#------------------------------------------------------------------------------ #$Date: 2014-09-20 02:24:01 +0300 (Sat, 20 Sep 2014) $ #$Revision: 124026 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/81/7218158.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_7218158 loop_ _publ_author_name 'Srirambhatla, Vijay' 'Kraft, Arno' 'Watt, Stephen' 'Powell, Anthony V.' _publ_section_title ; A robust two-dimensional hydrogen-bonded network for the predictable assembly of ternary co-crystals of furosemide ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C4CE01692K _journal_year 2014 _chemical_formula_moiety 'C12 H11 Cl N2 O5 S, C10 H8 N2, C H4 O ' _chemical_formula_sum 'C23 H23 Cl N4 O6 S' _chemical_formula_weight 518.98 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _cell_angle_alpha 80.525(6) _cell_angle_beta 82.376(6) _cell_angle_gamma 75.758(6) _cell_formula_units_Z 2 _cell_length_a 7.3552(9) _cell_length_b 9.3457(11) _cell_length_c 18.124(2) _cell_measurement_reflns_used 0 _cell_measurement_temperature 293 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 1185.5(2) _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.829 _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 0.031 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 38717 _diffrn_reflns_theta_full 25.084 _diffrn_reflns_theta_max 39.815 _diffrn_reflns_theta_min 1.144 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_T_max 0.9592 _exptl_absorpt_correction_T_min 0.9479 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 540 _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.64 _refine_diff_density_min -0.43 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0771 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 9112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0417 _refine_ls_shift/su_max 0.0013569 _refine_ls_shift/su_mean 0.0000632 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; Method, part 1, 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: 0.351 0.288 0.183 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0601 _refine_ls_wR_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.0447 _reflns_limit_h_max 12 _reflns_limit_h_min -12 _reflns_limit_k_max 15 _reflns_limit_k_min -14 _reflns_limit_l_max 31 _reflns_limit_l_min 0 _reflns_number_gt 9112 _reflns_number_total 12046 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0417 _oxford_refine_ls_scale 0.2955(3) _oxford_reflns_number_all 12030 _oxford_reflns_threshold_expression_ref I>2.0\s(I) _[local]_cod_data_source_file c4ce01692k2.cif _[local]_cod_data_source_block FUS-BP-MeOH(3) _[local]_cod_cif_authors_sg_H-M 'P -1 ' _[local]_cod_chemical_formula_sum_orig 'C23 H23 Cl1 N4 O6 S1' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_atom_sites_solution_primary' value 'Direct' changed to 'direct' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius ; _cod_database_code 7218158 _iucr_refine_instruction_details_constraints ; BLOCK SCALE X'S, U'S RIDE N ( 1,X'S) H ( 7,X'S) H ( 6,X'S) RIDE N ( 2,X'S) H ( 2,X'S) RIDE O ( 1,X'S) H ( 1,X'S) RIDE O ( 6,X'S) H ( 25,X'S) RIDE C ( 3,X'S) H ( 3,X'S) RIDE C ( 5,X'S) H ( 5,X'S) RIDE C ( 8,X'S) H ( 8,X'S) H ( 9,X'S) RIDE C ( 10,X'S) H ( 10,X'S) RIDE C ( 11,X'S) H ( 11,X'S) RIDE C ( 12,X'S) H ( 12,X'S) RIDE C ( 13,X'S) H ( 13,X'S) RIDE C ( 14,X'S) H ( 14,X'S) RIDE C ( 15,X'S) H ( 15,X'S) RIDE C ( 16,X'S) H ( 16,X'S) RIDE C ( 19,X'S) H ( 26,X'S) RIDE C ( 20,X'S) H ( 20,X'S) RIDE C ( 21,X'S) H ( 21,X'S) RIDE C ( 22,X'S) H ( 22,X'S) RIDE C ( 23,X'S) H ( 23,X'S) H ( 18,X'S) H ( 24,X'S) END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn H18 H 1.0574 1.0623 0.5865 0.0464 1.0000 Uiso R H23 H 0.8889 1.0607 0.6477 0.0464 1.0000 Uiso R H24 H 0.8687 1.0400 0.5662 0.0464 1.0000 Uiso R N3 N 0.37117(15) 0.33445(12) 0.51338(5) 0.0207 1.0000 Uani . N4 N -0.09539(12) 0.36748(9) 0.88275(4) 0.0129 1.0000 Uani . H25 H 0.9104 0.8446 0.6365 0.0500 1.0000 Uiso R H1 H 0.2238 0.6139 1.0235 0.0500 1.0000 Uiso R H2 H 0.3708 0.2061 0.9518 0.0500 1.0000 Uiso R H3 H 0.3857 0.6812 0.8558 0.0142 1.0000 Uiso R H5 H 0.5772 0.2144 0.7716 0.0145 1.0000 Uiso R H6 H 0.4725 0.7132 0.5940 0.0500 1.0000 Uiso R H7 H 0.2929 0.7793 0.6315 0.0500 1.0000 Uiso R H8 H 0.4168 0.0521 0.8408 0.0173 1.0000 Uiso R H9 H 0.4054 -0.0180 0.9246 0.0173 1.0000 Uiso R H10 H 0.7597 -0.0695 0.7692 0.0219 1.0000 Uiso R H11 H 1.0863 -0.1822 0.8181 0.0262 1.0000 Uiso R H12 H 1.0485 -0.1578 0.9533 0.0261 1.0000 Uiso R H13 H -0.1006 0.5835 0.8584 0.0171 1.0000 Uiso R H14 H -0.0593 0.1494 0.8859 0.0179 1.0000 Uiso R H15 H 0.0955 0.1297 0.7663 0.0169 1.0000 Uiso R H16 H 0.0555 0.5768 0.7378 0.0165 1.0000 Uiso R H26 H 0.3360 0.1269 0.6757 0.0194 1.0000 Uiso R H20 H 0.0720 0.5594 0.6160 0.0230 1.0000 Uiso R H21 H 0.2312 0.5450 0.4968 0.0283 1.0000 Uiso R H22 H 0.4802 0.1249 0.5536 0.0223 1.0000 Uiso R S1 S 0.51726(3) 0.74463(2) 0.703764(12) 0.0115 1.0000 Uani . N1 N 0.41754(12) 0.75673(10) 0.62903(4) 0.0155 1.0000 Uani . N2 N 0.42473(12) 0.19247(9) 0.91013(4) 0.0128 1.0000 Uani . O1 O 0.28326(11) 0.61391(8) 0.98424(4) 0.0139 1.0000 Uani . O2 O 0.26392(12) 0.37510(9) 1.01080(4) 0.0179 1.0000 Uani . O3 O 0.71559(11) 0.73548(9) 0.68036(4) 0.0168 1.0000 Uani . O4 O 0.41414(12) 0.86446(8) 0.74468(4) 0.0166 1.0000 Uani . O5 O 0.76792(11) -0.05664(8) 0.94184(4) 0.0165 1.0000 Uani . O6 O 1.01535(14) 0.86426(12) 0.62245(8) 0.0351 1.0000 Uani . C1 C 0.49722(12) 0.57838(10) 0.76383(5) 0.0109 1.0000 Uani . C2 C 0.55809(12) 0.43582(10) 0.74126(4) 0.0106 1.0000 Uani . C3 C 0.42167(12) 0.58656(10) 0.83846(5) 0.0111 1.0000 Uani . C4 C 0.39727(12) 0.46046(10) 0.88858(4) 0.0101 1.0000 Uani . C5 C 0.53541(13) 0.30846(10) 0.78907(5) 0.0114 1.0000 Uani . C6 C 0.45123(12) 0.31683(10) 0.86379(4) 0.0104 1.0000 Uani . C7 C 0.30959(13) 0.47803(10) 0.96664(5) 0.0114 1.0000 Uani . C8 C 0.46614(13) 0.04429(10) 0.88765(5) 0.0135 1.0000 Uani . C9 C 0.67241(13) -0.02835(10) 0.87873(5) 0.0132 1.0000 Uani . C10 C 0.79139(15) -0.07639(12) 0.81927(6) 0.0174 1.0000 Uani . C11 C 0.97297(16) -0.13930(12) 0.84641(7) 0.0210 1.0000 Uani . C12 C 0.95105(16) -0.12524(12) 0.92042(7) 0.0208 1.0000 Uani . C13 C -0.06033(14) 0.49061(11) 0.83915(5) 0.0137 1.0000 Uani . C14 C -0.03635(14) 0.23720(11) 0.85508(5) 0.0143 1.0000 Uani . C15 C 0.05684(14) 0.22414(10) 0.78377(5) 0.0133 1.0000 Uani . C16 C 0.03232(14) 0.48761(10) 0.76705(5) 0.0132 1.0000 Uani . C17 C 0.09208(12) 0.35207(10) 0.73763(5) 0.0108 1.0000 Uani . C18 C 0.18760(13) 0.34444(10) 0.66048(5) 0.0120 1.0000 Uani . C19 C 0.31128(14) 0.21458(11) 0.63998(5) 0.0154 1.0000 Uani . C20 C 0.15669(16) 0.46877(12) 0.60493(5) 0.0184 1.0000 Uani . C21 C 0.25218(18) 0.45858(13) 0.53353(6) 0.0226 1.0000 Uani . C22 C 0.39716(15) 0.21500(12) 0.56668(5) 0.0178 1.0000 Uani . C23 C 0.9526(2) 1.01943(18) 0.60422(11) 0.0386 1.0000 Uani . Cl1 Cl 0.66707(3) 0.41261(3) 0.651583(11) 0.0140 1.0000 Uani . 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 N3 0.0239(4) 0.0253(4) 0.0115(3) -0.0039(3) 0.0039(3) -0.0052(3) N4 0.0145(3) 0.0135(3) 0.0104(3) -0.0025(2) 0.0014(2) -0.0034(3) S1 0.01306(9) 0.01097(9) 0.00960(8) -0.00052(6) 0.00097(6) -0.00286(7) N1 0.0150(3) 0.0200(4) 0.0092(3) -0.0010(2) -0.0011(2) -0.0003(3) N2 0.0161(3) 0.0099(3) 0.0107(3) -0.0010(2) 0.0025(2) -0.0019(2) O1 0.0193(3) 0.0116(3) 0.0094(2) -0.00289(19) 0.0032(2) -0.0027(2) O2 0.0264(4) 0.0143(3) 0.0116(3) -0.0019(2) 0.0065(2) -0.0066(3) O3 0.0140(3) 0.0188(3) 0.0172(3) 0.0001(2) 0.0014(2) -0.0064(2) O4 0.0231(3) 0.0111(3) 0.0138(3) -0.0024(2) 0.0022(2) -0.0022(2) O5 0.0172(3) 0.0145(3) 0.0154(3) 0.0020(2) -0.0017(2) -0.0018(2) O6 0.0146(4) 0.0245(4) 0.0623(7) 0.0021(4) 0.0024(4) -0.0057(3) C1 0.0119(3) 0.0118(3) 0.0084(3) -0.0009(2) 0.0006(2) -0.0027(3) C2 0.0115(3) 0.0122(3) 0.0076(3) -0.0018(2) 0.0004(2) -0.0023(3) C3 0.0121(3) 0.0117(3) 0.0089(3) -0.0015(2) 0.0007(2) -0.0026(3) C4 0.0109(3) 0.0107(3) 0.0080(3) -0.0013(2) 0.0005(2) -0.0016(2) C5 0.0127(3) 0.0114(3) 0.0091(3) -0.0019(2) 0.0006(2) -0.0015(3) C6 0.0110(3) 0.0113(3) 0.0084(3) -0.0009(2) -0.0001(2) -0.0023(3) C7 0.0124(3) 0.0124(3) 0.0087(3) -0.0019(2) 0.0004(2) -0.0018(3) C8 0.0138(3) 0.0108(3) 0.0155(3) -0.0029(3) 0.0010(3) -0.0023(3) C9 0.0141(3) 0.0104(3) 0.0141(3) -0.0013(2) 0.0010(3) -0.0025(3) C10 0.0182(4) 0.0153(4) 0.0184(4) -0.0058(3) 0.0029(3) -0.0030(3) C11 0.0164(4) 0.0128(4) 0.0310(5) -0.0041(3) 0.0047(4) -0.0012(3) C12 0.0159(4) 0.0153(4) 0.0280(5) 0.0028(3) -0.0026(3) -0.0010(3) C13 0.0162(4) 0.0129(3) 0.0109(3) -0.0025(2) 0.0015(3) -0.0023(3) C14 0.0194(4) 0.0125(3) 0.0104(3) -0.0014(2) 0.0031(3) -0.0054(3) C15 0.0174(4) 0.0120(3) 0.0102(3) -0.0019(2) 0.0022(3) -0.0043(3) C16 0.0156(4) 0.0124(3) 0.0105(3) -0.0011(2) 0.0016(3) -0.0029(3) C17 0.0110(3) 0.0126(3) 0.0082(3) -0.0012(2) 0.0004(2) -0.0024(3) C18 0.0129(3) 0.0139(3) 0.0090(3) -0.0019(2) 0.0007(2) -0.0033(3) C19 0.0167(4) 0.0156(4) 0.0124(3) -0.0031(3) 0.0020(3) -0.0020(3) C20 0.0228(4) 0.0178(4) 0.0104(3) 0.0003(3) 0.0027(3) -0.0006(3) C21 0.0299(5) 0.0223(5) 0.0109(3) 0.0011(3) 0.0035(3) -0.0022(4) C22 0.0186(4) 0.0209(4) 0.0130(3) -0.0057(3) 0.0033(3) -0.0033(3) C23 0.0362(7) 0.0261(6) 0.0531(9) 0.0027(6) -0.0042(7) -0.0120(6) Cl1 0.01710(9) 0.01525(9) 0.00842(7) -0.00256(6) 0.00278(6) -0.00283(7) 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 C21 N3 C22 116.36(9) yes C13 N4 C14 117.93(8) yes N1 S1 O3 106.51(5) yes N1 S1 O4 108.07(5) yes O3 S1 O4 118.57(5) yes N1 S1 C1 110.23(5) yes O3 S1 C1 107.84(5) yes O4 S1 C1 105.53(4) yes H7 N1 H6 116.0 no H7 N1 S1 119.0 no H6 N1 S1 120.8 no H2 N2 C6 115.6 no H2 N2 C8 119.5 no C6 N2 C8 124.46(8) yes H1 O1 C7 106.1 no C9 O5 C12 106.48(8) yes H25 O6 C23 97.8 no S1 C1 C2 123.48(6) yes S1 C1 C3 119.14(7) yes C2 C1 C3 117.35(8) yes C1 C2 C5 121.96(8) yes C1 C2 Cl1 120.96(6) yes C5 C2 Cl1 117.08(7) yes H3 C3 C1 118.9 no H3 C3 C4 118.8 no C1 C3 C4 122.32(8) yes C3 C4 C6 119.70(7) yes C3 C4 C7 119.45(8) yes C6 C4 C7 120.82(7) yes H5 C5 C2 119.5 no H5 C5 C6 119.7 no C2 C5 C6 120.84(8) yes C4 C6 C5 117.69(8) yes C4 C6 N2 121.41(7) yes C5 C6 N2 120.89(8) yes C4 C7 O1 114.44(7) yes C4 C7 O2 122.87(8) yes O1 C7 O2 122.69(8) yes N2 C8 H8 108.4 no N2 C8 H9 108.7 no H8 C8 H9 109.1 no N2 C8 C9 114.14(8) yes H8 C8 C9 108.2 no H9 C8 C9 108.3 no C8 C9 O5 117.03(8) yes C8 C9 C10 132.98(9) yes O5 C9 C10 109.99(9) yes H10 C10 C9 126.3 no H10 C10 C11 126.9 no C9 C10 C11 106.76(10) yes C10 C11 H11 127.0 no C10 C11 C12 106.17(9) yes H11 C11 C12 126.8 no H12 C12 O5 124.4 no H12 C12 C11 125.0 no O5 C12 C11 110.59(10) yes H13 C13 N4 118.7 no H13 C13 C16 118.8 no N4 C13 C16 122.55(9) yes H14 C14 N4 118.4 no H14 C14 C15 118.3 no N4 C14 C15 123.30(8) yes H15 C15 C14 120.5 no H15 C15 C17 120.3 no C14 C15 C17 119.17(8) yes H16 C16 C13 120.3 no H16 C16 C17 120.0 no C13 C16 C17 119.67(8) yes C16 C17 C15 117.38(8) yes C16 C17 C18 121.40(8) yes C15 C17 C18 121.22(8) yes C17 C18 C19 122.02(8) yes C17 C18 C20 120.76(8) yes C19 C18 C20 117.22(8) yes H26 C19 C18 120.3 no H26 C19 C22 120.5 no C18 C19 C22 119.18(9) yes H20 C20 C18 120.3 no H20 C20 C21 120.5 no C18 C20 C21 119.19(10) yes H21 C21 C20 118.0 no H21 C21 N3 118.1 no C20 C21 N3 123.98(10) yes H22 C22 C19 118.0 no H22 C22 N3 118.0 no C19 C22 N3 124.06(10) yes O6 C23 H23 109.4 no O6 C23 H18 109.6 no H23 C23 H18 109.5 no O6 C23 H24 109.4 no H23 C23 H24 109.5 no H18 C23 H24 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag H18 C23 0.950 no H23 C23 0.950 no H24 C23 0.950 no N3 C21 1.3417(15) yes N3 C22 1.3435(15) yes N4 C13 1.3445(12) yes N4 C14 1.3438(12) yes H25 O6 0.834 no H1 O1 0.784 no H2 N2 0.820 no H3 C3 0.952 no H5 C5 0.949 no H6 N1 0.817 no H7 N1 0.885 no H8 C8 0.952 no H9 C8 0.952 no H10 C10 0.954 no H11 C11 0.953 no H12 C12 0.953 no H13 C13 0.953 no H14 C14 0.952 no H15 C15 0.951 no H16 C16 0.952 no H26 C19 0.952 no H20 C20 0.953 no H21 C21 0.953 no H22 C22 0.955 no S1 N1 1.5993(9) yes S1 O3 1.4497(8) yes S1 O4 1.4442(8) yes S1 C1 1.7703(9) yes N2 C6 1.3568(12) yes N2 C8 1.4566(12) yes O1 C7 1.3221(11) yes O2 C7 1.2301(11) yes O5 C9 1.3763(12) yes O5 C12 1.3764(14) yes O6 C23 1.4067(19) yes C1 C2 1.4072(12) yes C1 C3 1.3993(12) yes C2 C5 1.3839(12) yes C2 Cl1 1.7366(8) yes C3 C4 1.3980(12) yes C4 C6 1.4318(12) yes C4 C7 1.4922(11) yes C5 C6 1.4184(12) yes C8 C9 1.5010(13) yes C9 C10 1.3581(13) yes C10 C11 1.4367(17) yes C11 C12 1.3537(18) yes C13 C16 1.3925(13) yes C14 C15 1.3895(12) yes C15 C17 1.4006(13) yes C16 C17 1.4030(13) yes C17 C18 1.4837(12) yes C18 C19 1.3979(14) yes C18 C20 1.4003(13) yes C19 C22 1.3930(13) yes C20 C21 1.3940(14) yes 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 O6 H25 O3 . 161.44 0.834 1.969 2.7725(14) yes O1 H1 N4 2_567 173.25 0.784 1.844 2.6242(14) yes N2 H2 O2 . 138.55 0.820 1.994 2.6647(14) yes N2 H2 O5 2_657 136.27 0.820 2.449 3.0939(14) yes N1 H6 N3 2_666 162.45 0.817 2.179 2.9684(14) yes N1 H7 O6 1_455 169.06 0.885 2.018 2.8924(14) yes C12 H12 O1 1_645 136.12 0.953 2.428 3.1846(14) yes C13 H13 O2 2_567 126.40 0.953 2.556 3.2142(14) yes C14 H14 O5 1_455 158.27 0.952 2.563 3.4654(14) yes C14 H14 C12 1_455 156.59 0.952 2.524 3.4189(14) yes C19 H26 O4 1_545 167.11 0.952 2.529 3.4639(14) yes