#------------------------------------------------------------------------------ #$Date: 2023-11-10 04:20:50 +0200 (Fri, 10 Nov 2023) $ #$Revision: 287507 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247699.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_7247699 loop_ _publ_author_name 'Zheng, Yongpeng' 'Li, Jianxiao' 'Qi, Chaorong' 'Wu, Wanqing' 'Jiang, Huanfeng' _publ_section_title ; Rapid assembly of structurally diverse cyanamides and disulfanes via base-mediated aminoalkylation of aryl thiourea ; _journal_issue 47 _journal_name_full 'RSC Advances' _journal_page_first 33047 _journal_page_last 33052 _journal_paper_doi 10.1039/D3RA06051A _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C16 H14 N2 O2' _chemical_formula_sum 'C16 H14 N2 O2' _chemical_formula_weight 266.29 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-12-04 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-02-14 deposited with the CCDC. 2023-10-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.913(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.5729(5) _cell_length_b 29.957(2) _cell_length_c 6.9575(5) _cell_measurement_reflns_used 2523 _cell_measurement_temperature 170 _cell_measurement_theta_max 26.032 _cell_measurement_theta_min 2.720 _cell_volume 1345.19(17) _computing_cell_refinement 'SAINT V8.40A (?, 2016)' _computing_data_reduction 'SAINT V8.40A (?, 2016)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 170.0 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'D8 VENTURE' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_unetI/netI 0.0628 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 10375 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.357 _diffrn_reflns_theta_min 2.720 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5390 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1326 before and 0.0670 after correction. The Ratio of minimum to maximum transmission is 0.7231. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.315 _exptl_crystal_description block _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.200 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2743 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0505 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.2512P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.1288 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1819 _reflns_number_total 2743 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL 124z1085112_0m_a.res in P2(1)/n 124z1085112_0m.res created by SHELXL-2018/3 at 15:31:49 on 04-Dec-2022 REM Old TITL 124Z1085112_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.181, Rweak 0.008, Alpha 0.032, Orientation as input REM Formula found by SHELXT: C16 N2 O2 CELL 0.71073 6.5729 29.9571 6.9575 90 100.913 90 ZERR 4 0.0005 0.0021 0.0005 0 0.003 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 64 56 8 8 L.S. 4 PLAN 20 SIZE 0.12 0.08 0.05 TEMP -103.15 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.047800 0.251200 FVAR 1.34422 O2 4 0.634091 0.617733 0.379778 11.00000 0.03237 0.03011 = 0.04808 -0.00437 0.00301 0.00099 O1 4 0.899797 0.565822 0.444659 11.00000 0.02756 0.03280 = 0.04701 -0.00353 -0.00214 -0.00171 N1 3 0.446708 0.441031 0.195990 11.00000 0.02054 0.03034 = 0.03171 -0.00146 0.00207 0.00104 N2 3 0.090882 0.417084 0.044232 11.00000 0.02848 0.04514 = 0.05079 0.00364 -0.00017 -0.00286 C10 1 0.487157 0.487198 0.238388 11.00000 0.02520 0.03038 = 0.01885 0.00004 0.00413 0.00075 C11 1 0.326756 0.517993 0.198827 11.00000 0.02210 0.03596 = 0.02547 0.00088 0.00444 0.00300 AFIX 43 H11 2 0.190909 0.508171 0.143306 11.00000 -1.20000 AFIX 0 C8 1 0.613394 0.407290 0.240248 11.00000 0.02318 0.03110 = 0.02873 -0.00111 0.00223 0.00447 AFIX 23 H8A 2 0.671591 0.407821 0.382291 11.00000 -1.20000 H8B 2 0.725932 0.415149 0.169801 11.00000 -1.20000 AFIX 0 C9 1 0.255935 0.428223 0.114579 11.00000 0.02793 0.03281 = 0.03073 0.00244 0.00630 0.00247 C12 1 0.363054 0.563279 0.239820 11.00000 0.02765 0.03266 = 0.02820 0.00262 0.00724 0.00667 AFIX 43 H12 2 0.254208 0.584568 0.213534 11.00000 -1.20000 AFIX 0 C15 1 0.689948 0.500334 0.319284 11.00000 0.02477 0.03294 = 0.02632 0.00281 0.00408 0.00523 AFIX 43 H15 2 0.800752 0.479519 0.345969 11.00000 -1.20000 AFIX 0 C14 1 0.718840 0.544963 0.357566 11.00000 0.02397 0.03308 = 0.02428 0.00096 0.00257 0.00006 C13 1 0.560491 0.575724 0.318914 11.00000 0.02883 0.02910 = 0.02565 -0.00009 0.00622 0.00057 C7 1 0.536503 0.360269 0.181564 11.00000 0.03164 0.03328 = 0.04106 -0.00147 0.00283 -0.00264 AFIX 23 H7A 2 0.422011 0.352244 0.249254 11.00000 -1.20000 H7B 2 0.483527 0.358997 0.038664 11.00000 -1.20000 AFIX 0 C1 1 0.713667 0.327768 0.237212 11.00000 0.03056 0.02436 = 0.05436 -0.00217 0.00210 -0.00523 C16 1 0.855173 0.612657 0.428160 11.00000 0.03201 0.03211 = 0.04821 -0.00415 0.00465 -0.00136 AFIX 23 H16A 2 0.920352 0.626044 0.324626 11.00000 -1.20000 H16B 2 0.910539 0.627872 0.553465 11.00000 -1.20000 AFIX 0 C6 1 0.853218 0.321505 0.113171 11.00000 0.04299 0.03084 = 0.06366 -0.00917 0.00709 -0.00218 AFIX 43 H6 2 0.831339 0.336400 -0.009564 11.00000 -1.20000 AFIX 0 C2 1 0.746149 0.305644 0.414789 11.00000 0.04141 0.04394 = 0.06906 0.01672 0.00295 -0.00604 AFIX 43 H2 2 0.651661 0.309413 0.501320 11.00000 -1.20000 AFIX 0 C5 1 1.023310 0.294041 0.164630 11.00000 0.04854 0.03330 = 0.11387 -0.01224 0.01593 0.00645 AFIX 43 H5 2 1.117768 0.290180 0.078132 11.00000 -1.20000 AFIX 0 C3 1 0.917573 0.277818 0.466715 11.00000 0.05774 0.04565 = 0.10271 0.03384 -0.01160 -0.00781 AFIX 43 H3 2 0.939560 0.262599 0.588689 11.00000 -1.20000 AFIX 0 C4 1 1.055360 0.272267 0.342028 11.00000 0.04375 0.03388 = 0.14888 0.00880 -0.00298 0.00660 AFIX 43 H4 2 1.172512 0.253408 0.378484 11.00000 -1.20000 AFIX 0 HKLF 4 REM 124z1085112_0m_a.res in P2(1)/n REM wR2 = 0.1288, GooF = S = 1.071, Restrained GooF = 1.071 for all data REM R1 = 0.0505 for 1819 Fo > 4sig(Fo) and 0.0923 for all 2743 data REM 181 parameters refined using 0 restraints END WGHT 0.0476 0.2612 REM Highest difference peak 0.200, deepest hole -0.229, 1-sigma level 0.046 Q1 1 0.0493 0.5046 -0.0402 11.00000 0.05 0.20 Q2 1 -0.0791 0.4397 -0.0196 11.00000 0.05 0.17 Q3 1 0.9977 0.5188 0.4878 11.00000 0.05 0.17 Q4 1 0.9061 0.5009 0.5542 11.00000 0.05 0.17 Q5 1 0.1299 0.4678 -0.0457 11.00000 0.05 0.16 Q6 1 -0.0830 0.5143 0.1614 11.00000 0.05 0.16 Q7 1 0.4955 0.5706 0.2061 11.00000 0.05 0.16 Q8 1 0.7617 0.3565 0.4220 11.00000 0.05 0.16 Q9 1 0.3352 0.3307 0.0766 11.00000 0.05 0.16 Q10 1 1.0360 0.2793 0.4611 11.00000 0.05 0.15 Q11 1 0.6572 0.3319 -0.1041 11.00000 0.05 0.14 Q12 1 0.0692 0.5243 0.0726 11.00000 0.05 0.14 Q13 1 0.6149 0.6216 0.2377 11.00000 0.05 0.14 Q14 1 0.3487 0.4334 0.2131 11.00000 0.05 0.14 Q15 1 1.2448 0.2993 0.3392 11.00000 0.05 0.14 Q16 1 -0.0397 0.4182 0.1450 11.00000 0.05 0.14 Q17 1 0.0229 0.5402 0.1526 11.00000 0.05 0.14 Q18 1 0.4488 0.3217 0.1937 11.00000 0.05 0.13 Q19 1 0.7786 0.3233 0.3596 11.00000 0.05 0.13 Q20 1 0.9232 0.2907 -0.0413 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0505 for 1819 Fo > 4sig(Fo) and 0.0923 for all 10531 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.20, deepest hole -0.23 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0923 REM R1_gt = 0.0505 REM wR_ref = 0.1288 REM GOOF = 1.071 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 10531 REM Reflections_gt = 1819 REM Parameters = n/a REM Hole = -0.23 REM Peak = 0.20 REM Flack = n/a ; _cod_data_source_file d3ra06051a2.cif _cod_data_source_block 124z1085112_0m _cod_database_code 7247699 _shelx_shelxl_version_number 2018/3 _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 0.996 _shelx_estimated_absorpt_t_min 0.989 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C7(H7A,H7B), C16(H16A,H16B) 2.b Aromatic/amide H refined with riding coordinates: C11(H11), C12(H12), C15(H15), C6(H6), C2(H2), C5(H5), C3(H3), C4(H4) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_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_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 O2 O 0.6341(2) 0.61773(4) 0.3798(2) 0.0375(4) Uani 1 1 d . . . . . O1 O 0.89980(19) 0.56582(4) 0.4447(2) 0.0370(4) Uani 1 1 d . . . . . N1 N 0.4467(2) 0.44103(5) 0.1960(2) 0.0279(4) Uani 1 1 d . . . . . N2 N 0.0909(3) 0.41708(6) 0.0442(3) 0.0425(5) Uani 1 1 d . . . . . C10 C 0.4872(3) 0.48720(6) 0.2384(2) 0.0248(4) Uani 1 1 d . . . . . C11 C 0.3268(3) 0.51799(6) 0.1988(3) 0.0278(4) Uani 1 1 d . . . . . H11 H 0.190909 0.508171 0.143306 0.033 Uiso 1 1 calc R . . . . C8 C 0.6134(3) 0.40729(6) 0.2402(3) 0.0280(4) Uani 1 1 d . . . . . H8A H 0.671591 0.407821 0.382291 0.034 Uiso 1 1 calc R . . . . H8B H 0.725932 0.415149 0.169801 0.034 Uiso 1 1 calc R . . . . C9 C 0.2559(3) 0.42822(6) 0.1146(3) 0.0304(5) Uani 1 1 d . . . . . C12 C 0.3631(3) 0.56328(6) 0.2398(3) 0.0292(4) Uani 1 1 d . . . . . H12 H 0.254208 0.584568 0.213534 0.035 Uiso 1 1 calc R . . . . C15 C 0.6899(3) 0.50033(6) 0.3193(3) 0.0281(4) Uani 1 1 d . . . . . H15 H 0.800752 0.479519 0.345969 0.034 Uiso 1 1 calc R . . . . C14 C 0.7188(3) 0.54496(6) 0.3576(2) 0.0274(4) Uani 1 1 d . . . . . C13 C 0.5605(3) 0.57572(6) 0.3189(3) 0.0277(4) Uani 1 1 d . . . . . C7 C 0.5365(3) 0.36027(6) 0.1816(3) 0.0359(5) Uani 1 1 d . . . . . H7A H 0.422011 0.352244 0.249254 0.043 Uiso 1 1 calc R . . . . H7B H 0.483527 0.358997 0.038664 0.043 Uiso 1 1 calc R . . . . C1 C 0.7137(3) 0.32777(6) 0.2372(3) 0.0372(5) Uani 1 1 d . . . . . C16 C 0.8552(3) 0.61266(6) 0.4282(3) 0.0378(5) Uani 1 1 d . . . . . H16A H 0.920352 0.626044 0.324626 0.045 Uiso 1 1 calc R . . . . H16B H 0.910539 0.627872 0.553465 0.045 Uiso 1 1 calc R . . . . C6 C 0.8532(3) 0.32150(7) 0.1132(4) 0.0462(6) Uani 1 1 d . . . . . H6 H 0.831339 0.336400 -0.009564 0.055 Uiso 1 1 calc R . . . . C2 C 0.7461(4) 0.30564(8) 0.4148(4) 0.0525(6) Uani 1 1 d . . . . . H2 H 0.651661 0.309413 0.501320 0.063 Uiso 1 1 calc R . . . . C5 C 1.0233(4) 0.29404(8) 0.1646(5) 0.0652(8) Uani 1 1 d . . . . . H5 H 1.117768 0.290180 0.078132 0.078 Uiso 1 1 calc R . . . . C3 C 0.9176(4) 0.27782(8) 0.4667(5) 0.0722(9) Uani 1 1 d . . . . . H3 H 0.939560 0.262599 0.588689 0.087 Uiso 1 1 calc R . . . . C4 C 1.0554(4) 0.27227(8) 0.3420(6) 0.0783(10) Uani 1 1 d . . . . . H4 H 1.172512 0.253408 0.378484 0.094 Uiso 1 1 calc 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 O2 0.0324(8) 0.0301(8) 0.0481(9) -0.0044(6) 0.0030(7) 0.0010(6) O1 0.0276(8) 0.0328(8) 0.0470(9) -0.0035(6) -0.0021(6) -0.0017(6) N1 0.0205(9) 0.0303(9) 0.0317(9) -0.0015(7) 0.0021(7) 0.0010(7) N2 0.0285(10) 0.0451(11) 0.0508(11) 0.0036(8) -0.0002(9) -0.0029(8) C10 0.0252(10) 0.0304(10) 0.0189(9) 0.0000(7) 0.0041(7) 0.0008(8) C11 0.0221(10) 0.0360(10) 0.0255(9) 0.0009(8) 0.0044(8) 0.0030(8) C8 0.0232(10) 0.0311(10) 0.0287(10) -0.0011(8) 0.0022(8) 0.0045(8) C9 0.0279(12) 0.0328(11) 0.0307(10) 0.0024(8) 0.0063(9) 0.0025(9) C12 0.0277(11) 0.0327(10) 0.0282(10) 0.0026(8) 0.0072(9) 0.0067(8) C15 0.0248(10) 0.0329(10) 0.0263(10) 0.0028(8) 0.0041(8) 0.0052(8) C14 0.0240(10) 0.0331(11) 0.0243(9) 0.0010(8) 0.0026(8) 0.0001(8) C13 0.0288(11) 0.0291(10) 0.0256(10) -0.0001(8) 0.0062(8) 0.0006(8) C7 0.0316(11) 0.0333(11) 0.0411(12) -0.0015(9) 0.0028(9) -0.0026(9) C1 0.0306(11) 0.0244(10) 0.0544(13) -0.0022(9) 0.0021(10) -0.0052(9) C16 0.0320(12) 0.0321(11) 0.0482(13) -0.0041(9) 0.0046(10) -0.0014(9) C6 0.0430(14) 0.0308(11) 0.0637(15) -0.0092(10) 0.0071(12) -0.0022(10) C2 0.0414(14) 0.0439(13) 0.0691(17) 0.0167(12) 0.0029(12) -0.0060(11) C5 0.0485(16) 0.0333(13) 0.114(2) -0.0122(15) 0.0159(16) 0.0065(12) C3 0.0577(18) 0.0457(15) 0.103(2) 0.0338(15) -0.0116(17) -0.0078(13) C4 0.0437(17) 0.0339(14) 0.149(3) 0.0088(17) -0.0030(19) 0.0066(12) 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 C13 O2 C16 104.76(14) . . ? C14 O1 C16 105.19(14) . . ? C10 N1 C8 121.12(14) . . ? C9 N1 C10 119.37(15) . . ? C9 N1 C8 119.50(15) . . ? C11 C10 N1 119.84(16) . . ? C11 C10 C15 121.45(17) . . ? C15 C10 N1 118.71(16) . . ? C10 C11 H11 119.6 . . ? C10 C11 C12 120.70(17) . . ? C12 C11 H11 119.6 . . ? N1 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? N1 C8 C7 112.35(15) . . ? H8A C8 H8B 107.9 . . ? C7 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? N2 C9 N1 179.9(3) . . ? C11 C12 H12 121.3 . . ? C13 C12 C11 117.45(17) . . ? C13 C12 H12 121.3 . . ? C10 C15 H15 122.0 . . ? C14 C15 C10 116.01(17) . . ? C14 C15 H15 122.0 . . ? C15 C14 O1 127.19(17) . . ? C15 C14 C13 122.90(17) . . ? C13 C14 O1 109.86(16) . . ? C12 C13 O2 128.53(17) . . ? C12 C13 C14 121.50(17) . . ? C14 C13 O2 109.92(16) . . ? C8 C7 H7A 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C1 C7 C8 109.03(15) . . ? C1 C7 H7A 109.9 . . ? C1 C7 H7B 109.9 . . ? C6 C1 C7 119.76(19) . . ? C2 C1 C7 121.3(2) . . ? C2 C1 C6 118.9(2) . . ? O2 C16 H16A 110.2 . . ? O2 C16 H16B 110.2 . . ? O1 C16 O2 107.76(14) . . ? O1 C16 H16A 110.2 . . ? O1 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? C1 C6 H6 119.4 . . ? C5 C6 C1 121.2(2) . . ? C5 C6 H6 119.4 . . ? C1 C2 H2 120.0 . . ? C1 C2 C3 119.9(3) . . ? C3 C2 H2 120.0 . . ? C6 C5 H5 120.2 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? 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 O2 C13 1.385(2) . ? O2 C16 1.436(2) . ? O1 C14 1.378(2) . ? O1 C16 1.434(2) . ? N1 C10 1.429(2) . ? N1 C8 1.480(2) . ? N1 C9 1.331(2) . ? N2 C9 1.152(2) . ? C10 C11 1.389(2) . ? C10 C15 1.402(2) . ? C11 H11 0.9500 . ? C11 C12 1.397(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C7 1.526(3) . ? C12 H12 0.9500 . ? C12 C13 1.362(3) . ? C15 H15 0.9500 . ? C15 C14 1.369(3) . ? C14 C13 1.378(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C1 1.511(3) . ? C1 C6 1.386(3) . ? C1 C2 1.383(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C6 H6 0.9500 . ? C6 C5 1.380(3) . ? C2 H2 0.9500 . ? C2 C3 1.393(3) . ? C5 H5 0.9500 . ? C5 C4 1.377(4) . ? C3 H3 0.9500 . ? C3 C4 1.378(4) . ? C4 H4 0.9500 . ?