#------------------------------------------------------------------------------ #$Date: 2012-03-04 14:29:37 +0200 (Sun, 04 Mar 2012) $ #$Revision: 37814 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/29/4502992.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_4502992 loop_ _publ_author_name 'Ueto, Takamitsu' 'Takata, Noriyuki' 'Muroyama, Norihiro' 'Nedu, Akimitsu' 'Sasaki, Akito' 'Tanida, Satoshi' 'Terada, Katsuhide' _publ_section_title ; Polymorphs and a Hydrate of Furosemide--Nicotinamide 1:1 Cocrystal ; _journal_issue 1 _journal_name_full 'Crystal Growth & Design' _journal_page_first 485 _journal_volume 12 _journal_year 2012 _chemical_formula_moiety 'C12 H11 Cl N2 O5 S, C6 H6 N2 O' _chemical_formula_structural 'C12 H11 Cl N2 O5 S, C6 H6 N2 O' _chemical_formula_sum 'C18 H17 Cl N4 O6 S' _chemical_formula_weight 452.869 _chemical_name_common ; 'furosemide nicotinamide 1:1 cocrystal form IV' ; _chemical_name_systematic ; 4-chloro-2-[(2-furanylmethyl)amino]-5-sulfamoylbenzoic acid pyridine-3-carboxamide ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90 _cell_angle_beta 92.5034(13) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 40.6357(13) _cell_length_b 5.36051(15) _cell_length_c 18.3727(5) _cell_measurement_temperature 298 _cell_volume 3998.3(2) _computing_cell_refinement 'PDXL Version 1.8.1.0 (Rigaku, 2010)' _computing_data_collection 'Rigaku SmartLab' _computing_publication_material 'PDXL Version 1.8.1.0 (Rigaku, 2010)' _computing_structure_refinement 'PDXL Version 1.8.1.0 (Rigaku, 2010)' _computing_structure_solution 'PDXL Version 1.8.1.0 (Rigaku, 2010)' _diffrn_ambient_temperature 298 _diffrn_measurement_device_type 'Rigaku SmartLabGuidance' _diffrn_measurement_method \q/2\q _diffrn_radiation_type 'Cu K\a~1~' _diffrn_radiation_wavelength 1.540593 _exptl_crystal_density_diffrn 1.50 _exptl_crystal_F_000 1872.00 _pd_calc_method 'Rietveld Refinement' _pd_char_colour colourless _pd_meas_2theta_range_inc 0.0050 _pd_meas_2theta_range_max 100.0000 _pd_meas_2theta_range_min 3.0000 _pd_meas_number_of_points 19401 _pd_proc_ls_prof_R_factor 0.0261 _pd_proc_ls_prof_wR_expected 0.0256 _pd_proc_ls_prof_wR_factor 0.0357 _refine_ls_goodness_of_fit_all 1.3955 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 6 _refine_ls_number_parameters 45 _refine_ls_number_restraints 79 _refine_ls_shift/su_max 0.0060 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme sigma _reflns_d_resolution_high 1.0056 _reflns_d_resolution_low 20.2984 _reflns_limit_h_max 40 _reflns_limit_h_min 0 _reflns_limit_k_max 5 _reflns_limit_k_min 0 _reflns_limit_l_max 18 _reflns_limit_l_min -18 _reflns_number_total 2067 _[local]_cod_data_source_file cg2013232_si_001.cif _[local]_cod_data_source_block FS_NCT_cocrystal_form_IV _[local]_cod_chemical_formula_sum_orig 'C18 H17 Cl1 N4 O6 S1' _cod_database_code 4502992 _rigaku_reference_intensity_ratio 0.51 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 1/2+x,1/2+y,z 4 1/2+x,1/2-y,1/2+z 5 -x,-y,-z 6 -x,y,-1/2-z 7 -1/2-x,-1/2-y,-z 8 -1/2-x,-1/2+y,-1/2-z 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 C1 C 0.603869 0.100494 0.448876 0.019004 Uiso 1 C2 C 0.627267 -0.039594 0.487009 0.019004 Uiso 1 C3 C 0.634617 0.007449 0.562635 0.019004 Uiso 1 C4 C 0.617649 0.196498 0.599365 0.019004 Uiso 1 C5 C 0.594949 0.347036 0.559251 0.019004 Uiso 1 C6 C 0.588833 0.295933 0.484103 0.019004 Uiso 1 S1 S 0.628504 0.244066 0.690098 0.019004 Uiso 1 C7 C 0.644518 -0.245599 0.451585 0.019004 Uiso 1 N1 N 0.595526 0.053275 0.378066 0.019004 Uiso 1 C8 C 0.568736 0.186067 0.336529 0.019004 Uiso 1 C9 C 0.538449 0.062787 0.349688 0.019004 Uiso 1 O1 O 0.520975 0.146869 0.402223 0.211975 Uiso 1 C10 C 0.494987 -0.001097 0.405724 0.211975 Uiso 1 C11 C 0.524102 -0.130293 0.323122 0.211975 Uiso 1 C12 C 0.496222 -0.172686 0.361430 0.211975 Uiso 1 Cl1 Cl 0.571748 0.593917 0.596937 0.019004 Uiso 1 O2 O 0.655947 0.078044 0.705991 0.019004 Uiso 1 O3 O 0.602227 0.225343 0.729317 0.019004 Uiso 1 O4 O 0.638261 -0.314382 0.389297 0.077184 Uiso 1 O5 O 0.666885 -0.371236 0.499671 0.077184 Uiso 1 N2 N 0.643413 0.531314 0.699137 0.019004 Uiso 1 H1 H 0.478036 0.021689 0.437480 0.019004 Uiso 1 H2 H 0.606706 -0.063640 0.355215 0.019004 Uiso 1 H3 H 0.572791 0.181282 0.284910 0.019004 Uiso 1 H4 H 0.650629 -0.086762 0.587740 0.019004 Uiso 1 H5 H 0.574178 0.397372 0.457434 0.019004 Uiso 1 H6 H 0.567693 0.357918 0.352801 0.019004 Uiso 1 H7 H 0.677168 -0.492046 0.485390 0.019004 Uiso 1 H8 H 0.531206 -0.225924 0.284600 0.019004 Uiso 1 H9 H 0.481401 -0.303909 0.355104 0.019004 Uiso 1 H10 H 0.650379 0.556158 0.745165 0.019004 Uiso 1 H11 H 0.627679 0.641111 0.687050 0.019004 Uiso 1 O6 O 0.794749 0.244411 0.528573 0.098156 Uiso 1 C13 C 0.792939 0.310396 0.589172 0.045885 Uiso 1 C14 C 0.768856 0.488988 0.617025 0.045885 Uiso 1 C15 C 0.736890 0.442624 0.608973 0.222516 Uiso 1 C16 C 0.714937 0.604923 0.636850 0.222516 Uiso 1 C17 C 0.778730 0.704256 0.650528 0.222516 Uiso 1 N3 N 0.757320 0.873168 0.674112 0.222516 Uiso 1 C18 C 0.726137 0.816319 0.664872 0.222516 Uiso 1 N4 N 0.816268 0.237046 0.639533 0.098156 Uiso 1 H12 H 0.692580 0.567431 0.636123 0.222516 Uiso 1 H13 H 0.801167 0.735438 0.657330 0.222516 Uiso 1 H14 H 0.729484 0.300178 0.584445 0.222516 Uiso 1 H15 H 0.815645 0.291933 0.685170 0.222516 Uiso 1 H16 H 0.832228 0.133938 0.627004 0.222516 Uiso 1 H17 H 0.710780 0.933290 0.679074 0.222516 Uiso 1 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C C 0.017 0.0090 2.31000 1.02000 1.58860 0.865000 20.8439 10.2075 0.568700 51.6512 0.215600 ; International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999), and KEK Report 88-14, 1-136. ; Cl Cl 0.347 0.702 11.4604 7.19640 6.25560 1.64550 0.010400 1.16620 18.5194 47.7784 -9.5574 ; International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999), and KEK Report 88-14, 1-136. ; H H 0.000 0.000 0.489918 0.262003 0.196767 0.049879 20.6593 7.74039 49.5519 2.20159 0.001305 ; International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999). ; N N 0.029 0.018 12.2126 3.13220 2.01250 1.16630 0.005700 9.89330 28.9975 0.582600 -11.529 ; International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999), and KEK Report 88-14, 1-136. ; O O 0.046 0.032 3.04850 2.28680 1.54630 0.867000 13.2771 5.70110 0.323900 32.9089 0.250800 ; International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999), and KEK Report 88-14, 1-136. ; S S 0.319 0.557 6.90530 5.20340 1.43790 1.58630 1.46790 22.2151 0.253600 56.1720 0.866900 ; International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999), and KEK Report 88-14, 1-136. ; 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 O2 S1 O3 118.6006(16) yes O2 S1 N2 106.002(2) yes O3 S1 N2 108.4675(8) yes O4 C7 O5 123.0935(14) yes O6 C13 N4 119.3306(15) yes O6 C13 C14 126.4554(9) yes O1 C10 C12 111.0907(14) yes O1 C9 C11 108.0297(15) yes N1 C8 C9 108.033(2) yes C4 S1 O2 105.4575(11) yes C4 S1 O3 109.7619(18) yes C4 S1 N2 108.0951(5) yes C9 O1 C10 106.8683(17) yes C1 N1 C8 123.4928(11) yes C17 N3 C18 116.0823(17) yes C4 C5 Cl1 124.5623(15) yes C6 C5 Cl1 116.6303(10) yes C3 C4 S1 117.2530(12) yes C5 C4 S1 123.6966(11) yes C8 C9 O1 117.8496(15) yes C2 C7 O4 123.8768(10) yes C2 C7 O5 112.7575(16) yes C2 C1 N1 121.6481(12) yes C6 C1 N1 119.5116(10) yes C14 C13 N4 113.9787(17) yes C16 C18 N3 124.5851(5) yes C14 C17 N3 122.4442(18) yes C1 C2 C3 120.5048(12) yes C1 C2 C7 120.9468(15) yes C3 C2 C7 118.5226(10) yes C2 C3 C4 120.2936(11) yes C13 C14 C15 120.0868(16) yes C2 C1 C6 118.8374(16) yes C4 C5 C6 118.7639(12) yes C1 C6 C5 122.5348(9) yes C3 C4 C5 118.8568(16) yes C8 C9 C11 134.0060(8) yes C10 C12 C11 105.8184(12) yes C9 C11 C12 108.1045(13) yes C13 C14 C17 121.3366(18) yes C15 C14 C17 118.5728(5) yes C14 C15 C16 119.5660(16) yes C15 C16 C18 118.3997(18) yes S1 N2 H10 109.4712(5) no S1 N2 H11 109.471(2) no O1 C10 H1 124.4546(15) no N1 C8 H6 109.7568(12) no N1 C8 H3 109.7568(15) no N3 C17 H13 118.7779(16) no N3 C18 H17 117.7074(17) no C7 O5 H7 120.0000(15) no C1 N1 H2 118.2536(12) no C8 N1 H2 118.2536(16) no C13 N4 H15 120.0000(15) no C13 N4 H16 120.0000(16) no C2 C3 H4 119.8532(12) no C9 C11 H8 125.9478(14) no C12 C11 H8 125.9478(11) no C10 C12 H9 127.0908(13) no C11 C12 H9 127.0908(11) no C5 C6 H5 118.7326(12) no C9 C8 H6 109.7568(12) no C9 C8 H3 109.7568(10) no C14 C15 H14 120.2170(6) no C16 C15 H14 120.2170(18) no C12 C10 H1 124.4546(10) no C15 C16 H12 120.8002(16) no C18 C16 H12 120.8002(5) no C14 C17 H13 118.7779(5) no C1 C6 H5 118.7326(16) no C4 C3 H4 119.8532(16) no C16 C18 H17 117.7074(19) no H10 N2 H11 109.4712(11) no H15 N4 H16 120.0000(10) no H3 C8 H6 109.7568(6) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O2 1.44652(3) yes S1 O3 1.31783(3) yes S1 N2 1.66036(4) yes O6 C13 1.17356(3) yes O1 C10 1.32454(3) yes N1 C8 1.48380(3) yes N3 C18 1.30713(4) yes C5 Cl1 1.78234(3) yes C4 S1 1.72462(4) yes C7 O4 1.21854(3) yes C7 O5 1.41070(3) yes C9 O1 1.30341(3) yes C1 N1 1.35389(3) yes C13 N4 1.35380(3) yes C17 N3 1.34067(3) yes C1 C6 1.38722(3) yes C2 C3 1.43079(4) yes C2 C7 1.47456(3) yes C3 C4 1.41366(3) yes C1 C2 1.37859(3) yes C4 C5 1.40920(3) yes C5 C6 1.41884(4) yes C13 C14 1.47645(3) yes C8 C9 1.42683(4) yes C11 C12 1.37845(4) yes C10 C12 1.23062(2) yes C9 C11 1.27457(3) yes C14 C15 1.32441(4) yes C14 C17 1.36012(3) yes C15 C16 1.36197(3) yes C16 C18 1.31751(3) yes O5 H7 0.820000(16) no N2 H11 0.890000(19) no N4 H16 0.890000(19) no N1 H2 0.890000(16) no N2 H10 0.89000(2) no N4 H15 0.89000(2) no C3 H4 0.930000(19) no C6 H5 0.930000(18) no C8 H6 0.97000(2) no C10 H1 0.93000(2) no C8 H3 0.97000(2) no C11 H8 0.930000(17) no C15 H14 0.930000(19) no C12 H9 0.93000(2) no C17 H13 0.93000(3) no C18 H17 0.930000(19) no C16 H12 0.93000(3) no