Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email OCRYST@ICHO.EDU.PL _publ_contact_author_name 'Prof Zofia Urbanczyk-Lipowska' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_address ; Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka Str. 44/52 Warsaw 01-224 POLAND ; _publ_section_title ; Engineering anthracene-based binary systems dedicated for reactions in non-solvent conditions ; loop_ _publ_author_name 'Zofia Urbanczyk-Lipowska' 'B. Szczesna' data_antr_al1 _database_code_CSD 216547 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O2.25' _chemical_formula_weight 283.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P-421c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 19.0750(18) _cell_length_b 19.0750(18) _cell_length_c 8.5370(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3106.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 21.34 _cell_measurement_theta_max 23.78 _exptl_crystal_description plate _exptl_crystal_colour brownish _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.640 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal covered by epoxy glue ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type MACH3 _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 3600s _diffrn_standards_decay_% 21.0 _diffrn_reflns_number 1504 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 64.84 _reflns_number_total 947 _reflns_number_gt 744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express, Nonius BV' _computing_cell_refinement 'Express, Nonius BV' _computing_data_reduction 'OpenMoleN, Nonius BV' _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. Three H-atoms from quaternary amine group were refined with N-H fixed at 0.9 A. The highest shift/error ratio belongs to one of these. ; _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^)+(0.1331P)^2^+0.9877P] 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 0.0001(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 947 _refine_ls_number_parameters 204 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1793 _refine_ls_wR_factor_gt 0.1632 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 1.548 _refine_ls_shift/su_max 0.948 _refine_ls_shift/su_mean 0.036 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 O3 O 0.0000 0.0000 0.0000 0.44(7) Uiso 1 4 d S . . H1C H 0.411(5) 0.530(5) 0.315(7) 0.00(2) Uiso 1 1 d D . . C1 C 0.4236(9) 0.2833(9) 0.173(2) 0.060(5) Uani 1 1 d . . . C2 C 0.4611(10) 0.2243(9) 0.217(2) 0.067(5) Uani 1 1 d . . . C3 C 0.5257(12) 0.2275(11) 0.300(3) 0.084(6) Uani 1 1 d . . . H3 H 0.5445 0.2710 0.3257 0.101 Uiso 1 1 calc R . . C4 C 0.5604(14) 0.1687(15) 0.342(4) 0.113(8) Uani 1 1 d . . . H4 H 0.6023 0.1722 0.3976 0.135 Uiso 1 1 calc R . . C5 C 0.5335(19) 0.1015(15) 0.304(4) 0.124(10) Uani 1 1 d . . . H5 H 0.5570 0.0613 0.3358 0.149 Uiso 1 1 calc R . . C6 C 0.4743(18) 0.0960(12) 0.221(4) 0.113(9) Uani 1 1 d . . . H6 H 0.4584 0.0519 0.1911 0.136 Uiso 1 1 calc R . . C7 C 0.4356(12) 0.1557(10) 0.177(3) 0.076(6) Uani 1 1 d . . . C8 C 0.3734(13) 0.1514(10) 0.093(3) 0.085(7) Uani 1 1 d . . . H8 H 0.3575 0.1073 0.0635 0.102 Uiso 1 1 calc R . . C9 C 0.3347(11) 0.2083(11) 0.053(3) 0.076(6) Uani 1 1 d . . . C10 C 0.2691(13) 0.2042(14) -0.027(3) 0.100(8) Uani 1 1 d . . . H10 H 0.2512 0.1605 -0.0539 0.119 Uiso 1 1 calc R . . C11 C 0.2333(14) 0.2611(18) -0.065(3) 0.106(8) Uani 1 1 d . . . H11 H 0.1909 0.2558 -0.1168 0.127 Uiso 1 1 calc R . . C12 C 0.2557(13) 0.3281(16) -0.030(3) 0.100(8) Uani 1 1 d . . . H12 H 0.2294 0.3670 -0.0592 0.120 Uiso 1 1 calc R . . C13 C 0.3181(11) 0.3356(12) 0.050(3) 0.079(6) Uani 1 1 d . . . H13 H 0.3337 0.3804 0.0750 0.095 Uiso 1 1 calc R . . C14 C 0.3593(10) 0.2771(9) 0.095(3) 0.068(5) Uani 1 1 d . . . C15 C 0.4503(11) 0.3557(10) 0.216(3) 0.066(5) Uani 1 1 d . . . C16 C 0.3414(15) 0.5549(14) 0.280(3) 0.105(8) Uani 1 1 d . . . H16A H 0.3247 0.5950 0.2205 0.126 Uiso 1 1 calc R . . H16B H 0.3553 0.5712 0.3826 0.126 Uiso 1 1 calc R . . C17 C 0.2841(16) 0.504(2) 0.296(4) 0.125(10) Uani 1 1 d . . . H17 H 0.2925 0.4672 0.3658 0.150 Uiso 1 1 calc R . . C18 C 0.229(2) 0.502(2) 0.233(4) 0.141(11) Uani 1 1 d . . . H18A H 0.2171 0.5368 0.1614 0.169 Uiso 1 1 calc R . . H18B H 0.1977 0.4660 0.2548 0.169 Uiso 1 1 calc R . . N1 N 0.4010(11) 0.5252(11) 0.202(3) 0.100(6) Uani 1 1 d D . . H1A H 0.35(13) 0.56(17) 0.05(11) 2(4) Uiso 1 1 d D . . H1B H 0.439(10) 0.555(11) 0.21(4) 0.14(10) Uiso 1 1 d D . . O1 O 0.4258(9) 0.3842(8) 0.3354(19) 0.094(5) Uani 1 1 d . . . O2 O 0.4933(9) 0.3828(8) 0.1265(17) 0.089(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 0.065(11) 0.053(10) 0.062(12) -0.001(10) 0.012(10) -0.005(9) C2 0.071(12) 0.057(11) 0.071(13) 0.000(10) 0.019(11) 0.001(10) C3 0.089(14) 0.072(13) 0.091(16) 0.000(13) 0.003(13) 0.018(11) C4 0.103(17) 0.108(19) 0.13(2) 0.001(18) 0.001(18) 0.031(16) C5 0.13(2) 0.084(19) 0.15(3) 0.01(2) 0.01(2) 0.027(17) C6 0.13(2) 0.059(13) 0.15(3) 0.003(16) 0.02(2) 0.013(14) C7 0.089(14) 0.064(13) 0.074(14) -0.007(12) 0.007(14) -0.002(11) C8 0.114(18) 0.053(11) 0.088(17) -0.003(12) 0.025(15) -0.009(12) C9 0.079(13) 0.079(14) 0.069(14) -0.003(13) 0.013(13) -0.014(11) C10 0.098(17) 0.097(18) 0.10(2) -0.015(15) -0.009(17) -0.021(16) C11 0.091(18) 0.15(3) 0.082(17) -0.021(19) -0.011(15) -0.005(16) C12 0.087(16) 0.12(2) 0.092(19) -0.001(17) -0.016(16) 0.004(14) C13 0.086(14) 0.078(13) 0.075(16) -0.001(13) 0.006(13) 0.004(11) C14 0.077(12) 0.056(11) 0.071(13) -0.001(10) 0.018(11) -0.007(10) C15 0.075(13) 0.066(12) 0.057(12) 0.008(12) 0.003(12) -0.004(11) C16 0.115(19) 0.101(17) 0.099(18) 0.001(16) -0.004(18) 0.002(17) C17 0.092(18) 0.18(3) 0.104(19) 0.02(2) 0.020(18) 0.02(2) C18 0.12(2) 0.16(3) 0.14(3) 0.02(3) 0.00(3) 0.02(2) N1 0.093(15) 0.101(15) 0.105(16) -0.002(13) 0.011(14) -0.014(12) O1 0.129(12) 0.075(9) 0.079(10) -0.012(9) 0.004(11) -0.007(9) O2 0.102(10) 0.082(9) 0.084(10) 0.006(8) 0.005(10) -0.037(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 C1 C2 1.39(3) . ? C1 C14 1.40(3) . ? C1 C15 1.52(3) . ? C2 C3 1.42(3) . ? C2 C7 1.44(3) . ? C3 C4 1.35(3) . ? C3 H3 0.9300 . ? C4 C5 1.42(4) . ? C4 H4 0.9300 . ? C5 C6 1.34(4) . ? C5 H5 0.9300 . ? C6 C7 1.41(3) . ? C6 H6 0.9300 . ? C7 C8 1.39(3) . ? C8 C9 1.36(3) . ? C8 H8 0.9300 . ? C9 C10 1.43(3) . ? C9 C14 1.44(3) . ? C10 C11 1.32(3) . ? C10 H10 0.9300 . ? C11 C12 1.38(4) . ? C11 H11 0.9300 . ? C12 C13 1.38(3) . ? C12 H12 0.9300 . ? C13 C14 1.42(3) . ? C13 H13 0.9300 . ? C15 O2 1.23(2) . ? C15 O1 1.25(2) . ? C16 N1 1.43(3) . ? C16 C17 1.47(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.18(4) . ? C17 H17 0.9300 . ? C18 H18A 0.9300 . ? C18 H18B 0.9300 . ? N1 H1C 0.99(5) . ? N1 H1A 1.7(6) . ? N1 H1B 0.92(6) . ? 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 C14 120.8(16) . . ? C2 C1 C15 120.1(17) . . ? C14 C1 C15 119.1(16) . . ? C1 C2 C3 123.2(17) . . ? C1 C2 C7 120.1(18) . . ? C3 C2 C7 116.7(18) . . ? C4 C3 C2 121(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 121(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 121(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.4 . . ? C6 C7 C8 122(2) . . ? C6 C7 C2 120(2) . . ? C8 C7 C2 117.7(18) . . ? C9 C8 C7 123.3(18) . . ? C9 C8 H8 118.3 . . ? C7 C8 H8 118.4 . . ? C8 C9 C10 124(2) . . ? C8 C9 C14 119.2(19) . . ? C10 C9 C14 117(2) . . ? C11 C10 C9 122(2) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 123(3) . . ? C10 C11 H11 118.4 . . ? C12 C11 H11 118.3 . . ? C13 C12 C11 118(3) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C12 C13 C14 122(2) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C1 C14 C13 123.1(17) . . ? C1 C14 C9 118.7(17) . . ? C13 C14 C9 118.1(19) . . ? O2 C15 O1 125(2) . . ? O2 C15 C1 117.2(19) . . ? O1 C15 C1 117.9(19) . . ? N1 C16 C17 112(2) . . ? N1 C16 H16A 109.5 . . ? C17 C16 H16A 109.2 . . ? N1 C16 H16B 109.0 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 129(4) . . ? C18 C17 H17 115.4 . . ? C16 C17 H17 115.2 . . ? C17 C18 H18A 120.1 . . ? C17 C18 H18B 119.9 . . ? H18A C18 H18B 120.0 . . ? C16 N1 H1C 70(6) . . ? C16 N1 H1A 75(10) . . ? H1C N1 H1A 141(10) . . ? C16 N1 H1B 110(10) . . ? H1C N1 H1B 74(10) . . ? H1A N1 H1B 103(10) . . ? 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 C14 C1 C2 C3 -178.4(19) . . . . ? C15 C1 C2 C3 -1(3) . . . . ? C14 C1 C2 C7 2(3) . . . . ? C15 C1 C2 C7 180(2) . . . . ? C1 C2 C3 C4 179(2) . . . . ? C7 C2 C3 C4 -1(3) . . . . ? C2 C3 C4 C5 1(4) . . . . ? C3 C4 C5 C6 2(5) . . . . ? C4 C5 C6 C7 -3(5) . . . . ? C5 C6 C7 C8 -179(3) . . . . ? C5 C6 C7 C2 2(4) . . . . ? C1 C2 C7 C6 179(2) . . . . ? C3 C2 C7 C6 0(3) . . . . ? C1 C2 C7 C8 1(3) . . . . ? C3 C2 C7 C8 -179(2) . . . . ? C6 C7 C8 C9 179(2) . . . . ? C2 C7 C8 C9 -3(3) . . . . ? C7 C8 C9 C10 -177(2) . . . . ? C7 C8 C9 C14 1(3) . . . . ? C8 C9 C10 C11 -180(3) . . . . ? C14 C9 C10 C11 1(4) . . . . ? C9 C10 C11 C12 0(5) . . . . ? C10 C11 C12 C13 -1(4) . . . . ? C11 C12 C13 C14 1(4) . . . . ? C2 C1 C14 C13 178.6(19) . . . . ? C15 C1 C14 C13 1(3) . . . . ? C2 C1 C14 C9 -3(3) . . . . ? C15 C1 C14 C9 179.2(18) . . . . ? C12 C13 C14 C1 179(2) . . . . ? C12 C13 C14 C9 1(3) . . . . ? C8 C9 C14 C1 2(3) . . . . ? C10 C9 C14 C1 -180(2) . . . . ? C8 C9 C14 C13 180(2) . . . . ? C10 C9 C14 C13 -2(3) . . . . ? C2 C1 C15 O2 85(2) . . . . ? C14 C1 C15 O2 -97(2) . . . . ? C2 C1 C15 O1 -97(2) . . . . ? C14 C1 C15 O1 81(3) . . . . ? N1 C16 C17 C18 -110(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 N1 H1C O1 0.99(5) 2.80(10) 2.96(3) 89(6) . N1 H1B O2 0.92(6) 1.90(16) 2.75(3) 153(29) 2_665 _diffrn_measured_fraction_theta_max 0.633 _diffrn_reflns_theta_full 64.84 _diffrn_measured_fraction_theta_full 0.633 _refine_diff_density_max 0.150 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.041 #===END data_comp3b _database_code_CSD 216548 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O3' _chemical_formula_weight 323.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 21.3642(6) _cell_length_b 18.8560(9) _cell_length_c 8.7764(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3535.5(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12 _cell_measurement_theta_min 42.22 _cell_measurement_theta_max 43.78 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.655 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 93.31 _exptl_absorpt_correction_T_max 99.96 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type MACH3 _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 3600s _diffrn_standards_decay_% 11.8 _diffrn_reflns_number 2599 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 74.16 _reflns_number_total 2599 _reflns_number_gt 2599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express, Nonius BV' _computing_cell_refinement 'Express, Nonius BV' _computing_data_reduction 'OpenMoleN, Nonius BV' _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^)+(0.0601P)^2^+3.6212P] 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 0.0035(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2599 _refine_ls_number_parameters 257 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.2078 _refine_ls_wR_factor_gt 0.2078 _refine_ls_goodness_of_fit_ref 1.344 _refine_ls_restrained_S_all 1.343 _refine_ls_shift/su_max 0.063 _refine_ls_shift/su_mean 0.004 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 0.55745(17) 0.20547(19) 0.6771(4) 0.0512(9) Uani 1 1 d . . . H1 H 0.5876 0.2360 0.7160 0.061 Uiso 1 1 calc R . . C2 C 0.5170(2) 0.2296(2) 0.5696(5) 0.0626(11) Uani 1 1 d . . . H2 H 0.5206 0.2758 0.5341 0.075 Uiso 1 1 calc R . . C3 C 0.4697(2) 0.1854(2) 0.5113(6) 0.0733(13) Uani 1 1 d . . . H3 H 0.4421 0.2028 0.4385 0.088 Uiso 1 1 calc R . . C4 C 0.4643(2) 0.1180(3) 0.5607(6) 0.0725(13) Uani 1 1 d . . . H4 H 0.4325 0.0895 0.5219 0.087 Uiso 1 1 calc R . . C5 C 0.63505(19) 0.0059(2) 0.9961(5) 0.0590(10) Uani 1 1 d . . . H5 H 0.6670 0.0337 1.0362 0.071 Uiso 1 1 calc R . . C6 C 0.6293(2) -0.0630(2) 1.0419(6) 0.0723(13) Uani 1 1 d . . . H6 H 0.6570 -0.0817 1.1131 0.087 Uiso 1 1 calc R . . C7 C 0.5815(2) -0.1059(2) 0.9815(6) 0.0769(14) Uani 1 1 d . . . H7 H 0.5781 -0.1528 1.0132 0.092 Uiso 1 1 calc R . . C8 C 0.5406(2) -0.0802(2) 0.8786(6) 0.0683(12) Uani 1 1 d . . . H8 H 0.5094 -0.1097 0.8403 0.082 Uiso 1 1 calc R . . C9 C 0.59755(15) 0.10642(17) 0.8377(4) 0.0424(8) Uani 1 1 d . . . C10 C 0.50276(19) 0.0193(2) 0.7212(5) 0.0604(11) Uani 1 1 d . . . H10 H 0.4716 -0.0098 0.6820 0.072 Uiso 1 1 calc R . . C11 C 0.55462(16) 0.13392(18) 0.7319(4) 0.0444(8) Uani 1 1 d . . . C12 C 0.50630(17) 0.08939(19) 0.6714(5) 0.0523(9) Uani 1 1 d . . . C13 C 0.59311(16) 0.03583(18) 0.8885(4) 0.0463(9) Uani 1 1 d . . . C14 C 0.54424(19) -0.00837(19) 0.8275(4) 0.0529(9) Uani 1 1 d . . . C15 C 0.65089(18) 0.15263(18) 0.8935(5) 0.0513(9) Uani 1 1 d . . . C1A C 0.8425(2) 0.1228(3) 0.9028(6) 0.0784(14) Uani 1 1 d D . . H1'1 H 0.8865 0.1300 0.9248 0.094 Uiso 1 1 calc R A 3 H1'2 H 0.8364 0.1285 0.7940 0.094 Uiso 1 1 calc R A 3 C2A' C 0.8239(7) 0.0505(5) 0.949(2) 0.109(4) Uani 0.70 1 d PD B 3 H2A' H 0.7961 0.0411 0.8701 0.131 Uiso 0.70 1 calc PR B 3 C3A' C 0.8200(7) 0.0052(8) 1.0038(17) 0.133(4) Uani 0.70 1 d PD B 3 H3A1 H 0.8430 -0.0025 1.0923 0.159 Uiso 0.70 1 calc PR B 3 H3A2 H 0.7934 -0.0298 0.9672 0.159 Uiso 0.70 1 calc PR B 3 C2A C 0.8071(10) 0.0545(10) 0.894(2) 0.067(7) Uani 0.30 1 d PD B 4 H2A H 0.7667 0.0727 0.8974 0.080 Uiso 0.30 1 calc PR B 4 C3A C 0.7966(11) 0.0038(12) 0.887(4) 0.110(9) Uani 0.30 1 d PD B 4 H3A3 H 0.8284 -0.0298 0.8819 0.132 Uiso 0.30 1 calc PR B 4 H3A4 H 0.7550 -0.0104 0.8861 0.132 Uiso 0.30 1 calc PR B 4 N1 N 0.80475(19) 0.1762(2) 0.9857(6) 0.0681(11) Uani 1 1 d . B . O1 O 0.64984(16) 0.17632(16) 1.0249(4) 0.0801(10) Uani 1 1 d . . . O2 O 0.69481(14) 0.16420(18) 0.8022(4) 0.0787(10) Uani 1 1 d . . . C1D C 0.2808(7) 0.1882(6) 0.2390(15) 0.162(4) Uani 1 1 d . . . H1D1 H 0.2755 0.1734 0.1340 0.194 Uiso 1 1 calc R C 1 H1D2 H 0.3061 0.1530 0.2907 0.194 Uiso 1 1 calc R C 1 O2D O 0.2287(11) 0.1925(9) 0.302(2) 0.161(6) Uani 0.50 1 d P . 1 O2D' O 0.2174(8) 0.1877(8) 0.1779(16) 0.137(4) Uani 0.50 1 d P . 2 C3D C 0.3123(5) 0.2562(9) 0.2434(17) 0.172(4) Uani 1 1 d . . . H3D1 H 0.3492 0.2531 0.3075 0.207 Uiso 1 1 calc R . . H3D2 H 0.3255 0.2696 0.1416 0.207 Uiso 1 1 calc R . . H1A H 0.803(2) 0.169(3) 1.098(7) 0.091(17) Uiso 1 1 d . . . H1B H 0.762(3) 0.177(3) 0.952(6) 0.097(17) Uiso 1 1 d . . . H1C H 0.823(3) 0.220(3) 0.986(6) 0.098(17) 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 C1 0.050(2) 0.0441(18) 0.060(2) -0.0057(17) 0.0012(18) 0.0045(16) C2 0.067(3) 0.053(2) 0.067(3) -0.0016(19) -0.004(2) 0.0161(19) C3 0.069(3) 0.075(3) 0.077(3) -0.001(2) -0.024(2) 0.016(2) C4 0.057(2) 0.079(3) 0.082(3) -0.014(3) -0.022(2) -0.002(2) C5 0.062(2) 0.047(2) 0.068(3) 0.0034(19) -0.007(2) -0.0019(17) C6 0.078(3) 0.055(2) 0.083(3) 0.015(2) -0.008(3) 0.005(2) C7 0.089(3) 0.043(2) 0.099(4) 0.008(2) 0.003(3) -0.009(2) C8 0.074(3) 0.045(2) 0.085(3) -0.005(2) 0.003(3) -0.016(2) C9 0.0425(17) 0.0385(16) 0.0463(18) -0.0063(15) -0.0003(15) 0.0004(14) C10 0.052(2) 0.059(2) 0.071(3) -0.012(2) -0.007(2) -0.0147(19) C11 0.0428(18) 0.0434(18) 0.0471(19) -0.0085(15) 0.0044(15) -0.0006(14) C12 0.0434(19) 0.054(2) 0.059(2) -0.0092(18) -0.0019(17) -0.0003(16) C13 0.0473(19) 0.0413(17) 0.050(2) -0.0054(16) 0.0065(16) -0.0021(15) C14 0.057(2) 0.0429(18) 0.059(2) -0.0083(17) 0.0077(18) -0.0098(17) C15 0.054(2) 0.0365(17) 0.064(2) -0.0026(17) -0.0173(19) 0.0024(16) C1A 0.071(3) 0.102(4) 0.062(3) -0.003(3) -0.006(2) -0.017(3) C2A' 0.136(12) 0.074(7) 0.118(12) -0.003(6) -0.002(9) 0.016(7) C3A' 0.139(11) 0.120(10) 0.139(11) 0.016(9) -0.016(9) 0.022(8) C2A 0.057(9) 0.110(18) 0.033(8) -0.009(8) -0.031(7) 0.007(10) C3A 0.075(13) 0.095(16) 0.16(3) -0.050(17) 0.043(16) -0.028(12) N1 0.055(2) 0.052(2) 0.097(3) 0.022(2) -0.023(2) -0.0140(17) O1 0.091(2) 0.0713(19) 0.078(2) -0.0256(17) -0.0152(18) -0.0127(17) O2 0.0558(17) 0.097(2) 0.083(2) 0.0021(18) -0.0062(17) -0.0288(16) C1D 0.192(11) 0.137(9) 0.157(9) -0.006(7) 0.031(10) 0.031(9) O2D 0.190(16) 0.139(11) 0.155(13) 0.012(10) 0.054(12) -0.060(12) O2D' 0.154(12) 0.143(10) 0.113(9) -0.030(8) -0.005(8) -0.024(8) C3D 0.122(7) 0.187(11) 0.208(12) 0.045(11) -0.009(8) -0.021(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 C1 C2 1.358(5) . ? C1 C11 1.434(5) . ? C2 C3 1.405(6) . ? C3 C4 1.348(6) . ? C4 C12 1.428(6) . ? C5 C6 1.366(6) . ? C5 C13 1.420(5) . ? C6 C7 1.406(6) . ? C7 C8 1.347(6) . ? C8 C14 1.429(5) . ? C9 C11 1.404(5) . ? C9 C13 1.407(5) . ? C9 C15 1.516(5) . ? C10 C14 1.388(6) . ? C10 C12 1.394(5) . ? C11 C12 1.433(5) . ? C13 C14 1.439(5) . ? C15 O1 1.236(5) . ? C15 O2 1.253(5) . ? C1A N1 1.480(7) . ? C1A C2A' 1.477(11) . ? C1A C2A 1.496(16) . ? C2A' C3A' 0.984(12) . ? C2A C3A 0.983(18) . ? C1D O2D 1.244(18) . ? C1D O2D' 1.457(18) . ? C1D C3D 1.449(13) . ? O2D C3D 1.40(2) 2 ? O2D' C3D 1.361(18) 2 ? C3D O2D' 1.361(18) 2 ? C3D O2D 1.40(2) 2 ? 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 C11 121.4(4) . . ? C1 C2 C3 120.8(4) . . ? C4 C3 C2 120.3(4) . . ? C3 C4 C12 121.4(4) . . ? C6 C5 C13 121.2(4) . . ? C5 C6 C7 120.1(4) . . ? C8 C7 C6 121.2(4) . . ? C7 C8 C14 121.0(4) . . ? C11 C9 C13 121.0(3) . . ? C11 C9 C15 119.5(3) . . ? C13 C9 C15 119.5(3) . . ? C14 C10 C12 122.2(3) . . ? C9 C11 C12 120.0(3) . . ? C9 C11 C1 122.8(3) . . ? C12 C11 C1 117.2(3) . . ? C10 C12 C4 122.5(4) . . ? C10 C12 C11 118.6(3) . . ? C4 C12 C11 118.9(4) . . ? C9 C13 C5 123.0(3) . . ? C9 C13 C14 118.6(3) . . ? C5 C13 C14 118.4(3) . . ? C10 C14 C8 122.2(4) . . ? C10 C14 C13 119.7(3) . . ? C8 C14 C13 118.2(4) . . ? O1 C15 O2 123.2(4) . . ? O1 C15 C9 119.7(4) . . ? O2 C15 C9 117.2(4) . . ? N1 C1A C2A' 110.2(6) . . ? N1 C1A C2A 109.6(11) . . ? C2A' C1A C2A 23.5(7) . . ? C3A' C2A' C1A 163(2) . . ? C3A C2A C1A 163(3) . . ? O2D C1D O2D' 48.1(9) . . ? O2D C1D C3D 110.3(10) . . ? O2D' C1D C3D 116.7(10) . . ? C1D O2D C3D 116.3(14) . 2 ? C3D O2D' C1D 105.8(10) 2 . ? O2D' C3D O2D 47.7(8) 2 2 ? O2D' C3D C1D 117.4(10) 2 . ? O2D C3D C1D 109.2(10) 2 . ? 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 C11 C1 C2 C3 1.8(6) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C2 C3 C4 C12 -0.6(7) . . . . ? C13 C5 C6 C7 0.5(7) . . . . ? C5 C6 C7 C8 -0.2(8) . . . . ? C6 C7 C8 C14 -0.1(8) . . . . ? C13 C9 C11 C12 -1.4(5) . . . . ? C15 C9 C11 C12 176.2(3) . . . . ? C13 C9 C11 C1 -179.9(3) . . . . ? C15 C9 C11 C1 -2.3(5) . . . . ? C2 C1 C11 C9 177.0(4) . . . . ? C2 C1 C11 C12 -1.6(5) . . . . ? C14 C10 C12 C4 179.2(4) . . . . ? C14 C10 C12 C11 0.3(6) . . . . ? C3 C4 C12 C10 -178.2(4) . . . . ? C3 C4 C12 C11 0.7(6) . . . . ? C9 C11 C12 C10 0.7(5) . . . . ? C1 C11 C12 C10 179.3(3) . . . . ? C9 C11 C12 C4 -178.2(4) . . . . ? C1 C11 C12 C4 0.4(5) . . . . ? C11 C9 C13 C5 -179.5(3) . . . . ? C15 C9 C13 C5 2.9(5) . . . . ? C11 C9 C13 C14 1.2(5) . . . . ? C15 C9 C13 C14 -176.5(3) . . . . ? C6 C5 C13 C9 -179.7(4) . . . . ? C6 C5 C13 C14 -0.3(6) . . . . ? C12 C10 C14 C8 180.0(4) . . . . ? C12 C10 C14 C13 -0.5(6) . . . . ? C7 C8 C14 C10 179.8(4) . . . . ? C7 C8 C14 C13 0.3(6) . . . . ? C9 C13 C14 C10 -0.2(5) . . . . ? C5 C13 C14 C10 -179.6(4) . . . . ? C9 C13 C14 C8 179.4(3) . . . . ? C5 C13 C14 C8 -0.1(5) . . . . ? C11 C9 C15 O1 107.5(4) . . . . ? C13 C9 C15 O1 -74.8(4) . . . . ? C11 C9 C15 O2 -73.3(4) . . . . ? C13 C9 C15 O2 104.4(4) . . . . ? N1 C1A C2A' C3A' -84(6) . . . . ? C2A C1A C2A' C3A' -177(9) . . . . ? N1 C1A C2A C3A -152(9) . . . . ? C2A' C1A C2A C3A -56(9) . . . . ? O2D' C1D O2D C3D -51.5(15) . . . 2 ? C3D C1D O2D C3D 57(2) . . . 2 ? O2D C1D O2D' C3D 48.7(13) . . . 2 ? C3D C1D O2D' C3D -45.3(16) . . . 2 ? O2D C1D C3D O2D' -58(2) . . . 2 ? O2D' C1D C3D O2D' -6(2) . . . 2 ? O2D C1D C3D O2D -6.7(19) . . . 2 ? O2D' C1D C3D O2D 45.6(19) . . . 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 N1 H1B O2 0.96(6) 1.96(6) 2.857(5) 154(5) . N1 H1A O2 1.00(6) 1.79(6) 2.787(6) 174(5) 7_756 N1 H1C O1 0.91(6) 2.08(6) 2.966(5) 167(5) 2_655 _diffrn_measured_fraction_theta_max 0.722 _diffrn_reflns_theta_full 74.16 _diffrn_measured_fraction_theta_full 0.722 _refine_diff_density_max 0.216 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.043