# Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2009 data_global _journal_coden_Cambridge 171 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Pedro Aramendia' 'Miguel A. Garcia-Garibay' 'Pablo Ariel Hoijemberg' 'Steven D. Karlen' 'Carlos Norberto Sanrame' _publ_contact_author_name 'Pedro Aramendia' _publ_contact_author_email PEDRO@QI.FCEN.UBA.AR _publ_section_title ; Photolysis of an Asymmetrically Substituted Diazene in Solution and in the Crystalline State ; # Attachment 'GG1404SM.CIF' data_gg1404sm _database_code_depnum_ccdc_archive 'CCDC 724120' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H30 O' _chemical_formula_weight 418.55 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' 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 8.1279(9) _cell_length_b 6.3065(7) _cell_length_c 22.035(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.416(2) _cell_angle_gamma 90.00 _cell_volume 1120.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6856 _cell_measurement_theta_min 2.578 _cell_measurement_theta_max 28.249 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9456 _exptl_absorpt_correction_T_max 0.9723 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9614 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2720 _reflns_number_gt 2461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0551P)^2^+0.2940P] 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 2720 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 O1 O 0.7500 0.25171(16) 0.7500 0.0279(2) Uani 1 2 d S . . C1 C 0.30192(13) 1.00442(16) 0.97779(5) 0.0245(2) Uani 1 1 d . . . H1 H 0.3512 1.1149 0.9570 0.029 Uiso 1 1 calc R . . C2 C 0.23487(13) 1.04986(17) 1.03116(5) 0.0268(2) Uani 1 1 d . . . H2 H 0.2393 1.1905 1.0467 0.032 Uiso 1 1 calc R . . C3 C 0.16144(13) 0.89101(17) 1.06183(4) 0.0257(2) Uani 1 1 d . . . H3 H 0.1169 0.9218 1.0986 0.031 Uiso 1 1 calc R . . C4 C 0.15353(13) 0.68640(17) 1.03833(5) 0.0254(2) Uani 1 1 d . . . H4 H 0.1017 0.5773 1.0588 0.030 Uiso 1 1 calc R . . C5 C 0.22120(12) 0.64049(15) 0.98497(4) 0.0222(2) Uani 1 1 d . . . H5 H 0.2151 0.5000 0.9693 0.027 Uiso 1 1 calc R . . C6 C 0.29794(12) 0.79835(15) 0.95416(4) 0.0196(2) Uani 1 1 d . . . C7 C 0.37646(12) 0.74580(15) 0.89877(4) 0.0192(2) Uani 1 1 d . . . C8 C 0.45310(12) 0.54879(15) 0.89357(4) 0.0199(2) Uani 1 1 d . . . H8 H 0.4581 0.4507 0.9265 0.024 Uiso 1 1 calc R . . C9 C 0.52185(11) 0.49426(15) 0.84126(4) 0.0195(2) Uani 1 1 d . . . H9 H 0.5712 0.3585 0.8387 0.023 Uiso 1 1 calc R . . C10 C 0.51984(11) 0.63562(14) 0.79224(4) 0.0184(2) Uani 1 1 d . . . C11 C 0.44882(13) 0.83483(15) 0.79820(4) 0.0223(2) Uani 1 1 d . . . H11 H 0.4490 0.9355 0.7662 0.027 Uiso 1 1 calc R . . C12 C 0.37761(12) 0.88857(15) 0.85033(4) 0.0219(2) Uani 1 1 d . . . H12 H 0.3290 1.0247 0.8530 0.026 Uiso 1 1 calc R . . C13 C 0.58339(12) 0.56363(15) 0.73280(4) 0.0188(2) Uani 1 1 d . . . C14 C 0.7500 0.4443(2) 0.7500 0.0188(3) Uani 1 2 d S . . C15 C 0.45412(13) 0.40658(17) 0.70121(5) 0.0245(2) Uani 1 1 d . . . H15A H 0.3469 0.4784 0.6919 0.037 Uiso 1 1 calc R . . H15B H 0.4425 0.2864 0.7285 0.037 Uiso 1 1 calc R . . H15C H 0.4908 0.3552 0.6632 0.037 Uiso 1 1 calc R . . C16 C 0.60042(12) 0.74691(15) 0.68792(4) 0.0217(2) Uani 1 1 d . . . H16A H 0.6483 0.6933 0.6523 0.032 Uiso 1 1 calc R . . H16B H 0.6730 0.8565 0.7084 0.032 Uiso 1 1 calc R . . H16C H 0.4908 0.8076 0.6745 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0283(5) 0.0167(5) 0.0403(6) 0.000 0.0099(4) 0.000 C1 0.0284(5) 0.0204(5) 0.0261(5) -0.0006(4) 0.0091(4) -0.0023(4) C2 0.0312(5) 0.0230(5) 0.0274(5) -0.0060(4) 0.0083(4) -0.0010(4) C3 0.0289(5) 0.0290(5) 0.0207(5) -0.0029(4) 0.0086(4) 0.0011(4) C4 0.0291(5) 0.0259(5) 0.0227(5) 0.0018(4) 0.0097(4) -0.0020(4) C5 0.0259(5) 0.0194(4) 0.0224(5) -0.0011(3) 0.0074(4) -0.0013(4) C6 0.0199(4) 0.0207(5) 0.0187(4) -0.0005(3) 0.0044(3) 0.0002(3) C7 0.0198(4) 0.0191(4) 0.0192(4) -0.0003(3) 0.0052(3) -0.0019(3) C8 0.0221(4) 0.0191(4) 0.0192(4) 0.0028(3) 0.0050(3) -0.0004(3) C9 0.0211(4) 0.0169(4) 0.0215(4) 0.0017(3) 0.0059(3) 0.0016(3) C10 0.0189(4) 0.0183(4) 0.0188(4) 0.0006(3) 0.0057(3) -0.0008(3) C11 0.0280(5) 0.0188(4) 0.0214(5) 0.0042(3) 0.0080(4) 0.0020(4) C12 0.0262(5) 0.0173(4) 0.0235(5) 0.0014(4) 0.0081(4) 0.0026(3) C13 0.0216(4) 0.0177(4) 0.0181(4) 0.0008(3) 0.0063(3) 0.0004(3) C14 0.0231(6) 0.0180(6) 0.0169(6) 0.000 0.0083(5) 0.000 C15 0.0255(5) 0.0253(5) 0.0229(5) -0.0017(4) 0.0040(4) -0.0033(4) C16 0.0261(5) 0.0211(5) 0.0190(4) 0.0033(3) 0.0073(4) 0.0017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.2149(17) . ? C1 C2 1.3884(14) . ? C1 C6 1.3989(14) . ? C1 H1 0.9500 . ? C2 C3 1.3858(15) . ? C2 H2 0.9500 . ? C3 C4 1.3888(15) . ? C3 H3 0.9500 . ? C4 C5 1.3914(13) . ? C4 H4 0.9500 . ? C5 C6 1.3966(13) . ? C5 H5 0.9500 . ? C6 C7 1.4858(13) . ? C7 C12 1.3973(13) . ? C7 C8 1.4012(13) . ? C8 C9 1.3877(13) . ? C8 H8 0.9500 . ? C9 C10 1.3989(13) . ? C9 H9 0.9500 . ? C10 C11 1.3958(13) . ? C10 C13 1.5372(12) . ? C11 C12 1.3932(13) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C16 1.5390(13) . ? C13 C15 1.5430(13) . ? C13 C14 1.5527(11) . ? C14 C13 1.5527(11) 2_656 ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.95(9) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 120.31(9) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.47(9) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.27(9) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.84(9) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 118.14(9) . . ? C5 C6 C7 120.43(9) . . ? C1 C6 C7 121.41(9) . . ? C12 C7 C8 117.52(8) . . ? C12 C7 C6 121.98(9) . . ? C8 C7 C6 120.50(8) . . ? C9 C8 C7 121.24(8) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 121.17(9) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 117.69(8) . . ? C11 C10 C13 122.31(8) . . ? C9 C10 C13 119.86(8) . . ? C12 C11 C10 121.16(9) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C7 121.17(9) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C10 C13 C16 113.19(8) . . ? C10 C13 C15 106.85(7) . . ? C16 C13 C15 107.74(8) . . ? C10 C13 C14 108.27(6) . . ? C16 C13 C14 111.89(7) . . ? C15 C13 C14 108.71(8) . . ? O1 C14 C13 118.98(5) . 2_656 ? O1 C14 C13 118.98(6) . . ? C13 C14 C13 122.04(11) 2_656 . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.45(16) . . . . ? C1 C2 C3 C4 -0.82(16) . . . . ? C2 C3 C4 C5 1.04(16) . . . . ? C3 C4 C5 C6 -0.01(16) . . . . ? C4 C5 C6 C1 -1.22(15) . . . . ? C4 C5 C6 C7 177.26(9) . . . . ? C2 C1 C6 C5 1.45(15) . . . . ? C2 C1 C6 C7 -177.01(9) . . . . ? C5 C6 C7 C12 146.49(10) . . . . ? C1 C6 C7 C12 -35.08(14) . . . . ? C5 C6 C7 C8 -33.67(14) . . . . ? C1 C6 C7 C8 144.76(10) . . . . ? C12 C7 C8 C9 -2.46(14) . . . . ? C6 C7 C8 C9 177.69(9) . . . . ? C7 C8 C9 C10 1.19(14) . . . . ? C8 C9 C10 C11 1.08(14) . . . . ? C8 C9 C10 C13 -174.73(8) . . . . ? C9 C10 C11 C12 -2.03(15) . . . . ? C13 C10 C11 C12 173.67(9) . . . . ? C10 C11 C12 C7 0.74(16) . . . . ? C8 C7 C12 C11 1.51(15) . . . . ? C6 C7 C12 C11 -178.65(9) . . . . ? C11 C10 C13 C16 14.15(13) . . . . ? C9 C10 C13 C16 -170.24(9) . . . . ? C11 C10 C13 C15 -104.28(10) . . . . ? C9 C10 C13 C15 71.33(11) . . . . ? C11 C10 C13 C14 138.79(9) . . . . ? C9 C10 C13 C14 -45.60(11) . . . . ? C10 C13 C14 O1 99.94(6) . . . . ? C16 C13 C14 O1 -134.64(6) . . . . ? C15 C13 C14 O1 -15.78(7) . . . . ? C10 C13 C14 C13 -80.06(6) . . . 2_656 ? C16 C13 C14 C13 45.36(6) . . . 2_656 ? C15 C13 C14 C13 164.22(7) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.354 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.048 # Attachment 'GG1904SM.CIF' data_gg1904sm _database_code_depnum_ccdc_archive 'CCDC 724121' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 N2' _chemical_formula_weight 280.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.9800(7) _cell_length_b 8.0417(10) _cell_length_c 33.922(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1631.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14683 _cell_measurement_theta_min 2.603 _cell_measurement_theta_max 23.303 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9737 _exptl_absorpt_correction_T_max 0.9999 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14614 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0876 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3902 _reflns_number_gt 2466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0477P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 3902 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1086 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4958(3) 0.87729(19) 0.09129(4) 0.0219(4) Uani 1 1 d . . . N2 N 0.5939(3) 0.8528(2) 0.05984(5) 0.0249(4) Uani 1 1 d . . . C1 C 1.0079(3) 0.8297(3) 0.28087(6) 0.0274(5) Uani 1 1 d . . . H1 H 1.0901 0.8787 0.2599 0.033 Uiso 1 1 calc R . . C2 C 1.0950(4) 0.8340(3) 0.31876(6) 0.0322(5) Uani 1 1 d . . . H2 H 1.2341 0.8873 0.3235 0.039 Uiso 1 1 calc R . . C3 C 0.9810(4) 0.7614(3) 0.34959(6) 0.0307(5) Uani 1 1 d . . . H3 H 1.0408 0.7645 0.3755 0.037 Uiso 1 1 calc R . . C4 C 0.7799(4) 0.6845(3) 0.34243(6) 0.0295(5) Uani 1 1 d . . . H4 H 0.7012 0.6327 0.3634 0.035 Uiso 1 1 calc R . . C5 C 0.6919(4) 0.6821(3) 0.30480(5) 0.0263(5) Uani 1 1 d . . . H5 H 0.5519 0.6294 0.3004 0.032 Uiso 1 1 calc R . . C6 C 0.8035(3) 0.7553(2) 0.27294(5) 0.0206(4) Uani 1 1 d . . . C7 C 0.7055(3) 0.7530(2) 0.23271(5) 0.0193(4) Uani 1 1 d . . . C8 C 0.7847(3) 0.8550(3) 0.20257(5) 0.0228(5) Uani 1 1 d . . . H8 H 0.9034 0.9302 0.2079 0.027 Uiso 1 1 calc R . . C9 C 0.6948(3) 0.8494(2) 0.16500(5) 0.0236(5) Uani 1 1 d . . . H9 H 0.7530 0.9212 0.1453 0.028 Uiso 1 1 calc R . . C10 C 0.5224(3) 0.7420(2) 0.15541(5) 0.0198(4) Uani 1 1 d . . . C11 C 0.4397(4) 0.6427(3) 0.18552(6) 0.0285(5) Uani 1 1 d . . . H11 H 0.3188 0.5695 0.1802 0.034 Uiso 1 1 calc R . . C12 C 0.5287(4) 0.6473(3) 0.22304(5) 0.0286(5) Uani 1 1 d . . . H12 H 0.4680 0.5767 0.2428 0.034 Uiso 1 1 calc R . . C13 C 0.4350(3) 0.7223(2) 0.11334(5) 0.0209(5) Uani 1 1 d . . . C14 C 0.5301(4) 0.5636(2) 0.09543(5) 0.0255(5) Uani 1 1 d . . . H14A H 0.4783 0.5528 0.0681 0.038 Uiso 1 1 calc R . . H14B H 0.4793 0.4675 0.1108 0.038 Uiso 1 1 calc R . . H14C H 0.6938 0.5685 0.0959 0.038 Uiso 1 1 calc R . . C15 C 0.1798(3) 0.7211(3) 0.11224(6) 0.0304(5) Uani 1 1 d . . . H15A H 0.1225 0.8234 0.1243 0.046 Uiso 1 1 calc R . . H15B H 0.1239 0.6247 0.1269 0.046 Uiso 1 1 calc R . . H15C H 0.1290 0.7144 0.0848 0.046 Uiso 1 1 calc R . . C16 C 0.6510(3) 1.0071(2) 0.03731(6) 0.0230(5) Uani 1 1 d . . . C17 C 0.5592(4) 1.1652(2) 0.05560(6) 0.0296(5) Uani 1 1 d . . . H17A H 0.3955 1.1604 0.0559 0.044 Uiso 1 1 calc R . . H17B H 0.6077 1.2613 0.0400 0.044 Uiso 1 1 calc R . . H17C H 0.6152 1.1760 0.0826 0.044 Uiso 1 1 calc R . . C18 C 0.9047(4) 1.0115(3) 0.03615(7) 0.0399(6) Uani 1 1 d . . . H18A H 0.9541 1.1079 0.0208 0.060 Uiso 1 1 calc R . . H18B H 0.9607 0.9094 0.0238 0.060 Uiso 1 1 calc R . . H18C H 0.9631 1.0199 0.0631 0.060 Uiso 1 1 calc R . . C19 C 0.5569(4) 0.9793(3) -0.00371(6) 0.0385(6) Uani 1 1 d . . . H19A H 0.3934 0.9730 -0.0023 0.058 Uiso 1 1 calc R . . H19B H 0.6160 0.8751 -0.0145 0.058 Uiso 1 1 calc R . . H19C H 0.6005 1.0719 -0.0209 0.058 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 0.0272(11) 0.0203(9) 0.0182(9) 0.0014(7) 0.0004(8) 0.0019(8) N2 0.0332(11) 0.0184(9) 0.0230(9) 0.0014(8) 0.0067(8) 0.0010(9) C1 0.0266(12) 0.0304(12) 0.0253(11) 0.0025(10) 0.0004(10) -0.0054(10) C2 0.0290(13) 0.0377(14) 0.0299(12) -0.0020(11) -0.0053(10) -0.0026(11) C3 0.0356(14) 0.0310(13) 0.0254(11) -0.0015(10) -0.0073(10) 0.0075(12) C4 0.0372(14) 0.0291(13) 0.0223(11) 0.0034(9) 0.0029(10) 0.0013(11) C5 0.0284(12) 0.0274(12) 0.0232(11) 0.0013(9) 0.0002(10) -0.0007(10) C6 0.0242(11) 0.0162(10) 0.0215(11) 0.0001(8) 0.0016(9) 0.0027(10) C7 0.0215(10) 0.0167(10) 0.0196(10) 0.0006(8) 0.0028(9) 0.0016(10) C8 0.0223(11) 0.0228(11) 0.0231(11) 0.0002(9) 0.0007(9) -0.0061(10) C9 0.0258(12) 0.0240(11) 0.0210(11) 0.0046(9) 0.0047(9) -0.0038(11) C10 0.0223(11) 0.0178(10) 0.0193(10) -0.0026(8) 0.0013(9) 0.0022(10) C11 0.0308(13) 0.0267(12) 0.0279(12) 0.0037(10) -0.0026(10) -0.0122(11) C12 0.0360(13) 0.0301(12) 0.0197(11) 0.0073(9) 0.0012(10) -0.0116(11) C13 0.0268(12) 0.0180(11) 0.0178(10) 0.0007(8) 0.0010(9) -0.0005(9) C14 0.0366(14) 0.0185(10) 0.0213(11) -0.0020(9) 0.0022(11) -0.0002(10) C15 0.0290(13) 0.0344(13) 0.0277(12) 0.0045(10) -0.0002(10) -0.0003(11) C16 0.0327(13) 0.0153(11) 0.0212(11) 0.0026(9) 0.0056(9) 0.0019(10) C17 0.0435(14) 0.0173(11) 0.0282(12) 0.0023(9) 0.0027(10) 0.0027(11) C18 0.0368(14) 0.0337(14) 0.0491(15) 0.0196(12) 0.0143(12) 0.0050(12) C19 0.0607(17) 0.0332(14) 0.0217(12) 0.0035(10) 0.0048(12) -0.0059(13) _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 N2 1.2335(19) . ? N1 C13 1.498(2) . ? N2 C16 1.497(2) . ? C1 C2 1.387(3) . ? C1 C6 1.387(3) . ? C2 C3 1.378(3) . ? C3 C4 1.374(3) . ? C4 C5 1.381(3) . ? C5 C6 1.400(3) . ? C6 C7 1.485(2) . ? C7 C8 1.394(2) . ? C7 C12 1.396(3) . ? C8 C9 1.384(2) . ? C9 C10 1.384(3) . ? C10 C11 1.388(3) . ? C10 C13 1.528(3) . ? C11 C12 1.380(3) . ? C13 C14 1.524(2) . ? C13 C15 1.527(3) . ? C16 C17 1.517(3) . ? C16 C19 1.518(3) . ? C16 C18 1.518(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C13 114.48(15) . . ? N1 N2 C16 114.67(16) . . ? C2 C1 C6 121.41(19) . . ? C3 C2 C1 120.5(2) . . ? C4 C3 C2 119.29(19) . . ? C3 C4 C5 120.2(2) . . ? C4 C5 C6 121.8(2) . . ? C1 C6 C5 116.84(17) . . ? C1 C6 C7 122.09(17) . . ? C5 C6 C7 121.07(17) . . ? C8 C7 C12 116.31(17) . . ? C8 C7 C6 122.18(17) . . ? C12 C7 C6 121.51(17) . . ? C9 C8 C7 121.63(19) . . ? C10 C9 C8 121.75(18) . . ? C9 C10 C11 116.85(17) . . ? C9 C10 C13 122.63(17) . . ? C11 C10 C13 120.38(18) . . ? C12 C11 C10 121.74(19) . . ? C11 C12 C7 121.68(18) . . ? N1 C13 C14 114.01(15) . . ? N1 C13 C15 103.64(16) . . ? C14 C13 C15 110.96(18) . . ? N1 C13 C10 107.29(16) . . ? C14 C13 C10 109.37(15) . . ? C15 C13 C10 111.45(16) . . ? N2 C16 C17 113.80(15) . . ? N2 C16 C19 105.14(16) . . ? C17 C16 C19 111.35(17) . . ? N2 C16 C18 105.10(17) . . ? C17 C16 C18 110.7(2) . . ? C19 C16 C18 110.50(19) . . ? 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 C13 N1 N2 C16 178.86(16) . . . . ? C6 C1 C2 C3 1.1(3) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C2 C1 C6 C5 -1.3(3) . . . . ? C2 C1 C6 C7 178.58(19) . . . . ? C4 C5 C6 C1 0.4(3) . . . . ? C4 C5 C6 C7 -179.44(19) . . . . ? C1 C6 C7 C8 -14.6(3) . . . . ? C5 C6 C7 C8 165.21(19) . . . . ? C1 C6 C7 C12 165.1(2) . . . . ? C5 C6 C7 C12 -15.1(3) . . . . ? C12 C7 C8 C9 -1.0(3) . . . . ? C6 C7 C8 C9 178.75(18) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? C8 C9 C10 C13 -174.27(19) . . . . ? C9 C10 C11 C12 -1.6(3) . . . . ? C13 C10 C11 C12 174.27(19) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? C8 C7 C12 C11 0.9(3) . . . . ? C6 C7 C12 C11 -178.84(19) . . . . ? N2 N1 C13 C14 7.0(2) . . . . ? N2 N1 C13 C15 -113.70(18) . . . . ? N2 N1 C13 C10 128.29(18) . . . . ? C9 C10 C13 N1 -22.5(2) . . . . ? C11 C10 C13 N1 161.81(18) . . . . ? C9 C10 C13 C14 101.6(2) . . . . ? C11 C10 C13 C14 -74.0(2) . . . . ? C9 C10 C13 C15 -135.3(2) . . . . ? C11 C10 C13 C15 49.0(3) . . . . ? N1 N2 C16 C17 -5.2(2) . . . . ? N1 N2 C16 C19 -127.27(19) . . . . ? N1 N2 C16 C18 116.07(19) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.255 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.046