#------------------------------------------------------------------------------ #$Date: 2008-01-26 18:25:03 +0100 (Sat, 26 Jan 2008) $ #$Revision: 20 $ #$URL: svn://www.crystallography.net/cod/cif/2/2003297.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2003297 _journal_name_full 'Acta Crystallographica' _journal_year 1995 _journal_volume C51 _journal_page_first 502 _journal_page_last 505 _publ_section_title ; Diels-Alder Products of the Alkaloid (-)-Thebaine with \a- Chloroacrylnitrile and 1-Methoxy-1,3-cyclohexadiene with Tetracyanoethene ; _chemical_formula_sum 'C13 H10 N4 O' _chemical_formula_weight 238.25 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' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_length_a 7.5252(5) _cell_length_b 9.398(1) _cell_length_c 17.2900(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1222.8(2) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _cell_measurement_reflns_used 74 _cell_measurement_theta_min 65 _cell_measurement_theta_max 70 _exptl_absorpt_coefficient_mu 0.710 _cell_measurement_temperature 293(2) _exptl_crystal_description Rectangular _exptl_crystal_size_max 1.09 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.33 _exptl_crystal_colour Reddish _chemical_compound_source ; slow evaporation of chloroform solution of (2) ; _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 2648 _reflns_number_total 2277 _reflns_number_observed 2218 _reflns_observed_criterion >2\s(I) _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_theta_max 69.90 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 5 _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_obs 0.0527 _refine_ls_wR_factor_obs 0.1407 _refine_ls_wR_factor_all 0.1421 _refine_ls_goodness_of_fit_obs 1.031 _refine_ls_goodness_of_fit_all 1.027 _refine_ls_number_reflns 2277 _refine_ls_number_parameters 171 _refine_ls_hydrogen_treatment refU _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.1125P)^2^+0.1044P] _refine_ls_shift/esd_max -0.003 _refine_diff_density_max 0.225 _refine_diff_density_min -0.168 _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_extinction_coef 0.0038(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag 'C' 'C' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0181 0.009 'H' 'H' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 'N' 'N' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0311 0.018 'O' 'O' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0492 0.032 _refine_ls_abs_structure_details '\c = 0.4(4) (Flack, 1983)' _refine_ls_abs_structure_Flack 0.4(4) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv C1 1 0.1974(3) 0.3606(2) 0.87082(10) 0.0474(4) C2 1 0.2124(3) 0.3842(2) 0.78435(11) 0.0530(5) H2 1 0.1572(3) 0.3300(2) 0.76013(11) 0.088(11) C3 1 0.3525(3) 0.4664(3) 0.76335(11) 0.0581(6) H3 1 0.3816(3) 0.4963(3) 0.72023(11) 0.060(7) C4 1 0.4660(3) 0.5150(3) 0.83029(11) 0.0526(5) H4 1 0.5616(3) 0.5751(3) 0.81996(11) 0.077(9) C5 1 0.3425(2) 0.6074(2) 0.88505(10) 0.0431(4) C6 1 0.1732(2) 0.5136(2) 0.90747(9) 0.0391(4) C7 1 0.5264(3) 0.3858(3) 0.87587(14) 0.0645(6) H7A 1 0.5868(3) 0.3345(3) 0.84009(14) 0.100(9) H7B 1 0.5855(3) 0.4194(3) 0.91965(14) 0.100(9) C8 1 0.3714(4) 0.2977(3) 0.90137(13) 0.0641(6) H8A 1 0.3625(4) 0.2973(3) 0.96026(13) 0.111(9) H8B 1 0.3695(4) 0.2026(3) 0.88026(13) 0.111(9) C9 1 0.1501(2) 0.4995(2) 0.99205(10) 0.0462(4) N1 1 0.1305(3) 0.4860(2) 1.05666(9) 0.0663(5) C10 1 0.0086(2) 0.5750(2) 0.87629(11) 0.0469(4) N2 1 -0.1193(3) 0.6204(3) 0.84990(13) 0.0679(6) C11 1 0.4473(3) 0.6496(2) 0.95378(11) 0.0526(5) N3 1 0.5372(3) 0.6799(2) 1.00374(12) 0.0703(6) C12 1 0.2915(3) 0.7386(2) 0.84392(11) 0.0528(5) N4 1 0.2583(3) 0.8366(3) 0.80851(13) 0.0762(7) O1 1 0.0429(3) 0.2866(2) 0.89409(10) 0.0640(5) C13 1 0.0279(6) 0.1443(3) 0.8664(2) 0.0957(12) H13A 1 -0.0889(17) 0.1085(14) 0.8776(20) 0.154(12) H13B 1 0.1150(33) 0.0856(9) 0.8914(16) 0.154(12) H13C 1 0.0473(51) 0.1428(7) 0.8115(4) 0.154(12) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 C1 0.0514(11) -0.0021(8) 0.0020(8) 0.0483(9) -0.0035(7) 0.0424(9) C2 0.0528(11) -0.0027(9) -0.0009(8) 0.0653(12) -0.0121(8) 0.0408(9) C3 0.0527(12) 0.0056(10) 0.0064(8) 0.0848(15) -0.0060(9) 0.0369(8) C4 0.0347(9) -0.0009(9) 0.0054(7) 0.0760(13) -0.0018(9) 0.0473(9) C5 0.0386(8) -0.0051(7) -0.0013(7) 0.0541(9) 0.0032(7) 0.0365(8) C6 0.0368(8) -0.0013(7) 0.0002(6) 0.0482(8) 0.0014(6) 0.0324(7) C7 0.0507(12) 0.0147(11) -0.0046(9) 0.086(2) -0.0087(11) 0.0572(12) C8 0.071(2) 0.0208(11) -0.0031(10) 0.0674(13) -0.0024(10) 0.0540(11) C9 0.0474(10) -0.0012(8) 0.0031(7) 0.0528(9) 0.0015(7) 0.0385(9) N1 0.0776(13) -0.0068(11) 0.0057(7) 0.0836(13) 0.0046(8) 0.0378(8) C10 0.0393(10) -0.0016(8) 0.0000(7) 0.0581(10) 0.0025(8) 0.0433(8) N2 0.0435(10) 0.0008(9) -0.0088(9) 0.0868(14) 0.0139(10) 0.0733(12) C11 0.0525(10) -0.0084(8) -0.0031(8) 0.0593(10) -0.0002(8) 0.0460(9) N3 0.0691(12) -0.0126(11) -0.0191(9) 0.0814(13) -0.0093(10) 0.0603(11) C12 0.0457(10) -0.0038(9) 0.0034(8) 0.0643(11) 0.0108(9) 0.0484(10) N4 0.0765(14) 0.0015(11) 0.0106(11) 0.0761(13) 0.0306(11) 0.0759(14) O1 0.0723(11) -0.0193(7) 0.0148(7) 0.0560(8) -0.0072(7) 0.0638(9) C13 0.131(3) -0.034(2) 0.023(2) 0.0607(14) -0.0178(15) 0.095(2)