# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1156 # CIF-file generated for hynd2 #================================================================= data_global #================================================================= # 0. AUDIT DETAILS _audit_creation_date 10/05/1998 _audit_creation_method 'SHELXL' _audit_update_record ; ? ; #================================================================= # 1. SUBMISSION DETAILS # Name and address of author for correspondence _publ_contact_author_name 'Dr John C. Barnes' _publ_contact_author_address ; Department of Chemistry, University of Dundee, Nethergate, Dundee DD1 4HN, Scotland ; _publ_contact_author_phone '44-1382-344705' _publ_contact_author_fax '44-1382-345517' _publ_contact_author_email j.c.barnes@dundee.ac.uk _publ_requested_journal ? _publ_requested_coeditor_name ? _publ_requested_catagory ? _publ_contact_letter ; ; #================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; 6-Phenyl-8,8-dimethyl-10-aza-11-oxa-tricyclo[7.2.1.0]dodeca- 2,4,6,9tetraene ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Barnes, John C.' ; Department of Chemistry, University of Dundee, Nethergate, Dundee DD1 4HN, Scotland ; 'William M. Horspool' ; Department of Chemistry, University of Dundee, Nethergate, Dundee DD1 4HN, Scotland ; 'George Hynd' ; Department of Chemistry, University of Dundee, Nethergate, Dundee DD1 4HN, Scotland ; 'Diego Armesto' ; Department of Chemistry, University of Dundee, Nethergate, Dundee DD1 4HN, Scotland ; #================================================================= # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; Crystal data for 3a: C~18~ H~17~ N O, M = 263.33 , Orthorhombic, P212121, a = 8.6306(7) \%A , b = 10.610(2) \%A , c = 15.119(4) \%A , V = 384.4(5) \%A^3^, Z = 4, Dc = 1.263 Mg/m^3^, \m (Mo-Ka) = 0.078 mm^-1^, F(000) = 560. A colourless block of dimensions 0.18 x 0.14 x 0.14 mm was used. Reflections collected / unique 5768 / 2125 [R(int) = 0.0686] collected on the EPSRC FAST system at University of Wales, Cardiff. Structure solved by direct methods (SHELXS-97) and refined anisotropically using full matrix least squares based on F^2^ (SHELXL-97/2). Hydrogen atoms of the tricyclic portion located and refined, other hydrogen atoms placed on calculated positions, all isotropic. Largest diff. peak and hole 0.225 and -0.159 e.\%A^-3^. R1 = 0.030, wR2 = 0.068 for 1792 independent observed reflections [|Fo| > 4\sF , 2\q(max) 50\% and 207 parameters. The absolute chirality of 3a could not be unambiguously determined. Atomic coordinates, bond lengths and angles and thermal parameters have been deposited at CCDC (xxx/yyy) ; _publ_section_exptl_prep ; See text. ; _publ_section_references ; Enraf-Nonius (1993) CAD4/PC diffractometer Software. Version 1.2. Enraf-Nonius, Delft, The Netherlands. International Tables for Crystallography, Vol.C, 9.4-9.6. Sheldrick, G.M. (1997). In preparation for J. Appl. Cryst. Spek, A. L. (1992). PLATON-92, PLUTON-92. Programs for molecular geometry calculations. University of Utrecht, Netherlands. ; _publ_section_figure_captions ; Fig.1 : Structure of I showing 50 % probability displacement ellipsoids. ; _publ_section_acknowledgements ; Thanks to the EPSRC X-Ray Service, University of Wales, Cardiff, for the data collection and to the University of Dundee and the EC (ERBCHRXCT930151) for financial support. ; #================================================================= data_hynd2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-Phenyl-8,8-dimethyl-10-aza-11-oxa-tricyclo[7.2.1.0]dodeca- 2,4,6,9tetraene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O' _chemical_formula_weight 263.33 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' #================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.6306(7) _cell_length_b 10.610(2) _cell_length_c 15.119(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1384.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data collected using a FAST area detector system, details in Darr, Drake, Hursthouse and Malik, Inorg. Chem. 1993, 32, 5704. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius FAST system' _diffrn_measurement_method 'See Exptl Special details' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5768 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.06 _reflns_number_total 2125 _reflns_number_gt 1792 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON-92 (Spek, 1992)' _computing_publication_material ? _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^)+(0.0230P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.6(17) _refine_ls_number_reflns 2125 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_restrained_S_all 0.891 _refine_ls_shift/su_max 0.001 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.06304(16) 0.15737(12) 0.86412(9) 0.0302(4) Uani 1 1 d . . . N2 N 0.21783(19) 0.17472(15) 0.89444(12) 0.0264(4) Uani 1 1 d . . . C3 C 0.2607(2) 0.07599(19) 0.93523(13) 0.0207(5) Uani 1 1 d . . . C4 C 0.4233(2) 0.05027(18) 0.96690(12) 0.0219(5) Uani 1 1 d . . . C5 C 0.4615(2) -0.08285(19) 0.93737(13) 0.0231(5) Uani 1 1 d . . . H5 H 0.569(2) -0.1080(18) 0.9491(14) 0.035 Uiso 1 1 d . . . C6 C 0.3668(2) -0.16571(17) 0.89708(13) 0.0201(5) Uani 1 1 d . . . C7 C 0.2049(2) -0.13249(17) 0.87986(14) 0.0209(5) Uani 1 1 d . . . C8 C 0.1148(2) -0.17968(19) 0.81459(14) 0.0249(5) Uani 1 1 d . . . H8 H 0.159(2) -0.252(2) 0.7785(15) 0.037 Uiso 1 1 d . . . C9 C -0.0378(3) -0.1306(2) 0.79684(14) 0.0277(5) Uani 1 1 d . . . H9 H -0.099(3) -0.1739(19) 0.7530(15) 0.041 Uiso 1 1 d . . . C10 C -0.0936(2) -0.0281(2) 0.83624(13) 0.0264(5) Uani 1 1 d . . . H10 H -0.202(3) 0.0113(18) 0.8224(13) 0.040 Uiso 1 1 d . . . C11 C -0.0001(2) 0.04165(19) 0.90355(13) 0.0241(5) Uani 1 1 d . . . H11 H -0.068(2) 0.0749(18) 0.9505(14) 0.036 Uiso 1 1 d . . . C12 C 0.1425(2) -0.02796(18) 0.93701(14) 0.0221(5) Uani 1 1 d . . . H12 H 0.126(2) -0.0575(17) 0.9974(14) 0.033 Uiso 1 1 d . . . C13 C 0.4265(2) -0.29095(17) 0.86755(12) 0.0207(5) Uani 1 1 d . . . C14 C 0.5692(2) -0.30232(19) 0.82616(12) 0.0226(5) Uani 1 1 d . . . H14 H 0.6294 -0.2290 0.8153 0.034 Uiso 1 1 calc R . . C15 C 0.6253(2) -0.4190(2) 0.80035(13) 0.0257(5) Uani 1 1 d . . . H15 H 0.7234 -0.4251 0.7722 0.039 Uiso 1 1 calc R . . C16 C 0.5392(2) -0.52639(19) 0.81536(13) 0.0268(5) Uani 1 1 d . . . H16 H 0.5783 -0.6063 0.7978 0.040 Uiso 1 1 calc R . . C17 C 0.3963(2) -0.5178(2) 0.85585(13) 0.0272(5) Uani 1 1 d . . . H17 H 0.3366 -0.5916 0.8661 0.041 Uiso 1 1 calc R . . C18 C 0.3401(2) -0.40029(18) 0.88158(14) 0.0252(5) Uani 1 1 d . . . H18 H 0.2414 -0.3945 0.9091 0.038 Uiso 1 1 calc R . . C19 C 0.4280(3) 0.05698(19) 1.06870(12) 0.0302(5) Uani 1 1 d . . . H19A H 0.5314 0.0329 1.0895 0.045 Uiso 1 1 calc R . . H19B H 0.3508 -0.0009 1.0934 0.045 Uiso 1 1 calc R . . H19C H 0.4049 0.1432 1.0879 0.045 Uiso 1 1 calc R . . C20 C 0.5391(2) 0.14398(18) 0.92861(14) 0.0286(5) Uani 1 1 d . . . H20A H 0.6436 0.1228 0.9492 0.043 Uiso 1 1 calc R . . H20B H 0.5122 0.2293 0.9481 0.043 Uiso 1 1 calc R . . H20C H 0.5360 0.1400 0.8639 0.043 Uiso 1 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 O1 0.0289(9) 0.0241(9) 0.0374(9) 0.0040(7) -0.0055(7) 0.0020(6) N2 0.0236(10) 0.0236(11) 0.0320(11) -0.0019(9) 0.0007(8) 0.0006(8) C3 0.0234(12) 0.0221(13) 0.0166(11) -0.0059(9) 0.0036(9) -0.0002(10) C4 0.0236(12) 0.0182(12) 0.0240(12) -0.0038(8) 0.0007(9) 0.0008(8) C5 0.0215(12) 0.0234(13) 0.0244(12) 0.0013(9) 0.0001(9) 0.0016(10) C6 0.0205(11) 0.0177(11) 0.0222(12) 0.0030(9) 0.0003(9) -0.0011(9) C7 0.0237(12) 0.0143(11) 0.0246(12) 0.0032(9) 0.0020(9) -0.0010(8) C8 0.0251(13) 0.0200(13) 0.0296(13) -0.0020(10) 0.0016(10) -0.0028(9) C9 0.0225(13) 0.0318(15) 0.0287(13) -0.0040(10) -0.0016(10) -0.0043(10) C10 0.0209(12) 0.0304(13) 0.0277(12) -0.0002(10) -0.0007(9) 0.0017(10) C11 0.0249(12) 0.0235(13) 0.0239(12) 0.0000(10) 0.0043(9) 0.0035(9) C12 0.0246(12) 0.0247(12) 0.0170(11) 0.0011(9) 0.0024(9) -0.0008(9) C13 0.0234(12) 0.0193(13) 0.0194(12) 0.0009(8) -0.0024(9) 0.0003(9) C14 0.0235(12) 0.0220(13) 0.0222(12) 0.0032(9) 0.0004(9) -0.0003(9) C15 0.0287(13) 0.0291(13) 0.0195(12) 0.0012(10) 0.0035(9) 0.0069(11) C16 0.0389(14) 0.0189(13) 0.0227(12) -0.0027(10) -0.0068(10) 0.0071(10) C17 0.0334(14) 0.0182(13) 0.0300(13) 0.0002(9) -0.0068(10) -0.0013(9) C18 0.0242(12) 0.0206(12) 0.0307(13) 0.0002(10) -0.0003(10) -0.0003(10) C19 0.0322(13) 0.0307(14) 0.0277(12) -0.0055(10) -0.0023(10) -0.0014(10) C20 0.0262(13) 0.0243(13) 0.0351(13) -0.0071(10) 0.0017(10) -0.0032(9) _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 O1 N2 1.424(2) . yes O1 C11 1.470(2) . yes N2 C3 1.271(3) . yes C3 C12 1.503(3) . yes C3 C4 1.508(3) . yes C4 C5 1.518(3) . yes C4 C20 1.524(3) . ? C4 C19 1.541(3) . ? C5 C6 1.346(3) . yes C6 C7 1.465(3) . yes C6 C13 1.493(3) . ? C7 C8 1.352(3) . yes C7 C12 1.505(3) . yes C8 C9 1.441(3) . yes C9 C10 1.331(3) . yes C10 C11 1.495(3) . yes C11 C12 1.522(3) . yes C13 C14 1.387(3) . ? C13 C18 1.395(3) . ? C14 C15 1.386(3) . ? C15 C16 1.379(3) . ? C16 C17 1.380(3) . ? C17 C18 1.393(3) . ? 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 N2 O1 C11 108.97(14) . . yes C3 N2 O1 108.84(15) . . yes N2 C3 C12 114.58(18) . . yes N2 C3 C4 125.07(18) . . yes C12 C3 C4 119.57(18) . . yes C3 C4 C5 106.10(16) . . yes C3 C4 C20 111.82(17) . . ? C5 C4 C20 110.66(16) . . ? C3 C4 C19 109.48(17) . . ? C5 C4 C19 109.33(17) . . ? C20 C4 C19 109.38(17) . . ? C6 C5 C4 127.50(19) . . yes C5 C6 C7 120.18(18) . . yes C5 C6 C13 120.44(17) . . ? C7 C6 C13 119.36(16) . . ? C8 C7 C6 126.09(18) . . yes C8 C7 C12 119.08(18) . . yes C6 C7 C12 114.61(17) . . yes C7 C8 C9 121.8(2) . . yes C10 C9 C8 122.9(2) . . yes C9 C10 C11 120.9(2) . . yes O1 C11 C10 109.72(16) . . yes O1 C11 C12 103.92(15) . . yes C10 C11 C12 115.03(18) . . yes C3 C12 C7 106.71(16) . . yes C3 C12 C11 100.77(16) . . yes C7 C12 C11 117.12(18) . . yes C14 C13 C18 118.10(17) . . ? C14 C13 C6 121.25(17) . . ? C18 C13 C6 120.65(17) . . ? C15 C14 C13 121.01(18) . . ? C16 C15 C14 120.25(19) . . ? C17 C16 C15 119.99(19) . . ? C16 C17 C18 119.64(19) . . ? C17 C18 C13 121.01(18) . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.227 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.036