# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound_7_trifluoroatetate _database_code_depnum_ccdc_archive 'CCDC 871636' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Hydroxy-1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium trifluoroacetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N O, C2 F3 O2 ' _chemical_formula_sum 'C15 H14 F3 N O3' _chemical_formula_weight 313.27 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6837(3) _cell_length_b 12.8490(4) _cell_length_c 13.8588(5) _cell_angle_alpha 103.171(2) _cell_angle_beta 93.108(2) _cell_angle_gamma 106.795(2) _cell_volume 1429.42(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 61102 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9727 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type ; Bruker-Nonius APEX II CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5014 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5017 _reflns_number_gt 4621 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+2.7249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5017 _refine_ls_number_parameters 427 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.1630 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F2A F 0.4843(6) 0.2566(5) 0.8245(4) 0.0425(18) Uani 0.48 1 d PD A 1 F1B F 0.7245(5) 0.4028(6) 0.8102(7) 0.0305(16) Uiso 0.32 1 d PD A 2 F1A F 0.7253(4) 0.3549(6) 0.8166(4) 0.0472(16) Uani 0.48 1 d PD A 1 F2B F 0.5344(13) 0.2667(7) 0.8430(7) 0.0305(16) Uiso 0.32 1 d PD A 2 F3A F 0.5174(9) 0.4264(4) 0.8159(6) 0.042(2) Uani 0.48 1 d PD A 1 F3B F 0.4786(12) 0.4066(8) 0.8047(10) 0.0305(16) Uiso 0.32 1 d PD A 2 F4 F -0.1566(4) 0.2261(3) 0.14593(19) 0.0585(8) Uani 1 1 d . . . F5 F 0.0396(3) 0.1557(2) 0.13401(16) 0.0384(6) Uani 1 1 d . . . F6 F 0.0856(4) 0.3334(2) 0.1571(2) 0.0573(8) Uani 1 1 d . . . O1 O -0.0301(3) 0.1704(2) 0.50491(18) 0.0230(5) Uani 1 1 d . . . H1 H -0.0098 0.1829 0.4493 0.08(2) Uiso 1 1 calc R . . O1C O 0.4965(3) 0.3424(2) 0.61718(19) 0.0290(6) Uani 1 1 d . . . O3 O 0.5573(3) 0.1913(2) 0.6423(2) 0.0318(6) Uani 1 1 d . . . O21 O 0.5703(3) 0.3089(2) 0.43546(19) 0.0271(6) Uani 1 1 d . . . H21 H 0.5410 0.3189 0.4927 0.059(17) Uiso 1 1 calc R . . O22 O -0.0139(4) 0.3470(2) 0.3421(2) 0.0433(8) Uani 1 1 d . . . O23 O 0.0428(3) 0.1854(2) 0.32946(18) 0.0274(6) Uani 1 1 d . . . N1 N 0.0768(3) 0.3641(2) 0.6156(2) 0.0180(6) Uani 1 1 d . . . N2 N 0.4372(4) 0.1069(2) 0.3548(2) 0.0225(6) Uani 1 1 d . . . C1 C 0.1046(4) 0.3889(3) 0.7263(2) 0.0199(7) Uani 1 1 d . . . C2 C 0.1207(5) 0.4863(3) 0.7951(3) 0.0263(8) Uani 1 1 d . . . H2 H 0.1215 0.5531 0.7763 0.032 Uiso 1 1 calc R . . C3 C 0.1365(5) 0.4830(3) 0.8970(3) 0.0311(9) Uani 1 1 d . . . H3 H 0.1516 0.5505 0.9472 0.037 Uiso 1 1 calc R . . C4 C 0.1310(5) 0.3878(3) 0.9263(3) 0.0298(9) Uani 1 1 d . . . H4 H 0.1390 0.3896 0.9953 0.036 Uiso 1 1 calc R . . C5 C 0.1061(4) 0.1786(3) 0.8683(3) 0.0296(9) Uani 1 1 d . . . H5 H 0.1094 0.1684 0.9341 0.036 Uiso 1 1 calc R . . C6 C 0.0944(5) 0.0897(3) 0.7882(3) 0.0321(9) Uani 1 1 d . . . H6 H 0.0892 0.0189 0.8003 0.038 Uiso 1 1 calc R . . C7 C 0.0899(4) 0.0992(3) 0.6880(3) 0.0277(8) Uani 1 1 d . . . H7 H 0.0850 0.0372 0.6340 0.033 Uiso 1 1 calc R . . C8 C 0.0927(4) 0.2008(3) 0.6720(3) 0.0210(7) Uani 1 1 d . . . C9 C 0.1032(4) 0.2905(3) 0.7534(3) 0.0203(7) Uani 1 1 d . . . C10 C 0.1133(4) 0.2855(3) 0.8535(3) 0.0258(8) Uani 1 1 d . . . C11 C -0.0912(4) 0.3644(3) 0.5841(3) 0.0234(8) Uani 1 1 d . . . H11A H -0.1707 0.3061 0.6062 0.035 Uiso 1 1 calc R . . H11C H -0.1097 0.3491 0.5111 0.035 Uiso 1 1 calc R . . H11B H -0.1028 0.4380 0.6144 0.035 Uiso 1 1 calc R . . C12 C 0.1984(4) 0.4466(3) 0.5752(3) 0.0212(7) Uani 1 1 d . . . H12A H 0.1900 0.5221 0.6013 0.032 Uiso 1 1 calc R . . H12B H 0.1769 0.4258 0.5021 0.032 Uiso 1 1 calc R . . H12C H 0.3078 0.4460 0.5958 0.032 Uiso 1 1 calc R . . C13 C 0.0932(4) 0.2387(3) 0.5770(3) 0.0188(7) Uani 1 1 d . . . H13 H 0.1996 0.2439 0.5509 0.023 Uiso 1 1 calc R . . C14 C 0.5373(4) 0.2837(3) 0.6691(3) 0.0224(8) Uani 1 1 d . A . C15 C 0.5690(3) 0.3368(2) 0.7824(2) 0.0311(9) Uani 1 1 d D . . C21 C 0.3861(4) 0.0549(3) 0.2465(3) 0.0237(8) Uani 1 1 d . . . C22 C 0.3357(5) -0.0561(3) 0.1962(3) 0.0279(8) Uani 1 1 d . . . H22 H 0.3227 -0.1142 0.2299 0.033 Uiso 1 1 calc R . . C23 C 0.3041(5) -0.0797(3) 0.0907(3) 0.0328(9) Uani 1 1 d . . . H23 H 0.2638 -0.1560 0.0534 0.039 Uiso 1 1 calc R . . C24 C 0.3289(5) 0.0025(3) 0.0404(3) 0.0298(9) Uani 1 1 d . . . H24 H 0.3086 -0.0179 -0.0305 0.036 Uiso 1 1 calc R . . C25 C 0.4196(5) 0.2140(4) 0.0543(3) 0.0311(9) Uani 1 1 d . . . H25 H 0.4109 0.2053 -0.0159 0.037 Uiso 1 1 calc R . . C26 C 0.4661(5) 0.3197(4) 0.1177(3) 0.0342(9) Uani 1 1 d . . . H26 H 0.4898 0.3826 0.0896 0.041 Uiso 1 1 calc R . . C27 C 0.4802(5) 0.3394(3) 0.2229(3) 0.0295(9) Uani 1 1 d . . . H27 H 0.5079 0.4134 0.2650 0.035 Uiso 1 1 calc R . . C28 C 0.4523(4) 0.2476(3) 0.2617(3) 0.0239(8) Uani 1 1 d . . . C29 C 0.4073(4) 0.1403(3) 0.1971(3) 0.0231(8) Uani 1 1 d . . . C30 C 0.3846(4) 0.1177(3) 0.0925(3) 0.0275(8) Uani 1 1 d . . . C31 C 0.6022(4) 0.0993(3) 0.3823(3) 0.0290(8) Uani 1 1 d . . . H31A H 0.5987 0.0202 0.3657 0.044 Uiso 1 1 calc R . . H31B H 0.6356 0.1321 0.4542 0.044 Uiso 1 1 calc R . . H31C H 0.6802 0.1405 0.3450 0.044 Uiso 1 1 calc R . . C32 C 0.3205(5) 0.0535(3) 0.4185(3) 0.0268(8) Uani 1 1 d . . . H32A H 0.2124 0.0575 0.3994 0.040 Uiso 1 1 calc R . . H32B H 0.3569 0.0934 0.4889 0.040 Uiso 1 1 calc R . . H32C H 0.3159 -0.0254 0.4088 0.040 Uiso 1 1 calc R . . C33 C 0.4444(4) 0.2372(3) 0.3682(3) 0.0237(8) Uani 1 1 d . . . H33 H 0.3406 0.2473 0.3902 0.028 Uiso 1 1 calc R . . C34 C 0.0111(4) 0.2613(3) 0.2969(3) 0.0217(7) Uani 1 1 d . . . C35 C -0.0042(5) 0.2423(3) 0.1830(3) 0.0282(8) Uani 1 1 d . . . F2C F 0.6237(17) 0.2873(10) 0.8471(7) 0.050(2) Uiso 0.20 1 d PD A 3 F1C F 0.6933(11) 0.4316(6) 0.7898(10) 0.050(2) Uiso 0.20 1 d PD A 3 F3C F 0.4545(13) 0.3772(11) 0.8246(10) 0.050(2) Uiso 0.20 1 d PD A 3 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 F2A 0.051(4) 0.065(4) 0.025(3) 0.030(3) 0.009(3) 0.023(3) F1A 0.028(3) 0.068(4) 0.032(3) -0.003(3) -0.013(2) 0.010(3) F3A 0.078(6) 0.028(3) 0.021(3) -0.007(3) -0.004(4) 0.030(4) F4 0.0614(18) 0.076(2) 0.0355(14) -0.0144(14) -0.0198(13) 0.0445(16) F5 0.0658(17) 0.0380(13) 0.0243(12) 0.0088(10) 0.0126(11) 0.0338(12) F6 0.102(2) 0.0422(15) 0.0494(16) 0.0306(13) 0.0405(16) 0.0356(16) O1 0.0260(13) 0.0206(12) 0.0205(13) 0.0051(10) -0.0033(10) 0.0053(10) O1C 0.0324(15) 0.0350(15) 0.0256(13) 0.0104(12) 0.0007(11) 0.0179(12) O3 0.0372(16) 0.0275(15) 0.0333(15) 0.0085(12) 0.0034(12) 0.0134(12) O21 0.0278(14) 0.0269(14) 0.0224(14) 0.0081(11) -0.0041(11) 0.0021(11) O22 0.082(2) 0.0350(17) 0.0248(14) 0.0075(13) 0.0085(15) 0.0352(16) O23 0.0389(15) 0.0274(14) 0.0215(13) 0.0096(11) 0.0046(11) 0.0158(12) N1 0.0211(15) 0.0187(14) 0.0167(14) 0.0070(11) 0.0027(12) 0.0080(12) N2 0.0213(15) 0.0242(16) 0.0225(15) 0.0087(12) -0.0026(12) 0.0068(12) C1 0.0215(17) 0.0235(18) 0.0181(17) 0.0070(14) 0.0020(14) 0.0109(14) C2 0.032(2) 0.027(2) 0.0241(19) 0.0082(15) 0.0048(16) 0.0152(16) C3 0.037(2) 0.037(2) 0.0213(19) 0.0028(16) 0.0042(16) 0.0174(18) C4 0.030(2) 0.045(2) 0.0190(18) 0.0114(17) 0.0047(15) 0.0158(18) C5 0.0237(19) 0.039(2) 0.030(2) 0.0222(18) -0.0017(16) 0.0076(16) C6 0.034(2) 0.026(2) 0.039(2) 0.0192(18) -0.0039(18) 0.0082(17) C7 0.0260(19) 0.0237(19) 0.033(2) 0.0117(16) -0.0054(16) 0.0058(15) C8 0.0183(17) 0.0213(18) 0.0240(18) 0.0094(15) 0.0004(14) 0.0046(14) C9 0.0172(17) 0.0243(18) 0.0216(17) 0.0106(15) -0.0009(14) 0.0069(14) C10 0.0190(18) 0.036(2) 0.0245(19) 0.0150(16) -0.0001(15) 0.0061(16) C11 0.0203(18) 0.0277(19) 0.0275(19) 0.0114(15) 0.0019(15) 0.0122(15) C12 0.0244(18) 0.0180(17) 0.0219(17) 0.0080(14) 0.0027(14) 0.0055(14) C13 0.0176(17) 0.0182(17) 0.0238(17) 0.0065(14) 0.0004(14) 0.0099(13) C14 0.0151(17) 0.0264(19) 0.0275(19) 0.0105(16) 0.0031(14) 0.0063(14) C15 0.038(2) 0.037(2) 0.027(2) 0.0138(17) 0.0077(17) 0.0199(18) C21 0.0229(18) 0.0279(19) 0.0216(18) 0.0059(15) -0.0004(14) 0.0107(15) C22 0.028(2) 0.028(2) 0.029(2) 0.0058(16) 0.0005(16) 0.0118(16) C23 0.035(2) 0.033(2) 0.027(2) -0.0013(17) -0.0001(17) 0.0125(18) C24 0.028(2) 0.038(2) 0.0211(18) 0.0032(17) 0.0012(15) 0.0109(17) C25 0.026(2) 0.046(2) 0.0210(19) 0.0136(18) -0.0022(15) 0.0085(18) C26 0.033(2) 0.039(2) 0.031(2) 0.0196(18) -0.0049(17) 0.0039(18) C27 0.030(2) 0.029(2) 0.028(2) 0.0125(16) -0.0046(16) 0.0035(16) C28 0.0220(18) 0.0283(19) 0.0207(18) 0.0075(15) -0.0034(14) 0.0066(15) C29 0.0183(17) 0.0289(19) 0.0224(18) 0.0067(15) -0.0020(14) 0.0083(15) C30 0.0198(18) 0.040(2) 0.0241(19) 0.0088(17) 0.0008(15) 0.0119(16) C31 0.0219(19) 0.034(2) 0.033(2) 0.0129(17) -0.0034(16) 0.0091(16) C32 0.029(2) 0.0240(19) 0.0264(19) 0.0083(15) 0.0016(16) 0.0052(15) C33 0.0246(19) 0.0228(18) 0.0251(19) 0.0097(15) -0.0019(15) 0.0076(15) C34 0.0220(18) 0.0200(18) 0.0227(18) 0.0055(14) 0.0008(14) 0.0062(14) C35 0.038(2) 0.034(2) 0.0229(19) 0.0106(16) 0.0059(16) 0.0231(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 F2A C15 1.3519(11) . ? F1B C15 1.3503(11) . ? F1A C15 1.3478(10) . ? F2B C15 1.3502(11) . ? F3A C15 1.3484(11) . ? F3B C15 1.3500(11) . ? F4 C35 1.333(5) . ? F5 C35 1.331(4) . ? F6 C35 1.342(5) . ? O1 C13 1.362(4) . ? O1 H1 0.8400 . ? O1C C14 1.259(4) . ? O3 C14 1.226(4) . ? O21 C33 1.352(4) . ? O21 H21 0.8400 . ? O22 C34 1.221(4) . ? O23 C34 1.254(4) . ? N1 C1 1.486(4) . ? N1 C12 1.496(4) . ? N1 C11 1.501(4) . ? N1 C13 1.628(4) . ? N2 C21 1.482(4) . ? N2 C31 1.499(4) . ? N2 C32 1.500(5) . ? N2 C33 1.624(4) . ? C1 C2 1.355(5) . ? C1 C9 1.396(5) . ? C2 C3 1.424(5) . ? C2 H2 0.9500 . ? C3 C4 1.363(6) . ? C3 H3 0.9500 . ? C4 C10 1.425(6) . ? C4 H4 0.9500 . ? C5 C6 1.376(6) . ? C5 C10 1.419(5) . ? C5 H5 0.9500 . ? C6 C7 1.421(5) . ? C6 H6 0.9500 . ? C7 C8 1.366(5) . ? C7 H7 0.9500 . ? C8 C9 1.395(5) . ? C8 C13 1.504(5) . ? C9 C10 1.402(5) . ? C11 H11A 0.9800 . ? C11 H11C 0.9800 . ? C11 H11B 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13 1.0000 . ? C14 C15 1.538(4) . ? C15 F2C 1.3501(11) . ? C15 F3C 1.3503(11) . ? C15 F1C 1.3523(11) . ? C21 C22 1.366(5) . ? C21 C29 1.395(5) . ? C22 C23 1.418(5) . ? C22 H22 0.9500 . ? C23 C24 1.367(6) . ? C23 H23 0.9500 . ? C24 C30 1.416(6) . ? C24 H24 0.9500 . ? C25 C26 1.371(6) . ? C25 C30 1.415(6) . ? C25 H25 0.9500 . ? C26 C27 1.413(5) . ? C26 H26 0.9500 . ? C27 C28 1.371(5) . ? C27 H27 0.9500 . ? C28 C29 1.393(5) . ? C28 C33 1.515(5) . ? C29 C30 1.404(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33 1.0000 . ? C34 C35 1.534(5) . ? 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 C13 O1 H1 109.5 . . ? C33 O21 H21 109.5 . . ? C1 N1 C12 112.4(3) . . ? C1 N1 C11 109.1(3) . . ? C12 N1 C11 109.8(3) . . ? C1 N1 C13 104.4(2) . . ? C12 N1 C13 110.5(2) . . ? C11 N1 C13 110.5(2) . . ? C21 N2 C31 109.1(3) . . ? C21 N2 C32 112.8(3) . . ? C31 N2 C32 109.8(3) . . ? C21 N2 C33 104.2(2) . . ? C31 N2 C33 110.5(3) . . ? C32 N2 C33 110.3(3) . . ? C2 C1 C9 122.1(3) . . ? C2 C1 N1 128.9(3) . . ? C9 C1 N1 108.9(3) . . ? C1 C2 C3 116.3(3) . . ? C1 C2 H2 121.9 . . ? C3 C2 H2 121.9 . . ? C4 C3 C2 123.3(4) . . ? C4 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? C3 C4 C10 120.1(3) . . ? C3 C4 H4 119.9 . . ? C10 C4 H4 119.9 . . ? C6 C5 C10 120.5(3) . . ? C6 C5 H5 119.8 . . ? C10 C5 H5 119.8 . . ? C5 C6 C7 122.7(3) . . ? C5 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C8 C7 C6 117.7(4) . . ? C8 C7 H7 121.2 . . ? C6 C7 H7 121.2 . . ? C7 C8 C9 119.4(3) . . ? C7 C8 C13 130.7(3) . . ? C9 C8 C13 109.8(3) . . ? C8 C9 C1 113.3(3) . . ? C8 C9 C10 124.6(3) . . ? C1 C9 C10 122.1(3) . . ? C9 C10 C5 115.1(3) . . ? C9 C10 C4 116.1(3) . . ? C5 C10 C4 128.8(3) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 C8 113.1(3) . . ? O1 C13 N1 112.2(2) . . ? C8 C13 N1 102.1(3) . . ? O1 C13 H13 109.7 . . ? C8 C13 H13 109.7 . . ? N1 C13 H13 109.7 . . ? O3 C14 O1C 129.5(3) . . ? O3 C14 C15 115.5(3) . . ? O1C C14 C15 115.0(3) . . ? F1A C15 F3A 113.1(4) . . ? F1A C15 F3B 128.2(6) . . ? F3A C15 F3B 15.3(7) . . ? F1A C15 F2C 53.5(6) . . ? F3A C15 F2C 120.6(7) . . ? F3B C15 F2C 124.9(8) . . ? F1A C15 F2B 85.2(5) . . ? F3A C15 F2B 110.1(8) . . ? F3B C15 F2B 106.1(6) . . ? F2C C15 F2B 31.7(6) . . ? F1A C15 F1B 27.6(4) . . ? F3A C15 F1B 90.2(5) . . ? F3B C15 F1B 105.4(6) . . ? F2C C15 F1B 77.8(6) . . ? F2B C15 F1B 107.9(5) . . ? F1A C15 F3C 130.9(7) . . ? F3A C15 F3C 32.0(6) . . ? F3B C15 F3C 22.2(8) . . ? F2C C15 F3C 106.5(6) . . ? F2B C15 F3C 84.2(7) . . ? F1B C15 F3C 116.7(8) . . ? F1A C15 F2A 104.4(4) . . ? F3A C15 F2A 105.4(4) . . ? F3B C15 F2A 96.9(7) . . ? F2C C15 F2A 50.9(7) . . ? F2B C15 F2A 19.6(5) . . ? F1B C15 F2A 127.5(5) . . ? F3C C15 F2A 74.9(6) . . ? F1A C15 F1C 53.9(6) . . ? F3A C15 F1C 71.4(6) . . ? F3B C15 F1C 85.2(8) . . ? F2C C15 F1C 103.6(6) . . ? F2B C15 F1C 131.5(7) . . ? F1B C15 F1C 26.6(5) . . ? F3C C15 F1C 102.6(6) . . ? F2A C15 F1C 149.6(7) . . ? F1A C15 C14 110.0(3) . . ? F3A C15 C14 116.8(4) . . ? F3B C15 C14 108.5(6) . . ? F2C C15 C14 121.8(6) . . ? F2B C15 C14 117.4(5) . . ? F1B C15 C14 110.8(5) . . ? F3C C15 C14 117.4(7) . . ? F2A C15 C14 105.9(3) . . ? F1C C15 C14 102.0(6) . . ? C22 C21 C29 122.1(3) . . ? C22 C21 N2 129.2(3) . . ? C29 C21 N2 108.5(3) . . ? C21 C22 C23 116.1(4) . . ? C21 C22 H22 122.0 . . ? C23 C22 H22 122.0 . . ? C24 C23 C22 122.9(4) . . ? C24 C23 H23 118.5 . . ? C22 C23 H23 118.5 . . ? C23 C24 C30 121.0(3) . . ? C23 C24 H24 119.5 . . ? C30 C24 H24 119.5 . . ? C26 C25 C30 120.6(3) . . ? C26 C25 H25 119.7 . . ? C30 C25 H25 119.7 . . ? C25 C26 C27 123.0(4) . . ? C25 C26 H26 118.5 . . ? C27 C26 H26 118.5 . . ? C28 C27 C26 117.4(4) . . ? C28 C27 H27 121.3 . . ? C26 C27 H27 121.3 . . ? C27 C28 C29 119.4(3) . . ? C27 C28 C33 131.3(3) . . ? C29 C28 C33 109.0(3) . . ? C28 C29 C21 113.4(3) . . ? C28 C29 C30 124.6(3) . . ? C21 C29 C30 122.0(3) . . ? C29 C30 C25 114.9(4) . . ? C29 C30 C24 115.8(3) . . ? C25 C30 C24 129.3(4) . . ? N2 C31 H31A 109.5 . . ? N2 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N2 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N2 C32 H32A 109.5 . . ? N2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O21 C33 C28 115.2(3) . . ? O21 C33 N2 112.2(3) . . ? C28 C33 N2 101.2(3) . . ? O21 C33 H33 109.3 . . ? C28 C33 H33 109.3 . . ? N2 C33 H33 109.3 . . ? O22 C34 O23 129.7(3) . . ? O22 C34 C35 114.8(3) . . ? O23 C34 C35 115.5(3) . . ? F5 C35 F4 107.3(3) . . ? F5 C35 F6 106.7(3) . . ? F4 C35 F6 105.6(3) . . ? F5 C35 C34 115.1(3) . . ? F4 C35 C34 110.5(3) . . ? F6 C35 C34 111.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O23 0.84 1.75 2.581(4) 169.0 . O21 H21 O1C 0.84 1.77 2.603(4) 175.2 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.929 _refine_diff_density_min -0.827 _refine_diff_density_rms 0.070 _vrf_DIFMX01_twin5u ; PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 0.929 RESPONSE: One of the CF3 groups is disordered. It is modelled as three different orientations, but the highest residual electron density peaks are associated with this group. It can be noted that the biggest hole is similar in size to the biggest peak in the final electron density map. ; data_compound_7Cl _database_code_depnum_ccdc_archive 'CCDC 871637' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Hydroxy-1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N O, Cl' _chemical_formula_sum 'C13 H14 Cl N O' _chemical_formula_weight 235.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9646(4) _cell_length_b 11.9986(5) _cell_length_c 19.3145(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2309.27(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2868 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 29.09 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.074 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_T_min 0.98426 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 15.98 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7569 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 29.14 _reflns_number_total 2708 _reflns_number_gt 2301 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.7501P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2708 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.17574(5) 0.96972(4) 0.22215(2) 0.02765(14) Uani 1 1 d . . . O1 O 0.02398(13) 0.91445(10) 0.11623(6) 0.0272(3) Uani 1 1 d . . . H1 H -0.0225 0.9374 0.1496 0.033 Uiso 1 1 calc R . . N1 N 0.04645(13) 0.71213(11) 0.13969(7) 0.0177(3) Uani 1 1 d . . . C1 C 0.09674(16) 0.63381(14) 0.08645(8) 0.0176(3) Uani 1 1 d . . . C2 C 0.15422(17) 0.53254(14) 0.09548(9) 0.0225(4) Uani 1 1 d . . . H2 H 0.1647 0.5001 0.1400 0.027 Uiso 1 1 calc R . . C3 C 0.19787(18) 0.47776(15) 0.03419(9) 0.0243(4) Uani 1 1 d . . . H3 H 0.2372 0.4059 0.0383 0.029 Uiso 1 1 calc R . . C4 C 0.18606(17) 0.52336(14) -0.03047(9) 0.0233(4) Uani 1 1 d . . . H4 H 0.2195 0.4841 -0.0696 0.028 Uiso 1 1 calc R . . C5 C 0.10156(18) 0.68782(15) -0.10193(9) 0.0256(4) Uani 1 1 d . . . H5 H 0.1287 0.6566 -0.1449 0.031 Uiso 1 1 calc R . . C6 C 0.04003(19) 0.79047(16) -0.10014(9) 0.0288(4) Uani 1 1 d . . . H6 H 0.0271 0.8294 -0.1425 0.035 Uiso 1 1 calc R . . C7 C -0.00467(19) 0.84044(16) -0.03816(9) 0.0258(4) Uani 1 1 d . . . H7 H -0.0479 0.9110 -0.0386 0.031 Uiso 1 1 calc R . . C8 C 0.01602(17) 0.78430(14) 0.02242(9) 0.0201(4) Uani 1 1 d . . . C9 C 0.07966(16) 0.68101(14) 0.02137(8) 0.0168(3) Uani 1 1 d . . . C10 C 0.12428(17) 0.62883(14) -0.03950(8) 0.0203(4) Uani 1 1 d . . . C13 C -0.02206(17) 0.81376(14) 0.09546(8) 0.0206(4) Uani 1 1 d . . . H13 H -0.1219 0.8110 0.1006 0.025 Uiso 1 1 calc R . . C12 C -0.05761(19) 0.66076(15) 0.18566(9) 0.0266(4) Uani 1 1 d . . . H12A H -0.1313 0.6317 0.1573 0.040 Uiso 1 1 calc R . . H12C H -0.0924 0.7173 0.2176 0.040 Uiso 1 1 calc R . . H12B H -0.0173 0.5997 0.2122 0.040 Uiso 1 1 calc R . . C11 C 0.15996(19) 0.75415(15) 0.18323(9) 0.0277(4) Uani 1 1 d . . . H11B H 0.1983 0.6923 0.2098 0.042 Uiso 1 1 calc R . . H11C H 0.1267 0.8113 0.2151 0.042 Uiso 1 1 calc R . . H11A H 0.2292 0.7864 0.1533 0.042 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 Cl1 0.0342(3) 0.0288(3) 0.0200(2) -0.00639(17) 0.00202(18) -0.00224(19) O1 0.0393(8) 0.0194(7) 0.0229(6) -0.0024(5) 0.0065(6) 0.0010(6) N1 0.0201(7) 0.0184(7) 0.0146(7) 0.0007(5) 0.0008(6) -0.0014(6) C1 0.0171(8) 0.0206(9) 0.0152(8) -0.0014(6) -0.0001(6) -0.0025(7) C2 0.0233(8) 0.0228(9) 0.0213(8) 0.0026(7) -0.0024(7) 0.0011(7) C3 0.0232(9) 0.0211(9) 0.0286(9) -0.0023(7) -0.0010(7) 0.0022(7) C4 0.0222(9) 0.0251(10) 0.0227(9) -0.0073(7) 0.0006(7) -0.0006(7) C5 0.0273(10) 0.0346(11) 0.0150(8) -0.0026(7) 0.0014(7) -0.0029(8) C6 0.0339(10) 0.0341(11) 0.0184(9) 0.0066(7) -0.0022(8) 0.0007(8) C7 0.0308(10) 0.0234(10) 0.0232(9) 0.0045(7) -0.0015(8) 0.0028(8) C8 0.0203(8) 0.0223(9) 0.0178(8) -0.0005(7) 0.0013(7) -0.0007(7) C9 0.0152(7) 0.0198(8) 0.0153(7) -0.0003(6) -0.0008(6) -0.0035(6) C10 0.0177(8) 0.0254(9) 0.0178(8) -0.0014(7) 0.0010(7) -0.0042(7) C13 0.0226(9) 0.0195(9) 0.0196(8) 0.0034(7) 0.0001(7) 0.0028(7) C12 0.0316(10) 0.0273(10) 0.0209(9) 0.0029(7) 0.0100(8) -0.0010(8) C11 0.0311(10) 0.0277(10) 0.0242(9) -0.0029(8) -0.0101(8) -0.0040(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 C13 1.353(2) . ? O1 H1 0.8400 . ? N1 C1 1.480(2) . ? N1 C11 1.497(2) . ? N1 C12 1.498(2) . ? N1 C13 1.638(2) . ? C1 C2 1.355(2) . ? C1 C9 1.389(2) . ? C2 C3 1.422(2) . ? C2 H2 0.9500 . ? C3 C4 1.368(2) . ? C3 H3 0.9500 . ? C4 C10 1.418(2) . ? C4 H4 0.9500 . ? C5 C6 1.376(3) . ? C5 C10 1.416(2) . ? C5 H5 0.9500 . ? C6 C7 1.411(2) . ? C6 H6 0.9500 . ? C7 C8 1.366(2) . ? C7 H7 0.9500 . ? C8 C9 1.392(2) . ? C8 C13 1.503(2) . ? C9 C10 1.404(2) . ? C13 H13 1.0000 . ? C12 H12A 0.9800 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C11 H11A 0.9800 . ? 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 C13 O1 H1 109.5 . . ? C1 N1 C11 110.38(13) . . ? C1 N1 C12 112.63(13) . . ? C11 N1 C12 109.19(13) . . ? C1 N1 C13 104.56(11) . . ? C11 N1 C13 110.93(13) . . ? C12 N1 C13 109.09(13) . . ? C2 C1 C9 122.28(15) . . ? C2 C1 N1 128.54(15) . . ? C9 C1 N1 109.16(14) . . ? C1 C2 C3 115.89(16) . . ? C1 C2 H2 122.1 . . ? C3 C2 H2 122.1 . . ? C4 C3 C2 123.27(16) . . ? C4 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? C3 C4 C10 120.42(16) . . ? C3 C4 H4 119.8 . . ? C10 C4 H4 119.8 . . ? C6 C5 C10 119.81(16) . . ? C6 C5 H5 120.1 . . ? C10 C5 H5 120.1 . . ? C5 C6 C7 122.83(17) . . ? C5 C6 H6 118.6 . . ? C7 C6 H6 118.6 . . ? C8 C7 C6 118.01(17) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C7 C8 C9 119.69(16) . . ? C7 C8 C13 130.55(16) . . ? C9 C8 C13 109.75(14) . . ? C1 C9 C8 113.93(14) . . ? C1 C9 C10 122.48(16) . . ? C8 C9 C10 123.59(15) . . ? C9 C10 C5 116.06(16) . . ? C9 C10 C4 115.62(15) . . ? C5 C10 C4 128.32(16) . . ? O1 C13 C8 113.75(14) . . ? O1 C13 N1 111.63(13) . . ? C8 C13 N1 102.08(13) . . ? O1 C13 H13 109.7 . . ? C8 C13 H13 109.7 . . ? N1 C13 H13 109.7 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? N1 C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 Cl1 0.84 2.11 2.9302(13) 165.8 . _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.281 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.049 data_compound_8 _database_code_depnum_ccdc_archive 'CCDC 871638' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium-2-yl)-2,5 -dioxocyclopentan-1-ide monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O2, H2 O ' _chemical_formula_sum 'C18 H19 N O3' _chemical_formula_weight 297.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.5849(7) _cell_length_b 9.1076(3) _cell_length_c 19.5453(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.680(2) _cell_angle_gamma 90.00 _cell_volume 3052.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 33471 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31012 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.52 _reflns_number_total 6982 _reflns_number_gt 5042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.6179P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6982 _refine_ls_number_parameters 413 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.80658(7) 0.49151(12) 0.29845(7) 0.0258(3) Uani 1 1 d . . . O2A O 0.85725(7) 0.88026(13) 0.16339(7) 0.0280(3) Uani 1 1 d . . . N1A N 0.99693(7) 0.70211(14) 0.34459(7) 0.0190(3) Uani 1 1 d . . . C1A C 1.04297(9) 0.81723(17) 0.39727(9) 0.0200(3) Uani 1 1 d . . . C2A C 1.11862(10) 0.81477(19) 0.44637(10) 0.0278(4) Uani 1 1 d . . . H2A H 1.1507 0.7305 0.4529 0.033 Uiso 1 1 calc R . . C3A C 1.14641(10) 0.9465(2) 0.48726(11) 0.0321(4) Uani 1 1 d . . . H3A H 1.1983 0.9480 0.5233 0.038 Uiso 1 1 calc R . . C4A C 1.10228(10) 1.0713(2) 0.47746(10) 0.0282(4) Uani 1 1 d . . . H4A H 1.1244 1.1571 0.5052 0.034 Uiso 1 1 calc R . . C5A C 0.96886(10) 1.18875(18) 0.40964(10) 0.0263(4) Uani 1 1 d . . . H5A H 0.9839 1.2808 0.4338 0.032 Uiso 1 1 calc R . . C6A C 0.89417(10) 1.16879(18) 0.35899(10) 0.0290(4) Uani 1 1 d . . . H6A H 0.8590 1.2493 0.3473 0.035 Uiso 1 1 calc R . . C7A C 0.86747(10) 1.03144(18) 0.32325(10) 0.0245(4) Uani 1 1 d . . . H7A H 0.8150 1.0198 0.2893 0.029 Uiso 1 1 calc R . . C8A C 0.91856(9) 0.91748(17) 0.33876(9) 0.0186(3) Uani 1 1 d . . . C9A C 0.99604(9) 0.94108(17) 0.38785(9) 0.0184(3) Uani 1 1 d . . . C10A C 1.02373(9) 1.07276(17) 0.42607(9) 0.0223(4) Uani 1 1 d . . . C11A C 1.01833(10) 0.70145(19) 0.27787(10) 0.0265(4) Uani 1 1 d . . . H11C H 1.0073 0.7981 0.2540 0.040 Uiso 1 1 calc R . . H11A H 0.9876 0.6265 0.2427 0.040 Uiso 1 1 calc R . . H11B H 1.0740 0.6793 0.2934 0.040 Uiso 1 1 calc R . . C12A C 1.00736(10) 0.55187(17) 0.37793(10) 0.0241(4) Uani 1 1 d . . . H12B H 1.0598 0.5158 0.3864 0.036 Uiso 1 1 calc R . . H12C H 0.9684 0.4853 0.3440 0.036 Uiso 1 1 calc R . . H12A H 1.0007 0.5561 0.4253 0.036 Uiso 1 1 calc R . . C13A C 0.90807(8) 0.75535(17) 0.32247(9) 0.0179(3) Uani 1 1 d . . . H13A H 0.8910 0.7130 0.3610 0.021 Uiso 1 1 calc R . . C14A C 0.85248(9) 0.69878(17) 0.25068(9) 0.0183(3) Uani 1 1 d . . . C15A C 0.80617(9) 0.57267(17) 0.24636(9) 0.0200(3) Uani 1 1 d . . . C16A C 0.75186(10) 0.54598(18) 0.16631(9) 0.0250(4) Uani 1 1 d . . . H16A H 0.6969 0.5422 0.1615 0.030 Uiso 1 1 calc R . . H16B H 0.7648 0.4525 0.1478 0.030 Uiso 1 1 calc R . . C17A C 0.76520(9) 0.67666(18) 0.12332(9) 0.0238(4) Uani 1 1 d . . . H17B H 0.7808 0.6426 0.0830 0.029 Uiso 1 1 calc R . . H17A H 0.7172 0.7363 0.1015 0.029 Uiso 1 1 calc R . . C18A C 0.83049(9) 0.76574(18) 0.18034(9) 0.0211(4) Uani 1 1 d . . . O1B O 0.61022(6) 0.61362(12) 0.49523(7) 0.0266(3) Uani 1 1 d . . . O2B O 0.45895(6) 1.00397(12) 0.35215(6) 0.0234(3) Uani 1 1 d . . . N1B N 0.59770(7) 0.76512(14) 0.30762(7) 0.0177(3) Uani 1 1 d . . . C1B C 0.62438(8) 0.87429(17) 0.26649(9) 0.0179(3) Uani 1 1 d . . . C2B C 0.62699(9) 0.86209(19) 0.19796(9) 0.0252(4) Uani 1 1 d . . . H2B H 0.6126 0.7740 0.1699 0.030 Uiso 1 1 calc R . . C3B C 0.65240(10) 0.9883(2) 0.17066(10) 0.0288(4) Uani 1 1 d . . . H3B H 0.6551 0.9837 0.1231 0.035 Uiso 1 1 calc R . . C4B C 0.67318(9) 1.11660(19) 0.21038(10) 0.0257(4) Uani 1 1 d . . . H4B H 0.6902 1.1978 0.1900 0.031 Uiso 1 1 calc R . . C5B C 0.68799(9) 1.25350(18) 0.32933(10) 0.0234(4) Uani 1 1 d . . . H5B H 0.7069 1.3409 0.3156 0.028 Uiso 1 1 calc R . . C6B C 0.67830(9) 1.24662(18) 0.39540(10) 0.0243(4) Uani 1 1 d . . . H6B H 0.6897 1.3312 0.4262 0.029 Uiso 1 1 calc R . . C7B C 0.65177(9) 1.11773(17) 0.41955(9) 0.0208(3) Uani 1 1 d . . . H7B H 0.6451 1.1166 0.4653 0.025 Uiso 1 1 calc R . . C8B C 0.63610(8) 0.99535(16) 0.37557(9) 0.0168(3) Uani 1 1 d . . . C9B C 0.64440(8) 1.00394(16) 0.30748(9) 0.0164(3) Uani 1 1 d . . . C10B C 0.66966(8) 1.12976(17) 0.28151(9) 0.0200(3) Uani 1 1 d . . . C11B C 0.51244(9) 0.73564(19) 0.26667(9) 0.0249(4) Uani 1 1 d . . . H11F H 0.4833 0.8279 0.2599 0.037 Uiso 1 1 calc R . . H11D H 0.4944 0.6667 0.2952 0.037 Uiso 1 1 calc R . . H11E H 0.5038 0.6930 0.2181 0.037 Uiso 1 1 calc R . . C12B C 0.64211(10) 0.62345(17) 0.31856(10) 0.0259(4) Uani 1 1 d . . . H12D H 0.6298 0.5756 0.2705 0.039 Uiso 1 1 calc R . . H12E H 0.6273 0.5587 0.3510 0.039 Uiso 1 1 calc R . . H12F H 0.6982 0.6436 0.3413 0.039 Uiso 1 1 calc R . . C13B C 0.61480(8) 0.84051(16) 0.38778(8) 0.0163(3) Uani 1 1 d . . . H13B H 0.6631 0.7937 0.4241 0.020 Uiso 1 1 calc R . . C14B C 0.55291(8) 0.81854(16) 0.41621(8) 0.0169(3) Uani 1 1 d . . . C15B C 0.55843(9) 0.70956(17) 0.46958(9) 0.0193(3) Uani 1 1 d . . . C16B C 0.49031(9) 0.72575(19) 0.49394(9) 0.0241(4) Uani 1 1 d . . . H16C H 0.5091 0.7499 0.5474 0.029 Uiso 1 1 calc R . . H16D H 0.4595 0.6339 0.4848 0.029 Uiso 1 1 calc R . . C17B C 0.44128(9) 0.85149(18) 0.44686(9) 0.0205(3) Uani 1 1 d . . . H17D H 0.3882 0.8168 0.4157 0.025 Uiso 1 1 calc R . . H17C H 0.4369 0.9323 0.4789 0.025 Uiso 1 1 calc R . . C18B C 0.48399(9) 0.90310(16) 0.39862(8) 0.0173(3) Uani 1 1 d . . . O3 O 0.13581(9) 0.06188(18) 0.04961(8) 0.0476(4) Uani 1 1 d D . . H31 H 0.1704(9) 0.051(3) 0.0315(11) 0.071 Uiso 1 1 d D . . H32 H 0.1536(12) 0.024(3) 0.0927(6) 0.071 Uiso 1 1 d D . . O4 O 0.23615(7) 0.48726(16) 0.47400(7) 0.0374(3) Uani 1 1 d D . . H41 H 0.2071(8) 0.451(2) 0.4323(6) 0.056 Uiso 1 1 d D . . H42 H 0.2818(4) 0.453(2) 0.4844(10) 0.056 Uiso 1 1 d 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 O1A 0.0272(6) 0.0205(6) 0.0299(7) 0.0054(5) 0.0111(5) -0.0026(5) O2A 0.0268(6) 0.0292(7) 0.0263(7) 0.0071(5) 0.0085(5) -0.0064(5) N1A 0.0175(6) 0.0165(7) 0.0233(7) 0.0030(5) 0.0082(6) 0.0022(5) C1A 0.0187(7) 0.0191(8) 0.0235(9) 0.0022(7) 0.0097(7) -0.0013(6) C2A 0.0202(8) 0.0268(9) 0.0338(10) 0.0055(8) 0.0076(7) 0.0031(7) C3A 0.0187(8) 0.0350(10) 0.0342(11) 0.0035(8) 0.0010(7) -0.0048(8) C4A 0.0285(9) 0.0270(9) 0.0267(10) -0.0007(7) 0.0079(8) -0.0105(7) C5A 0.0361(10) 0.0156(8) 0.0311(10) -0.0004(7) 0.0173(8) -0.0022(7) C6A 0.0344(10) 0.0185(9) 0.0368(11) 0.0046(8) 0.0169(8) 0.0080(7) C7A 0.0201(8) 0.0244(9) 0.0278(9) 0.0038(7) 0.0078(7) 0.0046(7) C8A 0.0189(7) 0.0184(8) 0.0199(8) 0.0026(6) 0.0090(6) 0.0002(6) C9A 0.0195(8) 0.0165(8) 0.0204(8) 0.0045(6) 0.0090(7) -0.0001(6) C10A 0.0252(8) 0.0198(8) 0.0231(9) 0.0028(7) 0.0107(7) -0.0038(7) C11A 0.0250(8) 0.0303(10) 0.0289(10) 0.0010(8) 0.0156(8) 0.0038(7) C12A 0.0253(8) 0.0159(8) 0.0306(10) 0.0054(7) 0.0104(7) 0.0045(7) C13A 0.0143(7) 0.0191(8) 0.0210(8) 0.0033(6) 0.0077(6) 0.0027(6) C14A 0.0169(7) 0.0175(8) 0.0204(8) 0.0012(6) 0.0072(6) -0.0002(6) C15A 0.0181(7) 0.0180(8) 0.0251(9) 0.0017(7) 0.0096(7) 0.0037(6) C16A 0.0242(8) 0.0202(8) 0.0286(10) -0.0027(7) 0.0080(7) -0.0030(7) C17A 0.0234(8) 0.0265(9) 0.0205(9) -0.0016(7) 0.0076(7) -0.0012(7) C18A 0.0182(8) 0.0226(9) 0.0229(9) -0.0001(7) 0.0084(7) 0.0000(7) O1B 0.0223(6) 0.0236(6) 0.0306(7) 0.0102(5) 0.0065(5) 0.0038(5) O2B 0.0247(6) 0.0222(6) 0.0242(7) 0.0056(5) 0.0103(5) 0.0050(5) N1B 0.0171(6) 0.0153(6) 0.0203(7) -0.0033(5) 0.0068(5) 0.0002(5) C1B 0.0153(7) 0.0195(8) 0.0173(8) 0.0005(6) 0.0044(6) 0.0020(6) C2B 0.0226(8) 0.0316(10) 0.0187(9) -0.0021(7) 0.0048(7) 0.0059(7) C3B 0.0273(9) 0.0413(11) 0.0190(9) 0.0065(8) 0.0102(7) 0.0082(8) C4B 0.0220(8) 0.0309(10) 0.0254(9) 0.0119(8) 0.0105(7) 0.0056(7) C5B 0.0160(7) 0.0177(8) 0.0362(10) 0.0044(7) 0.0098(7) 0.0012(6) C6B 0.0219(8) 0.0163(8) 0.0343(10) -0.0046(7) 0.0106(7) -0.0013(7) C7B 0.0210(8) 0.0200(8) 0.0242(9) -0.0042(7) 0.0118(7) -0.0022(6) C8B 0.0124(7) 0.0181(8) 0.0193(8) 0.0003(6) 0.0057(6) 0.0008(6) C9B 0.0125(7) 0.0179(8) 0.0180(8) 0.0014(6) 0.0051(6) 0.0041(6) C10B 0.0134(7) 0.0213(8) 0.0259(9) 0.0058(7) 0.0083(6) 0.0043(6) C11B 0.0167(8) 0.0302(9) 0.0250(9) -0.0115(7) 0.0051(7) -0.0049(7) C12B 0.0318(9) 0.0171(8) 0.0294(10) -0.0010(7) 0.0126(8) 0.0066(7) C13B 0.0150(7) 0.0171(8) 0.0157(8) -0.0024(6) 0.0046(6) -0.0001(6) C14B 0.0171(7) 0.0152(8) 0.0184(8) 0.0001(6) 0.0070(6) -0.0017(6) C15B 0.0170(7) 0.0203(8) 0.0171(8) -0.0003(6) 0.0027(6) -0.0033(6) C16B 0.0223(8) 0.0293(9) 0.0215(9) 0.0042(7) 0.0091(7) -0.0036(7) C17B 0.0186(7) 0.0230(8) 0.0209(9) -0.0024(7) 0.0088(7) -0.0029(6) C18B 0.0188(7) 0.0169(8) 0.0160(8) -0.0026(6) 0.0064(6) -0.0022(6) O3 0.0503(9) 0.0611(10) 0.0334(8) 0.0039(7) 0.0182(7) 0.0251(8) O4 0.0274(7) 0.0493(8) 0.0327(8) -0.0197(6) 0.0082(6) 0.0024(6) _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 O1A C15A 1.256(2) . ? O2A C18A 1.2539(19) . ? N1A C1A 1.487(2) . ? N1A C12A 1.496(2) . ? N1A C11A 1.503(2) . ? N1A C13A 1.6120(18) . ? C1A C2A 1.363(2) . ? C1A C9A 1.394(2) . ? C2A C3A 1.424(3) . ? C3A C4A 1.371(3) . ? C4A C10A 1.418(2) . ? C5A C6A 1.371(3) . ? C5A C10A 1.416(2) . ? C6A C7A 1.425(2) . ? C7A C8A 1.360(2) . ? C8A C9A 1.405(2) . ? C8A C13A 1.507(2) . ? C9A C10A 1.402(2) . ? C13A C14A 1.478(2) . ? C14A C18A 1.413(2) . ? C14A C15A 1.418(2) . ? C15A C16A 1.519(2) . ? C16A C17A 1.531(2) . ? C17A C18A 1.526(2) . ? O1B C15B 1.2527(18) . ? O2B C18B 1.2489(18) . ? N1B C1B 1.479(2) . ? N1B C11B 1.4985(19) . ? N1B C12B 1.502(2) . ? N1B C13B 1.6257(19) . ? C1B C2B 1.363(2) . ? C1B C9B 1.395(2) . ? C2B C3B 1.423(3) . ? C3B C4B 1.373(3) . ? C4B C10B 1.422(2) . ? C5B C6B 1.372(2) . ? C5B C10B 1.419(2) . ? C6B C7B 1.422(2) . ? C7B C8B 1.369(2) . ? C8B C9B 1.400(2) . ? C8B C13B 1.508(2) . ? C9B C10B 1.405(2) . ? C13B C14B 1.471(2) . ? C14B C15B 1.415(2) . ? C14B C18B 1.419(2) . ? C15B C16B 1.522(2) . ? C16B C17B 1.530(2) . ? C17B C18B 1.522(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 C1A N1A C12A 113.57(12) . . ? C1A N1A C11A 109.23(12) . . ? C12A N1A C11A 109.95(13) . . ? C1A N1A C13A 103.30(11) . . ? C12A N1A C13A 109.84(12) . . ? C11A N1A C13A 110.79(12) . . ? C2A C1A C9A 121.96(15) . . ? C2A C1A N1A 129.63(14) . . ? C9A C1A N1A 108.38(13) . . ? C1A C2A C3A 115.72(16) . . ? C4A C3A C2A 123.51(16) . . ? C3A C4A C10A 120.28(16) . . ? C6A C5A C10A 120.31(15) . . ? C5A C6A C7A 122.30(15) . . ? C8A C7A C6A 118.65(15) . . ? C7A C8A C9A 118.62(15) . . ? C7A C8A C13A 132.72(15) . . ? C9A C8A C13A 108.01(13) . . ? C1A C9A C10A 122.65(14) . . ? C1A C9A C8A 112.99(14) . . ? C10A C9A C8A 124.32(14) . . ? C9A C10A C5A 115.66(15) . . ? C9A C10A C4A 115.82(15) . . ? C5A C10A C4A 128.50(16) . . ? C14A C13A C8A 121.89(13) . . ? C14A C13A N1A 114.75(12) . . ? C8A C13A N1A 101.68(11) . . ? C18A C14A C15A 110.51(14) . . ? C18A C14A C13A 127.41(14) . . ? C15A C14A C13A 121.67(14) . . ? O1A C15A C14A 127.93(15) . . ? O1A C15A C16A 122.33(14) . . ? C14A C15A C16A 109.74(14) . . ? C15A C16A C17A 104.89(13) . . ? C18A C17A C16A 105.30(13) . . ? O2A C18A C14A 128.37(15) . . ? O2A C18A C17A 122.27(14) . . ? C14A C18A C17A 109.35(14) . . ? C1B N1B C11B 109.70(12) . . ? C1B N1B C12B 111.95(12) . . ? C11B N1B C12B 109.39(12) . . ? C1B N1B C13B 104.94(11) . . ? C11B N1B C13B 111.35(11) . . ? C12B N1B C13B 109.46(12) . . ? C2B C1B C9B 122.05(15) . . ? C2B C1B N1B 128.72(14) . . ? C9B C1B N1B 109.15(13) . . ? C1B C2B C3B 116.45(16) . . ? C4B C3B C2B 122.48(16) . . ? C3B C4B C10B 121.04(16) . . ? C6B C5B C10B 119.88(15) . . ? C5B C6B C7B 122.55(15) . . ? C8B C7B C6B 118.73(15) . . ? C7B C8B C9B 118.48(14) . . ? C7B C8B C13B 131.86(15) . . ? C9B C8B C13B 109.54(13) . . ? C1B C9B C8B 113.33(14) . . ? C1B C9B C10B 122.37(15) . . ? C8B C9B C10B 124.30(14) . . ? C9B C10B C5B 116.01(15) . . ? C9B C10B C4B 115.60(15) . . ? C5B C10B C4B 128.39(15) . . ? C14B C13B C8B 118.55(13) . . ? C14B C13B N1B 114.56(12) . . ? C8B C13B N1B 102.01(12) . . ? C15B C14B C18B 111.19(13) . . ? C15B C14B C13B 121.94(13) . . ? C18B C14B C13B 126.80(14) . . ? O1B C15B C14B 127.63(14) . . ? O1B C15B C16B 123.09(14) . . ? C14B C15B C16B 109.28(13) . . ? C15B C16B C17B 104.99(13) . . ? C18B C17B C16B 105.77(12) . . ? O2B C18B C14B 128.61(14) . . ? O2B C18B C17B 122.72(14) . . ? C14B C18B C17B 108.67(13) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.230 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.053 data_Compound_9 _database_code_depnum_ccdc_archive 'CCDC 871639' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium-2-yl)-2,6- dioxocyclohexan-1-ide monhydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N O2, H2 O' _chemical_formula_sum 'C19 H21 N O3' _chemical_formula_weight 311.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4223(2) _cell_length_b 9.4076(3) _cell_length_c 10.8996(3) _cell_angle_alpha 85.508(2) _cell_angle_beta 73.336(2) _cell_angle_gamma 68.462(2) _cell_volume 769.22(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11474 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.67 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18722 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3522 _reflns_number_gt 2834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen atoms of the water molecule were modelled by constraining the O-H distance to 0.85 Ang, and the H---H distance to 1.37 Ang. ; _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^)+(0.0573P)^2^+0.2662P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3522 _refine_ls_number_parameters 216 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.43038(12) 1.01234(10) 0.20601(9) 0.0194(2) Uani 1 1 d . . . O2 O 0.42130(12) 0.51433(10) 0.21349(9) 0.0191(2) Uani 1 1 d . . . N1 N 0.07333(14) 0.87992(12) 0.26623(10) 0.0139(2) Uani 1 1 d . . . C1 C -0.06279(17) 0.83909(15) 0.36648(12) 0.0149(3) Uani 1 1 d . . . C2 C -0.23860(18) 0.87628(16) 0.37558(13) 0.0187(3) Uani 1 1 d . . . H2 H -0.2927 0.9401 0.3157 0.022 Uiso 1 1 calc R . . C3 C -0.33618(18) 0.81400(16) 0.48004(14) 0.0215(3) Uani 1 1 d . . . H3 H -0.4587 0.8369 0.4891 0.026 Uiso 1 1 calc R . . C4 C -0.26137(19) 0.72224(16) 0.56838(14) 0.0212(3) Uani 1 1 d . . . H4 H -0.3318 0.6820 0.6355 0.025 Uiso 1 1 calc R . . C5 C 0.0185(2) 0.59900(16) 0.64403(13) 0.0213(3) Uani 1 1 d . . . H5 H -0.0374 0.5533 0.7158 0.026 Uiso 1 1 calc R . . C6 C 0.1949(2) 0.58001(16) 0.62120(13) 0.0218(3) Uani 1 1 d . . . H6 H 0.2581 0.5204 0.6784 0.026 Uiso 1 1 calc R . . C7 C 0.28649(18) 0.64559(15) 0.51591(13) 0.0180(3) Uani 1 1 d . . . H7 H 0.4075 0.6318 0.5039 0.022 Uiso 1 1 calc R . . C8 C 0.19618(17) 0.72894(14) 0.43232(12) 0.0146(3) Uani 1 1 d . . . C9 C 0.01611(17) 0.74837(15) 0.45589(12) 0.0153(3) Uani 1 1 d . . . C10 C -0.07941(18) 0.68707(15) 0.56000(13) 0.0182(3) Uani 1 1 d . . . C11 C 0.11213(18) 0.79605(17) 0.14308(13) 0.0194(3) Uani 1 1 d . . . H11C H 0.1527 0.6857 0.1567 0.029 Uiso 1 1 calc R . . H11A H 0.2050 0.8202 0.0774 0.029 Uiso 1 1 calc R . . H11B H 0.0040 0.8275 0.1149 0.029 Uiso 1 1 calc R . . C12 C 0.01451(18) 1.04863(15) 0.24507(14) 0.0204(3) Uani 1 1 d . . . H12A H -0.0882 1.0804 0.2104 0.031 Uiso 1 1 calc R . . H12C H 0.1119 1.0722 0.1843 0.031 Uiso 1 1 calc R . . H12B H -0.0186 1.1036 0.3267 0.031 Uiso 1 1 calc R . . C13 C 0.24676(16) 0.82521(14) 0.32125(12) 0.0134(3) Uani 1 1 d . . . H13 H 0.2457 0.9188 0.3596 0.016 Uiso 1 1 calc R . . C14 C 0.41911(16) 0.76502(14) 0.22077(12) 0.0139(3) Uani 1 1 d . . . C15 C 0.49929(16) 0.87469(15) 0.16922(12) 0.0140(3) Uani 1 1 d . . . C16 C 0.67169(17) 0.82428(15) 0.06281(13) 0.0167(3) Uani 1 1 d . . . H16A H 0.7410 0.8877 0.0679 0.020 Uiso 1 1 calc R . . H16B H 0.6444 0.8418 -0.0208 0.020 Uiso 1 1 calc R . . C17 C 0.78427(17) 0.65643(15) 0.06943(13) 0.0187(3) Uani 1 1 d . . . H17A H 0.8269 0.6405 0.1469 0.022 Uiso 1 1 calc R . . H17B H 0.8892 0.6262 -0.0066 0.022 Uiso 1 1 calc R . . C18 C 0.67364(17) 0.55800(15) 0.07376(13) 0.0175(3) Uani 1 1 d . . . H18B H 0.6520 0.5591 -0.0110 0.021 Uiso 1 1 calc R . . H18A H 0.7429 0.4512 0.0896 0.021 Uiso 1 1 calc R . . C19 C 0.49559(17) 0.61007(15) 0.17602(12) 0.0151(3) Uani 1 1 d . . . O3 O 0.36634(13) 0.80257(11) 0.85173(10) 0.0242(2) Uani 1 1 d D . . H31 H 0.4269(16) 0.7083(5) 0.8342(17) 0.036 Uiso 1 1 d D . . H32 H 0.4380(15) 0.8504(14) 0.8302(17) 0.036 Uiso 1 1 d 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 0.0194(5) 0.0136(5) 0.0245(5) -0.0005(4) -0.0040(4) -0.0065(4) O2 0.0196(5) 0.0142(5) 0.0224(5) -0.0006(4) -0.0022(4) -0.0075(4) N1 0.0122(5) 0.0141(5) 0.0142(5) 0.0000(4) -0.0028(4) -0.0040(4) C1 0.0148(6) 0.0139(6) 0.0147(6) -0.0020(5) 0.0002(5) -0.0064(5) C2 0.0159(6) 0.0190(7) 0.0208(7) -0.0029(5) -0.0042(5) -0.0058(5) C3 0.0149(6) 0.0213(7) 0.0266(8) -0.0077(6) 0.0009(6) -0.0080(5) C4 0.0204(7) 0.0201(7) 0.0196(7) -0.0054(5) 0.0057(5) -0.0107(6) C5 0.0298(8) 0.0149(7) 0.0166(7) 0.0001(5) -0.0013(6) -0.0091(6) C6 0.0305(8) 0.0148(7) 0.0172(7) 0.0027(5) -0.0081(6) -0.0044(6) C7 0.0184(6) 0.0143(6) 0.0187(7) -0.0004(5) -0.0047(5) -0.0033(5) C8 0.0168(6) 0.0126(6) 0.0129(6) -0.0020(5) -0.0016(5) -0.0050(5) C9 0.0160(6) 0.0136(6) 0.0151(6) -0.0028(5) -0.0011(5) -0.0056(5) C10 0.0229(7) 0.0136(6) 0.0163(7) -0.0034(5) 0.0005(5) -0.0082(5) C11 0.0156(6) 0.0266(8) 0.0148(6) -0.0045(5) -0.0040(5) -0.0054(6) C12 0.0177(6) 0.0152(7) 0.0269(7) 0.0049(5) -0.0073(6) -0.0043(5) C13 0.0119(6) 0.0135(6) 0.0151(6) 0.0005(5) -0.0042(5) -0.0044(5) C14 0.0133(6) 0.0141(6) 0.0143(6) 0.0006(5) -0.0041(5) -0.0048(5) C15 0.0137(6) 0.0156(6) 0.0141(6) 0.0016(5) -0.0069(5) -0.0049(5) C16 0.0158(6) 0.0167(7) 0.0174(6) 0.0026(5) -0.0034(5) -0.0070(5) C17 0.0139(6) 0.0193(7) 0.0206(7) 0.0006(5) -0.0024(5) -0.0050(5) C18 0.0156(6) 0.0142(6) 0.0194(7) -0.0023(5) -0.0018(5) -0.0035(5) C19 0.0157(6) 0.0165(6) 0.0144(6) 0.0012(5) -0.0058(5) -0.0060(5) O3 0.0190(5) 0.0174(5) 0.0323(6) -0.0017(4) -0.0001(4) -0.0071(4) _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 C15 1.2532(16) . ? O2 C19 1.2566(16) . ? N1 C1 1.4816(16) . ? N1 C12 1.4995(17) . ? N1 C11 1.5020(17) . ? N1 C13 1.6310(16) . ? C1 C2 1.3658(19) . ? C1 C9 1.3944(19) . ? C2 C3 1.424(2) . ? C3 C4 1.374(2) . ? C4 C10 1.421(2) . ? C5 C6 1.378(2) . ? C5 C10 1.421(2) . ? C6 C7 1.4226(19) . ? C7 C8 1.3679(19) . ? C8 C9 1.4071(18) . ? C8 C13 1.5110(17) . ? C9 C10 1.4079(18) . ? C13 C14 1.4862(17) . ? C14 C19 1.4211(18) . ? C14 C15 1.4281(17) . ? C15 C16 1.5143(18) . ? C16 C17 1.5231(18) . ? C17 C18 1.5261(18) . ? C18 C19 1.5227(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C12 111.89(10) . . ? C1 N1 C11 109.30(10) . . ? C12 N1 C11 109.56(11) . . ? C1 N1 C13 104.69(9) . . ? C12 N1 C13 109.89(9) . . ? C11 N1 C13 111.44(9) . . ? C2 C1 C9 122.08(12) . . ? C2 C1 N1 128.64(12) . . ? C9 C1 N1 109.27(11) . . ? C1 C2 C3 116.17(13) . . ? C4 C3 C2 123.04(13) . . ? C3 C4 C10 120.45(13) . . ? C6 C5 C10 119.82(12) . . ? C5 C6 C7 122.98(13) . . ? C8 C7 C6 118.43(13) . . ? C7 C8 C9 118.49(12) . . ? C7 C8 C13 131.61(12) . . ? C9 C8 C13 109.46(11) . . ? C1 C9 C8 113.17(11) . . ? C1 C9 C10 122.21(12) . . ? C8 C9 C10 124.61(12) . . ? C9 C10 C4 116.03(13) . . ? C9 C10 C5 115.65(12) . . ? C4 C10 C5 128.32(13) . . ? C14 C13 C8 121.22(11) . . ? C14 C13 N1 113.99(10) . . ? C8 C13 N1 101.88(9) . . ? C19 C14 C15 122.35(12) . . ? C19 C14 C13 122.19(11) . . ? C15 C14 C13 115.43(11) . . ? O1 C15 C14 122.69(12) . . ? O1 C15 C16 118.42(11) . . ? C14 C15 C16 118.86(11) . . ? C15 C16 C17 112.71(11) . . ? C16 C17 C18 109.67(11) . . ? C19 C18 C17 113.89(11) . . ? O2 C19 C14 123.41(12) . . ? O2 C19 C18 117.96(12) . . ? C14 C19 C18 118.59(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.261 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.053 data_compound_10 _database_code_depnum_ccdc_archive 'CCDC 871640' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium-2-yl)-4,4- dimethyl-2,6-dioxocyclohexan-1-ide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N O2' _chemical_formula_sum 'C21 H23 N O2' _chemical_formula_weight 321.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6118(4) _cell_length_b 10.0248(6) _cell_length_c 18.7717(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.180(3) _cell_angle_gamma 90.00 _cell_volume 1761.13(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8909 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9862 _exptl_absorpt_correction_T_max 0.9885 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18095 _diffrn_reflns_av_R_equivalents 0.1218 _diffrn_reflns_av_sigmaI/netI 0.0859 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3103 _reflns_number_gt 1967 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.7376P] 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 0.0120(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3103 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1583 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0311(3) 0.2863(3) 0.20125(14) 0.0232(6) Uani 1 1 d . . . C2 C -0.0199(3) 0.3378(3) 0.25734(15) 0.0295(7) Uani 1 1 d . . . H2 H -0.0035 0.4278 0.2727 0.035 Uiso 1 1 calc R . . C3 C -0.0995(3) 0.2482(3) 0.29152(16) 0.0334(8) Uani 1 1 d . . . H3 H -0.1372 0.2804 0.3309 0.040 Uiso 1 1 calc R . . C4 C -0.1244(3) 0.1179(3) 0.27039(16) 0.0328(8) Uani 1 1 d . . . H4 H -0.1800 0.0629 0.2944 0.039 Uiso 1 1 calc R . . C5 C -0.0677(3) 0.0642(3) 0.21275(15) 0.0271(7) Uani 1 1 d . . . C6 C -0.0793(3) -0.0678(3) 0.18447(17) 0.0324(8) Uani 1 1 d . . . H6 H -0.1299 -0.1335 0.2049 0.039 Uiso 1 1 calc R . . C7 C -0.0177(3) -0.1006(3) 0.12762(17) 0.0310(7) Uani 1 1 d . . . H7 H -0.0285 -0.1890 0.1089 0.037 Uiso 1 1 calc R . . C8 C 0.0612(3) -0.0079(3) 0.09586(16) 0.0281(7) Uani 1 1 d . . . H8 H 0.1046 -0.0340 0.0574 0.034 Uiso 1 1 calc R . . C9 C 0.0738(3) 0.1206(3) 0.12186(14) 0.0223(7) Uani 1 1 d . . . C10 C 0.0103(3) 0.1540(3) 0.17913(14) 0.0228(6) Uani 1 1 d . . . C11 C 0.1374(3) 0.2429(3) 0.09542(14) 0.0220(6) Uani 1 1 d . . . H11 H 0.0716 0.2686 0.0481 0.026 Uiso 1 1 calc R . . C12 C 0.2557(3) 0.4017(3) 0.20200(17) 0.0343(8) Uani 1 1 d . . . H12A H 0.2377 0.4651 0.2386 0.052 Uiso 1 1 calc R . . H12B H 0.3115 0.4455 0.1710 0.052 Uiso 1 1 calc R . . H12C H 0.3092 0.3251 0.2267 0.052 Uiso 1 1 calc R . . C13 C 0.0349(3) 0.4715(3) 0.11628(17) 0.0342(8) Uani 1 1 d . . . H13A H -0.0593 0.4418 0.0888 0.051 Uiso 1 1 calc R . . H13B H 0.0881 0.5097 0.0824 0.051 Uiso 1 1 calc R . . H13C H 0.0230 0.5392 0.1521 0.051 Uiso 1 1 calc R . . C14 C 0.2818(3) 0.2335(3) 0.08071(14) 0.0215(6) Uani 1 1 d . . . C15 C 0.3027(3) 0.2934(3) 0.01528(15) 0.0238(7) Uani 1 1 d . . . C16 C 0.3908(3) 0.1585(3) 0.12807(15) 0.0226(6) Uani 1 1 d . . . C17 C 0.4400(3) 0.2644(3) -0.00858(14) 0.0246(7) Uani 1 1 d . . . H17A H 0.4626 0.3420 -0.0365 0.030 Uiso 1 1 calc R . . H17B H 0.4236 0.1870 -0.0422 0.030 Uiso 1 1 calc R . . C18 C 0.5280(3) 0.1287(3) 0.10333(15) 0.0252(7) Uani 1 1 d . . . H18A H 0.5165 0.0423 0.0770 0.030 Uiso 1 1 calc R . . H18B H 0.6069 0.1184 0.1472 0.030 Uiso 1 1 calc R . . C19 C 0.5706(3) 0.2345(3) 0.05378(14) 0.0236(6) Uani 1 1 d . . . C20 C 0.6182(3) 0.3612(3) 0.09847(16) 0.0293(7) Uani 1 1 d . . . H20A H 0.5392 0.3949 0.1184 0.044 Uiso 1 1 calc R . . H20B H 0.6460 0.4292 0.0668 0.044 Uiso 1 1 calc R . . H20C H 0.7000 0.3405 0.1387 0.044 Uiso 1 1 calc R . . C21 C 0.6938(3) 0.1845(3) 0.02168(15) 0.0300(7) Uani 1 1 d . . . H21A H 0.7765 0.1644 0.0615 0.045 Uiso 1 1 calc R . . H21B H 0.7196 0.2536 -0.0099 0.045 Uiso 1 1 calc R . . H21C H 0.6641 0.1036 -0.0071 0.045 Uiso 1 1 calc R . . N1 N 0.1157(2) 0.3548(2) 0.15538(12) 0.0247(6) Uani 1 1 d . . . O1 O 0.21052(19) 0.36558(19) -0.02526(10) 0.0303(5) Uani 1 1 d . . . O2 O 0.37857(19) 0.11507(19) 0.18894(10) 0.0286(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0200(13) 0.0290(16) 0.0205(14) 0.0019(12) 0.0043(11) 0.0016(12) C2 0.0264(15) 0.0388(18) 0.0215(15) -0.0032(13) 0.0017(13) 0.0033(13) C3 0.0284(15) 0.052(2) 0.0207(15) 0.0042(14) 0.0074(13) 0.0107(15) C4 0.0251(15) 0.047(2) 0.0270(17) 0.0146(15) 0.0069(13) 0.0051(14) C5 0.0204(14) 0.0333(17) 0.0269(16) 0.0102(13) 0.0040(13) 0.0006(13) C6 0.0240(15) 0.0302(17) 0.0421(19) 0.0107(14) 0.0057(14) -0.0048(13) C7 0.0281(16) 0.0252(16) 0.0359(18) -0.0007(13) -0.0006(14) -0.0032(13) C8 0.0236(14) 0.0260(16) 0.0341(17) -0.0036(13) 0.0053(13) -0.0003(12) C9 0.0172(13) 0.0274(16) 0.0201(15) 0.0008(12) -0.0006(11) -0.0019(12) C10 0.0183(13) 0.0273(15) 0.0213(14) 0.0030(12) 0.0014(12) 0.0034(12) C11 0.0209(13) 0.0267(15) 0.0188(14) -0.0020(12) 0.0053(11) -0.0001(12) C12 0.0255(15) 0.0398(18) 0.0383(18) -0.0169(15) 0.0085(14) -0.0063(13) C13 0.0417(18) 0.0261(17) 0.0402(18) 0.0081(14) 0.0205(15) 0.0084(14) C14 0.0210(14) 0.0238(15) 0.0195(14) 0.0013(11) 0.0043(11) 0.0007(12) C15 0.0216(14) 0.0226(15) 0.0250(15) -0.0033(12) 0.0009(12) 0.0006(12) C16 0.0229(14) 0.0208(15) 0.0240(15) -0.0009(12) 0.0051(12) -0.0023(11) C17 0.0263(14) 0.0291(15) 0.0191(14) 0.0017(12) 0.0064(12) 0.0016(12) C18 0.0200(13) 0.0286(16) 0.0263(16) 0.0004(12) 0.0036(12) -0.0005(12) C19 0.0245(14) 0.0256(15) 0.0213(14) 0.0014(12) 0.0066(12) -0.0015(12) C20 0.0260(15) 0.0295(16) 0.0328(17) -0.0021(13) 0.0076(13) -0.0024(13) C21 0.0288(15) 0.0364(17) 0.0256(15) -0.0031(13) 0.0074(12) 0.0036(13) N1 0.0220(12) 0.0248(13) 0.0279(13) -0.0016(10) 0.0070(10) 0.0001(10) O1 0.0262(10) 0.0348(12) 0.0293(11) 0.0092(9) 0.0055(9) 0.0041(9) O2 0.0286(11) 0.0347(12) 0.0228(11) 0.0077(9) 0.0064(9) 0.0000(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.361(4) . ? C1 C10 1.390(4) . ? C1 N1 1.481(4) . ? C2 C3 1.424(4) . ? C2 H2 0.9500 . ? C3 C4 1.370(4) . ? C3 H3 0.9500 . ? C4 C5 1.424(4) . ? C4 H4 0.9500 . ? C5 C10 1.409(4) . ? C5 C6 1.421(4) . ? C6 C7 1.373(4) . ? C6 H6 0.9500 . ? C7 C8 1.414(4) . ? C7 H7 0.9500 . ? C8 C9 1.374(4) . ? C8 H8 0.9500 . ? C9 C10 1.392(4) . ? C9 C11 1.503(4) . ? C11 C14 1.479(4) . ? C11 N1 1.636(3) . ? C11 H11 1.0000 . ? C12 N1 1.504(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N1 1.501(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.422(4) . ? C14 C16 1.424(4) . ? C15 O1 1.257(3) . ? C15 C17 1.515(4) . ? C16 O2 1.253(3) . ? C16 C18 1.524(4) . ? C17 C19 1.538(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.527(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C21 1.530(4) . ? C19 C20 1.533(4) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C2 C1 C10 122.7(3) . . ? C2 C1 N1 128.1(3) . . ? C10 C1 N1 109.2(2) . . ? C1 C2 C3 115.8(3) . . ? C1 C2 H2 122.1 . . ? C3 C2 H2 122.1 . . ? C4 C3 C2 123.1(3) . . ? C4 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C10 C5 C6 115.6(3) . . ? C10 C5 C4 115.7(3) . . ? C6 C5 C4 128.7(3) . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 122.6(3) . . ? C6 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C9 C8 C7 118.6(3) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 C10 118.8(3) . . ? C8 C9 C11 131.1(3) . . ? C10 C9 C11 110.0(2) . . ? C1 C10 C9 113.7(2) . . ? C1 C10 C5 122.0(3) . . ? C9 C10 C5 124.3(3) . . ? C14 C11 C9 118.7(2) . . ? C14 C11 N1 116.4(2) . . ? C9 C11 N1 101.9(2) . . ? C14 C11 H11 106.3 . . ? C9 C11 H11 106.3 . . ? N1 C11 H11 106.3 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C16 122.2(2) . . ? C15 C14 C11 117.2(2) . . ? C16 C14 C11 120.3(2) . . ? O1 C15 C14 123.2(2) . . ? O1 C15 C17 118.2(2) . . ? C14 C15 C17 118.6(2) . . ? O2 C16 C14 123.0(2) . . ? O2 C16 C18 118.5(2) . . ? C14 C16 C18 118.5(2) . . ? C15 C17 C19 115.3(2) . . ? C15 C17 H17A 108.5 . . ? C19 C17 H17A 108.5 . . ? C15 C17 H17B 108.5 . . ? C19 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C16 C18 C19 114.8(2) . . ? C16 C18 H18A 108.6 . . ? C19 C18 H18A 108.6 . . ? C16 C18 H18B 108.6 . . ? C19 C18 H18B 108.6 . . ? H18A C18 H18B 107.5 . . ? C18 C19 C21 110.6(2) . . ? C18 C19 C20 109.3(2) . . ? C21 C19 C20 109.0(2) . . ? C18 C19 C17 108.2(2) . . ? C21 C19 C17 109.6(2) . . ? C20 C19 C17 110.2(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 N1 C13 110.7(2) . . ? C1 N1 C12 110.1(2) . . ? C13 N1 C12 109.6(2) . . ? C1 N1 C11 104.80(19) . . ? C13 N1 C11 109.4(2) . . ? C12 N1 C11 112.17(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.210 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.055 data_compound_12 _database_code_depnum_ccdc_archive 'CCDC 871641' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N3 O3' _chemical_formula_sum 'C19 H19 N3 O3' _chemical_formula_weight 337.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3360(4) _cell_length_b 8.7036(3) _cell_length_c 12.1220(6) _cell_angle_alpha 89.456(3) _cell_angle_beta 85.190(2) _cell_angle_gamma 65.248(3) _cell_volume 795.56(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19881 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.645 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16118 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3656 _reflns_number_gt 2967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.1386P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3656 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.26715(14) 0.03266(13) 0.19876(9) 0.0218(3) Uani 1 1 d . . . O2 O 0.73167(14) 0.24432(13) 0.05345(8) 0.0216(3) Uani 1 1 d . . . O3 O 0.88786(14) -0.24745(13) 0.23948(9) 0.0235(3) Uani 1 1 d . . . N1 N 1.36070(16) -0.41177(14) 0.24705(9) 0.0171(3) Uani 1 1 d . . . N2 N 1.00091(16) 0.13595(14) 0.12375(10) 0.0168(3) Uani 1 1 d . . . N3 N 0.81517(15) -0.00592(15) 0.14194(10) 0.0172(3) Uani 1 1 d . . . C1 C 1.40165(19) -0.53018(18) 0.34039(12) 0.0176(3) Uani 1 1 d . . . C2 C 1.5311(2) -0.69053(19) 0.34403(12) 0.0226(3) Uani 1 1 d . . . H2 H 1.6218 -0.7381 0.2853 0.027 Uiso 1 1 calc R . . C3 C 1.5233(2) -0.78320(19) 0.44046(13) 0.0242(3) Uani 1 1 d . . . H3 H 1.6117 -0.8952 0.4456 0.029 Uiso 1 1 calc R . . C4 C 1.3931(2) -0.71716(18) 0.52631(12) 0.0225(3) Uani 1 1 d . . . H4 H 1.3913 -0.7848 0.5880 0.027 Uiso 1 1 calc R . . C5 C 1.1176(2) -0.45971(19) 0.60354(12) 0.0208(3) Uani 1 1 d . . . H5 H 1.1037 -0.5128 0.6703 0.025 Uiso 1 1 calc R . . C6 C 0.9987(2) -0.29711(19) 0.58464(12) 0.0207(3) Uani 1 1 d . . . H6 H 0.9034 -0.2402 0.6392 0.025 Uiso 1 1 calc R . . C7 C 1.01306(19) -0.21083(18) 0.48643(12) 0.0189(3) Uani 1 1 d . . . H7 H 0.9290 -0.0986 0.4756 0.023 Uiso 1 1 calc R . . C8 C 1.15039(19) -0.29310(17) 0.40810(11) 0.0169(3) Uani 1 1 d . . . C9 C 1.27059(19) -0.45881(18) 0.42761(11) 0.0172(3) Uani 1 1 d . . . C10 C 1.2608(2) -0.54799(18) 0.52340(11) 0.0187(3) Uani 1 1 d . . . C11 C 1.2830(2) -0.47792(18) 0.16151(12) 0.0211(3) Uani 1 1 d . . . H11A H 1.3707 -0.5892 0.1333 0.032 Uiso 1 1 calc R . . H11B H 1.2506 -0.3994 0.1003 0.032 Uiso 1 1 calc R . . H11C H 1.1771 -0.4884 0.1952 0.032 Uiso 1 1 calc R . . C12 C 1.5164(2) -0.38782(19) 0.19307(13) 0.0221(3) Uani 1 1 d . . . H12A H 1.5752 -0.3557 0.2495 0.033 Uiso 1 1 calc R . . H12B H 1.4759 -0.2983 0.1388 0.033 Uiso 1 1 calc R . . H12C H 1.6002 -0.4938 0.1555 0.033 Uiso 1 1 calc R . . C13 C 1.21523(18) -0.23355(17) 0.30319(11) 0.0166(3) Uani 1 1 d . . . H13 H 1.2847 -0.1719 0.3273 0.020 Uiso 1 1 calc R . . C14 C 1.08958(18) -0.11916(17) 0.22825(11) 0.0165(3) Uani 1 1 d . . . C15 C 0.93230(19) -0.13341(17) 0.20732(11) 0.0173(3) Uani 1 1 d . . . C16 C 0.84328(19) 0.13086(17) 0.10325(11) 0.0164(3) Uani 1 1 d . . . C17 C 1.13065(18) 0.01397(17) 0.18505(11) 0.0162(3) Uani 1 1 d . . . C18 C 0.6502(2) -0.0143(2) 0.11654(13) 0.0243(3) Uani 1 1 d . . . H18A H 0.5523 0.0601 0.1685 0.036 Uiso 1 1 calc R . . H18B H 0.6625 -0.1309 0.1234 0.036 Uiso 1 1 calc R . . H18C H 0.6253 0.0223 0.0407 0.036 Uiso 1 1 calc R . . C19 C 1.0284(2) 0.28417(18) 0.08458(12) 0.0214(3) Uani 1 1 d . . . H19A H 1.0138 0.2959 0.0051 0.032 Uiso 1 1 calc R . . H19B H 1.1483 0.2693 0.0978 0.032 Uiso 1 1 calc R . . H19C H 0.9413 0.3861 0.1247 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0165(5) 0.0235(6) 0.0275(6) 0.0031(4) -0.0025(4) -0.0104(4) O2 0.0195(6) 0.0202(5) 0.0226(5) 0.0050(4) -0.0047(4) -0.0055(4) O3 0.0225(6) 0.0224(6) 0.0300(6) 0.0087(4) -0.0065(5) -0.0130(5) N1 0.0155(6) 0.0164(6) 0.0182(6) 0.0020(5) -0.0030(5) -0.0053(5) N2 0.0161(6) 0.0156(6) 0.0190(6) 0.0026(5) -0.0015(5) -0.0069(5) N3 0.0143(6) 0.0169(6) 0.0206(6) 0.0027(5) -0.0031(5) -0.0066(5) C1 0.0183(7) 0.0168(7) 0.0183(7) 0.0019(5) -0.0045(6) -0.0074(6) C2 0.0212(8) 0.0205(7) 0.0230(8) -0.0011(6) -0.0035(6) -0.0055(6) C3 0.0258(8) 0.0158(7) 0.0288(8) 0.0037(6) -0.0105(7) -0.0052(6) C4 0.0287(8) 0.0186(7) 0.0227(7) 0.0053(6) -0.0100(6) -0.0112(6) C5 0.0253(8) 0.0251(8) 0.0181(7) 0.0042(6) -0.0050(6) -0.0161(6) C6 0.0209(7) 0.0269(8) 0.0174(7) -0.0030(6) 0.0000(6) -0.0134(6) C7 0.0171(7) 0.0174(7) 0.0222(7) -0.0005(5) -0.0035(6) -0.0070(6) C8 0.0175(7) 0.0172(7) 0.0179(7) 0.0020(5) -0.0042(5) -0.0086(6) C9 0.0175(7) 0.0180(7) 0.0182(7) 0.0016(5) -0.0051(6) -0.0088(6) C10 0.0214(8) 0.0199(7) 0.0186(7) 0.0031(5) -0.0069(6) -0.0114(6) C11 0.0227(8) 0.0204(7) 0.0193(7) -0.0009(6) -0.0055(6) -0.0077(6) C12 0.0165(7) 0.0228(8) 0.0256(8) 0.0007(6) 0.0034(6) -0.0077(6) C13 0.0150(7) 0.0150(7) 0.0192(7) 0.0001(5) -0.0013(5) -0.0058(5) C14 0.0153(7) 0.0156(7) 0.0174(7) 0.0019(5) -0.0019(5) -0.0054(5) C15 0.0167(7) 0.0154(7) 0.0185(7) 0.0015(5) -0.0010(5) -0.0056(6) C16 0.0168(7) 0.0161(7) 0.0145(6) -0.0005(5) 0.0006(5) -0.0056(6) C17 0.0152(7) 0.0157(7) 0.0158(7) -0.0015(5) -0.0003(5) -0.0047(6) C18 0.0169(7) 0.0263(8) 0.0319(8) 0.0052(6) -0.0070(6) -0.0103(6) C19 0.0228(8) 0.0174(7) 0.0255(8) 0.0042(6) -0.0026(6) -0.0099(6) _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 C17 1.2394(17) . ? O2 C16 1.2323(17) . ? O3 C15 1.2452(17) . ? N1 C1 1.4856(18) . ? N1 C12 1.4963(18) . ? N1 C11 1.5039(17) . ? N1 C13 1.6267(18) . ? N2 C16 1.3762(18) . ? N2 C17 1.4168(18) . ? N2 C19 1.4695(17) . ? N3 C16 1.3773(18) . ? N3 C15 1.4207(18) . ? N3 C18 1.4654(18) . ? C1 C2 1.364(2) . ? C1 C9 1.396(2) . ? C2 C3 1.426(2) . ? C3 C4 1.375(2) . ? C4 C10 1.425(2) . ? C5 C6 1.377(2) . ? C5 C10 1.418(2) . ? C6 C7 1.425(2) . ? C7 C8 1.367(2) . ? C8 C9 1.401(2) . ? C8 C13 1.5116(19) . ? C9 C10 1.406(2) . ? C13 C14 1.4774(19) . ? C14 C15 1.4111(19) . ? C14 C17 1.4229(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C12 114.71(11) . . ? C1 N1 C11 108.01(11) . . ? C12 N1 C11 108.86(11) . . ? C1 N1 C13 103.96(10) . . ? C12 N1 C13 109.86(10) . . ? C11 N1 C13 111.39(10) . . ? C16 N2 C17 124.23(11) . . ? C16 N2 C19 116.72(11) . . ? C17 N2 C19 118.94(11) . . ? C16 N3 C15 124.03(12) . . ? C16 N3 C18 116.88(12) . . ? C15 N3 C18 119.05(11) . . ? C2 C1 C9 121.77(13) . . ? C2 C1 N1 129.18(13) . . ? C9 C1 N1 108.74(12) . . ? C1 C2 C3 116.59(14) . . ? C4 C3 C2 122.73(14) . . ? C3 C4 C10 120.46(13) . . ? C6 C5 C10 119.97(13) . . ? C5 C6 C7 122.55(14) . . ? C8 C7 C6 118.56(13) . . ? C7 C8 C9 118.63(13) . . ? C7 C8 C13 131.91(13) . . ? C9 C8 C13 109.10(12) . . ? C1 C9 C8 113.07(13) . . ? C1 C9 C10 122.49(13) . . ? C8 C9 C10 124.43(14) . . ? C9 C10 C5 115.85(13) . . ? C9 C10 C4 115.93(14) . . ? C5 C10 C4 128.20(13) . . ? C14 C13 C8 121.21(12) . . ? C14 C13 N1 115.54(11) . . ? C8 C13 N1 101.36(10) . . ? C15 C14 C17 122.05(12) . . ? C15 C14 C13 122.14(12) . . ? C17 C14 C13 115.66(12) . . ? O3 C15 C14 126.33(13) . . ? O3 C15 N3 117.27(12) . . ? C14 C15 N3 116.40(12) . . ? O2 C16 N2 121.52(12) . . ? O2 C16 N3 121.52(13) . . ? N2 C16 N3 116.96(12) . . ? O1 C17 N2 118.38(12) . . ? O1 C17 C14 125.42(13) . . ? N2 C17 C14 116.17(12) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.394 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.149 data_compound_13 _database_code_depnum_ccdc_archive 'CCDC 871642' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H17 N O2' _chemical_formula_sum 'C22 H17 N O2' _chemical_formula_weight 327.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8717(3) _cell_length_b 11.5384(3) _cell_length_c 15.6190(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.980(3) _cell_angle_gamma 90.00 _cell_volume 1590.14(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4313 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 29.04 _exptl_crystal_description 'thick plate' _exptl_crystal_colour orange _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-89 ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9832 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7969 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 29.09 _reflns_number_total 3648 _reflns_number_gt 2836 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3648 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.39284(10) 0.84108(7) 0.06104(5) 0.0255(2) Uani 1 1 d . . . O2 O 0.52011(10) 0.59832(7) -0.16487(6) 0.0285(2) Uani 1 1 d . . . N1 N 0.32162(11) 0.88040(8) -0.19149(6) 0.0178(2) Uani 1 1 d . . . C1 C 0.18681(14) 0.95584(9) -0.19523(7) 0.0174(3) Uani 1 1 d . . . C2 C 0.15700(15) 1.05357(10) -0.24278(8) 0.0227(3) Uani 1 1 d . . . H2 H 0.2244 1.0813 -0.2816 0.027 Uiso 1 1 calc R . . C3 C 0.01942(15) 1.11188(11) -0.23115(8) 0.0265(3) Uani 1 1 d . . . H3 H -0.0052 1.1803 -0.2635 0.032 Uiso 1 1 calc R . . C4 C -0.07933(15) 1.07368(11) -0.17521(8) 0.0253(3) Uani 1 1 d . . . H4 H -0.1699 1.1157 -0.1696 0.030 Uiso 1 1 calc R . . C5 C -0.13381(14) 0.92228(11) -0.06374(8) 0.0224(3) Uani 1 1 d . . . H5 H -0.2272 0.9566 -0.0526 0.027 Uiso 1 1 calc R . . C6 C -0.08227(14) 0.82460(11) -0.01994(8) 0.0231(3) Uani 1 1 d . . . H6 H -0.1409 0.7933 0.0221 0.028 Uiso 1 1 calc R . . C7 C 0.05476(14) 0.76842(10) -0.03470(8) 0.0207(3) Uani 1 1 d . . . H7 H 0.0868 0.7005 -0.0035 0.025 Uiso 1 1 calc R . . C8 C 0.13999(13) 0.81379(9) -0.09472(7) 0.0166(3) Uani 1 1 d . . . C9 C 0.08835(13) 0.91468(9) -0.13842(7) 0.0167(3) Uani 1 1 d . . . C10 C -0.04687(14) 0.97173(10) -0.12569(8) 0.0200(3) Uani 1 1 d . . . C12 C 0.34606(17) 0.83527(11) -0.27892(8) 0.0287(3) Uani 1 1 d . . . H12A H 0.2497 0.8070 -0.3078 0.043 Uiso 1 1 calc R . . H12B H 0.4195 0.7716 -0.2731 0.043 Uiso 1 1 calc R . . H12C H 0.3849 0.8977 -0.3131 0.043 Uiso 1 1 calc R . . C11 C 0.45874(15) 0.94495(11) -0.15399(9) 0.0301(3) Uani 1 1 d . . . H11A H 0.4770 1.0109 -0.1911 0.045 Uiso 1 1 calc R . . H11B H 0.5468 0.8932 -0.1498 0.045 Uiso 1 1 calc R . . H11C H 0.4425 0.9732 -0.0965 0.045 Uiso 1 1 calc R . . C13 C 0.28282(13) 0.77073(9) -0.12925(7) 0.0162(3) Uani 1 1 d . . . H13 H 0.2528 0.7040 -0.1682 0.019 Uiso 1 1 calc R . . C14 C 0.41117(14) 0.73165(9) -0.06974(7) 0.0168(3) Uani 1 1 d . . . C15 C 0.51376(14) 0.64493(10) -0.09352(8) 0.0191(3) Uani 1 1 d . . . C16 C 0.62212(14) 0.62024(10) -0.01476(8) 0.0190(3) Uani 1 1 d . . . C17 C 0.74217(14) 0.54413(10) -0.00278(8) 0.0247(3) Uani 1 1 d . . . H17 H 0.7660 0.4940 -0.0477 0.030 Uiso 1 1 calc R . . C18 C 0.82800(15) 0.54294(11) 0.07777(9) 0.0281(3) Uani 1 1 d . . . H18 H 0.9105 0.4905 0.0880 0.034 Uiso 1 1 calc R . . C19 C 0.79393(15) 0.61722(11) 0.14260(8) 0.0266(3) Uani 1 1 d . . . H19 H 0.8540 0.6156 0.1966 0.032 Uiso 1 1 calc R . . C20 C 0.67260(14) 0.69439(11) 0.12980(8) 0.0226(3) Uani 1 1 d . . . H20 H 0.6499 0.7459 0.1741 0.027 Uiso 1 1 calc R . . C21 C 0.58632(14) 0.69382(10) 0.05080(8) 0.0182(3) Uani 1 1 d . . . C22 C 0.45070(14) 0.76674(10) 0.01746(8) 0.0181(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0249(5) 0.0271(5) 0.0247(5) -0.0084(4) 0.0032(4) 0.0037(4) O2 0.0304(5) 0.0318(5) 0.0231(5) -0.0084(4) 0.0025(4) 0.0085(4) N1 0.0167(5) 0.0177(5) 0.0194(5) 0.0006(4) 0.0032(4) -0.0010(4) C1 0.0173(6) 0.0170(6) 0.0173(6) -0.0036(5) -0.0009(5) 0.0003(5) C2 0.0238(7) 0.0232(6) 0.0207(6) 0.0021(5) 0.0000(5) -0.0023(5) C3 0.0293(7) 0.0203(6) 0.0279(7) 0.0031(5) -0.0056(6) 0.0025(6) C4 0.0220(7) 0.0246(6) 0.0281(7) -0.0044(5) -0.0035(6) 0.0057(6) C5 0.0138(6) 0.0283(7) 0.0248(7) -0.0078(5) 0.0017(5) 0.0007(5) C6 0.0193(7) 0.0288(7) 0.0221(7) -0.0033(5) 0.0064(5) -0.0064(6) C7 0.0212(7) 0.0203(6) 0.0208(6) 0.0014(5) 0.0027(5) -0.0015(5) C8 0.0149(6) 0.0167(6) 0.0177(6) -0.0035(5) -0.0004(5) -0.0024(5) C9 0.0170(6) 0.0172(6) 0.0155(6) -0.0039(5) -0.0006(5) -0.0019(5) C10 0.0184(6) 0.0216(6) 0.0192(6) -0.0046(5) -0.0023(5) 0.0012(5) C12 0.0376(8) 0.0282(7) 0.0228(7) 0.0010(6) 0.0156(6) 0.0032(6) C11 0.0212(7) 0.0272(7) 0.0398(8) 0.0098(6) -0.0059(6) -0.0090(6) C13 0.0173(6) 0.0144(5) 0.0173(6) 0.0007(5) 0.0030(5) -0.0027(5) C14 0.0167(6) 0.0158(6) 0.0180(6) 0.0005(5) 0.0023(5) -0.0004(5) C15 0.0191(6) 0.0183(6) 0.0203(6) -0.0009(5) 0.0033(5) -0.0012(5) C16 0.0170(6) 0.0186(6) 0.0214(6) 0.0027(5) 0.0023(5) -0.0023(5) C17 0.0244(7) 0.0207(6) 0.0286(7) -0.0002(5) 0.0017(6) 0.0033(5) C18 0.0231(7) 0.0239(7) 0.0360(8) 0.0055(6) -0.0032(6) 0.0048(6) C19 0.0251(7) 0.0301(7) 0.0234(7) 0.0074(6) -0.0037(6) -0.0034(6) C20 0.0218(7) 0.0256(6) 0.0209(6) 0.0016(5) 0.0047(5) -0.0049(5) C21 0.0163(6) 0.0184(6) 0.0201(6) 0.0030(5) 0.0036(5) -0.0037(5) C22 0.0159(6) 0.0180(6) 0.0212(6) 0.0003(5) 0.0054(5) -0.0028(5) _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 C22 1.2391(14) . ? O2 C15 1.2441(14) . ? N1 C1 1.4754(15) . ? N1 C11 1.4930(15) . ? N1 C12 1.4983(15) . ? N1 C13 1.6536(14) . ? C1 C2 1.3609(16) . ? C1 C9 1.3920(16) . ? C2 C3 1.4218(18) . ? C3 C4 1.3729(18) . ? C4 C10 1.4207(17) . ? C5 C6 1.3719(17) . ? C5 C10 1.4186(17) . ? C6 C7 1.4176(17) . ? C7 C8 1.3684(16) . ? C8 C9 1.4020(16) . ? C8 C13 1.5119(16) . ? C9 C10 1.4006(16) . ? C13 C14 1.4640(16) . ? C14 C15 1.4275(16) . ? C14 C22 1.4292(17) . ? C15 C16 1.5073(16) . ? C16 C17 1.3781(17) . ? C16 C21 1.3921(17) . ? C17 C18 1.4012(18) . ? C18 C19 1.3837(19) . ? C19 C20 1.3953(18) . ? C20 C21 1.3826(16) . ? C21 C22 1.5153(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 110.19(9) . . ? C1 N1 C12 111.26(9) . . ? C11 N1 C12 109.97(10) . . ? C1 N1 C13 104.91(8) . . ? C11 N1 C13 111.23(8) . . ? C12 N1 C13 109.19(8) . . ? C2 C1 C9 122.10(12) . . ? C2 C1 N1 128.40(11) . . ? C9 C1 N1 109.47(9) . . ? C1 C2 C3 116.30(12) . . ? C4 C3 C2 122.86(12) . . ? C3 C4 C10 120.38(12) . . ? C6 C5 C10 119.60(12) . . ? C5 C6 C7 122.79(12) . . ? C8 C7 C6 118.74(11) . . ? C7 C8 C9 118.38(11) . . ? C7 C8 C13 131.46(10) . . ? C9 C8 C13 110.04(10) . . ? C1 C9 C10 122.26(11) . . ? C1 C9 C8 113.50(11) . . ? C10 C9 C8 124.23(11) . . ? C9 C10 C5 116.25(11) . . ? C9 C10 C4 116.10(12) . . ? C5 C10 C4 127.63(12) . . ? C14 C13 C8 120.00(10) . . ? C14 C13 N1 114.41(9) . . ? C8 C13 N1 101.06(8) . . ? C15 C14 C22 110.28(11) . . ? C15 C14 C13 121.71(11) . . ? C22 C14 C13 127.96(11) . . ? O2 C15 C14 128.73(11) . . ? O2 C15 C16 124.39(11) . . ? C14 C15 C16 106.85(10) . . ? C17 C16 C21 121.41(11) . . ? C17 C16 C15 130.50(11) . . ? C21 C16 C15 108.06(10) . . ? C16 C17 C18 117.91(12) . . ? C19 C18 C17 120.75(12) . . ? C18 C19 C20 120.96(12) . . ? C21 C20 C19 118.16(12) . . ? C20 C21 C16 120.78(11) . . ? C20 C21 C22 130.54(11) . . ? C16 C21 C22 108.64(10) . . ? O1 C22 C14 130.17(11) . . ? O1 C22 C21 123.72(11) . . ? C14 C22 C21 106.11(10) . . ? _diffrn_measured_fraction_theta_max 0.856 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.241 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.040 data_compound_14 _database_code_depnum_ccdc_archive 'CCDC 871643' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(1!,1!-Diethyl-1!,2!-dihydrobenzo[cd]indol-1!-ium-2!-yl)-4,6- dioxo-1,3-dioxan-5-ide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N O4' _chemical_formula_sum 'C21 H23 N O4' _chemical_formula_weight 353.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall' '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1338(3) _cell_length_b 16.0686(5) _cell_length_c 10.9554(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.661(3) _cell_angle_gamma 90.00 _cell_volume 1775.23(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4406 _cell_measurement_theta_min 2.8982 _cell_measurement_theta_max 29.1206 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9832 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8335 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 29.19 _reflns_number_total 4116 _reflns_number_gt 3047 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4116 _refine_ls_number_parameters 239 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35854(8) 0.18540(5) 0.71470(8) 0.0246(2) Uani 1 1 d . . . O2 O 0.30431(9) 0.07149(5) 0.81178(8) 0.0249(2) Uani 1 1 d . . . O3 O 0.14952(8) -0.04144(5) 0.50453(8) 0.0238(2) Uani 1 1 d U . . O4 O 0.19860(9) -0.04227(5) 0.70663(8) 0.0259(2) Uani 1 1 d . . . N1 N 0.17211(10) 0.17611(6) 0.41828(9) 0.0176(2) Uani 1 1 d . . . C1 C 0.24600(12) 0.24658(7) 0.36984(11) 0.0183(3) Uani 1 1 d . . . C2 C 0.19823(13) 0.31215(8) 0.29977(11) 0.0232(3) Uani 1 1 d . . . H2 H 0.1062 0.3189 0.2760 0.028 Uiso 1 1 calc R . . C3 C 0.29385(13) 0.36979(8) 0.26429(12) 0.0253(3) Uani 1 1 d . . . H3 H 0.2638 0.4162 0.2154 0.030 Uiso 1 1 calc R . . C4 C 0.42733(13) 0.36159(7) 0.29725(12) 0.0245(3) Uani 1 1 d . . . H4 H 0.4869 0.4026 0.2728 0.029 Uiso 1 1 calc R . . C5 C 0.61131(13) 0.27113(8) 0.40489(12) 0.0239(3) Uani 1 1 d . . . H5 H 0.6805 0.3075 0.3866 0.029 Uiso 1 1 calc R . . C6 C 0.64127(13) 0.19850(8) 0.46706(12) 0.0252(3) Uani 1 1 d . . . H6 H 0.7316 0.1857 0.4912 0.030 Uiso 1 1 calc R . . C7 C 0.54244(12) 0.14189(8) 0.49663(12) 0.0222(3) Uani 1 1 d . . . H7 H 0.5659 0.0918 0.5394 0.027 Uiso 1 1 calc R . . C8 C 0.41274(12) 0.16061(7) 0.46264(11) 0.0181(3) Uani 1 1 d . . . C9 C 0.38166(12) 0.23517(7) 0.40102(11) 0.0178(3) Uani 1 1 d . . . C10 C 0.47703(12) 0.29228(7) 0.36762(11) 0.0202(3) Uani 1 1 d . . . C11 C 0.09252(12) 0.20282(8) 0.52289(11) 0.0216(3) Uani 1 1 d . . . H11A H 0.0463 0.1533 0.5516 0.026 Uiso 1 1 calc R . . H11B H 0.1554 0.2221 0.5919 0.026 Uiso 1 1 calc R . . C12 C -0.00922(13) 0.27062(8) 0.49291(13) 0.0265(3) Uani 1 1 d . . . H12A H 0.0361 0.3227 0.4764 0.040 Uiso 1 1 calc R . . H12B H -0.0616 0.2785 0.5626 0.040 Uiso 1 1 calc R . . H12C H -0.0680 0.2546 0.4203 0.040 Uiso 1 1 calc R . . C13 C 0.08092(13) 0.13332(8) 0.31912(12) 0.0255(3) Uani 1 1 d . . . H13A H 0.0469 0.0814 0.3532 0.031 Uiso 1 1 calc R . . H13B H 0.0040 0.1700 0.2960 0.031 Uiso 1 1 calc R . . C14 C 0.14687(15) 0.11229(9) 0.20501(12) 0.0318(3) Uani 1 1 d . . . H14A H 0.1746 0.1637 0.1668 0.048 Uiso 1 1 calc R . . H14B H 0.0841 0.0823 0.1471 0.048 Uiso 1 1 calc R . . H14C H 0.2247 0.0772 0.2272 0.048 Uiso 1 1 calc R . . C15 C 0.28931(11) 0.11019(7) 0.47348(11) 0.0174(3) Uani 1 1 d . . . H15 H 0.2902 0.0636 0.4131 0.021 Uiso 1 1 calc R . . C16 C 0.27290(12) 0.07233(7) 0.59310(11) 0.0181(3) Uani 1 1 d U . . C17 C 0.31629(12) 0.11407(8) 0.70356(11) 0.0193(3) Uani 1 1 d . . . C18 C 0.29353(13) -0.01770(8) 0.80517(12) 0.0247(3) Uani 1 1 d . . . C19 C 0.20515(12) -0.00512(7) 0.59336(11) 0.0188(3) Uani 1 1 d U . . C20 C 0.42874(14) -0.05461(8) 0.78969(13) 0.0307(3) Uani 1 1 d . . . H20A H 0.4209 -0.1152 0.7810 0.046 Uiso 1 1 calc R . . H20B H 0.4902 -0.0413 0.8618 0.046 Uiso 1 1 calc R . . H20C H 0.4624 -0.0312 0.7162 0.046 Uiso 1 1 calc R . . C21 C 0.23803(16) -0.04483(10) 0.92163(13) 0.0382(4) Uani 1 1 d . . . H21A H 0.1538 -0.0162 0.9289 0.057 Uiso 1 1 calc R . . H21B H 0.3011 -0.0308 0.9923 0.057 Uiso 1 1 calc R . . H21C H 0.2232 -0.1051 0.9194 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0247(5) 0.0252(5) 0.0237(5) -0.0058(4) 0.0008(4) -0.0039(4) O2 0.0308(5) 0.0280(5) 0.0162(5) 0.0012(4) 0.0032(4) 0.0034(4) O3 0.0232(5) 0.0216(4) 0.0260(5) -0.0005(4) -0.0011(4) -0.0036(4) O4 0.0254(5) 0.0278(5) 0.0242(5) 0.0085(4) 0.0004(4) -0.0057(4) N1 0.0159(5) 0.0199(5) 0.0168(5) 0.0007(4) 0.0006(4) -0.0025(4) C1 0.0200(6) 0.0188(6) 0.0164(6) -0.0013(5) 0.0028(5) -0.0041(5) C2 0.0228(7) 0.0246(6) 0.0217(7) 0.0011(6) 0.0003(5) 0.0001(5) C3 0.0330(8) 0.0198(6) 0.0230(7) 0.0051(5) 0.0024(6) -0.0003(6) C4 0.0300(7) 0.0209(6) 0.0237(7) 0.0001(5) 0.0076(6) -0.0078(6) C5 0.0196(6) 0.0285(7) 0.0244(7) -0.0032(6) 0.0068(5) -0.0084(5) C6 0.0170(6) 0.0319(7) 0.0272(7) -0.0043(6) 0.0041(5) -0.0022(6) C7 0.0203(6) 0.0237(6) 0.0229(7) 0.0008(5) 0.0034(5) 0.0009(5) C8 0.0187(6) 0.0200(6) 0.0162(6) -0.0020(5) 0.0049(5) -0.0010(5) C9 0.0192(6) 0.0199(6) 0.0147(6) -0.0020(5) 0.0036(5) -0.0023(5) C10 0.0221(6) 0.0217(6) 0.0174(6) -0.0026(5) 0.0046(5) -0.0039(5) C11 0.0173(6) 0.0298(7) 0.0182(6) 0.0011(5) 0.0039(5) 0.0001(5) C12 0.0201(7) 0.0329(7) 0.0270(7) 0.0008(6) 0.0040(6) 0.0036(6) C13 0.0238(7) 0.0280(7) 0.0229(7) -0.0018(6) -0.0065(5) -0.0089(6) C14 0.0439(9) 0.0297(7) 0.0204(7) -0.0031(6) -0.0045(6) -0.0051(7) C15 0.0168(6) 0.0178(5) 0.0174(6) -0.0015(5) 0.0008(5) 0.0006(5) C16 0.0169(6) 0.0194(5) 0.0179(6) 0.0011(5) 0.0019(5) -0.0010(5) C17 0.0154(6) 0.0239(6) 0.0187(6) 0.0017(5) 0.0027(5) 0.0040(5) C18 0.0274(7) 0.0255(6) 0.0206(7) 0.0043(6) -0.0003(6) 0.0007(6) C19 0.0152(6) 0.0206(6) 0.0209(6) 0.0022(5) 0.0029(5) 0.0022(5) C20 0.0318(8) 0.0330(7) 0.0262(8) 0.0018(6) -0.0021(6) 0.0072(6) C21 0.0429(9) 0.0461(9) 0.0264(8) 0.0130(7) 0.0066(7) 0.0000(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.2254(14) . ? O2 C17 1.3845(14) . ? O2 C18 1.4386(15) . ? O3 C19 1.2235(15) . ? O4 C19 1.3846(14) . ? O4 C18 1.4290(15) . ? N1 C1 1.4843(14) . ? N1 C13 1.5195(15) . ? N1 C11 1.5267(15) . ? N1 C15 1.6603(15) . ? C1 C2 1.3639(17) . ? C1 C9 1.3955(17) . ? C2 C3 1.4220(17) . ? C3 C4 1.3715(18) . ? C4 C10 1.4184(17) . ? C5 C6 1.3702(18) . ? C5 C10 1.4227(18) . ? C6 C7 1.4140(16) . ? C7 C8 1.3639(17) . ? C8 C9 1.3959(17) . ? C8 C15 1.5047(16) . ? C9 C10 1.4071(16) . ? C11 C12 1.5135(17) . ? C13 C14 1.5128(18) . ? C15 C16 1.4691(16) . ? C16 C17 1.4152(17) . ? C16 C19 1.4214(16) . ? C18 C21 1.5085(18) . ? C18 C20 1.5178(18) . ? 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 C17 O2 C18 117.51(10) . . ? C19 O4 C18 118.02(9) . . ? C1 N1 C13 112.48(9) . . ? C1 N1 C11 112.11(9) . . ? C13 N1 C11 109.57(9) . . ? C1 N1 C15 104.42(8) . . ? C13 N1 C15 109.54(8) . . ? C11 N1 C15 108.53(8) . . ? C2 C1 C9 121.71(11) . . ? C2 C1 N1 128.83(11) . . ? C9 C1 N1 109.38(10) . . ? C1 C2 C3 116.32(12) . . ? C4 C3 C2 123.12(12) . . ? C3 C4 C10 120.44(11) . . ? C6 C5 C10 120.32(11) . . ? C5 C6 C7 122.32(12) . . ? C8 C7 C6 118.75(12) . . ? C7 C8 C9 119.12(11) . . ? C7 C8 C15 130.24(11) . . ? C9 C8 C15 110.53(10) . . ? C1 C9 C8 113.64(10) . . ? C1 C9 C10 122.41(11) . . ? C8 C9 C10 123.88(11) . . ? C9 C10 C4 115.93(12) . . ? C9 C10 C5 115.57(11) . . ? C4 C10 C5 128.45(11) . . ? C12 C11 N1 116.01(10) . . ? C14 C13 N1 113.88(10) . . ? C16 C15 C8 117.48(10) . . ? C16 C15 N1 116.70(9) . . ? C8 C15 N1 101.43(9) . . ? C17 C16 C19 121.51(11) . . ? C17 C16 C15 120.90(10) . . ? C19 C16 C15 117.48(11) . . ? O1 C17 O2 115.86(11) . . ? O1 C17 C16 127.20(11) . . ? O2 C17 C16 116.87(10) . . ? O4 C18 O2 110.82(10) . . ? O4 C18 C21 106.25(11) . . ? O2 C18 C21 106.15(11) . . ? O4 C18 C20 110.82(11) . . ? O2 C18 C20 109.26(10) . . ? C21 C18 C20 113.43(11) . . ? O3 C19 O4 116.62(10) . . ? O3 C19 C16 126.93(11) . . ? O4 C19 C16 116.43(11) . . ? _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.220 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.039 data_compound_25 _database_code_depnum_ccdc_archive 'CCDC 871644' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1(1-(dimethylamino)naphth-8-yl)-2,2-bis(acetyl)ethene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N O2' _chemical_formula_sum 'C18 H19 N O2' _chemical_formula_weight 281.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8270(4) _cell_length_b 8.7630(5) _cell_length_c 13.1899(7) _cell_angle_alpha 102.408(4) _cell_angle_beta 98.689(4) _cell_angle_gamma 94.696(3) _cell_volume 756.45(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 21689 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15388 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3453 _reflns_number_gt 2384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.1001P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3453 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.00698(19) 0.36203(14) 0.07932(10) 0.0342(3) Uani 1 1 d . . . O2 O -0.23209(17) 0.65391(14) 0.24324(10) 0.0321(3) Uani 1 1 d . . . N1 N 0.2278(2) 0.96144(16) 0.18171(11) 0.0274(4) Uani 1 1 d . . . C1 C 0.2734(2) 1.06408(19) 0.28445(13) 0.0233(4) Uani 1 1 d . . . C2 C 0.3263(2) 1.2233(2) 0.30047(14) 0.0272(4) Uani 1 1 d . . . H2 H 0.3433 1.2670 0.2420 0.033 Uiso 1 1 calc R . . C3 C 0.3558(2) 1.3226(2) 0.40200(14) 0.0280(4) Uani 1 1 d . . . H3 H 0.3938 1.4322 0.4115 0.034 Uiso 1 1 calc R . . C4 C 0.3301(2) 1.2625(2) 0.48656(13) 0.0256(4) Uani 1 1 d . . . H4 H 0.3460 1.3309 0.5544 0.031 Uiso 1 1 calc R . . C5 C 0.2521(2) 1.0348(2) 0.56216(13) 0.0240(4) Uani 1 1 d . . . H5 H 0.2691 1.1028 0.6303 0.029 Uiso 1 1 calc R . . C6 C 0.2015(2) 0.8777(2) 0.54993(13) 0.0254(4) Uani 1 1 d . . . H6 H 0.1773 0.8373 0.6088 0.030 Uiso 1 1 calc R . . C7 C 0.1850(2) 0.7749(2) 0.45030(13) 0.0238(4) Uani 1 1 d . . . H7 H 0.1531 0.6652 0.4434 0.029 Uiso 1 1 calc R . . C8 C 0.2138(2) 0.82944(19) 0.36240(12) 0.0216(4) Uani 1 1 d . . . C9 C 0.2559(2) 0.99580(18) 0.37235(12) 0.0209(4) Uani 1 1 d . . . C10 C 0.2796(2) 1.09833(19) 0.47435(13) 0.0223(4) Uani 1 1 d . . . C11 C 0.3463(3) 0.9989(2) 0.10501(15) 0.0427(5) Uani 1 1 d . . . H11A H 0.3099 1.0963 0.0861 0.064 Uiso 1 1 calc R . . H11B H 0.3203 0.9128 0.0417 0.064 Uiso 1 1 calc R . . H11C H 0.4884 1.0128 0.1357 0.064 Uiso 1 1 calc R . . C12 C 0.0136(3) 0.9422(2) 0.13953(14) 0.0331(4) Uani 1 1 d . . . H12A H -0.0617 0.9121 0.1913 0.050 Uiso 1 1 calc R . . H12B H -0.0156 0.8599 0.0742 0.050 Uiso 1 1 calc R . . H12C H -0.0251 1.0416 0.1250 0.050 Uiso 1 1 calc R . . C13 C 0.2254(2) 0.71323(19) 0.26412(12) 0.0220(4) Uani 1 1 d . . . H13 H 0.3389 0.7286 0.2322 0.026 Uiso 1 1 calc R . . C14 C 0.0909(2) 0.58848(19) 0.21594(13) 0.0235(4) Uani 1 1 d . . . C15 C 0.1238(3) 0.4714(2) 0.12250(13) 0.0249(4) Uani 1 1 d . . . C16 C 0.3130(3) 0.4908(2) 0.07901(14) 0.0325(4) Uani 1 1 d . . . H16A H 0.3130 0.4025 0.0191 0.049 Uiso 1 1 calc R . . H16B H 0.4279 0.4930 0.1339 0.049 Uiso 1 1 calc R . . H16C H 0.3216 0.5896 0.0556 0.049 Uiso 1 1 calc R . . C17 C -0.1098(3) 0.5611(2) 0.24802(13) 0.0262(4) Uani 1 1 d . . . C18 C -0.1536(3) 0.4148(2) 0.28693(16) 0.0375(5) Uani 1 1 d . . . H18A H -0.2876 0.4113 0.3051 0.056 Uiso 0.50 1 calc PR . . H18B H -0.0552 0.4160 0.3495 0.056 Uiso 0.50 1 calc PR . . H18C H -0.1466 0.3219 0.2315 0.056 Uiso 0.50 1 calc PR . . H18D H -0.0387 0.3548 0.2857 0.056 Uiso 0.50 1 calc PR . . H18E H -0.2711 0.3501 0.2413 0.056 Uiso 0.50 1 calc PR . . H18F H -0.1797 0.4442 0.3592 0.056 Uiso 0.50 1 calc PR . . 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 0.0375(7) 0.0284(7) 0.0314(7) -0.0001(5) 0.0041(6) -0.0038(6) O2 0.0263(7) 0.0324(7) 0.0353(7) 0.0028(6) 0.0044(5) 0.0053(6) N1 0.0317(8) 0.0282(8) 0.0218(8) 0.0061(6) 0.0043(6) 0.0012(6) C1 0.0202(8) 0.0251(9) 0.0234(9) 0.0044(7) 0.0021(7) 0.0024(7) C2 0.0275(9) 0.0260(9) 0.0290(10) 0.0102(7) 0.0032(7) 0.0013(7) C3 0.0249(9) 0.0212(9) 0.0360(10) 0.0054(7) 0.0019(7) 0.0005(7) C4 0.0224(9) 0.0240(9) 0.0277(9) 0.0012(7) 0.0027(7) 0.0025(7) C5 0.0188(8) 0.0310(10) 0.0203(8) 0.0026(7) 0.0021(6) 0.0034(7) C6 0.0232(9) 0.0314(10) 0.0232(9) 0.0089(7) 0.0053(7) 0.0040(7) C7 0.0214(8) 0.0232(9) 0.0266(9) 0.0069(7) 0.0032(7) 0.0011(7) C8 0.0168(8) 0.0241(9) 0.0230(9) 0.0046(7) 0.0017(6) 0.0020(6) C9 0.0160(8) 0.0234(9) 0.0225(9) 0.0039(7) 0.0031(6) 0.0024(6) C10 0.0150(8) 0.0256(9) 0.0254(9) 0.0046(7) 0.0020(6) 0.0041(7) C11 0.0542(13) 0.0457(12) 0.0293(10) 0.0074(9) 0.0154(9) 0.0000(10) C12 0.0379(11) 0.0315(10) 0.0257(10) 0.0037(8) -0.0032(8) 0.0028(8) C13 0.0231(8) 0.0227(9) 0.0227(8) 0.0092(7) 0.0049(7) 0.0043(7) C14 0.0246(9) 0.0216(8) 0.0246(9) 0.0058(7) 0.0043(7) 0.0035(7) C15 0.0283(9) 0.0222(8) 0.0240(9) 0.0068(7) 0.0015(7) 0.0034(7) C16 0.0324(10) 0.0345(10) 0.0294(10) 0.0017(8) 0.0091(8) 0.0045(8) C17 0.0269(9) 0.0249(9) 0.0229(9) -0.0006(7) 0.0022(7) 0.0000(7) C18 0.0323(10) 0.0344(11) 0.0491(12) 0.0132(9) 0.0143(9) 0.0013(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 C15 1.2294(19) . ? O2 C17 1.217(2) . ? N1 C1 1.430(2) . ? N1 C11 1.461(2) . ? N1 C12 1.466(2) . ? C1 C2 1.375(2) . ? C1 C9 1.430(2) . ? C2 C3 1.407(2) . ? C2 H2 0.9500 . ? C3 C4 1.360(2) . ? C3 H3 0.9500 . ? C4 C10 1.420(2) . ? C4 H4 0.9500 . ? C5 C6 1.360(2) . ? C5 C10 1.419(2) . ? C5 H5 0.9500 . ? C6 C7 1.408(2) . ? C6 H6 0.9500 . ? C7 C8 1.379(2) . ? C7 H7 0.9500 . ? C8 C9 1.436(2) . ? C8 C13 1.483(2) . ? C9 C10 1.426(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.343(2) . ? C13 H13 0.9500 . ? C14 C15 1.483(2) . ? C14 C17 1.509(2) . ? C15 C16 1.503(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.504(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 H18D 0.9800 . ? C18 H18E 0.9800 . ? C18 H18F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 115.82(14) . . ? C1 N1 C12 111.45(14) . . ? C11 N1 C12 111.32(15) . . ? C2 C1 C9 119.96(15) . . ? C2 C1 N1 122.65(15) . . ? C9 C1 N1 117.36(14) . . ? C1 C2 C3 121.16(16) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 120.29(16) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C10 120.63(16) . . ? C3 C4 H4 119.7 . . ? C10 C4 H4 119.7 . . ? C6 C5 C10 120.75(15) . . ? C6 C5 H5 119.6 . . ? C10 C5 H5 119.6 . . ? C5 C6 C7 120.17(15) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 121.67(15) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 119.07(14) . . ? C7 C8 C13 118.51(14) . . ? C9 C8 C13 121.97(14) . . ? C10 C9 C1 118.23(14) . . ? C10 C9 C8 118.71(14) . . ? C1 C9 C8 123.06(14) . . ? C5 C10 C4 120.93(15) . . ? C5 C10 C9 119.49(15) . . ? C4 C10 C9 119.57(15) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C8 126.31(15) . . ? C14 C13 H13 116.8 . . ? C8 C13 H13 116.8 . . ? C13 C14 C15 122.25(15) . . ? C13 C14 C17 123.03(15) . . ? C15 C14 C17 114.62(13) . . ? O1 C15 C14 119.62(15) . . ? O1 C15 C16 120.57(15) . . ? C14 C15 C16 119.77(14) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 C18 120.83(16) . . ? O2 C17 C14 121.50(15) . . ? C18 C17 C14 117.67(15) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C18 H18D 109.5 . . ? H18A C18 H18D 141.1 . . ? H18B C18 H18D 56.3 . . ? H18C C18 H18D 56.3 . . ? C17 C18 H18E 109.5 . . ? H18A C18 H18E 56.3 . . ? H18B C18 H18E 141.1 . . ? H18C C18 H18E 56.3 . . ? H18D C18 H18E 109.5 . . ? C17 C18 H18F 109.5 . . ? H18A C18 H18F 56.3 . . ? H18B C18 H18F 56.3 . . ? H18C C18 H18F 141.1 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? 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 C11 N1 C1 C2 36.4(2) . . . . ? C12 N1 C1 C2 -92.18(19) . . . . ? C11 N1 C1 C9 -145.59(16) . . . . ? C12 N1 C1 C9 85.79(18) . . . . ? C9 C1 C2 C3 -2.7(3) . . . . ? N1 C1 C2 C3 175.22(15) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 C10 2.1(2) . . . . ? C10 C5 C6 C7 3.0(2) . . . . ? C5 C6 C7 C8 -1.7(2) . . . . ? C6 C7 C8 C9 -1.9(2) . . . . ? C6 C7 C8 C13 170.55(14) . . . . ? C2 C1 C9 C10 4.7(2) . . . . ? N1 C1 C9 C10 -173.37(14) . . . . ? C2 C1 C9 C8 -175.90(15) . . . . ? N1 C1 C9 C8 6.1(2) . . . . ? C7 C8 C9 C10 4.2(2) . . . . ? C13 C8 C9 C10 -168.02(14) . . . . ? C7 C8 C9 C1 -175.28(15) . . . . ? C13 C8 C9 C1 12.5(2) . . . . ? C6 C5 C10 C4 179.24(15) . . . . ? C6 C5 C10 C9 -0.6(2) . . . . ? C3 C4 C10 C5 -179.83(15) . . . . ? C3 C4 C10 C9 0.0(2) . . . . ? C1 C9 C10 C5 176.51(14) . . . . ? C8 C9 C10 C5 -3.0(2) . . . . ? C1 C9 C10 C4 -3.3(2) . . . . ? C8 C9 C10 C4 177.20(14) . . . . ? C7 C8 C13 C14 53.2(2) . . . . ? C9 C8 C13 C14 -134.58(17) . . . . ? C8 C13 C14 C15 -174.90(14) . . . . ? C8 C13 C14 C17 8.8(3) . . . . ? C13 C14 C15 O1 -177.69(16) . . . . ? C17 C14 C15 O1 -1.1(2) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C17 C14 C15 C16 176.59(15) . . . . ? C13 C14 C17 O2 61.7(2) . . . . ? C15 C14 C17 O2 -114.88(17) . . . . ? C13 C14 C17 C18 -117.99(19) . . . . ? C15 C14 C17 C18 65.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.279 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.054 data_compound_26 _database_code_depnum_ccdc_archive 'CCDC 871645' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1!-Ethyl-2,2,2!-trimethyl-2!,4!-dihydro-1!H-spiro((1,3)dioxane- 5,3!-naphtho[1,8-bc]azepine)-4,6-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N O4' _chemical_formula_sum 'C21 H23 N O4' _chemical_formula_weight 353.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.2818(6) _cell_length_b 7.09570(10) _cell_length_c 16.7814(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.3740(10) _cell_angle_gamma 90.00 _cell_volume 3554.96(11) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17533 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCDcamera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21840 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4070 _reflns_number_gt 3462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+2.3975P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4070 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.11559(4) 1.21950(16) 0.31209(7) 0.0362(3) Uani 1 1 d . . . O2 O 0.05613(3) 1.28761(13) 0.20884(6) 0.0249(2) Uani 1 1 d . . . O3 O 0.01767(3) 1.05708(13) 0.11299(6) 0.0240(2) Uani 1 1 d . . . O4 O 0.04226(3) 0.76909(14) 0.11292(7) 0.0314(3) Uani 1 1 d . . . N1 N 0.14905(3) 0.80982(16) 0.32427(6) 0.0199(2) Uani 1 1 d . . . C1 C 0.17572(4) 0.67892(18) 0.29880(8) 0.0189(3) Uani 1 1 d . . . C2 C 0.20739(4) 0.5692(2) 0.35485(8) 0.0244(3) Uani 1 1 d . . . H2 H 0.2138 0.5921 0.4130 0.029 Uiso 1 1 calc R . . C3 C 0.23021(5) 0.4248(2) 0.32739(9) 0.0273(3) Uani 1 1 d . . . H3 H 0.2527 0.3552 0.3671 0.033 Uiso 1 1 calc R . . C4 C 0.22058(5) 0.3826(2) 0.24445(9) 0.0270(3) Uani 1 1 d . . . H4 H 0.2342 0.2770 0.2271 0.032 Uiso 1 1 calc R . . C5 C 0.18121(5) 0.4611(2) 0.09807(9) 0.0297(3) Uani 1 1 d . . . H5 H 0.1930 0.3507 0.0804 0.036 Uiso 1 1 calc R . . C6 C 0.15588(5) 0.5829(2) 0.03965(9) 0.0319(3) Uani 1 1 d . . . H6 H 0.1493 0.5553 -0.0182 0.038 Uiso 1 1 calc R . . C7 C 0.13964(5) 0.7493(2) 0.06589(8) 0.0270(3) Uani 1 1 d . . . H7 H 0.1236 0.8371 0.0251 0.032 Uiso 1 1 calc R . . C8 C 0.14642(4) 0.78827(19) 0.14913(8) 0.0204(3) Uani 1 1 d . . . C9 C 0.16978(4) 0.65525(18) 0.21088(8) 0.0191(3) Uani 1 1 d . . . C10 C 0.19018(4) 0.49707(19) 0.18459(8) 0.0231(3) Uani 1 1 d . . . C11 C 0.10195(4) 0.81655(18) 0.27493(8) 0.0202(3) Uani 1 1 d . . . H11 H 0.0962 0.6963 0.2424 0.024 Uiso 1 1 calc R . . C12 C 0.09248(4) 0.97879(18) 0.20790(8) 0.0196(3) Uani 1 1 d . . . C13 C 0.13347(4) 0.97968(18) 0.17329(8) 0.0213(3) Uani 1 1 d . . . H13B H 0.1266 1.0629 0.1237 0.026 Uiso 1 1 calc R . . H13A H 0.1595 1.0343 0.2162 0.026 Uiso 1 1 calc R . . C14 C 0.16297(5) 0.8787(2) 0.40997(8) 0.0292(3) Uani 1 1 d . . . H14B H 0.1683 0.7699 0.4486 0.035 Uiso 1 1 calc R . . H14A H 0.1385 0.9548 0.4196 0.035 Uiso 1 1 calc R . . C15 C 0.20491(5) 0.9973(2) 0.42936(10) 0.0390(4) Uani 1 1 d . . . H15A H 0.2295 0.9217 0.4214 0.058 Uiso 1 1 calc R . . H15B H 0.2128 1.0406 0.4874 0.058 Uiso 1 1 calc R . . H15C H 0.1996 1.1065 0.3919 0.058 Uiso 1 1 calc R . . C16 C 0.06894(5) 0.8176(2) 0.32602(10) 0.0311(3) Uani 1 1 d . . . H16C H 0.0762 0.7146 0.3668 0.047 Uiso 1 1 calc R . . H16B H 0.0384 0.8006 0.2887 0.047 Uiso 1 1 calc R . . H16A H 0.0710 0.9381 0.3554 0.047 Uiso 1 1 calc R . . C17 C 0.08995(4) 1.17021(19) 0.24711(8) 0.0222(3) Uani 1 1 d . . . C18 C 0.02828(4) 1.25419(18) 0.12497(8) 0.0214(3) Uani 1 1 d . . . C19 C 0.04977(4) 0.92618(18) 0.14025(8) 0.0205(3) Uani 1 1 d . . . C20 C 0.05104(5) 1.32091(19) 0.06251(8) 0.0246(3) Uani 1 1 d . . . H20A H 0.0791 1.2515 0.0707 0.037 Uiso 1 1 calc R . . H20B H 0.0575 1.4560 0.0704 0.037 Uiso 1 1 calc R . . H20C H 0.0313 1.2986 0.0058 0.037 Uiso 1 1 calc R . . C21 C -0.01540(5) 1.3531(2) 0.11694(9) 0.0287(3) Uani 1 1 d . . . H21C H -0.0361 1.3310 0.0611 0.043 Uiso 1 1 calc R . . H21B H -0.0100 1.4887 0.1256 0.043 Uiso 1 1 calc R . . H21A H -0.0285 1.3040 0.1590 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0330(6) 0.0286(6) 0.0371(6) -0.0099(5) -0.0044(5) 0.0035(5) O2 0.0309(5) 0.0214(5) 0.0205(5) -0.0003(4) 0.0049(4) 0.0075(4) O3 0.0192(4) 0.0176(5) 0.0313(5) 0.0047(4) 0.0018(4) 0.0006(4) O4 0.0270(5) 0.0197(5) 0.0389(6) -0.0047(4) -0.0032(4) -0.0004(4) N1 0.0171(5) 0.0239(6) 0.0185(5) 0.0001(4) 0.0050(4) 0.0017(4) C1 0.0169(6) 0.0185(6) 0.0219(6) 0.0021(5) 0.0069(5) -0.0014(5) C2 0.0238(6) 0.0255(7) 0.0230(6) 0.0041(5) 0.0056(5) 0.0014(5) C3 0.0215(6) 0.0250(7) 0.0324(7) 0.0067(6) 0.0035(5) 0.0050(5) C4 0.0215(6) 0.0216(7) 0.0376(8) -0.0010(6) 0.0084(6) 0.0044(5) C5 0.0245(7) 0.0329(8) 0.0328(7) -0.0092(6) 0.0101(6) 0.0026(6) C6 0.0289(7) 0.0442(9) 0.0232(7) -0.0068(6) 0.0086(6) 0.0021(6) C7 0.0247(7) 0.0347(8) 0.0218(6) 0.0036(6) 0.0071(5) 0.0031(6) C8 0.0159(6) 0.0238(6) 0.0228(6) 0.0019(5) 0.0078(5) 0.0000(5) C9 0.0147(5) 0.0204(6) 0.0223(6) 0.0007(5) 0.0055(5) -0.0010(5) C10 0.0177(6) 0.0242(7) 0.0276(7) -0.0023(5) 0.0071(5) 0.0001(5) C11 0.0168(6) 0.0206(6) 0.0236(6) 0.0034(5) 0.0064(5) 0.0006(5) C12 0.0169(6) 0.0167(6) 0.0241(6) 0.0001(5) 0.0044(5) 0.0006(5) C13 0.0192(6) 0.0210(6) 0.0236(6) 0.0050(5) 0.0064(5) 0.0005(5) C14 0.0304(7) 0.0373(8) 0.0195(6) 0.0001(6) 0.0069(5) 0.0064(6) C15 0.0324(8) 0.0437(10) 0.0345(8) -0.0106(7) 0.0002(6) -0.0003(7) C16 0.0228(7) 0.0387(8) 0.0354(8) 0.0072(6) 0.0141(6) 0.0020(6) C17 0.0201(6) 0.0201(6) 0.0258(7) -0.0007(5) 0.0060(5) -0.0001(5) C18 0.0242(6) 0.0167(6) 0.0215(6) 0.0018(5) 0.0039(5) 0.0020(5) C19 0.0182(6) 0.0182(6) 0.0245(6) 0.0029(5) 0.0051(5) 0.0008(5) C20 0.0285(7) 0.0209(6) 0.0254(7) 0.0047(5) 0.0095(5) 0.0038(5) C21 0.0279(7) 0.0260(7) 0.0333(7) 0.0090(6) 0.0109(6) 0.0087(6) _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 C17 1.1969(16) . ? O2 C17 1.3490(16) . ? O2 C18 1.4366(15) . ? O3 C19 1.3440(16) . ? O3 C18 1.4376(16) . ? O4 C19 1.2016(16) . ? N1 C1 1.3981(17) . ? N1 C14 1.4570(17) . ? N1 C11 1.4593(16) . ? C1 C2 1.3841(18) . ? C1 C9 1.4407(17) . ? C2 C3 1.403(2) . ? C2 H2 0.9500 . ? C3 C4 1.367(2) . ? C3 H3 0.9500 . ? C4 C10 1.4154(19) . ? C4 H4 0.9500 . ? C5 C6 1.368(2) . ? C5 C10 1.4172(19) . ? C5 H5 0.9500 . ? C6 C7 1.407(2) . ? C6 H6 0.9500 . ? C7 C8 1.3768(19) . ? C7 H7 0.9500 . ? C8 C9 1.4305(18) . ? C8 C13 1.5071(18) . ? C9 C10 1.4247(18) . ? C11 C16 1.5264(18) . ? C11 C12 1.5746(18) . ? C11 H11 1.0000 . ? C12 C19 1.5188(17) . ? C12 C17 1.5216(18) . ? C12 C13 1.5577(18) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 C15 1.510(2) . ? C14 H14B 0.9900 . ? C14 H14A 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16C 0.9800 . ? C16 H16B 0.9800 . ? C16 H16A 0.9800 . ? C18 C21 1.5061(19) . ? C18 C20 1.5084(19) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21C 0.9800 . ? C21 H21B 0.9800 . ? C21 H21A 0.9800 . ? 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 C17 O2 C18 121.63(10) . . ? C19 O3 C18 120.46(10) . . ? C1 N1 C14 119.66(11) . . ? C1 N1 C11 116.22(10) . . ? C14 N1 C11 120.17(11) . . ? C2 C1 N1 122.50(12) . . ? C2 C1 C9 118.54(12) . . ? N1 C1 C9 118.96(11) . . ? C1 C2 C3 121.24(13) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 121.04(12) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C10 119.61(13) . . ? C3 C4 H4 120.2 . . ? C10 C4 H4 120.2 . . ? C6 C5 C10 121.04(14) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C5 C6 C7 119.45(13) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 121.68(13) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 119.55(12) . . ? C7 C8 C13 118.78(12) . . ? C9 C8 C13 121.33(11) . . ? C10 C9 C8 118.33(12) . . ? C10 C9 C1 118.44(11) . . ? C8 C9 C1 123.15(12) . . ? C4 C10 C5 120.61(13) . . ? C4 C10 C9 120.04(12) . . ? C5 C10 C9 119.29(12) . . ? N1 C11 C16 114.78(11) . . ? N1 C11 C12 111.84(10) . . ? C16 C11 C12 112.53(11) . . ? N1 C11 H11 105.6 . . ? C16 C11 H11 105.6 . . ? C12 C11 H11 105.6 . . ? C19 C12 C17 113.26(10) . . ? C19 C12 C13 111.14(10) . . ? C17 C12 C13 108.22(10) . . ? C19 C12 C11 106.87(10) . . ? C17 C12 C11 111.51(11) . . ? C13 C12 C11 105.61(10) . . ? C8 C13 C12 114.46(10) . . ? C8 C13 H13B 108.6 . . ? C12 C13 H13B 108.6 . . ? C8 C13 H13A 108.6 . . ? C12 C13 H13A 108.6 . . ? H13B C13 H13A 107.6 . . ? N1 C14 C15 112.59(12) . . ? N1 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? N1 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? H14B C14 H14A 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16C 109.5 . . ? C11 C16 H16B 109.5 . . ? H16C C16 H16B 109.5 . . ? C11 C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? O1 C17 O2 118.06(12) . . ? O1 C17 C12 123.20(12) . . ? O2 C17 C12 118.69(11) . . ? O2 C18 O3 110.17(10) . . ? O2 C18 C21 106.22(11) . . ? O3 C18 C21 105.99(11) . . ? O2 C18 C20 110.79(11) . . ? O3 C18 C20 110.21(11) . . ? C21 C18 C20 113.29(11) . . ? O4 C19 O3 118.04(11) . . ? O4 C19 C12 122.78(11) . . ? O3 C19 C12 119.05(11) . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21C 109.5 . . ? C18 C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? C18 C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? H21B C21 H21A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.438 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.094 data_compound_27 _database_code_depnum_ccdc_archive 'CCDC 871646' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Ethyl-2-methyl-1,2-dihydronaphtho[1,8-bc]azepine-3,3(4H)-dicarbonitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N3' _chemical_formula_sum 'C18 H17 N3' _chemical_formula_weight 275.35 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.0771(5) _cell_length_b 6.6633(2) _cell_length_c 15.5200(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.378(4) _cell_angle_gamma 90.00 _cell_volume 1470.86(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4098 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 29.06 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9832 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6898 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3365 _reflns_number_gt 2690 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.1325P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3365 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.48407(6) 0.57130(14) 0.22810(6) 0.0176(2) Uani 1 1 d . . . N2 N 0.39635(8) 1.08492(16) 0.25683(8) 0.0313(3) Uani 1 1 d . . . N3 N 0.45872(8) 0.76546(16) 0.51629(7) 0.0312(3) Uani 1 1 d . . . C1 C 0.56281(7) 0.44584(16) 0.24315(7) 0.0170(2) Uani 1 1 d . . . C2 C 0.57083(8) 0.31385(17) 0.17736(8) 0.0215(3) Uani 1 1 d . . . H2 H 0.5251 0.3165 0.1180 0.026 Uiso 1 1 calc R . . C3 C 0.64537(8) 0.17595(18) 0.19666(8) 0.0240(3) Uani 1 1 d . . . H3 H 0.6515 0.0922 0.1494 0.029 Uiso 1 1 calc R . . C4 C 0.70907(8) 0.16106(18) 0.28259(8) 0.0231(3) Uani 1 1 d . . . H4 H 0.7562 0.0602 0.2961 0.028 Uiso 1 1 calc R . . C5 C 0.77032(8) 0.28275(19) 0.44173(8) 0.0254(3) Uani 1 1 d . . . H5 H 0.8138 0.1746 0.4572 0.030 Uiso 1 1 calc R . . C6 C 0.77179(8) 0.4223(2) 0.50636(8) 0.0282(3) Uani 1 1 d . . . H6 H 0.8135 0.4072 0.5672 0.034 Uiso 1 1 calc R . . C7 C 0.71102(8) 0.58930(19) 0.48238(8) 0.0246(3) Uani 1 1 d . . . H7 H 0.7158 0.6914 0.5264 0.030 Uiso 1 1 calc R . . C8 C 0.64504(7) 0.60806(17) 0.39693(7) 0.0186(2) Uani 1 1 d . . . C9 C 0.63596(7) 0.45157(17) 0.33072(7) 0.0167(2) Uani 1 1 d . . . C10 C 0.70491(8) 0.29587(17) 0.35162(8) 0.0198(2) Uani 1 1 d . . . C11 C 0.44633(7) 0.58492(16) 0.30354(7) 0.0176(2) Uani 1 1 d . . . H11 H 0.4742 0.4711 0.3459 0.021 Uiso 1 1 calc R . . C12 C 0.48465(8) 0.78363(16) 0.35751(7) 0.0178(2) Uani 1 1 d . . . C13 C 0.59120(8) 0.80236(17) 0.37126(8) 0.0191(2) Uani 1 1 d . . . H13A H 0.5984 0.8533 0.3140 0.023 Uiso 1 1 calc R . . H13B H 0.6193 0.9026 0.4197 0.023 Uiso 1 1 calc R . . C14 C 0.42351(8) 0.6118(2) 0.13472(8) 0.0253(3) Uani 1 1 d . . . H14A H 0.3673 0.6866 0.1363 0.030 Uiso 1 1 calc R . . H14B H 0.4019 0.4828 0.1031 0.030 Uiso 1 1 calc R . . C15 C 0.47274(10) 0.7320(2) 0.08102(9) 0.0370(3) Uani 1 1 d . . . H15A H 0.4940 0.8603 0.1118 0.056 Uiso 1 1 calc R . . H15C H 0.4290 0.7570 0.0193 0.056 Uiso 1 1 calc R . . H15B H 0.5271 0.6564 0.0772 0.056 Uiso 1 1 calc R . . C16 C 0.33986(8) 0.56656(18) 0.27753(9) 0.0240(3) Uani 1 1 d . . . H16A H 0.3098 0.6839 0.2415 0.036 Uiso 1 1 calc R . . H16B H 0.3227 0.5594 0.3331 0.036 Uiso 1 1 calc R . . H16C H 0.3186 0.4446 0.2413 0.036 Uiso 1 1 calc R . . C17 C 0.43489(8) 0.95833(18) 0.30425(8) 0.0213(3) Uani 1 1 d . . . C18 C 0.46894(8) 0.77682(17) 0.44669(8) 0.0210(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0160(4) 0.0214(5) 0.0149(4) -0.0014(4) 0.0044(4) 0.0027(4) N2 0.0325(6) 0.0231(6) 0.0352(6) 0.0018(5) 0.0073(5) 0.0037(5) N3 0.0439(7) 0.0269(6) 0.0277(6) -0.0033(5) 0.0186(5) -0.0048(5) C1 0.0166(5) 0.0159(5) 0.0195(5) 0.0013(4) 0.0076(4) -0.0004(4) C2 0.0220(6) 0.0227(6) 0.0194(6) -0.0023(5) 0.0064(5) -0.0001(5) C3 0.0266(6) 0.0208(6) 0.0295(6) -0.0042(5) 0.0157(5) 0.0002(5) C4 0.0213(6) 0.0197(6) 0.0321(6) 0.0044(5) 0.0140(5) 0.0038(5) C5 0.0176(5) 0.0287(7) 0.0295(6) 0.0107(5) 0.0073(5) 0.0042(5) C6 0.0203(6) 0.0397(8) 0.0206(6) 0.0065(5) 0.0017(5) -0.0014(6) C7 0.0220(6) 0.0302(7) 0.0205(6) -0.0024(5) 0.0055(5) -0.0051(5) C8 0.0159(5) 0.0218(6) 0.0196(5) 0.0005(5) 0.0076(4) -0.0040(5) C9 0.0156(5) 0.0186(6) 0.0178(5) 0.0026(4) 0.0080(4) -0.0011(4) C10 0.0164(5) 0.0211(6) 0.0240(6) 0.0057(5) 0.0095(5) -0.0002(5) C11 0.0176(5) 0.0163(5) 0.0200(5) -0.0018(4) 0.0078(5) -0.0008(4) C12 0.0212(5) 0.0161(5) 0.0176(5) -0.0010(4) 0.0081(5) -0.0001(5) C13 0.0200(5) 0.0179(6) 0.0198(5) -0.0032(5) 0.0072(5) -0.0049(5) C14 0.0216(6) 0.0322(7) 0.0180(6) -0.0032(5) 0.0012(5) 0.0061(5) C15 0.0397(8) 0.0465(9) 0.0249(7) 0.0111(6) 0.0109(6) 0.0138(7) C16 0.0188(5) 0.0222(6) 0.0327(7) -0.0041(5) 0.0108(5) -0.0015(5) C17 0.0238(6) 0.0182(6) 0.0234(6) -0.0036(5) 0.0101(5) -0.0013(5) C18 0.0243(6) 0.0149(5) 0.0248(6) -0.0027(5) 0.0098(5) -0.0016(5) _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 C1 1.4067(14) . ? N1 C14 1.4591(14) . ? N1 C11 1.4644(13) . ? N2 C17 1.1432(15) . ? N3 C18 1.1431(15) . ? C1 C2 1.3830(15) . ? C1 C9 1.4388(15) . ? C2 C3 1.4049(16) . ? C3 C4 1.3642(17) . ? C4 C10 1.4154(17) . ? C5 C6 1.3625(18) . ? C5 C10 1.4216(16) . ? C6 C7 1.4106(18) . ? C7 C8 1.3743(15) . ? C8 C9 1.4382(15) . ? C8 C13 1.5097(16) . ? C9 C10 1.4278(15) . ? C11 C16 1.5248(15) . ? C11 C12 1.5708(15) . ? C12 C17 1.4798(16) . ? C12 C18 1.4804(15) . ? C12 C13 1.5538(15) . ? C14 C15 1.5157(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C14 119.36(9) . . ? C1 N1 C11 115.75(9) . . ? C14 N1 C11 120.10(9) . . ? C2 C1 N1 122.07(10) . . ? C2 C1 C9 119.14(10) . . ? N1 C1 C9 118.77(9) . . ? C1 C2 C3 121.22(11) . . ? C4 C3 C2 120.66(11) . . ? C3 C4 C10 120.01(10) . . ? C6 C5 C10 121.25(11) . . ? C5 C6 C7 119.58(11) . . ? C8 C7 C6 121.68(11) . . ? C7 C8 C9 119.36(11) . . ? C7 C8 C13 119.10(10) . . ? C9 C8 C13 121.19(10) . . ? C10 C9 C8 118.36(10) . . ? C10 C9 C1 117.86(10) . . ? C8 C9 C1 123.75(10) . . ? C4 C10 C5 121.00(10) . . ? C4 C10 C9 120.07(10) . . ? C5 C10 C9 118.90(10) . . ? N1 C11 C16 115.95(9) . . ? N1 C11 C12 107.87(8) . . ? C16 C11 C12 112.17(9) . . ? C17 C12 C18 109.73(9) . . ? C17 C12 C13 108.84(9) . . ? C18 C12 C13 110.67(9) . . ? C17 C12 C11 109.67(9) . . ? C18 C12 C11 109.16(9) . . ? C13 C12 C11 108.75(9) . . ? C8 C13 C12 114.09(9) . . ? N1 C14 C15 112.63(10) . . ? N2 C17 C12 174.39(12) . . ? N3 C18 C12 177.54(13) . . ? _diffrn_measured_fraction_theta_max 0.851 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.291 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.038 _vrf_PLAT230_et2babs ; PROBLEM: Hirshfeld Test Diff for C11 -- C13 8.69 su RESPONSE: This bond is from a sp3 C to the sp of a nitrile. The component of the atomic displacement parameter along the two bonds at the sp C is likely to express to some degree the large electron density in the adjacent triple bond. ; data_compound_28 _database_code_depnum_ccdc_archive 'CCDC 871647' #TrackingRef '10132_web_deposit_cif_file_0_PROFJOHNWALLIS_1331752951.ZWITS CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1!-Methyl-2!,4!-dihydro-1!H-spiro(indene-2,3!-naphtho[1,8-bc]azepine)-1,3-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H17 N O2' _chemical_formula_sum 'C22 H17 N O2' _chemical_formula_weight 327.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.9448(12) _cell_length_b 7.7430(6) _cell_length_c 26.4365(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3263.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3928 _cell_measurement_theta_min 2.9797 _cell_measurement_theta_max 28.9966 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9832 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10919 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 29.03 _reflns_number_total 3842 _reflns_number_gt 2281 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. DELU restraints were applied to N1 C11 C12 C20, C21 and C22. ; _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^)+(0.0608P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3842 _refine_ls_number_parameters 227 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.25561(6) 0.40244(18) 0.35661(4) 0.0665(4) Uani 1 1 d . . . O2 O 0.00398(6) 0.53308(19) 0.27166(5) 0.0762(4) Uani 1 1 d . . . N1 N 0.07171(8) 0.28807(17) 0.40968(6) 0.0585(4) Uani 1 1 d U . . C1 C -0.00130(9) 0.3408(2) 0.43454(7) 0.0520(4) Uani 1 1 d . . . C2 C -0.04113(13) 0.2363(3) 0.46943(7) 0.0703(6) Uani 1 1 d . . . H2 H -0.0169 0.1281 0.4780 0.084 Uiso 1 1 calc R . . C3 C -0.11612(14) 0.2858(4) 0.49244(8) 0.0786(7) Uani 1 1 d . . . H3 H -0.1418 0.2118 0.5166 0.094 Uiso 1 1 calc R . . C4 C -0.15219(11) 0.4370(4) 0.48078(7) 0.0709(6) Uani 1 1 d . . . H4 H -0.2041 0.4675 0.4960 0.085 Uiso 1 1 calc R . . C5 C -0.15051(10) 0.7127(3) 0.43564(7) 0.0691(6) Uani 1 1 d . . . H5 H -0.2033 0.7406 0.4502 0.083 Uiso 1 1 calc R . . C6 C -0.11231(11) 0.8284(3) 0.40550(8) 0.0705(6) Uani 1 1 d . . . H6 H -0.1385 0.9360 0.3986 0.085 Uiso 1 1 calc R . . C7 C -0.03308(10) 0.7901(2) 0.38395(7) 0.0587(5) Uani 1 1 d . . . H7 H -0.0065 0.8732 0.3629 0.070 Uiso 1 1 calc R . . C8 C 0.00581(8) 0.6353(2) 0.39292(6) 0.0435(4) Uani 1 1 d . . . C9 C -0.03550(8) 0.5076(2) 0.42320(6) 0.0451(4) Uani 1 1 d . . . C10 C -0.11400(8) 0.5517(3) 0.44610(6) 0.0550(5) Uani 1 1 d . . . C11 C 0.07038(10) 0.3039(2) 0.35502(7) 0.0593(4) Uani 1 1 d U . . H11A H 0.0115 0.2988 0.3433 0.071 Uiso 1 1 calc R . . H11B H 0.1005 0.2042 0.3401 0.071 Uiso 1 1 calc R . . C12 C 0.11059(8) 0.4719(2) 0.33537(6) 0.0455(4) Uani 1 1 d U . . C13 C 0.09550(8) 0.6150(2) 0.37504(6) 0.0448(4) Uani 1 1 d . . . H13B H 0.1312 0.5909 0.4048 0.054 Uiso 1 1 calc R . . H13A H 0.1142 0.7264 0.3605 0.054 Uiso 1 1 calc R . . C14 C 0.11963(13) 0.1438(3) 0.43023(9) 0.0887(7) Uani 1 1 d . . . H14A H 0.1258 0.1583 0.4669 0.133 Uiso 1 1 calc R . . H14B H 0.1752 0.1407 0.4144 0.133 Uiso 1 1 calc R . . H14C H 0.0901 0.0354 0.4232 0.133 Uiso 1 1 calc R . . C15 C 0.20522(8) 0.4579(2) 0.32633(6) 0.0457(4) Uani 1 1 d . . . C16 C 0.22396(8) 0.52387(19) 0.27503(6) 0.0403(4) Uani 1 1 d . . . C17 C 0.30097(8) 0.5446(2) 0.25130(6) 0.0467(4) Uani 1 1 d . . . H17 H 0.3516 0.5140 0.2680 0.056 Uiso 1 1 calc R . . C18 C 0.30204(9) 0.6107(2) 0.20288(7) 0.0505(4) Uani 1 1 d . . . H18 H 0.3541 0.6263 0.1860 0.061 Uiso 1 1 calc R . . C19 C 0.22771(9) 0.6550(2) 0.17841(7) 0.0579(5) Uani 1 1 d . . . H19 H 0.2297 0.7021 0.1453 0.069 Uiso 1 1 calc R . . C20 C 0.15096(9) 0.6310(2) 0.20191(7) 0.0584(5) Uani 1 1 d U . . H20 H 0.1002 0.6589 0.1850 0.070 Uiso 1 1 calc R . . C21 C 0.14989(8) 0.5657(2) 0.25054(7) 0.0450(4) Uani 1 1 d U . . C22 C 0.07742(8) 0.5259(2) 0.28375(6) 0.0519(4) Uani 1 1 d U . . 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 0.0328(5) 0.1018(10) 0.0648(8) -0.0158(7) -0.0072(5) 0.0167(6) O2 0.0184(5) 0.1161(12) 0.0939(10) -0.0191(8) -0.0094(5) 0.0058(6) N1 0.0552(8) 0.0381(8) 0.0820(10) -0.0152(7) 0.0047(8) 0.0002(7) C1 0.0413(8) 0.0434(10) 0.0715(12) -0.0152(9) -0.0011(8) -0.0161(8) C2 0.0804(14) 0.0521(12) 0.0785(14) -0.0053(10) -0.0075(11) -0.0307(11) C3 0.0727(14) 0.0951(19) 0.0681(14) -0.0122(12) 0.0082(11) -0.0523(14) C4 0.0391(9) 0.1143(19) 0.0593(12) -0.0210(12) 0.0072(9) -0.0365(12) C5 0.0321(8) 0.1120(18) 0.0631(13) -0.0201(12) 0.0036(8) 0.0156(10) C6 0.0595(11) 0.0801(15) 0.0720(13) -0.0154(11) -0.0019(10) 0.0352(11) C7 0.0544(10) 0.0518(12) 0.0698(12) -0.0093(9) 0.0111(8) 0.0110(9) C8 0.0280(7) 0.0419(10) 0.0607(11) -0.0145(7) 0.0053(6) -0.0015(7) C9 0.0245(7) 0.0496(10) 0.0610(11) -0.0134(8) 0.0011(7) -0.0094(7) C10 0.0245(7) 0.0834(14) 0.0571(11) -0.0194(10) -0.0005(7) -0.0099(9) C11 0.0449(9) 0.0474(10) 0.0856(11) -0.0299(8) 0.0062(8) -0.0109(8) C12 0.0204(6) 0.0485(9) 0.0677(9) -0.0224(7) 0.0016(6) -0.0034(6) C13 0.0287(7) 0.0384(9) 0.0674(11) -0.0169(7) 0.0097(7) -0.0087(7) C14 0.1029(16) 0.0459(13) 0.1173(18) -0.0188(11) -0.0091(13) 0.0173(12) C15 0.0242(7) 0.0513(10) 0.0616(11) -0.0257(9) -0.0028(7) 0.0031(7) C16 0.0217(6) 0.0400(9) 0.0593(11) -0.0251(8) -0.0032(6) 0.0026(6) C17 0.0224(7) 0.0574(11) 0.0601(11) -0.0291(9) -0.0030(7) 0.0029(7) C18 0.0316(8) 0.0524(10) 0.0675(12) -0.0224(9) 0.0056(7) -0.0019(7) C19 0.0497(9) 0.0533(11) 0.0707(12) -0.0054(9) 0.0018(8) 0.0096(9) C20 0.0360(8) 0.0588(12) 0.0804(12) -0.0040(9) -0.0077(8) 0.0159(8) C21 0.0242(7) 0.0447(10) 0.0661(10) -0.0182(8) -0.0054(6) 0.0059(7) C22 0.0217(7) 0.0563(10) 0.0778(11) -0.0239(8) -0.0045(6) 0.0020(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.2126(18) . ? O2 C22 1.2151(16) . ? N1 C1 1.398(2) . ? N1 C11 1.450(2) . ? N1 C14 1.459(2) . ? C1 C2 1.382(2) . ? C1 C9 1.434(2) . ? C2 C3 1.395(3) . ? C2 H2 0.9500 . ? C3 C4 1.340(3) . ? C3 H3 0.9500 . ? C4 C10 1.414(3) . ? C4 H4 0.9500 . ? C5 C6 1.344(3) . ? C5 C10 1.403(3) . ? C5 H5 0.9500 . ? C6 C7 1.417(2) . ? C6 H6 0.9500 . ? C7 C8 1.370(2) . ? C7 H7 0.9500 . ? C8 C9 1.433(2) . ? C8 C13 1.5142(18) . ? C9 C10 1.4316(19) . ? C11 C12 1.541(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C22 1.522(2) . ? C12 C15 1.5315(18) . ? C12 C13 1.545(2) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.480(2) . ? C16 C21 1.3853(19) . ? C16 C17 1.3882(19) . ? C17 C18 1.379(2) . ? C17 H17 0.9500 . ? C18 C19 1.393(2) . ? C18 H18 0.9500 . ? C19 C20 1.385(2) . ? C19 H19 0.9500 . ? C20 C21 1.382(2) . ? C20 H20 0.9500 . ? C21 C22 1.484(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 C1 N1 C11 115.57(14) . . ? C1 N1 C14 119.01(16) . . ? C11 N1 C14 116.32(14) . . ? C2 C1 N1 121.70(17) . . ? C2 C1 C9 119.50(16) . . ? N1 C1 C9 118.79(15) . . ? C1 C2 C3 121.6(2) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C10 120.85(18) . . ? C3 C4 H4 119.6 . . ? C10 C4 H4 119.6 . . ? C6 C5 C10 121.36(15) . . ? C6 C5 H5 119.3 . . ? C10 C5 H5 119.3 . . ? C5 C6 C7 120.18(18) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 121.13(18) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 119.49(13) . . ? C7 C8 C13 117.66(15) . . ? C9 C8 C13 122.48(14) . . ? C10 C9 C8 118.28(15) . . ? C10 C9 C1 117.32(15) . . ? C8 C9 C1 124.31(13) . . ? C5 C10 C4 120.46(18) . . ? C5 C10 C9 119.42(17) . . ? C4 C10 C9 120.05(19) . . ? N1 C11 C12 113.66(12) . . ? N1 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? N1 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C22 C12 C15 102.82(13) . . ? C22 C12 C11 112.93(12) . . ? C15 C12 C11 113.76(13) . . ? C22 C12 C13 110.95(13) . . ? C15 C12 C13 108.08(11) . . ? C11 C12 C13 108.18(13) . . ? C8 C13 C12 115.69(11) . . ? C8 C13 H13B 108.4 . . ? C12 C13 H13B 108.4 . . ? C8 C13 H13A 108.4 . . ? C12 C13 H13A 108.4 . . ? H13B C13 H13A 107.4 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 C16 126.40(13) . . ? O1 C15 C12 125.08(16) . . ? C16 C15 C12 108.51(13) . . ? C21 C16 C17 121.05(16) . . ? C21 C16 C15 109.69(12) . . ? C17 C16 C15 129.25(13) . . ? C18 C17 C16 118.26(13) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? C17 C18 C19 120.79(14) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 120.71(17) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C21 C20 C19 118.51(14) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C20 C21 C16 120.66(13) . . ? C20 C21 C22 129.52(13) . . ? C16 C21 C22 109.80(15) . . ? O2 C22 C21 125.84(16) . . ? O2 C22 C12 125.68(15) . . ? C21 C22 C12 108.48(12) . . ? _diffrn_measured_fraction_theta_max 0.881 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.180 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.030 #===END ##############################################################