#------------------------------------------------------------------------------ #$Date: 2021-11-18 03:19:04 +0200 (Thu, 18 Nov 2021) $ #$Revision: 270741 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061066.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_7061066 loop_ _publ_author_name 'Rokkam, Siva Kumar' 'Yadav, Mamta' 'Joshi, Mayank' 'Choudhury, Angshuman Roy' 'Sahal, Dinkar' 'Golakoti, Nageswara Rao' _publ_section_title ; Synthesis, in vitro anti-plasmodial potency, in-silico-cum-SPR binding with inhibition of PfPyridoxal synthase and rapid parasiticidal action by 3,5-bis{(E) arylidene}-N-methyl-4-piperidones ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04604G _journal_year 2021 _chemical_formula_moiety 'C20 H17 Cl2 N O' _chemical_formula_sum 'C20 H17 Cl2 N O' _chemical_formula_weight 358.24 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-10-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-18 deposited with the CCDC. 2021-10-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.323(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.4902(4) _cell_length_b 14.2399(8) _cell_length_c 23.1491(14) _cell_measurement_reflns_used 2251 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.7420 _cell_measurement_theta_min 2.8470 _cell_volume 1753.5(2) _computing_cell_refinement 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.7f (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 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.826 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -69.00 118.20 0.30 12.00 -- 29.89 54.00 47.00 624 2 \w -6.00 20.10 0.30 12.00 -- 29.89 54.00-180.00 87 3 \w -69.00 -18.00 0.30 12.00 -- 29.89 54.00-180.00 170 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0007693000 _diffrn_orient_matrix_UB_12 -0.0395275000 _diffrn_orient_matrix_UB_13 -0.0186835000 _diffrn_orient_matrix_UB_21 0.1160722000 _diffrn_orient_matrix_UB_22 -0.0151223000 _diffrn_orient_matrix_UB_23 0.0186985000 _diffrn_orient_matrix_UB_31 -0.0655487000 _diffrn_orient_matrix_UB_32 -0.0262675000 _diffrn_orient_matrix_UB_33 0.0173819000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_unetI/netI 0.0375 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.826 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 11576 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.826 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 32.795 _diffrn_reflns_theta_min 2.861 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.95399 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.357 _exptl_crystal_description block _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.190 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 5387 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0941 _refine_ls_R_factor_gt 0.0539 _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^)+(0.0741P)^2^+0.1853P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1383 _refine_ls_wR_factor_ref 0.1732 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3158 _reflns_number_total 5387 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL 4cl_nm_dbp_rt_a.res in P2(1)/c 4cl_nm_dbp_rt.res created by SHELXL-2017/1 at 12:32:49 on 14-Oct-2019 REM Old TITL 4Cl_NM_DBP_RT in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.167, Rweak 0.027, Alpha 0.016, Orientation as input REM Formula found by SHELXT: C20 N O Cl2 CELL 0.71073 5.4902 14.2399 23.1491 90 104.323 90 ZERR 4 0.0004 0.0008 0.0014 0 0.006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 80 68 8 4 4 L.S. 4 0 0 PLAN 20 list 4 HTAB BOND $H CONF fmap 2 53 acta 50 OMIT 1 0 0 OMIT 1 4 10 OMIT 1 3 2 OMIT 1 4 14 OMIT -1 5 12 OMIT 1 3 8 OMIT -1 4 3 OMIT -1 2 6 OMIT 1 0 2 OMIT -1 8 3 OMIT -1 1 8 OMIT 1 1 8 OMIT 1 6 0 OMIT 2 1 2 REM REM REM WGHT 0.074100 0.185300 FVAR 0.71192 CL2 3 0.875631 0.352197 0.739817 11.00000 0.09156 0.07386 = 0.05860 -0.00085 0.01348 -0.00046 CL1 3 0.160478 0.375330 0.013354 11.00000 0.11184 0.09749 = 0.05833 0.00806 0.02488 0.01495 O1 5 -0.009422 0.423198 0.375259 11.00000 0.06844 0.08627 = 0.07073 -0.00060 0.02158 0.02530 N1 4 0.442306 0.213372 0.374137 11.00000 0.07195 0.04409 = 0.05697 -0.00096 0.01814 0.00509 C1 1 0.434803 0.272932 0.322344 11.00000 0.05692 0.05229 = 0.05463 -0.00312 0.01359 0.00439 AFIX 23 H1A 2 0.391413 0.235313 0.286319 11.00000 -1.20000 H1B 2 0.599320 0.300306 0.325437 11.00000 -1.20000 AFIX 0 C5 1 0.536369 0.268217 0.428784 11.00000 0.06583 0.05228 = 0.05456 0.00181 0.01889 0.00500 AFIX 23 H5A 2 0.698500 0.295211 0.428705 11.00000 -1.20000 H5B 2 0.558211 0.227478 0.463270 11.00000 -1.20000 AFIX 0 C3 1 0.176526 0.376227 0.375459 11.00000 0.05455 0.04944 = 0.05984 -0.00023 0.01777 0.00143 C4 1 0.353215 0.345459 0.432592 11.00000 0.05538 0.04706 = 0.05563 0.00106 0.01909 -0.00020 C2 1 0.244071 0.349624 0.318877 11.00000 0.05315 0.04648 = 0.05843 -0.00174 0.01525 -0.00097 C13 1 0.334769 0.390205 0.482283 11.00000 0.05707 0.04870 = 0.05917 0.00060 0.02065 0.00185 AFIX 43 H13 2 0.208034 0.435113 0.476484 11.00000 -1.20000 AFIX 0 C7 1 0.153508 0.392450 0.208429 11.00000 0.05433 0.04651 = 0.05704 0.00098 0.01153 -0.00221 C14 1 0.480380 0.380312 0.544101 11.00000 0.05694 0.04438 = 0.05706 -0.00302 0.02113 -0.00244 C16 1 0.836645 0.328927 0.622157 11.00000 0.05653 0.05584 = 0.06489 -0.00273 0.01720 0.00281 AFIX 43 H16 2 0.992477 0.299561 0.633610 11.00000 -1.20000 AFIX 0 C6 1 0.128143 0.397435 0.269890 11.00000 0.05362 0.04879 = 0.05946 -0.00293 0.01264 0.00267 AFIX 43 H6 2 0.011535 0.441328 0.275968 11.00000 -1.20000 AFIX 0 C15 1 0.714477 0.336491 0.562592 11.00000 0.05750 0.05885 = 0.06137 -0.00553 0.02352 0.00111 AFIX 43 H15 2 0.789787 0.311828 0.534082 11.00000 -1.20000 AFIX 0 C17 1 0.724804 0.365501 0.664648 11.00000 0.06611 0.04890 = 0.05535 -0.00387 0.01751 -0.00937 C9 1 0.354293 0.345837 0.130703 11.00000 0.06293 0.05609 = 0.06717 0.00194 0.02146 0.00309 AFIX 43 H9 2 0.487837 0.317288 0.119463 11.00000 -1.20000 AFIX 0 C19 1 0.379245 0.419400 0.588899 11.00000 0.05681 0.05370 = 0.06466 -0.00714 0.02053 0.00293 AFIX 43 H19 2 0.227245 0.451486 0.577883 11.00000 -1.20000 AFIX 0 C12 1 -0.036642 0.433553 0.163977 11.00000 0.05898 0.05764 = 0.06716 0.00507 0.01476 0.00935 AFIX 43 H12 2 -0.167235 0.464781 0.174873 11.00000 -1.20000 AFIX 0 C8 1 0.350638 0.349752 0.190220 11.00000 0.05578 0.06030 = 0.06074 0.00522 0.01390 0.00430 AFIX 43 H8 2 0.482589 0.323317 0.218702 11.00000 -1.20000 AFIX 0 C18 1 0.497378 0.411768 0.648308 11.00000 0.06733 0.05947 = 0.06155 -0.01043 0.02521 -0.00089 AFIX 43 H18 2 0.425249 0.437387 0.677105 11.00000 -1.20000 AFIX 0 C10 1 0.159228 0.384423 0.088238 11.00000 0.06924 0.05217 = 0.05521 0.00494 0.01667 -0.00237 C11 1 -0.035989 0.429091 0.104418 11.00000 0.06657 0.06379 = 0.06338 0.01134 0.00879 0.00820 AFIX 43 H11 2 -0.165945 0.455958 0.075603 11.00000 -1.20000 AFIX 0 C20 1 0.603644 0.132055 0.374177 11.00000 0.10306 0.05241 = 0.07266 0.00117 0.02414 0.02102 AFIX 137 H20A 2 0.543313 0.097052 0.338019 11.00000 -1.50000 H20B 2 0.601432 0.092822 0.407768 11.00000 -1.50000 H20C 2 0.772436 0.152739 0.376771 11.00000 -1.50000 AFIX 0 HKLF 4 REM 4cl_nm_dbp_rt_a.res in P2(1)/c REM R1 = 0.0539 for 3158 Fo > 4sig(Fo) and 0.0941 for all 5387 data REM 218 parameters refined using 0 restraints END WGHT 0.0741 0.1853 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.190, deepest hole -0.358, 1-sigma level 0.046 Q1 1 0.2570 0.3608 0.4045 11.00000 0.05 0.19 Q2 1 0.0977 0.3839 0.2032 11.00000 0.05 0.18 Q3 1 0.3068 0.4135 0.0244 11.00000 0.05 0.18 Q4 1 0.4567 0.4018 0.5570 11.00000 0.05 0.16 Q5 1 0.3115 0.3198 0.3198 11.00000 0.05 0.16 Q6 1 0.8007 0.3555 0.6413 11.00000 0.05 0.16 Q7 1 0.3496 0.3568 0.4458 11.00000 0.05 0.15 Q8 1 0.6846 0.3672 0.5568 11.00000 0.05 0.15 Q9 1 0.4164 0.3842 0.5186 11.00000 0.05 0.15 Q10 1 0.8047 0.3576 0.5212 11.00000 0.05 0.14 Q11 1 0.8496 0.3218 0.4366 11.00000 0.05 0.14 Q12 1 0.7995 0.3560 0.6005 11.00000 0.05 0.14 Q13 1 0.5221 0.5444 0.6236 11.00000 0.05 0.13 Q14 1 1.0534 0.3783 0.7252 11.00000 0.05 0.13 Q15 1 0.6934 0.3480 0.3392 11.00000 0.05 0.13 Q16 1 0.3678 0.3614 0.1579 11.00000 0.05 0.13 Q17 1 0.7068 0.1409 0.5172 11.00000 0.05 0.12 Q18 1 1.1015 0.4251 0.7612 11.00000 0.05 0.12 Q19 1 0.8370 0.0214 0.4584 11.00000 0.05 0.12 Q20 1 0.2256 0.1647 0.2396 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0539 for 3158 Fo > 4sig(Fo) and 0.0941 for all 11858 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.19, deepest hole -0.36 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0941 REM R1_gt = 0.0539 REM wR_ref = 0.1732 REM GOOF = 1.032 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 11858 REM Reflections_gt = 3158 REM Parameters = n/a REM Hole = -0.36 REM Peak = 0.19 REM Flack = n/a ; _cod_data_source_file d1nj04604g2.cif _cod_data_source_block 4cl_nm_dbp_rt _cod_database_code 7061066 _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. ; _reflns_odcompleteness_completeness 99.50 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.30 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C5(H5A,H5B) 2.b Aromatic/amide H refined with riding coordinates: C13(H13), C16(H16), C6(H6), C15(H15), C9(H9), C19(H19), C12(H12), C8(H8), C18(H18), C11(H11) 2.c Idealised Me refined as rotating group: C20(H20A,H20B,H20C) ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.089 _oxdiff_exptl_absorpt_empirical_full_min 0.926 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Cl2 Cl 0.87563(13) 0.35220(5) 0.73982(3) 0.0756(2) Uani 1 1 d . . . . . Cl1 Cl 0.16048(15) 0.37533(6) 0.01335(3) 0.0885(3) Uani 1 1 d . . . . . O1 O -0.0094(3) 0.42320(13) 0.37526(7) 0.0744(5) Uani 1 1 d . . . . . N1 N 0.4423(3) 0.21337(12) 0.37414(7) 0.0573(4) Uani 1 1 d . . . . . C1 C 0.4348(4) 0.27293(14) 0.32234(9) 0.0547(4) Uani 1 1 d . . . . . H1A H 0.391413 0.235313 0.286319 0.066 Uiso 1 1 calc R . . . . H1B H 0.599320 0.300306 0.325437 0.066 Uiso 1 1 calc R . . . . C5 C 0.5364(4) 0.26822(14) 0.42878(9) 0.0569(5) Uani 1 1 d . . . . . H5A H 0.698500 0.295211 0.428705 0.068 Uiso 1 1 calc R . . . . H5B H 0.558211 0.227478 0.463270 0.068 Uiso 1 1 calc R . . . . C3 C 0.1765(4) 0.37623(14) 0.37546(9) 0.0540(5) Uani 1 1 d . . . . . C4 C 0.3532(4) 0.34546(14) 0.43259(9) 0.0517(4) Uani 1 1 d . . . . . C2 C 0.2441(4) 0.34962(14) 0.31888(9) 0.0524(4) Uani 1 1 d . . . . . C13 C 0.3348(4) 0.39020(14) 0.48228(9) 0.0539(5) Uani 1 1 d . . . . . H13 H 0.208034 0.435113 0.476484 0.065 Uiso 1 1 calc R . . . . C7 C 0.1535(4) 0.39245(14) 0.20843(9) 0.0530(4) Uani 1 1 d . . . . . C14 C 0.4804(4) 0.38031(13) 0.54410(9) 0.0516(4) Uani 1 1 d . . . . . C16 C 0.8366(4) 0.32893(15) 0.62216(9) 0.0587(5) Uani 1 1 d . . . . . H16 H 0.992477 0.299561 0.633610 0.070 Uiso 1 1 calc R . . . . C6 C 0.1281(4) 0.39744(14) 0.26989(9) 0.0542(4) Uani 1 1 d . . . . . H6 H 0.011535 0.441328 0.275968 0.065 Uiso 1 1 calc R . . . . C15 C 0.7145(4) 0.33649(15) 0.56259(9) 0.0577(5) Uani 1 1 d . . . . . H15 H 0.789787 0.311828 0.534082 0.069 Uiso 1 1 calc R . . . . C17 C 0.7248(4) 0.36550(14) 0.66465(9) 0.0564(5) Uani 1 1 d . . . . . C9 C 0.3543(4) 0.34584(16) 0.13070(10) 0.0611(5) Uani 1 1 d . . . . . H9 H 0.487837 0.317288 0.119463 0.073 Uiso 1 1 calc R . . . . C19 C 0.3792(4) 0.41940(15) 0.58890(9) 0.0574(5) Uani 1 1 d . . . . . H19 H 0.227245 0.451486 0.577883 0.069 Uiso 1 1 calc R . . . . C12 C -0.0366(4) 0.43355(16) 0.16398(10) 0.0614(5) Uani 1 1 d . . . . . H12 H -0.167235 0.464781 0.174873 0.074 Uiso 1 1 calc R . . . . C8 C 0.3506(4) 0.34975(15) 0.19022(10) 0.0590(5) Uani 1 1 d . . . . . H8 H 0.482589 0.323317 0.218702 0.071 Uiso 1 1 calc R . . . . C18 C 0.4974(4) 0.41177(16) 0.64831(10) 0.0612(5) Uani 1 1 d . . . . . H18 H 0.425249 0.437387 0.677105 0.073 Uiso 1 1 calc R . . . . C10 C 0.1592(4) 0.38442(15) 0.08824(9) 0.0587(5) Uani 1 1 d . . . . . C11 C -0.0360(4) 0.42909(17) 0.10442(10) 0.0659(6) Uani 1 1 d . . . . . H11 H -0.165945 0.455958 0.075603 0.079 Uiso 1 1 calc R . . . . C20 C 0.6036(6) 0.13205(16) 0.37418(11) 0.0756(7) Uani 1 1 d . . . . . H20A H 0.543313 0.097052 0.338019 0.113 Uiso 1 1 calc GR . . . . H20B H 0.601432 0.092822 0.407768 0.113 Uiso 1 1 calc GR . . . . H20C H 0.772436 0.152739 0.376771 0.113 Uiso 1 1 calc GR . . . . 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 Cl2 0.0916(5) 0.0739(4) 0.0586(3) -0.0008(3) 0.0135(3) -0.0005(3) Cl1 0.1118(6) 0.0975(5) 0.0583(4) 0.0081(3) 0.0249(3) 0.0150(4) O1 0.0684(10) 0.0863(12) 0.0707(10) -0.0006(8) 0.0216(7) 0.0253(9) N1 0.0719(11) 0.0441(9) 0.0570(10) -0.0010(7) 0.0181(8) 0.0051(8) C1 0.0569(11) 0.0523(11) 0.0546(11) -0.0031(8) 0.0136(8) 0.0044(9) C5 0.0658(12) 0.0523(11) 0.0546(11) 0.0018(8) 0.0189(9) 0.0050(9) C3 0.0545(11) 0.0494(11) 0.0598(12) -0.0002(8) 0.0178(9) 0.0014(8) C4 0.0554(10) 0.0471(10) 0.0556(11) 0.0011(8) 0.0191(8) -0.0002(8) C2 0.0532(10) 0.0465(10) 0.0584(11) -0.0017(8) 0.0153(8) -0.0010(8) C13 0.0571(11) 0.0487(10) 0.0592(11) 0.0006(8) 0.0207(9) 0.0018(8) C7 0.0543(11) 0.0465(10) 0.0570(11) 0.0010(8) 0.0115(8) -0.0022(8) C14 0.0569(11) 0.0444(10) 0.0571(11) -0.0030(8) 0.0211(8) -0.0024(8) C16 0.0565(11) 0.0558(12) 0.0649(13) -0.0027(9) 0.0172(9) 0.0028(9) C6 0.0536(10) 0.0488(11) 0.0595(12) -0.0029(8) 0.0126(8) 0.0027(8) C15 0.0575(11) 0.0588(12) 0.0614(12) -0.0055(9) 0.0235(9) 0.0011(9) C17 0.0661(13) 0.0489(11) 0.0554(11) -0.0039(8) 0.0175(9) -0.0094(9) C9 0.0629(12) 0.0561(12) 0.0672(13) 0.0019(9) 0.0215(10) 0.0031(9) C19 0.0568(11) 0.0537(11) 0.0647(12) -0.0071(9) 0.0205(9) 0.0029(9) C12 0.0590(12) 0.0576(12) 0.0672(13) 0.0051(10) 0.0148(9) 0.0094(9) C8 0.0558(11) 0.0603(12) 0.0607(12) 0.0052(9) 0.0139(9) 0.0043(9) C18 0.0673(13) 0.0595(12) 0.0616(12) -0.0104(9) 0.0252(10) -0.0009(10) C10 0.0692(13) 0.0522(11) 0.0552(11) 0.0049(9) 0.0167(9) -0.0024(10) C11 0.0666(13) 0.0638(14) 0.0634(13) 0.0113(10) 0.0088(10) 0.0082(10) C20 0.1031(19) 0.0524(13) 0.0727(15) 0.0012(10) 0.0241(13) 0.0210(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' 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 C1 N1 C5 109.33(16) . . ? C20 N1 C1 110.82(16) . . ? C20 N1 C5 109.75(17) . . ? N1 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? N1 C1 C2 110.11(15) . . ? H1A C1 H1B 108.2 . . ? C2 C1 H1A 109.6 . . ? C2 C1 H1B 109.6 . . ? N1 C5 H5A 109.7 . . ? N1 C5 H5B 109.7 . . ? N1 C5 C4 109.95(17) . . ? H5A C5 H5B 108.2 . . ? C4 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? O1 C3 C4 121.47(18) . . ? O1 C3 C2 121.62(19) . . ? C2 C3 C4 116.88(17) . . ? C3 C4 C5 117.20(16) . . ? C13 C4 C5 126.16(19) . . ? C13 C4 C3 116.64(18) . . ? C3 C2 C1 117.27(17) . . ? C6 C2 C1 126.41(18) . . ? C6 C2 C3 116.32(18) . . ? C4 C13 H13 114.6 . . ? C4 C13 C14 130.88(19) . . ? C14 C13 H13 114.6 . . ? C12 C7 C6 117.44(19) . . ? C8 C7 C6 125.59(18) . . ? C8 C7 C12 117.0(2) . . ? C15 C14 C13 125.54(17) . . ? C15 C14 C19 116.86(19) . . ? C19 C14 C13 117.59(19) . . ? C15 C16 H16 120.4 . . ? C15 C16 C17 119.3(2) . . ? C17 C16 H16 120.4 . . ? C2 C6 C7 131.11(19) . . ? C2 C6 H6 114.4 . . ? C7 C6 H6 114.4 . . ? C14 C15 H15 119.2 . . ? C16 C15 C14 121.58(18) . . ? C16 C15 H15 119.2 . . ? C16 C17 Cl2 118.95(18) . . ? C18 C17 Cl2 120.01(16) . . ? C18 C17 C16 121.0(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C10 C9 C8 119.6(2) . . ? C14 C19 H19 118.9 . . ? C18 C19 C14 122.2(2) . . ? C18 C19 H19 118.9 . . ? C7 C12 H12 119.0 . . ? C11 C12 C7 121.9(2) . . ? C11 C12 H12 119.0 . . ? C7 C8 H8 119.3 . . ? C9 C8 C7 121.5(2) . . ? C9 C8 H8 119.3 . . ? C17 C18 H18 120.5 . . ? C19 C18 C17 118.95(19) . . ? C19 C18 H18 120.5 . . ? C9 C10 Cl1 119.19(17) . . ? C11 C10 Cl1 120.07(17) . . ? C11 C10 C9 120.7(2) . . ? C12 C11 H11 120.4 . . ? C10 C11 C12 119.2(2) . . ? C10 C11 H11 120.4 . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 Cl2 C17 1.743(2) . ? Cl1 C10 1.740(2) . ? O1 C3 1.220(2) . ? N1 C1 1.461(2) . ? N1 C5 1.468(3) . ? N1 C20 1.458(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.501(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C4 1.508(3) . ? C3 C4 1.499(3) . ? C3 C2 1.496(3) . ? C4 C13 1.341(3) . ? C2 C6 1.341(3) . ? C13 H13 0.9300 . ? C13 C14 1.463(3) . ? C7 C6 1.465(3) . ? C7 C12 1.400(3) . ? C7 C8 1.394(3) . ? C14 C15 1.397(3) . ? C14 C19 1.407(3) . ? C16 H16 0.9300 . ? C16 C15 1.380(3) . ? C16 C17 1.384(3) . ? C6 H6 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.379(3) . ? C9 H9 0.9300 . ? C9 C8 1.384(3) . ? C9 C10 1.376(3) . ? C19 H19 0.9300 . ? C19 C18 1.372(3) . ? C12 H12 0.9300 . ? C12 C11 1.381(3) . ? C8 H8 0.9300 . ? C18 H18 0.9300 . ? C10 C11 1.376(3) . ? C11 H11 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C17 C18 C19 -178.44(16) . . . . ? Cl1 C10 C11 C12 178.42(17) . . . . ? O1 C3 C4 C5 164.5(2) . . . . ? O1 C3 C4 C13 -16.1(3) . . . . ? O1 C3 C2 C1 -165.0(2) . . . . ? O1 C3 C2 C6 15.4(3) . . . . ? N1 C1 C2 C3 23.3(2) . . . . ? N1 C1 C2 C6 -157.1(2) . . . . ? N1 C5 C4 C3 -22.3(2) . . . . ? N1 C5 C4 C13 158.51(19) . . . . ? C1 N1 C5 C4 65.2(2) . . . . ? C1 C2 C6 C7 -1.8(4) . . . . ? C5 N1 C1 C2 -65.8(2) . . . . ? C5 C4 C13 C14 1.5(4) . . . . ? C3 C4 C13 C14 -177.78(19) . . . . ? C3 C2 C6 C7 177.79(19) . . . . ? C4 C3 C2 C1 17.2(3) . . . . ? C4 C3 C2 C6 -162.47(18) . . . . ? C4 C13 C14 C15 16.8(3) . . . . ? C4 C13 C14 C19 -164.3(2) . . . . ? C2 C3 C4 C5 -17.6(3) . . . . ? C2 C3 C4 C13 161.68(18) . . . . ? C13 C14 C15 C16 -178.84(19) . . . . ? C13 C14 C19 C18 178.18(19) . . . . ? C7 C12 C11 C10 -1.2(4) . . . . ? C14 C19 C18 C17 1.0(3) . . . . ? C16 C17 C18 C19 1.5(3) . . . . ? C6 C7 C12 C11 -177.1(2) . . . . ? C6 C7 C8 C9 177.8(2) . . . . ? C15 C14 C19 C18 -2.8(3) . . . . ? C15 C16 C17 Cl2 177.91(16) . . . . ? C15 C16 C17 C18 -2.0(3) . . . . ? C17 C16 C15 C14 0.1(3) . . . . ? C9 C10 C11 C12 -1.1(3) . . . . ? C19 C14 C15 C16 2.3(3) . . . . ? C12 C7 C6 C2 164.0(2) . . . . ? C12 C7 C8 C9 -1.8(3) . . . . ? C8 C7 C6 C2 -15.7(4) . . . . ? C8 C7 C12 C11 2.6(3) . . . . ? C8 C9 C10 Cl1 -177.71(17) . . . . ? C8 C9 C10 C11 1.8(3) . . . . ? C10 C9 C8 C7 -0.3(3) . . . . ? C20 N1 C1 C2 173.07(19) . . . . ? C20 N1 C5 C4 -173.07(18) . . . . ?