#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/4/4000279.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_4000279 _journal_name_full 'Chemistry of Materials' _journal_year 2003 _publ_section_abstract ; We present the crystal and molecular structure of 5-(4-[N-tert-butyl- N-aminoxyl]phenyl)-1,3-benzenedicarboxylic acid, a stable nitroxide that forms hydrogen-bonded chains. The radical nitroxide units are not involved in the hydrogen bonding. This is the alpha allotrope, with is not formed very frequently. ; _chemical_formula_moiety 'C18 H18 N O5 ' _chemical_formula_sum 'C18 H18 N O5 ' _chemical_name_systematic ; 5-(4-[N-tert-butyl-N-aminoxyl]phenyl)-1,3-benzenedicarboxylic acid ; _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' _cell_length_a 9.7834(3) _cell_length_b 11.3596(4) _cell_length_c 15.4740(6) _cell_angle_alpha 80.3011(13) _cell_angle_beta 81.2087(13) _cell_angle_gamma 76.342(2) _cell_volume 1635.68(10) _chemical_formula_weight 328.344 _diffrn_radiation_type ' MoK\a' _diffrn_radiation_wavelength 0.71073 _diffrn_ambient_temperature 298 _exptl_crystal_f_000 692 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_number 10645 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_full 25.05 _cell_measurement_reflns_used 5556 _cell_measurement_theta_min 4.076 _cell_measurement_theta_max 25.028 _diffrn_measurement_method 'CCD' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_coefficient_mu 0.098 _reflns_number_total 5735 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _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^)+(0.0967P)^2^+0.8943P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5735 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1671 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.2353 _refine_ls_wR_factor_gt 0.1840 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0072(3) -0.2594(3) 0.63264(19) 0.0731(9) Uani 1 1 d . . . O2 O 0.0680(3) -0.1565(3) 0.50624(19) 0.0760(10) Uani 1 1 d . . . O3 O 0.3760(3) 0.1278(3) 0.49897(19) 0.0727(9) Uani 1 1 d . . . O4 O 0.4503(4) 0.1465(3) 0.6240(2) 0.0820(10) Uani 1 1 d . . . O5 O -0.0577(4) -0.2807(3) 1.4276(2) 0.0777(10) Uani 1 1 d . . . O6 O -0.1278(3) -0.3915(3) 1.55147(18) 0.0690(9) Uani 1 1 d . . . O7 O -0.4147(3) -0.6861(3) 1.5413(2) 0.0758(10) Uani 1 1 d . . . O8 O -0.4848(3) -0.7038(3) 1.4147(2) 0.0709(9) Uani 1 1 d . . . O9 O -0.1763(8) -0.2392(6) 0.8706(3) 0.199(3) Uani 1 1 d . . . O10 O 0.0520(4) -0.1965(5) 1.1862(2) 0.1215(17) Uani 1 1 d . . . N1 N 0.1678(4) -0.1666(4) 1.1496(2) 0.0778(12) Uani 1 1 d . . . N2 N -0.2335(5) -0.3284(5) 0.9039(3) 0.0953(16) Uani 1 1 d . . . C1 C 0.0597(4) -0.1843(4) 0.5905(3) 0.0535(11) Uani 1 1 d . . . C2 C 0.1396(4) -0.1219(4) 0.6360(3) 0.0508(10) Uani 1 1 d . . . C3 C 0.2973(4) 0.0122(4) 0.6313(3) 0.0532(11) Uani 1 1 d . . . C4 C 0.3797(4) 0.1006(4) 0.5818(3) 0.0557(11) Uani 1 1 d . . . C5 C 0.2131(4) -0.0934(4) 0.7723(3) 0.0507(10) Uani 1 1 d . . . C6 C 0.2076(4) -0.1170(4) 0.8699(3) 0.0564(11) Uani 1 1 d . . . C7 C 0.1888(5) -0.1518(4) 1.0560(3) 0.0633(12) Uani 1 1 d . . . C8 C 0.2664(5) -0.1537(5) 1.2107(3) 0.0717(14) Uani 1 1 d . . . C9 C -0.1197(4) -0.3613(4) 1.4681(3) 0.0540(11) Uani 1 1 d . . . C10 C -0.1901(4) -0.4259(4) 1.4180(3) 0.0522(10) Uani 1 1 d . . . C11 C -0.3324(4) -0.5684(4) 1.4127(3) 0.0514(10) Uani 1 1 d . . . C12 C -0.4158(4) -0.6594(4) 1.4587(3) 0.0538(11) Uani 1 1 d . . . C13 C -0.2460(4) -0.4554(4) 1.2769(3) 0.0508(10) Uani 1 1 d . . . C14 C -0.2380(4) -0.4244(4) 1.1795(3) 0.0515(10) Uani 1 1 d . . . C15 C -0.2343(5) -0.3649(5) 0.9963(3) 0.0674(13) Uani 1 1 d . . . C16 C -0.2805(5) -0.3881(5) 0.8395(3) 0.0722(14) Uani 1 1 d . . . C17 C -0.4055(6) -0.4455(6) 0.8817(4) 0.099(2) Uani 1 1 d . . . C18 C -0.1548(7) -0.4827(7) 0.8054(5) 0.122(2) Uani 1 1 d . . . C19 C -0.3250(6) -0.2906(6) 0.7638(3) 0.102(2) Uani 1 1 d . . . C20 C 0.3246(13) -0.0388(9) 1.1795(6) 0.212(5) Uani 1 1 d . . . C21 C 0.1890(8) -0.1393(12) 1.2972(5) 0.213(6) Uani 1 1 d . . . C22 C 0.3883(8) -0.2575(8) 1.2111(6) 0.160(4) Uani 1 1 d . . . C23 C 0.3099(6) -0.1284(6) 1.0045(3) 0.097(2) Uani 1 1 d . . . C24 C 0.3177(5) -0.1103(6) 0.9136(3) 0.0907(18) Uani 1 1 d . . . C25 C 0.0897(5) -0.1453(5) 0.9227(3) 0.0727(14) Uani 1 1 d . . . C26 C 0.0804(5) -0.1618(5) 1.0132(3) 0.0770(15) Uani 1 1 d . . . C27 C 0.2933(4) -0.0139(4) 0.7224(3) 0.0582(11) Uani 1 1 d . . . C28 C 0.2195(4) -0.0426(4) 0.5876(3) 0.0545(11) Uani 1 1 d . . . C29 C 0.1366(4) -0.1479(4) 0.7272(3) 0.0532(10) Uani 1 1 d . . . C30 C -0.2404(5) -0.2757(5) 1.0479(3) 0.0697(13) Uani 1 1 d . . . C31 C -0.2419(5) -0.3056(4) 1.1390(3) 0.0629(12) Uani 1 1 d . . . C32 C -0.2274(5) -0.5128(4) 1.1263(3) 0.0671(13) Uani 1 1 d . . . C33 C -0.2245(5) -0.4848(5) 1.0352(3) 0.0732(14) Uani 1 1 d . . . C34 C -0.1800(4) -0.3980(4) 1.3268(3) 0.0539(11) Uani 1 1 d . . . C35 C -0.2649(4) -0.5119(4) 1.4615(3) 0.0541(11) Uani 1 1 d . . . C36 C -0.3224(4) -0.5399(4) 1.3218(3) 0.0547(11) Uani 1 1 d . . . H2 H 0.0212 -0.1946 0.4864 0.114 Uiso 1 1 calc R . . H3 H 0.4256 0.1775 0.4792 0.109 Uiso 1 1 calc R . . H6 H -0.0857 -0.3509 1.5726 0.103 Uiso 1 1 calc R . . H7 H -0.4634 -0.7367 1.5603 0.114 Uiso 1 1 calc R . . H17A H -0.4823 -0.3834 0.9028 0.149 Uiso 1 1 calc R . . H17B H -0.3769 -0.5068 0.9302 0.149 Uiso 1 1 calc R . . H17C H -0.4357 -0.4825 0.8386 0.149 Uiso 1 1 calc R . . H18A H -0.0791 -0.4432 0.7786 0.184 Uiso 1 1 calc R . . H18B H -0.1826 -0.5214 0.7623 0.184 Uiso 1 1 calc R . . H18C H -0.1233 -0.5432 0.8536 0.184 Uiso 1 1 calc R . . H19A H -0.4040 -0.2302 0.7849 0.153 Uiso 1 1 calc R . . H19B H -0.3520 -0.3271 0.7192 0.153 Uiso 1 1 calc R . . H19C H -0.2474 -0.2523 0.7392 0.153 Uiso 1 1 calc R . . H20A H 0.3776 -0.0443 1.1223 0.318 Uiso 1 1 calc R . . H20B H 0.3854 -0.0310 1.2205 0.318 Uiso 1 1 calc R . . H20C H 0.2476 0.0315 1.1762 0.318 Uiso 1 1 calc R . . H21A H 0.1098 -0.0711 1.2921 0.319 Uiso 1 1 calc R . . H21B H 0.2503 -0.1249 1.3353 0.319 Uiso 1 1 calc R . . H21C H 0.1555 -0.2123 1.3214 0.319 Uiso 1 1 calc R . . H22A H 0.4348 -0.2618 1.1520 0.240 Uiso 1 1 calc R . . H22B H 0.3565 -0.3318 1.2333 0.240 Uiso 1 1 calc R . . H22C H 0.4535 -0.2470 1.2482 0.240 Uiso 1 1 calc R . . H23 H 0.3873 -0.1247 1.0314 0.117 Uiso 1 1 calc R . . H24 H 0.4001 -0.0929 0.8807 0.109 Uiso 1 1 calc R . . H25 H 0.0140 -0.1535 0.8962 0.087 Uiso 1 1 calc R . . H26 H -0.0015 -0.1801 1.0463 0.092 Uiso 1 1 calc R . . H27 H 0.3458 0.0227 0.7510 0.070 Uiso 1 1 calc R . . H28 H 0.2214 -0.0259 0.5266 0.065 Uiso 1 1 calc R . . H29 H 0.0831 -0.2023 0.7586 0.064 Uiso 1 1 calc R . . H30 H -0.2434 -0.1953 1.0218 0.084 Uiso 1 1 calc R . . H31 H -0.2455 -0.2448 1.1732 0.075 Uiso 1 1 calc R . . H32 H -0.2220 -0.5936 1.1521 0.080 Uiso 1 1 calc R . . H33 H -0.2160 -0.5463 1.0007 0.088 Uiso 1 1 calc R . . H34 H -0.1287 -0.3404 1.2984 0.065 Uiso 1 1 calc R . . H35 H -0.2701 -0.5317 1.5226 0.065 Uiso 1 1 calc R . . H36 H -0.3681 -0.5784 1.2901 0.066 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 0.088(2) 0.102(3) 0.0495(18) -0.0148(17) -0.0007(15) -0.060(2) O2 0.106(2) 0.095(3) 0.0475(19) -0.0079(17) -0.0176(16) -0.057(2) O3 0.090(2) 0.087(2) 0.054(2) 0.0039(16) -0.0143(16) -0.0493(19) O4 0.108(3) 0.096(3) 0.064(2) -0.0003(18) -0.0224(18) -0.064(2) O5 0.100(2) 0.094(3) 0.060(2) -0.0124(18) -0.0117(17) -0.060(2) O6 0.086(2) 0.090(2) 0.0479(19) -0.0107(16) -0.0156(15) -0.0459(18) O7 0.089(2) 0.092(3) 0.059(2) 0.0073(17) -0.0184(17) -0.053(2) O8 0.078(2) 0.087(2) 0.063(2) -0.0074(17) -0.0131(16) -0.0488(18) O9 0.379(9) 0.221(6) 0.076(3) 0.048(3) -0.085(4) -0.233(7) O10 0.107(3) 0.213(5) 0.060(2) 0.008(3) -0.007(2) -0.086(3) N1 0.078(3) 0.116(4) 0.044(2) 0.000(2) -0.0089(19) -0.038(2) N2 0.134(4) 0.124(4) 0.057(3) 0.013(3) -0.032(2) -0.089(3) C1 0.058(3) 0.068(3) 0.042(3) -0.011(2) -0.0058(19) -0.024(2) C2 0.056(2) 0.059(3) 0.044(2) -0.009(2) -0.0116(18) -0.020(2) C3 0.059(3) 0.058(3) 0.050(3) -0.007(2) -0.0099(19) -0.023(2) C4 0.070(3) 0.060(3) 0.045(3) -0.005(2) -0.011(2) -0.029(2) C5 0.059(3) 0.053(3) 0.045(2) -0.010(2) -0.0092(19) -0.017(2) C6 0.063(3) 0.066(3) 0.048(2) -0.010(2) -0.010(2) -0.024(2) C7 0.071(3) 0.078(3) 0.047(3) -0.009(2) -0.012(2) -0.025(2) C8 0.083(3) 0.086(4) 0.049(3) -0.010(3) -0.021(2) -0.014(3) C9 0.057(3) 0.067(3) 0.046(3) -0.012(2) -0.0066(19) -0.025(2) C10 0.052(2) 0.063(3) 0.049(3) -0.013(2) -0.0094(19) -0.020(2) C11 0.049(2) 0.056(3) 0.054(3) -0.005(2) -0.0105(19) -0.019(2) C12 0.054(2) 0.062(3) 0.052(3) -0.006(2) -0.010(2) -0.022(2) C13 0.049(2) 0.062(3) 0.047(2) -0.011(2) -0.0078(18) -0.020(2) C14 0.054(2) 0.059(3) 0.049(2) -0.007(2) -0.0149(19) -0.023(2) C15 0.083(3) 0.087(4) 0.048(3) -0.005(3) -0.019(2) -0.045(3) C16 0.076(3) 0.107(4) 0.046(3) -0.015(3) -0.008(2) -0.039(3) C17 0.089(4) 0.157(6) 0.077(4) -0.032(4) -0.004(3) -0.069(4) C18 0.099(5) 0.130(6) 0.131(6) -0.025(5) 0.013(4) -0.022(4) C19 0.100(4) 0.153(6) 0.062(3) -0.010(4) -0.020(3) -0.041(4) C20 0.365(15) 0.180(9) 0.163(8) 0.023(7) -0.145(9) -0.164(10) C21 0.110(6) 0.460(19) 0.087(5) -0.113(8) -0.003(4) -0.052(8) C22 0.132(6) 0.167(8) 0.196(9) -0.088(7) -0.093(6) 0.031(6) C23 0.089(4) 0.172(6) 0.051(3) -0.001(3) -0.022(3) -0.067(4) C24 0.083(3) 0.157(6) 0.051(3) -0.008(3) -0.013(2) -0.065(4) C25 0.070(3) 0.105(4) 0.054(3) -0.010(3) -0.011(2) -0.037(3) C26 0.071(3) 0.117(4) 0.053(3) -0.002(3) -0.009(2) -0.047(3) C27 0.068(3) 0.068(3) 0.049(3) -0.009(2) -0.015(2) -0.030(2) C28 0.064(3) 0.063(3) 0.041(2) -0.006(2) -0.0080(19) -0.023(2) C29 0.061(3) 0.057(3) 0.048(2) -0.008(2) -0.0081(19) -0.025(2) C30 0.086(3) 0.072(3) 0.062(3) 0.004(3) -0.024(2) -0.038(3) C31 0.077(3) 0.070(3) 0.053(3) -0.012(2) -0.017(2) -0.030(2) C32 0.093(3) 0.065(3) 0.052(3) -0.004(2) -0.019(2) -0.031(3) C33 0.109(4) 0.077(4) 0.052(3) -0.010(3) -0.016(3) -0.049(3) C34 0.059(3) 0.061(3) 0.049(3) -0.011(2) -0.0073(19) -0.026(2) C35 0.055(2) 0.063(3) 0.050(2) -0.005(2) -0.0101(19) -0.023(2) C36 0.057(3) 0.066(3) 0.051(3) -0.011(2) -0.0149(19) -0.026(2)