Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Zofia Urbanczyk-Lipkowska' _publ_contact_author_address ; Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka Str. 44/52 Warsaw 01-224 POLAND ; _publ_contact_author_email OCRYST@ICHO.EDU.PL _publ_section_title ; New crystalline form of 7-amino-4-methylcoumarin (coumarin 120) - a polymorph with (1:1) valence tautomers ; loop_ _publ_author_name 'Zofia Urbanczyk-Lipkowska' 'Dorota Niedzialek' data_C120_I _database_code_depnum_ccdc_archive 'CCDC 646960' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9 N O2' _chemical_formula_sum 'C10 H9 N O2' _chemical_formula_weight 175.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7981(8) _cell_length_b 7.1085(9) _cell_length_c 9.5555(10) _cell_angle_alpha 71.489(11) _cell_angle_beta 84.540(9) _cell_angle_gamma 69.982(12) _cell_volume 411.37(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10000 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 29.7 _exptl_crystal_description Planar _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 1024 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count '50 frames' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 4808 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1451 _reflns_number_gt 793 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisCCD _computing_cell_refinement CrysAlisRED _computing_data_reduction CrysAlisRED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2' _computing_publication_material SHELXTL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0292P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1451 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0546 _refine_ls_goodness_of_fit_ref 0.740 _refine_ls_restrained_S_all 0.740 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.6638(3) 0.5986(3) 0.80564(18) 0.0190(4) Uani 1 1 d . . . C3 C 0.7484(3) 0.3756(3) 0.83474(18) 0.0178(4) Uani 1 1 d . . . C4 C 0.8014(2) 0.2854(3) 0.72560(17) 0.0159(4) Uani 1 1 d . . . C5 C 0.8160(3) 0.3444(3) 0.44937(18) 0.0177(4) Uani 1 1 d . . . C6 C 0.7834(3) 0.4808(3) 0.30844(18) 0.0178(4) Uani 1 1 d . . . C7 C 0.7050(2) 0.6997(3) 0.28410(17) 0.0162(4) Uani 1 1 d . . . C8 C 0.6619(3) 0.7746(3) 0.40564(18) 0.0166(4) Uani 1 1 d . . . C9 C 0.6950(2) 0.6335(3) 0.54523(16) 0.0154(4) Uani 1 1 d . . . C10 C 0.7731(2) 0.4160(3) 0.57471(16) 0.0146(4) Uani 1 1 d . . . C12 C 0.8899(3) 0.0505(3) 0.7615(2) 0.0214(5) Uani 1 1 d . . . N13 N 0.6762(2) 0.8375(3) 0.14319(16) 0.0226(4) Uani 1 1 d . . . O1 O 0.64413(17) 0.72174(17) 0.65972(11) 0.0181(3) Uani 1 1 d . . . O2 O 0.60704(18) 0.69563(18) 0.89609(12) 0.0259(3) Uani 1 1 d . . . H5 H 0.873(2) 0.193(2) 0.4620(14) 0.014(4) Uiso 1 1 d . . . H3 H 0.760(2) 0.293(2) 0.9396(15) 0.017(4) Uiso 1 1 d . . . H8 H 0.603(2) 0.924(2) 0.3906(14) 0.012(4) Uiso 1 1 d . . . H6 H 0.815(2) 0.425(2) 0.2210(14) 0.010(4) Uiso 1 1 d . . . H12A H 0.893(2) -0.020(2) 0.8705(18) 0.030(5) Uiso 1 1 d . . . H13B H 0.675(2) 0.781(2) 0.0688(16) 0.023(5) Uiso 1 1 d . . . H12C H 0.809(2) -0.002(2) 0.7134(17) 0.035(5) Uiso 1 1 d . . . H12B H 1.034(3) 0.012(2) 0.7224(16) 0.033(5) Uiso 1 1 d . . . H13A H 0.594(3) 0.976(3) 0.1345(19) 0.046(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0179(10) 0.0244(11) 0.0176(10) -0.0063(9) 0.0017(8) -0.0111(9) C3 0.0201(10) 0.0190(12) 0.0148(10) -0.0041(9) 0.0013(8) -0.0082(9) C4 0.0109(9) 0.0172(11) 0.0202(9) -0.0048(8) 0.0010(8) -0.0064(8) C5 0.0162(10) 0.0168(12) 0.0224(10) -0.0103(9) 0.0013(8) -0.0044(9) C6 0.0169(10) 0.0232(12) 0.0167(10) -0.0119(9) 0.0020(8) -0.0059(9) C7 0.0113(9) 0.0210(11) 0.0169(10) -0.0056(9) -0.0005(8) -0.0060(8) C8 0.0145(10) 0.0139(11) 0.0209(10) -0.0064(9) 0.0015(8) -0.0035(9) C9 0.0137(10) 0.0225(12) 0.0150(10) -0.0122(9) 0.0033(8) -0.0070(9) C10 0.0105(10) 0.0161(12) 0.0192(10) -0.0074(8) 0.0017(8) -0.0055(8) C12 0.0257(12) 0.0178(12) 0.0204(11) -0.0055(9) 0.0021(9) -0.0076(9) N13 0.0267(9) 0.0245(11) 0.0163(9) -0.0081(8) -0.0006(7) -0.0060(8) O1 0.0225(7) 0.0162(7) 0.0161(6) -0.0075(5) 0.0018(5) -0.0051(6) O2 0.0374(8) 0.0254(8) 0.0195(7) -0.0132(6) 0.0051(6) -0.0111(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O2 1.226(2) . ? C2 O1 1.3814(18) . ? C2 C3 1.431(2) . ? C3 C4 1.350(2) . ? C3 H3 0.982(13) . ? C4 C10 1.435(2) . ? C4 C12 1.502(2) . ? C5 C6 1.372(2) . ? C5 C10 1.413(2) . ? C5 H5 0.982(14) . ? C6 C7 1.409(2) . ? C6 H6 1.009(13) . ? C7 N13 1.376(2) . ? C7 C8 1.393(2) . ? C8 C9 1.374(2) . ? C8 H8 0.965(14) . ? C9 O1 1.3874(17) . ? C9 C10 1.393(2) . ? C12 H12A 1.000(15) . ? C12 H12C 0.977(16) . ? C12 H12B 0.995(16) . ? N13 H13B 0.921(16) . ? N13 H13A 0.931(18) . ? 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 O2 C2 O1 115.23(16) . . ? O2 C2 C3 127.43(16) . . ? O1 C2 C3 117.34(16) . . ? C4 C3 C2 122.30(17) . . ? C4 C3 H3 122.5(9) . . ? C2 C3 H3 115.1(8) . . ? C3 C4 C10 119.42(18) . . ? C3 C4 C12 120.41(16) . . ? C10 C4 C12 120.17(16) . . ? C6 C5 C10 121.98(18) . . ? C6 C5 H5 118.2(8) . . ? C10 C5 H5 119.8(8) . . ? C5 C6 C7 120.50(17) . . ? C5 C6 H6 120.2(8) . . ? C7 C6 H6 119.3(8) . . ? N13 C7 C8 120.39(18) . . ? N13 C7 C6 120.86(16) . . ? C8 C7 C6 118.74(16) . . ? C9 C8 C7 119.22(18) . . ? C9 C8 H8 121.1(8) . . ? C7 C8 H8 119.6(8) . . ? C8 C9 O1 115.36(16) . . ? C8 C9 C10 124.08(16) . . ? O1 C9 C10 120.56(14) . . ? C9 C10 C5 115.48(15) . . ? C9 C10 C4 118.72(16) . . ? C5 C10 C4 125.80(16) . . ? C4 C12 H12A 111.1(9) . . ? C4 C12 H12C 111.2(10) . . ? H12A C12 H12C 109.0(12) . . ? C4 C12 H12B 108.8(9) . . ? H12A C12 H12B 109.8(12) . . ? H12C C12 H12B 106.8(13) . . ? C7 N13 H13B 116.0(10) . . ? C7 N13 H13A 115.9(11) . . ? H13B N13 H13A 120.2(15) . . ? C2 O1 C9 121.61(14) . . ? 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 O2 C2 C3 C4 178.45(17) . . . . ? O1 C2 C3 C4 -2.1(2) . . . . ? C2 C3 C4 C10 0.1(2) . . . . ? C2 C3 C4 C12 179.93(16) . . . . ? C10 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 N13 178.60(16) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? N13 C7 C8 C9 -179.06(16) . . . . ? C6 C7 C8 C9 -0.6(2) . . . . ? C7 C8 C9 O1 -178.81(14) . . . . ? C7 C8 C9 C10 1.0(2) . . . . ? C8 C9 C10 C5 -0.8(2) . . . . ? O1 C9 C10 C5 178.97(14) . . . . ? C8 C9 C10 C4 179.76(16) . . . . ? O1 C9 C10 C4 -0.5(2) . . . . ? C6 C5 C10 C9 0.3(2) . . . . ? C6 C5 C10 C4 179.71(17) . . . . ? C3 C4 C10 C9 1.2(2) . . . . ? C12 C4 C10 C9 -178.59(15) . . . . ? C3 C4 C10 C5 -178.18(16) . . . . ? C12 C4 C10 C5 2.0(2) . . . . ? O2 C2 O1 C9 -177.63(14) . . . . ? C3 C2 O1 C9 2.9(2) . . . . ? C8 C9 O1 C2 178.13(15) . . . . ? C10 C9 O1 C2 -1.6(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 N13 H13B O2 0.921(16) 2.070(17) 2.977(2) 167.7(14) 1_554 N13 H13A O2 0.931(18) 2.205(19) 3.136(2) 177.0(16) 2_676 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.154 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.038 # Attachment 'C120_II.CIF' data_C120_II _database_code_depnum_ccdc_archive 'CCDC 646961' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-amino-4-methylcoumarin ; _chemical_name_common 7-amino-4-methylcoumarin _chemical_melting_point 221-223 _chemical_formula_moiety 'C10 H9 N O2' _chemical_formula_sum 'C10 H9 N O2' _chemical_formula_weight 175.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.7381(10) _cell_length_b 25.655(3) _cell_length_c 13.6416(14) _cell_angle_alpha 90.00 _cell_angle_beta 105.040(9) _cell_angle_gamma 90.00 _cell_volume 3291.3(6) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10000 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 29.7 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 1024 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count '50 frames' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 8076 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2821 _reflns_number_gt 1538 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisCCD _computing_cell_refinement CrysAlisRED _computing_data_reduction CrysAlisRED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2' _computing_publication_material SHELXTL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2821 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1079 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 C2 C 0.6984(2) 0.05461(9) 1.0598(2) 0.0194(6) Uani 1 1 d . . . C3 C 0.6703(3) 0.05685(9) 0.9527(2) 0.0206(7) Uani 1 1 d . . . H3 H 0.5763 0.0552 0.9144 0.025 Uiso 1 1 calc R . . C4 C 0.7747(3) 0.06128(9) 0.9031(2) 0.0186(7) Uani 1 1 d . . . C5 C 1.0413(2) 0.06821(9) 0.9244(2) 0.0204(7) Uani 1 1 d . . . H5 H 1.0289 0.0697 0.8545 0.024 Uiso 1 1 calc R . . C6 C 1.1757(2) 0.07011(10) 0.9863(2) 0.0211(7) Uani 1 1 d . . . H6 H 1.2526 0.0727 0.9580 0.025 Uiso 1 1 calc R . . C7 C 1.1998(2) 0.06827(9) 1.0924(2) 0.0164(6) Uani 1 1 d . . . C8 C 1.0824(2) 0.06502(9) 1.1330(2) 0.0187(6) Uani 1 1 d . . . H8 H 1.0946 0.0646 1.2029 0.022 Uiso 1 1 calc R . . C9 C 0.9488(3) 0.06245(9) 1.0683(2) 0.0184(7) Uani 1 1 d . . . C10 C 0.9201(3) 0.06403(9) 0.9625(2) 0.0182(7) Uani 1 1 d . . . C12 C 0.7414(3) 0.06312(9) 0.7892(2) 0.0251(7) Uani 1 1 d . . . H12A H 0.6402 0.0625 0.7613 0.038 Uiso 1 1 calc R . . H12B H 0.7830 0.0335 0.7650 0.038 Uiso 1 1 calc R . . H12C H 0.7797 0.0945 0.7686 0.038 Uiso 1 1 calc R . . C15 C 0.6964(2) 0.31295(9) 1.06275(19) 0.0171(6) Uani 1 1 d . . . C16 C 0.6667(2) 0.31349(9) 0.9548(2) 0.0194(6) Uani 1 1 d . . . H16 H 0.5722 0.3138 0.9172 0.023 Uiso 1 1 calc R . . C17 C 0.7708(2) 0.31352(9) 0.90400(19) 0.0173(6) Uani 1 1 d . . . C18 C 1.0362(2) 0.31243(10) 0.92221(19) 0.0196(6) Uani 1 1 d . . . H18 H 1.0224 0.3127 0.8522 0.024 Uiso 1 1 calc R . . C19 C 1.1721(3) 0.31122(10) 0.9840(2) 0.0208(7) Uani 1 1 d . . . H19 H 1.2486 0.3104 0.9550 0.025 Uiso 1 1 calc R . . C20 C 1.1979(2) 0.31122(9) 1.0906(2) 0.0182(6) Uani 1 1 d . . . C21 C 1.0807(2) 0.31202(9) 1.1322(2) 0.0187(6) Uani 1 1 d . . . H21 H 1.0939 0.3119 1.2022 0.022 Uiso 1 1 calc R . . C22 C 0.9460(2) 0.31301(9) 1.06827(19) 0.0157(6) Uani 1 1 d . . . C23 C 0.9171(2) 0.31328(10) 0.96286(19) 0.0163(6) Uani 1 1 d . . . C25 C 0.7350(2) 0.31370(10) 0.79116(19) 0.0238(6) Uani 1 1 d . . . H25A H 0.6337 0.3150 0.7646 0.036 Uiso 1 1 calc R . . H25B H 0.7712 0.2826 0.7678 0.036 Uiso 1 1 calc R . . H25C H 0.7772 0.3436 0.7683 0.036 Uiso 1 1 calc R . . N13 N 1.3343(2) 0.07034(9) 1.1557(2) 0.0232(6) Uani 1 1 d . . . H13A H 1.346(3) 0.0601(9) 1.222(2) 0.038(9) Uiso 1 1 d . . . H13B H 1.404(3) 0.0655(8) 1.1238(19) 0.021(7) Uiso 1 1 d . . . N26 N 1.3312(2) 0.31000(10) 1.1528(2) 0.0233(6) Uani 1 1 d . . . H26A H 1.344(3) 0.3129(9) 1.223(2) 0.033(8) Uiso 1 1 d . . . H26B H 1.400(3) 0.3113(11) 1.136(2) 0.053(10) Uiso 1 1 d . . . O1 O 0.83881(17) 0.05759(6) 1.11562(14) 0.0201(5) Uani 1 1 d . . . O11 O 0.61261(18) 0.05013(6) 1.11061(14) 0.0262(5) Uani 1 1 d . . . O14 O 0.83671(16) 0.31324(6) 1.11650(13) 0.0178(4) Uani 1 1 d . . . O24 O 0.61107(17) 0.31221(6) 1.11409(14) 0.0218(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0095(13) 0.0238(14) 0.0254(19) -0.0011(12) 0.0053(13) 0.0020(10) C3 0.0091(13) 0.0245(15) 0.0266(19) -0.0017(12) 0.0019(12) 0.0004(10) C4 0.0152(13) 0.0186(14) 0.0194(18) -0.0014(11) -0.0001(12) 0.0013(11) C5 0.0198(15) 0.0238(14) 0.0210(18) -0.0008(12) 0.0115(13) -0.0006(11) C6 0.0083(13) 0.0220(15) 0.035(2) 0.0001(13) 0.0097(13) -0.0023(10) C7 0.0122(14) 0.0151(13) 0.0202(18) 0.0004(11) 0.0010(13) -0.0017(10) C8 0.0120(14) 0.0242(15) 0.0189(18) -0.0020(12) 0.0023(12) -0.0004(10) C9 0.0152(15) 0.0186(14) 0.0243(19) -0.0001(11) 0.0103(14) 0.0022(10) C10 0.0152(14) 0.0201(14) 0.0195(19) 0.0001(11) 0.0048(12) 0.0011(10) C12 0.0128(13) 0.0341(16) 0.0255(19) 0.0009(13) -0.0004(13) 0.0000(11) C15 0.0095(12) 0.0188(12) 0.0212(17) 0.0006(13) 0.0010(11) 0.0011(11) C16 0.0082(12) 0.0210(13) 0.0253(17) 0.0009(13) -0.0024(11) 0.0007(11) C17 0.0160(12) 0.0150(12) 0.0206(16) -0.0005(13) 0.0042(11) -0.0014(12) C18 0.0196(13) 0.0241(14) 0.0162(15) 0.0000(13) 0.0065(11) -0.0019(12) C19 0.0178(13) 0.0245(14) 0.0243(18) -0.0014(13) 0.0133(13) -0.0018(12) C20 0.0104(13) 0.0205(13) 0.0241(17) 0.0005(13) 0.0055(12) -0.0005(11) C21 0.0131(13) 0.0245(14) 0.0192(16) 0.0012(14) 0.0051(11) -0.0014(12) C22 0.0081(12) 0.0195(13) 0.0214(16) 0.0002(13) 0.0074(11) -0.0010(12) C23 0.0128(12) 0.0165(13) 0.0194(16) -0.0011(13) 0.0036(11) -0.0020(11) C25 0.0172(13) 0.0327(14) 0.0193(16) 0.0012(14) 0.0008(12) 0.0013(13) N13 0.0108(12) 0.0343(14) 0.0257(17) -0.0004(12) 0.0070(12) -0.0002(10) N26 0.0045(11) 0.0405(15) 0.0255(16) -0.0014(13) 0.0050(11) 0.0008(10) O1 0.0068(9) 0.0305(11) 0.0233(13) -0.0001(8) 0.0044(8) -0.0003(7) O11 0.0119(9) 0.0426(11) 0.0256(13) 0.0014(9) 0.0074(9) 0.0014(8) O14 0.0060(8) 0.0283(9) 0.0201(11) -0.0013(9) 0.0052(8) 0.0005(8) O24 0.0098(8) 0.0318(10) 0.0262(11) 0.0017(9) 0.0090(8) 0.0014(8) _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 C2 O11 1.222(3) . ? C2 O1 1.384(3) . ? C2 C3 1.416(4) . ? C3 C4 1.364(3) . ? C3 H3 0.9300 . ? C4 C10 1.439(3) . ? C4 C12 1.503(4) . ? C5 C6 1.362(3) . ? C5 C10 1.413(3) . ? C5 H5 0.9300 . ? C6 C7 1.405(3) . ? C6 H6 0.9300 . ? C7 N13 1.369(3) . ? C7 C8 1.397(3) . ? C8 C9 1.372(4) . ? C8 H8 0.9300 . ? C9 O1 1.392(3) . ? C9 C10 1.397(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C15 O24 1.218(3) . ? C15 O14 1.373(3) . ? C15 C16 1.425(3) . ? C16 C17 1.369(3) . ? C16 H16 0.9300 . ? C17 C23 1.442(3) . ? C17 C25 1.487(3) . ? C18 C19 1.372(3) . ? C18 C23 1.410(3) . ? C18 H18 0.9300 . ? C19 C20 1.410(3) . ? C19 H19 0.9300 . ? C20 N26 1.355(3) . ? C20 C21 1.400(3) . ? C21 C22 1.374(3) . ? C21 H21 0.9300 . ? C22 O14 1.389(2) . ? C22 C23 1.392(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? N13 H13A 0.92(3) . ? N13 H13B 0.90(2) . ? N26 H26A 0.94(3) . ? N26 H26B 0.77(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 C2 O1 114.6(3) . . ? O11 C2 C3 127.7(2) . . ? O1 C2 C3 117.7(2) . . ? C4 C3 C2 123.0(2) . . ? C4 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C3 C4 C10 118.4(3) . . ? C3 C4 C12 121.7(3) . . ? C10 C4 C12 119.8(2) . . ? C6 C5 C10 122.3(3) . . ? C6 C5 H5 118.8 . . ? C10 C5 H5 118.8 . . ? C5 C6 C7 121.0(2) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? N13 C7 C8 120.0(3) . . ? N13 C7 C6 121.7(2) . . ? C8 C7 C6 118.4(2) . . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 O1 114.9(2) . . ? C8 C9 C10 124.4(2) . . ? O1 C9 C10 120.6(2) . . ? C9 C10 C5 114.8(3) . . ? C9 C10 C4 119.0(2) . . ? C5 C10 C4 126.2(3) . . ? C4 C12 H12A 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O24 C15 O14 115.2(2) . . ? O24 C15 C16 127.5(2) . . ? O14 C15 C16 117.3(2) . . ? C17 C16 C15 123.0(2) . . ? C17 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? C16 C17 C23 118.2(2) . . ? C16 C17 C25 121.2(2) . . ? C23 C17 C25 120.6(2) . . ? C19 C18 C23 121.3(2) . . ? C19 C18 H18 119.4 . . ? C23 C18 H18 119.4 . . ? C18 C19 C20 121.2(2) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? N26 C20 C21 119.7(3) . . ? N26 C20 C19 122.1(2) . . ? C21 C20 C19 118.2(2) . . ? C22 C21 C20 119.1(3) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 O14 115.0(2) . . ? C21 C22 C23 124.1(2) . . ? O14 C22 C23 121.0(2) . . ? C22 C23 C18 116.1(2) . . ? C22 C23 C17 118.8(2) . . ? C18 C23 C17 125.1(2) . . ? C17 C25 H25A 109.5 . . ? C17 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C17 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C7 N13 H13A 117.6(17) . . ? C7 N13 H13B 113.8(17) . . ? H13A N13 H13B 121(2) . . ? C20 N26 H26A 119.5(16) . . ? C20 N26 H26B 125(3) . . ? H26A N26 H26B 114(3) . . ? C2 O1 C9 121.2(2) . . ? C15 O14 C22 121.73(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 C2 C3 C4 -179.2(2) . . . . ? O1 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 C10 -0.3(4) . . . . ? C2 C3 C4 C12 179.5(2) . . . . ? C10 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 N13 -179.7(2) . . . . ? C5 C6 C7 C8 -0.7(4) . . . . ? N13 C7 C8 C9 -179.4(2) . . . . ? C6 C7 C8 C9 1.6(4) . . . . ? C7 C8 C9 O1 178.0(2) . . . . ? C7 C8 C9 C10 -1.5(4) . . . . ? C8 C9 C10 C5 0.5(4) . . . . ? O1 C9 C10 C5 -179.03(19) . . . . ? C8 C9 C10 C4 -179.7(2) . . . . ? O1 C9 C10 C4 0.9(3) . . . . ? C6 C5 C10 C9 0.5(4) . . . . ? C6 C5 C10 C4 -179.4(3) . . . . ? C3 C4 C10 C9 -0.5(3) . . . . ? C12 C4 C10 C9 179.8(2) . . . . ? C3 C4 C10 C5 179.4(2) . . . . ? C12 C4 C10 C5 -0.4(4) . . . . ? O24 C15 C16 C17 -179.0(2) . . . . ? O14 C15 C16 C17 1.0(4) . . . . ? C15 C16 C17 C23 -0.4(4) . . . . ? C15 C16 C17 C25 179.5(2) . . . . ? C23 C18 C19 C20 -0.5(4) . . . . ? C18 C19 C20 N26 180.0(3) . . . . ? C18 C19 C20 C21 0.6(4) . . . . ? N26 C20 C21 C22 -179.7(2) . . . . ? C19 C20 C21 C22 -0.3(4) . . . . ? C20 C21 C22 O14 179.4(2) . . . . ? C20 C21 C22 C23 0.0(4) . . . . ? C21 C22 C23 C18 0.0(4) . . . . ? O14 C22 C23 C18 -179.3(2) . . . . ? C21 C22 C23 C17 179.0(3) . . . . ? O14 C22 C23 C17 -0.3(4) . . . . ? C19 C18 C23 C22 0.2(4) . . . . ? C19 C18 C23 C17 -178.7(3) . . . . ? C16 C17 C23 C22 0.0(4) . . . . ? C25 C17 C23 C22 -179.9(2) . . . . ? C16 C17 C23 C18 178.9(2) . . . . ? C25 C17 C23 C18 -1.0(4) . . . . ? O11 C2 O1 C9 179.6(2) . . . . ? C3 C2 O1 C9 -0.2(3) . . . . ? C8 C9 O1 C2 179.9(2) . . . . ? C10 C9 O1 C2 -0.5(3) . . . . ? O24 C15 O14 C22 178.7(2) . . . . ? C16 C15 O14 C22 -1.3(3) . . . . ? C21 C22 O14 C15 -178.4(2) . . . . ? C23 C22 O14 C15 1.0(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 N13 H13A O11 0.92(3) 2.23(3) 3.137(3) 169(2) 2_757 N13 H13B O11 0.90(2) 2.13(2) 2.976(3) 157(2) 1_655 N26 H26A O24 0.94(3) 2.15(3) 3.083(3) 174(2) 2_757 N26 H26B O24 0.77(3) 2.15(3) 2.908(3) 170(3) 1_655 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.313 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.054