data_2003296 _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 'C22 H23 Cl N2 O3' _chemical_formula_weight 398.87 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' _symmetry_space_group_name_H-M 'P 1' _cell_length_a 6.7639(2) _cell_length_b 8.0105(1) _cell_length_c 9.3111(1) _cell_angle_alpha 95.703(1) _cell_angle_beta 106.774(1) _cell_angle_gamma 92.499(2) _cell_volume 479.25(2) _cell_formula_units_Z 1 _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _cell_measurement_reflns_used 75 _cell_measurement_theta_min 65 _cell_measurement_theta_max 70 _exptl_absorpt_coefficient_mu 1.980 _cell_measurement_temperature 293(2) _exptl_crystal_description prism _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_colour 'light yellow' _chemical_compound_source ; diffusion of petroleum ether into a solution of (1) in ethyl acetate ; _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 3803 _reflns_number_total 3569 _reflns_number_observed 3558 _reflns_observed_criterion >2\s(I) _diffrn_reflns_av_R_equivalents 0.0075 _diffrn_reflns_theta_max 69.85 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _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 0.0475 _refine_ls_wR_factor_obs 0.1360 _refine_ls_wR_factor_all 0.1362 _refine_ls_goodness_of_fit_obs 1.126 _refine_ls_goodness_of_fit_all 1.126 _refine_ls_number_reflns 3569 _refine_ls_number_parameters 267 _refine_ls_hydrogen_treatment refU _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(Fo^2^) + (0.0909P)^2^ + 0.1397P] where P = (F~o~^2^+2F~c~^2^)/3 ; _refine_ls_shift/esd_max 0.020 _refine_diff_density_max 0.398 _refine_diff_density_min -0.323 _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_extinction_coef 0.0217(28) 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 'Cl' 'Cl' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.3639 0.7 _refine_ls_abs_structure_details '\c = 0.03(2) (Flack, 1983)' _refine_ls_abs_structure_Flack 0.03(2) 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 Cl1 1 0.14986(11) 0.45117(9) 0.15887(8) 0.0554(2) C1 1 0.5812(5) 0.6211(4) 1.0056(3) 0.0485(7) H1 1 0.7157(5) 0.6359(4) 1.0999(3) 0.064(11) C2 1 0.4441(5) 0.7383(4) 1.0310(3) 0.0480(7) H2 1 0.4910(5) 0.8182(4) 1.1199(3) 0.050(9) C3 1 0.2457(4) 0.7417(3) 0.9325(3) 0.0400(6) C4 1 0.1890(4) 0.6209(3) 0.8088(3) 0.0346(5) O1 1 0.0182(3) 0.6169(2) 0.6828(2) 0.0397(4) C5 1 0.0408(4) 0.4833(3) 0.5710(3) 0.0349(5) H5 1 -0.0794(4) 0.4185(3) 0.5193(3) 0.032(7) C6 1 0.0952(4) 0.5502(3) 0.4351(3) 0.0359(5) C7 1 0.1092(4) 0.3867(3) 0.3288(3) 0.0368(5) C8 1 0.2901(4) 0.2833(3) 0.4093(3) 0.0372(5) H8A 1 0.4113(4) 0.2848(3) 0.3804(3) 0.089(11) H8B 1 0.2437(4) 0.1872(3) 0.4397(3) 0.089(11) C9 1 0.5614(4) 0.2753(3) 0.6710(3) 0.0366(5) H9 1 0.6689(4) 0.2613(3) 0.6193(3) 0.038(8) C10 1 0.6610(4) 0.3791(4) 0.8299(3) 0.0413(6) H10A 1 0.7672(4) 0.4540(4) 0.8196(3) 0.053(7) H10B 1 0.6993(4) 0.2982(4) 0.8997(3) 0.053(7) C11 1 0.5184(4) 0.4956(3) 0.8850(3) 0.0372(5) C12 1 0.3157(4) 0.4945(3) 0.7948(3) 0.0334(5) C13 1 0.2200(3) 0.3812(3) 0.6523(3) 0.0308(5) C14 1 0.3892(4) 0.3694(3) 0.5708(3) 0.0322(5) C15 1 0.1419(4) 0.2078(3) 0.6793(3) 0.0389(6) H15A 1 0.0666(4) 0.1441(3) 0.5804(3) 0.073(9) H15B 1 0.0548(4) 0.2409(3) 0.7604(3) 0.073(9) N1 1 0.4768(4) 0.1036(3) 0.6755(3) 0.0412(5) C16 1 0.3206(5) 0.1066(3) 0.7561(4) 0.0452(6) H16A 1 0.3859(5) 0.1394(3) 0.8798(4) 0.044(6) H16B 1 0.2658(5) -0.0265(3) 0.7398(4) 0.044(6) C17 1 0.3089(4) 0.6381(3) 0.4853(3) 0.0387(6) H17 1 0.3512(4) 0.7577(3) 0.4797(3) 0.066(12) C18 1 0.4585(4) 0.5470(3) 0.5544(3) 0.0364(5) H18 1 0.6089(4) 0.5861(3) 0.5997(3) 0.046(9) O2 1 0.1058(4) 0.8581(3) 0.9446(3) 0.0530(5) C19 1 0.1517(8) 0.9652(6) 1.0814(5) 0.0798(14) H19A 1 0.0315(8) 1.0225(6) 1.0858(5) 0.116(13) H19B 1 0.2632(8) 1.0462(6) 1.0867(5) 0.116(13) H19C 1 0.1918(8) 0.8998(6) 1.1647(5) 0.116(13) O3 1 -0.0629(3) 0.6378(2) 0.3479(2) 0.0497(5) C20 1 -0.0909(6) 0.8015(4) 0.4090(4) 0.0595(9) H20A 1 -0.2045(6) 0.7959(4) 0.4512(4) 0.135(16) H20B 1 -0.1202(6) 0.8739(4) 0.3305(4) 0.135(16) H20C 1 0.0330(6) 0.8452(4) 0.4866(4) 0.135(16) C21 1 -0.0916(5) 0.2849(4) 0.2792(3) 0.0457(6) N2 1 -0.2399(5) 0.2025(4) 0.2458(4) 0.0678(9) C22 1 0.6392(5) -0.0062(4) 0.7404(4) 0.0548(8) H22A 1 0.5728(5) -0.1210(4) 0.7404(4) 0.073(7) H22B 1 0.7195(5) -0.0111(4) 0.6604(4) 0.073(7) H22C 1 0.7271(5) 0.0525(4) 0.8601(4) 0.073(7) 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 Cl1 0.0745(5) 0.0111(3) 0.0155(3) 0.0600(4) 0.0105(3) 0.0332(3) C1 0.045(2) 0.0059(12) -0.0035(12) 0.053(2) 0.0049(12) 0.0379(15) C2 0.057(2) 0.0044(12) 0.0001(12) 0.0471(15) -0.0047(11) 0.0302(13) C3 0.0487(15) 0.0083(11) 0.0136(11) 0.0399(13) 0.0031(10) 0.0325(13) C4 0.0350(12) 0.0021(9) 0.0058(9) 0.0396(13) 0.0057(10) 0.0274(12) O1 0.0372(9) 0.0115(7) 0.0046(7) 0.0439(10) 0.0001(7) 0.0341(9) C5 0.0322(11) 0.0028(9) 0.0018(10) 0.0328(12) 0.0004(10) 0.0339(13) C6 0.0431(13) 0.0079(9) 0.0015(9) 0.0314(11) 0.0013(9) 0.0277(12) C7 0.0430(13) 0.0036(10) 0.0049(10) 0.0366(12) 0.0000(9) 0.0267(11) C8 0.0426(13) 0.0091(10) 0.0097(10) 0.0354(12) 0.0012(9) 0.0328(12) C9 0.0314(11) 0.0082(9) 0.0079(10) 0.0359(12) 0.0066(10) 0.0416(14) C10 0.0314(12) 0.0064(10) 0.0012(11) 0.0420(14) 0.0053(11) 0.044(2) C11 0.0369(12) 0.0045(10) 0.0033(10) 0.0414(13) 0.0069(10) 0.0297(12) C12 0.0363(12) 0.0010(9) 0.0084(10) 0.0332(11) 0.0040(9) 0.0297(12) C13 0.0279(10) 0.0005(9) 0.0033(9) 0.0306(11) 0.0018(9) 0.0299(12) C14 0.0334(11) 0.0028(9) 0.0065(9) 0.0303(11) 0.0048(9) 0.0312(12) C15 0.0388(13) -0.0005(10) 0.0104(11) 0.0336(12) 0.0082(10) 0.0436(14) N1 0.0416(12) 0.0092(9) 0.0074(10) 0.0311(10) 0.0066(9) 0.0483(13) C16 0.0470(15) 0.0046(11) 0.0129(13) 0.0369(13) 0.0173(12) 0.053(2) C17 0.0477(14) 0.0006(10) 0.0101(11) 0.0310(11) 0.0060(9) 0.0362(13) C18 0.0381(13) -0.0018(10) 0.0104(11) 0.0347(12) 0.0034(10) 0.0357(13) O2 0.0646(13) 0.0211(10) 0.0138(9) 0.0512(12) -0.0053(9) 0.0411(11) C19 0.100(3) 0.034(2) 0.015(2) 0.079(3) -0.019(2) 0.053(2) O3 0.0576(12) 0.0171(8) -0.0102(9) 0.0380(10) 0.0007(8) 0.0384(10) C20 0.075(2) 0.0270(15) 0.003(2) 0.043(2) 0.0030(14) 0.052(2) C21 0.050(2) 0.0062(12) 0.0031(12) 0.0433(14) -0.0046(11) 0.0361(14) N2 0.058(2) -0.0034(14) 0.0009(15) 0.057(2) -0.0127(15) 0.072(2) C22 0.051(2) 0.0133(12) 0.0015(15) 0.0393(14) 0.0067(13) 0.065(2)