#------------------------------------------------------------------------------ #$Date: 2019-06-13 06:02:00 +0300 (Thu, 13 Jun 2019) $ #$Revision: 215911 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156913.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_7156913 loop_ _publ_author_name 'Schulze, Daniel' 'Traber, Juliane' 'Ritter, Marcel' 'G\"orls, Helmar' 'Pohnert, Georg' 'Westerhausen, Matthias' _publ_section_title ; Total Syntheses of the Bilirubin Oxidation End Product Z-BOX C and its Isomeric Form Z-BOX D ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB01117J _journal_year 2019 _chemical_formula_moiety 'C15 H15 N O6 S' _chemical_formula_sum 'C15 H15 N O6 S' _chemical_formula_weight 337.34 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _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 _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2019-05-13 deposited with the CCDC. 2019-06-07 downloaded from the CCDC. ; _cell_angle_alpha 68.144(3) _cell_angle_beta 73.035(3) _cell_angle_gamma 76.069(3) _cell_formula_units_Z 2 _cell_length_a 7.7698(4) _cell_length_b 9.8328(6) _cell_length_c 11.4487(7) _cell_measurement_reflns_used 6957 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.97 _cell_volume 767.82(8) _computing_cell_refinement DENZO _computing_data_collection COLLECT _computing_data_reduction DENZO _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 133(2) _diffrn_measured_fraction_theta_full 0.964 _diffrn_measured_fraction_theta_max 0.964 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _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 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6957 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 1.97 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6763 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker-AXS, 2002' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.108 _exptl_crystal_size_mid 0.102 _exptl_crystal_size_min 0.088 _refine_diff_density_max 0.325 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 268 _refine_ls_number_reflns 3396 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.109 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0407 _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^)+(0.0215P)^2^+0.6131P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0919 _refine_ls_wR_factor_ref 0.0985 _reflns_number_gt 3006 _reflns_number_total 3396 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c9ob01117j2.cif _cod_data_source_block FO6807 _cod_database_code 7156913 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag S1 S 0.71091(6) 0.65080(5) 0.24756(4) 0.02263(13) Uani 1 1 d O1 O 0.59972(17) 0.93656(14) 0.37221(12) 0.0257(3) Uani 1 1 d O2 O 0.52734(17) 0.77053(14) 0.22878(11) 0.0229(3) Uani 1 1 d O3 O -0.1801(2) 0.7963(2) 0.78926(15) 0.0471(4) Uani 1 1 d O4 O 0.05081(17) 0.92658(15) 0.71683(12) 0.0261(3) Uani 1 1 d O5 O 0.70435(18) 0.59063(15) 0.38281(12) 0.0278(3) Uani 1 1 d O6 O 0.85748(18) 0.72543(16) 0.16054(14) 0.0327(3) Uani 1 1 d N1 N 0.3099(2) 0.89683(17) 0.49881(15) 0.0214(3) Uani 1 1 d H1N1 H 0.304(3) 0.938(3) 0.552(2) 0.037(6) Uiso 1 1 d C1 C 0.4583(2) 0.88553(19) 0.40098(16) 0.0202(4) Uani 1 1 d C2 C 0.4115(2) 0.79735(19) 0.33747(17) 0.0210(4) Uani 1 1 d C3 C 0.2476(2) 0.75741(19) 0.39595(17) 0.0218(4) Uani 1 1 d C4 C 0.1795(2) 0.81741(19) 0.50469(17) 0.0215(4) Uani 1 1 d C5 C 0.0232(3) 0.7919(2) 0.59303(18) 0.0246(4) Uani 1 1 d H5 H -0.047(3) 0.733(2) 0.584(2) 0.032(6) Uiso 1 1 d C6 C -0.0464(3) 0.8367(2) 0.70851(18) 0.0273(4) Uani 1 1 d C7 C -0.0112(3) 0.9683(2) 0.83298(19) 0.0288(4) Uani 1 1 d H7C H -0.142(3) 1.016(2) 0.842(2) 0.030(6) Uiso 1 1 d H7B H -0.004(3) 0.881(2) 0.909(2) 0.028(5) Uiso 1 1 d H7A H 0.072(3) 1.035(3) 0.825(2) 0.046(7) Uiso 1 1 d C8 C 0.1468(3) 0.6671(2) 0.3666(2) 0.0278(4) Uani 1 1 d H8C H 0.205(3) 0.653(3) 0.284(2) 0.037(6) Uiso 1 1 d H8B H 0.022(3) 0.714(3) 0.362(2) 0.040(6) Uiso 1 1 d H8A H 0.138(3) 0.572(3) 0.435(2) 0.043(7) Uiso 1 1 d C9 C 0.6776(2) 0.51883(19) 0.19110(17) 0.0210(4) Uani 1 1 d C10 C 0.5656(2) 0.4138(2) 0.27249(17) 0.0233(4) Uani 1 1 d H10 H 0.511(3) 0.413(2) 0.357(2) 0.030(6) Uiso 1 1 d C11 C 0.5405(3) 0.3103(2) 0.22621(18) 0.0239(4) Uani 1 1 d H11 H 0.467(3) 0.237(2) 0.282(2) 0.027(5) Uiso 1 1 d C12 C 0.6271(2) 0.3087(2) 0.10076(18) 0.0238(4) Uani 1 1 d C13 C 0.7371(3) 0.4160(2) 0.02200(18) 0.0263(4) Uani 1 1 d H13 H 0.798(3) 0.419(3) -0.068(2) 0.039(6) Uiso 1 1 d C14 C 0.7624(2) 0.5226(2) 0.06559(18) 0.0245(4) Uani 1 1 d H14 H 0.838(3) 0.595(2) 0.010(2) 0.030(6) Uiso 1 1 d C15 C 0.6016(3) 0.1933(2) 0.0533(2) 0.0296(4) Uani 1 1 d H15C H 0.621(4) 0.095(3) 0.111(3) 0.059(8) Uiso 1 1 d H15B H 0.681(4) 0.196(3) -0.027(3) 0.052(7) Uiso 1 1 d H15A H 0.475(4) 0.207(3) 0.043(3) 0.069(9) Uiso 1 1 d 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 0.0224(2) 0.0234(2) 0.0254(2) -0.01089(18) -0.00648(17) -0.00336(17) O1 0.0252(7) 0.0273(7) 0.0289(7) -0.0138(6) -0.0015(5) -0.0098(5) O2 0.0282(7) 0.0207(6) 0.0213(6) -0.0094(5) -0.0075(5) 0.0003(5) O3 0.0393(9) 0.0724(12) 0.0376(9) -0.0250(8) 0.0093(7) -0.0333(8) O4 0.0246(7) 0.0281(7) 0.0264(7) -0.0113(6) -0.0010(5) -0.0074(5) O5 0.0323(7) 0.0286(7) 0.0264(7) -0.0109(6) -0.0137(6) 0.0002(6) O6 0.0287(7) 0.0371(8) 0.0376(8) -0.0182(7) -0.0003(6) -0.0134(6) N1 0.0222(8) 0.0218(8) 0.0232(8) -0.0105(6) -0.0023(6) -0.0069(6) C1 0.0224(9) 0.0168(8) 0.0222(8) -0.0066(7) -0.0059(7) -0.0025(7) C2 0.0259(9) 0.0171(8) 0.0216(8) -0.0075(7) -0.0075(7) -0.0018(7) C3 0.0252(9) 0.0174(8) 0.0244(9) -0.0049(7) -0.0113(7) -0.0021(7) C4 0.0233(9) 0.0179(9) 0.0236(9) -0.0041(7) -0.0093(7) -0.0031(7) C5 0.0234(9) 0.0236(10) 0.0275(9) -0.0065(8) -0.0061(7) -0.0069(7) C6 0.0228(9) 0.0299(10) 0.0290(10) -0.0079(8) -0.0054(7) -0.0067(8) C7 0.0306(10) 0.0290(11) 0.0267(10) -0.0115(8) -0.0050(8) -0.0019(9) C8 0.0309(10) 0.0262(10) 0.0313(10) -0.0076(8) -0.0119(8) -0.0102(8) C9 0.0207(8) 0.0205(9) 0.0240(9) -0.0103(7) -0.0062(7) -0.0005(7) C10 0.0259(9) 0.0222(9) 0.0211(9) -0.0078(7) -0.0048(7) -0.0015(7) C11 0.0259(9) 0.0209(9) 0.0245(9) -0.0065(7) -0.0056(7) -0.0044(7) C12 0.0213(9) 0.0239(9) 0.0294(9) -0.0131(8) -0.0110(7) 0.0046(7) C13 0.0249(9) 0.0284(10) 0.0257(9) -0.0134(8) -0.0040(7) 0.0011(8) C14 0.0208(9) 0.0254(10) 0.0253(9) -0.0099(8) -0.0015(7) -0.0019(7) C15 0.0323(11) 0.0279(11) 0.0337(11) -0.0168(9) -0.0098(9) 0.0001(8) 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' N N 0.0061 0.0033 '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' 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 O6 S1 O5 120.63(9) O6 S1 O2 105.72(8) O5 S1 O2 107.11(7) O6 S1 C9 109.73(8) O5 S1 C9 110.67(8) O2 S1 C9 100.99(7) C2 O2 S1 117.70(11) C6 O4 C7 115.32(15) C1 N1 C4 110.57(15) C1 N1 H1N1 124.2(16) C4 N1 H1N1 125.0(16) O1 C1 N1 127.71(16) O1 C1 C2 127.25(16) N1 C1 C2 105.04(14) C3 C2 O2 127.79(16) C3 C2 C1 111.02(15) O2 C2 C1 121.13(15) C2 C3 C4 106.04(15) C2 C3 C8 129.63(17) C4 C3 C8 124.31(17) C5 C4 N1 128.35(17) C5 C4 C3 124.38(16) N1 C4 C3 107.22(15) C4 C5 C6 127.76(17) C4 C5 H5 117.0(13) C6 C5 H5 115.1(13) O3 C6 O4 122.93(18) O3 C6 C5 122.93(18) O4 C6 C5 114.14(16) O4 C7 H7C 110.4(12) O4 C7 H7B 110.3(13) H7C C7 H7B 107.1(17) O4 C7 H7A 105.8(14) H7C C7 H7A 113.1(19) H7B C7 H7A 110.0(19) C3 C8 H8C 110.9(14) C3 C8 H8B 112.1(14) H8C C8 H8B 106.9(19) C3 C8 H8A 110.1(14) H8C C8 H8A 110.8(19) H8B C8 H8A 105.8(19) C14 C9 C10 121.68(16) C14 C9 S1 118.96(14) C10 C9 S1 119.35(13) C11 C10 C9 118.61(17) C11 C10 H10 121.2(13) C9 C10 H10 120.2(13) C10 C11 C12 121.29(18) C10 C11 H11 118.6(13) C12 C11 H11 120.1(13) C13 C12 C11 118.46(17) C13 C12 C15 121.04(17) C11 C12 C15 120.50(18) C12 C13 C14 121.37(17) C12 C13 H13 120.5(13) C14 C13 H13 118.1(14) C9 C14 C13 118.58(18) C9 C14 H14 121.6(13) C13 C14 H14 119.8(13) C12 C15 H15C 113.3(17) C12 C15 H15B 111.4(16) H15C C15 H15B 107(2) C12 C15 H15A 111.9(17) H15C C15 H15A 105(2) H15B C15 H15A 108(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O6 1.4226(14) S1 O5 1.4271(13) S1 O2 1.6274(13) S1 C9 1.7469(17) O1 C1 1.224(2) O2 C2 1.380(2) O3 C6 1.207(2) O4 C6 1.336(2) O4 C7 1.451(2) N1 C1 1.369(2) N1 C4 1.394(2) N1 H1N1 0.83(2) C1 C2 1.479(2) C2 C3 1.331(3) C3 C4 1.480(2) C3 C8 1.492(2) C4 C5 1.342(3) C5 C6 1.462(3) C5 H5 0.93(2) C7 H7C 1.01(2) C7 H7B 0.97(2) C7 H7A 0.98(3) C8 H8C 0.97(2) C8 H8B 0.98(2) C8 H8A 0.97(3) C9 C14 1.386(2) C9 C10 1.391(3) C10 C11 1.383(3) C10 H10 0.93(2) C11 C12 1.401(2) C11 H11 0.95(2) C12 C13 1.390(3) C12 C15 1.501(3) C13 C14 1.390(3) C13 H13 0.99(2) C14 H14 0.95(2) C15 H15C 0.95(3) C15 H15B 0.94(3) C15 H15A 0.99(3)