#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:18:19 +0300 (Thu, 07 May 2020) $ #$Revision: 251829 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240469.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_7240469 loop_ _publ_author_name 'Zhang, Guoshun' 'shang, xiaoqing' 'han, wei' 'zhang, lifeng' 'ren, guolian' 'Zhang, Shuqiu' _publ_section_title ; Synthesis, Structural Characterization, Physicochemical Properties and Transformations of Dehydroevodiamine and Its Hydrochloride Salts ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00136H _journal_year 2020 _chemical_formula_moiety 'C19 H16 N3 O, Cl' _chemical_formula_sum 'C19 H16 Cl N3 O' _chemical_formula_weight 337.80 _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 mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-01-29 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.805(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.8763(11) _cell_length_b 7.2318(5) _cell_length_c 14.9535(11) _cell_measurement_reflns_used 3885 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 28.273 _cell_measurement_theta_min 3.144 _cell_volume 1568.7(2) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type CCD _diffrn_measurement_method \w\k _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_unetI/netI 0.0350 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 16148 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.273 _diffrn_reflns_theta_min 3.144 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ' Higashi, T. (1995)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.430 _exptl_crystal_description needle-like _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.227 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 3885 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0454 _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^)+(0.0598P)^2^+0.3713P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1129 _refine_ls_wR_factor_ref 0.1271 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2670 _reflns_number_total 3885 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00136h2.cif _cod_data_source_block DHEDHCl _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240469 _shelx_shelxl_version_number 2014/7 _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_res_file ; 20191013.res created by SHELXL-2014/7 TITL 20191013.ins in P2(1)/n CELL 0.71073 14.8763 7.2318 14.9535 90 102.805 90 ZERR 4 0.0011 0.0005 0.0011 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Cl UNIT 76 64 12 4 4 L.S. 4 PLAN 20 TEMP 23.8 BOND BOND $H HTAB N1 Cl1 HTAB FMAP 2 ACTA REM REM REM WGHT 0.059800 0.371300 FVAR 0.85560 CL1 5 0.162368 0.128450 0.501541 11.00000 0.05222 0.06961 = 0.03004 -0.00260 0.00563 -0.00507 N1 3 0.230346 0.140961 0.715731 11.00000 0.04396 0.04495 = 0.02489 0.00127 0.00359 -0.00246 N2 3 0.110920 0.175181 0.908182 11.00000 0.05967 0.04906 = 0.02498 -0.00493 0.00965 -0.00443 N3 3 0.034685 0.113359 0.756547 11.00000 0.04702 0.03779 = 0.02703 -0.00415 0.01060 -0.00261 O1 4 0.031166 0.233002 1.018241 11.00000 0.09118 0.14254 = 0.03583 -0.02242 0.02340 0.00024 C1 1 0.382659 0.132310 0.670629 11.00000 0.05214 0.04986 = 0.03810 -0.00060 0.00888 -0.00443 AFIX 43 H1B 2 0.359783 0.152424 0.608306 11.00000 -1.20000 AFIX 0 C19 1 0.036236 0.050620 0.662755 11.00000 0.04645 0.05782 = 0.03130 -0.01449 0.00872 -0.00160 AFIX 137 H19A 2 -0.017280 -0.023599 0.639209 11.00000 -1.50000 H19B 2 0.090774 -0.021422 0.664369 11.00000 -1.50000 H19C 2 0.036219 0.156162 0.623812 11.00000 -1.50000 AFIX 0 C2 1 0.475267 0.110174 0.706062 11.00000 0.04996 0.05469 = 0.05611 -0.00215 0.01567 -0.00643 AFIX 43 H2A 2 0.515662 0.114361 0.666717 11.00000 -1.20000 AFIX 0 C3 1 0.510837 0.081294 0.800349 11.00000 0.04412 0.06073 = 0.06432 0.00172 0.00054 -0.00102 AFIX 43 H3A 2 0.573955 0.065290 0.821934 11.00000 -1.20000 AFIX 0 C4 1 0.454150 0.076436 0.860475 11.00000 0.05424 0.05743 = 0.04459 0.00472 -0.00400 -0.00100 AFIX 43 H4A 2 0.478321 0.059029 0.922790 11.00000 -1.20000 AFIX 0 C5 1 0.358616 0.098079 0.827117 11.00000 0.04912 0.03472 = 0.03500 0.00155 0.00053 -0.00525 C6 1 0.323586 0.123468 0.732016 11.00000 0.04580 0.03257 = 0.03466 -0.00148 0.00441 -0.00341 C7 1 0.204049 0.131416 0.799204 11.00000 0.05136 0.03246 = 0.02474 -0.00045 0.00650 -0.00234 C8 1 0.282313 0.107796 0.868415 11.00000 0.05430 0.03637 = 0.02896 0.00157 0.00282 -0.00339 C9 1 0.276734 0.100665 0.966376 11.00000 0.06688 0.06091 = 0.02807 0.00458 0.00129 -0.00197 AFIX 23 H9A 2 0.333413 0.146980 1.005004 11.00000 -1.20000 H9B 2 0.267799 -0.025832 0.984158 11.00000 -1.20000 AFIX 0 C10 1 0.196843 0.218182 0.977497 11.00000 0.07011 0.06293 = 0.02803 -0.01092 0.00419 -0.00850 AFIX 23 H10A 2 0.185859 0.199334 1.038409 11.00000 -1.20000 H10B 2 0.212393 0.347354 0.972107 11.00000 -1.20000 AFIX 0 C11 1 0.113337 0.140484 0.818435 11.00000 0.05321 0.03019 = 0.02714 -0.00017 0.00944 -0.00221 C12 1 -0.052488 0.140163 0.778005 11.00000 0.05185 0.03754 = 0.03638 0.00011 0.01861 -0.00146 C13 1 -0.055542 0.183079 0.868336 11.00000 0.06134 0.05079 = 0.03788 -0.00153 0.02095 -0.00376 C14 1 0.028361 0.198254 0.938144 11.00000 0.07267 0.06349 = 0.03469 -0.00543 0.02136 -0.00159 C15 1 -0.140524 0.215847 0.890835 11.00000 0.07366 0.06976 = 0.05081 -0.00531 0.03527 -0.00256 AFIX 43 H15A 2 -0.142387 0.245724 0.950888 11.00000 -1.20000 AFIX 0 C16 1 -0.220894 0.204519 0.825673 11.00000 0.05947 0.07422 = 0.06818 -0.00050 0.03477 0.00006 AFIX 43 H16A 2 -0.277210 0.226665 0.840977 11.00000 -1.20000 AFIX 0 C17 1 -0.217183 0.159532 0.736459 11.00000 0.05165 0.07263 = 0.05918 0.00094 0.01852 0.00040 AFIX 43 H17A 2 -0.271811 0.150246 0.692174 11.00000 -1.20000 AFIX 0 C18 1 -0.134212 0.128072 0.711608 11.00000 0.05217 0.05778 = 0.04240 -0.00280 0.01532 -0.00136 AFIX 43 H18A 2 -0.133106 0.099201 0.651256 11.00000 -1.20000 AFIX 0 H1A 2 0.197790 0.155053 0.662203 11.00000 0.06603 HKLF 4 REM 20191013.ins in P2(1)/n REM R1 = 0.0454 for 2670 Fo > 4sig(Fo) and 0.0753 for all 3885 data REM 222 parameters refined using 0 restraints END WGHT 0.0573 0.4025 REM Instructions for potential hydrogen bonds EQIV $1 -x, -y, -z+1 HTAB C19 Cl1_$1 HTAB C19 N1 HTAB C19 Cl1 EQIV $2 -x+1/2, y-1/2, -z+3/2 HTAB C9 Cl1_$2 EQIV $3 -x+1/2, y+1/2, -z+3/2 HTAB C10 Cl1_$3 HTAB C18 Cl1_$1 HTAB N1 Cl1 REM Highest difference peak 0.227, deepest hole -0.217, 1-sigma level 0.039 Q1 1 0.3441 0.1144 0.7797 11.00000 0.05 0.23 Q2 1 0.2420 0.0728 0.8358 11.00000 0.05 0.21 Q3 1 0.3530 0.1216 0.7024 11.00000 0.05 0.19 Q4 1 -0.0958 0.1409 0.8816 11.00000 0.05 0.19 Q5 1 0.0377 0.0838 0.7139 11.00000 0.05 0.18 Q6 1 0.1583 0.1884 0.8038 11.00000 0.05 0.18 Q7 1 0.2379 0.1648 0.8400 11.00000 0.05 0.18 Q8 1 -0.0582 0.1266 0.8290 11.00000 0.05 0.18 Q9 1 -0.0119 0.1383 0.7645 11.00000 0.05 0.17 Q10 1 0.4768 0.1345 0.8216 11.00000 0.05 0.17 Q11 1 0.1827 0.1953 0.5632 11.00000 0.05 0.16 Q12 1 0.3272 0.1385 0.8523 11.00000 0.05 0.16 Q13 1 0.4921 0.0679 0.7581 11.00000 0.05 0.16 Q14 1 -0.0159 0.1837 0.8963 11.00000 0.05 0.16 Q15 1 0.2142 0.1708 0.7643 11.00000 0.05 0.15 Q16 1 0.2788 0.0854 0.9073 11.00000 0.05 0.15 Q17 1 0.3224 0.0592 0.8493 11.00000 0.05 0.15 Q18 1 0.1026 0.1350 0.5176 11.00000 0.05 0.15 Q19 1 0.0571 0.3382 1.0028 11.00000 0.05 0.15 Q20 1 0.0744 0.1949 0.7787 11.00000 0.05 0.14 ; _shelx_res_checksum 33593 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 Cl1 Cl 0.16237(3) 0.12845(8) 0.50154(3) 0.05117(17) Uani 1 1 d . . . . . N1 N 0.23035(11) 0.1410(2) 0.71573(10) 0.0386(3) Uani 1 1 d . . . . . N2 N 0.11092(11) 0.1752(2) 0.90818(9) 0.0445(4) Uani 1 1 d . . . . . N3 N 0.03469(10) 0.1134(2) 0.75655(9) 0.0369(3) Uani 1 1 d . . . . . O1 O 0.03117(12) 0.2330(3) 1.01824(10) 0.0884(6) Uani 1 1 d . . . . . C1 C 0.38266(13) 0.1323(3) 0.67063(13) 0.0469(5) Uani 1 1 d . . . . . H1B H 0.3598 0.1524 0.6083 0.056 Uiso 1 1 calc R U . . . C19 C 0.03624(13) 0.0506(3) 0.66276(11) 0.0452(5) Uani 1 1 d . . . . . H19A H -0.0173 -0.0236 0.6392 0.068 Uiso 1 1 calc R U . . . H19B H 0.0908 -0.0214 0.6644 0.068 Uiso 1 1 calc R U . . . H19C H 0.0362 0.1562 0.6238 0.068 Uiso 1 1 calc R U . . . C2 C 0.47527(14) 0.1102(3) 0.70606(15) 0.0530(5) Uani 1 1 d . . . . . H2A H 0.5157 0.1144 0.6667 0.064 Uiso 1 1 calc R U . . . C3 C 0.51084(15) 0.0813(3) 0.80035(15) 0.0582(5) Uani 1 1 d . . . . . H3A H 0.5740 0.0653 0.8219 0.070 Uiso 1 1 calc R U . . . C4 C 0.45415(14) 0.0764(3) 0.86048(14) 0.0544(5) Uani 1 1 d . . . . . H4A H 0.4783 0.0590 0.9228 0.065 Uiso 1 1 calc R U . . . C5 C 0.35862(13) 0.0981(2) 0.82712(12) 0.0410(4) Uani 1 1 d . . . . . C6 C 0.32359(12) 0.1235(2) 0.73202(11) 0.0384(4) Uani 1 1 d . . . . . C7 C 0.20405(12) 0.1314(2) 0.79920(10) 0.0365(4) Uani 1 1 d . . . . . C8 C 0.28231(13) 0.1078(2) 0.86841(11) 0.0409(4) Uani 1 1 d . . . . . C9 C 0.27673(15) 0.1007(3) 0.96638(12) 0.0534(5) Uani 1 1 d . . . . . H9A H 0.3334 0.1470 1.0050 0.064 Uiso 1 1 calc R U . . . H9B H 0.2678 -0.0258 0.9842 0.064 Uiso 1 1 calc R U . . . C10 C 0.19684(15) 0.2182(3) 0.97750(12) 0.0547(5) Uani 1 1 d . . . . . H10A H 0.1859 0.1993 1.0384 0.066 Uiso 1 1 calc R U . . . H10B H 0.2124 0.3474 0.9721 0.066 Uiso 1 1 calc R U . . . C11 C 0.11334(13) 0.1405(2) 0.81844(11) 0.0368(4) Uani 1 1 d . . . . . C12 C -0.05249(13) 0.1402(2) 0.77801(12) 0.0406(4) Uani 1 1 d . . . . . C13 C -0.05554(14) 0.1831(3) 0.86834(13) 0.0485(5) Uani 1 1 d . . . . . C14 C 0.02836(16) 0.1983(3) 0.93814(13) 0.0555(5) Uani 1 1 d . . . . . C15 C -0.14052(17) 0.2158(3) 0.89083(15) 0.0614(6) Uani 1 1 d . . . . . H15A H -0.1424 0.2457 0.9509 0.074 Uiso 1 1 calc R U . . . C16 C -0.22089(17) 0.2045(4) 0.82567(16) 0.0641(6) Uani 1 1 d . . . . . H16A H -0.2772 0.2267 0.8410 0.077 Uiso 1 1 calc R U . . . C17 C -0.21718(15) 0.1595(3) 0.73646(16) 0.0602(6) Uani 1 1 d . . . . . H17A H -0.2718 0.1502 0.6922 0.072 Uiso 1 1 calc R U . . . C18 C -0.13421(14) 0.1281(3) 0.71161(14) 0.0500(5) Uani 1 1 d . . . . . H18A H -0.1331 0.0992 0.6513 0.060 Uiso 1 1 calc R U . . . H1A H 0.1978(16) 0.155(3) 0.6622(16) 0.066(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 Cl1 0.0522(3) 0.0696(4) 0.0300(2) -0.0026(2) 0.00563(17) -0.0051(2) N1 0.0440(9) 0.0449(9) 0.0249(7) 0.0013(6) 0.0036(6) -0.0025(7) N2 0.0597(10) 0.0491(9) 0.0250(7) -0.0049(6) 0.0096(6) -0.0044(8) N3 0.0470(8) 0.0378(8) 0.0270(7) -0.0041(6) 0.0106(6) -0.0026(7) O1 0.0912(13) 0.1425(19) 0.0358(8) -0.0224(10) 0.0234(8) 0.0002(12) C1 0.0521(12) 0.0499(11) 0.0381(9) -0.0006(8) 0.0089(8) -0.0044(9) C19 0.0464(10) 0.0578(12) 0.0313(9) -0.0145(8) 0.0087(7) -0.0016(9) C2 0.0500(12) 0.0547(13) 0.0561(12) -0.0022(10) 0.0157(9) -0.0064(10) C3 0.0441(11) 0.0607(14) 0.0643(13) 0.0017(11) 0.0005(9) -0.0010(10) C4 0.0542(12) 0.0574(13) 0.0446(11) 0.0047(9) -0.0040(9) -0.0010(10) C5 0.0491(11) 0.0347(10) 0.0350(9) 0.0015(7) 0.0005(7) -0.0053(8) C6 0.0458(10) 0.0326(9) 0.0347(8) -0.0015(7) 0.0044(7) -0.0034(8) C7 0.0514(10) 0.0325(9) 0.0247(7) -0.0004(6) 0.0065(7) -0.0023(8) C8 0.0543(11) 0.0364(10) 0.0290(8) 0.0016(7) 0.0028(7) -0.0034(8) C9 0.0669(13) 0.0609(13) 0.0281(9) 0.0046(8) 0.0013(8) -0.0020(11) C10 0.0701(14) 0.0629(13) 0.0280(9) -0.0109(9) 0.0042(8) -0.0085(11) C11 0.0532(11) 0.0302(8) 0.0271(8) -0.0002(6) 0.0094(7) -0.0022(8) C12 0.0518(11) 0.0375(9) 0.0364(9) 0.0001(7) 0.0186(7) -0.0015(8) C13 0.0613(13) 0.0508(11) 0.0379(10) -0.0015(8) 0.0209(8) -0.0038(10) C14 0.0727(15) 0.0635(13) 0.0347(10) -0.0054(9) 0.0214(9) -0.0016(11) C15 0.0737(16) 0.0698(15) 0.0508(12) -0.0053(11) 0.0353(11) -0.0026(12) C16 0.0595(14) 0.0742(16) 0.0682(15) -0.0005(12) 0.0348(12) 0.0001(12) C17 0.0516(13) 0.0726(16) 0.0592(13) 0.0009(11) 0.0185(10) 0.0004(11) C18 0.0522(12) 0.0578(12) 0.0424(10) -0.0028(9) 0.0153(8) -0.0014(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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C7 108.27(14) . . ? C6 N1 H1A 121.9(16) . . ? C7 N1 H1A 129.8(16) . . ? C11 N2 C14 123.12(16) . . ? C11 N2 C10 120.92(16) . . ? C14 N2 C10 115.38(15) . . ? C11 N3 C12 121.89(14) . . ? C11 N3 C19 120.44(14) . . ? C12 N3 C19 117.66(14) . . ? C2 C1 C6 117.53(17) . . ? C2 C1 H1B 121.2 . . ? C6 C1 H1B 121.2 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 C2 C3 121.79(19) . . ? C1 C2 H2A 119.1 . . ? C3 C2 H2A 119.1 . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 119.18(18) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C4 C5 C8 134.33(17) . . ? C4 C5 C6 119.29(18) . . ? C8 C5 C6 106.33(16) . . ? N1 C6 C1 129.73(16) . . ? N1 C6 C5 109.03(15) . . ? C1 C6 C5 121.21(17) . . ? C8 C7 N1 108.64(16) . . ? C8 C7 C11 121.66(15) . . ? N1 C7 C11 129.70(15) . . ? C7 C8 C5 107.69(15) . . ? C7 C8 C9 121.26(17) . . ? C5 C8 C9 131.04(17) . . ? C8 C9 C10 107.96(16) . . ? C8 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? C8 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? N2 C10 C9 112.55(16) . . ? N2 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? N3 C11 N2 119.68(16) . . ? N3 C11 C7 124.74(15) . . ? N2 C11 C7 115.56(15) . . ? C18 C12 C13 119.57(17) . . ? C18 C12 N3 121.92(15) . . ? C13 C12 N3 118.50(17) . . ? C12 C13 C15 119.7(2) . . ? C12 C13 C14 120.55(18) . . ? C15 C13 C14 119.75(18) . . ? O1 C14 N2 119.8(2) . . ? O1 C14 C13 124.3(2) . . ? N2 C14 C13 115.89(16) . . ? C16 C15 C13 120.84(19) . . ? C16 C15 H15A 119.6 . . ? C13 C15 H15A 119.6 . . ? C15 C16 C17 119.0(2) . . ? C15 C16 H16A 120.5 . . ? C17 C16 H16A 120.5 . . ? C18 C17 C16 121.7(2) . . ? C18 C17 H17A 119.2 . . ? C16 C17 H17A 119.2 . . ? C17 C18 C12 119.21(19) . . ? C17 C18 H18A 120.4 . . ? C12 C18 H18A 120.4 . . ? 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 N1 C6 1.360(2) . ? N1 C7 1.390(2) . ? N1 H1A 0.84(2) . ? N2 C11 1.374(2) . ? N2 C14 1.407(3) . ? N2 C10 1.489(2) . ? N3 C11 1.336(2) . ? N3 C12 1.417(2) . ? N3 C19 1.479(2) . ? O1 C14 1.215(2) . ? C1 C2 1.371(3) . ? C1 C6 1.406(3) . ? C1 H1B 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C2 C3 1.407(3) . ? C2 H2A 0.9300 . ? C3 C4 1.363(3) . ? C3 H3A 0.9300 . ? C4 C5 1.407(3) . ? C4 H4A 0.9300 . ? C5 C8 1.409(3) . ? C5 C6 1.414(2) . ? C7 C8 1.386(2) . ? C7 C11 1.442(3) . ? C8 C9 1.486(2) . ? C9 C10 1.500(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C18 1.392(3) . ? C12 C13 1.396(2) . ? C13 C15 1.399(3) . ? C13 C14 1.443(3) . ? C15 C16 1.367(3) . ? C15 H15A 0.9300 . ? C16 C17 1.386(3) . ? C16 H16A 0.9300 . ? C17 C18 1.384(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.84(2) 2.35(2) 3.1391(15) 156(2) .