# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 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_x _database_code_depnum_ccdc_archive 'CCDC 907725' #TrackingRef 'AMPPP-phenol.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(5-(pyren-1-yl)-3-(4-methoxyphenyl)-4,5-dihydropyrazol-1-yl)ethanone-phenol co-crystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H28 N2 O3' _chemical_formula_weight 512.585 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.9740(18) _cell_length_b 9.951(2) _cell_length_c 29.751(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.34(3) _cell_angle_gamma 90.00 _cell_volume 2656.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9838 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 5076 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.1470 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.37 _reflns_number_total 5076 _reflns_number_gt 2356 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0460P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(3) _refine_ls_number_reflns 5076 _refine_ls_number_parameters 697 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1614 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.1651 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _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 O1 O 0.5571(7) 0.4627(6) 0.75075(17) 0.0716(18) Uani 1 1 d . . . O2 O -0.0179(8) 0.1265(7) 0.4850(2) 0.092(2) Uani 1 1 d . . . O3 O 0.1744(9) -0.2193(7) 0.7041(2) 0.104(3) Uani 1 1 d . . . H3A H 0.1423 -0.1597 0.7205 0.155 Uiso 1 1 calc R . . N1 N 0.4080(9) 0.3764(8) 0.6961(2) 0.066(2) Uani 1 1 d . . . N2 N 0.3489(7) 0.3740(7) 0.65224(19) 0.0490(17) Uani 1 1 d . . . C1 C 0.2584(10) 0.2716(9) 0.8080(3) 0.060(2) Uani 1 1 d . . . C2 C 0.3451(11) 0.1539(10) 0.8174(3) 0.067(3) Uani 1 1 d . . . H2B H 0.3985 0.1137 0.7943 0.081 Uiso 1 1 calc R . . C3 C 0.3511(11) 0.0983(11) 0.8604(3) 0.080(3) Uani 1 1 d . . . H3B H 0.4093 0.0227 0.8659 0.096 Uiso 1 1 calc R . . C4 C 0.2672(12) 0.1582(12) 0.8964(4) 0.083(3) Uani 1 1 d . . . C5 C 0.1793(11) 0.2700(12) 0.8878(3) 0.078(3) Uani 1 1 d . . . C6 C 0.1666(10) 0.3263(10) 0.8430(3) 0.062(2) Uani 1 1 d . . . C7 C 0.2651(16) 0.1050(13) 0.9408(4) 0.114(5) Uani 1 1 d . . . H7A H 0.3231 0.0300 0.9474 0.136 Uiso 1 1 calc R . . C8 C 0.1818(16) 0.1598(17) 0.9739(4) 0.119(5) Uani 1 1 d . . . H8A H 0.1861 0.1244 1.0028 0.142 Uiso 1 1 calc R . . C9 C 0.0911(15) 0.2673(15) 0.9648(3) 0.101(4) Uani 1 1 d . . . H9A H 0.0298 0.3004 0.9874 0.121 Uiso 1 1 calc R . . C10 C 0.0882(14) 0.3276(14) 0.9231(4) 0.097(4) Uani 1 1 d . . . C11 C -0.0109(15) 0.4399(14) 0.9119(3) 0.105(4) Uani 1 1 d . . . H11A H -0.0732 0.4752 0.9338 0.126 Uiso 1 1 calc R . . C12 C -0.0131(14) 0.4935(11) 0.8694(3) 0.096(4) Uani 1 1 d . . . H12A H -0.0758 0.5652 0.8626 0.115 Uiso 1 1 calc R . . C13 C 0.0820(11) 0.4384(11) 0.8354(3) 0.068(3) Uani 1 1 d . . . C14 C 0.0703(10) 0.4942(9) 0.7898(3) 0.067(3) Uani 1 1 d . . . H14A H 0.0016 0.5616 0.7833 0.080 Uiso 1 1 calc R . . C15 C 0.1645(11) 0.4441(8) 0.7560(3) 0.066(3) Uani 1 1 d . . . H15A H 0.1686 0.4879 0.7284 0.079 Uiso 1 1 calc R . . C16 C 0.2518(10) 0.3300(10) 0.7632(3) 0.065(3) Uani 1 1 d . . . C17 C 0.3394(10) 0.2713(9) 0.7256(2) 0.062(2) Uani 1 1 d . . . H17A H 0.4178 0.2132 0.7379 0.075 Uiso 1 1 calc R . . C18 C 0.2448(11) 0.1925(9) 0.6927(2) 0.064(3) Uani 1 1 d . . . H18A H 0.1405 0.1934 0.7011 0.077 Uiso 1 1 calc R . . H18B H 0.2786 0.1003 0.6901 0.077 Uiso 1 1 calc R . . C19 C 0.2730(10) 0.2756(10) 0.6471(3) 0.060(2) Uani 1 1 d . . . C20 C 0.5064(11) 0.4662(9) 0.7103(3) 0.064(3) Uani 1 1 d . . . C21 C 0.5633(11) 0.5749(8) 0.6788(3) 0.071(3) Uani 1 1 d . . . H21A H 0.5152 0.5661 0.6501 0.107 Uiso 1 1 calc R . . H21B H 0.6691 0.5654 0.6753 0.107 Uiso 1 1 calc R . . H21C H 0.5416 0.6617 0.6913 0.107 Uiso 1 1 calc R . . C22 C 0.1902(11) 0.2332(9) 0.6064(3) 0.063(2) Uani 1 1 d . . . C23 C 0.0998(9) 0.1243(8) 0.6018(2) 0.053(2) Uani 1 1 d . . . H23A H 0.0817 0.0701 0.6267 0.064 Uiso 1 1 calc R . . C24 C 0.0360(12) 0.0934(10) 0.5621(3) 0.080(3) Uani 1 1 d . . . H24A H -0.0248 0.0179 0.5604 0.096 Uiso 1 1 calc R . . C25 C 0.0569(10) 0.1679(10) 0.5246(3) 0.065(3) Uani 1 1 d . . . C26 C 0.1457(9) 0.2813(10) 0.5257(3) 0.070(3) Uani 1 1 d . . . H26A H 0.1598 0.3327 0.5000 0.083 Uiso 1 1 calc R . . C27 C 0.2163(11) 0.3184(10) 0.5678(3) 0.069(3) Uani 1 1 d . . . H27A H 0.2763 0.3943 0.5699 0.083 Uiso 1 1 calc R . . C28 C -0.0037(14) 0.2043(11) 0.4472(3) 0.108(4) Uani 1 1 d . . . H28A H -0.0610 0.1656 0.4231 0.162 Uiso 1 1 calc R . . H28B H 0.0992 0.2085 0.4388 0.162 Uiso 1 1 calc R . . H28C H -0.0395 0.2933 0.4533 0.162 Uiso 1 1 calc R . . C29 C 0.0712(13) -0.2400(10) 0.6664(3) 0.077(3) Uani 1 1 d . . . C30 C -0.0522(12) -0.1759(10) 0.6619(3) 0.071(3) Uani 1 1 d . . . H30A H -0.0819 -0.1134 0.6833 0.085 Uiso 1 1 calc R . . C31 C -0.1447(13) -0.2035(11) 0.6225(3) 0.101(4) Uani 1 1 d . . . H31A H -0.2381 -0.1638 0.6198 0.121 Uiso 1 1 calc R . . C32 C -0.0936(13) -0.2896(11) 0.5887(4) 0.096 Uani 1 1 d . . . H32A H -0.1489 -0.3035 0.5626 0.115 Uiso 1 1 calc R . . C33 C 0.0447(11) -0.3550(10) 0.5955(3) 0.078(3) Uani 1 1 d . . . H33A H 0.0794 -0.4152 0.5740 0.093 Uiso 1 1 calc R . . C34 C 0.1284(16) -0.3304(10) 0.6334(3) 0.102(4) Uani 1 1 d . . . H34A H 0.2204 -0.3718 0.6376 0.123 Uiso 1 1 calc R . . O4 O 1.0494(8) -0.0164(6) 0.75338(19) 0.079(2) Uani 1 1 d . . . O5 O 0.5468(9) 0.2793(8) 1.0309(2) 0.102(2) Uani 1 1 d . . . O6 O 0.6765(10) -0.3402(7) 0.8005(2) 0.117(3) Uani 1 1 d . . . H6A H 0.6397 -0.4009 0.7854 0.176 Uiso 1 1 calc R . . N3 N 0.9159(8) 0.0611(8) 0.8101(2) 0.0585(19) Uani 1 1 d . . . N4 N 0.8728(8) 0.0632(7) 0.8554(2) 0.0563(19) Uani 1 1 d . . . C35 C 0.7464(10) 0.1696(9) 0.7006(3) 0.057(2) Uani 1 1 d . . . C36 C 0.8304(11) 0.2875(10) 0.6898(3) 0.072(3) Uani 1 1 d . . . H36A H 0.8855 0.3299 0.7123 0.087 Uiso 1 1 calc R . . C37 C 0.8316(13) 0.3385(10) 0.6478(3) 0.087(3) Uani 1 1 d . . . H37A H 0.8912 0.4129 0.6421 0.105 Uiso 1 1 calc R . . C38 C 0.7446(10) 0.2828(10) 0.6113(3) 0.059(2) Uani 1 1 d . . . C39 C 0.6610(11) 0.1681(12) 0.6221(3) 0.073(3) Uani 1 1 d . . . C40 C 0.6603(9) 0.1160(9) 0.6664(3) 0.053(2) Uani 1 1 d . . . C41 C 0.7410(16) 0.3370(12) 0.5693(3) 0.104(4) Uani 1 1 d . . . H41A H 0.7931 0.4156 0.5631 0.125 Uiso 1 1 calc R . . C42 C 0.6611(16) 0.2755(14) 0.5371(4) 0.104(4) Uani 1 1 d . . . H42A H 0.6688 0.3102 0.5082 0.125 Uiso 1 1 calc R . . C43 C 0.5635(13) 0.1596(13) 0.5429(3) 0.090(4) Uani 1 1 d . . . H43A H 0.5049 0.1228 0.5201 0.108 Uiso 1 1 calc R . . C44 C 0.5694(12) 0.1098(13) 0.5878(3) 0.079(3) Uani 1 1 d . . . C45 C 0.4811(17) -0.0034(13) 0.5998(4) 0.113(5) Uani 1 1 d . . . H45A H 0.4231 -0.0424 0.5774 0.136 Uiso 1 1 calc R . . C46 C 0.4748(14) -0.0564(11) 0.6394(3) 0.089(4) Uani 1 1 d . . . H46A H 0.4117 -0.1282 0.6456 0.107 Uiso 1 1 calc R . . C47 C 0.5720(13) 0.0018(10) 0.6742(3) 0.076(3) Uani 1 1 d . . . C48 C 0.5732(11) -0.0492(10) 0.7166(3) 0.078(3) Uani 1 1 d . . . H48A H 0.5113 -0.1218 0.7227 0.093 Uiso 1 1 calc R . . C49 C 0.6615(11) 0.0006(10) 0.7516(3) 0.069(3) Uani 1 1 d . . . H49A H 0.6598 -0.0401 0.7798 0.083 Uiso 1 1 calc R . . C50 C 0.7500(10) 0.1093(9) 0.7442(3) 0.061(2) Uani 1 1 d . . . C51 C 0.8463(10) 0.1660(8) 0.7825(2) 0.055(2) Uani 1 1 d . . . H51A H 0.9234 0.2250 0.7702 0.066 Uiso 1 1 calc R . . C52 C 0.7499(10) 0.2463(8) 0.8182(2) 0.059(2) Uani 1 1 d . . . H52A H 0.7827 0.3388 0.8212 0.071 Uiso 1 1 calc R . . H52B H 0.6445 0.2443 0.8108 0.071 Uiso 1 1 calc R . . C53 C 0.7853(9) 0.1645(9) 0.8596(2) 0.045(2) Uani 1 1 d . . . C54 C 1.0088(10) -0.0268(10) 0.7937(3) 0.061(2) Uani 1 1 d . . . C55 C 1.0756(12) -0.1354(9) 0.8259(3) 0.081(3) Uani 1 1 d . . . H55A H 1.0316 -0.1267 0.8550 0.121 Uiso 1 1 calc R . . H55B H 1.1814 -0.1231 0.8283 0.121 Uiso 1 1 calc R . . H55C H 1.0549 -0.2233 0.8140 0.121 Uiso 1 1 calc R . . C56 C 0.7162(11) 0.1964(10) 0.9038(3) 0.063(2) Uani 1 1 d . . . C57 C 0.7544(11) 0.1205(9) 0.9432(3) 0.069(3) Uani 1 1 d . . . H57A H 0.8232 0.0509 0.9412 0.083 Uiso 1 1 calc R . . C58 C 0.6894(13) 0.1501(9) 0.9846(3) 0.078(3) Uani 1 1 d . . . H58A H 0.7045 0.0957 1.0097 0.094 Uiso 1 1 calc R . . C59 C 0.6049(10) 0.2597(11) 0.9865(3) 0.065(3) Uani 1 1 d . . . C60 C 0.5653(13) 0.3373(9) 0.9496(3) 0.083(3) Uani 1 1 d . . . H60A H 0.4974 0.4076 0.9517 0.100 Uiso 1 1 calc R . . C61 C 0.6345(11) 0.3030(10) 0.9087(3) 0.068(3) Uani 1 1 d . . . H61A H 0.6209 0.3594 0.8841 0.082 Uiso 1 1 calc R . . C62 C 0.4464(12) 0.3884(11) 1.0373(4) 0.103(4) Uani 1 1 d . . . H62A H 0.4134 0.3894 1.0679 0.155 Uiso 1 1 calc R . . H62B H 0.3621 0.3780 1.0176 0.155 Uiso 1 1 calc R . . H62C H 0.4961 0.4714 1.0307 0.155 Uiso 1 1 calc R . . C63 C 0.5851(12) -0.3153(11) 0.8391(3) 0.083(3) Uani 1 1 d . . . C64 C 0.6455(15) -0.2318(11) 0.8698(3) 0.098(4) Uani 1 1 d . . . H64A H 0.7368 -0.1903 0.8649 0.118 Uiso 1 1 calc R . . C65 C 0.5646(12) -0.2094(10) 0.9099(4) 0.085(3) Uani 1 1 d . . . H65A H 0.5962 -0.1448 0.9304 0.102 Uiso 1 1 calc R . . C66 C 0.4448(13) -0.2809(11) 0.9177(3) 0.092(4) Uani 1 1 d . . . H66A H 0.3963 -0.2694 0.9449 0.110 Uiso 1 1 calc R . . C67 C 0.3856(14) -0.3749(11) 0.8866(4) 0.107(4) Uani 1 1 d . . . H67A H 0.2993 -0.4234 0.8925 0.128 Uiso 1 1 calc R . . C68 C 0.4667(12) -0.3908(10) 0.8457(3) 0.076(3) Uani 1 1 d . . . H68A H 0.4364 -0.4531 0.8242 0.092 Uiso 1 1 calc R . . 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 O1 0.078(4) 0.097(5) 0.039(3) -0.012(3) -0.005(3) -0.006(4) O2 0.120(6) 0.085(5) 0.070(4) -0.003(4) -0.025(4) -0.009(5) O3 0.135(6) 0.108(6) 0.068(4) -0.013(4) -0.020(4) 0.027(5) N1 0.084(6) 0.052(5) 0.063(5) 0.000(4) 0.000(4) 0.000(5) N2 0.055(4) 0.054(5) 0.038(4) -0.010(3) -0.003(3) 0.006(4) C1 0.074(6) 0.059(6) 0.047(5) -0.015(4) 0.019(5) -0.010(5) C2 0.086(7) 0.067(7) 0.049(5) 0.002(5) 0.004(5) -0.019(6) C3 0.084(8) 0.087(8) 0.068(6) 0.013(6) -0.016(6) -0.027(7) C4 0.077(7) 0.100(10) 0.072(7) 0.013(7) 0.002(6) -0.019(7) C5 0.070(6) 0.110(9) 0.056(6) -0.018(6) 0.018(5) -0.054(7) C6 0.058(5) 0.077(7) 0.052(5) -0.020(5) 0.002(4) -0.022(6) C7 0.148(12) 0.105(10) 0.088(8) 0.009(8) -0.017(9) -0.064(10) C8 0.116(12) 0.160(15) 0.080(9) 0.021(10) 0.004(9) -0.032(11) C9 0.103(10) 0.158(13) 0.042(6) 0.000(7) 0.023(6) -0.052(10) C10 0.097(9) 0.110(10) 0.086(8) -0.035(8) 0.034(7) -0.040(8) C11 0.121(10) 0.132(11) 0.063(7) -0.026(7) 0.048(7) -0.034(9) C12 0.144(11) 0.072(7) 0.072(7) -0.031(6) 0.009(7) -0.014(8) C13 0.063(6) 0.092(8) 0.048(5) -0.018(5) 0.005(5) -0.022(6) C14 0.075(6) 0.054(6) 0.071(6) -0.008(5) -0.007(5) 0.005(5) C15 0.094(7) 0.042(5) 0.060(6) 0.003(5) -0.003(5) 0.016(6) C16 0.074(6) 0.073(7) 0.049(5) -0.014(5) 0.007(5) -0.005(6) C17 0.073(6) 0.067(6) 0.047(5) -0.004(5) 0.007(4) 0.007(5) C18 0.089(7) 0.065(6) 0.038(4) -0.010(4) -0.006(5) 0.000(6) C19 0.064(6) 0.062(6) 0.054(5) -0.029(5) -0.005(5) 0.013(6) C20 0.081(7) 0.060(6) 0.052(6) -0.013(5) 0.017(5) 0.026(6) C21 0.092(7) 0.061(6) 0.062(5) -0.001(5) 0.012(5) -0.010(6) C22 0.081(6) 0.044(5) 0.064(6) -0.003(5) 0.013(5) 0.000(5) C23 0.065(5) 0.060(6) 0.034(4) 0.011(4) -0.030(4) -0.012(5) C24 0.111(9) 0.066(7) 0.063(6) 0.016(5) -0.023(6) -0.003(7) C25 0.066(6) 0.067(6) 0.062(6) -0.002(5) -0.024(5) 0.012(6) C26 0.057(6) 0.093(8) 0.059(5) -0.012(5) 0.006(4) -0.016(6) C27 0.078(6) 0.081(7) 0.047(5) -0.023(5) 0.000(5) -0.001(6) C28 0.140(11) 0.100(9) 0.084(7) 0.023(7) -0.038(7) 0.011(9) C29 0.095(8) 0.072(7) 0.064(6) 0.012(5) 0.042(6) 0.033(6) C30 0.093(7) 0.072(7) 0.048(5) -0.005(5) 0.022(5) 0.019(6) C31 0.107(9) 0.116(10) 0.079(7) 0.003(7) 0.048(7) 0.023(8) C32 0.096 0.096 0.096 0.000 0.001 0.000 C33 0.070(6) 0.104(8) 0.060(6) -0.016(6) -0.004(5) 0.033(7) C34 0.178(13) 0.060(7) 0.069(6) -0.007(5) 0.002(8) 0.039(8) O4 0.105(5) 0.065(4) 0.066(4) -0.006(3) 0.018(4) 0.001(4) O5 0.121(6) 0.097(6) 0.088(5) -0.001(4) 0.020(5) 0.003(6) O6 0.167(8) 0.115(6) 0.069(4) -0.007(5) 0.012(5) -0.051(6) N3 0.070(5) 0.070(5) 0.035(4) -0.007(4) -0.021(4) 0.005(4) N4 0.075(5) 0.054(5) 0.040(4) -0.002(3) -0.004(4) -0.002(4) C35 0.064(5) 0.064(6) 0.042(5) -0.006(5) 0.016(4) 0.021(5) C36 0.093(8) 0.069(7) 0.055(6) -0.001(5) 0.001(5) 0.028(6) C37 0.133(10) 0.083(8) 0.046(5) 0.001(5) -0.001(6) 0.003(7) C38 0.057(6) 0.071(7) 0.049(5) -0.004(5) -0.007(4) 0.018(5) C39 0.067(6) 0.107(9) 0.047(5) -0.011(6) -0.006(5) 0.023(7) C40 0.055(5) 0.056(6) 0.048(5) -0.004(4) -0.009(4) 0.022(5) C41 0.162(13) 0.092(9) 0.058(7) 0.011(6) 0.004(7) 0.019(9) C42 0.142(12) 0.115(11) 0.057(7) 0.002(7) 0.007(8) 0.056(10) C43 0.090(8) 0.122(10) 0.058(6) -0.021(7) -0.027(6) 0.035(8) C44 0.079(7) 0.108(9) 0.049(6) -0.002(6) 0.002(5) 0.031(7) C45 0.138(12) 0.094(10) 0.107(10) -0.047(8) -0.046(9) 0.049(10) C46 0.126(10) 0.081(8) 0.060(6) -0.028(6) -0.026(7) 0.009(7) C47 0.112(9) 0.070(7) 0.046(5) -0.016(5) -0.029(6) 0.037(7) C48 0.071(7) 0.071(7) 0.091(7) -0.021(6) 0.023(6) 0.000(6) C49 0.085(7) 0.086(7) 0.037(5) 0.003(5) 0.000(5) -0.004(6) C50 0.062(6) 0.042(5) 0.079(6) -0.011(5) -0.023(5) -0.008(5) C51 0.066(6) 0.052(5) 0.048(5) -0.005(4) 0.005(4) -0.011(5) C52 0.066(5) 0.061(6) 0.050(5) -0.008(4) -0.018(4) 0.005(5) C53 0.050(5) 0.055(5) 0.030(4) -0.006(4) -0.004(4) -0.011(5) C54 0.064(6) 0.073(7) 0.046(5) 0.005(5) -0.008(5) -0.003(6) C55 0.103(8) 0.061(6) 0.078(6) 0.007(5) 0.015(6) 0.013(6) C56 0.071(6) 0.063(6) 0.053(5) -0.004(5) 0.006(5) -0.007(6) C57 0.079(7) 0.063(6) 0.066(6) -0.003(5) -0.010(5) 0.014(6) C58 0.128(9) 0.052(6) 0.055(5) 0.006(5) 0.018(6) 0.009(7) C59 0.076(6) 0.073(7) 0.046(5) -0.017(5) 0.006(5) 0.001(6) C60 0.117(9) 0.051(6) 0.081(7) -0.030(5) -0.004(7) 0.025(6) C61 0.086(7) 0.062(6) 0.056(6) 0.002(5) -0.004(5) 0.010(6) C62 0.084(8) 0.098(9) 0.129(9) -0.043(8) 0.035(7) 0.001(7) C63 0.079(7) 0.093(8) 0.077(7) -0.032(6) -0.009(6) -0.053(7) C64 0.134(10) 0.095(9) 0.065(6) 0.026(6) 0.007(7) -0.024(8) C65 0.086(8) 0.071(7) 0.098(8) 0.011(6) -0.009(6) -0.040(6) C66 0.126(9) 0.095(8) 0.056(5) -0.026(6) 0.053(6) -0.031(8) C67 0.116(10) 0.101(9) 0.103(8) -0.027(7) 0.017(8) -0.052(8) C68 0.096(8) 0.080(7) 0.053(6) -0.029(5) -0.032(5) 0.014(7) _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 O1 C20 1.285(9) . ? O2 C28 1.371(10) . ? O2 C25 1.414(10) . ? O3 C29 1.466(12) . ? O3 H3A 0.8200 . ? N1 C20 1.324(11) . ? N1 N2 1.404(9) . ? N1 C17 1.501(10) . ? N2 C19 1.202(10) . ? C1 C2 1.433(12) . ? C1 C6 1.438(11) . ? C1 C16 1.456(11) . ? C2 C3 1.395(11) . ? C2 H2B 0.9300 . ? C3 C4 1.442(13) . ? C3 H3B 0.9300 . ? C4 C5 1.387(14) . ? C4 C7 1.423(14) . ? C5 C6 1.451(12) . ? C5 C10 1.453(13) . ? C6 C13 1.367(12) . ? C7 C8 1.355(16) . ? C7 H7A 0.9300 . ? C8 C9 1.370(17) . ? C8 H8A 0.9300 . ? C9 C10 1.378(15) . ? C9 H9A 0.9300 . ? C10 C11 1.466(16) . ? C11 C12 1.372(14) . ? C11 H11A 0.9300 . ? C12 C13 1.436(13) . ? C12 H12A 0.9300 . ? C13 C14 1.469(12) . ? C14 C15 1.409(11) . ? C14 H14A 0.9300 . ? C15 C16 1.395(11) . ? C15 H15A 0.9300 . ? C16 C17 1.488(10) . ? C17 C18 1.512(11) . ? C17 H17A 0.9800 . ? C18 C19 1.609(11) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C22 1.480(11) . ? C20 C21 1.521(11) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.360(11) . ? C22 C27 1.448(11) . ? C23 C24 1.345(10) . ? C23 H23A 0.9300 . ? C24 C25 1.354(11) . ? C24 H24A 0.9300 . ? C25 C26 1.381(12) . ? C26 C27 1.448(11) . ? C26 H26A 0.9300 . ? C27 H27A 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.284(12) . ? C29 C34 1.428(12) . ? C30 C31 1.460(14) . ? C30 H30A 0.9300 . ? C31 C32 1.400(13) . ? C31 H31A 0.9300 . ? C32 C33 1.414(13) . ? C32 H32A 0.9300 . ? C33 C34 1.375(13) . ? C33 H33A 0.9300 . ? C34 H34A 0.9300 . ? O4 C54 1.260(9) . ? O5 C62 1.425(11) . ? O5 C59 1.438(10) . ? O6 C63 1.438(12) . ? O6 H6A 0.8200 . ? N3 C54 1.305(10) . ? N3 N4 1.406(8) . ? N3 C51 1.465(10) . ? N4 C53 1.284(9) . ? C35 C40 1.382(11) . ? C35 C50 1.428(11) . ? C35 C36 1.433(12) . ? C36 C37 1.350(11) . ? C36 H36A 0.9300 . ? C37 C38 1.444(12) . ? C37 H37A 0.9300 . ? C38 C41 1.359(12) . ? C38 C39 1.404(13) . ? C39 C40 1.417(11) . ? C39 C44 1.429(13) . ? C40 C47 1.406(13) . ? C41 C42 1.341(15) . ? C41 H41A 0.9300 . ? C42 C43 1.459(15) . ? C42 H42A 0.9300 . ? C43 C44 1.425(13) . ? C43 H43A 0.9300 . ? C44 C45 1.425(15) . ? C45 C46 1.292(14) . ? C45 H45A 0.9300 . ? C46 C47 1.469(12) . ? C46 H46A 0.9300 . ? C47 C48 1.359(12) . ? C48 C49 1.396(12) . ? C48 H48A 0.9300 . ? C49 C50 1.361(12) . ? C49 H49A 0.9300 . ? C50 C51 1.535(11) . ? C51 C52 1.588(10) . ? C51 H51A 0.9800 . ? C52 C53 1.509(10) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C56 1.491(10) . ? C54 C55 1.561(12) . ? C55 H55A 0.9600 . ? C55 H55B 0.9600 . ? C55 H55C 0.9600 . ? C56 C61 1.298(11) . ? C56 C57 1.435(11) . ? C57 C58 1.397(11) . ? C57 H57A 0.9300 . ? C58 C59 1.329(12) . ? C58 H58A 0.9300 . ? C59 C60 1.386(12) . ? C60 C61 1.411(12) . ? C60 H60A 0.9300 . ? C61 H61A 0.9300 . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 C68 1.317(13) . ? C63 C64 1.347(13) . ? C64 C65 1.417(14) . ? C64 H64A 0.9300 . ? C65 C66 1.311(12) . ? C65 H65A 0.9300 . ? C66 C67 1.415(13) . ? C66 H66A 0.9300 . ? C67 C68 1.430(13) . ? C67 H67A 0.9300 . ? C68 H68A 0.9300 . ? 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 C28 O2 C25 118.2(8) . . ? C29 O3 H3A 109.5 . . ? C20 N1 N2 123.8(8) . . ? C20 N1 C17 123.9(7) . . ? N2 N1 C17 112.3(7) . . ? C19 N2 N1 109.9(7) . . ? C2 C1 C6 118.7(8) . . ? C2 C1 C16 121.6(8) . . ? C6 C1 C16 119.5(9) . . ? C3 C2 C1 121.4(9) . . ? C3 C2 H2B 119.3 . . ? C1 C2 H2B 119.3 . . ? C2 C3 C4 120.0(10) . . ? C2 C3 H3B 120.0 . . ? C4 C3 H3B 120.0 . . ? C5 C4 C7 117.3(12) . . ? C5 C4 C3 119.6(10) . . ? C7 C4 C3 123.1(13) . . ? C4 C5 C6 121.4(9) . . ? C4 C5 C10 120.3(11) . . ? C6 C5 C10 118.1(12) . . ? C13 C6 C1 120.6(8) . . ? C13 C6 C5 120.6(9) . . ? C1 C6 C5 118.5(10) . . ? C8 C7 C4 122.4(15) . . ? C8 C7 H7A 118.8 . . ? C4 C7 H7A 118.8 . . ? C7 C8 C9 120.1(13) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C8 C9 C10 121.7(12) . . ? C8 C9 H9A 119.2 . . ? C10 C9 H9A 119.2 . . ? C9 C10 C5 118.1(13) . . ? C9 C10 C11 123.1(11) . . ? C5 C10 C11 118.6(11) . . ? C12 C11 C10 120.8(11) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C13 119.7(11) . . ? C11 C12 H12A 120.2 . . ? C13 C12 H12A 120.2 . . ? C6 C13 C12 121.8(9) . . ? C6 C13 C14 119.9(8) . . ? C12 C13 C14 117.8(10) . . ? C15 C14 C13 119.0(8) . . ? C15 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? C16 C15 C14 121.2(8) . . ? C16 C15 H15A 119.4 . . ? C14 C15 H15A 119.4 . . ? C15 C16 C1 118.9(8) . . ? C15 C16 C17 120.2(8) . . ? C1 C16 C17 120.8(9) . . ? C16 C17 N1 112.8(8) . . ? C16 C17 C18 113.1(8) . . ? N1 C17 C18 102.2(6) . . ? C16 C17 H17A 109.5 . . ? N1 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C17 C18 C19 100.9(7) . . ? C17 C18 H18A 111.6 . . ? C19 C18 H18A 111.6 . . ? C17 C18 H18B 111.6 . . ? C19 C18 H18B 111.6 . . ? H18A C18 H18B 109.4 . . ? N2 C19 C22 128.1(9) . . ? N2 C19 C18 113.9(7) . . ? C22 C19 C18 117.6(8) . . ? O1 C20 N1 120.9(9) . . ? O1 C20 C21 118.5(9) . . ? N1 C20 C21 120.6(8) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 119.1(8) . . ? C23 C22 C19 127.3(8) . . ? C27 C22 C19 113.6(8) . . ? C24 C23 C22 121.4(8) . . ? C24 C23 H23A 119.3 . . ? C22 C23 H23A 119.3 . . ? C23 C24 C25 122.6(10) . . ? C23 C24 H24A 118.7 . . ? C25 C24 H24A 118.7 . . ? C24 C25 C26 120.7(8) . . ? C24 C25 O2 117.4(9) . . ? C26 C25 O2 121.9(8) . . ? C25 C26 C27 118.5(8) . . ? C25 C26 H26A 120.7 . . ? C27 C26 H26A 120.7 . . ? C22 C27 C26 117.7(9) . . ? C22 C27 H27A 121.1 . . ? C26 C27 H27A 121.1 . . ? O2 C28 H28A 109.5 . . ? O2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 C34 123.8(11) . . ? C30 C29 O3 123.4(9) . . ? C34 C29 O3 112.7(10) . . ? C29 C30 C31 118.4(10) . . ? C29 C30 H30A 120.8 . . ? C31 C30 H30A 120.8 . . ? C32 C31 C30 120.3(10) . . ? C32 C31 H31A 119.8 . . ? C30 C31 H31A 119.8 . . ? C31 C32 C33 118.1(11) . . ? C31 C32 H32A 121.0 . . ? C33 C32 H32A 121.0 . . ? C34 C33 C32 120.7(10) . . ? C34 C33 H33A 119.7 . . ? C32 C33 H33A 119.7 . . ? C33 C34 C29 118.6(12) . . ? C33 C34 H34A 120.7 . . ? C29 C34 H34A 120.7 . . ? C62 O5 C59 117.3(8) . . ? C63 O6 H6A 109.5 . . ? C54 N3 N4 123.3(7) . . ? C54 N3 C51 122.7(7) . . ? N4 N3 C51 114.1(7) . . ? C53 N4 N3 106.0(6) . . ? C40 C35 C50 121.1(9) . . ? C40 C35 C36 116.3(8) . . ? C50 C35 C36 122.6(8) . . ? C37 C36 C35 121.6(9) . . ? C37 C36 H36A 119.2 . . ? C35 C36 H36A 119.2 . . ? C36 C37 C38 123.0(10) . . ? C36 C37 H37A 118.5 . . ? C38 C37 H37A 118.5 . . ? C41 C38 C39 121.5(10) . . ? C41 C38 C37 123.2(11) . . ? C39 C38 C37 115.3(8) . . ? C38 C39 C40 121.0(9) . . ? C38 C39 C44 118.2(9) . . ? C40 C39 C44 120.7(11) . . ? C35 C40 C47 120.1(8) . . ? C35 C40 C39 122.7(9) . . ? C47 C40 C39 117.1(8) . . ? C42 C41 C38 118.9(12) . . ? C42 C41 H41A 120.5 . . ? C38 C41 H41A 120.5 . . ? C41 C42 C43 126.6(11) . . ? C41 C42 H42A 116.7 . . ? C43 C42 H42A 116.7 . . ? C44 C43 C42 111.4(10) . . ? C44 C43 H43A 124.3 . . ? C42 C43 H43A 124.3 . . ? C45 C44 C43 119.6(12) . . ? C45 C44 C39 117.3(10) . . ? C43 C44 C39 123.1(12) . . ? C46 C45 C44 125.5(12) . . ? C46 C45 H45A 117.3 . . ? C44 C45 H45A 117.3 . . ? C45 C46 C47 116.9(12) . . ? C45 C46 H46A 121.6 . . ? C47 C46 H46A 121.6 . . ? C48 C47 C40 117.0(9) . . ? C48 C47 C46 120.5(11) . . ? C40 C47 C46 122.3(9) . . ? C47 C48 C49 124.1(10) . . ? C47 C48 H48A 117.9 . . ? C49 C48 H48A 117.9 . . ? C50 C49 C48 119.3(8) . . ? C50 C49 H49A 120.3 . . ? C48 C49 H49A 120.3 . . ? C49 C50 C35 118.1(8) . . ? C49 C50 C51 119.9(8) . . ? C35 C50 C51 122.0(8) . . ? N3 C51 C50 113.0(7) . . ? N3 C51 C52 102.5(6) . . ? C50 C51 C52 112.0(7) . . ? N3 C51 H51A 109.7 . . ? C50 C51 H51A 109.7 . . ? C52 C51 H51A 109.7 . . ? C53 C52 C51 99.3(6) . . ? C53 C52 H52A 111.9 . . ? C51 C52 H52A 111.9 . . ? C53 C52 H52B 111.9 . . ? C51 C52 H52B 111.9 . . ? H52A C52 H52B 109.6 . . ? N4 C53 C56 120.7(8) . . ? N4 C53 C52 118.1(7) . . ? C56 C53 C52 121.2(8) . . ? O4 C54 N3 119.3(8) . . ? O4 C54 C55 121.9(9) . . ? N3 C54 C55 118.6(8) . . ? C54 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C54 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C61 C56 C57 118.0(8) . . ? C61 C56 C53 120.8(8) . . ? C57 C56 C53 120.6(9) . . ? C58 C57 C56 120.7(9) . . ? C58 C57 H57A 119.6 . . ? C56 C57 H57A 119.6 . . ? C59 C58 C57 116.8(9) . . ? C59 C58 H58A 121.6 . . ? C57 C58 H58A 121.6 . . ? C58 C59 C60 124.6(8) . . ? C58 C59 O5 111.0(9) . . ? C60 C59 O5 124.0(9) . . ? C59 C60 C61 115.8(9) . . ? C59 C60 H60A 122.1 . . ? C61 C60 H60A 122.1 . . ? C56 C61 C60 123.2(9) . . ? C56 C61 H61A 118.4 . . ? C60 C61 H61A 118.4 . . ? O5 C62 H62A 109.5 . . ? O5 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? O5 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C68 C63 C64 124.9(10) . . ? C68 C63 O6 119.0(8) . . ? C64 C63 O6 114.8(10) . . ? C63 C64 C65 117.5(11) . . ? C63 C64 H64A 121.3 . . ? C65 C64 H64A 121.3 . . ? C66 C65 C64 119.2(10) . . ? C66 C65 H65A 120.4 . . ? C64 C65 H65A 120.4 . . ? C65 C66 C67 123.3(9) . . ? C65 C66 H66A 118.4 . . ? C67 C66 H66A 118.4 . . ? C66 C67 C68 115.9(10) . . ? C66 C67 H67A 122.0 . . ? C68 C67 H67A 122.0 . . ? C63 C68 C67 118.6(9) . . ? C63 C68 H68A 120.7 . . ? C67 C68 H68A 120.7 . . ? 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 C20 N1 N2 C19 173.8(8) . . . . ? C17 N1 N2 C19 -10.0(9) . . . . ? C6 C1 C2 C3 -5.1(13) . . . . ? C16 C1 C2 C3 180.0(8) . . . . ? C1 C2 C3 C4 1.0(14) . . . . ? C2 C3 C4 C5 0.8(14) . . . . ? C2 C3 C4 C7 178.4(9) . . . . ? C7 C4 C5 C6 -176.0(9) . . . . ? C3 C4 C5 C6 1.7(14) . . . . ? C7 C4 C5 C10 -0.8(14) . . . . ? C3 C4 C5 C10 176.9(9) . . . . ? C2 C1 C6 C13 -179.9(8) . . . . ? C16 C1 C6 C13 -4.9(12) . . . . ? C2 C1 C6 C5 7.4(12) . . . . ? C16 C1 C6 C5 -177.6(8) . . . . ? C4 C5 C6 C13 -178.6(9) . . . . ? C10 C5 C6 C13 6.1(13) . . . . ? C4 C5 C6 C1 -5.8(12) . . . . ? C10 C5 C6 C1 178.8(8) . . . . ? C5 C4 C7 C8 -0.1(17) . . . . ? C3 C4 C7 C8 -177.7(11) . . . . ? C4 C7 C8 C9 2(2) . . . . ? C7 C8 C9 C10 -4(2) . . . . ? C8 C9 C10 C5 3.0(17) . . . . ? C8 C9 C10 C11 177.9(12) . . . . ? C4 C5 C10 C9 -0.6(15) . . . . ? C6 C5 C10 C9 174.8(9) . . . . ? C4 C5 C10 C11 -175.7(10) . . . . ? C6 C5 C10 C11 -0.4(14) . . . . ? C9 C10 C11 C12 -177.8(10) . . . . ? C5 C10 C11 C12 -2.9(16) . . . . ? C10 C11 C12 C13 0.5(17) . . . . ? C1 C6 C13 C12 178.6(8) . . . . ? C5 C6 C13 C12 -8.8(13) . . . . ? C1 C6 C13 C14 7.4(12) . . . . ? C5 C6 C13 C14 -180.0(8) . . . . ? C11 C12 C13 C6 5.4(15) . . . . ? C11 C12 C13 C14 176.8(9) . . . . ? C6 C13 C14 C15 -9.9(12) . . . . ? C12 C13 C14 C15 178.6(9) . . . . ? C13 C14 C15 C16 9.8(13) . . . . ? C14 C15 C16 C1 -7.3(13) . . . . ? C14 C15 C16 C17 174.1(8) . . . . ? C2 C1 C16 C15 179.5(9) . . . . ? C6 C1 C16 C15 4.7(13) . . . . ? C2 C1 C16 C17 -2.0(13) . . . . ? C6 C1 C16 C17 -176.8(8) . . . . ? C15 C16 C17 N1 39.0(12) . . . . ? C1 C16 C17 N1 -139.5(9) . . . . ? C15 C16 C17 C18 -76.4(11) . . . . ? C1 C16 C17 C18 105.1(9) . . . . ? C20 N1 C17 C16 61.4(11) . . . . ? N2 N1 C17 C16 -114.8(8) . . . . ? C20 N1 C17 C18 -176.8(8) . . . . ? N2 N1 C17 C18 6.9(9) . . . . ? C16 C17 C18 C19 119.4(8) . . . . ? N1 C17 C18 C19 -2.2(8) . . . . ? N1 N2 C19 C22 -179.9(8) . . . . ? N1 N2 C19 C18 8.3(10) . . . . ? C17 C18 C19 N2 -3.7(10) . . . . ? C17 C18 C19 C22 -176.5(7) . . . . ? N2 N1 C20 O1 -179.6(7) . . . . ? C17 N1 C20 O1 4.6(13) . . . . ? N2 N1 C20 C21 -0.3(12) . . . . ? C17 N1 C20 C21 -176.1(8) . . . . ? N2 C19 C22 C23 -177.0(9) . . . . ? C18 C19 C22 C23 -5.4(13) . . . . ? N2 C19 C22 C27 5.1(13) . . . . ? C18 C19 C22 C27 176.7(8) . . . . ? C27 C22 C23 C24 0.9(14) . . . . ? C19 C22 C23 C24 -176.9(9) . . . . ? C22 C23 C24 C25 -0.2(15) . . . . ? C23 C24 C25 C26 -0.4(15) . . . . ? C23 C24 C25 O2 -179.1(9) . . . . ? C28 O2 C25 C24 176.9(9) . . . . ? C28 O2 C25 C26 -1.8(13) . . . . ? C24 C25 C26 C27 0.2(13) . . . . ? O2 C25 C26 C27 178.9(8) . . . . ? C23 C22 C27 C26 -1.0(13) . . . . ? C19 C22 C27 C26 177.1(7) . . . . ? C25 C26 C27 C22 0.4(12) . . . . ? C34 C29 C30 C31 4.4(15) . . . . ? O3 C29 C30 C31 179.0(8) . . . . ? C29 C30 C31 C32 -5.1(15) . . . . ? C30 C31 C32 C33 4.1(15) . . . . ? C31 C32 C33 C34 -2.3(16) . . . . ? C32 C33 C34 C29 1.5(17) . . . . ? C30 C29 C34 C33 -2.7(17) . . . . ? O3 C29 C34 C33 -177.8(9) . . . . ? C54 N3 N4 C53 178.0(8) . . . . ? C51 N3 N4 C53 -2.4(9) . . . . ? C40 C35 C36 C37 -3.6(13) . . . . ? C50 C35 C36 C37 176.4(9) . . . . ? C35 C36 C37 C38 2.7(15) . . . . ? C36 C37 C38 C41 177.3(10) . . . . ? C36 C37 C38 C39 -1.9(14) . . . . ? C41 C38 C39 C40 -177.1(9) . . . . ? C37 C38 C39 C40 2.1(12) . . . . ? C41 C38 C39 C44 -0.7(14) . . . . ? C37 C38 C39 C44 178.5(9) . . . . ? C50 C35 C40 C47 1.2(12) . . . . ? C36 C35 C40 C47 -178.8(8) . . . . ? C50 C35 C40 C39 -176.0(8) . . . . ? C36 C35 C40 C39 4.0(12) . . . . ? C38 C39 C40 C35 -3.4(13) . . . . ? C44 C39 C40 C35 -179.7(9) . . . . ? C38 C39 C40 C47 179.3(8) . . . . ? C44 C39 C40 C47 3.0(12) . . . . ? C39 C38 C41 C42 -3.2(16) . . . . ? C37 C38 C41 C42 177.6(10) . . . . ? C38 C41 C42 C43 6.0(18) . . . . ? C41 C42 C43 C44 -4.2(16) . . . . ? C42 C43 C44 C45 179.9(10) . . . . ? C42 C43 C44 C39 -0.2(14) . . . . ? C38 C39 C44 C45 -177.7(9) . . . . ? C40 C39 C44 C45 -1.3(14) . . . . ? C38 C39 C44 C43 2.4(14) . . . . ? C40 C39 C44 C43 178.8(9) . . . . ? C43 C44 C45 C46 -178.8(11) . . . . ? C39 C44 C45 C46 1.2(18) . . . . ? C44 C45 C46 C47 -2.7(18) . . . . ? C35 C40 C47 C48 1.7(13) . . . . ? C39 C40 C47 C48 179.1(8) . . . . ? C35 C40 C47 C46 178.0(8) . . . . ? C39 C40 C47 C46 -4.7(13) . . . . ? C45 C46 C47 C48 -179.3(11) . . . . ? C45 C46 C47 C40 4.6(15) . . . . ? C40 C47 C48 C49 -3.3(14) . . . . ? C46 C47 C48 C49 -179.6(9) . . . . ? C47 C48 C49 C50 1.9(15) . . . . ? C48 C49 C50 C35 1.1(13) . . . . ? C48 C49 C50 C51 179.4(8) . . . . ? C40 C35 C50 C49 -2.6(13) . . . . ? C36 C35 C50 C49 177.4(8) . . . . ? C40 C35 C50 C51 179.2(8) . . . . ? C36 C35 C50 C51 -0.8(13) . . . . ? C54 N3 C51 C50 60.9(11) . . . . ? N4 N3 C51 C50 -118.6(7) . . . . ? C54 N3 C51 C52 -178.4(8) . . . . ? N4 N3 C51 C52 2.1(8) . . . . ? C49 C50 C51 N3 40.8(11) . . . . ? C35 C50 C51 N3 -141.1(8) . . . . ? C49 C50 C51 C52 -74.4(10) . . . . ? C35 C50 C51 C52 103.7(9) . . . . ? N3 C51 C52 C53 -1.0(8) . . . . ? C50 C51 C52 C53 120.4(7) . . . . ? N3 N4 C53 C56 179.3(7) . . . . ? N3 N4 C53 C52 1.7(9) . . . . ? C51 C52 C53 N4 -0.4(9) . . . . ? C51 C52 C53 C56 -177.9(7) . . . . ? N4 N3 C54 O4 -175.3(7) . . . . ? C51 N3 C54 O4 5.2(13) . . . . ? N4 N3 C54 C55 0.1(13) . . . . ? C51 N3 C54 C55 -179.4(8) . . . . ? N4 C53 C56 C61 176.1(8) . . . . ? C52 C53 C56 C61 -6.4(12) . . . . ? N4 C53 C56 C57 4.5(12) . . . . ? C52 C53 C56 C57 -178.0(8) . . . . ? C61 C56 C57 C58 8.4(14) . . . . ? C53 C56 C57 C58 -179.8(8) . . . . ? C56 C57 C58 C59 -7.3(15) . . . . ? C57 C58 C59 C60 6.9(16) . . . . ? C57 C58 C59 O5 -179.2(8) . . . . ? C62 O5 C59 C58 -176.1(9) . . . . ? C62 O5 C59 C60 -2.2(14) . . . . ? C58 C59 C60 C61 -7.0(16) . . . . ? O5 C59 C60 C61 179.8(9) . . . . ? C57 C56 C61 C60 -8.8(14) . . . . ? C53 C56 C61 C60 179.4(9) . . . . ? C59 C60 C61 C56 8.1(15) . . . . ? C68 C63 C64 C65 -9.1(18) . . . . ? O6 C63 C64 C65 -176.4(9) . . . . ? C63 C64 C65 C66 7.5(17) . . . . ? C64 C65 C66 C67 -4.0(18) . . . . ? C65 C66 C67 C68 1.4(18) . . . . ? C64 C63 C68 C67 6.5(18) . . . . ? O6 C63 C68 C67 173.4(10) . . . . ? C66 C67 C68 C63 -2.3(16) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.157 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.040 data_1 _database_code_depnum_ccdc_archive 'CCDC 907726' #TrackingRef 'AMPPP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(5-(pyren-1-yl)-3-(4-methoxyphenyl)-4,5-dihydropyrazol-1-yl)ethanone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 N2 O2' _chemical_formula_weight 418.48 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7264(17) _cell_length_b 13.335(3) _cell_length_c 19.060(4) _cell_angle_alpha 84.69(3) _cell_angle_beta 86.33(3) _cell_angle_gamma 75.72(3) _cell_volume 2138.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20185 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0782 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8405 _reflns_number_gt 4429 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0879P)^2^+0.0000P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0102(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8405 _refine_ls_number_parameters 578 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1317 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1947 _refine_ls_wR_factor_gt 0.1656 _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 0.5505(3) 0.88803(17) 0.14821(12) 0.0552(6) Uani 1 1 d . . . N2 N 0.5244(3) 0.95944(17) 0.19999(12) 0.0543(6) Uani 1 1 d . . . N3 N 1.1041(3) 0.83744(19) 0.70140(14) 0.0640(7) Uani 1 1 d . . . N4 N 1.0349(3) 0.92698(19) 0.73530(13) 0.0593(7) Uani 1 1 d . . . O1 O 0.4640(3) 0.82877(19) 0.05652(12) 0.0851(7) Uani 1 1 d . . . O2 O 1.2936(3) 0.69095(19) 0.69260(15) 0.0944(8) Uani 1 1 d . . . O3 O 0.6279(2) 1.12364(14) 0.49436(10) 0.0645(6) Uani 1 1 d . . . O4 O 0.5844(3) 1.38249(16) 0.76191(11) 0.0684(6) Uani 1 1 d . . . C1 C 0.8389(3) 0.60245(18) 0.49135(14) 0.0424(6) Uani 1 1 d . . . C2 C 0.9433(3) 0.71747(19) 0.56037(14) 0.0439(6) Uani 1 1 d . . . C3 C 0.9165(3) 0.63566(19) 0.42862(14) 0.0463(7) Uani 1 1 d . . . C4 C 0.8520(3) 0.64268(18) 0.55668(14) 0.0419(6) Uani 1 1 d . . . C5 C 1.1050(3) 0.5199(2) 0.07039(14) 0.0498(7) Uani 1 1 d . . . C6 C 0.7739(3) 0.6079(2) 0.61824(14) 0.0459(7) Uani 1 1 d . . . C7 C 0.9035(3) 0.5939(2) 0.36527(15) 0.0557(8) Uani 1 1 d . . . H7 H 0.9546 0.6151 0.3243 0.067 Uiso 1 1 calc R . . C8 C 1.0227(3) 0.6261(2) 0.07434(13) 0.0471(7) Uani 1 1 d . . . C9 C 0.6106(3) 1.0756(2) 0.43616(14) 0.0493(7) Uani 1 1 d . . . C10 C 0.8041(3) 0.7581(2) 0.12122(14) 0.0474(7) Uani 1 1 d . . . C11 C 0.9547(3) 0.7547(2) 0.62541(15) 0.0512(7) Uani 1 1 d . . . C12 C 0.7883(3) 0.6479(2) 0.68197(15) 0.0569(8) Uani 1 1 d . . . H12 H 0.7369 0.6262 0.7227 0.068 Uiso 1 1 calc R . . C13 C 1.0065(3) 0.7102(2) 0.43430(15) 0.0514(7) Uani 1 1 d . . . H13 H 1.0591 0.7322 0.3940 0.062 Uiso 1 1 calc R . . C14 C 0.7395(3) 0.4890(2) 0.42318(16) 0.0561(8) Uani 1 1 d . . . H14 H 0.6803 0.4403 0.4207 0.067 Uiso 1 1 calc R . . C15 C 0.6729(3) 0.4952(2) 0.55181(16) 0.0536(7) Uani 1 1 d . . . H15 H 0.6149 0.4456 0.5505 0.064 Uiso 1 1 calc R . . C16 C 0.6034(3) 0.9704(2) 0.31708(14) 0.0458(6) Uani 1 1 d . . . C17 C 0.7027(3) 0.9766(2) 0.43117(15) 0.0554(7) Uani 1 1 d . . . H17 H 0.7673 0.9443 0.4678 0.067 Uiso 1 1 calc R . . C18 C 0.6061(3) 0.9158(2) 0.25329(14) 0.0463(6) Uani 1 1 d . . . C19 C 0.8856(3) 0.6533(2) 0.12042(13) 0.0468(7) Uani 1 1 d . . . C20 C 0.7493(3) 0.5275(2) 0.48802(15) 0.0476(7) Uani 1 1 d . . . C21 C 1.0537(3) 0.4410(2) 0.11273(15) 0.0544(7) Uani 1 1 d . . . C22 C 0.6823(3) 0.5335(2) 0.61233(17) 0.0545(7) Uani 1 1 d . . . H22 H 0.6282 0.5118 0.6522 0.065 Uiso 1 1 calc R . . C23 C 0.6588(3) 0.7879(2) 0.17016(14) 0.0509(7) Uani 1 1 d . . . H23 H 0.6013 0.7330 0.1740 0.061 Uiso 1 1 calc R . . C24 C 0.8150(4) 0.5212(2) 0.36316(17) 0.0610(8) Uani 1 1 d . . . H24 H 0.8066 0.4941 0.3207 0.073 Uiso 1 1 calc R . . C25 C 0.6482(3) 1.2481(2) 0.68756(14) 0.0537(7) Uani 1 1 d . . . H25 H 0.5706 1.2872 0.6582 0.064 Uiso 1 1 calc R . . C26 C 1.0186(3) 0.7501(2) 0.49554(15) 0.0497(7) Uani 1 1 d . . . H26 H 1.0767 0.7999 0.4961 0.060 Uiso 1 1 calc R . . C27 C 0.5063(3) 1.0680(2) 0.32458(15) 0.0575(8) Uani 1 1 d . . . H27 H 0.4373 1.0987 0.2892 0.069 Uiso 1 1 calc R . . C28 C 0.6783(4) 1.2871(2) 0.74837(15) 0.0549(7) Uani 1 1 d . . . C29 C 0.9399(3) 0.9895(2) 0.69243(15) 0.0503(7) Uani 1 1 d . . . C30 C 1.0437(4) 0.8378(2) 0.63122(16) 0.0578(8) Uani 1 1 d . . . H30 H 1.1312 0.8305 0.5957 0.069 Uiso 1 1 calc R . . C31 C 1.0784(3) 0.7044(2) 0.03293(15) 0.0556(7) Uani 1 1 d . . . C32 C 0.8779(3) 0.7195(2) 0.68535(15) 0.0572(8) Uani 1 1 d . . . H32 H 0.8871 0.7445 0.7285 0.069 Uiso 1 1 d R . . C33 C 0.8510(3) 1.0909(2) 0.71228(14) 0.0511(7) Uani 1 1 d . . . C34 C 0.5088(3) 1.1215(2) 0.38323(15) 0.0570(8) Uani 1 1 d . . . H34 H 0.4429 1.1874 0.3870 0.068 Uiso 1 1 d R . . C35 C 1.1342(4) 0.3374(2) 0.10730(18) 0.0707(9) Uani 1 1 d . . . H35 H 1.1014 0.2848 0.1351 0.085 Uiso 1 1 d R . . C36 C 0.8603(4) 0.8331(2) 0.08012(15) 0.0570(8) Uani 1 1 d . . . H36 H 0.8058 0.9024 0.0809 0.068 Uiso 1 1 d R . . C37 C 0.9189(4) 0.4711(2) 0.15924(15) 0.0601(8) Uani 1 1 d . . . H37 H 0.8850 0.4199 0.1881 0.072 Uiso 1 1 d R . . C38 C 0.6997(3) 0.9253(2) 0.37244(15) 0.0556(8) Uani 1 1 d . . . H38 H 0.7638 0.8587 0.3696 0.067 Uiso 1 1 d R . . C39 C 0.7325(3) 1.1512(2) 0.67021(15) 0.0529(7) Uani 1 1 d . . . H39 H 0.7098 1.1256 0.6294 0.063 Uiso 1 1 d R . . C40 C 0.8385(3) 0.5709(2) 0.16323(14) 0.0517(7) Uani 1 1 d . . . H40 H 0.7509 0.5866 0.1943 0.062 Uiso 1 1 d R . . C41 C 1.2902(4) 0.5751(3) -0.01720(16) 0.0706(9) Uani 1 1 d . . . H41 H 1.3776 0.5583 -0.0483 0.085 Uiso 1 1 d R . . C42 C 0.9965(4) 0.8069(2) 0.03779(15) 0.0624(8) Uani 1 1 d . . . H42 H 1.0339 0.8592 0.0119 0.075 Uiso 1 1 d R . . C43 C 1.3146(4) 0.3891(3) 0.01881(19) 0.0736(10) Uani 1 1 d . . . H43 H 1.4009 0.3706 -0.0126 0.088 Uiso 1 1 d R . . C44 C 1.2185(4) 0.6740(3) -0.01241(16) 0.0663(9) Uani 1 1 d . . . H44 H 1.2588 0.7248 -0.0386 0.080 Uiso 1 1 calc R . . C45 C 0.6999(3) 0.8077(2) 0.24446(14) 0.0506(7) Uani 1 1 d . . . H45A H 0.6685 0.7591 0.2801 0.061 Uiso 1 1 d R . . H45B H 0.8123 0.8024 0.2470 0.061 Uiso 1 1 d R . . C46 C 1.2393(3) 0.4932(3) 0.02318(15) 0.0586(8) Uani 1 1 d . . . C47 C 0.8807(4) 1.1329(2) 0.77245(16) 0.0636(8) Uani 1 1 d . . . H47 H 0.9595 1.0946 0.8016 0.076 Uiso 1 1 d R . . C48 C 0.7976(4) 1.2293(2) 0.79041(16) 0.0635(8) Uani 1 1 d . . . H48 H 0.8214 1.2558 0.8307 0.076 Uiso 1 1 d R . . C49 C 1.2633(4) 0.3134(3) 0.0603(2) 0.0799(11) Uani 1 1 d . . . H49 H 1.3162 0.2443 0.0569 0.096 Uiso 1 1 d R . . C50 C 0.9353(4) 0.9484(2) 0.62229(15) 0.0587(8) Uani 1 1 d . . . H50A H 0.9759 0.9902 0.5847 0.070 Uiso 1 1 d R . . H50B H 0.8285 0.9466 0.6123 0.070 Uiso 1 1 d R . . C51 C 0.4511(4) 0.8999(3) 0.09453(16) 0.0637(8) Uani 1 1 d . . . C52 C 0.5362(4) 1.2273(2) 0.49947(18) 0.0857(11) Uani 1 1 d . . . H52A H 0.5514 1.2685 0.4568 0.129 Uiso 1 1 d R . . H52B H 0.5692 1.2560 0.5386 0.129 Uiso 1 1 d R . . H52C H 0.4263 1.2272 0.5064 0.129 Uiso 1 1 d R . . C53 C 0.3313(4) 1.0018(3) 0.08468(19) 0.0889(11) Uani 1 1 d . . . H53A H 0.2431 0.9924 0.0606 0.133 Uiso 1 1 d R . . H53B H 0.3788 1.0511 0.0573 0.133 Uiso 1 1 d R . . H53C H 0.2953 1.0269 0.1299 0.133 Uiso 1 1 d R . . C54 C 1.2851(5) 0.7803(3) 0.79655(19) 0.0925(12) Uani 1 1 d . . . H54A H 1.1986 0.7854 0.8309 0.139 Uiso 1 1 d R . . H54B H 1.3213 0.8430 0.7932 0.139 Uiso 1 1 d R . . H54C H 1.3700 0.7225 0.8107 0.139 Uiso 1 1 d R . . C55 C 0.6176(5) 1.4302(3) 0.82140(18) 0.0897(12) Uani 1 1 d . . . H55A H 0.6056 1.3872 0.8637 0.135 Uiso 1 1 d R . . H55B H 0.5453 1.4970 0.8240 0.135 Uiso 1 1 d R . . H55C H 0.7241 1.4383 0.8165 0.135 Uiso 1 1 d R . . C56 C 1.2314(4) 0.7646(3) 0.7267(2) 0.0712(9) Uani 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 N1 0.0563(14) 0.0509(14) 0.0521(14) -0.0116(12) -0.0056(12) 0.0025(12) N2 0.0576(14) 0.0495(14) 0.0525(15) -0.0079(12) -0.0038(12) -0.0049(12) N3 0.0624(16) 0.0592(16) 0.0721(18) -0.0095(14) -0.0188(14) -0.0126(14) N4 0.0594(15) 0.0596(16) 0.0623(16) -0.0072(13) -0.0098(13) -0.0185(13) O1 0.0859(16) 0.0918(17) 0.0743(16) -0.0344(14) -0.0165(13) -0.0020(14) O2 0.0796(17) 0.0712(16) 0.128(2) -0.0160(16) -0.0193(16) -0.0035(14) O3 0.0715(13) 0.0517(12) 0.0647(13) -0.0168(10) -0.0229(11) 0.0052(10) O4 0.0780(14) 0.0624(13) 0.0634(13) -0.0170(11) 0.0036(11) -0.0116(12) C1 0.0331(13) 0.0337(14) 0.0535(17) 0.0007(12) -0.0032(12) 0.0038(11) C2 0.0359(14) 0.0392(15) 0.0523(17) -0.0013(12) -0.0051(12) -0.0009(12) C3 0.0399(14) 0.0400(15) 0.0526(17) 0.0041(13) -0.0051(13) 0.0004(12) C4 0.0337(13) 0.0334(14) 0.0540(17) 0.0004(12) -0.0037(12) -0.0005(11) C5 0.0452(15) 0.0585(18) 0.0451(16) -0.0188(14) -0.0064(13) -0.0048(14) C6 0.0380(14) 0.0427(15) 0.0524(17) 0.0036(13) -0.0005(12) -0.0040(12) C7 0.0553(17) 0.0526(18) 0.0500(18) -0.0013(14) -0.0062(14) 0.0041(15) C8 0.0480(15) 0.0566(17) 0.0393(15) -0.0082(13) -0.0050(13) -0.0151(14) C9 0.0496(16) 0.0480(17) 0.0498(17) -0.0066(13) -0.0078(13) -0.0086(14) C10 0.0483(15) 0.0523(17) 0.0410(15) -0.0077(13) -0.0043(13) -0.0090(14) C11 0.0427(15) 0.0446(16) 0.0632(19) -0.0023(14) -0.0027(14) -0.0055(13) C12 0.0540(17) 0.0624(19) 0.0515(18) 0.0042(15) 0.0020(14) -0.0131(16) C13 0.0447(15) 0.0509(17) 0.0529(18) 0.0037(14) 0.0045(13) -0.0051(14) C14 0.0488(17) 0.0455(17) 0.072(2) -0.0090(15) -0.0107(15) -0.0039(14) C15 0.0435(15) 0.0423(16) 0.073(2) 0.0017(15) -0.0028(15) -0.0080(13) C16 0.0466(15) 0.0413(15) 0.0469(16) -0.0034(12) 0.0001(13) -0.0064(13) C17 0.0537(17) 0.0519(18) 0.0532(18) -0.0055(14) -0.0108(14) 0.0041(15) C18 0.0424(14) 0.0447(16) 0.0488(16) -0.0029(13) 0.0016(13) -0.0062(13) C19 0.0473(15) 0.0501(17) 0.0401(15) -0.0092(13) -0.0025(13) -0.0040(14) C20 0.0369(14) 0.0378(15) 0.0621(19) -0.0012(13) -0.0084(13) 0.0030(12) C21 0.0541(17) 0.0560(18) 0.0493(17) -0.0147(14) -0.0088(14) -0.0008(15) C22 0.0441(16) 0.0482(17) 0.068(2) 0.0078(15) 0.0024(14) -0.0117(14) C23 0.0511(16) 0.0420(16) 0.0537(17) -0.0059(13) 0.0008(14) -0.0001(13) C24 0.0617(19) 0.0591(19) 0.058(2) -0.0132(16) -0.0126(16) -0.0014(16) C25 0.0541(17) 0.0606(19) 0.0480(17) -0.0058(14) -0.0010(14) -0.0165(15) C26 0.0436(15) 0.0402(15) 0.0620(19) 0.0040(14) -0.0009(14) -0.0070(13) C27 0.0554(17) 0.0557(18) 0.0552(18) -0.0074(15) -0.0141(14) 0.0027(15) C28 0.0616(18) 0.0550(18) 0.0531(18) -0.0095(15) 0.0102(15) -0.0252(16) C29 0.0515(16) 0.0531(17) 0.0498(17) -0.0008(14) -0.0066(14) -0.0196(15) C30 0.0585(18) 0.0586(19) 0.0595(19) -0.0118(15) -0.0044(15) -0.0170(15) C31 0.0553(17) 0.066(2) 0.0470(17) -0.0091(15) -0.0038(14) -0.0156(16) C32 0.0586(18) 0.0590(19) 0.0530(18) -0.0064(15) -0.0014(15) -0.0114(16) C33 0.0565(17) 0.0544(17) 0.0474(17) -0.0047(14) -0.0046(14) -0.0224(15) C34 0.0559(17) 0.0454(16) 0.0628(19) -0.0089(14) -0.0096(15) 0.0046(14) C35 0.078(2) 0.057(2) 0.075(2) -0.0210(17) -0.0109(19) -0.0030(18) C36 0.0623(19) 0.0493(17) 0.0569(18) -0.0023(14) -0.0037(15) -0.0095(15) C37 0.071(2) 0.0508(18) 0.0580(19) -0.0027(15) -0.0032(16) -0.0149(16) C38 0.0590(18) 0.0434(16) 0.0582(19) -0.0046(14) -0.0063(15) 0.0006(14) C39 0.0605(18) 0.0544(18) 0.0483(17) -0.0082(14) 0.0004(14) -0.0219(15) C40 0.0555(17) 0.0499(17) 0.0478(17) -0.0087(13) 0.0055(13) -0.0095(15) C41 0.059(2) 0.104(3) 0.0523(19) -0.024(2) 0.0058(16) -0.023(2) C42 0.069(2) 0.065(2) 0.0541(19) 0.0033(16) 0.0046(16) -0.0225(18) C43 0.0567(19) 0.088(3) 0.075(2) -0.041(2) -0.0060(17) -0.003(2) C44 0.0590(19) 0.090(3) 0.0521(19) -0.0089(17) 0.0087(15) -0.0245(19) C45 0.0500(16) 0.0456(16) 0.0506(17) -0.0041(13) 0.0048(13) -0.0026(13) C46 0.0484(17) 0.074(2) 0.0551(18) -0.0259(17) -0.0050(15) -0.0096(17) C47 0.071(2) 0.067(2) 0.0575(19) -0.0059(16) -0.0164(16) -0.0217(18) C48 0.079(2) 0.065(2) 0.0517(18) -0.0135(16) -0.0126(17) -0.0224(18) C49 0.075(2) 0.066(2) 0.090(3) -0.035(2) -0.016(2) 0.013(2) C50 0.0688(19) 0.0508(17) 0.0593(19) -0.0072(14) -0.0071(15) -0.0175(15) C51 0.0620(19) 0.069(2) 0.0542(19) -0.0069(17) -0.0079(16) -0.0022(17) C52 0.107(3) 0.057(2) 0.079(2) -0.0261(17) -0.032(2) 0.0211(19) C53 0.086(3) 0.087(3) 0.080(2) -0.001(2) -0.024(2) 0.009(2) C54 0.090(3) 0.099(3) 0.090(3) 0.014(2) -0.036(2) -0.025(2) C55 0.119(3) 0.080(2) 0.074(2) -0.039(2) -0.004(2) -0.019(2) C56 0.066(2) 0.064(2) 0.085(3) 0.0057(19) -0.0145(19) -0.0197(19) _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 C51 1.357(4) . ? N1 N2 1.404(3) . ? N1 C23 1.475(3) . ? N2 C18 1.288(3) . ? N3 C56 1.364(4) . ? N3 N4 1.395(3) . ? N3 C30 1.468(4) . ? N4 C29 1.292(3) . ? O1 C51 1.225(4) . ? O2 C56 1.221(4) . ? O3 O3 0.000(6) 1 ? O3 C9 1.365(3) . ? O3 C52 1.424(3) . ? O4 C28 1.370(3) . ? O4 C55 1.428(3) . ? C1 C20 1.420(4) . ? C1 C4 1.422(4) . ? C1 C3 1.425(4) . ? C2 C11 1.396(4) . ? C2 C4 1.431(3) . ? C2 C26 1.444(4) . ? C3 C7 1.398(4) . ? C3 C13 1.426(4) . ? C4 C6 1.417(3) . ? C5 C21 1.410(4) . ? C5 C46 1.424(4) . ? C5 C8 1.427(4) . ? C6 C12 1.396(4) . ? C6 C22 1.435(4) . ? C7 C24 1.385(4) . ? C7 H7 0.9300 . ? C8 C31 1.414(4) . ? C8 C19 1.430(4) . ? C9 O3 1.365(3) 1 ? C9 C17 1.375(4) . ? C9 C34 1.383(4) . ? C10 C36 1.379(4) . ? C10 C19 1.405(4) . ? C10 C23 1.518(4) . ? C11 C32 1.390(4) . ? C11 C30 1.517(4) . ? C12 C32 1.383(4) . ? C12 H12 0.9300 . ? C13 C26 1.347(4) . ? C13 H13 0.9300 . ? C14 C24 1.371(4) . ? C14 C20 1.397(4) . ? C14 H14 0.9300 . ? C15 C22 1.319(4) . ? C15 C20 1.431(4) . ? C15 H15 0.9300 . ? C16 C27 1.381(4) . ? C16 C38 1.389(4) . ? C16 C18 1.469(4) . ? C17 C38 1.369(4) . ? C17 H17 0.9300 . ? C18 C45 1.490(4) . ? C19 C40 1.433(4) . ? C21 C35 1.397(4) . ? C21 C37 1.425(4) . ? C22 H22 0.9300 . ? C23 C45 1.544(4) . ? C23 H23 0.9800 . ? C24 H24 0.9300 . ? C25 C39 1.377(4) . ? C25 C28 1.379(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C34 1.385(4) . ? C27 H27 0.9300 . ? C28 C48 1.384(4) . ? C29 C33 1.453(4) . ? C29 C50 1.497(4) . ? C30 C50 1.544(4) . ? C30 H30 0.9800 . ? C31 C42 1.386(4) . ? C31 C44 1.446(4) . ? C32 H32 0.9300 . ? C33 C47 1.388(4) . ? C33 C39 1.392(4) . ? C34 H34 0.9300 . ? C35 C49 1.385(5) . ? C35 H35 0.9300 . ? C36 C42 1.382(4) . ? C36 H36 0.9300 . ? C37 C40 1.350(4) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 C44 1.322(4) . ? C41 C46 1.422(4) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C43 C49 1.369(5) . ? C43 C46 1.390(4) . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C47 C48 1.373(4) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? C49 H49 0.9300 . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C53 1.501(4) . ? C52 O3 1.424(3) 1 ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C54 C56 1.489(5) . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C55 H55A 0.9600 . ? C55 H55B 0.9600 . ? C55 H55C 0.9600 . ? 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 C51 N1 N2 121.3(2) . . ? C51 N1 C23 123.0(2) . . ? N2 N1 C23 113.0(2) . . ? C18 N2 N1 107.8(2) . . ? C56 N3 N4 122.6(3) . . ? C56 N3 C30 123.3(3) . . ? N4 N3 C30 113.4(2) . . ? C29 N4 N3 108.0(2) . . ? O3 O3 C9 0(10) 1 . ? O3 O3 C52 0(10) 1 . ? C9 O3 C52 117.2(2) . . ? C28 O4 C55 118.0(3) . . ? C20 C1 C4 120.2(2) . . ? C20 C1 C3 119.1(3) . . ? C4 C1 C3 120.7(2) . . ? C11 C2 C4 118.9(2) . . ? C11 C2 C26 123.8(3) . . ? C4 C2 C26 117.3(2) . . ? C7 C3 C13 123.1(3) . . ? C7 C3 C1 119.6(3) . . ? C13 C3 C1 117.4(3) . . ? C6 C4 C1 119.4(2) . . ? C6 C4 C2 120.2(2) . . ? C1 C4 C2 120.4(2) . . ? C21 C5 C46 119.6(3) . . ? C21 C5 C8 120.4(2) . . ? C46 C5 C8 119.9(3) . . ? C12 C6 C4 118.7(2) . . ? C12 C6 C22 122.7(3) . . ? C4 C6 C22 118.6(3) . . ? C24 C7 C3 120.4(3) . . ? C24 C7 H7 119.8 . . ? C3 C7 H7 119.8 . . ? C31 C8 C5 119.6(3) . . ? C31 C8 C19 120.1(3) . . ? C5 C8 C19 120.2(3) . . ? O3 C9 O3 0.00(8) 1 . ? O3 C9 C17 116.5(2) 1 . ? O3 C9 C17 116.5(2) . . ? O3 C9 C34 123.7(2) 1 . ? O3 C9 C34 123.7(2) . . ? C17 C9 C34 119.8(3) . . ? C36 C10 C19 119.9(3) . . ? C36 C10 C23 120.7(2) . . ? C19 C10 C23 119.3(2) . . ? C32 C11 C2 120.2(3) . . ? C32 C11 C30 119.0(3) . . ? C2 C11 C30 120.7(3) . . ? C32 C12 C6 120.8(3) . . ? C32 C12 H12 119.6 . . ? C6 C12 H12 119.6 . . ? C26 C13 C3 122.7(3) . . ? C26 C13 H13 118.6 . . ? C3 C13 H13 118.6 . . ? C24 C14 C20 121.6(3) . . ? C24 C14 H14 119.2 . . ? C20 C14 H14 119.2 . . ? C22 C15 C20 122.1(3) . . ? C22 C15 H15 118.9 . . ? C20 C15 H15 118.9 . . ? C27 C16 C38 117.3(3) . . ? C27 C16 C18 121.9(2) . . ? C38 C16 C18 120.9(2) . . ? C38 C17 C9 120.2(3) . . ? C38 C17 H17 119.9 . . ? C9 C17 H17 119.9 . . ? N2 C18 C16 121.3(2) . . ? N2 C18 C45 114.6(2) . . ? C16 C18 C45 124.1(2) . . ? C10 C19 C8 118.8(3) . . ? C10 C19 C40 123.6(2) . . ? C8 C19 C40 117.6(2) . . ? C14 C20 C1 118.9(3) . . ? C14 C20 C15 123.1(3) . . ? C1 C20 C15 118.0(3) . . ? C35 C21 C5 119.6(3) . . ? C35 C21 C37 122.6(3) . . ? C5 C21 C37 117.8(3) . . ? C15 C22 C6 121.7(3) . . ? C15 C22 H22 119.2 . . ? C6 C22 H22 119.2 . . ? N1 C23 C10 113.9(2) . . ? N1 C23 C45 101.5(2) . . ? C10 C23 C45 112.7(2) . . ? N1 C23 H23 109.5 . . ? C10 C23 H23 109.5 . . ? C45 C23 H23 109.5 . . ? C14 C24 C7 120.5(3) . . ? C14 C24 H24 119.8 . . ? C7 C24 H24 119.8 . . ? C39 C25 C28 120.2(3) . . ? C39 C25 H25 119.9 . . ? C28 C25 H25 119.9 . . ? C13 C26 C2 121.5(3) . . ? C13 C26 H26 119.2 . . ? C2 C26 H26 119.2 . . ? C16 C27 C34 121.9(3) . . ? C16 C27 H27 119.0 . . ? C34 C27 H27 119.0 . . ? O4 C28 C25 115.6(3) . . ? O4 C28 C48 125.2(3) . . ? C25 C28 C48 119.2(3) . . ? N4 C29 C33 121.2(3) . . ? N4 C29 C50 113.9(3) . . ? C33 C29 C50 124.9(2) . . ? N3 C30 C11 113.9(2) . . ? N3 C30 C50 101.3(2) . . ? C11 C30 C50 112.3(2) . . ? N3 C30 H30 109.7 . . ? C11 C30 H30 109.7 . . ? C50 C30 H30 109.7 . . ? C42 C31 C8 118.5(3) . . ? C42 C31 C44 123.0(3) . . ? C8 C31 C44 118.5(3) . . ? C12 C32 C11 121.2(3) . . ? C12 C32 H32 119.4 . . ? C11 C32 H32 119.4 . . ? C47 C33 C39 116.9(3) . . ? C47 C33 C29 122.5(3) . . ? C39 C33 C29 120.7(3) . . ? C27 C34 C9 119.1(3) . . ? C27 C34 H34 120.4 . . ? C9 C34 H34 120.5 . . ? C49 C35 C21 119.6(3) . . ? C49 C35 H35 120.2 . . ? C21 C35 H35 120.2 . . ? C10 C36 C42 121.0(3) . . ? C10 C36 H36 119.5 . . ? C42 C36 H36 119.5 . . ? C40 C37 C21 122.6(3) . . ? C40 C37 H37 118.7 . . ? C21 C37 H37 118.7 . . ? C17 C38 C16 121.6(3) . . ? C17 C38 H38 119.2 . . ? C16 C38 H38 119.2 . . ? C25 C39 C33 121.6(3) . . ? C25 C39 H39 119.2 . . ? C33 C39 H39 119.2 . . ? C37 C40 C19 121.2(3) . . ? C37 C40 H40 119.4 . . ? C19 C40 H40 119.4 . . ? C44 C41 C46 122.7(3) . . ? C44 C41 H41 118.6 . . ? C46 C41 H41 118.6 . . ? C36 C42 C31 121.5(3) . . ? C36 C42 H42 119.2 . . ? C31 C42 H42 119.2 . . ? C49 C43 C46 120.7(3) . . ? C49 C43 H43 119.6 . . ? C46 C43 H43 119.7 . . ? C41 C44 C31 121.1(3) . . ? C41 C44 H44 119.5 . . ? C31 C44 H44 119.5 . . ? C18 C45 C23 103.1(2) . . ? C18 C45 H45A 111.1 . . ? C23 C45 H45A 111.1 . . ? C18 C45 H45B 111.1 . . ? C23 C45 H45B 111.1 . . ? H45A C45 H45B 109.1 . . ? C43 C46 C41 123.1(3) . . ? C43 C46 C5 118.8(3) . . ? C41 C46 C5 118.1(3) . . ? C48 C47 C33 122.2(3) . . ? C48 C47 H47 118.9 . . ? C33 C47 H47 118.9 . . ? C47 C48 C28 119.9(3) . . ? C47 C48 H48 120.1 . . ? C28 C48 H48 120.1 . . ? C43 C49 C35 121.6(3) . . ? C43 C49 H49 119.2 . . ? C35 C49 H49 119.2 . . ? C29 C50 C30 103.0(2) . . ? C29 C50 H50A 111.2 . . ? C30 C50 H50A 111.2 . . ? C29 C50 H50B 111.2 . . ? C30 C50 H50B 111.1 . . ? H50A C50 H50B 109.1 . . ? O1 C51 N1 119.3(3) . . ? O1 C51 C53 123.5(3) . . ? N1 C51 C53 117.2(3) . . ? O3 C52 O3 0.00(17) 1 . ? O3 C52 H52A 109.4 1 . ? O3 C52 H52A 109.4 . . ? O3 C52 H52B 109.5 1 . ? O3 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O3 C52 H52C 109.5 1 . ? O3 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.4 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C56 C54 H54A 109.5 . . ? C56 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C56 C54 H54C 109.4 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? O4 C55 H55A 109.5 . . ? O4 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? O4 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? O2 C56 N3 119.9(3) . . ? O2 C56 C54 123.7(3) . . ? N3 C56 C54 116.4(3) . . ? 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 C39 H39 O3 0.93 2.72 3.604(3) 159.4 1 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.8 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.053 data_x _database_code_depnum_ccdc_archive 'CCDC 912953' #TrackingRef 'AMPPP-naphthol.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(5-(pyren-1-yl)-3-(4-methoxyphenyl)-4,5-dihydropyrazol- 1-yl)ethanone-2-naphthol co-crystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H30 N2 O3' _chemical_formula_weight 562.64 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.133(2) _cell_length_b 8.7760(18) _cell_length_c 16.458(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.60(3) _cell_angle_gamma 90.00 _cell_volume 1462.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 5361 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0765 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 25.39 _reflns_number_total 5361 _reflns_number_gt 2684 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0400P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 5361 _refine_ls_number_parameters 388 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _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 C1 C 0.4615(4) 0.9364(4) 1.0862(2) 0.0551(11) Uani 1 1 d . . . N2 N 0.7533(4) 0.9756(4) 0.8647(2) 0.0669(10) Uani 1 1 d . . . O1 O 0.7565(3) 1.2068(3) 1.03909(18) 0.0831(10) Uani 1 1 d . . . O2 O 0.6771(4) 0.5864(4) 0.53933(19) 0.1043(12) Uani 1 1 d . . . N1 N 0.7180(4) 1.0417(4) 0.9376(2) 0.0674(10) Uani 1 1 d . . . C2 C 0.3453(5) 1.0214(5) 1.0593(3) 0.0658(12) Uani 1 1 d . . . H2A H 0.3447 1.0740 1.0102 0.079 Uiso 1 1 calc R . . C3 C 0.2369(5) 1.0253(5) 1.1050(3) 0.0783(14) Uani 1 1 d . . . H3A H 0.1643 1.0831 1.0870 0.094 Uiso 1 1 calc R . . O3 O 0.1541(3) 0.9171(4) 0.8559(2) 0.0884(10) Uani 1 1 d . . . H3B H 0.1813 0.8530 0.8888 0.133 Uiso 1 1 calc R . . C4 C 0.2309(5) 0.9440(6) 1.1792(3) 0.0777(14) Uani 1 1 d . . . C5 C 0.3402(5) 0.8563(5) 1.2055(3) 0.0663(12) Uani 1 1 d . . . C6 C 0.4556(5) 0.8568(4) 1.1602(2) 0.0553(11) Uani 1 1 d . . . C7 C 0.1165(6) 0.9455(7) 1.2231(4) 0.110(2) Uani 1 1 d . . . H7A H 0.0440 1.0040 1.2058 0.132 Uiso 1 1 calc R . . C8 C 0.1129(8) 0.8584(9) 1.2927(5) 0.133(3) Uani 1 1 d . . . H8A H 0.0372 0.8597 1.3227 0.159 Uiso 1 1 calc R . . C9 C 0.2172(9) 0.7702(8) 1.3189(4) 0.126(3) Uani 1 1 d . . . H9A H 0.2104 0.7103 1.3651 0.151 Uiso 1 1 calc R . . C10 C 0.3342(7) 0.7687(6) 1.2772(3) 0.0855(16) Uani 1 1 d . . . C11 C 0.4456(8) 0.6848(6) 1.3038(3) 0.1002(19) Uani 1 1 d . . . H11A H 0.4411 0.6263 1.3507 0.120 Uiso 1 1 calc R . . C12 C 0.5594(6) 0.6854(6) 1.2639(3) 0.0869(15) Uani 1 1 d . . . H12A H 0.6326 0.6314 1.2843 0.104 Uiso 1 1 calc R . . C13 C 0.5659(5) 0.7703(5) 1.1898(3) 0.0655(12) Uani 1 1 d . . . C14 C 0.6780(5) 0.7690(5) 1.1448(3) 0.0721(13) Uani 1 1 d . . . H14A H 0.7516 0.7142 1.1638 0.086 Uiso 1 1 calc R . . C15 C 0.6829(4) 0.8475(5) 1.0723(3) 0.0658(12) Uani 1 1 d . . . H15A H 0.7594 0.8437 1.0432 0.079 Uiso 1 1 calc R . . C16 C 0.5766(4) 0.9314(4) 1.0421(2) 0.0545(10) Uani 1 1 d . . . C17 C 0.5830(4) 1.0096(5) 0.9606(2) 0.0601(11) Uani 1 1 d . . . H17A H 0.5319 1.1044 0.9608 0.072 Uiso 1 1 calc R . . C18 C 0.5338(4) 0.9089(5) 0.8888(2) 0.0606(11) Uani 1 1 d . . . H18A H 0.5089 0.8084 0.9073 0.073 Uiso 1 1 calc R . . H18B H 0.4590 0.9551 0.8594 0.073 Uiso 1 1 calc R . . C19 C 0.6518(5) 0.9009(5) 0.8370(3) 0.0608(11) Uani 1 1 d . . . C20 C 0.7977(5) 1.1431(5) 0.9782(3) 0.0673(12) Uani 1 1 d . . . C21 C 0.9331(4) 1.1656(6) 0.9487(3) 0.0897(16) Uani 1 1 d . . . H21A H 0.9796 1.2386 0.9827 0.135 Uiso 1 1 calc R . . H21B H 0.9274 1.2022 0.8937 0.135 Uiso 1 1 calc R . . H21C H 0.9798 1.0703 0.9508 0.135 Uiso 1 1 calc R . . C22 C 0.6556(4) 0.8202(5) 0.7589(3) 0.0585(11) Uani 1 1 d . . . C23 C 0.5475(5) 0.7409(5) 0.7280(3) 0.0730(13) Uani 1 1 d . . . H23A H 0.4707 0.7408 0.7568 0.088 Uiso 1 1 calc R . . C24 C 0.5494(5) 0.6604(6) 0.6546(3) 0.0774(14) Uani 1 1 d . . . H24A H 0.4749 0.6075 0.6352 0.093 Uiso 1 1 calc R . . C25 C 0.6627(6) 0.6607(6) 0.6116(3) 0.0803(14) Uani 1 1 d . . . C26 C 0.7717(5) 0.7389(6) 0.6422(3) 0.0893(16) Uani 1 1 d . . . H26A H 0.8486 0.7389 0.6134 0.107 Uiso 1 1 calc R . . C27 C 0.7693(5) 0.8173(6) 0.7148(3) 0.0785(14) Uani 1 1 d . . . H27A H 0.8444 0.8687 0.7344 0.094 Uiso 1 1 calc R . . C28 C 0.5727(5) 0.4913(7) 0.5098(3) 0.108(2) Uani 1 1 d . . . H28A H 0.5959 0.4459 0.4593 0.161 Uiso 1 1 calc R . . H28B H 0.4939 0.5510 0.5012 0.161 Uiso 1 1 calc R . . H28C H 0.5576 0.4127 0.5488 0.161 Uiso 1 1 calc R . . C29 C 0.1529(4) 0.8576(6) 0.7800(3) 0.0726(13) Uani 1 1 d . . . C30 C 0.1161(4) 0.9573(6) 0.7161(3) 0.0840(15) Uani 1 1 d . . . H30A H 0.0927 1.0573 0.7274 0.101 Uiso 1 1 calc R . . C31 C 0.1148(5) 0.9084(7) 0.6385(4) 0.0935(17) Uani 1 1 d . . . H31A H 0.0920 0.9768 0.5971 0.112 Uiso 1 1 calc R . . C32 C 0.1465(5) 0.7571(7) 0.6176(3) 0.0761(14) Uani 1 1 d . . . C33 C 0.1423(6) 0.7012(10) 0.5381(4) 0.110(2) Uani 1 1 d . . . H33A H 0.1184 0.7663 0.4953 0.132 Uiso 1 1 calc R . . C34 C 0.1724(6) 0.5544(10) 0.5219(4) 0.116(2) Uani 1 1 d . . . H34A H 0.1673 0.5198 0.4684 0.139 Uiso 1 1 calc R . . C35 C 0.2112(5) 0.4544(7) 0.5843(4) 0.1061(18) Uani 1 1 d . . . H35A H 0.2337 0.3541 0.5730 0.127 Uiso 1 1 calc R . . C36 C 0.2152(5) 0.5073(7) 0.6626(3) 0.0929(16) Uani 1 1 d . . . H36A H 0.2405 0.4409 0.7045 0.112 Uiso 1 1 calc R . . C37 C 0.1829(4) 0.6570(6) 0.6819(3) 0.0694(12) Uani 1 1 d . . . C38 C 0.1863(4) 0.7126(6) 0.7625(3) 0.0718(13) Uani 1 1 d . . . H38A H 0.2122 0.6474 0.8048 0.086 Uiso 1 1 calc R . . 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 C1 0.071(3) 0.041(2) 0.054(3) -0.004(2) 0.007(2) -0.001(2) N2 0.076(3) 0.069(3) 0.056(2) -0.005(2) 0.012(2) -0.010(2) O1 0.113(3) 0.068(2) 0.068(2) -0.0093(17) 0.0037(19) -0.0095(19) O2 0.119(3) 0.122(3) 0.073(2) -0.028(2) 0.016(2) -0.002(3) N1 0.076(3) 0.065(2) 0.062(2) -0.004(2) 0.006(2) -0.016(2) C2 0.076(3) 0.057(3) 0.064(3) -0.001(2) -0.001(3) 0.005(3) C3 0.066(3) 0.082(4) 0.088(4) -0.010(3) 0.014(3) 0.007(3) O3 0.092(2) 0.080(2) 0.092(2) 0.006(2) -0.005(2) 0.008(2) C4 0.095(4) 0.067(3) 0.074(3) -0.016(3) 0.036(3) -0.004(3) C5 0.094(4) 0.048(3) 0.058(3) -0.014(2) 0.016(3) -0.011(3) C6 0.079(3) 0.044(2) 0.043(2) -0.004(2) 0.000(2) -0.003(2) C7 0.119(5) 0.096(5) 0.119(5) -0.009(4) 0.047(4) -0.004(4) C8 0.145(7) 0.113(6) 0.147(7) -0.024(5) 0.080(6) -0.025(5) C9 0.191(8) 0.105(5) 0.088(4) -0.004(4) 0.070(5) -0.016(5) C10 0.133(5) 0.063(3) 0.061(3) -0.006(3) 0.022(4) -0.013(4) C11 0.163(6) 0.081(4) 0.057(3) 0.013(3) 0.003(4) -0.019(5) C12 0.122(5) 0.075(3) 0.063(3) 0.011(3) -0.004(3) -0.007(3) C13 0.089(4) 0.056(3) 0.051(3) -0.001(2) -0.005(3) -0.008(3) C14 0.081(4) 0.060(3) 0.074(3) 0.004(3) -0.016(3) 0.005(3) C15 0.072(3) 0.055(3) 0.070(3) 0.003(3) 0.005(3) -0.001(3) C16 0.072(3) 0.043(2) 0.047(2) 0.001(2) -0.001(2) 0.000(2) C17 0.069(3) 0.052(3) 0.060(3) 0.001(2) 0.008(2) 0.000(2) C18 0.066(3) 0.060(3) 0.056(3) 0.002(2) 0.008(2) 0.005(2) C19 0.075(3) 0.053(3) 0.054(3) 0.002(2) 0.007(2) 0.005(2) C20 0.081(3) 0.058(3) 0.063(3) 0.011(3) 0.000(3) -0.001(3) C21 0.079(4) 0.097(4) 0.092(4) -0.002(3) -0.010(3) -0.018(3) C22 0.053(3) 0.056(3) 0.067(3) 0.000(2) 0.006(2) -0.002(2) C23 0.067(3) 0.081(4) 0.071(3) 0.000(3) 0.010(3) -0.002(3) C24 0.077(3) 0.090(4) 0.064(3) -0.010(3) -0.001(3) -0.011(3) C25 0.090(4) 0.089(4) 0.062(3) -0.012(3) 0.010(3) -0.003(3) C26 0.086(4) 0.113(5) 0.070(3) -0.010(3) 0.025(3) -0.009(3) C27 0.076(4) 0.088(4) 0.072(3) -0.019(3) 0.016(3) -0.012(3) C28 0.115(4) 0.126(5) 0.080(3) -0.034(4) -0.019(3) -0.003(4) C29 0.066(3) 0.072(4) 0.079(4) 0.015(3) 0.001(3) -0.002(3) C30 0.072(3) 0.083(4) 0.096(4) 0.016(3) -0.009(3) -0.001(3) C31 0.081(4) 0.106(5) 0.093(4) 0.035(4) -0.012(3) -0.001(4) C32 0.062(3) 0.098(4) 0.068(3) 0.017(3) 0.000(3) -0.009(3) C33 0.107(5) 0.146(7) 0.076(4) 0.016(4) -0.001(3) -0.014(5) C34 0.118(5) 0.155(7) 0.074(4) 0.002(5) 0.005(4) -0.019(5) C35 0.113(5) 0.113(5) 0.094(4) -0.011(4) 0.017(4) -0.004(4) C36 0.103(4) 0.096(4) 0.081(4) -0.001(3) 0.016(3) 0.001(3) C37 0.054(3) 0.083(4) 0.071(3) 0.011(3) 0.002(2) -0.004(3) C38 0.072(3) 0.074(4) 0.068(3) 0.016(3) -0.002(2) 0.003(3) _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 C1 C16 1.402(5) . ? C1 C6 1.408(5) . ? C1 C2 1.446(5) . ? N2 C19 1.286(5) . ? N2 N1 1.394(4) . ? O1 C20 1.237(5) . ? O2 C25 1.370(5) . ? O2 C28 1.416(5) . ? N1 C20 1.357(5) . ? N1 C17 1.463(5) . ? C2 C3 1.360(5) . ? C2 H2A 0.9300 . ? C3 C4 1.419(6) . ? C3 H3A 0.9300 . ? O3 C29 1.353(5) . ? O3 H3B 0.8200 . ? C4 C7 1.393(6) . ? C4 C5 1.401(6) . ? C5 C10 1.412(6) . ? C5 C6 1.414(6) . ? C6 C13 1.419(6) . ? C7 C8 1.379(8) . ? C7 H7A 0.9300 . ? C8 C9 1.364(8) . ? C8 H8A 0.9300 . ? C9 C10 1.396(8) . ? C9 H9A 0.9300 . ? C10 C11 1.401(7) . ? C11 C12 1.353(7) . ? C11 H11A 0.9300 . ? C12 C13 1.433(6) . ? C12 H12A 0.9300 . ? C13 C14 1.383(6) . ? C14 C15 1.381(5) . ? C14 H14A 0.9300 . ? C15 C16 1.378(5) . ? C15 H15A 0.9300 . ? C16 C17 1.511(5) . ? C17 C18 1.540(5) . ? C17 H17A 0.9800 . ? C18 C19 1.501(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C22 1.469(5) . ? C20 C21 1.489(6) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.376(5) . ? C22 C27 1.390(5) . ? C23 C24 1.400(6) . ? C23 H23A 0.9300 . ? C24 C25 1.376(6) . ? C24 H24A 0.9300 . ? C25 C26 1.376(6) . ? C26 C27 1.380(6) . ? C26 H26A 0.9300 . ? C27 H27A 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C38 1.351(6) . ? C29 C30 1.406(6) . ? C30 C31 1.346(6) . ? C30 H30A 0.9300 . ? C31 C32 1.412(7) . ? C31 H31A 0.9300 . ? C32 C33 1.397(7) . ? C32 C37 1.411(6) . ? C33 C34 1.353(8) . ? C33 H33A 0.9300 . ? C34 C35 1.395(8) . ? C34 H34A 0.9300 . ? C35 C36 1.368(7) . ? C35 H35A 0.9300 . ? C36 C37 1.395(6) . ? C36 H36A 0.9300 . ? C37 C38 1.412(6) . ? C38 H38A 0.9300 . ? 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 C16 C1 C6 120.1(4) . . ? C16 C1 C2 122.9(4) . . ? C6 C1 C2 117.1(4) . . ? C19 N2 N1 106.6(3) . . ? C25 O2 C28 118.1(4) . . ? C20 N1 N2 121.8(4) . . ? C20 N1 C17 122.8(4) . . ? N2 N1 C17 115.0(3) . . ? C3 C2 C1 120.7(4) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C2 C3 C4 122.1(5) . . ? C2 C3 H3A 119.0 . . ? C4 C3 H3A 119.0 . . ? C29 O3 H3B 109.5 . . ? C7 C4 C5 120.7(5) . . ? C7 C4 C3 120.7(6) . . ? C5 C4 C3 118.5(4) . . ? C4 C5 C10 119.5(5) . . ? C4 C5 C6 119.8(4) . . ? C10 C5 C6 120.7(5) . . ? C1 C6 C5 121.7(4) . . ? C1 C6 C13 119.9(4) . . ? C5 C6 C13 118.3(4) . . ? C8 C7 C4 118.6(6) . . ? C8 C7 H7A 120.7 . . ? C4 C7 H7A 120.7 . . ? C9 C8 C7 121.8(7) . . ? C9 C8 H8A 119.1 . . ? C7 C8 H8A 119.1 . . ? C8 C9 C10 120.9(7) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C9 C10 C11 122.7(6) . . ? C9 C10 C5 118.4(6) . . ? C11 C10 C5 118.9(6) . . ? C12 C11 C10 122.6(5) . . ? C12 C11 H11A 118.7 . . ? C10 C11 H11A 118.7 . . ? C11 C12 C13 119.3(5) . . ? C11 C12 H12A 120.4 . . ? C13 C12 H12A 120.4 . . ? C14 C13 C6 118.3(4) . . ? C14 C13 C12 121.5(5) . . ? C6 C13 C12 120.3(5) . . ? C15 C14 C13 121.4(4) . . ? C15 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C16 C15 C14 121.3(4) . . ? C16 C15 H15A 119.3 . . ? C14 C15 H15A 119.3 . . ? C15 C16 C1 119.0(4) . . ? C15 C16 C17 119.9(4) . . ? C1 C16 C17 121.0(4) . . ? N1 C17 C16 113.3(4) . . ? N1 C17 C18 100.7(3) . . ? C16 C17 C18 113.3(3) . . ? N1 C17 H17A 109.7 . . ? C16 C17 H17A 109.7 . . ? C18 C17 H17A 109.7 . . ? C19 C18 C17 103.0(3) . . ? C19 C18 H18A 111.2 . . ? C17 C18 H18A 111.2 . . ? C19 C18 H18B 111.2 . . ? C17 C18 H18B 111.2 . . ? H18A C18 H18B 109.1 . . ? N2 C19 C22 120.2(4) . . ? N2 C19 C18 114.8(4) . . ? C22 C19 C18 124.9(4) . . ? O1 C20 N1 118.7(4) . . ? O1 C20 C21 123.6(5) . . ? N1 C20 C21 117.6(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 117.5(4) . . ? C23 C22 C19 121.0(4) . . ? C27 C22 C19 121.4(4) . . ? C22 C23 C24 122.2(5) . . ? C22 C23 H23A 118.9 . . ? C24 C23 H23A 118.9 . . ? C25 C24 C23 119.1(5) . . ? C25 C24 H24A 120.4 . . ? C23 C24 H24A 120.4 . . ? O2 C25 C24 124.8(5) . . ? O2 C25 C26 116.1(5) . . ? C24 C25 C26 119.2(4) . . ? C25 C26 C27 121.3(5) . . ? C25 C26 H26A 119.3 . . ? C27 C26 H26A 119.3 . . ? C26 C27 C22 120.6(5) . . ? C26 C27 H27A 119.7 . . ? C22 C27 H27A 119.7 . . ? O2 C28 H28A 109.5 . . ? O2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C38 C29 O3 124.7(5) . . ? C38 C29 C30 119.1(5) . . ? O3 C29 C30 116.2(5) . . ? C31 C30 C29 120.1(5) . . ? C31 C30 H30A 119.9 . . ? C29 C30 H30A 119.9 . . ? C30 C31 C32 122.6(5) . . ? C30 C31 H31A 118.7 . . ? C32 C31 H31A 118.7 . . ? C33 C32 C37 118.7(6) . . ? C33 C32 C31 124.1(6) . . ? C37 C32 C31 117.2(5) . . ? C34 C33 C32 121.4(7) . . ? C34 C33 H33A 119.3 . . ? C32 C33 H33A 119.3 . . ? C33 C34 C35 120.8(6) . . ? C33 C34 H34A 119.6 . . ? C35 C34 H34A 119.6 . . ? C36 C35 C34 118.4(6) . . ? C36 C35 H35A 120.8 . . ? C34 C35 H35A 120.8 . . ? C35 C36 C37 122.5(5) . . ? C35 C36 H36A 118.8 . . ? C37 C36 H36A 118.8 . . ? C36 C37 C32 118.1(5) . . ? C36 C37 C38 122.9(5) . . ? C32 C37 C38 118.9(5) . . ? C29 C38 C37 122.0(5) . . ? C29 C38 H38A 119.0 . . ? C37 C38 H38A 119.0 . . ? 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 C19 N2 N1 C20 -172.3(4) . . . . ? C19 N2 N1 C17 -0.1(5) . . . . ? C16 C1 C2 C3 -178.7(4) . . . . ? C6 C1 C2 C3 1.2(6) . . . . ? C1 C2 C3 C4 -1.7(7) . . . . ? C2 C3 C4 C7 -177.5(5) . . . . ? C2 C3 C4 C5 -0.6(7) . . . . ? C7 C4 C5 C10 -0.1(7) . . . . ? C3 C4 C5 C10 -177.0(4) . . . . ? C7 C4 C5 C6 -179.8(4) . . . . ? C3 C4 C5 C6 3.3(6) . . . . ? C16 C1 C6 C5 -178.6(4) . . . . ? C2 C1 C6 C5 1.6(5) . . . . ? C16 C1 C6 C13 -0.6(5) . . . . ? C2 C1 C6 C13 179.6(4) . . . . ? C4 C5 C6 C1 -3.9(6) . . . . ? C10 C5 C6 C1 176.4(4) . . . . ? C4 C5 C6 C13 178.1(4) . . . . ? C10 C5 C6 C13 -1.6(6) . . . . ? C5 C4 C7 C8 -0.2(8) . . . . ? C3 C4 C7 C8 176.6(5) . . . . ? C4 C7 C8 C9 -0.8(9) . . . . ? C7 C8 C9 C10 2.1(11) . . . . ? C8 C9 C10 C11 177.3(6) . . . . ? C8 C9 C10 C5 -2.3(9) . . . . ? C4 C5 C10 C9 1.3(7) . . . . ? C6 C5 C10 C9 -179.0(5) . . . . ? C4 C5 C10 C11 -178.3(4) . . . . ? C6 C5 C10 C11 1.4(6) . . . . ? C9 C10 C11 C12 -179.0(5) . . . . ? C5 C10 C11 C12 0.7(8) . . . . ? C10 C11 C12 C13 -2.4(8) . . . . ? C1 C6 C13 C14 1.0(6) . . . . ? C5 C6 C13 C14 179.0(4) . . . . ? C1 C6 C13 C12 -178.2(4) . . . . ? C5 C6 C13 C12 -0.2(6) . . . . ? C11 C12 C13 C14 -177.0(5) . . . . ? C11 C12 C13 C6 2.1(7) . . . . ? C6 C13 C14 C15 -1.0(6) . . . . ? C12 C13 C14 C15 178.2(4) . . . . ? C13 C14 C15 C16 0.6(6) . . . . ? C14 C15 C16 C1 -0.2(6) . . . . ? C14 C15 C16 C17 -177.0(4) . . . . ? C6 C1 C16 C15 0.2(6) . . . . ? C2 C1 C16 C15 180.0(4) . . . . ? C6 C1 C16 C17 177.0(4) . . . . ? C2 C1 C16 C17 -3.2(6) . . . . ? C20 N1 C17 C16 -66.7(5) . . . . ? N2 N1 C17 C16 121.2(4) . . . . ? C20 N1 C17 C18 172.0(4) . . . . ? N2 N1 C17 C18 -0.1(4) . . . . ? C15 C16 C17 N1 -24.4(5) . . . . ? C1 C16 C17 N1 158.8(3) . . . . ? C15 C16 C17 C18 89.5(5) . . . . ? C1 C16 C17 C18 -87.3(5) . . . . ? N1 C17 C18 C19 0.2(4) . . . . ? C16 C17 C18 C19 -121.1(4) . . . . ? N1 N2 C19 C22 178.4(3) . . . . ? N1 N2 C19 C18 0.3(5) . . . . ? C17 C18 C19 N2 -0.4(5) . . . . ? C17 C18 C19 C22 -178.4(4) . . . . ? N2 N1 C20 O1 174.5(4) . . . . ? C17 N1 C20 O1 2.9(6) . . . . ? N2 N1 C20 C21 -8.5(6) . . . . ? C17 N1 C20 C21 180.0(4) . . . . ? N2 C19 C22 C23 -179.4(4) . . . . ? C18 C19 C22 C23 -1.5(6) . . . . ? N2 C19 C22 C27 2.5(6) . . . . ? C18 C19 C22 C27 -179.6(4) . . . . ? C27 C22 C23 C24 -0.5(6) . . . . ? C19 C22 C23 C24 -178.6(4) . . . . ? C22 C23 C24 C25 -0.2(7) . . . . ? C28 O2 C25 C24 -5.9(7) . . . . ? C28 O2 C25 C26 173.4(4) . . . . ? C23 C24 C25 O2 179.9(4) . . . . ? C23 C24 C25 C26 0.6(7) . . . . ? O2 C25 C26 C27 -179.6(4) . . . . ? C24 C25 C26 C27 -0.3(8) . . . . ? C25 C26 C27 C22 -0.4(8) . . . . ? C23 C22 C27 C26 0.8(7) . . . . ? C19 C22 C27 C26 178.9(4) . . . . ? C38 C29 C30 C31 -0.2(7) . . . . ? O3 C29 C30 C31 178.7(4) . . . . ? C29 C30 C31 C32 1.4(7) . . . . ? C30 C31 C32 C33 178.0(5) . . . . ? C30 C31 C32 C37 -1.1(7) . . . . ? C37 C32 C33 C34 -0.1(8) . . . . ? C31 C32 C33 C34 -179.2(6) . . . . ? C32 C33 C34 C35 -1.2(10) . . . . ? C33 C34 C35 C36 1.4(9) . . . . ? C34 C35 C36 C37 -0.3(8) . . . . ? C35 C36 C37 C32 -0.9(8) . . . . ? C35 C36 C37 C38 179.7(5) . . . . ? C33 C32 C37 C36 1.1(6) . . . . ? C31 C32 C37 C36 -179.7(5) . . . . ? C33 C32 C37 C38 -179.5(4) . . . . ? C31 C32 C37 C38 -0.3(6) . . . . ? O3 C29 C38 C37 179.9(4) . . . . ? C30 C29 C38 C37 -1.2(7) . . . . ? C36 C37 C38 C29 -179.1(5) . . . . ? C32 C37 C38 C29 1.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.144 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.036