#------------------------------------------------------------------------------ #$Date: 2020-05-16 06:10:06 +0300 (Sat, 16 May 2020) $ #$Revision: 252079 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240541.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_7240541 loop_ _publ_author_name 'Samunuri, Ramakrishnamraju' 'Toyama, Masaaki' 'Pallaka, Renuka Sivasankar' 'Neeladri, Seshubabu' 'Jha, Ashok Kumar' 'Baba, Masanori' 'Bal, Chandralata' _publ_section_title ; Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D0MD00059K _journal_year 2020 _chemical_formula_moiety 'C14 H17 Cl N4 O3' _chemical_formula_sum 'C14 H17 Cl N4 O3' _chemical_formula_weight 324.76 _chemical_melting_point 499 _chemical_name_common 'carbocyclic nucleoside' _chemical_name_systematic (1S,2R,3R,5R)-5-(4-amino-5-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3-(hydroxymethyl)-3-methyl-4-methylenecyclopentane-1,2-diol _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-12-01 _audit_creation_method ; Olex2 1.2-alpha (compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532) ; _audit_update_record ; 2019-12-01 deposited with the CCDC. 2020-05-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.344(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.6168(4) _cell_length_b 6.7974(3) _cell_length_c 13.2395(5) _cell_measurement_reflns_used 3022 _cell_measurement_temperature 293 _cell_measurement_theta_max 28.6430 _cell_measurement_theta_min 4.2720 _cell_volume 765.17(6) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.4324 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Xcalibur, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0125 _diffrn_reflns_av_unetI/netI 0.0198 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 6412 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.367 _diffrn_reflns_theta_min 3.379 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_meas ? _exptl_crystal_description block _exptl_crystal_F_000 340 _exptl_crystal_preparation Synthesis _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Methanol' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.173 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.033 _refine_ls_abs_structure_details ; Flack x determined using 1203 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.011(19) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3143 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0323 _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^)+(0.0388P)^2^+0.1156P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0755 _refine_ls_wR_factor_ref 0.0792 _reflns_Friedel_coverage 0.841 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 2861 _reflns_number_total 3143 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0md00059k2.cif _cod_data_source_block as368184 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 765.18(5) _cod_database_code 7240541 _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 0.948 _shelx_estimated_absorpt_t_min 0.924 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C10(H10), C13(H13), C14(H14) 2.b Aromatic/amide H refined with riding coordinates: C9(H9) 2.c X=CH2 refined with riding coordinates: N22(H22A,H22B) 2.d Idealised Me refined as rotating group: C19(H19A,H19B,H19C) 2.e Idealised tetrahedral OH refined as rotating group: O17(H17), O18(H18) ; _shelx_res_file ; TITL as_c0368_184_a.res in P2(1) as368184.res created by SHELXL-2018/3 at 12:08:50 on 01-Dec-2019 CELL 0.71073 8.616806 6.797401 13.23953 90 99.3435 90 ZERR 2 0.000353 0.000282 0.000453 0 0.0038 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Cl N O UNIT 28 34 2 8 6 L.S. 20 PLAN 25 SIZE 0.3 0.25 0.2 BOND $H fmap 2 ACTA SHEL 59 0.8 OMIT -3 0 6 REM REM REM WGHT 0.038800 0.115600 FVAR 1.19327 CL21 3 0.325159 0.683479 0.516806 11.00000 0.11038 0.09535 = 0.05746 -0.04455 0.04559 -0.02992 O17 5 0.685144 0.623899 -0.003389 11.00000 0.08081 0.04257 = 0.02565 0.00306 0.00960 -0.00253 AFIX 147 H17 2 0.660230 0.672572 -0.060387 11.00000 -1.50000 AFIX 0 O18 5 0.387385 0.725623 0.041652 11.00000 0.05996 0.04924 = 0.06038 -0.00177 -0.01557 0.00067 AFIX 147 H18 2 0.351299 0.834696 0.025074 11.00000 -1.50000 AFIX 0 O16 5 0.917183 0.875970 0.331105 11.00000 0.06370 0.09131 = 0.03492 -0.00097 0.01051 -0.04086 N3 4 0.344547 0.222590 0.208821 11.00000 0.05068 0.04538 = 0.03160 -0.00989 0.01801 -0.01579 N1 4 0.459459 0.535695 0.260245 11.00000 0.05090 0.04061 = 0.03585 -0.00884 0.01793 -0.01184 N5 4 0.186113 0.089350 0.325191 11.00000 0.05391 0.06073 = 0.04341 -0.00833 0.02109 -0.02276 N22 4 0.145362 0.238843 0.473470 11.00000 0.06196 0.08360 = 0.03996 -0.00919 0.02660 -0.01996 AFIX 93 H22A 2 0.088592 0.139827 0.484960 11.00000 -1.20000 H22B 2 0.159253 0.334901 0.516260 11.00000 -1.20000 AFIX 0 C2 1 0.368990 0.377532 0.272532 11.00000 0.03637 0.04198 = 0.02832 -0.00354 0.00852 -0.00475 C7 1 0.306184 0.399400 0.363057 11.00000 0.03528 0.04977 = 0.02758 -0.00610 0.00762 -0.00192 C11 1 0.731374 0.561861 0.218356 11.00000 0.04573 0.03639 = 0.02904 0.00085 0.01162 -0.00340 C10 1 0.555181 0.559498 0.179224 11.00000 0.04571 0.03130 = 0.03033 -0.00377 0.01292 -0.00771 AFIX 13 H10 2 0.533243 0.447434 0.132518 11.00000 -1.20000 AFIX 0 C12 1 0.805218 0.727474 0.165594 11.00000 0.04688 0.04256 = 0.03155 0.00416 0.01027 -0.00941 C13 1 0.677770 0.770338 0.072641 11.00000 0.06133 0.03095 = 0.03001 0.00417 0.00956 -0.00823 AFIX 13 H13 2 0.688212 0.903146 0.045731 11.00000 -1.20000 AFIX 0 C6 1 0.212212 0.243454 0.388845 11.00000 0.03561 0.06141 = 0.03154 -0.00168 0.01043 -0.00474 C14 1 0.523966 0.746269 0.115929 11.00000 0.04790 0.03319 = 0.03616 -0.00232 0.00182 -0.00190 AFIX 13 H14 2 0.510985 0.857402 0.160969 11.00000 -1.20000 AFIX 0 C9 1 0.457805 0.659315 0.342717 11.00000 0.06555 0.04531 = 0.04625 -0.01742 0.02082 -0.01613 AFIX 43 H9 2 0.511955 0.777756 0.353644 11.00000 -1.20000 AFIX 0 C8 1 0.364782 0.580443 0.405031 11.00000 0.05516 0.05627 = 0.03486 -0.01874 0.01671 -0.00607 C15 1 0.823742 0.911111 0.234944 11.00000 0.06288 0.05067 = 0.04430 -0.00384 0.00822 -0.02107 C19 1 0.963818 0.672459 0.135673 11.00000 0.05359 0.08251 = 0.05208 0.00690 0.02087 -0.01030 AFIX 137 H19A 2 1.040315 0.655542 0.196376 11.00000 -1.50000 H19B 2 0.997411 0.775373 0.094496 11.00000 -1.50000 H19C 2 0.953256 0.551938 0.097370 11.00000 -1.50000 AFIX 0 C4 1 0.252285 0.089417 0.240548 11.00000 0.05911 0.05054 = 0.04024 -0.01352 0.01989 -0.02084 C20 1 0.804113 0.436532 0.284464 11.00000 0.06418 0.06481 = 0.05213 0.02138 0.01214 0.00574 H20A 2 0.915434 0.442116 0.305155 11.00000 0.05809 H20B 2 0.745832 0.338575 0.314552 11.00000 0.08001 H15A 2 0.869495 1.012026 0.198857 11.00000 0.05316 H16 2 1.011457 0.919928 0.336647 11.00000 0.07570 H15B 2 0.720106 0.962511 0.250212 11.00000 0.06019 H4 2 0.230375 -0.023411 0.198776 11.00000 0.03858 HKLF 4 REM as_c0368_184_a.res in P2(1) REM wR2 = 0.0792, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0323 for 2861 Fo > 4sig(Fo) and 0.0370 for all 3143 data REM 226 parameters refined using 1 restraints END WGHT 0.0388 0.1156 REM Highest difference peak 0.173, deepest hole -0.213, 1-sigma level 0.033 Q1 1 0.3433 0.7992 0.4982 11.00000 0.05 0.17 Q2 1 0.4156 0.1883 0.1748 11.00000 0.05 0.14 Q3 1 0.6463 0.5736 0.2060 11.00000 0.05 0.12 Q4 1 0.7771 0.6441 0.1928 11.00000 0.05 0.12 Q5 1 0.2232 0.3784 0.3592 11.00000 0.05 0.11 Q6 1 0.2836 0.5284 0.3720 11.00000 0.05 0.11 Q7 1 0.5960 0.7693 0.0970 11.00000 0.05 0.11 Q8 1 0.7279 0.2276 0.1969 11.00000 0.05 0.10 Q9 1 0.7532 0.7689 0.1250 11.00000 0.05 0.10 Q10 1 0.4111 0.6143 0.5241 11.00000 0.05 0.10 Q11 1 0.2483 0.6803 0.4626 11.00000 0.05 0.10 Q12 1 0.5566 0.5906 0.5606 11.00000 0.05 0.10 Q13 1 0.8111 0.7973 0.2017 11.00000 0.05 0.10 Q14 1 0.5372 0.1661 0.1996 11.00000 0.05 0.09 Q15 1 0.3334 0.3737 0.3249 11.00000 0.05 0.09 Q16 1 0.6231 0.7256 0.3687 11.00000 0.05 0.09 Q17 1 0.7626 0.4585 0.2148 11.00000 0.05 0.09 Q18 1 0.5306 1.0492 0.3209 11.00000 0.05 0.09 Q19 1 0.9720 0.8126 0.3007 11.00000 0.05 0.09 Q20 1 0.4785 0.8676 0.3203 11.00000 0.05 0.09 Q21 1 1.0617 0.5533 0.2762 11.00000 0.05 0.09 Q22 1 1.1417 0.6958 0.3189 11.00000 0.05 0.09 Q23 1 0.3504 0.1091 0.2415 11.00000 0.05 0.09 Q24 1 0.0036 0.4460 0.4988 11.00000 0.05 0.09 Q25 1 0.8573 0.6808 0.1461 11.00000 0.05 0.08 ; _shelx_res_checksum 87865 _olex2_submission_original_sample_id as368184 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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_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 Cl21 Cl 0.32516(12) 0.68348(15) 0.51681(7) 0.0842(3) Uani 1 1 d . . . . . O17 O 0.6851(2) 0.6239(3) -0.00339(13) 0.0496(5) Uani 1 1 d . . . . . H17 H 0.660230 0.672572 -0.060387 0.074 Uiso 1 1 calc GR . . . . O18 O 0.3874(2) 0.7256(3) 0.04165(17) 0.0593(6) Uani 1 1 d . . . . . H18 H 0.351299 0.834696 0.025074 0.089 Uiso 1 1 calc GR . . . . O16 O 0.9172(3) 0.8760(4) 0.33110(15) 0.0630(6) Uani 1 1 d . . . . . N3 N 0.3445(2) 0.2226(3) 0.20882(15) 0.0413(5) Uani 1 1 d . . . . . N1 N 0.4595(3) 0.5357(3) 0.26025(15) 0.0412(5) Uani 1 1 d . . . . . N5 N 0.1861(3) 0.0894(4) 0.32519(17) 0.0512(6) Uani 1 1 d . . . . . N22 N 0.1454(3) 0.2388(4) 0.47347(17) 0.0598(7) Uani 1 1 d . . . . . H22A H 0.088592 0.139827 0.484960 0.072 Uiso 1 1 calc R . . . . H22B H 0.159253 0.334901 0.516260 0.072 Uiso 1 1 calc R . . . . C2 C 0.3690(3) 0.3775(4) 0.27253(17) 0.0352(5) Uani 1 1 d . . . . . C7 C 0.3062(3) 0.3994(4) 0.36306(18) 0.0373(5) Uani 1 1 d . . . . . C11 C 0.7314(3) 0.5619(4) 0.21836(17) 0.0364(5) Uani 1 1 d . . . . . C10 C 0.5552(3) 0.5595(3) 0.17922(17) 0.0350(5) Uani 1 1 d . . . . . H10 H 0.533243 0.447434 0.132518 0.042 Uiso 1 1 calc R . . . . C12 C 0.8052(3) 0.7275(4) 0.16559(17) 0.0399(5) Uani 1 1 d . . . . . C13 C 0.6778(3) 0.7703(4) 0.07264(18) 0.0405(6) Uani 1 1 d . . . . . H13 H 0.688212 0.903146 0.045731 0.049 Uiso 1 1 calc R . . . . C6 C 0.2122(3) 0.2435(4) 0.38884(18) 0.0423(6) Uani 1 1 d . . . . . C14 C 0.5240(3) 0.7463(4) 0.11593(19) 0.0396(5) Uani 1 1 d . . . . . H14 H 0.510985 0.857402 0.160969 0.048 Uiso 1 1 calc R . . . . C9 C 0.4578(3) 0.6593(4) 0.3427(2) 0.0511(7) Uani 1 1 d . . . . . H9 H 0.511955 0.777756 0.353644 0.061 Uiso 1 1 calc R . . . . C8 C 0.3648(3) 0.5804(4) 0.40503(19) 0.0477(6) Uani 1 1 d . . . . . C15 C 0.8237(4) 0.9111(5) 0.2349(2) 0.0527(7) Uani 1 1 d . . . . . C19 C 0.9638(3) 0.6725(6) 0.1357(2) 0.0614(8) Uani 1 1 d . . . . . H19A H 1.040315 0.655542 0.196376 0.092 Uiso 1 1 calc GR . . . . H19B H 0.997411 0.775373 0.094496 0.092 Uiso 1 1 calc GR . . . . H19C H 0.953256 0.551938 0.097370 0.092 Uiso 1 1 calc GR . . . . C4 C 0.2523(3) 0.0894(4) 0.2405(2) 0.0486(7) Uani 1 1 d . . . . . C20 C 0.8041(4) 0.4365(5) 0.2845(2) 0.0601(8) Uani 1 1 d . . . . . H20A H 0.915(4) 0.442(5) 0.305(2) 0.058(9) Uiso 1 1 d . . . . . H20B H 0.746(4) 0.339(6) 0.315(3) 0.080(12) Uiso 1 1 d . . . . . H15A H 0.869(3) 1.012(5) 0.199(2) 0.053(8) Uiso 1 1 d . . . . . H16 H 1.011(5) 0.920(6) 0.337(3) 0.076(11) Uiso 1 1 d . . . . . H15B H 0.720(4) 0.963(5) 0.250(2) 0.060(9) Uiso 1 1 d . . . . . H4 H 0.230(3) -0.023(4) 0.199(2) 0.039(7) 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 Cl21 0.1104(7) 0.0953(7) 0.0575(5) -0.0446(5) 0.0456(5) -0.0299(6) O17 0.0808(13) 0.0426(10) 0.0256(8) 0.0031(7) 0.0096(8) -0.0025(9) O18 0.0600(11) 0.0492(12) 0.0604(12) -0.0018(10) -0.0156(10) 0.0007(10) O16 0.0637(13) 0.0913(17) 0.0349(10) -0.0010(10) 0.0105(9) -0.0409(13) N3 0.0507(11) 0.0454(12) 0.0316(10) -0.0099(9) 0.0180(9) -0.0158(10) N1 0.0509(11) 0.0406(12) 0.0359(10) -0.0088(9) 0.0179(9) -0.0118(10) N5 0.0539(13) 0.0607(15) 0.0434(12) -0.0083(11) 0.0211(10) -0.0228(12) N22 0.0620(14) 0.084(2) 0.0400(12) -0.0092(13) 0.0266(11) -0.0200(14) C2 0.0364(11) 0.0420(13) 0.0283(11) -0.0035(10) 0.0085(9) -0.0047(10) C7 0.0353(11) 0.0498(14) 0.0276(11) -0.0061(11) 0.0076(9) -0.0019(11) C11 0.0457(12) 0.0364(12) 0.0290(11) 0.0009(10) 0.0116(10) -0.0034(11) C10 0.0457(12) 0.0313(12) 0.0303(11) -0.0038(9) 0.0129(10) -0.0077(10) C12 0.0469(12) 0.0426(14) 0.0315(11) 0.0042(11) 0.0103(10) -0.0094(11) C13 0.0613(15) 0.0310(12) 0.0300(12) 0.0042(9) 0.0096(11) -0.0082(11) C6 0.0356(11) 0.0614(17) 0.0315(12) -0.0017(12) 0.0104(9) -0.0047(12) C14 0.0479(13) 0.0332(12) 0.0362(12) -0.0023(10) 0.0018(10) -0.0019(11) C9 0.0656(16) 0.0453(15) 0.0463(15) -0.0174(12) 0.0208(13) -0.0161(14) C8 0.0552(14) 0.0563(16) 0.0349(12) -0.0187(12) 0.0167(11) -0.0061(13) C15 0.0629(18) 0.0507(16) 0.0443(15) -0.0038(13) 0.0082(14) -0.0211(16) C19 0.0536(15) 0.083(2) 0.0521(16) 0.0069(17) 0.0209(13) -0.0103(17) C4 0.0591(16) 0.0505(16) 0.0402(13) -0.0135(13) 0.0199(12) -0.0208(14) C20 0.064(2) 0.065(2) 0.0521(18) 0.0214(16) 0.0121(16) 0.0057(17) 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' Cl Cl 0.1484 0.1585 '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 O17 H17 109.5 . . ? C14 O18 H18 109.5 . . ? C15 O16 H16 114(3) . . ? C4 N3 C2 112.3(2) . . ? C2 N1 C10 125.4(2) . . ? C2 N1 C9 108.0(2) . . ? C9 N1 C10 126.3(2) . . ? C4 N5 C6 118.4(2) . . ? H22A N22 H22B 120.0 . . ? C6 N22 H22A 120.0 . . ? C6 N22 H22B 120.0 . . ? N3 C2 N1 125.6(2) . . ? N3 C2 C7 125.2(2) . . ? N1 C2 C7 109.2(2) . . ? C2 C7 C6 116.4(2) . . ? C2 C7 C8 105.5(2) . . ? C6 C7 C8 138.1(2) . . ? C12 C11 C10 108.7(2) . . ? C20 C11 C10 124.4(3) . . ? C20 C11 C12 126.9(3) . . ? N1 C10 C11 113.64(19) . . ? N1 C10 H10 107.6 . . ? N1 C10 C14 115.2(2) . . ? C11 C10 H10 107.6 . . ? C14 C10 C11 104.84(19) . . ? C14 C10 H10 107.6 . . ? C11 C12 C13 102.15(19) . . ? C11 C12 C15 109.7(2) . . ? C11 C12 C19 113.4(2) . . ? C13 C12 C15 108.3(2) . . ? C19 C12 C13 113.0(2) . . ? C19 C12 C15 110.0(2) . . ? O17 C13 C12 109.0(2) . . ? O17 C13 H13 111.7 . . ? O17 C13 C14 109.2(2) . . ? C12 C13 H13 111.7 . . ? C14 C13 C12 103.21(18) . . ? C14 C13 H13 111.7 . . ? N5 C6 N22 117.1(2) . . ? N5 C6 C7 118.7(2) . . ? N22 C6 C7 124.2(2) . . ? O18 C14 C10 110.7(2) . . ? O18 C14 C13 115.0(2) . . ? O18 C14 H14 109.6 . . ? C10 C14 C13 102.03(19) . . ? C10 C14 H14 109.6 . . ? C13 C14 H14 109.6 . . ? N1 C9 H9 125.5 . . ? C8 C9 N1 109.0(2) . . ? C8 C9 H9 125.5 . . ? C7 C8 Cl21 125.9(2) . . ? C9 C8 Cl21 125.7(2) . . ? C9 C8 C7 108.4(2) . . ? O16 C15 C12 112.9(3) . . ? O16 C15 H15A 110.5(19) . . ? O16 C15 H15B 105.8(19) . . ? C12 C15 H15A 107.1(19) . . ? C12 C15 H15B 112.9(19) . . ? H15A C15 H15B 108(3) . . ? C12 C19 H19A 109.5 . . ? C12 C19 H19B 109.5 . . ? C12 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C4 N5 129.0(3) . . ? N3 C4 H4 116.3(16) . . ? N5 C4 H4 114.7(16) . . ? C11 C20 H20A 121(2) . . ? C11 C20 H20B 120(2) . . ? H20A C20 H20B 119(3) . . ? 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 Cl21 C8 1.721(2) . ? O17 H17 0.8200 . ? O17 C13 1.424(3) . ? O18 H18 0.8200 . ? O18 C14 1.413(3) . ? O16 C15 1.412(4) . ? O16 H16 0.86(4) . ? N3 C2 1.344(3) . ? N3 C4 1.318(3) . ? N1 C2 1.353(3) . ? N1 C10 1.464(3) . ? N1 C9 1.380(3) . ? N5 C6 1.340(3) . ? N5 C4 1.337(3) . ? N22 H22A 0.8600 . ? N22 H22B 0.8600 . ? N22 C6 1.341(3) . ? C2 C7 1.401(3) . ? C7 C6 1.409(4) . ? C7 C8 1.410(4) . ? C11 C10 1.523(3) . ? C11 C12 1.518(3) . ? C11 C20 1.306(4) . ? C10 H10 0.9800 . ? C10 C14 1.521(3) . ? C12 C13 1.538(3) . ? C12 C15 1.542(4) . ? C12 C19 1.530(4) . ? C13 H13 0.9800 . ? C13 C14 1.536(4) . ? C14 H14 0.9800 . ? C9 H9 0.9300 . ? C9 C8 1.351(4) . ? C15 H15A 0.96(3) . ? C15 H15B 1.01(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C4 H4 0.95(3) . ? C20 H20A 0.95(3) . ? C20 H20B 0.96(4) . ?