# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x12117 #=============================================================================== # 5. CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39.07 H42.07 Cl0.22 N4' _chemical_formula_weight 575.59 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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-y+3/4, x+1/4, z+1/4' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-y+5/4, x+3/4, z+3/4' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'x, y-1/2, -z' 'y-3/4, -x-1/4, -z-1/4' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 30.805(7) _cell_length_b 30.805(7) _cell_length_c 14.937(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 14174(4) _cell_formula_units_Z 16 _cell_measurement_temperature 110 _cell_measurement_reflns_used 9730 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 30.54 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.079 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4933 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9711 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Kappa Axis X8 Apex2' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 157107 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 33.79 _reflns_number_total 13754 _reflns_number_gt 8823 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex2 _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution SIR92 _computing_structure_refinement XL _computing_molecular_graphics NRCVAX _computing_publication_material cif2tables.py _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The chloroform solvent forms disordered around the 4~1~ screw axis with a site occupancy of roughly 7%. The central C of the solvent was located as a peak in the difference map with a residual density of less than 0.5 e^-^/\%A^3^. The close approach of the chloroform H is likely caused by the fact that the disordered molecule was restrained to hold a chemically reasonable shape and the calculated placement of the H at a fixed distance from C is only an approximate model for this disordered region of the structure. Bond lengths and angles for the partially occupied chloroform were restrained as indicated in the refinement instructions shown below: TITL x12117: 110K CELL 0.71073 30.80508 30.80508 14.93668 90.0000 90.0000 90.0000 ZERR 16 0.00659 0.00000 0.00326 0.0000 0.0000 0.0000 LATT 2 SYMM -X, 0.50000-Y,Z SYMM 0.75000-Y, 0.25000+X, 0.25000+Z SYMM 0.25000+Y, 0.25000-X, 0.25000+Z SFAC C H CL N UNIT 625.18 673.18 3.55 64 TEMP -163 SIZE 0.500 0.465 0.371 ACTA MERG 2 DFIX 1.75 0.02 C1X CL1X C1X CL2X C1X CL3X DFIX 2.87 0.03 CL1X CL2X CL1X CL3X CL2X CL3X L.S. 12 FMAP 2 PLAN 25 BOND $H CONF WGHT 0.077200 3.723000 FVAR 0.05282 0.07315 MOLE 1 N1 4 0.070934 0.031788 0.636662 11.00000 0.02518 0.02033 = 0.02609 -0.00328 -0.00573 0.00085 N2 4 0.007008 0.066545 0.523538 11.00000 0.02700 0.02363 = 0.02625 -0.00209 -0.00567 -0.00107 H2 2 0.014007 0.068672 0.580677 11.00000 0.04155 N3 4 -0.021720 0.119832 0.671361 11.00000 0.02111 0.02309 = 0.02826 0.00021 -0.00248 0.00043 N4 4 0.051218 0.089291 0.757846 11.00000 0.02117 0.02606 = 0.02605 -0.00453 -0.00401 0.00419 H4 2 0.032116 0.083728 0.713334 11.00000 0.04145 C1 1 0.100917 0.030387 0.714240 11.00000 0.02317 0.02184 = 0.02828 -0.00490 -0.00632 0.00276 C2 1 0.146695 0.034575 0.672912 11.00000 0.02249 0.03251 = 0.03571 -0.01325 -0.00468 0.00462 H2A 2 0.169021 0.016104 0.704929 11.00000 0.03613 H2B 2 0.155845 0.065456 0.676301 11.00000 0.03241 C3 1 0.141252 0.021551 0.573710 11.00000 0.02672 0.03568 = 0.03510 -0.01390 -0.00255 0.00674 C4 1 0.092304 0.027212 0.563107 11.00000 0.02688 0.01909 = 0.03003 -0.00646 -0.00299 0.00213 C5 1 0.071526 0.027424 0.476071 11.00000 0.03177 0.02359 = 0.02694 -0.00548 -0.00171 -0.00119 H5 2 0.087727 0.016388 0.426596 11.00000 0.02960 C6 1 0.031793 0.045295 0.460320 11.00000 0.03142 0.01950 = 0.02618 -0.00176 -0.00325 -0.00513 C7 1 0.008733 0.050482 0.375077 11.00000 0.03465 0.02227 = 0.02630 -0.00005 -0.00706 -0.00870 C8 1 -0.027412 0.074412 0.391538 11.00000 0.03268 0.02424 = 0.03002 0.00121 -0.00908 -0.00694 H8 2 -0.049215 0.084032 0.346135 11.00000 0.03734 C9 1 -0.029041 0.085497 0.485702 11.00000 0.02597 0.02225 = 0.03074 0.00109 -0.00810 -0.00603 C10 1 -0.058460 0.111656 0.528581 11.00000 0.02403 0.02602 = 0.03383 0.00192 -0.00851 -0.00261 H10 2 -0.082658 0.121441 0.491965 11.00000 0.03474 C11 1 -0.054132 0.128924 0.616854 11.00000 0.02024 0.02298 = 0.03414 0.00242 -0.00380 -0.00093 C12 1 -0.084791 0.162881 0.653353 11.00000 0.02417 0.03419 = 0.04152 -0.00167 -0.00601 0.00705 H12A 2 -0.114214 0.150936 0.654484 11.00000 0.04742 H12B 2 -0.085507 0.189147 0.612305 11.00000 0.05140 C13 1 -0.066294 0.173638 0.746044 11.00000 0.02325 0.03312 = 0.03522 -0.00113 -0.00028 0.00906 C14 1 -0.025092 0.145897 0.747974 11.00000 0.02058 0.02398 = 0.02887 -0.00050 0.00173 0.00315 C15 1 0.004961 0.147026 0.814407 11.00000 0.02225 0.02585 = 0.02738 -0.00301 0.00173 0.00399 H15 2 0.000697 0.168263 0.863248 11.00000 0.03478 C16 1 0.043847 0.121017 0.819761 11.00000 0.02101 0.02359 = 0.02336 -0.00211 0.00070 0.00197 C17 1 0.078385 0.119312 0.880753 11.00000 0.02076 0.02243 = 0.02140 -0.00076 0.00086 0.00008 C18 1 0.105881 0.084598 0.852358 11.00000 0.02036 0.02367 = 0.02405 -0.00159 -0.00112 0.00147 H18 2 0.133856 0.075825 0.880772 11.00000 0.03037 C19 1 0.088375 0.067151 0.775517 11.00000 0.02025 0.02219 = 0.02574 -0.00186 -0.00204 0.00221 C20 1 0.094481 -0.012528 0.765088 11.00000 0.04182 0.02410 = 0.03614 -0.00009 -0.01339 0.00114 H20A 2 0.063422 -0.015648 0.784237 11.00000 0.04021 H20B 2 0.113564 -0.012239 0.820087 11.00000 0.04169 H20C 2 0.101935 -0.036896 0.726526 11.00000 0.04734 C21 1 0.153058 -0.026133 0.555609 11.00000 0.04726 0.04816 = 0.05503 -0.02913 -0.01472 0.02474 H21A 2 0.147272 -0.032950 0.490679 11.00000 0.07286 H21B 2 0.136067 -0.046897 0.597895 11.00000 0.07894 H21C 2 0.184921 -0.030316 0.563900 11.00000 0.05715 C22 1 0.167103 0.051152 0.511491 11.00000 0.03258 0.07070 = 0.04429 -0.01312 0.00839 -0.00426 H22A 2 0.163064 0.044353 0.446879 11.00000 0.06105 H22B 2 0.199111 0.048537 0.525874 11.00000 0.06934 H22C 2 0.157984 0.081709 0.521361 11.00000 0.06127 C23 1 -0.097033 0.160027 0.821069 11.00000 0.02821 0.10494 = 0.05034 0.02093 0.01074 0.02547 H23A 2 -0.103991 0.126975 0.816112 11.00000 0.08462 H23B 2 -0.124059 0.177710 0.816590 11.00000 0.07727 H23C 2 -0.084601 0.163981 0.880419 11.00000 0.07447 C24 1 -0.055376 0.221815 0.754161 11.00000 0.05029 0.03373 = 0.08147 -0.01533 -0.02669 0.01863 AFIX 137 H24A 2 -0.082187 0.238896 0.751680 11.00000 -1.50000 H24B 2 -0.036278 0.230352 0.704730 11.00000 -1.50000 H24C 2 -0.040653 0.227123 0.811282 11.00000 -1.50000 AFIX 0 C25 1 0.023592 0.033176 0.288490 11.00000 0.03474 0.02867 = 0.02473 -0.00011 -0.00487 -0.00965 C26 1 0.038314 -0.009446 0.280454 11.00000 0.04774 0.02854 = 0.02663 -0.00033 0.00034 -0.00939 H26 2 0.038688 -0.028127 0.333640 11.00000 0.03710 C27 1 0.050197 -0.026127 0.197745 11.00000 0.05590 0.03531 = 0.03182 -0.00565 0.00210 -0.00744 H27 2 0.059709 -0.056130 0.193028 11.00000 0.05226 C28 1 0.048704 -0.000817 0.120676 11.00000 0.05195 0.05284 = 0.02632 -0.00432 -0.00069 -0.01160 C29 1 0.034391 0.041627 0.128858 11.00000 0.05195 0.05112 = 0.02721 0.00752 -0.00630 -0.00843 H29 2 0.033178 0.060221 0.077241 11.00000 0.05655 C30 1 0.021670 0.058621 0.211078 11.00000 0.04339 0.03646 = 0.03025 0.00463 -0.00719 -0.00641 H30 2 0.011002 0.088983 0.216536 11.00000 0.04769 C31 1 0.063535 -0.019218 0.031685 11.00000 0.08738 0.07956 = 0.02778 -0.00871 0.00338 -0.00361 AFIX 23 H31A 2 0.048143 -0.046897 0.020431 11.00000 -1.20000 H31B 2 0.055557 0.001262 -0.016670 11.00000 -1.20000 AFIX 0 C32 1 0.111965 -0.027228 0.028621 11.00000 0.11682 0.13260 = 0.04717 0.00571 0.02308 0.05068 AFIX 137 H32A 2 0.127382 0.000473 0.034089 11.00000 -1.50000 H32B 2 0.119592 -0.041005 -0.028388 11.00000 -1.50000 H32C 2 0.120295 -0.046342 0.078176 11.00000 -1.50000 AFIX 0 C33 1 0.085375 0.147635 0.958260 11.00000 0.02198 0.02421 = 0.02330 -0.00160 0.00228 -0.00076 C34 1 0.074569 0.191775 0.955959 11.00000 0.02802 0.02444 = 0.02796 -0.00035 0.00158 0.00000 H34 2 0.063257 0.203923 0.900318 11.00000 0.03340 C35 1 0.079542 0.217674 1.031335 11.00000 0.03624 0.02481 = 0.03539 -0.00596 0.00384 -0.00010 H35 2 0.071165 0.248102 1.027079 11.00000 0.03273 C36 1 0.095818 0.200909 1.110986 11.00000 0.03917 0.03490 = 0.03011 -0.01053 0.00160 -0.00238 C37 1 0.107888 0.157512 1.112396 11.00000 0.04636 0.03879 = 0.02443 -0.00409 -0.00450 0.00298 H37 2 0.119711 0.144680 1.167055 11.00000 0.04726 C38 1 0.102835 0.131217 1.037556 11.00000 0.03649 0.02617 = 0.02603 -0.00276 -0.00284 0.00356 H38 2 0.110973 0.100611 1.040690 11.00000 0.03241 C39 1 0.099722 0.228964 1.193285 11.00000 0.06639 0.04663 = 0.03645 -0.01922 0.00177 -0.00292 H39A 2 0.104041 0.259676 1.175805 11.00000 0.08417 H39B 2 0.122497 0.219005 1.236529 11.00000 0.07469 H39C 2 0.072976 0.227279 1.228587 11.00000 0.07235 MOLE 2 PART -1 C1X 1 0.191589 0.064167 1.185618 21.00000 0.06386 0.08643 = 0.13925 0.03448 0.03811 -0.01728 AFIX 13 H1X 2 0.189360 0.095263 1.166958 21.00000 -1.20000 AFIX 0 CL1X 3 0.143012 0.048102 1.231838 21.00000 0.06041 0.10916 = 0.11335 0.02750 -0.00804 -0.01693 CL2X 3 0.203687 0.032656 1.092645 21.00000 0.26837 0.12500 = 0.26584 -0.00604 0.16719 -0.04312 CL3X 3 0.233964 0.058641 1.262086 21.00000 0.08764 0.18591 = 0.40080 0.03617 -0.01046 -0.05413 PART 0 MOLE 0 HKLF 4 REM x12117: 110K REM R1 = 0.0530 for 8823 Fo > 4sig(Fo) and 0.0963 for all 13754 data REM 563 parameters refined using 6 restraints END WGHT 0.0747 3.8797 REM Highest difference peak 0.556, deepest hole -0.232, 1-sigma level 0.045 Q1 1 0.0672 -0.0566 0.0174 11.00000 0.05 0.56 Q2 1 0.0804 0.0243 0.5209 11.00000 0.05 0.33 Q3 1 0.0794 0.2014 0.9995 11.00000 0.05 0.32 Q4 1 0.0222 0.0475 0.4147 11.00000 0.05 0.32 Q5 1 -0.0297 0.0788 0.4392 11.00000 0.05 0.31 Q6 1 0.0968 0.0494 0.7484 11.00000 0.05 0.31 Q7 1 0.0923 0.0688 0.8250 11.00000 0.05 0.30 Q8 1 0.1023 0.0813 0.8041 11.00000 0.05 0.30 Q9 1 -0.0107 0.1413 0.7851 11.00000 0.05 0.29 Q10 1 0.0809 0.1329 0.9247 11.00000 0.05 0.29 Q11 1 0.0609 0.1221 0.8532 11.00000 0.05 0.29 Q12 1 0.1423 0.0279 0.6239 11.00000 0.05 0.29 Q13 1 -0.0564 0.1176 0.5749 11.00000 0.05 0.29 Q14 1 0.0818 0.1688 0.9635 11.00000 0.05 0.28 Q15 1 0.0929 0.1406 1.0000 11.00000 0.05 0.27 Q16 1 -0.0479 0.1607 0.7423 11.00000 0.05 0.27 Q17 1 0.0226 0.0443 0.2449 11.00000 0.05 0.27 Q18 1 -0.0398 0.1214 0.6500 11.00000 0.05 0.27 Q19 1 -0.0770 0.1693 0.7026 11.00000 0.05 0.26 Q20 1 -0.0216 0.1332 0.7141 11.00000 0.05 0.26 Q21 1 0.1024 0.1461 1.0717 11.00000 0.05 0.25 Q22 1 0.0879 0.2096 1.0693 11.00000 0.05 0.25 Q23 1 -0.0802 0.1676 0.7799 11.00000 0.05 0.25 Q24 1 0.0440 -0.0147 0.2339 11.00000 0.05 0.25 Q25 1 0.0181 0.0408 0.3361 11.00000 0.05 0.24 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+3.7230P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13754 _refine_ls_number_parameters 563 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.07093(3) 0.03179(3) 0.63666(6) 0.02387(17) Uani 1 1 d . . . N2 N 0.00701(3) 0.06654(3) 0.52354(6) 0.02563(18) Uani 1 1 d . . . H2 H 0.0140(5) 0.0687(5) 0.5807(10) 0.042(4) Uiso 1 1 d . . . N3 N -0.02172(3) 0.11983(3) 0.67136(6) 0.02415(17) Uani 1 1 d . . . N4 N 0.05122(3) 0.08929(3) 0.75785(6) 0.02443(17) Uani 1 1 d . . . H4 H 0.0321(5) 0.0837(5) 0.7133(10) 0.041(4) Uiso 1 1 d . . . C1 C 0.10092(3) 0.03039(3) 0.71424(7) 0.02443(19) Uani 1 1 d . . . C2 C 0.14669(3) 0.03457(4) 0.67291(8) 0.0302(2) Uani 1 1 d . . . H2A H 0.1690(5) 0.0161(4) 0.7049(9) 0.036(3) Uiso 1 1 d . . . H2B H 0.1558(4) 0.0655(4) 0.6763(8) 0.032(3) Uiso 1 1 d . . . C3 C 0.14125(4) 0.02155(4) 0.57371(8) 0.0325(2) Uani 1 1 d . . . C4 C 0.09230(3) 0.02721(3) 0.56311(7) 0.0253(2) Uani 1 1 d . . . C5 C 0.07153(4) 0.02742(3) 0.47607(7) 0.0274(2) Uani 1 1 d . . . H5 H 0.0877(4) 0.0164(4) 0.4266(9) 0.030(3) Uiso 1 1 d . . . C6 C 0.03179(3) 0.04530(3) 0.46032(7) 0.0257(2) Uani 1 1 d . . . C7 C 0.00873(4) 0.05048(3) 0.37508(7) 0.0277(2) Uani 1 1 d . . . C8 C -0.02741(4) 0.07441(3) 0.39154(7) 0.0290(2) Uani 1 1 d . . . H8 H -0.0492(5) 0.0840(4) 0.3461(9) 0.037(3) Uiso 1 1 d . . . C9 C -0.02904(3) 0.08550(3) 0.48570(7) 0.0263(2) Uani 1 1 d . . . C10 C -0.05846(3) 0.11166(3) 0.52858(7) 0.0280(2) Uani 1 1 d . . . H10 H -0.0827(4) 0.1214(4) 0.4920(9) 0.035(3) Uiso 1 1 d . . . C11 C -0.05413(3) 0.12892(3) 0.61685(7) 0.0258(2) Uani 1 1 d . . . C12 C -0.08479(4) 0.16288(4) 0.65335(8) 0.0333(2) Uani 1 1 d . . . H12A H -0.1142(5) 0.1509(5) 0.6545(10) 0.047(4) Uiso 1 1 d . . . H12B H -0.0855(5) 0.1891(5) 0.6123(11) 0.051(4) Uiso 1 1 d . . . C13 C -0.06629(3) 0.17364(4) 0.74604(8) 0.0305(2) Uani 1 1 d . . . C14 C -0.02509(3) 0.14590(3) 0.74797(7) 0.02447(19) Uani 1 1 d . . . C15 C 0.00496(3) 0.14703(3) 0.81441(7) 0.0252(2) Uani 1 1 d . . . H15 H 0.0007(4) 0.1683(4) 0.8632(9) 0.035(3) Uiso 1 1 d . . . C16 C 0.04385(3) 0.12102(3) 0.81976(6) 0.02265(18) Uani 1 1 d . . . C17 C 0.07839(3) 0.11931(3) 0.88075(6) 0.02153(18) Uani 1 1 d . . . C18 C 0.10588(3) 0.08460(3) 0.85236(6) 0.02269(18) Uani 1 1 d . . . H18 H 0.1339(4) 0.0758(4) 0.8808(8) 0.030(3) Uiso 1 1 d . . . C19 C 0.08838(3) 0.06715(3) 0.77552(7) 0.02273(18) Uani 1 1 d . . . C20 C 0.09448(4) -0.01253(4) 0.76509(8) 0.0340(2) Uani 1 1 d . . . H20A H 0.0634(5) -0.0156(5) 0.7842(9) 0.040(4) Uiso 1 1 d . . . H20B H 0.1136(5) -0.0122(5) 0.8201(10) 0.042(4) Uiso 1 1 d . . . H20C H 0.1019(5) -0.0369(5) 0.7265(10) 0.047(4) Uiso 1 1 d . . . C21 C 0.15306(5) -0.02613(5) 0.55561(11) 0.0502(4) Uani 1 1 d . . . H21A H 0.1473(6) -0.0330(6) 0.4907(13) 0.073(5) Uiso 1 1 d . . . H21B H 0.1361(7) -0.0469(7) 0.5979(13) 0.079(6) Uiso 1 1 d . . . H21C H 0.1849(6) -0.0303(5) 0.5639(10) 0.057(5) Uiso 1 1 d . . . C22 C 0.16710(5) 0.05115(6) 0.51149(10) 0.0492(3) Uani 1 1 d . . . H22A H 0.1631(6) 0.0444(6) 0.4469(12) 0.061(5) Uiso 1 1 d . . . H22B H 0.1991(6) 0.0485(6) 0.5259(12) 0.069(5) Uiso 1 1 d . . . H22C H 0.1580(6) 0.0817(6) 0.5214(11) 0.061(5) Uiso 1 1 d . . . C23 C -0.09703(5) 0.16003(8) 0.82107(12) 0.0612(5) Uani 1 1 d . . . H23A H -0.1040(7) 0.1270(8) 0.8161(14) 0.085(7) Uiso 1 1 d . . . H23B H -0.1241(7) 0.1777(6) 0.8166(12) 0.077(6) Uiso 1 1 d . . . H23C H -0.0846(6) 0.1640(6) 0.8804(14) 0.074(6) Uiso 1 1 d . . . C24 C -0.05538(5) 0.22181(4) 0.75416(12) 0.0552(4) Uani 1 1 d . . . H24A H -0.0822 0.2389 0.7517 0.083 Uiso 1 1 calc R . . H24B H -0.0363 0.2304 0.7047 0.083 Uiso 1 1 calc R . . H24C H -0.0407 0.2271 0.8113 0.083 Uiso 1 1 calc R . . C25 C 0.02359(4) 0.03318(3) 0.28849(7) 0.0294(2) Uani 1 1 d . . . C26 C 0.03831(4) -0.00945(4) 0.28045(8) 0.0343(2) Uani 1 1 d . . . H26 H 0.0387(4) -0.0281(4) 0.3336(9) 0.037(3) Uiso 1 1 d . . . C27 C 0.05020(5) -0.02613(4) 0.19775(8) 0.0410(3) Uani 1 1 d . . . H27 H 0.0597(5) -0.0561(5) 0.1930(10) 0.052(4) Uiso 1 1 d . . . C28 C 0.04870(5) -0.00082(5) 0.12068(8) 0.0437(3) Uani 1 1 d . . . C29 C 0.03439(5) 0.04163(5) 0.12886(8) 0.0434(3) Uani 1 1 d . . . H29 H 0.0332(5) 0.0602(5) 0.0772(11) 0.057(4) Uiso 1 1 d . . . C30 C 0.02167(4) 0.05862(4) 0.21108(8) 0.0367(3) Uani 1 1 d . . . H30 H 0.0110(5) 0.0890(5) 0.2165(10) 0.048(4) Uiso 1 1 d . . . C31 C 0.06353(6) -0.01922(6) 0.03169(10) 0.0649(5) Uani 1 1 d . . . H31A H 0.0481 -0.0469 0.0204 0.078 Uiso 1 1 calc R . . H31B H 0.0556 0.0013 -0.0167 0.078 Uiso 1 1 calc R . . C32 C 0.11197(9) -0.02723(9) 0.02862(13) 0.0989(8) Uani 1 1 d . . . H32A H 0.1274 0.0005 0.0341 0.148 Uiso 1 1 calc R . . H32B H 0.1196 -0.0410 -0.0284 0.148 Uiso 1 1 calc R . . H32C H 0.1203 -0.0463 0.0782 0.148 Uiso 1 1 calc R . . C33 C 0.08537(3) 0.14764(3) 0.95826(6) 0.02317(18) Uani 1 1 d . . . C34 C 0.07457(3) 0.19178(3) 0.95596(7) 0.0268(2) Uani 1 1 d . . . H34 H 0.0633(4) 0.2039(4) 0.9003(9) 0.033(3) Uiso 1 1 d . . . C35 C 0.07954(4) 0.21767(4) 1.03134(8) 0.0321(2) Uani 1 1 d . . . H35 H 0.0712(4) 0.2481(4) 1.0271(9) 0.033(3) Uiso 1 1 d . . . C36 C 0.09582(4) 0.20091(4) 1.11099(8) 0.0347(2) Uani 1 1 d . . . C37 C 0.10789(4) 0.15751(4) 1.11240(8) 0.0365(3) Uani 1 1 d . . . H37 H 0.1197(5) 0.1447(5) 1.1671(10) 0.047(4) Uiso 1 1 d . . . C38 C 0.10283(4) 0.13122(4) 1.03756(7) 0.0296(2) Uani 1 1 d . . . H38 H 0.1110(4) 0.1006(4) 1.0407(9) 0.032(3) Uiso 1 1 d . . . C39 C 0.09972(6) 0.22896(5) 1.19328(10) 0.0498(3) Uani 1 1 d . . . H39A H 0.1040(6) 0.2597(7) 1.1758(13) 0.084(6) Uiso 1 1 d . . . H39B H 0.1225(6) 0.2190(6) 1.2365(13) 0.075(6) Uiso 1 1 d . . . H39C H 0.0730(7) 0.2273(6) 1.2286(13) 0.072(6) Uiso 1 1 d . . . C1X C 0.1916(5) 0.0642(8) 1.1856(14) 0.097(11) Uani 0.0731(16) 1 d PD A -1 H1X H 0.1894 0.0953 1.1670 0.116 Uiso 0.0731(16) 1 calc PR A -1 Cl1X Cl 0.1430(2) 0.0481(3) 1.2318(6) 0.094(3) Uani 0.0731(16) 1 d PD A -1 Cl2X Cl 0.2037(6) 0.0327(5) 1.0926(12) 0.220(11) Uani 0.0731(16) 1 d PD A -1 Cl3X Cl 0.2340(4) 0.0586(6) 1.2621(14) 0.225(10) Uani 0.0731(16) 1 d PD A -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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0252(4) 0.0203(4) 0.0261(4) -0.0033(3) -0.0057(3) 0.0008(3) N2 0.0270(4) 0.0236(4) 0.0262(4) -0.0021(3) -0.0057(3) -0.0011(3) N3 0.0211(4) 0.0231(4) 0.0283(4) 0.0002(3) -0.0025(3) 0.0004(3) N4 0.0212(4) 0.0261(4) 0.0261(4) -0.0045(3) -0.0040(3) 0.0042(3) C1 0.0232(4) 0.0218(4) 0.0283(5) -0.0049(4) -0.0063(4) 0.0028(3) C2 0.0225(5) 0.0325(5) 0.0357(6) -0.0132(4) -0.0047(4) 0.0046(4) C3 0.0267(5) 0.0357(6) 0.0351(6) -0.0139(4) -0.0026(4) 0.0067(4) C4 0.0269(5) 0.0191(4) 0.0300(5) -0.0065(4) -0.0030(4) 0.0021(3) C5 0.0318(5) 0.0236(5) 0.0269(5) -0.0055(4) -0.0017(4) -0.0012(4) C6 0.0314(5) 0.0195(4) 0.0262(5) -0.0018(3) -0.0033(4) -0.0051(4) C7 0.0346(5) 0.0223(5) 0.0263(5) -0.0001(4) -0.0071(4) -0.0087(4) C8 0.0327(5) 0.0242(5) 0.0300(5) 0.0012(4) -0.0091(4) -0.0069(4) C9 0.0260(5) 0.0222(4) 0.0307(5) 0.0011(4) -0.0081(4) -0.0060(4) C10 0.0240(5) 0.0260(5) 0.0338(5) 0.0019(4) -0.0085(4) -0.0026(4) C11 0.0202(4) 0.0230(5) 0.0341(5) 0.0024(4) -0.0038(4) -0.0009(3) C12 0.0242(5) 0.0342(6) 0.0415(6) -0.0017(5) -0.0060(4) 0.0070(4) C13 0.0233(5) 0.0331(5) 0.0352(6) -0.0011(4) -0.0003(4) 0.0091(4) C14 0.0206(4) 0.0240(4) 0.0289(5) -0.0005(4) 0.0017(4) 0.0031(3) C15 0.0223(4) 0.0259(5) 0.0274(5) -0.0030(4) 0.0017(4) 0.0040(4) C16 0.0210(4) 0.0236(4) 0.0234(4) -0.0021(3) 0.0007(3) 0.0020(3) C17 0.0208(4) 0.0224(4) 0.0214(4) -0.0008(3) 0.0009(3) 0.0001(3) C18 0.0204(4) 0.0237(4) 0.0241(4) -0.0016(3) -0.0011(3) 0.0015(3) C19 0.0202(4) 0.0222(4) 0.0257(4) -0.0019(3) -0.0020(3) 0.0022(3) C20 0.0418(6) 0.0241(5) 0.0361(6) -0.0001(4) -0.0134(5) 0.0011(4) C21 0.0473(8) 0.0482(8) 0.0550(9) -0.0291(7) -0.0147(7) 0.0247(6) C22 0.0326(7) 0.0707(10) 0.0443(8) -0.0131(7) 0.0084(6) -0.0043(6) C23 0.0282(6) 0.1049(15) 0.0503(9) 0.0209(9) 0.0107(6) 0.0255(8) C24 0.0503(8) 0.0337(6) 0.0815(11) -0.0153(7) -0.0267(7) 0.0186(6) C25 0.0347(5) 0.0287(5) 0.0247(5) -0.0001(4) -0.0049(4) -0.0096(4) C26 0.0477(7) 0.0285(5) 0.0266(5) -0.0003(4) 0.0003(5) -0.0094(5) C27 0.0559(8) 0.0353(6) 0.0318(6) -0.0057(5) 0.0021(5) -0.0074(5) C28 0.0520(8) 0.0528(8) 0.0263(6) -0.0043(5) -0.0007(5) -0.0116(6) C29 0.0520(8) 0.0511(8) 0.0272(6) 0.0075(5) -0.0063(5) -0.0084(6) C30 0.0434(7) 0.0365(6) 0.0303(6) 0.0046(5) -0.0072(5) -0.0064(5) C31 0.0874(13) 0.0796(12) 0.0278(7) -0.0087(7) 0.0034(7) -0.0036(10) C32 0.1168(19) 0.133(2) 0.0472(10) 0.0057(11) 0.0231(11) 0.0507(16) C33 0.0220(4) 0.0242(4) 0.0233(4) -0.0016(3) 0.0023(3) -0.0008(3) C34 0.0280(5) 0.0244(5) 0.0280(5) -0.0004(4) 0.0016(4) 0.0000(4) C35 0.0362(6) 0.0248(5) 0.0354(6) -0.0060(4) 0.0038(4) -0.0001(4) C36 0.0392(6) 0.0349(6) 0.0301(5) -0.0105(4) 0.0016(4) -0.0024(5) C37 0.0464(7) 0.0388(6) 0.0244(5) -0.0041(4) -0.0045(5) 0.0030(5) C38 0.0365(6) 0.0262(5) 0.0260(5) -0.0028(4) -0.0028(4) 0.0036(4) C39 0.0664(10) 0.0466(8) 0.0365(7) -0.0192(6) 0.0018(7) -0.0029(7) C1X 0.064(16) 0.09(2) 0.14(3) 0.03(2) 0.038(18) -0.017(14) Cl1X 0.060(4) 0.109(6) 0.113(6) 0.028(5) -0.008(4) -0.017(4) Cl2X 0.27(2) 0.125(10) 0.27(2) -0.006(12) 0.167(18) -0.043(12) Cl3X 0.088(8) 0.186(15) 0.40(3) 0.036(17) -0.010(12) -0.054(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C4 1.2885(14) . ? N1 C1 1.4825(13) . ? N2 C9 1.3760(13) . ? N2 C6 1.3795(14) . ? N2 H2 0.883(15) . ? N3 C11 1.3184(13) . ? N3 C14 1.4018(13) . ? N4 C19 1.3583(12) . ? N4 C16 1.3645(12) . ? N4 H4 0.904(15) . ? C1 C19 1.5065(13) . ? C1 C20 1.5375(15) . ? C1 C2 1.5448(15) . ? C2 C3 1.5442(16) . ? C2 H2A 1.013(14) . ? C2 H2B 0.993(13) . ? C3 C4 1.5261(15) . ? C3 C22 1.526(2) . ? C3 C21 1.5372(17) . ? C4 C5 1.4491(14) . ? C5 C6 1.3625(15) . ? C5 H5 0.954(13) . ? C6 C7 1.4667(14) . ? C7 C8 1.3578(16) . ? C7 C25 1.4719(15) . ? C8 C9 1.4482(15) . ? C8 H8 0.999(14) . ? C9 C10 1.3714(16) . ? C10 C11 1.4280(15) . ? C10 H10 0.972(14) . ? C11 C12 1.5111(15) . ? C12 C13 1.5334(17) . ? C12 H12A 0.978(16) . ? C12 H12B 1.015(16) . ? C13 C23 1.5259(19) . ? C13 C24 1.5266(18) . ? C13 C14 1.5304(14) . ? C14 C15 1.3576(14) . ? C15 C16 1.4434(14) . ? C15 H15 0.989(13) . ? C16 C17 1.4017(13) . ? C17 C18 1.4286(13) . ? C17 C33 1.4656(13) . ? C18 C19 1.3773(14) . ? C18 H18 0.998(13) . ? C20 H20A 1.003(15) . ? C20 H20B 1.010(14) . ? C20 H20C 0.974(16) . ? C21 H21A 1.008(19) . ? C21 H21B 1.04(2) . ? C21 H21C 0.998(18) . ? C22 H22A 0.995(18) . ? C22 H22B 1.012(19) . ? C22 H22C 0.993(18) . ? C23 H23A 1.04(2) . ? C23 H23B 1.00(2) . ? C23 H23C 0.97(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.3942(16) . ? C25 C30 1.3982(16) . ? C26 C27 1.3872(17) . ? C26 H26 0.981(14) . ? C27 C28 1.3911(18) . ? C27 H27 0.972(16) . ? C28 C29 1.385(2) . ? C28 C31 1.5155(19) . ? C29 C30 1.3913(19) . ? C29 H29 0.961(17) . ? C30 H30 0.995(16) . ? C31 C32 1.513(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C38 1.3957(15) . ? C33 C34 1.4003(14) . ? C34 C35 1.3884(15) . ? C34 H34 0.976(14) . ? C35 C36 1.3905(17) . ? C35 H35 0.974(13) . ? C36 C37 1.3878(17) . ? C36 C39 1.5075(17) . ? C37 C38 1.3892(15) . ? C37 H37 0.977(16) . ? C38 H38 0.977(13) . ? C39 H39A 0.99(2) . ? C39 H39B 1.00(2) . ? C39 H39C 0.98(2) . ? C1X Cl1X 1.721(15) . ? C1X Cl2X 1.735(18) . ? C1X Cl3X 1.743(18) . ? C1X H1X 1.0000 . ? 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 C4 N1 C1 110.18(8) . . ? C9 N2 C6 111.52(9) . . ? C9 N2 H2 124.2(9) . . ? C6 N2 H2 124.2(9) . . ? C11 N3 C14 109.05(8) . . ? C19 N4 C16 111.60(8) . . ? C19 N4 H4 126.6(9) . . ? C16 N4 H4 121.7(9) . . ? N1 C1 C19 107.05(8) . . ? N1 C1 C20 109.32(8) . . ? C19 C1 C20 108.25(9) . . ? N1 C1 C2 104.71(8) . . ? C19 C1 C2 114.46(8) . . ? C20 C1 C2 112.76(9) . . ? C3 C2 C1 105.23(8) . . ? C3 C2 H2A 112.4(8) . . ? C1 C2 H2A 112.6(8) . . ? C3 C2 H2B 109.2(7) . . ? C1 C2 H2B 108.6(8) . . ? H2A C2 H2B 108.7(11) . . ? C4 C3 C22 112.59(11) . . ? C4 C3 C21 108.95(10) . . ? C22 C3 C21 109.90(12) . . ? C4 C3 C2 100.21(8) . . ? C22 C3 C2 111.86(10) . . ? C21 C3 C2 113.04(11) . . ? N1 C4 C5 122.60(9) . . ? N1 C4 C3 115.39(9) . . ? C5 C4 C3 122.01(9) . . ? C6 C5 C4 123.61(10) . . ? C6 C5 H5 118.7(8) . . ? C4 C5 H5 117.5(8) . . ? C5 C6 N2 124.80(9) . . ? C5 C6 C7 128.97(10) . . ? N2 C6 C7 105.93(9) . . ? C8 C7 C6 107.40(9) . . ? C8 C7 C25 127.64(10) . . ? C6 C7 C25 124.94(10) . . ? C7 C8 C9 109.41(9) . . ? C7 C8 H8 126.1(8) . . ? C9 C8 H8 124.5(8) . . ? C10 C9 N2 126.21(10) . . ? C10 C9 C8 127.95(10) . . ? N2 C9 C8 105.72(9) . . ? C9 C10 C11 126.04(9) . . ? C9 C10 H10 115.2(8) . . ? C11 C10 H10 118.4(8) . . ? N3 C11 C10 124.18(9) . . ? N3 C11 C12 113.43(9) . . ? C10 C11 C12 122.18(9) . . ? C11 C12 C13 104.07(8) . . ? C11 C12 H12A 109.0(9) . . ? C13 C12 H12A 114.2(9) . . ? C11 C12 H12B 110.3(9) . . ? C13 C12 H12B 112.4(9) . . ? H12A C12 H12B 106.9(12) . . ? C23 C13 C24 110.21(13) . . ? C23 C13 C14 110.33(10) . . ? C24 C13 C14 111.02(9) . . ? C23 C13 C12 111.91(11) . . ? C24 C13 C12 111.32(10) . . ? C14 C13 C12 101.80(8) . . ? C15 C14 N3 124.11(9) . . ? C15 C14 C13 124.41(9) . . ? N3 C14 C13 111.47(8) . . ? C14 C15 C16 126.32(9) . . ? C14 C15 H15 117.8(8) . . ? C16 C15 H15 115.9(8) . . ? N4 C16 C17 106.70(8) . . ? N4 C16 C15 119.88(9) . . ? C17 C16 C15 133.37(9) . . ? C16 C17 C18 106.57(8) . . ? C16 C17 C33 127.06(9) . . ? C18 C17 C33 126.37(9) . . ? C19 C18 C17 107.90(8) . . ? C19 C18 H18 125.9(7) . . ? C17 C18 H18 126.0(7) . . ? N4 C19 C18 107.21(8) . . ? N4 C19 C1 118.39(8) . . ? C18 C19 C1 134.36(9) . . ? C1 C20 H20A 110.3(8) . . ? C1 C20 H20B 108.6(8) . . ? H20A C20 H20B 108.9(11) . . ? C1 C20 H20C 109.9(9) . . ? H20A C20 H20C 108.6(12) . . ? H20B C20 H20C 110.5(12) . . ? C3 C21 H21A 109.1(11) . . ? C3 C21 H21B 111.2(11) . . ? H21A C21 H21B 111.5(15) . . ? C3 C21 H21C 109.5(10) . . ? H21A C21 H21C 105.5(14) . . ? H21B C21 H21C 109.9(15) . . ? C3 C22 H22A 113.5(10) . . ? C3 C22 H22B 109.4(10) . . ? H22A C22 H22B 108.1(14) . . ? C3 C22 H22C 109.2(10) . . ? H22A C22 H22C 107.9(14) . . ? H22B C22 H22C 108.6(15) . . ? C13 C23 H23A 110.1(12) . . ? C13 C23 H23B 108.6(11) . . ? H23A C23 H23B 110.9(16) . . ? C13 C23 H23C 113.0(12) . . ? H23A C23 H23C 105.5(16) . . ? H23B C23 H23C 108.7(16) . . ? C13 C24 H24A 109.5 . . ? C13 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C13 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 118.07(11) . . ? C26 C25 C7 121.19(10) . . ? C30 C25 C7 120.69(10) . . ? C27 C26 C25 120.75(11) . . ? C27 C26 H26 120.1(8) . . ? C25 C26 H26 119.1(8) . . ? C26 C27 C28 121.37(13) . . ? C26 C27 H27 119.8(9) . . ? C28 C27 H27 118.9(9) . . ? C29 C28 C27 117.81(12) . . ? C29 C28 C31 121.76(13) . . ? C27 C28 C31 120.41(14) . . ? C28 C29 C30 121.51(12) . . ? C28 C29 H29 120.3(10) . . ? C30 C29 H29 118.2(10) . . ? C29 C30 C25 120.47(12) . . ? C29 C30 H30 121.3(9) . . ? C25 C30 H30 118.3(9) . . ? C32 C31 C28 112.63(15) . . ? C32 C31 H31A 109.1 . . ? C28 C31 H31A 109.1 . . ? C32 C31 H31B 109.1 . . ? C28 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C38 C33 C34 117.67(9) . . ? C38 C33 C17 120.75(9) . . ? C34 C33 C17 121.59(9) . . ? C35 C34 C33 120.79(10) . . ? C35 C34 H34 120.6(8) . . ? C33 C34 H34 118.6(8) . . ? C34 C35 C36 121.35(10) . . ? C34 C35 H35 118.1(8) . . ? C36 C35 H35 120.6(8) . . ? C37 C36 C35 117.86(10) . . ? C37 C36 C39 121.23(12) . . ? C35 C36 C39 120.90(12) . . ? C36 C37 C38 121.29(11) . . ? C36 C37 H37 120.1(9) . . ? C38 C37 H37 118.6(9) . . ? C37 C38 C33 120.98(10) . . ? C37 C38 H38 119.7(8) . . ? C33 C38 H38 119.3(8) . . ? C36 C39 H39A 110.1(12) . . ? C36 C39 H39B 114.0(11) . . ? H39A C39 H39B 111.6(16) . . ? C36 C39 H39C 110.0(11) . . ? H39A C39 H39C 107.8(16) . . ? H39B C39 H39C 103.0(15) . . ? Cl1X C1X Cl2X 110.3(12) . . ? Cl1X C1X Cl3X 111.1(12) . . ? Cl2X C1X Cl3X 108.0(15) . . ? Cl1X C1X H1X 109.1 . . ? Cl2X C1X H1X 109.1 . . ? Cl3X C1X H1X 109.1 . . ? 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 C4 N1 C1 C19 134.61(9) . . . . ? C4 N1 C1 C20 -108.35(10) . . . . ? C4 N1 C1 C2 12.71(10) . . . . ? N1 C1 C2 C3 -20.03(10) . . . . ? C19 C1 C2 C3 -136.94(9) . . . . ? C20 C1 C2 C3 98.73(10) . . . . ? C1 C2 C3 C4 19.08(11) . . . . ? C1 C2 C3 C22 138.60(10) . . . . ? C1 C2 C3 C21 -96.71(12) . . . . ? C1 N1 C4 C5 -179.76(9) . . . . ? C1 N1 C4 C3 0.19(12) . . . . ? C22 C3 C4 N1 -131.78(11) . . . . ? C21 C3 C4 N1 106.04(12) . . . . ? C2 C3 C4 N1 -12.78(12) . . . . ? C22 C3 C4 C5 48.18(14) . . . . ? C21 C3 C4 C5 -74.00(14) . . . . ? C2 C3 C4 C5 167.17(9) . . . . ? N1 C4 C5 C6 21.20(16) . . . . ? C3 C4 C5 C6 -158.76(10) . . . . ? C4 C5 C6 N2 2.23(16) . . . . ? C4 C5 C6 C7 175.06(10) . . . . ? C9 N2 C6 C5 172.83(10) . . . . ? C9 N2 C6 C7 -1.38(11) . . . . ? C5 C6 C7 C8 -173.18(10) . . . . ? N2 C6 C7 C8 0.70(11) . . . . ? C5 C6 C7 C25 5.67(17) . . . . ? N2 C6 C7 C25 179.55(9) . . . . ? C6 C7 C8 C9 0.19(11) . . . . ? C25 C7 C8 C9 -178.63(10) . . . . ? C6 N2 C9 C10 -174.78(10) . . . . ? C6 N2 C9 C8 1.48(11) . . . . ? C7 C8 C9 C10 175.18(10) . . . . ? C7 C8 C9 N2 -1.00(11) . . . . ? N2 C9 C10 C11 9.14(17) . . . . ? C8 C9 C10 C11 -166.30(10) . . . . ? C14 N3 C11 C10 173.43(9) . . . . ? C14 N3 C11 C12 -1.36(12) . . . . ? C9 C10 C11 N3 -3.91(17) . . . . ? C9 C10 C11 C12 170.44(11) . . . . ? N3 C11 C12 C13 -1.53(13) . . . . ? C10 C11 C12 C13 -176.44(9) . . . . ? C11 C12 C13 C23 -114.41(12) . . . . ? C11 C12 C13 C24 121.75(11) . . . . ? C11 C12 C13 C14 3.40(11) . . . . ? C11 N3 C14 C15 -174.80(10) . . . . ? C11 N3 C14 C13 3.81(11) . . . . ? C23 C13 C14 C15 -66.95(16) . . . . ? C24 C13 C14 C15 55.53(15) . . . . ? C12 C13 C14 C15 174.10(10) . . . . ? C23 C13 C14 N3 114.44(13) . . . . ? C24 C13 C14 N3 -123.08(11) . . . . ? C12 C13 C14 N3 -4.50(11) . . . . ? N3 C14 C15 C16 -2.64(17) . . . . ? C13 C14 C15 C16 178.92(10) . . . . ? C19 N4 C16 C17 0.22(11) . . . . ? C19 N4 C16 C15 -177.57(9) . . . . ? C14 C15 C16 N4 -5.64(16) . . . . ? C14 C15 C16 C17 177.27(11) . . . . ? N4 C16 C17 C18 -0.96(11) . . . . ? C15 C16 C17 C18 176.40(11) . . . . ? N4 C16 C17 C33 178.63(9) . . . . ? C15 C16 C17 C33 -4.01(18) . . . . ? C16 C17 C18 C19 1.37(11) . . . . ? C33 C17 C18 C19 -178.23(9) . . . . ? C16 N4 C19 C18 0.65(12) . . . . ? C16 N4 C19 C1 178.97(9) . . . . ? C17 C18 C19 N4 -1.24(11) . . . . ? C17 C18 C19 C1 -179.16(11) . . . . ? N1 C1 C19 N4 8.88(12) . . . . ? C20 C1 C19 N4 -108.87(10) . . . . ? C2 C1 C19 N4 124.43(10) . . . . ? N1 C1 C19 C18 -173.38(11) . . . . ? C20 C1 C19 C18 68.88(14) . . . . ? C2 C1 C19 C18 -57.82(16) . . . . ? C8 C7 C25 C26 -134.80(12) . . . . ? C6 C7 C25 C26 46.58(15) . . . . ? C8 C7 C25 C30 42.61(16) . . . . ? C6 C7 C25 C30 -136.01(11) . . . . ? C30 C25 C26 C27 -0.73(18) . . . . ? C7 C25 C26 C27 176.75(11) . . . . ? C25 C26 C27 C28 1.3(2) . . . . ? C26 C27 C28 C29 -0.8(2) . . . . ? C26 C27 C28 C31 177.57(14) . . . . ? C27 C28 C29 C30 -0.3(2) . . . . ? C31 C28 C29 C30 -178.64(14) . . . . ? C28 C29 C30 C25 0.9(2) . . . . ? C26 C25 C30 C29 -0.35(18) . . . . ? C7 C25 C30 C29 -177.84(11) . . . . ? C29 C28 C31 C32 109.96(19) . . . . ? C27 C28 C31 C32 -68.3(2) . . . . ? C16 C17 C33 C38 143.26(11) . . . . ? C18 C17 C33 C38 -37.23(15) . . . . ? C16 C17 C33 C34 -36.22(15) . . . . ? C18 C17 C33 C34 143.29(10) . . . . ? C38 C33 C34 C35 -2.50(15) . . . . ? C17 C33 C34 C35 176.99(10) . . . . ? C33 C34 C35 C36 0.77(17) . . . . ? C34 C35 C36 C37 1.36(18) . . . . ? C34 C35 C36 C39 -178.00(12) . . . . ? C35 C36 C37 C38 -1.73(19) . . . . ? C39 C36 C37 C38 177.63(13) . . . . ? C36 C37 C38 C33 -0.04(19) . . . . ? C34 C33 C38 C37 2.14(16) . . . . ? C17 C33 C38 C37 -177.36(10) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 32.52 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.556 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 941758'