# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_added_by_encifer _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3736-D4 _chemical_melting_point ? _chemical_formula_moiety 'C17 H11 Br N2 O' _chemical_formula_sum 'C17 H11 Br N2 O' _chemical_formula_weight 339.19 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 14.5336(5) _cell_length_b 6.3146(2) _cell_length_c 15.7054(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.490(2) _cell_angle_gamma 90.00 _cell_volume 1366.94(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3739 _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 24.99 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.006 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5270 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details sadabs _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 'Bruker APEX-II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9004 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2408 _reflns_number_gt 1782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0262P)^2^+0.6253P] 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 SHELXL _refine_ls_extinction_coef 0.0000(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 2408 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 1.892 _refine_ls_shift/su_mean 0.010 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 Br1 Br 0.47279(2) 1.19738(7) 1.11707(3) 0.0836(2) Uani 1 1 d . . . O1 O 0.13949(14) 0.5882(3) 1.04461(13) 0.0507(5) Uani 1 1 d . . . H9 H 0.091(2) 0.640(5) 1.003(2) 0.076 Uiso 1 1 d . . . N1 N -0.12585(14) 0.7459(3) 0.83469(14) 0.0413(5) Uani 1 1 d . . . H8 H -0.1296 0.6222 0.8563 0.050 Uiso 1 1 calc R . . N2 N 0.03373(14) 0.8387(3) 0.92862(13) 0.0364(5) Uani 1 1 d . . . C1 C -0.3403(2) 0.8882(6) 0.64078(19) 0.0589(8) Uani 1 1 d . . . H1 H -0.3999 0.8386 0.6040 0.071 Uiso 1 1 calc R . . C2 C -0.2858(2) 0.7625(5) 0.71051(19) 0.0515(7) Uani 1 1 d . . . H7 H -0.3077 0.6300 0.7214 0.062 Uiso 1 1 calc R . . C3 C -0.19717(18) 0.8420(4) 0.76367(17) 0.0397(6) Uani 1 1 d . . . C4 C -0.04924(17) 0.8821(4) 0.86392(16) 0.0343(6) Uani 1 1 d . . . C5 C 0.10381(17) 0.9890(4) 0.94659(16) 0.0356(6) Uani 1 1 d . . . C6 C 0.19721(17) 0.9314(4) 1.01453(16) 0.0368(6) Uani 1 1 d . . . C7 C 0.27714(18) 1.0679(5) 1.03450(18) 0.0471(7) Uani 1 1 d . . . H11 H 0.2704 1.2005 1.0074 0.057 Uiso 1 1 calc R . . C8 C 0.3652(2) 1.0091(5) 1.09345(19) 0.0522(8) Uani 1 1 d . . . C9 C 0.3785(2) 0.8147(5) 1.1348(2) 0.0578(8) Uani 1 1 d . . . H2 H 0.4388 0.7764 1.1742 0.069 Uiso 1 1 calc R . . C10 C -0.3085(2) 1.0866(6) 0.62403(19) 0.0579(8) Uani 1 1 d . . . H6 H -0.3465 1.1663 0.5759 0.069 Uiso 1 1 calc R . . C11 C -0.2215(2) 1.1664(5) 0.67771(18) 0.0500(7) Uani 1 1 d . . . H5 H -0.2010 1.3003 0.6668 0.060 Uiso 1 1 calc R . . C12 C -0.16432(17) 1.0436(4) 0.74893(17) 0.0396(6) Uani 1 1 d . . . C13 C -0.06921(17) 1.0710(4) 0.81377(16) 0.0362(6) Uani 1 1 d . . . C14 C 0.0021(2) 1.2240(4) 0.83479(18) 0.0427(6) Uani 1 1 d . . . H4 H -0.0080 1.3532 0.8048 0.051 Uiso 1 1 calc R . . C15 C 0.08885(19) 1.1828(4) 0.90093(17) 0.0411(6) Uani 1 1 d . . . H3 H 0.1377 1.2845 0.9153 0.049 Uiso 1 1 calc R . . C16 C 0.21119(18) 0.7343(4) 1.05818(17) 0.0399(6) Uani 1 1 d . . . C17 C 0.3018(2) 0.6787(5) 1.11708(19) 0.0549(8) Uani 1 1 d . . . H10 H 0.3101 0.5468 1.1448 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0523(2) 0.0958(3) 0.0862(3) 0.0056(2) -0.00159(18) -0.02958(18) O1 0.0488(11) 0.0421(11) 0.0538(12) 0.0145(10) 0.0058(9) -0.0042(9) N1 0.0398(12) 0.0353(12) 0.0439(13) 0.0069(10) 0.0061(10) -0.0033(9) N2 0.0388(11) 0.0340(12) 0.0362(12) 0.0035(10) 0.0119(9) -0.0019(9) C1 0.0412(16) 0.088(2) 0.0439(18) 0.0003(17) 0.0079(13) 0.0081(16) C2 0.0437(15) 0.0610(19) 0.0474(17) 0.0022(15) 0.0112(13) 0.0003(14) C3 0.0384(14) 0.0467(16) 0.0345(14) 0.0039(12) 0.0120(11) 0.0054(12) C4 0.0387(13) 0.0330(14) 0.0319(13) 0.0024(11) 0.0122(11) 0.0015(11) C5 0.0398(13) 0.0366(15) 0.0331(14) -0.0021(12) 0.0153(11) -0.0023(11) C6 0.0401(13) 0.0382(15) 0.0340(14) -0.0034(12) 0.0143(11) -0.0028(12) C7 0.0480(16) 0.0462(17) 0.0453(16) 0.0010(14) 0.0123(13) -0.0091(13) C8 0.0453(16) 0.063(2) 0.0443(16) -0.0042(15) 0.0081(13) -0.0143(14) C9 0.0408(15) 0.079(2) 0.0473(17) 0.0092(17) 0.0045(13) 0.0003(15) C10 0.0470(17) 0.080(2) 0.0456(17) 0.0186(17) 0.0134(14) 0.0202(16) C11 0.0514(17) 0.0562(19) 0.0466(17) 0.0164(15) 0.0213(14) 0.0163(14) C12 0.0418(14) 0.0430(16) 0.0372(14) 0.0049(13) 0.0171(12) 0.0088(12) C13 0.0437(14) 0.0352(15) 0.0332(14) 0.0055(12) 0.0174(11) 0.0056(12) C14 0.0534(16) 0.0314(14) 0.0478(16) 0.0099(12) 0.0226(13) 0.0054(12) C15 0.0461(15) 0.0332(15) 0.0457(16) -0.0004(13) 0.0171(12) -0.0061(12) C16 0.0436(14) 0.0401(16) 0.0354(14) 0.0000(12) 0.0117(11) -0.0032(12) C17 0.0517(17) 0.060(2) 0.0477(17) 0.0144(15) 0.0081(14) 0.0035(14) _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 Br1 C8 1.904(3) . ? O1 C16 1.357(3) . ? O1 H9 0.85(3) . ? N1 C4 1.366(3) . ? N1 C3 1.398(3) . ? N1 H8 0.8600 . ? N2 C4 1.336(3) . ? N2 C5 1.355(3) . ? C1 C2 1.380(4) . ? C1 C10 1.389(5) . ? C1 H1 0.9300 . ? C2 C3 1.388(4) . ? C2 H7 0.9300 . ? C3 C12 1.404(4) . ? C4 C13 1.408(3) . ? C5 C15 1.400(3) . ? C5 C6 1.481(3) . ? C6 C7 1.400(4) . ? C6 C16 1.404(4) . ? C7 C8 1.372(4) . ? C7 H11 0.9300 . ? C8 C9 1.373(4) . ? C9 C17 1.365(4) . ? C9 H2 0.9300 . ? C10 C11 1.373(4) . ? C10 H6 0.9300 . ? C11 C12 1.398(4) . ? C11 H5 0.9300 . ? C12 C13 1.444(3) . ? C13 C14 1.379(4) . ? C14 C15 1.380(4) . ? C14 H4 0.9300 . ? C15 H3 0.9300 . ? C16 C17 1.393(4) . ? C17 H10 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 O1 H9 105(2) . . ? C4 N1 C3 108.3(2) . . ? C4 N1 H8 125.8 . . ? C3 N1 H8 125.8 . . ? C4 N2 C5 116.9(2) . . ? C2 C1 C10 121.8(3) . . ? C2 C1 H1 119.1 . . ? C10 C1 H1 119.1 . . ? C1 C2 C3 117.3(3) . . ? C1 C2 H7 121.4 . . ? C3 C2 H7 121.4 . . ? C2 C3 N1 129.4(2) . . ? C2 C3 C12 121.9(2) . . ? N1 C3 C12 108.7(2) . . ? N2 C4 N1 124.7(2) . . ? N2 C4 C13 125.1(2) . . ? N1 C4 C13 110.1(2) . . ? N2 C5 C15 121.4(2) . . ? N2 C5 C6 115.8(2) . . ? C15 C5 C6 122.8(2) . . ? C7 C6 C16 117.1(2) . . ? C7 C6 C5 121.1(2) . . ? C16 C6 C5 121.8(2) . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H11 119.5 . . ? C6 C7 H11 119.5 . . ? C7 C8 C9 121.5(3) . . ? C7 C8 Br1 119.7(2) . . ? C9 C8 Br1 118.9(2) . . ? C17 C9 C8 118.9(3) . . ? C17 C9 H2 120.6 . . ? C8 C9 H2 120.6 . . ? C11 C10 C1 120.7(3) . . ? C11 C10 H6 119.6 . . ? C1 C10 H6 119.6 . . ? C10 C11 C12 119.1(3) . . ? C10 C11 H5 120.5 . . ? C12 C11 H5 120.5 . . ? C11 C12 C3 119.2(2) . . ? C11 C12 C13 133.8(3) . . ? C3 C12 C13 107.0(2) . . ? C14 C13 C4 117.0(2) . . ? C14 C13 C12 137.0(2) . . ? C4 C13 C12 105.9(2) . . ? C13 C14 C15 119.1(2) . . ? C13 C14 H4 120.5 . . ? C15 C14 H4 120.5 . . ? C14 C15 C5 120.4(2) . . ? C14 C15 H3 119.8 . . ? C5 C15 H3 119.8 . . ? O1 C16 C17 116.7(2) . . ? O1 C16 C6 122.7(2) . . ? C17 C16 C6 120.5(2) . . ? C9 C17 C16 121.1(3) . . ? C9 C17 H10 119.5 . . ? C16 C17 H10 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 N1 -176.2(3) . . . . ? C1 C2 C3 C12 1.3(4) . . . . ? C4 N1 C3 C2 177.3(3) . . . . ? C4 N1 C3 C12 -0.5(3) . . . . ? C5 N2 C4 N1 177.3(2) . . . . ? C5 N2 C4 C13 -0.3(4) . . . . ? C3 N1 C4 N2 -177.0(2) . . . . ? C3 N1 C4 C13 0.9(3) . . . . ? C4 N2 C5 C15 1.6(3) . . . . ? C4 N2 C5 C6 -176.3(2) . . . . ? N2 C5 C6 C7 175.8(2) . . . . ? C15 C5 C6 C7 -2.1(4) . . . . ? N2 C5 C6 C16 -0.9(3) . . . . ? C15 C5 C6 C16 -178.7(2) . . . . ? C16 C6 C7 C8 0.7(4) . . . . ? C5 C6 C7 C8 -176.0(3) . . . . ? C6 C7 C8 C9 0.2(4) . . . . ? C6 C7 C8 Br1 178.8(2) . . . . ? C7 C8 C9 C17 -0.6(5) . . . . ? Br1 C8 C9 C17 -179.2(2) . . . . ? C2 C1 C10 C11 -1.0(5) . . . . ? C1 C10 C11 C12 1.0(4) . . . . ? C10 C11 C12 C3 0.0(4) . . . . ? C10 C11 C12 C13 175.8(3) . . . . ? C2 C3 C12 C11 -1.2(4) . . . . ? N1 C3 C12 C11 176.7(2) . . . . ? C2 C3 C12 C13 -178.0(2) . . . . ? N1 C3 C12 C13 -0.1(3) . . . . ? N2 C4 C13 C14 -1.4(4) . . . . ? N1 C4 C13 C14 -179.3(2) . . . . ? N2 C4 C13 C12 176.9(2) . . . . ? N1 C4 C13 C12 -0.9(3) . . . . ? C11 C12 C13 C14 2.3(5) . . . . ? C3 C12 C13 C14 178.4(3) . . . . ? C11 C12 C13 C4 -175.6(3) . . . . ? C3 C12 C13 C4 0.6(3) . . . . ? C4 C13 C14 C15 1.7(4) . . . . ? C12 C13 C14 C15 -175.9(3) . . . . ? C13 C14 C15 C5 -0.6(4) . . . . ? N2 C5 C15 C14 -1.2(4) . . . . ? C6 C5 C15 C14 176.5(2) . . . . ? C7 C6 C16 O1 180.0(2) . . . . ? C5 C6 C16 O1 -3.3(4) . . . . ? C7 C6 C16 C17 -1.3(4) . . . . ? C5 C6 C16 C17 175.5(3) . . . . ? C8 C9 C17 C16 0.0(5) . . . . ? O1 C16 C17 C9 179.8(3) . . . . ? C6 C16 C17 C9 0.9(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.216 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 955664' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2013253_0ma _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N2' _chemical_formula_weight 272.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8242(17) _cell_length_b 12.372(4) _cell_length_c 12.693(5) _cell_angle_alpha 104.81(2) _cell_angle_beta 95.57(2) _cell_angle_gamma 90.93(2) _cell_volume 728.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9712 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10627 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2556 _reflns_number_gt 1826 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0666P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2556 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3088(3) 1.00908(11) 0.10514(10) 0.0525(4) Uani 1 1 d . . . H8 H 0.2505 1.0493 0.0621 0.063 Uiso 1 1 calc R . . N2 N -0.0030(3) 0.85090(12) 0.02942(10) 0.0515(4) Uani 1 1 d . . . C19 C 0.8189(5) 0.45830(19) 0.3070(2) 0.1036(8) Uani 1 1 d . . . H1 H 1.0130 0.4751 0.3316 0.155 Uiso 1 1 calc R . . H13 H 0.7961 0.4286 0.2289 0.155 Uiso 1 1 calc R . . H12 H 0.7491 0.4041 0.3412 0.155 Uiso 1 1 calc R . . C15 C 0.6591(4) 0.56387(15) 0.33756(17) 0.0658(5) Uani 1 1 d . . . C14 C 0.5349(4) 0.61034(15) 0.25672(15) 0.0579(5) Uani 1 1 d . . . H14 H 0.5429 0.5734 0.1835 0.069 Uiso 1 1 calc R . . C13 C 0.3993(3) 0.71048(15) 0.28240(13) 0.0526(4) Uani 1 1 d . . . C4 C 0.2732(3) 0.75943(14) 0.19447(12) 0.0499(4) Uani 1 1 d . . . C3 C 0.3493(3) 0.86583(14) 0.18650(12) 0.0466(4) Uani 1 1 d . . . C2 C 0.5571(3) 0.95238(13) 0.24196(12) 0.0473(4) Uani 1 1 d . . . C11 C 0.7696(3) 0.96415(15) 0.32747(13) 0.0558(5) Uani 1 1 d . . . H11 H 0.7949 0.9081 0.3639 0.067 Uiso 1 1 calc R . . C10 C 0.9408(4) 1.05892(16) 0.35738(14) 0.0622(5) Uani 1 1 d . . . H10 H 1.0820 1.0669 0.4145 0.075 Uiso 1 1 calc R . . C9 C 0.9062(4) 1.14323(15) 0.30356(15) 0.0638(5) Uani 1 1 d . . . H2 H 1.0245 1.2068 0.3253 0.077 Uiso 1 1 calc R . . C16 C 0.6362(4) 0.61892(18) 0.44587(17) 0.0734(6) Uani 1 1 d . . . H3 H 0.7151 0.5888 0.5013 0.088 Uiso 1 1 calc R . . C17 C 0.4994(4) 0.71692(19) 0.47290(15) 0.0752(6) Uani 1 1 d . . . H16 H 0.4849 0.7521 0.5461 0.090 Uiso 1 1 calc R . . C18 C 0.3834(4) 0.76345(17) 0.39213(14) 0.0678(5) Uani 1 1 d . . . H15 H 0.2940 0.8307 0.4111 0.081 Uiso 1 1 calc R . . C8 C 0.6992(4) 1.13414(15) 0.21847(14) 0.0585(5) Uani 1 1 d . . . H9 H 0.6772 1.1904 0.1822 0.070 Uiso 1 1 calc R . . C1 C 0.5252(3) 1.03887(14) 0.18866(12) 0.0489(4) Uani 1 1 d . . . C7 C 0.2036(3) 0.90515(14) 0.10263(12) 0.0464(4) Uani 1 1 d . . . C6 C -0.0675(3) 0.74689(15) 0.03612(13) 0.0532(4) Uani 1 1 d . . . C12 C -0.2930(4) 0.68247(16) -0.04624(14) 0.0710(6) Uani 1 1 d . . . H4 H -0.4689 0.7150 -0.0311 0.107 Uiso 1 1 calc R . . H6 H -0.3003 0.6061 -0.0420 0.107 Uiso 1 1 calc R . . H5 H -0.2547 0.6849 -0.1184 0.107 Uiso 1 1 calc R . . C5 C 0.0663(3) 0.70046(15) 0.11569(13) 0.0574(5) Uani 1 1 d . . . H7 H 0.0155 0.6277 0.1161 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0585(9) 0.0594(9) 0.0436(8) 0.0230(7) -0.0028(6) 0.0083(7) N2 0.0548(8) 0.0610(10) 0.0401(8) 0.0165(7) 0.0005(6) 0.0082(7) C19 0.1153(19) 0.0740(15) 0.123(2) 0.0388(14) -0.0211(15) 0.0239(14) C15 0.0611(11) 0.0610(12) 0.0807(14) 0.0356(10) -0.0121(10) -0.0017(9) C14 0.0601(11) 0.0578(11) 0.0572(10) 0.0223(9) -0.0058(8) -0.0006(9) C13 0.0508(9) 0.0602(11) 0.0525(10) 0.0271(8) -0.0012(8) 0.0033(8) C4 0.0530(10) 0.0574(11) 0.0428(9) 0.0190(8) 0.0047(7) 0.0120(8) C3 0.0467(9) 0.0577(11) 0.0381(8) 0.0163(8) 0.0057(7) 0.0130(8) C2 0.0475(9) 0.0572(10) 0.0392(8) 0.0151(8) 0.0056(7) 0.0140(8) C11 0.0567(10) 0.0666(12) 0.0464(9) 0.0202(8) -0.0001(8) 0.0151(9) C10 0.0560(11) 0.0741(13) 0.0519(10) 0.0126(9) -0.0081(8) 0.0113(10) C9 0.0593(11) 0.0655(12) 0.0615(11) 0.0098(10) -0.0020(9) 0.0052(9) C16 0.0724(13) 0.0878(15) 0.0699(13) 0.0473(12) -0.0161(10) -0.0020(12) C17 0.0811(14) 0.0995(17) 0.0533(11) 0.0360(11) 0.0028(10) 0.0097(12) C18 0.0761(13) 0.0823(14) 0.0514(11) 0.0282(10) 0.0060(9) 0.0192(10) C8 0.0606(11) 0.0605(12) 0.0556(10) 0.0189(9) 0.0012(8) 0.0085(9) C1 0.0492(9) 0.0571(11) 0.0416(9) 0.0148(8) 0.0039(7) 0.0130(8) C7 0.0491(9) 0.0553(11) 0.0373(8) 0.0163(7) 0.0046(7) 0.0100(8) C6 0.0544(10) 0.0617(12) 0.0438(9) 0.0157(8) 0.0003(7) 0.0066(8) C12 0.0754(13) 0.0740(13) 0.0600(11) 0.0168(10) -0.0094(10) 0.0007(10) C5 0.0606(11) 0.0594(11) 0.0554(10) 0.0224(9) 0.0003(9) 0.0041(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.366(2) . ? N1 C1 1.386(2) . ? N1 H8 0.8600 . ? N2 C7 1.337(2) . ? N2 C6 1.345(2) . ? C19 C15 1.511(3) . ? C19 H1 0.9600 . ? C19 H13 0.9600 . ? C19 H12 0.9600 . ? C15 C16 1.385(3) . ? C15 C14 1.391(2) . ? C14 C13 1.390(2) . ? C14 H14 0.9300 . ? C13 C18 1.390(2) . ? C13 C4 1.486(2) . ? C4 C5 1.392(2) . ? C4 C3 1.392(2) . ? C3 C7 1.412(2) . ? C3 C2 1.446(2) . ? C2 C11 1.396(2) . ? C2 C1 1.408(2) . ? C11 C10 1.372(3) . ? C11 H11 0.9300 . ? C10 C9 1.389(3) . ? C10 H10 0.9300 . ? C9 C8 1.379(2) . ? C9 H2 0.9300 . ? C16 C17 1.371(3) . ? C16 H3 0.9300 . ? C17 C18 1.377(2) . ? C17 H16 0.9300 . ? C18 H15 0.9300 . ? C8 C1 1.384(2) . ? C8 H9 0.9300 . ? C6 C5 1.396(2) . ? C6 C12 1.496(2) . ? C12 H4 0.9600 . ? C12 H6 0.9600 . ? C12 H5 0.9600 . ? C5 H7 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C1 108.65(13) . . ? C7 N1 H8 125.7 . . ? C1 N1 H8 125.7 . . ? C7 N2 C6 115.01(14) . . ? C15 C19 H1 109.5 . . ? C15 C19 H13 109.5 . . ? H1 C19 H13 109.5 . . ? C15 C19 H12 109.5 . . ? H1 C19 H12 109.5 . . ? H13 C19 H12 109.5 . . ? C16 C15 C14 117.83(18) . . ? C16 C15 C19 121.66(18) . . ? C14 C15 C19 120.5(2) . . ? C13 C14 C15 121.81(17) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C18 C13 C14 118.45(15) . . ? C18 C13 C4 120.83(15) . . ? C14 C13 C4 120.72(15) . . ? C5 C4 C3 116.24(15) . . ? C5 C4 C13 120.93(16) . . ? C3 C4 C13 122.82(15) . . ? C4 C3 C7 117.38(15) . . ? C4 C3 C2 136.28(15) . . ? C7 C3 C2 106.31(14) . . ? C11 C2 C1 118.64(16) . . ? C11 C2 C3 135.06(16) . . ? C1 C2 C3 106.25(14) . . ? C10 C11 C2 119.53(17) . . ? C10 C11 H11 120.2 . . ? C2 C11 H11 120.2 . . ? C11 C10 C9 120.93(16) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C8 C9 C10 121.06(18) . . ? C8 C9 H2 119.5 . . ? C10 C9 H2 119.5 . . ? C17 C16 C15 121.26(17) . . ? C17 C16 H3 119.4 . . ? C15 C16 H3 119.4 . . ? C16 C17 C18 120.31(19) . . ? C16 C17 H16 119.8 . . ? C18 C17 H16 119.8 . . ? C17 C18 C13 120.33(18) . . ? C17 C18 H15 119.8 . . ? C13 C18 H15 119.8 . . ? C9 C8 C1 118.06(17) . . ? C9 C8 H9 121.0 . . ? C1 C8 H9 121.0 . . ? C8 C1 N1 128.98(15) . . ? C8 C1 C2 121.77(15) . . ? N1 C1 C2 109.22(15) . . ? N2 C7 N1 123.67(14) . . ? N2 C7 C3 126.76(16) . . ? N1 C7 C3 109.56(14) . . ? N2 C6 C5 122.36(16) . . ? N2 C6 C12 116.57(14) . . ? C5 C6 C12 121.07(16) . . ? C6 C12 H4 109.5 . . ? C6 C12 H6 109.5 . . ? H4 C12 H6 109.5 . . ? C6 C12 H5 109.5 . . ? H4 C12 H5 109.5 . . ? H6 C12 H5 109.5 . . ? C4 C5 C6 122.17(17) . . ? C4 C5 H7 118.9 . . ? C6 C5 H7 118.9 . . ? 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 C16 C15 C14 C13 2.0(3) . . . . ? C19 C15 C14 C13 -176.55(16) . . . . ? C15 C14 C13 C18 -1.5(3) . . . . ? C15 C14 C13 C4 178.79(15) . . . . ? C18 C13 C4 C5 -120.37(19) . . . . ? C14 C13 C4 C5 59.4(2) . . . . ? C18 C13 C4 C3 58.6(2) . . . . ? C14 C13 C4 C3 -121.65(18) . . . . ? C5 C4 C3 C7 2.3(2) . . . . ? C13 C4 C3 C7 -176.72(14) . . . . ? C5 C4 C3 C2 -175.04(16) . . . . ? C13 C4 C3 C2 5.9(3) . . . . ? C4 C3 C2 C11 0.1(3) . . . . ? C7 C3 C2 C11 -177.43(16) . . . . ? C4 C3 C2 C1 177.57(17) . . . . ? C7 C3 C2 C1 0.03(16) . . . . ? C1 C2 C11 C10 0.1(2) . . . . ? C3 C2 C11 C10 177.28(16) . . . . ? C2 C11 C10 C9 -0.2(2) . . . . ? C11 C10 C9 C8 -0.1(3) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C19 C15 C16 C17 177.58(18) . . . . ? C15 C16 C17 C18 -0.6(3) . . . . ? C16 C17 C18 C13 1.2(3) . . . . ? C14 C13 C18 C17 -0.2(3) . . . . ? C4 C13 C18 C17 179.56(17) . . . . ? C10 C9 C8 C1 0.5(2) . . . . ? C9 C8 C1 N1 -178.25(14) . . . . ? C9 C8 C1 C2 -0.6(2) . . . . ? C7 N1 C1 C8 177.09(15) . . . . ? C7 N1 C1 C2 -0.77(17) . . . . ? C11 C2 C1 C8 0.4(2) . . . . ? C3 C2 C1 C8 -177.60(14) . . . . ? C11 C2 C1 N1 178.40(13) . . . . ? C3 C2 C1 N1 0.45(16) . . . . ? C6 N2 C7 N1 176.40(14) . . . . ? C6 N2 C7 C3 -2.4(2) . . . . ? C1 N1 C7 N2 -178.18(13) . . . . ? C1 N1 C7 C3 0.79(17) . . . . ? C4 C3 C7 N2 0.3(2) . . . . ? C2 C3 C7 N2 178.43(14) . . . . ? C4 C3 C7 N1 -178.59(13) . . . . ? C2 C3 C7 N1 -0.50(17) . . . . ? C7 N2 C6 C5 1.7(2) . . . . ? C7 N2 C6 C12 -178.56(14) . . . . ? C3 C4 C5 C6 -2.9(2) . . . . ? C13 C4 C5 C6 176.11(15) . . . . ? N2 C6 C5 C4 0.9(3) . . . . ? C12 C6 C5 C4 -178.80(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.133 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 955665'