#------------------------------------------------------------------------------ #$Date: 2015-06-20 04:57:43 +0300 (Sat, 20 Jun 2015) $ #$Revision: 139447 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/08/2240853.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2240853 loop_ _publ_author_name 'Suresh, M.' 'Padusha, M. Syed Ali' 'Novina, J. Josephine' 'Vasuki, G.' 'Viswanathan, Vijayan' 'Velmurugan, Devadasan' _publ_section_title ; Crystal structure of ethyl 6-chloromethyl-2-oxo-4-(2,3,4-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate ; _journal_coeditor_code LH5770 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 821 _journal_page_last 823 _journal_paper_doi 10.1107/S2056989015011688 _journal_volume 71 _journal_year 2015 _chemical_formula_iupac 'C17 H21 Cl N2 O6' _chemical_formula_moiety 'C17 H21 Cl N2 O6' _chemical_formula_sum 'C17 H21 Cl N2 O6' _chemical_formula_weight 384.81 _chemical_name_systematic ;Ethyl 6-chloromethyl-2-oxo-4-(2,3,4-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 108.552(5) _cell_angle_beta 102.886(5) _cell_angle_gamma 94.406(5) _cell_formula_units_Z 2 _cell_length_a 9.479(5) _cell_length_b 10.080(5) _cell_length_c 10.320(5) _cell_measurement_reflns_used 3737 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.64 _cell_measurement_theta_min 0.98 _cell_volume 899.5(8) _computing_cell_refinement ; APEX2 and SAINT (Bruker, 2008) ; _computing_data_collection ; APEX2 (Bruker, 2008) ; _computing_data_reduction ; SAINT and XPREP (Bruker, 2008) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) ; _computing_publication_material ; PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 2008) ; _computing_structure_solution ; SIR92 (Altomare et al., 1993) ; _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method '\w and \f 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 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12878 _diffrn_reflns_theta_full 26.64 _diffrn_reflns_theta_max 26.64 _diffrn_reflns_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_T_max 0.9755 _exptl_absorpt_correction_T_min 0.9519 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2008) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 404 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.245 _refine_diff_density_min -0.283 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 3737 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0412 _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^)+(0.0599P)^2^+0.3029P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1129 _refine_ls_wR_factor_ref 0.1212 _reflns_number_gt 3025 _reflns_number_total 3737 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL joshpine_bca5_0m in P -1 CELL 0.71073 9.4790 10.0800 10.3200 108.552 102.886 94.406 ZERR 2.00 0.0050 0.0050 0.0050 0.005 0.005 0.005 LATT 1 SFAC C H N O CL UNIT 34 42 4 12 2 MERG 2 MPLA 6 C1 C2 C3 C4 C5 C6 MPLA 6 N1 C11 C12 c13 N2 C14 EQIV $1 -X+1, -Y+1, -Z+1 HTAB N1 O6_$1 EQIV $2 -X, -Y, -Z HTAB N2 O4_$2 FMAP 2 PLAN 25 SIZE 0.10 0.15 0.20 ACTA BOND $H CONF L.S. 10 WGHT 0.059900 0.302900 FVAR 0.22671 C7 1 0.337970 -0.217164 -0.324830 11.00000 0.07238 0.05610 = 0.06637 -0.00029 0.02023 0.01670 AFIX 137 H7A 2 0.399859 -0.150066 -0.344436 11.00000 -1.50000 H7B 2 0.321267 -0.307659 -0.398901 11.00000 -1.50000 H7C 2 0.384801 -0.226006 -0.236020 11.00000 -1.50000 AFIX 0 C4 1 0.205171 -0.039829 -0.221119 11.00000 0.04952 0.03515 = 0.03514 0.00817 0.00887 0.00037 C5 1 0.331697 0.047882 -0.127475 11.00000 0.03842 0.04385 = 0.04397 0.01228 0.01203 0.00248 AFIX 43 H5 2 0.422974 0.020644 -0.129334 11.00000 -1.20000 AFIX 0 C6 1 0.320773 0.176120 -0.031403 11.00000 0.03547 0.03958 = 0.03824 0.00969 0.00332 -0.00582 AFIX 43 H6 2 0.405848 0.233769 0.031676 11.00000 -1.20000 AFIX 0 C1 1 0.187918 0.221037 -0.026275 11.00000 0.03714 0.03166 = 0.03239 0.01063 0.00344 -0.00344 C2 1 0.060344 0.133223 -0.121896 11.00000 0.03549 0.03460 = 0.03710 0.01193 0.00162 -0.00104 C3 1 0.069319 0.002172 -0.217295 11.00000 0.04114 0.03399 = 0.03693 0.00819 -0.00032 -0.00662 C8 1 -0.144084 -0.059587 -0.412231 11.00000 0.06290 0.07101 = 0.04755 0.01269 -0.01234 -0.01651 AFIX 137 H8A 2 -0.157540 0.037705 -0.378081 11.00000 -1.50000 H8B 2 -0.237740 -0.119746 -0.446650 11.00000 -1.50000 H8C 2 -0.096853 -0.073994 -0.487697 11.00000 -1.50000 AFIX 0 C9 1 -0.170666 0.109886 -0.072595 11.00000 0.06687 0.07834 = 0.08918 0.04952 0.03951 0.02498 AFIX 137 H9A 2 -0.176923 0.009185 -0.114860 11.00000 -1.50000 H9B 2 -0.265784 0.135820 -0.097034 11.00000 -1.50000 H9C 2 -0.136480 0.137252 0.028483 11.00000 -1.50000 AFIX 0 C13 1 0.178023 0.359006 0.085165 11.00000 0.03431 0.03516 = 0.03162 0.00869 0.00205 -0.00300 AFIX 13 H13 2 0.078669 0.380655 0.060064 11.00000 -1.20000 AFIX 0 C12 1 0.286240 0.483339 0.094002 11.00000 0.03802 0.02942 = 0.03483 0.00780 0.00592 0.00127 C11 1 0.395610 0.548451 0.211211 11.00000 0.03935 0.03197 = 0.03706 0.00892 0.00776 -0.00098 C14 1 0.317320 0.402064 0.336678 11.00000 0.04388 0.03849 = 0.03512 0.01066 0.00250 -0.00591 C10 1 0.507625 0.673705 0.236505 11.00000 0.04688 0.03731 = 0.04256 0.00820 0.00761 -0.00752 AFIX 23 H10A 2 0.509401 0.685108 0.146999 11.00000 -1.20000 H10B 2 0.604059 0.658157 0.279253 11.00000 -1.20000 AFIX 0 C15 1 0.265896 0.526875 -0.031680 11.00000 0.04239 0.03366 = 0.03837 0.00997 0.00884 0.00515 C16 1 0.109493 0.483784 -0.260163 11.00000 0.06290 0.06108 = 0.04021 0.02198 0.00575 0.01242 AFIX 23 H16A 2 0.194008 0.473909 -0.298867 11.00000 -1.20000 H16B 2 0.086922 0.578690 -0.246905 11.00000 -1.20000 AFIX 0 C17 1 -0.018229 0.376414 -0.357632 11.00000 0.09971 0.07345 = 0.04657 0.01136 -0.01173 0.00008 AFIX 137 H17A 2 0.006705 0.283153 -0.372536 11.00000 -1.50000 H17B 2 -0.043772 0.391595 -0.446633 11.00000 -1.50000 H17C 2 -0.100067 0.385184 -0.316646 11.00000 -1.50000 AFIX 0 N2 3 0.203063 0.340766 0.224262 11.00000 0.04221 0.04074 = 0.03276 0.00963 0.00345 -0.01148 AFIX 43 H2N 2 0.136666 0.284356 0.234055 11.00000 -1.20000 AFIX 0 N1 3 0.413332 0.504536 0.326537 11.00000 0.04631 0.04816 = 0.03685 0.01604 -0.00665 -0.01681 AFIX 43 H1N 2 0.489391 0.543931 0.396437 11.00000 -1.20000 AFIX 0 O5 4 0.202389 -0.169662 -0.317658 11.00000 0.06151 0.04360 = 0.05315 -0.00303 0.01019 0.00606 O4 4 -0.055277 -0.093291 -0.299915 11.00000 0.04831 0.03833 = 0.05349 0.00655 -0.00753 -0.01104 O3 4 -0.071858 0.179596 -0.123144 11.00000 0.03587 0.03982 = 0.05814 0.01541 0.00152 -0.00010 O1 4 0.349308 0.608633 -0.052898 11.00000 0.06044 0.06751 = 0.05574 0.03342 0.00363 -0.01278 O2 4 0.139723 0.459130 -0.126632 11.00000 0.05188 0.05108 = 0.03858 0.01803 -0.00161 -0.00402 O6 4 0.336709 0.371838 0.445103 11.00000 0.06282 0.06300 = 0.04117 0.02505 -0.00842 -0.02349 CL 5 0.464013 0.830043 0.350722 11.00000 0.07705 0.03753 = 0.07159 0.00718 0.01449 0.00201 HKLF 4 REM joshpine_bca5_0m in P -1 REM R1 = 0.0412 for 3025 Fo > 4sig(Fo) and 0.0515 for all 3737 data REM 239 parameters refined using 0 restraints END WGHT 0.0599 0.3029 REM Highest difference peak 0.245, deepest hole -0.283, 1-sigma level 0.042 Q1 1 -0.1417 0.0285 -0.0441 11.00000 0.05 0.24 Q2 1 -0.1063 0.0206 -0.4295 11.00000 0.05 0.23 Q3 1 0.2437 0.4169 0.0894 11.00000 0.05 0.22 Q4 1 0.3068 0.5388 0.1647 11.00000 0.05 0.22 Q5 1 0.1281 0.1821 -0.0547 11.00000 0.05 0.21 Q6 1 0.4022 0.8066 0.2644 11.00000 0.05 0.20 Q7 1 -0.2439 0.1694 -0.0369 11.00000 0.05 0.20 Q8 1 0.3476 0.5005 0.1425 11.00000 0.05 0.20 Q9 1 0.2751 0.5026 0.0445 11.00000 0.05 0.19 Q10 1 0.2537 0.2211 -0.0616 11.00000 0.05 0.19 Q11 1 -0.2653 0.0374 -0.1946 11.00000 0.05 0.18 Q12 1 0.3870 0.5354 0.2695 11.00000 0.05 0.17 Q13 1 -0.0513 0.1654 -0.0387 11.00000 0.05 0.17 Q14 1 -0.0172 -0.0676 -0.3590 11.00000 0.05 0.16 Q15 1 0.0819 0.3466 -0.3756 11.00000 0.05 0.16 Q16 1 0.1358 -0.0334 -0.1831 11.00000 0.05 0.15 Q17 1 0.1791 0.2384 0.2249 11.00000 0.05 0.15 Q18 1 0.1469 0.0001 -0.2521 11.00000 0.05 0.15 Q19 1 -0.2000 -0.1709 -0.4940 11.00000 0.05 0.15 Q20 1 0.0854 0.4182 -0.1051 11.00000 0.05 0.15 Q21 1 0.2232 0.3964 0.2851 11.00000 0.05 0.14 Q22 1 0.3647 0.8223 0.3823 11.00000 0.05 0.14 Q23 1 0.2385 0.1821 0.0009 11.00000 0.05 0.14 Q24 1 0.2680 0.3404 0.4566 11.00000 0.05 0.14 Q25 1 0.2662 0.0226 -0.1982 11.00000 0.05 0.14 ; _cod_data_source_file lh5770sup1.cif _cod_data_source_block I _cod_database_code 2240853 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity C C7 0.3380(3) -0.2172(2) -0.3248(3) 0.0695(6) Uani d . 1 1 H H7A 0.3999 -0.1501 -0.3444 0.104 Uiso calc R 1 1 H H7B 0.3213 -0.3077 -0.3989 0.104 Uiso calc R 1 1 H H7C 0.3848 -0.2260 -0.2360 0.104 Uiso calc R 1 1 C C4 0.2052(2) -0.03983(17) -0.22112(17) 0.0417(4) Uani d . 1 1 C C5 0.33170(19) 0.04788(18) -0.12747(18) 0.0428(4) Uani d . 1 1 H H5 0.4230 0.0206 -0.1293 0.051 Uiso calc R 1 1 C C6 0.32077(18) 0.17612(18) -0.03140(17) 0.0404(4) Uani d . 1 1 H H6 0.4058 0.2338 0.0317 0.049 Uiso calc R 1 1 C C1 0.18792(17) 0.22104(16) -0.02627(16) 0.0353(3) Uani d . 1 1 C C2 0.06034(17) 0.13322(17) -0.12190(17) 0.0375(4) Uani d . 1 1 C C3 0.06932(19) 0.00217(17) -0.21729(17) 0.0409(4) Uani d . 1 1 C C8 -0.1441(3) -0.0596(3) -0.4122(2) 0.0685(6) Uani d . 1 1 H H8A -0.1575 0.0377 -0.3781 0.103 Uiso calc R 1 1 H H8B -0.2377 -0.1197 -0.4467 0.103 Uiso calc R 1 1 H H8C -0.0969 -0.0740 -0.4877 0.103 Uiso calc R 1 1 C C9 -0.1707(3) 0.1099(3) -0.0726(3) 0.0690(6) Uani d . 1 1 H H9A -0.1769 0.0092 -0.1149 0.104 Uiso calc R 1 1 H H9B -0.2658 0.1358 -0.0970 0.104 Uiso calc R 1 1 H H9C -0.1365 0.1373 0.0285 0.104 Uiso calc R 1 1 C C13 0.17802(17) 0.35901(16) 0.08517(16) 0.0360(3) Uani d . 1 1 H H13 0.0787 0.3807 0.0601 0.043 Uiso calc R 1 1 C C12 0.28624(17) 0.48334(16) 0.09400(16) 0.0357(3) Uani d . 1 1 C C11 0.39561(18) 0.54845(16) 0.21121(17) 0.0376(4) Uani d . 1 1 C C14 0.31732(19) 0.40206(18) 0.33668(17) 0.0417(4) Uani d . 1 1 C C10 0.5076(2) 0.67371(18) 0.23650(19) 0.0451(4) Uani d . 1 1 H H10A 0.5094 0.6851 0.1470 0.054 Uiso calc R 1 1 H H10B 0.6041 0.6582 0.2793 0.054 Uiso calc R 1 1 C C15 0.26590(19) 0.52688(17) -0.03168(17) 0.0391(4) Uani d . 1 1 C C16 0.1095(2) 0.4838(2) -0.2602(2) 0.0548(5) Uani d . 1 1 H H16A 0.1940 0.4739 -0.2989 0.066 Uiso calc R 1 1 H H16B 0.0869 0.5787 -0.2469 0.066 Uiso calc R 1 1 C C17 -0.0182(3) 0.3764(3) -0.3576(2) 0.0816(8) Uani d . 1 1 H H17A 0.0067 0.2832 -0.3725 0.122 Uiso calc R 1 1 H H17B -0.0438 0.3916 -0.4466 0.122 Uiso calc R 1 1 H H17C -0.1001 0.3852 -0.3166 0.122 Uiso calc R 1 1 N N2 0.20306(15) 0.34077(15) 0.22426(14) 0.0414(3) Uani d . 1 1 H H2N 0.1367 0.2844 0.2341 0.050 Uiso calc R 1 1 N N1 0.41333(16) 0.50454(16) 0.32654(15) 0.0478(4) Uani d . 1 1 H H1N 0.4894 0.5439 0.3964 0.057 Uiso calc R 1 1 O O5 0.20239(16) -0.16966(14) -0.31766(15) 0.0586(4) Uani d . 1 1 O O4 -0.05528(14) -0.09329(13) -0.29991(14) 0.0536(4) Uani d . 1 1 O O3 -0.07186(13) 0.17960(13) -0.12314(14) 0.0471(3) Uani d . 1 1 O O1 0.34931(16) 0.60863(16) -0.05290(15) 0.0615(4) Uani d . 1 1 O O2 0.13972(14) 0.45913(14) -0.12663(13) 0.0495(3) Uani d . 1 1 O O6 0.33671(15) 0.37184(15) 0.44510(13) 0.0595(4) Uani d . 1 1 Cl Cl 0.46401(7) 0.83004(5) 0.35072(6) 0.06618(19) Uani d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C7 0.0724(15) 0.0561(13) 0.0664(14) 0.0167(11) 0.0202(11) -0.0003(10) C4 0.0495(10) 0.0351(8) 0.0351(8) 0.0004(7) 0.0089(7) 0.0082(7) C5 0.0384(9) 0.0438(9) 0.0440(9) 0.0025(7) 0.0120(7) 0.0123(7) C6 0.0355(8) 0.0396(8) 0.0382(8) -0.0058(7) 0.0033(6) 0.0097(7) C1 0.0371(8) 0.0317(7) 0.0324(7) -0.0034(6) 0.0034(6) 0.0106(6) C2 0.0355(8) 0.0346(8) 0.0371(8) -0.0010(6) 0.0016(6) 0.0119(6) C3 0.0411(9) 0.0340(8) 0.0369(8) -0.0066(7) -0.0003(7) 0.0082(7) C8 0.0629(13) 0.0710(14) 0.0475(11) -0.0165(11) -0.0123(9) 0.0127(10) C9 0.0669(14) 0.0783(15) 0.0892(17) 0.0250(12) 0.0395(13) 0.0495(14) C13 0.0343(8) 0.0352(8) 0.0316(7) -0.0030(6) 0.0020(6) 0.0087(6) C12 0.0380(8) 0.0294(7) 0.0348(8) 0.0013(6) 0.0059(6) 0.0078(6) C11 0.0393(9) 0.0320(8) 0.0371(8) -0.0010(6) 0.0078(7) 0.0089(6) C14 0.0439(9) 0.0385(8) 0.0351(8) -0.0059(7) 0.0025(7) 0.0107(7) C10 0.0469(10) 0.0373(9) 0.0426(9) -0.0075(7) 0.0076(7) 0.0082(7) C15 0.0424(9) 0.0337(8) 0.0384(8) 0.0052(7) 0.0088(7) 0.0100(7) C16 0.0629(12) 0.0611(12) 0.0402(9) 0.0124(10) 0.0058(8) 0.0220(9) C17 0.0997(19) 0.0735(16) 0.0466(12) 0.0001(14) -0.0117(12) 0.0114(11) N2 0.0422(8) 0.0407(7) 0.0328(7) -0.0115(6) 0.0035(6) 0.0096(6) N1 0.0463(8) 0.0482(8) 0.0369(7) -0.0168(7) -0.0066(6) 0.0160(6) O5 0.0615(9) 0.0436(7) 0.0531(8) 0.0061(6) 0.0102(6) -0.0030(6) O4 0.0483(7) 0.0383(6) 0.0535(7) -0.0110(5) -0.0075(6) 0.0066(6) O3 0.0359(6) 0.0398(6) 0.0581(8) -0.0001(5) 0.0015(5) 0.0154(6) O1 0.0604(9) 0.0675(9) 0.0557(8) -0.0128(7) 0.0036(6) 0.0334(7) O2 0.0519(7) 0.0511(7) 0.0386(6) -0.0040(6) -0.0016(5) 0.0180(5) O6 0.0628(9) 0.0630(9) 0.0412(7) -0.0235(7) -0.0084(6) 0.0250(6) Cl 0.0771(4) 0.0375(3) 0.0716(4) 0.0020(2) 0.0145(3) 0.0072(2) 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' 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 O5 C7 H7A 109.5 O5 C7 H7B 109.5 H7A C7 H7B 109.5 O5 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 O5 C4 C5 124.55(17) O5 C4 C3 115.73(15) C5 C4 C3 119.71(16) C6 C5 C4 119.45(17) C6 C5 H5 120.3 C4 C5 H5 120.3 C1 C6 C5 122.07(15) C1 C6 H6 119.0 C5 C6 H6 119.0 C6 C1 C2 118.47(15) C6 C1 C13 121.07(13) C2 C1 C13 120.39(15) O3 C2 C3 120.68(14) O3 C2 C1 119.18(15) C3 C2 C1 120.11(16) O4 C3 C4 118.51(15) O4 C3 C2 121.07(16) C4 C3 C2 120.16(14) O4 C8 H8A 109.5 O4 C8 H8B 109.5 H8A C8 H8B 109.5 O4 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 O3 C9 H9A 109.5 O3 C9 H9B 109.5 H9A C9 H9B 109.5 O3 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 N2 C13 C1 109.46(13) N2 C13 C12 109.91(12) C1 C13 C12 112.61(13) N2 C13 H13 108.2 C1 C13 H13 108.2 C12 C13 H13 108.2 C11 C12 C15 122.12(15) C11 C12 C13 120.78(14) C15 C12 C13 117.09(13) C12 C11 N1 120.98(14) C12 C11 C10 126.74(15) N1 C11 C10 112.26(14) O6 C14 N2 123.26(15) O6 C14 N1 120.67(14) N2 C14 N1 116.06(15) C11 C10 Cl 109.90(13) C11 C10 H10A 109.7 Cl C10 H10A 109.7 C11 C10 H10B 109.7 Cl C10 H10B 109.7 H10A C10 H10B 108.2 O1 C15 O2 122.11(16) O1 C15 C12 127.08(15) O2 C15 C12 110.79(14) O2 C16 C17 107.07(17) O2 C16 H16A 110.3 C17 C16 H16A 110.3 O2 C16 H16B 110.3 C17 C16 H16B 110.3 H16A C16 H16B 108.6 C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C14 N2 C13 127.23(14) C14 N2 H2N 116.4 C13 N2 H2N 116.4 C14 N1 C11 124.02(14) C14 N1 H1N 118.0 C11 N1 H1N 118.0 C4 O5 C7 117.72(15) C3 O4 C8 117.15(15) C2 O3 C9 116.65(15) C15 O2 C16 117.05(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C7 O5 1.415(3) C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C4 O5 1.364(2) C4 C5 1.389(2) C4 C3 1.391(3) C5 C6 1.384(3) C5 H5 0.9300 C6 C1 1.377(3) C6 H6 0.9300 C1 C2 1.403(2) C1 C13 1.522(2) C2 O3 1.370(2) C2 C3 1.396(2) C3 O4 1.3791(19) C8 O4 1.424(3) C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 C9 O3 1.412(2) C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 C13 N2 1.474(2) C13 C12 1.523(2) C13 H13 0.9800 C12 C11 1.341(2) C12 C15 1.475(2) C11 N1 1.378(2) C11 C10 1.500(2) C14 O6 1.230(2) C14 N2 1.335(2) C14 N1 1.369(2) C10 Cl 1.783(2) C10 H10A 0.9700 C10 H10B 0.9700 C15 O1 1.202(2) C15 O2 1.335(2) C16 O2 1.448(2) C16 C17 1.487(3) C16 H16A 0.9700 C16 H16B 0.9700 C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 N2 H2N 0.8600 N1 H1N 0.8600 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_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1N O6 2_666 0.86 1.95 2.812(2) 178.4 N2 H2N O4 2 0.86 2.37 3.160(2) 153.4 C17 H17C Cg 2_567 0.96 2.83 3.676(4) 147 C10 H10A O1 . 0.97 2.14 2.864(3) 131 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 O5 C4 C5 C6 -178.30(16) C3 C4 C5 C6 0.0(3) C4 C5 C6 C1 -0.7(3) C5 C6 C1 C2 0.0(2) C5 C6 C1 C13 176.89(15) C6 C1 C2 O3 -176.62(14) C13 C1 C2 O3 6.5(2) C6 C1 C2 C3 1.4(2) C13 C1 C2 C3 -175.49(14) O5 C4 C3 O4 5.7(2) C5 C4 C3 O4 -172.75(15) O5 C4 C3 C2 179.86(15) C5 C4 C3 C2 1.4(3) O3 C2 C3 O4 -10.1(2) C1 C2 C3 O4 171.86(15) O3 C2 C3 C4 175.89(15) C1 C2 C3 C4 -2.1(2) C6 C1 C13 N2 -72.80(18) C2 C1 C13 N2 104.02(16) C6 C1 C13 C12 49.8(2) C2 C1 C13 C12 -133.40(15) N2 C13 C12 C11 7.4(2) C1 C13 C12 C11 -114.95(17) N2 C13 C12 C15 -173.26(14) C1 C13 C12 C15 64.41(19) C15 C12 C11 N1 -179.15(15) C13 C12 C11 N1 0.2(3) C15 C12 C11 C10 2.3(3) C13 C12 C11 C10 -178.40(16) C12 C11 C10 Cl 103.68(19) N1 C11 C10 Cl -75.01(18) C11 C12 C15 O1 9.9(3) C13 C12 C15 O1 -169.41(18) C11 C12 C15 O2 -171.87(16) C13 C12 C15 O2 8.8(2) O6 C14 N2 C13 -173.33(17) N1 C14 N2 C13 7.7(3) C1 C13 N2 C14 112.29(19) C12 C13 N2 C14 -11.9(2) O6 C14 N1 C11 -177.08(18) N2 C14 N1 C11 1.9(3) C12 C11 N1 C14 -5.6(3) C10 C11 N1 C14 173.14(17) C5 C4 O5 C7 -1.3(3) C3 C4 O5 C7 -179.67(18) C4 C3 O4 C8 -114.3(2) C2 C3 O4 C8 71.6(2) C3 C2 O3 C9 71.6(2) C1 C2 O3 C9 -110.4(2) O1 C15 O2 C16 2.5(3) C12 C15 O2 C16 -175.83(15) C17 C16 O2 C15 168.35(19) _cod_database_fobs_code 2240853