# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Venkataraman, D.' 'Field, Jason E.' _publ_requested_journal 'Chemical Communications' _audit_creation_method 'maXus' _publ_contact_author_name 'Dr D Venkataraman' _publ_contact_author_address ; Chemistry University of Massachusetts 710 N. Pleasant Street LGRT Amherst Massachusetts 01002 UNITED STATES OF AMERICA ; _publ_contact_author_email 'DV@CHEM.UMASS.EDU' _publ_contact_author_fax '413 545-2290 ' _publ_contact_author_phone '413 545-2028' _publ_section_title ; Helix vs. Zig-Zag: Control of Supramolecular Topology via Carboxylic Acid Conformations in ortho-Substituted Arylamines ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of Gottingen, Germany. ; data_1 _database_code_CSD 173736 _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Cube' _exptl_crystal_colour 'Yellow' _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment 'noref' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 251.269 _diffrn_radiation_type ' MoK\a' 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' '-X,+Y,-Z+ 1/2' '+X,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,+Z+ 1/2' '-X+ 1/2,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C14 H11 N O4 ' _chemical_formula_sum 'C14 H11 N O4 ' _chemical_name_systematic ; ? ; _cell_length_a 13.1691(7) _cell_length_b 8.3651(5) _cell_length_c 11.7215(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.639(3) _cell_angle_gamma 90.00 _cell_volume 1208.38(11) _diffrn_reflns_number 2452 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_full 27.49 _cell_measurement_reflns_used 3823 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' 'O' 'O' 0.0106 0.0060 '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' _exptl_absorpt_coefficient_mu 0.105 _reflns_number_total 1387 _reflns_number_gt 1119 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0630P)^2^+0.4942P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1387 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 O1 O 0.49827(10) 0.12557(12) 0.39104(11) 0.0589(4) Uani 1 1 d . . . O2 O 0.41316(9) 0.15244(13) 0.52326(10) 0.0584(4) Uani 1 1 d . . . N1 N 0.5000 0.3796(2) 0.2500 0.0483(4) Uani 1 2 d S . . C1 C 0.43350(11) 0.45101(17) 0.30427(11) 0.0405(3) Uani 1 1 d . . . C2 C 0.40129(10) 0.36709(16) 0.39045(11) 0.0394(3) Uani 1 1 d . . . C3 C 0.32810(12) 0.43805(18) 0.43733(13) 0.0478(4) Uani 1 1 d . . . C4 C 0.28792(13) 0.5891(2) 0.40330(15) 0.0570(4) Uani 1 1 d . . . C5 C 0.32167(12) 0.6730(2) 0.32115(14) 0.0557(4) Uani 1 1 d . . . C6 C 0.39159(13) 0.60549(18) 0.27137(13) 0.0497(4) Uani 1 1 d . . . C7 C 0.44187(11) 0.20580(16) 0.43337(12) 0.0422(3) Uani 1 1 d . . . H2 H 0.4383 0.0627 0.5428 0.070 Uiso 1 1 d R . . H1 H 0.5000 0.2767 0.2500 0.058 Uiso 1 2 d SR . . H3 H 0.3063 0.3816 0.4931 0.057 Uiso 1 1 d R . . H4 H 0.2387 0.6342 0.4347 0.068 Uiso 1 1 d R . . H5 H 0.2967 0.7767 0.2995 0.067 Uiso 1 1 d R . . H6 H 0.4116 0.6632 0.2149 0.060 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0857(8) 0.0469(6) 0.0659(7) 0.0091(5) 0.0538(6) 0.0140(5) O2 0.0791(8) 0.0511(6) 0.0659(7) 0.0122(5) 0.0515(6) 0.0103(5) N1 0.0706(11) 0.0385(8) 0.0504(9) 0.000 0.0395(8) 0.000 C1 0.0458(7) 0.0436(7) 0.0340(6) -0.0046(5) 0.0165(5) -0.0012(5) C2 0.0426(7) 0.0416(7) 0.0368(6) -0.0044(5) 0.0175(5) -0.0023(5) C3 0.0499(8) 0.0536(8) 0.0462(7) -0.0049(6) 0.0248(6) -0.0002(6) C4 0.0540(9) 0.0607(9) 0.0615(9) -0.0068(7) 0.0269(7) 0.0115(7) C5 0.0580(9) 0.0500(8) 0.0559(9) 0.0027(7) 0.0161(7) 0.0134(7) C6 0.0593(9) 0.0482(8) 0.0416(7) 0.0042(6) 0.0179(6) 0.0031(6) C7 0.0487(7) 0.0431(7) 0.0422(7) -0.0029(5) 0.0252(6) -0.0045(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 O1 C7 1.2281(16) . ? O2 C7 1.3165(15) . ? N1 C1 1.3862(14) 2_655 ? N1 C1 1.3862(14) . ? C1 C6 1.405(2) . ? C1 C2 1.4125(18) . ? C2 C3 1.3988(18) . ? C2 C7 1.4729(19) . ? C3 C4 1.374(2) . ? C4 C5 1.385(2) . ? C5 C6 1.373(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 C1 N1 C1 128.91(16) 2_655 . ? N1 C1 C6 121.42(12) . . ? N1 C1 C2 120.76(13) . . ? C6 C1 C2 117.75(12) . . ? C3 C2 C1 119.49(13) . . ? C3 C2 C7 118.15(12) . . ? C1 C2 C7 122.36(11) . . ? C4 C3 C2 121.64(14) . . ? C3 C4 C5 118.87(14) . . ? C6 C5 C4 120.94(14) . . ? C5 C6 C1 121.28(14) . . ? O1 C7 O2 121.55(13) . . ? O1 C7 C2 124.12(12) . . ? O2 C7 C2 114.33(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.129 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.041 #==END data_2 _database_code_CSD 173737 _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Cube' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment 'noref' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.03148 _diffrn_orient_matrix_UB_12 0.08877 _diffrn_orient_matrix_UB_13 -0.04517 _diffrn_orient_matrix_UB_21 -0.03009 _diffrn_orient_matrix_UB_22 -0.08258 _diffrn_orient_matrix_UB_23 -0.05880 _diffrn_orient_matrix_UB_31 -0.06063 _diffrn_orient_matrix_UB_32 0.08707 _diffrn_orient_matrix_UB_33 -0.00972 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 258.229 _diffrn_radiation_type ' MoK\a' 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' '-X,+Y,-Z+ 1/2' '+X,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,+Z+ 1/2' '-X+ 1/2,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C14 H10 O5 ' _chemical_formula_sum 'C14 H10 O5 ' _chemical_name_systematic ; ? ; _cell_length_a 13.5889(5) _cell_length_b 6.6994(3) _cell_length_c 13.5648(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.660(2) _cell_angle_gamma 90.00 _cell_volume 1217.39(9) _diffrn_reflns_number 1972 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_av_R_equivalents 0.023 _cell_measurement_reflns_used 1123 _cell_measurement_theta_min 4.076 _cell_measurement_theta_max 25.028 _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _exptl_absorpt_coefficient_mu 0.108 _reflns_number_total 1057 _reflns_number_gt 872 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0649P)^2^+1.1907P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1057 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1455 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 O1 O 0.0000 0.3989(3) 0.2500 0.0669(7) Uani 1 2 d S . . O2 O -0.02215(13) 0.1571(3) 0.09682(14) 0.0820(7) Uani 1 1 d . . . O3 O 0.09325(14) 0.1623(3) 0.00074(14) 0.0832(7) Uani 1 1 d . . . C1 C 0.06804(14) 0.5014(3) 0.20476(14) 0.0472(6) Uani 1 1 d . . . C2 C 0.09719(14) 0.4181(3) 0.11979(14) 0.0457(5) Uani 1 1 d . . . C3 C 0.17277(16) 0.5137(4) 0.07966(16) 0.0573(6) Uani 1 1 d . . . C4 C 0.21614(17) 0.6858(4) 0.12109(18) 0.0657(7) Uani 1 1 d . . . C5 C 0.18519(16) 0.7673(4) 0.20370(17) 0.0613(7) Uani 1 1 d . . . C6 C 0.11287(16) 0.6745(3) 0.24667(16) 0.0572(6) Uani 1 1 d . . . C8 C 0.05399(14) 0.2347(3) 0.06939(15) 0.0498(6) Uani 1 1 d . . . H2 H -0.0388 0.0573 0.0631 0.123 Uiso 1 1 calc R . . H3 H 0.1948 0.4417 0.0249 0.069 Uiso 1 1 d R . . H4 H 0.2665 0.7473 0.0935 0.079 Uiso 1 1 d R . . H5 H 0.2163 0.9016 0.2333 0.074 Uiso 1 1 d R . . H6 H 0.0892 0.7332 0.3089 0.069 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0852(16) 0.0480(12) 0.0823(15) 0.000 0.0566(13) 0.000 O2 0.0793(12) 0.0853(13) 0.0919(13) -0.0284(10) 0.0449(10) -0.0314(10) O3 0.0966(13) 0.0795(13) 0.0870(13) -0.0267(10) 0.0548(11) -0.0268(10) C1 0.0458(11) 0.0497(12) 0.0498(11) 0.0084(9) 0.0187(9) 0.0048(9) C2 0.0448(10) 0.0503(12) 0.0429(10) 0.0061(8) 0.0105(8) 0.0006(9) C3 0.0588(13) 0.0685(15) 0.0482(11) -0.0005(10) 0.0194(10) -0.0086(11) C4 0.0612(14) 0.0767(17) 0.0625(14) 0.0025(12) 0.0201(11) -0.0210(12) C5 0.0547(13) 0.0640(15) 0.0646(14) -0.0039(11) 0.0085(10) -0.0106(10) C6 0.0584(13) 0.0620(14) 0.0535(12) -0.0042(10) 0.0156(10) 0.0008(10) C8 0.0484(11) 0.0556(13) 0.0488(11) 0.0050(9) 0.0174(9) -0.0009(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.376(2) . ? O1 C1 1.376(2) 2 ? O2 C8 1.268(2) . ? O3 C8 1.246(2) . ? C1 C6 1.387(3) . ? C1 C2 1.397(3) . ? C2 C3 1.396(3) . ? C2 C8 1.479(3) . ? C3 C4 1.372(3) . ? C4 C5 1.374(3) . ? C5 C6 1.373(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 C1 O1 C1 120.1(2) . 2 ? O1 C1 C6 121.10(17) . . ? O1 C1 C2 118.24(19) . . ? C6 C1 C2 120.45(18) . . ? C3 C2 C1 117.87(19) . . ? C3 C2 C8 117.50(18) . . ? C1 C2 C8 124.63(17) . . ? C4 C3 C2 121.3(2) . . ? C3 C4 C5 119.9(2) . . ? C6 C5 C4 120.3(2) . . ? C5 C6 C1 120.1(2) . . ? O3 C8 O2 122.2(2) . . ? O3 C8 C2 118.82(18) . . ? O2 C8 C2 119.02(18) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.163 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.034 #==END data_3 _database_code_CSD 173738 _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Cube' _exptl_crystal_colour 'yellow' _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment 'noref' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.10848 _diffrn_orient_matrix_UB_12 -0.00024 _diffrn_orient_matrix_UB_13 -0.00793 _diffrn_orient_matrix_UB_21 -0.00670 _diffrn_orient_matrix_UB_22 0.00940 _diffrn_orient_matrix_UB_23 -0.09195 _diffrn_orient_matrix_UB_31 0.00856 _diffrn_orient_matrix_UB_32 0.05949 _diffrn_orient_matrix_UB_33 0.00546 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 333.343 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C20 H15 N O4 ' _chemical_formula_sum 'C20 H15 N O4 ' _chemical_name_systematic ; ? ; _cell_length_a 9.2755(2) _cell_length_b 10.7912(4) _cell_length_c 16.7186(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.629(2) _cell_angle_gamma 90.00 _cell_volume 1658.61(8) _diffrn_reflns_number 5471 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_full 25.03 _cell_measurement_reflns_used 2977 _cell_measurement_theta_min 4.076 _cell_measurement_theta_max 25.028 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.094 _reflns_number_total 2901 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0619P)^2^+0.2818P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2901 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 O1 O 0.30521(14) 0.14402(11) 0.27518(7) 0.0630(4) Uani 1 1 d . . . O2 O 0.31727(14) -0.05084(12) 0.31186(7) 0.0625(4) Uani 1 1 d . . . O3 O 0.38832(14) 0.28880(14) 0.16470(7) 0.0740(4) Uani 1 1 d . . . O7 O 0.47321(16) 0.38644(17) 0.06617(8) 0.0899(5) Uani 1 1 d . . . N1 N 0.14096(13) 0.14111(11) 0.11463(7) 0.0427(3) Uani 1 1 d . . . C1 C 0.01895(15) 0.10641(14) 0.15389(8) 0.0403(4) Uani 1 1 d . . . C2 C -0.06476(19) 0.19814(17) 0.18343(10) 0.0536(4) Uani 1 1 d . . . C3 C -0.1847(2) 0.1667(2) 0.22004(11) 0.0664(5) Uani 1 1 d . . . C4 C -0.2217(2) 0.0450(2) 0.22897(12) 0.0678(5) Uani 1 1 d . . . C5 C -0.13840(19) -0.04613(19) 0.20062(11) 0.0619(5) Uani 1 1 d . . . C6 C -0.01891(17) -0.01605(15) 0.16282(9) 0.0483(4) Uani 1 1 d . . . C7 C 0.24703(15) 0.04820(14) 0.10511(9) 0.0418(4) Uani 1 1 d . . . C8 C 0.27231(17) 0.01038(16) 0.02863(9) 0.0493(4) Uani 1 1 d . . . C9 C 0.36583(19) -0.08617(18) 0.01901(11) 0.0592(5) Uani 1 1 d . . . C10 C 0.43536(19) -0.14794(19) 0.08520(11) 0.0621(5) Uani 1 1 d . . . C11 C 0.41309(18) -0.11080(17) 0.16151(11) 0.0549(4) Uani 1 1 d . . . C12 C 0.32243(16) -0.01153(15) 0.17269(9) 0.0451(4) Uani 1 1 d . . . C13 C 0.11986(17) 0.23537(14) 0.05376(9) 0.0441(4) Uani 1 1 d . . . C14 C -0.01236(19) 0.24383(16) 0.00410(10) 0.0540(4) Uani 1 1 d . . . C15 C -0.0322(2) 0.32704(18) -0.05874(10) 0.0628(5) Uani 1 1 d . . . C16 C 0.0792(2) 0.40245(18) -0.07496(11) 0.0668(5) Uani 1 1 d . . . C17 C 0.2099(2) 0.39776(18) -0.02560(11) 0.0624(5) Uani 1 1 d . . . C18 C 0.23221(18) 0.31636(15) 0.04016(9) 0.0490(4) Uani 1 1 d . . . C19 C 0.31333(16) 0.02520(16) 0.25777(9) 0.0483(4) Uani 1 1 d . . . C20 C 0.36932(19) 0.32653(16) 0.09611(10) 0.0542(4) Uani 1 1 d . . . H1 H 0.3062 0.1851 0.2340 0.095 Uiso 1 1 calc R . . H7 H 0.5360 0.4072 0.1029 0.135 Uiso 1 1 calc R . . H2 H -0.0399 0.2810 0.1785 0.064 Uiso 1 1 d R . . H3 H -0.2410 0.2289 0.2388 0.080 Uiso 1 1 d R . . H4 H -0.3022 0.0244 0.2539 0.081 Uiso 1 1 d R . . H5 H -0.1625 -0.1289 0.2068 0.074 Uiso 1 1 d R . . H6 H 0.0360 -0.0786 0.1434 0.058 Uiso 1 1 d R . . H8 H 0.2255 0.0508 -0.0166 0.059 Uiso 1 1 d R . . H9 H 0.3820 -0.1097 -0.0326 0.071 Uiso 1 1 d R . . H10 H 0.4968 -0.2141 0.0785 0.075 Uiso 1 1 d R . . H11 H 0.4595 -0.1528 0.2062 0.066 Uiso 1 1 d R . . H14 H -0.0887 0.1923 0.0135 0.065 Uiso 1 1 d R . . H15 H -0.1222 0.3322 -0.0906 0.075 Uiso 1 1 d R . . H16 H 0.0665 0.4561 -0.1188 0.080 Uiso 1 1 d R . . H17 H 0.2852 0.4497 -0.0361 0.075 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0874(9) 0.0572(8) 0.0431(6) -0.0030(5) 0.0035(6) -0.0106(7) O2 0.0665(8) 0.0701(8) 0.0507(7) 0.0139(6) 0.0073(5) 0.0128(6) O3 0.0738(9) 0.0898(10) 0.0541(8) 0.0130(7) -0.0073(6) -0.0392(8) O7 0.0784(10) 0.1306(14) 0.0595(8) 0.0122(8) 0.0048(7) -0.0555(10) N1 0.0420(7) 0.0433(7) 0.0424(7) 0.0024(5) 0.0043(5) -0.0037(6) C1 0.0384(8) 0.0440(9) 0.0367(8) -0.0001(6) -0.0011(6) -0.0024(7) C2 0.0575(10) 0.0501(10) 0.0533(10) -0.0035(7) 0.0083(7) 0.0011(8) C3 0.0611(12) 0.0778(14) 0.0627(11) -0.0021(9) 0.0174(9) 0.0122(10) C4 0.0475(10) 0.0888(15) 0.0691(12) 0.0161(10) 0.0151(8) -0.0011(10) C5 0.0514(10) 0.0627(12) 0.0705(12) 0.0165(9) 0.0038(8) -0.0114(9) C6 0.0449(9) 0.0447(9) 0.0543(9) 0.0029(7) 0.0027(7) -0.0032(7) C7 0.0369(8) 0.0434(8) 0.0449(8) -0.0023(6) 0.0049(6) -0.0079(7) C8 0.0459(9) 0.0572(10) 0.0445(9) -0.0043(7) 0.0048(6) -0.0117(8) C9 0.0529(10) 0.0697(12) 0.0570(11) -0.0161(9) 0.0151(8) -0.0080(9) C10 0.0501(10) 0.0665(12) 0.0718(12) -0.0089(9) 0.0154(8) 0.0066(9) C11 0.0442(9) 0.0597(11) 0.0605(10) 0.0045(8) 0.0061(7) 0.0045(8) C12 0.0371(8) 0.0517(9) 0.0460(8) 0.0006(7) 0.0044(6) -0.0032(7) C13 0.0517(9) 0.0410(8) 0.0389(8) -0.0003(6) 0.0037(6) -0.0035(7) C14 0.0559(10) 0.0524(10) 0.0513(9) 0.0023(8) -0.0019(7) -0.0064(8) C15 0.0676(12) 0.0662(12) 0.0511(10) 0.0066(9) -0.0050(8) 0.0050(10) C16 0.0860(14) 0.0609(12) 0.0525(10) 0.0152(8) 0.0055(9) 0.0009(10) C17 0.0760(13) 0.0584(11) 0.0537(10) 0.0077(8) 0.0114(9) -0.0132(9) C18 0.0567(10) 0.0481(9) 0.0426(8) 0.0004(7) 0.0075(7) -0.0083(8) C19 0.0391(8) 0.0585(11) 0.0461(9) 0.0039(8) 0.0012(6) 0.0007(7) C20 0.0595(11) 0.0562(10) 0.0476(10) -0.0018(8) 0.0097(7) -0.0183(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 O1 C19 1.319(2) . ? O2 C19 1.2182(19) . ? O3 C20 1.208(2) . ? O7 C20 1.313(2) . ? N1 C7 1.428(2) . ? N1 C1 1.4315(19) . ? N1 C13 1.4338(19) . ? C1 C6 1.380(2) . ? C1 C2 1.389(2) . ? C2 C3 1.381(3) . ? C3 C4 1.371(3) . ? C4 C5 1.373(3) . ? C5 C6 1.385(2) . ? C7 C8 1.392(2) . ? C7 C12 1.404(2) . ? C8 C9 1.379(3) . ? C9 C10 1.377(3) . ? C10 C11 1.379(2) . ? C11 C12 1.390(2) . ? C12 C19 1.490(2) . ? C13 C14 1.390(2) . ? C13 C18 1.402(2) . ? C14 C15 1.376(2) . ? C15 C16 1.371(3) . ? C16 C17 1.374(3) . ? C17 C18 1.401(2) . ? C18 C20 1.479(2) . ? O1 H1 0.8200 . ? O7 H7 0.8200 . ? C2 H2 0.9299 . ? C3 H3 0.9299 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6 0.9301 . ? C8 H8 0.9300 . ? C9 H9 0.9301 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C14 H14 0.9300 . ? C15 H15 0.9301 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C1 117.76(12) . . ? C7 N1 C13 116.75(12) . . ? C1 N1 C13 117.99(12) . . ? C6 C1 C2 118.79(14) . . ? C6 C1 N1 121.86(14) . . ? C2 C1 N1 119.35(14) . . ? C3 C2 C1 120.25(17) . . ? C4 C3 C2 120.76(18) . . ? C3 C4 C5 119.23(17) . . ? C4 C5 C6 120.69(18) . . ? C1 C6 C5 120.27(16) . . ? C8 C7 C12 118.56(15) . . ? C8 C7 N1 120.72(13) . . ? C12 C7 N1 120.63(13) . . ? C9 C8 C7 120.95(15) . . ? C10 C9 C8 120.46(16) . . ? C9 C10 C11 119.43(17) . . ? C10 C11 C12 121.08(17) . . ? C11 C12 C7 119.42(15) . . ? C11 C12 C19 116.46(14) . . ? C7 C12 C19 124.12(14) . . ? C14 C13 C18 118.58(14) . . ? C14 C13 N1 119.81(14) . . ? C18 C13 N1 121.54(13) . . ? C15 C14 C13 121.14(16) . . ? C16 C15 C14 120.71(17) . . ? C15 C16 C17 119.20(17) . . ? C16 C17 C18 121.40(17) . . ? C17 C18 C13 118.87(15) . . ? C17 C18 C20 118.34(15) . . ? C13 C18 C20 122.62(14) . . ? O2 C19 O1 119.20(15) . . ? O2 C19 C12 121.99(16) . . ? O1 C19 C12 118.78(14) . . ? O3 C20 O7 120.39(16) . . ? O3 C20 C18 125.47(15) . . ? O7 C20 C18 114.09(15) . . ? C19 O1 H1 109.5 . . ? C20 O7 H7 109.5 . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.8 . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.4 . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.7 . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.266 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.031 #==END