#------------------------------------------------------------------------------ #$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $ #$Revision: 176467 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/99/4509914.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_4509914 loop_ _publ_author_name 'Harriss, Bethany I.' 'Vella-Zarb, Liana' 'Wilson, Claire' 'Evans, Ivana Radosavljevic' _publ_section_title ; Furosemide Cocrystals: Structures, Hydrogen Bonding, and Implications for Properties ; _journal_issue 2 _journal_name_full 'Crystal Growth & Design' _journal_page_first 783 _journal_paper_doi 10.1021/cg401662d _journal_volume 14 _journal_year 2014 _chemical_formula_moiety 'C12 H11 Cl N2 O5 S, C6 H6 N2 O' _chemical_formula_sum 'C18 H17 Cl N4 O6 S' _chemical_formula_weight 452.88 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 93.291(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.8206(3) _cell_length_b 20.6135(14) _cell_length_c 19.1406(12) _cell_measurement_reflns_used 0 _cell_measurement_temperature 100 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 1898.9(2) _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device Serial _diffrn_measurement_device_type Unknown _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.089 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 19263 _diffrn_reflns_theta_full 25.015 _diffrn_reflns_theta_max 25.015 _diffrn_reflns_theta_min 1.453 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 936 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.73 _refine_diff_density_min -0.73 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9293 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 3336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0445 _refine_ls_shift/su_max 0.0006060 _refine_ls_shift/su_mean 0.0000308 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 19.3 25.4 12.8 3.50 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0908 _refine_ls_wR_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.0908 _reflns_limit_h_max 5 _reflns_limit_h_min -5 _reflns_limit_k_max 24 _reflns_limit_k_min 0 _reflns_limit_l_max 22 _reflns_limit_l_min 0 _reflns_number_gt 2406 _reflns_number_total 3347 _reflns_threshold_expression I>2.0\s(I) _cod_data_source_file cg401662d_si_002.cif _cod_data_source_block global _cod_original_sg_symbol_H-M 'P 1 21/n 1 ' _cod_original_formula_sum 'C18 H17 Cl1 N4 O6 S1' _cod_database_code 4509914 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn Cl1 Cl 0.88065(17) 0.61013(4) 0.48926(4) 0.0199 1.0000 Uani . C2 C 0.6801(6) 0.59781(15) 0.56101(15) 0.0142 1.0000 Uani . C3 C 0.6630(7) 0.53486(15) 0.58455(17) 0.0178 1.0000 Uani . C4 C 0.4927(6) 0.51908(15) 0.63978(16) 0.0161 1.0000 Uani . N5 N 0.4816(6) 0.45748(12) 0.66313(14) 0.0181 1.0000 Uani . C6 C 0.6764(6) 0.40765(15) 0.64293(17) 0.0171 1.0000 Uani . C7 C 0.6381(7) 0.34561(15) 0.68040(17) 0.0176 1.0000 Uani . O8 O 0.4235(5) 0.30657(11) 0.65465(12) 0.0229 1.0000 Uani . C9 C 0.4310(7) 0.25246(16) 0.69646(18) 0.0235 1.0000 Uani . C10 C 0.6379(8) 0.25693(17) 0.74587(18) 0.0261 1.0000 Uani . C11 C 0.7713(8) 0.31701(17) 0.73559(18) 0.0264 1.0000 Uani . H111 H 0.9257 0.3340 0.7628 0.0318 1.0000 Uiso R H101 H 0.6866 0.2258 0.7810 0.0307 1.0000 Uiso R H91 H 0.3071 0.2167 0.6912 0.0284 1.0000 Uiso R H62 H 0.8602 0.4227 0.6535 0.0206 1.0000 Uiso R H61 H 0.6501 0.4002 0.5940 0.0206 1.0000 Uiso R H51 H 0.3411 0.4461 0.6937 0.0221 1.0000 Uiso R C12 C 0.3361(6) 0.57000(15) 0.66888(16) 0.0146 1.0000 Uani . C13 C 0.3665(6) 0.63277(15) 0.64470(16) 0.0154 1.0000 Uani . C14 C 0.5370(6) 0.64861(15) 0.59125(16) 0.0152 1.0000 Uani . S15 S 0.55497(16) 0.73055(4) 0.56453(4) 0.0154 1.0000 Uani . O16 O 0.4213(4) 0.76780(10) 0.61579(11) 0.0189 1.0000 Uani . O17 O 0.8377(4) 0.74549(11) 0.55065(12) 0.0224 1.0000 Uani . N18 N 0.3774(6) 0.73928(14) 0.49117(15) 0.0204 1.0000 Uani . H182 H 0.206(9) 0.731(2) 0.494(2) 0.037(12) 1.0000 Uiso . H181 H 0.446(9) 0.721(2) 0.456(2) 0.037(12) 1.0000 Uiso . H131 H 0.2658 0.6665 0.6656 0.0181 1.0000 Uiso R C19 C 0.1420(6) 0.55658(15) 0.72491(16) 0.0160 1.0000 Uani . O20 O 0.0364(5) 0.60823(11) 0.75261(12) 0.0225 1.0000 Uani . H201 H -0.106(13) 0.598(3) 0.793(3) 0.10(2) 1.0000 Uiso . O21 O 0.0856(4) 0.50071(11) 0.74298(11) 0.0189 1.0000 Uani . H31 H 0.7671 0.5018 0.5635 0.0213 1.0000 Uiso R O22 O 0.0375(5) 0.42924(11) 0.91488(12) 0.0242 1.0000 Uani . C23 C 0.2810(7) 0.43701(16) 0.90021(16) 0.0177 1.0000 Uani . N24 N 0.4491(6) 0.38852(15) 0.88484(16) 0.0226 1.0000 Uani . H241 H 0.388(8) 0.349(2) 0.8916(19) 0.028(10) 1.0000 Uiso . H242 H 0.618(8) 0.3931(18) 0.8845(19) 0.023(10) 1.0000 Uiso . C25 C 0.3991(6) 0.50433(16) 0.89754(16) 0.0171 1.0000 Uani . C26 C 0.5999(6) 0.52082(15) 0.85176(16) 0.0161 1.0000 Uani . N27 N 0.6975(5) 0.58129(13) 0.84632(14) 0.0185 1.0000 Uani . C28 C 0.6019(7) 0.62756(16) 0.88802(17) 0.0209 1.0000 Uani . C29 C 0.4040(7) 0.61520(16) 0.93562(18) 0.0221 1.0000 Uani . C30 C 0.2984(7) 0.55297(16) 0.93980(17) 0.0189 1.0000 Uani . H301 H 0.1579 0.5436 0.9711 0.0231 1.0000 Uiso R H291 H 0.3416 0.6487 0.9650 0.0262 1.0000 Uiso R H281 H 0.6724 0.6704 0.8846 0.0246 1.0000 Uiso R H261 H 0.6716 0.4879 0.8231 0.0193 1.0000 Uiso 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 Cl1 0.0230(4) 0.0182(4) 0.0194(4) 0.0015(3) 0.0092(3) 0.0005(3) C2 0.0145(15) 0.0165(16) 0.0118(15) 0.0011(12) 0.0034(12) 0.0004(13) C3 0.0182(16) 0.0154(16) 0.0202(17) -0.0031(13) 0.0036(13) -0.0010(13) C4 0.0140(15) 0.0156(16) 0.0185(16) -0.0010(13) -0.0022(13) -0.0019(13) N5 0.0202(14) 0.0135(13) 0.0214(15) 0.0013(11) 0.0089(12) -0.0002(11) C6 0.0165(16) 0.0138(16) 0.0214(17) -0.0010(13) 0.0035(13) 0.0027(13) C7 0.0202(17) 0.0125(15) 0.0204(17) -0.0033(13) 0.0059(13) -0.0013(13) O8 0.0253(13) 0.0181(12) 0.0247(13) 0.0040(10) -0.0017(10) -0.0050(10) C9 0.0306(19) 0.0142(16) 0.0262(19) 0.0053(14) 0.0063(15) -0.0053(14) C10 0.035(2) 0.0201(18) 0.0235(18) 0.0055(15) 0.0016(16) 0.0008(15) C11 0.0281(19) 0.0248(19) 0.0255(19) 0.0004(16) -0.0046(16) 0.0001(16) C12 0.0141(15) 0.0146(16) 0.0152(15) 0.0010(13) 0.0004(12) -0.0017(12) C13 0.0130(15) 0.0165(16) 0.0170(16) -0.0039(13) 0.0028(13) 0.0026(13) C14 0.0169(16) 0.0124(15) 0.0162(15) 0.0007(12) 0.0002(13) -0.0007(13) S15 0.0137(4) 0.0126(4) 0.0201(4) 0.0017(3) 0.0030(3) -0.0003(3) O16 0.0194(11) 0.0141(11) 0.0234(12) -0.0009(10) 0.0025(9) 0.0020(10) O17 0.0154(11) 0.0179(12) 0.0339(14) 0.0026(10) 0.0033(10) -0.0019(9) N18 0.0198(15) 0.0226(15) 0.0193(15) 0.0017(13) 0.0065(12) 0.0005(13) C19 0.0137(15) 0.0175(17) 0.0166(16) -0.0012(13) -0.0010(12) 0.0000(13) O20 0.0275(13) 0.0147(11) 0.0271(13) -0.0021(10) 0.0156(10) -0.0001(10) O21 0.0217(11) 0.0157(11) 0.0200(12) 0.0007(10) 0.0058(9) -0.0017(10) O22 0.0167(12) 0.0251(13) 0.0317(14) 0.0022(11) 0.0073(10) -0.0026(10) C23 0.0178(17) 0.0205(17) 0.0150(16) -0.0009(13) 0.0028(13) -0.0022(14) N24 0.0171(16) 0.0168(16) 0.0348(17) 0.0008(13) 0.0089(13) -0.0022(13) C25 0.0152(15) 0.0193(16) 0.0167(16) 0.0004(13) 0.0011(13) 0.0006(13) C26 0.0150(16) 0.0156(16) 0.0176(16) 0.0008(13) -0.0015(13) 0.0006(13) N27 0.0171(14) 0.0183(14) 0.0203(14) 0.0021(12) 0.0034(11) 0.0001(12) C28 0.0229(18) 0.0161(17) 0.0239(18) 0.0013(14) 0.0039(14) 0.0014(14) C29 0.0255(18) 0.0192(17) 0.0221(17) -0.0031(14) 0.0064(14) 0.0025(15) C30 0.0165(16) 0.0242(18) 0.0162(16) 0.0020(14) 0.0033(13) 0.0027(14) loop_ _atom_type_symbol _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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 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 Cl1 C2 C3 116.2(2) yes Cl1 C2 C14 121.8(2) yes C3 C2 C14 122.0(3) yes C2 C3 C4 120.6(3) yes C2 C3 H31 119.7 no C4 C3 H31 119.7 no C3 C4 N5 120.1(3) yes C3 C4 C12 117.8(3) yes N5 C4 C12 122.1(3) yes C4 N5 C6 122.5(3) yes C4 N5 H51 118.7 no C6 N5 H51 118.8 no N5 C6 C7 112.3(3) yes N5 C6 H62 108.6 no C7 C6 H62 108.7 no N5 C6 H61 108.9 no C7 C6 H61 108.9 no H62 C6 H61 109.5 no C6 C7 O8 116.2(3) yes C6 C7 C11 133.9(3) yes O8 C7 C11 109.9(3) yes C7 O8 C9 105.8(3) yes O8 C9 C10 110.5(3) yes O8 C9 H91 124.9 no C10 C9 H91 124.6 no C9 C10 C11 106.7(3) yes C9 C10 H101 126.7 no C11 C10 H101 126.5 no C10 C11 C7 107.1(3) yes C10 C11 H111 126.4 no C7 C11 H111 126.5 no C4 C12 C13 119.3(3) yes C4 C12 C19 120.9(3) yes C13 C12 C19 119.8(3) yes C12 C13 C14 123.0(3) yes C12 C13 H131 118.5 no C14 C13 H131 118.5 no C2 C14 C13 117.2(3) yes C2 C14 S15 124.2(2) yes C13 C14 S15 118.6(2) yes C14 S15 O16 106.46(14) yes C14 S15 O17 108.72(14) yes O16 S15 O17 118.82(14) yes C14 S15 N18 109.04(15) yes O16 S15 N18 107.48(15) yes O17 S15 N18 106.07(15) yes S15 N18 H182 113(3) no S15 N18 H181 116(3) no H182 N18 H181 112(4) no C12 C19 O20 114.6(3) yes C12 C19 O21 122.1(3) yes O20 C19 O21 123.3(3) yes C19 O20 H201 114(3) no O22 C23 N24 123.6(3) yes O22 C23 C25 119.7(3) yes N24 C23 C25 116.7(3) yes C23 N24 H241 117(2) no C23 N24 H242 122(3) no H241 N24 H242 116(4) no C23 C25 C26 121.9(3) yes C23 C25 C30 120.0(3) yes C26 C25 C30 118.1(3) yes C25 C26 N27 122.6(3) yes C25 C26 H261 118.7 no N27 C26 H261 118.6 no C26 N27 C28 118.8(3) yes N27 C28 C29 122.4(3) yes N27 C28 H281 118.9 no C29 C28 H281 118.7 no C28 C29 C30 118.7(3) yes C28 C29 H291 120.7 no C30 C29 H291 120.6 no C25 C30 C29 119.5(3) yes C25 C30 H301 120.3 no C29 C30 H301 120.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C2 1.743(3) yes C2 C3 1.378(4) yes C2 C14 1.398(4) yes C3 C4 1.413(4) yes C3 H31 0.950 no C4 N5 1.348(4) yes C4 C12 1.425(4) yes N5 C6 1.459(4) yes N5 H51 0.950 no C6 C7 1.483(4) yes C6 H62 0.950 no C6 H61 0.950 no C7 O8 1.379(4) yes C7 C11 1.341(5) yes O8 C9 1.372(4) yes C9 C10 1.338(5) yes C9 H91 0.950 no C10 C11 1.414(5) yes C10 H101 0.950 no C11 H111 0.950 no C12 C13 1.385(4) yes C12 C19 1.489(4) yes C13 C14 1.388(4) yes C13 H131 0.950 no C14 S15 1.768(3) yes S15 O16 1.428(2) yes S15 O17 1.437(2) yes S15 N18 1.612(3) yes N18 H182 0.85(4) no N18 H181 0.86(4) no C19 O20 1.306(4) yes C19 O21 1.237(4) yes O20 H201 1.08(6) no O22 C23 1.233(4) yes C23 N24 1.330(4) yes C23 C25 1.502(4) yes N24 H241 0.89(4) no N24 H242 0.82(4) no C25 C26 1.385(4) yes C25 C30 1.393(4) yes C26 N27 1.339(4) yes C26 H261 0.950 no N27 C28 1.342(4) yes C28 C29 1.380(5) yes C28 H281 0.950 no C29 C30 1.384(5) yes C29 H291 0.950 no C30 H301 0.950 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N18 H182 O17 1_455 147(4) 0.85(4) 2.16(4) 2.902(5) yes O20 H201 N27 1_455 177(6) 1.08(6) 1.48(6) 2.555(5) yes N24 H241 O16 3_546 155(3) 0.89(4) 2.23(4) 3.062(5) yes N24 H242 O22 1_655 159(3) 0.82(4) 2.20(4) 2.982(5) yes