Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global #============================================================================== _journal_coden_Cambridge 188 # 0. AUDIT DETAILS _audit_creation_date 'Mar 5 14:45:02 2001' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Prof L W Jenneskens' _publ_contact_author_address ; Prof L W Jenneskens Debye Institute Utrecht University Dept of Physical Org Chemistry Padualaan 8 Utrecht CH 3584 THE NETHERLANDS ; _publ_contact_author_email 'JENNESK@CHEM.UU.NL' _publ_contact_author_fax '+31 30 2533940' _publ_contact_author_phone '+31 30 2532533' _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 2' _publ_contact_letter ; Date of submission: March, 2001 L.S. This CIF submission is intended as supporting information for a paper to be submitted to J. Chem. Soc., Perkin Trans. 2 Yours faithfully, Huub Kooijman ; #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; The occurence of through-bond orbital interactions in an \a,\w donor-acceptor substituted bi(cyclohexylidene) and bi(cyclohexyl). X-ray diffraction, UV-Vis absorption and photoelectron spectroscopy, Ab Initio SCF-MO and natural bond orbital analyses. ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name 'Wibren D. Oosterbaan' 'Remco W.A. Havenith' 'van Walree, Cornelis A.' 'Leonardus W. Jenneskens' 'Rolf Gleiter' 'Huub Kooijman' 'Anthony L. Spek' #=============================================================================== # 4. TEXT _publ_section_references ; Nonius (1998). Collect Software, Nonius, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany, 1997. Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of G\"ottingen, Germany, 1986. Sheldrick, G.M. SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany, 1997. Spek, A.L. (2001). PLATON, A multi-purpose crystallographic tool, Utrecht University, The Netherlands. Internet: http://www.cryst.chem.uu.nl/platon/ Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; This work was supported in part (ALS) by the Council for the Chemical Sciences of the Netherlands Organization for Scientific Research (CW-NWO). ; #=============================================================================== data_1 _database_code_CSD 160667 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N3' _chemical_formula_structural ? _chemical_formula_sum 'C20 H21 N3' _chemical_formula_weight 303.40 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 21/m' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z -x,-y,-z x,1/2-y,z _cell_length_a 7.0681(12) _cell_length_b 11.9013(12) _cell_length_c 9.3556(12) _cell_angle_alpha 90 _cell_angle_beta 90.931(7) _cell_angle_gamma 90 _cell_volume 786.89(19) _cell_formula_units_Z 2 _cell_measurement_temperature 125 _cell_measurement_reflns_used 140 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _cell_special_details ; Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set. ; _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.077 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 125 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Nonius Kappa CCD area detector' _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 4836 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measured_fraction_theta_full 0.99 _diffrn_reflns_reduction_process ; ? ; # number of unique reflections _reflns_number_total 1871 _reflns_number_gt 1492 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'PLATON (Spek, 2001)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2 > 2sigma(F^2) is used only for calculating -R-factor-obs 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 'w=1/[\s^2^(F~o~^2^)+(0.0569P)^2^+0.09P] where P=(F~o~^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 ? _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 1871 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.318 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.044 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N5 N Uani -0.04765(16) 0.25000 0.39751(13) 1.000 0.0170(3) . . N15 N Uani 1.10838(13) 0.07197(8) -0.17520(10) 1.000 0.0299(3) . . C1 C Uani -0.5406(2) 0.25000 0.64926(16) 1.000 0.0230(4) . . C2 C Uani -0.45608(15) 0.15010(9) 0.60988(11) 1.000 0.0232(3) . . C3 C Uani -0.29052(14) 0.14922(9) 0.53154(12) 1.000 0.0210(3) . . C4 C Uani -0.20457(19) 0.25000 0.48817(14) 1.000 0.0161(4) . . C6 C Uani 0.06731(14) 0.14791(8) 0.38697(11) 1.000 0.0181(3) . . C7 C Uani 0.17668(14) 0.14544(8) 0.24698(11) 1.000 0.0185(3) . . C8 C Uani 0.29307(19) 0.25000 0.22334(15) 1.000 0.0169(4) . . C9 C Uani 0.47379(19) 0.25000 0.18047(14) 1.000 0.0160(4) . . C10 C Uani 0.58700(14) 0.14545(8) 0.14933(11) 1.000 0.0171(3) . . C11 C Uani 0.64686(15) 0.14335(8) -0.00955(11) 1.000 0.0179(3) . . C12 C Uani 0.7458(2) 0.25000 -0.04797(15) 1.000 0.0172(4) . . C13 C Uani 0.9179(2) 0.25000 -0.11053(15) 1.000 0.0175(4) . . C14 C Uani 1.01873(15) 0.14870(8) -0.14577(11) 1.000 0.0199(3) . . H1 H Uiso -0.667(2) 0.25000 0.7055(18) 1.000 0.0280 . . H2 H Uiso -0.5097(18) 0.0793(10) 0.6369(13) 1.000 0.0280 . . H3 H Uiso -0.2383(17) 0.0759(10) 0.5055(12) 1.000 0.0250 . . H6A H Uiso 0.1569(16) 0.1426(9) 0.4711(13) 1.000 0.0220 . . H6B H Uiso -0.0146(16) 0.0817(10) 0.3898(12) 1.000 0.0220 . . H7A H Uiso 0.0811(16) 0.1371(9) 0.1637(13) 1.000 0.0220 . . H7B H Uiso 0.2539(16) 0.0756(10) 0.2463(12) 1.000 0.0220 . . H10A H Uiso 0.7035(16) 0.1456(9) 0.2111(12) 1.000 0.0200 . . H10B H Uiso 0.5159(16) 0.0736(9) 0.1695(12) 1.000 0.0200 . . H11A H Uiso 0.5301(16) 0.1367(9) -0.0716(12) 1.000 0.0210 . . H11B H Uiso 0.7243(16) 0.0763(9) -0.0291(12) 1.000 0.0210 . . 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 N5 0.0147(6) 0.0149(6) 0.0215(6) 0.0000 0.0051(5) 0.0000 N15 0.0271(5) 0.0219(5) 0.0411(6) -0.0017(4) 0.0090(4) 0.0007(4) C1 0.0173(7) 0.0337(9) 0.0182(7) 0.0000 0.0027(6) 0.0000 C2 0.0206(5) 0.0264(6) 0.0228(6) 0.0052(4) 0.0037(4) -0.0029(4) C3 0.0201(5) 0.0202(6) 0.0227(5) 0.0032(4) 0.0039(4) 0.0016(4) C4 0.0135(6) 0.0208(7) 0.0141(7) 0.0000 -0.0001(5) 0.0000 C6 0.0176(5) 0.0140(5) 0.0229(6) 0.0012(4) 0.0041(4) 0.0003(4) C7 0.0170(5) 0.0146(5) 0.0242(6) -0.0017(4) 0.0052(4) -0.0005(4) C8 0.0173(7) 0.0149(7) 0.0187(7) 0.0000 0.0027(5) 0.0000 C9 0.0172(7) 0.0143(7) 0.0165(7) 0.0000 0.0017(5) 0.0000 C10 0.0163(5) 0.0150(5) 0.0201(5) 0.0014(4) 0.0036(4) 0.0011(4) C11 0.0196(5) 0.0147(5) 0.0195(5) -0.0012(4) 0.0042(4) -0.0003(4) C12 0.0197(7) 0.0164(7) 0.0156(7) 0.0000 0.0010(5) 0.0000 C13 0.0197(7) 0.0147(7) 0.0183(7) 0.0000 0.0034(5) 0.0000 C14 0.0185(5) 0.0183(5) 0.0230(5) 0.0006(4) 0.0051(4) -0.0031(4) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N5 C4 1.4072(18) . . yes N5 C6 1.4659(12) . . yes N15 C14 1.1476(14) . . yes C1 C2 1.3832(13) . . no C2 C3 1.3909(15) . . no C3 C4 1.4072(13) . . no C6 C7 1.5319(15) . . no C7 C8 1.5100(13) . . no C8 C9 1.3450(19) . . no C9 C10 1.5103(13) . . no C10 C11 1.5523(15) . . no C11 C12 1.4958(13) . . no C12 C13 1.358(2) . . no C13 C14 1.4414(13) . . no C1 H1 1.044(15) . . no C2 H2 0.960(12) . . no C3 H3 0.980(12) . . no C6 H6A 1.004(12) . . no C6 H6B 0.978(12) . . no C7 H7A 1.028(12) . . no C7 H7B 0.994(12) . . no C10 H10A 0.998(11) . . no C10 H10B 1.011(11) . . no C11 H11A 1.004(11) . . no C11 H11B 0.986(11) . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N5 C6 118.93(6) . . . yes C4 N5 C6 118.93(6) . . 4_555 yes C6 N5 C6 111.96(9) . . 4_555 yes C2 C1 C2 118.53(12) . . 4_555 no C1 C2 C3 121.17(10) . . . no C2 C3 C4 121.09(10) . . . no N5 C4 C3 121.47(6) . . . yes N5 C4 C3 121.47(6) . . 4_555 yes C3 C4 C3 116.93(11) . . 4_555 no N5 C6 C7 111.19(9) . . . yes C6 C7 C8 113.15(9) . . . no C7 C8 C9 124.47(6) . . . no C7 C8 C7 111.00(10) . . 4_555 no C7 C8 C9 124.47(6) 4_555 . . no C8 C9 C10 124.49(6) . . . no C8 C9 C10 124.49(6) . . 4_555 no C10 C9 C10 110.95(10) . . 4_555 no C9 C10 C11 110.58(9) . . . no C10 C11 C12 110.62(9) . . . no C11 C12 C13 121.93(6) . . . no C11 C12 C11 116.11(11) . . 4_555 no C11 C12 C13 121.93(6) 4_555 . . no C12 C13 C14 123.23(6) . . . no C12 C13 C14 123.23(6) . . 4_555 no C14 C13 C14 113.52(11) . . 4_555 no N15 C14 C13 175.89(11) . . . yes C2 C1 H1 120.73(7) . . . no C2 C1 H1 120.73(7) 4_555 . . no C1 C2 H2 120.7(8) . . . no C3 C2 H2 118.1(8) . . . no C2 C3 H3 117.5(7) . . . no C4 C3 H3 121.4(7) . . . no N5 C6 H6A 110.0(6) . . . no N5 C6 H6B 109.7(7) . . . no C7 C6 H6A 110.4(7) . . . no C7 C6 H6B 108.3(7) . . . no H6A C6 H6B 107.1(9) . . . no C6 C7 H7A 108.4(7) . . . no C6 C7 H7B 107.8(7) . . . no C8 C7 H7A 108.8(6) . . . no C8 C7 H7B 112.8(7) . . . no H7A C7 H7B 105.6(9) . . . no C9 C10 H10A 108.8(6) . . . no C9 C10 H10B 113.2(6) . . . no C11 C10 H10A 108.6(6) . . . no C11 C10 H10B 108.0(6) . . . no H10A C10 H10B 107.5(9) . . . no C10 C11 H11A 108.7(7) . . . no C10 C11 H11B 110.6(7) . . . no C12 C11 H11A 108.1(6) . . . no C12 C11 H11B 112.3(7) . . . no H11A C11 H11B 106.4(9) . . . 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 C6 N5 C4 C3 -20.94(18) . . . . no C6 N5 C4 C3 163.48(11) . . . 4_555 no C6 N5 C4 C3 -163.48(11) 4_555 . . . no C4 N5 C6 C7 157.54(10) . . . . no C6 N5 C6 C7 -57.49(12) 4_555 . . . no C2 C1 C2 C3 -0.46(19) 4_555 . . . no C1 C2 C3 C4 -0.78(18) . . . . no C2 C3 C4 N5 -173.83(11) . . . . no C2 C3 C4 C3 1.93(17) . . . 4_555 no N5 C6 C7 C8 53.38(12) . . . . no C6 C7 C8 C7 -48.79(13) . . . 4_555 no C6 C7 C8 C9 134.08(13) . . . . no C7 C8 C9 C10 176.62(11) . . . 4_555 no C7 C8 C9 C10 -176.62(11) 4_555 . . . no C7 C8 C9 C10 0.1(2) . . . . no C8 C9 C10 C11 117.93(13) . . . . no C10 C9 C10 C11 -58.98(12) 4_555 . . . no C9 C10 C11 C12 53.16(12) . . . . no C10 C11 C12 C13 127.74(13) . . . . no C10 C11 C12 C11 -50.50(14) . . . 4_555 no C11 C12 C13 C14 -178.51(11) . . . 4_555 no C11 C12 C13 C14 178.51(11) 4_555 . . . no C11 C12 C13 C14 0.4(2) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N15 C7 3.3409(15) . 3_655 no N15 C10 3.3724(15) . 3_755 no N5 H10A 2.753(11) . 1_455 no N5 H10A 2.753(11) . 4_455 no N15 H1 2.883(10) . 1_754 no N15 H6B 2.788(12) . 3_655 no N15 H7A 2.829(11) . 3_655 no N15 H10A 2.933(11) . 3_755 no N15 H11B 2.845(11) . 3_755 no N15 H1 2.883(10) . 4_754 no C1 C12 3.455(2) . 1_456 no C1 C12 3.455(2) . 4_456 no C7 N15 3.3409(15) . 3_655 no C10 N15 3.3724(15) . 3_755 no C12 C1 3.455(2) . 4_654 no C12 C1 3.455(2) . 1_654 no C1 H11A 2.974(11) . 4_456 no C1 H11A 2.974(11) . 1_456 no C1 H6A 2.978(12) . 1_455 no C1 H6A 2.978(12) . 4_455 no C2 H11A 2.987(11) . 1_456 no C2 H6A 3.010(12) . 1_455 no C3 H6B 2.508(11) . . no C3 H10A 2.998(11) . 1_455 no C4 H10A 2.938(11) . 4_455 no C4 H10A 2.938(11) . 1_455 no C6 H3 3.087(12) . 3_556 no C6 H10A 3.030(11) . 1_455 no C6 H3 2.590(12) . . no C7 H10B 2.657(11) . . no C10 H7B 2.670(11) . . no C14 H1 2.902(14) . 1_754 no C14 H7A 2.925(12) . 1_655 no C14 H11B 2.518(11) . . no C14 H1 2.902(14) . 4_754 no H1 N15 2.883(10) . 1_356 no H1 C14 2.902(14) . 1_356 no H1 N15 2.883(10) . 4_356 no H1 C14 2.902(14) . 4_356 no H2 H10B 2.568(16) . 3_556 no H3 C6 2.590(12) . . no H3 H6B 1.932(16) . . no H3 C6 3.087(12) . 3_556 no H6A C1 2.978(12) . 1_655 no H6A C2 3.010(12) . 1_655 no H6A C1 2.978(12) . 4_655 no H6A H6A 2.556(15) . 4_555 no H6B C3 2.508(11) . . no H6B H3 1.932(16) . . no H6B N15 2.788(12) . 3_655 no H7A C14 2.925(12) . 1_455 no H7A N15 2.829(11) . 3_655 no H7B C10 2.670(11) . . no H7B H10B 1.997(16) . . no H10A N5 2.753(11) . 1_655 no H10A C3 2.998(11) . 1_655 no H10A C4 2.938(11) . 1_655 no H10A C6 3.030(11) . 1_655 no H10A N15 2.933(11) . 3_755 no H10A N5 2.753(11) . 4_655 no H10A C4 2.938(11) . 4_655 no H10A H10A 2.485(15) . 4_555 no H10B C7 2.657(11) . . no H10B H7B 1.997(16) . . no H10B H2 2.568(16) . 3_556 no H11A C1 2.974(11) . 1_654 no H11A C2 2.987(11) . 1_654 no H11A C1 2.974(11) . 4_654 no H11B C14 2.518(11) . . no H11B N15 2.845(11) . 3_755 no #===END data_2 _database_code_CSD 160668 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H23 N3' _chemical_formula_structural ? _chemical_formula_sum 'C20 H23 N3' _chemical_formula_weight 305.41 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 21/m' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z -x,-y,-z x,1/2-y,z _cell_length_a 7.0137(10) _cell_length_b 11.941(2) _cell_length_c 9.6449(17) _cell_angle_alpha 90 _cell_angle_beta 92.286(11) _cell_angle_gamma 90 _cell_volume 807.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 365 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _cell_special_details ; Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set. ; _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.075 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Nonius Kappa CCD area detector' _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 4545 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.42 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measured_fraction_theta_full 0.99 _diffrn_reflns_reduction_process ; ? ; # number of unique reflections _reflns_number_total 1724 _reflns_number_gt 1346 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'PLATON (Spek, 2001)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2 > 2sigma(F^2) is used only for calculating -R-factor-obs 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 'w=1/[\s^2^(F~o~^2^)+(0.01P)^2^+0.75P] where P=(F~o~^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 ? _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 1724 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.357 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.050 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N5 N Uani 0.5573(3) 0.25000 0.6062(2) 1.000 0.0262(6) . . N15 N Uani -0.6223(2) 0.07133(15) 1.17616(17) 1.000 0.0415(6) . . C1 C Uani 1.0384(4) 0.25000 0.3529(3) 1.000 0.0333(8) . . C2 C Uani 0.9555(2) 0.15011(17) 0.39285(19) 1.000 0.0338(6) . . C3 C Uani 0.7952(2) 0.14959(16) 0.47282(18) 1.000 0.0289(6) . . C4 C Uani 0.7110(3) 0.25000 0.5163(2) 1.000 0.0245(7) . . C6 C Uani 0.4427(2) 0.14750(15) 0.61181(19) 1.000 0.0275(5) . . C7 C Uani 0.3142(2) 0.14699(15) 0.73624(18) 1.000 0.0276(5) . . C8 C Uani 0.1854(3) 0.25000 0.7420(2) 1.000 0.0237(7) . . C9 C Uani 0.0644(3) 0.25000 0.8719(2) 1.000 0.0227(7) . . C10 C Uani -0.0621(2) 0.14663(15) 0.88118(17) 1.000 0.0250(5) . . C11 C Uani -0.1656(2) 0.14325(15) 1.01893(18) 1.000 0.0266(5) . . C12 C Uani -0.2675(3) 0.25000 1.0493(2) 1.000 0.0252(7) . . C13 C Uani -0.4382(3) 0.25000 1.1104(2) 1.000 0.0246(7) . . C14 C Uani -0.5362(2) 0.14896(15) 1.14596(17) 1.000 0.0277(5) . . H1 H Uiso 1.177(4) 0.25000 0.295(3) 1.000 0.0400 . . H2 H Uiso 1.010(3) 0.0750(19) 0.368(2) 1.000 0.0410 . . H3 H Uiso 0.747(3) 0.0786(18) 0.4997(19) 1.000 0.0350 . . H6A H Uiso 0.364(3) 0.1376(16) 0.523(2) 1.000 0.0330 . . H6B H Uiso 0.527(3) 0.0805(17) 0.6213(18) 1.000 0.0330 . . H7A H Uiso 0.397(3) 0.1404(16) 0.827(2) 1.000 0.0330 . . H7B H Uiso 0.238(3) 0.0778(17) 0.7328(18) 1.000 0.0330 . . H8 H Uiso 0.097(4) 0.25000 0.655(3) 1.000 0.0280 . . H9 H Uiso 0.156(4) 0.25000 0.953(3) 1.000 0.0270 . . H10A H Uiso -0.157(3) 0.1481(16) 0.8026(19) 1.000 0.0300 . . H10B H Uiso 0.008(3) 0.0742(17) 0.8744(18) 1.000 0.0300 . . H11A H Uiso -0.071(3) 0.1313(16) 1.0972(19) 1.000 0.0320 . . H11B H Uiso -0.255(3) 0.0783(17) 1.0231(19) 1.000 0.0320 . . 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 N5 0.0232(10) 0.0248(11) 0.0311(11) 0.0000 0.0086(8) 0.0000 N15 0.0388(9) 0.0352(10) 0.0515(11) 0.0007(8) 0.0136(7) -0.0031(8) C1 0.0287(13) 0.0438(17) 0.0279(13) 0.0000 0.0062(10) 0.0000 C2 0.0300(9) 0.0395(12) 0.0321(10) -0.0064(9) 0.0053(7) 0.0028(8) C3 0.0269(9) 0.0291(11) 0.0311(9) -0.0032(8) 0.0055(7) -0.0022(7) C4 0.0203(11) 0.0311(14) 0.0221(11) 0.0000 0.0022(9) 0.0000 C6 0.0264(8) 0.0234(10) 0.0335(10) -0.0008(8) 0.0100(7) -0.0004(7) C7 0.0275(9) 0.0233(10) 0.0327(9) 0.0009(8) 0.0110(7) 0.0006(7) C8 0.0212(11) 0.0262(13) 0.0241(12) 0.0000 0.0055(9) 0.0000 C9 0.0230(11) 0.0225(13) 0.0229(11) 0.0000 0.0040(9) 0.0000 C10 0.0268(8) 0.0218(9) 0.0271(9) -0.0016(7) 0.0081(7) -0.0005(7) C11 0.0284(9) 0.0228(9) 0.0293(9) 0.0007(7) 0.0087(7) 0.0003(7) C12 0.0262(12) 0.0234(13) 0.0263(12) 0.0000 0.0042(9) 0.0000 C13 0.0273(12) 0.0213(13) 0.0254(12) 0.0000 0.0037(9) 0.0000 C14 0.0255(8) 0.0274(10) 0.0306(9) -0.0014(8) 0.0079(7) 0.0018(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N5 C4 1.410(3) . . yes N5 C6 1.466(2) . . yes N15 C14 1.150(2) . . yes C1 C2 1.388(2) . . no C2 C3 1.389(2) . . no C3 C4 1.408(2) . . no C6 C7 1.529(2) . . no C7 C8 1.528(2) . . no C8 C9 1.541(3) . . no C9 C10 1.525(2) . . no C10 C11 1.540(2) . . no C11 C12 1.496(2) . . no C12 C13 1.355(3) . . no C13 C14 1.437(2) . . no C1 H1 1.14(3) . . no C2 H2 1.01(2) . . no C3 H3 0.95(2) . . no C6 H6A 1.01(2) . . no C6 H6B 1.00(2) . . no C7 H7A 1.03(2) . . no C7 H7B 0.98(2) . . no C8 H8 1.02(3) . . no C9 H9 0.99(3) . . no C10 H10A 0.989(19) . . no C10 H10B 1.00(2) . . no C11 H11A 1.00(2) . . no C11 H11B 1.00(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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N5 C6 117.15(11) . . . yes C4 N5 C6 117.15(11) . . 4_555 yes C6 N5 C6 113.15(16) . . 4_555 yes C2 C1 C2 118.5(2) . . 4_555 no C1 C2 C3 121.02(19) . . . no C2 C3 C4 121.35(17) . . . no N5 C4 C3 121.55(10) . . . yes N5 C4 C3 121.55(10) . . 4_555 yes C3 C4 C3 116.79(17) . . 4_555 no N5 C6 C7 111.92(15) . . . yes C6 C7 C8 113.14(15) . . . no C7 C8 C9 112.02(11) . . . no C7 C8 C7 107.17(15) . . 4_555 no C7 C8 C9 112.02(11) 4_555 . . no C8 C9 C10 112.85(11) . . . no C8 C9 C10 112.85(11) . . 4_555 no C10 C9 C10 108.09(15) . . 4_555 no C9 C10 C11 111.55(14) . . . no C10 C11 C12 113.08(15) . . . no C11 C12 C13 121.49(9) . . . no C11 C12 C11 116.87(16) . . 4_555 no C11 C12 C13 121.49(9) 4_555 . . no C12 C13 C14 122.89(9) . . . no C12 C13 C14 122.89(9) . . 4_555 no C14 C13 C14 114.22(16) . . 4_555 no N15 C14 C13 176.57(17) . . . yes C2 C1 H1 120.71(14) . . . no C2 C1 H1 120.71(14) 4_555 . . no C1 C2 H2 122.1(12) . . . no C3 C2 H2 116.8(12) . . . no C2 C3 H3 117.3(13) . . . no C4 C3 H3 121.3(12) . . . no N5 C6 H6A 110.4(11) . . . no N5 C6 H6B 110.4(12) . . . no C7 C6 H6A 110.3(12) . . . no C7 C6 H6B 106.9(11) . . . no H6A C6 H6B 106.7(15) . . . no C6 C7 H7A 109.6(11) . . . no C6 C7 H7B 108.3(11) . . . no C8 C7 H7A 110.1(11) . . . no C8 C7 H7B 110.9(12) . . . no H7A C7 H7B 104.5(15) . . . no C7 C8 H8 108.1(9) . . . no C9 C8 H8 109.4(16) . . . no C7 C8 H8 108.1(9) 4_555 . . no C8 C9 H9 106.3(16) . . . no C10 C9 H9 108.3(8) . . . no C10 C9 H9 108.3(8) 4_555 . . no C9 C10 H10A 108.4(11) . . . no C9 C10 H10B 114.1(12) . . . no C11 C10 H10A 109.6(12) . . . no C11 C10 H10B 106.5(11) . . . no H10A C10 H10B 106.5(16) . . . no C10 C11 H11A 109.6(11) . . . no C10 C11 H11B 111.9(11) . . . no C12 C11 H11A 106.4(11) . . . no C12 C11 H11B 110.4(12) . . . no H11A C11 H11B 105.0(16) . . . 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 C6 N5 C4 C3 -22.3(3) . . . . no C6 N5 C4 C3 161.74(17) . . . 4_555 no C6 N5 C4 C3 -161.74(17) 4_555 . . . no C4 N5 C6 C7 166.03(16) . . . . no C6 N5 C6 C7 -53.0(2) 4_555 . . . no C2 C1 C2 C3 -1.0(3) 4_555 . . . no C1 C2 C3 C4 0.0(3) . . . . no C2 C3 C4 N5 -175.08(18) . . . . no C2 C3 C4 C3 1.0(3) . . . 4_555 no N5 C6 C7 C8 54.83(18) . . . . no C6 C7 C8 C7 -54.08(18) . . . 4_555 no C6 C7 C8 C9 -177.34(14) . . . . no C7 C8 C9 C10 178.79(14) . . . 4_555 no C7 C8 C9 C10 -178.79(14) 4_555 . . . no C7 C8 C9 C10 -58.3(2) . . . . no C8 C9 C10 C11 174.25(14) . . . . no C10 C9 C10 C11 -60.23(18) 4_555 . . . no C9 C10 C11 C12 50.99(18) . . . . no C10 C11 C12 C13 142.87(18) . . . . no C10 C11 C12 C11 -41.6(2) . . . 4_555 no C11 C12 C13 C14 177.47(17) . . . 4_555 no C11 C12 C13 C14 -177.47(17) 4_555 . . . no C11 C12 C13 C14 -2.1(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N15 C10 3.447(2) . 3_457 no N15 H1 2.824(19) . 1_356 no N15 H6B 2.729(19) . 3_557 no N15 H11B 2.738(19) . 3_457 no N15 H1 2.824(19) . 4_356 no C1 C12 3.560(4) . 1_654 no C1 C12 3.560(4) . 4_654 no C10 N15 3.447(2) . 3_457 no C12 C1 3.560(4) . 4_456 no C12 C1 3.560(4) . 1_456 no C1 H6A 3.07(2) . 4_655 no C1 H11A 2.920(19) . 1_654 no C1 H11A 2.920(19) . 4_654 no C1 H6A 3.07(2) . 1_655 no C1 H8 2.93(3) . 1_655 no C1 H8 2.93(3) . 4_655 no C2 H11A 2.859(18) . 1_654 no C2 H6A 3.09(2) . 1_655 no C2 H8 2.93(3) . 4_655 no C2 H8 2.93(3) . 1_655 no C3 H6A 3.09(2) . . no C3 H8 2.95(3) . 4_655 no C3 H6B 2.55(2) . . no C3 H8 2.95(3) . 1_655 no C4 H8 2.97(3) . 1_655 no C4 H8 2.97(3) . 4_655 no C6 H3 2.57(2) . . no C7 H10B 2.72(2) . . no C10 H7B 2.72(2) . . no C11 H10B 2.99(2) . 3_557 no C14 H1 2.79(3) . 1_356 no C14 H7A 3.095(19) . 1_455 no C14 H9 3.04(3) . 1_455 no C14 H11B 2.49(2) . . no C14 H1 2.79(3) . 4_356 no C14 H9 3.04(3) . 4_455 no H1 N15 2.824(19) . 1_754 no H1 C14 2.79(3) . 1_754 no H1 N15 2.824(19) . 4_754 no H1 C14 2.79(3) . 4_754 no H3 C6 2.57(2) . . no H3 H6B 1.98(3) . . no H6A C1 3.07(2) . 1_455 no H6A C2 3.09(2) . 1_455 no H6A C3 3.09(2) . . no H6A C1 3.07(2) . 4_455 no H6B C3 2.55(2) . . no H6B H3 1.98(3) . . no H6B N15 2.729(19) . 3_557 no H7A C14 3.095(19) . 1_655 no H7B C10 2.72(2) . . no H7B H10B 2.16(3) . . no H8 C1 2.93(3) . 1_455 no H8 C2 2.93(3) . 1_455 no H8 C3 2.95(3) . 1_455 no H8 C4 2.97(3) . 1_455 no H8 C1 2.93(3) . 4_455 no H8 C2 2.93(3) . 4_455 no H8 C3 2.95(3) . 4_455 no H8 C4 2.97(3) . 4_455 no H9 C14 3.04(3) . 1_655 no H9 H7A 2.49(3) . . no H9 H11A 2.58(3) . . no H9 C14 3.04(3) . 4_655 no H9 H7A 2.49(3) . 4_555 no H9 H11A 2.58(3) . 4_555 no H10A H10A 2.43(3) . 4_555 no H10B C7 2.72(2) . . no H10B H7B 2.16(3) . . no H10B C11 2.99(2) . 3_557 no H10B H11A 2.51(3) . 3_557 no H11A C1 2.920(19) . 1_456 no H11A C2 2.859(18) . 1_456 no H11A H10B 2.51(3) . 3_557 no H11A C1 2.920(19) . 4_456 no H11B C14 2.49(2) . . no H11B N15 2.74(2) . 3_457 no # End of Crystallographic Information File #====END