# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'John Gallagher' _publ_contact_author_email JOHN.GALLAGHER@DCU.IE _publ_section_title ; Synthesis, structural and conformational analysis of a 3x3 isomer grid based on nine Methyl-N-(pyridyl)benzamides ; loop_ _publ_author_name 'John Gallagher' 'Alan J Lough' 'Pavle Mocilac' 'Mark Tallon' # Attachment 'Mxx-9cifs.cif' # [25th January 2010] # # File 9-12 c:\x\9-12\9-isomers\Mxx-9cifs.cif #============================================================ data_Mpp-[8-11] _database_code_depnum_ccdc_archive 'CCDC 765524' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mpp _chemical_melting_point 453.5 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.6975(4) _cell_length_b 16.8860(13) _cell_length_c 11.0191(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.594(4) _cell_angle_gamma 90.00 _cell_volume 1038.49(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2871 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 6020 _diffrn_standards_decay_% ? _diffrn_reflns_number 7570 _diffrn_reflns_av_R_equivalents 0.0715 _diffrn_reflns_av_sigmaI/netI 0.0895 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.55 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.984 _reflns_number_total 2367 _reflns_number_gt 1262 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.1121P)^2^] 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 2367 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1424 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2015 _refine_ls_wR_factor_gt 0.1546 _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 _refine_diff_density_max 0.35 _refine_diff_density_min -0.29 _refine_diff_density_rms 0.07 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 0.4141(3) 0.09042(11) 0.55766(16) 0.0353(5) Uani 1 1 d . . . C1 C 0.6320(4) 0.08475(15) 0.5907(2) 0.0262(6) Uani 1 1 d . . . N1 N 0.7918(4) 0.12622(13) 0.5376(2) 0.0298(6) Uani 1 1 d . . . H1 H 0.929(5) 0.1314(16) 0.580(2) 0.028(8) Uiso 1 1 d . . . C11 C 0.7422(4) 0.03005(15) 0.6935(2) 0.0276(6) Uani 1 1 d . . . C12 C 0.6147(5) 0.01297(16) 0.7848(2) 0.0301(7) Uani 1 1 d . . . H12 H 0.4638 0.0374 0.7829 0.036 Uiso 1 1 calc R . . C13 C 0.7067(5) -0.03994(16) 0.8796(2) 0.0304(7) Uani 1 1 d . . . H13 H 0.6186 -0.0503 0.9426 0.037 Uiso 1 1 calc R . . C14 C 0.9240(5) -0.07770(16) 0.8838(2) 0.0294(6) Uani 1 1 d . . . C15 C 1.0491(5) -0.06038(16) 0.7906(2) 0.0311(7) Uani 1 1 d . . . H15 H 1.1977 -0.0860 0.7912 0.037 Uiso 1 1 calc R . . C16 C 0.9627(5) -0.00679(17) 0.6970(2) 0.0314(7) Uani 1 1 d . . . H16 H 1.0531 0.0048 0.6355 0.038 Uiso 1 1 calc R . . C17 C 1.0226(5) -0.13637(17) 0.9835(2) 0.0388(7) Uani 1 1 d . . . H17A H 0.9887 -0.1182 1.0627 0.058 Uiso 0.50 1 calc PR . . H17B H 1.1962 -0.1411 0.9903 0.058 Uiso 0.50 1 calc PR . . H17C H 0.9471 -0.1881 0.9625 0.058 Uiso 0.50 1 calc PR . . H17D H 1.0993 -0.1800 0.9476 0.058 Uiso 0.50 1 calc PR . . H17E H 0.8918 -0.1572 1.0200 0.058 Uiso 0.50 1 calc PR . . H17F H 1.1409 -0.1102 1.0478 0.058 Uiso 0.50 1 calc PR . . C21 C 0.7384(4) 0.17732(15) 0.4355(2) 0.0261(6) Uani 1 1 d . . . C22 C 0.9216(5) 0.22644(15) 0.4113(2) 0.0287(6) Uani 1 1 d . . . H22 H 1.0764 0.2254 0.4633 0.034 Uiso 1 1 calc R . . C23 C 0.8721(5) 0.27655(16) 0.3099(2) 0.0320(7) Uani 1 1 d . . . H23 H 0.9976 0.3098 0.2947 0.038 Uiso 1 1 calc R . . N24 N 0.6608(4) 0.28140(14) 0.2322(2) 0.0339(6) Uani 1 1 d . . . C25 C 0.4903(5) 0.23251(15) 0.2560(2) 0.0305(7) Uani 1 1 d . . . H25 H 0.3383 0.2341 0.2015 0.037 Uiso 1 1 calc R . . C26 C 0.5192(4) 0.17972(16) 0.3543(2) 0.0280(6) Uani 1 1 d . . . H26 H 0.3917 0.1461 0.3655 0.034 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 0.0293(11) 0.0413(13) 0.0352(10) 0.0054(9) 0.0062(8) 0.0021(9) C1 0.0270(15) 0.0257(15) 0.0264(13) -0.0048(11) 0.0061(11) 0.0000(11) N1 0.0259(14) 0.0320(14) 0.0303(12) 0.0053(10) 0.0029(11) -0.0025(10) C11 0.0313(15) 0.0272(15) 0.0249(13) -0.0024(11) 0.0071(12) -0.0036(11) C12 0.0295(15) 0.0292(16) 0.0326(14) -0.0030(12) 0.0081(12) -0.0008(11) C13 0.0373(16) 0.0292(16) 0.0273(13) -0.0001(11) 0.0125(12) -0.0062(12) C14 0.0283(14) 0.0297(16) 0.0281(13) 0.0001(11) 0.0010(11) -0.0058(12) C15 0.0268(14) 0.0309(16) 0.0345(14) 0.0006(12) 0.0037(12) -0.0004(12) C16 0.0281(15) 0.0379(18) 0.0297(14) -0.0008(12) 0.0093(12) -0.0033(12) C17 0.0432(18) 0.0351(19) 0.0361(15) 0.0041(13) 0.0031(13) -0.0038(13) C21 0.0279(14) 0.0250(16) 0.0258(13) -0.0021(11) 0.0064(11) 0.0008(11) C22 0.0265(14) 0.0307(16) 0.0280(14) -0.0007(12) 0.0033(11) -0.0010(12) C23 0.0290(15) 0.0323(17) 0.0362(15) 0.0015(12) 0.0099(13) -0.0026(12) N24 0.0346(14) 0.0335(14) 0.0327(13) 0.0001(10) 0.0047(11) -0.0015(11) C25 0.0286(15) 0.0321(17) 0.0289(14) -0.0020(12) 0.0016(12) 0.0000(12) C26 0.0278(15) 0.0271(15) 0.0287(14) -0.0031(11) 0.0046(11) -0.0032(11) _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 C1 1.225(3) . ? C1 N1 1.370(3) . ? C1 C11 1.498(4) . ? N1 C21 1.401(3) . ? N1 H1 0.83(3) . ? C11 C12 1.385(3) . ? C11 C16 1.395(4) . ? C12 C13 1.394(4) . ? C12 H12 0.9500 . ? C13 C14 1.386(4) . ? C13 H13 0.9500 . ? C14 C15 1.394(4) . ? C14 C17 1.501(4) . ? C15 C16 1.386(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H17D 0.9800 . ? C17 H17E 0.9800 . ? C17 H17F 0.9800 . ? C21 C26 1.383(4) . ? C21 C22 1.400(3) . ? C22 C23 1.385(4) . ? C22 H22 0.9500 . ? C23 N24 1.333(3) . ? C23 H23 0.9500 . ? N24 C25 1.340(3) . ? C25 C26 1.387(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 O1 C1 N1 123.6(2) . . ? O1 C1 C11 121.2(2) . . ? N1 C1 C11 115.1(2) . . ? C1 N1 C21 127.0(2) . . ? C1 N1 H1 116.7(18) . . ? C21 N1 H1 114.2(18) . . ? C12 C11 C16 119.2(2) . . ? C12 C11 C1 118.4(2) . . ? C16 C11 C1 122.3(2) . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 117.7(2) . . ? C13 C14 C17 121.9(2) . . ? C15 C14 C17 120.4(2) . . ? C16 C15 C14 121.9(3) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C11 119.7(2) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C14 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C14 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C26 C21 C22 118.0(2) . . ? C26 C21 N1 124.0(2) . . ? C22 C21 N1 117.9(2) . . ? C23 C22 C21 118.5(2) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? N24 C23 C22 124.6(2) . . ? N24 C23 H23 117.7 . . ? C22 C23 H23 117.7 . . ? C23 N24 C25 115.7(2) . . ? N24 C25 C26 124.9(2) . . ? N24 C25 H25 117.6 . . ? C26 C25 H25 117.6 . . ? C21 C26 C25 118.3(2) . . ? C21 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? 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 O1 C1 N1 C21 -3.6(4) . . . . ? C11 C1 N1 C21 175.8(2) . . . . ? O1 C1 C11 C12 -28.1(4) . . . . ? N1 C1 C11 C12 152.4(2) . . . . ? O1 C1 C11 C16 148.9(3) . . . . ? N1 C1 C11 C16 -30.6(4) . . . . ? C16 C11 C12 C13 0.5(4) . . . . ? C1 C11 C12 C13 177.6(2) . . . . ? C11 C12 C13 C14 -1.2(4) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C12 C13 C14 C17 -178.4(3) . . . . ? C13 C14 C15 C16 0.7(4) . . . . ? C17 C14 C15 C16 179.7(3) . . . . ? C14 C15 C16 C11 -1.4(4) . . . . ? C12 C11 C16 C15 0.7(4) . . . . ? C1 C11 C16 C15 -176.2(2) . . . . ? C1 N1 C21 C26 -16.0(4) . . . . ? C1 N1 C21 C22 167.0(2) . . . . ? C26 C21 C22 C23 2.0(4) . . . . ? N1 C21 C22 C23 179.2(2) . . . . ? C21 C22 C23 N24 -0.3(4) . . . . ? C22 C23 N24 C25 -1.1(4) . . . . ? C23 N24 C25 C26 0.8(4) . . . . ? C22 C21 C26 C25 -2.2(4) . . . . ? N1 C21 C26 C25 -179.3(2) . . . . ? N24 C25 C26 C21 0.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N24 0.83(3) 2.42(3) 3.105(3) 141(2) 4_666 yes C26 H26 O1 0.95 2.30 2.862(3) 118 . yes C26 H26 Cg1 0.95 2.81 3.490(3) 129 3_656 yes # Specific data for C26 above # C26 H26 C11 0.95 3.11 3.838(4) 135 3_656 yes # C26 H26 C12 0.95 3.15 3.612(4) 112 3_656 yes # C26 H26 C13 0.95 3.20 3.541(4) 104 3_656 yes # C26 H26 C14 0.95 3.18 3.683(4) 115 3_656 yes # C26 H26 C15 0.95 3.10 3.875(4) 140 3_656 yes # C26 H26 C16 0.95 3.09 3.970(4) 156 3_656 yes #========================================================================= data_Mmp-[9-01] _database_code_depnum_ccdc_archive 'CCDC 765525' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mmp _chemical_melting_point 347 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1453(6) _cell_length_b 9.1925(8) _cell_length_c 14.5347(15) _cell_angle_alpha 87.088(5) _cell_angle_beta 88.102(6) _cell_angle_gamma 76.456(6) _cell_volume 1056.41(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25579 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 12766 _diffrn_standards_decay_% ? _diffrn_reflns_number 12766 _diffrn_reflns_av_R_equivalents 0.0953 _diffrn_reflns_av_sigmaI/netI 0.1017 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.53 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.984 _reflns_number_total 4782 _reflns_number_gt 2593 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0825P)^2^] 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 4782 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1829 _refine_ls_wR_factor_gt 0.1464 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.056 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 0.62678(19) 0.14237(19) 0.08566(12) 0.0459(5) Uani 1 1 d . . . C1A C 0.4821(3) 0.1237(3) 0.08679(17) 0.0359(6) Uani 1 1 d . . . N1A N 0.4328(2) 0.0155(2) 0.14169(14) 0.0363(5) Uani 1 1 d . . . H1A H 0.320(3) 0.020(3) 0.1445(17) 0.049(8) Uiso 1 1 d . . . C11A C 0.3490(3) 0.2199(3) 0.02726(17) 0.0346(6) Uani 1 1 d . . . C12A C 0.1978(3) 0.1826(3) 0.00720(17) 0.0364(6) Uani 1 1 d . . . H12A H 0.1744 0.0925 0.0332 0.044 Uiso 1 1 calc R . . C13A C 0.0809(3) 0.2759(3) -0.05042(17) 0.0370(6) Uani 1 1 d . . . C14A C 0.1167(3) 0.4075(3) -0.08703(18) 0.0414(6) Uani 1 1 d . . . H14A H 0.0370 0.4728 -0.1255 0.050 Uiso 1 1 calc R . . C15A C 0.2673(3) 0.4455(3) -0.06847(18) 0.0426(6) Uani 1 1 d . . . H15A H 0.2910 0.5354 -0.0946 0.051 Uiso 1 1 calc R . . C16A C 0.3824(3) 0.3510(3) -0.01157(18) 0.0406(6) Uani 1 1 d . . . H16A H 0.4857 0.3763 0.0010 0.049 Uiso 1 1 calc R . . C17A C -0.0787(3) 0.2312(3) -0.07485(19) 0.0467(7) Uani 1 1 d . . . H17A H -0.1589 0.3185 -0.1015 0.070 Uiso 1 1 calc R . . H17B H -0.1291 0.1935 -0.0192 0.070 Uiso 1 1 calc R . . H17C H -0.0516 0.1526 -0.1197 0.070 Uiso 1 1 calc R . . C21A C 0.5331(3) -0.0922(3) 0.20110(16) 0.0348(6) Uani 1 1 d . . . C22A C 0.6951(3) -0.0892(3) 0.22760(17) 0.0373(6) Uani 1 1 d . . . H22A H 0.7474 -0.0123 0.2043 0.045 Uiso 1 1 calc R . . C23A C 0.7783(3) -0.2005(3) 0.28869(18) 0.0393(6) Uani 1 1 d . . . H23A H 0.8874 -0.1957 0.3074 0.047 Uiso 1 1 calc R . . N24A N 0.7155(2) -0.3142(2) 0.32303(14) 0.0404(5) Uani 1 1 d . . . C25A C 0.5598(3) -0.3161(3) 0.29602(18) 0.0403(6) Uani 1 1 d . . . H25A H 0.5119 -0.3959 0.3190 0.048 Uiso 1 1 calc R . . C26A C 0.4657(3) -0.2091(3) 0.23708(17) 0.0396(6) Uani 1 1 d . . . H26A H 0.3555 -0.2152 0.2211 0.048 Uiso 1 1 calc R . . O1B O 0.0817(2) 0.74626(19) 0.43036(12) 0.0479(5) Uani 1 1 d . . . C1B C 0.1468(3) 0.6259(3) 0.46952(18) 0.0384(6) Uani 1 1 d . . . N1B N 0.1359(2) 0.6006(2) 0.56256(14) 0.0370(5) Uani 1 1 d . . . H1B H 0.185(3) 0.507(3) 0.593(2) 0.062(9) Uiso 1 1 d . . . C11B C 0.2473(3) 0.5005(3) 0.41449(17) 0.0365(6) Uani 1 1 d . . . C12B C 0.3704(3) 0.3830(3) 0.45154(18) 0.0394(6) Uani 1 1 d . . . H12B H 0.3877 0.3763 0.5161 0.047 Uiso 1 1 calc R . . C13B C 0.4689(3) 0.2747(3) 0.39652(19) 0.0400(6) Uani 1 1 d . . . C14B C 0.4419(3) 0.2875(3) 0.30289(19) 0.0454(7) Uani 1 1 d . . . H14B H 0.5100 0.2163 0.2640 0.054 Uiso 1 1 calc R . . C15B C 0.3176(3) 0.4021(3) 0.2642(2) 0.0481(7) Uani 1 1 d . . . H15B H 0.2993 0.4077 0.1998 0.058 Uiso 1 1 calc R . . C16B C 0.2204(3) 0.5084(3) 0.32048(18) 0.0417(6) Uani 1 1 d . . . H16B H 0.1350 0.5869 0.2945 0.050 Uiso 1 1 calc R . . C17B C 0.5977(3) 0.1448(3) 0.4385(2) 0.0509(7) Uani 1 1 d . . . H17D H 0.7075 0.1387 0.4073 0.076 Uiso 1 1 calc R . . H17E H 0.5617 0.0515 0.4311 0.076 Uiso 1 1 calc R . . H17F H 0.6073 0.1597 0.5042 0.076 Uiso 1 1 calc R . . C21B C 0.0589(3) 0.7081(3) 0.62619(17) 0.0354(6) Uani 1 1 d . . . C22B C -0.0597(3) 0.8400(3) 0.60311(18) 0.0434(7) Uani 1 1 d . . . H22B H -0.0939 0.8638 0.5412 0.052 Uiso 1 1 calc R . . C23B C -0.1259(3) 0.9349(3) 0.67251(18) 0.0441(7) Uani 1 1 d . . . H23B H -0.2068 1.0240 0.6556 0.053 Uiso 1 1 calc R . . N24B N -0.0863(2) 0.9125(2) 0.76126(15) 0.0432(6) Uani 1 1 d . . . C25B C 0.0295(3) 0.7853(3) 0.78190(19) 0.0421(6) Uani 1 1 d . . . H25B H 0.0620 0.7649 0.8443 0.051 Uiso 1 1 calc R . . C26B C 0.1040(3) 0.6828(3) 0.71784(18) 0.0383(6) Uani 1 1 d . . . H26B H 0.1857 0.5954 0.7365 0.046 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 O1A 0.0377(10) 0.0496(11) 0.0493(12) 0.0087(9) -0.0001(8) -0.0104(8) C1A 0.0404(14) 0.0319(14) 0.0335(15) -0.0030(11) 0.0021(10) -0.0045(10) N1A 0.0344(11) 0.0353(12) 0.0373(13) 0.0043(10) -0.0005(9) -0.0055(9) C11A 0.0387(13) 0.0309(13) 0.0329(15) -0.0023(11) 0.0038(10) -0.0058(10) C12A 0.0412(13) 0.0309(13) 0.0367(15) -0.0026(11) 0.0055(11) -0.0084(10) C13A 0.0378(13) 0.0371(14) 0.0338(15) -0.0022(11) 0.0027(10) -0.0041(10) C14A 0.0429(14) 0.0403(15) 0.0372(16) 0.0013(12) -0.0009(11) -0.0025(11) C15A 0.0471(14) 0.0358(14) 0.0440(17) 0.0067(12) 0.0015(12) -0.0097(11) C16A 0.0403(13) 0.0392(15) 0.0429(16) 0.0003(12) -0.0025(11) -0.0107(11) C17A 0.0440(14) 0.0479(16) 0.0469(18) 0.0014(13) -0.0019(12) -0.0087(12) C21A 0.0358(12) 0.0330(13) 0.0323(14) -0.0009(11) 0.0037(10) -0.0021(10) C22A 0.0354(12) 0.0364(14) 0.0389(16) -0.0008(12) 0.0039(10) -0.0067(10) C23A 0.0342(12) 0.0393(14) 0.0418(16) 0.0022(12) 0.0029(10) -0.0041(11) N24A 0.0393(11) 0.0398(12) 0.0388(13) 0.0017(10) 0.0005(9) -0.0031(9) C25A 0.0434(14) 0.0344(14) 0.0425(16) 0.0019(12) 0.0027(11) -0.0088(11) C26A 0.0391(13) 0.0392(14) 0.0394(16) 0.0003(12) 0.0016(11) -0.0075(11) O1B 0.0572(11) 0.0425(11) 0.0388(11) 0.0039(9) -0.0015(8) -0.0025(8) C1B 0.0382(13) 0.0408(15) 0.0362(16) 0.0002(12) 0.0004(11) -0.0099(11) N1B 0.0401(11) 0.0354(12) 0.0335(13) 0.0002(10) 0.0031(9) -0.0058(9) C11B 0.0376(13) 0.0379(14) 0.0355(15) -0.0002(12) 0.0010(11) -0.0126(11) C12B 0.0401(13) 0.0403(15) 0.0385(16) -0.0018(12) 0.0040(11) -0.0112(11) C13B 0.0359(13) 0.0394(14) 0.0466(18) -0.0024(12) 0.0036(11) -0.0128(11) C14B 0.0442(14) 0.0462(16) 0.0476(18) -0.0093(13) 0.0063(12) -0.0140(12) C15B 0.0484(15) 0.0552(17) 0.0412(17) -0.0051(14) 0.0018(12) -0.0125(13) C16B 0.0372(13) 0.0450(15) 0.0423(17) -0.0004(13) 0.0009(11) -0.0091(11) C17B 0.0459(14) 0.0440(16) 0.061(2) -0.0028(14) 0.0057(13) -0.0082(12) C21B 0.0332(12) 0.0364(14) 0.0359(16) 0.0005(12) 0.0045(10) -0.0078(10) C22B 0.0424(14) 0.0459(16) 0.0378(16) 0.0050(13) 0.0010(11) -0.0036(12) C23B 0.0435(14) 0.0424(15) 0.0401(17) 0.0033(13) 0.0053(12) 0.0003(11) N24B 0.0401(11) 0.0390(12) 0.0481(15) -0.0004(11) 0.0018(10) -0.0050(9) C25B 0.0425(14) 0.0424(15) 0.0405(17) -0.0009(13) -0.0002(11) -0.0083(11) C26B 0.0367(12) 0.0357(14) 0.0398(16) 0.0026(12) 0.0021(11) -0.0047(10) _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 1.229(3) . ? C1A N1A 1.369(3) . ? C1A C11A 1.497(3) . ? N1A C21A 1.405(3) . ? N1A H1A 0.91(2) . ? C11A C16A 1.385(3) . ? C11A C12A 1.397(3) . ? C12A C13A 1.393(3) . ? C12A H12A 0.9500 . ? C13A C14A 1.386(3) . ? C13A C17A 1.510(3) . ? C14A C15A 1.390(3) . ? C14A H14A 0.9500 . ? C15A C16A 1.384(3) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C21A C26A 1.390(3) . ? C21A C22A 1.393(3) . ? C22A C23A 1.385(3) . ? C22A H22A 0.9500 . ? C23A N24A 1.335(3) . ? C23A H23A 0.9500 . ? N24A C25A 1.345(3) . ? C25A C26A 1.375(3) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? O1B C1B 1.229(3) . ? C1B N1B 1.364(3) . ? C1B C11B 1.499(3) . ? N1B C21B 1.410(3) . ? N1B H1B 0.95(3) . ? C11B C16B 1.387(4) . ? C11B C12B 1.390(3) . ? C12B C13B 1.392(3) . ? C12B H12B 0.9500 . ? C13B C14B 1.381(4) . ? C13B C17B 1.510(3) . ? C14B C15B 1.389(3) . ? C14B H14B 0.9500 . ? C15B C16B 1.388(4) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C21B C26B 1.387(3) . ? C21B C22B 1.396(3) . ? C22B C23B 1.379(4) . ? C22B H22B 0.9500 . ? C23B N24B 1.334(3) . ? C23B H23B 0.9500 . ? N24B C25B 1.347(3) . ? C25B C26B 1.381(4) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? 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 O1A C1A N1A 122.7(2) . . ? O1A C1A C11A 121.2(2) . . ? N1A C1A C11A 116.1(2) . . ? C1A N1A C21A 127.63(19) . . ? C1A N1A H1A 115.8(15) . . ? C21A N1A H1A 116.2(15) . . ? C16A C11A C12A 119.1(2) . . ? C16A C11A C1A 117.1(2) . . ? C12A C11A C1A 123.8(2) . . ? C13A C12A C11A 120.8(2) . . ? C13A C12A H12A 119.6 . . ? C11A C12A H12A 119.6 . . ? C14A C13A C12A 118.7(2) . . ? C14A C13A C17A 120.9(2) . . ? C12A C13A C17A 120.3(2) . . ? C13A C14A C15A 121.2(2) . . ? C13A C14A H14A 119.4 . . ? C15A C14A H14A 119.4 . . ? C16A C15A C14A 119.3(2) . . ? C16A C15A H15A 120.3 . . ? C14A C15A H15A 120.3 . . ? C15A C16A C11A 120.9(2) . . ? C15A C16A H16A 119.6 . . ? C11A C16A H16A 119.6 . . ? C13A C17A H17A 109.5 . . ? C13A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C13A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C26A C21A C22A 117.4(2) . . ? C26A C21A N1A 117.9(2) . . ? C22A C21A N1A 124.7(2) . . ? C23A C22A C21A 118.6(2) . . ? C23A C22A H22A 120.7 . . ? C21A C22A H22A 120.7 . . ? N24A C23A C22A 124.5(2) . . ? N24A C23A H23A 117.8 . . ? C22A C23A H23A 117.8 . . ? C23A N24A C25A 116.1(2) . . ? N24A C25A C26A 123.8(2) . . ? N24A C25A H25A 118.1 . . ? C26A C25A H25A 118.1 . . ? C25A C26A C21A 119.6(2) . . ? C25A C26A H26A 120.2 . . ? C21A C26A H26A 120.2 . . ? O1B C1B N1B 123.0(2) . . ? O1B C1B C11B 119.7(2) . . ? N1B C1B C11B 117.3(2) . . ? C1B N1B C21B 125.5(2) . . ? C1B N1B H1B 122.9(18) . . ? C21B N1B H1B 111.6(18) . . ? C16B C11B C12B 119.0(2) . . ? C16B C11B C1B 117.1(2) . . ? C12B C11B C1B 123.8(2) . . ? C11B C12B C13B 121.7(2) . . ? C11B C12B H12B 119.1 . . ? C13B C12B H12B 119.1 . . ? C14B C13B C12B 118.0(2) . . ? C14B C13B C17B 121.1(2) . . ? C12B C13B C17B 120.9(2) . . ? C13B C14B C15B 121.5(2) . . ? C13B C14B H14B 119.2 . . ? C15B C14B H14B 119.2 . . ? C16B C15B C14B 119.5(3) . . ? C16B C15B H15B 120.3 . . ? C14B C15B H15B 120.3 . . ? C11B C16B C15B 120.3(2) . . ? C11B C16B H16B 119.9 . . ? C15B C16B H16B 119.9 . . ? C13B C17B H17D 109.5 . . ? C13B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C13B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C26B C21B C22B 117.3(2) . . ? C26B C21B N1B 118.4(2) . . ? C22B C21B N1B 124.3(2) . . ? C23B C22B C21B 118.2(2) . . ? C23B C22B H22B 120.9 . . ? C21B C22B H22B 120.9 . . ? N24B C23B C22B 125.7(2) . . ? N24B C23B H23B 117.1 . . ? C22B C23B H23B 117.1 . . ? C23B N24B C25B 115.1(2) . . ? N24B C25B C26B 123.9(2) . . ? N24B C25B H25B 118.0 . . ? C26B C25B H25B 118.0 . . ? C25B C26B C21B 119.8(2) . . ? C25B C26B H26B 120.1 . . ? C21B C26B H26B 120.1 . . ? 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 O1A C1A N1A C21A -2.4(4) . . . . ? C11A C1A N1A C21A 177.6(2) . . . . ? O1A C1A C11A C16A -15.1(4) . . . . ? N1A C1A C11A C16A 164.9(2) . . . . ? O1A C1A C11A C12A 163.0(2) . . . . ? N1A C1A C11A C12A -17.0(4) . . . . ? C16A C11A C12A C13A -0.5(4) . . . . ? C1A C11A C12A C13A -178.6(2) . . . . ? C11A C12A C13A C14A -0.5(4) . . . . ? C11A C12A C13A C17A 177.4(2) . . . . ? C12A C13A C14A C15A 1.1(4) . . . . ? C17A C13A C14A C15A -176.7(2) . . . . ? C13A C14A C15A C16A -0.7(4) . . . . ? C14A C15A C16A C11A -0.3(4) . . . . ? C12A C11A C16A C15A 0.9(4) . . . . ? C1A C11A C16A C15A 179.1(2) . . . . ? C1A N1A C21A C26A -167.9(2) . . . . ? C1A N1A C21A C22A 12.9(4) . . . . ? C26A C21A C22A C23A -0.9(3) . . . . ? N1A C21A C22A C23A 178.3(2) . . . . ? C21A C22A C23A N24A 1.6(4) . . . . ? C22A C23A N24A C25A -1.0(4) . . . . ? C23A N24A C25A C26A -0.4(4) . . . . ? N24A C25A C26A C21A 1.0(4) . . . . ? C22A C21A C26A C25A -0.3(4) . . . . ? N1A C21A C26A C25A -179.5(2) . . . . ? O1B C1B N1B C21B -3.8(4) . . . . ? C11B C1B N1B C21B 174.7(2) . . . . ? O1B C1B C11B C16B -19.4(3) . . . . ? N1B C1B C11B C16B 162.2(2) . . . . ? O1B C1B C11B C12B 157.1(2) . . . . ? N1B C1B C11B C12B -21.4(3) . . . . ? C16B C11B C12B C13B 1.1(3) . . . . ? C1B C11B C12B C13B -175.3(2) . . . . ? C11B C12B C13B C14B 0.4(3) . . . . ? C11B C12B C13B C17B -177.8(2) . . . . ? C12B C13B C14B C15B -1.7(4) . . . . ? C17B C13B C14B C15B 176.5(2) . . . . ? C13B C14B C15B C16B 1.4(4) . . . . ? C12B C11B C16B C15B -1.4(4) . . . . ? C1B C11B C16B C15B 175.3(2) . . . . ? C14B C15B C16B C11B 0.1(4) . . . . ? C1B N1B C21B C26B -159.1(2) . . . . ? C1B N1B C21B C22B 20.4(4) . . . . ? C26B C21B C22B C23B -0.9(3) . . . . ? N1B C21B C22B C23B 179.5(2) . . . . ? C21B C22B C23B N24B 0.2(4) . . . . ? C22B C23B N24B C25B 0.4(4) . . . . ? C23B N24B C25B C26B -0.3(4) . . . . ? N24B C25B C26B C21B -0.5(4) . . . . ? C22B C21B C26B C25B 1.1(3) . . . . ? N1B C21B C26B C25B -179.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A N24B 0.91(2) 2.29(3) 3.058(3) 142(2) 2_566 yes N1B H1B N24A 0.95(3) 2.12(3) 3.059(3) 172(3) 2_656 yes C12B H12B N24A 0.95 2.54 3.387(3) 148 2_656 yes C17A H17B O1A 0.98 2.58 3.496(3) 155 1_455 yes C22A H22A O1A 0.95 2.27 2.859(3) 119 . yes C22B H22B O1B 0.95 2.26 2.817(3) 117 . yes C23A H23A O1B 0.95 2.38 3.202(3) 144 1_645 yes C25A H25A Cg1 0.95 2.65 3.593(3) 170 1_545 yes # Specific data for C25A above # C25A H25A C11B 0.95 2.85 3.703(3) 150 1_545 yes # C25A H25A C12B 0.95 3.12 4.034(3) 162 1_545 yes # C25A H25A C13B 0.95 3.27 4.184(4) 162 1_545 yes # C25A H25A C14B 0.95 3.12 3.976(4) 151 1_545 yes # C25A H25A C15B 0.95 2.86 3.659(4) 142 1_545 yes # C25A H25A C16B 0.95 2.72 3.513(3) 142 1_545 yes #========================================================================= data_Mop-[8-12] _database_code_depnum_ccdc_archive 'CCDC 765526' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mop _chemical_melting_point 402 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 'P c' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 6.1091(4) _cell_length_b 25.558(2) _cell_length_c 7.7455(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.700(2) _cell_angle_gamma 90.00 _cell_volume 1123.65(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16113 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.837 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 8456 _diffrn_standards_decay_% ? _diffrn_reflns_number 8309 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.988 _reflns_number_total 2545 _reflns_number_gt 1491 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0904P)^2^] 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_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2545 _refine_ls_number_parameters 341 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1610 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.179 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.044 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 0.2087(5) 0.33966(15) 0.6745(4) 0.0459(11) Uani 0.899(6) 1 d P A -1 C1A C 0.3646(7) 0.36734(19) 0.7809(5) 0.0337(12) Uani 0.899(6) 1 d P A -1 N1A N 0.3422(6) 0.42067(15) 0.7909(5) 0.0370(12) Uani 0.899(6) 1 d P A -1 H1A H 0.484(8) 0.4400(18) 0.860(6) 0.044 Uiso 0.899(6) 1 d P A -1 C11A C 0.5923(7) 0.34567(17) 0.9079(5) 0.0340(13) Uani 0.899(6) 1 d P A -1 C12A C 0.7304(7) 0.31480(18) 0.8392(5) 0.0360(12) Uani 0.899(6) 1 d P A -1 C13A C 0.9422(8) 0.29503(19) 0.9635(7) 0.0441(14) Uani 0.899(6) 1 d P A -1 H13A H 1.0372 0.2747 0.9199 0.053 Uiso 0.899(6) 1 calc PR A -1 C14A C 1.0130(8) 0.3055(2) 1.1532(6) 0.0514(15) Uani 0.899(6) 1 d P A -1 H14A H 1.1552 0.2922 1.2346 0.062 Uiso 0.899(6) 1 calc PR A -1 C15A C 0.8769(8) 0.3351(2) 1.2213(6) 0.0488(14) Uani 0.899(6) 1 d P A -1 H15A H 0.9244 0.3412 1.3483 0.059 Uiso 0.899(6) 1 calc PR A -1 C16A C 0.6672(8) 0.3560(2) 1.0991(6) 0.0411(13) Uani 0.899(6) 1 d P A -1 H16A H 0.5757 0.3769 1.1441 0.049 Uiso 0.899(6) 1 calc PR A -1 C17A C 0.6585(8) 0.30174(19) 0.6351(6) 0.0468(14) Uani 0.899(6) 1 d P A -1 H17A H 0.5736 0.2693 0.6094 0.070 Uiso 0.899(6) 1 calc PR A -1 H17B H 0.7967 0.2986 0.6046 0.070 Uiso 0.899(6) 1 calc PR A -1 H17C H 0.5597 0.3291 0.5618 0.070 Uiso 0.899(6) 1 calc PR A -1 C21A C 0.1428(7) 0.45014(18) 0.6902(5) 0.0339(12) Uani 0.899(6) 1 d P A -1 C22A C 0.1690(7) 0.50275(18) 0.6568(6) 0.0368(12) Uani 0.899(6) 1 d P A -1 H22A H 0.3186 0.5175 0.6950 0.044 Uiso 0.899(6) 1 calc PR A -1 C23A C -0.0271(7) 0.53311(19) 0.5668(6) 0.0405(13) Uani 0.899(6) 1 d P A -1 H23A H -0.0051 0.5683 0.5470 0.049 Uiso 0.899(6) 1 calc PR A -1 N24A N -0.2484(6) 0.51434(16) 0.5064(5) 0.0438(12) Uani 0.899(6) 1 d P A -1 C25A C -0.2702(7) 0.4636(2) 0.5397(6) 0.0419(14) Uani 0.899(6) 1 d P A -1 H25A H -0.4217 0.4498 0.4996 0.050 Uiso 0.899(6) 1 calc PR A -1 C26A C -0.0854(7) 0.43011(18) 0.6290(6) 0.0406(13) Uani 0.899(6) 1 d P A -1 H26A H -0.1126 0.3951 0.6477 0.049 Uiso 0.899(6) 1 calc PR A -1 O1B O 0.6576(5) 0.16046(11) 0.6060(4) 0.0504(10) Uani 1 1 d . B -1 C1B C 0.8130(7) 0.13242(18) 0.7124(5) 0.0430(12) Uani 1 1 d . B -1 N1B N 0.7904(6) 0.07919(14) 0.7208(5) 0.0421(11) Uani 1 1 d . B -1 H1B H 0.932(8) 0.0600(17) 0.784(6) 0.050 Uiso 1 1 d . C -1 C11B C 1.0414(7) 0.15362(16) 0.8400(5) 0.0406(12) Uani 1 1 d . B -1 C12B C 1.1805(7) 0.18458(17) 0.7714(6) 0.0448(12) Uani 1 1 d . B -1 C13B C 1.3950(7) 0.20364(17) 0.8976(6) 0.0497(13) Uani 1 1 d . B -1 H13B H 1.4919 0.2234 0.8543 0.060 Uiso 1 1 calc R B -1 C14B C 1.4650(8) 0.19334(18) 1.0864(7) 0.0562(14) Uani 1 1 d . B -1 H14B H 1.6070 0.2066 1.1687 0.067 Uiso 1 1 calc R B -1 C15B C 1.3254(8) 0.16370(18) 1.1516(6) 0.0548(14) Uani 1 1 d . B -1 H15B H 1.3720 0.1574 1.2784 0.066 Uiso 1 1 calc R B -1 C16B C 1.1163(8) 0.14316(18) 1.0305(5) 0.0481(13) Uani 1 1 d . B -1 H16B H 1.0247 0.1223 1.0756 0.058 Uiso 1 1 calc R B -1 C17B C 1.1092(8) 0.19926(18) 0.5710(6) 0.0534(13) Uani 1 1 d . B -1 H17D H 1.0235 0.2316 0.5487 0.080 Uiso 1 1 calc R B -1 H17E H 1.0110 0.1723 0.4949 0.080 Uiso 1 1 calc R B -1 H17F H 1.2473 0.2033 0.5410 0.080 Uiso 1 1 calc R B -1 C21B C 0.5913(7) 0.04997(17) 0.6202(5) 0.0422(12) Uani 1 1 d . B -1 C22B C 0.3626(7) 0.06996(17) 0.5576(5) 0.0437(12) Uani 1 1 d . B -1 H22B H 0.3353 0.1049 0.5760 0.052 Uiso 1 1 calc R B -1 C23B C 0.1789(7) 0.03675(18) 0.4681(6) 0.0478(12) Uani 1 1 d . B -1 H23B H 0.0277 0.0508 0.4269 0.057 Uiso 1 1 calc R B -1 N24B N 0.1989(6) -0.01394(14) 0.4353(5) 0.0490(11) Uani 1 1 d . B -1 C25B C 0.4203(8) -0.03260(17) 0.4966(6) 0.0470(12) Uani 1 1 d . B -1 H25B H 0.4415 -0.0679 0.4774 0.056 Uiso 1 1 calc R B -1 C26B C 0.6172(7) -0.00289(17) 0.5858(6) 0.0442(12) Uani 1 1 d . B -1 H26B H 0.7664 -0.0178 0.6230 0.053 Uiso 1 1 calc R B -1 O1C O 0.113(5) 0.3412(10) 0.534(4) 0.039(7) Uiso 0.101(6) 1 d P A -2 C1C C 0.269(7) 0.3636(17) 0.649(6) 0.028(10) Uiso 0.101(6) 1 d P A -2 N1C N 0.229(7) 0.4194(17) 0.638(6) 0.064(12) Uiso 0.101(6) 1 d P A -2 H1C H 0.3535 0.4369 0.7013 0.077 Uiso 0.101(6) 1 calc PR A -2 C11C C 0.499(4) 0.3469(10) 0.771(3) 0.034(5) Uiso 0.101(6) 1 d PG A -2 C12C C 0.640(5) 0.3156(11) 0.708(3) 0.034(5) Uiso 0.101(6) 1 d PGD A -2 C13C C 0.850(5) 0.2955(10) 0.833(4) 0.034(5) Uiso 0.101(6) 1 d PG A -2 H13C H 0.9446 0.2746 0.7912 0.041 Uiso 0.101(6) 1 calc PR A -2 C14C C 0.919(4) 0.3067(11) 1.022(3) 0.034(5) Uiso 0.101(6) 1 d PG A -2 H14C H 1.0596 0.2933 1.1055 0.041 Uiso 0.101(6) 1 calc PR A -2 C15C C 0.778(5) 0.3380(11) 1.085(3) 0.034(5) Uiso 0.101(6) 1 d PG A -2 H15C H 0.8240 0.3454 1.2107 0.041 Uiso 0.101(6) 1 calc PR A -2 C16C C 0.568(5) 0.3581(11) 0.959(4) 0.034(5) Uiso 0.101(6) 1 d PG A -2 H16C H 0.4733 0.3790 1.0016 0.041 Uiso 0.101(6) 1 calc PR A -2 C17C C 0.556(6) 0.3001(14) 0.503(3) 0.035(9) Uiso 0.101(6) 1 d PD A -2 H17G H 0.6838 0.2841 0.4786 0.053 Uiso 0.101(6) 1 calc PR A -2 H17H H 0.5041 0.3306 0.4272 0.053 Uiso 0.101(6) 1 calc PR A -2 H17I H 0.4282 0.2757 0.4757 0.053 Uiso 0.101(6) 1 calc PR A -2 C21C C 0.045(7) 0.4499(16) 0.553(6) 0.041(6) Uiso 0.101(6) 1 d PD A -2 C22C C 0.067(8) 0.5028(17) 0.516(5) 0.041(6) Uiso 0.101(6) 1 d PD A -2 H22C H 0.2161 0.5179 0.5547 0.049 Uiso 0.101(6) 1 calc PR A -2 C23C C -0.120(7) 0.5318(17) 0.426(5) 0.041(6) Uiso 0.101(6) 1 d PD A -2 H23C H -0.0975 0.5667 0.4029 0.049 Uiso 0.101(6) 1 calc PR A -2 N24C N -0.341(6) 0.5130(13) 0.368(5) 0.041(6) Uiso 0.101(6) 1 d PD A -2 C25C C -0.389(7) 0.4600(15) 0.392(6) 0.041(6) Uiso 0.101(6) 1 d PD A -2 H25C H -0.5394 0.4455 0.3425 0.049 Uiso 0.101(6) 1 calc PR A -2 C26C C -0.180(7) 0.4302(17) 0.502(6) 0.041(6) Uiso 0.101(6) 1 d PD A -2 H26C H -0.2000 0.3966 0.5398 0.049 Uiso 0.101(6) 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 0.0338(19) 0.049(3) 0.046(2) -0.0032(15) 0.0041(16) -0.0021(15) C1A 0.031(2) 0.036(3) 0.030(2) -0.0011(17) 0.0065(19) -0.0065(19) N1A 0.0251(18) 0.040(3) 0.040(2) -0.0002(15) 0.0045(17) -0.0028(15) C11A 0.028(2) 0.036(3) 0.033(3) 0.0003(18) 0.006(2) -0.0022(18) C12A 0.030(2) 0.036(3) 0.042(3) -0.0024(18) 0.013(2) -0.0059(18) C13A 0.038(2) 0.040(3) 0.051(3) 0.002(2) 0.013(2) 0.005(2) C14A 0.034(2) 0.052(4) 0.054(4) 0.009(2) -0.001(2) 0.004(2) C15A 0.041(3) 0.064(4) 0.031(2) 0.004(2) 0.003(2) 0.002(2) C16A 0.032(2) 0.053(4) 0.037(3) -0.001(2) 0.010(2) 0.004(2) C17A 0.050(3) 0.049(4) 0.042(3) -0.003(2) 0.018(2) -0.006(2) C21A 0.026(2) 0.040(3) 0.029(2) -0.0040(17) 0.0030(18) 0.0008(18) C22A 0.025(2) 0.044(3) 0.037(3) -0.0024(19) 0.0056(19) -0.0040(18) C23A 0.035(2) 0.041(3) 0.041(3) 0.0030(19) 0.009(2) 0.001(2) N24A 0.033(2) 0.046(3) 0.045(3) 0.0033(17) 0.0051(19) 0.0027(17) C25A 0.023(2) 0.051(4) 0.048(3) 0.002(2) 0.008(2) 0.0026(19) C26A 0.034(2) 0.043(3) 0.041(3) 0.0022(19) 0.010(2) -0.002(2) O1B 0.0486(19) 0.040(2) 0.054(2) 0.0038(14) 0.0098(15) 0.0039(14) C1B 0.047(2) 0.039(3) 0.044(2) -0.0037(18) 0.017(2) -0.001(2) N1B 0.042(2) 0.034(3) 0.045(2) 0.0024(14) 0.0105(18) 0.0026(15) C11B 0.045(2) 0.033(3) 0.043(2) -0.0007(17) 0.016(2) 0.0008(18) C12B 0.050(3) 0.036(3) 0.049(3) -0.0024(18) 0.019(2) 0.0049(19) C13B 0.051(3) 0.039(3) 0.062(3) -0.0023(19) 0.023(3) -0.009(2) C14B 0.051(3) 0.047(3) 0.061(3) -0.015(2) 0.010(2) -0.004(2) C15B 0.062(3) 0.051(3) 0.049(3) -0.004(2) 0.017(2) -0.001(2) C16B 0.055(3) 0.045(3) 0.043(3) -0.0012(19) 0.017(2) -0.003(2) C17B 0.062(3) 0.047(3) 0.058(3) 0.004(2) 0.031(2) 0.005(2) C21B 0.041(2) 0.043(3) 0.040(2) -0.0006(17) 0.0123(19) -0.0033(18) C22B 0.045(3) 0.037(3) 0.049(3) -0.0027(18) 0.018(2) -0.0005(18) C23B 0.043(2) 0.047(3) 0.050(3) -0.001(2) 0.014(2) 0.002(2) N24B 0.049(2) 0.042(3) 0.053(2) -0.0063(16) 0.0146(18) -0.0027(17) C25B 0.052(3) 0.036(3) 0.049(3) -0.0032(19) 0.014(2) 0.001(2) C26B 0.044(3) 0.039(3) 0.046(2) -0.0010(18) 0.013(2) 0.0032(18) _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 1.227(5) . ? C1A N1A 1.375(6) . ? C1A C11A 1.482(6) . ? N1A C21A 1.399(5) . ? N1A H1A 0.97(5) . ? C11A C12A 1.396(7) . ? C11A C16A 1.404(6) . ? C12A C13A 1.391(6) . ? C12A C17A 1.513(6) . ? C13A C14A 1.396(7) . ? C13A H13A 0.9300 . ? C14A C15A 1.366(7) . ? C14A H14A 0.9300 . ? C15A C16A 1.387(6) . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? C21A C22A 1.390(6) . ? C21A C26A 1.393(6) . ? C22A C23A 1.380(6) . ? C22A H22A 0.9300 . ? C23A N24A 1.345(5) . ? C23A H23A 0.9300 . ? N24A C25A 1.339(6) . ? C25A C26A 1.381(6) . ? C25A H25A 0.9300 . ? C26A H26A 0.9300 . ? O1B C1B 1.231(5) . ? C1B N1B 1.372(5) . ? C1B C11B 1.482(6) . ? N1B C21B 1.394(5) . ? N1B H1B 0.96(4) . ? C11B C16B 1.400(6) . ? C11B C12B 1.401(6) . ? C12B C13B 1.401(6) . ? C12B C17B 1.496(6) . ? C13B C14B 1.389(7) . ? C13B H13B 0.9300 . ? C14B C15B 1.369(6) . ? C14B H14B 0.9300 . ? C15B C16B 1.379(6) . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B H17D 0.9600 . ? C17B H17E 0.9600 . ? C17B H17F 0.9600 . ? C21B C22B 1.395(5) . ? C21B C26B 1.397(6) . ? C22B C23B 1.373(6) . ? C22B H22B 0.9300 . ? C23B N24B 1.335(6) . ? C23B H23B 0.9300 . ? N24B C25B 1.344(5) . ? C25B C26B 1.373(6) . ? C25B H25B 0.9300 . ? C26B H26B 0.9300 . ? O1C C1C 1.18(5) . ? C1C C11C 1.44(4) . ? C1C N1C 1.44(6) . ? N1C C21C 1.33(6) . ? N1C H1C 0.8600 . ? C11C C12C 1.3900 . ? C11C C16C 1.3900 . ? C12C C13C 1.3900 . ? C12C C17C 1.528(10) . ? C13C C14C 1.3900 . ? C13C H13C 0.9300 . ? C14C C15C 1.3900 . ? C14C H14C 0.9300 . ? C15C C16C 1.3900 . ? C15C H15C 0.9300 . ? C16C H16C 0.9300 . ? C17C H17G 0.9600 . ? C17C H17H 0.9600 . ? C17C H17I 0.9600 . ? C21C C26C 1.38(5) . ? C21C C22C 1.40(6) . ? C22C C23C 1.32(6) . ? C22C H22C 0.9300 . ? C23C N24C 1.35(5) . ? C23C H23C 0.9300 . ? N24C C25C 1.41(5) . ? C25C C26C 1.46(6) . ? C25C H25C 0.9300 . ? C26C H26C 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 O1A C1A N1A 122.7(4) . . ? O1A C1A C11A 122.3(4) . . ? N1A C1A C11A 115.0(4) . . ? C1A N1A C21A 125.9(3) . . ? C1A N1A H1A 117(3) . . ? C21A N1A H1A 117(3) . . ? C12A C11A C16A 120.1(4) . . ? C12A C11A C1A 120.6(4) . . ? C16A C11A C1A 119.3(5) . . ? C13A C12A C11A 118.7(4) . . ? C13A C12A C17A 118.6(5) . . ? C11A C12A C17A 122.7(4) . . ? C12A C13A C14A 120.3(5) . . ? C12A C13A H13A 119.8 . . ? C14A C13A H13A 119.8 . . ? C15A C14A C13A 121.2(4) . . ? C15A C14A H14A 119.4 . . ? C13A C14A H14A 119.4 . . ? C14A C15A C16A 119.3(4) . . ? C14A C15A H15A 120.4 . . ? C16A C15A H15A 120.4 . . ? C15A C16A C11A 120.4(5) . . ? C15A C16A H16A 119.8 . . ? C11A C16A H16A 119.8 . . ? C22A C21A C26A 117.5(4) . . ? C22A C21A N1A 119.2(4) . . ? C26A C21A N1A 123.2(4) . . ? C23A C22A C21A 120.0(4) . . ? C23A C22A H22A 120.0 . . ? C21A C22A H22A 120.0 . . ? N24A C23A C22A 123.2(4) . . ? N24A C23A H23A 118.4 . . ? C22A C23A H23A 118.4 . . ? C25A N24A C23A 115.9(4) . . ? N24A C25A C26A 125.2(4) . . ? N24A C25A H25A 117.4 . . ? C26A C25A H25A 117.4 . . ? C25A C26A C21A 118.2(4) . . ? C25A C26A H26A 120.9 . . ? C21A C26A H26A 120.9 . . ? O1B C1B N1B 122.9(4) . . ? O1B C1B C11B 122.4(4) . . ? N1B C1B C11B 114.7(4) . . ? C1B N1B C21B 126.0(3) . . ? C1B N1B H1B 116(3) . . ? C21B N1B H1B 117(3) . . ? C16B C11B C12B 120.0(4) . . ? C16B C11B C1B 119.6(4) . . ? C12B C11B C1B 120.4(4) . . ? C11B C12B C13B 118.3(4) . . ? C11B C12B C17B 123.4(4) . . ? C13B C12B C17B 118.3(4) . . ? C14B C13B C12B 120.9(4) . . ? C14B C13B H13B 119.6 . . ? C12B C13B H13B 119.6 . . ? C15B C14B C13B 120.2(4) . . ? C15B C14B H14B 119.9 . . ? C13B C14B H14B 119.9 . . ? C14B C15B C16B 120.4(4) . . ? C14B C15B H15B 119.8 . . ? C16B C15B H15B 119.8 . . ? C15B C16B C11B 120.3(5) . . ? C15B C16B H16B 119.9 . . ? C11B C16B H16B 119.9 . . ? N1B C21B C22B 123.6(4) . . ? N1B C21B C26B 119.2(4) . . ? C22B C21B C26B 117.2(4) . . ? C23B C22B C21B 118.4(4) . . ? C23B C22B H22B 120.8 . . ? C21B C22B H22B 120.8 . . ? N24B C23B C22B 125.5(4) . . ? N24B C23B H23B 117.3 . . ? C22B C23B H23B 117.3 . . ? C23B N24B C25B 115.4(4) . . ? N24B C25B C26B 124.1(4) . . ? N24B C25B H25B 117.9 . . ? C26B C25B H25B 117.9 . . ? C25B C26B C21B 119.4(4) . . ? C25B C26B H26B 120.3 . . ? C21B C26B H26B 120.3 . . ? O1C C1C C11C 132(4) . . ? O1C C1C N1C 111(4) . . ? C11C C1C N1C 116(4) . . ? C21C N1C C1C 135(4) . . ? C21C N1C H1C 112.7 . . ? C1C N1C H1C 112.7 . . ? C12C C11C C16C 120.0 . . ? C12C C11C C1C 121(2) . . ? C16C C11C C1C 118(2) . . ? C13C C12C C11C 120.0 . . ? C13C C12C C17C 120(2) . . ? C11C C12C C17C 120(2) . . ? C14C C13C C12C 120.0 . . ? C14C C13C H13C 120.0 . . ? C12C C13C H13C 120.0 . . ? C13C C14C C15C 120.0 . . ? C13C C14C H14C 120.0 . . ? C15C C14C H14C 120.0 . . ? C16C C15C C14C 120.0 . . ? C16C C15C H15C 120.0 . . ? C14C C15C H15C 120.0 . . ? C15C C16C C11C 120.0 . . ? C15C C16C H16C 120.0 . . ? C11C C16C H16C 120.0 . . ? C12C C17C H17G 109.5 . . ? C12C C17C H17H 109.5 . . ? H17G C17C H17H 109.5 . . ? C12C C17C H17I 109.5 . . ? H17G C17C H17I 109.5 . . ? H17H C17C H17I 109.5 . . ? N1C C21C C26C 120(4) . . ? N1C C21C C22C 123(4) . . ? C26C C21C C22C 117(4) . . ? C23C C22C C21C 121(4) . . ? C23C C22C H22C 119.4 . . ? C21C C22C H22C 119.4 . . ? C22C C23C N24C 123(4) . . ? C22C C23C H23C 118.6 . . ? N24C C23C H23C 118.6 . . ? C23C N24C C25C 122(3) . . ? N24C C25C C26C 113(3) . . ? N24C C25C H25C 123.3 . . ? C26C C25C H25C 123.3 . . ? C21C C26C C25C 123(4) . . ? C21C C26C H26C 118.6 . . ? C25C C26C H26C 118.6 . . ? 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 O1A C1A N1A C21A 2.4(7) . . . . ? C11A C1A N1A C21A -177.9(4) . . . . ? O1A C1A C11A C12A 54.1(6) . . . . ? N1A C1A C11A C12A -125.5(5) . . . . ? O1A C1A C11A C16A -125.1(5) . . . . ? N1A C1A C11A C16A 55.2(5) . . . . ? C16A C11A C12A C13A -0.4(7) . . . . ? C1A C11A C12A C13A -179.6(4) . . . . ? C16A C11A C12A C17A 179.3(4) . . . . ? C1A C11A C12A C17A 0.1(7) . . . . ? C11A C12A C13A C14A 0.7(7) . . . . ? C17A C12A C13A C14A -179.0(4) . . . . ? C12A C13A C14A C15A 0.2(7) . . . . ? C13A C14A C15A C16A -1.4(8) . . . . ? C14A C15A C16A C11A 1.7(7) . . . . ? C12A C11A C16A C15A -0.8(7) . . . . ? C1A C11A C16A C15A 178.5(4) . . . . ? C1A N1A C21A C22A -155.2(4) . . . . ? C1A N1A C21A C26A 28.3(7) . . . . ? C26A C21A C22A C23A 0.4(6) . . . . ? N1A C21A C22A C23A -176.4(4) . . . . ? C21A C22A C23A N24A -0.6(6) . . . . ? C22A C23A N24A C25A 0.5(6) . . . . ? C23A N24A C25A C26A -0.3(7) . . . . ? N24A C25A C26A C21A 0.1(7) . . . . ? C22A C21A C26A C25A -0.1(6) . . . . ? N1A C21A C26A C25A 176.5(4) . . . . ? O1B C1B N1B C21B -3.0(6) . . . . ? C11B C1B N1B C21B 177.8(4) . . . . ? O1B C1B C11B C16B 125.2(4) . . . . ? N1B C1B C11B C16B -55.6(5) . . . . ? O1B C1B C11B C12B -53.9(6) . . . . ? N1B C1B C11B C12B 125.3(4) . . . . ? C16B C11B C12B C13B 1.0(6) . . . . ? C1B C11B C12B C13B -179.9(4) . . . . ? C16B C11B C12B C17B -177.6(4) . . . . ? C1B C11B C12B C17B 1.4(6) . . . . ? C11B C12B C13B C14B -1.8(6) . . . . ? C17B C12B C13B C14B 177.0(4) . . . . ? C12B C13B C14B C15B 0.8(7) . . . . ? C13B C14B C15B C16B 1.0(7) . . . . ? C14B C15B C16B C11B -1.8(7) . . . . ? C12B C11B C16B C15B 0.7(7) . . . . ? C1B C11B C16B C15B -178.3(4) . . . . ? C1B N1B C21B C22B -27.4(6) . . . . ? C1B N1B C21B C26B 155.5(4) . . . . ? N1B C21B C22B C23B -176.6(4) . . . . ? C26B C21B C22B C23B 0.5(6) . . . . ? C21B C22B C23B N24B 0.2(6) . . . . ? C22B C23B N24B C25B -0.1(6) . . . . ? C23B N24B C25B C26B -0.6(6) . . . . ? N24B C25B C26B C21B 1.3(7) . . . . ? N1B C21B C26B C25B 176.1(4) . . . . ? C22B C21B C26B C25B -1.2(6) . . . . ? O1C C1C N1C C21C 14(7) . . . . ? C11C C1C N1C C21C -176(4) . . . . ? O1C C1C C11C C12C 43(6) . . . . ? N1C C1C C11C C12C -124(3) . . . . ? O1C C1C C11C C16C -130(4) . . . . ? N1C C1C C11C C16C 62(4) . . . . ? C16C C11C C12C C13C 0.0 . . . . ? C1C C11C C12C C13C -173(3) . . . . ? C16C C11C C12C C17C 176(3) . . . . ? C1C C11C C12C C17C 2(3) . . . . ? C11C C12C C13C C14C 0.0 . . . . ? C17C C12C C13C C14C -176(3) . . . . ? C12C C13C C14C C15C 0.0 . . . . ? C13C C14C C15C C16C 0.0 . . . . ? C14C C15C C16C C11C 0.0 . . . . ? C12C C11C C16C C15C 0.0 . . . . ? C1C C11C C16C C15C 173(3) . . . . ? C1C N1C C21C C26C 23(7) . . . . ? C1C N1C C21C C22C -159(4) . . . . ? N1C C21C C22C C23C 178(4) . . . . ? C26C C21C C22C C23C -4(3) . . . . ? C21C C22C C23C N24C 1(4) . . . . ? C22C C23C N24C C25C -2(5) . . . . ? C23C N24C C25C C26C 6(5) . . . . ? N1C C21C C26C C25C -174(4) . . . . ? C22C C21C C26C C25C 8(5) . . . . ? N24C C25C C26C C21C -9(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A N24A 0.97(5) 1.99(5) 2.952(5) 174(4) 2_665 yes N1B H1B N24B 0.96(4) 2.00(4) 2.950(5) 171(4) 2_655 yes N1C H1C N24C 0.86 2.24 3.10(5) 176 2_665 yes C15A H15A O1A 0.93 2.48 3.344(5) 154 1_656 yes C15B H15B O1B 0.93 2.49 3.351(5) 154 1_656 yes C15C H15C O1C 0.93 2.48 3.32(3) 151 1_656 yes #========================================================================= data_Mpm_9-05 _database_code_depnum_ccdc_archive 'CCDC 765527' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mpm _chemical_melting_point 401.5 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.2023(2) _cell_length_b 7.7661(4) _cell_length_c 26.5219(12) _cell_angle_alpha 89.078(3) _cell_angle_beta 89.687(3) _cell_angle_gamma 90.024(2) _cell_volume 1071.37(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 34966 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 14973 _diffrn_standards_decay_% ? _diffrn_reflns_number 14972 _diffrn_reflns_av_R_equivalents 0.106 _diffrn_reflns_av_sigmaI/netI 0.086 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.73 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.947 _reflns_number_total 4770 _reflns_number_gt 3453 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.2613P] 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_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4770 _refine_ls_number_parameters 597 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.23 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.05 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 0.4339(6) 0.0163(5) 0.16578(13) 0.0462(8) Uani 1 1 d . . . C1A C 0.2082(9) 0.0090(6) 0.15172(19) 0.0385(11) Uani 1 1 d . . . N1A N 0.0074(8) -0.0002(5) 0.18439(16) 0.0379(9) Uani 1 1 d . . . H1A H -0.115(11) 0.024(8) 0.172(2) 0.06(2) Uiso 1 1 d . . . C11A C 0.1413(9) 0.0059(5) 0.09674(17) 0.0363(10) Uani 1 1 d . . . C12A C 0.3066(9) 0.0874(6) 0.06389(18) 0.0412(11) Uani 1 1 d . . . H12A H 0.4550 0.1438 0.0763 0.049 Uiso 1 1 calc R . . C13A C 0.2576(10) 0.0878(6) 0.01265(18) 0.0431(11) Uani 1 1 d . . . H13A H 0.3717 0.1469 -0.0097 0.052 Uiso 1 1 calc R . . C14A C 0.0403(9) 0.0015(6) -0.00727(18) 0.0400(11) Uani 1 1 d . . . C15A C -0.1211(9) -0.0806(5) 0.02562(18) 0.0408(11) Uani 1 1 d . . . H15A H -0.2665 -0.1401 0.0132 0.049 Uiso 1 1 calc R . . C16A C -0.0760(8) -0.0786(5) 0.07728(18) 0.0389(11) Uani 1 1 d . . . H16A H -0.1929 -0.1348 0.0997 0.047 Uiso 1 1 calc R . . C17A C -0.0151(11) 0.0016(7) -0.06327(19) 0.0522(13) Uani 1 1 d . . . H17A H -0.0996 -0.1066 -0.0720 0.078 Uiso 1 1 calc R . . H17B H 0.1466 0.0129 -0.0822 0.078 Uiso 1 1 calc R . . H17C H -0.1280 0.0986 -0.0718 0.078 Uiso 1 1 calc R . . C21A C 0.0305(8) -0.0032(5) 0.23761(17) 0.0353(10) Uani 1 1 d . . . C22A C -0.1582(9) 0.0793(6) 0.26634(18) 0.0407(11) Uani 1 1 d . . . H22A H -0.2943 0.1368 0.2493 0.049 Uiso 1 1 calc R . . N23A N -0.1551(7) 0.0806(5) 0.31692(15) 0.0446(10) Uani 1 1 d . . . C24A C 0.0391(9) -0.0007(6) 0.33985(19) 0.0441(11) Uani 1 1 d . . . H24A H 0.0432 -0.0017 0.3757 0.053 Uiso 1 1 calc R . . C25A C 0.2341(9) -0.0832(6) 0.31435(19) 0.0429(11) Uani 1 1 d . . . H25A H 0.3703 -0.1369 0.3324 0.052 Uiso 1 1 calc R . . C26A C 0.2291(9) -0.0871(6) 0.26220(19) 0.0418(11) Uani 1 1 d . . . H26A H 0.3585 -0.1458 0.2438 0.050 Uiso 1 1 calc R . . O1B O 0.1696(6) 0.4870(5) 0.12199(13) 0.0468(9) Uani 1 1 d . . . C1B C 0.3961(8) 0.4944(5) 0.13664(18) 0.0362(10) Uani 1 1 d . . . N1B N 0.5975(8) 0.5011(5) 0.10461(15) 0.0362(9) Uani 1 1 d . . . H1B H 0.750(9) 0.491(5) 0.1175(17) 0.028(12) Uiso 1 1 d . . . C11B C 0.4592(8) 0.4958(5) 0.19129(17) 0.0347(10) Uani 1 1 d . . . C12B C 0.2919(8) 0.4145(6) 0.22415(17) 0.0375(10) Uani 1 1 d . . . H12B H 0.1438 0.3582 0.2116 0.045 Uiso 1 1 calc R . . C13B C 0.3390(9) 0.4147(6) 0.27578(18) 0.0432(11) Uani 1 1 d . . . H13B H 0.2241 0.3554 0.2980 0.052 Uiso 1 1 calc R . . C14B C 0.5512(9) 0.5000(6) 0.29582(18) 0.0416(11) Uani 1 1 d . . . C15B C 0.7168(9) 0.5812(6) 0.26358(18) 0.0414(11) Uani 1 1 d . . . H15B H 0.8617 0.6400 0.2765 0.050 Uiso 1 1 calc R . . C16B C 0.6764(9) 0.5791(6) 0.21176(18) 0.0409(11) Uani 1 1 d . . . H16B H 0.7964 0.6344 0.1898 0.049 Uiso 1 1 calc R . . C17B C 0.6039(11) 0.5000(7) 0.35190(18) 0.0538(13) Uani 1 1 d . . . H17D H 0.7296 0.4101 0.3602 0.081 Uiso 1 1 calc R . . H17E H 0.4438 0.4775 0.3705 0.081 Uiso 1 1 calc R . . H17F H 0.6725 0.6125 0.3613 0.081 Uiso 1 1 calc R . . C21B C 0.5785(8) 0.5044(5) 0.05119(16) 0.0343(10) Uani 1 1 d . . . C22B C 0.7723(9) 0.4257(6) 0.02325(18) 0.0393(10) Uani 1 1 d . . . H22B H 0.9061 0.3687 0.0412 0.047 Uiso 1 1 calc R . . N23B N 0.7816(8) 0.4254(5) -0.02720(15) 0.0443(10) Uani 1 1 d . . . C24B C 0.5884(9) 0.5059(6) -0.05106(19) 0.0422(11) Uani 1 1 d . . . H24B H 0.5886 0.5074 -0.0869 0.051 Uiso 1 1 calc R . . C25B C 0.3875(9) 0.5873(6) -0.02614(18) 0.0415(11) Uani 1 1 d . . . H25B H 0.2549 0.6425 -0.0448 0.050 Uiso 1 1 calc R . . C26B C 0.3819(9) 0.5875(6) 0.02625(18) 0.0391(11) Uani 1 1 d . . . H26B H 0.2476 0.6429 0.0442 0.047 Uiso 1 1 calc R . . O1C O 0.9618(6) 0.0606(4) 0.61612(12) 0.0454(8) Uani 1 1 d . . . C1C C 0.7363(9) 0.0327(5) 0.62682(17) 0.0362(10) Uani 1 1 d . . . N1C N 0.5422(8) 0.0423(5) 0.59224(15) 0.0379(9) Uani 1 1 d . . . H1C H 0.415(9) 0.041(5) 0.6018(16) 0.020(12) Uiso 1 1 d . . . C11C C 0.6569(8) -0.0168(5) 0.67910(16) 0.0359(9) Uani 1 1 d . . . C12C C 0.8166(9) 0.0332(5) 0.71893(17) 0.0387(10) Uani 1 1 d . . . H12C H 0.9685 0.0971 0.7117 0.046 Uiso 1 1 calc R . . C13C C 0.7566(9) -0.0089(6) 0.76790(18) 0.0419(10) Uani 1 1 d . . . H13C H 0.8629 0.0285 0.7946 0.050 Uiso 1 1 calc R . . C14C C 0.5380(10) -0.1070(5) 0.77817(17) 0.0430(11) Uani 1 1 d . . . C15C C 0.3820(9) -0.1588(5) 0.73778(18) 0.0423(10) Uani 1 1 d . . . H15C H 0.2333 -0.2264 0.7446 0.051 Uiso 1 1 calc R . . C16C C 0.4406(9) -0.1134(5) 0.68865(17) 0.0399(10) Uani 1 1 d . . . H16C H 0.3331 -0.1484 0.6618 0.048 Uiso 1 1 calc R . . C17C C 0.4717(11) -0.1589(6) 0.83143(18) 0.0528(12) Uani 1 1 d . . . H17G H 0.2877 -0.1853 0.8338 0.079 Uiso 1 1 calc R . . H17H H 0.5125 -0.0642 0.8540 0.079 Uiso 1 1 calc R . . H17I H 0.5714 -0.2610 0.8412 0.079 Uiso 1 1 calc R . . C21C C 0.5669(8) 0.0667(5) 0.54008(17) 0.0351(10) Uani 1 1 d . . . C22C C 0.3781(9) -0.0012(6) 0.50787(18) 0.0420(10) Uani 1 1 d . . . H22C H 0.2399 -0.0627 0.5233 0.050 Uiso 1 1 calc R . . N23C N 0.3773(7) 0.0136(5) 0.45810(15) 0.0459(9) Uani 1 1 d . . . C24C C 0.5730(10) 0.1000(6) 0.43789(19) 0.0453(11) Uani 1 1 d . . . H24C H 0.5802 0.1130 0.4022 0.054 Uiso 1 1 calc R . . C25C C 0.7687(9) 0.1727(5) 0.46623(18) 0.0431(10) Uani 1 1 d . . . H25C H 0.9047 0.2328 0.4496 0.052 Uiso 1 1 calc R . . C26C C 0.7677(8) 0.1584(5) 0.51886(16) 0.0389(10) Uani 1 1 d . . . H26C H 0.8978 0.2090 0.5388 0.047 Uiso 1 1 calc R . . O1D O 0.4684(6) 0.4309(4) 0.67603(12) 0.0438(8) Uani 1 1 d . . . C1D C 0.2434(9) 0.4588(5) 0.66480(17) 0.0370(10) Uani 1 1 d . . . N1D N 0.0487(8) 0.4479(5) 0.69880(14) 0.0366(9) Uani 1 1 d . . . H1D H -0.108(10) 0.467(6) 0.6902(19) 0.048(15) Uiso 1 1 d . . . C11D C 0.1651(8) 0.5065(5) 0.61267(16) 0.0362(9) Uani 1 1 d . . . C12D C 0.3218(9) 0.4581(5) 0.57312(17) 0.0409(10) Uani 1 1 d . . . H12D H 0.4736 0.3941 0.5800 0.049 Uiso 1 1 calc R . . C13D C 0.2618(9) 0.5010(6) 0.52365(17) 0.0428(11) Uani 1 1 d . . . H13D H 0.3700 0.4634 0.4970 0.051 Uiso 1 1 calc R . . C14D C 0.0479(9) 0.5971(6) 0.51278(19) 0.0429(11) Uani 1 1 d . . . C15D C -0.1111(9) 0.6492(5) 0.55301(18) 0.0433(11) Uani 1 1 d . . . H15D H -0.2602 0.7160 0.5461 0.052 Uiso 1 1 calc R . . C16D C -0.0533(9) 0.6046(5) 0.60202(18) 0.0424(10) Uani 1 1 d . . . H16D H -0.1623 0.6406 0.6287 0.051 Uiso 1 1 calc R . . C17D C -0.0204(11) 0.6473(6) 0.45994(19) 0.0560(13) Uani 1 1 d . . . H17J H 0.0502 0.7616 0.4520 0.084 Uiso 1 1 calc R . . H17K H -0.2079 0.6501 0.4565 0.084 Uiso 1 1 calc R . . H17L H 0.0516 0.5632 0.4366 0.084 Uiso 1 1 calc R . . C21D C 0.0752(8) 0.4245(5) 0.75135(17) 0.0356(10) Uani 1 1 d . . . C22D C -0.1147(9) 0.4947(6) 0.78178(17) 0.0411(10) Uani 1 1 d . . . H22D H -0.2512 0.5562 0.7661 0.049 Uiso 1 1 calc R . . N23D N -0.1149(8) 0.4802(5) 0.83194(15) 0.0464(9) Uani 1 1 d . . . C24D C 0.0775(9) 0.3953(6) 0.85298(19) 0.0439(11) Uani 1 1 d . . . H24D H 0.0806 0.3844 0.8887 0.053 Uiso 1 1 calc R . . C25D C 0.2750(9) 0.3214(6) 0.82564(17) 0.0428(11) Uani 1 1 d . . . H25D H 0.4106 0.2629 0.8426 0.051 Uiso 1 1 calc R . . C26D C 0.2737(9) 0.3332(5) 0.77356(17) 0.0408(10) Uani 1 1 d . . . H26D H 0.4040 0.2807 0.7538 0.049 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 O1A 0.0343(19) 0.061(2) 0.043(2) 0.0004(16) 0.0017(14) -0.0024(15) C1A 0.035(3) 0.034(2) 0.046(3) -0.0044(19) 0.001(2) 0.0012(18) N1A 0.035(2) 0.043(2) 0.035(2) 0.0014(17) 0.0004(18) -0.0006(17) C11A 0.036(3) 0.034(2) 0.038(3) 0.0015(18) 0.0005(19) 0.0017(18) C12A 0.041(3) 0.035(2) 0.048(3) -0.005(2) -0.002(2) -0.0037(19) C13A 0.051(3) 0.036(2) 0.042(3) 0.003(2) 0.003(2) -0.001(2) C14A 0.049(3) 0.034(2) 0.037(3) -0.0011(19) -0.002(2) 0.007(2) C15A 0.040(3) 0.038(2) 0.044(3) 0.000(2) -0.001(2) -0.0029(19) C16A 0.038(3) 0.037(2) 0.042(3) 0.004(2) -0.001(2) -0.0029(19) C17A 0.065(4) 0.049(3) 0.042(3) 0.002(2) 0.000(2) 0.004(2) C21A 0.036(2) 0.032(2) 0.038(3) 0.0018(18) 0.0008(19) -0.0061(17) C22A 0.039(3) 0.043(2) 0.040(3) 0.002(2) 0.002(2) -0.0024(19) N23A 0.045(2) 0.050(2) 0.039(2) -0.0019(18) 0.0036(18) -0.0005(18) C24A 0.047(3) 0.049(3) 0.037(3) 0.000(2) -0.006(2) -0.007(2) C25A 0.048(3) 0.040(2) 0.041(3) 0.004(2) -0.005(2) 0.000(2) C26A 0.041(3) 0.038(2) 0.047(3) 0.001(2) -0.001(2) 0.002(2) O1B 0.0347(19) 0.061(2) 0.045(2) 0.0017(16) -0.0022(14) -0.0017(15) C1B 0.035(3) 0.032(2) 0.042(3) 0.0024(19) 0.002(2) -0.0023(18) N1B 0.031(2) 0.041(2) 0.037(2) 0.0005(16) -0.0024(17) -0.0009(16) C11B 0.029(2) 0.037(2) 0.038(3) 0.0027(19) -0.0005(18) 0.0000(18) C12B 0.032(2) 0.040(2) 0.040(3) 0.0041(19) 0.0013(19) -0.0011(18) C13B 0.048(3) 0.039(2) 0.042(3) 0.004(2) 0.004(2) -0.002(2) C14B 0.052(3) 0.037(2) 0.036(3) 0.0019(19) -0.004(2) 0.005(2) C15B 0.044(3) 0.038(2) 0.043(3) -0.004(2) -0.008(2) 0.003(2) C16B 0.042(3) 0.041(2) 0.040(3) 0.002(2) 0.001(2) -0.003(2) C17B 0.072(4) 0.058(3) 0.032(3) 0.000(2) -0.006(2) 0.002(3) C21B 0.038(3) 0.034(2) 0.031(3) -0.0008(18) 0.0004(18) -0.0080(18) C22B 0.036(3) 0.039(2) 0.043(3) -0.0012(19) -0.002(2) -0.0005(18) N23B 0.045(2) 0.047(2) 0.040(3) -0.0019(17) 0.0028(18) -0.0021(18) C24B 0.046(3) 0.044(3) 0.036(3) 0.000(2) 0.000(2) -0.006(2) C25B 0.043(3) 0.041(2) 0.041(3) 0.0024(19) -0.007(2) -0.001(2) C26B 0.033(2) 0.040(2) 0.044(3) 0.001(2) -0.002(2) -0.0065(19) O1C 0.0396(19) 0.0492(18) 0.047(2) 0.0037(14) 0.0004(14) -0.0041(14) C1C 0.038(3) 0.028(2) 0.042(3) 0.0016(17) -0.0005(19) 0.0006(17) N1C 0.033(2) 0.041(2) 0.040(3) 0.0059(16) 0.0039(19) -0.0021(17) C11C 0.041(3) 0.031(2) 0.035(2) 0.0005(17) -0.0007(19) 0.0012(18) C12C 0.039(2) 0.035(2) 0.043(3) -0.0005(18) -0.0052(19) 0.0012(18) C13C 0.046(3) 0.038(2) 0.042(3) -0.0013(19) -0.007(2) 0.0013(19) C14C 0.059(3) 0.031(2) 0.039(3) 0.0026(19) -0.003(2) 0.006(2) C15C 0.044(3) 0.034(2) 0.048(3) 0.0044(19) -0.001(2) -0.0038(19) C16C 0.042(3) 0.035(2) 0.043(3) 0.0032(18) -0.004(2) -0.0026(18) C17C 0.066(3) 0.048(3) 0.044(3) 0.006(2) 0.003(2) 0.002(2) C21C 0.039(2) 0.033(2) 0.033(3) 0.0019(17) -0.0030(18) -0.0005(17) C22C 0.039(3) 0.040(2) 0.047(3) -0.0002(19) -0.001(2) -0.0033(19) N23C 0.048(2) 0.048(2) 0.042(2) 0.0033(17) -0.0019(18) -0.0051(18) C24C 0.055(3) 0.047(3) 0.034(3) 0.004(2) 0.004(2) -0.003(2) C25C 0.044(3) 0.039(2) 0.046(3) 0.0065(19) 0.006(2) -0.0037(19) C26C 0.040(3) 0.036(2) 0.041(3) -0.0009(18) 0.0004(19) -0.0026(18) O1D 0.0362(19) 0.0488(17) 0.046(2) 0.0065(14) 0.0017(14) 0.0019(14) C1D 0.039(3) 0.0277(19) 0.044(3) 0.0002(17) -0.003(2) -0.0033(17) N1D 0.034(2) 0.041(2) 0.034(2) 0.0012(16) -0.0004(17) 0.0012(16) C11D 0.036(2) 0.033(2) 0.039(2) 0.0026(17) -0.0019(18) -0.0026(17) C12D 0.046(3) 0.034(2) 0.043(3) -0.0006(18) -0.001(2) -0.0033(18) C13D 0.055(3) 0.038(2) 0.035(2) 0.0008(18) 0.005(2) -0.009(2) C14D 0.052(3) 0.033(2) 0.044(3) 0.0036(19) -0.005(2) -0.010(2) C15D 0.046(3) 0.035(2) 0.049(3) 0.0070(19) -0.004(2) -0.0010(19) C16D 0.043(3) 0.035(2) 0.048(3) 0.0030(19) 0.001(2) 0.0008(19) C17D 0.072(4) 0.048(3) 0.048(3) 0.005(2) -0.007(3) -0.009(3) C21D 0.039(3) 0.031(2) 0.037(3) 0.0033(18) -0.0020(19) -0.0043(18) C22D 0.041(3) 0.040(2) 0.042(3) 0.0026(18) -0.0023(19) 0.0010(18) N23D 0.048(2) 0.050(2) 0.041(2) 0.0026(17) 0.0029(18) 0.0010(18) C24D 0.052(3) 0.044(3) 0.036(3) 0.002(2) -0.002(2) -0.009(2) C25D 0.043(3) 0.041(2) 0.044(3) 0.0099(19) -0.004(2) -0.0047(19) C26D 0.041(3) 0.040(2) 0.042(3) 0.0040(18) -0.0003(19) -0.0007(19) _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 1.235(5) . ? C1A N1A 1.355(6) . ? C1A C11A 1.502(7) . ? N1A C21A 1.417(6) . ? N1A H1A 0.74(6) . ? C11A C12A 1.369(6) . ? C11A C16A 1.411(6) . ? C12A C13A 1.384(6) . ? C12A H12A 0.9500 . ? C13A C14A 1.422(7) . ? C13A H13A 0.9500 . ? C14A C15A 1.359(6) . ? C14A C17A 1.514(6) . ? C15A C16A 1.392(6) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C21A C26A 1.383(6) . ? C21A C22A 1.401(7) . ? C22A N23A 1.342(6) . ? C22A H22A 0.9500 . ? N23A C24A 1.336(6) . ? C24A C25A 1.380(7) . ? C24A H24A 0.9500 . ? C25A C26A 1.384(6) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? O1B C1B 1.244(5) . ? C1B N1B 1.346(6) . ? C1B C11B 1.488(6) . ? N1B C21B 1.421(6) . ? N1B H1B 0.87(5) . ? C11B C12B 1.375(6) . ? C11B C16B 1.417(6) . ? C12B C13B 1.392(6) . ? C12B H12B 0.9500 . ? C13B C14B 1.399(7) . ? C13B H13B 0.9500 . ? C14B C15B 1.358(7) . ? C14B C17B 1.514(6) . ? C15B C16B 1.392(6) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C21B C26B 1.376(6) . ? C21B C22B 1.395(6) . ? C22B N23B 1.339(6) . ? C22B H22B 0.9500 . ? N23B C24B 1.340(6) . ? C24B C25B 1.391(7) . ? C24B H24B 0.9500 . ? C25B C26B 1.390(6) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? O1C C1C 1.224(5) . ? C1C N1C 1.369(6) . ? C1C C11C 1.489(6) . ? N1C C21C 1.398(6) . ? N1C H1C 0.71(4) . ? C11C C16C 1.373(6) . ? C11C C12C 1.407(6) . ? C12C C13C 1.369(6) . ? C12C H12C 0.9500 . ? C13C C14C 1.392(7) . ? C13C H13C 0.9500 . ? C14C C15C 1.411(6) . ? C14C C17C 1.501(7) . ? C15C C16C 1.377(6) . ? C15C H15C 0.9500 . ? C16C H16C 0.9500 . ? C17C H17G 0.9800 . ? C17C H17H 0.9800 . ? C17C H17I 0.9800 . ? C21C C26C 1.377(6) . ? C21C C22C 1.413(6) . ? C22C N23C 1.323(6) . ? C22C H22C 0.9500 . ? N23C C24C 1.325(6) . ? C24C C25C 1.394(7) . ? C24C H24C 0.9500 . ? C25C C26C 1.398(6) . ? C25C H25C 0.9500 . ? C26C H26C 0.9500 . ? O1D C1D 1.228(5) . ? C1D N1D 1.354(6) . ? C1D C11D 1.485(6) . ? N1D C21D 1.410(6) . ? N1D H1D 0.86(5) . ? C11D C12D 1.382(6) . ? C11D C16D 1.396(6) . ? C12D C13D 1.386(6) . ? C12D H12D 0.9500 . ? C13D C14D 1.370(7) . ? C13D H13D 0.9500 . ? C14D C15D 1.411(7) . ? C14D C17D 1.493(7) . ? C15D C16D 1.375(6) . ? C15D H15D 0.9500 . ? C16D H16D 0.9500 . ? C17D H17J 0.9800 . ? C17D H17K 0.9800 . ? C17D H17L 0.9800 . ? C21D C26D 1.382(6) . ? C21D C22D 1.390(6) . ? C22D N23D 1.333(6) . ? C22D H22D 0.9500 . ? N23D C24D 1.320(6) . ? C24D C25D 1.385(7) . ? C24D H24D 0.9500 . ? C25D C26D 1.383(6) . ? C25D H25D 0.9500 . ? C26D H26D 0.9500 . ? 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 O1A C1A N1A 122.7(5) . . ? O1A C1A C11A 121.4(4) . . ? N1A C1A C11A 115.9(4) . . ? C1A N1A C21A 124.6(4) . . ? C1A N1A H1A 112(5) . . ? C21A N1A H1A 121(5) . . ? C12A C11A C16A 118.8(4) . . ? C12A C11A C1A 117.1(4) . . ? C16A C11A C1A 124.1(4) . . ? C11A C12A C13A 120.0(4) . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C12A C13A C14A 121.5(4) . . ? C12A C13A H13A 119.3 . . ? C14A C13A H13A 119.3 . . ? C15A C14A C13A 118.0(4) . . ? C15A C14A C17A 120.2(4) . . ? C13A C14A C17A 121.8(4) . . ? C14A C15A C16A 120.8(4) . . ? C14A C15A H15A 119.6 . . ? C16A C15A H15A 119.6 . . ? C15A C16A C11A 120.8(4) . . ? C15A C16A H16A 119.6 . . ? C11A C16A H16A 119.6 . . ? C14A C17A H17A 109.5 . . ? C14A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C14A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C26A C21A C22A 118.9(4) . . ? C26A C21A N1A 122.5(4) . . ? C22A C21A N1A 118.6(4) . . ? N23A C22A C21A 122.8(4) . . ? N23A C22A H22A 118.6 . . ? C21A C22A H22A 118.6 . . ? C24A N23A C22A 117.2(4) . . ? N23A C24A C25A 123.5(5) . . ? N23A C24A H24A 118.2 . . ? C25A C24A H24A 118.2 . . ? C24A C25A C26A 119.3(4) . . ? C24A C25A H25A 120.3 . . ? C26A C25A H25A 120.3 . . ? C21A C26A C25A 118.2(4) . . ? C21A C26A H26A 120.9 . . ? C25A C26A H26A 120.9 . . ? O1B C1B N1B 122.7(4) . . ? O1B C1B C11B 121.3(4) . . ? N1B C1B C11B 116.0(4) . . ? C1B N1B C21B 124.8(4) . . ? C1B N1B H1B 117(3) . . ? C21B N1B H1B 117(3) . . ? C12B C11B C16B 117.9(4) . . ? C12B C11B C1B 117.7(4) . . ? C16B C11B C1B 124.4(4) . . ? C11B C12B C13B 120.1(4) . . ? C11B C12B H12B 119.9 . . ? C13B C12B H12B 119.9 . . ? C12B C13B C14B 121.7(4) . . ? C12B C13B H13B 119.2 . . ? C14B C13B H13B 119.2 . . ? C15B C14B C13B 118.5(4) . . ? C15B C14B C17B 119.6(5) . . ? C13B C14B C17B 121.9(4) . . ? C14B C15B C16B 120.7(4) . . ? C14B C15B H15B 119.7 . . ? C16B C15B H15B 119.7 . . ? C15B C16B C11B 121.1(4) . . ? C15B C16B H16B 119.5 . . ? C11B C16B H16B 119.5 . . ? C14B C17B H17D 109.5 . . ? C14B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C14B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C26B C21B C22B 119.2(4) . . ? C26B C21B N1B 122.4(4) . . ? C22B C21B N1B 118.3(4) . . ? N23B C22B C21B 124.1(4) . . ? N23B C22B H22B 118.0 . . ? C21B C22B H22B 118.0 . . ? C22B N23B C24B 116.1(4) . . ? N23B C24B C25B 123.5(5) . . ? N23B C24B H24B 118.3 . . ? C25B C24B H24B 118.3 . . ? C26B C25B C24B 119.6(4) . . ? C26B C25B H25B 120.2 . . ? C24B C25B H25B 120.2 . . ? C21B C26B C25B 117.5(4) . . ? C21B C26B H26B 121.3 . . ? C25B C26B H26B 121.3 . . ? O1C C1C N1C 123.2(4) . . ? O1C C1C C11C 121.2(4) . . ? N1C C1C C11C 115.6(4) . . ? C1C N1C C21C 127.1(4) . . ? C1C N1C H1C 117(4) . . ? C21C N1C H1C 116(4) . . ? C16C C11C C12C 120.3(4) . . ? C16C C11C C1C 121.8(4) . . ? C12C C11C C1C 117.9(4) . . ? C13C C12C C11C 121.0(4) . . ? C13C C12C H12C 119.5 . . ? C11C C12C H12C 119.5 . . ? C12C C13C C14C 119.3(4) . . ? C12C C13C H13C 120.4 . . ? C14C C13C H13C 120.4 . . ? C13C C14C C15C 119.1(4) . . ? C13C C14C C17C 120.4(4) . . ? C15C C14C C17C 120.6(5) . . ? C16C C15C C14C 121.4(4) . . ? C16C C15C H15C 119.3 . . ? C14C C15C H15C 119.3 . . ? C11C C16C C15C 118.8(4) . . ? C11C C16C H16C 120.6 . . ? C15C C16C H16C 120.6 . . ? C14C C17C H17G 109.5 . . ? C14C C17C H17H 109.5 . . ? H17G C17C H17H 109.5 . . ? C14C C17C H17I 109.5 . . ? H17G C17C H17I 109.5 . . ? H17H C17C H17I 109.5 . . ? C26C C21C N1C 122.1(4) . . ? C26C C21C C22C 118.5(4) . . ? N1C C21C C22C 119.5(4) . . ? N23C C22C C21C 125.6(4) . . ? N23C C22C H22C 117.2 . . ? C21C C22C H22C 117.2 . . ? C22C N23C C24C 115.6(4) . . ? N23C C24C C25C 123.4(5) . . ? N23C C24C H24C 118.3 . . ? C25C C24C H24C 118.3 . . ? C24C C25C C26C 120.9(4) . . ? C24C C25C H25C 119.6 . . ? C26C C25C H25C 119.6 . . ? C21C C26C C25C 116.0(4) . . ? C21C C26C H26C 122.0 . . ? C25C C26C H26C 122.0 . . ? O1D C1D N1D 122.7(4) . . ? O1D C1D C11D 122.2(4) . . ? N1D C1D C11D 115.1(4) . . ? C1D N1D C21D 126.0(4) . . ? C1D N1D H1D 121(3) . . ? C21D N1D H1D 112(3) . . ? C12D C11D C16D 118.6(4) . . ? C12D C11D C1D 118.5(4) . . ? C16D C11D C1D 122.9(4) . . ? C11D C12D C13D 121.3(4) . . ? C11D C12D H12D 119.4 . . ? C13D C12D H12D 119.4 . . ? C14D C13D C12D 120.6(4) . . ? C14D C13D H13D 119.7 . . ? C12D C13D H13D 119.7 . . ? C13D C14D C15D 118.5(4) . . ? C13D C14D C17D 121.9(5) . . ? C15D C14D C17D 119.6(4) . . ? C16D C15D C14D 120.9(4) . . ? C16D C15D H15D 119.6 . . ? C14D C15D H15D 119.6 . . ? C15D C16D C11D 120.2(5) . . ? C15D C16D H16D 119.9 . . ? C11D C16D H16D 119.9 . . ? C14D C17D H17J 109.5 . . ? C14D C17D H17K 109.5 . . ? H17J C17D H17K 109.5 . . ? C14D C17D H17L 109.5 . . ? H17J C17D H17L 109.5 . . ? H17K C17D H17L 109.5 . . ? C26D C21D C22D 119.1(4) . . ? C26D C21D N1D 123.8(4) . . ? C22D C21D N1D 117.1(4) . . ? N23D C22D C21D 123.3(4) . . ? N23D C22D H22D 118.4 . . ? C21D C22D H22D 118.4 . . ? C24D N23D C22D 117.3(4) . . ? N23D C24D C25D 123.4(5) . . ? N23D C24D H24D 118.3 . . ? C25D C24D H24D 118.3 . . ? C26D C25D C24D 119.6(4) . . ? C26D C25D H25D 120.2 . . ? C24D C25D H25D 120.2 . . ? C21D C26D C25D 117.3(4) . . ? C21D C26D H26D 121.3 . . ? C25D C26D H26D 121.3 . . ? 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 O1A C1A N1A C21A -0.2(7) . . . . ? C11A C1A N1A C21A 178.5(4) . . . . ? O1A C1A C11A C12A -29.3(6) . . . . ? N1A C1A C11A C12A 152.0(4) . . . . ? O1A C1A C11A C16A 149.1(4) . . . . ? N1A C1A C11A C16A -29.6(6) . . . . ? C16A C11A C12A C13A 0.8(6) . . . . ? C1A C11A C12A C13A 179.3(4) . . . . ? C11A C12A C13A C14A -1.4(7) . . . . ? C12A C13A C14A C15A 0.7(7) . . . . ? C12A C13A C14A C17A 179.8(4) . . . . ? C13A C14A C15A C16A 0.7(6) . . . . ? C17A C14A C15A C16A -178.5(4) . . . . ? C14A C15A C16A C11A -1.2(6) . . . . ? C12A C11A C16A C15A 0.5(6) . . . . ? C1A C11A C16A C15A -177.9(4) . . . . ? C1A N1A C21A C26A -36.3(6) . . . . ? C1A N1A C21A C22A 145.0(5) . . . . ? C26A C21A C22A N23A 0.0(7) . . . . ? N1A C21A C22A N23A 178.8(4) . . . . ? C21A C22A N23A C24A 0.3(7) . . . . ? C22A N23A C24A C25A 0.5(7) . . . . ? N23A C24A C25A C26A -1.5(7) . . . . ? C22A C21A C26A C25A -1.0(6) . . . . ? N1A C21A C26A C25A -179.7(4) . . . . ? C24A C25A C26A C21A 1.7(7) . . . . ? O1B C1B N1B C21B 1.5(7) . . . . ? C11B C1B N1B C21B -178.7(4) . . . . ? O1B C1B C11B C12B 28.6(6) . . . . ? N1B C1B C11B C12B -151.1(4) . . . . ? O1B C1B C11B C16B -149.6(4) . . . . ? N1B C1B C11B C16B 30.6(6) . . . . ? C16B C11B C12B C13B -0.4(6) . . . . ? C1B C11B C12B C13B -178.8(4) . . . . ? C11B C12B C13B C14B 1.7(7) . . . . ? C12B C13B C14B C15B -1.4(7) . . . . ? C12B C13B C14B C17B -179.8(4) . . . . ? C13B C14B C15B C16B -0.1(7) . . . . ? C17B C14B C15B C16B 178.3(4) . . . . ? C14B C15B C16B C11B 1.4(7) . . . . ? C12B C11B C16B C15B -1.1(6) . . . . ? C1B C11B C16B C15B 177.1(4) . . . . ? C1B N1B C21B C26B 34.9(6) . . . . ? C1B N1B C21B C22B -147.6(4) . . . . ? C26B C21B C22B N23B 0.1(7) . . . . ? N1B C21B C22B N23B -177.5(4) . . . . ? C21B C22B N23B C24B -0.5(6) . . . . ? C22B N23B C24B C25B 0.4(7) . . . . ? N23B C24B C25B C26B 0.1(7) . . . . ? C22B C21B C26B C25B 0.4(6) . . . . ? N1B C21B C26B C25B 177.9(4) . . . . ? C24B C25B C26B C21B -0.5(6) . . . . ? O1C C1C N1C C21C 6.9(7) . . . . ? C11C C1C N1C C21C -172.3(4) . . . . ? O1C C1C C11C C16C -153.0(4) . . . . ? N1C C1C C11C C16C 26.2(6) . . . . ? O1C C1C C11C C12C 24.6(6) . . . . ? N1C C1C C11C C12C -156.1(4) . . . . ? C16C C11C C12C C13C -1.9(6) . . . . ? C1C C11C C12C C13C -179.5(4) . . . . ? C11C C12C C13C C14C 1.9(6) . . . . ? C12C C13C C14C C15C -0.8(6) . . . . ? C12C C13C C14C C17C 178.4(4) . . . . ? C13C C14C C15C C16C -0.4(6) . . . . ? C17C C14C C15C C16C -179.6(4) . . . . ? C12C C11C C16C C15C 0.6(6) . . . . ? C1C C11C C16C C15C 178.2(4) . . . . ? C14C C15C C16C C11C 0.5(6) . . . . ? C1C N1C C21C C26C -30.1(6) . . . . ? C1C N1C C21C C22C 151.4(4) . . . . ? C26C C21C C22C N23C 0.9(7) . . . . ? N1C C21C C22C N23C 179.5(4) . . . . ? C21C C22C N23C C24C 0.1(7) . . . . ? C22C N23C C24C C25C -0.4(7) . . . . ? N23C C24C C25C C26C -0.3(7) . . . . ? N1C C21C C26C C25C 180.0(4) . . . . ? C22C C21C C26C C25C -1.4(6) . . . . ? C24C C25C C26C C21C 1.2(6) . . . . ? O1D C1D N1D C21D 8.0(6) . . . . ? C11D C1D N1D C21D -172.3(4) . . . . ? O1D C1D C11D C12D 24.3(6) . . . . ? N1D C1D C11D C12D -155.5(4) . . . . ? O1D C1D C11D C16D -152.8(4) . . . . ? N1D C1D C11D C16D 27.5(6) . . . . ? C16D C11D C12D C13D -1.8(6) . . . . ? C1D C11D C12D C13D -179.0(4) . . . . ? C11D C12D C13D C14D 1.8(7) . . . . ? C12D C13D C14D C15D -0.8(7) . . . . ? C12D C13D C14D C17D 179.2(4) . . . . ? C13D C14D C15D C16D -0.1(6) . . . . ? C17D C14D C15D C16D 179.9(4) . . . . ? C14D C15D C16D C11D 0.0(6) . . . . ? C12D C11D C16D C15D 0.9(6) . . . . ? C1D C11D C16D C15D 177.9(4) . . . . ? C1D N1D C21D C26D -31.4(6) . . . . ? C1D N1D C21D C22D 150.2(4) . . . . ? C26D C21D C22D N23D 0.7(7) . . . . ? N1D C21D C22D N23D 179.1(4) . . . . ? C21D C22D N23D C24D 0.4(7) . . . . ? C22D N23D C24D C25D -0.3(7) . . . . ? N23D C24D C25D C26D -0.9(7) . . . . ? C22D C21D C26D C25D -1.8(6) . . . . ? N1D C21D C26D C25D 179.8(4) . . . . ? C24D C25D C26D C21D 1.9(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A O1A 0.74(6) 2.35(6) 3.029(6) 153(6) 1_455 yes N1B H1B O1B 0.87(5) 2.19(5) 3.016(5) 160(4) 1_655 yes N1C H1C O1C 0.71(4) 2.39(4) 3.085(6) 167(5) 1_455 yes N1D H1D O1D 0.86(5) 2.26(5) 3.085(5) 162(5) 1_455 yes C26A H26A O1A 0.95 2.43 2.868(6) 108 . yes C26B H26B O1B 0.95 2.41 2.860(6) 109 . yes C26C H26C O1C 0.95 2.36 2.866(5) 113 . yes C26D H26D O1D 0.95 2.38 2.864(6) 111 . yes #========================================================================= data_Mmm_[9-02] _database_code_depnum_ccdc_archive 'CCDC 765528' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mmm _chemical_melting_point 363 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4025(4) _cell_length_b 9.8640(5) _cell_length_c 12.4783(7) _cell_angle_alpha 86.077(2) _cell_angle_beta 85.800(3) _cell_angle_gamma 69.390(3) _cell_volume 1079.21(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6306 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.635 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 7177 _diffrn_standards_decay_% ? _diffrn_reflns_number 4867 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.120 _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 -2 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.52 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.979 _reflns_number_total 4867 _reflns_number_gt 2397 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.1319P)^2^] 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 4867 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1624 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.2535 _refine_ls_wR_factor_gt 0.1873 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.40 _refine_diff_density_min -0.34 _refine_diff_density_rms 0.07 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 0.0800(3) 0.1632(3) -0.02098(18) 0.0440(6) Uani 1 1 d . . . C1A C 0.1728(4) 0.0426(4) -0.0376(3) 0.0356(8) Uani 1 1 d . . . N1A N 0.2309(3) -0.0013(3) -0.1380(2) 0.0362(7) Uani 1 1 d . . . H1A H 0.311(4) -0.092(5) -0.148(3) 0.058(12) Uiso 1 1 d . . . C11A C 0.2342(4) -0.0676(4) 0.0514(3) 0.0351(8) Uani 1 1 d . . . C12A C 0.2316(4) -0.0152(4) 0.1522(3) 0.0359(8) Uani 1 1 d . . . H12A H 0.1872 0.0861 0.1617 0.043 Uiso 1 1 calc R . . C13A C 0.2930(4) -0.1081(4) 0.2401(3) 0.0380(8) Uani 1 1 d . . . C14A C 0.3554(4) -0.2555(4) 0.2245(3) 0.0398(9) Uani 1 1 d . . . H14A H 0.3994 -0.3203 0.2827 0.048 Uiso 1 1 calc R . . C15A C 0.3547(4) -0.3097(4) 0.1253(3) 0.0413(9) Uani 1 1 d . . . H15A H 0.3949 -0.4113 0.1165 0.050 Uiso 1 1 calc R . . C16A C 0.2951(4) -0.2156(4) 0.0384(3) 0.0391(8) Uani 1 1 d . . . H16A H 0.2962 -0.2531 -0.0300 0.047 Uiso 1 1 calc R . . C17A C 0.2884(4) -0.0472(4) 0.3481(3) 0.0477(9) Uani 1 1 d . . . H17A H 0.3686 -0.1152 0.3912 0.072 Uiso 1 1 calc R . . H17B H 0.1890 -0.0325 0.3853 0.072 Uiso 1 1 calc R . . H17C H 0.3047 0.0458 0.3382 0.072 Uiso 1 1 calc R . . C21A C 0.1960(3) 0.0830(4) -0.2358(3) 0.0340(8) Uani 1 1 d . . . C22A C 0.0544(4) 0.1854(4) -0.2553(3) 0.0375(8) Uani 1 1 d . . . H22A H -0.0226 0.2054 -0.1989 0.045 Uiso 1 1 calc R . . N23A N 0.0214(3) 0.2580(3) -0.3513(2) 0.0393(7) Uani 1 1 d . . . C24A C 0.1319(4) 0.2282(4) -0.4296(3) 0.0399(8) Uani 1 1 d . . . H24A H 0.1098 0.2776 -0.4978 0.048 Uiso 1 1 calc R . . C25A C 0.2755(4) 0.1297(4) -0.4159(3) 0.0391(8) Uani 1 1 d . . . H25A H 0.3511 0.1131 -0.4732 0.047 Uiso 1 1 calc R . . C26A C 0.3086(4) 0.0557(4) -0.3186(3) 0.0391(8) Uani 1 1 d . . . H26A H 0.4072 -0.0134 -0.3078 0.047 Uiso 1 1 calc R . . O1B O 0.4473(3) 0.3443(3) 0.50980(19) 0.0415(6) Uani 1 1 d . . . C1B C 0.3341(4) 0.4542(4) 0.4986(3) 0.0354(8) Uani 1 1 d . . . N1B N 0.2641(3) 0.4935(3) 0.4031(2) 0.0336(7) Uani 1 1 d . . . H1B H 0.172(3) 0.578(3) 0.404(2) 0.024(8) Uiso 1 1 d . . . C11B C 0.2611(3) 0.5491(4) 0.5902(3) 0.0336(8) Uani 1 1 d . . . C12B C 0.2636(3) 0.4840(4) 0.6924(3) 0.0356(8) Uani 1 1 d . . . H12B H 0.3111 0.3819 0.7017 0.043 Uiso 1 1 calc R . . C13B C 0.1983(4) 0.5648(4) 0.7810(3) 0.0388(9) Uani 1 1 d . . . C14B C 0.1326(4) 0.7143(4) 0.7659(3) 0.0410(9) Uani 1 1 d . . . H14B H 0.0891 0.7718 0.8261 0.049 Uiso 1 1 calc R . . C15B C 0.1296(4) 0.7806(4) 0.6641(3) 0.0412(9) Uani 1 1 d . . . H15B H 0.0838 0.8829 0.6550 0.049 Uiso 1 1 calc R . . C16B C 0.1927(4) 0.6987(4) 0.5759(3) 0.0372(8) Uani 1 1 d . . . H16B H 0.1895 0.7441 0.5060 0.045 Uiso 1 1 calc R . . C17B C 0.2001(4) 0.4921(5) 0.8920(3) 0.0512(10) Uani 1 1 d . . . H17D H 0.1540 0.4172 0.8909 0.077 Uiso 1 1 calc R . . H17E H 0.1420 0.5645 0.9436 0.077 Uiso 1 1 calc R . . H17F H 0.3053 0.4475 0.9134 0.077 Uiso 1 1 calc R . . C21B C 0.3035(3) 0.4135(3) 0.3093(3) 0.0333(8) Uani 1 1 d . . . C22B C 0.4520(4) 0.3292(4) 0.2783(3) 0.0348(8) Uani 1 1 d . . . H22B H 0.5313 0.3227 0.3236 0.042 Uiso 1 1 calc R . . N23B N 0.4880(3) 0.2566(3) 0.1872(2) 0.0380(7) Uani 1 1 d . . . C24B C 0.3740(4) 0.2680(4) 0.1243(3) 0.0380(8) Uani 1 1 d . . . H24B H 0.3981 0.2173 0.0596 0.046 Uiso 1 1 calc R . . C25B C 0.2244(4) 0.3492(4) 0.1486(3) 0.0362(8) Uani 1 1 d . . . H25B H 0.1475 0.3551 0.1013 0.043 Uiso 1 1 calc R . . C26B C 0.1882(4) 0.4217(4) 0.2426(3) 0.0362(8) Uani 1 1 d . . . H26B H 0.0854 0.4768 0.2619 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0497(15) 0.0339(15) 0.0398(15) -0.0031(11) -0.0029(11) -0.0035(12) C1A 0.0358(18) 0.030(2) 0.041(2) -0.0024(16) -0.0021(15) -0.0106(15) N1A 0.0360(16) 0.0294(17) 0.0350(17) -0.0020(13) -0.0003(12) -0.0014(13) C11A 0.0330(17) 0.032(2) 0.040(2) -0.0043(16) 0.0018(14) -0.0111(15) C12A 0.0336(17) 0.034(2) 0.039(2) -0.0033(16) -0.0004(14) -0.0110(15) C13A 0.0346(18) 0.042(2) 0.039(2) -0.0011(17) 0.0021(15) -0.0159(16) C14A 0.0306(18) 0.041(2) 0.044(2) 0.0036(17) -0.0036(15) -0.0079(16) C15A 0.043(2) 0.031(2) 0.050(2) -0.0014(17) -0.0003(16) -0.0131(16) C16A 0.0382(19) 0.039(2) 0.041(2) -0.0087(17) 0.0037(15) -0.0135(16) C17A 0.050(2) 0.047(2) 0.044(2) 0.0000(18) -0.0084(17) -0.0131(18) C21A 0.0351(18) 0.0315(19) 0.0339(19) -0.0046(15) -0.0011(14) -0.0093(15) C22A 0.0337(18) 0.039(2) 0.040(2) -0.0073(16) -0.0007(14) -0.0121(16) N23A 0.0392(16) 0.0412(18) 0.0358(17) -0.0009(14) -0.0040(13) -0.0117(14) C24A 0.043(2) 0.039(2) 0.039(2) -0.0005(16) -0.0025(16) -0.0153(17) C25A 0.0371(19) 0.038(2) 0.040(2) -0.0068(17) 0.0060(15) -0.0105(16) C26A 0.0316(18) 0.037(2) 0.043(2) -0.0011(17) -0.0013(15) -0.0051(15) O1B 0.0379(13) 0.0362(15) 0.0436(15) -0.0015(11) -0.0022(11) -0.0046(11) C1B 0.0325(18) 0.037(2) 0.037(2) 0.0016(16) -0.0026(14) -0.0125(16) N1B 0.0332(15) 0.0299(17) 0.0316(16) -0.0039(12) -0.0032(12) -0.0027(13) C11B 0.0307(17) 0.034(2) 0.036(2) -0.0025(15) -0.0044(14) -0.0109(15) C12B 0.0304(17) 0.039(2) 0.035(2) -0.0039(16) -0.0012(14) -0.0099(15) C13B 0.0310(18) 0.052(2) 0.035(2) -0.0059(17) 0.0001(14) -0.0168(17) C14B 0.0345(19) 0.046(2) 0.042(2) -0.0124(18) -0.0012(15) -0.0117(16) C15B 0.0344(19) 0.037(2) 0.050(2) -0.0126(18) -0.0020(16) -0.0079(16) C16B 0.0381(18) 0.035(2) 0.038(2) -0.0028(16) -0.0059(15) -0.0121(16) C17B 0.052(2) 0.063(3) 0.038(2) -0.0049(19) 0.0024(17) -0.020(2) C21B 0.0324(17) 0.0285(19) 0.0364(19) -0.0014(15) -0.0005(14) -0.0077(14) C22B 0.0336(18) 0.035(2) 0.0320(19) 0.0001(15) -0.0016(14) -0.0084(15) N23B 0.0399(16) 0.0397(18) 0.0330(17) -0.0046(13) 0.0012(12) -0.0120(13) C24B 0.043(2) 0.036(2) 0.035(2) -0.0060(16) -0.0014(15) -0.0123(16) C25B 0.0405(19) 0.036(2) 0.0336(19) -0.0044(15) -0.0053(14) -0.0136(16) C26B 0.0320(18) 0.034(2) 0.040(2) -0.0011(16) 0.0013(14) -0.0086(15) _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 1.223(4) . ? C1A N1A 1.365(4) . ? C1A C11A 1.495(5) . ? N1A C21A 1.420(4) . ? N1A H1A 0.96(4) . ? C11A C16A 1.384(5) . ? C11A C12A 1.388(5) . ? C12A C13A 1.400(5) . ? C12A H12A 0.9500 . ? C13A C14A 1.385(5) . ? C13A C17A 1.504(5) . ? C14A C15A 1.383(5) . ? C14A H14A 0.9500 . ? C15A C16A 1.391(5) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C21A C22A 1.385(5) . ? C21A C26A 1.392(4) . ? C22A N23A 1.350(4) . ? C22A H22A 0.9500 . ? N23A C24A 1.340(4) . ? C24A C25A 1.373(5) . ? C24A H24A 0.9500 . ? C25A C26A 1.371(5) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? O1B C1B 1.231(4) . ? C1B N1B 1.370(4) . ? C1B C11B 1.494(5) . ? N1B C21B 1.410(4) . ? N1B H1B 0.97(3) . ? C11B C12B 1.386(5) . ? C11B C16B 1.391(5) . ? C12B C13B 1.382(5) . ? C12B H12B 0.9500 . ? C13B C14B 1.390(5) . ? C13B C17B 1.514(5) . ? C14B C15B 1.386(5) . ? C14B H14B 0.9500 . ? C15B C16B 1.381(5) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C21B C26B 1.391(4) . ? C21B C22B 1.393(4) . ? C22B N23B 1.343(4) . ? C22B H22B 0.9500 . ? N23B C24B 1.342(4) . ? C24B C25B 1.375(4) . ? C24B H24B 0.9500 . ? C25B C26B 1.374(5) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? 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 O1A C1A N1A 123.0(3) . . ? O1A C1A C11A 122.4(3) . . ? N1A C1A C11A 114.6(3) . . ? C1A N1A C21A 126.2(3) . . ? C1A N1A H1A 121(2) . . ? C21A N1A H1A 112(2) . . ? C16A C11A C12A 119.1(3) . . ? C16A C11A C1A 124.2(3) . . ? C12A C11A C1A 116.7(3) . . ? C11A C12A C13A 121.6(3) . . ? C11A C12A H12A 119.2 . . ? C13A C12A H12A 119.2 . . ? C14A C13A C12A 118.1(3) . . ? C14A C13A C17A 121.8(3) . . ? C12A C13A C17A 120.0(3) . . ? C15A C14A C13A 121.0(3) . . ? C15A C14A H14A 119.5 . . ? C13A C14A H14A 119.5 . . ? C14A C15A C16A 120.1(3) . . ? C14A C15A H15A 119.9 . . ? C16A C15A H15A 119.9 . . ? C11A C16A C15A 120.1(3) . . ? C11A C16A H16A 120.0 . . ? C15A C16A H16A 120.0 . . ? C13A C17A H17A 109.5 . . ? C13A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C13A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C22A C21A C26A 118.3(3) . . ? C22A C21A N1A 123.8(3) . . ? C26A C21A N1A 117.9(3) . . ? N23A C22A C21A 122.6(3) . . ? N23A C22A H22A 118.7 . . ? C21A C22A H22A 118.7 . . ? C24A N23A C22A 117.6(3) . . ? N23A C24A C25A 123.1(3) . . ? N23A C24A H24A 118.5 . . ? C25A C24A H24A 118.5 . . ? C26A C25A C24A 119.2(3) . . ? C26A C25A H25A 120.4 . . ? C24A C25A H25A 120.4 . . ? C25A C26A C21A 119.2(3) . . ? C25A C26A H26A 120.4 . . ? C21A C26A H26A 120.4 . . ? O1B C1B N1B 122.2(3) . . ? O1B C1B C11B 121.7(3) . . ? N1B C1B C11B 116.0(3) . . ? C1B N1B C21B 126.0(3) . . ? C1B N1B H1B 115.8(17) . . ? C21B N1B H1B 117.8(17) . . ? C12B C11B C16B 119.7(3) . . ? C12B C11B C1B 118.0(3) . . ? C16B C11B C1B 122.3(3) . . ? C13B C12B C11B 121.3(3) . . ? C13B C12B H12B 119.4 . . ? C11B C12B H12B 119.4 . . ? C12B C13B C14B 118.4(3) . . ? C12B C13B C17B 120.7(3) . . ? C14B C13B C17B 120.8(3) . . ? C15B C14B C13B 120.7(3) . . ? C15B C14B H14B 119.6 . . ? C13B C14B H14B 119.6 . . ? C16B C15B C14B 120.4(3) . . ? C16B C15B H15B 119.8 . . ? C14B C15B H15B 119.8 . . ? C15B C16B C11B 119.4(3) . . ? C15B C16B H16B 120.3 . . ? C11B C16B H16B 120.3 . . ? C13B C17B H17D 109.5 . . ? C13B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C13B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C26B C21B C22B 118.0(3) . . ? C26B C21B N1B 118.3(3) . . ? C22B C21B N1B 123.7(3) . . ? N23B C22B C21B 122.9(3) . . ? N23B C22B H22B 118.6 . . ? C21B C22B H22B 118.6 . . ? C24B N23B C22B 117.5(3) . . ? N23B C24B C25B 123.5(3) . . ? N23B C24B H24B 118.3 . . ? C25B C24B H24B 118.3 . . ? C26B C25B C24B 118.8(3) . . ? C26B C25B H25B 120.6 . . ? C24B C25B H25B 120.6 . . ? C25B C26B C21B 119.4(3) . . ? C25B C26B H26B 120.3 . . ? C21B C26B H26B 120.3 . . ? 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 O1A C1A N1A C21A 0.8(5) . . . . ? C11A C1A N1A C21A -177.9(3) . . . . ? O1A C1A C11A C16A 156.8(3) . . . . ? N1A C1A C11A C16A -24.4(4) . . . . ? O1A C1A C11A C12A -24.6(4) . . . . ? N1A C1A C11A C12A 154.1(3) . . . . ? C16A C11A C12A C13A 1.8(5) . . . . ? C1A C11A C12A C13A -176.8(3) . . . . ? C11A C12A C13A C14A -0.8(4) . . . . ? C11A C12A C13A C17A 179.9(3) . . . . ? C12A C13A C14A C15A -1.2(4) . . . . ? C17A C13A C14A C15A 178.2(3) . . . . ? C13A C14A C15A C16A 2.1(5) . . . . ? C12A C11A C16A C15A -0.9(4) . . . . ? C1A C11A C16A C15A 177.6(3) . . . . ? C14A C15A C16A C11A -1.0(5) . . . . ? C1A N1A C21A C22A -34.0(5) . . . . ? C1A N1A C21A C26A 149.4(3) . . . . ? C26A C21A C22A N23A 0.7(5) . . . . ? N1A C21A C22A N23A -175.8(3) . . . . ? C21A C22A N23A C24A -0.1(5) . . . . ? C22A N23A C24A C25A -0.8(5) . . . . ? N23A C24A C25A C26A 1.1(5) . . . . ? C24A C25A C26A C21A -0.5(5) . . . . ? C22A C21A C26A C25A -0.4(5) . . . . ? N1A C21A C26A C25A 176.4(3) . . . . ? O1B C1B N1B C21B 3.8(5) . . . . ? C11B C1B N1B C21B -173.6(3) . . . . ? O1B C1B C11B C12B -33.4(4) . . . . ? N1B C1B C11B C12B 144.0(3) . . . . ? O1B C1B C11B C16B 146.1(3) . . . . ? N1B C1B C11B C16B -36.4(4) . . . . ? C16B C11B C12B C13B 0.4(5) . . . . ? C1B C11B C12B C13B -180.0(3) . . . . ? C11B C12B C13B C14B -1.4(5) . . . . ? C11B C12B C13B C17B 179.2(3) . . . . ? C12B C13B C14B C15B 1.4(5) . . . . ? C17B C13B C14B C15B -179.3(3) . . . . ? C13B C14B C15B C16B -0.3(5) . . . . ? C14B C15B C16B C11B -0.7(5) . . . . ? C12B C11B C16B C15B 0.7(4) . . . . ? C1B C11B C16B C15B -178.9(3) . . . . ? C1B N1B C21B C26B 147.5(3) . . . . ? C1B N1B C21B C22B -33.9(5) . . . . ? C26B C21B C22B N23B 0.3(5) . . . . ? N1B C21B C22B N23B -178.3(3) . . . . ? C21B C22B N23B C24B 0.3(5) . . . . ? C22B N23B C24B C25B -0.1(5) . . . . ? N23B C24B C25B C26B -0.7(5) . . . . ? C24B C25B C26B C21B 1.3(5) . . . . ? C22B C21B C26B C25B -1.1(5) . . . . ? N1B C21B C26B C25B 177.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A N23B 0.96(4) 2.06(4) 2.998(4) 166(3) 2_655 yes N1B H1B N23A 0.97(3) 2.08(3) 3.006(4) 160(2) 2_565 yes C22A H22A O1A 0.95 2.44 2.938(4) 113 . yes C22B H22B O1B 0.95 2.40 2.899(4) 113 . yes C22A H22A Cg1 0.95 2.78 3.563(4) 141 2 yes C22B H22B Cg2 0.95 2.75 3.544(4) 142 2_666 yes # Cg1 and Cg2 are the C~6~ aromatic rings located at sites 2 and 2_666 # Complete details for the C-H...\p(arene) interaction # C22A H22A C11A 0.95 3.20 3.999(4) 143.3 2 # C22A H22A C12A 0.95 3.16 3.753(4) 121.9 2 # C22A H22A C13A 0.95 3.10 3.596(4) 114.0 2 # C22A H22A C14A 0.95 3.03 3.663(4) 125.5 2 # C22A H22A C15A 0.95 3.02 3.869(5) 150.1 2 # C22A H22A C16A 0.95 3.11 4.041(5) 166.5 2 # C22B H22B C11B 0.95 2.97 3.822(4) 150.6 2_666 # C22B H22B C12B 0.95 3.14 3.793(4) 127.2 2_666 # C22B H22B C13B 0.95 3.27 3.796(4) 116.9 2_666 # C22B H22B C14B 0.95 3.18 3.779(4) 123.0 2_666 # C22B H22B C15B 0.95 3.00 3.805(4) 143.5 2_666 # C22B H22B C16B 0.95 2.90 3.836(4) 169.2 2_666 #========================================================================= data_Mom_[9-03] _database_code_depnum_ccdc_archive 'CCDC 765529' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mom _chemical_melting_point 381 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.5170(2) _cell_length_b 10.4800(3) _cell_length_c 9.1960(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1109.94(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10053 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 9558 _diffrn_standards_decay_% ? _diffrn_reflns_number 8920 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.041 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 2500 _reflns_number_gt 2086 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.031P)^2^+0.3571P] 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 0.018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2500 _refine_ls_number_parameters 151 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.17 _refine_diff_density_min -0.17 _refine_diff_density_rms 0.04 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 0.13338(11) 0.25089(13) 0.4562(2) 0.0385(4) Uani 1 1 d . . . C1 C 0.23560(16) 0.27492(18) 0.4821(2) 0.0277(4) Uani 1 1 d . . . N1 N 0.27231(14) 0.38254(15) 0.55189(19) 0.0276(4) Uani 1 1 d . . . H1 H 0.351(2) 0.386(2) 0.576(3) 0.057(7) Uiso 1 1 d . . . C11 C 0.33249(16) 0.18724(18) 0.43756(19) 0.0269(4) Uani 1 1 d . . . C12 C 0.33298(16) 0.05941(17) 0.4803(2) 0.0258(4) Uani 1 1 d . . . C13 C 0.42296(17) -0.01759(19) 0.4284(2) 0.0293(4) Uani 1 1 d . . . H13 H 0.4264 -0.1044 0.4579 0.035 Uiso 1 1 calc R . . C14 C 0.50687(19) 0.0290(2) 0.3356(2) 0.0337(5) Uani 1 1 d . . . H14 H 0.5659 -0.0261 0.3002 0.040 Uiso 1 1 calc R . . C15 C 0.50521(18) 0.1556(2) 0.2940(2) 0.0346(5) Uani 1 1 d . . . H15 H 0.5630 0.1879 0.2301 0.042 Uiso 1 1 calc R . . C16 C 0.41876(18) 0.23508(19) 0.3462(2) 0.0312(4) Uani 1 1 d . . . H16 H 0.4182 0.3227 0.3196 0.037 Uiso 1 1 calc R . . C17 C 0.24306(17) 0.00528(19) 0.5821(2) 0.0332(4) Uani 1 1 d . . . H17A H 0.1674 0.0040 0.5334 0.050 Uiso 1 1 calc R . . H17B H 0.2384 0.0585 0.6695 0.050 Uiso 1 1 calc R . . H17C H 0.2650 -0.0818 0.6095 0.050 Uiso 1 1 calc R . . C21 C 0.20194(15) 0.48105(16) 0.6068(2) 0.0250(4) Uani 1 1 d . . . C22 C 0.08522(16) 0.49745(18) 0.5713(2) 0.0283(4) Uani 1 1 d . . . H22 H 0.0506 0.4399 0.5043 0.034 Uiso 1 1 calc R . . N23 N 0.01967(13) 0.59113(15) 0.62758(19) 0.0313(4) Uani 1 1 d . . . C24 C 0.06867(18) 0.6729(2) 0.7198(2) 0.0351(5) Uani 1 1 d . . . H24 H 0.0225 0.7394 0.7596 0.042 Uiso 1 1 calc R . . C25 C 0.18434(18) 0.6648(2) 0.7599(2) 0.0387(5) Uani 1 1 d . . . H25 H 0.2170 0.7252 0.8252 0.046 Uiso 1 1 calc R . . C26 C 0.25144(18) 0.56750(18) 0.7037(2) 0.0328(5) Uani 1 1 d . . . H26 H 0.3307 0.5596 0.7308 0.039 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 0.0238(6) 0.0315(8) 0.0603(9) -0.0102(7) -0.0100(7) 0.0011(6) C1 0.0270(9) 0.0245(9) 0.0316(10) 0.0017(8) -0.0032(8) 0.0018(8) N1 0.0223(8) 0.0228(8) 0.0378(9) -0.0024(7) -0.0024(7) -0.0001(7) C11 0.0270(10) 0.0273(10) 0.0263(10) -0.0040(8) -0.0058(8) 0.0031(8) C12 0.0276(9) 0.0256(9) 0.0242(9) -0.0036(8) -0.0051(8) 0.0021(8) C13 0.0331(10) 0.0272(10) 0.0276(10) -0.0031(8) -0.0039(8) 0.0043(8) C14 0.0330(10) 0.0363(12) 0.0318(10) -0.0047(9) 0.0002(9) 0.0071(10) C15 0.0328(11) 0.0391(12) 0.0320(11) -0.0032(9) 0.0042(9) -0.0018(10) C16 0.0345(10) 0.0260(10) 0.0330(10) 0.0018(8) -0.0016(9) 0.0013(8) C17 0.0326(10) 0.0335(10) 0.0334(10) 0.0031(8) 0.0005(9) 0.0029(9) C21 0.0237(8) 0.0197(9) 0.0315(10) 0.0022(8) 0.0029(8) -0.0001(7) C22 0.0235(9) 0.0244(9) 0.0370(10) -0.0009(8) -0.0030(8) 0.0007(8) N23 0.0242(8) 0.0251(8) 0.0447(10) -0.0006(7) 0.0011(7) 0.0020(7) C24 0.0295(10) 0.0282(10) 0.0477(12) -0.0045(9) 0.0057(9) 0.0044(9) C25 0.0318(11) 0.0346(12) 0.0495(13) -0.0156(10) -0.0035(10) -0.0006(9) C26 0.0234(9) 0.0316(10) 0.0434(12) -0.0049(10) -0.0033(9) 0.0000(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 O1 C1 1.227(2) . ? C1 N1 1.365(2) . ? C1 C11 1.503(3) . ? N1 C21 1.406(2) . ? N1 H1 0.93(3) . ? C11 C16 1.394(3) . ? C11 C12 1.396(3) . ? C12 C13 1.398(3) . ? C12 C17 1.506(3) . ? C13 C14 1.379(3) . ? C13 H13 0.9500 . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 C26 1.393(3) . ? C21 C22 1.394(2) . ? C22 N23 1.342(2) . ? C22 H22 0.9500 . ? N23 C24 1.331(3) . ? C24 C25 1.385(3) . ? C24 H24 0.9500 . ? C25 C26 1.380(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 O1 C1 N1 123.92(17) . . ? O1 C1 C11 122.27(17) . . ? N1 C1 C11 113.80(16) . . ? C1 N1 C21 126.65(16) . . ? C1 N1 H1 116.2(16) . . ? C21 N1 H1 116.6(16) . . ? C16 C11 C12 120.79(17) . . ? C16 C11 C1 118.27(17) . . ? C12 C11 C1 120.86(17) . . ? C11 C12 C13 117.43(17) . . ? C11 C12 C17 122.25(17) . . ? C13 C12 C17 120.30(17) . . ? C14 C13 C12 121.79(18) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 120.12(19) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 119.49(19) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C11 120.35(18) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 C21 C22 117.67(17) . . ? C26 C21 N1 118.11(16) . . ? C22 C21 N1 124.21(17) . . ? N23 C22 C21 122.83(18) . . ? N23 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? C24 N23 C22 118.57(16) . . ? N23 C24 C25 122.54(19) . . ? N23 C24 H24 118.7 . . ? C25 C24 H24 118.7 . . ? C26 C25 C24 119.0(2) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C25 C26 C21 119.41(19) . . ? C25 C26 H26 120.3 . . ? C21 C26 H26 120.3 . . ? 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 O1 C1 N1 C21 1.0(3) . . . . ? C11 C1 N1 C21 -179.55(17) . . . . ? O1 C1 C11 C16 121.3(2) . . . . ? N1 C1 C11 C16 -58.1(2) . . . . ? O1 C1 C11 C12 -55.4(3) . . . . ? N1 C1 C11 C12 125.15(19) . . . . ? C16 C11 C12 C13 0.2(3) . . . . ? C1 C11 C12 C13 176.81(17) . . . . ? C16 C11 C12 C17 178.33(18) . . . . ? C1 C11 C12 C17 -5.0(3) . . . . ? C11 C12 C13 C14 -1.6(3) . . . . ? C17 C12 C13 C14 -179.77(19) . . . . ? C12 C13 C14 C15 1.5(3) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C11 -1.4(3) . . . . ? C12 C11 C16 C15 1.3(3) . . . . ? C1 C11 C16 C15 -175.45(18) . . . . ? C1 N1 C21 C26 165.12(19) . . . . ? C1 N1 C21 C22 -14.4(3) . . . . ? C26 C21 C22 N23 -0.8(3) . . . . ? N1 C21 C22 N23 178.72(18) . . . . ? C21 C22 N23 C24 0.9(3) . . . . ? C22 N23 C24 C25 -0.2(3) . . . . ? N23 C24 C25 C26 -0.7(4) . . . . ? C24 C25 C26 C21 0.8(3) . . . . ? C22 C21 C26 C25 -0.1(3) . . . . ? N1 C21 C26 C25 -179.65(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N23 0.93(3) 2.01(3) 2.946(2) 175(2) 4_565 yes C22 H22 O1 0.95 2.24 2.847(2) 121 . yes C24 H24 O1 0.95 2.55 3.283(3) 134 2_565 yes C17 H17B Cg1 0.98 2.76 3.542(2) 138 3 yes # Cg1 is the C~6~ aromatic rings located at symmetry operator 3 # Complete details for the C-H...\p(arene) interaction # C17 H17B C11 0.98 2.93 3.883(3) 165.7 3 # C17 H17B C12 0.98 2.97 3.808(3) 143.7 3 # C17 H17B C13 0.98 3.12 3.722(3) 120.9 3 # C17 H17B C14 0.98 3.23 3.713(3) 112.5 3 # C17 H17B C15 0.98 3.20 3.802(3) 121.6 3 # C17 H17B C16 0.98 3.06 3.895(3) 144.4 3 #================================================= data_Mpo-[9-12] _database_code_depnum_ccdc_archive 'CCDC 765530' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mpo _chemical_melting_point 378 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9079(3) _cell_length_b 7.7140(4) _cell_length_c 12.2606(8) _cell_angle_alpha 97.406(2) _cell_angle_beta 94.029(2) _cell_angle_gamma 107.463(2) _cell_volume 525.04(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4673 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.648 _exptl_absorpt_correction_T_max 0.756 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device BrukerAPEXII _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 6070 _diffrn_standards_decay_% ? _diffrn_reflns_number 6050 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.028 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.53 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.978 _reflns_number_total 2365 _reflns_number_gt 1978 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker software (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.1751P] 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 2365 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.32 _refine_diff_density_min -0.19 _refine_diff_density_rms 0.04 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 0.07663(16) 0.34940(13) 0.14113(8) 0.0252(2) Uani 1 1 d . . . N1 N -0.25770(19) 0.40404(15) 0.06554(9) 0.0197(2) Uani 1 1 d . . . H1 H -0.342(3) 0.480(2) 0.0739(14) 0.029(4) Uiso 1 1 d . . . C1 C -0.0811(2) 0.42194(17) 0.14865(10) 0.0185(3) Uani 1 1 d . . . C11 C -0.0982(2) 0.53272(17) 0.25551(10) 0.0182(3) Uani 1 1 d . . . C12 C 0.1132(2) 0.63960(18) 0.32095(11) 0.0218(3) Uani 1 1 d . . . H12 H 0.2626 0.6511 0.2935 0.026 Uiso 1 1 calc R . . C13 C 0.1061(2) 0.72881(19) 0.42566(11) 0.0247(3) Uani 1 1 d . . . H13 H 0.2510 0.8023 0.4688 0.030 Uiso 1 1 calc R . . C14 C -0.1100(2) 0.71258(18) 0.46873(10) 0.0218(3) Uani 1 1 d . . . C15 C -0.3199(2) 0.60786(18) 0.40216(10) 0.0215(3) Uani 1 1 d . . . H15 H -0.4692 0.5970 0.4296 0.026 Uiso 1 1 calc R . . C16 C -0.3157(2) 0.51875(18) 0.29631(10) 0.0202(3) Uani 1 1 d . . . H16 H -0.4610 0.4487 0.2522 0.024 Uiso 1 1 calc R . . C17 C -0.1179(3) 0.8036(2) 0.58436(11) 0.0291(3) Uani 1 1 d . . . H17A H -0.2726 0.8247 0.5893 0.044 Uiso 1 1 calc R . . H17B H 0.0103 0.9216 0.6014 0.044 Uiso 1 1 calc R . . H17C H -0.0965 0.7236 0.6375 0.044 Uiso 1 1 calc R . . C21 C -0.3314(2) 0.26804(17) -0.02894(10) 0.0180(3) Uani 1 1 d . . . N22 N -0.53180(18) 0.27069(14) -0.08689(9) 0.0196(2) Uani 1 1 d . . . C23 C -0.6289(2) 0.13429(18) -0.17246(11) 0.0220(3) Uani 1 1 d . . . H23 H -0.7719 0.1334 -0.2135 0.026 Uiso 1 1 calc R . . C24 C -0.5333(2) -0.00461(18) -0.20425(11) 0.0239(3) Uani 1 1 d . . . H24 H -0.6102 -0.1000 -0.2643 0.029 Uiso 1 1 calc R . . C25 C -0.3209(2) -0.00085(19) -0.14579(11) 0.0244(3) Uani 1 1 d . . . H25 H -0.2487 -0.0930 -0.1664 0.029 Uiso 1 1 calc R . . C26 C -0.2154(2) 0.13840(18) -0.05716(11) 0.0223(3) Uani 1 1 d . . . H26 H -0.0687 0.1452 -0.0170 0.027 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 0.0235(5) 0.0302(5) 0.0260(5) 0.0013(4) 0.0003(4) 0.0163(4) N1 0.0231(5) 0.0205(5) 0.0191(5) 0.0007(4) 0.0004(4) 0.0136(5) C1 0.0183(6) 0.0185(6) 0.0201(6) 0.0047(5) 0.0018(5) 0.0073(5) C11 0.0202(6) 0.0172(6) 0.0184(6) 0.0042(5) -0.0002(5) 0.0078(5) C12 0.0179(6) 0.0223(6) 0.0254(7) 0.0033(5) 0.0001(5) 0.0072(5) C13 0.0237(6) 0.0216(6) 0.0262(7) 0.0000(5) -0.0056(5) 0.0067(5) C14 0.0294(7) 0.0188(6) 0.0188(6) 0.0032(5) -0.0006(5) 0.0108(5) C15 0.0222(6) 0.0247(7) 0.0208(6) 0.0061(5) 0.0036(5) 0.0107(5) C16 0.0181(6) 0.0217(6) 0.0204(6) 0.0038(5) -0.0012(5) 0.0062(5) C17 0.0396(8) 0.0277(7) 0.0211(7) -0.0004(6) -0.0006(6) 0.0148(6) C21 0.0201(6) 0.0183(6) 0.0171(6) 0.0041(5) 0.0037(5) 0.0075(5) N22 0.0205(5) 0.0201(5) 0.0199(5) 0.0027(4) 0.0016(4) 0.0092(4) C23 0.0211(6) 0.0225(6) 0.0220(6) 0.0041(5) 0.0002(5) 0.0066(5) C24 0.0278(7) 0.0192(6) 0.0223(6) 0.0000(5) 0.0015(5) 0.0055(5) C25 0.0311(7) 0.0206(6) 0.0254(7) 0.0023(5) 0.0057(5) 0.0139(6) C26 0.0247(6) 0.0242(7) 0.0215(6) 0.0036(5) 0.0023(5) 0.0133(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2254(15) . ? N1 C1 1.3688(16) . ? N1 C21 1.4049(16) . ? N1 H1 0.875(18) . ? C1 C11 1.4963(17) . ? C11 C16 1.3906(17) . ? C11 C12 1.3981(17) . ? C12 C13 1.3860(19) . ? C12 H12 0.9500 . ? C13 C14 1.3930(19) . ? C13 H13 0.9500 . ? C14 C15 1.3938(18) . ? C14 C17 1.5090(18) . ? C15 C16 1.3937(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 N22 1.3443(16) . ? C21 C26 1.3947(18) . ? N22 C23 1.3437(16) . ? C23 C24 1.3805(19) . ? C23 H23 0.9500 . ? C24 C25 1.3909(19) . ? C24 H24 0.9500 . ? C25 C26 1.3876(19) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C21 127.04(11) . . ? C1 N1 H1 117.2(11) . . ? C21 N1 H1 115.6(11) . . ? O1 C1 N1 124.61(12) . . ? O1 C1 C11 120.51(11) . . ? N1 C1 C11 114.82(11) . . ? C16 C11 C12 119.18(12) . . ? C16 C11 C1 122.06(11) . . ? C12 C11 C1 118.47(11) . . ? C13 C12 C11 120.35(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.15(12) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 118.01(12) . . ? C13 C14 C17 121.28(12) . . ? C15 C14 C17 120.72(12) . . ? C16 C15 C14 121.50(12) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C11 C16 C15 119.80(12) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N22 C21 C26 123.36(12) . . ? N22 C21 N1 112.93(11) . . ? C26 C21 N1 123.65(11) . . ? C23 N22 C21 117.11(11) . . ? N22 C23 C24 123.89(12) . . ? N22 C23 H23 118.1 . . ? C24 C23 H23 118.1 . . ? C23 C24 C25 118.06(12) . . ? C23 C24 H24 121.0 . . ? C25 C24 H24 121.0 . . ? C26 C25 C24 119.56(12) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 117.91(12) . . ? C25 C26 H26 121.0 . . ? C21 C26 H26 121.0 . . ? 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 C21 N1 C1 O1 18.2(2) . . . . ? C21 N1 C1 C11 -159.04(12) . . . . ? O1 C1 C11 C16 -137.39(13) . . . . ? N1 C1 C11 C16 39.97(16) . . . . ? O1 C1 C11 C12 36.29(17) . . . . ? N1 C1 C11 C12 -146.36(12) . . . . ? C16 C11 C12 C13 0.70(19) . . . . ? C1 C11 C12 C13 -173.17(11) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C12 C13 C14 C15 -1.74(19) . . . . ? C12 C13 C14 C17 177.64(12) . . . . ? C13 C14 C15 C16 1.13(19) . . . . ? C17 C14 C15 C16 -178.25(12) . . . . ? C12 C11 C16 C15 -1.29(18) . . . . ? C1 C11 C16 C15 172.34(11) . . . . ? C14 C15 C16 C11 0.38(19) . . . . ? C1 N1 C21 N22 170.74(11) . . . . ? C1 N1 C21 C26 -6.5(2) . . . . ? C26 C21 N22 C23 3.67(18) . . . . ? N1 C21 N22 C23 -173.61(11) . . . . ? C21 N22 C23 C24 -0.90(19) . . . . ? N22 C23 C24 C25 -1.5(2) . . . . ? C23 C24 C25 C26 1.2(2) . . . . ? C24 C25 C26 C21 1.3(2) . . . . ? N22 C21 C26 C25 -3.9(2) . . . . ? N1 C21 C26 C25 173.09(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.875(18) 2.255(18) 3.1081(15) 164.6(15) 2_465 yes C25 H25 O1 0.95 2.52 3.4165(16) 157 2 yes C26 H26 O1 0.95 2.27 2.8707(16) 121 . yes #========================================================= data_Mmo-[9-11] _database_code_depnum_ccdc_archive 'CCDC 765531' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Mmo _chemical_melting_point 353 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 '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 5.1480(3) _cell_length_b 13.9239(14) _cell_length_c 15.0042(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.000(5) _cell_angle_gamma 90.00 _cell_volume 1065.04(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3092 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 5222 _diffrn_standards_decay_% ? _diffrn_reflns_number 6938 _diffrn_reflns_av_R_equivalents 0.073 _diffrn_reflns_av_sigmaI/netI 0.086 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 2433 _reflns_number_gt 1322 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.101P)^2^] 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 2433 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1358 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1954 _refine_ls_wR_factor_gt 0.1544 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.35 _refine_diff_density_min -0.30 _refine_diff_density_rms 0.07 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 0.4997(3) 0.28509(13) 0.69291(12) 0.0457(5) Uani 1 1 d . . . C1 C 0.5417(4) 0.37032(18) 0.67933(16) 0.0358(6) Uani 1 1 d . . . N1 N 0.4292(4) 0.41860(16) 0.60375(13) 0.0341(5) Uani 1 1 d . . . H1 H 0.501(5) 0.470(2) 0.5896(19) 0.055(9) Uiso 1 1 d . . . C11 C 0.7148(4) 0.42840(17) 0.74620(15) 0.0340(6) Uani 1 1 d . . . C12 C 0.9311(4) 0.38514(18) 0.79574(15) 0.0346(6) Uani 1 1 d . . . H12 H 0.9724 0.3206 0.7827 0.042 Uiso 1 1 calc R . . C13 C 1.0885(5) 0.43342(18) 0.86365(16) 0.0364(6) Uani 1 1 d . . . C14 C 1.0205(5) 0.52791(19) 0.88204(16) 0.0405(6) Uani 1 1 d . . . H14 H 1.1260 0.5627 0.9281 0.049 Uiso 1 1 calc R . . C15 C 0.8026(5) 0.57172(19) 0.83456(16) 0.0415(7) Uani 1 1 d . . . H15 H 0.7572 0.6355 0.8489 0.050 Uiso 1 1 calc R . . C16 C 0.6508(5) 0.52229(18) 0.76599(16) 0.0375(6) Uani 1 1 d . . . H16 H 0.5031 0.5525 0.7325 0.045 Uiso 1 1 calc R . . C17 C 1.3220(5) 0.38467(19) 0.91722(17) 0.0422(7) Uani 1 1 d . . . H12A H 1.4751 0.4271 0.9209 0.063 Uiso 0.67 1 calc PR . . H12B H 1.3594 0.3246 0.8875 0.063 Uiso 0.67 1 calc PR . . H12C H 1.2832 0.3707 0.9780 0.063 Uiso 0.67 1 calc PR . . H12D H 1.2700 0.3212 0.9367 0.063 Uiso 0.33 1 calc PR . . H12E H 1.3857 0.4237 0.9701 0.063 Uiso 0.33 1 calc PR . . H12F H 1.4619 0.3775 0.8796 0.063 Uiso 0.33 1 calc PR . . C21 C 0.2259(4) 0.38361(17) 0.53981(15) 0.0333(6) Uani 1 1 d . . . N22 N 0.2140(4) 0.42166(14) 0.45778(13) 0.0358(5) Uani 1 1 d . . . C23 C 0.0136(4) 0.39396(19) 0.39581(17) 0.0395(6) Uani 1 1 d . . . H23 H 0.0015 0.4211 0.3373 0.047 Uiso 1 1 calc R . . C24 C -0.1762(5) 0.32817(18) 0.41220(17) 0.0390(6) Uani 1 1 d . . . H24 H -0.3133 0.3099 0.3662 0.047 Uiso 1 1 calc R . . C25 C -0.1587(5) 0.28994(18) 0.49815(17) 0.0394(7) Uani 1 1 d . . . H25 H -0.2859 0.2450 0.5122 0.047 Uiso 1 1 calc R . . C26 C 0.0437(4) 0.31730(17) 0.56311(16) 0.0358(6) Uani 1 1 d . . . H26 H 0.0587 0.2917 0.6223 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0497(11) 0.0361(11) 0.0488(12) 0.0051(8) -0.0017(8) -0.0057(8) C1 0.0357(13) 0.0366(15) 0.0348(14) 0.0010(11) 0.0034(10) 0.0022(11) N1 0.0370(11) 0.0332(12) 0.0313(12) 0.0009(9) 0.0015(9) -0.0037(9) C11 0.0357(13) 0.0345(14) 0.0318(13) 0.0035(11) 0.0053(10) -0.0027(11) C12 0.0372(13) 0.0337(13) 0.0335(14) 0.0024(11) 0.0064(10) -0.0004(11) C13 0.0378(14) 0.0423(15) 0.0295(13) 0.0011(11) 0.0056(10) -0.0045(11) C14 0.0446(15) 0.0414(15) 0.0341(14) -0.0027(11) 0.0002(11) -0.0039(12) C15 0.0512(15) 0.0358(15) 0.0373(15) -0.0006(12) 0.0050(12) -0.0006(12) C16 0.0408(14) 0.0391(15) 0.0331(14) 0.0031(11) 0.0064(10) -0.0006(11) C17 0.0404(14) 0.0501(17) 0.0349(15) 0.0023(12) 0.0014(11) 0.0016(12) C21 0.0343(13) 0.0355(14) 0.0304(14) -0.0010(11) 0.0053(10) 0.0045(11) N22 0.0369(11) 0.0401(12) 0.0299(11) -0.0020(9) 0.0031(9) -0.0011(9) C23 0.0397(14) 0.0455(15) 0.0333(14) 0.0003(12) 0.0054(11) 0.0014(12) C24 0.0355(13) 0.0387(15) 0.0416(15) -0.0021(12) 0.0011(11) -0.0004(11) C25 0.0365(14) 0.0373(15) 0.0442(16) -0.0006(12) 0.0044(11) -0.0019(11) C26 0.0365(13) 0.0353(14) 0.0359(14) 0.0018(11) 0.0063(10) 0.0013(11) _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 C1 1.228(3) . ? C1 N1 1.375(3) . ? C1 C11 1.485(3) . ? N1 C21 1.405(3) . ? N1 H1 0.84(3) . ? C11 C12 1.387(3) . ? C11 C16 1.390(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.399(3) . ? C13 C17 1.511(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H12A 0.9800 . ? C17 H12B 0.9800 . ? C17 H12C 0.9800 . ? C17 H12D 0.9800 . ? C17 H12E 0.9800 . ? C17 H12F 0.9800 . ? C21 N22 1.334(3) . ? C21 C26 1.395(3) . ? N22 C23 1.345(3) . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C24 C25 1.386(3) . ? C24 H24 0.9500 . ? C25 C26 1.378(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 O1 C1 N1 123.0(2) . . ? O1 C1 C11 121.1(2) . . ? N1 C1 C11 115.8(2) . . ? C1 N1 C21 125.6(2) . . ? C1 N1 H1 118.1(19) . . ? C21 N1 H1 115.6(19) . . ? C12 C11 C16 119.3(2) . . ? C12 C11 C1 119.1(2) . . ? C16 C11 C1 121.2(2) . . ? C13 C12 C11 121.8(2) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 117.7(2) . . ? C12 C13 C17 120.9(2) . . ? C14 C13 C17 121.3(2) . . ? C15 C14 C13 121.3(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 119.7(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C11 120.0(2) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C13 C17 H12A 109.5 . . ? C13 C17 H12B 109.5 . . ? H12A C17 H12B 109.5 . . ? C13 C17 H12C 109.5 . . ? H12A C17 H12C 109.5 . . ? H12B C17 H12C 109.5 . . ? C13 C17 H12D 109.5 . . ? H12A C17 H12D 141.1 . . ? H12B C17 H12D 56.3 . . ? H12C C17 H12D 56.3 . . ? C13 C17 H12E 109.5 . . ? H12A C17 H12E 56.3 . . ? H12B C17 H12E 141.1 . . ? H12C C17 H12E 56.3 . . ? H12D C17 H12E 109.5 . . ? C13 C17 H12F 109.5 . . ? H12A C17 H12F 56.3 . . ? H12B C17 H12F 56.3 . . ? H12C C17 H12F 141.1 . . ? H12D C17 H12F 109.5 . . ? H12E C17 H12F 109.5 . . ? N22 C21 C26 123.2(2) . . ? N22 C21 N1 115.3(2) . . ? C26 C21 N1 121.4(2) . . ? C21 N22 C23 117.1(2) . . ? N22 C23 C24 124.0(2) . . ? N22 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C23 C24 C25 117.6(2) . . ? C23 C24 H24 121.2 . . ? C25 C24 H24 121.2 . . ? C26 C25 C24 119.8(2) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C21 118.3(2) . . ? C25 C26 H26 120.8 . . ? C21 C26 H26 120.8 . . ? 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 O1 C1 N1 C21 10.2(4) . . . . ? C11 C1 N1 C21 -168.23(19) . . . . ? O1 C1 C11 C12 34.9(3) . . . . ? N1 C1 C11 C12 -146.6(2) . . . . ? O1 C1 C11 C16 -139.0(2) . . . . ? N1 C1 C11 C16 39.5(3) . . . . ? C16 C11 C12 C13 -1.1(3) . . . . ? C1 C11 C12 C13 -175.1(2) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? C11 C12 C13 C17 179.6(2) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C17 C13 C14 C15 -178.3(2) . . . . ? C13 C14 C15 C16 -1.5(4) . . . . ? C14 C15 C16 C11 1.2(4) . . . . ? C12 C11 C16 C15 0.0(3) . . . . ? C1 C11 C16 C15 173.9(2) . . . . ? C1 N1 C21 N22 -155.1(2) . . . . ? C1 N1 C21 C26 28.0(3) . . . . ? C26 C21 N22 C23 0.4(3) . . . . ? N1 C21 N22 C23 -176.5(2) . . . . ? C21 N22 C23 C24 -0.8(4) . . . . ? N22 C23 C24 C25 0.9(4) . . . . ? C23 C24 C25 C26 -0.5(4) . . . . ? C24 C25 C26 C21 0.2(4) . . . . ? N22 C21 C26 C25 -0.1(4) . . . . ? N1 C21 C26 C25 176.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.84(3) 2.29(3) 3.106(3) 164(3) 3_666 yes C15 H15 O1 0.95 2.50 3.352(3) 149.2 2_656 yes C26 H26 O1 0.95 2.37 2.869(3) 112 . yes C23 H23 Cg1 0.95 2.84 3.749(3) 161 3_666 yes # Cg1 is the C~6~ aromatic ring centroid located at 3_666. # Complete details for the C23-H23...\p(arene) interaction. # C23 H23 C11 0.95 2.93 3.666(3) 135.0 3_666 # C23 H23 C12 0.95 3.40 4.246(3) 149.2 3_666 # C23 H23 C14 0.95 3.35 4.289(3) 168.6 3_666 # C23 H23 C15 0.95 2.90 3.739(3) 148.2 3_666 # C23 H23 C16 0.95 2.65 3.377(3) 134.2 3_666 #========================================================= data_Moo-[9-10] _database_code_depnum_ccdc_archive 'CCDC 765532' #TrackingRef 'Mxx-9cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Moo _chemical_melting_point 389 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2376(4) _cell_length_b 8.5035(6) _cell_length_c 9.0024(5) _cell_angle_alpha 92.327(3) _cell_angle_beta 97.349(3) _cell_angle_gamma 95.259(3) _cell_volume 546.42(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2520 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 3843 _diffrn_standards_decay_% ? _diffrn_reflns_number 5136 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.049 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _reflns_number_total 2467 _reflns_number_gt 1785 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.1186P)^2^] 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 2467 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1844 _refine_ls_wR_factor_gt 0.1627 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.43 _refine_diff_density_min -0.29 _refine_diff_density_rms 0.06 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 0.73771(17) 0.64058(16) 0.45208(13) 0.0378(4) Uani 1 1 d . . . C1 C 0.6267(2) 0.6536(2) 0.33988(18) 0.0284(4) Uani 1 1 d . . . N1 N 0.6234(2) 0.56880(17) 0.20768(16) 0.0305(4) Uani 1 1 d . . . H1 H 0.529(3) 0.580(2) 0.136(2) 0.035(5) Uiso 1 1 d . . . C11 C 0.4798(2) 0.7672(2) 0.34172(18) 0.0284(4) Uani 1 1 d . . . C12 C 0.5048(2) 0.9151(2) 0.28014(18) 0.0313(4) Uani 1 1 d . . . C13 C 0.3699(2) 1.0205(2) 0.29443(19) 0.0347(4) Uani 1 1 d . . . H13A H 0.3849 1.1222 0.2551 0.042 Uiso 1 1 calc R . . C14 C 0.2147(2) 0.9789(2) 0.3649(2) 0.0374(5) Uani 1 1 d . . . H14 H 0.1240 1.0518 0.3726 0.045 Uiso 1 1 calc R . . C15 C 0.1906(2) 0.8324(2) 0.4241(2) 0.0363(4) Uani 1 1 d . . . H15 H 0.0830 0.8040 0.4713 0.044 Uiso 1 1 calc R . . C16 C 0.3244(2) 0.7267(2) 0.41434(19) 0.0326(4) Uani 1 1 d . . . H16 H 0.3101 0.6268 0.4572 0.039 Uiso 1 1 calc R . . C17 C 0.6707(3) 0.9624(2) 0.2009(2) 0.0430(5) Uani 1 1 d . . . H17A H 0.7804 0.9149 0.2481 0.064 Uiso 1 1 calc R . . H17B H 0.6963 1.0778 0.2080 0.064 Uiso 1 1 calc R . . H17C H 0.6435 0.9253 0.0952 0.064 Uiso 1 1 calc R . . C21 C 0.7551(2) 0.46601(19) 0.16984(17) 0.0266(4) Uani 1 1 d . . . N22 N 0.71020(19) 0.39533(17) 0.03275(15) 0.0303(4) Uani 1 1 d . . . C23 C 0.8334(2) 0.3021(2) -0.01485(18) 0.0331(4) Uani 1 1 d . . . H23 H 0.8038 0.2510 -0.1119 0.040 Uiso 1 1 calc R . . C24 C 1.0003(2) 0.2759(2) 0.06877(18) 0.0334(4) Uani 1 1 d . . . H24 H 1.0834 0.2092 0.0303 0.040 Uiso 1 1 calc R . . C25 C 1.0429(2) 0.3500(2) 0.21047(19) 0.0321(4) Uani 1 1 d . . . H25 H 1.1566 0.3349 0.2712 0.038 Uiso 1 1 calc R . . C26 C 0.9188(2) 0.4459(2) 0.26286(18) 0.0314(4) Uani 1 1 d . . . H26 H 0.9447 0.4970 0.3601 0.038 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 0.0399(7) 0.0427(8) 0.0299(6) -0.0026(5) -0.0041(5) 0.0136(6) C1 0.0280(8) 0.0292(9) 0.0270(8) 0.0013(7) 0.0015(6) 0.0015(7) N1 0.0282(7) 0.0355(9) 0.0270(7) -0.0027(6) -0.0022(6) 0.0093(6) C11 0.0282(8) 0.0286(9) 0.0276(8) -0.0025(7) 0.0011(6) 0.0040(7) C12 0.0308(8) 0.0331(10) 0.0293(8) 0.0010(7) 0.0015(7) 0.0034(7) C13 0.0354(9) 0.0276(9) 0.0406(10) 0.0015(7) 0.0012(8) 0.0053(7) C14 0.0336(9) 0.0367(11) 0.0420(10) -0.0051(8) 0.0034(8) 0.0095(8) C15 0.0314(9) 0.0416(11) 0.0365(10) -0.0031(8) 0.0084(7) 0.0034(8) C16 0.0337(8) 0.0318(10) 0.0320(9) 0.0008(7) 0.0043(7) 0.0012(7) C17 0.0392(10) 0.0424(12) 0.0501(11) 0.0105(9) 0.0120(9) 0.0070(9) C21 0.0263(8) 0.0264(9) 0.0269(8) 0.0022(6) 0.0026(6) 0.0027(6) N22 0.0285(7) 0.0326(8) 0.0298(7) -0.0004(6) 0.0028(6) 0.0063(6) C23 0.0331(9) 0.0371(10) 0.0290(9) -0.0024(7) 0.0024(7) 0.0071(7) C24 0.0316(9) 0.0359(10) 0.0342(9) 0.0011(8) 0.0052(7) 0.0100(7) C25 0.0263(8) 0.0359(10) 0.0336(9) 0.0034(7) 0.0007(7) 0.0052(7) C26 0.0316(8) 0.0347(10) 0.0273(8) -0.0003(7) 0.0009(7) 0.0059(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2233(19) . ? C1 N1 1.363(2) . ? C1 C11 1.501(2) . ? N1 C21 1.414(2) . ? N1 H1 0.90(2) . ? C11 C16 1.395(2) . ? C11 C12 1.401(2) . ? C12 C13 1.399(2) . ? C12 C17 1.505(2) . ? C13 C14 1.385(3) . ? C13 H13A 0.9500 . ? C14 C15 1.380(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 N22 1.338(2) . ? C21 C26 1.389(2) . ? N22 C23 1.344(2) . ? C23 C24 1.381(2) . ? C23 H23 0.9500 . ? C24 C25 1.385(2) . ? C24 H24 0.9500 . ? C25 C26 1.381(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 O1 C1 N1 124.26(15) . . ? O1 C1 C11 120.44(14) . . ? N1 C1 C11 115.30(14) . . ? C1 N1 C21 127.25(14) . . ? C1 N1 H1 117.0(12) . . ? C21 N1 H1 115.8(12) . . ? C16 C11 C12 120.75(15) . . ? C16 C11 C1 118.72(15) . . ? C12 C11 C1 120.40(14) . . ? C13 C12 C11 117.93(15) . . ? C13 C12 C17 119.96(16) . . ? C11 C12 C17 122.12(15) . . ? C14 C13 C12 121.05(17) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C15 C14 C13 120.56(16) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.60(16) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 120.09(16) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N22 C21 C26 123.36(14) . . ? N22 C21 N1 113.23(13) . . ? C26 C21 N1 123.35(15) . . ? C21 N22 C23 116.89(14) . . ? N22 C23 C24 124.01(16) . . ? N22 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C23 C24 C25 117.87(16) . . ? C23 C24 H24 121.1 . . ? C25 C24 H24 121.1 . . ? C26 C25 C24 119.51(15) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 118.35(15) . . ? C25 C26 H26 120.8 . . ? C21 C26 H26 120.8 . . ? 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 O1 C1 N1 C21 -7.4(3) . . . . ? C11 C1 N1 C21 173.29(14) . . . . ? O1 C1 C11 C16 -75.7(2) . . . . ? N1 C1 C11 C16 103.64(17) . . . . ? O1 C1 C11 C12 100.19(19) . . . . ? N1 C1 C11 C12 -80.5(2) . . . . ? C16 C11 C12 C13 0.3(2) . . . . ? C1 C11 C12 C13 -175.55(14) . . . . ? C16 C11 C12 C17 -179.93(15) . . . . ? C1 C11 C12 C17 4.3(2) . . . . ? C11 C12 C13 C14 -1.1(3) . . . . ? C17 C12 C13 C14 179.08(16) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C11 -1.6(3) . . . . ? C12 C11 C16 C15 1.1(3) . . . . ? C1 C11 C16 C15 176.97(16) . . . . ? C1 N1 C21 N22 177.87(15) . . . . ? C1 N1 C21 C26 -4.9(3) . . . . ? C26 C21 N22 C23 -0.7(3) . . . . ? N1 C21 N22 C23 176.59(13) . . . . ? C21 N22 C23 C24 0.1(3) . . . . ? N22 C23 C24 C25 0.2(3) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C24 C25 C26 C21 -0.7(3) . . . . ? N22 C21 C26 C25 1.0(3) . . . . ? N1 C21 C26 C25 -176.01(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.90(2) 2.18(2) 3.076(2) 177.6(16) 2_665 yes C16 H16 O1 0.95 2.46 3.405(2) 175 2_666 yes C25 H25 O1 0.95 2.51 3.237(2) 134 2_766 yes C26 H26 O1 0.95 2.23 2.846(2) 121 . yes C23 H23 Cg1 0.95 2.46 3.3875(18) 167 2_665 yes # Cg1 is the C~6~ aromatic ring centroid located at site 2_665 # Complete details for the C-H...\p(arene) interaction (not normalised) # C23 H23 C11 0.95 2.71 3.472(2) 137.6 2_665 # C23 H23 C12 0.95 2.77 3.525(2) 137.2 2_665 # C23 H23 C13 0.95 2.87 3.711(2) 148.1 2_665 # C23 H23 C14 0.95 2.92 3.836(3) 161.8 2_665 # C23 H23 C15 0.95 2.88 3.791(2) 161.8 2_665 # C23 H23 C16 0.95 2.78 3.623(2) 148.1 2_665 #=========================================================