4) Uani 0.503(10) 1 d PDU A 3 H12E H 0.7156 0.5342 0.8768 0.046 Uiso 0.503(10) 1 calc PR A 3 H12F H 0.4816 0.5109 0.7934 0.046 Uiso 0.503(10) 1 calc PR A 3 C13A C 0.519(2) 0.3091(5) 0.9789(11) 0.051(5) Uani 0.503(10) 1 d PDU A 3 H13G H 0.3743 0.2878 1.0151 0.076 Uiso 0.503(10) 1 calc PR A 3 H13H H 0.6681 0.3163 1.0297 0.076 Uiso 0.503(10) 1 calc PR A 3 H13I H 0.5671 0.2757 0.9228 0.076 Uiso 0.503(10) 1 calc PR A 3 C8B C 0.143(5) 0.4572(8) 0.5114(17) 0.052(9) Uani 0.298(11) 1 d PDU B 4 C9B C -0.021(5) 0.4798(8) 0.5971(17) 0.053(8) Uani 0.298(11) 1 d PDU B 4 H9B1 H 0.0413 0.4577 0.6654 0.063 Uiso 0.298(11) 1 calc PR B 4 H9B2 H -0.2048 0.4655 0.5809 0.063 Uiso 0.298(11) 1 calc PR B 4 C10B C 0.008(3) 0.5635(8) 0.5995(14) 0.056(7) Uani 0.298(11) 1 d PDU B 4 H10B H 0.1722 0.5775 0.6413 0.068 Uiso 0.298(11) 1 calc PR B 4 C11B C 0.031(6) 0.5823(11) 0.4830(18) 0.107(15) Uani 0.298(11) 1 d PDU B 4 H11G H -0.1435 0.5843 0.4453 0.128 Uiso 0.298(11) 1 calc PR B 4 H11H H 0.1170 0.6305 0.4755 0.128 Uiso 0.298(11) 1 calc PR B 4 C12B C 0.193(4) 0.5207(10) 0.4394(15) 0.036(6) Uani 0.298(11) 1 d PDU B 4 H12G H 0.1346 0.5092 0.3652 0.043 Uiso 0.298(11) 1 calc PR B 4 H12H H 0.3792 0.5339 0.4430 0.043 Uiso 0.298(11) 1 calc PR B 4 C13B C -0.223(3) 0.6025(9) 0.6436(16) 0.043(7) Uani 0.298(11) 1 d PDU B 4 H13J H -0.2356 0.5885 0.7177 0.065 Uiso 0.298(11) 1 calc PR B 4 H13K H -0.3829 0.5881 0.6027 0.065 Uiso 0.298(11) 1 calc PR B 4 H13L H -0.1998 0.6559 0.6388 0.065 Uiso 0.298(11) 1 calc PR B 4 N1A N 0.2854(11) 0.6270(3) 0.9091(5) 0.0513(18) Uani 1 1 d D A . H1N H 0.4363 0.6356 0.8959 0.062 Uiso 1 1 d R . . N2A N 0.2348(11) 0.5691(3) 0.9774(5) 0.0516(18) Uani 1 1 d D . . N1B N 0.2251(12) 0.3420(3) 0.5949(5) 0.0560(19) Uani 1 1 d D B . H2N H 0.0739 0.3407 0.6263 0.067 Uiso 1 1 d R . . N2B N 0.2778(10) 0.3994(3) 0.5277(6) 0.059(2) Uani 1 1 d D . . O1A O 0.3335(10) 0.9085(3) 0.6128(5) 0.0600(16) Uani 1 1 d . . . H1A H 0.4607 0.8981 0.5775 0.072 Uiso 1 1 calc R . . O1B O 0.1650(10) 0.0586(4) 0.8859(5) 0.0677(17) Uani 1 1 d . . . H1B H 0.0452 0.0689 0.9251 0.081 Uiso 1 1 calc R . . O2A O -0.1329(8) 0.6645(3) 0.9052(5) 0.0582(16) Uani 1 1 d D . . O2B O 0.6429(10) 0.3037(4) 0.5982(5) 0.0645(17) Uani 1 1 d 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 C1A 0.053(5) 0.065(6) 0.050(5) 0.006(5) 0.014(4) -0.003(5) C2A 0.053(5) 0.056(6) 0.071(6) 0.023(5) 0.033(4) 0.013(4) C3A 0.041(4) 0.062(6) 0.070(6) 0.022(5) 0.022(4) 0.011(4) C4A 0.036(4) 0.038(5) 0.051(5) 0.013(4) 0.001(4) 0.000(4) C5A 0.044(4) 0.052(6) 0.060(5) 0.022(5) 0.005(4) 0.021(4) C6A 0.044(4) 0.049(5) 0.044(5) 0.014(4) 0.012(4) 0.011(4) C7A 0.044(4) 0.040(5) 0.044(5) 0.015(4) 0.020(3) -0.011(4) C1B 0.034(4) 0.035(5) 0.064(5) -0.002(4) -0.002(4) 0.002(4) C2B 0.059(5) 0.061(6) 0.071(6) -0.012(5) 0.005(4) 0.024(4) C3B 0.048(5) 0.061(6) 0.073(7) -0.019(5) 0.016(4) 0.006(4) C4B 0.042(4) 0.057(6) 0.072(6) -0.020(5) 0.011(4) -0.003(4) C5B 0.049(4) 0.038(5) 0.089(7) -0.018(5) 0.017(4) -0.001(4) C6B 0.040(4) 0.064(7) 0.093(7) -0.020(6) 0.022(4) -0.002(5) C7B 0.049(5) 0.052(6) 0.091(7) -0.031(5) -0.007(5) 0.007(5) C8D 0.036(7) 0.060(9) 0.025(8) 0.015(6) -0.013(6) -0.012(6) C9D 0.041(4) 0.041(4) 0.042(4) 0.0001(11) 0.0024(11) 0.0002(11) C10D 0.054(7) 0.059(7) 0.042(7) -0.006(6) 0.017(6) 0.011(6) C11D 0.034(5) 0.039(7) 0.037(7) 0.003(5) 0.018(5) 0.002(5) C12D 0.060(7) 0.041(7) 0.056(8) 0.000(6) 0.006(6) -0.011(5) C13D 0.104(11) 0.112(11) 0.108(11) -0.009(9) 0.032(8) -0.001(8) C8C 0.042(3) 0.042(3) 0.042(3) -0.0002(11) 0.0024(11) -0.0004(11) C9C 0.071(7) 0.080(8) 0.078(8) 0.003(6) 0.025(6) -0.013(5) C10C 0.059(6) 0.052(6) 0.058(7) 0.010(5) 0.000(5) 0.010(5) C11C 0.070(4) 0.070(4) 0.070(4) 0.0003(11) 0.0048(11) 0.0000(11) C12C 0.060(4) 0.060(4) 0.060(4) -0.0003(11) 0.0044(11) 0.0002(11) C13C 0.095(8) 0.063(7) 0.093(8) -0.001(6) 0.018(6) 0.009(6) C8A 0.036(7) 0.036(7) 0.035(9) 0.013(5) -0.006(6) -0.011(5) C9A 0.027(3) 0.026(3) 0.026(3) 0.0002(11) 0.0024(11) 0.0002(11) C10A 0.035(6) 0.036(6) 0.026(6) -0.007(5) -0.006(5) 0.009(5) C11A 0.034(6) 0.056(7) 0.037(7) -0.006(5) 0.012(5) 0.001(5) C12A 0.037(6) 0.037(6) 0.043(7) 0.008(5) 0.011(5) 0.001(5) C13A 0.046(7) 0.050(8) 0.054(8) 0.001(6) -0.009(6) -0.004(6) C8B 0.052(9) 0.053(9) 0.052(9) 0.0000(11) 0.0034(12) -0.0001(11) C9B 0.059(11) 0.051(11) 0.046(11) 0.011(8) -0.013(9) 0.008(8) C10B 0.056(10) 0.052(10) 0.064(11) 0.004(9) 0.022(9) 0.001(8) C11B 0.107(15) 0.107(15) 0.107(15) 0.0001(11) 0.0071(15) 0.0000(11) C12B 0.036(6) 0.036(6) 0.036(6) 0.0003(11) 0.0027(11) 0.0001(11) C13B 0.045(9) 0.037(10) 0.051(10) -0.016(7) 0.023(7) 0.007(7) N1A 0.042(4) 0.049(4) 0.063(4) 0.016(4) 0.007(3) 0.003(3) N2A 0.045(3) 0.050(5) 0.059(4) 0.027(4) 0.002(3) -0.006(3) N1B 0.042(4) 0.040(4) 0.088(5) 0.002(4) 0.023(4) 0.002(3) N2B 0.035(3) 0.039(4) 0.103(6) 0.003(4) 0.010(4) -0.003(3) O1A 0.054(3) 0.049(4) 0.080(4) 0.018(3) 0.025(3) 0.010(3) O1B 0.057(3) 0.065(4) 0.082(4) -0.010(4) 0.021(3) 0.012(3) O2A 0.030(3) 0.059(4) 0.087(4) 0.008(3) 0.011(3) 0.000(3) O2B 0.044(3) 0.071(4) 0.080(4) 0.013(3) 0.017(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1A C6A 1.369(8) . no C1A O1A 1.375(9) . no C1A C2A 1.379(8) . no C2A C3A 1.367(8) . no C2A H2A 0.9500 . no C3A C4A 1.376(8) . no C3A H3A 0.9500 . no C4A C5A 1.364(8) . no C4A C7A 1.510(9) . no C5A C6A 1.385(8) . no C5A H5A 0.9500 . no C6A H6A 0.9500 . no C7A O2A 1.235(6) . no C7A N1A 1.356(8) . no C1B O1B 1.354(9) . no C1B C6B 1.367(9) . no C1B C2B 1.399(9) . no C2B C3B 1.388(9) . no C2B H2B 0.9500 . no C3B C4B 1.374(9) . no C3B H3B 0.9500 . no C4B C5B 1.411(9) . no C4B C7B 1.448(12) . no C5B C6B 1.357(9) . no C5B H5B 0.9500 . no C6B H6B 0.9500 . no C7B O2B 1.237(8) . no C7B N1B 1.365(8) . no C8D N2A 1.250(7) . no C8D C9D 1.478(7) . no C8D C12D 1.499(8) . no C9D C10D 1.522(7) . no C9D H9D1 0.9900 . no C9D H9D2 0.9900 . no C10D C11D 1.521(7) . no C10D C13D 1.524(9) . no C10D H10D 1.0000 . no C11D C12D 1.527(7) . no C11D H11A 0.9900 . no C11D H11B 0.9900 . no C12D H12A 0.9900 . no C12D H12B 0.9900 . no C13D H13A 0.9800 . no C13D H13B 0.9800 . no C13D H13C 0.9800 . no C8C N2B 1.297(6) . no C8C C9C 1.490(9) . no C8C C12C 1.519(9) . no C9C C10C 1.521(9) . no C9C H9C1 0.9900 . no C9C H9C2 0.9900 . no C10C C11C 1.526(9) . no C10C C13C 1.531(9) . no C10C H10C 1.0000 . no C11C C12C 1.530(9) . no C11C H11C 0.9900 . no C11C H11D 0.9900 . no C12C H12C 0.9900 . no C12C H12D 0.9900 . no C13C H13D 0.9800 . no C13C H13E 0.9800 . no C13C H13F 0.9800 . no C8A N2A 1.319(7) . no C8A C9A 1.494(9) . no C8A C12A 1.524(10) . no C9A C10A 1.528(9) . no C9A H9A1 0.9900 . no C9A H9A2 0.9900 . no C10A C13A 1.521(9) . no C10A C11A 1.523(9) . no C10A H10A 1.0000 . no C11A C12A 1.525(9) . no C11A H11E 0.9900 . no C11A H11F 0.9900 . no C12A H12E 0.9900 . no C12A H12F 0.9900 . no C13A H13G 0.9800 . no C13A H13H 0.9800 . no C13A H13I 0.9800 . no C8B N2B 1.269(8) . no C8B C9B 1.480(10) . no C8B C12B 1.505(11) . no C9B C10B 1.529(10) . no C9B H9B1 0.9900 . no C9B H9B2 0.9900 . no C10B C13B 1.526(10) . no C10B C11B 1.528(10) . no C10B H10B 1.0000 . no C11B C12B 1.523(10) . no C11B H11G 0.9900 . no C11B H11H 0.9900 . no C12B H12G 0.9900 . no C12B H12H 0.9900 . no C13B H13J 0.9800 . no C13B H13K 0.9800 . no C13B H13L 0.9800 . no N1A N2A 1.398(7) . no N1A H1N 0.8223 . no N1B N2B 1.386(7) . no N1B H2N 0.8987 . no O1A H1A 0.8400 . no O1B H1B 0.8400 . no 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 C6A C1A O1A 121.0(6) . . no C6A C1A C2A 120.4(7) . . no O1A C1A C2A 118.5(7) . . no C3A C2A C1A 119.1(7) . . no C3A C2A H2A 120.4 . . no C1A C2A H2A 120.4 . . no C2A C3A C4A 120.8(7) . . no C2A C3A H3A 119.6 . . no C4A C3A H3A 119.6 . . no C5A C4A C3A 120.0(7) . . no C5A C4A C7A 122.6(6) . . no C3A C4A C7A 117.4(6) . . no C4A C5A C6A 119.7(7) . . no C4A C5A H5A 120.2 . . no C6A C5A H5A 120.2 . . no C1A C6A C5A 119.9(6) . . no C1A C6A H6A 120.1 . . no C5A C6A H6A 120.1 . . no O2A C7A N1A 121.5(6) . . no O2A C7A C4A 123.4(6) . . no N1A C7A C4A 115.1(5) . . no O1B C1B C6B 124.2(6) . . no O1B C1B C2B 116.3(7) . . no C6B C1B C2B 119.2(8) . . no C3B C2B C1B 118.9(8) . . no C3B C2B H2B 120.5 . . no C1B C2B H2B 120.5 . . no C4B C3B C2B 123.1(8) . . no C4B C3B H3B 118.4 . . no C2B C3B H3B 118.4 . . no C3B C4B C5B 115.3(8) . . no C3B C4B C7B 121.2(7) . . no C5B C4B C7B 123.5(7) . . no C6B C5B C4B 123.0(8) . . no C6B C5B H5B 118.5 . . no C4B C5B H5B 118.5 . . no C5B C6B C1B 120.4(7) . . no C5B C6B H6B 119.8 . . no C1B C6B H6B 119.8 . . no O2B C7B N1B 120.8(8) . . no O2B C7B C4B 123.2(7) . . no N1B C7B C4B 116.1(7) . . no N2A C8D C9D 123.3(9) . . no N2A C8D C12D 123.4(10) . . no C9D C8D C12D 112.4(6) . . no C8D C9D C10D 103.1(6) . . no C8D C9D H9D1 111.1 . . no C10D C9D H9D1 111.1 . . no C8D C9D H9D2 111.1 . . no C10D C9D H9D2 111.1 . . no H9D1 C9D H9D2 109.1 . . no C11D C10D C9D 104.9(7) . . no C11D C10D C13D 112.3(9) . . no C9D C10D C13D 114.4(10) . . no C11D C10D H10D 108.3 . . no C9D C10D H10D 108.3 . . no C13D C10D H10D 108.3 . . no C10D C11D C12D 103.7(7) . . no C10D C11D H11A 111.0 . . no C12D C11D H11A 111.0 . . no C10D C11D H11B 111.0 . . no C12D C11D H11B 111.0 . . no H11A C11D H11B 109.0 . . no C8D C12D C11D 100.9(7) . . no C8D C12D H12A 111.6 . . no C11D C12D H12A 111.6 . . no C8D C12D H12B 111.6 . . no C11D C12D H12B 111.6 . . no H12A C12D H12B 109.4 . . no C10D C13D H13A 109.5 . . no C10D C13D H13B 109.5 . . no H13A C13D H13B 109.5 . . no C10D C13D H13C 109.5 . . no H13A C13D H13C 109.5 . . no H13B C13D H13C 109.5 . . no N2B C8C C9C 121.7(8) . . no N2B C8C C12C 129.4(8) . . no C9C C8C C12C 108.9(6) . . no C8C C9C C10C 105.9(6) . . no C8C C9C H9C1 110.6 . . no C10C C9C H9C1 110.6 . . no C8C C9C H9C2 110.6 . . no C10C C9C H9C2 110.6 . . no H9C1 C9C H9C2 108.7 . . no C9C C10C C11C 103.3(7) . . no C9C C10C C13C 115.7(8) . . no C11C C10C C13C 110.8(8) . . no C9C C10C H10C 108.9 . . no C11C C10C H10C 108.9 . . no C13C C10C H10C 108.9 . . no C10C C11C C12C 104.0(7) . . no C10C C11C H11C 111.0 . . no C12C C11C H11C 111.0 . . no C10C C11C H11D 111.0 . . no C12C C11C H11D 111.0 . . no H11C C11C H11D 109.0 . . no C8C C12C C11C 103.3(6) . . no C8C C12C H12C 111.1 . . no C11C C12C H12C 111.1 . . no C8C C12C H12D 111.1 . . no C11C C12C H12D 111.1 . . no H12C C12C H12D 109.1 . . no C10C C13C H13D 109.5 . . no C10C C13C H13E 109.5 . . no H13D C13C H13E 109.5 . . no C10C C13C H13F 109.5 . . no H13D C13C H13F 109.5 . . no H13E C13C H13F 109.5 . . no N2A C8A C9A 119.7(9) . . no N2A C8A C12A 133.0(9) . . no C9A C8A C12A 107.2(6) . . no C8A C9A C10A 104.1(7) . . no C8A C9A H9A1 110.9 . . no C10A C9A H9A1 110.9 . . no C8A C9A H9A2 110.9 . . no C10A C9A H9A2 110.9 . . no H9A1 C9A H9A2 109.0 . . no C13A C10A C11A 113.3(8) . . no C13A C10A C9A 115.5(8) . . no C11A C10A C9A 102.4(7) . . no C13A C10A H10A 108.4 . . no C11A C10A H10A 108.4 . . no C9A C10A H10A 108.4 . . no C10A C11A C12A 104.8(6) . . no C10A C11A H11E 110.8 . . no C12A C11A H11E 110.8 . . no C10A C11A H11F 110.8 . . no C12A C11A H11F 110.8 . . no H11E C11A H11F 108.9 . . no C8A C12A C11A 105.6(6) . . no C8A C12A H12E 110.6 . . no C11A C12A H12E 110.6 . . no C8A C12A H12F 110.6 . . no C11A C12A H12F 110.6 . . no H12E C12A H12F 108.8 . . no C10A C13A H13G 109.5 . . no C10A C13A H13H 109.5 . . no H13G C13A H13H 109.5 . . no C10A C13A H13I 109.5 . . no H13G C13A H13I 109.5 . . no H13H C13A H13I 109.5 . . no N2B C8B C9B 116.4(14) . . no N2B C8B C12B 128.3(17) . . no C9B C8B C12B 111.2(8) . . no C8B C9B C10B 103.3(9) . . no C8B C9B H9B1 111.1 . . no C10B C9B H9B1 111.1 . . no C8B C9B H9B2 111.1 . . no C10B C9B H9B2 111.1 . . no H9B1 C9B H9B2 109.1 . . no C13B C10B C11B 111.2(11) . . no C13B C10B C9B 112.8(11) . . no C11B C10B C9B 102.5(10) . . no C13B C10B H10B 110.0 . . no C11B C10B H10B 110.0 . . no C9B C10B H10B 110.0 . . no C12B C11B C10B 105.4(9) . . no C12B C11B H11G 110.7 . . no C10B C11B H11G 110.7 . . no C12B C11B H11H 110.7 . . no C10B C11B H11H 110.7 . . no H11G C11B H11H 108.8 . . no C8B C12B C11B 102.9(8) . . no C8B C12B H12G 111.2 . . no C11B C12B H12G 111.2 . . no C8B C12B H12H 111.2 . . no C11B C12B H12H 111.2 . . no H12G C12B H12H 109.1 . . no C10B C13B H13J 109.5 . . no C10B C13B H13K 109.5 . . no H13J C13B H13K 109.5 . . no C10B C13B H13L 109.5 . . no H13J C13B H13L 109.5 . . no H13K C13B H13L 109.5 . . no C7A N1A N2A 119.1(5) . . no C7A N1A H1N 121.2 . . no N2A N1A H1N 119.2 . . no C8D N2A C8A 23.1(10) . . no C8D N2A N1A 124.1(8) . . no C8A N2A N1A 107.4(7) . . no C7B N1B N2B 119.0(6) . . no C7B N1B H2N 119.9 . . no N2B N1B H2N 120.2 . . no C8B N2B C8C 21.1(11) . . no C8B N2B N1B 126.5(11) . . no C8C N2B N1B 110.5(7) . . no C1A O1A H1A 109.5 . . no C1B O1B H1B 109.5 . . no 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 C6A C1A C2A C3A 2.7(12) . . . . no O1A C1A C2A C3A 179.1(7) . . . . no C1A C2A C3A C4A -0.5(13) . . . . no C2A C3A C4A C5A 0.3(13) . . . . no C2A C3A C4A C7A 179.8(7) . . . . no C3A C4A C5A C6A -2.2(12) . . . . no C7A C4A C5A C6A 178.3(7) . . . . no O1A C1A C6A C5A 179.1(7) . . . . no C2A C1A C6A C5A -4.6(13) . . . . no C4A C5A C6A C1A 4.4(12) . . . . no C5A C4A C7A O2A -153.8(8) . . . . no C3A C4A C7A O2A 26.6(12) . . . . no C5A C4A C7A N1A 25.1(11) . . . . no C3A C4A C7A N1A -154.4(7) . . . . no O1B C1B C2B C3B 178.9(7) . . . . no C6B C1B C2B C3B 4.0(12) . . . . no C1B C2B C3B C4B -3.9(13) . . . . no C2B C3B C4B C5B 2.3(13) . . . . no C2B C3B C4B C7B -179.1(8) . . . . no C3B C4B C5B C6B -1.1(12) . . . . no C7B C4B C5B C6B -179.6(9) . . . . no C4B C5B C6B C1B 1.4(13) . . . . no O1B C1B C6B C5B -177.4(7) . . . . no C2B C1B C6B C5B -2.9(12) . . . . no C3B C4B C7B O2B -26.2(13) . . . . no C5B C4B C7B O2B 152.2(9) . . . . no C3B C4B C7B N1B 154.7(8) . . . . no C5B C4B C7B N1B -26.8(12) . . . . no N2A C8D C9D C10D -171.7(15) . . . . no C12D C8D C9D C10D -1.8(17) . . . . no C8D C9D C10D C11D 24.6(14) . . . . no C8D C9D C10D C13D 148.1(13) . . . . no C9D C10D C11D C12D -38.3(12) . . . . no C13D C10D C11D C12D -163.2(12) . . . . no N2A C8D C12D C11D 148.7(16) . . . . no C9D C8D C12D C11D -21.2(17) . . . . no C10D C11D C12D C8D 35.4(14) . . . . no N2B C8C C9C C10C 170.9(11) . . . . no C12C C8C C9C C10C -7.9(14) . . . . no C8C C9C C10C C11C 28.5(12) . . . . no C8C C9C C10C C13C 149.8(10) . . . . no C9C C10C C11C C12C -38.4(11) . . . . no C13C C10C C11C C12C -162.9(10) . . . . no N2B C8C C12C C11C 165.5(13) . . . . no C9C C8C C12C C11C -15.8(14) . . . . no C10C C11C C12C C8C 33.3(13) . . . . no N2A C8A C9A C10A 156.2(14) . . . . no C12A C8A C9A C10A -26.6(15) . . . . no C8A C9A C10A C13A 162.7(11) . . . . no C8A C9A C10A C11A 39.1(12) . . . . no C13A C10A C11A C12A -162.0(11) . . . . no C9A C10A C11A C12A -36.8(12) . . . . no N2A C8A C12A C11A -179.7(18) . . . . no C9A C8A C12A C11A 3.6(17) . . . . no C10A C11A C12A C8A 20.8(15) . . . . no N2B C8B C9B C10B 140(2) . . . . no C12B C8B C9B C10B -20(3) . . . . no C8B C9B C10B C13B 154.4(17) . . . . no C8B C9B C10B C11B 35(2) . . . . no C13B C10B C11B C12B -159(2) . . . . no C9B C10B C11B C12B -38(2) . . . . no N2B C8B C12B C11B -160(3) . . . . no C9B C8B C12B C11B -4(3) . . . . no C10B C11B C12B C8B 26(3) . . . . no O2A C7A N1A N2A -1.7(11) . . . . no C4A C7A N1A N2A 179.3(6) . . . . no C9D C8D N2A C8A 31(2) . . . . no C12D C8D N2A C8A -138(5) . . . . no C9D C8D N2A N1A -17(2) . . . . no C12D C8D N2A N1A 174.4(11) . . . . no C9A C8A N2A C8D 39(3) . . . . no C12A C8A N2A C8D -137(5) . . . . no C9A C8A N2A N1A 178.8(12) . . . . no C12A C8A N2A N1A 2(2) . . . . no C7A N1A N2A C8D 160.4(12) . . . . no C7A N1A N2A C8A 142.7(11) . . . . no O2B C7B N1B N2B 2.6(12) . . . . no C4B C7B N1B N2B -178.3(7) . . . . no C9B C8B N2B C8C -20(3) . . . . no C12B C8B N2B C8C 135(6) . . . . no C9B C8B N2B N1B 25(3) . . . . no C12B C8B N2B N1B 179.9(18) . . . . no C9C C8C N2B C8B -35(4) . . . . no C12C C8C N2B C8B 144(5) . . . . no C9C C8C N2B N1B -177.7(10) . . . . no C12C C8C N2B N1B 0.8(16) . . . . no C7B N1B N2B C8B -162.0(16) . . . . no C7B N1B N2B C8C -146.3(9) . . . . no _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.198 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.047 _chemical_name_common "R-N'-3-methylcyclopentylidene-4-hydroxy benzohydrazide" data_1ortLT _database_code_depnum_ccdc_archive 'CCDC 905799' #TrackingRef '1ortLTdepnew.cif' _audit_creation_method SHELXL-97 _database_code_depnum_ccdc_archive 905799 _chemical_name_systematic ; rac-N'-3-methylcyclopentylidene-4-hydroxy benzohydrazide ; _chemical_enantioexcess_crystal 0.0 _chemical_formula_moiety 'C13 H16 N2 O2' _chemical_formula_sum 'C13 H16 N2 O2' _chemical_formula_weight 232.28 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 9.586(3) _cell_length_b 10.369(5) _cell_length_c 12.306(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1223.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 55 _cell_measurement_theta_min 2.571 _cell_measurement_theta_max 10.210 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9663 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_detector 'CCD plate' _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method ; CCD rotation images, thick slices ; loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _diffrn_reflns_number 6779 _diffrn_reflns_av_R_equivalents 0.0720 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2411 _reflns_number_gt 1273 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement ; Dirax/lsq (Duisenberg et al., 2000) ; _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_structure_solution 'SIR97 (Altomare at al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al, 2008). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.7734P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2411 _refine_ls_number_parameters 189 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.1442 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1678(5) 1.1158(5) 0.1138(5) 0.0609(12) Uani 1 1 d . . . C2 C 0.0227(5) 1.1063(5) 0.1118(5) 0.0749(15) Uani 1 1 d . . . H2 H -0.0309 1.1640 0.0687 0.090 Uiso 1 1 calc R . . C3 C -0.0418(5) 1.0130(6) 0.1724(5) 0.0813(17) Uani 1 1 d . . . H3 H -0.1406 1.0071 0.1709 0.098 Uiso 1 1 calc R . . C4 C 0.0336(5) 0.9263(5) 0.2363(4) 0.0582(13) Uani 1 1 d . . . C5 C 0.1770(5) 0.9392(5) 0.2387(5) 0.0597(13) Uani 1 1 d . . . H5 H 0.2308 0.8827 0.2828 0.072 Uiso 1 1 calc R . . C6 C 0.2434(5) 1.0330(5) 0.1782(5) 0.0628(13) Uani 1 1 d . . . H6 H 0.3421 1.0404 0.1811 0.075 Uiso 1 1 calc R . . C7 C -0.0457(5) 0.8315(5) 0.2989(4) 0.0580(12) Uani 1 1 d . . . N1 N 0.0237(3) 0.7323(3) 0.3466(3) 0.0525(9) Uani 1 1 d . A . H1N H 0.1161 0.7122 0.3368 0.063 Uiso 1 1 d R . . N2 N -0.0526(4) 0.6583(3) 0.4206(4) 0.0548(10) Uani 1 1 d D . . O1 O 0.2378(3) 1.2063(3) 0.0553(3) 0.0719(10) Uani 1 1 d . . . H1O H 0.1795 1.2497 0.0046 0.086 Uiso 1 1 d R . . O2 O -0.1739(3) 0.8380(3) 0.3089(3) 0.0794(11) Uani 1 1 d . . . C8A C -0.025(2) 0.5523(10) 0.4538(16) 0.048(3) Uiso 0.367(9) 1 d PD A 1 C9A C 0.0644(14) 0.4606(9) 0.3927(12) 0.051(3) Uiso 0.367(9) 1 d PD A 1 H9A1 H 0.1609 0.4613 0.4212 0.062 Uiso 0.367(9) 1 calc PR A 1 H9A2 H 0.0664 0.4827 0.3144 0.062 Uiso 0.367(9) 1 calc PR A 1 C10A C -0.0045(15) 0.3286(9) 0.4109(9) 0.059(4) Uiso 0.367(9) 1 d PD A 1 H10A H -0.0824 0.3167 0.3578 0.071 Uiso 0.367(9) 1 calc PR A 1 C11A C -0.0639(18) 0.3448(12) 0.5247(10) 0.079(5) Uiso 0.367(9) 1 d PD A 1 H11A H -0.1416 0.2834 0.5365 0.094 Uiso 0.367(9) 1 calc PR A 1 H11B H 0.0091 0.3278 0.5798 0.094 Uiso 0.367(9) 1 calc PR A 1 C12A C -0.116(2) 0.4819(13) 0.5348(16) 0.065(3) Uiso 0.367(9) 1 d PD A 1 H12A H -0.2158 0.4885 0.5153 0.078 Uiso 0.367(9) 1 calc PR A 1 H12B H -0.1021 0.5156 0.6093 0.078 Uiso 0.367(9) 1 calc PR A 1 C13A C 0.0954(18) 0.2166(12) 0.4027(15) 0.103(5) Uiso 0.367(9) 1 d PD A 1 H13A H 0.1347 0.2133 0.3293 0.154 Uiso 0.367(9) 1 calc PR A 1 H13B H 0.0454 0.1361 0.4179 0.154 Uiso 0.367(9) 1 calc PR A 1 H13C H 0.1708 0.2277 0.4557 0.154 Uiso 0.367(9) 1 calc PR A 1 C8B C -0.004(3) 0.5344(12) 0.410(3) 0.048(4) Uiso 0.280(10) 1 d PD A 2 C9B C -0.077(2) 0.4303(14) 0.4700(19) 0.061(5) Uiso 0.280(10) 1 d PD A 2 H9B1 H -0.1682 0.4102 0.4357 0.073 Uiso 0.280(10) 1 calc PR A 2 H9B2 H -0.0937 0.4558 0.5465 0.073 Uiso 0.280(10) 1 calc PR A 2 C10B C 0.0211(15) 0.3146(11) 0.4636(11) 0.045(4) Uiso 0.280(10) 1 d PD A 2 H10B H 0.0939 0.3195 0.5217 0.055 Uiso 0.280(10) 1 calc PR A 2 C11B C 0.0862(18) 0.3343(14) 0.3513(12) 0.067(5) Uiso 0.280(10) 1 d PD A 2 H11C H 0.1770 0.2892 0.3469 0.081 Uiso 0.280(10) 1 calc PR A 2 H11D H 0.0239 0.2992 0.2944 0.081 Uiso 0.280(10) 1 calc PR A 2 C12B C 0.106(2) 0.4770(15) 0.3353(19) 0.061(4) Uiso 0.280(10) 1 d PD A 2 H12C H 0.0900 0.5020 0.2587 0.074 Uiso 0.280(10) 1 calc PR A 2 H12D H 0.2011 0.5043 0.3572 0.074 Uiso 0.280(10) 1 calc PR A 2 C13B C -0.054(2) 0.1863(15) 0.4677(18) 0.097(7) Uiso 0.280(10) 1 d PD A 2 H13D H -0.1059 0.1795 0.5362 0.145 Uiso 0.280(10) 1 calc PR A 2 H13E H 0.0137 0.1160 0.4629 0.145 Uiso 0.280(10) 1 calc PR A 2 H13F H -0.1197 0.1806 0.4066 0.145 Uiso 0.280(10) 1 calc PR A 2 C8C C -0.024(4) 0.537(2) 0.442(3) 0.048(3) Uiso 0.202(8) 1 d PD A 3 C9C C 0.102(3) 0.4650(17) 0.407(2) 0.051(3) Uiso 0.202(8) 1 d PD A 3 H9C1 H 0.1871 0.4993 0.4426 0.062 Uiso 0.202(8) 1 calc PR A 3 H9C2 H 0.1146 0.4704 0.3270 0.062 Uiso 0.202(8) 1 calc PR A 3 C10C C 0.074(2) 0.3256(16) 0.4422(15) 0.059(4) Uiso 0.202(8) 1 d PD A 3 H10C H 0.1649 0.2827 0.4602 0.071 Uiso 0.202(8) 1 calc PR A 3 C11C C -0.008(3) 0.347(2) 0.5460(16) 0.079(5) Uiso 0.202(8) 1 d PD A 3 H11E H -0.0652 0.2693 0.5627 0.094 Uiso 0.202(8) 1 calc PR A 3 H11F H 0.0556 0.3624 0.6078 0.094 Uiso 0.202(8) 1 calc PR A 3 C12C C -0.102(4) 0.462(3) 0.528(3) 0.065(3) Uiso 0.202(8) 1 d PD A 3 H12E H -0.1118 0.5129 0.5959 0.078 Uiso 0.202(8) 1 calc PR A 3 H12F H -0.1950 0.4354 0.5025 0.078 Uiso 0.202(8) 1 calc PR A 3 C13C C -0.003(3) 0.245(2) 0.360(2) 0.103(5) Uiso 0.202(8) 1 d PD A 3 H13G H 0.0608 0.2194 0.3018 0.154 Uiso 0.202(8) 1 calc PR A 3 H13H H -0.0798 0.2960 0.3291 0.154 Uiso 0.202(8) 1 calc PR A 3 H13I H -0.0409 0.1682 0.3954 0.154 Uiso 0.202(8) 1 calc PR A 3 C8D C 0.000(6) 0.536(2) 0.417(6) 0.048(4) Uiso 0.151(9) 1 d PD A 4 C9D C -0.072(4) 0.443(2) 0.489(4) 0.061(5) Uiso 0.151(9) 1 d PD A 4 H9D1 H -0.1729 0.4610 0.4935 0.073 Uiso 0.151(9) 1 calc PR A 4 H9D2 H -0.0315 0.4443 0.5631 0.073 Uiso 0.151(9) 1 calc PR A 4 C10D C -0.045(2) 0.313(2) 0.434(2) 0.045(4) Uiso 0.151(9) 1 d PD A 4 H10D H -0.1086 0.3017 0.3701 0.055 Uiso 0.151(9) 1 calc PR A 4 C11D C 0.105(3) 0.332(2) 0.394(3) 0.067(5) Uiso 0.151(9) 1 d PD A 4 H11G H 0.1717 0.3141 0.4537 0.081 Uiso 0.151(9) 1 calc PR A 4 H11H H 0.1256 0.2721 0.3333 0.081 Uiso 0.151(9) 1 calc PR A 4 C12D C 0.118(4) 0.470(3) 0.357(4) 0.061(4) Uiso 0.151(9) 1 d PD A 4 H12G H 0.1069 0.4768 0.2771 0.074 Uiso 0.151(9) 1 calc PR A 4 H12H H 0.2100 0.5065 0.3777 0.074 Uiso 0.151(9) 1 calc PR A 4 C13D C -0.056(4) 0.198(3) 0.508(3) 0.097(7) Uiso 0.151(9) 1 d PD A 4 H13J H -0.0435 0.1183 0.4665 0.145 Uiso 0.151(9) 1 calc PR A 4 H13K H -0.1488 0.1973 0.5424 0.145 Uiso 0.151(9) 1 calc PR A 4 H13L H 0.0155 0.2034 0.5648 0.145 Uiso 0.151(9) 1 calc PR A 4 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 C1 0.035(2) 0.072(3) 0.076(3) 0.014(3) -0.002(3) -0.011(2) C2 0.039(3) 0.087(3) 0.099(4) 0.037(3) -0.004(3) -0.003(3) C3 0.034(3) 0.113(4) 0.097(4) 0.040(4) -0.007(3) -0.006(3) C4 0.032(2) 0.070(3) 0.073(3) 0.010(3) -0.011(3) -0.008(2) C5 0.035(2) 0.065(3) 0.080(3) 0.006(3) -0.008(3) 0.000(2) C6 0.029(3) 0.075(3) 0.085(3) 0.013(3) -0.006(3) -0.006(2) C7 0.034(3) 0.072(3) 0.068(3) 0.006(3) -0.005(3) -0.007(2) N1 0.0322(19) 0.054(2) 0.071(2) -0.002(2) 0.000(2) -0.0015(17) N2 0.038(2) 0.054(2) 0.073(2) 0.007(2) -0.0048(19) -0.0054(17) O1 0.046(2) 0.085(2) 0.084(2) 0.022(2) -0.0025(19) -0.0198(17) O2 0.0371(18) 0.089(2) 0.112(3) 0.041(2) -0.008(2) -0.0075(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 O1 1.360(5) . no C1 C6 1.376(6) . no C1 C2 1.394(6) . no C2 C3 1.369(7) . no C2 H2 0.9500 . no C3 C4 1.396(6) . no C3 H3 0.9500 . no C4 C5 1.381(6) . no C4 C7 1.462(6) . no C5 C6 1.380(7) . no C5 H5 0.9500 . no C6 H6 0.9500 . no C7 O2 1.237(5) . no C7 N1 1.359(6) . no N1 N2 1.398(5) . no N1 H1N 0.9172 . no N2 C8A 1.202(11) . no N2 C8C 1.315(15) . no N2 C8D 1.361(19) . no N2 C8B 1.374(12) . no O1 H1O 0.9513 . no C8A C9A 1.485(7) . no C8A C12A 1.510(7) . no C9A C10A 1.536(8) . no C9A H9A1 0.9900 . no C9A H9A2 0.9900 . no C10A C13A 1.508(8) . no C10A C11A 1.521(8) . no C10A H10A 1.0000 . no C11A C12A 1.511(8) . no C11A H11A 0.9900 . no C11A H11B 0.9900 . no C12A H12A 0.9900 . no C12A H12B 0.9900 . no C13A H13A 0.9800 . no C13A H13B 0.9800 . no C13A H13C 0.9800 . no C8B C9B 1.487(10) . no C8B C12B 1.519(10) . no C9B C10B 1.529(11) . no C9B H9B1 0.9900 . no C9B H9B2 0.9900 . no C10B C13B 1.515(11) . no C10B C11B 1.530(12) . no C10B H10B 1.0000 . no C11B C12B 1.505(11) . no C11B H11C 0.9900 . no C11B H11D 0.9900 . no C12B H12C 0.9900 . no C12B H12D 0.9900 . no C13B H13D 0.9800 . no C13B H13E 0.9800 . no C13B H13F 0.9800 . no C8C C9C 1.484(11) . no C8C C12C 1.517(10) . no C9C C10C 1.533(11) . no C9C H9C1 0.9900 . no C9C H9C2 0.9900 . no C10C C13C 1.507(11) . no C10C C11C 1.520(12) . no C10C H10C 1.0000 . no C11C C12C 1.508(11) . no C11C H11E 0.9900 . no C11C H11F 0.9900 . no C12C H12E 0.9900 . no C12C H12F 0.9900 . no C13C H13G 0.9800 . no C13C H13H 0.9800 . no C13C H13I 0.9800 . no C8D C9D 1.489(11) . no C8D C12D 1.519(11) . no C9D C10D 1.533(11) . no C9D H9D1 0.9900 . no C9D H9D2 0.9900 . no C10D C13D 1.508(11) . no C10D C11D 1.528(12) . no C10D H10D 1.0000 . no C11D C12D 1.508(11) . no C11D H11G 0.9900 . no C11D H11H 0.9900 . no C12D H12G 0.9900 . no C12D H12H 0.9900 . no C13D H13J 0.9800 . no C13D H13K 0.9800 . no C13D H13L 0.9800 . no 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 O1 C1 C6 118.4(4) . . no O1 C1 C2 122.1(5) . . no C6 C1 C2 119.4(5) . . no C3 C2 C1 119.4(5) . . no C3 C2 H2 120.3 . . no C1 C2 H2 120.3 . . no C2 C3 C4 121.9(5) . . no C2 C3 H3 119.1 . . no C4 C3 H3 119.1 . . no C5 C4 C3 117.7(5) . . no C5 C4 C7 124.8(4) . . no C3 C4 C7 117.4(4) . . no C6 C5 C4 121.0(5) . . no C6 C5 H5 119.5 . . no C4 C5 H5 119.5 . . no C1 C6 C5 120.5(5) . . no C1 C6 H6 119.7 . . no C5 C6 H6 119.7 . . no O2 C7 N1 119.0(5) . . no O2 C7 C4 122.2(5) . . no N1 C7 C4 118.8(4) . . no C7 N1 N2 116.2(3) . . no C7 N1 H1N 126.0 . . no N2 N1 H1N 117.8 . . no C8A N2 C8C 8(3) . . no C8A N2 C8D 23(3) . . no C8C N2 C8D 16(2) . . no C8A N2 C8B 26.3(15) . . no C8C N2 C8B 18.7(19) . . no C8D N2 C8B 4(5) . . no C8A N2 N1 127.5(8) . . no C8C N2 N1 123.0(14) . . no C8D N2 N1 106.9(18) . . no C8B N2 N1 105.8(9) . . no C1 O1 H1O 112.5 . . no N2 C8A C9A 122.7(12) . . no N2 C8A C12A 122.7(12) . . no C9A C8A C12A 111.0(7) . . no C8A C9A C10A 104.4(7) . . no C8A C9A H9A1 110.9 . . no C10A C9A H9A1 110.9 . . no C8A C9A H9A2 110.9 . . no C10A C9A H9A2 110.9 . . no H9A1 C9A H9A2 108.9 . . no C13A C10A C11A 112.6(10) . . no C13A C10A C9A 113.8(10) . . no C11A C10A C9A 101.3(8) . . no C13A C10A H10A 109.6 . . no C11A C10A H10A 109.6 . . no C9A C10A H10A 109.6 . . no C12A C11A C10A 107.6(8) . . no C12A C11A H11A 110.2 . . no C10A C11A H11A 110.2 . . no C12A C11A H11B 110.2 . . no C10A C11A H11B 110.2 . . no H11A C11A H11B 108.5 . . no C8A C12A C11A 102.2(7) . . no C8A C12A H12A 111.3 . . no C11A C12A H12A 111.3 . . no C8A C12A H12B 111.3 . . no C11A C12A H12B 111.3 . . no H12A C12A H12B 109.2 . . no C10A C13A H13A 109.5 . . no C10A C13A H13B 109.5 . . no H13A C13A H13B 109.5 . . no C10A C13A H13C 109.5 . . no H13A C13A H13C 109.5 . . no H13B C13A H13C 109.5 . . no N2 C8B C9B 117.9(14) . . no N2 C8B C12B 131.4(15) . . no C9B C8B C12B 110.3(8) . . no C8B C9B C10B 104.5(9) . . no C8B C9B H9B1 110.8 . . no C10B C9B H9B1 110.8 . . no C8B C9B H9B2 110.8 . . no C10B C9B H9B2 110.8 . . no H9B1 C9B H9B2 108.9 . . no C13B C10B C9B 113.1(11) . . no C13B C10B C11B 110.0(11) . . no C9B C10B C11B 101.2(9) . . no C13B C10B H10B 110.7 . . no C9B C10B H10B 110.7 . . no C11B C10B H10B 110.7 . . no C12B C11B C10B 107.6(9) . . no C12B C11B H11C 110.2 . . no C10B C11B H11C 110.2 . . no C12B C11B H11D 110.2 . . no C10B C11B H11D 110.2 . . no H11C C11B H11D 108.5 . . no C11B C12B C8B 102.6(8) . . no C11B C12B H12C 111.3 . . no C8B C12B H12C 111.3 . . no C11B C12B H12D 111.3 . . no C8B C12B H12D 111.3 . . no H12C C12B H12D 109.2 . . no C10B C13B H13D 109.5 . . no C10B C13B H13E 109.5 . . no H13D C13B H13E 109.5 . . no C10B C13B H13F 109.5 . . no H13D C13B H13F 109.5 . . no H13E C13B H13F 109.5 . . no N2 C8C C9C 127(2) . . no N2 C8C C12C 122(2) . . no C9C C8C C12C 110.3(9) . . no C8C C9C C10C 104.4(9) . . no C8C C9C H9C1 110.9 . . no C10C C9C H9C1 110.9 . . no C8C C9C H9C2 110.9 . . no C10C C9C H9C2 110.9 . . no H9C1 C9C H9C2 108.9 . . no C13C C10C C11C 112.7(13) . . no C13C C10C C9C 114.6(12) . . no C11C C10C C9C 101.3(10) . . no C13C C10C H10C 109.3 . . no C11C C10C H10C 109.3 . . no C9C C10C H10C 109.3 . . no C12C C11C C10C 107.5(11) . . no C12C C11C H11E 110.2 . . no C10C C11C H11E 110.2 . . no C12C C11C H11F 110.2 . . no C10C C11C H11F 110.2 . . no H11E C11C H11F 108.5 . . no C11C C12C C8C 102.5(10) . . no C11C C12C H12E 111.3 . . no C8C C12C H12E 111.3 . . no C11C C12C H12F 111.3 . . no C8C C12C H12F 111.3 . . no H12E C12C H12F 109.2 . . no C10C C13C H13G 109.5 . . no C10C C13C H13H 109.5 . . no H13G C13C H13H 109.5 . . no C10C C13C H13I 109.5 . . no H13G C13C H13I 109.5 . . no H13H C13C H13I 109.5 . . no N2 C8D C9D 114(3) . . no N2 C8D C12D 136(3) . . no C9D C8D C12D 109.7(10) . . no C8D C9D C10D 103.3(13) . . no C8D C9D H9D1 111.1 . . no C10D C9D H9D1 111.1 . . no C8D C9D H9D2 111.1 . . no C10D C9D H9D2 111.1 . . no H9D1 C9D H9D2 109.1 . . no C13D C10D C11D 111.5(13) . . no C13D C10D C9D 114.2(14) . . no C11D C10D C9D 100.7(11) . . no C13D C10D H10D 110.0 . . no C11D C10D H10D 110.0 . . no C9D C10D H10D 110.0 . . no C12D C11D C10D 107.4(12) . . no C12D C11D H11G 110.2 . . no C10D C11D H11G 110.2 . . no C12D C11D H11H 110.2 . . no C10D C11D H11H 110.2 . . no H11G C11D H11H 108.5 . . no C11D C12D C8D 102.8(9) . . no C11D C12D H12G 111.2 . . no C8D C12D H12G 111.2 . . no C11D C12D H12H 111.2 . . no C8D C12D H12H 111.2 . . no H12G C12D H12H 109.1 . . no C10D C13D H13J 109.5 . . no C10D C13D H13K 109.5 . . no H13J C13D H13K 109.5 . . no C10D C13D H13L 109.5 . . no H13J C13D H13L 109.5 . . no H13K C13D H13L 109.5 . . no _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.178 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.040 _chemical_name_common "rac-N'-3-methylcyclopentylidene-4-hydroxy benzohydrazide" data_1monoLT _database_code_depnum_ccdc_archive 'CCDC 915064' #TrackingRef '1monoLTdepnew.cif' _audit_creation_method SHELXL-97 _database_code_depnum_ccdc_archive 915064 _chemical_name_systematic ; rac-N'-3-methylcyclopentylidene-4- hydroxybenzohydrazide ; _chemical_enantioexcess_crystal 0.0 _chemical_melting_point 465 _chemical_formula_moiety 'C13 H16 N2 O2' _chemical_formula_sum 'C13 H16 N2 O2' _chemical_formula_weight 232.28 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 5.190(3) _cell_length_b 18.133(6) _cell_length_c 12.562(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.79(3) _cell_angle_gamma 90.00 _cell_volume 1179.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 114 _cell_measurement_theta_min 3.95 _cell_measurement_theta_max 12.10 _exptl_crystal_description 'flat needle' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9567 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_detector 'CCD plate' _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method ; CCD rotation images, thick slices ; loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _diffrn_reflns_number 7910 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.0746 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2001 _reflns_number_gt 1138 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement ; Dirax/lsq (Duisenberg et al., 2000) ; _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_structure_solution 'SIR97 (Altomare at al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al, 2008). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+1.9730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0116(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2001 _refine_ls_number_parameters 194 _refine_ls_number_restraints 109 _refine_ls_R_factor_all 0.1463 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.1604 _refine_ls_wR_factor_gt 0.1366 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0314(7) 0.3665(2) 0.5733(3) 0.0457(11) Uani 1 1 d . . . C2 C 0.1733(8) 0.3718(2) 0.5093(4) 0.0563(12) Uani 1 1 d . . . H2 H 0.2738 0.4156 0.5092 0.068 Uiso 1 1 calc R . . C3 C 0.2310(8) 0.3135(2) 0.4458(4) 0.0531(12) Uani 1 1 d . . . H3 H 0.3740 0.3173 0.4026 0.064 Uiso 1 1 calc R . . C4 C 0.0880(7) 0.2495(2) 0.4426(3) 0.0424(10) Uani 1 1 d . . . C5 C -0.1172(8) 0.2455(2) 0.5069(3) 0.0497(12) Uani 1 1 d . . . H5 H -0.2199 0.2021 0.5057 0.060 Uiso 1 1 calc R . . C6 C -0.1766(8) 0.3030(2) 0.5727(3) 0.0505(12) Uani 1 1 d . . . H6 H -0.3167 0.2988 0.6173 0.061 Uiso 1 1 calc R . . C7 C 0.1620(8) 0.1885(2) 0.3725(3) 0.0460(11) Uani 1 1 d . A . N2A N 0.004(4) 0.0801(8) 0.2759(18) 0.038(4) Uiso 0.334(9) 1 d PD A 1 C8A C -0.136(5) 0.0241(7) 0.2942(19) 0.037(3) Uiso 0.334(9) 1 d PD A 1 C9A C -0.103(4) -0.0474(6) 0.2384(11) 0.040(2) Uiso 0.334(9) 1 d PD A 1 H9A1 H 0.0775 -0.0542 0.2195 0.048 Uiso 0.334(9) 1 calc PR A 1 H9A2 H -0.2193 -0.0505 0.1728 0.048 Uiso 0.334(9) 1 calc PR A 1 C10A C -0.1767(19) -0.1042(5) 0.3212(9) 0.040(3) Uiso 0.334(9) 1 d PD A 1 H10A H -0.0293 -0.1097 0.3760 0.048 Uiso 0.334(9) 1 calc PR A 1 C11A C -0.400(2) -0.0660(7) 0.3726(13) 0.045(3) Uiso 0.334(9) 1 d PD A 1 H11A H -0.5641 -0.0734 0.3289 0.053 Uiso 0.334(9) 1 calc PR A 1 H11B H -0.4204 -0.0859 0.4450 0.053 Uiso 0.334(9) 1 calc PR A 1 C12A C -0.329(4) 0.0155(7) 0.3778(16) 0.039(3) Uiso 0.334(9) 1 d PD A 1 H12A H -0.4826 0.0468 0.3613 0.047 Uiso 0.334(9) 1 calc PR A 1 H12B H -0.2514 0.0287 0.4493 0.047 Uiso 0.334(9) 1 calc PR A 1 C13A C -0.247(4) -0.1794(6) 0.2765(15) 0.058(3) Uiso 0.334(9) 1 d PD A 1 H13A H -0.0947 -0.2017 0.2472 0.087 Uiso 0.334(9) 1 calc PR A 1 H13B H -0.3847 -0.1744 0.2198 0.087 Uiso 0.334(9) 1 calc PR A 1 H13C H -0.3062 -0.2108 0.3334 0.087 Uiso 0.334(9) 1 calc PR A 1 N2C N 0.044(4) 0.0784(8) 0.288(2) 0.038(4) Uiso 0.233(9) 1 d PD A 2 C8C C -0.117(7) 0.0261(10) 0.301(2) 0.037(3) Uiso 0.233(9) 1 d PD A 2 C9C C -0.122(5) -0.0413(10) 0.2341(18) 0.040(2) Uiso 0.233(9) 1 d PD A 2 H9C1 H 0.0468 -0.0669 0.2413 0.048 Uiso 0.233(9) 1 calc PR A 2 H9C2 H -0.1613 -0.0287 0.1581 0.048 Uiso 0.233(9) 1 calc PR A 2 C10C C -0.334(3) -0.0900(7) 0.2752(13) 0.040(3) Uiso 0.233(9) 1 d PD A 2 H10C H -0.5009 -0.0787 0.2339 0.048 Uiso 0.233(9) 1 calc PR A 2 C11C C -0.352(4) -0.0643(10) 0.3908(14) 0.045(3) Uiso 0.233(9) 1 d PD A 2 H11C H -0.5267 -0.0738 0.4150 0.053 Uiso 0.233(9) 1 calc PR A 2 H11D H -0.2240 -0.0907 0.4389 0.053 Uiso 0.233(9) 1 calc PR A 2 C12C C -0.295(5) 0.0183(9) 0.391(2) 0.039(3) Uiso 0.233(9) 1 d PD A 2 H12C H -0.4549 0.0473 0.3761 0.047 Uiso 0.233(9) 1 calc PR A 2 H12D H -0.2091 0.0343 0.4595 0.047 Uiso 0.233(9) 1 calc PR A 2 C13C C -0.281(5) -0.1717(8) 0.269(2) 0.058(3) Uiso 0.233(9) 1 d PD A 2 H13D H -0.2699 -0.1859 0.1938 0.087 Uiso 0.233(9) 1 calc PR A 2 H13E H -0.4214 -0.1991 0.2991 0.087 Uiso 0.233(9) 1 calc PR A 2 H13F H -0.1175 -0.1831 0.3087 0.087 Uiso 0.233(9) 1 calc PR A 2 N2B N 0.015(4) 0.0911(7) 0.2588(14) 0.038(5) Uiso 0.328(10) 1 d PD A 3 C8B C -0.107(4) 0.0297(7) 0.2605(14) 0.040(3) Uiso 0.328(10) 1 d PD A 3 C9B C -0.306(3) 0.0091(7) 0.3346(13) 0.043(3) Uiso 0.328(10) 1 d PD A 3 H9B1 H -0.4475 0.0459 0.3319 0.051 Uiso 0.328(10) 1 calc PR A 3 H9B2 H -0.2301 0.0056 0.4088 0.051 Uiso 0.328(10) 1 calc PR A 3 C10B C -0.406(2) -0.0661(6) 0.2949(10) 0.040(3) Uiso 0.328(10) 1 d PD A 3 H10B H -0.5506 -0.0588 0.2394 0.048 Uiso 0.328(10) 1 calc PR A 3 C11B C -0.172(2) -0.0989(6) 0.2424(13) 0.047(4) Uiso 0.328(10) 1 d PD A 3 H11E H -0.0442 -0.1192 0.2968 0.057 Uiso 0.328(10) 1 calc PR A 3 H11F H -0.2258 -0.1384 0.1914 0.057 Uiso 0.328(10) 1 calc PR A 3 C12B C -0.060(3) -0.0332(6) 0.1849(11) 0.040(3) Uiso 0.328(10) 1 d PD A 3 H12E H 0.1270 -0.0399 0.1758 0.047 Uiso 0.328(10) 1 calc PR A 3 H12F H -0.1511 -0.0251 0.1142 0.047 Uiso 0.328(10) 1 calc PR A 3 C13B C -0.495(3) -0.1151(9) 0.3822(13) 0.073(5) Uiso 0.328(10) 1 d PD A 3 H13G H -0.6464 -0.0930 0.4124 0.110 Uiso 0.328(10) 1 calc PR A 3 H13H H -0.3560 -0.1205 0.4382 0.110 Uiso 0.328(10) 1 calc PR A 3 H13I H -0.5414 -0.1637 0.3526 0.110 Uiso 0.328(10) 1 calc PR A 3 N2D N 0.028(15) 0.085(3) 0.270(7) 0.038(5) Uiso 0.105(9) 1 d PD A 4 C8D C -0.129(10) 0.0310(15) 0.258(4) 0.040(3) Uiso 0.105(9) 1 d PD A 4 C9D C -0.287(11) 0.0028(18) 0.344(4) 0.043(3) Uiso 0.105(9) 1 d PD A 4 H9D1 H -0.4723 0.0147 0.3285 0.051 Uiso 0.105(9) 1 calc PR A 4 H9D2 H -0.2281 0.0235 0.4139 0.051 Uiso 0.105(9) 1 calc PR A 4 C10D C -0.240(6) -0.0805(18) 0.340(2) 0.040(3) Uiso 0.105(9) 1 d PD A 4 H10D H -0.0682 -0.0917 0.3766 0.048 Uiso 0.105(9) 1 calc PR A 4 C11D C -0.228(10) -0.0956(15) 0.220(3) 0.047(4) Uiso 0.105(9) 1 d PD A 4 H11G H -0.1142 -0.1384 0.2088 0.057 Uiso 0.105(9) 1 calc PR A 4 H11H H -0.4020 -0.1066 0.1873 0.057 Uiso 0.105(9) 1 calc PR A 4 C12D C -0.119(10) -0.0265(18) 0.171(2) 0.040(3) Uiso 0.105(9) 1 d PD A 4 H12G H 0.0603 -0.0346 0.1515 0.047 Uiso 0.105(9) 1 calc PR A 4 H12H H -0.2262 -0.0115 0.1064 0.047 Uiso 0.105(9) 1 calc PR A 4 C13D C -0.443(10) -0.126(2) 0.390(4) 0.073(5) Uiso 0.105(9) 1 d PD A 4 H13J H -0.4479 -0.1125 0.4655 0.110 Uiso 0.105(9) 1 calc PR A 4 H13K H -0.4011 -0.1784 0.3842 0.110 Uiso 0.105(9) 1 calc PR A 4 H13L H -0.6122 -0.1163 0.3533 0.110 Uiso 0.105(9) 1 calc PR A 4 N1 N -0.0323(6) 0.14198(17) 0.3421(3) 0.0488(9) Uani 1 1 d D . . H1N H -0.2042 0.1501 0.3568 0.059 Uiso 1 1 d R A . O1 O -0.0857(6) 0.42533(15) 0.6345(2) 0.0590(9) Uani 1 1 d . . . H1O H -0.2184 0.4164 0.6672 0.071 Uiso 1 1 calc R . . O2 O 0.3815(5) 0.17966(15) 0.3445(2) 0.0550(9) 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 C1 0.041(2) 0.042(3) 0.054(3) 0.004(2) 0.003(2) -0.0001(19) C2 0.052(3) 0.051(3) 0.068(3) -0.007(2) 0.017(2) -0.021(2) C3 0.043(2) 0.055(3) 0.063(3) -0.004(2) 0.017(2) -0.008(2) C4 0.035(2) 0.042(2) 0.050(3) 0.002(2) 0.005(2) 0.0014(18) C5 0.044(2) 0.041(3) 0.064(3) 0.000(2) 0.008(2) -0.0103(19) C6 0.041(2) 0.052(3) 0.060(3) -0.004(2) 0.012(2) -0.006(2) C7 0.035(2) 0.041(2) 0.062(3) 0.005(2) 0.002(2) -0.0016(19) N1 0.0375(19) 0.045(2) 0.065(3) -0.0108(18) 0.0121(17) 0.0005(16) O1 0.0533(18) 0.0519(19) 0.075(2) -0.0069(17) 0.0244(16) -0.0078(14) O2 0.0331(16) 0.0591(19) 0.073(2) -0.0104(16) 0.0089(15) 0.0016(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 O1 1.355(5) . no C1 C6 1.377(5) . no C1 C2 1.378(6) . no C2 C3 1.370(6) . no C2 H2 0.9500 . no C3 C4 1.376(5) . no C3 H3 0.9500 . no C4 C5 1.380(5) . no C4 C7 1.480(6) . no C5 C6 1.378(6) . no C5 H5 0.9500 . no C6 H6 0.9500 . no C7 O2 1.225(4) . no C7 N1 1.350(5) . no N2A C8A 1.277(8) . no N2A N1 1.417(7) . no C8A C9A 1.489(7) . no C8A C12A 1.507(7) . no C9A C10A 1.5301(11) . no C9A H9A1 0.9900 . no C9A H9A2 0.9900 . no C10A C13A 1.509(7) . no C10A C11A 1.5301(12) . no C10A H10A 1.0000 . no C11A C12A 1.524(7) . no C11A H11A 0.9900 . no C11A H11B 0.9900 . no C12A H12A 0.9900 . no C12A H12B 0.9900 . no C13A H13A 0.9800 . no C13A H13B 0.9800 . no C13A H13C 0.9800 . no N2C C8C 1.280(9) . no N2C N1 1.408(8) . no C8C C9C 1.482(10) . no C8C C12C 1.509(10) . no C9C C10C 1.528(9) . no C9C H9C1 0.9900 . no C9C H9C2 0.9900 . no C10C C13C 1.511(10) . no C10C C11C 1.534(9) . no C10C H10C 1.0000 . no C11C C12C 1.527(10) . no C11C H11C 0.9900 . no C11C H11D 0.9900 . no C12C H12C 0.9900 . no C12C H12D 0.9900 . no C13C H13D 0.9800 . no C13C H13E 0.9800 . no C13C H13F 0.9800 . no N2B C8B 1.280(8) . no N2B N1 1.428(7) . no C8B C9B 1.484(10) . no C8B C12B 1.514(10) . no C9B C10B 1.530(9) . no C9B H9B1 0.9900 . no C9B H9B2 0.9900 . no C10B C13B 1.509(10) . no C10B C11B 1.540(9) . no C10B H10B 1.0000 . no C11B C12B 1.529(9) . no C11B H11E 0.9900 . no C11B H11F 0.9900 . no C12B H12E 0.9900 . no C12B H12F 0.9900 . no C13B H13G 0.9800 . no C13B H13H 0.9800 . no C13B H13I 0.9800 . no N2D C8D 1.281(10) . no N2D N1 1.418(9) . no C8D C9D 1.489(10) . no C8D C12D 1.511(10) . no C9D C10D 1.532(10) . no C9D H9D1 0.9900 . no C9D H9D2 0.9900 . no C10D C13D 1.507(11) . no C10D C11D 1.531(10) . no C10D H10D 1.0000 . no C11D C12D 1.522(10) . no C11D H11G 0.9900 . no C11D H11H 0.9900 . no C12D H12G 0.9900 . no C12D H12H 0.9900 . no C13D H13J 0.9800 . no C13D H13K 0.9800 . no C13D H13L 0.9800 . no N1 H1N 0.9345 . no O1 H1O 0.8400 . no 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 O1 C1 C6 121.9(4) . . no O1 C1 C2 118.3(4) . . no C6 C1 C2 119.8(4) . . no C3 C2 C1 119.6(4) . . no C3 C2 H2 120.2 . . no C1 C2 H2 120.2 . . no C2 C3 C4 121.9(4) . . no C2 C3 H3 119.0 . . no C4 C3 H3 119.0 . . no C3 C4 C5 117.6(4) . . no C3 C4 C7 119.1(4) . . no C5 C4 C7 123.3(4) . . no C6 C5 C4 121.5(4) . . no C6 C5 H5 119.2 . . no C4 C5 H5 119.2 . . no C1 C6 C5 119.5(4) . . no C1 C6 H6 120.2 . . no C5 C6 H6 120.2 . . no O2 C7 N1 121.9(4) . . no O2 C7 C4 123.5(4) . . no N1 C7 C4 114.7(4) . . no C8A N2A N1 115.1(9) . . no N2A C8A C9A 121.5(9) . . no N2A C8A C12A 128.4(8) . . no C9A C8A C12A 109.8(7) . . no C8A C9A C10A 103.0(8) . . no C8A C9A H9A1 111.2 . . no C10A C9A H9A1 111.2 . . no C8A C9A H9A2 111.2 . . no C10A C9A H9A2 111.2 . . no H9A1 C9A H9A2 109.1 . . no C13A C10A C11A 113.2(8) . . no C13A C10A C9A 114.8(8) . . no C11A C10A C9A 102.3(7) . . no C13A C10A H10A 108.7 . . no C11A C10A H10A 108.7 . . no C9A C10A H10A 108.7 . . no C12A C11A C10A 105.5(7) . . no C12A C11A H11A 110.6 . . no C10A C11A H11A 110.6 . . no C12A C11A H11B 110.6 . . no C10A C11A H11B 110.6 . . no H11A C11A H11B 108.8 . . no C8A C12A C11A 104.0(6) . . no C8A C12A H12A 111.0 . . no C11A C12A H12A 111.0 . . no C8A C12A H12B 111.0 . . no C11A C12A H12B 111.0 . . no H12A C12A H12B 109.0 . . no C10A C13A H13A 109.5 . . no C10A C13A H13B 109.5 . . no H13A C13A H13B 109.5 . . no C10A C13A H13C 109.5 . . no H13A C13A H13C 109.5 . . no H13B C13A H13C 109.5 . . no C8C N2C N1 109.8(11) . . no N2C C8C C9C 121.7(10) . . no N2C C8C C12C 127.0(12) . . no C9C C8C C12C 110.8(7) . . no C8C C9C C10C 105.8(8) . . no C8C C9C H9C1 110.6 . . no C10C C9C H9C1 110.6 . . no C8C C9C H9C2 110.6 . . no C10C C9C H9C2 110.6 . . no H9C1 C9C H9C2 108.7 . . no C13C C10C C9C 114.2(11) . . no C13C C10C C11C 111.8(11) . . no C9C C10C C11C 103.6(8) . . no C13C C10C H10C 109.0 . . no C9C C10C H10C 109.0 . . no C11C C10C H10C 109.0 . . no C12C C11C C10C 105.7(9) . . no C12C C11C H11C 110.6 . . no C10C C11C H11C 110.6 . . no C12C C11C H11D 110.6 . . no C10C C11C H11D 110.6 . . no H11C C11C H11D 108.7 . . no C8C C12C C11C 102.9(8) . . no C8C C12C H12C 111.2 . . no C11C C12C H12C 111.2 . . no C8C C12C H12D 111.2 . . no C11C C12C H12D 111.2 . . no H12C C12C H12D 109.1 . . no C10C C13C H13D 109.5 . . no C10C C13C H13E 109.5 . . no H13D C13C H13E 109.5 . . no C10C C13C H13F 109.5 . . no H13D C13C H13F 109.5 . . no H13E C13C H13F 109.5 . . no C8B N2B N1 116.2(9) . . no N2B C8B C9B 126.4(9) . . no N2B C8B C12B 122.9(9) . . no C9B C8B C12B 110.6(7) . . no C8B C9B C10B 104.7(7) . . no C8B C9B H9B1 110.8 . . no C10B C9B H9B1 110.8 . . no C8B C9B H9B2 110.8 . . no C10B C9B H9B2 110.8 . . no H9B1 C9B H9B2 108.9 . . no C13B C10B C9B 113.7(9) . . no C13B C10B C11B 111.9(9) . . no C9B C10B C11B 103.0(7) . . no C13B C10B H10B 109.4 . . no C9B C10B H10B 109.4 . . no C11B C10B H10B 109.4 . . no C12B C11B C10B 103.7(7) . . no C12B C11B H11E 111.0 . . no C10B C11B H11E 111.0 . . no C12B C11B H11F 111.0 . . no C10B C11B H11F 111.0 . . no H11E C11B H11F 109.0 . . no C8B C12B C11B 102.0(7) . . no C8B C12B H12E 111.4 . . no C11B C12B H12E 111.4 . . no C8B C12B H12F 111.4 . . no C11B C12B H12F 111.4 . . no H12E C12B H12F 109.2 . . no C10B C13B H13G 109.5 . . no C10B C13B H13H 109.5 . . no H13G C13B H13H 109.5 . . no C10B C13B H13I 109.5 . . no H13G C13B H13I 109.5 . . no H13H C13B H13I 109.5 . . no C8D N2D N1 118(2) . . no N2D C8D C9D 123.5(17) . . no N2D C8D C12D 124.5(15) . . no C9D C8D C12D 109.3(9) . . no C8D C9D C10D 102.7(11) . . no C8D C9D H9D1 111.2 . . no C10D C9D H9D1 111.2 . . no C8D C9D H9D2 111.2 . . no C10D C9D H9D2 111.2 . . no H9D1 C9D H9D2 109.1 . . no C13D C10D C11D 113.0(13) . . no C13D C10D C9D 114.1(14) . . no C11D C10D C9D 103.0(11) . . no C13D C10D H10D 108.8 . . no C11D C10D H10D 108.8 . . no C9D C10D H10D 108.8 . . no C12D C11D C10D 107.0(10) . . no C12D C11D H11G 110.3 . . no C10D C11D H11G 110.3 . . no C12D C11D H11H 110.3 . . no C10D C11D H11H 110.3 . . no H11G C11D H11H 108.6 . . no C8D C12D C11D 104.2(9) . . no C8D C12D H12G 110.9 . . no C11D C12D H12G 110.9 . . no C8D C12D H12H 110.9 . . no C11D C12D H12H 110.9 . . no H12G C12D H12H 108.9 . . no C10D C13D H13J 109.5 . . no C10D C13D H13K 109.5 . . no H13J C13D H13K 109.5 . . no C10D C13D H13L 109.5 . . no H13J C13D H13L 109.5 . . no H13K C13D H13L 109.5 . . no C7 N1 N2C 114.8(9) . . no C7 N1 N2A 122.4(8) . . no N2C N1 N2A 10(2) . . no C7 N1 N2D 116(2) . . no N2C N1 N2D 11(5) . . no N2A N1 N2D 7.2(16) . . no C7 N1 N2B 116.8(8) . . no N2C N1 N2B 18.2(11) . . no N2A N1 N2B 12.2(11) . . no N2D N1 N2B 8(6) . . no C7 N1 H1N 123.4 . . no N2C N1 H1N 121.8 . . no N2A N1 H1N 113.9 . . no N2D N1 H1N 119.7 . . no N2B N1 H1N 117.3 . . no C1 O1 H1O 109.5 . . no 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 C1 C2 C3 -179.3(4) . . . . no C6 C1 C2 C3 -0.3(7) . . . . no C1 C2 C3 C4 0.9(7) . . . . no C2 C3 C4 C5 -0.5(7) . . . . no C2 C3 C4 C7 -179.7(4) . . . . no C3 C4 C5 C6 -0.6(6) . . . . no C7 C4 C5 C6 178.6(4) . . . . no O1 C1 C6 C5 178.3(4) . . . . no C2 C1 C6 C5 -0.8(6) . . . . no C4 C5 C6 C1 1.2(6) . . . . no C3 C4 C7 O2 25.2(6) . . . . no C5 C4 C7 O2 -154.0(4) . . . . no C3 C4 C7 N1 -155.6(4) . . . . no C5 C4 C7 N1 25.3(6) . . . . no N1 N2A C8A C9A -174(2) . . . . no N1 N2A C8A C12A -1(5) . . . . no N2A C8A C9A C10A 149(3) . . . . no C12A C8A C9A C10A -26(2) . . . . no C8A C9A C10A C13A 160.8(16) . . . . no C8A C9A C10A C11A 37.7(17) . . . . no C13A C10A C11A C12A -161.2(13) . . . . no C9A C10A C11A C12A -37.0(15) . . . . no N2A C8A C12A C11A -171(3) . . . . no C9A C8A C12A C11A 3(3) . . . . no C10A C11A C12A C8A 22(2) . . . . no N1 N2C C8C C9C 166(3) . . . . no N1 N2C C8C C12C -23(5) . . . . no N2C C8C C9C C10C 179(3) . . . . no C12C C8C C9C C10C 7(3) . . . . no C8C C9C C10C C13C -146(2) . . . . no C8C C9C C10C C11C -25(3) . . . . no C13C C10C C11C C12C 157.5(18) . . . . no C9C C10C C11C C12C 34(2) . . . . no N2C C8C C12C C11C -158(4) . . . . no C9C C8C C12C C11C 14(3) . . . . no C10C C11C C12C C8C -30(3) . . . . no N1 N2B C8B C9B 5(3) . . . . no N1 N2B C8B C12B -173.8(19) . . . . no N2B C8B C9B C10B 174(2) . . . . no C12B C8B C9B C10B -6.2(18) . . . . no C8B C9B C10B C13B 149.4(13) . . . . no C8B C9B C10B C11B 28.2(15) . . . . no C13B C10B C11B C12B -162.5(11) . . . . no C9B C10B C11B C12B -40.1(12) . . . . no N2B C8B C12B C11B 161.0(19) . . . . no C9B C8B C12B C11B -18.4(17) . . . . no C10B C11B C12B C8B 35.5(14) . . . . no N1 N2D C8D C9D -31(11) . . . . no N1 N2D C8D C12D 169(7) . . . . no N2D C8D C9D C10D -132(7) . . . . no C12D C8D C9D C10D 31(3) . . . . no C8D C9D C10D C13D -160(3) . . . . no C8D C9D C10D C11D -37(3) . . . . no C13D C10D C11D C12D 154(3) . . . . no C9D C10D C11D C12D 31(3) . . . . no N2D C8D C12D C11D 150(7) . . . . no C9D C8D C12D C11D -12(4) . . . . no C10D C11D C12D C8D -12(4) . . . . no O2 C7 N1 N2C 7.7(15) . . . . no C4 C7 N1 N2C -171.6(14) . . . . no O2 C7 N1 N2A -0.1(15) . . . . no C4 C7 N1 N2A -179.3(14) . . . . no O2 C7 N1 N2D -4(5) . . . . no C4 C7 N1 N2D 177(5) . . . . no O2 C7 N1 N2B -12.5(12) . . . . no C4 C7 N1 N2B 168.2(11) . . . . no C8C N2C N1 C7 153(2) . . . . no C8C N2C N1 N2A -67(6) . . . . no C8C N2C N1 N2D -107(13) . . . . no C8C N2C N1 N2B -106(4) . . . . no C8A N2A N1 C7 147(2) . . . . no C8A N2A N1 N2C 103(9) . . . . no C8A N2A N1 N2D 177(45) . . . . no C8A N2A N1 N2B -147(9) . . . . no C8D N2D N1 C7 165(6) . . . . no C8D N2D N1 N2C 79(9) . . . . no C8D N2D N1 N2A 13(37) . . . . no C8D N2D N1 N2B -99(22) . . . . no C8B N2B N1 C7 150.7(15) . . . . no C8B N2B N1 N2C 62(3) . . . . no C8B N2B N1 N2A 30(7) . . . . no C8B N2B N1 N2D 64(16) . . . . no _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.196 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.046 _chemical_name_common rac-N'-3-methylcyclopentylidene-4-hydroxybenzohydrazide