# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Gautam Radhakrishna Desiraju' 'Archan Dey' 'Judith A. K. Howard' 'Raju Mondal' _publ_contact_author_name 'Prof Gautam Radhakrishna Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad School of Chemistry, University of Hyderabad Andhra Pradesh 500 046 INDIA ; _publ_contact_author_email DESIRAJU@UOHYD.ERNET.IN _publ_requested_journal 'Chemical Communications' _publ_section_title ; Crystal engineering in the aminophenols. Novel carborundum network in a supramolecular homologous series. ; data_03rmd063 _database_code_depnum_ccdc_archive 'CCDC 238933' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '228 \% C' _chemical_formula_moiety (C12H10O2).(C12H12N2O) _chemical_formula_sum 'C24 H22 N2 O3' _chemical_formula_weight 386.44 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.46470(10) _cell_length_b 7.9338(2) _cell_length_c 43.4412(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1883.43(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5658 _cell_measurement_theta_min 3.750 _cell_measurement_theta_max 27.998 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'smart 6k CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15236 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 56 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2165 _reflns_number_gt 1801 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0587P)^2^+0.6645P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2165 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.03106(18) 0.82429(12) 0.109120(19) 0.0249(2) Uani 1 1 d . . . C19 C 0.2082(2) 0.82134(16) 0.05805(3) 0.0216(3) Uani 1 1 d . . . C15 C -0.1681(2) 0.96621(16) 0.06811(3) 0.0209(3) Uani 1 1 d . . . C16 C -0.1785(2) 1.01616(16) 0.03754(3) 0.0202(3) Uani 1 1 d . . . C14 C 0.0268(2) 0.86948(15) 0.07861(3) 0.0187(3) Uani 1 1 d . . . C17 C 0.0047(2) 0.97209(14) 0.01633(2) 0.0159(3) Uani 1 1 d . . . C18 C 0.1963(2) 0.87273(16) 0.02752(3) 0.0206(3) Uani 1 1 d . . . N1 N 0.0301(2) 0.19942(15) 0.13176(2) 0.0258(3) Uani 1 1 d . . . O3 O 0.0000 0.47330(16) 0.2500 0.0294(3) Uani 1 2 d S . . C5 C -0.1833(2) 0.42954(16) 0.20138(3) 0.0231(3) Uani 1 1 d . . . C6 C -0.1751(2) 0.36489(16) 0.17174(3) 0.0232(3) Uani 1 1 d . . . C3 C 0.1823(2) 0.27598(16) 0.21410(3) 0.0224(3) Uani 1 1 d . . . C1 C 0.0126(2) 0.25786(15) 0.16288(3) 0.0197(3) Uani 1 1 d . . . C4 C -0.0033(2) 0.38616(15) 0.22225(3) 0.0197(3) Uani 1 1 d . . . C2 C 0.1905(2) 0.21214(16) 0.18429(3) 0.0222(3) Uani 1 1 d . . . H16 H -0.316(3) 1.0873(19) 0.0315(3) 0.025(4) Uiso 1 1 d . . . H3 H 0.304(3) 0.244(2) 0.2294(3) 0.035(4) Uiso 1 1 d . . . H2 H 0.320(3) 0.137(2) 0.1783(3) 0.030(4) Uiso 1 1 d . . . H18 H 0.329(3) 0.832(2) 0.0135(4) 0.035(4) Uiso 1 1 d . . . H15 H -0.296(3) 1.001(2) 0.0828(3) 0.031(4) Uiso 1 1 d . . . H5 H -0.311(3) 0.505(2) 0.2073(3) 0.028(4) Uiso 1 1 d . . . H112 H 0.060(3) 0.091(2) 0.1307(4) 0.038(5) Uiso 1 1 d . . . H6 H -0.301(3) 0.397(2) 0.1569(4) 0.037(4) Uiso 1 1 d . . . H19 H 0.341(3) 0.753(2) 0.0649(3) 0.030(4) Uiso 1 1 d . . . H111 H -0.114(4) 0.221(2) 0.1211(4) 0.051(5) Uiso 1 1 d . . . H1 H 0.179(4) 0.778(3) 0.1148(4) 0.056(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0296(5) 0.0302(5) 0.0147(4) 0.0032(4) 0.0012(3) 0.0055(4) C19 0.0240(6) 0.0224(6) 0.0184(6) 0.0003(5) -0.0019(4) 0.0065(5) C15 0.0203(6) 0.0247(6) 0.0176(6) -0.0006(5) 0.0032(4) 0.0016(5) C16 0.0177(6) 0.0241(6) 0.0187(6) 0.0012(5) -0.0006(4) 0.0023(5) C14 0.0237(6) 0.0188(5) 0.0136(5) -0.0002(4) -0.0010(4) -0.0016(4) C17 0.0182(6) 0.0156(5) 0.0139(6) -0.0017(4) -0.0013(4) -0.0016(4) C18 0.0220(6) 0.0227(6) 0.0170(6) -0.0004(5) 0.0022(4) 0.0046(5) N1 0.0362(7) 0.0245(6) 0.0167(5) -0.0013(4) 0.0009(4) -0.0054(5) O3 0.0551(9) 0.0188(6) 0.0144(6) 0.000 0.0012(5) 0.000 C5 0.0227(6) 0.0220(6) 0.0246(7) 0.0001(5) 0.0025(5) 0.0036(5) C6 0.0230(6) 0.0251(6) 0.0215(6) 0.0028(5) -0.0051(5) 0.0006(5) C3 0.0234(6) 0.0236(6) 0.0201(6) 0.0022(5) -0.0044(5) 0.0010(5) C1 0.0250(6) 0.0187(6) 0.0155(6) 0.0013(4) 0.0014(4) -0.0051(5) C4 0.0274(6) 0.0175(6) 0.0142(6) 0.0004(4) 0.0019(4) -0.0025(4) C2 0.0221(6) 0.0223(6) 0.0223(6) 0.0014(5) 0.0027(5) 0.0034(5) _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 C14 1.3733(14) . ? O1 H1 0.92(2) . ? C19 C14 1.3876(17) . ? C19 C18 1.3888(16) . ? C19 H19 0.955(16) . ? C15 C16 1.3873(16) . ? C15 C14 1.3897(17) . ? C15 H15 0.984(15) . ? C16 C17 1.4046(16) . ? C16 H16 0.977(15) . ? C17 C18 1.3977(16) . ? C17 C17 1.487(2) 5_575 ? C18 H18 0.998(16) . ? N1 C1 1.4324(15) . ? N1 H112 0.880(19) . ? N1 H111 0.93(2) . ? O3 C4 1.3896(13) . ? O3 C4 1.3896(13) 3 ? C5 C4 1.3814(17) . ? C5 C6 1.3870(17) . ? C5 H5 0.956(16) . ? C6 C1 1.3858(18) . ? C6 H6 0.978(17) . ? C3 C4 1.3849(17) . ? C3 C2 1.3914(17) . ? C3 H3 0.977(16) . ? C1 C2 1.3931(17) . ? C2 H2 0.959(16) . ? 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 C14 O1 H1 112.1(11) . . ? C14 C19 C18 120.02(11) . . ? C14 C19 H19 119.9(9) . . ? C18 C19 H19 120.1(9) . . ? C16 C15 C14 120.22(11) . . ? C16 C15 H15 120.8(9) . . ? C14 C15 H15 118.9(9) . . ? C15 C16 C17 121.84(11) . . ? C15 C16 H16 117.0(8) . . ? C17 C16 H16 121.1(8) . . ? O1 C14 C19 122.50(11) . . ? O1 C14 C15 118.28(10) . . ? C19 C14 C15 119.22(11) . . ? C18 C17 C16 116.50(10) . . ? C18 C17 C17 121.71(12) . 5_575 ? C16 C17 C17 121.80(13) . 5_575 ? C19 C18 C17 122.19(11) . . ? C19 C18 H18 116.9(9) . . ? C17 C18 H18 120.9(9) . . ? C1 N1 H112 112.4(11) . . ? C1 N1 H111 110.9(12) . . ? H112 N1 H111 107.9(17) . . ? C4 O3 C4 120.33(13) . 3 ? C4 C5 C6 119.61(11) . . ? C4 C5 H5 120.1(9) . . ? C6 C5 H5 120.3(9) . . ? C1 C6 C5 120.55(11) . . ? C1 C6 H6 120.0(10) . . ? C5 C6 H6 119.4(10) . . ? C4 C3 C2 119.43(11) . . ? C4 C3 H3 119.5(10) . . ? C2 C3 H3 121.1(10) . . ? C6 C1 C2 119.38(11) . . ? C6 C1 N1 120.64(11) . . ? C2 C1 N1 119.93(11) . . ? C5 C4 C3 120.72(11) . . ? C5 C4 O3 117.03(10) . . ? C3 C4 O3 121.76(10) . . ? C3 C2 C1 120.26(11) . . ? C3 C2 H2 120.0(9) . . ? C1 C2 H2 119.7(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.310 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.045 ############################################################# # ***durham university chemical crystallography group*** # # this structure was solved by Raju Mondal on 25/03/2004 ############################################################# data_03rmd122 _database_code_depnum_ccdc_archive 'CCDC 238934' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '191.1 \% C' _chemical_formula_moiety (C6H6O2)(C12H12N2O) _chemical_formula_sum 'C18 H18 N2 O3' _chemical_formula_weight 310.34 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.4523(2) _cell_length_b 7.9556(2) _cell_length_c 35.1453(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1524.47(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4524 _cell_measurement_theta_min 2.318 _cell_measurement_theta_max 27.481 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.869048 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0242 before correction' _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 'smart 1k CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12094 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1754 _reflns_number_gt 1480 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0584P)^2^+0.3184P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1754 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 0.04037(17) 0.08440(11) 0.07622(2) 0.0263(2) Uani 1 1 d . . . C15 C 0.2013(2) 0.09407(13) 0.01182(3) 0.0199(3) Uani 1 1 d . . . C16 C 0.1757(2) 0.04950(13) -0.02621(3) 0.0201(3) Uani 1 1 d . . . C14 C 0.0252(2) 0.04398(13) 0.03822(3) 0.0195(3) Uani 1 1 d . . . O2 O 0.0000 0.43921(14) 0.2500 0.0289(3) Uani 1 2 d S . . C2 C 0.1871(2) 0.69940(13) 0.16853(3) 0.0216(3) Uani 1 1 d . . . N1 N 0.0225(2) 0.71171(13) 0.10380(3) 0.0252(3) Uani 1 1 d . . . C6 C -0.1803(2) 0.54706(14) 0.15348(3) 0.0228(3) Uani 1 1 d . . . C5 C -0.1865(2) 0.48260(14) 0.19014(3) 0.0228(3) Uani 1 1 d . . . C3 C 0.1810(2) 0.63607(14) 0.20535(3) 0.0222(3) Uani 1 1 d . . . C1 C 0.0076(2) 0.65425(13) 0.14222(3) 0.0191(3) Uani 1 1 d . . . C4 C -0.0048(2) 0.52569(13) 0.21569(3) 0.0195(3) Uani 1 1 d . . . H16 H 0.297(2) 0.0852(18) -0.0448(4) 0.027(3) Uiso 1 1 d . . . H15 H 0.342(2) 0.1615(16) 0.0198(4) 0.022(3) Uiso 1 1 d . . . H2 H 0.317(3) 0.7751(19) 0.1613(4) 0.031(4) Uiso 1 1 d . . . H6 H -0.312(3) 0.5190(19) 0.1357(4) 0.031(4) Uiso 1 1 d . . . H5 H -0.315(3) 0.4074(19) 0.1980(4) 0.032(4) Uiso 1 1 d . . . H3 H 0.309(3) 0.6658(18) 0.2236(4) 0.032(4) Uiso 1 1 d . . . H112 H -0.122(3) 0.693(2) 0.0909(5) 0.047(5) Uiso 1 1 d . . . H111 H 0.054(3) 0.821(2) 0.1020(5) 0.041(4) Uiso 1 1 d . . . H1 H 0.194(4) 0.128(3) 0.0824(5) 0.068(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0302(5) 0.0340(5) 0.0146(4) -0.0029(3) 0.0009(3) -0.0072(4) C15 0.0193(6) 0.0212(5) 0.0193(5) 0.0006(4) -0.0015(4) -0.0018(4) C16 0.0200(5) 0.0225(5) 0.0177(5) 0.0022(4) 0.0029(4) -0.0006(4) C14 0.0230(6) 0.0208(5) 0.0147(5) -0.0002(4) -0.0003(4) 0.0014(4) O2 0.0539(8) 0.0195(5) 0.0132(6) 0.000 0.0000(5) 0.000 C2 0.0210(6) 0.0230(5) 0.0208(6) -0.0006(4) 0.0022(4) -0.0029(4) N1 0.0349(6) 0.0249(5) 0.0158(5) 0.0009(4) 0.0005(4) 0.0046(4) C6 0.0224(6) 0.0254(5) 0.0205(6) -0.0028(4) -0.0053(4) -0.0004(4) C5 0.0219(6) 0.0236(5) 0.0228(6) -0.0004(4) 0.0021(4) -0.0030(4) C3 0.0236(6) 0.0243(5) 0.0186(6) -0.0027(4) -0.0036(4) -0.0014(4) C1 0.0239(6) 0.0191(5) 0.0144(5) -0.0015(4) 0.0017(4) 0.0041(4) C4 0.0274(6) 0.0181(5) 0.0131(5) -0.0007(4) 0.0015(4) 0.0023(4) _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 C14 1.3762(13) . ? O1 H1 0.93(2) . ? C15 C16 1.3895(15) . ? C15 C14 1.3935(15) . ? C15 H15 0.979(13) . ? C16 C14 1.3897(15) 5 ? C16 H16 0.972(14) . ? C14 C16 1.3897(15) 5 ? O2 C4 1.3885(12) . ? O2 C4 1.3886(12) 3 ? C2 C3 1.3893(15) . ? C2 C1 1.3934(16) . ? C2 H2 0.965(15) . ? N1 C1 1.4279(14) . ? N1 H112 0.923(18) . ? N1 H111 0.891(18) . ? C6 C5 1.3873(16) . ? C6 C1 1.3907(16) . ? C6 H6 0.979(15) . ? C5 C4 1.3800(16) . ? C5 H5 0.963(15) . ? C3 C4 1.3892(16) . ? C3 H3 0.977(15) . ? 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 C14 O1 H1 111.6(11) . . ? C16 C15 C14 119.87(10) . . ? C16 C15 H15 119.6(7) . . ? C14 C15 H15 120.6(8) . . ? C15 C16 C14 120.52(10) . 5 ? C15 C16 H16 120.2(8) . . ? C14 C16 H16 119.3(8) 5 . ? O1 C14 C16 117.85(10) . 5 ? O1 C14 C15 122.54(10) . . ? C16 C14 C15 119.60(10) 5 . ? C4 O2 C4 120.59(11) . 3 ? C3 C2 C1 120.53(10) . . ? C3 C2 H2 119.3(8) . . ? C1 C2 H2 120.1(8) . . ? C1 N1 H112 111.4(10) . . ? C1 N1 H111 113.1(10) . . ? H112 N1 H111 106.6(15) . . ? C5 C6 C1 120.57(10) . . ? C5 C6 H6 119.5(9) . . ? C1 C6 H6 119.9(9) . . ? C4 C5 C6 119.69(10) . . ? C4 C5 H5 119.5(9) . . ? C6 C5 H5 120.8(9) . . ? C2 C3 C4 119.36(10) . . ? C2 C3 H3 120.3(9) . . ? C4 C3 H3 120.3(8) . . ? C6 C1 C2 119.13(10) . . ? C6 C1 N1 120.48(10) . . ? C2 C1 N1 120.35(10) . . ? C5 C4 C3 120.68(10) . . ? C5 C4 O2 117.10(9) . . ? C3 C4 O2 121.77(9) . . ? 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 O1 H1 N1 0.93(2) 1.84(2) 2.7653(14) 169.4(17) 8_655 N1 H111 O1 0.891(18) 2.281(18) 3.1209(13) 157.0(14) 1_565 N1 H112 O1 0.923(18) 2.491(19) 3.3738(15) 160.2(14) 8_565 C6 H6 O1 0.979(15) 2.486(15) 3.3637(14) 149.0(12) 8_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.223 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.047 ############################################################# # ***durham university chemical crystallography group*** # # this structure was solved by Raju Mondal on 27/04/2004 ############################################################# data_04rmd041 _database_code_depnum_ccdc_archive 'CCDC 238935' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '246.0 \% C' _chemical_formula_moiety (C18H14O2).(C12H12N2O) _chemical_formula_sum 'C30 H26 N2 O3' _chemical_formula_weight 462.53 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.4581(2) _cell_length_b 7.9851(3) _cell_length_c 51.7327(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2254.69(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3794 _cell_measurement_theta_min 3.54 _cell_measurement_theta_max 27.39 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'SMART 6K CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15411 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -63 _diffrn_reflns_limit_l_max 63 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2201 _reflns_number_gt 1638 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0845P)^2^+0.6836P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2201 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.4726(3) 0.24983(16) 0.13177(2) 0.0284(4) Uani 1 1 d . . . C19 C 0.2950(3) 0.2573(2) 0.08900(3) 0.0255(4) Uani 1 1 d . . . C16 C 0.6775(3) 0.0614(2) 0.07132(3) 0.0243(4) Uani 1 1 d . . . C17 C 0.4942(3) 0.1080(2) 0.05378(3) 0.0187(4) Uani 1 1 d . . . C20 C 0.4980(3) 0.0527(2) 0.02632(3) 0.0183(4) Uani 1 1 d . . . C18 C 0.3049(3) 0.2075(2) 0.06331(3) 0.0248(4) Uani 1 1 d . . . C14 C 0.4761(3) 0.2066(2) 0.10606(3) 0.0211(4) Uani 1 1 d . . . C15 C 0.6686(3) 0.1101(2) 0.09708(3) 0.0250(4) Uani 1 1 d . . . C22 C 0.3202(4) 0.0990(4) 0.00906(4) 0.0600(9) Uani 1 1 d . . . C21 C 0.6779(4) -0.0473(4) 0.01656(4) 0.0589(9) Uani 1 1 d . . . O3 O 0.5000 0.6030(2) 0.2500 0.0328(5) Uani 1 2 d S . . N1 N 0.4671(3) 0.8753(2) 0.15081(3) 0.0288(4) Uani 1 1 d . . . C5 C 0.3182(3) 0.7999(2) 0.21996(3) 0.0264(4) Uani 1 1 d . . . C3 C 0.6812(3) 0.6455(2) 0.20903(3) 0.0261(4) Uani 1 1 d . . . C6 C 0.3101(3) 0.8633(2) 0.19501(3) 0.0259(4) Uani 1 1 d . . . C2 C 0.6726(3) 0.7098(2) 0.18417(3) 0.0262(4) Uani 1 1 d . . . C1 C 0.4860(3) 0.8173(2) 0.17688(3) 0.0220(4) Uani 1 1 d . . . C4 C 0.5028(3) 0.6895(2) 0.22669(3) 0.0232(4) Uani 1 1 d . . . H6 H 0.176(4) 0.938(3) 0.1903(3) 0.028(5) Uiso 1 1 d . . . H3 H 0.812(4) 0.571(3) 0.2137(4) 0.029(5) Uiso 1 1 d . . . H19 H 0.162(4) 0.329(3) 0.0946(4) 0.034(5) Uiso 1 1 d . . . H16 H 0.813(4) -0.016(3) 0.0661(4) 0.036(6) Uiso 1 1 d . . . H18 H 0.180(4) 0.250(3) 0.0521(4) 0.039(6) Uiso 1 1 d . . . H5 H 0.196(4) 0.831(3) 0.2328(4) 0.036(6) Uiso 1 1 d . . . H15 H 0.796(4) 0.072(3) 0.1088(4) 0.040(6) Uiso 1 1 d . . . H112 H 0.433(4) 0.984(3) 0.1503(4) 0.043(6) Uiso 1 1 d . . . H2 H 0.801(4) 0.680(3) 0.1714(4) 0.032(5) Uiso 1 1 d . . . H111 H 0.610(5) 0.854(3) 0.1415(5) 0.062(8) Uiso 1 1 d . . . H1 H 0.312(6) 0.295(4) 0.1364(5) 0.076(9) Uiso 1 1 d . . . H21 H 0.793(7) -0.099(5) 0.0283(7) 0.125(13) Uiso 1 1 d . . . H22 H 0.204(7) 0.175(5) 0.0142(6) 0.105(12) 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 O1 0.0345(8) 0.0354(8) 0.0154(7) -0.0032(5) -0.0022(5) 0.0054(6) C19 0.0290(10) 0.0285(10) 0.0191(9) -0.0011(7) 0.0008(7) 0.0086(8) C16 0.0235(9) 0.0295(10) 0.0198(8) -0.0010(7) 0.0009(6) 0.0038(8) C17 0.0222(9) 0.0187(9) 0.0151(8) 0.0017(6) 0.0011(6) -0.0028(7) C20 0.0211(9) 0.0180(9) 0.0159(8) 0.0022(6) 0.0014(6) -0.0025(6) C18 0.0271(10) 0.0297(10) 0.0178(8) 0.0004(7) -0.0038(7) 0.0054(8) C14 0.0282(9) 0.0220(9) 0.0131(8) -0.0003(6) -0.0004(6) -0.0023(7) C15 0.0252(9) 0.0320(10) 0.0177(9) 0.0015(7) -0.0036(7) 0.0027(8) C22 0.0517(15) 0.101(2) 0.0272(12) -0.0264(12) -0.0137(9) 0.0530(15) C21 0.0545(15) 0.101(2) 0.0214(11) -0.0221(12) -0.0169(9) 0.0517(15) O3 0.0599(13) 0.0244(10) 0.0141(9) 0.000 -0.0007(8) 0.000 N1 0.0407(10) 0.0281(10) 0.0175(8) 0.0006(6) -0.0011(7) -0.0049(8) C5 0.0283(10) 0.0302(10) 0.0208(9) -0.0038(7) 0.0051(7) 0.0009(8) C3 0.0255(10) 0.0272(10) 0.0257(10) -0.0009(7) -0.0026(7) 0.0031(8) C6 0.0278(10) 0.0275(10) 0.0224(9) -0.0020(7) -0.0022(7) 0.0037(8) C2 0.0263(10) 0.0307(10) 0.0215(9) -0.0041(7) 0.0048(7) 0.0004(8) C1 0.0289(9) 0.0223(9) 0.0149(8) -0.0022(7) -0.0016(6) -0.0063(7) C4 0.0325(10) 0.0221(9) 0.0149(9) -0.0005(7) -0.0030(7) -0.0039(7) _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 C14 1.3745(19) . ? O1 H1 0.98(3) . ? C19 C14 1.386(2) . ? C19 C18 1.388(2) . ? C19 H19 0.97(2) . ? C16 C15 1.389(2) . ? C16 C17 1.401(2) . ? C16 H16 1.00(2) . ? C17 C18 1.394(2) . ? C17 C20 1.488(2) . ? C20 C21 1.363(3) . ? C20 C22 1.369(3) . ? C18 H18 0.96(2) . ? C14 C15 1.383(2) . ? C15 H15 0.97(2) . ? C22 C21 1.389(3) 5_655 ? C22 H22 0.92(4) . ? C21 C22 1.389(3) 5_655 ? C21 H21 0.97(4) . ? O3 C4 1.3899(19) 3_655 ? O3 C4 1.3899(19) . ? N1 C1 1.430(2) . ? N1 H112 0.89(3) . ? N1 H111 0.93(3) . ? C5 C4 1.383(3) . ? C5 C6 1.387(2) . ? C5 H5 0.97(2) . ? C3 C4 1.381(2) . ? C3 C2 1.386(2) . ? C3 H3 0.96(2) . ? C6 C1 1.391(2) . ? C6 H6 0.98(2) . ? C2 C1 1.384(3) . ? C2 H2 0.99(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 C14 O1 H1 110.2(15) . . ? C14 C19 C18 119.88(16) . . ? C14 C19 H19 121.2(12) . . ? C18 C19 H19 119.0(12) . . ? C15 C16 C17 121.48(16) . . ? C15 C16 H16 117.2(12) . . ? C17 C16 H16 121.2(12) . . ? C18 C17 C16 116.85(15) . . ? C18 C17 C20 121.15(14) . . ? C16 C17 C20 122.00(15) . . ? C21 C20 C22 115.29(18) . . ? C21 C20 C17 122.51(15) . . ? C22 C20 C17 122.19(16) . . ? C19 C18 C17 122.07(16) . . ? C19 C18 H18 116.7(13) . . ? C17 C18 H18 121.2(13) . . ? O1 C14 C15 118.38(15) . . ? O1 C14 C19 122.20(15) . . ? C15 C14 C19 119.41(15) . . ? C14 C15 C16 120.29(16) . . ? C14 C15 H15 120.6(12) . . ? C16 C15 H15 119.0(13) . . ? C20 C22 C21 122.5(2) . 5_655 ? C20 C22 H22 119(2) . . ? C21 C22 H22 119(2) 5_655 . ? C20 C21 C22 122.24(19) . 5_655 ? C20 C21 H21 119(2) . . ? C22 C21 H21 118(2) 5_655 . ? C4 O3 C4 120.4(2) 3_655 . ? C1 N1 H112 111.2(14) . . ? C1 N1 H111 111.7(16) . . ? H112 N1 H111 110(2) . . ? C4 C5 C6 119.32(16) . . ? C4 C5 H5 119.4(12) . . ? C6 C5 H5 121.3(12) . . ? C4 C3 C2 119.70(17) . . ? C4 C3 H3 121.0(12) . . ? C2 C3 H3 119.3(12) . . ? C5 C6 C1 120.59(17) . . ? C5 C6 H6 118.6(11) . . ? C1 C6 H6 120.8(11) . . ? C1 C2 C3 120.50(16) . . ? C1 C2 H2 119.2(12) . . ? C3 C2 H2 120.3(12) . . ? C2 C1 C6 119.21(16) . . ? C2 C1 N1 120.72(16) . . ? C6 C1 N1 120.02(17) . . ? C3 C4 C5 120.66(16) . . ? C3 C4 O3 117.06(16) . . ? C5 C4 O3 121.80(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.312 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.055