#------------------------------------------------------------------------------ #$Date: 2014-10-25 18:23:10 +0100 (Sat, 25 Oct 2014) $ #$Revision: 125873 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/52/2105298.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2105298 loop_ _publ_author_name 'Bibila Mayaya Bisseyou, Yvon' 'Bouhmaida, Nouhza' 'Guillot, Benoit' 'Lecomte, Claude' 'Lugan, Noel' 'Ghermani, Noureddine' 'Jelsch, Christian' _publ_contact_author 'Christian Jelsch' _publ_section_title ; Experimental and database-transferred electron-density analysis and evaluation of electrostatic forces in coumarin-102 dye ; _journal_coeditor_code GW5019 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 646 _journal_page_last 660 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C16 H17 N O2' _chemical_formula_sum 'C16 H17 N O2' _chemical_formula_weight 255.300 _chemical_name_common coumarin-102 _chemical_name_systematic ; 8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo(de)anthracen-10-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method MoPro12 _cell_angle_alpha 90.00 _cell_angle_beta 95.249(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.5755(3) _cell_length_b 10.1627(3) _cell_length_c 14.2676(2) _cell_measurement_reflns_used 77717 _cell_measurement_temperature 100(1) _cell_measurement_theta_max 51.16 _cell_measurement_theta_min 2.67 _cell_volume 1238.21(6) _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009) ; _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009) ; _computing_molecular_graphics ; ORTEP (Farrugia, 1997) PLATON (Spek, 2003) MoPro (Jelsch et al., 2005) ; _computing_publication_material 'MoPro (Jelsch et al., 2005)' _computing_structure_refinement ; SHELX97 (Sheldrick, 2008) MoPro (Jelsch et al., 2005) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 100(1) _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device_type 'Oxford diffraction Xcalibur 4-circles' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_sigmaI/netI 0.02912 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 77717 _diffrn_reflns_theta_full 44.48 _diffrn_reflns_theta_max 51.16 _diffrn_reflns_theta_min 2.67 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'Oxford Diffraction, (Clark & Reid, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.92 _exptl_crystal_size_mid 0.65 _exptl_crystal_size_min 0.33 _refine_diff_density_max 0.37 _refine_diff_density_min -0.23 _refine_diff_density_rms 0.05 _refine_ls_extinction_coef 0.43316 _refine_ls_extinction_method 'Isotropic Gaussian' _refine_ls_goodness_of_fit_ref 1.908 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 612 _refine_ls_number_reflns 12801 _refine_ls_number_restraints 343 _refine_ls_restrained_S_all 0.353 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0200 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0160 _refine_ls_wR_factor_ref 0.0174 _reflns_number_gt 9801 _reflns_number_total 12801 _reflns_threshold_expression >2.0sigma(I) _iucr_refine_instructions_details ; MoPro molecular file ; _[local]_cod_data_source_file gw5019.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2105298 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' loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 O1 C2 bX O1 C9 Y O11 C2 X O11 O1 Y C2 O1 bX C2 O11 Y C3 C2 bX C3 C4 Y H3 C3 Z H3 C2 X C4 C10 bX C4 C3 Y C5 C6 bX C5 C10 Y H5 C5 Z H5 C6 X C6 C7 bX C6 C12 Y C7 C8 bX C7 C6 Y C8 C9 bX C8 C7 Y C9 C8 bX C9 C10 Y C10 C4 bX C10 C5 Y C23 C4 Z C23 H23C X H23A C23 Z H23A C4 X H23B C23 Z H23B C4 X H23C C23 Z H23C C4 X C12 C6 bZ C12 C13 X H12A C12 Z H12A C6 X H12B C12 Z H12B C6 X C13 C14 bZ C13 C12 X H13A C13 Z H13A C14 X H13B C13 Z H13B C14 X C14 N15 bZ C14 C13 X H14A C14 Z H14A N15 X H14B C14 Z H14B N15 X C16 N15 bZ C16 C17 X H16A C16 Z H16A N15 X H16B C16 Z H16B N15 X C17 C16 bZ C17 C18 X H17A C17 Z H17A C16 X H17B C17 Z H17B C16 X C18 C8 bZ C18 C17 X H18A C18 Z H18A C8 X H18B C18 Z H18B C8 X N15 C16 bX N15 C14 Y loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 O1 6.22(2) 0. -0.061(5) -0.017(5) -0.009(5) 0.012(6) 0.012(5) -0.012(5) 0.041(5) 0.011(5) -0.0010(41) -0.014(4) -0.0030(37) -0.007(4) 0.0000(37) -0.080(4) 0.013(4) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.996(1) 1.131(2) 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O11 6.22(2) 0. -0.039(7) -0.008(6) 0.009(6) -0.075(7) 0.011(6) -0.019(6) -0.030(6) -0.013(6) -0.005(5) 0.012(4) -0.011(4) -0.007(4) 0.007(4) 0.022(4) -0.015(4) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.992(2) 1.127(2) 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 C2 3.92(3) 0. -0.034(8) 0.114(7) 0.0020(61) -0.257(8) -0.011(6) 0.012(6) 0.009(7) 0.143(8) 0.0050(71) -0.016(7) 0.0020(68) -0.0040(72) -0.0040(70) -0.344(9) 0.0020(80) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.015(3) 0.931(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 C3 3.90(4) 0. 0.04(1) 0.037(9) -0.008(6) -0.130(8) 0.009(6) -0.0030(66) -0.0070(86) 0.012(8) -0.0010(73) 0.032(7) 0.037(7) 0.016(7) -0.0020(72) -0.244(9) 0.0020(79) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.019(3) 0.943(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H3 1.02(3) 0. 0. 0. 0.16(1) 0.09(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.12(1) 1.229(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C4 4.08(3) 0. 0.039(8) 0.063(8) -0.009(6) -0.240(7) -0.0020(58) 0.017(6) -0.012(7) 0.044(7) -0.0010(67) 0.025(6) 0.019(6) 0.0010(68) 0.010(7) -0.269(8) -0.0030(79) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.008(3) 0.976(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 C5 3.92(4) 0. 0.049(10) -0.0070(82) 0.0020(61) -0.175(7) 0.0050(59) 0.018(6) -0.035(8) 0.011(7) -0.015(7) 0.010(6) -0.0030(65) -0.0040(71) 0.011(7) -0.246(9) 0.043(7) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.019(3) 0.943(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H5 1.01(3) 0. 0. 0. 0.17(1) 0.09(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.12(1) 1.229(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C6 4.10(3) 0. -0.023(8) -0.0050(68) -0.024(6) -0.167(6) 0.014(6) -0.0050(54) 0.030(7) -0.0010(68) 0.019(7) -0.028(6) -0.011(6) 0.008(7) -0.011(7) -0.265(7) -0.0030(74) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.008(3) 0.976(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 C7 3.91(3) 0. 0.081(7) -0.012(7) -0.0040(56) -0.186(7) 0.006(6) -0.0040(59) -0.048(7) 0.0010(69) 0.0020(67) 0.007(6) -0.0010(62) -0.0050(67) 0.0050(67) -0.253(8) -0.0060(77) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.016(3) 0.950(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 C8 4.08(3) 0. -0.018(7) -0.028(8) -0.0030(58) -0.149(7) 0.0000(55) -0.014(6) -0.017(7) 0.013(7) 0.0020(64) 0.027(6) 0.0030(61) 0.012(6) 0.0040(67) -0.257(7) -0.014(7) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.010(3) 0.974(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 C9 3.94(3) 0. 0.127(7) 0.044(7) -0.016(6) -0.149(7) -0.0050(54) -0.020(6) -0.087(7) -0.020(7) 0.0000(66) 0.035(6) -0.012(6) 0.0040(66) -0.0050(65) -0.294(8) 0.0030(74) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.016(3) 0.951(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 C10 4.04(3) 0. 0.0020(75) 0.008(8) 0.0010(59) -0.140(7) 0.007(6) -0.028(6) -0.020(7) 0.018(7) 0.009(7) 0.0010(61) 0.012(6) -0.0040(67) -0.014(7) -0.227(8) 0.020(8) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.010(3) 0.974(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 C23 3.82(9) 0. -0.04(1) 0.04(1) 0.000(11) -0.019(9) -0.015(8) 0.0010(73) -0.011(8) -0.036(8) 0.218(10) 0.0000(74) 0.008(7) 0.018(8) 0.033(8) 0.160(9) -0.017(8) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.023(6) 0.945(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H23A 1.00(3) 0. 0. 0. 0.11(1) 0.06(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.13(1) 1.193(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H23B 1.05(3) 0. 0. 0. 0.12(1) 0.06(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.13(1) 1.193(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H23C 1.02(3) 0. 0. 0. 0.13(1) 0.04(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.13(1) 1.193(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C12 3.91(3) 0. -0.0020(67) -0.023(9) -0.0050(85) 0.015(6) 0.020(6) 0.0030(77) 0.012(8) -0.016(6) -0.0030(71) -0.0030(69) 0.024(7) 0.290(8) 0.020(7) 0.019(6) -0.028(7) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.018(2) 0.958(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H12A 1.03(2) 0. 0. 0. 0.144(9) 0.063(9) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H12B 1.01(2) 0. 0. 0. 0.130(9) 0.046(10) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C13 3.95(3) 0. -0.017(7) -0.032(9) 0.012(9) 0.025(6) 0.018(7) -0.0010(81) 0.0040(78) 0.0050(60) -0.0070(73) -0.028(7) 0.014(7) 0.311(8) 0.030(7) 0.030(6) -0.016(7) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.018(2) 0.958(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H13A 1.03(2) 0. 0. 0. 0.149(9) 0.063(10) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H13B 1.01(2) 0. 0. 0. 0.127(9) 0.050(10) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C14 3.69(5) 0. 0.029(6) -0.050(9) 0.016(9) 0.013(6) 0.043(7) 0.014(8) -0.0060(81) 0.0050(59) -0.044(7) -0.018(7) 0.027(7) 0.284(8) -0.0040(64) 0.0000(66) -0.016(7) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.027(4) 0.994(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H14A 1.11(2) 0. 0. 0. 0.15(1) 0.09(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.11(1) 1.207(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H14B 1.05(2) 0. 0. 0. 0.16(1) 0.08(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.11(1) 1.207(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C16 3.71(5) 0. 0.076(6) -0.016(9) 0.016(9) 0.007(6) 0.077(6) 0.0020(78) 0.0030(77) 0.018(6) -0.034(7) -0.011(7) 0.029(7) 0.283(8) -0.0050(64) 0.014(6) -0.0010(66) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.027(4) 0.994(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H16A 1.08(2) 0. 0. 0. 0.16(1) 0.07(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.11(1) 1.207(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H16B 1.08(2) 0. 0. 0. 0.16(1) 0.08(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.11(1) 1.207(2) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C17 3.95(3) 0. 0.022(7) -0.032(9) -0.0050(87) 0.015(6) 0.008(7) 0.030(8) -0.0020(78) -0.0050(58) -0.0010(72) -0.010(7) 0.009(7) 0.301(8) 0.025(7) 0.025(6) -0.015(7) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.018(2) 0.958(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H17A 1.02(2) 0. 0. 0. 0.141(9) 0.058(9) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H17B 0.99(2) 0. 0. 0. 0.130(9) 0.03(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 C18 3.91(3) 0. -0.0030(63) 0.014(9) -0.048(9) 0.009(6) 0.024(6) -0.012(8) -0.038(7) -0.007(6) 0.0000(73) 0.0000(65) -0.0050(69) 0.296(8) 0.009(6) 0.016(6) -0.008(7) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.018(2) 0.958(2) 2 3.176 2 3.176 2 3.176 3 3.176 4 3.176 H18A 0.98(2) 0. 0. 0. 0.117(9) 0.078(10) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 H18B 1.00(2) 0. 0. 0. 0.125(9) 0.05(1) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.138(9) 1.246(1) 1 2.000 1 2.000 2 2.000 2 2.000 2 2.000 N15 5.23(3) 0. -0.036(6) -0.042(6) 0.011(5) 0.027(6) 0.017(6) -0.015(5) 0.011(6) 0.012(6) 0.0000(57) -0.027(5) 0.006(5) 0.015(5) -0.0050(55) -0.216(6) -0.0050(58) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.995(2) 0.924(2) 2 3.839 2 3.839 2 3.839 3 3.839 4 3.839 loop_ _atom_site_type_symbol _atom_site_label _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_calc_flag O O1 0.62321(3) 0.54842(2) -0.17206(2) 0.0134(2) Uani 1 d O O11 0.56277(4) 0.65946(3) -0.30357(2) 0.0189(2) Uani 1 d C C2 0.63367(2) 0.66057(2) -0.22535(1) 0.0139(1) Uani 1 d C C3 0.72648(2) 0.76777(2) -0.18394(2) 0.0149(1) Uani 1 d H H3 0.7345(5) 0.8542(4) -0.2276(2) 0.03315 Uani 1 d C C4 0.80212(2) 0.75924(2) -0.09539(2) 0.0131(1) Uani 1 d C C5 0.86283(2) 0.62046(2) 0.04932(1) 0.0122(1) Uani 1 d H H5 0.9344(5) 0.6994(3) 0.0810(2) 0.02768 Uani 1 d C C6 0.84666(2) 0.50407(2) 0.09709(1) 0.0113(1) Uani 1 d C C7 0.75060(2) 0.40135(2) 0.05468(1) 0.0106(1) Uani 1 d C C8 0.67611(2) 0.41815(2) -0.03711(1) 0.0108(1) Uani 1 d C C9 0.69769(2) 0.53672(2) -0.08279(1) 0.0108(1) Uani 1 d C C10 0.78880(2) 0.64072(2) -0.04210(1) 0.0114(1) Uani 1 d C C23 0.89940(3) 0.87153(2) -0.05449(2) 0.0185(1) Uani 1 d H H23A 0.8977(4) 0.9510(3) -0.1022(3) 0.04044 Uani 1 d H H23B 1.0173(3) 0.8416(3) -0.0385(3) 0.03777 Uani 1 d H H23C 0.8563(4) 0.9053(3) 0.0086(2) 0.03756 Uani 1 d C C12 0.92625(2) 0.48213(2) 0.19428(1) 0.0136(1) Uani 1 d H H12A 0.9553(4) 0.5749(3) 0.2296(1) 0.03039 Uani 1 d H H12B 1.0365(3) 0.4284(4) 0.1910(1) 0.02988 Uani 1 d C C13 0.81734(3) 0.40229(2) 0.25129(1) 0.0155(1) Uani 1 d H H13A 0.8726(4) 0.3868(2) 0.3224(2) 0.03380 Uani 1 d H H13B 0.7080(3) 0.4562(2) 0.2558(3) 0.03077 Uani 1 d C C14 0.78469(3) 0.27096(2) 0.20253(1) 0.0163(1) Uani 1 d H H14A 0.8900(4) 0.2104(3) 0.2083(2) 0.03182 Uani 1 d H H14B 0.6934(5) 0.2182(3) 0.2360(2) 0.03299 Uani 1 d C C16 0.64863(3) 0.17364(2) 0.06024(2) 0.0150(1) Uani 1 d H H16A 0.5307(4) 0.1724(4) 0.0827(2) 0.03192 Uani 1 d H H16B 0.7079(5) 0.0840(3) 0.0871(2) 0.03239 Uani 1 d C C17 0.64245(3) 0.17673(2) -0.04651(1) 0.0145(1) Uani 1 d H H17A 0.5682(5) 0.0975(2) -0.0765(1) 0.03260 Uani 1 d H H17B 0.7602(4) 0.1628(3) -0.0687(1) 0.02937 Uani 1 d C C18 0.57795(2) 0.30898(2) -0.08314(1) 0.0132(1) Uani 1 d H H18A 0.5792(5) 0.3123(1) -0.1596(2) 0.02879 Uani 1 d H H18B 0.4559(3) 0.3184(1) -0.0680(3) 0.02929 Uani 1 d N N15 0.73229(2) 0.28657(2) 0.10296(1) 0.0136(1) Uani 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0149(8) 0.0134(8) 0.0115(8) -0.00045(6) -0.00098(9) 0.00120(6) O11 0.0220(8) 0.0207(8) 0.0136(8) 0.00261(9) -0.0018(1) 0.00386(8) C2 0.0146(7) 0.0142(7) 0.0127(8) 0.00244(5) 0.00118(9) 0.00238(5) C3 0.0156(7) 0.0123(7) 0.0170(8) 0.00174(5) 0.00216(9) 0.00331(6) H3 0.0423 0.0237 0.0334 -0.0012 0.0027 0.0120 C4 0.0128(7) 0.0099(7) 0.0167(7) 0.00050(5) 0.00232(9) 0.00078(5) C5 0.0120(7) 0.0107(7) 0.0135(7) -0.00099(5) 0.000023(8) -0.00149(5) H5 0.0290 0.0221 0.0307 -0.0080 -0.0042 -0.0050 C6 0.0113(7) 0.0110(7) 0.0112(7) -0.00044(5) -0.00053(8) -0.00120(5) C7 0.0112(7) 0.0098(7) 0.0105(7) -0.00060(5) -0.000018(8) -0.00049(5) C8 0.0115(7) 0.0103(7) 0.0105(7) -0.00114(5) -0.00032(8) -0.00030(5) C9 0.0110(7) 0.0105(7) 0.0108(7) -0.00030(5) 0.00034(8) 0.00031(5) C10 0.0116(7) 0.0099(7) 0.0128(7) -0.00055(5) 0.00093(8) -0.00012(5) C23 0.0193(8) 0.0110(7) 0.0252(8) -0.00224(6) 0.00121(10) 0.00028(7) H23A 0.0517 0.0249 0.0440 -0.0077 0.0004 0.0117 H23B 0.0237 0.0303 0.0582 0.0012 -0.0017 -0.0036 H23C 0.0415 0.0348 0.0381 -0.0076 0.0130 -0.0109 C12 0.0128(7) 0.0150(7) 0.0125(8) 0.00081(5) -0.00148(8) -0.00217(5) H12A 0.0383 0.0247 0.0273 -0.0041 -0.0018 -0.0079 H12B 0.0256 0.0336 0.0301 0.0090 0.0003 0.0006 C13 0.0182(7) 0.0169(8) 0.0112(7) 0.00066(6) 0.00047(9) -0.00124(6) H13A 0.0427 0.0381 0.0189 -0.0006 -0.0063 0.0026 H13B 0.0271 0.0310 0.0345 0.0041 0.0043 -0.0014 C14 0.0221(7) 0.0142(7) 0.0121(8) -0.00037(7) -0.00074(9) 0.00148(6) H14A 0.0330 0.0314 0.0299 0.0090 -0.0027 -0.0002 H14B 0.0375 0.0350 0.0273 -0.0089 0.0073 0.0039 C16 0.0182(8) 0.0121(7) 0.0145(8) -0.00316(6) 0.00079(9) 0.00072(6) H16A 0.0274 0.0357 0.0333 -0.0071 0.0063 -0.0017 H16B 0.0428 0.0209 0.0323 0.0034 -0.0030 0.0037 C17 0.0170(7) 0.0116(7) 0.0145(8) -0.00099(5) -0.00020(9) -0.00187(5) H17A 0.0398 0.0229 0.0336 -0.0114 -0.0049 -0.0034 H17B 0.0269 0.0313 0.0303 0.0025 0.0042 0.0014 C18 0.0136(7) 0.0124(8) 0.0133(7) -0.00199(5) -0.00141(9) -0.00049(5) H18A 0.0390 0.0288 0.0182 -0.0028 0.0004 -0.0015 H18B 0.0206 0.0298 0.0378 -0.0030 0.0044 -0.0019 N15 0.0179(8) 0.0112(7) 0.0112(7) -0.00210(5) -0.00097(9) 0.00087(5) 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 'Su & Coppens, Acta. Cryst. (1997) A53, 749 ' H H 0.0000 0.0000 'Su & Coppens, Acta. Cryst. (1997) A53, 749 ' N N 0.0061 0.0033 'Su & Coppens, Acta. Cryst. (1997) A53, 749 ' O O 0.0106 0.0060 'Su & Coppens, Acta. Cryst. (1997) A53, 749 ' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C2 O11 116.40(3) O1 C2 C3 117.38(2) O1 C9 C8 115.98(2) O1 C9 C10 120.64(2) O11 C2 C3 126.22(3) C2 O1 C9 122.27(2) C2 C3 C4 121.79(2) C2 C3 H3 116.0(1) C3 C4 C10 119.23(2) C3 C4 C23 120.70(2) H3 C3 C4 122.2(1) C4 C10 C9 118.68(2) C4 C10 C5 124.12(2) C4 C23 H23A 110.9(2) C4 C23 H23C 110.6(2) C4 C23 H23B 110.6(2) C5 C6 C7 119.84(2) C5 C6 C12 121.67(2) C5 C10 C9 117.19(2) H5 C5 C6 120.6(1) H5 C5 C10 117.8(1) C6 C7 N15 119.78(2) C6 C7 C8 119.86(2) C6 C12 C13 108.76(1) C6 C12 H12A 111.3(1) C6 C12 H12B 110.8(1) C6 C5 C10 121.64(2) C7 N15 C16 122.32(2) C7 N15 C14 122.85(2) C7 C8 C9 118.07(2) C7 C8 C18 120.12(2) C7 C6 C12 118.49(2) C8 C9 C10 123.37(2) C8 C7 N15 120.35(2) C8 C18 C17 109.18(2) C8 C18 H18B 110.9(1) C8 C18 H18A 110.9(1) C9 C8 C18 121.80(2) C10 C4 C23 120.07(2) H23A C23 H23C 108.4(3) H23A C23 H23B 108.4(2) H23B C23 H23C 108.0(3) C12 C13 C14 108.60(2) C12 C13 H13A 109.7(1) C12 C13 H13B 109.6(1) H12A C12 C13 109.9(1) H12A C12 H12B 106.8(3) H12B C12 C13 109.3(1) C13 C14 N15 112.20(2) C13 C14 H14A 110.2(2) C13 C14 H14B 109.9(2) H13A C13 C14 110.2(1) H13A C13 H13B 108.6(3) H13B C13 C14 110.1(1) C14 N15 C16 114.69(2) H14A C14 N15 108.3(2) H14A C14 H14B 108.1(3) H14B C14 N15 108.0(2) C16 C17 C18 109.85(2) C16 C17 H17A 110.1(1) C16 C17 H17B 109.8(1) H16A C16 N15 108.7(2) H16A C16 C17 110.3(2) H16A C16 H16B 107.6(4) H16B C16 N15 108.3(2) H16B C16 C17 109.9(2) C17 C16 N15 111.94(2) C17 C18 H18B 109.4(1) C17 C18 H18A 109.4(1) H17A C17 C18 109.6(1) H17A C17 H17B 108.2(3) H17B C17 C18 109.2(1) H18A C18 H18B 107.0(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.3776(3) O1 C9 1.3768(3) O11 C2 1.2211(4) C2 C3 1.4434(3) C3 C4 1.3692(3) C3 H3 1.083(4) C4 C10 1.4344(3) C4 C23 1.4999(3) C5 C6 1.3785(3) C5 C10 1.4126(3) C5 H5 1.083(4) C6 C7 1.4295(2) C6 C12 1.5051(3) C7 N15 1.3710(3) C7 C8 1.4140(3) C8 C9 1.3903(2) C8 C18 1.5066(3) C9 C10 1.4077(3) C23 H23A 1.056(3) C23 H23C 1.061(3) C23 H23B 1.061(3) C12 C13 1.5269(3) C12 H12A 1.087(3) C12 H12B 1.096(3) C13 C14 1.5192(3) C13 H13A 1.091(3) C13 H13B 1.093(3) C14 N15 1.4589(3) C14 H14A 1.090(3) C14 H14B 1.094(3) C16 N15 1.4572(3) C16 C17 1.5195(3) C16 H16A 1.089(3) C16 H16B 1.095(3) C17 C18 1.5273(3) C17 H17A 1.089(3) C17 H17B 1.095(3) C18 H18B 1.092(3) C18 H18A 1.092(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 C18 H18A O1 1.092(3) 2.438(1) 2.7878(4) 96.86(9) 1_555 C5 H5 O11 1.083(4) 2.377(4) 3.4189(5) 160.8(3) 4_676 C17 H17B O11 1.095(3) 2.477(2) 3.4620(7) 149.1(2) 2_644 C23 H23A O11 1.056(3) 2.548(3) 3.5900(5) 169.0(2) 2_654 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 O1 C2 C3 C4 0.24(2) O1 C2 C3 H3 179.0(3) O1 C9 C8 C7 179.85(2) O1 C9 C8 C18 0.42(2) O1 C9 C10 C4 0.19(2) O1 C9 C10 C5 -179.31(2) O11 C2 O1 C9 179.89(3) O11 C2 C3 C4 -179.84(3) O11 C2 C3 H3 -1.0(1) C2 O1 C9 C8 179.70(2) C2 O1 C9 C10 -0.03(2) C2 C3 C4 C10 -0.09(2) C2 C3 C4 C23 179.25(2) C3 C2 O1 C9 -0.18(2) C3 C4 C10 C9 -0.12(2) C3 C4 C10 C5 179.33(2) C3 C4 C23 H23A 0.4(2) C3 C4 C23 H23C 120.7(2) C3 C4 C23 H23B -119.8(2) H3 C3 C4 C10 -178.8(3) H3 C3 C4 C23 0.5(1) C4 C10 C9 C8 -179.53(2) C4 C10 C5 C6 -179.61(2) C4 C10 C5 H5 -0.2(1) C5 C6 C7 N15 -178.80(2) C5 C6 C7 C8 1.75(2) C5 C6 C12 C13 143.13(2) C5 C6 C12 H12A 21.96(8) C5 C6 C12 H12B -96.8(1) C5 C10 C9 C8 0.98(2) C5 C10 C4 C23 -0.02(2) H5 C5 C6 C7 179.4(3) H5 C5 C6 C12 0.2(1) H5 C5 C10 C9 179.3(3) C6 C7 N15 C16 -173.89(2) C6 C7 N15 C14 10.64(2) C6 C7 C8 C9 -0.95(2) C6 C7 C8 C18 178.49(2) C6 C12 C13 C14 60.39(2) C6 C12 C13 H13A -179.1(2) C6 C12 C13 H13B -59.9(2) C6 C5 C10 C9 -0.14(2) C7 N15 C16 C17 22.17(2) C7 N15 C16 H16A -99.9(2) C7 N15 C16 H16B 143.5(2) C7 N15 C14 C13 16.14(2) C7 N15 C14 H14A -105.7(2) C7 N15 C14 H14B 137.4(2) C7 C8 C9 C10 -0.42(2) C7 C8 C18 C17 -30.09(2) C7 C8 C18 H18B 90.6(2) C7 C8 C18 H18A -150.7(2) C7 C6 C12 C13 -36.04(2) C7 C6 C12 H12A -157.2(2) C7 C6 C12 H12B 84.0(2) C7 C6 C5 C10 -1.19(2) C8 C7 N15 C16 5.55(2) C8 C7 N15 C14 -169.91(2) C8 C7 C6 C12 -179.06(2) C8 C18 C17 C16 55.74(2) C8 C18 C17 H17A 176.8(2) C8 C18 C17 H17B -64.7(2) C9 C8 C7 N15 179.61(2) C9 C8 C18 C17 149.33(2) C9 C8 C18 H18B -90.0(1) C9 C8 C18 H18A 28.67(8) C9 C10 C4 C23 -179.47(2) C10 C9 C8 C18 -179.85(2) C10 C4 C23 H23A 179.8(2) C10 C4 C23 H23C -60.0(2) C10 C4 C23 H23B 59.6(2) C10 C5 C6 C12 179.64(2) C12 C6 C7 N15 0.39(2) C12 C13 C14 N15 -51.35(2) C12 C13 C14 H14A 69.4(2) C12 C13 C14 H14B -171.5(2) H12A C12 C13 C14 -177.5(2) H12A C12 C13 H13A -57.0(2) H12A C12 C13 H13B 62.1(2) H12B C12 C13 C14 -60.6(2) H12B C12 C13 H13A 59.9(3) H12B C12 C13 H13B 179.0(3) C13 C14 N15 C16 -159.64(2) H13A C13 C14 N15 -171.5(2) H13A C13 C14 H14A -50.8(3) H13A C13 C14 H14B 68.3(2) H13B C13 C14 N15 68.7(2) H13B C13 C14 H14A -170.5(3) H13B C13 C14 H14B -51.5(3) C14 N15 C16 C17 -162.02(2) C14 N15 C16 H16A 75.9(2) C14 N15 C16 H16B -40.7(2) H14A C14 N15 C16 78.5(2) H14B C14 N15 C16 -38.4(2) C16 C17 C18 H18B -65.8(2) C16 C17 C18 H18A 177.3(2) H16A C16 C17 C18 68.4(2) H16A C16 C17 H17A -52.4(3) H16A C16 C17 H17B -171.4(3) H16B C16 C17 C18 -173.1(2) H16B C16 C17 H17A 66.1(2) H16B C16 C17 H17B -53.0(3) H17A C17 C16 N15 -173.6(2) H17A C17 C18 H18B 55.3(3) H17A C17 C18 H18A -61.6(2) H17B C17 C16 N15 67.4(2) H17B C17 C18 H18B 173.7(3) H17B C17 C18 H18A 56.8(3) C18 C8 C7 N15 -0.95(2) C18 C17 C16 N15 -52.77(2) _journal_paper_doi 10.1107/S0108768112042826