#------------------------------------------------------------------------------ #$Date: 2008-03-04 16:06:16 +0000 (Tue, 04 Mar 2008) $ #$Revision: 218 $ #$URL: svn://www.crystallography.net/cod/cif/2/2003815.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_2003815 _journal_name_full 'Acta Crystallographica' _journal_year 1995 _journal_volume C51 _journal_page_first 1675 _journal_page_last 1680 _publ_section_title ; Three Stereoisomers of a Novel and Selective \m-Opioid Analgesic ; _chemical_formula_sum 'C21 H33 Cl N2 O2' _chemical_formula_analytical 'C21 H33 Cl N2 O2' _chemical_formula_weight 380.96 _symmetry_cell_setting 'orthorhombic' 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 7.494(1) _cell_length_b 7.538(3) _cell_length_c 38.30(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2164(5) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _cell_measurement_radiation 'CuK\a~1~' _cell_measurement_wavelength 1.5405620 _diffrn_radiation_type 'CuK\a' _diffrn_radiation_wavelength 1.5405620 _cell_measurement_reflns_used 30 _cell_measurement_theta_min 18.28 _cell_measurement_theta_max 35.46 _exptl_absorpt_coefficient_mu 1.683 _cell_measurement_temperature 293(2) _exptl_crystal_description ; elongated prism ; _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_colour 'colourless' _chemical_compound_source ; chemical synthesis ; _diffrn_measurement_device 'Siemens-AED diffractometer' _diffrn_measurement_method '\q/2\q scan' _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 4470 _reflns_number_total 4068 _reflns_number_observed 1084 _reflns_observed_criterion 'I>2\s(I)' _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_theta_max 70.40 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 46 _diffrn_standards_number 1 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'within statistical fluctuation' _refine_ls_structure_factor_coef 'Fsqd' _refine_ls_R_factor_obs 0.0784 _refine_ls_wR_factor_obs 0.2139 _refine_ls_wR_factor_all 0.3270 _refine_ls_goodness_of_fit_obs 1.236 _refine_ls_goodness_of_fit_all 0.904 _refine_ls_number_reflns 4066 _refine_ls_number_parameters 237 _refine_ls_hydrogen_treatment 'refU' _refine_ls_weighting_scheme 'w=1/[\s^2^(F~o~^2^)+(0.1692P)^2^] where P=(F~o~^2^+2F~c~^2^)/3' _refine_ls_shift/esd_max 0.000 _refine_diff_density_max 0.30 _refine_diff_density_min -0.37 _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_extinction_coef 0.003(1) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag 'Cl' 'Chlorine ' 'IntTabC, 4.2.6.8, 6.1.1.4' 0.3639 0.7018 'O ' 'Oxygen ' 'IntTabC, 4.2.6.8, 6.1.1.4' 0.0492 0.0322 'N ' 'Nitrogen ' 'IntTabC, 4.2.6.8, 6.1.1.4' 0.0311 0.0180 'C ' 'Carbon ' 'IntTabC, 4.2.6.8, 6.1.1.4' 0.0181 0.0091 'H ' 'Hydrogen ' 'IntTabC, 4.2.6.8, 6.1.1.4' 0.0000 0.0000 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.03(7) ## 'ORTEP (Johnson, 1965); PLUTO (Motherwell & Clegg, 1978)' ## 'PARST (Nardelli, 1983); PARSTCIF (Nardelli, 1991)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv Cl -0.4818(4) -0.5672(3) -0.01160(6) 0.097(1) O1 -0.7993(10) -1.0426(11) -0.0870(2) 0.102(3) O2 -0.0785(9) -1.1839(10) -0.1224(2) 0.086(3) N1 -0.4962(12) -1.0438(9) -0.0806(2) 0.067(3) N2 -0.1947(11) -0.9195(10) -0.1745(2) 0.075(3) C1 -0.4845(13) -0.7845(10) 0.0034(3) 0.069(3) C2 -0.4812(14) -0.8116(14) 0.0383(3) 0.081(4) C3 -0.4920(17) -0.9832(14) 0.0517(2) 0.088(4) C4 -0.4941(17) -1.1223(12) 0.0291(3) 0.086(4) C5 -0.4923(15) -1.0932(11) -0.0066(2) 0.071(4) C6 -0.4872(12) -0.9227(11) -0.0213(2) 0.055(3) C7 -0.4884(15) -0.8856(10) -0.0591(2) 0.071(4) C8 -0.6535(17) -1.1164(14) -0.0914(3) 0.077(4) C9 -0.6162(14) -1.2830(15) -0.1106(3) 0.094(5) C10 -0.4267(15) -1.3273(14) -0.1020(3) 0.081(4) C11 -0.3380(12) -1.1539(14) -0.0893(3) 0.071(4) C12 -0.2206(12) -1.0613(13) -0.1163(2) 0.071(3) C13 -0.3078(12) -1.0263(12) -0.1519(2) 0.069(4) C14 -0.1859(15) -0.9726(15) -0.2114(2) 0.085(4) C15 -0.064(2) -1.1336(15) -0.2150(3) 0.107(6) C16 0.119(2) -1.099(2) -0.2076(3) 0.134(6) C17 -0.3693(17) -1.0116(19) -0.2289(3) 0.127(6) C18 -0.210(2) -0.7277(14) -0.1678(3) 0.104(5) C19 -0.037(3) -0.6294(15) -0.1735(4) 0.135(8) C20 0.113(2) -0.692(2) -0.1500(4) 0.150(8) C21 -0.358(2) -0.6303(18) -0.1872(3) 0.161(9) H2 0.0148(33) -1.1431(72) -0.1145(29) 0.129 H2A -0.4717(14) -0.7155(14) 0.0534(3) 0.122 H3 -0.4976(17) -1.0023(14) 0.0757(2) 0.132 H4 -0.4969(17) -1.2377(12) 0.0377(3) 0.130 H5 -0.4945(15) -1.1908(11) -0.0214(2) 0.107 H7A -0.5904(15) -0.8113(10) -0.0645(2) 0.107 H7B -0.3816(15) -0.8195(10) -0.0650(2) 0.107 H9A -0.6309(14) -1.2659(15) -0.1355(3) 0.141 H9B -0.6956(14) -1.3770(15) -0.1030(3) 0.141 H10A -0.3657(15) -1.3723(14) -0.1225(3) 0.122 H10B -0.4219(15) -1.4170(14) -0.0839(3) 0.122 H11 -0.2686(12) -1.1773(14) -0.0681(3) 0.106 H12 -0.1733(12) -0.9505(13) -0.1067(2) 0.106 H13A -0.3325(12) -1.1387(12) -0.1632(2) 0.104 H13B -0.4206(12) -0.9656(12) -0.1484(2) 0.104 H14 -0.1304(15) -0.8749(15) -0.2243(2) 0.128 H15A -0.1063(20) -1.2256(15) -0.1993(3) 0.160 H15B -0.0740(20) -1.1788(15) -0.2386(3) 0.160 H16A 0.1872(20) -1.2057(22) -0.2104(3) 0.201 H16B 0.1308(20) -1.0568(22) -0.1840(3) 0.201 H16C 0.1632(20) -1.0099(22) -0.2234(3) 0.201 H17A -0.4454(17) -0.9099(19) -0.2266(3) 0.190 H17B -0.4241(17) -1.1118(19) -0.2177(3) 0.190 H17C -0.3517(17) -1.0374(19) -0.2532(3) 0.190 H18 -0.2379(20) -0.7156(14) -0.1429(3) 0.156 H19A -0.0001(26) -0.6445(15) -0.1976(4) 0.203 H19B -0.0565(26) -0.5038(15) -0.1696(4) 0.203 H20A 0.2186(21) -0.6245(22) -0.1548(4) 0.224 H20B 0.1352(21) -0.8151(22) -0.1541(4) 0.224 H20C 0.0788(21) -0.6744(22) -0.1260(4) 0.224 H21A -0.4688(24) -0.6912(18) -0.1838(3) 0.242 H21B -0.3298(24) -0.6269(18) -0.2117(3) 0.242 H21C -0.3672(24) -0.5115(18) -0.1784(3) 0.242 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 Cl 0.1252(24) -0.0064(14) 0.0047(19) 0.0629(13) -0.0087(21) 0.1025(20) O1 0.0744(48) -0.0204(50) 0.0050(45) 0.1116(58) 0.0153(48) 0.1215(59) O2 0.0756(44) -0.0103(39) 0.0065(40) 0.0997(48) 0.0064(42) 0.0832(50) N1 0.0702(49) -0.0080(34) -0.0082(44) 0.0722(45) -0.0001(56) 0.0583(42) N2 0.0943(56) 0.0016(43) 0.0158(45) 0.0661(47) 0.0092(49) 0.0648(46) C1 0.0597(58) 0.0015(42) -0.0026(62) 0.0584(55) 0.0006(56) 0.0888(68) C2 0.0720(67) -0.0275(58) -0.0034(64) 0.1010(74) 0.0028(74) 0.0704(62) C3 0.0991(81) 0.0032(57) 0.0045(68) 0.0974(72) 0.0019(90) 0.0683(61) C4 0.1104(83) 0.0203(49) 0.0039(78) 0.0788(64) -0.0048(74) 0.0702(65) C5 0.0904(68) -0.0054(41) 0.0016(62) 0.0623(53) 0.0083(66) 0.0612(56) C6 0.0632(52) -0.0072(37) 0.0060(44) 0.0632(46) -0.0057(58) 0.0395(40) C7 0.0762(62) -0.0056(42) 0.0025(56) 0.0734(56) -0.0049(60) 0.0646(56) C8 0.0900(81) -0.0037(55) 0.0163(61) 0.0834(80) 0.0018(65) 0.0571(63) C9 0.0729(78) -0.0280(74) 0.0105(66) 0.0969(95) -0.0224(66) 0.1121(91) C10 0.0949(79) -0.0063(54) -0.0096(56) 0.0684(58) -0.0046(63) 0.0796(71) C11 0.0576(58) 0.0012(54) -0.0011(50) 0.0909(70) -0.0036(59) 0.0636(60) C12 0.0747(61) -0.0025(54) 0.0173(54) 0.0623(55) 0.0037(57) 0.0759(59) C13 0.0597(56) 0.0132(50) 0.0032(49) 0.0802(64) -0.0106(53) 0.0672(59) C14 0.0986(84) 0.0038(57) -0.0068(59) 0.0974(81) 0.0047(71) 0.0603(63) C15 0.147(12) -0.022(6) 0.031(9) 0.073(7) -0.005(8) 0.100(9) C16 0.127(12) -0.007(10) 0.042(9) 0.165(15) 0.036(12) 0.109(10) C17 0.123(11) 0.023(9) -0.006(8) 0.150(11) -0.014(10) 0.108(9) C18 0.139(11) 0.007(6) 0.014(9) 0.066(8) 0.008(8) 0.106(9) C19 0.208(18) 0.010(7) 0.008(12) 0.076(8) -0.035(11) 0.122(11) C20 0.144(14) -0.052(11) 0.034(11) 0.146(13) -0.077(12) 0.159(15) C21 0.223(18) 0.030(10) 0.029(12) 0.132(12) 0.090(12) 0.129(12)