# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yoshitane Imai' _publ_contact_author_email Y-IMAI@APCH.KINDAI.AC.JP _publ_section_title ; Formation and crystal structure of the chiral charge-transfer complex with axially chiral 1,1'-Bi-2-naphthol derivatives and tetracyanobenzene ; loop_ _publ_author_name 'Yoshitane Imai' 'Takunori Harada' 'Kensaku Kamon' 'Shingo Kido' 'Reiko Kuroda' 'Yoshio Matsubara' 'Tomohiro Sato' ; N.Tajima ; # Attachment 'Rimai711.cif' data_imai711_1 _database_code_depnum_ccdc_archive 'CCDC 658542' #data_im7570b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H8 Br N4 O' _chemical_formula_weight 400.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.349(4) _cell_length_b 7.3596(11) _cell_length_c 8.8067(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.072(2) _cell_angle_gamma 90.00 _cell_volume 1676.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3429 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 2.469 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3189 _exptl_absorpt_correction_T_max 0.7903 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7309 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3752 _reflns_number_gt 3429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.1458P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(8) _refine_ls_number_reflns 3752 _refine_ls_number_parameters 236 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.002 _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 C1 C 0.47147(9) 0.7302(3) 0.9921(3) 0.0124(5) Uani 1 1 d . . . C2 C 0.44919(10) 0.8143(4) 1.1030(3) 0.0141(5) Uani 1 1 d . . . C3 C 0.39535(10) 0.8100(4) 1.0957(3) 0.0162(6) Uani 1 1 d . . . H3 H 0.3810 0.8599 1.1776 0.019 Uiso 1 1 calc R . . C4 C 0.36367(11) 0.7340(4) 0.9706(3) 0.0155(6) Uani 1 1 d . . . H4 H 0.3274 0.7316 0.9662 0.019 Uiso 1 1 calc R . . C5 C 0.35163(10) 0.5951(4) 0.7105(3) 0.0152(6) Uani 1 1 d . . . H5 H 0.3151 0.6008 0.7005 0.018 Uiso 1 1 calc R . . C6 C 0.37282(10) 0.5263(4) 0.5945(3) 0.0161(6) Uani 1 1 d . . . C7 C 0.42650(10) 0.5081(3) 0.6073(3) 0.0161(6) Uani 1 1 d . . . H7 H 0.4404 0.4550 0.5258 0.019 Uiso 1 1 calc R . . C8 C 0.45856(10) 0.5679(3) 0.7388(3) 0.0148(5) Uani 1 1 d . . . H8 H 0.4949 0.5534 0.7485 0.018 Uiso 1 1 calc R . . C9 C 0.43891(10) 0.6511(4) 0.8614(3) 0.0129(5) Uani 1 1 d . . . C10 C 0.38441(10) 0.6588(4) 0.8476(3) 0.0135(6) Uani 1 1 d . . . O2 O 0.48097(7) 0.9061(2) 1.2173(2) 0.0170(5) Uani 1 1 d . . . H2 H 0.4655 0.9252 1.2908 0.026 Uiso 1 1 calc R . . Br6 Br 0.329965(9) 0.44855(5) 0.40649(3) 0.02015(8) Uani 1 1 d . . . C11 C 0.30159(11) 1.1349(4) 0.7507(3) 0.0170(6) Uani 1 1 d . . . H11 H 0.2649 1.1317 0.7267 0.020 Uiso 1 1 calc R . . C12 C 0.32695(10) 1.2064(4) 0.8904(3) 0.0163(6) Uani 1 1 d . . . C13 C 0.38138(11) 1.2080(4) 0.9277(3) 0.0143(6) Uani 1 1 d . . . C14 C 0.41007(11) 1.1417(4) 0.8234(3) 0.0165(6) Uani 1 1 d . . . H14 H 0.4468 1.1427 0.8480 0.020 Uiso 1 1 calc R . . C15 C 0.38426(10) 1.0736(4) 0.6823(3) 0.0159(6) Uani 1 1 d . . . C16 C 0.33022(11) 1.0682(3) 0.6464(3) 0.0155(6) Uani 1 1 d . . . C17 C 0.29650(11) 1.2818(4) 0.9966(3) 0.0204(6) Uani 1 1 d . . . N18 N 0.27190(10) 1.3426(4) 1.0761(3) 0.0310(6) Uani 1 1 d . . . C19 C 0.40766(11) 1.2757(4) 1.0763(3) 0.0168(6) Uani 1 1 d . . . N20 N 0.42914(10) 1.3246(4) 1.1943(3) 0.0249(6) Uani 1 1 d . . . C21 C 0.41303(10) 1.0146(4) 0.5675(3) 0.0192(6) Uani 1 1 d . . . N22 N 0.43418(8) 0.9737(5) 0.4715(2) 0.0254(6) Uani 1 1 d . . . C23 C 0.30432(10) 0.9956(3) 0.4989(3) 0.0183(7) Uani 1 1 d . . . N24 N 0.28487(8) 0.9397(5) 0.3817(3) 0.0276(5) 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 C1 0.0106(13) 0.0126(13) 0.0138(13) 0.0036(10) 0.0017(10) -0.0003(10) C2 0.0132(13) 0.0155(13) 0.0130(13) 0.0021(11) 0.0015(11) -0.0005(11) C3 0.0168(15) 0.0171(14) 0.0163(14) 0.0022(11) 0.0071(11) 0.0030(11) C4 0.0108(14) 0.0156(14) 0.0209(15) 0.0048(12) 0.0050(12) 0.0004(11) C5 0.0104(13) 0.0154(14) 0.0191(14) 0.0043(11) 0.0008(11) 0.0001(11) C6 0.0174(14) 0.0159(12) 0.0118(13) -0.0006(10) -0.0049(11) -0.0044(11) C7 0.0170(14) 0.0162(14) 0.0152(13) 0.0001(10) 0.0034(11) -0.0001(10) C8 0.0114(13) 0.0148(13) 0.0180(14) 0.0030(11) 0.0026(11) 0.0008(11) C9 0.0121(13) 0.0130(13) 0.0134(13) 0.0039(10) 0.0019(10) 0.0003(11) C10 0.0144(14) 0.0112(13) 0.0142(14) 0.0035(11) 0.0011(11) 0.0000(11) O2 0.0121(9) 0.0261(15) 0.0129(9) -0.0055(8) 0.0024(7) 0.0004(8) Br6 0.01890(13) 0.02326(13) 0.01561(12) -0.00202(16) -0.00344(9) -0.00008(17) C11 0.0138(14) 0.0162(14) 0.0201(15) 0.0010(11) 0.0010(11) 0.0002(11) C12 0.0179(15) 0.0149(14) 0.0168(14) 0.0005(11) 0.0049(12) -0.0004(11) C13 0.0136(14) 0.0144(14) 0.0150(15) 0.0040(12) 0.0033(12) -0.0011(11) C14 0.0145(14) 0.0176(14) 0.0176(15) 0.0044(11) 0.0035(11) 0.0002(11) C15 0.0185(14) 0.0152(14) 0.0146(13) 0.0043(11) 0.0045(11) 0.0006(11) C16 0.0199(15) 0.0110(13) 0.0150(13) 0.0015(11) 0.0018(11) -0.0015(11) C17 0.0155(15) 0.0238(16) 0.0193(15) -0.0037(12) -0.0029(12) -0.0016(12) N18 0.0215(14) 0.0457(17) 0.0251(15) -0.0127(13) 0.0028(12) -0.0019(12) C19 0.0142(14) 0.0167(14) 0.0201(15) 0.0012(11) 0.0051(12) 0.0004(11) N20 0.0233(14) 0.0300(15) 0.0209(14) -0.0012(12) 0.0028(11) -0.0021(11) C21 0.0130(14) 0.0242(15) 0.0189(14) 0.0026(11) -0.0005(12) -0.0003(11) N22 0.0211(11) 0.0371(18) 0.0179(11) -0.0025(13) 0.0039(9) 0.0046(13) C23 0.0175(14) 0.0183(17) 0.0196(14) -0.0005(11) 0.0048(12) -0.0006(10) N24 0.0252(12) 0.0318(14) 0.0244(12) -0.0070(17) 0.0014(10) -0.0051(17) _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 C1 C2 1.379(3) . ? C1 C9 1.421(4) . ? C1 C1 1.483(5) 2_657 ? C2 O2 1.359(3) . ? C2 C3 1.408(4) . ? C3 C4 1.367(4) . ? C4 C10 1.417(4) . ? C5 C6 1.354(4) . ? C5 C10 1.422(4) . ? C6 C7 1.404(4) . ? C6 Br6 1.904(3) . ? C7 C8 1.369(4) . ? C8 C9 1.423(4) . ? C9 C10 1.419(4) . ? C11 C16 1.386(4) . ? C11 C12 1.386(4) . ? C12 C13 1.409(4) . ? C12 C17 1.454(4) . ? C13 C14 1.385(4) . ? C13 C19 1.447(4) . ? C14 C15 1.391(4) . ? C15 C16 1.398(4) . ? C15 C21 1.442(4) . ? C16 C23 1.449(4) . ? C17 N18 1.134(4) . ? C19 N20 1.142(4) . ? C21 N22 1.139(3) . ? C23 N24 1.138(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 C2 C1 C9 119.0(2) . . ? C2 C1 C1 119.7(3) . 2_657 ? C9 C1 C1 121.3(2) . 2_657 ? O2 C2 C1 117.5(2) . . ? O2 C2 C3 121.2(2) . . ? C1 C2 C3 121.3(2) . . ? C4 C3 C2 120.0(3) . . ? C3 C4 C10 120.7(3) . . ? C6 C5 C10 119.5(3) . . ? C5 C6 C7 122.0(2) . . ? C5 C6 Br6 120.5(2) . . ? C7 C6 Br6 117.47(19) . . ? C8 C7 C6 119.1(2) . . ? C7 C8 C9 121.7(3) . . ? C10 C9 C1 119.8(2) . . ? C10 C9 C8 117.5(2) . . ? C1 C9 C8 122.7(2) . . ? C4 C10 C9 118.9(3) . . ? C4 C10 C5 121.1(3) . . ? C9 C10 C5 120.0(3) . . ? C16 C11 C12 119.5(3) . . ? C11 C12 C13 120.4(2) . . ? C11 C12 C17 119.0(2) . . ? C13 C12 C17 120.7(3) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 C19 119.6(3) . . ? C12 C13 C19 120.2(3) . . ? C13 C14 C15 118.9(3) . . ? C14 C15 C16 121.0(3) . . ? C14 C15 C21 120.2(3) . . ? C16 C15 C21 118.8(2) . . ? C11 C16 C15 120.0(3) . . ? C11 C16 C23 120.2(3) . . ? C15 C16 C23 119.8(2) . . ? N18 C17 C12 178.2(3) . . ? N20 C19 C13 178.1(3) . . ? N22 C21 C15 176.5(3) . . ? N24 C23 C16 178.5(3) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.615 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.065 #===END data_imai711_2 _database_code_depnum_ccdc_archive 'CCDC 658543' #data_im7571b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 N4 O' _chemical_formula_weight 335.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.469(3) _cell_length_b 7.2740(8) _cell_length_c 8.7625(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.479(2) _cell_angle_gamma 90.00 _cell_volume 1658.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3061 _cell_measurement_theta_min 1.56 _cell_measurement_theta_max 27.87 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9621 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7325 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0636 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3683 _reflns_number_gt 3061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(2) _refine_ls_number_reflns 3683 _refine_ls_number_parameters 237 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 C1 C 0.47143(8) 0.7302(3) 0.9931(2) 0.0141(5) Uani 1 1 d . . . C2 C 0.44935(8) 0.8156(3) 1.1051(2) 0.0151(5) Uani 1 1 d . . . C3 C 0.39559(9) 0.8107(3) 1.0997(3) 0.0185(5) Uani 1 1 d . . . H3 H 0.3814 0.8620 1.1823 0.022 Uiso 1 1 calc R . . C4 C 0.36411(9) 0.7328(3) 0.9767(3) 0.0183(5) Uani 1 1 d . . . H4 H 0.3281 0.7294 0.9744 0.022 Uiso 1 1 calc R . . C5 C 0.35214(9) 0.5912(3) 0.7149(3) 0.0176(5) Uani 1 1 d . . . H5 H 0.3159 0.5958 0.7085 0.021 Uiso 1 1 calc R . . C6 C 0.37153(9) 0.5219(3) 0.5924(3) 0.0196(5) Uani 1 1 d . . . C7 C 0.42565(9) 0.5066(3) 0.6077(3) 0.0192(5) Uani 1 1 d . . . H7 H 0.4397 0.4537 0.5256 0.023 Uiso 1 1 calc R . . C8 C 0.45790(9) 0.5661(3) 0.7376(3) 0.0172(5) Uani 1 1 d . . . H8 H 0.4939 0.5517 0.7448 0.021 Uiso 1 1 calc R . . C9 C 0.43871(9) 0.6494(3) 0.8629(3) 0.0153(5) Uani 1 1 d . . . C10 C 0.38449(8) 0.6566(3) 0.8517(3) 0.0153(5) Uani 1 1 d . . . O2 O 0.48105(6) 0.9106(2) 1.21801(18) 0.0201(4) Uani 1 1 d . . . H2 H 0.4657 0.9314 1.2922 0.030 Uiso 1 1 calc R . . C6M C 0.33741(9) 0.4633(4) 0.4429(3) 0.0240(6) Uani 1 1 d . . . H6M1 H 0.3375 0.5588 0.3641 0.036 Uiso 1 1 calc R . . H6M2 H 0.3023 0.4449 0.4609 0.036 Uiso 1 1 calc R . . H6M3 H 0.3504 0.3480 0.4067 0.036 Uiso 1 1 calc R . . C11 C 0.30202(9) 1.1305(3) 0.7614(3) 0.0188(5) Uani 1 1 d . . . H11 H 0.2656 1.1243 0.7385 0.023 Uiso 1 1 calc R . . C12 C 0.32690(9) 1.2049(3) 0.9010(3) 0.0182(5) Uani 1 1 d . . . C13 C 0.38090(9) 1.2109(3) 0.9370(3) 0.0169(5) Uani 1 1 d . . . C14 C 0.40979(9) 1.1439(3) 0.8319(3) 0.0176(5) Uani 1 1 d . . . H14 H 0.4463 1.1458 0.8563 0.021 Uiso 1 1 calc R . . C15 C 0.38490(9) 1.0744(3) 0.6910(3) 0.0168(5) Uani 1 1 d . . . C16 C 0.33090(9) 1.0654(3) 0.6560(3) 0.0179(5) Uani 1 1 d . . . C17 C 0.29680(9) 1.2782(4) 1.0083(3) 0.0243(6) Uani 1 1 d . . . N18 N 0.27277(8) 1.3391(4) 1.0917(3) 0.0367(6) Uani 1 1 d . . . C19 C 0.40610(9) 1.2801(3) 1.0860(3) 0.0186(5) Uani 1 1 d . . . N20 N 0.42597(8) 1.3308(3) 1.2042(2) 0.0276(5) Uani 1 1 d . . . C21 C 0.41333(9) 1.0170(4) 0.5749(3) 0.0206(5) Uani 1 1 d . . . N22 N 0.43444(8) 0.9774(3) 0.4770(2) 0.0278(5) Uani 1 1 d . . . C23 C 0.30611(9) 0.9885(3) 0.5093(3) 0.0221(5) Uani 1 1 d . . . N24 N 0.28672(9) 0.9294(4) 0.3935(3) 0.0318(5) 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 C1 0.0137(11) 0.0145(11) 0.0142(12) 0.0034(9) 0.0027(9) -0.0011(9) C2 0.0143(11) 0.0174(11) 0.0130(11) 0.0041(9) 0.0005(9) 0.0007(9) C3 0.0194(12) 0.0186(12) 0.0189(12) 0.0023(10) 0.0073(9) 0.0033(10) C4 0.0122(11) 0.0205(13) 0.0223(13) 0.0046(10) 0.0039(9) 0.0001(9) C5 0.0128(11) 0.0156(12) 0.0223(13) 0.0059(9) -0.0020(9) -0.0020(9) C6 0.0209(12) 0.0163(12) 0.0199(12) 0.0012(10) -0.0013(10) -0.0043(10) C7 0.0220(12) 0.0189(12) 0.0176(12) -0.0006(10) 0.0055(10) -0.0005(10) C8 0.0159(11) 0.0163(12) 0.0197(12) 0.0001(10) 0.0040(9) 0.0015(9) C9 0.0171(11) 0.0153(11) 0.0135(11) 0.0036(9) 0.0024(9) 0.0000(10) C10 0.0147(11) 0.0126(11) 0.0181(12) 0.0061(9) 0.0019(9) -0.0002(9) O2 0.0177(8) 0.0267(9) 0.0165(8) -0.0059(7) 0.0052(6) -0.0014(7) C6M 0.0222(13) 0.0269(14) 0.0209(12) -0.0005(10) -0.0015(10) -0.0017(11) C11 0.0148(11) 0.0192(12) 0.0225(13) 0.0034(10) 0.0033(10) -0.0012(10) C12 0.0171(12) 0.0176(12) 0.0210(13) 0.0022(10) 0.0063(10) 0.0010(10) C13 0.0189(12) 0.0143(12) 0.0175(12) 0.0023(9) 0.0035(10) 0.0010(9) C14 0.0148(11) 0.0181(12) 0.0199(12) 0.0043(10) 0.0032(9) 0.0002(10) C15 0.0195(12) 0.0148(12) 0.0167(12) 0.0006(9) 0.0051(9) 0.0012(10) C16 0.0195(12) 0.0139(12) 0.0189(12) -0.0001(10) -0.0003(10) -0.0009(10) C17 0.0157(12) 0.0290(14) 0.0271(14) -0.0049(11) 0.0005(10) -0.0023(11) N18 0.0214(12) 0.0534(16) 0.0361(13) -0.0174(12) 0.0072(10) 0.0024(11) C19 0.0159(11) 0.0191(13) 0.0212(13) 0.0015(10) 0.0051(10) 0.0005(10) N20 0.0268(12) 0.0323(13) 0.0231(12) -0.0017(10) 0.0033(9) -0.0041(10) C21 0.0186(12) 0.0232(13) 0.0186(12) 0.0005(10) -0.0001(10) 0.0009(10) N22 0.0254(11) 0.0382(14) 0.0201(11) -0.0019(10) 0.0044(9) 0.0028(10) C23 0.0189(12) 0.0230(13) 0.0253(13) -0.0007(11) 0.0063(10) -0.0008(10) N24 0.0311(13) 0.0330(13) 0.0287(12) -0.0077(11) -0.0012(10) -0.0026(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 C1 C2 1.378(3) . ? C1 C9 1.427(3) . ? C1 C1 1.495(4) 2_657 ? C2 O2 1.363(3) . ? C2 C3 1.416(3) . ? C3 C4 1.360(3) . ? C4 C10 1.418(3) . ? C5 C6 1.368(3) . ? C5 C10 1.422(3) . ? C6 C7 1.419(3) . ? C6 C6M 1.511(3) . ? C7 C8 1.363(3) . ? C8 C9 1.426(3) . ? C9 C10 1.422(3) . ? C11 C16 1.385(3) . ? C11 C12 1.389(3) . ? C12 C13 1.407(3) . ? C12 C17 1.441(3) . ? C13 C14 1.388(3) . ? C13 C19 1.444(3) . ? C14 C15 1.385(3) . ? C15 C16 1.408(3) . ? C15 C21 1.433(3) . ? C16 C23 1.445(3) . ? C17 N18 1.141(3) . ? C19 N20 1.134(3) . ? C21 N22 1.142(3) . ? C23 N24 1.135(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 C2 C1 C9 118.71(19) . . ? C2 C1 C1 119.7(2) . 2_657 ? C9 C1 C1 121.5(2) . 2_657 ? O2 C2 C1 117.43(19) . . ? O2 C2 C3 121.29(19) . . ? C1 C2 C3 121.2(2) . . ? C4 C3 C2 120.3(2) . . ? C3 C4 C10 120.7(2) . . ? C6 C5 C10 122.0(2) . . ? C5 C6 C7 118.1(2) . . ? C5 C6 C6M 122.3(2) . . ? C7 C6 C6M 119.6(2) . . ? C8 C7 C6 121.5(2) . . ? C7 C8 C9 121.4(2) . . ? C10 C9 C8 117.3(2) . . ? C10 C9 C1 119.9(2) . . ? C8 C9 C1 122.7(2) . . ? C4 C10 C9 118.8(2) . . ? C4 C10 C5 121.7(2) . . ? C9 C10 C5 119.4(2) . . ? C16 C11 C12 119.3(2) . . ? C11 C12 C13 120.6(2) . . ? C11 C12 C17 119.3(2) . . ? C13 C12 C17 120.1(2) . . ? C14 C13 C12 120.0(2) . . ? C14 C13 C19 120.2(2) . . ? C12 C13 C19 119.8(2) . . ? C15 C14 C13 119.3(2) . . ? C14 C15 C16 120.7(2) . . ? C14 C15 C21 120.9(2) . . ? C16 C15 C21 118.4(2) . . ? C11 C16 C15 120.0(2) . . ? C11 C16 C23 120.6(2) . . ? C15 C16 C23 119.4(2) . . ? N18 C17 C12 178.8(3) . . ? N20 C19 C13 178.5(3) . . ? N22 C21 C15 176.4(3) . . ? N24 C23 C16 179.4(3) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.247 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.060 #===END