# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address A.F.Khlebnikov ; Department of Chemistry Saint Petersburg State University Universitetskii pr. 26 198504 St.Petersburg Russia ; M.S.Novikov ; Department of Chemistry Saint Petersburg State University Universitetskii pr. 26 198504 St.Petersburg Russia ; M.V.Golovkina ; Department of Chemistry Saint Petersburg State University Universitetskii pr. 26 198504 St.Petersburg Russia ; 'Petrovskii, Petr P.' ; Department of Chemistry Saint Petersburg State University Universitetskii pr. 26 198504 St.Petersburg Russia ; ; A.S.Konev ; ; Department of Chemistry Saint Petersburg State University Universitetskii pr. 26 198504 St.Petersburg Russia ; D.S.Yufit ; Department of Chemistry Durham University South Rd. Durham DH1 3LE UK ; H.Stoeckli-Evans ; Institute of Physics rue Emile-Argand 11 Case postale 158 CH-2000 Neuchatel Switzerland ; _publ_contact_author_address ; Department of Chemistry Durham University South Rd. Durham DH1 3LE UK ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_author_name 'Dmitry Yufit' _publ_contact_letter ; The CIF file contains data for the structure 13 from the paper "New approach to azepino-fused heterocycles. Conformations of dibenzo[c,f]pyrrolo[1,2-a]azepine systems" by A.F.Khlebnikov, M.S.Novikov, M.V.Golovkina, P.P.Petrovskii, A.S.Konev, D.S.Yufit and H.Stoeckli-Evans The paper will be submitted to Org.Biomol.Chem. ; data_2b _database_code_depnum_ccdc_archive 'CCDC 809443' #TrackingRef '- 2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl N' _chemical_formula_sum 'C21 H16 Cl N' _chemical_formula_weight 317.80 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 11.5596(6) _cell_length_b 9.9041(5) _cell_length_c 13.9757(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.254(4) _cell_angle_gamma 90.00 _cell_volume 1599.66(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 17451 _cell_measurement_theta_min 1.46 _cell_measurement_theta_max 27.18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6143 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'STOE IPDS-2' _diffrn_measurement_method '\f + \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16074 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26.74 _reflns_number_total 3392 _reflns_number_gt 2979 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area V1.52 (Stoe & Cie, 2009)' _computing_cell_refinement 'X-Area V1.52' _computing_data_reduction 'X-RED32 V1.48 (Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL-97 _refine_special_details ; The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.95, 0.99 and 1.0 \%A for CH(aromatic), CH~2~, and CH(methine) H-atoms, respectively, with U~iso~(H) = 1.2U~eq~(C). ; _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^)+(0.0383P)^2^+0.6473P] 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 0.008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3392 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl1 Cl Uani 0.02583(4) 0.76754(4) 0.42065(4) 1.000 0.0508(2) . . N1 N Uani 0.37957(10) 0.24743(12) 0.56555(8) 1.000 0.0280(3) . . C1 C Uani 0.11285(13) 0.64848(14) 0.47976(12) 1.000 0.0332(4) . . C2 C Uani 0.20466(13) 0.59323(15) 0.43182(12) 1.000 0.0354(5) . . C3 C Uani 0.27303(13) 0.49776(16) 0.47803(11) 1.000 0.0325(4) . . C4 C Uani 0.25086(12) 0.45781(14) 0.57157(10) 1.000 0.0267(4) . . C5 C Uani 0.32319(11) 0.35476(14) 0.62198(10) 1.000 0.0262(4) . . C6 C Uani 0.45214(11) 0.34985(14) 0.61288(10) 1.000 0.0251(4) . . C7 C Uani 0.52974(11) 0.32295(14) 0.69633(10) 1.000 0.0262(4) . . C8 C Uani 0.60182(11) 0.20952(15) 0.69835(10) 1.000 0.0262(4) . . C9 C Uani 0.59224(12) 0.10497(15) 0.61952(10) 1.000 0.0304(4) . . C10 C Uani 0.47544(12) 0.03601(15) 0.61922(10) 1.000 0.0285(4) . . C11 C Uani 0.37477(12) 0.11030(15) 0.59848(10) 1.000 0.0277(4) . . C12 C Uani 0.26691(13) 0.04690(16) 0.60031(11) 1.000 0.0338(4) . . C13 C Uani 0.25871(14) -0.08938(17) 0.62150(11) 1.000 0.0385(5) . . C14 C Uani 0.35753(16) -0.16373(17) 0.64188(11) 1.000 0.0402(5) . . C15 C Uani 0.46493(14) -0.10055(16) 0.64132(11) 1.000 0.0355(5) . . C16 C Uani 0.68129(12) 0.19478(16) 0.77436(10) 1.000 0.0300(4) . . C17 C Uani 0.68883(13) 0.28983(16) 0.84679(11) 1.000 0.0340(4) . . C18 C Uani 0.61733(13) 0.40156(16) 0.84488(11) 1.000 0.0348(5) . . C19 C Uani 0.53790(12) 0.41851(15) 0.76941(11) 1.000 0.0315(4) . . C20 C Uani 0.15814(12) 0.51655(15) 0.61807(11) 1.000 0.0301(4) . . C21 C Uani 0.08817(13) 0.61173(15) 0.57247(12) 1.000 0.0343(4) . . H2 H Uiso 0.22060 0.62030 0.36820 1.000 0.0420 calc R H3 H Uiso 0.33610 0.45880 0.44550 1.000 0.0390 calc R H5 H Uiso 0.29380 0.32520 0.68540 1.000 0.0310 calc R H6 H Uiso 0.48300 0.41900 0.56800 1.000 0.0300 calc R H9A H Uiso 0.60350 0.14920 0.55690 1.000 0.0360 calc R H9B H Uiso 0.65390 0.03660 0.62870 1.000 0.0360 calc R H12 H Uiso 0.19870 0.09760 0.58690 1.000 0.0410 calc R H13 H Uiso 0.18500 -0.13190 0.62200 1.000 0.0460 calc R H14 H Uiso 0.35200 -0.25730 0.65620 1.000 0.0480 calc R H15 H Uiso 0.53250 -0.15150 0.65630 1.000 0.0430 calc R H16 H Uiso 0.73090 0.11830 0.77640 1.000 0.0360 calc R H17 H Uiso 0.74340 0.27820 0.89800 1.000 0.0410 calc R H18 H Uiso 0.62230 0.46650 0.89480 1.000 0.0420 calc R H19 H Uiso 0.48900 0.49560 0.76770 1.000 0.0380 calc R H20 H Uiso 0.14250 0.49110 0.68200 1.000 0.0360 calc R H21 H Uiso 0.02460 0.65080 0.60440 1.000 0.0410 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 Cl1 0.0450(3) 0.0352(2) 0.0717(3) 0.0184(2) -0.0113(2) 0.0047(2) N1 0.0228(6) 0.0327(6) 0.0284(6) -0.0012(5) -0.0018(4) -0.0010(5) C1 0.0302(7) 0.0226(7) 0.0464(9) 0.0052(6) -0.0078(6) -0.0037(6) C2 0.0392(8) 0.0317(8) 0.0351(8) 0.0088(6) -0.0003(6) -0.0045(6) C3 0.0299(7) 0.0340(8) 0.0336(7) 0.0028(6) 0.0034(6) 0.0008(6) C4 0.0252(7) 0.0246(7) 0.0301(7) -0.0004(5) -0.0016(5) -0.0038(5) C5 0.0239(6) 0.0284(7) 0.0262(6) -0.0002(5) -0.0012(5) -0.0024(5) C6 0.0210(6) 0.0277(7) 0.0264(7) 0.0030(5) -0.0019(5) -0.0029(5) C7 0.0202(6) 0.0304(7) 0.0279(7) 0.0034(5) -0.0020(5) -0.0050(5) C8 0.0201(6) 0.0323(7) 0.0261(7) 0.0018(6) 0.0002(5) -0.0028(5) C9 0.0237(7) 0.0380(8) 0.0294(7) -0.0028(6) 0.0010(5) 0.0041(6) C10 0.0295(7) 0.0333(7) 0.0226(6) -0.0065(6) 0.0018(5) -0.0004(6) C11 0.0273(7) 0.0333(7) 0.0226(6) -0.0056(6) 0.0000(5) -0.0026(6) C12 0.0282(7) 0.0421(9) 0.0312(7) -0.0081(6) 0.0016(6) -0.0055(6) C13 0.0395(9) 0.0432(9) 0.0329(8) -0.0100(7) 0.0054(6) -0.0140(7) C14 0.0555(10) 0.0321(8) 0.0334(8) -0.0074(6) 0.0080(7) -0.0096(7) C15 0.0427(9) 0.0343(8) 0.0296(7) -0.0065(6) 0.0028(6) 0.0040(7) C16 0.0238(7) 0.0350(8) 0.0312(7) 0.0046(6) -0.0023(5) 0.0004(6) C17 0.0302(7) 0.0402(8) 0.0311(7) 0.0036(6) -0.0104(6) -0.0059(6) C18 0.0357(8) 0.0336(8) 0.0347(8) -0.0051(6) -0.0076(6) -0.0071(6) C19 0.0280(7) 0.0278(7) 0.0386(8) -0.0008(6) -0.0042(6) -0.0026(6) C20 0.0285(7) 0.0294(7) 0.0323(7) 0.0018(6) 0.0012(6) -0.0030(6) C21 0.0278(7) 0.0278(7) 0.0472(9) -0.0004(6) 0.0016(6) 0.0005(6) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.7460(16) . . yes N1 C5 1.4830(18) . . yes N1 C6 1.4649(18) . . yes N1 C11 1.4355(19) . . yes C1 C2 1.381(2) . . no C1 C21 1.382(2) . . no C2 C3 1.383(2) . . no C3 C4 1.395(2) . . no C4 C5 1.4870(19) . . no C4 C20 1.393(2) . . no C5 C6 1.4996(18) . . no C6 C7 1.4799(19) . . no C7 C8 1.399(2) . . no C7 C19 1.394(2) . . no C8 C9 1.514(2) . . no C8 C16 1.3968(19) . . no C9 C10 1.513(2) . . no C10 C11 1.402(2) . . no C10 C15 1.393(2) . . no C11 C12 1.397(2) . . no C12 C13 1.386(2) . . no C13 C14 1.384(2) . . no C14 C15 1.391(2) . . no C16 C17 1.384(2) . . no C17 C18 1.381(2) . . no C18 C19 1.393(2) . . no C20 C21 1.388(2) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 1.0000 . . no C6 H6 1.0000 . . no C9 H9A 0.9900 . . no C9 H9B 0.9900 . . no C12 H12 0.9500 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C15 H15 0.9500 . . no C16 H16 0.9500 . . no C17 H17 0.9500 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C21 H21 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C6 61.15(9) . . . yes C5 N1 C11 119.16(11) . . . yes C6 N1 C11 122.42(11) . . . yes Cl1 C1 C2 118.63(13) . . . yes Cl1 C1 C21 119.54(12) . . . yes C2 C1 C21 121.83(14) . . . no C1 C2 C3 118.80(15) . . . no C2 C3 C4 121.11(14) . . . no C3 C4 C5 121.72(13) . . . no C3 C4 C20 118.54(13) . . . no C5 C4 C20 119.74(13) . . . no N1 C5 C4 119.28(12) . . . yes N1 C5 C6 58.83(9) . . . yes C4 C5 C6 122.12(12) . . . no N1 C6 C5 60.02(9) . . . yes N1 C6 C7 124.23(12) . . . yes C5 C6 C7 121.70(12) . . . no C6 C7 C8 120.74(12) . . . no C6 C7 C19 119.03(12) . . . no C8 C7 C19 119.99(13) . . . no C7 C8 C9 120.04(12) . . . no C7 C8 C16 118.75(13) . . . no C9 C8 C16 121.22(13) . . . no C8 C9 C10 111.21(11) . . . no C9 C10 C11 120.03(13) . . . no C9 C10 C15 121.32(13) . . . no C11 C10 C15 118.65(13) . . . no N1 C11 C10 121.68(12) . . . yes N1 C11 C12 118.16(13) . . . yes C10 C11 C12 119.84(14) . . . no C11 C12 C13 120.47(14) . . . no C12 C13 C14 120.16(15) . . . no C13 C14 C15 119.51(15) . . . no C10 C15 C14 121.35(15) . . . no C8 C16 C17 121.01(14) . . . no C16 C17 C18 120.19(14) . . . no C17 C18 C19 119.69(14) . . . no C7 C19 C18 120.38(13) . . . no C4 C20 C21 121.07(14) . . . no C1 C21 C20 118.64(14) . . . no C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C2 C3 H3 119.00 . . . no C4 C3 H3 119.00 . . . no N1 C5 H5 115.00 . . . no C4 C5 H5 115.00 . . . no C6 C5 H5 115.00 . . . no N1 C6 H6 114.00 . . . no C5 C6 H6 114.00 . . . no C7 C6 H6 114.00 . . . no C8 C9 H9A 109.00 . . . no C8 C9 H9B 109.00 . . . no C10 C9 H9A 109.00 . . . no C10 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no C11 C12 H12 120.00 . . . no C13 C12 H12 120.00 . . . no C12 C13 H13 120.00 . . . no C14 C13 H13 120.00 . . . no C13 C14 H14 120.00 . . . no C15 C14 H14 120.00 . . . no C10 C15 H15 119.00 . . . no C14 C15 H15 119.00 . . . no C8 C16 H16 120.00 . . . no C17 C16 H16 119.00 . . . no C16 C17 H17 120.00 . . . no C18 C17 H17 120.00 . . . no C17 C18 H18 120.00 . . . no C19 C18 H18 120.00 . . . no C7 C19 H19 120.00 . . . no C18 C19 H19 120.00 . . . no C4 C20 H20 120.00 . . . no C21 C20 H20 119.00 . . . no C1 C21 H21 121.00 . . . no C20 C21 H21 121.00 . . . no 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 C6 N1 C5 C4 111.92(14) . . . . no C11 N1 C5 C4 -134.90(13) . . . . no C11 N1 C5 C6 113.18(13) . . . . no C5 N1 C6 C7 109.96(15) . . . . no C11 N1 C6 C5 -108.00(13) . . . . no C11 N1 C6 C7 1.96(19) . . . . no C5 N1 C11 C10 -121.02(14) . . . . no C5 N1 C11 C12 65.42(17) . . . . no C6 N1 C11 C10 -48.49(19) . . . . no C6 N1 C11 C12 137.95(14) . . . . no Cl1 C1 C2 C3 -179.29(12) . . . . no C21 C1 C2 C3 0.5(2) . . . . no Cl1 C1 C21 C20 179.77(12) . . . . no C2 C1 C21 C20 0.0(2) . . . . no C1 C2 C3 C4 -0.4(2) . . . . no C2 C3 C4 C5 179.66(14) . . . . no C2 C3 C4 C20 -0.2(2) . . . . no C3 C4 C5 N1 -29.76(19) . . . . no C3 C4 C5 C6 39.8(2) . . . . no C20 C4 C5 N1 150.10(13) . . . . no C20 C4 C5 C6 -140.30(14) . . . . no C3 C4 C20 C21 0.7(2) . . . . no C5 C4 C20 C21 -179.17(13) . . . . no N1 C5 C6 C7 -114.01(14) . . . . no C4 C5 C6 N1 -107.17(14) . . . . no C4 C5 C6 C7 138.82(14) . . . . no N1 C6 C7 C8 45.34(19) . . . . no N1 C6 C7 C19 -140.38(14) . . . . no C5 C6 C7 C8 118.47(15) . . . . no C5 C6 C7 C19 -67.25(18) . . . . no C6 C7 C8 C9 -6.4(2) . . . . no C6 C7 C8 C16 174.10(13) . . . . no C19 C7 C8 C9 179.41(13) . . . . no C19 C7 C8 C16 -0.1(2) . . . . no C6 C7 C19 C18 -174.55(13) . . . . no C8 C7 C19 C18 -0.2(2) . . . . no C7 C8 C9 C10 -64.32(17) . . . . no C16 C8 C9 C10 115.20(14) . . . . no C7 C8 C16 C17 0.3(2) . . . . no C9 C8 C16 C17 -179.27(13) . . . . no C8 C9 C10 C11 64.90(17) . . . . no C8 C9 C10 C15 -113.68(15) . . . . no C9 C10 C11 N1 7.9(2) . . . . no C9 C10 C11 C12 -178.62(13) . . . . no C15 C10 C11 N1 -173.46(13) . . . . no C15 C10 C11 C12 0.0(2) . . . . no C9 C10 C15 C14 179.43(14) . . . . no C11 C10 C15 C14 0.8(2) . . . . no N1 C11 C12 C13 173.00(13) . . . . no C10 C11 C12 C13 -0.7(2) . . . . no C11 C12 C13 C14 0.6(2) . . . . no C12 C13 C14 C15 0.3(2) . . . . no C13 C14 C15 C10 -1.0(2) . . . . no C8 C16 C17 C18 0.0(2) . . . . no C16 C17 C18 C19 -0.3(2) . . . . no C17 C18 C19 C7 0.4(2) . . . . no C4 C20 C21 C1 -0.6(2) . . . . no _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.74 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.256 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.038 # Attachment '- 13.cif' data_13_DAX16 _database_code_depnum_ccdc_archive 'CCDC 809444' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C27 H25 N O4' _chemical_formula_sum 'C27 H25 N O4' _chemical_formula_weight 427.48 _chemical_melting_point '179 C' _chemical_name_common ? _chemical_name_systematic ; Dimethyl (1RS,2RS,3RS,13bRS)-3-phenyl-2,3,9,13b-tetrahydro-1H -dibenzo[c,f]pyrrolo[1,2-a]azepine-1,2-dicarboxylate ; 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' _space_group_IT_number 14 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 104.460(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.0710(2) _cell_length_b 25.9843(5) _cell_length_c 17.0032(3) _cell_measurement_reflns_used 6621 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 30.575 _cell_measurement_theta_min 2.595 _cell_volume 4308.58(20) _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_F_000 1808 _exptl_crystal_colour less _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier brownish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_special_details ? _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 52462 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 1.57 _diffrn_source_current 5.0 _diffrn_source_power 0.1 _diffrn_source_voltage 20.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6044 _reflns_number_total 11451 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution ; A short history of SHELX (Sheldrick, 2007)/Bruker ; _refine_diff_density_max 0.265 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.050 _refine_ls_R_factor_all 0.0965 _refine_ls_R_factor_gt 0.0458 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 777 _refine_ls_number_reflns 11451 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.0949 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.54066(11) 0.56017(4) 0.35503(7) 0.0382(3) Uani 1 1 d . . . O2 O 0.65391(12) 0.49088(4) 0.41521(7) 0.0392(3) Uani 1 1 d . . . O3 O 1.05955(10) 0.55649(4) 0.41302(6) 0.0325(3) Uani 1 1 d . . . O4 O 0.87467(11) 0.60783(4) 0.37557(7) 0.0377(3) Uani 1 1 d . . . N4 N 0.79862(12) 0.47812(5) 0.20278(7) 0.0280(3) Uani 1 1 d . . . C1 C 0.70866(15) 0.52513(6) 0.29575(9) 0.0258(3) Uani 1 1 d . . . C2 C 0.86219(15) 0.51987(6) 0.32937(9) 0.0266(3) Uani 1 1 d . . . C3 C 0.91447(16) 0.50666(6) 0.25334(9) 0.0271(4) Uani 1 1 d . . . C4A C 0.82245(15) 0.44221(6) 0.14637(9) 0.0260(3) Uani 1 1 d . . . C5 C 0.94330(17) 0.44655(6) 0.11976(10) 0.0302(4) Uani 1 1 d . . . C6 C 0.97082(17) 0.41389(6) 0.06164(10) 0.0327(4) Uani 1 1 d . . . C7 C 0.87906(17) 0.37562(6) 0.02795(10) 0.0323(4) Uani 1 1 d . . . C8 C 0.76099(17) 0.37057(6) 0.05455(10) 0.0306(4) Uani 1 1 d . . . C8A C 0.72988(15) 0.40233(6) 0.11303(9) 0.0271(3) Uani 1 1 d . . . C9 C 0.59727(17) 0.39240(6) 0.13682(10) 0.0306(4) Uani 1 1 d . . . C9A C 0.50453(16) 0.43871(6) 0.12285(9) 0.0298(4) Uani 1 1 d . . . C10 C 0.38407(17) 0.43957(7) 0.06100(10) 0.0356(4) Uani 1 1 d . . . C11 C 0.30133(19) 0.48282(8) 0.04882(11) 0.0416(5) Uani 1 1 d . . . C12 C 0.33741(18) 0.52526(7) 0.09849(11) 0.0400(4) Uani 1 1 d . . . C13 C 0.45799(16) 0.52511(6) 0.15929(10) 0.0324(4) Uani 1 1 d . . . C13A C 0.54349(15) 0.48222(6) 0.17170(9) 0.0273(3) Uani 1 1 d . . . C13B C 0.67647(15) 0.47944(6) 0.23687(9) 0.0251(3) Uani 1 1 d . . . C14 C 0.63322(16) 0.52267(6) 0.36203(10) 0.0292(4) Uani 1 1 d . . . C15 C 0.4641(2) 0.56075(9) 0.41696(14) 0.0455(5) Uani 1 1 d . . . C16 C 0.92955(16) 0.56682(6) 0.37426(9) 0.0278(4) Uani 1 1 d . . . C17 C 1.13901(19) 0.60001(7) 0.45104(12) 0.0370(4) Uani 1 1 d . . . C18 C 0.95485(16) 0.55449(6) 0.21351(9) 0.0278(3) Uani 1 1 d . . . C19 C 1.08928(18) 0.57222(7) 0.23799(10) 0.0352(4) Uani 1 1 d . . . C20 C 1.1268(2) 0.61879(7) 0.21015(11) 0.0432(5) Uani 1 1 d . . . C21 C 1.0302(2) 0.64745(7) 0.15635(11) 0.0445(5) Uani 1 1 d . . . C22 C 0.8968(2) 0.62958(7) 0.12835(11) 0.0397(4) Uani 1 1 d . . . C23 C 0.85923(18) 0.58312(6) 0.15708(10) 0.0320(4) Uani 1 1 d . . . H1 H 0.6883(13) 0.5566(5) 0.2676(8) 0.019(4) Uiso 1 1 d . . . H2 H 0.8816(14) 0.4904(5) 0.3673(8) 0.023(4) Uiso 1 1 d . . . H3 H 0.9966(14) 0.4849(5) 0.2694(8) 0.019(4) Uiso 1 1 d . . . H5 H 1.0110(14) 0.4742(5) 0.1415(8) 0.024(4) Uiso 1 1 d . . . H6 H 1.0562(15) 0.4180(5) 0.0463(9) 0.029(4) Uiso 1 1 d . . . H7 H 0.8943(16) 0.3524(6) -0.0128(9) 0.038(5) Uiso 1 1 d . . . H8 H 0.6945(15) 0.3432(6) 0.0325(9) 0.035(4) Uiso 1 1 d . . . H9A H 0.5498(15) 0.3632(6) 0.1022(9) 0.036(4) Uiso 1 1 d . . . H9B H 0.6180(14) 0.3802(5) 0.1933(9) 0.028(4) Uiso 1 1 d . . . H10 H 0.3625(14) 0.4112(5) 0.0267(9) 0.021(4) Uiso 1 1 d . . . H11 H 0.2207(17) 0.4836(6) 0.0059(10) 0.045(5) Uiso 1 1 d . . . H12 H 0.2807(17) 0.5542(7) 0.0933(10) 0.048(5) Uiso 1 1 d . . . H13 H 0.4828(15) 0.5552(6) 0.1955(9) 0.035(5) Uiso 1 1 d . . . H13A H 0.6733(13) 0.4486(5) 0.2713(8) 0.021(4) Uiso 1 1 d . . . H15A H 0.4079(19) 0.5294(7) 0.4123(11) 0.060(6) Uiso 1 1 d . . . H15B H 0.530(2) 0.5632(8) 0.4703(14) 0.084(8) Uiso 1 1 d . . . H15C H 0.417(2) 0.5928(8) 0.4066(12) 0.066(6) Uiso 1 1 d . . . H17A H 1.2243(18) 0.5841(6) 0.4877(10) 0.049(5) Uiso 1 1 d . . . H17B H 1.0870(18) 0.6201(7) 0.4846(11) 0.057(6) Uiso 1 1 d . . . H17C H 1.1585(16) 0.6219(6) 0.4069(10) 0.046(5) Uiso 1 1 d . . . H19 H 1.1585(16) 0.5508(6) 0.2766(10) 0.041(5) Uiso 1 1 d . . . H20 H 1.2191(18) 0.6297(6) 0.2309(10) 0.049(5) Uiso 1 1 d . . . H21 H 1.0580(17) 0.6809(7) 0.1358(10) 0.049(5) Uiso 1 1 d . . . H22 H 0.8248(17) 0.6488(6) 0.0877(10) 0.043(5) Uiso 1 1 d . . . H23 H 0.7640(16) 0.5696(6) 0.1374(9) 0.037(5) Uiso 1 1 d . . . O21 O 0.42915(11) 0.23087(4) 0.08756(7) 0.0368(3) Uani 1 1 d . . . O22 O 0.32588(12) 0.30036(4) 0.02160(7) 0.0405(3) Uani 1 1 d . . . O23 O -0.08901(11) 0.23140(4) 0.02464(7) 0.0374(3) Uani 1 1 d . . . O24 O 0.10066(11) 0.18378(4) 0.07128(7) 0.0400(3) Uani 1 1 d . . . N34 N 0.16040(12) 0.32492(5) 0.22074(7) 0.0274(3) Uani 1 1 d . . . C31 C 0.25826(15) 0.27039(6) 0.13970(9) 0.0247(3) Uani 1 1 d . . . C32 C 0.10436(15) 0.27369(6) 0.10408(9) 0.0265(3) Uani 1 1 d . . . C33 C 0.05082(16) 0.29082(6) 0.17796(9) 0.0262(3) Uani 1 1 d . . . C34A C 0.13797(15) 0.35909(5) 0.27930(9) 0.0256(3) Uani 1 1 d . . . C35 C 0.01582(16) 0.35510(6) 0.30517(9) 0.0286(4) Uani 1 1 d . . . C36 C -0.00772(17) 0.38556(6) 0.36657(10) 0.0317(4) Uani 1 1 d . . . C37 C 0.08775(17) 0.42104(6) 0.40568(10) 0.0317(4) Uani 1 1 d . . . C38 C 0.20527(17) 0.42718(6) 0.37803(9) 0.0294(4) Uani 1 1 d . . . C38A C 0.23109(15) 0.39828(6) 0.31464(9) 0.0260(3) Uani 1 1 d . . . C39 C 0.36067(17) 0.40903(6) 0.28770(10) 0.0292(4) Uani 1 1 d . . . C39A C 0.45598(15) 0.36366(6) 0.30448(9) 0.0276(4) Uani 1 1 d . . . C40 C 0.57477(16) 0.36456(7) 0.36662(10) 0.0312(4) Uani 1 1 d . . . C41 C 0.65778(17) 0.32123(7) 0.38445(10) 0.0348(4) Uani 1 1 d . . . C42 C 0.62269(17) 0.27695(7) 0.33972(11) 0.0354(4) Uani 1 1 d . . . C43 C 0.50284(16) 0.27527(6) 0.27736(10) 0.0306(4) Uani 1 1 d . . . C43A C 0.41798(15) 0.31818(6) 0.25981(9) 0.0257(3) Uani 1 1 d . . . C43B C 0.28747(15) 0.31947(6) 0.19207(9) 0.0248(3) Uani 1 1 d . . . C44 C 0.33928(16) 0.26979(6) 0.07589(10) 0.0283(4) Uani 1 1 d . . . C45 C 0.5176(2) 0.22874(8) 0.03198(14) 0.0418(5) Uani 1 1 d . . . C46 C 0.04136(16) 0.22442(6) 0.06572(9) 0.0299(4) Uani 1 1 d . . . C47 C -0.1613(2) 0.18522(9) -0.01061(14) 0.0471(5) Uani 1 1 d . . . C48 C 0.02149(16) 0.24657(6) 0.23003(9) 0.0277(3) Uani 1 1 d . . . C49 C -0.10823(18) 0.22435(7) 0.21234(11) 0.0365(4) Uani 1 1 d . . . C50 C -0.1375(2) 0.18472(7) 0.26043(13) 0.0464(5) Uani 1 1 d . . . C51 C -0.0386(2) 0.16773(7) 0.32680(13) 0.0476(5) Uani 1 1 d . . . C52 C 0.0904(2) 0.18930(7) 0.34438(12) 0.0446(5) Uani 1 1 d . . . C53 C 0.12080(18) 0.22850(6) 0.29657(10) 0.0342(4) Uani 1 1 d . . . H31 H 0.2792(13) 0.2388(5) 0.1736(8) 0.021(4) Uiso 1 1 d . . . H32 H 0.0808(15) 0.3009(6) 0.0637(9) 0.030(4) Uiso 1 1 d . . . H33 H -0.0360(14) 0.3106(5) 0.1576(8) 0.019(4) Uiso 1 1 d . . . H35 H -0.0529(14) 0.3300(5) 0.2803(8) 0.019(4) Uiso 1 1 d . . . H36 H -0.0947(16) 0.3817(6) 0.3795(9) 0.033(4) Uiso 1 1 d . . . H37 H 0.0749(15) 0.4426(6) 0.4506(9) 0.034(4) Uiso 1 1 d . . . H38 H 0.2721(14) 0.4524(5) 0.4026(8) 0.024(4) Uiso 1 1 d . . . H39A H 0.3403(14) 0.4191(5) 0.2316(9) 0.024(4) Uiso 1 1 d . . . H39B H 0.4068(15) 0.4405(6) 0.3170(9) 0.029(4) Uiso 1 1 d . . . H40 H 0.5975(15) 0.3951(6) 0.3969(9) 0.033(4) Uiso 1 1 d . . . H41 H 0.7374(16) 0.3219(5) 0.4278(9) 0.032(4) Uiso 1 1 d . . . H42 H 0.6823(15) 0.2456(6) 0.3522(9) 0.034(4) Uiso 1 1 d . . . H43 H 0.4779(16) 0.2427(6) 0.2450(10) 0.039(5) Uiso 1 1 d . . . H43A H 0.2910(14) 0.3482(5) 0.1541(9) 0.028(4) Uiso 1 1 d . . . H45A H 0.5733(19) 0.1966(7) 0.0476(11) 0.061(6) Uiso 1 1 d . . . H45B H 0.4627(19) 0.2302(7) -0.0243(12) 0.058(6) Uiso 1 1 d . . . H45C H 0.5737(17) 0.2600(7) 0.0378(10) 0.049(5) Uiso 1 1 d . . . H47A H -0.1081(18) 0.1685(7) -0.0442(11) 0.055(6) Uiso 1 1 d . . . H47B H -0.1720(19) 0.1626(8) 0.0356(12) 0.067(7) Uiso 1 1 d . . . H47C H -0.2503(19) 0.1983(7) -0.0443(11) 0.054(6) Uiso 1 1 d . . . H49 H -0.1781(16) 0.2382(6) 0.1655(10) 0.039(5) Uiso 1 1 d . . . H50 H -0.2250(18) 0.1718(6) 0.2481(10) 0.049(5) Uiso 1 1 d . . . H51 H -0.0613(17) 0.1404(7) 0.3612(10) 0.054(6) Uiso 1 1 d . . . H52 H 0.1607(18) 0.1779(7) 0.3910(11) 0.053(6) Uiso 1 1 d . . . H53 H 0.2111(16) 0.2452(6) 0.3114(9) 0.033(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0360(7) 0.0370(7) 0.0460(7) 0.0004(6) 0.0184(6) 0.0081(5) O2 0.0495(8) 0.0343(7) 0.0386(7) 0.0049(6) 0.0198(6) 0.0046(6) O3 0.0264(6) 0.0347(6) 0.0334(6) -0.0054(5) 0.0020(5) -0.0013(5) O4 0.0364(7) 0.0297(6) 0.0437(7) -0.0072(5) 0.0040(6) 0.0030(5) N4 0.0244(7) 0.0290(7) 0.0316(7) -0.0065(6) 0.0090(6) -0.0041(6) C1 0.0265(9) 0.0222(8) 0.0289(8) 0.0011(7) 0.0072(7) 0.0005(7) C2 0.0272(9) 0.0255(8) 0.0262(8) 0.0007(7) 0.0048(7) -0.0005(7) C3 0.0242(9) 0.0271(8) 0.0291(9) -0.0005(7) 0.0047(7) 0.0012(7) C4A 0.0296(9) 0.0238(8) 0.0239(8) 0.0022(7) 0.0056(7) 0.0039(7) C5 0.0307(9) 0.0273(9) 0.0331(9) 0.0019(7) 0.0087(8) 0.0010(7) C6 0.0309(10) 0.0360(10) 0.0337(9) 0.0042(8) 0.0127(8) 0.0060(8) C7 0.0384(10) 0.0313(9) 0.0273(9) -0.0008(8) 0.0082(8) 0.0079(8) C8 0.0371(10) 0.0270(9) 0.0263(8) 0.0004(7) 0.0052(8) 0.0014(7) C8A 0.0304(9) 0.0257(8) 0.0246(8) 0.0032(7) 0.0055(7) 0.0009(7) C9 0.0362(10) 0.0292(9) 0.0272(9) -0.0046(7) 0.0095(8) -0.0089(7) C9A 0.0287(9) 0.0341(9) 0.0281(8) 0.0002(7) 0.0098(7) -0.0067(7) C10 0.0355(10) 0.0419(11) 0.0300(9) -0.0027(8) 0.0091(8) -0.0106(8) C11 0.0300(10) 0.0562(12) 0.0336(10) 0.0092(9) -0.0016(8) -0.0062(9) C12 0.0330(10) 0.0410(11) 0.0434(11) 0.0111(9) 0.0050(9) 0.0015(9) C13 0.0299(9) 0.0316(9) 0.0356(9) 0.0039(8) 0.0081(8) -0.0021(7) C13A 0.0237(8) 0.0313(9) 0.0267(8) 0.0041(7) 0.0062(7) -0.0041(7) C13B 0.0264(8) 0.0234(8) 0.0262(8) 0.0009(7) 0.0077(7) -0.0009(6) C14 0.0286(9) 0.0245(8) 0.0340(9) -0.0061(7) 0.0069(7) -0.0032(7) C15 0.0431(12) 0.0435(12) 0.0588(14) -0.0077(11) 0.0295(11) 0.0021(10) C16 0.0263(9) 0.0323(9) 0.0255(8) -0.0002(7) 0.0077(7) -0.0016(7) C17 0.0307(10) 0.0418(11) 0.0362(10) -0.0106(9) 0.0039(9) -0.0069(8) C18 0.0315(9) 0.0280(8) 0.0261(8) -0.0043(7) 0.0111(7) -0.0019(7) C19 0.0339(10) 0.0410(10) 0.0321(9) -0.0023(8) 0.0109(8) -0.0058(8) C20 0.0466(12) 0.0472(11) 0.0405(11) -0.0089(9) 0.0197(10) -0.0180(10) C21 0.0705(15) 0.0303(10) 0.0417(11) -0.0049(9) 0.0310(11) -0.0088(10) C22 0.0566(13) 0.0345(10) 0.0328(10) 0.0020(8) 0.0202(10) 0.0067(9) C23 0.0362(10) 0.0332(9) 0.0291(9) -0.0014(7) 0.0126(8) 0.0032(8) O21 0.0354(7) 0.0342(6) 0.0455(7) -0.0003(6) 0.0191(6) 0.0049(5) O22 0.0492(8) 0.0416(7) 0.0339(7) 0.0060(6) 0.0163(6) 0.0064(6) O23 0.0280(6) 0.0431(7) 0.0376(7) -0.0122(6) 0.0016(5) -0.0020(5) O24 0.0351(7) 0.0318(7) 0.0521(8) -0.0087(6) 0.0086(6) -0.0004(5) N34 0.0235(7) 0.0289(7) 0.0305(7) -0.0058(6) 0.0081(6) -0.0031(5) C31 0.0254(8) 0.0234(8) 0.0252(8) 0.0009(7) 0.0058(7) -0.0002(6) C32 0.0266(8) 0.0266(8) 0.0245(8) 0.0004(7) 0.0031(7) 0.0013(7) C33 0.0221(8) 0.0270(8) 0.0274(8) -0.0013(7) 0.0023(7) 0.0011(7) C34A 0.0292(9) 0.0226(8) 0.0244(8) 0.0029(7) 0.0057(7) 0.0018(6) C35 0.0286(9) 0.0257(9) 0.0306(9) -0.0001(7) 0.0057(7) 0.0010(7) C36 0.0317(9) 0.0315(9) 0.0339(9) 0.0033(7) 0.0118(8) 0.0031(7) C37 0.0392(10) 0.0286(9) 0.0280(9) -0.0006(7) 0.0093(8) 0.0066(7) C38 0.0324(9) 0.0247(8) 0.0278(9) -0.0008(7) 0.0013(8) -0.0002(7) C38A 0.0269(8) 0.0234(8) 0.0262(8) 0.0029(7) 0.0036(7) 0.0030(6) C39 0.0326(9) 0.0248(9) 0.0307(9) -0.0013(7) 0.0091(8) -0.0043(7) C39A 0.0272(9) 0.0291(9) 0.0283(8) 0.0010(7) 0.0103(7) -0.0045(7) C40 0.0298(9) 0.0336(9) 0.0305(9) -0.0062(8) 0.0079(8) -0.0091(7) C41 0.0246(9) 0.0418(10) 0.0346(10) 0.0003(8) 0.0011(8) -0.0049(8) C42 0.0275(9) 0.0354(10) 0.0411(10) 0.0023(8) 0.0049(8) 0.0029(8) C43 0.0281(9) 0.0300(9) 0.0330(9) -0.0007(8) 0.0066(8) -0.0022(7) C43A 0.0241(8) 0.0282(8) 0.0260(8) 0.0019(7) 0.0086(7) -0.0038(6) C43B 0.0249(8) 0.0243(8) 0.0256(8) 0.0005(7) 0.0070(7) -0.0011(6) C44 0.0302(9) 0.0249(8) 0.0284(8) -0.0053(7) 0.0046(7) -0.0023(7) C45 0.0388(11) 0.0400(11) 0.0550(13) -0.0020(10) 0.0271(11) 0.0004(9) C46 0.0268(9) 0.0354(9) 0.0272(8) -0.0049(7) 0.0060(7) -0.0011(7) C47 0.0312(11) 0.0566(13) 0.0509(13) -0.0297(11) 0.0054(10) -0.0074(10) C48 0.0300(9) 0.0257(8) 0.0299(9) -0.0026(7) 0.0120(7) 0.0003(7) C49 0.0383(11) 0.0369(10) 0.0361(10) -0.0048(8) 0.0122(9) -0.0063(8) C50 0.0498(13) 0.0402(11) 0.0576(13) -0.0130(10) 0.0293(11) -0.0171(10) C51 0.0710(15) 0.0303(10) 0.0529(12) 0.0045(9) 0.0369(12) 0.0031(10) C52 0.0515(13) 0.0458(12) 0.0419(11) 0.0123(9) 0.0219(10) 0.0175(10) C53 0.0340(10) 0.0358(10) 0.0354(10) 0.0037(8) 0.0133(8) 0.0054(8) _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 C14 1.3332(18) . ? O1 C15 1.452(2) . ? O2 C14 1.2038(18) . ? O3 C16 1.3378(17) . ? O3 C17 1.4418(19) . ? O4 C16 1.2032(17) . ? N4 C3 1.4661(19) . ? N4 C4A 1.4011(18) . ? N4 C13B 1.4854(18) . ? C1 C2 1.515(2) . ? C1 C13B 1.535(2) . ? C1 C14 1.510(2) . ? C1 H1 0.943(14) . ? C2 C3 1.551(2) . ? C2 C16 1.507(2) . ? C2 H2 0.989(14) . ? C3 C18 1.518(2) . ? C3 H3 0.983(13) . ? C4A C5 1.405(2) . ? C4A C8A 1.414(2) . ? C5 C6 1.382(2) . ? C5 H5 0.995(14) . ? C6 C7 1.381(2) . ? C6 H6 0.964(15) . ? C7 C8 1.380(2) . ? C7 H7 0.959(16) . ? C8 C8A 1.387(2) . ? C8 H8 0.985(15) . ? C8A C9 1.511(2) . ? C9 C9A 1.505(2) . ? C9 H9A 1.005(15) . ? C9 H9B 0.983(15) . ? C9A C10 1.393(2) . ? C9A C13A 1.400(2) . ? C10 C11 1.383(2) . ? C10 H10 0.932(14) . ? C11 C12 1.381(3) . ? C11 H11 0.947(16) . ? C12 C13 1.384(2) . ? C12 H12 0.935(17) . ? C13 C13A 1.392(2) . ? C13 H13 0.987(15) . ? C13A C13B 1.512(2) . ? C13B H13A 0.997(14) . ? C15 H15A 0.984(19) . ? C15 H15B 0.98(2) . ? C15 H15C 0.95(2) . ? C17 H17A 1.016(18) . ? C17 H17B 1.011(18) . ? C17 H17C 1.000(17) . ? C18 C19 1.392(2) . ? C18 C23 1.393(2) . ? C19 C20 1.386(2) . ? C19 H19 0.999(16) . ? C20 C21 1.376(3) . ? C20 H20 0.951(17) . ? C21 C22 1.389(3) . ? C21 H21 1.002(17) . ? C22 C23 1.390(2) . ? C22 H22 1.002(16) . ? C23 H23 0.998(15) . ? O21 C44 1.3384(18) . ? O21 C45 1.453(2) . ? O22 C44 1.1996(17) . ? O23 C46 1.3367(18) . ? O23 C47 1.453(2) . ? O24 C46 1.2052(18) . ? N34 C33 1.4598(18) . ? N34 C34A 1.3941(18) . ? N34 C43B 1.4854(18) . ? C31 C32 1.519(2) . ? C31 C43B 1.541(2) . ? C31 C44 1.512(2) . ? C31 H31 0.996(14) . ? C32 C33 1.551(2) . ? C32 C46 1.503(2) . ? C32 H32 0.972(15) . ? C33 C48 1.525(2) . ? C33 H33 0.999(13) . ? C34A C35 1.410(2) . ? C34A C38A 1.413(2) . ? C35 C36 1.377(2) . ? C35 H35 0.967(13) . ? C36 C37 1.377(2) . ? C36 H36 0.960(15) . ? C37 C38 1.387(2) . ? C37 H37 0.982(15) . ? C38 C38A 1.390(2) . ? C38 H38 0.957(14) . ? C38A C39 1.513(2) . ? C39 C39A 1.502(2) . ? C39 H39A 0.960(15) . ? C39 H39B 1.008(15) . ? C39A C40 1.384(2) . ? C39A C43A 1.405(2) . ? C40 C41 1.390(2) . ? C40 H40 0.942(15) . ? C41 C42 1.376(2) . ? C41 H41 0.944(15) . ? C42 C43 1.394(2) . ? C42 H42 1.002(15) . ? C43 C43A 1.391(2) . ? C43 H43 1.007(16) . ? C43A C43B 1.516(2) . ? C43B H43A 0.993(14) . ? C45 H45A 1.003(19) . ? C45 H45B 0.980(19) . ? C45 H45C 0.980(17) . ? C47 H47A 0.977(18) . ? C47 H47B 1.01(2) . ? C47 H47C 0.995(18) . ? C48 C49 1.391(2) . ? C48 C53 1.391(2) . ? C49 C50 1.392(2) . ? C49 H49 0.989(16) . ? C50 C51 1.378(3) . ? C50 H50 0.917(17) . ? C51 C52 1.377(3) . ? C51 H51 0.983(17) . ? C52 C53 1.384(2) . ? C52 H52 0.969(17) . ? C53 H53 0.982(15) . ? 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 O1 C14 C1 111.93(14) . . ? O1 C15 H15A 109.4(11) . . ? O1 C15 H15B 108.3(13) . . ? O1 C15 H15C 101.9(12) . . ? O2 C14 O1 123.68(15) . . ? O2 C14 C1 124.39(14) . . ? O3 C16 C2 110.39(13) . . ? O3 C17 H17A 104.2(9) . . ? O3 C17 H17B 110.5(10) . . ? O3 C17 H17C 107.5(9) . . ? O4 C16 O3 124.48(14) . . ? O4 C16 C2 125.13(14) . . ? N4 C3 C2 102.39(12) . . ? N4 C3 C18 114.52(13) . . ? N4 C3 H3 111.3(8) . . ? N4 C4A C5 118.51(14) . . ? N4 C4A C8A 123.63(13) . . ? N4 C13B C1 102.23(12) . . ? N4 C13B C13A 112.54(12) . . ? N4 C13B H13A 111.2(8) . . ? C1 C2 C3 103.43(12) . . ? C1 C2 H2 109.4(8) . . ? C1 C13B H13A 105.7(8) . . ? C2 C1 C13B 101.88(12) . . ? C2 C1 H1 110.0(8) . . ? C2 C3 H3 109.5(8) . . ? C3 N4 C13B 112.01(11) . . ? C3 C2 H2 108.6(8) . . ? C4A N4 C3 119.41(12) . . ? C4A N4 C13B 125.63(12) . . ? C4A C5 H5 120.4(8) . . ? C4A C8A C9 123.77(14) . . ? C5 C4A C8A 117.84(14) . . ? C5 C6 H6 118.5(9) . . ? C6 C5 C4A 121.70(16) . . ? C6 C5 H5 117.8(8) . . ? C6 C7 H7 122.7(9) . . ? C7 C6 C5 120.39(16) . . ? C7 C6 H6 121.1(9) . . ? C7 C8 C8A 123.09(16) . . ? C7 C8 H8 120.2(9) . . ? C8 C7 C6 118.33(16) . . ? C8 C7 H7 118.9(9) . . ? C8 C8A C4A 118.62(14) . . ? C8 C8A C9 117.60(14) . . ? C8A C8 H8 116.7(9) . . ? C8A C9 H9A 107.2(9) . . ? C8A C9 H9B 109.3(9) . . ? C9A C9 C8A 112.11(13) . . ? C9A C9 H9A 109.0(9) . . ? C9A C9 H9B 112.5(8) . . ? C9A C10 H10 118.9(9) . . ? C9A C13A C13B 117.52(14) . . ? C10 C9A C9 121.40(15) . . ? C10 C9A C13A 119.81(15) . . ? C10 C11 H11 120.0(10) . . ? C11 C10 C9A 120.29(17) . . ? C11 C10 H10 120.8(9) . . ? C11 C12 C13 120.14(18) . . ? C11 C12 H12 121.5(11) . . ? C12 C11 C10 120.02(17) . . ? C12 C11 H11 119.9(10) . . ? C12 C13 C13A 120.63(17) . . ? C12 C13 H13 120.1(9) . . ? C13 C12 H12 118.3(11) . . ? C13 C13A C9A 119.06(15) . . ? C13 C13A C13B 123.41(14) . . ? C13A C9A C9 118.76(14) . . ? C13A C13 H13 119.2(9) . . ? C13A C13B C1 116.44(13) . . ? C13A C13B H13A 108.4(8) . . ? C13B C1 H1 110.8(8) . . ? C14 O1 C15 115.39(14) . . ? C14 C1 C2 111.78(13) . . ? C14 C1 C13B 112.99(12) . . ? C14 C1 H1 109.2(8) . . ? C16 O3 C17 115.40(13) . . ? C16 C2 C1 113.95(13) . . ? C16 C2 C3 113.42(13) . . ? C16 C2 H2 107.9(8) . . ? C18 C3 C2 112.03(12) . . ? C18 C3 H3 107.1(8) . . ? C18 C19 H19 118.7(9) . . ? C18 C23 H23 119.0(9) . . ? C19 C18 C3 119.11(14) . . ? C19 C18 C23 118.86(15) . . ? C19 C20 H20 117.2(11) . . ? C20 C19 C18 120.99(17) . . ? C20 C19 H19 120.4(9) . . ? C20 C21 C22 120.66(18) . . ? C20 C21 H21 119.3(10) . . ? C21 C20 C19 119.47(18) . . ? C21 C20 H20 123.3(11) . . ? C21 C22 C23 119.67(18) . . ? C21 C22 H22 122.8(9) . . ? C22 C21 H21 120.0(10) . . ? C22 C23 C18 120.27(17) . . ? C22 C23 H23 120.7(9) . . ? C23 C18 C3 121.89(14) . . ? C23 C22 H22 117.6(10) . . ? H9A C9 H9B 106.5(12) . . ? H15A C15 H15B 111.6(17) . . ? H15A C15 H15C 117.2(16) . . ? H15B C15 H15C 107.7(17) . . ? H17A C17 H17B 110.0(13) . . ? H17A C17 H17C 113.5(13) . . ? H17B C17 H17C 110.9(14) . . ? O21 C44 C31 111.57(13) . . ? O21 C45 H45A 104.6(10) . . ? O21 C45 H45B 110.2(11) . . ? O21 C45 H45C 109.5(10) . . ? O22 C44 O21 123.80(14) . . ? O22 C44 C31 124.62(14) . . ? O23 C46 C32 111.36(13) . . ? O23 C47 H47A 108.4(10) . . ? O23 C47 H47B 107.4(11) . . ? O23 C47 H47C 104.0(10) . . ? O24 C46 O23 124.24(15) . . ? O24 C46 C32 124.40(15) . . ? N34 C33 C32 101.84(12) . . ? N34 C33 C48 113.60(12) . . ? N34 C33 H33 110.3(8) . . ? N34 C34A C35 119.06(14) . . ? N34 C34A C38A 123.64(13) . . ? N34 C43B C31 102.28(11) . . ? N34 C43B C43A 114.03(12) . . ? N34 C43B H43A 108.4(8) . . ? C31 C32 C33 102.70(12) . . ? C31 C32 H32 111.5(9) . . ? C31 C43B H43A 106.2(8) . . ? C32 C31 C43B 102.25(12) . . ? C32 C31 H31 109.0(8) . . ? C32 C33 H33 108.6(8) . . ? C33 N34 C43B 112.63(11) . . ? C33 C32 H32 106.9(9) . . ? C34A N34 C33 120.35(12) . . ? C34A N34 C43B 126.99(12) . . ? C34A C35 H35 119.8(8) . . ? C34A C38A C39 122.37(14) . . ? C35 C34A C38A 117.29(14) . . ? C35 C36 C37 121.28(16) . . ? C35 C36 H36 117.0(9) . . ? C36 C35 C34A 121.54(15) . . ? C36 C35 H35 118.6(8) . . ? C36 C37 C38 117.71(15) . . ? C36 C37 H37 123.1(9) . . ? C37 C36 H36 121.7(9) . . ? C37 C38 C38A 122.76(15) . . ? C37 C38 H38 119.8(8) . . ? C38 C37 H37 119.2(9) . . ? C38 C38A C34A 119.08(14) . . ? C38 C38A C39 118.52(14) . . ? C38A C38 H38 117.4(9) . . ? C38A C39 H39A 111.3(9) . . ? C38A C39 H39B 109.0(8) . . ? C39A C39 C38A 110.87(13) . . ? C39A C39 H39A 111.7(8) . . ? C39A C39 H39B 110.4(8) . . ? C39A C40 C41 120.73(16) . . ? C39A C40 H40 118.5(9) . . ? C39A C43A C43B 117.35(13) . . ? C40 C39A C39 121.42(15) . . ? C40 C39A C43A 119.56(15) . . ? C40 C41 H41 120.2(9) . . ? C41 C40 H40 120.8(9) . . ? C41 C42 C43 120.05(16) . . ? C41 C42 H42 120.3(9) . . ? C42 C41 C40 119.95(16) . . ? C42 C41 H41 119.9(9) . . ? C42 C43 H43 119.5(9) . . ? C43 C42 H42 119.6(9) . . ? C43 C43A C39A 119.24(14) . . ? C43 C43A C43B 123.37(14) . . ? C43A C39A C39 118.85(14) . . ? C43A C43 C42 120.44(15) . . ? C43A C43 H43 120.1(9) . . ? C43A C43B C31 115.14(13) . . ? C43A C43B H43A 110.2(8) . . ? C43B C31 H31 111.5(8) . . ? C44 O21 C45 115.74(14) . . ? C44 C31 C32 113.22(12) . . ? C44 C31 C43B 111.35(12) . . ? C44 C31 H31 109.4(8) . . ? C46 O23 C47 115.42(14) . . ? C46 C32 C31 113.76(13) . . ? C46 C32 C33 113.66(13) . . ? C46 C32 H32 108.1(9) . . ? C48 C33 C32 114.27(12) . . ? C48 C33 H33 108.1(8) . . ? C48 C49 C50 120.37(18) . . ? C48 C49 H49 117.7(9) . . ? C48 C53 H53 119.5(9) . . ? C49 C48 C33 119.68(14) . . ? C49 C48 C53 118.79(16) . . ? C49 C50 H50 118.0(11) . . ? C50 C49 H49 121.9(9) . . ? C50 C51 H51 119.4(10) . . ? C51 C50 C49 120.15(19) . . ? C51 C50 H50 121.8(11) . . ? C51 C52 C53 120.47(19) . . ? C51 C52 H52 120.7(11) . . ? C52 C51 C50 119.80(18) . . ? C52 C51 H51 120.8(10) . . ? C52 C53 C48 120.40(17) . . ? C52 C53 H53 120.0(9) . . ? C53 C48 C33 121.51(14) . . ? C53 C52 H52 118.9(11) . . ? H39A C39 H39B 103.2(11) . . ? H45A C45 H45B 115.8(15) . . ? H45A C45 H45C 113.1(14) . . ? H45B C45 H45C 103.7(15) . . ? H47A C47 H47B 112.2(15) . . ? H47A C47 H47C 111.2(14) . . ? H47B C47 H47C 113.1(15) . . ? # Attachment '- 16.cif' data_16_DAX17 _database_code_depnum_ccdc_archive 'CCDC 809445' _audit_creation_method SHELXL-97 _chemical_formula_moiety '4(C25 H19 N3), 0.5(C H2 Cl2)' _chemical_formula_sum 'C25.06 H19.13 Cl0.13 N3' _chemical_formula_weight 366.74 _chemical_melting_point '190 C' _chemical_name_common ? _chemical_name_systematic ; (1RS,2SR,3SR,13bRS)-3-Phenyl-2,3,9,13b-tetrahydro-1H-dibenzo[c,f]pyrrolo [1,2-a]azepine-1,2-dicarbonitrile ; 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' _space_group_IT_number 15 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 113.740(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 32 _cell_length_a 36.9379(14) _cell_length_b 28.7704(11) _cell_length_c 15.8020(6) _cell_measurement_reflns_used 6150 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 24.30 _cell_measurement_theta_min 2.42 _cell_volume 15372.1(12) _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_F_000 6164 _exptl_crystal_colour brownish _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier brownish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f angles and each scan (20.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD 6000' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator Parallel,graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1100 _diffrn_reflns_av_sigmaI/netI 0.1143 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 69184 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.42 _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 7919 _reflns_number_total 16751 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution ; A short history of SHELX (Sheldrick, 2007)/Bruker ; _refine_diff_density_max 0.876 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.060 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.0606 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 1021 _refine_ls_number_reflns 16751 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1357 _refine_ls_wR_factor_ref 0.1546 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.71895(8) 0.34941(10) 0.6528(2) 0.0498(8) Uani 1 1 d . . . N2 N 0.61574(8) 0.36308(9) 0.61418(19) 0.0435(7) Uani 1 1 d . . . N4 N 0.67134(6) 0.50262(7) 0.57159(16) 0.0266(5) Uani 1 1 d . . . C1 C 0.69879(8) 0.43602(9) 0.65688(19) 0.0269(6) Uani 1 1 d . . . H1 H 0.7161 0.4494 0.7165 0.032 Uiso 1 1 calc R . . C2 C 0.65521(8) 0.44105(9) 0.64632(19) 0.0266(6) Uani 1 1 d . . . H2 H 0.6554 0.4542 0.7037 0.032 Uiso 1 1 calc R . . C3 C 0.63631(8) 0.47710(10) 0.5678(2) 0.0289(7) Uani 1 1 d . . . H3 H 0.6239 0.4610 0.5083 0.035 Uiso 1 1 calc R . . C4A C 0.66628(8) 0.53699(10) 0.5017(2) 0.0296(7) Uani 1 1 d . . . C5 C 0.63461(9) 0.53705(10) 0.4158(2) 0.0349(7) Uani 1 1 d . . . H5 H 0.6152 0.5142 0.4011 0.042 Uiso 1 1 calc R . . C6 C 0.63220(10) 0.57165(12) 0.3521(2) 0.0468(9) Uani 1 1 d . . . H6 H 0.6109 0.5721 0.2948 0.056 Uiso 1 1 calc R . . C7 C 0.66108(11) 0.60523(12) 0.3734(3) 0.0495(9) Uani 1 1 d . . . H7 H 0.6594 0.6282 0.3305 0.059 Uiso 1 1 calc R . . C8 C 0.69229(11) 0.60463(11) 0.4583(3) 0.0472(9) Uani 1 1 d . . . H8 H 0.7118 0.6272 0.4720 0.057 Uiso 1 1 calc R . . C8A C 0.69546(9) 0.57126(10) 0.5240(2) 0.0333(7) Uani 1 1 d . . . C9 C 0.72886(9) 0.56935(10) 0.6172(2) 0.0389(8) Uani 1 1 d . . . H9A H 0.7184 0.5654 0.6641 0.047 Uiso 1 1 calc R . . H9B H 0.7433 0.5984 0.6292 0.047 Uiso 1 1 calc R . . C9A C 0.75670(8) 0.52953(10) 0.62309(19) 0.0314(7) Uani 1 1 d . . . C10 C 0.79629(9) 0.53897(11) 0.6423(2) 0.0385(8) Uani 1 1 d . . . H10F H 0.8056 0.5692 0.6567 0.046 Uiso 1 1 calc R . . C11 C 0.82200(9) 0.50470(12) 0.6405(2) 0.0387(8) Uani 1 1 d . . . H11D H 0.8485 0.5117 0.6559 0.046 Uiso 1 1 calc R . . C12 C 0.80837(8) 0.45981(11) 0.6159(2) 0.0354(7) Uani 1 1 d . . . H12 H 0.8254 0.4367 0.6129 0.043 Uiso 1 1 calc R . . C13 C 0.76931(8) 0.44965(10) 0.59588(19) 0.0299(7) Uani 1 1 d . . . H13 H 0.7602 0.4195 0.5788 0.036 Uiso 1 1 calc R . . C13A C 0.74293(8) 0.48362(10) 0.60054(19) 0.0274(6) Uani 1 1 d . . . C13B C 0.70121(7) 0.46675(9) 0.57899(19) 0.0269(6) Uani 1 1 d . . . H13A H 0.6919 0.4487 0.5215 0.032 Uiso 1 1 calc R . . C14 C 0.71052(8) 0.38786(11) 0.6543(2) 0.0329(7) Uani 1 1 d . . . C15 C 0.63300(8) 0.39742(10) 0.6275(2) 0.0317(7) Uani 1 1 d . . . C16 C 0.60623(8) 0.50789(9) 0.5830(2) 0.0273(6) Uani 1 1 d . . . C17 C 0.56815(9) 0.51118(10) 0.5165(2) 0.0371(7) Uani 1 1 d . . . H17 H 0.5610 0.4950 0.4612 0.045 Uiso 1 1 calc R . . C18 C 0.54011(9) 0.53896(11) 0.5323(3) 0.0464(9) Uani 1 1 d . . . H18 H 0.5145 0.5417 0.4872 0.056 Uiso 1 1 calc R . . C19 C 0.55102(10) 0.56216(10) 0.6159(3) 0.0446(9) Uani 1 1 d . . . H19 H 0.5326 0.5801 0.6274 0.054 Uiso 1 1 calc R . . C20 C 0.58901(9) 0.55869(10) 0.6817(2) 0.0403(8) Uani 1 1 d . . . H20 H 0.5962 0.5744 0.7375 0.048 Uiso 1 1 calc R . . C21 C 0.61652(8) 0.53223(10) 0.6657(2) 0.0318(7) Uani 1 1 d . . . H21 H 0.6423 0.5305 0.7104 0.038 Uiso 1 1 calc R . . N21 N 0.54823(9) 0.40686(10) 0.3563(2) 0.0599(9) Uani 1 1 d . . . N22 N 0.65295(9) 0.38568(10) 0.4083(2) 0.0538(8) Uani 1 1 d . . . N34 N 0.58714(6) 0.25162(7) 0.43725(15) 0.0253(5) Uani 1 1 d . . . C31 C 0.56547(8) 0.31920(9) 0.3514(2) 0.0308(7) Uani 1 1 d . . . H31 H 0.5491 0.3065 0.2903 0.037 Uiso 1 1 calc R . . C32 C 0.60989(8) 0.31064(9) 0.3707(2) 0.0294(7) Uani 1 1 d . . . H32 H 0.6113 0.2960 0.3161 0.035 Uiso 1 1 calc R . . C33 C 0.62444(8) 0.27509(9) 0.4516(2) 0.0281(6) Uani 1 1 d . . . H33 H 0.6341 0.2918 0.5106 0.034 Uiso 1 1 calc R . . C34A C 0.58834(8) 0.21625(9) 0.5016(2) 0.0262(6) Uani 1 1 d . . . C35 C 0.61875(8) 0.21164(10) 0.5883(2) 0.0288(7) Uani 1 1 d . . . H35 H 0.6395 0.2329 0.6081 0.035 Uiso 1 1 calc R . . C36 C 0.61825(9) 0.17528(10) 0.6458(2) 0.0331(7) Uani 1 1 d . . . H36 H 0.6391 0.1715 0.7032 0.040 Uiso 1 1 calc R . . C37 C 0.58666(9) 0.14458(10) 0.6177(2) 0.0347(7) Uani 1 1 d . . . H37 H 0.5860 0.1207 0.6567 0.042 Uiso 1 1 calc R . . C38 C 0.55605(9) 0.14949(9) 0.5315(2) 0.0324(7) Uani 1 1 d . . . H38 H 0.5348 0.1290 0.5134 0.039 Uiso 1 1 calc R . . C38A C 0.55655(8) 0.18450(9) 0.4717(2) 0.0282(6) Uani 1 1 d . . . C39 C 0.52472(8) 0.19081(9) 0.3757(2) 0.0307(7) Uani 1 1 d . . . H39B H 0.5369 0.1950 0.3320 0.037 Uiso 1 1 calc R . . H39A H 0.5083 0.1631 0.3580 0.037 Uiso 1 1 calc R . . C39A C 0.49932(8) 0.23235(10) 0.37216(19) 0.0274(6) Uani 1 1 d . . . C40 C 0.45913(8) 0.22616(10) 0.35196(19) 0.0320(7) Uani 1 1 d . . . H40 H 0.4481 0.1968 0.3349 0.038 Uiso 1 1 calc R . . C41 C 0.43543(8) 0.26218(11) 0.3565(2) 0.0324(7) Uani 1 1 d . . . H41 H 0.4087 0.2570 0.3419 0.039 Uiso 1 1 calc R . . C42 C 0.45130(8) 0.30602(11) 0.3829(2) 0.0336(7) Uani 1 1 d . . . H42 H 0.4355 0.3305 0.3860 0.040 Uiso 1 1 calc R . . C43 C 0.49124(8) 0.31283(10) 0.40469(19) 0.0300(7) Uani 1 1 d . . . H43 H 0.5021 0.3421 0.4235 0.036 Uiso 1 1 calc R . . C43A C 0.51557(8) 0.27682(9) 0.39917(19) 0.0263(6) Uani 1 1 d . . . C43B C 0.55874(8) 0.28945(9) 0.42578(19) 0.0256(6) Uani 1 1 d . . . H43A H 0.5679 0.3074 0.4834 0.031 Uiso 1 1 calc R . . C44 C 0.55537(9) 0.36850(11) 0.3531(2) 0.0391(8) Uani 1 1 d . . . C45 C 0.63409(9) 0.35290(11) 0.3922(2) 0.0363(7) Uani 1 1 d . . . C46 C 0.65643(8) 0.24331(9) 0.4495(2) 0.0292(7) Uani 1 1 d . . . C47 C 0.65107(9) 0.21632(10) 0.3725(2) 0.0353(7) Uani 1 1 d . . . H47 H 0.6270 0.2172 0.3214 0.042 Uiso 1 1 calc R . . C48 C 0.68147(10) 0.18790(11) 0.3713(3) 0.0469(9) Uani 1 1 d . . . H48 H 0.6777 0.1702 0.3192 0.056 Uiso 1 1 calc R . . C49 C 0.71692(10) 0.18596(11) 0.4471(3) 0.0502(10) Uani 1 1 d . . . H49 H 0.7371 0.1668 0.4463 0.060 Uiso 1 1 calc R . . C50 C 0.72263(9) 0.21256(11) 0.5245(3) 0.0453(9) Uani 1 1 d . . . H50 H 0.7465 0.2111 0.5760 0.054 Uiso 1 1 calc R . . C51 C 0.69250(8) 0.24137(10) 0.5250(2) 0.0361(7) Uani 1 1 d . . . H51 H 0.6966 0.2596 0.5767 0.043 Uiso 1 1 calc R . . Cl1A Cl 0.53950(10) 0.54061(13) 0.2316(3) 0.0401(10) Uiso 0.25 1 d P . 1 Cl1B Cl 0.53505(10) 0.53419(13) 0.2552(3) 0.0359(9) Uiso 0.25 1 d P A 2 C1SB C 0.5067(3) 0.5076(3) 0.2421(9) 0.021(2) Uiso 0.25 1 d P . 1 H1SB H 0.5210 0.4881 0.2972 0.025 Uiso 0.25 1 d PR . 1 H1SA H 0.4933 0.4929 0.1807 0.025 Uiso 0.25 1 d PR . 1 N31 N 0.52309(9) 0.12271(10) 0.8757(2) 0.0557(8) Uani 1 1 d . . . N32 N 0.61930(8) 0.09601(9) 0.8634(2) 0.0488(7) Uani 1 1 d . . . N64 N 0.60618(6) 0.25188(7) 0.92688(16) 0.0257(5) Uani 1 1 d . . . C61 C 0.55905(8) 0.19523(9) 0.84697(19) 0.0271(6) Uani 1 1 d . . . H61 H 0.5418 0.2092 0.7879 0.033 Uiso 1 1 calc R . . C62 C 0.59957(8) 0.18361(9) 0.8427(2) 0.0283(6) Uani 1 1 d . . . H62 H 0.5987 0.1941 0.7829 0.034 Uiso 1 1 calc R . . C63 C 0.63045(8) 0.21325(9) 0.9197(2) 0.0266(6) Uani 1 1 d . . . H63 H 0.6411 0.1958 0.9779 0.032 Uiso 1 1 calc R . . C64A C 0.62513(8) 0.28384(9) 1.00163(19) 0.0257(6) Uani 1 1 d . . . C65 C 0.65693(8) 0.27282(10) 1.0818(2) 0.0345(7) Uani 1 1 d . . . H65 H 0.6680 0.2432 1.0899 0.041 Uiso 1 1 calc R . . C66 C 0.67257(9) 0.30615(11) 1.1510(2) 0.0430(8) Uani 1 1 d . . . H66 H 0.6943 0.2989 1.2050 0.052 Uiso 1 1 calc R . . C67 C 0.65594(10) 0.34966(12) 1.1399(2) 0.0452(9) Uani 1 1 d . . . H67 H 0.6659 0.3714 1.1873 0.054 Uiso 1 1 calc R . . C68 C 0.62455(9) 0.36127(11) 1.0586(2) 0.0382(8) Uani 1 1 d . . . H68 H 0.6139 0.3910 1.0511 0.046 Uiso 1 1 calc R . . C68A C 0.60868(8) 0.32886(10) 0.9877(2) 0.0299(7) Uani 1 1 d . . . C69 C 0.57463(8) 0.33943(10) 0.8979(2) 0.0341(7) Uani 1 1 d . . . H69A H 0.5818 0.3306 0.8474 0.041 Uiso 1 1 calc R . . H69B H 0.5699 0.3727 0.8937 0.041 Uiso 1 1 calc R . . C69A C 0.53664(8) 0.31473(10) 0.8864(2) 0.0309(7) Uani 1 1 d . . . C70 C 0.50238(9) 0.34130(11) 0.8631(2) 0.0406(8) Uani 1 1 d . . . H70 H 0.5036 0.3731 0.8538 0.049 Uiso 1 1 calc R . . C71 C 0.46693(9) 0.32222(12) 0.8535(2) 0.0431(8) Uani 1 1 d . . . H71 H 0.4444 0.3407 0.8362 0.052 Uiso 1 1 calc R . . C72 C 0.46491(9) 0.27532(12) 0.8698(2) 0.0403(8) Uani 1 1 d . . . H72 H 0.4412 0.2621 0.8646 0.048 Uiso 1 1 calc R . . C73 C 0.49872(8) 0.24812(11) 0.8940(2) 0.0338(7) Uani 1 1 d . . . H73 H 0.4974 0.2166 0.9055 0.041 Uiso 1 1 calc R . . C73A C 0.53468(8) 0.26714(10) 0.90127(18) 0.0270(6) Uani 1 1 d . . . C73B C 0.56877(7) 0.23263(9) 0.92364(19) 0.0269(6) Uani 1 1 d . . . H73A H 0.5736 0.2174 0.9826 0.032 Uiso 1 1 calc R . . C74 C 0.53898(9) 0.15439(11) 0.8635(2) 0.0357(7) Uani 1 1 d . . . C75 C 0.61026(9) 0.13465(11) 0.8539(2) 0.0362(7) Uani 1 1 d . . . C76 C 0.66378(8) 0.22860(9) 0.8930(2) 0.0284(6) Uani 1 1 d . . . C77 C 0.69949(9) 0.20549(12) 0.9263(2) 0.0461(9) Uani 1 1 d . . . H77 H 0.7038 0.1813 0.9683 0.055 Uiso 1 1 calc R . . C78 C 0.72919(10) 0.21797(13) 0.8978(3) 0.0592(11) Uani 1 1 d . . . H78 H 0.7533 0.2024 0.9212 0.071 Uiso 1 1 calc R . . C79 C 0.72273(9) 0.25353(12) 0.8347(3) 0.0490(9) Uani 1 1 d . . . H79 H 0.7425 0.2619 0.8154 0.059 Uiso 1 1 calc R . . C80 C 0.68706(9) 0.27666(10) 0.8004(2) 0.0396(8) Uani 1 1 d . . . H80 H 0.6827 0.3006 0.7579 0.048 Uiso 1 1 calc R . . C81 C 0.65744(9) 0.26402(10) 0.8294(2) 0.0354(7) Uani 1 1 d . . . H81 H 0.6333 0.2795 0.8059 0.042 Uiso 1 1 calc R . . N41 N 0.70865(9) -0.14029(10) 0.6223(2) 0.0573(8) Uani 1 1 d . . . N42 N 0.61213(8) -0.15807(9) 0.6305(2) 0.0534(8) Uani 1 1 d . . . N94 N 0.63561(6) -0.00333(7) 0.57395(15) 0.0242(5) Uani 1 1 d . . . C91 C 0.67785(7) -0.06415(9) 0.65360(19) 0.0256(6) Uani 1 1 d . . . H91 H 0.6952 -0.0517 0.7142 0.031 Uiso 1 1 calc R . . C92 C 0.63593(7) -0.07180(9) 0.6524(2) 0.0262(6) Uani 1 1 d . . . H92 H 0.6362 -0.0604 0.7111 0.031 Uiso 1 1 calc R . . C93 C 0.60793(7) -0.04006(9) 0.57398(19) 0.0238(6) Uani 1 1 d . . . H93 H 0.5980 -0.0567 0.5149 0.029 Uiso 1 1 calc R . . C94A C 0.62121(7) 0.03157(9) 0.50332(19) 0.0238(6) Uani 1 1 d . . . C95 C 0.59122(8) 0.02430(10) 0.4167(2) 0.0296(7) Uani 1 1 d . . . H95 H 0.5785 -0.0043 0.4018 0.035 Uiso 1 1 calc R . . C96 C 0.58025(8) 0.06044(10) 0.3517(2) 0.0315(7) Uani 1 1 d . . . H96 H 0.5604 0.0557 0.2932 0.038 Uiso 1 1 calc R . . C97 C 0.59870(8) 0.10295(10) 0.3741(2) 0.0328(7) Uani 1 1 d . . . H97 H 0.5910 0.1270 0.3311 0.039 Uiso 1 1 calc R . . C98 C 0.62865(8) 0.11001(10) 0.4605(2) 0.0301(7) Uani 1 1 d . . . H98 H 0.6412 0.1387 0.4747 0.036 Uiso 1 1 calc R . . C98A C 0.64013(8) 0.07504(9) 0.52606(19) 0.0265(6) Uani 1 1 d . . . C99 C 0.67379(8) 0.08019(9) 0.61892(19) 0.0283(7) Uani 1 1 d . . . H99A H 0.6656 0.0694 0.6666 0.034 Uiso 1 1 calc R . . H99B H 0.6809 0.1128 0.6303 0.034 Uiso 1 1 calc R . . C99A C 0.70964(8) 0.05252(10) 0.62385(19) 0.0269(6) Uani 1 1 d . . . C100 C 0.74505(8) 0.07617(10) 0.6441(2) 0.0328(7) Uani 1 1 d . . . H10 H 0.7462 0.1078 0.6571 0.039 Uiso 1 1 calc R . . C101 C 0.77860(8) 0.05401(11) 0.6456(2) 0.0346(7) Uani 1 1 d . . . H10A H 0.8019 0.0706 0.6596 0.042 Uiso 1 1 calc R . . C102 C 0.77725(8) 0.00716(11) 0.6261(2) 0.0327(7) Uani 1 1 d . . . H10B H 0.7997 -0.0081 0.6275 0.039 Uiso 1 1 calc R . . C103 C 0.74216(7) -0.01685(10) 0.60455(19) 0.0281(6) Uani 1 1 d . . . H10C H 0.7411 -0.0483 0.5900 0.034 Uiso 1 1 calc R . . C104 C 0.70817(7) 0.00500(9) 0.60406(18) 0.0254(6) Uani 1 1 d . . . C105 C 0.67197(7) -0.02632(9) 0.57968(19) 0.0244(6) Uani 1 1 d . . . H10D H 0.6668 -0.0416 0.5205 0.029 Uiso 1 1 calc R . . C106 C 0.69555(8) -0.10652(11) 0.6368(2) 0.0351(7) Uani 1 1 d . . . C107 C 0.62237(8) -0.12030(11) 0.6407(2) 0.0361(7) Uani 1 1 d . . . C108 C 0.57409(7) -0.02295(9) 0.59498(19) 0.0243(6) Uani 1 1 d . . . C109 C 0.53951(8) -0.04931(10) 0.5684(2) 0.0297(7) Uani 1 1 d . . . H10E H 0.5368 -0.0761 0.5335 0.036 Uiso 1 1 calc R . . C110 C 0.50930(8) -0.03572(10) 0.5938(2) 0.0316(7) Uani 1 1 d . . . H11 H 0.4865 -0.0536 0.5762 0.038 Uiso 1 1 calc R . . C111 C 0.51283(8) 0.00422(10) 0.64487(19) 0.0300(7) Uani 1 1 d . . . H11A H 0.4924 0.0133 0.6615 0.036 Uiso 1 1 calc R . . C112 C 0.54687(8) 0.03067(10) 0.6713(2) 0.0309(7) Uani 1 1 d . . . H11B H 0.5492 0.0578 0.7052 0.037 Uiso 1 1 calc R . . C113 C 0.57756(8) 0.01707(9) 0.64754(19) 0.0284(6) Uani 1 1 d . . . H11C H 0.6006 0.0347 0.6667 0.034 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 N1 0.0598(19) 0.0405(18) 0.064(2) 0.0103(15) 0.0400(16) 0.0074(14) N2 0.0469(17) 0.0373(16) 0.0513(18) -0.0053(14) 0.0250(14) -0.0122(13) N4 0.0345(14) 0.0238(13) 0.0284(13) 0.0024(11) 0.0199(11) 0.0033(10) C1 0.0266(16) 0.0283(16) 0.0272(16) -0.0002(13) 0.0122(13) -0.0027(11) C2 0.0305(16) 0.0239(15) 0.0293(16) -0.0013(13) 0.0160(13) -0.0023(11) C3 0.0333(17) 0.0290(16) 0.0278(16) -0.0055(13) 0.0159(13) -0.0025(12) C4A 0.0408(18) 0.0263(16) 0.0298(17) 0.0008(13) 0.0227(14) 0.0094(13) C5 0.0479(19) 0.0318(17) 0.0371(18) 0.0031(15) 0.0296(16) 0.0108(14) C6 0.069(2) 0.047(2) 0.037(2) 0.0110(17) 0.0349(18) 0.0264(18) C7 0.089(3) 0.0302(19) 0.050(2) 0.0105(17) 0.050(2) 0.0165(18) C8 0.082(3) 0.0243(17) 0.057(2) -0.0002(17) 0.051(2) 0.0016(16) C8A 0.056(2) 0.0201(15) 0.0397(19) -0.0037(14) 0.0366(16) -0.0004(13) C9 0.055(2) 0.0320(18) 0.041(2) -0.0076(15) 0.0317(17) -0.0122(14) C9A 0.0402(18) 0.0351(17) 0.0246(16) -0.0041(14) 0.0189(14) -0.0043(13) C10 0.045(2) 0.046(2) 0.0322(18) -0.0077(16) 0.0243(15) -0.0189(15) C11 0.0353(18) 0.059(2) 0.0261(17) -0.0005(16) 0.0171(14) -0.0113(15) C12 0.0321(17) 0.051(2) 0.0276(17) 0.0092(15) 0.0169(14) 0.0060(14) C13 0.0371(18) 0.0329(17) 0.0236(15) -0.0012(13) 0.0162(13) 0.0005(13) C13A 0.0342(17) 0.0297(16) 0.0230(15) -0.0004(13) 0.0163(13) -0.0029(12) C13B 0.0310(16) 0.0259(15) 0.0250(15) -0.0019(13) 0.0126(13) -0.0006(12) C14 0.0378(18) 0.0290(17) 0.0379(18) 0.0019(14) 0.0217(15) 0.0003(13) C15 0.0347(17) 0.0313(17) 0.0353(18) -0.0002(14) 0.0206(14) -0.0015(13) C16 0.0257(16) 0.0252(15) 0.0328(17) -0.0008(13) 0.0136(13) -0.0025(11) C17 0.0366(18) 0.0336(17) 0.0404(19) 0.0004(15) 0.0146(15) -0.0002(13) C18 0.0309(18) 0.042(2) 0.065(3) 0.0095(19) 0.0177(17) 0.0026(14) C19 0.045(2) 0.0300(18) 0.072(3) 0.0052(18) 0.0376(19) 0.0068(14) C20 0.051(2) 0.0294(18) 0.050(2) -0.0044(16) 0.0309(18) -0.0008(14) C21 0.0385(17) 0.0279(16) 0.0337(17) -0.0016(14) 0.0194(14) 0.0013(13) N21 0.070(2) 0.0336(17) 0.092(3) 0.0187(17) 0.0488(19) 0.0066(14) N22 0.065(2) 0.0464(18) 0.0500(19) 0.0010(15) 0.0232(16) -0.0255(15) N34 0.0276(13) 0.0232(12) 0.0289(13) 0.0013(10) 0.0154(11) -0.0024(9) C31 0.0324(17) 0.0284(16) 0.0328(17) 0.0015(14) 0.0144(14) -0.0041(12) C32 0.0349(17) 0.0270(16) 0.0308(17) -0.0034(13) 0.0179(14) -0.0074(12) C33 0.0336(16) 0.0257(15) 0.0302(16) -0.0076(13) 0.0182(13) -0.0049(12) C34A 0.0330(16) 0.0214(15) 0.0329(17) -0.0029(13) 0.0225(14) 0.0010(11) C35 0.0338(17) 0.0281(16) 0.0312(17) -0.0008(13) 0.0201(14) 0.0024(12) C36 0.0453(19) 0.0310(17) 0.0309(17) 0.0010(14) 0.0236(15) 0.0105(14) C37 0.054(2) 0.0217(16) 0.0394(19) 0.0041(14) 0.0305(17) 0.0060(14) C38 0.0466(19) 0.0208(15) 0.0409(19) -0.0045(14) 0.0290(16) -0.0028(13) C38A 0.0341(17) 0.0226(15) 0.0357(17) -0.0020(13) 0.0221(14) 0.0001(12) C39 0.0378(17) 0.0263(16) 0.0331(17) -0.0067(14) 0.0196(14) -0.0082(12) C39A 0.0342(17) 0.0284(16) 0.0235(15) -0.0017(13) 0.0155(13) -0.0004(12) C40 0.0334(17) 0.0397(18) 0.0251(16) -0.0026(14) 0.0140(13) -0.0080(13) C41 0.0298(16) 0.0455(19) 0.0266(16) 0.0032(15) 0.0162(13) -0.0004(14) C42 0.0361(18) 0.0412(19) 0.0306(17) 0.0083(15) 0.0208(14) 0.0084(14) C43 0.0381(18) 0.0308(16) 0.0261(16) 0.0006(13) 0.0181(14) -0.0001(13) C43A 0.0278(15) 0.0290(16) 0.0254(15) 0.0020(13) 0.0141(13) -0.0010(12) C43B 0.0345(16) 0.0219(15) 0.0234(15) -0.0024(12) 0.0147(13) -0.0034(12) C44 0.045(2) 0.0317(19) 0.049(2) 0.0102(16) 0.0275(17) 0.0007(14) C45 0.0365(18) 0.0389(19) 0.0356(19) 0.0016(15) 0.0166(15) -0.0069(14) C46 0.0324(17) 0.0230(15) 0.0390(18) -0.0001(14) 0.0215(14) -0.0051(12) C47 0.0462(19) 0.0268(16) 0.0419(19) -0.0066(15) 0.0269(16) -0.0077(13) C48 0.064(2) 0.0302(18) 0.066(3) -0.0136(17) 0.046(2) -0.0060(16) C49 0.053(2) 0.0299(19) 0.085(3) -0.0063(19) 0.046(2) 0.0009(15) C50 0.0380(19) 0.0363(19) 0.067(3) 0.0010(18) 0.0261(18) -0.0016(14) C51 0.0399(19) 0.0270(17) 0.049(2) -0.0042(15) 0.0258(16) -0.0026(13) N31 0.071(2) 0.0425(18) 0.059(2) -0.0043(16) 0.0321(17) -0.0238(15) N32 0.0525(18) 0.0291(16) 0.060(2) -0.0041(14) 0.0172(15) -0.0003(13) N64 0.0276(13) 0.0237(12) 0.0308(13) -0.0041(11) 0.0170(11) -0.0040(9) C61 0.0332(16) 0.0251(15) 0.0241(15) 0.0024(13) 0.0127(13) -0.0027(12) C62 0.0386(17) 0.0237(15) 0.0266(16) 0.0007(13) 0.0175(13) -0.0038(12) C63 0.0351(16) 0.0203(14) 0.0286(16) -0.0006(13) 0.0173(13) 0.0001(11) C64A 0.0290(16) 0.0263(15) 0.0282(16) -0.0063(13) 0.0182(13) -0.0073(11) C65 0.0350(18) 0.0319(17) 0.0394(19) -0.0080(15) 0.0178(15) -0.0042(13) C66 0.0384(19) 0.049(2) 0.041(2) -0.0103(17) 0.0157(16) -0.0094(15) C67 0.049(2) 0.043(2) 0.051(2) -0.0246(18) 0.0283(19) -0.0204(16) C68 0.046(2) 0.0289(17) 0.051(2) -0.0091(15) 0.0309(18) -0.0082(14) C68A 0.0340(17) 0.0256(16) 0.0391(18) -0.0038(14) 0.0241(14) -0.0072(12) C69 0.0427(19) 0.0241(16) 0.044(2) 0.0050(14) 0.0262(16) -0.0003(13) C69A 0.0389(18) 0.0339(17) 0.0275(16) 0.0021(14) 0.0215(14) 0.0009(13) C70 0.048(2) 0.043(2) 0.0387(19) 0.0098(16) 0.0265(16) 0.0106(15) C71 0.0361(19) 0.067(2) 0.0308(18) 0.0092(17) 0.0182(15) 0.0186(16) C72 0.0303(18) 0.068(2) 0.0265(17) -0.0040(17) 0.0152(14) -0.0042(15) C73 0.0350(18) 0.0422(19) 0.0274(16) -0.0040(14) 0.0158(14) -0.0056(14) C73A 0.0275(16) 0.0361(17) 0.0191(15) -0.0005(13) 0.0110(12) -0.0017(12) C73B 0.0310(16) 0.0288(16) 0.0227(15) -0.0013(13) 0.0128(12) -0.0082(12) C74 0.0424(19) 0.0330(18) 0.0333(18) -0.0047(14) 0.0170(15) -0.0115(14) C75 0.0398(19) 0.0312(18) 0.0379(19) -0.0048(15) 0.0161(15) -0.0062(14) C76 0.0325(17) 0.0247(15) 0.0323(17) -0.0023(13) 0.0175(13) -0.0019(12) C77 0.044(2) 0.048(2) 0.054(2) 0.0169(18) 0.0277(18) 0.0070(15) C78 0.041(2) 0.068(3) 0.080(3) 0.019(2) 0.036(2) 0.0129(18) C79 0.046(2) 0.050(2) 0.067(3) 0.002(2) 0.0394(19) -0.0051(16) C80 0.049(2) 0.0292(17) 0.054(2) 0.0048(16) 0.0338(17) -0.0027(14) C81 0.0420(18) 0.0269(16) 0.047(2) -0.0006(15) 0.0285(16) 0.0015(13) N41 0.069(2) 0.0438(18) 0.071(2) 0.0079(17) 0.0412(18) 0.0214(15) N42 0.0507(18) 0.0312(17) 0.077(2) 0.0084(16) 0.0246(16) -0.0046(13) N94 0.0273(13) 0.0222(12) 0.0277(13) 0.0033(10) 0.0158(11) 0.0003(9) C91 0.0261(15) 0.0267(15) 0.0252(15) -0.0009(13) 0.0115(12) 0.0000(11) C92 0.0312(16) 0.0233(15) 0.0297(16) -0.0038(13) 0.0180(13) -0.0020(11) C93 0.0259(15) 0.0235(15) 0.0241(15) -0.0023(12) 0.0122(12) -0.0030(11) C94A 0.0225(14) 0.0257(15) 0.0265(15) 0.0036(13) 0.0133(12) 0.0025(11) C95 0.0301(16) 0.0262(16) 0.0360(17) -0.0021(14) 0.0171(14) -0.0032(12) C96 0.0344(17) 0.0315(17) 0.0299(17) 0.0044(14) 0.0142(14) 0.0082(13) C97 0.0407(18) 0.0292(17) 0.0338(18) 0.0072(14) 0.0205(15) 0.0103(13) C98 0.0355(17) 0.0259(16) 0.0358(18) 0.0002(14) 0.0216(14) -0.0010(12) C98A 0.0298(16) 0.0275(16) 0.0298(16) -0.0033(13) 0.0200(13) 0.0008(12) C99 0.0337(17) 0.0256(16) 0.0309(17) -0.0051(13) 0.0184(14) -0.0018(12) C99A 0.0286(16) 0.0331(16) 0.0211(15) -0.0002(13) 0.0123(12) -0.0011(12) C100 0.0383(18) 0.0344(17) 0.0277(17) -0.0039(14) 0.0155(14) -0.0049(13) C101 0.0304(17) 0.048(2) 0.0272(17) 0.0002(15) 0.0132(14) -0.0094(14) C102 0.0287(17) 0.0461(19) 0.0281(17) 0.0020(15) 0.0163(13) 0.0015(13) C103 0.0260(16) 0.0317(16) 0.0286(16) 0.0024(13) 0.0131(13) 0.0016(12) C104 0.0255(15) 0.0322(16) 0.0209(15) -0.0027(13) 0.0118(12) -0.0013(12) C105 0.0252(15) 0.0255(15) 0.0254(15) 0.0000(13) 0.0133(12) 0.0017(11) C106 0.0371(18) 0.0331(18) 0.0387(19) 0.0041(15) 0.0191(15) 0.0070(14) C107 0.0336(18) 0.0308(18) 0.046(2) 0.0068(16) 0.0185(15) 0.0023(13) C108 0.0270(15) 0.0220(14) 0.0262(15) 0.0003(12) 0.0132(12) -0.0007(11) C109 0.0318(17) 0.0258(16) 0.0322(17) -0.0061(13) 0.0136(13) -0.0041(12) C110 0.0281(16) 0.0337(17) 0.0367(18) -0.0030(14) 0.0168(14) -0.0062(12) C111 0.0255(16) 0.0342(17) 0.0327(17) -0.0012(14) 0.0142(13) 0.0022(12) C112 0.0318(17) 0.0263(16) 0.0374(18) -0.0031(14) 0.0167(14) 0.0007(12) C113 0.0282(16) 0.0249(15) 0.0326(17) -0.0044(13) 0.0127(13) -0.0027(11) _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 C14 1.152(4) . ? N2 C15 1.149(3) . ? N4 C3 1.468(3) . ? N4 C4A 1.438(3) . ? N4 C13B 1.481(3) . ? C1 H1 0.9800 . ? C1 C2 1.557(3) . ? C1 C13B 1.547(4) . ? C1 C14 1.457(4) . ? C2 H2 0.9800 . ? C2 C3 1.551(4) . ? C2 C15 1.463(4) . ? C3 H3 0.9800 . ? C3 C16 1.514(4) . ? C4A C5 1.390(4) . ? C4A C8A 1.397(4) . ? C5 H5 0.9300 . ? C5 C6 1.393(4) . ? C6 H6 0.9300 . ? C6 C7 1.377(5) . ? C7 H7 0.9300 . ? C7 C8 1.372(5) . ? C8 H8 0.9300 . ? C8 C8A 1.385(4) . ? C8A C9 1.493(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C9A 1.517(4) . ? C9A C10 1.396(4) . ? C9A C13A 1.409(4) . ? C10 H10F 0.9300 . ? C10 C11 1.377(4) . ? C11 H11D 0.9300 . ? C11 C12 1.384(4) . ? C12 H12 0.9300 . ? C12 C13 1.378(4) . ? C13 H13 0.9300 . ? C13 C13A 1.403(4) . ? C13A C13B 1.518(4) . ? C13B H13A 0.9800 . ? C16 C17 1.379(4) . ? C16 C21 1.394(4) . ? C17 H17 0.9300 . ? C17 C18 1.408(4) . ? C18 H18 0.9300 . ? C18 C19 1.387(5) . ? C19 H19 0.9300 . ? C19 C20 1.373(4) . ? C20 H20 0.9300 . ? C20 C21 1.372(4) . ? C21 H21 0.9300 . ? N21 C44 1.140(4) . ? N22 C45 1.139(4) . ? N34 C33 1.467(3) . ? N34 C34A 1.427(3) . ? N34 C43B 1.471(3) . ? C31 H31 0.9800 . ? C31 C32 1.563(4) . ? C31 C43B 1.553(4) . ? C31 C44 1.470(4) . ? C32 H32 0.9800 . ? C32 C33 1.554(4) . ? C32 C45 1.466(4) . ? C33 H33 0.9800 . ? C33 C46 1.505(4) . ? C34A C35 1.385(4) . ? C34A C38A 1.411(4) . ? C35 H35 0.9300 . ? C35 C36 1.390(4) . ? C36 H36 0.9300 . ? C36 C37 1.386(4) . ? C37 H37 0.9300 . ? C37 C38 1.383(4) . ? C38 H38 0.9300 . ? C38 C38A 1.386(4) . ? C38A C39 1.510(4) . ? C39 H39B 0.9700 . ? C39 H39A 0.9700 . ? C39 C39A 1.506(4) . ? C39A C40 1.399(4) . ? C39A C43A 1.405(4) . ? C40 H40 0.9300 . ? C40 C41 1.377(4) . ? C41 H41 0.9300 . ? C41 C42 1.383(4) . ? C42 H42 0.9300 . ? C42 C43 1.387(4) . ? C43 H43 0.9300 . ? C43 C43A 1.397(4) . ? C43A C43B 1.520(4) . ? C43B H43A 0.9800 . ? C46 C47 1.389(4) . ? C46 C51 1.386(4) . ? C47 H47 0.9300 . ? C47 C48 1.396(4) . ? C48 H48 0.9300 . ? C48 C49 1.374(5) . ? C49 H49 0.9300 . ? C49 C50 1.386(5) . ? C50 H50 0.9300 . ? C50 C51 1.390(4) . ? C51 H51 0.9300 . ? Cl1A C1SB 2.136(9) 2_655 ? Cl1A C1SB 1.598(9) . ? Cl1B H1SB 1.6561 . ? C1SB Cl1A 2.136(9) 2_655 ? C1SB C1SB 0.640(16) 2_655 ? C1SB H1SB 0.9902 . ? C1SB H1SA 0.9899 . ? N31 C74 1.141(4) . ? N32 C75 1.153(4) . ? N64 C63 1.460(3) . ? N64 C64A 1.437(3) . ? N64 C73B 1.470(3) . ? C61 H61 0.9800 . ? C61 C62 1.562(4) . ? C61 C73B 1.551(4) . ? C61 C74 1.468(4) . ? C62 H62 0.9800 . ? C62 C63 1.547(4) . ? C62 C75 1.454(4) . ? C63 H63 0.9800 . ? C63 C76 1.519(4) . ? C64A C65 1.374(4) . ? C64A C68A 1.410(4) . ? C65 H65 0.9300 . ? C65 C66 1.393(4) . ? C66 H66 0.9300 . ? C66 C67 1.374(4) . ? C67 H67 0.9300 . ? C67 C68 1.381(4) . ? C68 H68 0.9300 . ? C68 C68A 1.392(4) . ? C68A C69 1.500(4) . ? C69 H69A 0.9700 . ? C69 H69B 0.9700 . ? C69 C69A 1.517(4) . ? C69A C70 1.395(4) . ? C69A C73A 1.396(4) . ? C70 H70 0.9300 . ? C70 C71 1.371(4) . ? C71 H71 0.9300 . ? C71 C72 1.381(4) . ? C72 H72 0.9300 . ? C72 C73 1.391(4) . ? C73 H73 0.9300 . ? C73 C73A 1.398(4) . ? C73A C73B 1.529(4) . ? C73B H73A 0.9800 . ? C76 C77 1.378(4) . ? C76 C81 1.384(4) . ? C77 H77 0.9300 . ? C77 C78 1.390(4) . ? C78 H78 0.9300 . ? C78 C79 1.381(5) . ? C79 H79 0.9300 . ? C79 C80 1.378(4) . ? C80 H80 0.9300 . ? C80 C81 1.394(4) . ? C81 H81 0.9300 . ? N41 C106 1.149(4) . ? N42 C107 1.141(4) . ? N94 C93 1.471(3) . ? N94 C94A 1.435(3) . ? N94 C105 1.467(3) . ? C91 H91 0.9800 . ? C91 C92 1.556(3) . ? C91 C105 1.547(4) . ? C91 C106 1.457(4) . ? C92 H92 0.9800 . ? C92 C93 1.551(4) . ? C92 C107 1.469(4) . ? C93 H93 0.9800 . ? C93 C108 1.500(3) . ? C94A C95 1.387(4) . ? C94A C98A 1.407(4) . ? C95 H95 0.9300 . ? C95 C96 1.401(4) . ? C96 H96 0.9300 . ? C96 C97 1.375(4) . ? C97 H97 0.9300 . ? C97 C98 1.383(4) . ? C98 H98 0.9300 . ? C98 C98A 1.382(4) . ? C98A C99 1.501(4) . ? C99 H99A 0.9700 . ? C99 H99B 0.9700 . ? C99 C99A 1.520(4) . ? C99A C100 1.393(4) . ? C99A C104 1.399(4) . ? C100 H10 0.9300 . ? C100 C101 1.386(4) . ? C101 H10A 0.9300 . ? C101 C102 1.379(4) . ? C102 H10B 0.9300 . ? C102 C103 1.385(4) . ? C103 H10C 0.9300 . ? C103 C104 1.401(4) . ? C104 C105 1.528(4) . ? C105 H10D 0.9800 . ? C108 C109 1.397(4) . ? C108 C113 1.395(4) . ? C109 H10E 0.9300 . ? C109 C110 1.385(4) . ? C110 H11 0.9300 . ? C110 C111 1.380(4) . ? C111 H11A 0.9300 . ? C111 C112 1.383(4) . ? C112 H11B 0.9300 . ? C112 C113 1.386(4) . ? C113 H11C 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 N1 C14 C1 178.1(3) . . ? N2 C15 C2 179.0(3) . . ? N4 C3 C2 101.3(2) . . ? N4 C3 H3 109.8 . . ? N4 C3 C16 113.1(2) . . ? N4 C13B C1 100.44(19) . . ? N4 C13B C13A 116.9(2) . . ? N4 C13B H13A 108.9 . . ? C1 C2 H2 108.3 . . ? C1 C13B H13A 108.9 . . ? C2 C1 H1 108.3 . . ? C2 C3 H3 109.8 . . ? C3 N4 C13B 105.7(2) . . ? C3 C2 C1 105.1(2) . . ? C3 C2 H2 108.3 . . ? C4A N4 C3 118.2(2) . . ? C4A N4 C13B 113.7(2) . . ? C4A C5 H5 120.3 . . ? C4A C5 C6 119.4(3) . . ? C4A C8A C9 118.1(3) . . ? C5 C4A N4 123.3(3) . . ? C5 C4A C8A 120.4(3) . . ? C5 C6 H6 119.8 . . ? C6 C5 H5 120.3 . . ? C6 C7 H7 120.2 . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6 119.8 . . ? C7 C8 H8 119.1 . . ? C7 C8 C8A 121.7(3) . . ? C8 C7 C6 119.6(3) . . ? C8 C7 H7 120.2 . . ? C8 C8A C4A 118.4(3) . . ? C8 C8A C9 123.5(3) . . ? C8A C4A N4 116.3(3) . . ? C8A C8 H8 119.1 . . ? C8A C9 H9A 109.4 . . ? C8A C9 H9B 109.4 . . ? C8A C9 C9A 111.1(2) . . ? H9A C9 H9B 108.0 . . ? C9A C9 H9A 109.4 . . ? C9A C9 H9B 109.4 . . ? C9A C10 H10F 119.1 . . ? C9A C13A C13B 126.0(2) . . ? C10 C9A C9 119.4(3) . . ? C10 C9A C13A 118.5(3) . . ? C10 C11 H11D 120.1 . . ? C10 C11 C12 119.9(3) . . ? C11 C10 C9A 121.8(3) . . ? C11 C10 H10F 119.1 . . ? C11 C12 H12 120.3 . . ? C12 C11 H11D 120.1 . . ? C12 C13 H13 119.2 . . ? C12 C13 C13A 121.7(3) . . ? C13 C12 C11 119.4(3) . . ? C13 C12 H12 120.3 . . ? C13 C13A C9A 118.6(3) . . ? C13 C13A C13B 115.4(2) . . ? C13A C9A C9 121.7(3) . . ? C13A C13 H13 119.2 . . ? C13A C13B C1 112.5(2) . . ? C13A C13B H13A 108.9 . . ? C13B C1 H1 108.3 . . ? C13B C1 C2 104.5(2) . . ? C14 C1 H1 108.3 . . ? C14 C1 C2 113.1(2) . . ? C14 C1 C13B 114.1(2) . . ? C15 C2 C1 114.4(2) . . ? C15 C2 H2 108.3 . . ? C15 C2 C3 112.1(2) . . ? C16 C3 C2 112.8(2) . . ? C16 C3 H3 109.8 . . ? C16 C17 H17 119.9 . . ? C16 C17 C18 120.1(3) . . ? C16 C21 H21 119.7 . . ? C17 C16 C3 120.5(3) . . ? C17 C16 C21 119.3(3) . . ? C17 C18 H18 120.4 . . ? C18 C17 H17 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C18 C17 119.3(3) . . ? C19 C18 H18 120.4 . . ? C19 C20 H20 119.7 . . ? C20 C19 C18 120.2(3) . . ? C20 C19 H19 119.9 . . ? C20 C21 C16 120.6(3) . . ? C20 C21 H21 119.7 . . ? C21 C16 C3 120.1(2) . . ? C21 C20 C19 120.5(3) . . ? C21 C20 H20 119.7 . . ? N21 C44 C31 178.5(4) . . ? N22 C45 C32 179.5(4) . . ? N34 C33 C32 100.6(2) . . ? N34 C33 H33 109.4 . . ? N34 C33 C46 114.4(2) . . ? N34 C43B C31 100.2(2) . . ? N34 C43B C43A 118.3(2) . . ? N34 C43B H43A 108.2 . . ? C31 C32 H32 108.5 . . ? C31 C43B H43A 108.2 . . ? C32 C31 H31 108.5 . . ? C32 C33 H33 109.4 . . ? C33 N34 C43B 104.9(2) . . ? C33 C32 C31 104.6(2) . . ? C33 C32 H32 108.5 . . ? C34A N34 C33 117.4(2) . . ? C34A N34 C43B 115.5(2) . . ? C34A C35 H35 120.0 . . ? C34A C35 C36 120.0(3) . . ? C34A C38A C39 117.7(2) . . ? C35 C34A N34 123.6(2) . . ? C35 C34A C38A 120.2(3) . . ? C35 C36 H36 120.0 . . ? C36 C35 H35 120.0 . . ? C36 C37 H37 120.0 . . ? C37 C36 C35 120.0(3) . . ? C37 C36 H36 120.0 . . ? C37 C38 H38 119.5 . . ? C37 C38 C38A 121.0(3) . . ? C38 C37 C36 120.0(3) . . ? C38 C37 H37 120.0 . . ? C38 C38A C34A 118.7(3) . . ? C38 C38A C39 123.6(3) . . ? C38A C34A N34 116.1(3) . . ? C38A C38 H38 119.5 . . ? C38A C39 H39B 109.5 . . ? C38A C39 H39A 109.5 . . ? H39B C39 H39A 108.1 . . ? C39A C39 C38A 110.7(2) . . ? C39A C39 H39B 109.5 . . ? C39A C39 H39A 109.5 . . ? C39A C40 H40 119.0 . . ? C39A C43A C43B 125.0(2) . . ? C40 C39A C39 119.7(2) . . ? C40 C39A C43A 118.0(2) . . ? C40 C41 H41 120.0 . . ? C40 C41 C42 120.1(3) . . ? C41 C40 C39A 122.1(3) . . ? C41 C40 H40 119.0 . . ? C41 C42 H42 120.6 . . ? C41 C42 C43 118.9(3) . . ? C42 C41 H41 120.0 . . ? C42 C43 H43 119.1 . . ? C42 C43 C43A 121.8(3) . . ? C43 C42 H42 120.6 . . ? C43 C43A C39A 119.2(2) . . ? C43 C43A C43B 115.8(2) . . ? C43A C39A C39 121.9(2) . . ? C43A C43 H43 119.1 . . ? C43A C43B C31 113.1(2) . . ? C43A C43B H43A 108.2 . . ? C43B C31 H31 108.5 . . ? C43B C31 C32 103.9(2) . . ? C44 C31 H31 108.5 . . ? C44 C31 C32 113.7(2) . . ? C44 C31 C43B 113.5(2) . . ? C45 C32 C31 114.1(2) . . ? C45 C32 H32 108.5 . . ? C45 C32 C33 112.3(2) . . ? C46 C33 C32 113.4(2) . . ? C46 C33 H33 109.4 . . ? C46 C47 H47 119.7 . . ? C46 C47 C48 120.5(3) . . ? C46 C51 C50 120.9(3) . . ? C46 C51 H51 119.6 . . ? C47 C46 C33 121.5(3) . . ? C47 C48 H48 119.9 . . ? C48 C47 H47 119.7 . . ? C48 C49 H49 120.0 . . ? C48 C49 C50 120.0(3) . . ? C49 C48 C47 120.1(3) . . ? C49 C48 H48 119.9 . . ? C49 C50 H50 120.1 . . ? C49 C50 C51 119.8(3) . . ? C50 C49 H49 120.0 . . ? C50 C51 H51 119.6 . . ? C51 C46 C33 119.8(3) . . ? C51 C46 C47 118.7(3) . . ? C51 C50 H50 120.1 . . ? Cl1A C1SB Cl1A 116.9(5) . 2_655 ? Cl1A C1SB H1SB 105.6 . . ? Cl1A C1SB H1SB 105.4 2_655 . ? Cl1A C1SB H1SA 104.8 2_655 . ? Cl1A C1SB H1SA 104.8 . . ? C1SB Cl1A C1SB 10.8(4) . 2_655 ? C1SB C1SB Cl1A 141.2(9) 2_655 . ? C1SB C1SB Cl1A 27.9(7) 2_655 2_655 ? C1SB C1SB H1SB 83.1 2_655 . ? C1SB C1SB H1SA 102.6 2_655 . ? H1SB C1SB H1SA 120.0 . . ? N31 C74 C61 179.4(4) . . ? N32 C75 C62 179.0(4) . . ? N64 C63 C62 101.5(2) . . ? N64 C63 H63 110.2 . . ? N64 C63 C76 113.1(2) . . ? N64 C73B C61 102.0(2) . . ? N64 C73B C73A 116.0(2) . . ? N64 C73B H73A 109.1 . . ? C61 C62 H62 108.5 . . ? C61 C73B H73A 109.1 . . ? C62 C61 H61 108.4 . . ? C62 C63 H63 110.2 . . ? C63 N64 C73B 108.0(2) . . ? C63 C62 C61 105.3(2) . . ? C63 C62 H62 108.5 . . ? C64A N64 C63 116.1(2) . . ? C64A N64 C73B 114.2(2) . . ? C64A C65 H65 120.1 . . ? C64A C65 C66 119.7(3) . . ? C64A C68A C69 118.6(3) . . ? C65 C64A N64 124.3(2) . . ? C65 C64A C68A 120.7(3) . . ? C65 C66 H66 119.9 . . ? C66 C65 H65 120.1 . . ? C66 C67 H67 119.9 . . ? C66 C67 C68 120.3(3) . . ? C67 C66 C65 120.2(3) . . ? C67 C66 H66 119.9 . . ? C67 C68 H68 119.7 . . ? C67 C68 C68A 120.7(3) . . ? C68 C67 H67 119.9 . . ? C68 C68A C64A 118.3(3) . . ? C68 C68A C69 123.1(3) . . ? C68A C64A N64 115.0(2) . . ? C68A C68 H68 119.7 . . ? C68A C69 H69A 108.8 . . ? C68A C69 H69B 108.8 . . ? C68A C69 C69A 113.6(2) . . ? H69A C69 H69B 107.7 . . ? C69A C69 H69A 108.8 . . ? C69A C69 H69B 108.8 . . ? C69A C70 H70 118.8 . . ? C69A C73A C73 118.8(3) . . ? C69A C73A C73B 125.6(2) . . ? C70 C69A C69 118.2(3) . . ? C70 C69A C73A 118.6(3) . . ? C70 C71 H71 120.3 . . ? C70 C71 C72 119.4(3) . . ? C71 C70 C69A 122.3(3) . . ? C71 C70 H70 118.8 . . ? C71 C72 H72 120.3 . . ? C71 C72 C73 119.4(3) . . ? C72 C71 H71 120.3 . . ? C72 C73 H73 119.3 . . ? C72 C73 C73A 121.4(3) . . ? C73 C72 H72 120.3 . . ? C73 C73A C73B 115.6(3) . . ? C73A C69A C69 123.2(2) . . ? C73A C73 H73 119.3 . . ? C73A C73B C61 111.1(2) . . ? C73A C73B H73A 109.1 . . ? C73B C61 H61 108.4 . . ? C73B C61 C62 104.9(2) . . ? C74 C61 H61 108.4 . . ? C74 C61 C62 113.5(2) . . ? C74 C61 C73B 113.0(2) . . ? C75 C62 C61 114.8(2) . . ? C75 C62 H62 108.5 . . ? C75 C62 C63 111.1(2) . . ? C76 C63 C62 111.4(2) . . ? C76 C63 H63 110.2 . . ? C76 C77 H77 119.7 . . ? C76 C77 C78 120.7(3) . . ? C76 C81 C80 120.4(3) . . ? C76 C81 H81 119.8 . . ? C77 C76 C63 120.8(3) . . ? C77 C76 C81 119.3(3) . . ? C77 C78 H78 120.1 . . ? C78 C77 H77 119.7 . . ? C78 C79 H79 119.9 . . ? C79 C78 C77 119.7(3) . . ? C79 C78 H78 120.1 . . ? C79 C80 H80 120.1 . . ? C79 C80 C81 119.8(3) . . ? C80 C79 C78 120.2(3) . . ? C80 C79 H79 119.9 . . ? C80 C81 H81 119.8 . . ? C81 C76 C63 119.8(2) . . ? C81 C80 H80 120.1 . . ? N41 C106 C91 178.4(4) . . ? N42 C107 C92 178.8(4) . . ? N94 C93 C92 100.5(2) . . ? N94 C93 H93 110.2 . . ? N94 C93 C108 113.9(2) . . ? N94 C105 C91 102.17(19) . . ? N94 C105 C104 115.9(2) . . ? N94 C105 H10D 108.7 . . ? C91 C92 H92 108.0 . . ? C91 C105 H10D 108.7 . . ? C92 C91 H91 108.6 . . ? C92 C93 H93 110.2 . . ? C93 C92 C91 105.5(2) . . ? C93 C92 H92 108.0 . . ? C94A N94 C93 117.6(2) . . ? C94A N94 C105 114.04(19) . . ? C94A C95 H95 120.3 . . ? C94A C95 C96 119.5(3) . . ? C94A C98A C99 117.9(2) . . ? C95 C94A N94 124.1(2) . . ? C95 C94A C98A 120.2(3) . . ? C95 C96 H96 119.9 . . ? C96 C95 H95 120.3 . . ? C96 C97 H97 120.0 . . ? C96 C97 C98 120.1(3) . . ? C97 C96 C95 120.3(3) . . ? C97 C96 H96 119.9 . . ? C97 C98 H98 119.5 . . ? C98 C97 H97 120.0 . . ? C98 C98A C94A 119.0(3) . . ? C98 C98A C99 123.0(2) . . ? C98A C94A N94 115.6(2) . . ? C98A C98 C97 121.0(3) . . ? C98A C98 H98 119.5 . . ? C98A C99 H99A 109.4 . . ? C98A C99 H99B 109.4 . . ? C98A C99 C99A 111.1(2) . . ? H99A C99 H99B 108.0 . . ? C99A C99 H99A 109.4 . . ? C99A C99 H99B 109.4 . . ? C99A C100 H10 119.0 . . ? C99A C104 C103 118.9(2) . . ? C99A C104 C105 125.7(2) . . ? C100 C99A C99 118.3(2) . . ? C100 C99A C104 118.5(2) . . ? C100 C101 H10A 120.2 . . ? C101 C100 C99A 122.0(3) . . ? C101 C100 H10 119.0 . . ? C101 C102 H10B 120.4 . . ? C101 C102 C103 119.3(3) . . ? C102 C101 C100 119.6(3) . . ? C102 C101 H10A 120.2 . . ? C102 C103 H10C 119.2 . . ? C102 C103 C104 121.7(3) . . ? C103 C102 H10B 120.4 . . ? C103 C104 C105 115.4(2) . . ? C104 C99A C99 123.1(2) . . ? C104 C103 H10C 119.2 . . ? C104 C105 C91 112.5(2) . . ? C104 C105 H10D 108.7 . . ? C105 N94 C93 107.18(19) . . ? C105 C91 H91 108.6 . . ? C105 C91 C92 104.7(2) . . ? C106 C91 H91 108.6 . . ? C106 C91 C92 113.4(2) . . ? C106 C91 C105 112.8(2) . . ? C107 C92 C91 115.0(2) . . ? C107 C92 H92 108.0 . . ? C107 C92 C93 112.0(2) . . ? C108 C93 C92 111.3(2) . . ? C108 C93 H93 110.2 . . ? C108 C109 H10E 119.8 . . ? C108 C113 H11C 119.8 . . ? C109 C108 C93 119.9(2) . . ? C109 C110 H11 119.8 . . ? C110 C109 C108 120.3(3) . . ? C110 C109 H10E 119.8 . . ? C110 C111 H11A 120.2 . . ? C110 C111 C112 119.7(2) . . ? C111 C110 C109 120.5(3) . . ? C111 C110 H11 119.8 . . ? C111 C112 H11B 119.8 . . ? C111 C112 C113 120.4(3) . . ? C112 C111 H11A 120.2 . . ? C112 C113 C108 120.3(3) . . ? C112 C113 H11C 119.8 . . ? C113 C108 C93 121.2(2) . . ? C113 C108 C109 118.8(2) . . ? C113 C112 H11B 119.8 . . ? # Attachment '- 18.cif' data_18_DAX18 _database_code_depnum_ccdc_archive 'CCDC 809446' _audit_creation_method SHELXL-97 _chemical_absolute_configuration unk _chemical_formula_moiety 'C25 H19 N3' _chemical_formula_sum 'C25 H19 N3' _chemical_formula_weight 361.43 _chemical_melting_point '205 C' _chemical_name_common ? _chemical_name_systematic ; (1RS,2RS,3SR,13bRS)-3-Phenyl-2,3,9,13b-tetrahydro-1H- dibenzo[c,f]pyrrolo[1,2-a]azepine-1,2-dicarbonitrile ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_IT_number 4 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_angle_alpha 90.00 _cell_angle_beta 99.290(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 12.6196(2) _cell_length_b 5.85170(10) _cell_length_c 12.6336(2) _cell_measurement_reflns_used 2594 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 57.631 _cell_measurement_theta_min 3.545 _cell_volume 920.71(3) _exptl_absorpt_coefficient_mu 0.604 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0499 before and 0.0335 after correction. The Ratio of minimum to maximum transmission is 0.871. The \l/2 correction factor is Not present ; _exptl_crystal_F_000 380 _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier whitish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_special_details ? _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.926 _diffrn_measured_fraction_theta_max 0.926 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_source 'Microstar rotating anode' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54188 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3871 _diffrn_reflns_theta_full 55.92 _diffrn_reflns_theta_max 55.92 _diffrn_reflns_theta_min 3.54 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1946 _reflns_number_total 2041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution ; A short history of SHELX (Sheldrick, 2007)/Bruker ; _refine_diff_density_max 0.120 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.035 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0331 _refine_ls_abs_structure_Flack -0.1(6) _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 329 _refine_ls_number_reflns 2041 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.0822 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap 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 0.10387(16) 0.0784(4) 0.49534(17) 0.0293(5) Uani 1 1 d . . . N2 N 0.02791(18) 0.9060(4) 0.72339(17) 0.0313(6) Uani 1 1 d . . . N4 N 0.27495(14) 0.5760(3) 0.73444(15) 0.0189(5) Uani 1 1 d . . . C1 C 0.14131(18) 0.4788(4) 0.5853(2) 0.0206(6) Uani 1 1 d . . . C2 C 0.09507(18) 0.4906(4) 0.69168(19) 0.0200(6) Uani 1 1 d . . . C3 C 0.19439(18) 0.4366(4) 0.77615(19) 0.0186(5) Uani 1 1 d . . . C4A C 0.38283(18) 0.5835(4) 0.79101(18) 0.0187(6) Uani 1 1 d . . . C5 C 0.42750(18) 0.4187(4) 0.86398(18) 0.0199(6) Uani 1 1 d . . . C6 C 0.53159(18) 0.4422(5) 0.91690(19) 0.0225(6) Uani 1 1 d . . . C7 C 0.59175(19) 0.6307(4) 0.89843(19) 0.0226(6) Uani 1 1 d . . . C8 C 0.54707(19) 0.7967(4) 0.8268(2) 0.0208(6) Uani 1 1 d . . . C8A C 0.44295(19) 0.7759(4) 0.77192(18) 0.0193(6) Uani 1 1 d . . . C9 C 0.39203(19) 0.9531(4) 0.6941(2) 0.0217(6) Uani 1 1 d . . . C9A C 0.36882(18) 0.8762(4) 0.57868(19) 0.0200(6) Uani 1 1 d . . . C10 C 0.40486(19) 1.0124(5) 0.5005(2) 0.0243(6) Uani 1 1 d . . . C11 C 0.3836(2) 0.9554(5) 0.3928(2) 0.0279(6) Uani 1 1 d . . . C12 C 0.3284(2) 0.7585(5) 0.3609(2) 0.0271(6) Uani 1 1 d . . . C13 C 0.29393(19) 0.6190(5) 0.4375(2) 0.0242(6) Uani 1 1 d . . . C13A C 0.31213(18) 0.6776(4) 0.5459(2) 0.0201(6) Uani 1 1 d . . . C13B C 0.26547(17) 0.5139(4) 0.61982(18) 0.0180(5) Uani 1 1 d . . . C14 C 0.11925(18) 0.2566(5) 0.5336(2) 0.0221(6) Uani 1 1 d . . . C15 C 0.05594(18) 0.7236(5) 0.70915(19) 0.0222(6) Uani 1 1 d . . . C16 C 0.17860(17) 0.4818(4) 0.89029(19) 0.0194(6) Uani 1 1 d . . . C17 C 0.12533(18) 0.3140(4) 0.9407(2) 0.0236(6) Uani 1 1 d . . . C18 C 0.10418(19) 0.3483(4) 1.0438(2) 0.0250(6) Uani 1 1 d . . . C19 C 0.13667(18) 0.5462(4) 1.0980(2) 0.0259(6) Uani 1 1 d . . . C20 C 0.18923(18) 0.7145(5) 1.0485(2) 0.0265(6) Uani 1 1 d . . . C21 C 0.20925(19) 0.6814(4) 0.9448(2) 0.0229(6) Uani 1 1 d . . . H1 H 0.1118(17) 0.597(4) 0.5354(18) 0.014(6) Uiso 1 1 d . . . H2 H 0.032(2) 0.384(5) 0.698(2) 0.036(7) Uiso 1 1 d . . . H3 H 0.2089(18) 0.272(5) 0.7651(17) 0.017(6) Uiso 1 1 d . . . H5 H 0.3862(18) 0.292(4) 0.8769(18) 0.014(6) Uiso 1 1 d . . . H6 H 0.5605(16) 0.325(4) 0.9674(19) 0.009(6) Uiso 1 1 d . . . H7 H 0.6632(18) 0.648(4) 0.9393(17) 0.017(6) Uiso 1 1 d . . . H8 H 0.5880(18) 0.935(4) 0.8147(17) 0.012(5) Uiso 1 1 d . . . H9A H 0.3257(18) 1.002(4) 0.7178(18) 0.010(5) Uiso 1 1 d . . . H9B H 0.4364(18) 1.096(5) 0.6974(17) 0.018(6) Uiso 1 1 d . . . H10 H 0.4460(19) 1.140(5) 0.5209(19) 0.023(7) Uiso 1 1 d . . . H11 H 0.409(2) 1.059(5) 0.337(2) 0.037(7) Uiso 1 1 d . . . H12 H 0.3109(19) 0.711(4) 0.283(2) 0.027(7) Uiso 1 1 d . . . H13 H 0.260(2) 0.481(5) 0.4143(19) 0.023(7) Uiso 1 1 d . . . H13A H 0.2987(16) 0.361(4) 0.6145(17) 0.010(6) Uiso 1 1 d . . . H17 H 0.1034(19) 0.173(5) 0.9007(19) 0.026(7) Uiso 1 1 d . . . H18 H 0.062(2) 0.227(5) 1.076(2) 0.037(7) Uiso 1 1 d . . . H19 H 0.124(2) 0.571(5) 1.168(2) 0.030(7) Uiso 1 1 d . . . H20 H 0.211(2) 0.860(5) 1.085(2) 0.028(7) Uiso 1 1 d . . . H21 H 0.2431(18) 0.797(4) 0.9133(18) 0.015(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0223(11) 0.0372(15) 0.0287(13) -0.0043(12) 0.0045(10) -0.0009(10) N2 0.0388(13) 0.0316(14) 0.0249(12) -0.0009(11) 0.0096(10) 0.0053(11) N4 0.0171(9) 0.0233(11) 0.0172(11) 0.0011(8) 0.0058(9) -0.0026(8) C1 0.0197(12) 0.0235(14) 0.0179(14) -0.0008(12) 0.0005(11) 0.0008(10) C2 0.0201(12) 0.0221(14) 0.0191(14) -0.0001(11) 0.0064(12) -0.0003(11) C3 0.0190(11) 0.0193(14) 0.0187(13) 0.0001(10) 0.0069(10) 0.0006(10) C4A 0.0200(12) 0.0242(14) 0.0130(12) -0.0021(10) 0.0061(11) 0.0003(11) C5 0.0233(13) 0.0231(15) 0.0151(13) -0.0005(11) 0.0087(11) 0.0004(11) C6 0.0254(13) 0.0275(15) 0.0149(13) -0.0014(11) 0.0039(11) 0.0029(11) C7 0.0188(13) 0.0318(15) 0.0173(14) -0.0072(11) 0.0034(12) 0.0014(11) C8 0.0223(13) 0.0239(15) 0.0190(14) -0.0043(11) 0.0121(11) -0.0025(11) C8A 0.0235(12) 0.0220(13) 0.0142(13) -0.0031(10) 0.0083(11) 0.0026(10) C9 0.0208(12) 0.0212(15) 0.0245(15) -0.0028(11) 0.0075(12) -0.0004(12) C9A 0.0186(11) 0.0221(14) 0.0194(14) 0.0039(11) 0.0035(11) 0.0057(11) C10 0.0226(12) 0.0222(15) 0.0282(15) 0.0040(12) 0.0040(12) 0.0011(12) C11 0.0248(12) 0.0372(17) 0.0235(15) 0.0078(13) 0.0093(12) 0.0010(12) C12 0.0265(13) 0.0378(17) 0.0178(14) 0.0007(13) 0.0059(12) 0.0039(13) C13 0.0238(13) 0.0268(16) 0.0228(15) -0.0012(12) 0.0063(12) -0.0014(12) C13A 0.0187(12) 0.0246(15) 0.0172(13) 0.0023(10) 0.0034(10) 0.0061(11) C13B 0.0206(11) 0.0189(14) 0.0152(13) -0.0001(10) 0.0048(10) 0.0005(10) C14 0.0173(12) 0.0315(16) 0.0182(13) -0.0005(13) 0.0053(10) -0.0011(11) C15 0.0194(12) 0.0317(17) 0.0161(13) 0.0022(11) 0.0050(11) -0.0034(12) C16 0.0159(11) 0.0213(14) 0.0207(14) 0.0029(10) 0.0022(10) 0.0007(10) C17 0.0238(13) 0.0247(16) 0.0227(15) 0.0017(11) 0.0044(12) -0.0012(11) C18 0.0255(13) 0.0309(16) 0.0202(15) 0.0051(11) 0.0085(12) -0.0020(12) C19 0.0227(12) 0.0368(17) 0.0198(15) -0.0018(12) 0.0083(12) 0.0011(12) C20 0.0259(14) 0.0308(16) 0.0234(15) -0.0033(12) 0.0054(12) -0.0018(12) C21 0.0215(13) 0.0265(16) 0.0219(14) 0.0022(11) 0.0072(12) -0.0039(11) _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 C14 1.153(3) . ? N2 C15 1.148(3) . ? N4 C3 1.466(3) . ? N4 C4A 1.432(3) . ? N4 C13B 1.479(3) . ? C1 C2 1.551(3) . ? C1 C13B 1.571(3) . ? C1 C14 1.461(4) . ? C1 H1 0.97(2) . ? C2 C3 1.542(3) . ? C2 C15 1.479(4) . ? C2 H2 1.03(3) . ? C3 C16 1.510(3) . ? C3 H3 1.00(3) . ? C4A C5 1.389(3) . ? C4A C8A 1.400(4) . ? C5 C6 1.381(3) . ? C5 H5 0.94(3) . ? C6 C7 1.380(4) . ? C6 H6 0.97(2) . ? C7 C8 1.384(4) . ? C7 H7 0.97(2) . ? C8 C8A 1.389(3) . ? C8 H8 0.99(2) . ? C8A C9 1.501(3) . ? C9 C9A 1.509(3) . ? C9 H9A 0.98(2) . ? C9 H9B 1.00(3) . ? C9A C10 1.401(3) . ? C9A C13A 1.392(3) . ? C10 C11 1.385(4) . ? C10 H10 0.92(3) . ? C11 C12 1.372(4) . ? C11 H11 1.02(3) . ? C12 C13 1.389(4) . ? C12 H12 1.02(3) . ? C13 C13A 1.394(4) . ? C13 H13 0.94(3) . ? C13A C13B 1.522(3) . ? C13B H13A 1.00(2) . ? C16 C17 1.400(3) . ? C16 C21 1.379(3) . ? C17 C18 1.386(4) . ? C17 H17 0.98(3) . ? C18 C19 1.374(4) . ? C18 H18 1.01(3) . ? C19 C20 1.391(4) . ? C19 H19 0.93(3) . ? C20 C21 1.388(4) . ? C20 H20 0.99(3) . ? C21 H21 0.92(2) . ? 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 N1 C14 C1 178.0(3) . . ? N2 C15 C2 178.5(3) . . ? N4 C3 C2 99.82(18) . . ? N4 C3 C16 116.87(19) . . ? N4 C3 H3 109.6(13) . . ? N4 C13B C1 102.92(17) . . ? N4 C13B C13A 117.91(19) . . ? N4 C13B H13A 108.6(13) . . ? C1 C2 H2 116.3(15) . . ? C1 C13B H13A 106.0(12) . . ? C2 C1 C13B 104.55(17) . . ? C2 C1 H1 111.9(14) . . ? C2 C3 H3 104.4(13) . . ? C3 N4 C13B 105.31(17) . . ? C3 C2 C1 102.32(18) . . ? C3 C2 H2 112.5(15) . . ? C4A N4 C3 119.74(18) . . ? C4A N4 C13B 114.59(18) . . ? C4A C5 H5 119.2(13) . . ? C4A C8A C9 118.8(2) . . ? C5 C4A N4 124.1(2) . . ? C5 C4A C8A 120.0(2) . . ? C5 C6 H6 118.4(12) . . ? C6 C5 C4A 120.3(2) . . ? C6 C5 H5 120.5(13) . . ? C6 C7 C8 119.6(2) . . ? C6 C7 H7 119.0(13) . . ? C7 C6 C5 120.2(2) . . ? C7 C6 H6 121.4(12) . . ? C7 C8 C8A 121.2(2) . . ? C7 C8 H8 120.7(12) . . ? C8 C7 H7 121.3(14) . . ? C8 C8A C4A 118.7(2) . . ? C8 C8A C9 122.5(2) . . ? C8A C4A N4 115.88(19) . . ? C8A C8 H8 118.1(12) . . ? C8A C9 C9A 115.0(2) . . ? C8A C9 H9A 107.5(13) . . ? C8A C9 H9B 111.8(12) . . ? C9A C9 H9A 110.0(13) . . ? C9A C9 H9B 108.0(13) . . ? C9A C10 H10 119.7(15) . . ? C9A C13A C13 119.5(2) . . ? C9A C13A C13B 125.0(2) . . ? C10 C9A C9 118.5(2) . . ? C10 C11 H11 120.4(15) . . ? C11 C10 C9A 121.5(3) . . ? C11 C10 H10 118.8(15) . . ? C11 C12 C13 119.4(2) . . ? C11 C12 H12 122.5(15) . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 119.6(15) . . ? C12 C13 C13A 121.3(3) . . ? C12 C13 H13 117.9(15) . . ? C13 C12 H12 118.2(15) . . ? C13 C13A C13B 115.4(2) . . ? C13A C9A C9 123.2(2) . . ? C13A C9A C10 118.3(2) . . ? C13A C13 H13 120.8(15) . . ? C13A C13B C1 112.28(19) . . ? C13A C13B H13A 108.4(13) . . ? C13B C1 H1 110.5(13) . . ? C14 C1 C2 110.8(2) . . ? C14 C1 C13B 110.5(2) . . ? C14 C1 H1 108.5(13) . . ? C15 C2 C1 110.61(19) . . ? C15 C2 C3 109.83(19) . . ? C15 C2 H2 105.4(15) . . ? C16 C3 C2 114.03(18) . . ? C16 C3 H3 111.0(13) . . ? C16 C17 H17 118.1(15) . . ? C16 C21 C20 120.7(2) . . ? C16 C21 H21 121.0(15) . . ? C17 C16 C3 117.3(2) . . ? C17 C18 H18 118.4(17) . . ? C18 C17 C16 120.3(2) . . ? C18 C17 H17 121.5(15) . . ? C18 C19 C20 119.9(2) . . ? C18 C19 H19 121.2(17) . . ? C19 C18 C17 120.2(2) . . ? C19 C18 H18 121.3(16) . . ? C19 C20 H20 121.2(15) . . ? C20 C19 H19 118.9(17) . . ? C20 C21 H21 118.3(15) . . ? C21 C16 C3 123.7(2) . . ? C21 C16 C17 118.9(2) . . ? C21 C20 C19 119.9(3) . . ? C21 C20 H20 118.9(15) . . ? H9A C9 H9B 104.0(18) . . ? # Attachment '- 20.cif' data_20DAX12 _database_code_depnum_ccdc_archive 'CCDC 809447' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C31 H23 Cl N2 O2' _chemical_formula_sum 'C31 H23 Cl N2 O2' _chemical_formula_weight 490.96 _chemical_melting_point '222 C' _chemical_name_common ? _chemical_name_systematic ; (3aRS,3bRS,14SR,14aSR)-14-(4-Chlorophenyl)-2-phenyl-3b,8,14,14a- tetrahydro-dibenzo[c,f]pyrrolo[3',4':3,4]pyrrolo[1,2-a]azepine- 1,3(2H,3aH)-dione ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, z' 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 90.1420(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.6905(2) _cell_length_b 7.67060(10) _cell_length_c 29.1159(4) _cell_measurement_reflns_used 4666 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 55.105 _cell_measurement_theta_min 3.035 _cell_volume 2387.57(6) _exptl_absorpt_coefficient_mu 1.675 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.8391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0768 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.8391. The \l/2 correction factor is Not present ; _exptl_crystal_F_000 1024 _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_special_details ? _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type 'CU K\a' _diffrn_radiation_wavelength 1.54188 _diffrn_reflns_av_R_equivalents 0.0909 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 8647 _diffrn_reflns_theta_full 52.50 _diffrn_reflns_theta_max 52.50 _diffrn_reflns_theta_min 3.04 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2229 _reflns_number_total 2697 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.383 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.051 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0426 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 417 _refine_ls_number_reflns 2697 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1130 _refine_ls_wR_factor_ref 0.1178 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl1 Cl 0.48912(7) 1.37081(11) 0.45725(3) 0.0389(3) Uani 1 1 d . . . O1 O 0.49721(19) 0.6737(3) 0.31405(7) 0.0243(5) Uani 1 1 d . . . O2 O 0.80909(18) 0.2875(3) 0.28172(7) 0.0304(6) Uani 1 1 d . . . N2 N 0.6346(2) 0.4545(3) 0.29376(7) 0.0172(6) Uani 1 1 d . . . N12A N 0.8508(2) 0.6894(3) 0.39283(8) 0.0184(6) Uani 1 1 d . . . C1 C 0.6026(3) 0.6188(4) 0.31198(9) 0.0187(7) Uani 1 1 d . . . C3 C 0.7618(3) 0.4207(4) 0.29609(9) 0.0197(7) Uani 1 1 d . . . C3A C 0.8257(3) 0.5738(4) 0.31912(10) 0.0178(7) Uani 1 1 d . . . C3B C 0.8879(3) 0.5337(4) 0.36647(9) 0.0188(7) Uani 1 1 d . . . C3C C 1.0259(3) 0.4897(4) 0.36510(9) 0.0189(7) Uani 1 1 d . . . C4 C 1.0564(3) 0.3244(4) 0.34820(10) 0.0235(8) Uani 1 1 d . . . C5 C 1.1796(3) 0.2708(5) 0.34413(10) 0.0249(8) Uani 1 1 d . . . C6 C 1.2743(3) 0.3817(4) 0.35723(10) 0.0278(8) Uani 1 1 d . . . C7 C 1.2461(3) 0.5443(5) 0.37464(10) 0.0252(8) Uani 1 1 d . . . C7A C 1.1226(3) 0.6018(4) 0.37926(9) 0.0200(7) Uani 1 1 d . . . C8 C 1.0976(3) 0.7751(4) 0.40173(11) 0.0219(8) Uani 1 1 d . . . C8A C 1.0197(3) 0.7535(4) 0.44454(10) 0.0207(7) Uani 1 1 d . . . C9 C 1.0673(3) 0.7784(4) 0.48838(10) 0.0236(8) Uani 1 1 d . . . C10 C 0.9910(3) 0.7549(4) 0.52645(11) 0.0271(8) Uani 1 1 d . . . C11 C 0.8682(3) 0.7063(4) 0.52073(11) 0.0249(8) Uani 1 1 d . . . C12 C 0.8191(3) 0.6793(4) 0.47737(10) 0.0218(8) Uani 1 1 d . . . C12A C 0.8950(3) 0.7029(4) 0.43924(10) 0.0189(7) Uani 1 1 d . . . C13 C 0.7187(3) 0.7132(4) 0.38326(10) 0.0190(7) Uani 1 1 d . . . C13A C 0.7201(3) 0.7011(4) 0.33006(10) 0.0188(7) Uani 1 1 d . . . C14 C 0.6630(3) 0.8799(4) 0.40176(9) 0.0207(8) Uani 1 1 d . . . C15 C 0.7337(3) 1.0296(4) 0.40640(10) 0.0225(7) Uani 1 1 d . . . C16 C 0.6789(3) 1.1797(5) 0.42400(11) 0.0245(8) Uani 1 1 d . . . C17 C 0.5550(3) 1.1806(4) 0.43549(10) 0.0264(8) Uani 1 1 d . . . C18 C 0.4833(3) 1.0331(5) 0.43041(13) 0.0406(10) Uani 1 1 d . . . C19 C 0.5385(3) 0.8835(5) 0.41454(12) 0.0338(9) Uani 1 1 d . . . C20 C 0.5420(3) 0.3399(4) 0.27497(9) 0.0168(7) Uani 1 1 d . . . C21 C 0.5290(3) 0.1727(4) 0.29216(11) 0.0182(7) Uani 1 1 d . . . C22 C 0.4367(3) 0.0661(4) 0.27474(10) 0.0206(8) Uani 1 1 d . . . C23 C 0.3568(3) 0.1271(4) 0.24089(11) 0.0222(8) Uani 1 1 d . . . C24 C 0.3701(3) 0.2940(4) 0.22429(11) 0.0203(8) Uani 1 1 d . . . C25 C 0.4633(3) 0.4004(5) 0.24101(10) 0.0182(8) Uani 1 1 d . . . H3A H 0.886(3) 0.618(4) 0.3001(10) 0.015(8) Uiso 1 1 d . . . H3B H 0.840(2) 0.428(4) 0.3792(9) 0.016(7) Uiso 1 1 d . . . H4 H 0.987(3) 0.247(4) 0.3366(10) 0.028(8) Uiso 1 1 d . . . H5 H 1.199(3) 0.157(4) 0.3318(10) 0.026(8) Uiso 1 1 d . . . H6 H 1.363(3) 0.345(4) 0.3546(10) 0.034(9) Uiso 1 1 d . . . H7 H 1.311(3) 0.622(4) 0.3844(10) 0.027(9) Uiso 1 1 d . . . H8A H 1.046(3) 0.852(4) 0.3823(10) 0.023(8) Uiso 1 1 d . . . H8B H 1.176(2) 0.828(3) 0.4107(8) 0.001(6) Uiso 1 1 d . . . H9 H 1.151(3) 0.812(4) 0.4910(11) 0.034(9) Uiso 1 1 d . . . H10 H 1.025(3) 0.773(4) 0.5559(13) 0.043(10) Uiso 1 1 d . . . H11 H 0.818(3) 0.687(4) 0.5442(11) 0.022(8) Uiso 1 1 d . . . H12 H 0.735(3) 0.645(4) 0.4734(10) 0.025(9) Uiso 1 1 d . . . H13 H 0.667(2) 0.606(4) 0.3947(9) 0.018(7) Uiso 1 1 d . . . H13A H 0.733(2) 0.815(4) 0.3169(9) 0.013(7) Uiso 1 1 d . . . H15 H 0.823(3) 1.029(4) 0.3985(9) 0.021(8) Uiso 1 1 d . . . H16 H 0.728(3) 1.275(4) 0.4294(9) 0.012(7) Uiso 1 1 d . . . H18 H 0.395(4) 1.028(5) 0.4403(13) 0.062(11) Uiso 1 1 d . . . H19 H 0.490(3) 0.772(5) 0.4110(13) 0.056(11) Uiso 1 1 d . . . H21 H 0.578(3) 0.137(4) 0.3144(10) 0.018(9) Uiso 1 1 d . . . H22 H 0.428(3) -0.042(4) 0.2851(10) 0.020(8) Uiso 1 1 d . . . H23 H 0.298(3) 0.059(4) 0.2287(10) 0.029(9) Uiso 1 1 d . . . H24 H 0.321(3) 0.334(4) 0.2015(10) 0.011(8) Uiso 1 1 d . . . H25 H 0.471(2) 0.497(4) 0.2317(9) 0.003(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0375(5) 0.0318(6) 0.0475(6) -0.0156(4) 0.0035(4) 0.0068(4) O1 0.0243(13) 0.0222(12) 0.0264(12) -0.0050(10) -0.0017(9) 0.0042(10) O2 0.0216(12) 0.0357(15) 0.0339(13) -0.0136(12) -0.0010(10) 0.0036(11) N2 0.0203(14) 0.0138(14) 0.0176(13) -0.0031(11) 0.0027(10) -0.0011(11) N12A 0.0194(14) 0.0199(14) 0.0158(14) -0.0019(11) -0.0011(10) 0.0034(11) C1 0.0222(19) 0.0218(19) 0.0121(15) 0.0027(14) 0.0003(13) -0.0043(15) C3 0.0199(17) 0.024(2) 0.0155(16) -0.0005(15) 0.0050(13) 0.0034(15) C3A 0.0193(16) 0.0209(18) 0.0132(16) 0.0003(14) 0.0043(14) -0.0031(14) C3B 0.0208(16) 0.0171(17) 0.0185(16) -0.0019(14) 0.0024(13) -0.0018(14) C3C 0.0227(16) 0.0215(18) 0.0125(15) 0.0038(14) 0.0042(12) 0.0019(14) C4 0.0265(19) 0.0264(19) 0.0176(17) 0.0021(15) 0.0007(14) 0.0010(16) C5 0.030(2) 0.025(2) 0.0205(18) -0.0014(16) 0.0056(14) 0.0094(17) C6 0.027(2) 0.036(2) 0.0201(17) 0.0003(16) 0.0045(15) 0.0085(17) C7 0.0229(19) 0.034(2) 0.0184(17) 0.0037(16) 0.0005(14) -0.0030(17) C7A 0.0255(18) 0.0205(18) 0.0139(15) 0.0051(14) 0.0041(13) -0.0025(14) C8 0.0173(18) 0.027(2) 0.0211(18) -0.0017(16) -0.0014(14) -0.0050(16) C8A 0.0252(18) 0.0163(16) 0.0206(18) 0.0001(14) 0.0010(14) 0.0001(14) C9 0.0243(19) 0.0220(19) 0.025(2) -0.0006(15) -0.0027(15) 0.0027(15) C10 0.037(2) 0.0257(19) 0.0183(19) 0.0005(15) -0.0063(17) 0.0036(16) C11 0.036(2) 0.025(2) 0.0140(19) 0.0049(15) 0.0073(16) 0.0034(15) C12 0.027(2) 0.0157(17) 0.022(2) 0.0010(14) 0.0025(16) 0.0000(15) C12A 0.0263(18) 0.0151(17) 0.0153(17) 0.0001(13) -0.0022(14) 0.0008(14) C13 0.0192(17) 0.0183(18) 0.0196(17) 0.0007(14) -0.0004(13) -0.0013(14) C13A 0.0272(18) 0.0140(18) 0.0151(16) 0.0021(14) 0.0015(13) -0.0030(14) C14 0.0218(18) 0.025(2) 0.0150(16) -0.0027(14) -0.0008(13) 0.0021(15) C15 0.0223(18) 0.0214(19) 0.0240(18) 0.0037(15) -0.0002(14) -0.0007(16) C16 0.030(2) 0.0192(19) 0.0242(18) 0.0014(15) -0.0015(15) -0.0043(17) C17 0.031(2) 0.0227(19) 0.0254(18) -0.0078(15) -0.0006(14) 0.0097(16) C18 0.024(2) 0.037(2) 0.060(3) -0.024(2) 0.0083(17) -0.0022(18) C19 0.026(2) 0.027(2) 0.048(2) -0.0136(18) 0.0032(16) -0.0034(17) C20 0.0193(16) 0.0172(18) 0.0140(15) -0.0054(14) 0.0039(13) 0.0038(14) C21 0.0214(17) 0.0170(19) 0.0161(17) 0.0001(15) 0.0027(15) 0.0072(15) C22 0.0267(19) 0.0125(19) 0.0227(18) -0.0010(15) 0.0078(15) -0.0001(15) C23 0.0192(18) 0.023(2) 0.0247(18) -0.0106(16) 0.0061(15) -0.0029(16) C24 0.0201(17) 0.024(2) 0.0170(17) -0.0041(16) 0.0001(15) 0.0064(15) C25 0.0249(19) 0.012(2) 0.0175(17) 0.0019(16) 0.0051(14) 0.0031(16) _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 Cl1 C17 1.740(3) . ? O1 C1 1.204(3) . ? O2 C3 1.214(3) . ? N2 C1 1.410(4) . ? N2 C3 1.386(4) . ? N2 C20 1.431(4) . ? N12A C3B 1.475(4) . ? N12A C12A 1.434(4) . ? N12A C13 1.450(4) . ? C1 C13A 1.501(4) . ? C3 C3A 1.514(4) . ? C3A C3B 1.560(4) . ? C3A C13A 1.527(4) . ? C3A H3A 0.91(3) . ? C3B C3C 1.514(4) . ? C3B H3B 1.03(3) . ? C3C C4 1.399(4) . ? C3C C7A 1.405(4) . ? C4 C5 1.385(4) . ? C4 H4 1.01(3) . ? C5 C6 1.376(5) . ? C5 H5 0.96(3) . ? C6 C7 1.380(5) . ? C6 H6 0.99(3) . ? C7 C7A 1.399(4) . ? C7 H7 0.96(3) . ? C7A C8 1.506(4) . ? C8 C8A 1.510(4) . ? C8 H8A 0.99(3) . ? C8 H8B 0.97(3) . ? C8A C9 1.386(4) . ? C8A C12A 1.397(4) . ? C9 C10 1.389(5) . ? C9 H9 0.93(3) . ? C10 C11 1.375(5) . ? C10 H10 0.94(4) . ? C11 C12 1.382(4) . ? C11 H11 0.89(3) . ? C12 C12A 1.388(4) . ? C12 H12 0.94(3) . ? C13 C13A 1.552(4) . ? C13 C14 1.511(4) . ? C13 H13 1.05(3) . ? C13A H13A 0.96(3) . ? C14 C15 1.381(4) . ? C14 C19 1.383(4) . ? C15 C16 1.390(4) . ? C15 H15 0.98(3) . ? C16 C17 1.368(4) . ? C16 H16 0.91(3) . ? C17 C18 1.375(5) . ? C18 C19 1.371(5) . ? C18 H18 0.98(4) . ? C19 H19 1.00(4) . ? C20 C21 1.384(4) . ? C20 C25 1.377(4) . ? C21 C22 1.377(4) . ? C21 H21 0.87(3) . ? C22 C23 1.384(4) . ? C22 H22 0.88(3) . ? C23 C24 1.376(5) . ? C23 H23 0.89(3) . ? C24 C25 1.377(4) . ? C24 H24 0.90(3) . ? C25 H25 0.79(3) . ? 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 O1 C1 N2 124.0(3) . . ? O1 C1 C13A 128.1(3) . . ? O2 C3 N2 123.3(3) . . ? O2 C3 C3A 128.1(3) . . ? N2 C1 C13A 107.7(2) . . ? N2 C3 C3A 108.5(2) . . ? N12A C3B C3A 100.7(2) . . ? N12A C3B C3C 117.3(2) . . ? N12A C3B H3B 108.6(15) . . ? N12A C13 C13A 99.9(2) . . ? N12A C13 C14 115.0(2) . . ? N12A C13 H13 110.8(14) . . ? C1 N2 C20 121.6(2) . . ? C1 C13A C3A 106.0(2) . . ? C1 C13A C13 111.4(2) . . ? C1 C13A H13A 111.1(16) . . ? C3 N2 C1 112.8(2) . . ? C3 N2 C20 125.6(2) . . ? C3 C3A C3B 115.4(2) . . ? C3 C3A C13A 104.8(2) . . ? C3 C3A H3A 109.6(17) . . ? C3A C3B H3B 105.3(14) . . ? C3A C13A C13 104.8(2) . . ? C3A C13A H13A 113.0(16) . . ? C3B C3A H3A 108.0(17) . . ? C3C C3B C3A 115.7(2) . . ? C3C C3B H3B 108.4(14) . . ? C3C C4 H4 118.8(17) . . ? C3C C7A C8 122.5(3) . . ? C4 C3C C3B 116.0(3) . . ? C4 C3C C7A 119.1(3) . . ? C4 C5 H5 120.1(18) . . ? C5 C4 C3C 121.4(3) . . ? C5 C4 H4 119.7(17) . . ? C5 C6 C7 119.9(3) . . ? C5 C6 H6 120.4(18) . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.4(17) . . ? C6 C7 C7A 121.8(3) . . ? C6 C7 H7 120.8(18) . . ? C7 C6 H6 119.7(18) . . ? C7 C7A C3C 118.2(3) . . ? C7 C7A C8 119.2(3) . . ? C7A C3C C3B 124.9(3) . . ? C7A C7 H7 117.3(18) . . ? C7A C8 C8A 111.1(2) . . ? C7A C8 H8A 112.5(17) . . ? C7A C8 H8B 109.7(14) . . ? C8A C8 H8A 103.4(17) . . ? C8A C8 H8B 107.6(14) . . ? C8A C9 C10 120.2(3) . . ? C8A C9 H9 117.6(19) . . ? C8A C12A N12A 115.9(2) . . ? C9 C8A C8 122.9(3) . . ? C9 C8A C12A 119.2(3) . . ? C9 C10 H10 119(2) . . ? C10 C9 H9 122(2) . . ? C10 C11 C12 120.8(3) . . ? C10 C11 H11 122.5(19) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 121(2) . . ? C11 C12 C12A 119.3(3) . . ? C11 C12 H12 120.9(18) . . ? C12 C11 H11 116.7(19) . . ? C12 C12A N12A 123.5(3) . . ? C12 C12A C8A 120.5(3) . . ? C12A N12A C3B 117.4(2) . . ? C12A N12A C13 119.4(2) . . ? C12A C8A C8 117.9(3) . . ? C12A C12 H12 119.8(18) . . ? C13 N12A C3B 105.4(2) . . ? C13 C13A H13A 110.3(16) . . ? C13A C3A C3B 104.8(2) . . ? C13A C3A H3A 114.3(17) . . ? C13A C13 H13 106.1(14) . . ? C14 C13 C13A 114.3(2) . . ? C14 C13 H13 110.1(14) . . ? C14 C15 C16 119.6(3) . . ? C14 C15 H15 120.2(17) . . ? C14 C19 H19 117(2) . . ? C15 C14 C13 121.5(3) . . ? C15 C14 C19 119.0(3) . . ? C15 C16 H16 119.2(17) . . ? C16 C15 H15 120.2(17) . . ? C16 C17 Cl1 119.1(3) . . ? C16 C17 C18 120.7(3) . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 120.5(16) . . ? C17 C18 H18 122(2) . . ? C18 C17 Cl1 120.2(2) . . ? C18 C19 C14 121.5(3) . . ? C18 C19 H19 122(2) . . ? C19 C14 C13 119.5(3) . . ? C19 C18 C17 119.0(3) . . ? C19 C18 H18 119(2) . . ? C20 C21 H21 120(2) . . ? C20 C25 H25 120(2) . . ? C21 C20 N2 120.1(3) . . ? C21 C22 C23 120.1(3) . . ? C21 C22 H22 120.2(19) . . ? C22 C21 C20 119.3(3) . . ? C22 C21 H21 121(2) . . ? C22 C23 H23 121(2) . . ? C23 C22 H22 119.6(19) . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H24 121.1(18) . . ? C24 C23 C22 120.0(3) . . ? C24 C23 H23 119(2) . . ? C24 C25 C20 119.7(3) . . ? C24 C25 H25 120.8(19) . . ? C25 C20 N2 119.2(3) . . ? C25 C20 C21 120.7(3) . . ? C25 C24 H24 118.6(18) . . ? H8A C8 H8B 112(2) . . ? 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 Cl1 C17 C18 C19 -177.9(3) . . . . ? O1 C1 C13A C3A 178.6(3) . . . . ? O1 C1 C13A C13 65.2(4) . . . . ? O2 C3 C3A C3B -64.8(4) . . . . ? O2 C3 C3A C13A -179.5(3) . . . . ? N2 C1 C13A C3A 2.3(3) . . . . ? N2 C1 C13A C13 -111.2(3) . . . . ? N2 C3 C3A C3B 114.8(3) . . . . ? N2 C3 C3A C13A 0.1(3) . . . . ? N2 C20 C21 C22 177.9(2) . . . . ? N2 C20 C25 C24 -176.9(2) . . . . ? N12A C3B C3C C4 167.4(2) . . . . ? N12A C3B C3C C7A -12.8(4) . . . . ? N12A C13 C13A C1 146.6(2) . . . . ? N12A C13 C13A C3A 32.4(3) . . . . ? N12A C13 C14 C15 30.3(4) . . . . ? N12A C13 C14 C19 -149.5(3) . . . . ? C1 N2 C3 O2 -179.0(3) . . . . ? C1 N2 C3 C3A 1.4(3) . . . . ? C1 N2 C20 C21 -123.3(3) . . . . ? C1 N2 C20 C25 54.1(3) . . . . ? C3 N2 C1 O1 -178.9(3) . . . . ? C3 N2 C1 C13A -2.3(3) . . . . ? C3 N2 C20 C21 57.1(4) . . . . ? C3 N2 C20 C25 -125.5(3) . . . . ? C3 C3A C3B N12A -137.8(2) . . . . ? C3 C3A C3B C3C 94.8(3) . . . . ? C3 C3A C13A C1 -1.4(3) . . . . ? C3 C3A C13A C13 116.5(2) . . . . ? C3A C3B C3C C4 -74.0(3) . . . . ? C3A C3B C3C C7A 105.9(3) . . . . ? C3B N12A C12A C8A 77.2(3) . . . . ? C3B N12A C12A C12 -106.9(3) . . . . ? C3B N12A C13 C13A -49.5(3) . . . . ? C3B N12A C13 C14 -172.3(2) . . . . ? C3B C3A C13A C1 -123.4(2) . . . . ? C3B C3A C13A C13 -5.4(3) . . . . ? C3B C3C C4 C5 178.3(3) . . . . ? C3B C3C C7A C7 -178.1(3) . . . . ? C3B C3C C7A C8 5.8(4) . . . . ? C3C C4 C5 C6 0.5(4) . . . . ? C3C C7A C8 C8A 57.3(4) . . . . ? C4 C3C C7A C7 1.7(4) . . . . ? C4 C3C C7A C8 -174.4(3) . . . . ? C4 C5 C6 C7 0.5(4) . . . . ? C5 C6 C7 C7A -0.4(5) . . . . ? C6 C7 C7A C3C -0.7(4) . . . . ? C6 C7 C7A C8 175.5(3) . . . . ? C7 C7A C8 C8A -118.8(3) . . . . ? C7A C3C C4 C5 -1.6(4) . . . . ? C7A C8 C8A C9 109.5(3) . . . . ? C7A C8 C8A C12A -69.3(4) . . . . ? C8 C8A C9 C10 -179.4(3) . . . . ? C8 C8A C12A N12A -4.6(4) . . . . ? C8 C8A C12A C12 179.4(3) . . . . ? C8A C9 C10 C11 0.3(5) . . . . ? C9 C8A C12A N12A 176.6(3) . . . . ? C9 C8A C12A C12 0.6(4) . . . . ? C9 C10 C11 C12 0.3(5) . . . . ? C10 C11 C12 C12A -0.4(5) . . . . ? C11 C12 C12A N12A -175.7(3) . . . . ? C11 C12 C12A C8A 0.0(4) . . . . ? C12A N12A C3B C3A -178.2(2) . . . . ? C12A N12A C3B C3C -51.7(3) . . . . ? C12A N12A C13 C13A 175.9(2) . . . . ? C12A N12A C13 C14 53.0(3) . . . . ? C12A C8A C9 C10 -0.7(5) . . . . ? C13 N12A C3B C3A 46.1(3) . . . . ? C13 N12A C3B C3C 172.6(2) . . . . ? C13 N12A C12A C8A -153.4(3) . . . . ? C13 N12A C12A C12 22.5(4) . . . . ? C13 C14 C15 C16 -179.4(3) . . . . ? C13 C14 C19 C18 -178.3(3) . . . . ? C13A C3A C3B N12A -23.0(3) . . . . ? C13A C3A C3B C3C -150.5(3) . . . . ? C13A C13 C14 C15 -84.5(3) . . . . ? C13A C13 C14 C19 95.7(3) . . . . ? C14 C13 C13A C1 -90.1(3) . . . . ? C14 C13 C13A C3A 155.7(2) . . . . ? C14 C15 C16 C17 -1.8(5) . . . . ? C15 C14 C19 C18 1.9(5) . . . . ? C15 C16 C17 Cl1 -179.8(2) . . . . ? C15 C16 C17 C18 0.9(5) . . . . ? C16 C17 C18 C19 1.4(5) . . . . ? C17 C18 C19 C14 -2.8(6) . . . . ? C19 C14 C15 C16 0.4(4) . . . . ? C20 N2 C1 O1 1.5(4) . . . . ? C20 N2 C1 C13A 178.0(2) . . . . ? C20 N2 C3 O2 0.6(4) . . . . ? C20 N2 C3 C3A -179.0(2) . . . . ? C20 C21 C22 C23 -1.0(4) . . . . ? C21 C20 C25 C24 0.6(4) . . . . ? C21 C22 C23 C24 0.6(4) . . . . ? C22 C23 C24 C25 0.4(4) . . . . ? C23 C24 C25 C20 -1.0(4) . . . . ? C25 C20 C21 C22 0.4(4) . . . . ?