#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/15/2001545.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_2001545 loop_ _publ_author_name 'Schouten, A.' 'Kanters, J. A.' 'Poonia, N. S.' _publ_contact_author ; A. Schouten Department of Crystal and Structural Chemistry Bijvoet Center for Biomolecular Research University of Utrecht Padualaan 8 3584 CH Utrecht, The Netherlands. ; _publ_section_title ; Structure of the benzo-15-crown-5--3,5-dinitrobenzoic acid--water (1/1/1) complex ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1376 _journal_page_last 1378 _journal_volume 49 _journal_year 1993 _chemical_formula_moiety 'C7 H4 N2 O6, C14 H20 O5, H2 O' _chemical_formula_sum 'C21 H26 N2 O12' _chemical_formula_weight 498.44 _chemical_melting_point 373.0(5) _chemical_name_systematic ; (3,5-dinitrobenzoic acid)(benzo-15-crown-5)monohydrate ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method 'PLATON_TABLE_ACC option' _cell_angle_alpha 90 _cell_angle_beta 106.916(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.0711(4) _cell_length_b 15.0900(10) _cell_length_c 11.1925(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 100 _cell_measurement_theta_max 17.51 _cell_measurement_theta_min 10.62 _cell_volume 1142.60(12) _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_collection 'CAD4 software (Enraf-Nonius, 1985)' _computing_data_reduction 'HELENA (Spek, 1990)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 100 _diffrn_measurement_device 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator 'Zr filter' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6772 _diffrn_reflns_theta_max 30.26 _diffrn_reflns_theta_min 1.35 _diffrn_standards_decay_% 2.3 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.449 _exptl_crystal_description rod _exptl_crystal_F_000 524 _exptl_crystal_size_max 0.78 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.27 _refine_diff_density_min -0.26 _refine_ls_abs_structure_details ; ; _refine_ls_extinction_coef 0.0016 _refine_ls_extinction_method SHELX76 _refine_ls_goodness_of_fit_obs 1.49 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 420 _refine_ls_number_reflns 2992 _refine_ls_R_factor_obs 0.0332 _refine_ls_shift/esd_max 0.037 _refine_ls_shift/esd_mean 0.0050 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = 1/[\s^2^(F)]' _refine_ls_wR_factor_obs 0.0297 _reflns_number_observed 2992 _reflns_number_total 3413 _reflns_observed_criterion >2.5sigma(I) _[local]_cod_data_source_file ha1021.cif _[local]_cod_data_source_block default _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_database_code 2001545 loop_ _symmetry_equiv_pos_as_xyz '+x, +y, +z' '-x, 1/2+y, -z' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 2 2 -2 1 0 -1 0 -2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.002 0.002 International_Tables_Vol_IV_Table_2.2B H 0 0 International_Tables_Vol_IV_Table_2.2B N 0.004 0.003 International_Tables_Vol_IV_Table_2.2B O 0.008 0.006 International_Tables_Vol_IV_Table_2.2B loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O7 0.7759(2) 0.1483(2) 0.85950(10) 0.0165(4) Uani O8 0.9036(2) 0.0920(2) 1.10660(10) 0.0201(4) Uani O9 0.7704(2) 0.2561(2) 1.20360(10) 0.0222(5) Uani O10 0.8236(2) 0.4062(2) 1.05740(10) 0.0203(4) Uani O11 0.7285(2) 0.3141(2) 0.83120(10) 0.0167(4) Uani C8 0.8208(3) 0.1279(2) 0.6531(2) 0.0173(6) Uani C9 0.7891(3) 0.1795(2) 0.7476(2) 0.0148(5) Uani C10 0.7624(3) 0.2714(2) 0.7320(2) 0.0145(5) Uani C11 0.7659(3) 0.3108(2) 0.6204(2) 0.0191(6) Uani C12 0.7939(3) 0.2578(2) 0.5236(2) 0.0200(6) Uani C13 0.8213(3) 0.1683(2) 0.5400(2) 0.0204(6) Uani C14 0.8237(3) 0.0574(2) 0.8892(2) 0.0189(6) Uani C15 0.7750(3) 0.0410(2) 1.0091(2) 0.0200(6) Uani C16 0.8293(4) 0.1011(2) 1.2125(2) 0.0230(6) Uani C17 0.6742(3) 0.1724(2) 1.1962(2) 0.0223(6) Uani C18 0.6354(3) 0.3284(2) 1.1757(2) 0.0247(6) Uani C19 0.7501(4) 0.4103(2) 1.1639(2) 0.0237(6) Uani C20 0.6815(4) 0.4375(2) 0.9465(2) 0.0219(6) Uani C21 0.7379(3) 0.4089(2) 0.8334(2) 0.0197(6) Uani O1 1.3613(3) 0.0807(2) 0.3648(2) 0.0354(6) Uani O2 1.3940(3) 0.0041(2) 0.5335(2) 0.0355(5) Uani O3 1.2881(2) 0.1395(2) 0.90410(10) 0.0237(4) Uani O4 1.2216(2) 0.2852(2) 0.89890(10) 0.0209(4) Uani O5 1.1720(3) 0.4538(2) 0.5268(2) 0.0466(8) Uani O6 1.2328(3) 0.3946(2) 0.36590(10) 0.0312(5) Uani N1 1.3635(3) 0.0736(2) 0.4745(2) 0.0264(6) Uani N2 1.2203(3) 0.3911(2) 0.4725(2) 0.0251(6) Uani C1 1.2955(3) 0.23311 0.4740(2) 0.0189(6) Uani C2 1.3267(3) 0.1542(2) 0.5389(2) 0.0195(6) Uani C3 1.3228(3) 0.1465(2) 0.6614(2) 0.0181(6) Uani C4 1.2849(3) 0.2215(2) 0.7227(2) 0.0156(5) Uani C5 1.2533(3) 0.3026(2) 0.6615(2) 0.0167(6) Uani C6 1.2602(3) 0.3060(2) 0.5391(2) 0.0189(6) Uani C7 1.2673(3) 0.2111(2) 0.8522(2) 0.0174(6) Uani O22 1.1016(2) 0.2578(2) 1.0873(2) 0.0238(5) Uani H81 0.841(3) 0.066(2) 0.669(2) 0.015(5) Uiso H111 0.748(3) 0.3730(10) 0.613(2) 0.013(5) Uiso H121 0.791(4) 0.285(2) 0.452(2) 0.024(6) Uiso H131 0.843(3) 0.131(2) 0.476(2) 0.024(6) Uiso H141 0.968(3) 0.0500(10) 0.896(2) 0.016(6) Uiso H142 0.751(4) 0.021(2) 0.826(2) 0.021(6) Uiso H151 0.793(3) -0.019(2) 1.028(2) 0.022(6) Uiso H152 0.637(3) 0.0600(10) 1.001(2) 0.010(5) Uiso H161 0.770(4) 0.046(2) 1.231(2) 0.024(6) Uiso H162 0.940(4) 0.112(2) 1.278(2) 0.020(6) Uiso H171 0.574(3) 0.1650(10) 1.115(2) 0.016(5) Uiso H172 0.611(4) 0.171(2) 1.267(2) 0.029(6) Uiso H181 0.526(3) 0.314(2) 1.091(2) 0.021(6) Uiso H182 0.576(3) 0.337(2) 1.243(2) 0.027(6) Uiso H191 0.863(4) 0.414(2) 1.233(2) 0.029(7) Uiso H192 0.679(3) 0.461(2) 1.160(2) 0.015(6) Uiso H201 0.675(3) 0.503(2) 0.949(2) 0.018(6) Uiso H202 0.548(3) 0.410(2) 0.939(2) 0.021(6) Uiso H211 0.868(4) 0.426(2) 0.836(2) 0.021(6) Uiso H212 0.641(3) 0.4350(10) 0.759(2) 0.016(6) Uiso H11 1.293(3) 0.237(2) 0.386(2) 0.021(6) Uiso H31 1.341(3) 0.091(2) 0.703(2) 0.011(5) Uiso H41 1.187(4) 0.272(2) 0.960(2) 0.029(7) Uiso H51 1.222(3) 0.355(2) 0.699(2) 0.022(6) Uiso H221 1.009(4) 0.294(2) 1.084(2) 0.039(8) Uiso H222 1.044(5) 0.212(3) 1.083(3) 0.060(10) Uiso 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 O7 0.0240(8) 0.0125(7) 0.0146(7) 0.0023(6) 0.0081(6) 0.0007(5) O8 0.0202(8) 0.0234(8) 0.0165(7) -0.0012(6) 0.0052(6) 0.0028(6) O9 0.0184(8) 0.0270(8) 0.0213(8) -0.0005(7) 0.0060(6) -0.0009(6) O10 0.0204(8) 0.0204(7) 0.0196(7) 0.0008(6) 0.0048(6) -0.0042(6) O11 0.0233(8) 0.0116(7) 0.0161(6) 0.0004(6) 0.0072(6) -0.0007(5) C8 0.0140(10) 0.0210(10) 0.0166(9) -0.0004(8) 0.0039(8) -0.0031(8) C9 0.0127(9) 0.0180(10) 0.0129(9) -0.0007(8) 0.0023(8) 0.0000(7) C10 0.0131(9) 0.0180(10) 0.0126(9) -0.0009(8) 0.0041(7) -0.0014(7) C11 0.0170(10) 0.0220(10) 0.0169(9) -0.0010(9) 0.0027(8) 0.0021(9) C12 0.0160(10) 0.0330(10) 0.0112(9) -0.0034(9) 0.0044(8) 0.0035(8) C13 0.0160(10) 0.0320(10) 0.0141(9) -0.0012(9) 0.0058(8) -0.0061(9) C14 0.0240(10) 0.0130(10) 0.0190(10) 0.0013(8) 0.0053(9) 0.0000(7) C15 0.0230(10) 0.0160(10) 0.0210(10) -0.0028(9) 0.0062(9) 0.0038(8) C16 0.0270(10) 0.0280(10) 0.0140(9) -0.0030(10) 0.0060(9) 0.0038(9) C17 0.0200(10) 0.0320(10) 0.0159(9) -0.0060(10) 0.0066(9) 0.0014(9) C18 0.0220(10) 0.0350(10) 0.0190(10) 0.0040(10) 0.0090(9) -0.0011(9) C19 0.0260(10) 0.0260(10) 0.0180(10) 0.0040(10) 0.0046(9) -0.0073(9) C20 0.0270(10) 0.0140(10) 0.0240(10) 0.0040(9) 0.0065(9) -0.0027(8) C21 0.0240(10) 0.0130(10) 0.0220(10) -0.0006(9) 0.0065(9) 0.0007(8) O1 0.0400(10) 0.0390(10) 0.0296(9) -0.0029(9) 0.0137(8) -0.0160(8) O2 0.0430(10) 0.0189(8) 0.0430(10) 0.0027(8) 0.0102(9) -0.0077(8) O3 0.0224(8) 0.0245(8) 0.0232(7) 0.0015(7) 0.0052(6) 0.0068(6) O4 0.0231(8) 0.0234(8) 0.0183(7) -0.0008(6) 0.0091(6) 0.0003(6) O5 0.085(2) 0.0203(9) 0.0470(10) 0.0130(10) 0.0390(10) 0.0099(8) O6 0.0430(10) 0.0288(9) 0.0212(8) -0.0069(8) 0.0084(7) 0.0054(7) N1 0.0185(9) 0.0250(10) 0.0340(10) -0.0026(8) 0.0051(8) -0.0138(9) N2 0.0290(10) 0.0201(9) 0.0280(10) -0.0018(8) 0.0113(8) 0.0054(8) C1 0.0140(10) 0.0250(10) 0.0178(9) -0.0048(8) 0.0048(8) -0.0024(8) C2 0.0150(10) 0.0180(10) 0.0250(10) -0.0009(8) 0.0051(8) -0.0063(8) C3 0.0130(10) 0.0150(10) 0.0250(10) -0.0013(8) 0.0035(8) 0.0009(8) C4 0.0120(10) 0.0164(9) 0.0178(9) -0.0019(8) 0.0033(8) 0.0004(8) C5 0.0140(10) 0.0160(10) 0.0200(10) -0.0011(8) 0.0050(8) -0.0022(8) C6 0.0170(10) 0.0170(10) 0.0230(10) -0.0018(8) 0.0065(8) 0.0038(8) C7 0.0110(10) 0.0220(10) 0.0180(10) -0.0017(8) 0.0022(8) 0.0011(8) O22 0.0218(9) 0.0254(9) 0.0273(8) -0.0037(8) 0.0121(7) -0.0036(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O7 C9 . . 1.366(3) yes O7 C14 . . 1.429(4) yes O8 C15 . . 1.426(3) yes O8 C16 . . 1.436(3) yes O9 C17 . . 1.426(4) yes O9 C18 . . 1.423(4) yes O10 C19 . . 1.434(3) yes O10 C20 . . 1.431(3) yes O11 C10 . . 1.364(3) yes O11 C21 . . 1.432(4) yes C8 C9 . . 1.383(3) yes C8 C13 . . 1.406(3) yes C9 C10 . . 1.404(4) yes C10 C11 . . 1.390(3) yes C11 C12 . . 1.406(3) yes C12 C13 . . 1.369(4) yes C14 C15 . . 1.500(3) yes C16 C17 . . 1.509(4) yes C18 C19 . . 1.505(4) yes C20 C21 . . 1.497(3) yes C8 H81 . . 0.95(3) no C11 H111 . . 0.95(2) no C12 H121 . . 0.90(2) no C13 H131 . . 0.96(3) no C14 H141 . . 1.01(2) no C14 H142 . . 0.92(3) no C15 H151 . . 0.93(3) no C15 H152 . . 1.00(2) no C16 H161 . . 0.98(3) no C16 H162 . . 0.92(3) no C17 H171 . . 0.98(2) no C17 H172 . . 1.02(3) no C18 H181 . . 1.06(2) no C18 H182 . . 0.97(2) no C19 H191 . . 0.94(2) no C19 H192 . . 0.91(3) no C20 H201 . . 0.99(3) no C20 H202 . . 1.01(2) no C21 H211 . . 0.95(3) no C21 H212 . . 0.99(2) no O1 N1 . . 1.228(3) yes O2 N1 . . 1.225(4) yes O3 C7 . . 1.215(4) yes O4 C7 . . 1.314(4) yes O5 N2 . . 1.226(4) yes O6 N2 . . 1.223(3) yes N1 C2 . . 1.475(4) yes N2 C6 . . 1.470(4) yes C1 C2 . . 1.379(3) yes C1 C6 . . 1.382(3) yes C2 C3 . . 1.384(3) yes C3 C4 . . 1.389(4) yes C4 C5 . . 1.388(4) yes C4 C7 . . 1.499(3) yes C5 C6 . . 1.386(3) yes O4 H41 . . 0.82(2) no C1 H11 . . 0.98(2) no C3 H31 . . 0.95(3) no C5 H51 . . 0.95(3) no O22 H221 . . 0.85(3) no O22 H222 . . 0.80(4) no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C9 O7 C14 . . . 118.0(2) yes C15 O8 C16 . . . 112.2(2) yes C17 O9 C18 . . . 112.8(2) yes C19 O10 C20 . . . 112.0(2) yes C10 O11 C21 . . . 117.9(2) yes C9 C8 C13 . . . 119.2(3) yes O7 C9 C8 . . . 125.2(3) yes O7 C9 C10 . . . 114.3(2) yes C8 C9 C10 . . . 120.5(2) yes O11 C10 C9 . . . 114.5(2) yes O11 C10 C11 . . . 125.6(3) yes C9 C10 C11 . . . 119.8(2) yes C10 C11 C12 . . . 119.5(3) yes C11 C12 C13 . . . 120.3(2) yes C8 C13 C12 . . . 120.7(2) yes O7 C14 C15 . . . 105.4(2) yes O8 C15 C14 . . . 109.5(2) yes O8 C16 C17 . . . 113.3(2) yes O9 C17 C16 . . . 107.9(2) yes O9 C18 C19 . . . 107.7(2) yes O10 C19 C18 . . . 111.9(2) yes O10 C20 C21 . . . 110.2(2) yes O11 C21 C20 . . . 106.3(2) yes C9 C8 H81 . . . 117.0(10) no C13 C8 H81 . . . 124.0(10) no C10 C11 H111 . . . 118.0(10) no C12 C11 H111 . . . 123.0(10) no C11 C12 H121 . . . 117(2) no C13 C12 H121 . . . 123(2) no C8 C13 H131 . . . 117(2) no C12 C13 H131 . . . 122(2) no O7 C14 H141 . . . 106.9(9) no O7 C14 H142 . . . 111(2) no C15 C14 H141 . . . 114.0(10) no C15 C14 H142 . . . 111(2) no H141 C14 H142 . . . 109(2) no O8 C15 H151 . . . 110.0(10) no O8 C15 H152 . . . 108.0(10) no C14 C15 H151 . . . 108.0(10) no C14 C15 H152 . . . 110.0(10) no H151 C15 H152 . . . 112(2) no O8 C16 H161 . . . 112.0(10) no O8 C16 H162 . . . 104(2) no C17 C16 H161 . . . 107(2) no C17 C16 H162 . . . 113(2) no H161 C16 H162 . . . 108(2) no O9 C17 H171 . . . 111.0(10) no O9 C17 H172 . . . 106(2) no C16 C17 H171 . . . 110.0(10) no C16 C17 H172 . . . 111(2) no H171 C17 H172 . . . 111(2) no O9 C18 H181 . . . 108(2) no O9 C18 H182 . . . 110(2) no C19 C18 H181 . . . 111(2) no C19 C18 H182 . . . 109(2) no H181 C18 H182 . . . 111(2) no O10 C19 H191 . . . 105(2) no O10 C19 H192 . . . 109.0(10) no C18 C19 H191 . . . 109(2) no C18 C19 H192 . . . 113(2) no H191 C19 H192 . . . 108(2) no O10 C20 H201 . . . 109.0(10) no O10 C20 H202 . . . 110.0(10) no C21 C20 H201 . . . 110.0(10) no C21 C20 H202 . . . 106.0(10) no H201 C20 H202 . . . 111(2) no O11 C21 H211 . . . 108(2) no O11 C21 H212 . . . 111.0(10) no C20 C21 H211 . . . 113.0(10) no C20 C21 H212 . . . 108.0(10) no H211 C21 H212 . . . 110(2) no O1 N1 O2 . . . 124.3(3) yes O1 N1 C2 . . . 117.6(3) yes O2 N1 C2 . . . 118.1(2) yes O5 N2 O6 . . . 124.1(3) yes O5 N2 C6 . . . 117.6(2) yes O6 N2 C6 . . . 118.3(3) yes C2 C1 C6 . . . 115.8(2) yes N1 C2 C1 . . . 118.6(2) yes N1 C2 C3 . . . 118.2(3) yes C1 C2 C3 . . . 123.2(2) yes C2 C3 C4 . . . 118.9(3) yes C3 C4 C5 . . . 120.1(2) yes C3 C4 C7 . . . 118.3(2) yes C5 C4 C7 . . . 121.5(2) yes C4 C5 C6 . . . 118.3(3) yes N2 C6 C1 . . . 117.7(2) yes N2 C6 C5 . . . 118.5(2) yes C1 C6 C5 . . . 123.7(3) yes O3 C7 O4 . . . 125.2(2) yes O3 C7 C4 . . . 121.5(2) yes O4 C7 C4 . . . 113.3(2) yes C7 O4 H41 . . . 107(2) no C2 C1 H11 . . . 122(2) no C6 C1 H11 . . . 122(2) no C2 C3 H31 . . . 121.0(10) no C4 C3 H31 . . . 120.0(10) no C4 C5 H51 . . . 123.0(10) no C6 C5 H51 . . . 119.0(10) no H221 O22 H222 . . . 100(3) no