# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1099 data_global #==================================================================== # 1. SUBMISSION DETAILS _publ_contact author ; Mark Thornton-Pett School of Chemistry University of Leeds Leeds LS2 9JT UK ; _publ_contact_author_phone '+44 (0)113 2336423' _publ_contact_author_fax '+44 (0)113 2336565' _publ_contact_author_email marktp@chem.leeds.ac.uk _publ_requested_journal 'J. Chem. Soc., Chem. Commun.' _publ_contact_letter ; The following two sets of data are for the structures included in the paper below which we have just submitted to you. ; #======================================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; "Facile synthesis of amino-functionalised ferrocenes and vanadocenes" ; loop_ _publ_author_name _publ_author_address 'Patrick McGowan' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Samantha Bradley' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Karrie Oughton' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Mark Thornton-Pett' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Mark Walsh' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; #================================================================= data_PM1 _audit_creation_date 97-11-17 _audit_creation_method 'STADI4, X-RED' _audit_author_name 'J. Richter' _audit_contact_author 'J. Richter' _audit_contact_author_address ; STOE & CIE GmbH Hilpertstr. 10 D-64295 Darmstadt Germany ; _audit_contact_author_email 100066.3306@compuserve.com _audit_contact_author_fax '+49 6151 891293 ' _audit_contact_author_phone '+49 6151 891225 / 899174' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H32 Fe N2' _chemical_formula_weight 380.35 _chemical_melting_point ? _chemical_compound_source ? 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' 'Fe' 'Fe' 0.3463 0.8444 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1259(5) _cell_length_b 10.7296(10) _cell_length_c 13.4298(11) _cell_angle_alpha 103.584(8) _cell_angle_beta 96.905(7) _cell_angle_gamma 101.691(8) _cell_volume 962.08(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 78 _cell_measurement_theta_min 17.6 _cell_measurement_theta_max 22.5 _exptl_crystal_description block _exptl_crystal_colour prism _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method ? _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.790 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6157 _exptl_absorpt_correction_T_max 0.7429 _exptl_absorpt_process_details ; Psi Scan Reflections used Mu * R = 0.20 H K L 2Theta Chi Imin/Imax 3 -2 0 17.8 -83.4 0.834 -3 2 0 17.8 83.4 0.835 4 -2 -1 23.3 -85.3 0.834 -4 2 1 23.3 85.3 0.824 5 -3 0 29.6 -85.5 0.825 -5 3 0 29.6 85.5 0.834 6 -4 0 36.0 -83.4 0.828 -6 4 0 36.0 83.4 0.830 -7 4 0 41.7 86.2 0.820 7 -4 0 41.7 -86.2 0.786 -8 3 2 47.1 84.3 0.821 8 -3 -2 47.1 -84.3 0.832 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_collimation '0.8 mm' _diffrn_radiation_detector 'NaI(Tl) scintillation counter' _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_polarisn_norm 90 _diffrn_measurement_device_type 'STOE STADI4 4-circle-diffractometer' _diffrn_measurement_method ; Scan width (omega) = 1.65 - 1.80, scan ratio 2theta:omega = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987) ; _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3780 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0080 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.98 _reflns_number_total 3780 _reflns_number_observed 3678 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'STADI4 (STOE, 1996)' _computing_cell_refinement 'STADI4 (STOE, 1996)' _computing_data_reduction 'X-RED (STOE, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 7 with very negative F^2^ or 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 w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.4452P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0647(24) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3773 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0256 _refine_ls_R_factor_obs 0.0248 _refine_ls_wR_factor_all 0.0695 _refine_ls_wR_factor_obs 0.0668 _refine_ls_goodness_of_fit_all 1.066 _refine_ls_goodness_of_fit_obs 1.067 _refine_ls_restrained_S_all 1.093 _refine_ls_restrained_S_obs 1.067 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe Fe 0.19073(2) 0.29740(2) 0.054332(13) 0.01602(8) Uani 1 d . . C1 C 0.1168(2) 0.19955(13) -0.10311(10) 0.0185(3) Uani 1 d . . C2 C 0.2033(2) 0.12263(13) -0.04565(10) 0.0197(3) Uani 1 d . . H2 H 0.1443(2) 0.03612(13) -0.04278(10) 0.024 Uiso 1 calc R . C3 C 0.3936(2) 0.19787(14) 0.00673(10) 0.0219(3) Uani 1 d . . H3 H 0.4824(2) 0.17041(14) 0.05062(10) 0.026 Uiso 1 calc R . C4 C 0.4262(2) 0.32141(14) -0.01862(11) 0.0218(3) Uani 1 d . . H4 H 0.5411(2) 0.39061(14) 0.00499(11) 0.026 Uiso 1 calc R . C5 C 0.2560(2) 0.32271(13) -0.08566(10) 0.0205(3) Uani 1 d . . H5 H 0.2379(2) 0.39349(13) -0.11404(10) 0.025 Uiso 1 calc R . C6 C -0.0769(2) 0.15631(13) -0.17505(10) 0.0199(3) Uani 1 d . . H6 H -0.1172(2) 0.23722(13) -0.18497(10) 0.024 Uiso 1 calc R . C7 C -0.0621(2) 0.07225(15) -0.28224(11) 0.0251(3) Uani 1 d . . H7A H 0.0340(2) 0.12433(15) -0.31341(11) 0.030 Uiso 1 calc R . H7B H -0.0161(2) -0.00646(15) -0.27399(11) 0.030 Uiso 1 calc R . C8 C -0.2591(2) 0.0286(2) -0.35432(11) 0.0289(3) Uani 1 d . . H8A H -0.3008(2) 0.1073(2) -0.36607(11) 0.035 Uiso 1 calc R . H8B H -0.2468(2) -0.0264(2) -0.42245(11) 0.035 Uiso 1 calc R . N9 N -0.4065(2) -0.04680(12) -0.31037(9) 0.0256(3) Uani 1 d . . C9 C -0.5940(2) -0.0907(2) -0.38087(13) 0.0368(4) Uani 1 d . . H9A H -0.5795(5) -0.1451(11) -0.4478(4) 0.055 Uiso 1 calc R . H9B H -0.6390(10) -0.0136(2) -0.3916(8) 0.055 Uiso 1 calc R . H9C H -0.6893(6) -0.1428(11) -0.3505(5) 0.055 Uiso 1 calc R . C10 C -0.4292(2) 0.0335(2) -0.21030(12) 0.0296(3) Uani 1 d . . H10A H -0.5304(2) -0.0183(2) -0.18176(12) 0.036 Uiso 1 calc R . H10B H -0.4724(2) 0.1124(2) -0.22056(12) 0.036 Uiso 1 calc R . C11 C -0.2381(2) 0.0767(2) -0.13332(11) 0.0257(3) Uani 1 d . . H11A H -0.1987(2) -0.0021(2) -0.12016(11) 0.031 Uiso 1 calc R . H11B H -0.2565(2) 0.1314(2) -0.06643(11) 0.031 Uiso 1 calc R . C12 C 0.2661(2) 0.42762(13) 0.20217(10) 0.0188(3) Uani 1 d . . C13 C 0.1755(2) 0.29803(14) 0.20716(10) 0.0208(3) Uani 1 d . . H13 H 0.2320(2) 0.24655(14) 0.24524(10) 0.025 Uiso 1 calc R . C14 C -0.0144(2) 0.25929(15) 0.14513(11) 0.0245(3) Uani 1 d . . H14 H -0.1066(2) 0.17802(15) 0.13544(11) 0.029 Uiso 1 calc R . C15 C -0.0420(2) 0.36336(15) 0.10033(11) 0.0251(3) Uani 1 d . . H15 H -0.1550(2) 0.36362(15) 0.05503(11) 0.030 Uiso 1 calc R . C16 C 0.1308(2) 0.46742(14) 0.13567(11) 0.0221(3) Uani 1 d . . H16 H 0.1523(2) 0.54924(14) 0.11800(11) 0.027 Uiso 1 calc R . C17 C 0.4597(2) 0.51238(13) 0.26250(10) 0.0195(3) Uani 1 d . . H17 H 0.5034(2) 0.58238(13) 0.22687(10) 0.023 Uiso 1 calc R . C18 C 0.6192(2) 0.43679(15) 0.27034(11) 0.0247(3) Uani 1 d . . H18A H 0.5769(2) 0.36468(15) 0.30308(11) 0.030 Uiso 1 calc R . H18B H 0.6409(2) 0.39673(15) 0.19966(11) 0.030 Uiso 1 calc R . C19 C 0.8089(2) 0.5289(2) 0.33474(11) 0.0261(3) Uani 1 d . . H19A H 0.9102(2) 0.4784(2) 0.33865(11) 0.031 Uiso 1 calc R . H19B H 0.8540(2) 0.5989(2) 0.30043(11) 0.031 Uiso 1 calc R . N20 N 0.7818(2) 0.58932(12) 0.43989(9) 0.0247(3) Uani 1 d . . C20 C 0.9652(2) 0.6737(2) 0.50198(12) 0.0342(4) Uani 1 d . . H20A H 1.0627(6) 0.6214(3) 0.5044(8) 0.051 Uiso 1 calc R . H20B H 0.9456(5) 0.7111(10) 0.5728(3) 0.051 Uiso 1 calc R . H20C H 1.0105(10) 0.7454(7) 0.4705(6) 0.051 Uiso 1 calc R . C21 C 0.6341(2) 0.66556(15) 0.43674(11) 0.0273(3) Uani 1 d . . H21A H 0.6791(2) 0.73894(15) 0.40573(11) 0.033 Uiso 1 calc R . H21B H 0.6173(2) 0.70444(15) 0.50866(11) 0.033 Uiso 1 calc R . C22 C 0.4385(2) 0.58086(14) 0.37355(11) 0.0235(3) Uani 1 d . . H22A H 0.3450(2) 0.63714(14) 0.37006(11) 0.028 Uiso 1 calc R . H22B H 0.3862(2) 0.51325(14) 0.40862(11) 0.028 Uiso 1 calc R . 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 Fe 0.01597(12) 0.01644(12) 0.01437(12) 0.00167(7) 0.00225(7) 0.00412(7) C1 0.0213(6) 0.0185(6) 0.0143(6) 0.0014(5) 0.0040(5) 0.0047(5) C2 0.0241(7) 0.0169(6) 0.0182(6) 0.0024(5) 0.0048(5) 0.0067(5) C3 0.0209(7) 0.0270(7) 0.0182(6) 0.0027(5) 0.0045(5) 0.0099(6) C4 0.0176(6) 0.0254(7) 0.0206(6) 0.0030(5) 0.0058(5) 0.0031(5) C5 0.0228(7) 0.0202(6) 0.0180(6) 0.0050(5) 0.0055(5) 0.0030(5) C6 0.0235(7) 0.0181(6) 0.0161(6) 0.0026(5) 0.0001(5) 0.0045(5) C7 0.0287(7) 0.0262(7) 0.0162(6) 0.0023(5) 0.0040(5) 0.0013(6) C8 0.0369(8) 0.0293(8) 0.0159(6) 0.0020(6) -0.0005(6) 0.0050(6) N9 0.0246(6) 0.0251(6) 0.0205(6) 0.0005(5) -0.0047(5) 0.0026(5) C9 0.0306(8) 0.0398(9) 0.0287(8) -0.0028(7) -0.0092(7) 0.0056(7) C10 0.0231(7) 0.0373(8) 0.0225(7) 0.0013(6) 0.0004(6) 0.0039(6) C11 0.0223(7) 0.0339(8) 0.0163(6) 0.0027(6) 0.0018(5) 0.0022(6) C12 0.0196(6) 0.0196(6) 0.0157(6) 0.0007(5) 0.0044(5) 0.0053(5) C13 0.0237(7) 0.0223(7) 0.0149(6) 0.0026(5) 0.0059(5) 0.0037(5) C14 0.0204(7) 0.0260(7) 0.0215(7) -0.0016(5) 0.0075(5) 0.0000(5) C15 0.0181(6) 0.0321(8) 0.0217(7) -0.0023(6) 0.0025(5) 0.0100(6) C16 0.0245(7) 0.0208(7) 0.0207(7) 0.0007(5) 0.0038(5) 0.0103(5) C17 0.0195(6) 0.0194(6) 0.0166(6) 0.0023(5) 0.0028(5) 0.0013(5) C18 0.0220(7) 0.0280(7) 0.0203(7) -0.0002(6) 0.0023(5) 0.0064(6) C19 0.0209(7) 0.0346(8) 0.0201(7) 0.0046(6) 0.0027(5) 0.0040(6) N20 0.0220(6) 0.0291(6) 0.0175(6) 0.0027(5) -0.0001(5) -0.0002(5) C20 0.0281(8) 0.0401(9) 0.0240(8) 0.0038(7) -0.0037(6) -0.0045(7) C21 0.0288(8) 0.0248(7) 0.0214(7) -0.0015(6) 0.0018(6) 0.0017(6) C22 0.0231(7) 0.0242(7) 0.0194(7) -0.0002(5) 0.0039(5) 0.0044(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 Fe C15 2.0369(14) . ? Fe C3 2.0410(13) . ? Fe C4 2.0448(13) . ? Fe C16 2.0483(13) . ? Fe C14 2.0524(14) . ? Fe C5 2.0551(13) . ? Fe C2 2.0595(13) . ? Fe C13 2.0668(13) . ? Fe C1 2.0774(13) . ? Fe C12 2.0782(13) . ? C1 C2 1.431(2) . ? C1 C5 1.433(2) . ? C1 C6 1.504(2) . ? C2 C3 1.430(2) . ? C3 C4 1.426(2) . ? C4 C5 1.426(2) . ? C6 C11 1.531(2) . ? C6 C7 1.537(2) . ? C7 C8 1.524(2) . ? C8 N9 1.461(2) . ? N9 C9 1.461(2) . ? N9 C10 1.463(2) . ? C10 C11 1.523(2) . ? C12 C13 1.430(2) . ? C12 C16 1.431(2) . ? C12 C17 1.504(2) . ? C13 C14 1.427(2) . ? C14 C15 1.422(2) . ? C15 C16 1.429(2) . ? C17 C18 1.532(2) . ? C17 C22 1.540(2) . ? C18 C19 1.526(2) . ? C19 N20 1.462(2) . ? N20 C20 1.459(2) . ? N20 C21 1.460(2) . ? C21 C22 1.526(2) . ? 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 C15 Fe C3 169.48(6) . . ? C15 Fe C4 148.58(6) . . ? C3 Fe C4 40.85(6) . . ? C15 Fe C16 40.94(6) . . ? C3 Fe C16 148.53(6) . . ? C4 Fe C16 115.94(6) . . ? C15 Fe C14 40.71(6) . . ? C3 Fe C14 130.72(6) . . ? C4 Fe C14 169.34(6) . . ? C16 Fe C14 68.32(6) . . ? C15 Fe C5 116.26(6) . . ? C3 Fe C5 68.51(6) . . ? C4 Fe C5 40.70(5) . . ? C16 Fe C5 108.37(6) . . ? C14 Fe C5 149.16(6) . . ? C15 Fe C2 130.55(6) . . ? C3 Fe C2 40.82(5) . . ? C4 Fe C2 68.45(6) . . ? C16 Fe C2 169.33(5) . . ? C14 Fe C2 109.21(6) . . ? C5 Fe C2 68.06(5) . . ? C15 Fe C13 68.46(6) . . ? C3 Fe C13 108.68(6) . . ? C4 Fe C13 130.38(6) . . ? C16 Fe C13 68.08(6) . . ? C14 Fe C13 40.53(6) . . ? C5 Fe C13 168.99(5) . . ? C2 Fe C13 117.31(5) . . ? C15 Fe C1 108.33(5) . . ? C3 Fe C1 68.65(5) . . ? C4 Fe C1 68.57(5) . . ? C16 Fe C1 130.43(5) . . ? C14 Fe C1 116.91(5) . . ? C5 Fe C1 40.57(5) . . ? C2 Fe C1 40.48(5) . . ? C13 Fe C1 149.51(5) . . ? C15 Fe C12 68.66(5) . . ? C3 Fe C12 116.23(5) . . ? C4 Fe C12 108.14(5) . . ? C16 Fe C12 40.58(5) . . ? C14 Fe C12 68.20(5) . . ? C5 Fe C12 130.33(5) . . ? C2 Fe C12 149.26(5) . . ? C13 Fe C12 40.36(5) . . ? C1 Fe C12 169.04(5) . . ? C2 C1 C5 107.03(12) . . ? C2 C1 C6 126.82(12) . . ? C5 C1 C6 125.98(12) . . ? C2 C1 Fe 69.09(7) . . ? C5 C1 Fe 68.88(7) . . ? C6 C1 Fe 130.60(9) . . ? C3 C2 C1 108.54(12) . . ? C3 C2 Fe 68.89(7) . . ? C1 C2 Fe 70.43(7) . . ? C4 C3 C2 107.86(12) . . ? C4 C3 Fe 69.72(8) . . ? C2 C3 Fe 70.29(8) . . ? C3 C4 C5 107.90(12) . . ? C3 C4 Fe 69.43(8) . . ? C5 C4 Fe 70.04(8) . . ? C4 C5 C1 108.67(12) . . ? C4 C5 Fe 69.26(8) . . ? C1 C5 Fe 70.55(7) . . ? C1 C6 C11 113.53(11) . . ? C1 C6 C7 111.12(11) . . ? C11 C6 C7 107.95(11) . . ? C8 C7 C6 110.68(12) . . ? N9 C8 C7 111.34(12) . . ? C8 N9 C9 111.05(12) . . ? C8 N9 C10 110.27(12) . . ? C9 N9 C10 109.29(12) . . ? N9 C10 C11 110.79(12) . . ? C10 C11 C6 111.12(12) . . ? C13 C12 C16 107.25(12) . . ? C13 C12 C17 126.88(12) . . ? C16 C12 C17 125.66(12) . . ? C13 C12 Fe 69.39(7) . . ? C16 C12 Fe 68.59(7) . . ? C17 C12 Fe 131.19(9) . . ? C14 C13 C12 108.31(12) . . ? C14 C13 Fe 69.19(8) . . ? C12 C13 Fe 70.25(7) . . ? C15 C14 C13 108.22(12) . . ? C15 C14 Fe 69.06(8) . . ? C13 C14 Fe 70.28(8) . . ? C14 C15 C16 107.73(12) . . ? C14 C15 Fe 70.23(8) . . ? C16 C15 Fe 69.96(8) . . ? C15 C16 C12 108.50(13) . . ? C15 C16 Fe 69.10(8) . . ? C12 C16 Fe 70.84(7) . . ? C12 C17 C18 113.99(11) . . ? C12 C17 C22 110.21(11) . . ? C18 C17 C22 108.29(11) . . ? C19 C18 C17 110.70(12) . . ? N20 C19 C18 110.81(12) . . ? C20 N20 C21 110.11(12) . . ? C20 N20 C19 110.46(12) . . ? C21 N20 C19 110.78(11) . . ? N20 C21 C22 112.03(12) . . ? C21 C22 C17 111.06(11) . . ? _refine_diff_density_max 0.334 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.049 #===END data_sb1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 N2 V' _chemical_formula_weight 375.44 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' 'V' 'V' 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6238(2) _cell_length_b 10.4591(3) _cell_length_c 13.8715(2) _cell_angle_alpha 102.695(2) _cell_angle_beta 98.438(2) _cell_angle_gamma 101.3270(12) _cell_volume 1036.97(4) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 9214 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 0.485 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8926 _exptl_absorpt_correction_T_max 0.9009 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 25mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12278 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 30.18 _reflns_number_total 4434 _reflns_number_gt 3629 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KCCD (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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 w=1/[\s^2^(Fo^2^)+(0.0452P)^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 SHELXL _refine_ls_extinction_coef 0.072(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4434 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group V1 V 0.21278(3) 0.30149(2) 0.057908(14) 0.03414(11) Uani 1 d . . . C1 C 0.1493(2) 0.18940(13) -0.11055(9) 0.0347(3) Uani 1 d . . . C2 C 0.2292(2) 0.11021(14) -0.05239(10) 0.0384(3) Uani 1 d . . . H2 H 0.1694 0.0240 -0.0472 0.046 Uiso 1 calc R . . C3 C 0.4176(2) 0.18229(16) -0.00196(11) 0.0453(4) Uani 1 d . . . H3 H 0.4995 0.1506 0.0403 0.054 Uiso 1 calc R . . C4 C 0.4547(2) 0.30641(16) -0.02757(11) 0.0456(4) Uani 1 d . . . H4 H 0.5657 0.3739 -0.0059 0.055 Uiso 1 calc R . . C5 C 0.2904(2) 0.31169(14) -0.09362(10) 0.0395(3) Uani 1 d . . . H5 H 0.2776 0.3852 -0.1217 0.047 Uiso 1 calc R . . C11 C -0.04105(19) 0.15176(13) -0.18151(9) 0.0354(3) Uani 1 d . . . H11 H -0.0674 0.2374 -0.1938 0.043 Uiso 1 calc R . . C12 C -0.2050(2) 0.08189(17) -0.14054(10) 0.0464(4) Uani 1 d . . . H12A H -0.2138 0.1427 -0.0767 0.056 Uiso 1 calc R . . H12B H -0.1801 -0.0017 -0.1252 0.056 Uiso 1 calc R . . C13 C -0.3937(2) 0.04522(18) -0.21598(11) 0.0510(4) Uani 1 d . . . H13A H -0.4904 -0.0022 -0.1871 0.061 Uiso 1 calc R . . H13B H -0.4260 0.1287 -0.2272 0.061 Uiso 1 calc R . . N14 N -0.38107(17) -0.04126(12) -0.31166(9) 0.0427(3) Uani 1 d . . . C14 C -0.5652(2) -0.07738(19) -0.38069(13) 0.0577(4) Uani 1 d . . . H14A H -0.6561 -0.1276 -0.3510 0.087 Uiso 1 calc R . . H14B H -0.5593 -0.1333 -0.4463 0.087 Uiso 1 calc R . . H14C H -0.6000 0.0053 -0.3896 0.087 Uiso 1 calc R . . C15 C -0.2304(2) 0.02699(15) -0.35438(10) 0.0447(3) Uani 1 d . . . H15A H -0.2572 0.1115 -0.3667 0.054 Uiso 1 calc R . . H15B H -0.2273 -0.0322 -0.4201 0.054 Uiso 1 calc R . . C16 C -0.0366(2) 0.06133(14) -0.28355(9) 0.0390(3) Uani 1 d . . . H16A H -0.0042 -0.0229 -0.2742 0.047 Uiso 1 calc R . . H16B H 0.0568 0.1082 -0.3147 0.047 Uiso 1 calc R . . C6 C 0.27921(19) 0.44481(13) 0.21659(9) 0.0344(3) Uani 1 d . . . C7 C 0.1538(2) 0.49056(15) 0.15049(10) 0.0433(3) Uani 1 d . . . H7 H 0.1811 0.5738 0.1326 0.052 Uiso 1 calc R . . C8 C -0.0199(2) 0.39114(18) 0.11535(12) 0.0519(4) Uani 1 d . . . H8 H -0.1240 0.3977 0.0715 0.062 Uiso 1 calc R . . C9 C -0.0039(2) 0.28356(17) 0.15890(11) 0.0484(4) Uani 1 d . . . H9 H -0.0962 0.2039 0.1499 0.058 Uiso 1 calc R . . C10 C 0.1806(2) 0.31571(14) 0.22087(10) 0.0396(3) Uani 1 d . . . H10 H 0.2271 0.2593 0.2581 0.048 Uiso 1 calc R . . C61 C 0.47162(18) 0.52624(13) 0.27687(9) 0.0343(3) Uani 1 d . . . H61 H 0.5103 0.6020 0.2456 0.041 Uiso 1 calc R . . C62 C 0.45824(19) 0.58944(14) 0.38552(9) 0.0372(3) Uani 1 d . . . H62A H 0.4111 0.5177 0.4177 0.045 Uiso 1 calc R . . H62B H 0.3727 0.6494 0.3855 0.045 Uiso 1 calc R . . C63 C 0.6528(2) 0.67267(14) 0.44640(10) 0.0422(3) Uani 1 d . . . H63A H 0.6907 0.7507 0.4184 0.051 Uiso 1 calc R . . H63B H 0.6440 0.7085 0.5173 0.051 Uiso 1 calc R . . N64 N 0.79857(16) 0.59457(12) 0.44517(8) 0.0395(3) Uani 1 d . . . C64 C 0.9811(2) 0.67815(17) 0.50463(12) 0.0511(4) Uani 1 d . . . H64A H 1.0703 0.6222 0.5026 0.077 Uiso 1 calc R . . H64B H 0.9714 0.7133 0.5747 0.077 Uiso 1 calc R . . H64C H 1.0208 0.7536 0.4754 0.077 Uiso 1 calc R . . C65 C 0.8170(2) 0.53820(15) 0.34189(10) 0.0424(3) Uani 1 d . . . H65A H 0.9092 0.4835 0.3424 0.051 Uiso 1 calc R . . H65B H 0.8582 0.6120 0.3103 0.051 Uiso 1 calc R . . C66 C 0.6276(2) 0.44771(15) 0.27980(10) 0.0398(3) Uani 1 d . . . H66A H 0.5919 0.3712 0.3097 0.048 Uiso 1 calc R . . H66B H 0.6404 0.4100 0.2099 0.048 Uiso 1 calc R . . 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 V1 0.03595(16) 0.03769(16) 0.02560(16) 0.00126(9) 0.00437(9) 0.01039(10) C1 0.0430(8) 0.0348(7) 0.0244(6) 0.0021(5) 0.0079(5) 0.0103(6) C2 0.0481(8) 0.0370(7) 0.0293(7) 0.0030(5) 0.0069(5) 0.0149(6) C3 0.0435(8) 0.0571(9) 0.0348(8) 0.0019(6) 0.0050(6) 0.0242(7) C4 0.0368(8) 0.0532(9) 0.0398(8) 0.0018(6) 0.0093(6) 0.0044(7) C5 0.0446(8) 0.0412(7) 0.0305(7) 0.0069(5) 0.0101(5) 0.0053(6) C11 0.0442(8) 0.0324(7) 0.0273(6) 0.0039(5) 0.0035(5) 0.0105(6) C12 0.0427(8) 0.0629(10) 0.0282(7) 0.0051(6) 0.0054(6) 0.0086(7) C13 0.0413(9) 0.0668(11) 0.0374(9) 0.0019(7) 0.0055(6) 0.0102(8) N14 0.0424(7) 0.0439(7) 0.0341(6) 0.0024(5) -0.0011(5) 0.0073(5) C14 0.0493(10) 0.0638(11) 0.0458(9) -0.0033(7) -0.0082(7) 0.0127(8) C15 0.0554(9) 0.0455(8) 0.0277(7) 0.0035(5) 0.0014(6) 0.0111(7) C16 0.0465(8) 0.0400(7) 0.0263(7) 0.0032(5) 0.0066(5) 0.0071(6) C6 0.0392(7) 0.0355(7) 0.0257(7) -0.0002(5) 0.0071(5) 0.0108(5) C7 0.0515(9) 0.0441(8) 0.0344(7) 0.0013(5) 0.0055(6) 0.0238(7) C8 0.0397(8) 0.0674(11) 0.0424(9) -0.0053(7) 0.0016(6) 0.0248(8) C9 0.0389(8) 0.0540(9) 0.0403(8) -0.0072(6) 0.0128(6) 0.0013(7) C10 0.0444(8) 0.0409(7) 0.0303(7) 0.0040(5) 0.0112(5) 0.0053(6) C61 0.0403(7) 0.0338(7) 0.0269(6) 0.0052(5) 0.0067(5) 0.0073(6) C62 0.0420(8) 0.0380(7) 0.0284(7) 0.0009(5) 0.0074(5) 0.0103(6) C63 0.0494(9) 0.0391(7) 0.0317(7) 0.0009(5) 0.0055(6) 0.0069(6) N64 0.0404(7) 0.0436(7) 0.0296(6) 0.0048(4) 0.0031(5) 0.0071(5) C64 0.0464(9) 0.0571(10) 0.0402(8) 0.0078(6) -0.0009(6) 0.0021(7) C65 0.0403(8) 0.0516(9) 0.0336(8) 0.0063(6) 0.0085(6) 0.0114(7) C66 0.0414(8) 0.0433(8) 0.0310(7) 0.0006(5) 0.0067(5) 0.0119(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 V1 C7 2.2726(13) . ? V1 C2 2.2734(13) . ? V1 C5 2.2845(13) . ? V1 C10 2.2852(13) . ? V1 C6 2.2963(12) . ? V1 C1 2.3044(13) . ? V1 C3 2.3177(14) . ? V1 C9 2.3235(15) . ? V1 C8 2.3239(15) . ? V1 C4 2.3325(15) . ? C1 C2 1.4336(19) . ? C1 C5 1.4498(19) . ? C1 C11 1.5544(19) . ? C2 C3 1.473(2) . ? C3 C4 1.407(2) . ? C4 C5 1.457(2) . ? C11 C16 1.5288(18) . ? C11 C12 1.566(2) . ? C12 C13 1.573(2) . ? C13 N14 1.4604(19) . ? N14 C15 1.498(2) . ? N14 C14 1.5060(19) . ? C15 C16 1.5769(19) . ? C6 C10 1.4289(19) . ? C6 C7 1.4489(19) . ? C6 C61 1.5532(18) . ? C7 C8 1.456(2) . ? C8 C9 1.406(2) . ? C9 C10 1.470(2) . ? C61 C62 1.5338(17) . ? C61 C66 1.5731(19) . ? C62 C63 1.5727(19) . ? C63 N64 1.5027(19) . ? N64 C65 1.4631(17) . ? N64 C64 1.4997(19) . ? C65 C66 1.569(2) . ? 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 C7 V1 C2 170.64(5) . . ? C7 V1 C5 116.82(5) . . ? C2 V1 C5 60.09(5) . . ? C7 V1 C10 60.12(5) . . ? C2 V1 C10 124.46(5) . . ? C5 V1 C10 170.55(5) . . ? C7 V1 C6 36.97(5) . . ? C2 V1 C6 151.69(5) . . ? C5 V1 C6 135.57(5) . . ? C10 V1 C6 36.34(5) . . ? C7 V1 C1 135.48(5) . . ? C2 V1 C1 36.49(5) . . ? C5 V1 C1 36.83(5) . . ? C10 V1 C1 151.90(5) . . ? C6 V1 C1 170.57(5) . . ? C7 V1 C3 150.56(6) . . ? C2 V1 C3 37.40(5) . . ? C5 V1 C3 60.01(6) . . ? C10 V1 C3 117.59(5) . . ? C6 V1 C3 121.84(5) . . ? C1 V1 C3 61.97(5) . . ? C7 V1 C9 59.95(6) . . ? C2 V1 C9 117.79(5) . . ? C5 V1 C9 150.87(6) . . ? C10 V1 C9 37.20(5) . . ? C6 V1 C9 61.70(5) . . ? C1 V1 C9 122.22(5) . . ? C3 V1 C9 138.41(6) . . ? C7 V1 C8 36.90(6) . . ? C2 V1 C8 135.75(6) . . ? C5 V1 C8 123.10(6) . . ? C10 V1 C8 60.71(6) . . ? C6 V1 C8 62.21(5) . . ? C1 V1 C8 115.29(5) . . ? C3 V1 C8 171.83(6) . . ? C9 V1 C8 35.22(6) . . ? C7 V1 C4 123.00(6) . . ? C2 V1 C4 60.67(5) . . ? C5 V1 C4 36.77(5) . . ? C10 V1 C4 135.75(5) . . ? C6 V1 C4 115.30(5) . . ? C1 V1 C4 62.08(5) . . ? C3 V1 C4 35.22(6) . . ? C9 V1 C4 171.73(6) . . ? C8 V1 C4 151.83(7) . . ? C2 C1 C5 104.63(12) . . ? C2 C1 C11 128.61(12) . . ? C5 C1 C11 126.67(12) . . ? C2 C1 V1 70.58(7) . . ? C5 C1 V1 70.84(7) . . ? C11 C1 V1 125.28(9) . . ? C1 C2 C3 109.92(13) . . ? C1 C2 V1 72.93(7) . . ? C3 C2 V1 72.93(8) . . ? C4 C3 C2 107.80(13) . . ? C4 C3 V1 72.96(8) . . ? C2 C3 V1 69.67(7) . . ? C3 C4 C5 106.95(13) . . ? C3 C4 V1 71.82(8) . . ? C5 C4 V1 69.82(8) . . ? C1 C5 C4 110.69(13) . . ? C1 C5 V1 72.33(7) . . ? C4 C5 V1 73.40(8) . . ? C16 C11 C1 110.34(11) . . ? C16 C11 C12 108.36(11) . . ? C1 C11 C12 116.06(11) . . ? C11 C12 C13 113.71(12) . . ? N14 C13 C12 109.43(12) . . ? C13 N14 C15 110.45(12) . . ? C13 N14 C14 107.88(12) . . ? C15 N14 C14 113.30(12) . . ? N14 C15 C16 113.40(11) . . ? C11 C16 C15 109.15(11) . . ? C10 C6 C7 104.99(12) . . ? C10 C6 C61 128.19(12) . . ? C7 C6 C61 126.58(12) . . ? C10 C6 V1 71.40(7) . . ? C7 C6 V1 70.63(7) . . ? C61 C6 V1 126.47(9) . . ? C6 C7 C8 110.53(14) . . ? C6 C7 V1 72.40(7) . . ? C8 C7 V1 73.46(8) . . ? C9 C8 C7 106.75(13) . . ? C9 C8 V1 72.37(8) . . ? C7 C8 V1 69.63(8) . . ? C8 C9 C10 108.13(13) . . ? C8 C9 V1 72.40(9) . . ? C10 C9 V1 69.98(8) . . ? C6 C10 C9 109.59(13) . . ? C6 C10 V1 72.25(7) . . ? C9 C10 V1 72.82(8) . . ? C62 C61 C6 109.23(11) . . ? C62 C61 C66 108.61(10) . . ? C6 C61 C66 116.89(10) . . ? C61 C62 C63 109.25(11) . . ? N64 C63 C62 114.81(10) . . ? C65 N64 C64 108.78(12) . . ? C65 N64 C63 111.01(11) . . ? C64 N64 C63 112.73(11) . . ? N64 C65 C66 109.11(11) . . ? C65 C66 C61 113.26(11) . . ? _diffrn_measured_fraction_theta_max 0.721 _diffrn_reflns_theta_full 30.18 _diffrn_measured_fraction_theta_full 0.721 _refine_diff_density_max 0.222 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.037