#------------------------------------------------------------------------------ #$Date: 2016-03-24 03:30:43 +0200 (Thu, 24 Mar 2016) $ #$Revision: 179634 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/98/4509861.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_4509861 loop_ _publ_author_name 'Minkov, Vasily S.' 'Beloborodova, Alina A.' 'Drebushchak, Valeri A.' 'Boldyreva, Elena V.' _publ_section_title ; Furosemide Solvates: Can They Serve As Precursors to Different Polymorphs of Furosemide? ; _journal_issue 2 _journal_name_full 'Crystal Growth & Design' _journal_page_first 513 _journal_paper_doi 10.1021/cg401257w _journal_volume 14 _journal_year 2014 _chemical_formula_moiety 'C12 H11 Cl1 N2 O5 S1, C4 H8 O1' _chemical_formula_sum 'C16 H19 Cl N2 O6 S' _chemical_formula_weight 402.85 _chemical_name_common 'furosemide tetrahydrofuran solvate' _chemical_name_systematic ; ? ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.024(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.9529(5) _cell_length_b 8.3816(3) _cell_length_c 20.0071(9) _cell_measurement_reflns_used 20056 _cell_measurement_temperature 150 _cell_measurement_theta_max 29.60 _cell_measurement_theta_min 2.04 _cell_volume 1829.65(13) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150 _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 20116 _diffrn_reflns_theta_full 29.15 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 2.04 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'X-SHAPE; Stoe & Cie, 2003' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.293 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 4916 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0349 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.0703P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0825 _refine_ls_wR_factor_ref 0.0865 _reflns_number_gt 3849 _reflns_number_total 4916 _reflns_threshold_expression >2sigma(I) _cod_data_source_file cg401257w_si_002.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 4509861 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' '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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.43293(3) 0.45423(4) 0.388037(16) 0.02092(8) Uani 1 1 d . . . Cl1 Cl 0.45364(4) 0.83016(5) 0.434203(17) 0.03290(10) Uani 1 1 d . . . O5 O 0.55413(10) 0.46965(13) 0.42169(5) 0.0269(2) Uani 1 1 d . . . O2 O 0.36095(10) 0.74838(12) 0.09622(5) 0.0248(2) Uani 1 1 d . . . O1 O 0.35296(12) 0.49890(13) 0.13337(5) 0.0338(3) Uani 1 1 d . . . H1 H 0.3448(18) 0.479(2) 0.0892(11) 0.041 Uiso 1 1 d . . . O4 O 0.40360(10) 0.31206(12) 0.34977(5) 0.0264(2) Uani 1 1 d . . . N2 N 0.33432(13) 0.47479(16) 0.44262(6) 0.0250(3) Uani 1 1 d . . . H4 H 0.3686(18) 0.500(2) 0.4818(10) 0.030 Uiso 1 1 d . . . H3 H 0.2828(18) 0.401(2) 0.4376(9) 0.030 Uiso 1 1 d . . . C4 C 0.42748(13) 0.77718(17) 0.35013(7) 0.0224(3) Uani 1 1 d . . . C1 C 0.38425(13) 0.70033(16) 0.21464(7) 0.0202(3) Uani 1 1 d . . . C7 C 0.36448(13) 0.65336(16) 0.14319(7) 0.0219(3) Uani 1 1 d . . . C5 C 0.41237(13) 0.61612(16) 0.33151(6) 0.0208(3) Uani 1 1 d . . . C3 C 0.42172(13) 0.89810(17) 0.30340(7) 0.0228(3) Uani 1 1 d . . . H5 H 0.4338(16) 1.001(2) 0.3187(9) 0.027 Uiso 1 1 d . . . N1 N 0.39468(12) 0.98044(14) 0.18737(6) 0.0240(2) Uani 1 1 d . . . H2 H 0.3895(17) 0.945(2) 0.1467(10) 0.029 Uiso 1 1 d . . . C6 C 0.39040(13) 0.58173(16) 0.26358(6) 0.0200(3) Uani 1 1 d . . . H6 H 0.3818(15) 0.471(2) 0.2495(8) 0.024 Uiso 1 1 d . . . O3 O 0.62134(12) 1.12536(15) 0.15368(6) 0.0394(3) Uani 1 1 d . . . C12 C 0.55912(14) 1.18090(16) 0.20544(7) 0.0256(3) Uani 1 1 d . . . C2 C 0.40078(12) 0.86350(15) 0.23399(6) 0.0202(3) Uani 1 1 d . . . C8 C 0.42453(14) 1.14792(16) 0.19988(8) 0.0251(3) Uani 1 1 d . . . H7 H 0.3909(17) 1.187(2) 0.2405(9) 0.030 Uiso 1 1 d . . . H8 H 0.3834(17) 1.209(2) 0.1626(9) 0.030 Uiso 1 1 d . . . C9 C 0.63629(16) 1.2574(2) 0.25012(8) 0.0345(4) Uani 1 1 d . . . H9 H 0.6149(19) 1.306(2) 0.2890(10) 0.041 Uiso 1 1 d . . . C10 C 0.75507(17) 1.2496(2) 0.22587(10) 0.0411(4) Uani 1 1 d . . . H10 H 0.828(2) 1.292(3) 0.2460(11) 0.049 Uiso 1 1 d . . . C11 C 0.74173(17) 1.1693(2) 0.16855(10) 0.0427(4) Uani 1 1 d . . . H11 H 0.793(2) 1.140(3) 0.1364(11) 0.051 Uiso 1 1 d . . . O6 O 0.35514(15) 0.42962(16) 0.00908(6) 0.0493(4) Uani 1 1 d D A . C13 C 0.37455(19) 0.2708(2) -0.01434(9) 0.0412(4) Uani 1 1 d D A . H13A H 0.3338 0.1921 0.0131 0.049 Uiso 1 1 calc R . . H13B H 0.4632 0.2461 -0.0118 0.049 Uiso 1 1 calc R . . C16 C 0.2969(3) 0.5246(3) -0.04381(10) 0.0585(6) Uani 1 1 d D . . H16A H 0.3585 0.5852 -0.0669 0.070 Uiso 0.709(7) 1 calc PR A 1 H16B H 0.2389 0.6010 -0.0260 0.070 Uiso 0.709(7) 1 calc PR A 1 H16C H 0.3363 0.6307 -0.0456 0.070 Uiso 0.291(7) 1 d PR A 2 H16D H 0.2087 0.5391 -0.0381 0.070 Uiso 0.291(7) 1 d PR A 2 C14 C 0.3196(2) 0.2662(3) -0.08646(10) 0.0493(5) Uani 1 1 d D . . H14A H 0.2755 0.1646 -0.0964 0.059 Uiso 0.709(7) 1 calc PR A 1 H14B H 0.3837 0.2791 -0.1180 0.059 Uiso 0.709(7) 1 calc PR A 1 H14C H 0.3717 0.2035 -0.1148 0.059 Uiso 0.291(7) 1 d PR A 2 H14D H 0.2364 0.2189 -0.0896 0.059 Uiso 0.291(7) 1 d PR A 2 C15A C 0.2301(3) 0.4089(3) -0.09109(13) 0.0438(9) Uani 0.709(7) 1 d PD A 1 H15A H 0.2186 0.4521 -0.1373 0.053 Uiso 0.709(7) 1 calc PR A 1 H15B H 0.1494 0.3795 -0.0760 0.053 Uiso 0.709(7) 1 calc PR A 1 C15B C 0.3152(9) 0.4301(8) -0.1065(3) 0.048(2) Uani 0.291(7) 1 d PD A 2 H15C H 0.2465 0.4486 -0.1412 0.058 Uiso 0.291(7) 1 calc PR A 2 H15D H 0.3926 0.4615 -0.1250 0.058 Uiso 0.291(7) 1 calc PR A 2 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 S1 0.02424(18) 0.02224(16) 0.01619(14) 0.00036(11) 0.00123(12) 0.00046(13) Cl1 0.0494(3) 0.02973(18) 0.01928(16) -0.00574(13) 0.00125(15) -0.00598(16) O5 0.0237(5) 0.0359(6) 0.0209(5) 0.0030(4) 0.0007(4) 0.0011(4) O2 0.0305(6) 0.0240(5) 0.0199(4) 0.0028(4) 0.0015(4) 0.0033(4) O1 0.0607(8) 0.0219(5) 0.0178(5) -0.0015(4) -0.0020(5) -0.0036(5) O4 0.0388(6) 0.0205(5) 0.0199(5) -0.0006(4) 0.0025(4) 0.0013(4) N2 0.0276(7) 0.0297(6) 0.0178(5) -0.0025(5) 0.0020(5) -0.0069(5) C4 0.0244(7) 0.0237(6) 0.0190(6) -0.0027(5) 0.0009(5) -0.0002(5) C1 0.0192(7) 0.0215(6) 0.0199(6) 0.0002(5) 0.0007(5) 0.0013(5) C7 0.0226(7) 0.0220(6) 0.0207(6) 0.0002(5) 0.0001(5) 0.0016(5) C5 0.0226(7) 0.0220(6) 0.0177(6) -0.0008(5) 0.0012(5) -0.0006(5) C3 0.0252(7) 0.0195(6) 0.0239(6) -0.0033(5) 0.0024(5) -0.0001(5) N1 0.0323(7) 0.0179(5) 0.0212(5) 0.0004(4) 0.0001(5) 0.0001(5) C6 0.0211(7) 0.0197(6) 0.0190(6) -0.0004(5) 0.0003(5) 0.0004(5) O3 0.0394(7) 0.0396(7) 0.0417(6) -0.0107(5) 0.0169(6) -0.0023(5) C12 0.0300(8) 0.0201(6) 0.0274(7) 0.0026(5) 0.0075(6) 0.0022(5) C2 0.0178(7) 0.0208(6) 0.0219(6) -0.0003(5) 0.0011(5) 0.0011(5) C8 0.0280(8) 0.0184(6) 0.0286(7) 0.0010(5) 0.0003(6) 0.0014(5) C9 0.0305(9) 0.0433(9) 0.0298(8) -0.0003(7) 0.0032(7) -0.0010(7) C10 0.0268(9) 0.0532(11) 0.0434(10) 0.0062(8) 0.0038(8) -0.0024(8) C11 0.0333(10) 0.0459(10) 0.0519(11) 0.0021(8) 0.0195(8) 0.0017(8) O6 0.0833(11) 0.0390(7) 0.0242(6) -0.0061(5) -0.0029(6) 0.0080(7) C13 0.0463(11) 0.0383(9) 0.0398(9) -0.0095(7) 0.0085(8) 0.0008(8) C16 0.0981(19) 0.0399(10) 0.0330(9) 0.0010(8) -0.0196(11) -0.0026(11) C14 0.0421(11) 0.0611(12) 0.0448(10) -0.0242(9) 0.0032(9) -0.0058(9) C15A 0.053(2) 0.0432(15) 0.0338(13) -0.0073(10) -0.0014(13) -0.0074(12) C15B 0.065(6) 0.050(4) 0.029(3) -0.008(3) 0.001(3) 0.000(3) 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' S S 0.1246 0.1234 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O4 S1 O5 118.50(7) O4 S1 N2 108.54(7) O5 S1 N2 108.58(7) O4 S1 C5 106.59(6) O5 S1 C5 106.89(6) N2 S1 C5 107.22(7) C7 O1 H1 109.5(13) S1 N2 H4 112.1(12) S1 N2 H3 108.8(12) H4 N2 H3 121.6(17) C3 C4 C5 121.97(12) C3 C4 Cl1 117.57(11) C5 C4 Cl1 120.46(10) C6 C1 C2 119.70(12) C6 C1 C7 118.89(12) C2 C1 C7 121.38(12) O2 C7 O1 121.85(13) O2 C7 C1 123.90(12) O1 C7 C1 114.23(12) C6 C5 C4 117.68(12) C6 C5 S1 117.89(10) C4 C5 S1 124.19(10) C4 C3 C2 120.57(13) C4 C3 H5 117.9(11) C2 C3 H5 121.5(11) C2 N1 C8 125.68(12) C2 N1 H2 113.5(12) C8 N1 H2 119.1(12) C5 C6 C1 122.22(12) C5 C6 H6 119.0(10) C1 C6 H6 118.7(10) C12 O3 C11 106.03(14) C9 C12 O3 109.91(14) C9 C12 C8 134.37(14) O3 C12 C8 115.70(13) N1 C2 C3 121.47(12) N1 C2 C1 120.67(12) C3 C2 C1 117.85(12) N1 C8 C12 113.32(12) N1 C8 H7 111.6(11) C12 C8 H7 108.5(11) N1 C8 H8 106.7(11) C12 C8 H8 110.2(11) H7 C8 H8 106.2(15) C12 C9 C10 106.96(15) C12 C9 H9 125.4(13) C10 C9 H9 127.6(13) C11 C10 C9 106.38(17) C11 C10 H10 126.3(13) C9 C10 H10 127.3(13) C10 C11 O3 110.71(15) C10 C11 H11 135.4(14) O3 C11 H11 113.9(14) C16 O6 C13 110.17(14) O6 C13 C14 106.10(16) O6 C13 H13A 110.5 C14 C13 H13A 110.5 O6 C13 H13B 110.5 C14 C13 H13B 110.5 H13A C13 H13B 108.7 O6 C16 C15A 105.55(18) O6 C16 C15B 103.8(3) C15A C16 C15B 39.7(3) O6 C16 H16A 110.6 C15A C16 H16A 110.6 C15B C16 H16A 74.7 O6 C16 H16B 110.6 C15A C16 H16B 110.6 C15B C16 H16B 140.7 H16A C16 H16B 108.8 O6 C16 H16C 111.1 C15A C16 H16C 138.4 C15B C16 H16C 110.5 H16A C16 H16C 37.4 H16B C16 H16C 74.2 O6 C16 H16D 111.1 C15A C16 H16D 74.0 C15B C16 H16D 111.2 H16A C16 H16D 134.6 H16B C16 H16D 38.4 H16C C16 H16D 109.1 C15B C14 C13 104.1(3) C15B C14 C15A 40.0(4) C13 C14 C15A 103.58(16) C15B C14 H14A 140.0 C13 C14 H14A 111.0 C15A C14 H14A 111.0 C15B C14 H14B 74.0 C13 C14 H14B 111.0 C15A C14 H14B 111.0 H14A C14 H14B 109.0 C15B C14 H14C 110.8 C13 C14 H14C 110.9 C15A C14 H14C 140.5 H14A C14 H14C 74.0 H14B C14 H14C 38.4 C15B C14 H14D 111.0 C13 C14 H14D 111.0 C15A C14 H14D 74.4 H14A C14 H14D 38.2 H14B C14 H14D 134.6 H14C C14 H14D 109.0 C16 C15A C14 101.0(2) C16 C15A H16D 37.8 C14 C15A H16D 129.5 C16 C15A H15A 111.6 C14 C15A H15A 111.6 H16D C15A H15A 111.4 C16 C15A H15B 111.6 C14 C15A H15B 111.6 H16D C15A H15B 77.0 H15A C15A H15B 109.4 C14 C15B C16 105.9(4) C14 C15B H15C 110.6 C16 C15B H15C 110.6 C14 C15B H15D 110.6 C16 C15B H15D 110.6 H15C C15B H15D 108.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O4 1.4373(10) S1 O5 1.4407(11) S1 N2 1.6110(12) S1 C5 1.7681(14) Cl1 C4 1.7390(14) O2 C7 1.2297(16) O1 C7 1.3138(17) O1 H1 0.90(2) N2 H4 0.87(2) N2 H3 0.84(2) C4 C3 1.377(2) C4 C5 1.4063(19) C1 C6 1.3928(18) C1 C2 1.4286(18) C1 C7 1.4803(18) C5 C6 1.3896(18) C3 C2 1.4174(19) C3 H5 0.923(19) N1 C2 1.3506(17) N1 C8 1.4580(18) N1 H2 0.863(19) C6 H6 0.974(17) O3 C12 1.3701(17) O3 C11 1.376(2) C12 C9 1.339(2) C12 C8 1.494(2) C8 H7 0.976(18) C8 H8 0.980(19) C9 C10 1.429(2) C9 H9 0.92(2) C10 C11 1.327(3) C10 H10 0.93(2) C11 H11 0.92(2) O6 C16 1.429(2) O6 C13 1.433(2) C13 C14 1.515(3) C13 H13A 0.9900 C13 H13B 0.9900 C16 C15A 1.500(3) C16 C15B 1.512(6) C16 H16A 0.9900 C16 H16B 0.9900 C16 H16C 0.9900 C16 H16D 0.9900 C14 C15B 1.431(7) C14 C15A 1.544(4) C14 H14A 0.9900 C14 H14B 0.9900 C14 H14C 0.9900 C14 H14D 0.9900 C15A H16D 1.5528 C15A H15A 0.9900 C15A H15B 0.9900 C15B H15C 0.9900 C15B H15D 0.9900 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H2 O2 0.863(19) 1.945(19) 2.6697(16) 140.7(16) . O1 H1 O6 0.90(2) 1.67(2) 2.5557(15) 170(2) . N2 H4 Cl1 0.87(2) 3.097(18) 3.2629(14) 93.3(13) . N2 H3 O2 0.84(2) 2.09(2) 2.9135(17) 165.8(18) 2_545 N2 H4 O5 0.87(2) 2.05(2) 2.9153(17) 172.7(18) 3_666 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 C6 C1 C7 O2 -177.99(14) C2 C1 C7 O2 0.1(2) C6 C1 C7 O1 0.80(19) C2 C1 C7 O1 178.86(13) C3 C4 C5 C6 -0.4(2) Cl1 C4 C5 C6 179.31(11) C3 C4 C5 S1 173.78(11) Cl1 C4 C5 S1 -6.55(18) O4 S1 C5 C6 -8.38(13) O5 S1 C5 C6 119.26(12) N2 S1 C5 C6 -124.47(12) O4 S1 C5 C4 177.48(12) O5 S1 C5 C4 -54.88(13) N2 S1 C5 C4 61.40(14) C5 C4 C3 C2 -0.4(2) Cl1 C4 C3 C2 179.94(11) C4 C5 C6 C1 0.6(2) S1 C5 C6 C1 -173.94(11) C2 C1 C6 C5 0.0(2) C7 C1 C6 C5 178.04(13) C11 O3 C12 C9 0.66(18) C11 O3 C12 C8 179.50(13) C8 N1 C2 C3 9.0(2) C8 N1 C2 C1 -172.04(13) C4 C3 C2 N1 179.92(14) C4 C3 C2 C1 0.9(2) C6 C1 C2 N1 -179.72(13) C7 C1 C2 N1 2.2(2) C6 C1 C2 C3 -0.69(19) C7 C1 C2 C3 -178.73(13) C2 N1 C8 C12 79.43(18) C9 C12 C8 N1 -129.54(18) O3 C12 C8 N1 51.98(17) O3 C12 C9 C10 -0.39(19) C8 C12 C9 C10 -178.93(16) C12 C9 C10 C11 0.0(2) C9 C10 C11 O3 0.5(2) C12 O3 C11 C10 -0.7(2) C16 O6 C13 C14 -2.3(2) C13 O6 C16 C15A 24.8(3) C13 O6 C16 C15B -16.3(4) O6 C13 C14 C15B 21.1(4) O6 C13 C14 C15A -20.2(2) O6 C16 C15A C14 -35.8(3) C15B C16 C15A C14 57.3(4) C15B C14 C15A C16 -62.1(4) C13 C14 C15A C16 33.7(2) C13 C14 C15B C16 -31.0(6) C15A C14 C15B C16 63.5(4) O6 C16 C15B C14 29.8(6) C15A C16 C15B C14 -67.9(5)