# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Roberto Centore' _publ_contact_author_email roberto.centore@unina.it _publ_author_name 'Roberto Centore' data_denaturato _database_code_depnum_ccdc_archive 'CCDC 835986' #TrackingRef '1LTdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-2-butylidene-4-hydroxybenzohydrazide ; _chemical_formula_moiety 'C11 H14 N2 O2' _chemical_formula_sum 'C11 H14 N2 O2' _chemical_formula_weight 206.24 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 9.916(7) _cell_length_b 9.185(6) _cell_length_c 11.738(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1069.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 525 _cell_measurement_theta_min 3.415 _cell_measurement_theta_max 23.180 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9905 _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 7382 _diffrn_reflns_av_R_equivalents 0.0948 _diffrn_reflns_av_sigmaI/netI 0.1233 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 28.13 _reflns_number_total 2404 _reflns_number_gt 1262 _reflns_threshold_expression >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)' _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. The methyl group C11 is affected by static disorder by rotation around the bond C8-C10. The two split positions were refined without constraints. The occupancy of the two positions is 0.57 for C11a and 0.43 for C11b. ; _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^)+(0.0479P)^2^+0.0000P] 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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5(2) _refine_ls_number_reflns 2404 _refine_ls_number_parameters 153 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1495 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 -0.1568(3) 1.1563(3) 0.1111(3) 0.0330(7) Uani 1 1 d . . . C2 C -0.0213(3) 1.1197(3) 0.1006(3) 0.0334(7) Uani 1 1 d . . . H2 H 0.0360 1.1729 0.0508 0.040 Uiso 1 1 calc R . . C3 C 0.0284(3) 1.0059(3) 0.1631(3) 0.0345(7) Uani 1 1 d . . . H3 H 0.1210 0.9810 0.1558 0.041 Uiso 1 1 calc R . . C4 C -0.0515(3) 0.9261(3) 0.2363(2) 0.0272(7) Uani 1 1 d . . . C5 C -0.1853(3) 0.9650(3) 0.2481(3) 0.0345(8) Uani 1 1 d . . . H5 H -0.2417 0.9131 0.2994 0.041 Uiso 1 1 calc R . . C6 C -0.2371(3) 1.0795(3) 0.1852(3) 0.0385(9) Uani 1 1 d . . . H6 H -0.3293 1.1054 0.1934 0.046 Uiso 1 1 calc R . . C7 C 0.0142(3) 0.8072(3) 0.3010(3) 0.0314(7) Uani 1 1 d . . . C8 C -0.0573(4) 0.4729(4) 0.4235(3) 0.0524(10) Uani 1 1 d . . . C9 C -0.1783(5) 0.4204(4) 0.3599(5) 0.0909(17) Uani 1 1 d . . . H9A H -0.1703 0.4478 0.2795 0.136 Uiso 1 1 calc R . . H9B H -0.2596 0.4648 0.3923 0.136 Uiso 1 1 calc R . . H9C H -0.1844 0.3142 0.3662 0.136 Uiso 1 1 calc R . . C10 C 0.0057(5) 0.3643(5) 0.5011(5) 0.0923(18) Uani 1 1 d . . . H10A H 0.0049 0.2707 0.4637 0.111 Uiso 0.572(11) 1 d PR . . H10B H -0.0550 0.3579 0.5672 0.111 Uiso 0.572(11) 1 d PR . . H10C H -0.0674 0.3098 0.5348 0.111 Uiso 0.428(11) 1 d PR . . H10D H 0.0476 0.4204 0.5624 0.111 Uiso 0.428(11) 1 d PR . . N1 N -0.0634(3) 0.6989(3) 0.3428(2) 0.0331(6) Uani 1 1 d . . . H1 H -0.148(3) 0.696(3) 0.331(3) 0.040 Uiso 1 1 d . . . N2 N -0.0012(3) 0.5980(3) 0.4149(3) 0.0401(7) Uani 1 1 d . . . O1 O -0.2116(2) 1.2685(2) 0.0514(2) 0.0465(6) Uani 1 1 d . . . H1O H -0.151(3) 1.299(3) -0.012(3) 0.056 Uiso 1 1 d . . . O2 O 0.13724(19) 0.8043(2) 0.3150(2) 0.0436(6) Uani 1 1 d . . . C11A C 0.1337(7) 0.3892(9) 0.5431(6) 0.058(3) Uani 0.572(11) 1 d P . . H11A H 0.1952 0.4107 0.4799 0.087 Uiso 0.572(11) 1 d PR . . H11B H 0.1314 0.4722 0.5956 0.087 Uiso 0.572(11) 1 d PR . . H11C H 0.1651 0.3025 0.5837 0.087 Uiso 0.572(11) 1 d PR . . C11B C 0.0904(17) 0.2705(17) 0.4671(14) 0.126(9) Uani 0.428(11) 1 d P . . H11D H 0.1230 0.2142 0.5324 0.189 Uiso 0.428(11) 1 d PR . . H11E H 0.0459 0.2051 0.4129 0.189 Uiso 0.428(11) 1 d PR . . H11F H 0.1667 0.3186 0.4297 0.189 Uiso 0.428(11) 1 d PR . . 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 0.0323(18) 0.0259(15) 0.0408(18) 0.0039(15) 0.0005(17) 0.0034(13) C2 0.0260(16) 0.0390(17) 0.0351(18) 0.0086(17) 0.0027(15) -0.0046(14) C3 0.0241(15) 0.0406(18) 0.0388(17) -0.0028(15) 0.0012(16) 0.0032(15) C4 0.0245(16) 0.0252(15) 0.0320(18) -0.0007(13) 0.0011(16) -0.0002(13) C5 0.0256(16) 0.0333(17) 0.045(2) 0.0011(16) 0.0051(16) -0.0003(14) C6 0.0239(18) 0.0394(19) 0.052(2) 0.0066(17) 0.0072(16) 0.0078(14) C7 0.0273(17) 0.0318(15) 0.0353(19) -0.0091(15) 0.0066(16) 0.0018(15) C8 0.047(2) 0.042(2) 0.068(3) 0.012(2) -0.005(2) 0.0034(17) C9 0.092(4) 0.045(2) 0.136(5) 0.009(3) -0.046(3) -0.013(2) C10 0.059(3) 0.083(3) 0.135(5) 0.069(3) -0.003(3) 0.011(3) N1 0.0320(13) 0.0310(13) 0.0364(16) 0.0027(13) -0.0061(15) 0.0028(13) N2 0.0389(16) 0.0358(15) 0.0454(16) 0.0097(16) -0.0052(13) 0.0028(13) O1 0.0355(13) 0.0460(14) 0.0579(15) 0.0189(12) 0.0124(13) 0.0119(11) O2 0.0257(12) 0.0454(12) 0.0597(16) 0.0074(12) -0.0012(12) 0.0040(11) C11A 0.058(5) 0.060(5) 0.055(5) 0.017(4) -0.012(4) -0.005(3) C11B 0.141(13) 0.109(13) 0.127(13) 0.063(11) 0.073(11) 0.067(11) _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(4) . no C1 C6 1.374(4) . no C1 C2 1.391(4) . no C2 C3 1.369(4) . no C2 H2 0.9500 . no C3 C4 1.379(4) . no C3 H3 0.9500 . no C4 C5 1.380(4) . no C4 C7 1.481(4) . no C5 C6 1.385(4) . no C5 H5 0.9500 . no C6 H6 0.9500 . no C7 O2 1.231(3) . no C7 N1 1.350(4) . no C8 N2 1.281(4) . no C8 C10 1.488(5) . no C8 C9 1.493(5) . no C9 H9A 0.9800 . no C9 H9B 0.9800 . no C9 H9C 0.9800 . no C10 C11B 1.268(13) . no C10 C11A 1.381(8) . no C10 H10A 0.9657 . no C10 H10B 0.9829 . no C10 H10C 0.9651 . no C10 H10D 0.9778 . no N1 N2 1.398(4) . no N1 H1 0.85(3) . no O1 H1O 1.00(4) . no C11A C11B 1.473(19) . no C11A H10D 0.9285 . no C11A H11A 0.9800 . no C11A H11B 0.9800 . no C11A H11C 0.9800 . no C11A H11F 1.5170 . no C11B H10A 0.8486 . no C11B H11C 1.5845 . no C11B H11D 0.9800 . no C11B H11E 0.9800 . no C11B H11F 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 119.0(3) . . no O1 C1 C2 121.6(3) . . no C6 C1 C2 119.4(3) . . no C3 C2 C1 119.0(3) . . no C3 C2 H2 120.5 . . no C1 C2 H2 120.5 . . no C2 C3 C4 122.2(3) . . no C2 C3 H3 118.9 . . no C4 C3 H3 118.9 . . no C3 C4 C5 118.5(3) . . no C3 C4 C7 117.3(3) . . no C5 C4 C7 124.2(3) . . no C4 C5 C6 119.9(3) . . no C4 C5 H5 120.0 . . no C6 C5 H5 120.0 . . no C1 C6 C5 120.9(3) . . no C1 C6 H6 119.6 . . no C5 C6 H6 119.6 . . no O2 C7 N1 120.0(3) . . no O2 C7 C4 121.3(3) . . no N1 C7 C4 118.6(3) . . no N2 C8 C10 117.9(4) . . no N2 C8 C9 126.8(4) . . no C10 C8 C9 115.3(4) . . no C8 C9 H9A 109.5 . . no C8 C9 H9B 109.5 . . no H9A C9 H9B 109.5 . . no C8 C9 H9C 109.5 . . no H9A C9 H9C 109.5 . . no H9B C9 H9C 109.5 . . no C11B C10 C11A 67.4(9) . . no C11B C10 C8 122.7(8) . . no C11A C10 C8 119.5(5) . . no C11B C10 H10A 42.0 . . no C11A C10 H10A 108.5 . . no C8 C10 H10A 108.4 . . no C11B C10 H10B 127.8 . . no C11A C10 H10B 106.9 . . no C8 C10 H10B 105.5 . . no H10A C10 H10B 107.5 . . no C11B C10 H10C 105.9 . . no C11A C10 H10C 129.1 . . no C8 C10 H10C 106.5 . . no H10A C10 H10C 73.7 . . no H10B C10 H10C 35.6 . . no C11B C10 H10D 108.0 . . no C11A C10 H10D 42.2 . . no C8 C10 H10D 106.0 . . no H10A C10 H10D 143.9 . . no H10B C10 H10D 73.2 . . no H10C C10 H10D 106.9 . . no C7 N1 N2 117.2(3) . . no C7 N1 H1 122(2) . . no N2 N1 H1 121(2) . . no C8 N2 N1 116.8(3) . . no C1 O1 H1O 111.2(19) . . no C10 C11A C11B 52.6(6) . . no C10 C11A H10D 45.0 . . no C11B C11A H10D 96.2 . . no C10 C11A H11A 109.6 . . no C11B C11A H11A 82.6 . . no H10D C11A H11A 134.0 . . no C10 C11A H11B 109.4 . . no C11B C11A H11B 161.8 . . no H10D C11A H11B 65.6 . . no H11A C11A H11B 109.5 . . no C10 C11A H11C 109.4 . . no C11B C11A H11C 77.6 . . no H10D C11A H11C 115.2 . . no H11A C11A H11C 109.5 . . no H11B C11A H11C 109.5 . . no C10 C11A H11F 79.3 . . no C11B C11A H11F 38.2 . . no H10D C11A H11F 123.0 . . no H11A C11A H11F 44.6 . . no H11B C11A H11F 152.8 . . no H11C C11A H11F 90.6 . . no C10 C11B C11A 59.9(8) . . no C10 C11B H10A 49.6 . . no C11A C11B H10A 108.6 . . no C10 C11B H11C 84.9 . . no C11A C11B H11C 37.2 . . no H10A C11B H11C 120.5 . . no C10 C11B H11D 109.3 . . no C11A C11B H11D 79.7 . . no H10A C11B H11D 111.5 . . no H11C C11B H11D 42.9 . . no C10 C11B H11E 108.8 . . no C11A C11B H11E 168.0 . . no H10A C11B H11E 61.3 . . no H11C C11B H11E 152.3 . . no H11D C11B H11E 109.5 . . no C10 C11B H11F 110.3 . . no C11A C11B H11F 73.3 . . no H10A C11B H11F 138.6 . . no H11C C11B H11F 86.7 . . no H11D C11B H11F 109.5 . . no H11E C11B H11F 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 179.8(3) . . . . no C6 C1 C2 C3 1.2(5) . . . . no C1 C2 C3 C4 0.0(5) . . . . no C2 C3 C4 C5 -1.3(5) . . . . no C2 C3 C4 C7 -178.9(3) . . . . no C3 C4 C5 C6 1.5(5) . . . . no C7 C4 C5 C6 178.9(3) . . . . no O1 C1 C6 C5 -179.7(3) . . . . no C2 C1 C6 C5 -1.0(5) . . . . no C4 C5 C6 C1 -0.4(5) . . . . no C3 C4 C7 O2 20.1(5) . . . . no C5 C4 C7 O2 -157.3(3) . . . . no C3 C4 C7 N1 -158.4(3) . . . . no C5 C4 C7 N1 24.2(5) . . . . no N2 C8 C10 C11B -93.4(13) . . . . no C9 C8 C10 C11B 84.4(13) . . . . no N2 C8 C10 C11A -12.7(8) . . . . no C9 C8 C10 C11A 165.1(6) . . . . no O2 C7 N1 N2 9.0(4) . . . . no C4 C7 N1 N2 -172.4(3) . . . . no C10 C8 N2 N1 -179.1(4) . . . . no C9 C8 N2 N1 3.4(6) . . . . no C7 N1 N2 C8 -157.1(3) . . . . no C8 C10 C11A C11B -115.9(9) . . . . no C8 C10 C11B C11A 111.5(9) . . . . no _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.13 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.159 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.043 # Attachment '2phaseIIILTdep.cif' data_imacetiii-100 _database_code_depnum_ccdc_archive 'CCDC 835987' #TrackingRef '2phaseIIILTdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-2-propylidene-4-hydroxybenzohydrazide ; _chemical_formula_moiety 'C10 H12 N2 O2' _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 9.835(3) _cell_length_b 9.153(3) _cell_length_c 11.370(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1023.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 453 _cell_measurement_theta_min 3.409 _cell_measurement_theta_max 23.195 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9615 _exptl_absorpt_correction_T_max 0.9742 _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 5467 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1904 _reflns_number_gt 1722 _reflns_threshold_expression >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)' _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^)+(0.0646P)^2^+0.2261P] 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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(16) _refine_ls_number_reflns 1904 _refine_ls_number_parameters 135 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.8503(2) 1.1728(2) 0.7450(2) 0.0300(5) Uani 1 1 d . . . C2 C 0.9822(2) 1.1238(2) 0.7274(2) 0.0313(5) Uani 1 1 d . . . H2 H 1.0410 1.1742 0.6749 0.038 Uiso 1 1 calc R . . C3 C 1.0276(2) 1.0017(2) 0.7865(2) 0.0305(5) Uani 1 1 d . . . H3 H 1.1181 0.9689 0.7741 0.037 Uiso 1 1 calc R . . C4 C 0.9440(2) 0.92500(19) 0.8640(2) 0.0279(4) Uani 1 1 d . . . C5 C 0.8112(2) 0.9757(2) 0.8815(2) 0.0309(5) Uani 1 1 d . . . H5 H 0.7524 0.9256 0.9341 0.037 Uiso 1 1 calc R . . C6 C 0.7651(2) 1.0987(2) 0.8223(2) 0.0321(5) Uani 1 1 d . . . H6 H 0.6749 1.1325 0.8347 0.039 Uiso 1 1 calc R . . C7 C 1.0058(2) 0.8001(2) 0.9280(2) 0.0284(4) Uani 1 1 d . . . C8 C 0.9255(2) 0.4705(2) 1.0639(2) 0.0331(5) Uani 1 1 d . . . C9 C 0.7953(3) 0.4215(2) 1.0091(3) 0.0478(7) Uani 1 1 d . . . H9A H 0.7981 0.4405 0.9243 0.072 Uiso 1 1 calc R . . H9B H 0.7193 0.4752 1.0443 0.072 Uiso 1 1 calc R . . H9C H 0.7831 0.3166 1.0228 0.072 Uiso 1 1 calc R . . C10 C 0.9915(3) 0.3683(3) 1.1490(3) 0.0509(7) Uani 1 1 d . . . H10A H 1.0800 0.4079 1.1728 0.076 Uiso 1 1 calc R . . H10B H 1.0045 0.2729 1.1117 0.076 Uiso 1 1 calc R . . H10C H 0.9334 0.3573 1.2185 0.076 Uiso 1 1 calc R . . N1 N 0.92364(18) 0.69341(17) 0.97038(17) 0.0275(4) Uani 1 1 d . . . N2 N 0.98526(18) 0.59306(18) 1.04596(18) 0.0307(4) Uani 1 1 d . . . O1 O 0.80151(16) 1.29432(16) 0.69023(17) 0.0387(4) Uani 1 1 d . . . O2 O 1.12989(14) 0.79273(16) 0.93969(18) 0.0370(4) Uani 1 1 d . . . H1N H 0.836(3) 0.697(3) 0.963(3) 0.044 Uiso 1 1 d . . . H1O H 0.861(3) 1.317(3) 0.620(3) 0.044 Uiso 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 0.0279(10) 0.0268(8) 0.0353(12) 0.0015(9) -0.0023(9) 0.0011(7) C2 0.0271(10) 0.0320(10) 0.0350(12) 0.0018(9) 0.0023(9) -0.0010(7) C3 0.0238(9) 0.0320(9) 0.0356(12) -0.0008(9) 0.0015(9) 0.0019(7) C4 0.0253(9) 0.0231(8) 0.0353(12) -0.0012(8) 0.0008(8) 0.0004(7) C5 0.0242(10) 0.0268(9) 0.0418(14) 0.0028(9) 0.0045(9) -0.0011(7) C6 0.0235(9) 0.0308(9) 0.0420(14) 0.0023(9) 0.0034(9) 0.0037(7) C7 0.0263(9) 0.0262(8) 0.0327(12) -0.0029(8) -0.0029(9) 0.0015(7) C8 0.0322(10) 0.0280(9) 0.0391(13) 0.0004(9) 0.0007(9) 0.0033(8) C9 0.0453(13) 0.0313(10) 0.0669(19) 0.0039(12) -0.0116(14) -0.0087(9) C10 0.0535(15) 0.0388(12) 0.0603(19) 0.0159(13) -0.0047(14) 0.0044(10) N1 0.0243(9) 0.0251(7) 0.0332(11) 0.0023(7) -0.0024(7) 0.0020(6) N2 0.0303(9) 0.0268(7) 0.0349(10) 0.0018(7) -0.0034(7) 0.0035(6) O1 0.0322(8) 0.0359(8) 0.0480(11) 0.0125(8) 0.0063(7) 0.0092(6) O2 0.0209(7) 0.0351(8) 0.0549(12) 0.0059(7) 0.0001(7) 0.0022(5) _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 1.362(3) . no C1 C2 1.388(3) . no C1 C6 1.391(3) . no C2 C3 1.378(3) . no C2 H2 0.9500 . no C3 C4 1.395(3) . no C3 H3 0.9500 . no C4 C5 1.400(3) . no C4 C7 1.486(3) . no C5 C6 1.388(3) . no C5 H5 0.9500 . no C6 H6 0.9500 . no C7 O2 1.229(3) . no C7 N1 1.356(3) . no C8 N2 1.283(3) . no C8 C9 1.492(3) . no C8 C10 1.494(3) . no C9 H9A 0.9800 . no C9 H9B 0.9800 . no C9 H9C 0.9800 . no C10 H10A 0.9800 . no C10 H10B 0.9800 . no C10 H10C 0.9800 . no N1 N2 1.396(2) . no N1 H1N 0.86(3) . no O1 H1O 1.01(3) . 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 C2 121.8(2) . . no O1 C1 C6 118.38(19) . . no C2 C1 C6 119.78(19) . . no C3 C2 C1 119.6(2) . . no C3 C2 H2 120.2 . . no C1 C2 H2 120.2 . . no C2 C3 C4 121.69(17) . . no C2 C3 H3 119.2 . . no C4 C3 H3 119.2 . . no C3 C4 C5 118.22(18) . . no C3 C4 C7 117.09(17) . . no C5 C4 C7 124.58(19) . . no C6 C5 C4 120.30(19) . . no C6 C5 H5 119.8 . . no C4 C5 H5 119.8 . . no C5 C6 C1 120.36(19) . . no C5 C6 H6 119.8 . . no C1 C6 H6 119.8 . . no O2 C7 N1 120.93(19) . . no O2 C7 C4 120.11(18) . . no N1 C7 C4 118.94(17) . . no N2 C8 C9 126.1(2) . . no N2 C8 C10 116.8(2) . . no C9 C8 C10 117.1(2) . . no C8 C9 H9A 109.5 . . no C8 C9 H9B 109.5 . . no H9A C9 H9B 109.5 . . no C8 C9 H9C 109.5 . . no H9A C9 H9C 109.5 . . no H9B C9 H9C 109.5 . . no C8 C10 H10A 109.5 . . no C8 C10 H10B 109.5 . . no H10A C10 H10B 109.5 . . no C8 C10 H10C 109.5 . . no H10A C10 H10C 109.5 . . no H10B C10 H10C 109.5 . . no C7 N1 N2 115.69(17) . . no C7 N1 H1N 121.7(18) . . no N2 N1 H1N 121.5(19) . . no C8 N2 N1 118.30(18) . . no C1 O1 H1O 109.0(15) . . 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 178.9(2) . . . . no C6 C1 C2 C3 0.2(3) . . . . no C1 C2 C3 C4 0.1(4) . . . . no C2 C3 C4 C5 -0.3(3) . . . . no C2 C3 C4 C7 -176.6(2) . . . . no C3 C4 C5 C6 0.3(3) . . . . no C7 C4 C5 C6 176.2(2) . . . . no C4 C5 C6 C1 0.1(3) . . . . no O1 C1 C6 C5 -179.0(2) . . . . no C2 C1 C6 C5 -0.3(3) . . . . no C3 C4 C7 O2 21.3(3) . . . . no C5 C4 C7 O2 -154.7(2) . . . . no C3 C4 C7 N1 -157.1(2) . . . . no C5 C4 C7 N1 26.9(3) . . . . no O2 C7 N1 N2 12.0(3) . . . . no C4 C7 N1 N2 -169.64(18) . . . . no C9 C8 N2 N1 1.4(4) . . . . no C10 C8 N2 N1 -177.6(2) . . . . no C7 N1 N2 C8 -161.8(2) . . . . no _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.178 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.049 # Attachment '2phaseIIIRTdep.cif' data_imacetiii _database_code_depnum_ccdc_archive 'CCDC 835988' #TrackingRef '2phaseIIIRTdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-2-propylidene-4-hydroxybenzohydrazide ; _chemical_formula_moiety 'C10 H12 N2 O2' _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 9.875(2) _cell_length_b 9.103(3) _cell_length_c 11.590(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1041.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 472 _cell_measurement_theta_min 3.427 _cell_measurement_theta_max 20.186 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9621 _exptl_absorpt_correction_T_max 0.9750 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 293(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 5744 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2305 _reflns_number_gt 1777 _reflns_threshold_expression >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)' _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^)+(0.0383P)^2^+0.1263P] 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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.9(16) _refine_ls_number_reflns 2305 _refine_ls_number_parameters 135 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.1525(2) 1.1666(2) 0.0845(2) 0.0424(5) Uani 1 1 d . . . C2 C 0.0199(2) 1.1218(2) 0.06920(19) 0.0447(5) Uani 1 1 d . . . H2 H -0.0363 1.1719 0.0183 0.054 Uiso 1 1 calc R . . C3 C -0.02858(19) 1.0034(2) 0.1292(2) 0.0445(5) Uani 1 1 d . . . H3 H -0.1180 0.9744 0.1185 0.053 Uiso 1 1 calc R . . C4 C 0.05236(18) 0.9257(2) 0.20542(17) 0.0369(5) Uani 1 1 d . . . C5 C 0.1854(2) 0.9722(2) 0.2210(2) 0.0445(5) Uani 1 1 d . . . H5 H 0.2415 0.9221 0.2720 0.053 Uiso 1 1 calc R . . C6 C 0.2345(2) 1.0914(2) 0.1616(2) 0.0475(6) Uani 1 1 d . . . H6 H 0.3233 1.1219 0.1732 0.057 Uiso 1 1 calc R . . C7 C -0.01207(18) 0.8029(2) 0.26978(19) 0.0387(4) Uani 1 1 d . . . C8 C 0.0617(2) 0.4711(3) 0.4016(2) 0.0504(6) Uani 1 1 d . . . C9 C 0.1875(3) 0.4183(3) 0.3470(3) 0.0800(9) Uani 1 1 d . . . H9A H 0.2641 0.4604 0.3857 0.120 Uiso 1 1 calc R . . H9B H 0.1885 0.4469 0.2673 0.120 Uiso 1 1 calc R . . H9C H 0.1917 0.3131 0.3524 0.120 Uiso 1 1 calc R . . C10 C -0.0061(4) 0.3711(3) 0.4858(3) 0.0856(10) Uani 1 1 d . . . H10A H -0.0257 0.2789 0.4491 0.128 Uiso 1 1 calc R . . H10B H -0.0889 0.4151 0.5119 0.128 Uiso 1 1 calc R . . H10C H 0.0528 0.3548 0.5505 0.128 Uiso 1 1 calc R . . N1 N 0.06719(17) 0.69479(19) 0.31114(15) 0.0396(4) Uani 1 1 d . . . H1 H 0.156(3) 0.688(3) 0.310(2) 0.048 Uiso 1 1 d . . . N2 N 0.00517(19) 0.5950(2) 0.38578(17) 0.0450(4) Uani 1 1 d . . . O1 O 0.20457(16) 1.28463(19) 0.02802(16) 0.0576(5) Uani 1 1 d . . . H1O H 0.134(3) 1.322(3) -0.030(3) 0.069 Uiso 1 1 d . . . O2 O -0.13515(13) 0.79935(18) 0.28202(16) 0.0550(5) 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 0.0381(10) 0.0419(10) 0.0472(11) 0.0027(10) -0.0002(9) -0.0050(9) C2 0.0356(10) 0.0523(12) 0.0463(12) 0.0083(10) -0.0028(9) 0.0007(9) C3 0.0306(9) 0.0528(12) 0.0501(12) 0.0048(10) -0.0039(9) -0.0040(9) C4 0.0320(9) 0.0362(10) 0.0424(11) -0.0012(9) 0.0007(8) -0.0003(8) C5 0.0360(10) 0.0455(12) 0.0521(13) 0.0043(10) -0.0075(9) 0.0014(9) C6 0.0292(9) 0.0518(13) 0.0615(15) 0.0064(11) -0.0071(9) -0.0080(9) C7 0.0340(9) 0.0392(9) 0.0428(11) -0.0036(9) -0.0031(9) -0.0027(9) C8 0.0601(14) 0.0394(11) 0.0516(14) 0.0024(10) -0.0032(11) -0.0067(10) C9 0.0862(19) 0.0477(14) 0.106(3) 0.0049(16) 0.0161(18) 0.0177(14) C10 0.098(2) 0.0605(17) 0.099(3) 0.0288(17) 0.0096(19) -0.0097(16) N1 0.0358(8) 0.0369(8) 0.0462(10) 0.0040(7) 0.0061(8) -0.0018(7) N2 0.0474(10) 0.0407(9) 0.0469(10) 0.0044(8) 0.0052(8) -0.0045(8) O1 0.0457(8) 0.0589(10) 0.0681(11) 0.0215(9) -0.0110(8) -0.0144(8) O2 0.0309(7) 0.0559(9) 0.0783(12) 0.0132(9) 0.0019(8) -0.0035(7) _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 1.359(3) . no C1 C2 1.384(3) . no C1 C6 1.386(3) . no C2 C3 1.369(3) . no C2 H2 0.9300 . no C3 C4 1.385(3) . no C3 H3 0.9300 . no C4 C5 1.392(3) . no C4 C7 1.487(3) . no C5 C6 1.373(3) . no C5 H5 0.9300 . no C6 H6 0.9300 . no C7 O2 1.224(2) . no C7 N1 1.346(3) . no C8 N2 1.272(3) . no C8 C9 1.474(4) . no C8 C10 1.493(4) . no C9 H9A 0.9600 . no C9 H9B 0.9600 . no C9 H9C 0.9600 . no C10 H10A 0.9600 . no C10 H10B 0.9600 . no C10 H10C 0.9600 . no N1 N2 1.396(2) . no N1 H1 0.88(2) . no O1 H1O 1.03(3) . 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 C2 121.97(19) . . no O1 C1 C6 118.70(18) . . no C2 C1 C6 119.31(19) . . no C3 C2 C1 119.9(2) . . no C3 C2 H2 120.1 . . no C1 C2 H2 120.1 . . no C2 C3 C4 121.61(18) . . no C2 C3 H3 119.2 . . no C4 C3 H3 119.2 . . no C3 C4 C5 118.17(19) . . no C3 C4 C7 117.18(16) . . no C5 C4 C7 124.56(18) . . no C6 C5 C4 120.54(19) . . no C6 C5 H5 119.7 . . no C4 C5 H5 119.7 . . no C5 C6 C1 120.48(18) . . no C5 C6 H6 119.8 . . no C1 C6 H6 119.8 . . no O2 C7 N1 121.1(2) . . no O2 C7 C4 120.18(19) . . no N1 C7 C4 118.66(16) . . no N2 C8 C9 126.7(2) . . no N2 C8 C10 116.0(2) . . no C9 C8 C10 117.3(2) . . no C8 C9 H9A 109.5 . . no C8 C9 H9B 109.5 . . no H9A C9 H9B 109.5 . . no C8 C9 H9C 109.5 . . no H9A C9 H9C 109.5 . . no H9B C9 H9C 109.5 . . no C8 C10 H10A 109.5 . . no C8 C10 H10B 109.5 . . no H10A C10 H10B 109.5 . . no C8 C10 H10C 109.5 . . no H10A C10 H10C 109.5 . . no H10B C10 H10C 109.5 . . no C7 N1 N2 116.19(16) . . no C7 N1 H1 128.9(16) . . no N2 N1 H1 113.5(16) . . no C8 N2 N1 118.26(19) . . no C1 O1 H1O 108.9(15) . . 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 -179.1(2) . . . . no C6 C1 C2 C3 -0.6(3) . . . . no C1 C2 C3 C4 -0.3(4) . . . . no C2 C3 C4 C5 0.7(3) . . . . no C2 C3 C4 C7 177.5(2) . . . . no C3 C4 C5 C6 -0.3(3) . . . . no C7 C4 C5 C6 -176.8(2) . . . . no C4 C5 C6 C1 -0.5(4) . . . . no O1 C1 C6 C5 179.6(2) . . . . no C2 C1 C6 C5 1.0(3) . . . . no C3 C4 C7 O2 -21.6(3) . . . . no C5 C4 C7 O2 155.0(2) . . . . no C3 C4 C7 N1 156.7(2) . . . . no C5 C4 C7 N1 -26.8(3) . . . . no O2 C7 N1 N2 -11.5(3) . . . . no C4 C7 N1 N2 170.31(18) . . . . no C9 C8 N2 N1 -1.2(4) . . . . no C10 C8 N2 N1 177.7(2) . . . . no C7 N1 N2 C8 160.8(2) . . . . no _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.167 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.034 # Attachment '- 2phaseIIdep.cif' data_imacetii _database_code_depnum_ccdc_archive 'CCDC 835989' #TrackingRef '- 2phaseIIdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-2-propylidene-4-hydroxybenzohydrazide ; _chemical_formula_moiety 'C10 H12 N2 O2' _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 9.968(5) _cell_length_b 8.082(5) _cell_length_c 13.267(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1068.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 368(2) _cell_measurement_reflns_used 395 _cell_measurement_theta_min 3.686 _cell_measurement_theta_max 20.228 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9630 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 368(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 4875 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1607 _reflns_number_gt 1122 _reflns_threshold_expression >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)' _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. Because of the lack of heavy atoms, the Flack parameter was not considered. ; _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^)+(0.0850P)^2^+0.4220P] 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 none _refine_ls_number_reflns 1607 _refine_ls_number_parameters 135 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.2047 _refine_ls_wR_factor_gt 0.1763 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 0.1696(5) 1.1403(7) 0.0160(5) 0.0730(15) Uani 1 1 d . . . C2 C 0.0304(5) 1.1215(7) 0.0127(4) 0.0707(14) Uani 1 1 d . . . H2 H -0.0195 1.1773 -0.0358 0.085 Uiso 1 1 calc R . . C3 C -0.0323(5) 1.0209(6) 0.0808(5) 0.0714(14) Uani 1 1 d . . . H3 H -0.1253 1.0114 0.0793 0.086 Uiso 1 1 calc R . . C4 C 0.0398(5) 0.9334(6) 0.1518(4) 0.0634(13) Uani 1 1 d . . . C5 C 0.1789(6) 0.9552(7) 0.1534(5) 0.0825(17) Uani 1 1 d . . . H5 H 0.2294 0.8985 0.2011 0.099 Uiso 1 1 calc R . . C6 C 0.2431(5) 1.0581(8) 0.0863(5) 0.0864(17) Uani 1 1 d . . . H6 H 0.3357 1.0713 0.0890 0.104 Uiso 1 1 calc R . . C7 C -0.0350(5) 0.8239(7) 0.2209(4) 0.0655(14) Uani 1 1 d . . . C8 C 0.0087(6) 0.4504(7) 0.3440(5) 0.0904(19) Uani 1 1 d . . . C9 C 0.1187(9) 0.3708(8) 0.2884(10) 0.140(3) Uani 1 1 d . . . H9A H 0.1051 0.3853 0.2173 0.211 Uiso 1 1 calc R . . H9B H 0.1205 0.2548 0.3040 0.211 Uiso 1 1 calc R . . H9C H 0.2025 0.4202 0.3076 0.211 Uiso 1 1 calc R . . C10 C -0.0611(11) 0.3549(9) 0.4235(8) 0.139(3) Uani 1 1 d . . . H10A H -0.1257 0.4245 0.4564 0.209 Uiso 1 1 calc R . . H10B H 0.0031 0.3163 0.4720 0.209 Uiso 1 1 calc R . . H10C H -0.1061 0.2619 0.3936 0.209 Uiso 1 1 calc R . . N1 N 0.0310(5) 0.6910(5) 0.2573(4) 0.0682(12) Uani 1 1 d . . . N2 N -0.0353(5) 0.5971(5) 0.3291(4) 0.0748(13) Uani 1 1 d . . . O1 O 0.2352(4) 1.2401(6) -0.0499(4) 0.0967(14) Uani 1 1 d . . . O2 O -0.1537(3) 0.8505(4) 0.2420(4) 0.0876(13) Uani 1 1 d . . . H1N H 0.114(7) 0.679(8) 0.241(6) 0.105 Uiso 1 1 d . . . H1O H 0.167(8) 1.293(8) -0.098(5) 0.105 Uiso 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 0.057(3) 0.086(3) 0.076(3) 0.003(3) 0.001(3) -0.010(3) C2 0.057(3) 0.079(3) 0.076(4) 0.011(3) -0.004(3) -0.001(3) C3 0.045(2) 0.074(3) 0.096(4) 0.004(3) 0.001(3) 0.003(2) C4 0.052(2) 0.065(3) 0.074(3) -0.001(3) -0.003(3) 0.001(2) C5 0.069(3) 0.084(3) 0.095(4) 0.021(3) -0.017(3) -0.002(3) C6 0.044(2) 0.109(4) 0.106(4) 0.018(4) -0.001(4) -0.003(3) C7 0.054(3) 0.067(3) 0.076(4) -0.005(3) -0.002(3) -0.002(2) C8 0.077(3) 0.071(3) 0.122(5) 0.015(4) -0.016(4) -0.010(3) C9 0.113(6) 0.071(4) 0.238(11) 0.004(5) 0.014(6) 0.018(4) C10 0.155(7) 0.105(6) 0.158(8) 0.048(6) -0.002(6) -0.017(5) N1 0.064(2) 0.064(2) 0.077(3) 0.006(2) 0.003(3) 0.006(2) N2 0.073(3) 0.071(3) 0.080(3) 0.005(3) 0.001(2) 0.000(2) O1 0.062(2) 0.130(4) 0.098(3) 0.028(3) -0.004(2) -0.023(2) O2 0.0530(19) 0.079(2) 0.130(4) 0.015(2) 0.010(2) 0.0005(16) _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 1.357(7) . no C1 C6 1.359(8) . no C1 C2 1.396(7) . no C2 C3 1.367(8) . no C2 H2 0.9300 . no C3 C4 1.379(7) . no C3 H3 0.9300 . no C4 C5 1.397(7) . no C4 C7 1.476(7) . no C5 C6 1.376(8) . no C5 H5 0.9300 . no C6 H6 0.9300 . no C7 O2 1.235(6) . no C7 N1 1.349(6) . no C8 N2 1.279(7) . no C8 C9 1.470(11) . no C8 C10 1.481(11) . no C9 H9A 0.9600 . no C9 H9B 0.9600 . no C9 H9C 0.9600 . no C10 H10A 0.9600 . no C10 H10B 0.9600 . no C10 H10C 0.9600 . no N1 N2 1.386(6) . no N1 H1N 0.86(7) . no O1 H1O 1.02(8) . 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 118.2(5) . . no O1 C1 C2 121.5(5) . . no C6 C1 C2 120.3(5) . . no C3 C2 C1 119.9(5) . . no C3 C2 H2 120.1 . . no C1 C2 H2 120.1 . . no C2 C3 C4 121.2(5) . . no C2 C3 H3 119.4 . . no C4 C3 H3 119.4 . . no C3 C4 C5 117.6(5) . . no C3 C4 C7 117.9(4) . . no C5 C4 C7 124.5(5) . . no C6 C5 C4 121.8(5) . . no C6 C5 H5 119.1 . . no C4 C5 H5 119.1 . . no C1 C6 C5 119.3(5) . . no C1 C6 H6 120.4 . . no C5 C6 H6 120.4 . . no O2 C7 N1 121.6(5) . . no O2 C7 C4 121.4(5) . . no N1 C7 C4 116.9(4) . . no N2 C8 C9 125.8(6) . . no N2 C8 C10 115.6(7) . . no C9 C8 C10 118.7(6) . . no C8 C9 H9A 109.5 . . no C8 C9 H9B 109.5 . . no H9A C9 H9B 109.5 . . no C8 C9 H9C 109.5 . . no H9A C9 H9C 109.5 . . no H9B C9 H9C 109.5 . . no C8 C10 H10A 109.5 . . no C8 C10 H10B 109.5 . . no H10A C10 H10B 109.5 . . no C8 C10 H10C 109.5 . . no H10A C10 H10C 109.5 . . no H10B C10 H10C 109.5 . . no C7 N1 N2 116.7(4) . . no C7 N1 H1N 118(5) . . no N2 N1 H1N 124(5) . . no C8 N2 N1 116.7(5) . . no C1 O1 H1O 109(4) . . 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 -179.4(5) . . . . no C6 C1 C2 C3 0.4(9) . . . . no C1 C2 C3 C4 -1.7(8) . . . . no C2 C3 C4 C5 1.9(8) . . . . no C2 C3 C4 C7 -178.3(5) . . . . no C3 C4 C5 C6 -0.8(9) . . . . no C7 C4 C5 C6 179.4(6) . . . . no O1 C1 C6 C5 -179.5(6) . . . . no C2 C1 C6 C5 0.6(9) . . . . no C4 C5 C6 C1 -0.4(10) . . . . no C3 C4 C7 O2 -26.2(8) . . . . no C5 C4 C7 O2 153.6(6) . . . . no C3 C4 C7 N1 151.9(5) . . . . no C5 C4 C7 N1 -28.4(8) . . . . no O2 C7 N1 N2 -7.7(7) . . . . no C4 C7 N1 N2 174.3(4) . . . . no C9 C8 N2 N1 -3.1(10) . . . . no C10 C8 N2 N1 178.0(6) . . . . no C7 N1 N2 C8 161.8(5) . . . . no _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.172 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.042 _chemical_name_common N'-2-propylidene-4-hydroxybenzohydrazide # Attachment '2phaseILTdep.cif' data_imaceti-100 _database_code_depnum_ccdc_archive 'CCDC 835990' #TrackingRef '2phaseILTdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-2-propylidene-4-hydroxybenzohydrazide ; _chemical_formula_moiety 'C10 H12 N2 O2' _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 9.0080(10) _cell_length_b 7.0640(10) _cell_length_c 15.833(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1007.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 560 _cell_measurement_theta_min 3.757 _cell_measurement_theta_max 23.196 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9780 _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 6407 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2231 _reflns_number_gt 2021 _reflns_threshold_expression >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)' _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^)+(0.0737P)^2^+0.1006P] 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 0.042(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.6(11) _refine_ls_number_reflns 2231 _refine_ls_number_parameters 136 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.910 _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 0.67183(18) 0.4205(2) 0.11998(9) 0.0246(3) Uani 1 1 d . . . C2 C 0.51736(18) 0.4133(2) 0.12491(10) 0.0286(4) Uani 1 1 d . . . H2 H 0.4612 0.3629 0.0794 0.034 Uiso 1 1 calc R . . C3 C 0.44651(16) 0.4797(2) 0.19615(10) 0.0276(3) Uani 1 1 d . . . H3 H 0.3414 0.4725 0.1996 0.033 Uiso 1 1 calc R . . C4 C 0.52571(16) 0.5567(2) 0.26292(9) 0.0230(3) Uani 1 1 d . . . C5 C 0.68047(17) 0.5556(2) 0.25926(10) 0.0273(3) Uani 1 1 d . . . H5 H 0.7364 0.6022 0.3057 0.033 Uiso 1 1 calc R . . C7 C 0.75308(16) 0.4873(2) 0.18859(11) 0.0291(3) Uani 1 1 d . . . H7 H 0.8585 0.4861 0.1868 0.035 Uiso 1 1 calc R . . C8 C 0.44132(15) 0.63642(19) 0.33546(9) 0.0231(3) Uani 1 1 d . . . C9 C 0.45422(17) 1.0298(2) 0.46543(10) 0.0269(3) Uani 1 1 d . . . C10 C 0.5394(2) 1.1673(3) 0.41270(13) 0.0414(4) Uani 1 1 d . . . H10A H 0.6460 1.1455 0.4203 0.062 Uiso 1 1 calc R . . H10B H 0.5148 1.2967 0.4301 0.062 Uiso 1 1 calc R . . H10C H 0.5133 1.1499 0.3531 0.062 Uiso 1 1 calc R . . C14 C 0.3850(2) 1.1017(3) 0.54513(13) 0.0415(4) Uani 1 1 d . . . H14A H 0.3312 0.9985 0.5730 0.062 Uiso 1 1 calc R . . H14B H 0.3158 1.2044 0.5317 0.062 Uiso 1 1 calc R . . H14C H 0.4628 1.1491 0.5829 0.062 Uiso 1 1 calc R . . N1 N 0.50447(15) 0.78463(18) 0.37607(8) 0.0254(3) Uani 1 1 d . . . H1N H 0.585(2) 0.822(3) 0.3650(14) 0.030 Uiso 1 1 d . . . N2 N 0.43367(15) 0.85501(17) 0.44783(9) 0.0244(3) Uani 1 1 d . . . O1 O 0.74789(13) 0.36592(17) 0.05027(7) 0.0317(3) Uani 1 1 d . . . H1O H 0.690(2) 0.314(3) 0.0128(14) 0.038 Uiso 1 1 d . . . O2 O 0.31654(12) 0.57951(15) 0.35430(7) 0.0293(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0259(8) 0.0241(7) 0.0240(8) -0.0005(5) 0.0025(6) 0.0006(5) C2 0.0276(8) 0.0336(8) 0.0247(8) -0.0031(6) -0.0053(6) -0.0020(6) C3 0.0208(7) 0.0326(7) 0.0294(8) -0.0031(6) 0.0012(7) -0.0019(6) C4 0.0221(7) 0.0222(6) 0.0247(7) 0.0014(5) -0.0003(6) 0.0000(5) C5 0.0221(7) 0.0331(8) 0.0265(8) -0.0049(6) -0.0050(6) -0.0022(6) C7 0.0185(7) 0.0358(8) 0.0329(8) -0.0052(7) -0.0019(7) -0.0004(6) C8 0.0221(7) 0.0226(6) 0.0248(7) 0.0022(5) -0.0019(6) 0.0019(5) C9 0.0236(7) 0.0287(7) 0.0284(9) -0.0001(6) -0.0037(6) 0.0058(6) C10 0.0467(10) 0.0251(7) 0.0523(11) 0.0008(7) 0.0092(9) 0.0031(7) C14 0.0462(11) 0.0385(9) 0.0397(11) -0.0119(8) 0.0049(8) 0.0027(8) N1 0.0223(6) 0.0283(6) 0.0254(6) -0.0020(5) 0.0029(5) -0.0008(5) N2 0.0244(7) 0.0286(6) 0.0202(6) -0.0016(5) 0.0003(5) 0.0024(5) O1 0.0257(6) 0.0440(7) 0.0255(6) -0.0080(5) 0.0013(5) -0.0008(5) O2 0.0234(5) 0.0306(5) 0.0341(7) -0.0010(4) 0.0056(5) -0.0016(4) _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 1.3550(19) . no C1 C7 1.392(2) . no C1 C2 1.395(2) . no C2 C3 1.378(2) . no C2 H2 0.9500 . no C3 C4 1.387(2) . no C3 H3 0.9500 . no C4 C5 1.395(2) . no C4 C8 1.488(2) . no C5 C7 1.383(2) . no C5 H5 0.9500 . no C7 H7 0.9500 . no C8 O2 1.2305(18) . no C8 N1 1.354(2) . no C9 N2 1.279(2) . no C9 C10 1.493(2) . no C9 C14 1.496(2) . no C10 H10A 0.9800 . no C10 H10B 0.9800 . no C10 H10C 0.9800 . no C14 H14A 0.9800 . no C14 H14B 0.9800 . no C14 H14C 0.9800 . no N1 N2 1.3947(19) . no N1 H1N 0.79(2) . no O1 H1O 0.87(2) . 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 C7 117.79(14) . . no O1 C1 C2 122.67(14) . . no C7 C1 C2 119.54(14) . . no C3 C2 C1 119.70(14) . . no C3 C2 H2 120.1 . . no C1 C2 H2 120.1 . . no C2 C3 C4 121.28(14) . . no C2 C3 H3 119.4 . . no C4 C3 H3 119.4 . . no C3 C4 C5 118.71(13) . . no C3 C4 C8 118.30(13) . . no C5 C4 C8 122.99(13) . . no C7 C5 C4 120.53(14) . . no C7 C5 H5 119.7 . . no C4 C5 H5 119.7 . . no C5 C7 C1 120.07(14) . . no C5 C7 H7 120.0 . . no C1 C7 H7 120.0 . . no O2 C8 N1 121.42(14) . . no O2 C8 C4 122.01(13) . . no N1 C8 C4 116.40(13) . . no N2 C9 C10 125.47(15) . . no N2 C9 C14 116.80(15) . . no C10 C9 C14 117.72(15) . . no C9 C10 H10A 109.5 . . no C9 C10 H10B 109.5 . . no H10A C10 H10B 109.5 . . no C9 C10 H10C 109.5 . . no H10A C10 H10C 109.5 . . no H10B C10 H10C 109.5 . . no C9 C14 H14A 109.5 . . no C9 C14 H14B 109.5 . . no H14A C14 H14B 109.5 . . no C9 C14 H14C 109.5 . . no H14A C14 H14C 109.5 . . no H14B C14 H14C 109.5 . . no C8 N1 N2 118.06(13) . . no C8 N1 H1N 122.5(16) . . no N2 N1 H1N 118.8(16) . . no C9 N2 N1 117.09(13) . . no C1 O1 H1O 111.9(14) . . no _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.190 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.034 # Attachment '2phaseIRTdep.cif' data_imaceti _database_code_depnum_ccdc_archive 'CCDC 835991' #TrackingRef '2phaseIRTdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-2-propylidene-4-hydroxybenzohydrazide ; _chemical_formula_moiety 'C10 H12 N2 O2' _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 9.157(4) _cell_length_b 7.196(3) _cell_length_c 15.566(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1025.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 515 _cell_measurement_theta_min 3.597 _cell_measurement_theta_max 22.347 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 293(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 5769 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1935 _reflns_number_gt 1628 _reflns_threshold_expression >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)' _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^)+(0.0468P)^2^+0.1065P] 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 0.071(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(15) _refine_ls_number_reflns 1935 _refine_ls_number_parameters 136 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.1717(2) 1.0853(3) 0.04745(13) 0.0428(5) Uani 1 1 d . . . C2 C 0.0204(2) 1.0917(3) 0.05250(13) 0.0484(5) Uani 1 1 d . . . H2 H -0.0336 1.1431 0.0078 0.058 Uiso 1 1 calc R . . C3 C -0.0494(2) 1.0218(3) 0.12351(14) 0.0477(5) Uani 1 1 d . . . H3 H -0.1507 1.0291 0.1269 0.057 Uiso 1 1 calc R . . C4 C 0.0272(2) 0.9411(2) 0.18989(13) 0.0385(4) Uani 1 1 d . . . C5 C 0.1787(2) 0.9422(3) 0.18565(14) 0.0490(5) Uani 1 1 d . . . H5 H 0.2326 0.8936 0.2310 0.059 Uiso 1 1 calc R . . C6 C 0.2496(2) 1.0138(3) 0.11580(15) 0.0514(5) Uani 1 1 d . . . H6 H 0.3512 1.0143 0.1143 0.062 Uiso 1 1 calc R . . C7 C -0.0559(2) 0.8593(2) 0.26219(13) 0.0393(4) Uani 1 1 d . . . C8 C -0.0425(2) 0.4680(3) 0.39032(14) 0.0479(5) Uani 1 1 d . . . C9 C 0.0449(4) 0.3369(3) 0.3373(2) 0.0768(8) Uani 1 1 d . . . H9A H 0.0212 0.3538 0.2777 0.115 Uiso 1 1 calc R . . H9B H 0.0230 0.2115 0.3540 0.115 Uiso 1 1 calc R . . H9C H 0.1471 0.3606 0.3459 0.115 Uiso 1 1 calc R . . C10 C -0.1126(3) 0.3944(4) 0.4697(2) 0.0754(8) Uani 1 1 d . . . H10A H -0.1667 0.4919 0.4973 0.113 Uiso 1 1 calc R . . H10B H -0.0387 0.3490 0.5081 0.113 Uiso 1 1 calc R . . H10C H -0.1777 0.2948 0.4549 0.113 Uiso 1 1 calc R . . N1 N 0.0058(2) 0.7123(2) 0.30206(11) 0.0440(4) Uani 1 1 d . . . H1 H 0.084(3) 0.670(3) 0.2907(17) 0.053 Uiso 1 1 d . . . N2 N -0.06472(19) 0.6386(2) 0.37345(11) 0.0429(4) Uani 1 1 d . . . O1 O 0.24690(18) 1.1452(3) -0.02181(11) 0.0575(4) Uani 1 1 d . . . H1O H 0.195(3) 1.193(4) -0.0601(19) 0.069 Uiso 1 1 d . . . O2 O -0.17790(16) 0.9140(2) 0.28215(10) 0.0515(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0420(11) 0.0465(11) 0.0399(11) 0.0009(8) 0.0012(10) -0.0018(8) C2 0.0431(12) 0.0580(12) 0.0442(12) 0.0105(9) -0.0094(10) 0.0029(9) C3 0.0355(9) 0.0558(11) 0.0520(13) 0.0078(10) -0.0005(11) 0.0038(9) C4 0.0370(10) 0.0369(9) 0.0415(10) -0.0008(7) -0.0026(9) 0.0014(7) C5 0.0378(11) 0.0630(13) 0.0462(12) 0.0129(9) -0.0076(10) 0.0046(9) C6 0.0312(9) 0.0670(12) 0.0560(13) 0.0105(11) -0.0040(12) -0.0001(9) C7 0.0382(9) 0.0385(9) 0.0411(11) -0.0037(7) -0.0013(9) -0.0024(8) C8 0.0455(11) 0.0444(11) 0.0539(14) 0.0041(9) -0.0068(10) -0.0089(9) C9 0.0853(18) 0.0437(12) 0.101(2) 0.0000(12) 0.0159(17) -0.0029(12) C10 0.084(2) 0.0687(15) 0.0735(19) 0.0219(13) 0.0072(17) -0.0081(14) N1 0.0434(9) 0.0445(9) 0.0442(10) 0.0030(8) 0.0047(9) 0.0033(7) N2 0.0446(9) 0.0486(9) 0.0355(8) 0.0023(7) 0.0002(7) -0.0031(7) O1 0.0454(9) 0.0834(11) 0.0438(9) 0.0154(8) 0.0005(7) -0.0017(8) O2 0.0412(7) 0.0529(8) 0.0605(10) 0.0044(6) 0.0108(8) 0.0051(6) _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 1.350(3) . no C1 C6 1.381(3) . no C1 C2 1.388(3) . no C2 C3 1.372(3) . no C2 H2 0.9300 . no C3 C4 1.377(3) . no C3 H3 0.9300 . no C4 C5 1.389(3) . no C4 C7 1.481(3) . no C5 C6 1.367(3) . no C5 H5 0.9300 . no C6 H6 0.9300 . no C7 O2 1.224(2) . no C7 N1 1.351(3) . no C8 N2 1.271(3) . no C8 C9 1.488(3) . no C8 C10 1.491(4) . no C9 H9A 0.9600 . no C9 H9B 0.9600 . no C9 H9C 0.9600 . no C10 H10A 0.9600 . no C10 H10B 0.9600 . no C10 H10C 0.9600 . no N1 N2 1.390(3) . no N1 H1 0.80(3) . no O1 H1O 0.83(3) . 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 118.07(19) . . no O1 C1 C2 122.96(19) . . no C6 C1 C2 118.97(19) . . no C3 C2 C1 119.90(19) . . no C3 C2 H2 120.0 . . no C1 C2 H2 120.0 . . no C2 C3 C4 121.43(18) . . no C2 C3 H3 119.3 . . no C4 C3 H3 119.3 . . no C3 C4 C5 118.08(19) . . no C3 C4 C7 118.44(17) . . no C5 C4 C7 123.47(18) . . no C6 C5 C4 120.96(19) . . no C6 C5 H5 119.5 . . no C4 C5 H5 119.5 . . no C5 C6 C1 120.50(19) . . no C5 C6 H6 119.8 . . no C1 C6 H6 119.8 . . no O2 C7 N1 121.15(19) . . no O2 C7 C4 122.25(17) . . no N1 C7 C4 116.47(18) . . no N2 C8 C9 125.7(2) . . no N2 C8 C10 116.5(2) . . no C9 C8 C10 117.8(2) . . no C8 C9 H9A 109.5 . . no C8 C9 H9B 109.5 . . no H9A C9 H9B 109.5 . . no C8 C9 H9C 109.5 . . no H9A C9 H9C 109.5 . . no H9B C9 H9C 109.5 . . no C8 C10 H10A 109.5 . . no C8 C10 H10B 109.5 . . no H10A C10 H10B 109.5 . . no C8 C10 H10C 109.5 . . no H10A C10 H10C 109.5 . . no H10B C10 H10C 109.5 . . no C7 N1 N2 118.12(17) . . no C7 N1 H1 124.9(19) . . no N2 N1 H1 116.6(19) . . no C8 N2 N1 117.30(17) . . no C1 O1 H1O 114.2(19) . . 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 177.5(2) . . . . no C6 C1 C2 C3 -2.1(3) . . . . no C1 C2 C3 C4 -1.4(3) . . . . no C2 C3 C4 C5 3.9(3) . . . . no C2 C3 C4 C7 -176.60(18) . . . . no C3 C4 C5 C6 -2.9(3) . . . . no C7 C4 C5 C6 177.59(19) . . . . no C4 C5 C6 C1 -0.5(3) . . . . no O1 C1 C6 C5 -176.5(2) . . . . no C2 C1 C6 C5 3.1(3) . . . . no C3 C4 C7 O2 -26.8(3) . . . . no C5 C4 C7 O2 152.7(2) . . . . no C3 C4 C7 N1 149.17(18) . . . . no C5 C4 C7 N1 -31.3(3) . . . . no O2 C7 N1 N2 -7.8(3) . . . . no C4 C7 N1 N2 176.24(16) . . . . no C9 C8 N2 N1 -4.2(3) . . . . no C10 C8 N2 N1 176.8(2) . . . . no C7 N1 N2 C8 153.58(19) . . . . no _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.200 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.051 # Attachment '3RTdep.cif' data_ciclhex _database_code_depnum_ccdc_archive 'CCDC 835992' #TrackingRef '3RTdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-cyclohexylidene-4-hydroxybenzohydrazide' ; _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 9.818(6) _cell_length_b 10.485(8) _cell_length_c 11.333(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1166.6(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 422 _cell_measurement_theta_min 3.601 _cell_measurement_theta_max 20.896 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9650 _exptl_absorpt_correction_T_max 0.9930 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 293(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 8248 _diffrn_reflns_av_R_equivalents 0.0902 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2479 _reflns_number_gt 1566 _reflns_threshold_expression >2sigma(I) _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)' _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^)+(0.0456P)^2^+0.4249P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 2479 _refine_ls_number_parameters 161 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1047 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1382 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.1526(3) 1.1253(3) 0.2003(3) 0.0360(8) Uani 1 1 d . . . C2 C 0.0156(3) 1.0982(3) 0.1854(3) 0.0431(9) Uani 1 1 d . . . H2 H -0.0379 1.1496 0.1373 0.052 Uiso 1 1 calc R . . C3 C -0.0408(3) 0.9953(3) 0.2421(4) 0.0425(8) Uani 1 1 d . . . H3 H -0.1325 0.9771 0.2304 0.051 Uiso 1 1 calc R . . C4 C 0.0343(3) 0.9181(3) 0.3156(3) 0.0328(7) Uani 1 1 d . . . C5 C 0.1717(3) 0.9473(3) 0.3316(3) 0.0379(8) Uani 1 1 d . . . H5 H 0.2250 0.8967 0.3807 0.045 Uiso 1 1 calc R . . C6 C 0.2287(3) 1.0500(3) 0.2753(3) 0.0388(8) Uani 1 1 d . . . H6 H 0.3200 1.0692 0.2879 0.047 Uiso 1 1 calc R . . C7 C -0.0364(3) 0.8134(3) 0.3762(3) 0.0341(7) Uani 1 1 d . . . C8 C 0.0205(3) 0.5301(3) 0.5285(3) 0.0400(8) Uani 1 1 d . . . C9 C 0.1402(4) 0.4678(3) 0.4713(4) 0.0455(9) Uani 1 1 d . . . H9A H 0.2135 0.4593 0.5281 0.055 Uiso 1 1 calc R . . H9B H 0.1724 0.5205 0.4067 0.055 Uiso 1 1 calc R . . C10 C 0.1008(4) 0.3377(3) 0.4252(4) 0.0515(10) Uani 1 1 d . . . H10A H 0.0398 0.3479 0.3586 0.062 Uiso 1 1 calc R . . H10B H 0.1819 0.2941 0.3975 0.062 Uiso 1 1 calc R . . C11 C 0.0321(5) 0.2568(3) 0.5179(5) 0.0651(12) Uani 1 1 d . . . H11A H 0.0964 0.2383 0.5807 0.078 Uiso 1 1 calc R . . H11B H 0.0040 0.1765 0.4831 0.078 Uiso 1 1 calc R . . C12 C -0.0909(4) 0.3239(3) 0.5689(4) 0.0582(11) Uani 1 1 d . . . H12A H -0.1593 0.3341 0.5079 0.070 Uiso 1 1 calc R . . H12B H -0.1297 0.2720 0.6313 0.070 Uiso 1 1 calc R . . C13 C -0.0532(4) 0.4526(3) 0.6176(4) 0.0508(10) Uani 1 1 d . . . H13A H -0.1352 0.4972 0.6417 0.061 Uiso 1 1 calc R . . H13B H 0.0039 0.4416 0.6867 0.061 Uiso 1 1 calc R . . N1 N 0.0395(3) 0.7191(2) 0.4257(3) 0.0373(7) Uani 1 1 d . . . H1 H 0.127(4) 0.715(3) 0.416(4) 0.045 Uiso 1 1 d . . . N2 N -0.0283(3) 0.6407(2) 0.5067(3) 0.0396(7) Uani 1 1 d . . . O1 O 0.2158(3) 1.2240(2) 0.1468(3) 0.0478(7) Uani 1 1 d . . . H1O H 0.162(4) 1.268(4) 0.108(4) 0.057 Uiso 1 1 d . . . O2 O -0.1613(2) 0.8091(2) 0.3805(2) 0.0496(7) 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 0.0350(17) 0.0348(16) 0.038(2) -0.0028(14) 0.0011(15) -0.0040(14) C2 0.0319(17) 0.0460(19) 0.051(2) 0.0077(19) -0.0100(16) -0.0016(14) C3 0.0265(16) 0.0448(17) 0.056(2) 0.0031(17) -0.0073(16) -0.0039(15) C4 0.0296(15) 0.0266(14) 0.042(2) -0.0051(14) 0.0008(15) 0.0008(13) C5 0.0315(16) 0.0352(16) 0.047(2) -0.0010(15) -0.0038(15) 0.0070(14) C6 0.0284(15) 0.0427(17) 0.045(2) -0.0018(15) -0.0035(15) -0.0043(14) C7 0.0322(15) 0.0242(13) 0.046(2) -0.0036(14) 0.0009(16) 0.0001(13) C8 0.0396(19) 0.0352(16) 0.045(2) -0.0035(15) 0.0022(17) -0.0050(15) C9 0.044(2) 0.0355(17) 0.057(2) 0.0018(17) 0.0095(18) 0.0048(14) C10 0.061(2) 0.0361(17) 0.057(3) -0.0027(18) 0.000(2) 0.0084(17) C11 0.077(3) 0.0303(16) 0.088(3) 0.005(2) -0.007(3) -0.004(2) C12 0.057(2) 0.047(2) 0.070(3) 0.016(2) -0.009(2) -0.0117(18) C13 0.048(2) 0.046(2) 0.058(3) 0.0104(19) 0.0094(19) -0.0049(17) N1 0.0312(13) 0.0337(12) 0.0469(18) 0.0029(13) 0.0057(14) -0.0009(12) N2 0.0397(15) 0.0337(13) 0.0455(18) 0.0018(14) 0.0056(14) -0.0035(12) O1 0.0377(13) 0.0487(14) 0.0572(18) 0.0128(13) -0.0038(13) -0.0080(11) O2 0.0269(11) 0.0487(13) 0.073(2) 0.0083(13) 0.0032(12) -0.0007(10) _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 1.350(4) . no C1 C6 1.380(5) . no C1 C2 1.385(5) . no C2 C3 1.373(5) . no C2 H2 0.9300 . no C3 C4 1.375(4) . no C3 H3 0.9300 . no C4 C5 1.395(4) . no C4 C7 1.470(4) . no C5 C6 1.371(5) . no C5 H5 0.9300 . no C6 H6 0.9300 . no C7 O2 1.228(4) . no C7 N1 1.359(4) . no C8 N2 1.279(4) . no C8 C13 1.484(5) . no C8 C9 1.493(5) . no C9 C10 1.511(5) . no C9 H9A 0.9700 . no C9 H9B 0.9700 . no C10 C11 1.509(6) . no C10 H10A 0.9700 . no C10 H10B 0.9700 . no C11 C12 1.512(6) . no C11 H11A 0.9700 . no C11 H11B 0.9700 . no C12 C13 1.504(5) . no C12 H12A 0.9700 . no C12 H12B 0.9700 . no C13 H13A 0.9700 . no C13 H13B 0.9700 . no N1 N2 1.401(4) . no N1 H1 0.86(4) . no O1 H1O 0.82(4) . 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 117.8(3) . . no O1 C1 C2 123.3(3) . . no C6 C1 C2 118.9(3) . . no C3 C2 C1 119.8(3) . . no C3 C2 H2 120.1 . . no C1 C2 H2 120.1 . . no C2 C3 C4 121.9(3) . . no C2 C3 H3 119.0 . . no C4 C3 H3 119.0 . . no C3 C4 C5 117.9(3) . . no C3 C4 C7 118.0(3) . . no C5 C4 C7 124.0(3) . . no C6 C5 C4 120.4(3) . . no C6 C5 H5 119.8 . . no C4 C5 H5 119.8 . . no C5 C6 C1 121.0(3) . . no C5 C6 H6 119.5 . . no C1 C6 H6 119.5 . . no O2 C7 N1 120.3(3) . . no O2 C7 C4 121.1(3) . . no N1 C7 C4 118.5(2) . . no N2 C8 C13 116.5(3) . . no N2 C8 C9 127.4(3) . . no C13 C8 C9 116.1(3) . . no C8 C9 C10 110.1(3) . . no C8 C9 H9A 109.6 . . no C10 C9 H9A 109.6 . . no C8 C9 H9B 109.6 . . no C10 C9 H9B 109.6 . . no H9A C9 H9B 108.2 . . no C11 C10 C9 112.4(4) . . no C11 C10 H10A 109.1 . . no C9 C10 H10A 109.1 . . no C11 C10 H10B 109.1 . . no C9 C10 H10B 109.1 . . no H10A C10 H10B 107.9 . . no C10 C11 C12 111.2(3) . . no C10 C11 H11A 109.4 . . no C12 C11 H11A 109.4 . . no C10 C11 H11B 109.4 . . no C12 C11 H11B 109.4 . . no H11A C11 H11B 108.0 . . no C13 C12 C11 111.2(3) . . no C13 C12 H12A 109.4 . . no C11 C12 H12A 109.4 . . no C13 C12 H12B 109.4 . . no C11 C12 H12B 109.4 . . no H12A C12 H12B 108.0 . . no C8 C13 C12 111.2(4) . . no C8 C13 H13A 109.4 . . no C12 C13 H13A 109.4 . . no C8 C13 H13B 109.4 . . no C12 C13 H13B 109.4 . . no H13A C13 H13B 108.0 . . no C7 N1 N2 115.9(3) . . no C7 N1 H1 122(2) . . no N2 N1 H1 122(3) . . no C8 N2 N1 118.8(3) . . no C1 O1 H1O 112(3) . . 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(3) . . . . no C6 C1 C2 C3 -2.1(5) . . . . no C1 C2 C3 C4 1.1(6) . . . . no C2 C3 C4 C5 -0.1(5) . . . . no C2 C3 C4 C7 177.5(3) . . . . no C3 C4 C5 C6 0.1(5) . . . . no C7 C4 C5 C6 -177.3(3) . . . . no C4 C5 C6 C1 -1.2(5) . . . . no O1 C1 C6 C5 -179.2(3) . . . . no C2 C1 C6 C5 2.2(5) . . . . no C3 C4 C7 O2 -14.1(5) . . . . no C5 C4 C7 O2 163.2(3) . . . . no C3 C4 C7 N1 164.4(3) . . . . no C5 C4 C7 N1 -18.2(5) . . . . no N2 C8 C9 C10 -126.9(4) . . . . no C13 C8 C9 C10 50.6(5) . . . . no C8 C9 C10 C11 -51.6(5) . . . . no C9 C10 C11 C12 55.7(5) . . . . no C10 C11 C12 C13 -55.7(5) . . . . no N2 C8 C13 C12 125.9(3) . . . . no C9 C8 C13 C12 -51.9(5) . . . . no C11 C12 C13 C8 52.8(5) . . . . no O2 C7 N1 N2 -17.1(5) . . . . no C4 C7 N1 N2 164.3(3) . . . . no C13 C8 N2 N1 178.3(3) . . . . no C9 C8 N2 N1 -4.2(5) . . . . no C7 N1 N2 C8 158.7(3) . . . . no _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.170 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.046 # Attachment '4RTdep.cif' data_ciclobut _database_code_depnum_ccdc_archive 'CCDC 835993' #TrackingRef '4RTdep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N'-cyclobutylidene-4-hydroxybenzohydrazide' ; _chemical_formula_moiety 'C11 H12 N2 O2' _chemical_formula_sum 'C11 H12 N2 O2' _chemical_formula_weight 204.23 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 'C 1 c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.415(4) _cell_length_b 16.247(7) _cell_length_c 7.729(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.60(3) _cell_angle_gamma 90.00 _cell_volume 975.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 532 _cell_measurement_theta_min 5.913 _cell_measurement_theta_max 22.565 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9630 _exptl_absorpt_correction_T_max 0.9750 _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _diffrn_ambient_temperature 293(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 3226 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1682 _reflns_number_gt 1402 _reflns_threshold_expression >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)' _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^)+(0.0614P)^2^+0.0472P] 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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.6(18) _refine_ls_number_reflns 1682 _refine_ls_number_parameters 142 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.108 _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 0.1449(3) 0.11038(19) -0.1919(3) 0.0446(6) Uani 1 1 d . . . C2 C 0.2468(4) 0.17416(19) -0.0867(4) 0.0458(7) Uani 1 1 d . . . H2 H 0.2185 0.2286 -0.1227 0.055 Uiso 1 1 calc R . . C3 C 0.3905(3) 0.15608(16) 0.0717(3) 0.0405(6) Uani 1 1 d . . . H3 H 0.4576 0.1988 0.1431 0.049 Uiso 1 1 calc R . . C4 C 0.4361(3) 0.07547(14) 0.1258(3) 0.0364(5) Uani 1 1 d . . . C5 C 0.3316(4) 0.01275(15) 0.0193(4) 0.0425(6) Uani 1 1 d . . . H5 H 0.3594 -0.0418 0.0546 0.051 Uiso 1 1 calc R . . C6 C 0.1876(4) 0.03039(18) -0.1375(4) 0.0474(7) Uani 1 1 d . . . H6 H 0.1188 -0.0122 -0.2072 0.057 Uiso 1 1 calc R . . C7 C 0.5878(3) 0.05931(15) 0.3032(3) 0.0382(5) Uani 1 1 d . . . C8 C 0.8235(3) -0.11273(16) 0.4915(3) 0.0401(6) Uani 1 1 d . . . C9 C 0.7353(4) -0.18511(17) 0.3734(4) 0.0499(7) Uani 1 1 d . . . H9A H 0.7505 -0.1887 0.2554 0.060 Uiso 1 1 calc R . . H9B H 0.6151 -0.1906 0.3548 0.060 Uiso 1 1 calc R . . C10 C 0.8571(5) -0.24102(18) 0.5281(4) 0.0582(8) Uani 1 1 d . . . H10A H 0.9324 -0.2740 0.4875 0.070 Uiso 1 1 calc R . . H10B H 0.7982 -0.2751 0.5878 0.070 Uiso 1 1 calc R . . C11 C 0.9470(4) -0.16531(18) 0.6460(4) 0.0515(7) Uani 1 1 d . . . H11A H 0.9333 -0.1608 0.7646 0.062 Uiso 1 1 calc R . . H11B H 1.0666 -0.1591 0.6624 0.062 Uiso 1 1 calc R . . N1 N 0.6651(3) -0.01297(14) 0.3118(3) 0.0424(6) Uani 1 1 d . . . H1 H 0.647(5) -0.0373(19) 0.219(5) 0.051 Uiso 1 1 d . . . N2 N 0.8010(3) -0.03581(13) 0.4785(3) 0.0421(5) Uani 1 1 d . . . O1 O 0.0040(3) 0.13155(18) -0.3459(3) 0.0671(7) Uani 1 1 d . . . H1O H -0.044(7) 0.092(3) -0.392(6) 0.081 Uiso 1 1 d . . . O2 O 0.6323(3) 0.10792(12) 0.4345(3) 0.0588(6) 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 0.0311(13) 0.0639(16) 0.0340(13) -0.0002(12) 0.0073(10) -0.0020(12) C2 0.0409(15) 0.0440(14) 0.0457(15) 0.0037(10) 0.0091(11) 0.0009(11) C3 0.0368(13) 0.0402(12) 0.0406(14) -0.0041(10) 0.0103(10) -0.0055(11) C4 0.0344(12) 0.0392(12) 0.0333(11) -0.0022(10) 0.0103(10) -0.0010(10) C5 0.0455(15) 0.0359(12) 0.0399(14) -0.0043(10) 0.0095(11) -0.0001(11) C6 0.0409(15) 0.0523(16) 0.0413(14) -0.0103(12) 0.0072(11) -0.0090(13) C7 0.0371(12) 0.0393(13) 0.0313(11) -0.0030(10) 0.0055(10) -0.0018(11) C8 0.0360(13) 0.0481(14) 0.0325(12) -0.0029(11) 0.0089(10) 0.0035(11) C9 0.0488(17) 0.0484(16) 0.0438(15) -0.0019(11) 0.0083(13) -0.0014(12) C10 0.072(2) 0.0490(16) 0.0473(16) 0.0030(13) 0.0158(14) 0.0029(15) C11 0.0575(18) 0.0499(15) 0.0380(14) 0.0056(11) 0.0084(12) 0.0142(14) N1 0.0421(14) 0.0471(12) 0.0272(10) -0.0044(9) 0.0014(9) 0.0047(10) N2 0.0389(12) 0.0486(12) 0.0306(10) -0.0017(9) 0.0043(8) 0.0061(10) O1 0.0439(12) 0.0881(18) 0.0483(12) 0.0067(11) -0.0057(9) 0.0052(11) O2 0.0649(14) 0.0473(11) 0.0410(10) -0.0129(8) -0.0054(9) 0.0090(10) _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 1.362(3) . no C1 C6 1.371(4) . no C1 C2 1.391(4) . no C2 C3 1.382(4) . no C2 H2 0.9300 . no C3 C4 1.383(4) . no C3 H3 0.9300 . no C4 C5 1.390(4) . no C4 C7 1.494(3) . no C5 C6 1.375(4) . no C5 H5 0.9300 . no C6 H6 0.9300 . no C7 O2 1.225(3) . no C7 N1 1.332(3) . no C8 N2 1.262(3) . no C8 C9 1.499(4) . no C8 C11 1.511(3) . no C9 C10 1.537(4) . no C9 H9A 0.9700 . no C9 H9B 0.9700 . no C10 C11 1.545(4) . no C10 H10A 0.9700 . no C10 H10B 0.9700 . no C11 H11A 0.9700 . no C11 H11B 0.9700 . no N1 N2 1.405(3) . no N1 H1 0.78(4) . no O1 H1O 0.77(5) . 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 123.0(2) . . no O1 C1 C2 117.2(3) . . no C6 C1 C2 119.8(2) . . no C3 C2 C1 119.5(3) . . no C3 C2 H2 120.2 . . no C1 C2 H2 120.2 . . no C2 C3 C4 121.0(2) . . no C2 C3 H3 119.5 . . no C4 C3 H3 119.5 . . no C3 C4 C5 118.4(2) . . no C3 C4 C7 118.9(2) . . no C5 C4 C7 122.5(2) . . no C6 C5 C4 120.8(2) . . no C6 C5 H5 119.6 . . no C4 C5 H5 119.6 . . no C1 C6 C5 120.4(2) . . no C1 C6 H6 119.8 . . no C5 C6 H6 119.8 . . no O2 C7 N1 122.6(2) . . no O2 C7 C4 121.9(2) . . no N1 C7 C4 115.4(2) . . no N2 C8 C9 134.8(2) . . no N2 C8 C11 131.2(2) . . no C9 C8 C11 93.8(2) . . no C8 C9 C10 87.9(2) . . no C8 C9 H9A 114.0 . . no C10 C9 H9A 114.0 . . no C8 C9 H9B 114.0 . . no C10 C9 H9B 114.0 . . no H9A C9 H9B 111.2 . . no C9 C10 C11 91.0(2) . . no C9 C10 H10A 113.5 . . no C11 C10 H10A 113.5 . . no C9 C10 H10B 113.5 . . no C11 C10 H10B 113.5 . . no H10A C10 H10B 110.8 . . no C8 C11 C10 87.2(2) . . no C8 C11 H11A 114.1 . . no C10 C11 H11A 114.1 . . no C8 C11 H11B 114.1 . . no C10 C11 H11B 114.1 . . no H11A C11 H11B 111.3 . . no C7 N1 N2 119.3(2) . . no C7 N1 H1 119(2) . . no N2 N1 H1 121(2) . . no C8 N2 N1 112.3(2) . . no C1 O1 H1O 109(3) . . 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 179.5(3) . . . . no C6 C1 C2 C3 0.0(4) . . . . no C1 C2 C3 C4 1.0(4) . . . . no C2 C3 C4 C5 -1.5(4) . . . . no C2 C3 C4 C7 -177.1(2) . . . . no C3 C4 C5 C6 0.9(4) . . . . no C7 C4 C5 C6 176.3(3) . . . . no O1 C1 C6 C5 179.9(3) . . . . no C2 C1 C6 C5 -0.6(4) . . . . no C4 C5 C6 C1 0.1(5) . . . . no C3 C4 C7 O2 28.3(4) . . . . no C5 C4 C7 O2 -147.1(3) . . . . no C3 C4 C7 N1 -154.9(2) . . . . no C5 C4 C7 N1 29.7(4) . . . . no N2 C8 C9 C10 -175.5(3) . . . . no C11 C8 C9 C10 0.6(2) . . . . no C8 C9 C10 C11 -0.6(2) . . . . no N2 C8 C11 C10 175.7(3) . . . . no C9 C8 C11 C10 -0.6(2) . . . . no C9 C10 C11 C8 0.6(2) . . . . no O2 C7 N1 N2 1.3(4) . . . . no C4 C7 N1 N2 -175.5(2) . . . . no C9 C8 N2 N1 -2.4(4) . . . . no C11 C8 N2 N1 -177.2(3) . . . . no C7 N1 N2 C8 157.8(2) . . . . no _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.220 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.043