#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/06/2010665.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010665 loop_ _publ_author_name 'Tam, William' 'Handerson, Sean' 'Ferguson, George' _publ_section_title 2,3,3a,4,5a,6,7,8-Octahydro-5a-methyl-6,9-methano-1H,9H-5-oxa-4-azacyclopenta[c]indene _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e71 _journal_page_last e71 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H15 N O' _chemical_formula_sum 'C12 H15 N O' _chemical_formula_weight 189.25 _chemical_name_systematic ; 2,3,3a,4,5a,6,7,8-Octahydro-5a-methyl-6,9-methano-1H,9H-5-oxa-4-azacyclo- penta[c]indene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.00 _cell_angle_beta 91.668(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.640(2) _cell_length_b 12.7121(14) _cell_length_c 10.2205(7) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 12.13 _cell_measurement_theta_min 9.47 _cell_volume 992.2(3) _computing_cell_refinement 'SET4 and CELDIM (Enraf-Nonius, 1992)' _computing_data_collection 'CAD-4-PC Software (Enraf-Nonius, 1992)' _computing_data_reduction 'DATRD2 in NRCVAX96 (Gabe et al., 1989)' _computing_publication_material 'NRCVAX96, SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)' _computing_structure_refinement 'NRCVAX96 and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SOLVER in NRCVAX96' _diffrn_ambient_temperature 294.0(10) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .7107 _diffrn_reflns_av_R_equivalents .011 _diffrn_reflns_av_sigmaI/netI .0352 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1997 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 2.55 _diffrn_standards_decay_% 6.2 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .080 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 408 _exptl_crystal_size_max .42 _exptl_crystal_size_mid .42 _exptl_crystal_size_min .19 _refine_diff_density_max .171 _refine_diff_density_min -.137 _refine_ls_extinction_coef .103(7) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1860 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all .0668 _refine_ls_R_factor_gt .0442 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0760P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1090 _reflns_number_gt 1314 _reflns_number_total 1860 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qa0212.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2010665 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .21653(16) .27567(10) .05223(11) .0467(4) Uani d . 1 . . O N1 .0809(2) .35228(11) .03739(14) .0453(4) Uani d . 1 . . N C1 .1863(3) .11372(14) .18024(18) .0474(5) Uani d . 1 . . C C2 .2196(2) .23317(13) .18701(16) .0373(4) Uani d . 1 . . C C3 .0493(2) .27558(12) .24506(15) .0330(4) Uani d . 1 . . C C4 -.0637(2) .17320(13) .25784(17) .0428(5) Uani d . 1 . . C C5 .0261(3) .11096(13) .36577(19) .0482(5) Uani d . 1 . . C C6 .1746(3) .07582(14) .31991(18) .0527(5) Uani d . 1 . . C C7 -.0072(3) .11142(14) .13816(19) .0532(5) Uani d . 1 . . C C8 .0429(3) .34903(14) .36314(17) .0447(5) Uani d . 1 . . C C9 -.1187(3) .41804(16) .3352(2) .0585(6) Uani d . 1 . . C C10 -.1428(3) .42595(15) .18525(19) .0545(5) Uani d . 1 . . C C11 -.0108(2) .34888(13) .13890(16) .0374(4) Uani d . 1 . . C C12 .3923(2) .26523(17) .2496(2) .0563(5) Uani d . 1 . . C H1 .2651 .0737 .1249 .057 Uiso calc R 1 . . H H4 -.1901 .1837 .2658 .051 Uiso calc R 1 . . H H5 -.0155 .0995 .4492 .058 Uiso calc R 1 . . H H6 .2572 .0351 .3653 .063 Uiso calc R 1 . . H H7A -.0314 .1481 .0564 .064 Uiso calc R 1 . . H H7B -.0554 .0408 .1345 .064 Uiso calc R 1 . . H H8A .1482 .3915 .3706 .054 Uiso calc R 1 . . H H8B .0306 .3094 .4434 .054 Uiso calc R 1 . . H H9A -.1014 .4874 .3729 .070 Uiso calc R 1 . . H H9B -.2214 .3867 .3729 .070 Uiso calc R 1 . . H H10A -.2605 .4062 .1568 .065 Uiso calc R 1 . . H H10B -.1182 .4964 .1545 .065 Uiso calc R 1 . . H H12A .4861 .2380 .1991 .085 Uiso calc R 1 . . H H12B .4012 .2376 .3369 .085 Uiso calc R 1 . . H H12C .3996 .3406 .2525 .085 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0524(8) .0509(7) .0375(7) .0057(6) .0117(6) .0058(6) N1 .0510(10) .0444(9) .0404(9) -.0002(7) -.0006(7) .0079(7) C1 .0587(13) .0366(10) .0475(11) .0085(9) .0113(9) -.0035(8) C2 .0382(9) .0395(9) .0344(9) .0031(8) .0044(7) .0030(7) C3 .0339(9) .0314(8) .0337(9) .0004(7) .0015(7) .0043(7) C4 .0391(10) .0367(9) .0527(11) -.0046(8) .0040(8) .0069(8) C5 .0591(13) .0360(10) .0502(11) .0003(9) .0122(9) .0111(8) C6 .0675(14) .0350(10) .0558(12) .0104(10) .0042(10) .0103(9) C7 .0680(14) .0371(10) .0542(12) -.0133(9) -.0031(10) -.0014(8) C8 .0556(12) .0417(10) .0372(10) .0022(9) .0072(8) .0007(8) C9 .0668(14) .0478(11) .0615(13) .0152(10) .0154(11) .0012(9) C10 .0504(12) .0489(11) .0644(13) .0096(10) .0063(10) .0168(10) C11 .0382(10) .0370(9) .0368(9) -.0036(8) -.0025(8) .0049(7) C12 .0394(11) .0666(13) .0629(13) .0011(10) -.0009(9) .0071(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 N1 . 1.4269(19) no O1 C2 . 1.479(2) no N1 C11 . 1.269(2) no C1 C2 . 1.541(2) no C1 C6 . 1.512(3) no C1 C7 . 1.528(3) no C2 C3 . 1.543(2) no C2 C12 . 1.505(3) no C3 C4 . 1.570(2) no C3 C8 . 1.528(2) no C3 C11 . 1.492(2) no C4 C5 . 1.506(2) no C4 C7 . 1.527(2) no C5 C6 . 1.318(3) no C8 C9 . 1.535(3) no C9 C10 . 1.541(3) no C10 C11 . 1.493(2) no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -4 4 1 3 4 1 3 5 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag N1 O1 C2 109.89(11) no O1 N1 C11 107.83(13) no C2 C1 C6 106.62(14) no C2 C1 C7 100.90(14) no C6 C1 C7 100.15(16) no O1 C2 C1 108.66(13) no O1 C2 C12 106.66(14) no C1 C2 C12 115.32(15) no O1 C2 C3 103.86(12) no C1 C2 C3 102.78(13) no C3 C2 C12 118.72(14) no C2 C3 C8 124.32(14) no C2 C3 C11 100.59(13) no C8 C3 C11 100.17(13) no C2 C3 C4 102.39(13) no C4 C3 C8 114.25(13) no C4 C3 C11 114.82(14) no C3 C4 C5 104.86(14) no C3 C4 C7 101.00(13) no C5 C4 C7 100.55(15) no C4 C5 C6 107.22(17) no C1 C6 C5 107.64(17) no C1 C7 C4 93.35(14) no C3 C8 C9 104.25(15) no C8 C9 C10 107.16(15) no C9 C10 C11 102.12(15) no N1 C11 C3 116.74(15) no N1 C11 C10 129.12(16) no C3 C11 C10 112.05(14) 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_publ_flag C2 O1 N1 C11 -9.29(18) no N1 O1 C2 C12 -115.47(15) no N1 O1 C2 C1 119.62(14) no N1 O1 C2 C3 10.72(16) no C6 C1 C2 O1 -175.05(14) no C7 C1 C2 O1 -70.88(16) no C6 C1 C2 C12 65.3(2) no C7 C1 C2 C12 169.48(15) no C6 C1 C2 C3 -65.42(17) no C7 C1 C2 C3 38.75(16) no O1 C2 C3 C11 -7.89(15) no C12 C2 C3 C11 110.28(17) no C1 C2 C3 C11 -121.09(14) no O1 C2 C3 C8 -118.07(16) no C12 C2 C3 C8 .1(2) no C1 C2 C3 C8 128.73(16) no O1 C2 C3 C4 110.69(13) no C12 C2 C3 C4 -131.15(16) no C1 C2 C3 C4 -2.51(16) no C11 C3 C4 C5 177.65(14) no C8 C3 C4 C5 -67.41(18) no C2 C3 C4 C5 69.65(16) no C11 C3 C4 C7 73.49(17) no C8 C3 C4 C7 -171.57(14) no C2 C3 C4 C7 -34.50(16) no C7 C4 C5 C6 33.84(19) no C3 C4 C5 C6 -70.64(18) no C4 C5 C6 C1 -.2(2) no C7 C1 C6 C5 -33.45(19) no C2 C1 C6 C5 71.3(2) no C5 C4 C7 C1 -50.59(15) no C3 C4 C7 C1 56.98(15) no C6 C1 C7 C4 50.21(15) no C2 C1 C7 C4 -59.08(15) no C11 C3 C8 C9 36.73(17) no C2 C3 C8 C9 147.12(16) no C4 C3 C8 C9 -86.54(17) no C3 C8 C9 C10 -28.7(2) no C8 C9 C10 C11 8.0(2) no O1 N1 C11 C3 3.7(2) no O1 N1 C11 C10 165.83(18) no C8 C3 C11 N1 130.97(16) no C2 C3 C11 N1 2.93(19) no C4 C3 C11 N1 -106.16(17) no C8 C3 C11 C10 -34.13(18) no C2 C3 C11 C10 -162.17(15) no C4 C3 C11 C10 88.74(18) no C9 C10 C11 N1 -146.04(19) no C9 C10 C11 C3 16.7(2) no _cod_database_fobs_code 2010665 _journal_paper_doi 10.1107/S0108270100001086