#------------------------------------------------------------------------------ #$Date: 2020-08-28 04:45:36 +0300 (Fri, 28 Aug 2020) $ #$Revision: 255704 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705292.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_7705292 loop_ _publ_author_name 'Kumar, Priyaranjan' 'Mondal, Indranil' 'Kulshreshtha, Ritu' 'Patra, Ashis Kumar' _publ_section_title ; Development of Novel Ruthenium(II)-Arene Complexes Displaying Potent Anticancer Effects in Glioblastoma ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02167A _journal_year 2020 _chemical_formula_moiety '2(C20 H14 N2 O), 0.5(H4 O2)' _chemical_formula_sum 'C40 H30 N4 O3' _chemical_formula_weight 614.68 _chemical_name_systematic AQNA _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' _atom_sites_solution_hydrogens mixed _audit_creation_date 2020-02-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-05-27 deposited with the CCDC. 2020-08-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 122.361(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 32.1158(18) _cell_length_b 4.7986(3) _cell_length_c 22.4568(14) _cell_measurement_reflns_used 4253 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 26.98 _cell_measurement_theta_min 2.59 _cell_volume 2923.3(3) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve (Bourhis et al., 2015)' _diffrn_ambient_temperature 273.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_unetI/netI 0.0454 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 16548 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.049 _diffrn_reflns_theta_max 25.049 _diffrn_reflns_theta_min 2.594 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1362 before and 0.0559 after correction. The Ratio of minimum to maximum transmission is 0.8466. The \l/2 correction factor is 0.00150.' _exptl_crystal_colour 'clear orangish yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier orangish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.397 _exptl_crystal_description block _exptl_crystal_F_000 1288 _exptl_crystal_recrystallization_method 'Slow Evaporation' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.177 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 214 _refine_ls_number_reflns 2593 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0452 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+1.9058P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0964 _refine_ls_wR_factor_ref 0.1092 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1797 _reflns_number_total 2593 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02167a2.cif _cod_data_source_block 20junb_a_a _cod_database_code 7705292 _shelx_shelxl_version_number 2017/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.991 _shelx_estimated_absorpt_t_min 0.982 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All O(H) groups, All O(H,H) groups 2. Others Fixed Sof: H2A(0.5) H2B(0.5) 3.a Free rotating group: O2(H2A,H2B) 3.b Aromatic/amide H refined with riding coordinates: C11(H11), C13(H13), C20(H20), C8(H8), C15(H15), C2(H2), C3(H3), C5(H5), C7(H7), C16(H16), C18(H18), C17(H17), C6(H6) 3.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL 20junb_a_a.res in C2/c 20junb_a_a.res created by SHELXL-2017/1 at 01:13:22 on 07-Feb-2020 REM Old TITL 20junb_a.res in C2/c REM SHELXT solution in C2/c REM R1 0.149, Rweak 0.008, Alpha 0.035, Orientation as input REM Formula found by SHELXT: C40 N4 O2 CELL 0.71073 32.1158 4.7986 22.4568 90 122.361 90 ZERR 4 0.0018 0.0003 0.0014 0 0.003 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 160 120 16 12 L.S. 10 PLAN 5 SIZE 0.1 0.15 0.2 TEMP 0 BOND $H fmap 2 acta OMIT -2 50.1 REM REM REM WGHT 0.048800 1.905800 FVAR 0.28605 O1 4 0.721628 0.509295 0.325354 11.00000 0.02494 0.02758 = 0.03297 0.00310 0.01506 -0.00133 AFIX 147 H1 2 0.708939 0.402393 0.339653 11.00000 -1.50000 AFIX 0 N1 3 0.653097 0.281364 0.332991 11.00000 0.02275 0.01862 = 0.02079 -0.00211 0.01208 0.00009 N2 3 0.575976 -0.219992 0.358458 11.00000 0.02047 0.01924 = 0.02177 -0.00029 0.01210 0.00040 C14 1 0.610632 -0.325509 0.423207 11.00000 0.02474 0.01663 = 0.01991 -0.00006 0.01425 0.00641 C11 1 0.621321 0.425580 0.278865 11.00000 0.02067 0.01794 = 0.02321 -0.00321 0.01278 -0.00076 AFIX 43 H11 2 0.587879 0.398983 0.260383 11.00000 -1.20000 AFIX 0 C12 1 0.638337 0.081048 0.364132 11.00000 0.02313 0.01541 = 0.01953 -0.00360 0.01344 0.00084 C13 1 0.589461 -0.025042 0.331245 11.00000 0.02302 0.01963 = 0.01894 -0.00009 0.01123 0.00268 AFIX 43 H13 2 0.565607 0.048542 0.287738 11.00000 -1.20000 AFIX 0 C9 1 0.600839 0.798696 0.188662 11.00000 0.02713 0.01597 = 0.02106 -0.00531 0.01601 -0.00189 C20 1 0.672872 -0.025404 0.428402 11.00000 0.01853 0.02023 = 0.02334 -0.00505 0.01149 0.00079 AFIX 43 H20 2 0.705202 0.038389 0.451181 11.00000 -1.20000 AFIX 0 C19 1 0.660074 -0.230910 0.460616 11.00000 0.02394 0.01840 = 0.02037 -0.00248 0.01260 0.00544 C10 1 0.636463 0.626335 0.246520 11.00000 0.02531 0.01464 = 0.02230 -0.00464 0.01571 -0.00182 C4 1 0.617482 0.991847 0.158054 11.00000 0.03087 0.01806 = 0.02266 -0.00569 0.01771 -0.00281 C1 1 0.686318 0.656908 0.270808 11.00000 0.02375 0.01819 = 0.02300 -0.00465 0.01357 -0.00048 C8 1 0.549649 0.790877 0.161320 11.00000 0.02590 0.02078 = 0.02487 0.00116 0.01657 0.00034 AFIX 43 H8 2 0.537549 0.665592 0.180070 11.00000 -1.20000 AFIX 0 C15 1 0.596176 -0.533880 0.452429 11.00000 0.02806 0.02174 = 0.02688 -0.00271 0.01838 0.00101 AFIX 43 H15 2 0.563688 -0.595724 0.427896 11.00000 -1.20000 AFIX 0 C2 1 0.701779 0.847606 0.238627 11.00000 0.02763 0.02555 = 0.03528 -0.00682 0.02170 -0.00701 AFIX 43 H2 2 0.735108 0.864071 0.255105 11.00000 -1.20000 AFIX 0 C3 1 0.668426 1.006606 0.183960 11.00000 0.03437 0.02187 = 0.02952 -0.00294 0.02345 -0.00596 AFIX 43 H3 2 0.679251 1.128720 0.162867 11.00000 -1.20000 AFIX 0 C5 1 0.583280 1.166242 0.102712 11.00000 0.03824 0.01990 = 0.02508 -0.00225 0.02102 -0.00457 AFIX 43 H5 2 0.594363 1.291670 0.082604 11.00000 -1.20000 AFIX 0 C7 1 0.517778 0.963346 0.108074 11.00000 0.02694 0.02527 = 0.02730 -0.00176 0.01481 0.00089 AFIX 43 H7 2 0.484305 0.954203 0.091180 11.00000 -1.20000 AFIX 0 C16 1 0.629538 -0.646199 0.516643 11.00000 0.04322 0.02238 = 0.02972 0.00291 0.02615 0.00609 AFIX 43 H16 2 0.619839 -0.786253 0.535335 11.00000 -1.20000 AFIX 0 C18 1 0.693440 -0.348101 0.527501 11.00000 0.02479 0.02762 = 0.02310 -0.00126 0.01066 0.00440 AFIX 43 H18 2 0.725922 -0.286282 0.553296 11.00000 -1.20000 AFIX 0 C17 1 0.678534 -0.550570 0.554577 11.00000 0.03906 0.02805 = 0.02236 0.00495 0.01717 0.01056 AFIX 43 H17 2 0.700965 -0.626293 0.598561 11.00000 -1.20000 AFIX 0 C6 1 0.534476 1.153985 0.078336 11.00000 0.03560 0.02309 = 0.02291 0.00182 0.01414 0.00369 AFIX 43 H6 2 0.512329 1.271410 0.042156 11.00000 -1.20000 AFIX 6 O2 4 0.500000 0.434398 0.250000 10.50000 0.02844 H2A 2 0.487344 0.526626 0.211850 10.50000 -1.50000 H2B 2 0.521697 0.542602 0.281153 10.50000 -1.50000 AFIX 0 HKLF 4 REM 20junb_a_a.res in C2/c REM R1 = 0.0452 for 1797 Fo > 4sig(Fo) and 0.0792 for all 2593 data REM 214 parameters refined using 0 restraints END WGHT 0.0488 1.9058 REM Highest difference peak 0.177, deepest hole -0.273, 1-sigma level 0.054 Q1 1 0.6912 -0.5627 0.5228 11.00000 0.05 0.18 Q2 1 0.7522 -0.2680 0.5859 11.00000 0.05 0.17 Q3 1 0.4998 1.3033 0.1105 11.00000 0.05 0.17 Q4 1 0.5750 0.7139 0.1617 11.00000 0.05 0.17 Q5 1 0.5284 1.1407 0.1697 11.00000 0.05 0.17 ; _shelx_res_checksum 26877 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.72163(5) 0.5093(3) 0.32535(7) 0.0287(4) Uani 1 1 d . . . . . H1 H 0.708939 0.402393 0.339653 0.043 Uiso 1 1 calc GR . . . . N1 N 0.65310(6) 0.2814(3) 0.33299(8) 0.0205(4) Uani 1 1 d . . . . . N2 N 0.57598(6) -0.2200(3) 0.35846(8) 0.0201(4) Uani 1 1 d . . . . . C14 C 0.61063(7) -0.3255(4) 0.42321(10) 0.0193(5) Uani 1 1 d . . . . . C11 C 0.62132(7) 0.4256(4) 0.27886(10) 0.0201(5) Uani 1 1 d . . . . . H11 H 0.587879 0.398983 0.260383 0.024 Uiso 1 1 calc R . . . . C12 C 0.63834(7) 0.0810(4) 0.36413(10) 0.0183(4) Uani 1 1 d . . . . . C13 C 0.58946(7) -0.0250(4) 0.33125(10) 0.0205(5) Uani 1 1 d . . . . . H13 H 0.565607 0.048542 0.287738 0.025 Uiso 1 1 calc R . . . . C9 C 0.60084(7) 0.7987(4) 0.18866(10) 0.0198(5) Uani 1 1 d . . . . . C20 C 0.67287(7) -0.0254(4) 0.42840(10) 0.0206(5) Uani 1 1 d . . . . . H20 H 0.705202 0.038389 0.451181 0.025 Uiso 1 1 calc R . . . . C19 C 0.66007(7) -0.2309(4) 0.46062(10) 0.0205(5) Uani 1 1 d . . . . . C10 C 0.63646(7) 0.6263(4) 0.24652(10) 0.0193(5) Uani 1 1 d . . . . . C4 C 0.61748(7) 0.9918(4) 0.15805(10) 0.0222(5) Uani 1 1 d . . . . . C1 C 0.68632(7) 0.6569(4) 0.27081(10) 0.0211(5) Uani 1 1 d . . . . . C8 C 0.54965(7) 0.7909(4) 0.16132(10) 0.0224(5) Uani 1 1 d . . . . . H8 H 0.537549 0.665592 0.180070 0.027 Uiso 1 1 calc R . . . . C15 C 0.59618(7) -0.5339(4) 0.45243(10) 0.0237(5) Uani 1 1 d . . . . . H15 H 0.563688 -0.595724 0.427896 0.028 Uiso 1 1 calc R . . . . C2 C 0.70178(8) 0.8476(4) 0.23863(11) 0.0271(5) Uani 1 1 d . . . . . H2 H 0.735108 0.864071 0.255105 0.032 Uiso 1 1 calc R . . . . C3 C 0.66843(7) 1.0066(4) 0.18396(10) 0.0254(5) Uani 1 1 d . . . . . H3 H 0.679251 1.128720 0.162867 0.030 Uiso 1 1 calc R . . . . C5 C 0.58328(8) 1.1662(4) 0.10271(10) 0.0257(5) Uani 1 1 d . . . . . H5 H 0.594363 1.291670 0.082604 0.031 Uiso 1 1 calc R . . . . C7 C 0.51778(8) 0.9633(4) 0.10807(10) 0.0264(5) Uani 1 1 d . . . . . H7 H 0.484305 0.954203 0.091180 0.032 Uiso 1 1 calc R . . . . C16 C 0.62954(8) -0.6462(4) 0.51664(11) 0.0285(5) Uani 1 1 d . . . . . H16 H 0.619839 -0.786253 0.535335 0.034 Uiso 1 1 calc R . . . . C18 C 0.69344(8) -0.3481(4) 0.52750(10) 0.0262(5) Uani 1 1 d . . . . . H18 H 0.725922 -0.286282 0.553296 0.031 Uiso 1 1 calc R . . . . C17 C 0.67853(8) -0.5506(4) 0.55458(11) 0.0295(5) Uani 1 1 d . . . . . H17 H 0.700965 -0.626293 0.598561 0.035 Uiso 1 1 calc R . . . . C6 C 0.53448(8) 1.1540(4) 0.07834(11) 0.0280(5) Uani 1 1 d . . . . . H6 H 0.512329 1.271410 0.042156 0.034 Uiso 1 1 calc R . . . . O2 O 0.500000 0.4344(4) 0.250000 0.0284(5) Uiso 1 2 d S T P . . H2A H 0.487344 0.526626 0.211850 0.043 Uiso 0.5 1 d G . . . . H2B H 0.521697 0.542602 0.281153 0.043 Uiso 0.5 1 d G . . . . 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 O1 0.0249(8) 0.0276(9) 0.0330(9) 0.0031(7) 0.0151(7) -0.0013(7) N1 0.0228(9) 0.0186(9) 0.0208(9) -0.0021(8) 0.0121(8) 0.0001(8) N2 0.0205(9) 0.0192(9) 0.0218(9) -0.0003(8) 0.0121(8) 0.0004(7) C14 0.0247(11) 0.0166(10) 0.0199(10) -0.0001(9) 0.0143(9) 0.0064(9) C11 0.0207(11) 0.0179(10) 0.0232(11) -0.0032(9) 0.0128(10) -0.0008(9) C12 0.0231(11) 0.0154(10) 0.0195(10) -0.0036(9) 0.0134(9) 0.0008(9) C13 0.0230(11) 0.0196(11) 0.0189(10) -0.0001(9) 0.0112(9) 0.0027(9) C9 0.0271(11) 0.0160(10) 0.0211(10) -0.0053(9) 0.0160(10) -0.0019(9) C20 0.0185(11) 0.0202(11) 0.0233(11) -0.0050(9) 0.0115(9) 0.0008(9) C19 0.0239(11) 0.0184(11) 0.0204(10) -0.0025(9) 0.0126(9) 0.0054(9) C10 0.0253(11) 0.0146(10) 0.0223(11) -0.0046(9) 0.0157(10) -0.0018(9) C4 0.0309(12) 0.0181(11) 0.0227(11) -0.0057(9) 0.0177(10) -0.0028(10) C1 0.0238(11) 0.0182(11) 0.0230(11) -0.0046(9) 0.0136(10) -0.0005(9) C8 0.0259(12) 0.0208(11) 0.0249(11) 0.0012(9) 0.0166(10) 0.0003(9) C15 0.0281(12) 0.0217(11) 0.0269(12) -0.0027(10) 0.0184(10) 0.0010(10) C2 0.0276(12) 0.0255(12) 0.0353(13) -0.0068(11) 0.0217(11) -0.0070(10) C3 0.0344(13) 0.0219(11) 0.0295(12) -0.0029(10) 0.0235(11) -0.0060(10) C5 0.0382(14) 0.0199(11) 0.0251(12) -0.0023(10) 0.0210(11) -0.0046(10) C7 0.0269(12) 0.0253(12) 0.0273(12) -0.0018(10) 0.0148(10) 0.0009(10) C16 0.0432(14) 0.0224(12) 0.0297(12) 0.0029(10) 0.0261(12) 0.0061(11) C18 0.0248(12) 0.0276(12) 0.0231(11) -0.0013(10) 0.0107(10) 0.0044(10) C17 0.0391(14) 0.0281(12) 0.0224(11) 0.0050(10) 0.0172(11) 0.0106(11) C6 0.0356(13) 0.0231(12) 0.0229(11) 0.0018(10) 0.0141(11) 0.0037(10) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C11 N1 C12 121.68(17) . . ? C13 N2 C14 118.36(17) . . ? N2 C14 C19 121.81(17) . . ? N2 C14 C15 118.37(18) . . ? C15 C14 C19 119.82(18) . . ? N1 C11 H11 119.2 . . ? N1 C11 C10 121.55(18) . . ? C10 C11 H11 119.2 . . ? N1 C12 C13 123.76(17) . . ? C20 C12 N1 118.73(17) . . ? C20 C12 C13 117.47(18) . . ? N2 C13 C12 124.11(18) . . ? N2 C13 H13 117.9 . . ? C12 C13 H13 117.9 . . ? C4 C9 C10 119.16(18) . . ? C8 C9 C10 123.49(17) . . ? C8 C9 C4 117.33(18) . . ? C12 C20 H20 119.7 . . ? C12 C20 C19 120.68(18) . . ? C19 C20 H20 119.7 . . ? C20 C19 C14 117.56(18) . . ? C20 C19 C18 124.11(19) . . ? C18 C19 C14 118.33(18) . . ? C11 C10 C9 121.20(17) . . ? C1 C10 C11 120.01(18) . . ? C1 C10 C9 118.79(17) . . ? C3 C4 C9 119.11(18) . . ? C5 C4 C9 119.80(19) . . ? C5 C4 C3 121.09(18) . . ? O1 C1 C10 122.24(18) . . ? O1 C1 C2 116.92(17) . . ? C10 C1 C2 120.84(18) . . ? C9 C8 H8 119.4 . . ? C7 C8 C9 121.20(19) . . ? C7 C8 H8 119.4 . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.8 . . ? C1 C2 H2 119.8 . . ? C3 C2 C1 120.40(19) . . ? C3 C2 H2 119.8 . . ? C4 C3 H3 119.2 . . ? C2 C3 C4 121.66(19) . . ? C2 C3 H3 119.2 . . ? C4 C5 H5 119.5 . . ? C6 C5 C4 121.08(19) . . ? C6 C5 H5 119.5 . . ? C8 C7 H7 119.4 . . ? C8 C7 C6 121.1(2) . . ? C6 C7 H7 119.4 . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.1(2) . . ? C17 C16 H16 119.9 . . ? C19 C18 H18 119.6 . . ? C17 C18 C19 120.7(2) . . ? C17 C18 H18 119.6 . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C5 C6 C7 119.4(2) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? H2A O2 H2A 117.2 . 2_655 ? H2A O2 H2B 104.5 2_655 2_655 ? H2A O2 H2B 104.5 . . ? H2A O2 H2B 27.5 . 2_655 ? H2B O2 H2A 27.5 . 2_655 ? H2B O2 H2B 104.7 . 2_655 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1 0.8200 . ? O1 C1 1.342(2) . ? N1 C11 1.292(2) . ? N1 C12 1.412(2) . ? N2 C14 1.370(2) . ? N2 C13 1.311(2) . ? C14 C19 1.416(3) . ? C14 C15 1.404(3) . ? C11 H11 0.9300 . ? C11 C10 1.439(3) . ? C12 C13 1.424(3) . ? C12 C20 1.364(3) . ? C13 H13 0.9300 . ? C9 C10 1.446(3) . ? C9 C4 1.418(3) . ? C9 C8 1.414(3) . ? C20 H20 0.9300 . ? C20 C19 1.408(3) . ? C19 C18 1.413(3) . ? C10 C1 1.396(3) . ? C4 C3 1.415(3) . ? C4 C5 1.411(3) . ? C1 C2 1.411(3) . ? C8 H8 0.9300 . ? C8 C7 1.361(3) . ? C15 H15 0.9300 . ? C15 C16 1.365(3) . ? C2 H2 0.9300 . ? C2 C3 1.352(3) . ? C3 H3 0.9300 . ? C5 H5 0.9300 . ? C5 C6 1.357(3) . ? C7 H7 0.9300 . ? C7 C6 1.398(3) . ? C16 H16 0.9300 . ? C16 C17 1.406(3) . ? C18 H18 0.9300 . ? C18 C17 1.362(3) . ? C17 H17 0.9300 . ? C6 H6 0.9300 . ? O2 H2A 0.85(6) 2_655 ? O2 H2A 0.8499 . ? O2 H2B 0.85(7) 2_655 ? O2 H2B 0.8501 . ?