#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/56/2005685.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_2005685 loop_ _publ_author_name 'Gonz\'alez, O. A.' 'Mombr\'u, A. W.' 'Suescun, L. P.' 'Mariezcurrena, R. A.' 'Manta, E.' 'Prandi, C.' _publ_section_title ; Acetoxymethyl 4-Chloro-N-furfuryl-5-sulfamoylanthranilate, an Absorption Furosemide Prodrug ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2875 _journal_page_last 2878 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C15 H15 Cl N2 O7 S' _chemical_formula_weight 402.80 _chemical_melting_point 421.5(5) _chemical_name_systematic ; acetyloxymethyl 4-chloro-N-furfuryl-5-sulfamoylanthranilate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL _cell_angle_alpha 72.01 _cell_angle_beta 74.57 _cell_angle_gamma 72.74 _cell_formula_units_Z 2 _cell_length_a 8.502(2) _cell_length_b 9.653(3) _cell_length_c 11.767(2) _cell_measurement_reflns_used 40 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 7.5 _cell_volume 860.8(4) _computing_cell_refinement P3/P4/PC _computing_data_collection 'P3/P4/PC (Siemens, 1991)' _computing_data_reduction 'XDISK in SHELXTL/PC (Sheldrick, 1990b)' _computing_molecular_graphics 'ZORTEP (Zsolnai & Pritzkow, 1995)' _computing_publication_material 'CIFTAB in SHELXL93' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990a)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens R3m difractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0937 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4213 _diffrn_reflns_theta_max 24.05 _diffrn_reflns_theta_min 1.85 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.554 _exptl_crystal_description Prismatic _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.298 _refine_diff_density_min -0.449 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.930 _refine_ls_goodness_of_fit_obs 1.088 _refine_ls_hydrogen_treatment 'For H atoms, U~eq~ fixed at 1.2U~iso~ of parent atom' _refine_ls_matrix_type full _refine_ls_number_parameters 269 _refine_ls_number_reflns 2722 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.930 _refine_ls_restrained_S_obs 1.088 _refine_ls_R_factor_all 0.1086 _refine_ls_R_factor_obs 0.0511 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0687P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1437 _refine_ls_wR_factor_obs 0.1179 _reflns_number_observed 1461 _reflns_number_total 2722 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file sx1003.cif _[local]_cod_data_source_block pdpub _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '421-422 K' was changed to '421.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2005685 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol C1 1 0.5006(6) 0.4033(5) -0.1054(4) 0.0335(12) Uani d . C C2 1 0.6547(6) 0.2968(5) -0.0865(4) 0.0380(12) Uani d . C C3 1 0.6462(7) 0.1662(6) 0.0104(4) 0.0419(14) Uani d . C H4 1 0.7469(62) 0.0938(52) 0.0207(42) 0.050 Uiso d . H C4 1 0.4962(6) 0.1429(5) 0.0816(4) 0.0398(13) Uani d . C C5 1 0.3443(6) 0.2507(5) 0.0662(4) 0.0371(12) Uani d . C C6 1 0.3500(6) 0.3784(5) -0.0275(4) 0.0376(13) Uani d . C H5 1 0.2494(58) 0.4551(49) -0.0454(39) 0.045 Uiso d . H C7 1 0.4984(6) 0.5405(5) -0.2055(4) 0.0344(12) Uani d . C O1 1 0.6199(4) 0.5714(4) -0.2821(3) 0.0530(10) Uani d . O O2 1 0.3457(4) 0.6354(3) -0.2026(3) 0.0434(9) Uani d . O C8 1 0.3254(7) 0.7637(5) -0.3003(4) 0.0459(15) Uani d . C H6 1 0.4232(34) 0.7997(15) -0.3285(10) 0.055 Uiso calc R H H7 1 0.2362(31) 0.8397(28) -0.2763(10) 0.055 Uiso calc R H O3 1 0.2909(5) 0.7158(4) -0.3927(3) 0.0496(10) Uani d . O C9 1 0.2515(7) 0.8236(6) -0.4914(5) 0.0500(15) Uani d . C O4 1 0.2549(6) 0.9510(4) -0.5056(3) 0.0751(14) Uani d . O C10 1 0.2022(11) 0.7653(9) -0.5758(7) 0.081(2) Uani d . C H8 1 0.1429(83) 0.6847(70) -0.5355(59) 0.097 Uiso d . H H9 1 0.1723(84) 0.8295(73) -0.6354(60) 0.097 Uiso d . H H10 1 0.3071(89) 0.7087(74) -0.6159(62) 0.097 Uiso d . H N1 1 0.8048(5) 0.3166(5) -0.1581(4) 0.0467(12) Uani d . N H1 1 0.7998(63) 0.4130(53) -0.2162(44) 0.056 Uiso d . H C11 1 0.9666(6) 0.2225(6) -0.1361(5) 0.0509(15) Uani d . C H11 1 0.9658(6) 0.1183(6) -0.1225(5) 0.061 Uiso calc R H H12 1 0.9893(6) 0.2346(6) -0.0637(5) 0.061 Uiso calc R H C12 1 1.1006(6) 0.2629(6) -0.2421(5) 0.0431(13) Uani d . C C13 1 1.1766(8) 0.3764(7) -0.2864(6) 0.058(2) Uani d . C H13 1 1.1574(72) 0.4453(61) -0.2399(50) 0.070 Uiso d . H C14 1 1.2891(8) 0.3522(7) -0.3950(6) 0.061(2) Uani d . C H14 1 1.3494(73) 0.4121(62) -0.4465(52) 0.073 Uiso d . H C15 1 1.2745(8) 0.2281(8) -0.4101(5) 0.061(2) Uani d . C H15 1 1.3108(72) 0.1873(61) -0.4761(52) 0.074 Uiso d . H O5 1 1.1573(5) 0.1685(4) -0.3185(4) 0.0574(10) Uani d . O S 1 0.1468(2) 0.2306(2) 0.15933(12) 0.0447(4) Uani d . S O6 1 0.0319(4) 0.3679(4) 0.1196(3) 0.0604(11) Uani d . O O7 1 0.1150(5) 0.0940(4) 0.1583(3) 0.0594(11) Uani d . O N2 1 0.1540(6) 0.2188(5) 0.2983(4) 0.0509(12) Uani d . N H2 1 0.2110(64) 0.1125(58) 0.3322(45) 0.061 Uiso d . H H3 1 0.1662(65) 0.3088(59) 0.3215(46) 0.061 Uiso d . H Cl 1 0.5000(2) -0.02080(15) 0.19650(13) 0.0593(5) Uani d . Cl 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 C1 0.033(3) 0.033(3) 0.033(3) -0.006(2) -0.006(2) -0.007(2) C2 0.033(3) 0.051(3) 0.032(3) -0.007(2) -0.011(2) -0.011(2) C3 0.033(3) 0.042(3) 0.038(3) 0.002(2) -0.011(3) 0.002(2) C4 0.040(3) 0.038(3) 0.032(3) -0.003(2) -0.010(2) 0.000(2) C5 0.031(3) 0.042(3) 0.032(3) -0.006(2) -0.007(2) -0.001(2) C6 0.029(3) 0.043(3) 0.033(3) -0.004(2) -0.008(2) -0.001(2) C7 0.029(3) 0.044(3) 0.032(3) -0.011(2) -0.008(2) -0.006(2) O1 0.036(2) 0.057(2) 0.047(2) -0.013(2) 0.000(2) 0.008(2) O2 0.037(2) 0.038(2) 0.039(2) -0.003(2) -0.007(2) 0.007(2) C8 0.043(3) 0.040(3) 0.046(3) -0.006(3) -0.016(3) 0.003(2) O3 0.063(3) 0.039(2) 0.048(2) -0.018(2) -0.024(2) 0.006(2) C9 0.043(3) 0.050(4) 0.044(3) -0.004(3) -0.011(3) 0.003(3) O4 0.123(4) 0.046(2) 0.051(3) -0.018(3) -0.034(3) 0.008(2) C10 0.103(6) 0.086(6) 0.059(5) -0.038(5) -0.044(5) 0.012(4) N1 0.028(2) 0.055(3) 0.040(3) -0.006(2) -0.004(2) 0.005(2) C11 0.037(3) 0.057(3) 0.047(3) -0.001(3) -0.012(3) -0.002(3) C12 0.029(3) 0.051(3) 0.039(3) 0.001(3) -0.002(2) -0.010(3) C13 0.049(4) 0.053(4) 0.065(4) -0.009(3) -0.002(3) -0.013(3) C14 0.045(4) 0.055(4) 0.063(4) -0.013(3) 0.004(3) 0.002(3) C15 0.052(4) 0.079(5) 0.047(4) -0.018(4) 0.003(3) -0.014(3) O5 0.042(2) 0.066(3) 0.061(3) -0.018(2) -0.003(2) -0.014(2) S 0.0325(8) 0.0514(8) 0.0389(8) -0.0115(6) -0.0048(6) 0.0043(6) O6 0.035(2) 0.061(2) 0.056(2) 0.003(2) -0.006(2) 0.010(2) O7 0.054(3) 0.063(2) 0.065(3) -0.033(2) -0.009(2) -0.005(2) N2 0.059(3) 0.048(3) 0.034(3) -0.011(2) -0.007(2) 0.003(2) Cl 0.0489(9) 0.0499(8) 0.0543(9) -0.0051(7) -0.0112(7) 0.0167(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C6 C1 C7 119.5(4) yes N1 C2 C3 120.4(4) yes C3 C4 Cl 117.4(4) yes C6 C5 S 118.2(4) yes O1 C7 O2 121.7(4) yes O2 C7 C1 112.8(4) yes O2 C8 O3 105.3(4) yes O4 C9 O3 122.5(6) yes O3 C9 C10 111.8(5) yes N1 C11 C12 110.3(4) yes C13 C12 C11 135.0(6) yes C12 C13 C14 106.9(6) yes C14 C15 O5 111.0(6) yes O6 S O7 118.8(2) yes O7 S N2 107.2(2) yes C2 C1 C7 120.7(4) yes N1 C2 C1 122.3(4) yes C5 C4 Cl 121.0(4) yes C4 C5 S 123.8(3) yes O1 C7 C1 125.5(4) yes C7 O2 C8 117.6(4) yes C9 O3 C8 116.0(4) yes O4 C9 C10 125.7(5) yes C2 N1 C11 125.1(4) yes C13 C12 O5 109.6(5) yes O5 C12 C11 115.3(5) yes C15 C14 C13 106.9(6) yes C15 O5 C12 105.6(5) yes O6 S N2 106.8(3) yes C6 C1 C2 119.8(4) ? C3 C2 C1 117.4(4) ? C4 C3 C2 121.2(5) ? C4 C3 H4 121.(3) ? C2 C3 H4 118.(3) ? C3 C4 C5 121.6(4) ? C6 C5 C4 118.0(4) ? C5 C6 C1 122.0(4) ? C5 C6 H5 122.(3) ? C1 C6 H5 116.(3) ? O2 C8 H6 110.7(3) ? O3 C8 H6 110.7(3) ? O2 C8 H7 110.7(3) ? O3 C8 H7 110.7(2) ? H6 C8 H7 108.8 ? C9 C10 H8 114.(4) ? C9 C10 H9 114.(5) ? H8 C10 H9 120.(6) ? C9 C10 H10 106.(4) ? H8 C10 H10 100.(6) ? H9 C10 H10 100.(6) ? C2 N1 H1 114.(3) ? C11 N1 H1 119.(3) ? N1 C11 H11 109.6(3) ? C12 C11 H11 109.6(3) ? N1 C11 H12 109.6(3) ? C12 C11 H12 109.6(3) ? H11 C11 H12 108.1 ? C12 C13 H13 119.(4) ? C14 C13 H13 134.(4) ? C15 C14 H14 126.(4) ? C13 C14 H14 127.(4) ? C14 C15 H15 132.(4) ? O5 C15 H15 116.(4) ? O6 S C5 105.4(2) ? O7 S C5 109.7(2) ? N2 S C5 108.6(2) ? S N2 H2 106.(3) ? S N2 H3 121.(3) ? H2 N2 H3 124.(4) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 1.400(6) yes C1 C7 1.475(6) yes C2 C3 1.420(6) yes C4 C5 1.412(6) yes C5 C6 1.380(6) yes C7 O1 1.220(5) yes O2 C8 1.409(5) yes O3 C9 1.340(6) yes C9 C10 1.479(9) yes C11 C12 1.487(7) yes C12 O5 1.373(6) yes C14 C15 1.309(9) yes S O6 1.422(3) yes S N2 1.620(5) yes C1 C2 1.427(6) yes C2 N1 1.359(6) yes C3 C4 1.366(7) yes C4 Cl 1.732(5) yes C5 S 1.772(5) yes C7 O2 1.347(5) yes C8 O3 1.429(6) yes C9 O4 1.197(6) yes N1 C11 1.445(6) yes C12 C13 1.333(7) yes C13 C14 1.416(8) yes C15 O5 1.367(6) yes S O7 1.427(4) yes C3 H4 0.94(5) ? C6 H5 0.97(4) ? C8 H6 0.94(3) ? C8 H7 0.94(3) ? C10 H8 0.98(6) ? C10 H9 0.82(6) ? C10 H10 0.98(7) ? N1 H1 0.97(5) ? C11 H11 0.97 ? C11 H12 0.97 ? C13 H13 0.94(5) ? C14 H14 0.87(5) ? C15 H15 0.92(5) ? N2 H2 1.00(5) ? N2 H3 1.03(5) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C7 C1 C2 N1 0.5(7) yes C2 C3 C4 Cl 179.5(4) yes S C5 C6 C1 -180.0(4) yes C2 C1 C7 O1 4.0(8) yes O1 C7 O2 C8 8.0(7) yes O2 C8 O3 C9 174.1(4) yes C2 N1 C11 C12 171.4(5) yes C12 C13 C14 C15 0.3(7) yes C13 C12 O5 C15 1.4(6) yes C6 C5 S O7 123.7(4) yes N1 C2 C3 C4 -178.6(5) yes Cl C4 C5 S -0.3(7) yes C7 C1 C6 C5 178.7(5) yes C6 C1 C7 O2 5.7(6) yes C7 O2 C8 O3 84.5(5) yes C8 O3 C9 O4 4.5(8) yes C3 C2 N1 C11 -7.9(8) yes N1 C11 C12 C13 73.9(8) yes O5 C12 C13 C14 -1.1(6) yes C14 C15 O5 C12 -1.2(7) yes C6 C5 S O6 -5.3(5) yes C6 C5 S N2 -119.4(4) yes C6 C1 C2 N1 -178.8(5) ? C6 C1 C2 C3 1.8(7) ? C7 C1 C2 C3 -178.9(5) ? C1 C2 C3 C4 0.8(8) ? C2 C3 C4 C5 -3.4(8) ? C3 C4 C5 C6 3.2(8) ? Cl C4 C5 C6 -179.7(4) ? C3 C4 C5 S -177.4(4) ? C4 C5 C6 C1 -0.5(8) ? C2 C1 C6 C5 -1.9(7) ? C6 C1 C7 O1 -176.7(5) ? C2 C1 C7 O2 -173.6(4) ? C1 C7 O2 C8 -174.3(4) ? C8 O3 C9 C10 -174.5(5) ? C1 C2 N1 C11 172.7(5) ? N1 C11 C12 O5 -101.9(5) ? C11 C12 C13 C14 -177.0(6) ? C13 C14 C15 O5 0.6(7) ? C11 C12 O5 C15 178.2(4) ? C4 C5 S O6 175.3(4) ? C4 C5 S O7 -55.7(5) ? C4 C5 S N2 61.2(5) ?