# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'J. Wallis' 'Xavier Formosa' ; Jane O'Leary ; 'Wolfgang Skranc' _publ_contact_author_name 'Dr John Wallis' _publ_contact_author_address ; School of Biomedical and Natural Sciences The Nottingham Trent University Clifton Lane Nottingham NG11 8NS ; _publ_contact_author_email JOHN.WALLIS@NTU.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Structural Studies of Peri-Interactions and Bond Formation Between Electron-rich Atomic Centres and N-Phenylcarboxamides or Nitroalkenyl Groups ; data_methoxy-N-phenylamide _database_code_depnum_ccdc_archive 'CCDC 270918' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-Phenyl-8-methoxy-1-naphthamide ; _chemical_name_common ? _chemical_melting_point 461-463 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O2' _chemical_formula_weight 277.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7709(4) _cell_length_b 12.8905(5) _cell_length_c 13.2494(6) _cell_angle_alpha 70.822(2) _cell_angle_beta 68.5730(18) _cell_angle_gamma 76.360(2) _cell_volume 1454.45(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20782 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.637 _exptl_absorpt_correction_T_max 0.637 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) ; _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20782 _diffrn_reflns_av_R_equivalents 0.0993 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6430 _reflns_number_gt 3576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. One molecule is disordered over two positions, its orientations are labelled B and C, and the structure was refined in blocks, the last cycle containing only the non-disordered molecule A. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1040P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6430 _refine_ls_number_parameters 554 _refine_ls_number_restraints 162 _refine_ls_R_factor_all 0.1308 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1759 _refine_ls_wR_factor_gt 0.1522 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.071 _refine_ls_shift/su_mean 0.018 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 0.79806(16) 0.92679(11) 0.07929(11) 0.0409(4) Uani 1 1 d D . . O2A O 0.64247(14) 0.77117(11) 0.28970(12) 0.0386(4) Uani 1 1 d D . . N1A N 0.89056(17) 0.74260(12) 0.26264(14) 0.0330(4) Uani 1 1 d D . . C1A C 0.8088(2) 1.02118(14) 0.10021(14) 0.0340(5) Uani 1 1 d D . . C2A C 0.8372(2) 1.11915(16) 0.01957(16) 0.0431(5) Uani 1 1 d D . . C3A C 0.8423(3) 1.21240(17) 0.05086(18) 0.0496(6) Uani 1 1 d D . . C4A C 0.8155(2) 1.20772(16) 0.16002(16) 0.0441(6) Uani 1 1 d D . . C5A C 0.7418(2) 1.10466(17) 0.36048(15) 0.0400(5) Uani 1 1 d D . . C6A C 0.7076(3) 1.01025(17) 0.44267(17) 0.0447(6) Uani 1 1 d D . . C7A C 0.7155(2) 0.91206(17) 0.41401(16) 0.0417(5) Uani 1 1 d D . . C8A C 0.7520(2) 0.91154(13) 0.30399(13) 0.0315(5) Uani 1 1 d D . . C9A C 0.7827(2) 1.01133(13) 0.21632(13) 0.0312(5) Uani 1 1 d D . . C10A C 0.7813(2) 1.10857(14) 0.24583(14) 0.0349(5) Uani 1 1 d D . . C11A C 0.75581(19) 0.80292(14) 0.28247(15) 0.0313(5) Uani 1 1 d D . . C12A C 0.93387(19) 0.64301(14) 0.22868(15) 0.0303(4) Uani 1 1 d D . . C13A C 1.0687(2) 0.58288(15) 0.23813(18) 0.0347(5) Uani 1 1 d D . . C14A C 1.1240(2) 0.48910(17) 0.19924(19) 0.0419(5) Uani 1 1 d D . . C15A C 1.0443(2) 0.45303(18) 0.1533(2) 0.0457(6) Uani 1 1 d D . . C16A C 0.9091(2) 0.51208(17) 0.14598(19) 0.0418(5) Uani 1 1 d D . . C17A C 0.8524(2) 0.60660(16) 0.18334(17) 0.0361(5) Uani 1 1 d D . . C18A C 0.7977(3) 0.9346(3) -0.03088(19) 0.0508(6) Uani 1 1 d D . . H1A H 0.967(2) 0.7719(17) 0.2640(16) 0.035(6) Uiso 1 1 d . . . H2A H 0.855(2) 1.1261(17) -0.0625(19) 0.043(6) Uiso 1 1 d . . . H3A H 0.865(3) 1.282(2) -0.009(2) 0.076(8) Uiso 1 1 d . . . H4A H 0.820(2) 1.273(2) 0.1846(19) 0.054(7) Uiso 1 1 d . . . H5A H 0.745(3) 1.171(2) 0.3800(19) 0.055(7) Uiso 1 1 d . . . H6A H 0.686(3) 1.011(2) 0.522(2) 0.079(8) Uiso 1 1 d . . . H7A H 0.688(2) 0.8453(19) 0.4759(19) 0.044(6) Uiso 1 1 d . . . H13A H 1.124(2) 0.6073(15) 0.2689(15) 0.024(5) Uiso 1 1 d . . . H14A H 1.221(3) 0.4513(19) 0.1997(19) 0.055(7) Uiso 1 1 d . . . H15A H 1.086(2) 0.384(2) 0.1231(19) 0.056(7) Uiso 1 1 d . . . H16A H 0.855(2) 0.4868(18) 0.1150(18) 0.045(6) Uiso 1 1 d . . . H17A H 0.759(2) 0.6487(18) 0.1784(18) 0.045(6) Uiso 1 1 d . . . H18X H 0.893(3) 0.9540(18) -0.0873(19) 0.043(6) Uiso 1 1 d . . . H18Y H 0.781(3) 0.858(2) -0.023(2) 0.063(8) Uiso 1 1 d . . . H18Z H 0.714(3) 0.989(2) -0.049(2) 0.065(8) Uiso 1 1 d . . . O1B O 0.2621 0.6563 0.4400 0.042 Uani 0.85 1 d PD A 1 O2B O 0.1588 0.8147 0.2519 0.035 Uani 0.85 1 d PD A 1 N1B N 0.3635 0.8671 0.2547 0.030 Uani 0.85 1 d PD A 1 C1B C 0.3404 0.5662 0.4023 0.035 Uani 0.85 1 d PD A 1 C2B C 0.3578 0.4618 0.4717 0.042 Uani 0.85 1 d PD A 1 C3B C 0.4419 0.3748 0.4231 0.050 Uani 0.85 1 d PD A 1 C4B C 0.5028 0.3925 0.3102 0.046 Uani 0.85 1 d PD A 1 C5B C 0.5539 0.5203 0.1189 0.041 Uani 0.85 1 d PD A 1 C6B C 0.5424 0.6238 0.0494 0.045 Uani 0.85 1 d PD A 1 C7B C 0.4601 0.7135 0.0946 0.039 Uani 0.85 1 d PD A 1 C8B C 0.3900 0.6975 0.2080 0.032 Uani 0.85 1 d PD A 1 C9B C 0.4056 0.5900 0.2827 0.030 Uani 0.85 1 d PD A 1 C10B C 0.4887 0.5002 0.2365 0.037 Uani 0.85 1 d PD A 1 C11B C 0.2912 0.7967 0.2444 0.029 Uani 0.85 1 d PD A 1 C12B C 0.3043 0.9727 0.2756 0.030 Uani 0.85 1 d PD A 1 C13B C 0.4040 1.0472 0.2426 0.040 Uani 0.85 1 d PD A 1 C14B C 0.3561 1.1504 0.2636 0.049 Uani 0.85 1 d PD A 1 C15B C 0.2082 1.1800 0.3168 0.053 Uani 0.85 1 d PD A 1 C16B C 0.1090 1.1063 0.3473 0.055 Uani 0.85 1 d PD A 1 C17B C 0.1554 1.0020 0.3286 0.038 Uani 0.85 1 d PD A 1 C18B C 0.1784 0.6362 0.5566 0.059 Uani 0.85 1 d PD A 1 H2B H 0.3127 0.4471 0.5629 0.089 Uiso 0.85 1 d P A 1 H3B H 0.4480 0.3000 0.4810 0.089 Uiso 0.85 1 d P A 1 H5B H 0.6147 0.4547 0.0842 0.089 Uiso 0.85 1 d P A 1 H6B H 0.5901 0.6476 -0.0384 0.089 Uiso 0.85 1 d P A 1 H7B H 0.4521 0.7844 0.0432 0.089 Uiso 0.85 1 d P A 1 H13B H 0.5186 1.0205 0.2047 0.089 Uiso 0.85 1 d P A 1 H15B H 0.1677 1.2567 0.3389 0.089 Uiso 0.85 1 d P A 1 H18C H 0.1018 0.5876 0.5742 0.089 Uiso 0.85 1 d P A 1 H18D H 0.1209 0.7049 0.5656 0.089 Uiso 0.85 1 d P A 1 H18E H 0.2450 0.6056 0.6141 0.089 Uiso 0.85 1 d P A 1 H1B H 0.4516 0.8405 0.2524 0.042 Uiso 0.85 1 d P A 1 H4B H 0.5704 0.3288 0.2738 0.059 Uiso 0.85 1 d P A 1 H14B H 0.4276 1.2038 0.2372 0.047 Uiso 0.85 1 d P A 1 H16B H 0.0033 1.1272 0.3842 0.057 Uiso 0.85 1 d P A 1 H17B H 0.0880 0.9582 0.3456 0.033 Uiso 0.85 1 d P A 1 O1C O 0.4280 0.7353 0.1205 0.042 Uani 0.15 1 d PD A 2 O2C O 0.1332 0.8072 0.2926 0.035 Uani 0.15 1 d PD A 2 N1C N 0.3366 0.8507 0.3068 0.030 Uani 0.15 1 d PD A 2 H1C H 0.4196 0.8215 0.3229 0.046 Uiso 0.15 1 calc PR A 2 C1C C 0.4551 0.6236 0.1642 0.035 Uani 0.15 1 d PD A 2 C2C C 0.5276 0.5504 0.1002 0.042 Uani 0.15 1 d PD A 2 H2C H 0.5607 0.5759 0.0204 0.063 Uiso 0.15 1 calc PR A 2 C3C C 0.5521 0.4367 0.1548 0.050 Uani 0.15 1 d PD A 2 H3C H 0.6027 0.3857 0.1109 0.075 Uiso 0.15 1 calc PR A 2 C4C C 0.5049 0.3989 0.2684 0.046 Uani 0.15 1 d PD A 2 H4C H 0.5246 0.3221 0.3030 0.069 Uiso 0.15 1 calc PR A 2 C5C C 0.3783 0.4344 0.4548 0.041 Uani 0.15 1 d PD A 2 H5C H 0.3978 0.3578 0.4899 0.061 Uiso 0.15 1 calc PR A 2 C6C C 0.3043 0.5051 0.5197 0.045 Uani 0.15 1 d PD A 2 H6C H 0.2751 0.4784 0.5994 0.068 Uiso 0.15 1 calc PR A 2 C7C C 0.2711 0.6190 0.4679 0.039 Uani 0.15 1 d PD A 2 H7C H 0.2204 0.6683 0.5137 0.059 Uiso 0.15 1 calc PR A 2 C8C C 0.3104 0.6594 0.3533 0.032 Uani 0.15 1 d PD A 2 C9C C 0.3901 0.5864 0.2837 0.030 Uani 0.15 1 d PD A 2 C10C C 0.4265 0.4725 0.3366 0.037 Uani 0.15 1 d PD A 2 C11C C 0.2548 0.7795 0.3083 0.029 Uani 0.15 1 d PD A 2 C12C C 0.3041 0.9679 0.2822 0.030 Uani 0.15 1 d PD A 2 C13C C 0.4240 1.0272 0.2371 0.040 Uani 0.15 1 d PD A 2 H13C H 0.5221 0.9895 0.2187 0.060 Uiso 0.15 1 calc PR A 2 C14C C 0.4009 1.1412 0.2190 0.049 Uani 0.15 1 d PD A 2 H14C H 0.4831 1.1819 0.1845 0.074 Uiso 0.15 1 calc PR A 2 C15C C 0.2593 1.1956 0.2509 0.053 Uani 0.15 1 d PD A 2 H15C H 0.2434 1.2733 0.2416 0.080 Uiso 0.15 1 calc PR A 2 C16C C 0.1405 1.1360 0.2964 0.055 Uani 0.15 1 d PD A 2 H16C H 0.0432 1.1724 0.3232 0.083 Uiso 0.15 1 calc PR A 2 C17C C 0.1610 1.0239 0.3038 0.038 Uani 0.15 1 d PD A 2 H17C H 0.0786 0.9861 0.3232 0.056 Uiso 0.15 1 calc PR A 2 C18C C 0.5009 0.7797 0.0033 0.059 Uani 0.15 1 d PD A 2 H18J H 0.4494 0.7658 -0.0411 0.089 Uiso 0.15 1 calc PR A 2 H18K H 0.6039 0.7440 -0.0166 0.089 Uiso 0.15 1 calc PR A 2 H18L H 0.4995 0.8597 -0.0127 0.089 Uiso 0.15 1 calc PR A 2 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 0.0472(9) 0.0460(10) 0.0325(8) -0.0114(7) -0.0171(7) -0.0028(7) O2A 0.0302(8) 0.0376(9) 0.0520(9) -0.0115(7) -0.0186(7) -0.0032(6) N1A 0.0305(9) 0.0311(10) 0.0413(10) -0.0078(8) -0.0175(8) -0.0037(8) C1A 0.0269(10) 0.0366(13) 0.0361(11) -0.0071(10) -0.0122(9) 0.0002(9) C2A 0.0373(12) 0.0462(15) 0.0370(12) -0.0025(11) -0.0118(10) -0.0014(10) C3A 0.0444(14) 0.0347(14) 0.0528(15) 0.0011(12) -0.0097(12) -0.0014(11) C4A 0.0351(12) 0.0330(13) 0.0567(15) -0.0110(12) -0.0096(11) -0.0001(10) C5A 0.0363(12) 0.0402(14) 0.0503(14) -0.0192(12) -0.0169(10) -0.0015(10) C6A 0.0542(14) 0.0511(15) 0.0388(13) -0.0173(12) -0.0221(11) -0.0051(12) C7A 0.0485(14) 0.0431(14) 0.0359(12) -0.0063(12) -0.0182(10) -0.0087(11) C8A 0.0317(11) 0.0329(12) 0.0323(11) -0.0073(9) -0.0156(9) -0.0020(9) C9A 0.0240(10) 0.0338(12) 0.0364(11) -0.0103(10) -0.0124(8) 0.0009(9) C10A 0.0263(10) 0.0335(12) 0.0443(12) -0.0117(10) -0.0118(9) 0.0003(9) C11A 0.0310(11) 0.0324(12) 0.0305(10) -0.0023(9) -0.0149(9) -0.0045(9) C12A 0.0336(11) 0.0287(11) 0.0281(10) -0.0027(9) -0.0128(9) -0.0054(9) C13A 0.0332(11) 0.0321(12) 0.0420(12) -0.0073(10) -0.0176(10) -0.0045(9) C14A 0.0321(12) 0.0366(13) 0.0534(14) -0.0091(11) -0.0143(11) -0.0008(10) C15A 0.0430(13) 0.0433(15) 0.0524(14) -0.0186(12) -0.0136(11) -0.0026(11) C16A 0.0458(13) 0.0442(14) 0.0443(13) -0.0170(11) -0.0189(11) -0.0069(11) C17A 0.0338(12) 0.0380(13) 0.0397(12) -0.0091(10) -0.0171(10) -0.0031(10) C18A 0.0563(17) 0.065(2) 0.0385(14) -0.0171(13) -0.0239(13) -0.0020(15) O1B 0.050 0.035 0.033 -0.010 -0.007 0.001 O2B 0.028 0.038 0.044 -0.015 -0.015 -0.002 N1B 0.024 0.032 0.038 -0.013 -0.013 0.001 C1B 0.031 0.033 0.042 -0.011 -0.011 -0.005 C2B 0.042 0.030 0.047 -0.005 -0.011 -0.004 C3B 0.042 0.035 0.065 -0.002 -0.018 -0.005 C4B 0.038 0.033 0.070 -0.017 -0.018 -0.002 C5B 0.039 0.045 0.049 -0.024 -0.021 0.003 C6B 0.039 0.059 0.043 -0.025 -0.015 0.002 C7B 0.036 0.044 0.039 -0.015 -0.016 0.002 C8B 0.026 0.036 0.036 -0.015 -0.012 0.000 C9B 0.023 0.030 0.040 -0.011 -0.014 -0.003 C10B 0.029 0.035 0.054 -0.018 -0.018 0.000 C11B 0.029 0.028 0.028 -0.004 -0.013 -0.003 C12B 0.034 0.028 0.033 -0.007 -0.020 -0.001 C13B 0.041 0.038 0.046 -0.009 -0.019 -0.008 C14B 0.063 0.036 0.059 -0.006 -0.031 -0.014 C15B 0.067 0.032 0.075 -0.017 -0.045 0.008 C16B 0.042 0.046 0.093 -0.039 -0.032 0.013 C17B 0.033 0.038 0.048 -0.018 -0.016 -0.002 C18B 0.070 0.053 0.041 -0.014 0.001 -0.010 O1C 0.050 0.035 0.033 -0.010 -0.007 0.001 O2C 0.028 0.038 0.044 -0.015 -0.015 -0.002 N1C 0.024 0.032 0.038 -0.013 -0.013 0.001 C1C 0.031 0.033 0.042 -0.011 -0.011 -0.005 C2C 0.042 0.030 0.047 -0.005 -0.011 -0.004 C3C 0.042 0.035 0.065 -0.002 -0.018 -0.005 C4C 0.038 0.033 0.070 -0.017 -0.018 -0.002 C5C 0.039 0.045 0.049 -0.024 -0.021 0.003 C6C 0.039 0.059 0.043 -0.025 -0.015 0.002 C7C 0.036 0.044 0.039 -0.015 -0.016 0.002 C8C 0.026 0.036 0.036 -0.015 -0.012 0.000 C9C 0.023 0.030 0.040 -0.011 -0.014 -0.003 C10C 0.029 0.035 0.054 -0.018 -0.018 0.000 C11C 0.029 0.028 0.028 -0.004 -0.013 -0.003 C12C 0.034 0.028 0.033 -0.007 -0.020 -0.001 C13C 0.041 0.038 0.046 -0.009 -0.019 -0.008 C14C 0.063 0.036 0.059 -0.006 -0.031 -0.014 C15C 0.067 0.032 0.075 -0.017 -0.045 0.008 C16C 0.042 0.046 0.093 -0.039 -0.032 0.013 C17C 0.033 0.038 0.048 -0.018 -0.016 -0.002 C18C 0.070 0.053 0.041 -0.014 0.001 -0.010 _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 C1A 1.3680(19) . ? O1A C18A 1.431(2) . ? O2A C11A 1.2303(19) . ? N1A C11A 1.344(2) . ? N1A C12A 1.4190(19) . ? C1A C2A 1.369(2) . ? C1A C9A 1.431(2) . ? C2A C3A 1.411(2) . ? C3A C4A 1.355(2) . ? C4A C10A 1.417(2) . ? C5A C6A 1.354(2) . ? C5A C10A 1.410(2) . ? C6A C7A 1.414(2) . ? C7A C8A 1.370(2) . ? C8A C9A 1.428(2) . ? C8A C11A 1.508(2) . ? C9A C10A 1.426(2) . ? C12A C17A 1.387(2) . ? C12A C13A 1.388(2) . ? C13A C14A 1.384(2) . ? C14A C15A 1.377(2) . ? C15A C16A 1.380(2) . ? C16A C17A 1.383(2) . ? O1B C1B 1.3659 . ? O1B C18B 1.4281 . ? O2B C11B 1.2310 . ? N1B C11B 1.3401 . ? N1B C12B 1.4225 . ? C1B C2B 1.3709 . ? C1B C9B 1.4312 . ? C2B C3B 1.4143 . ? C3B C4B 1.3542 . ? C4B C10B 1.4194 . ? C5B C6B 1.3561 . ? C5B C10B 1.4090 . ? C6B C7B 1.4169 . ? C7B C8B 1.3715 . ? C8B C9B 1.4261 . ? C8B C11B 1.5108 . ? C9B C10B 1.4260 . ? C12B C13B 1.3845 . ? C12B C17B 1.3863 . ? C13B C14B 1.3851 . ? C14B C15B 1.3791 . ? C15B C16B 1.3795 . ? C16B C17B 1.3862 . ? O1C C1C 1.3653 . ? O1C C18C 1.4303 . ? O2C C11C 1.2309 . ? N1C C11C 1.3435 . ? N1C C12C 1.4199 . ? C1C C2C 1.3722 . ? C1C C9C 1.4315 . ? C2C C3C 1.4121 . ? C3C C4C 1.3541 . ? C4C C10C 1.4206 . ? C5C C6C 1.3572 . ? C5C C10C 1.4076 . ? C6C C7C 1.4165 . ? C7C C8C 1.3690 . ? C8C C9C 1.4283 . ? C8C C11C 1.5104 . ? C9C C10C 1.4268 . ? C12C C13C 1.3863 . ? C12C C17C 1.3878 . ? C13C C14C 1.3854 . ? C14C C15C 1.3770 . ? C15C C16C 1.3800 . ? C16C C17C 1.3868 . ? 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 O1A C18A 117.75(17) . . ? C11A N1A C12A 127.70(15) . . ? O1A C1A C2A 124.29(15) . . ? O1A C1A C9A 114.29(14) . . ? C2A C1A C9A 121.39(15) . . ? C1A C2A C3A 119.62(17) . . ? C4A C3A C2A 121.13(18) . . ? C3A C4A C10A 120.60(18) . . ? C6A C5A C10A 121.40(17) . . ? C5A C6A C7A 119.90(17) . . ? C8A C7A C6A 121.04(18) . . ? C7A C8A C9A 119.87(14) . . ? C7A C8A C11A 116.90(15) . . ? C9A C8A C11A 123.23(14) . . ? C10A C9A C8A 118.58(13) . . ? C10A C9A C1A 117.54(14) . . ? C8A C9A C1A 123.82(14) . . ? C5A C10A C4A 121.31(16) . . ? C5A C10A C9A 119.10(15) . . ? C4A C10A C9A 119.57(15) . . ? O2A C11A N1A 124.06(15) . . ? O2A C11A C8A 121.78(15) . . ? N1A C11A C8A 114.02(15) . . ? C17A C12A C13A 119.61(15) . . ? C17A C12A N1A 123.65(15) . . ? C13A C12A N1A 116.69(15) . . ? C14A C13A C12A 120.28(16) . . ? C15A C14A C13A 120.37(17) . . ? C14A C15A C16A 119.06(18) . . ? C15A C16A C17A 121.47(17) . . ? C16A C17A C12A 119.18(17) . . ? C1B O1B C18B 117.0 . . ? C11B N1B C12B 127.3 . . ? O1B C1B C2B 123.8 . . ? O1B C1B C9B 114.1 . . ? C2B C1B C9B 122.1 . . ? C1B C2B C3B 118.8 . . ? C4B C3B C2B 121.4 . . ? C3B C4B C10B 121.0 . . ? C6B C5B C10B 121.2 . . ? C5B C6B C7B 119.9 . . ? C8B C7B C6B 121.1 . . ? C7B C8B C9B 119.7 . . ? C7B C8B C11B 116.1 . . ? C9B C8B C11B 124.1 . . ? C10B C9B C8B 118.7 . . ? C10B C9B C1B 117.6 . . ? C8B C9B C1B 123.6 . . ? C5B C10B C4B 121.7 . . ? C5B C10B C9B 119.3 . . ? C4B C10B C9B 119.1 . . ? O2B C11B N1B 124.2 . . ? O2B C11B C8B 121.3 . . ? N1B C11B C8B 114.1 . . ? C13B C12B C17B 119.8 . . ? C13B C12B N1B 116.8 . . ? C17B C12B N1B 123.4 . . ? C12B C13B C14B 120.4 . . ? C15B C14B C13B 120.2 . . ? C14B C15B C16B 119.2 . . ? C15B C16B C17B 121.4 . . ? C16B C17B C12B 119.1 . . ? C1C O1C C18C 117.3 . . ? C11C N1C C12C 127.3 . . ? O1C C1C C2C 123.9 . . ? O1C C1C C9C 114.3 . . ? C2C C1C C9C 121.6 . . ? C1C C2C C3C 118.9 . . ? C4C C3C C2C 121.4 . . ? C3C C4C C10C 120.8 . . ? C6C C5C C10C 121.3 . . ? C5C C6C C7C 119.6 . . ? C8C C7C C6C 121.4 . . ? C7C C8C C9C 119.8 . . ? C7C C8C C11C 116.4 . . ? C9C C8C C11C 123.6 . . ? C10C C9C C8C 118.4 . . ? C10C C9C C1C 117.3 . . ? C8C C9C C1C 123.6 . . ? C5C C10C C4C 121.4 . . ? C5C C10C C9C 119.4 . . ? C4C C10C C9C 119.1 . . ? O2C C11C N1C 124.0 . . ? O2C C11C C8C 121.4 . . ? N1C C11C C8C 113.6 . . ? C13C C12C C17C 119.7 . . ? C13C C12C N1C 116.8 . . ? C17C C12C N1C 123.5 . . ? C14C C13C C12C 120.2 . . ? C15C C14C C13C 120.2 . . ? C14C C15C C16C 119.3 . . ? C15C C16C C17C 121.1 . . ? C16C C17C C12C 118.7 . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.209 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.060 data_dimethylamino-N-phenylamide _database_code_depnum_ccdc_archive 'CCDC 270919' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-(Dimethylamino)-N-phenyl-1-naphthamide ; _chemical_name_common ? _chemical_melting_point 466 _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N2 O' _chemical_formula_weight 290.35 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' 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 P2(1)/c 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 9.3770(2) _cell_length_b 9.7055(2) _cell_length_c 16.7953(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.3607(12) _cell_angle_gamma 90.00 _cell_volume 1528.08(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16763 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 27.57 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; SADABS V2.10 (G.M.Shedrick, 2003) ; _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 95mm 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 16763 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3504 _reflns_number_gt 2884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (R.W.W. Hooft, 1998)' _computing_cell_refinement ; DENZO (Otwinowski & Minor, 1997 & COLLECT (R.W.W. Hooft, 1998) ; #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction ; DENZO (Otwinowski & Minor, 1997 & COLLECT (R.W.W. Hooft, 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^)+(0.0819P)^2^+0.1221P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3504 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.003 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 0.47133(8) 0.09799(8) 0.73147(5) 0.0214(2) Uani 1 1 d . . . N1 N 0.36441(10) 0.19723(10) 0.88974(6) 0.0229(2) Uani 1 1 d . . . N2 N 0.40517(10) 0.32564(10) 0.72657(6) 0.0188(2) Uani 1 1 d . . . C1 C 0.48153(12) 0.26326(12) 0.93067(7) 0.0200(3) Uani 1 1 d . . . C2 C 0.47779(14) 0.30084(13) 1.00954(7) 0.0271(3) Uani 1 1 d . . . C3 C 0.59833(15) 0.35927(14) 1.04832(7) 0.0300(3) Uani 1 1 d . . . C4 C 0.72294(14) 0.37368(13) 1.00891(7) 0.0274(3) Uani 1 1 d . . . C5 C 0.86048(13) 0.35147(12) 0.88567(8) 0.0248(3) Uani 1 1 d . . . C6 C 0.86609(13) 0.32393(12) 0.80613(8) 0.0248(3) Uani 1 1 d . . . C7 C 0.74123(12) 0.28176(12) 0.76413(7) 0.0214(3) Uani 1 1 d . . . C8 C 0.61478(12) 0.26349(11) 0.80269(6) 0.0175(2) Uani 1 1 d . . . C9 C 0.60718(11) 0.28725(11) 0.88630(6) 0.0181(3) Uani 1 1 d . . . C10 C 0.73175(12) 0.33747(11) 0.92737(7) 0.0211(3) Uani 1 1 d . . . C11 C 0.48729(11) 0.21861(11) 0.75281(6) 0.0176(2) Uani 1 1 d . . . C12 C 0.27386(11) 0.31923(11) 0.68350(6) 0.0177(2) Uani 1 1 d . . . C13 C 0.22186(13) 0.44150(12) 0.65048(7) 0.0248(3) Uani 1 1 d . . . C14 C 0.09179(13) 0.44451(13) 0.60916(8) 0.0270(3) Uani 1 1 d . . . C15 C 0.01219(13) 0.32521(12) 0.60014(7) 0.0254(3) Uani 1 1 d . . . C16 C 0.06383(13) 0.20375(13) 0.63294(8) 0.0275(3) Uani 1 1 d . . . C17 C 0.19423(13) 0.19877(12) 0.67448(7) 0.0243(3) Uani 1 1 d . . . C18 C 0.22663(14) 0.26339(17) 0.89953(9) 0.0357(3) Uani 1 1 d . . . C19 C 0.35863(16) 0.04948(14) 0.90643(9) 0.0331(3) Uani 1 1 d . . . HN2 H 0.4359(14) 0.4121(15) 0.7392(8) 0.024(3) Uiso 1 1 d . . . H2 H 0.3913(17) 0.2850(16) 1.0411(9) 0.037(4) Uiso 1 1 d . . . H3 H 0.5892(16) 0.3867(16) 1.1033(10) 0.042(4) Uiso 1 1 d . . . H4 H 0.8064(15) 0.4166(15) 1.0351(9) 0.028(4) Uiso 1 1 d . . . H5 H 0.9491(16) 0.3844(15) 0.9172(9) 0.033(4) Uiso 1 1 d . . . H6 H 0.9552(16) 0.3348(14) 0.7763(9) 0.028(4) Uiso 1 1 d . . . H7 H 0.7477(14) 0.2679(14) 0.7055(8) 0.025(3) Uiso 1 1 d . . . H13 H 0.2783(15) 0.5268(16) 0.6559(8) 0.031(4) Uiso 1 1 d . . . H14 H 0.0565(16) 0.5319(17) 0.5877(9) 0.039(4) Uiso 1 1 d . . . H15 H -0.0819(17) 0.3238(14) 0.5713(9) 0.034(4) Uiso 1 1 d . . . H16 H 0.0084(16) 0.1158(16) 0.6279(9) 0.034(4) Uiso 1 1 d . . . H17 H 0.2289(15) 0.1146(16) 0.6962(9) 0.032(4) Uiso 1 1 d . . . H18A H 0.2312(15) 0.3634(17) 0.8841(9) 0.033(4) Uiso 1 1 d . . . H18B H 0.1569(17) 0.2151(16) 0.8618(9) 0.036(4) Uiso 1 1 d . . . H18C H 0.1936(17) 0.2628(19) 0.9562(11) 0.048(5) Uiso 1 1 d . . . H19A H 0.3311(16) 0.0299(17) 0.9627(10) 0.043(4) Uiso 1 1 d . . . H19B H 0.2836(17) 0.0079(18) 0.8685(9) 0.044(4) Uiso 1 1 d . . . H19C H 0.4540(17) 0.0061(16) 0.8979(9) 0.036(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0231(4) 0.0173(4) 0.0238(4) -0.0021(3) -0.0010(3) 0.0013(3) N1 0.0183(5) 0.0243(5) 0.0262(5) -0.0006(4) 0.0031(4) -0.0003(4) N2 0.0174(5) 0.0165(5) 0.0222(5) -0.0007(3) -0.0033(4) -0.0012(4) C1 0.0210(6) 0.0185(5) 0.0203(5) 0.0020(4) -0.0003(4) 0.0043(4) C2 0.0315(7) 0.0286(7) 0.0213(6) 0.0032(5) 0.0047(5) 0.0054(5) C3 0.0423(8) 0.0306(7) 0.0168(6) -0.0013(5) -0.0043(5) 0.0090(6) C4 0.0328(7) 0.0241(6) 0.0247(6) -0.0023(5) -0.0101(5) 0.0060(5) C5 0.0197(6) 0.0206(6) 0.0336(7) 0.0009(5) -0.0073(5) 0.0011(4) C6 0.0165(6) 0.0252(6) 0.0329(7) 0.0031(5) 0.0020(5) 0.0005(5) C7 0.0199(6) 0.0217(6) 0.0226(6) 0.0015(4) 0.0016(5) 0.0012(4) C8 0.0174(5) 0.0143(5) 0.0208(5) 0.0010(4) -0.0012(4) 0.0024(4) C9 0.0194(6) 0.0144(5) 0.0203(6) 0.0000(4) -0.0013(4) 0.0038(4) C10 0.0214(6) 0.0175(5) 0.0242(6) 0.0010(4) -0.0061(5) 0.0041(4) C11 0.0172(5) 0.0186(6) 0.0169(5) 0.0002(4) 0.0030(4) -0.0001(4) C12 0.0166(5) 0.0202(6) 0.0164(5) -0.0017(4) -0.0004(4) -0.0003(4) C13 0.0233(6) 0.0180(6) 0.0328(7) 0.0002(5) -0.0046(5) -0.0015(5) C14 0.0254(6) 0.0227(6) 0.0326(7) 0.0027(5) -0.0062(5) 0.0043(5) C15 0.0204(6) 0.0281(6) 0.0274(6) -0.0036(5) -0.0046(5) 0.0019(5) C16 0.0239(6) 0.0222(6) 0.0360(7) -0.0023(5) -0.0067(5) -0.0033(5) C17 0.0229(6) 0.0186(6) 0.0312(7) 0.0017(4) -0.0049(5) -0.0007(5) C18 0.0202(7) 0.0456(9) 0.0414(8) -0.0067(7) 0.0035(6) 0.0055(6) C19 0.0370(8) 0.0268(7) 0.0357(8) 0.0036(5) 0.0045(6) -0.0069(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 C11 1.2325(13) . ? N1 C1 1.4330(15) . ? N1 C18 1.4555(16) . ? N1 C19 1.4624(16) . ? N2 C11 1.3602(14) . ? N2 C12 1.4145(14) . ? C1 C2 1.3752(17) . ? C1 C9 1.4281(16) . ? C2 C3 1.4101(19) . ? C3 C4 1.364(2) . ? C4 C10 1.4181(17) . ? C5 C6 1.3646(19) . ? C5 C10 1.4164(17) . ? C6 C7 1.4131(16) . ? C7 C8 1.3760(16) . ? C8 C9 1.4264(15) . ? C8 C11 1.5077(15) . ? C9 C10 1.4282(16) . ? C12 C13 1.3931(16) . ? C12 C17 1.3935(16) . ? C13 C14 1.3892(16) . ? C14 C15 1.3840(17) . ? C15 C16 1.3838(17) . ? C16 C17 1.3942(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 C18 114.88(10) . . ? C1 N1 C19 112.21(10) . . ? C18 N1 C19 111.96(11) . . ? C11 N2 C12 127.68(10) . . ? C2 C1 C9 119.97(11) . . ? C2 C1 N1 122.95(11) . . ? C9 C1 N1 117.06(10) . . ? C1 C2 C3 120.87(12) . . ? C4 C3 C2 120.24(11) . . ? C3 C4 C10 120.90(11) . . ? C6 C5 C10 121.22(11) . . ? C5 C6 C7 119.65(11) . . ? C8 C7 C6 121.02(11) . . ? C7 C8 C9 120.42(10) . . ? C7 C8 C11 117.16(10) . . ? C9 C8 C11 122.42(10) . . ? C8 C9 C1 123.26(10) . . ? C8 C9 C10 118.11(10) . . ? C1 C9 C10 118.62(10) . . ? C5 C10 C4 121.57(11) . . ? C5 C10 C9 119.39(10) . . ? C4 C10 C9 119.03(11) . . ? O1 C11 N2 124.56(10) . . ? O1 C11 C8 121.68(10) . . ? N2 C11 C8 113.25(9) . . ? C13 C12 C17 119.33(10) . . ? C13 C12 N2 117.28(10) . . ? C17 C12 N2 123.38(10) . . ? C14 C13 C12 120.77(11) . . ? C15 C14 C13 120.13(11) . . ? C16 C15 C14 119.10(11) . . ? C15 C16 C17 121.55(11) . . ? C12 C17 C16 119.12(11) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.298 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.151 data_acylurea _database_code_depnum_ccdc_archive 'CCDC 270920' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(8-Dimethylamino-1-naphthoyl)-N,N-diphenylurea ; _chemical_name_common ? _chemical_melting_point 412 _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 N3 O2' _chemical_formula_weight 409.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8308(2) _cell_length_b 9.6640(3) _cell_length_c 12.0688(3) _cell_angle_alpha 85.4547(15) _cell_angle_beta 68.6506(14) _cell_angle_gamma 78.8152(15) _cell_volume 1047.58(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 22049 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 27.56 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; SADABS V2.10 (G.M. Sheldrick, 2003) ; _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 95mm 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 22049 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.56 _reflns_number_total 4800 _reflns_number_gt 3570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (R.W.W. Hooft, 1998)' _computing_cell_refinement ; DENZO (Otwinowski & Minor, 1997 & COLLECT (R.W.W. Hooft, 1998) ; #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction ; DENZO (Otwinowski & Minor, 1997 & COLLECT (R.W.W. Hooft, 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^)+(0.0856P)^2^+0.0747P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4800 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 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 0.49141(11) 0.63251(11) 0.59303(8) 0.0306(3) Uani 1 1 d . . . O2 O 0.26689(11) 0.54661(11) 0.94412(8) 0.0327(3) Uani 1 1 d . . . N1 N 0.74503(13) 0.50949(12) 0.68436(10) 0.0306(3) Uani 1 1 d . . . N2 N 0.42187(12) 0.66296(12) 0.79410(9) 0.0231(3) Uani 1 1 d . . . N3 N 0.33014(12) 0.47080(12) 0.75465(10) 0.0251(3) Uani 1 1 d . . . C1 C 0.81440(15) 0.62306(15) 0.69150(11) 0.0275(3) Uani 1 1 d . . . C2 C 0.93763(17) 0.6063(2) 0.72324(14) 0.0407(4) Uani 1 1 d . . . C3 C 1.01036(19) 0.7202(2) 0.71551(16) 0.0489(5) Uani 1 1 d . . . C4 C 0.96324(17) 0.8483(2) 0.67406(14) 0.0414(4) Uani 1 1 d . . . C5 C 0.77372(17) 1.00837(16) 0.61220(12) 0.0326(3) Uani 1 1 d . . . C6 C 0.63946(18) 1.03429(16) 0.59783(12) 0.0329(3) Uani 1 1 d . . . C7 C 0.55456(16) 0.92593(15) 0.62078(12) 0.0283(3) Uani 1 1 d . . . C8 C 0.60750(14) 0.79243(14) 0.65257(11) 0.0224(3) Uani 1 1 d . . . C9 C 0.75075(14) 0.76067(14) 0.66287(10) 0.0237(3) Uani 1 1 d . . . C10 C 0.83024(15) 0.87367(16) 0.64783(11) 0.0288(3) Uani 1 1 d . . . C11 C 0.50679(14) 0.68520(14) 0.67600(11) 0.0237(3) Uani 1 1 d . . . C12 C 0.41839(14) 0.75027(14) 0.88814(11) 0.0229(3) Uani 1 1 d . . . C13 C 0.51259(15) 0.70762(16) 0.95115(11) 0.0272(3) Uani 1 1 d . . . C14 C 0.49849(17) 0.78848(17) 1.04607(12) 0.0327(3) Uani 1 1 d . . . C15 C 0.39056(17) 0.90818(16) 1.07828(13) 0.0349(4) Uani 1 1 d . . . C16 C 0.29760(16) 0.95031(16) 1.01474(13) 0.0334(3) Uani 1 1 d . . . C17 C 0.31135(15) 0.87143(15) 0.91879(12) 0.0280(3) Uani 1 1 d . . . C18 C 0.79173(18) 0.46154(17) 0.56134(13) 0.0330(3) Uani 1 1 d . . . C19 C 0.7619(3) 0.38707(19) 0.76079(15) 0.0516(5) Uani 1 1 d . . . C20 C 0.33277(14) 0.55546(14) 0.83766(11) 0.0234(3) Uani 1 1 d . . . C21 C 0.24491(14) 0.36180(14) 0.77677(11) 0.0231(3) Uani 1 1 d . . . C22 C 0.26860(15) 0.27845(15) 0.68002(12) 0.0256(3) Uani 1 1 d . . . C23 C 0.18584(16) 0.17363(16) 0.69257(13) 0.0308(3) Uani 1 1 d . . . C24 C 0.07888(16) 0.14979(16) 0.80189(13) 0.0320(3) Uani 1 1 d . . . C25 C 0.05626(16) 0.23226(16) 0.89768(13) 0.0318(3) Uani 1 1 d . . . C26 C 0.13799(15) 0.33828(15) 0.88684(12) 0.0282(3) Uani 1 1 d . . . HN3 H 0.382(2) 0.4915(19) 0.6777(18) 0.049(5) Uiso 1 1 d . . . H2 H 0.9755(19) 0.5177(19) 0.7483(15) 0.044(5) Uiso 1 1 d . . . H3 H 1.102(2) 0.705(2) 0.7316(19) 0.070(6) Uiso 1 1 d . . . H4 H 1.016(2) 0.9277(19) 0.6636(16) 0.046(5) Uiso 1 1 d . . . H5 H 0.833(2) 1.0847(19) 0.5978(15) 0.045(5) Uiso 1 1 d . . . H6 H 0.5958(19) 1.1281(19) 0.5747(16) 0.045(5) Uiso 1 1 d . . . H7 H 0.4542(18) 0.9471(16) 0.6155(13) 0.031(4) Uiso 1 1 d . . . H13 H 0.5867(17) 0.6202(17) 0.9304(14) 0.031(4) Uiso 1 1 d . . . H14 H 0.5632(18) 0.7564(17) 1.0912(15) 0.036(4) Uiso 1 1 d . . . H15 H 0.3856(18) 0.9636(17) 1.1453(16) 0.040(4) Uiso 1 1 d . . . H16 H 0.226(2) 1.0383(19) 1.0345(16) 0.047(5) Uiso 1 1 d . . . H17 H 0.2466(17) 0.9009(17) 0.8719(14) 0.032(4) Uiso 1 1 d . . . H18A H 0.7906(16) 0.5442(17) 0.5071(14) 0.029(4) Uiso 1 1 d . . . H18B H 0.895(2) 0.4033(18) 0.5375(16) 0.045(5) Uiso 1 1 d . . . H18C H 0.720(2) 0.4002(18) 0.5550(15) 0.044(5) Uiso 1 1 d . . . H19A H 0.742(2) 0.4185(19) 0.8448(18) 0.047(5) Uiso 1 1 d . . . H19B H 0.692(3) 0.320(3) 0.761(2) 0.079(7) Uiso 1 1 d . . . H19C H 0.863(2) 0.331(2) 0.7328(18) 0.062(6) Uiso 1 1 d . . . H22 H 0.3402(17) 0.2984(16) 0.6038(14) 0.029(4) Uiso 1 1 d . . . H23 H 0.2017(18) 0.1150(18) 0.6226(16) 0.041(4) Uiso 1 1 d . . . H24 H 0.0174(18) 0.0761(17) 0.8096(14) 0.036(4) Uiso 1 1 d . . . H25 H -0.0208(18) 0.2182(17) 0.9736(15) 0.037(4) Uiso 1 1 d . . . H26 H 0.1193(18) 0.3968(17) 0.9543(15) 0.035(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0343(5) 0.0401(6) 0.0191(5) 0.0012(4) -0.0070(4) -0.0158(4) O2 0.0392(6) 0.0368(6) 0.0195(5) -0.0013(4) -0.0022(4) -0.0168(4) N1 0.0336(6) 0.0263(6) 0.0221(6) 0.0036(5) -0.0006(5) -0.0024(5) N2 0.0220(5) 0.0273(6) 0.0183(5) 0.0003(4) -0.0045(4) -0.0063(4) N3 0.0255(6) 0.0300(6) 0.0184(6) 0.0002(5) -0.0040(5) -0.0095(5) C1 0.0252(7) 0.0349(8) 0.0161(6) -0.0016(5) -0.0020(5) -0.0007(6) C2 0.0312(8) 0.0542(11) 0.0311(8) -0.0056(7) -0.0120(7) 0.0093(8) C3 0.0294(8) 0.0760(14) 0.0447(10) -0.0193(9) -0.0191(7) 0.0013(8) C4 0.0292(8) 0.0598(12) 0.0370(8) -0.0183(8) -0.0071(7) -0.0142(8) C5 0.0421(8) 0.0320(8) 0.0223(7) -0.0062(6) -0.0030(6) -0.0175(7) C6 0.0474(9) 0.0244(8) 0.0230(7) 0.0006(6) -0.0076(6) -0.0075(7) C7 0.0307(8) 0.0312(8) 0.0215(7) 0.0016(5) -0.0085(6) -0.0045(6) C8 0.0253(6) 0.0260(7) 0.0143(6) 0.0002(5) -0.0046(5) -0.0059(5) C9 0.0236(6) 0.0314(8) 0.0132(6) -0.0015(5) -0.0019(5) -0.0066(5) C10 0.0291(7) 0.0377(8) 0.0179(6) -0.0086(6) -0.0024(5) -0.0109(6) C11 0.0231(6) 0.0273(7) 0.0189(6) 0.0020(5) -0.0060(5) -0.0042(5) C12 0.0224(6) 0.0259(7) 0.0171(6) 0.0002(5) -0.0012(5) -0.0084(5) C13 0.0276(7) 0.0326(8) 0.0202(6) 0.0032(6) -0.0057(5) -0.0093(6) C14 0.0396(8) 0.0406(9) 0.0214(7) 0.0048(6) -0.0106(6) -0.0182(7) C15 0.0448(9) 0.0355(9) 0.0217(7) -0.0027(6) -0.0013(6) -0.0210(7) C16 0.0325(8) 0.0273(8) 0.0315(8) -0.0036(6) 0.0020(6) -0.0098(6) C17 0.0239(7) 0.0300(8) 0.0275(7) 0.0008(6) -0.0046(6) -0.0085(6) C18 0.0356(8) 0.0296(8) 0.0268(7) -0.0014(6) -0.0035(6) -0.0042(7) C19 0.0712(13) 0.0345(10) 0.0279(9) 0.0071(7) -0.0018(8) 0.0053(9) C20 0.0207(6) 0.0247(7) 0.0227(7) 0.0013(5) -0.0058(5) -0.0036(5) C21 0.0201(6) 0.0248(7) 0.0236(6) 0.0022(5) -0.0075(5) -0.0039(5) C22 0.0233(7) 0.0304(8) 0.0214(7) 0.0001(5) -0.0068(5) -0.0035(5) C23 0.0299(7) 0.0335(8) 0.0291(7) -0.0054(6) -0.0096(6) -0.0056(6) C24 0.0285(7) 0.0325(8) 0.0357(8) -0.0010(6) -0.0097(6) -0.0105(6) C25 0.0269(7) 0.0380(9) 0.0268(7) 0.0003(6) -0.0026(6) -0.0113(6) C26 0.0268(7) 0.0322(8) 0.0235(7) -0.0028(6) -0.0044(6) -0.0079(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 C11 1.2271(16) . ? O2 C20 1.2149(16) . ? N1 C1 1.4231(19) . ? N1 C19 1.463(2) . ? N1 C18 1.4697(19) . ? N2 C11 1.3890(16) . ? N2 C20 1.4332(17) . ? N2 C12 1.4538(16) . ? N3 C20 1.3530(17) . ? N3 C21 1.4205(17) . ? C1 C2 1.376(2) . ? C1 C9 1.429(2) . ? C2 C3 1.404(3) . ? C3 C4 1.358(3) . ? C4 C10 1.426(2) . ? C5 C6 1.366(2) . ? C5 C10 1.412(2) . ? C6 C7 1.412(2) . ? C7 C8 1.3744(19) . ? C8 C9 1.4306(18) . ? C8 C11 1.5106(18) . ? C9 C10 1.4256(19) . ? C12 C13 1.3860(19) . ? C12 C17 1.386(2) . ? C13 C14 1.388(2) . ? C14 C15 1.382(2) . ? C15 C16 1.380(2) . ? C16 C17 1.388(2) . ? C21 C22 1.3946(19) . ? C21 C26 1.3961(18) . ? C22 C23 1.384(2) . ? C23 C24 1.391(2) . ? C24 C25 1.383(2) . ? C25 C26 1.391(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 C19 116.27(14) . . ? C1 N1 C18 111.71(11) . . ? C19 N1 C18 108.87(12) . . ? C11 N2 C20 125.93(11) . . ? C11 N2 C12 121.09(11) . . ? C20 N2 C12 112.97(10) . . ? C20 N3 C21 125.78(11) . . ? C2 C1 N1 123.60(14) . . ? C2 C1 C9 119.51(14) . . ? N1 C1 C9 116.89(12) . . ? C1 C2 C3 120.55(16) . . ? C4 C3 C2 121.03(15) . . ? C3 C4 C10 120.45(16) . . ? C6 C5 C10 120.85(13) . . ? C5 C6 C7 119.78(14) . . ? C8 C7 C6 121.07(13) . . ? C7 C8 C9 120.28(12) . . ? C7 C8 C11 116.56(12) . . ? C9 C8 C11 123.16(12) . . ? C10 C9 C1 119.05(12) . . ? C10 C9 C8 117.82(12) . . ? C1 C9 C8 123.09(12) . . ? C5 C10 C9 119.91(13) . . ? C5 C10 C4 121.51(14) . . ? C9 C10 C4 118.53(14) . . ? O1 C11 N2 122.56(12) . . ? O1 C11 C8 120.42(11) . . ? N2 C11 C8 116.61(11) . . ? C13 C12 C17 120.99(12) . . ? C13 C12 N2 120.57(12) . . ? C17 C12 N2 118.27(12) . . ? C12 C13 C14 118.90(14) . . ? C15 C14 C13 120.42(14) . . ? C16 C15 C14 120.31(14) . . ? C15 C16 C17 119.95(14) . . ? C12 C17 C16 119.41(14) . . ? O2 C20 N3 125.29(12) . . ? O2 C20 N2 118.61(12) . . ? N3 C20 N2 116.10(11) . . ? C22 C21 C26 119.65(13) . . ? C22 C21 N3 116.51(11) . . ? C26 C21 N3 123.81(12) . . ? C23 C22 C21 120.29(12) . . ? C22 C23 C24 120.39(13) . . ? C25 C24 C23 119.11(14) . . ? C24 C25 C26 121.38(13) . . ? C25 C26 C21 119.18(13) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.534 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.215 data_nitro2 _database_code_depnum_ccdc_archive 'CCDC 270921' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(8-Dimethylaminonaphth-1-yl)-2-nitroethene ; _chemical_name_common ? _chemical_melting_point 412-413 _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N2 O2' _chemical_formula_weight 242.27 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 15.8700(3) _cell_length_b 5.48170(10) _cell_length_c 28.7715(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.0295(8) _cell_angle_gamma 90.00 _cell_volume 2456.73(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8520 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.573 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8520 _diffrn_reflns_av_R_equivalents 0.1182 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2785 _reflns_number_gt 2023 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0669P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2785 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.068 _refine_ls_shift/su_mean 0.015 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 0.38016(7) -0.13116(19) 0.52339(4) 0.0379(3) Uani 1 1 d . . . O2 O 0.30145(7) -0.36159(16) 0.55869(4) 0.0371(3) Uani 1 1 d . . . N1 N 0.10002(6) 0.04749(19) 0.58929(4) 0.0211(3) Uani 1 1 d . . . N2 N 0.33271(7) -0.1631(2) 0.55204(4) 0.0254(3) Uani 1 1 d . . . C1 C 0.09660(8) 0.1944(2) 0.62935(5) 0.0207(3) Uani 1 1 d . . . C2 C 0.02211(9) 0.2394(3) 0.64582(5) 0.0253(3) Uani 1 1 d . . . C3 C 0.02086(10) 0.4059(3) 0.68296(6) 0.0295(4) Uani 1 1 d . . . C4 C 0.09251(9) 0.5324(3) 0.70250(5) 0.0284(4) Uani 1 1 d . . . C5 C 0.24792(10) 0.6069(3) 0.70955(6) 0.0293(4) Uani 1 1 d . . . C6 C 0.32502(10) 0.5477(3) 0.69847(6) 0.0314(4) Uani 1 1 d . . . C7 C 0.33000(9) 0.3606(2) 0.66577(5) 0.0268(3) Uani 1 1 d . . . C8 C 0.25783(8) 0.2362(2) 0.64340(5) 0.0213(3) Uani 1 1 d . . . C9 C 0.17181(9) 0.4852(2) 0.68812(5) 0.0244(3) Uani 1 1 d . . . C10 C 0.17528(8) 0.3035(2) 0.65305(5) 0.0202(3) Uani 1 1 d . . . C11 C 0.26917(8) 0.0284(2) 0.61265(5) 0.0218(3) Uani 1 1 d . . . C12 C 0.31551(8) 0.0466(2) 0.57913(5) 0.0244(3) Uani 1 1 d . . . C13 C 0.03413(10) -0.1405(3) 0.57808(6) 0.0283(4) Uani 1 1 d . . . C14 C 0.10644(10) 0.1917(3) 0.54698(5) 0.0239(3) Uani 1 1 d . . . H2 H -0.0314(10) 0.155(3) 0.6308(6) 0.035(4) Uiso 1 1 d . . . H3 H -0.0338(10) 0.431(3) 0.6937(6) 0.035(4) Uiso 1 1 d . . . H4 H 0.0898(10) 0.652(3) 0.7263(6) 0.037(4) Uiso 1 1 d . . . H5 H 0.2445(9) 0.732(3) 0.7317(6) 0.037(4) Uiso 1 1 d . . . H6 H 0.3745(11) 0.627(3) 0.7144(6) 0.045(5) Uiso 1 1 d . . . H7 H 0.3880(10) 0.310(3) 0.6591(5) 0.029(4) Uiso 1 1 d . . . H11 H 0.2448(9) -0.130(3) 0.6184(5) 0.028(4) Uiso 1 1 d . . . H12 H 0.3405(9) 0.185(3) 0.5695(5) 0.026(4) Uiso 1 1 d . . . H13A H -0.0247(10) -0.070(3) 0.5668(6) 0.033(4) Uiso 1 1 d . . . H13B H 0.0334(8) -0.238(3) 0.6056(6) 0.028(4) Uiso 1 1 d . . . H13C H 0.0497(9) -0.247(3) 0.5542(6) 0.033(4) Uiso 1 1 d . . . H14A H 0.0501(10) 0.267(3) 0.5335(6) 0.031(4) Uiso 1 1 d . . . H14B H 0.1492(9) 0.321(3) 0.5548(5) 0.026(4) Uiso 1 1 d . . . H14C H 0.1233(9) 0.080(3) 0.5238(6) 0.030(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0443(6) 0.0378(6) 0.0372(7) 0.0018(5) 0.0221(6) 0.0044(5) O2 0.0461(7) 0.0198(5) 0.0490(8) -0.0005(5) 0.0180(6) -0.0001(4) N1 0.0232(6) 0.0196(6) 0.0201(6) 0.0000(5) 0.0030(5) -0.0015(4) N2 0.0250(6) 0.0229(6) 0.0285(7) 0.0036(5) 0.0056(5) 0.0039(5) C1 0.0253(7) 0.0175(6) 0.0192(7) 0.0029(5) 0.0042(6) 0.0008(5) C2 0.0237(7) 0.0259(7) 0.0265(8) 0.0033(6) 0.0052(6) 0.0011(6) C3 0.0343(8) 0.0294(7) 0.0278(9) 0.0034(6) 0.0137(7) 0.0070(6) C4 0.0412(9) 0.0254(7) 0.0201(8) -0.0006(6) 0.0094(7) 0.0045(6) C5 0.0432(9) 0.0233(7) 0.0197(8) -0.0010(6) 0.0015(7) -0.0046(6) C6 0.0346(8) 0.0282(7) 0.0279(9) 0.0023(7) -0.0027(7) -0.0112(6) C7 0.0257(7) 0.0268(7) 0.0268(8) 0.0050(6) 0.0021(6) -0.0033(6) C8 0.0240(7) 0.0195(6) 0.0196(7) 0.0052(6) 0.0025(6) -0.0011(5) C9 0.0337(8) 0.0207(6) 0.0182(7) 0.0033(6) 0.0033(6) 0.0003(5) C10 0.0250(7) 0.0184(6) 0.0169(7) 0.0030(5) 0.0033(6) 0.0005(5) C11 0.0176(6) 0.0205(7) 0.0258(8) 0.0039(6) 0.0003(6) 0.0013(5) C12 0.0243(7) 0.0188(7) 0.0304(9) 0.0025(6) 0.0059(6) 0.0005(5) C13 0.0323(8) 0.0239(7) 0.0280(9) -0.0018(7) 0.0036(7) -0.0061(6) C14 0.0280(8) 0.0250(7) 0.0183(8) 0.0002(6) 0.0033(6) 0.0004(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 N2 1.2307(14) . ? O2 N2 1.2259(14) . ? N1 C1 1.4158(17) . ? N1 C13 1.4595(17) . ? N1 C14 1.4712(17) . ? N2 C12 1.4441(17) . ? C1 C2 1.3772(18) . ? C1 C10 1.4337(18) . ? C2 C3 1.408(2) . ? C3 C4 1.359(2) . ? C4 C9 1.4216(19) . ? C5 C6 1.361(2) . ? C5 C9 1.4140(19) . ? C6 C7 1.404(2) . ? C7 C8 1.3819(19) . ? C8 C10 1.4382(19) . ? C8 C11 1.4740(19) . ? C9 C10 1.4265(19) . ? C11 C12 1.3237(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 C13 116.36(11) . . ? C1 N1 C14 112.79(10) . . ? C13 N1 C14 110.91(12) . . ? O2 N2 O1 123.27(12) . . ? O2 N2 C12 119.89(12) . . ? O1 N2 C12 116.82(11) . . ? C2 C1 N1 123.44(12) . . ? C2 C1 C10 119.25(13) . . ? N1 C1 C10 117.30(11) . . ? C1 C2 C3 120.97(14) . . ? C4 C3 C2 120.84(13) . . ? C3 C4 C9 120.27(13) . . ? C6 C5 C9 121.10(14) . . ? C5 C6 C7 119.96(13) . . ? C8 C7 C6 121.65(13) . . ? C7 C8 C10 119.20(13) . . ? C7 C8 C11 118.39(12) . . ? C10 C8 C11 122.30(12) . . ? C5 C9 C4 121.14(13) . . ? C5 C9 C10 119.51(12) . . ? C4 C9 C10 119.29(12) . . ? C9 C10 C1 118.65(11) . . ? C9 C10 C8 118.39(12) . . ? C1 C10 C8 122.95(12) . . ? C12 C11 C8 121.86(12) . . ? C11 C12 N2 121.47(13) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.209 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.072 data_me2nno2me _database_code_depnum_ccdc_archive 'CCDC 270922' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(8-Dimethylaminonaphth-1-yl)-2-nitropropene ; _chemical_name_common ? _chemical_melting_point 341-342 _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N2 O2' _chemical_formula_weight 256.30 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 P2(1)/n 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 10.3347(3) _cell_length_b 7.0992(2) _cell_length_c 18.2556(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.897(2) _cell_angle_gamma 90.00 _cell_volume 1305.59(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17274 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.47 _exptl_crystal_description slab _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.615 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17273 _diffrn_reflns_av_R_equivalents 0.0889 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2980 _reflns_number_gt 2599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1082P)^2^+0.3251P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2980 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1664 _refine_ls_wR_factor_gt 0.1579 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 1.14762(13) 0.64249(19) 0.45551(6) 0.0412(3) Uani 1 1 d . . . O2 O 0.96101(15) 0.7282(2) 0.47932(7) 0.0496(4) Uani 1 1 d . . . N1 N 1.09222(11) 0.18677(16) 0.31855(6) 0.0208(3) Uani 1 1 d . . . N2 N 1.02653(14) 0.66250(18) 0.43734(7) 0.0284(3) Uani 1 1 d . . . C1 C 1.08019(13) 0.18804(19) 0.23946(7) 0.0194(3) Uani 1 1 d . . . C2 C 1.12672(14) 0.0444(2) 0.20173(8) 0.0244(3) Uani 1 1 d . . . C3 C 1.10354(15) 0.0440(2) 0.12254(8) 0.0271(3) Uani 1 1 d . . . C4 C 1.03046(14) 0.1831(2) 0.08156(8) 0.0248(3) Uani 1 1 d . . . C5 C 0.90677(14) 0.4817(2) 0.07569(7) 0.0237(3) Uani 1 1 d . . . C6 C 0.86436(14) 0.6326(2) 0.11028(8) 0.0251(3) Uani 1 1 d . . . C7 C 0.90175(14) 0.6491(2) 0.18917(8) 0.0224(3) Uani 1 1 d . . . C8 C 0.97581(13) 0.51151(19) 0.23317(7) 0.0183(3) Uani 1 1 d . . . C9 C 1.01339(12) 0.34527(19) 0.19818(7) 0.0175(3) Uani 1 1 d . . . C10 C 0.98277(13) 0.3363(2) 0.11791(7) 0.0201(3) Uani 1 1 d . . . C11 C 1.02740(13) 0.55196(18) 0.31409(7) 0.0190(3) Uani 1 1 d . . . C12 C 0.95363(14) 0.60882(19) 0.36140(7) 0.0214(3) Uani 1 1 d . . . C13 C 0.80659(15) 0.6226(2) 0.34956(9) 0.0280(3) Uani 1 1 d . . . C14 C 0.96708(15) 0.1384(2) 0.33909(8) 0.0241(3) Uani 1 1 d . . . C15 C 1.20206(16) 0.0762(2) 0.36215(9) 0.0306(4) Uani 1 1 d . . . H2 H 1.1737(19) -0.069(3) 0.2302(11) 0.033(5) Uiso 1 1 d . . . H3 H 1.139(2) -0.056(3) 0.0969(11) 0.039(5) Uiso 1 1 d . . . H4 H 1.0089(19) 0.183(3) 0.0267(11) 0.034(5) Uiso 1 1 d . . . H5 H 0.8873(18) 0.472(2) 0.0209(10) 0.026(4) Uiso 1 1 d . . . H6 H 0.8129(19) 0.736(3) 0.0817(10) 0.028(4) Uiso 1 1 d . . . H7 H 0.8787(18) 0.763(3) 0.2114(10) 0.029(4) Uiso 1 1 d . . . H11 H 1.1221(17) 0.548(2) 0.3299(9) 0.019(4) Uiso 1 1 d . . . H13A H 0.7643(19) 0.562(3) 0.3022(11) 0.031(5) Uiso 1 1 d . . . H13B H 0.779(2) 0.753(3) 0.3501(11) 0.040(5) Uiso 1 1 d . . . H13C H 0.776(2) 0.557(3) 0.3907(12) 0.041(5) Uiso 1 1 d . . . H14A H 0.894(2) 0.220(3) 0.3093(11) 0.033(5) Uiso 1 1 d . . . H14B H 0.944(2) 0.004(3) 0.3285(11) 0.037(5) Uiso 1 1 d . . . H14C H 0.975(2) 0.157(3) 0.3919(12) 0.039(5) Uiso 1 1 d . . . H15A H 1.2867(19) 0.107(3) 0.3500(10) 0.029(5) Uiso 1 1 d . . . H15B H 1.207(2) 0.105(3) 0.4148(13) 0.045(6) Uiso 1 1 d . . . H15C H 1.188(2) -0.061(3) 0.3545(12) 0.039(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0403(7) 0.0547(8) 0.0229(5) -0.0076(5) -0.0053(5) -0.0075(6) O2 0.0642(9) 0.0612(9) 0.0267(6) -0.0173(6) 0.0168(6) -0.0004(7) N1 0.0224(6) 0.0208(6) 0.0168(5) 0.0010(4) -0.0010(4) 0.0016(4) N2 0.0416(8) 0.0262(7) 0.0170(6) -0.0028(5) 0.0060(5) -0.0057(5) C1 0.0177(6) 0.0198(6) 0.0197(6) -0.0013(5) 0.0018(5) -0.0018(5) C2 0.0227(7) 0.0220(7) 0.0270(7) -0.0031(5) 0.0026(5) 0.0009(5) C3 0.0276(7) 0.0273(8) 0.0273(7) -0.0095(6) 0.0083(6) 0.0001(6) C4 0.0251(7) 0.0303(8) 0.0193(6) -0.0063(5) 0.0059(5) -0.0053(5) C5 0.0233(7) 0.0301(8) 0.0165(6) 0.0018(5) 0.0021(5) -0.0052(5) C6 0.0253(7) 0.0269(7) 0.0208(7) 0.0061(5) 0.0006(5) 0.0019(6) C7 0.0228(7) 0.0223(7) 0.0211(7) 0.0007(5) 0.0031(5) 0.0023(5) C8 0.0177(6) 0.0196(6) 0.0169(6) 0.0006(5) 0.0024(5) -0.0014(5) C9 0.0155(6) 0.0199(6) 0.0166(6) -0.0006(5) 0.0027(5) -0.0023(5) C10 0.0179(6) 0.0241(7) 0.0180(6) -0.0019(5) 0.0034(5) -0.0055(5) C11 0.0218(7) 0.0152(6) 0.0185(6) 0.0001(5) 0.0013(5) -0.0007(5) C12 0.0288(7) 0.0179(6) 0.0168(6) -0.0011(5) 0.0035(5) -0.0019(5) C13 0.0282(7) 0.0286(8) 0.0296(7) -0.0020(6) 0.0118(6) 0.0001(6) C14 0.0281(7) 0.0241(7) 0.0197(6) 0.0001(5) 0.0047(5) -0.0035(6) C15 0.0305(8) 0.0283(8) 0.0275(7) 0.0051(6) -0.0052(6) 0.0074(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 N2 1.2293(19) . ? O2 N2 1.2228(18) . ? N1 C1 1.4212(17) . ? N1 C15 1.4612(18) . ? N1 C14 1.4655(18) . ? N2 C12 1.4725(17) . ? C1 C2 1.3762(19) . ? C1 C9 1.4346(18) . ? C2 C3 1.412(2) . ? C3 C4 1.362(2) . ? C4 C10 1.418(2) . ? C5 C6 1.364(2) . ? C5 C10 1.417(2) . ? C6 C7 1.4101(19) . ? C7 C8 1.3821(19) . ? C8 C9 1.4361(18) . ? C8 C11 1.4823(17) . ? C9 C10 1.4299(17) . ? C11 C12 1.3357(19) . ? C12 C13 1.490(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 C15 115.98(12) . . ? C1 N1 C14 112.30(10) . . ? C15 N1 C14 110.94(12) . . ? O2 N2 O1 123.21(13) . . ? O2 N2 C12 116.76(14) . . ? O1 N2 C12 120.02(12) . . ? C2 C1 N1 122.86(12) . . ? C2 C1 C9 119.65(12) . . ? N1 C1 C9 117.47(11) . . ? C1 C2 C3 121.05(13) . . ? C4 C3 C2 120.51(13) . . ? C3 C4 C10 120.48(13) . . ? C6 C5 C10 121.11(12) . . ? C5 C6 C7 119.65(13) . . ? C8 C7 C6 121.67(13) . . ? C7 C8 C9 119.45(12) . . ? C7 C8 C11 118.15(12) . . ? C9 C8 C11 121.98(12) . . ? C10 C9 C1 118.30(12) . . ? C10 C9 C8 118.20(12) . . ? C1 C9 C8 123.50(11) . . ? C5 C10 C4 120.83(12) . . ? C5 C10 C9 119.60(12) . . ? C4 C10 C9 119.56(12) . . ? C12 C11 C8 124.94(12) . . ? C11 C12 N2 116.17(13) . . ? C11 C12 C13 129.57(13) . . ? N2 C12 C13 114.24(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.233 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.070g data_xavier _database_code_depnum_ccdc_archive 'CCDC 270923' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1-Dimethylbenzo(cd)indolium-2-benzoylnitromethide ; _chemical_name_common ? _chemical_melting_point 434-435 _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N2 O3' _chemical_formula_weight 346.37 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 P2(1)/c 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 7.7283(2) _cell_length_b 13.6696(4) _cell_length_c 15.7465(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.5779(12) _cell_angle_gamma 90.00 _cell_volume 1655.63(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10095 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.620 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10095 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3764 _reflns_number_gt 2820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0712P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3764 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 0.68623(12) 0.29362(8) 0.12973(7) 0.0265(3) Uani 1 1 d . . . O2 O 0.39982(13) 0.00178(7) 0.09591(6) 0.0250(3) Uani 1 1 d . . . O3 O 0.31488(13) 0.13105(8) 0.02060(6) 0.0269(3) Uani 1 1 d . . . N1 N 0.81456(14) 0.04652(8) 0.17050(7) 0.0167(3) Uani 1 1 d . . . N2 N 0.41032(15) 0.09305(9) 0.08141(7) 0.0196(3) Uani 1 1 d . . . C1 C 0.95563(17) 0.07795(10) 0.23539(8) 0.0171(3) Uani 1 1 d . . . C2 C 1.12527(18) 0.04820(11) 0.24517(9) 0.0213(3) Uani 1 1 d . . . C3 C 1.23214(18) 0.09104(11) 0.31351(9) 0.0229(3) Uani 1 1 d . . . C4 C 1.17256(18) 0.15949(11) 0.36792(9) 0.0223(3) Uani 1 1 d . . . C5 C 0.91039(19) 0.25533(11) 0.40916(9) 0.0222(3) Uani 1 1 d . . . C6 C 0.7356(2) 0.27413(11) 0.39107(9) 0.0238(3) Uani 1 1 d . . . C7 C 0.63330(19) 0.22823(11) 0.32229(9) 0.0216(3) Uani 1 1 d . . . C8 C 0.71225(17) 0.16335(10) 0.27220(8) 0.0175(3) Uani 1 1 d . . . C9 C 0.99579(17) 0.18896(10) 0.35787(8) 0.0187(3) Uani 1 1 d . . . C10 C 0.89035(17) 0.14548(10) 0.29016(8) 0.0169(3) Uani 1 1 d . . . C11 C 0.63904(17) 0.09972(10) 0.19901(8) 0.0174(3) Uani 1 1 d . . . C12 C 0.52863(16) 0.14909(10) 0.13078(8) 0.0181(3) Uani 1 1 d . . . C13 C 0.54155(16) 0.25464(10) 0.11872(8) 0.0174(3) Uani 1 1 d . . . C18 C 0.7910(2) -0.06253(11) 0.17186(10) 0.0222(3) Uani 1 1 d . . . C19 C 0.8543(2) 0.07922(12) 0.08340(8) 0.0221(3) Uani 1 1 d . . . C21 C 0.38416(16) 0.31805(10) 0.10475(8) 0.0169(3) Uani 1 1 d . . . C22 C 0.40373(18) 0.41375(11) 0.07567(9) 0.0200(3) Uani 1 1 d . . . C23 C 0.26257(19) 0.47691(11) 0.06712(9) 0.0236(3) Uani 1 1 d . . . C24 C 0.10154(19) 0.44499(11) 0.08826(9) 0.0237(3) Uani 1 1 d . . . C25 C 0.08147(18) 0.35122(11) 0.11878(9) 0.0223(3) Uani 1 1 d . . . C26 C 0.22224(18) 0.28777(11) 0.12729(9) 0.0195(3) Uani 1 1 d . . . H2 H 1.168(2) 0.0011(13) 0.2098(10) 0.026(4) Uiso 1 1 d . . . H3 H 1.351(2) 0.0720(12) 0.3217(10) 0.025(4) Uiso 1 1 d . . . H4 H 1.249(2) 0.1904(12) 0.4143(10) 0.021(4) Uiso 1 1 d . . . H5 H 0.978(2) 0.2899(12) 0.4554(10) 0.026(4) Uiso 1 1 d . . . H6 H 0.677(2) 0.3182(12) 0.4254(11) 0.027(4) Uiso 1 1 d . . . H7 H 0.510(2) 0.2432(12) 0.3111(10) 0.026(4) Uiso 1 1 d . . . H11 H 0.5750(18) 0.0439(11) 0.2205(9) 0.015(4) Uiso 1 1 d . . . H18A H 0.694(2) -0.0808(12) 0.1296(11) 0.027(4) Uiso 1 1 d . . . H18B H 0.760(2) -0.0808(13) 0.2299(12) 0.034(5) Uiso 1 1 d . . . H18C H 0.895(2) -0.0948(14) 0.1576(11) 0.035(5) Uiso 1 1 d . . . H19A H 0.972(2) 0.0534(12) 0.0746(11) 0.030(4) Uiso 1 1 d . . . H19B H 0.761(2) 0.0540(11) 0.0395(10) 0.022(4) Uiso 1 1 d . . . H19C H 0.859(2) 0.1512(12) 0.0816(10) 0.021(4) Uiso 1 1 d . . . H22 H 0.517(2) 0.4321(12) 0.0626(10) 0.023(4) Uiso 1 1 d . . . H23 H 0.278(2) 0.5446(13) 0.0491(11) 0.031(4) Uiso 1 1 d . . . H24 H -0.002(2) 0.4884(14) 0.0833(11) 0.037(5) Uiso 1 1 d . . . H25 H -0.031(2) 0.3299(12) 0.1346(10) 0.028(4) Uiso 1 1 d . . . H26 H 0.2125(19) 0.2213(11) 0.1510(9) 0.016(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0171(5) 0.0245(6) 0.0374(6) 0.0054(5) -0.0002(4) -0.0012(4) O2 0.0287(6) 0.0178(5) 0.0273(6) -0.0040(4) -0.0027(4) -0.0036(4) O3 0.0275(6) 0.0301(6) 0.0206(5) -0.0045(4) -0.0104(4) 0.0069(5) N1 0.0204(6) 0.0155(6) 0.0137(6) -0.0010(4) -0.0009(4) 0.0027(5) N2 0.0195(6) 0.0207(7) 0.0181(6) -0.0031(5) -0.0014(4) 0.0009(5) C1 0.0193(7) 0.0192(7) 0.0123(6) 0.0036(5) -0.0007(5) -0.0008(6) C2 0.0219(7) 0.0228(8) 0.0195(7) 0.0024(6) 0.0043(5) 0.0045(6) C3 0.0172(7) 0.0287(8) 0.0227(8) 0.0071(6) 0.0016(5) 0.0000(6) C4 0.0196(7) 0.0259(8) 0.0204(7) 0.0060(6) -0.0028(5) -0.0059(6) C5 0.0292(7) 0.0201(7) 0.0165(7) -0.0022(6) -0.0017(6) -0.0040(6) C6 0.0314(8) 0.0198(8) 0.0202(7) -0.0047(6) 0.0030(6) 0.0013(6) C7 0.0227(7) 0.0214(8) 0.0204(7) -0.0014(6) 0.0008(6) 0.0020(6) C8 0.0199(7) 0.0170(7) 0.0150(6) 0.0012(5) -0.0012(5) -0.0010(6) C9 0.0218(7) 0.0190(7) 0.0149(7) 0.0034(5) -0.0009(5) -0.0029(6) C10 0.0208(7) 0.0165(7) 0.0135(7) 0.0034(5) 0.0012(5) -0.0008(5) C11 0.0176(7) 0.0173(7) 0.0175(7) -0.0009(5) 0.0024(5) 0.0010(6) C12 0.0171(7) 0.0185(7) 0.0183(7) -0.0010(5) -0.0009(5) -0.0001(6) C13 0.0161(7) 0.0213(7) 0.0145(6) 0.0008(5) 0.0000(5) -0.0003(6) C18 0.0285(8) 0.0139(7) 0.0229(8) -0.0015(6) -0.0034(6) 0.0027(6) C19 0.0279(8) 0.0256(8) 0.0127(7) 0.0012(6) 0.0019(6) 0.0040(7) C21 0.0187(7) 0.0184(7) 0.0129(6) -0.0017(5) -0.0013(5) 0.0009(6) C22 0.0206(7) 0.0208(8) 0.0184(7) 0.0014(6) 0.0013(5) -0.0002(6) C23 0.0299(8) 0.0196(7) 0.0207(7) 0.0006(6) -0.0005(6) 0.0036(6) C24 0.0233(7) 0.0283(8) 0.0181(7) -0.0054(6) -0.0047(5) 0.0095(7) C25 0.0164(7) 0.0282(8) 0.0219(7) -0.0065(6) 0.0001(5) -0.0006(6) C26 0.0192(7) 0.0206(7) 0.0183(7) -0.0023(6) -0.0003(5) -0.0003(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 C13 1.2355(17) . ? O2 N2 1.2722(15) . ? O3 N2 1.2623(15) . ? N1 C1 1.4835(16) . ? N1 C18 1.5022(18) . ? N1 C19 1.5024(18) . ? N1 C11 1.6397(17) . ? N2 C12 1.3745(17) . ? C1 C2 1.3670(19) . ? C1 C10 1.3910(19) . ? C2 C3 1.418(2) . ? C3 C4 1.378(2) . ? C4 C9 1.4183(19) . ? C5 C6 1.377(2) . ? C5 C9 1.419(2) . ? C6 C7 1.423(2) . ? C7 C8 1.369(2) . ? C8 C10 1.3995(19) . ? C8 C11 1.5094(19) . ? C9 C10 1.4089(19) . ? C11 C12 1.4696(18) . ? C12 C13 1.4600(19) . ? C13 C21 1.4924(19) . ? C21 C26 1.3963(19) . ? C21 C22 1.3990(19) . ? C22 C23 1.387(2) . ? C23 C24 1.389(2) . ? C24 C25 1.383(2) . ? C25 C26 1.388(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 C18 111.06(10) . . ? C1 N1 C19 109.92(10) . . ? C18 N1 C19 110.12(11) . . ? C1 N1 C11 104.78(9) . . ? C18 N1 C11 109.37(10) . . ? C19 N1 C11 111.48(10) . . ? O3 N2 O2 119.79(11) . . ? O3 N2 C12 120.48(12) . . ? O2 N2 C12 119.71(11) . . ? C2 C1 C10 121.95(12) . . ? C2 C1 N1 128.61(13) . . ? C10 C1 N1 109.43(11) . . ? C1 C2 C3 116.37(13) . . ? C4 C3 C2 123.18(13) . . ? C3 C4 C9 120.00(13) . . ? C6 C5 C9 120.17(13) . . ? C5 C6 C7 122.43(14) . . ? C8 C7 C6 118.57(13) . . ? C7 C8 C10 118.77(12) . . ? C7 C8 C11 131.17(12) . . ? C10 C8 C11 109.99(12) . . ? C10 C9 C4 116.40(13) . . ? C10 C9 C5 115.70(12) . . ? C4 C9 C5 127.89(13) . . ? C1 C10 C8 113.54(12) . . ? C1 C10 C9 122.09(12) . . ? C8 C10 C9 124.36(13) . . ? C12 C11 C8 116.20(12) . . ? C12 C11 N1 116.13(11) . . ? C8 C11 N1 101.89(10) . . ? N2 C12 C13 121.83(12) . . ? N2 C12 C11 117.69(12) . . ? C13 C12 C11 120.45(11) . . ? O1 C13 C12 118.70(12) . . ? O1 C13 C21 118.93(13) . . ? C12 C13 C21 121.88(12) . . ? C26 C21 C22 119.24(12) . . ? C26 C21 C13 121.87(13) . . ? C22 C21 C13 118.61(12) . . ? C23 C22 C21 120.30(14) . . ? C22 C23 C24 119.70(14) . . ? C25 C24 C23 120.51(14) . . ? C24 C25 C26 119.97(14) . . ? C25 C26 C21 120.24(14) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.252 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.062