# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email averma@acbr.du.ac.in _publ_contact_author_name 'Verma, Akhilesh' loop_ _publ_author_name 'Vineeta Rustagi' 'Trapti Aggarwal' 'Akhilesh Verma' data_3a _database_code_depnum_ccdc_archive 'CCDC 818980' #TrackingRef '- 3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common pyrrolo(2,1-a)quinoxaline' _chemical_melting_point 418 _chemical_formula_moiety 'C25 H18 N2' _chemical_formula_sum 'C25 H18 N2' _chemical_formula_weight 346.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.8589(3) _cell_length_b 10.2068(4) _cell_length_c 11.4469(4) _cell_angle_alpha 64.251(4) _cell_angle_beta 84.500(3) _cell_angle_gamma 74.527(3) _cell_volume 898.24(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5055 _cell_measurement_theta_min 4.2857 _cell_measurement_theta_max 72.7363 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86357 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9853 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7733 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0185 _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 4.29 _diffrn_reflns_theta_max 72.50 _reflns_number_total 3524 _reflns_number_gt 3128 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.1348P] 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 3524 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.55241(17) -0.06433(15) 0.73538(15) 0.0555(4) Uani 1 1 d . . . H1 H 0.5445 -0.1230 0.6939 0.067 Uiso 1 1 calc R . . C2 C 0.67754(18) -0.08258(17) 0.80474(17) 0.0652(4) Uani 1 1 d . . . H2 H 0.7712 -0.1561 0.8193 0.078 Uiso 1 1 calc R . . C3 C 0.64176(17) 0.02914(17) 0.85130(16) 0.0601(4) Uani 1 1 d . . . H3 H 0.7070 0.0426 0.9020 0.072 Uiso 1 1 calc R . . C4 C 0.49407(14) 0.11364(14) 0.80841(12) 0.0431(3) Uani 1 1 d . . . C5 C 0.39543(13) 0.24810(13) 0.82423(11) 0.0382(3) Uani 1 1 d . . . H5 H 0.4119 0.2307 0.9138 0.046 Uiso 1 1 calc R . . C6 C 0.43249(13) 0.39762(13) 0.73663(11) 0.0388(3) Uani 1 1 d . . . C7 C 0.56992(15) 0.41385(15) 0.66959(13) 0.0462(3) Uani 1 1 d . . . H7 H 0.6461 0.3295 0.6729 0.055 Uiso 1 1 calc R . . C8 C 0.59379(17) 0.55608(17) 0.59743(14) 0.0526(3) Uani 1 1 d . . . H8 H 0.6861 0.5670 0.5525 0.063 Uiso 1 1 calc R . . C9 C 0.48075(17) 0.68144(16) 0.59224(14) 0.0538(3) Uani 1 1 d . . . H9 H 0.4965 0.7766 0.5424 0.065 Uiso 1 1 calc R . . C10 C 0.34448(17) 0.66654(15) 0.66053(14) 0.0501(3) Uani 1 1 d . . . H10 H 0.2700 0.7515 0.6581 0.060 Uiso 1 1 calc R . . C11 C 0.31819(14) 0.52439(14) 0.73310(12) 0.0412(3) Uani 1 1 d . . . C12 C 0.17389(14) 0.50247(14) 0.80355(12) 0.0432(3) Uani 1 1 d . . . H12 H 0.1138 0.5767 0.8271 0.052 Uiso 1 1 calc R . . C13 C 0.12626(13) 0.37717(13) 0.83501(11) 0.0382(3) Uani 1 1 d . . . C14 C -0.02297(14) 0.35073(14) 0.89842(12) 0.0404(3) Uani 1 1 d . . . C15 C -0.15605(16) 0.46874(16) 0.87535(14) 0.0518(3) Uani 1 1 d . . . H15 H -0.1518 0.5660 0.8183 0.062 Uiso 1 1 calc R . . C16 C -0.29438(17) 0.44298(19) 0.93635(17) 0.0625(4) Uani 1 1 d . . . H16 H -0.3827 0.5227 0.9195 0.075 Uiso 1 1 calc R . . C17 C -0.30230(17) 0.29981(19) 1.02210(16) 0.0617(4) Uani 1 1 d . . . H17 H -0.3952 0.2830 1.0640 0.074 Uiso 1 1 calc R . . C18 C -0.17239(18) 0.18252(18) 1.04516(16) 0.0620(4) Uani 1 1 d . . . H18 H -0.1774 0.0858 1.1029 0.074 Uiso 1 1 calc R . . C19 C -0.03350(15) 0.20674(15) 0.98324(14) 0.0509(3) Uani 1 1 d . . . H19 H 0.0534 0.1259 0.9986 0.061 Uiso 1 1 calc R . . C20 C 0.18516(13) 0.23020(12) 0.70883(11) 0.0379(3) Uani 1 1 d . . . C21 C 0.04089(15) 0.30151(16) 0.64347(13) 0.0501(3) Uani 1 1 d . . . H21 H -0.0290 0.3750 0.6628 0.060 Uiso 1 1 calc R . . C22 C -0.00003(18) 0.2644(2) 0.54997(16) 0.0644(4) Uani 1 1 d . . . H22 H -0.0977 0.3119 0.5083 0.077 Uiso 1 1 calc R . . C23 C 0.10302(19) 0.1577(2) 0.51823(16) 0.0653(4) Uani 1 1 d . . . H23 H 0.0747 0.1324 0.4560 0.078 Uiso 1 1 calc R . . C24 C 0.24841(17) 0.08858(16) 0.57936(14) 0.0529(3) Uani 1 1 d . . . H24 H 0.3190 0.0182 0.5568 0.063 Uiso 1 1 calc R . . C25 C 0.28979(14) 0.12342(13) 0.67423(12) 0.0407(3) Uani 1 1 d . . . N1 N 0.43823(12) 0.05714(11) 0.73706(10) 0.0430(3) Uani 1 1 d . . . N2 N 0.22800(11) 0.25816(10) 0.80968(10) 0.0375(2) 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 0.0579(8) 0.0443(7) 0.0635(9) -0.0271(6) 0.0122(7) -0.0083(6) C2 0.0520(8) 0.0535(8) 0.0785(11) -0.0282(8) 0.0011(7) 0.0054(6) C3 0.0460(7) 0.0586(8) 0.0711(10) -0.0297(7) -0.0077(7) 0.0008(6) C4 0.0401(6) 0.0411(6) 0.0454(7) -0.0167(5) 0.0038(5) -0.0101(5) C5 0.0337(6) 0.0417(6) 0.0393(6) -0.0170(5) 0.0005(4) -0.0098(5) C6 0.0383(6) 0.0446(6) 0.0381(6) -0.0191(5) 0.0002(5) -0.0151(5) C7 0.0401(6) 0.0559(7) 0.0487(7) -0.0259(6) 0.0051(5) -0.0169(5) C8 0.0507(8) 0.0680(9) 0.0500(7) -0.0281(7) 0.0138(6) -0.0313(7) C9 0.0664(9) 0.0527(7) 0.0510(7) -0.0211(6) 0.0103(6) -0.0333(7) C10 0.0559(8) 0.0445(7) 0.0562(8) -0.0238(6) 0.0061(6) -0.0203(6) C11 0.0426(6) 0.0436(6) 0.0435(6) -0.0209(5) 0.0034(5) -0.0169(5) C12 0.0428(6) 0.0417(6) 0.0486(7) -0.0229(5) 0.0062(5) -0.0117(5) C13 0.0358(6) 0.0395(6) 0.0393(6) -0.0172(5) 0.0028(5) -0.0094(5) C14 0.0369(6) 0.0448(6) 0.0422(6) -0.0208(5) 0.0041(5) -0.0115(5) C15 0.0446(7) 0.0480(7) 0.0593(8) -0.0230(6) 0.0076(6) -0.0083(6) C16 0.0406(7) 0.0705(10) 0.0764(10) -0.0381(8) 0.0111(7) -0.0054(6) C17 0.0435(7) 0.0825(11) 0.0685(9) -0.0389(8) 0.0206(7) -0.0257(7) C18 0.0566(9) 0.0606(9) 0.0651(9) -0.0199(7) 0.0168(7) -0.0263(7) C19 0.0419(7) 0.0462(7) 0.0576(8) -0.0168(6) 0.0075(6) -0.0114(5) C20 0.0391(6) 0.0376(6) 0.0383(6) -0.0136(5) 0.0065(5) -0.0180(5) C21 0.0431(7) 0.0582(8) 0.0505(7) -0.0242(6) 0.0004(6) -0.0129(6) C22 0.0526(8) 0.0858(11) 0.0624(9) -0.0360(8) -0.0074(7) -0.0185(8) C23 0.0698(10) 0.0849(11) 0.0613(9) -0.0426(9) 0.0014(7) -0.0313(8) C24 0.0606(8) 0.0550(8) 0.0558(8) -0.0311(6) 0.0132(6) -0.0256(6) C25 0.0433(6) 0.0379(6) 0.0426(6) -0.0154(5) 0.0094(5) -0.0189(5) N1 0.0432(6) 0.0380(5) 0.0472(6) -0.0181(4) 0.0084(4) -0.0121(4) N2 0.0332(5) 0.0384(5) 0.0427(5) -0.0185(4) 0.0042(4) -0.0109(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 C1 C2 1.351(2) . ? C1 N1 1.3815(16) . ? C1 H1 0.9300 . ? C2 C3 1.410(2) . ? C2 H2 0.9300 . ? C3 C4 1.3601(19) . ? C3 H3 0.9300 . ? C4 N1 1.3723(17) . ? C4 C5 1.4918(16) . ? C5 N2 1.4798(14) . ? C5 C6 1.5222(16) . ? C5 H5 0.9800 . ? C6 C7 1.3845(17) . ? C6 C11 1.4016(17) . ? C7 C8 1.3867(19) . ? C7 H7 0.9300 . ? C8 C9 1.380(2) . ? C8 H8 0.9300 . ? C9 C10 1.3803(19) . ? C9 H9 0.9300 . ? C10 C11 1.3947(17) . ? C10 H10 0.9300 . ? C11 C12 1.4605(17) . ? C12 C13 1.3423(17) . ? C12 H12 0.9300 . ? C13 N2 1.4296(15) . ? C13 C14 1.4778(16) . ? C14 C19 1.3882(18) . ? C14 C15 1.3915(18) . ? C15 C16 1.381(2) . ? C15 H15 0.9300 . ? C16 C17 1.378(2) . ? C16 H16 0.9300 . ? C17 C18 1.370(2) . ? C17 H17 0.9300 . ? C18 C19 1.3857(19) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.3918(18) . ? C20 C25 1.4034(17) . ? C20 N2 1.4093(15) . ? C21 C22 1.385(2) . ? C21 H21 0.9300 . ? C22 C23 1.379(2) . ? C22 H22 0.9300 . ? C23 C24 1.380(2) . ? C23 H23 0.9300 . ? C24 C25 1.3862(19) . ? C24 H24 0.9300 . ? C25 N1 1.4100(16) . ? 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 N1 107.75(13) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C1 C2 C3 108.21(13) . . ? C1 C2 H2 125.9 . . ? C3 C2 H2 125.9 . . ? C4 C3 C2 107.30(14) . . ? C4 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? C3 C4 N1 108.13(12) . . ? C3 C4 C5 131.76(13) . . ? N1 C4 C5 120.09(11) . . ? N2 C5 C4 109.50(10) . . ? N2 C5 C6 110.15(9) . . ? C4 C5 C6 116.19(10) . . ? N2 C5 H5 106.8 . . ? C4 C5 H5 106.8 . . ? C6 C5 H5 106.8 . . ? C7 C6 C11 120.21(11) . . ? C7 C6 C5 125.04(11) . . ? C11 C6 C5 114.64(10) . . ? C6 C7 C8 119.91(12) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.12(12) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.49(12) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C11 120.14(13) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 119.11(12) . . ? C10 C11 C12 122.42(12) . . ? C6 C11 C12 118.45(11) . . ? C13 C12 C11 121.27(11) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 N2 118.38(11) . . ? C12 C13 C14 124.56(11) . . ? N2 C13 C14 117.03(10) . . ? C19 C14 C15 118.27(12) . . ? C19 C14 C13 120.56(11) . . ? C15 C14 C13 121.17(11) . . ? C16 C15 C14 120.68(13) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 120.40(14) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 119.52(13) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 120.59(14) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 120.53(13) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? C21 C20 C25 118.07(12) . . ? C21 C20 N2 122.75(11) . . ? C25 C20 N2 119.17(11) . . ? C22 C21 C20 120.86(13) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C23 C22 C21 120.46(14) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 119.61(14) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C23 C24 C25 120.40(13) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C20 120.57(12) . . ? C24 C25 N1 121.98(12) . . ? C20 C25 N1 117.43(11) . . ? C4 N1 C1 108.60(11) . . ? C4 N1 C25 122.44(10) . . ? C1 N1 C25 128.90(12) . . ? C20 N2 C13 118.12(9) . . ? C20 N2 C5 117.65(9) . . ? C13 N2 C5 112.40(9) . . ? 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 N1 C1 C2 C3 0.11(18) . . . . ? C1 C2 C3 C4 -0.08(19) . . . . ? C2 C3 C4 N1 0.02(17) . . . . ? C2 C3 C4 C5 -178.56(13) . . . . ? C3 C4 C5 N2 -156.00(14) . . . . ? N1 C4 C5 N2 25.55(15) . . . . ? C3 C4 C5 C6 78.44(18) . . . . ? N1 C4 C5 C6 -100.00(13) . . . . ? N2 C5 C6 C7 -142.22(11) . . . . ? C4 C5 C6 C7 -17.00(17) . . . . ? N2 C5 C6 C11 41.47(13) . . . . ? C4 C5 C6 C11 166.69(11) . . . . ? C11 C6 C7 C8 -0.78(18) . . . . ? C5 C6 C7 C8 -176.89(11) . . . . ? C6 C7 C8 C9 -0.1(2) . . . . ? C7 C8 C9 C10 1.2(2) . . . . ? C8 C9 C10 C11 -1.5(2) . . . . ? C9 C10 C11 C6 0.67(19) . . . . ? C9 C10 C11 C12 -177.87(12) . . . . ? C7 C6 C11 C10 0.48(18) . . . . ? C5 C6 C11 C10 176.98(11) . . . . ? C7 C6 C11 C12 179.07(11) . . . . ? C5 C6 C11 C12 -4.43(16) . . . . ? C10 C11 C12 C13 157.11(13) . . . . ? C6 C11 C12 C13 -21.43(18) . . . . ? C11 C12 C13 N2 6.25(18) . . . . ? C11 C12 C13 C14 -175.83(11) . . . . ? C12 C13 C14 C19 -147.66(14) . . . . ? N2 C13 C14 C19 30.29(17) . . . . ? C12 C13 C14 C15 32.13(19) . . . . ? N2 C13 C14 C15 -149.92(12) . . . . ? C19 C14 C15 C16 0.6(2) . . . . ? C13 C14 C15 C16 -179.21(13) . . . . ? C14 C15 C16 C17 0.6(2) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? C17 C18 C19 C14 1.1(2) . . . . ? C15 C14 C19 C18 -1.4(2) . . . . ? C13 C14 C19 C18 178.39(13) . . . . ? C25 C20 C21 C22 2.07(19) . . . . ? N2 C20 C21 C22 -176.27(12) . . . . ? C20 C21 C22 C23 -1.2(2) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? C22 C23 C24 C25 1.5(2) . . . . ? C23 C24 C25 C20 -0.5(2) . . . . ? C23 C24 C25 N1 -178.83(12) . . . . ? C21 C20 C25 C24 -1.23(17) . . . . ? N2 C20 C25 C24 177.17(11) . . . . ? C21 C20 C25 N1 177.16(10) . . . . ? N2 C20 C25 N1 -4.44(15) . . . . ? C3 C4 N1 C1 0.04(15) . . . . ? C5 C4 N1 C1 178.82(11) . . . . ? C3 C4 N1 C25 -177.42(11) . . . . ? C5 C4 N1 C25 1.36(17) . . . . ? C2 C1 N1 C4 -0.09(16) . . . . ? C2 C1 N1 C25 177.16(13) . . . . ? C24 C25 N1 C4 164.88(11) . . . . ? C20 C25 N1 C4 -13.49(17) . . . . ? C24 C25 N1 C1 -12.03(19) . . . . ? C20 C25 N1 C1 169.60(11) . . . . ? C21 C20 N2 C13 -7.48(16) . . . . ? C25 C20 N2 C13 174.20(10) . . . . ? C21 C20 N2 C5 -147.63(11) . . . . ? C25 C20 N2 C5 34.05(14) . . . . ? C12 C13 N2 C20 -108.98(13) . . . . ? C14 C13 N2 C20 72.94(13) . . . . ? C12 C13 N2 C5 33.15(15) . . . . ? C14 C13 N2 C5 -144.94(10) . . . . ? C4 C5 N2 C20 -42.81(13) . . . . ? C6 C5 N2 C20 86.14(12) . . . . ? C4 C5 N2 C13 174.87(9) . . . . ? C6 C5 N2 C13 -56.18(12) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 72.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.213 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.030 # Attachment '- R.cif' data_R _database_code_depnum_ccdc_archive 'CCDC 819358' #TrackingRef '- R.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 453 _chemical_formula_moiety 'C25 H18 N2' _chemical_formula_sum 'C25 H18 N2' _chemical_formula_weight 346.41 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 'P 21/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 9.309(5) _cell_length_b 28.239(5) _cell_length_c 7.304(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 102.501(5) _cell_angle_gamma 90.000(5) _cell_volume 1874.5(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8588 _cell_measurement_theta_min 3.1272 _cell_measurement_theta_max 72.8134 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9853 _diffrn_standards_number 16855 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16646 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 26.15 _reflns_number_total 3715 _reflns_number_gt 3192 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.2225P] 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 3715 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.004 _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 0.74161(16) 0.22821(5) 0.6592(2) 0.0537(3) Uani 1 1 d . . . H1 H 0.7662 0.2520 0.7486 0.064 Uiso 1 1 calc R . . C2 C 0.60642(16) 0.21968(5) 0.5531(2) 0.0585(4) Uani 1 1 d . . . H2 H 0.5214 0.2366 0.5569 0.070 Uiso 1 1 calc R . . C3 C 0.61599(15) 0.18054(5) 0.43504(18) 0.0519(3) Uani 1 1 d . . . H3 H 0.5391 0.1671 0.3477 0.062 Uiso 1 1 calc R . . C4 C 0.75916(14) 0.16626(4) 0.47363(16) 0.0424(3) Uani 1 1 d . . . C5 C 0.99054(15) 0.19191(4) 0.67648(17) 0.0448(3) Uani 1 1 d . . . C6 C 1.06514(17) 0.21383(5) 0.8385(2) 0.0607(4) Uani 1 1 d . . . H6 H 1.0130 0.2301 0.9138 0.073 Uiso 1 1 calc R . . C7 C 1.21648(18) 0.21168(6) 0.8890(2) 0.0695(4) Uani 1 1 d . . . H7 H 1.2664 0.2266 0.9977 0.083 Uiso 1 1 calc R . . C8 C 1.29353(17) 0.18737(6) 0.7783(2) 0.0657(4) Uani 1 1 d . . . H8 H 1.3957 0.1863 0.8114 0.079 Uiso 1 1 calc R . . C9 C 1.22003(16) 0.16464(5) 0.6184(2) 0.0575(3) Uani 1 1 d . . . H9 H 1.2733 0.1480 0.5454 0.069 Uiso 1 1 calc R . . C10 C 1.06739(14) 0.16615(4) 0.56454(18) 0.0457(3) Uani 1 1 d . . . C11 C 0.84265(14) 0.12638(4) 0.40948(16) 0.0436(3) Uani 1 1 d . . . H11 H 0.8560 0.1011 0.5034 0.052 Uiso 1 1 calc R . . C12 C 0.76584(13) 0.10636(4) 0.22199(16) 0.0421(3) Uani 1 1 d . . . C13 C 0.74121(16) 0.13472(5) 0.06289(18) 0.0533(3) Uani 1 1 d . . . H13 H 0.7701 0.1663 0.0736 0.064 Uiso 1 1 calc R . . C14 C 0.67482(17) 0.11698(5) -0.11060(18) 0.0581(4) Uani 1 1 d . . . H14 H 0.6575 0.1367 -0.2151 0.070 Uiso 1 1 calc R . . C15 C 0.63403(16) 0.06995(5) -0.12911(18) 0.0565(3) Uani 1 1 d . . . H15 H 0.5910 0.0578 -0.2465 0.068 Uiso 1 1 calc R . . C16 C 0.65700(14) 0.04107(5) 0.02600(18) 0.0500(3) Uani 1 1 d . . . H16 H 0.6298 0.0094 0.0126 0.060 Uiso 1 1 calc R . . C17 C 0.72068(13) 0.05880(4) 0.20324(16) 0.0403(3) Uani 1 1 d . . . C18 C 0.73939(13) 0.02752(4) 0.36229(17) 0.0438(3) Uani 1 1 d . . . C19 C 0.75143(14) 0.00013(4) 0.48967(18) 0.0465(3) Uani 1 1 d . . . C20 C 0.77239(14) -0.03077(4) 0.64939(17) 0.0433(3) Uani 1 1 d . . . C21 C 0.90826(14) -0.03219(5) 0.77329(19) 0.0502(3) Uani 1 1 d . . . H21 H 0.9853 -0.0137 0.7504 0.060 Uiso 1 1 calc R . . C22 C 0.93009(16) -0.06068(5) 0.9301(2) 0.0566(3) Uani 1 1 d . . . H22 H 1.0216 -0.0614 1.0122 0.068 Uiso 1 1 calc R . . C23 C 0.81667(17) -0.08806(5) 0.96554(19) 0.0578(4) Uani 1 1 d . . . H23 H 0.8317 -0.1073 1.0712 0.069 Uiso 1 1 calc R . . C24 C 0.68081(18) -0.08685(5) 0.8440(2) 0.0604(4) Uani 1 1 d . . . H24 H 0.6041 -0.1051 0.8686 0.072 Uiso 1 1 calc R . . C25 C 0.65802(15) -0.05862(5) 0.68577(19) 0.0527(3) Uani 1 1 d . . . H25 H 0.5665 -0.0582 0.6036 0.063 Uiso 1 1 calc R . . N1 N 0.83682(12) 0.19542(3) 0.61142(14) 0.0445(2) Uani 1 1 d . . . N2 N 0.98773(13) 0.14557(4) 0.39946(15) 0.0509(3) Uani 1 1 d . . . H26 H 1.0413(18) 0.1254(6) 0.349(2) 0.066(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 C1 0.0693(9) 0.0415(7) 0.0555(8) -0.0035(6) 0.0252(7) 0.0070(6) C2 0.0624(9) 0.0560(8) 0.0627(9) 0.0090(6) 0.0261(7) 0.0157(6) C3 0.0537(8) 0.0567(8) 0.0465(7) 0.0071(6) 0.0136(6) -0.0005(6) C4 0.0539(7) 0.0385(6) 0.0369(6) 0.0018(5) 0.0143(5) -0.0031(5) C5 0.0554(7) 0.0342(6) 0.0461(6) -0.0026(5) 0.0140(5) -0.0045(5) C6 0.0702(9) 0.0522(8) 0.0602(9) -0.0173(6) 0.0152(7) -0.0078(7) C7 0.0703(10) 0.0666(10) 0.0669(10) -0.0164(8) 0.0043(8) -0.0196(8) C8 0.0532(8) 0.0668(9) 0.0743(10) 0.0007(8) 0.0075(7) -0.0125(7) C9 0.0545(8) 0.0575(8) 0.0631(8) -0.0015(7) 0.0184(7) -0.0021(6) C10 0.0540(7) 0.0382(6) 0.0466(7) -0.0006(5) 0.0149(5) -0.0038(5) C11 0.0569(7) 0.0361(6) 0.0382(6) -0.0007(5) 0.0108(5) -0.0019(5) C12 0.0512(7) 0.0380(6) 0.0377(6) -0.0007(5) 0.0112(5) 0.0015(5) C13 0.0757(9) 0.0405(7) 0.0443(7) 0.0037(5) 0.0148(6) 0.0008(6) C14 0.0732(9) 0.0621(9) 0.0389(7) 0.0090(6) 0.0120(6) 0.0090(7) C15 0.0598(8) 0.0679(9) 0.0380(7) -0.0074(6) 0.0026(6) 0.0013(7) C16 0.0486(7) 0.0487(7) 0.0511(7) -0.0072(6) 0.0074(6) -0.0066(5) C17 0.0401(6) 0.0396(6) 0.0419(6) 0.0004(5) 0.0102(5) 0.0004(5) C18 0.0450(6) 0.0390(6) 0.0482(7) -0.0011(5) 0.0119(5) -0.0029(5) C19 0.0516(7) 0.0399(6) 0.0494(7) 0.0004(5) 0.0139(6) -0.0003(5) C20 0.0509(7) 0.0355(6) 0.0455(6) -0.0001(5) 0.0147(5) 0.0025(5) C21 0.0463(7) 0.0482(7) 0.0578(8) 0.0013(6) 0.0155(6) -0.0001(5) C22 0.0545(8) 0.0580(8) 0.0547(8) 0.0026(6) 0.0061(6) 0.0091(6) C23 0.0753(10) 0.0496(7) 0.0483(7) 0.0105(6) 0.0135(7) 0.0044(7) C24 0.0696(9) 0.0534(8) 0.0605(8) 0.0066(7) 0.0192(7) -0.0145(7) C25 0.0513(7) 0.0525(8) 0.0525(7) 0.0030(6) 0.0072(6) -0.0072(6) N1 0.0552(6) 0.0367(5) 0.0442(5) -0.0041(4) 0.0168(5) 0.0007(4) N2 0.0547(6) 0.0528(6) 0.0486(6) -0.0134(5) 0.0184(5) -0.0009(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 C1 C2 1.349(2) . ? C1 N1 1.3779(16) . ? C1 H1 0.9300 . ? C2 C3 1.416(2) . ? C2 H2 0.9300 . ? C3 C4 1.3623(19) . ? C3 H3 0.9300 . ? C4 N1 1.3778(16) . ? C4 C11 1.4999(17) . ? C5 C6 1.3824(19) . ? C5 C10 1.4010(18) . ? C5 N1 1.4103(18) . ? C6 C7 1.378(2) . ? C6 H6 0.9300 . ? C7 C8 1.375(2) . ? C7 H7 0.9300 . ? C8 C9 1.377(2) . ? C8 H8 0.9300 . ? C9 C10 1.391(2) . ? C9 H9 0.9300 . ? C10 N2 1.3980(17) . ? C11 N2 1.4716(18) . ? C11 C12 1.5107(18) . ? C11 H11 0.9800 . ? C12 C13 1.3888(18) . ? C12 C17 1.4053(16) . ? C13 C14 1.378(2) . ? C13 H13 0.9300 . ? C14 C15 1.380(2) . ? C14 H14 0.9300 . ? C15 C16 1.375(2) . ? C15 H15 0.9300 . ? C16 C17 1.3949(18) . ? C16 H16 0.9300 . ? C17 C18 1.4396(17) . ? C18 C19 1.1963(18) . ? C19 C20 1.4360(18) . ? C20 C21 1.3874(19) . ? C20 C25 1.3947(18) . ? C21 C22 1.378(2) . ? C21 H21 0.9300 . ? C22 C23 1.378(2) . ? C22 H22 0.9300 . ? C23 C24 1.379(2) . ? C23 H23 0.9300 . ? C24 C25 1.382(2) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? N2 H26 0.888(16) . ? 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 N1 107.81(12) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C1 C2 C3 108.37(12) . . ? C1 C2 H2 125.8 . . ? C3 C2 H2 125.8 . . ? C4 C3 C2 107.01(12) . . ? C4 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? C3 C4 N1 108.03(11) . . ? C3 C4 C11 135.03(12) . . ? N1 C4 C11 116.84(11) . . ? C6 C5 C10 120.46(13) . . ? C6 C5 N1 122.83(12) . . ? C10 C5 N1 116.67(11) . . ? C7 C6 C5 120.29(14) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 119.84(14) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.30(15) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 121.02(14) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 N2 123.38(12) . . ? C9 C10 C5 118.06(12) . . ? N2 C10 C5 118.47(12) . . ? N2 C11 C4 106.40(10) . . ? N2 C11 C12 110.62(10) . . ? C4 C11 C12 112.87(11) . . ? N2 C11 H11 109.0 . . ? C4 C11 H11 109.0 . . ? C12 C11 H11 109.0 . . ? C13 C12 C17 118.54(11) . . ? C13 C12 C11 120.18(11) . . ? C17 C12 C11 121.26(10) . . ? C14 C13 C12 121.32(13) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 119.93(13) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 119.99(12) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.73(13) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C12 119.44(11) . . ? C16 C17 C18 118.79(11) . . ? C12 C17 C18 121.76(11) . . ? C19 C18 C17 177.23(13) . . ? C18 C19 C20 176.45(14) . . ? C21 C20 C25 119.03(12) . . ? C21 C20 C19 119.46(12) . . ? C25 C20 C19 121.49(12) . . ? C22 C21 C20 120.56(13) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.18(13) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C24 119.88(13) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C25 120.39(13) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C20 119.95(13) . . ? C24 C25 H25 120.0 . . ? C20 C25 H25 120.0 . . ? C4 N1 C1 108.77(12) . . ? C4 N1 C5 122.54(10) . . ? C1 N1 C5 128.56(11) . . ? C10 N2 C11 115.55(10) . . ? C10 N2 H26 112.6(10) . . ? C11 N2 H26 112.8(10) . . ? 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 N1 C1 C2 C3 -0.03(15) . . . . ? C1 C2 C3 C4 -0.02(15) . . . . ? C2 C3 C4 N1 0.06(14) . . . . ? C2 C3 C4 C11 176.08(13) . . . . ? C10 C5 C6 C7 1.8(2) . . . . ? N1 C5 C6 C7 -175.84(13) . . . . ? C5 C6 C7 C8 -0.4(2) . . . . ? C6 C7 C8 C9 -0.8(2) . . . . ? C7 C8 C9 C10 0.7(2) . . . . ? C8 C9 C10 N2 176.99(13) . . . . ? C8 C9 C10 C5 0.7(2) . . . . ? C6 C5 C10 C9 -1.94(19) . . . . ? N1 C5 C10 C9 175.86(11) . . . . ? C6 C5 C10 N2 -178.42(12) . . . . ? N1 C5 C10 N2 -0.63(17) . . . . ? C3 C4 C11 N2 143.98(14) . . . . ? N1 C4 C11 N2 -40.26(14) . . . . ? C3 C4 C11 C12 22.48(19) . . . . ? N1 C4 C11 C12 -161.76(10) . . . . ? N2 C11 C12 C13 -56.73(16) . . . . ? C4 C11 C12 C13 62.35(15) . . . . ? N2 C11 C12 C17 121.90(12) . . . . ? C4 C11 C12 C17 -119.03(12) . . . . ? C17 C12 C13 C14 -0.4(2) . . . . ? C11 C12 C13 C14 178.30(13) . . . . ? C12 C13 C14 C15 -1.3(2) . . . . ? C13 C14 C15 C16 1.3(2) . . . . ? C14 C15 C16 C17 0.4(2) . . . . ? C15 C16 C17 C12 -1.98(19) . . . . ? C15 C16 C17 C18 178.53(12) . . . . ? C13 C12 C17 C16 1.96(18) . . . . ? C11 C12 C17 C16 -176.69(11) . . . . ? C13 C12 C17 C18 -178.56(12) . . . . ? C11 C12 C17 C18 2.79(18) . . . . ? C25 C20 C21 C22 0.01(19) . . . . ? C19 C20 C21 C22 178.40(12) . . . . ? C20 C21 C22 C23 -0.1(2) . . . . ? C21 C22 C23 C24 -0.2(2) . . . . ? C22 C23 C24 C25 0.5(2) . . . . ? C23 C24 C25 C20 -0.6(2) . . . . ? C21 C20 C25 C24 0.4(2) . . . . ? C19 C20 C25 C24 -177.98(12) . . . . ? C3 C4 N1 C1 -0.09(14) . . . . ? C11 C4 N1 C1 -176.93(10) . . . . ? C3 C4 N1 C5 -176.31(11) . . . . ? C11 C4 N1 C5 6.85(16) . . . . ? C2 C1 N1 C4 0.07(14) . . . . ? C2 C1 N1 C5 176.00(12) . . . . ? C6 C5 N1 C4 -166.37(12) . . . . ? C10 C5 N1 C4 15.90(17) . . . . ? C6 C5 N1 C1 18.2(2) . . . . ? C10 C5 N1 C1 -159.52(12) . . . . ? C9 C10 N2 C11 146.73(13) . . . . ? C5 C10 N2 C11 -36.98(16) . . . . ? C4 C11 N2 C10 55.57(14) . . . . ? C12 C11 N2 C10 178.49(10) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.172 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.031