# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Amit Delori' _publ_contact_author_email amitdelori@gmail.com loop_ _publ_author_name D.Yan A.Delori G.Lloyd B.Patel T.Friscic G.Day D.-K.Bucar ; W.Jones ; J.Lu M.Wei D.G.Evans X.Duan data_wj1109 _database_code_depnum_ccdc_archive 'CCDC 851664' #TrackingRef 'coumarin-3-carboxylic acid+4,4-bipyridine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic "coumarin-3-carboxylic acid+4,4'-bipyridine" _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C10 H6 O4), C10 H8 N2' _chemical_formula_sum 'C30 H20 N2 O8' _chemical_formula_weight 536.48 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.90990(10) _cell_length_b 20.2636(3) _cell_length_c 15.3093(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.3460(10) _cell_angle_gamma 90.00 _cell_volume 1212.60(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14319 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 21475 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.02 _diffrn_reflns_theta_max 33.73 _reflns_number_total 4793 _reflns_number_gt 2851 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material '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^)+(0.0718P)^2^+0.1858P] 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_number_reflns 4793 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1073 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1405 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _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 -0.2984(4) 0.37304(9) 0.73852(9) 0.0501(4) Uani 1 1 d . . . H1 H -0.4208 0.3984 0.7796 0.060 Uiso 1 1 calc R . . C2 C -0.2070(4) 0.30836(9) 0.75869(9) 0.0470(4) Uani 1 1 d . . . H2 H -0.2665 0.2901 0.8134 0.056 Uiso 1 1 calc R . . C3 C -0.0305(4) 0.27048(8) 0.69981(9) 0.0422(3) Uani 1 1 d . . . H3 H 0.0337 0.2264 0.7135 0.051 Uiso 1 1 calc R . . C4 C 0.0509(4) 0.29848(7) 0.62019(8) 0.0362(3) Uani 1 1 d . . . C5 C 0.3359(4) 0.28210(7) 0.48277(9) 0.0431(3) Uani 1 1 d . . . C6 C 0.2478(4) 0.35018(7) 0.45975(8) 0.0366(3) Uani 1 1 d . . . C7 C 0.0711(4) 0.38755(7) 0.51612(9) 0.0384(3) Uani 1 1 d . . . H7 H 0.0155 0.4317 0.5003 0.046 Uiso 1 1 calc R . . C8 C -0.0352(4) 0.36322(7) 0.59867(8) 0.0372(3) Uani 1 1 d . . . C9 C -0.2141(4) 0.40077(8) 0.66000(9) 0.0461(4) Uani 1 1 d . . . H9 H -0.2763 0.4451 0.6472 0.055 Uiso 1 1 calc R . . C10 C 0.3603(4) 0.38179(7) 0.37662(9) 0.0409(3) Uani 1 1 d . . . C11 C 0.7082(5) 0.38022(7) 0.09734(9) 0.0522(4) Uani 1 1 d . . . H11 H 0.6386 0.3358 0.0884 0.063 Uiso 1 1 calc R . . C12 C 0.8317(5) 0.41518(7) 0.02677(9) 0.0528(5) Uani 1 1 d . . . H12 H 0.8467 0.3944 -0.0286 0.063 Uiso 1 1 calc R . . C13 C 0.9329(3) 0.48016(6) 0.03688(7) 0.0279(2) Uani 1 1 d . . . C14 C 0.8998(4) 0.50669(6) 0.11951(8) 0.0368(3) Uani 1 1 d . . . H14 H 0.9611 0.5514 0.1301 0.044 Uiso 1 1 calc R . . C15 C 0.7779(4) 0.46832(7) 0.18680(9) 0.0401(3) Uani 1 1 d . . . H15 H 0.7617 0.4876 0.2431 0.048 Uiso 1 1 calc R . . N1 N 0.6826(3) 0.40581(6) 0.17654(7) 0.0365(3) Uani 1 1 d . . . O1 O 0.3460(5) 0.44085(6) 0.36752(9) 0.0772(5) Uani 1 1 d . . . O2 O 0.4715(3) 0.34158(5) 0.31709(6) 0.0470(3) Uani 1 1 d . . . H2W H 0.5178 0.3630 0.2719 0.087(7) Uiso 1 1 calc R . . O3 O 0.5025(4) 0.24339(6) 0.44237(8) 0.0713(4) Uani 1 1 d . . . O4 O 0.2255(3) 0.25981(5) 0.56281(6) 0.0427(3) 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 0.0571(9) 0.0599(10) 0.0332(7) -0.0149(6) 0.0016(6) 0.0139(8) C2 0.0522(9) 0.0623(10) 0.0268(6) -0.0017(6) 0.0056(6) 0.0060(7) C3 0.0514(8) 0.0464(8) 0.0293(6) 0.0065(5) 0.0065(5) 0.0093(6) C4 0.0426(7) 0.0386(7) 0.0275(5) 0.0021(5) 0.0044(5) 0.0107(6) C5 0.0569(9) 0.0411(7) 0.0318(6) 0.0118(5) 0.0145(6) 0.0155(6) C6 0.0443(7) 0.0357(7) 0.0297(6) 0.0081(5) 0.0013(5) 0.0053(6) C7 0.0497(8) 0.0316(6) 0.0338(6) 0.0040(5) -0.0038(5) 0.0065(6) C8 0.0466(7) 0.0350(6) 0.0298(6) -0.0012(5) -0.0018(5) 0.0095(6) C9 0.0585(9) 0.0426(8) 0.0369(7) -0.0094(6) -0.0045(6) 0.0144(7) C10 0.0498(8) 0.0390(7) 0.0339(6) 0.0109(5) 0.0015(6) 0.0020(6) C11 0.0895(12) 0.0341(7) 0.0327(7) 0.0077(5) -0.0030(7) -0.0254(8) C12 0.0997(13) 0.0335(7) 0.0251(6) 0.0039(5) -0.0027(7) -0.0269(8) C13 0.0305(6) 0.0264(5) 0.0267(5) 0.0054(4) -0.0024(4) -0.0044(4) C14 0.0477(7) 0.0270(6) 0.0363(6) -0.0013(5) 0.0146(5) -0.0065(5) C15 0.0516(8) 0.0354(7) 0.0340(6) 0.0009(5) 0.0148(5) -0.0041(6) N1 0.0424(6) 0.0348(6) 0.0323(5) 0.0098(4) 0.0027(4) -0.0061(5) O1 0.1354(14) 0.0375(6) 0.0603(8) 0.0189(6) 0.0338(8) 0.0137(7) O2 0.0714(7) 0.0398(6) 0.0302(5) 0.0080(4) 0.0102(4) -0.0076(5) O3 0.1100(11) 0.0593(7) 0.0464(6) 0.0220(5) 0.0406(6) 0.0458(7) O4 0.0595(6) 0.0381(5) 0.0313(4) 0.0107(4) 0.0161(4) 0.0180(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 C1 C9 1.374(2) . ? C1 C2 1.391(2) . ? C1 H1 0.9500 . ? C2 C3 1.381(2) . ? C2 H2 0.9500 . ? C3 C4 1.3882(17) . ? C3 H3 0.9500 . ? C4 O4 1.3712(15) . ? C4 C8 1.3919(19) . ? C5 O3 1.2004(17) . ? C5 O4 1.3845(15) . ? C5 C6 1.4630(19) . ? C6 C7 1.3504(19) . ? C6 C10 1.4997(18) . ? C7 C8 1.4275(19) . ? C7 H7 0.9500 . ? C8 C9 1.4074(19) . ? C9 H9 0.9500 . ? C10 O1 1.2061(18) . ? C10 O2 1.3047(18) . ? C11 N1 1.3247(18) . ? C11 C12 1.3881(19) . ? C11 H11 0.9500 . ? C12 C13 1.3826(18) . ? C12 H12 0.9500 . ? C13 C14 1.3832(17) . ? C13 C13 1.492(2) 3_765 ? C14 C15 1.3843(17) . ? C14 H14 0.9500 . ? C15 N1 1.3287(18) . ? C15 H15 0.9500 . ? O2 H2W 0.8400 . ? 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 C9 C1 C2 120.91(13) . . ? C9 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C3 C2 C1 120.56(13) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 118.31(14) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? O4 C4 C3 117.17(12) . . ? O4 C4 C8 120.55(11) . . ? C3 C4 C8 122.28(12) . . ? O3 C5 O4 115.28(12) . . ? O3 C5 C6 128.29(13) . . ? O4 C5 C6 116.38(12) . . ? C7 C6 C5 119.74(12) . . ? C7 C6 C10 117.86(12) . . ? C5 C6 C10 122.35(12) . . ? C6 C7 C8 122.41(12) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C4 C8 C9 118.22(13) . . ? C4 C8 C7 117.48(12) . . ? C9 C8 C7 124.29(13) . . ? C1 C9 C8 119.72(14) . . ? C1 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? O1 C10 O2 123.66(13) . . ? O1 C10 C6 120.54(14) . . ? O2 C10 C6 115.80(12) . . ? N1 C11 C12 123.21(13) . . ? N1 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C13 C12 C11 120.19(13) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 116.10(11) . . ? C12 C13 C13 122.24(13) . 3_765 ? C14 C13 C13 121.66(13) . 3_765 ? C13 C14 C15 120.23(12) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? N1 C15 C14 123.23(12) . . ? N1 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C11 N1 C15 117.03(11) . . ? C10 O2 H2W 109.5 . . ? C4 O4 C5 123.42(10) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 33.73 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.229 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.057 # Attachment 'coumarin-3-carboxylic acid+4,4-bipyridylethane.cif' data_wj1113 _database_code_depnum_ccdc_archive 'CCDC 851665' #TrackingRef 'coumarin-3-carboxylic acid+4,4-bipyridylethane.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic "coumarin-3-carboxylic acid+4,4'-bipyridylethane" _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2, 2(C10 H6 O4)' _chemical_formula_sum 'C32 H24 N2 O8' _chemical_formula_weight 564.53 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.3933(6) _cell_length_b 4.8921(2) _cell_length_c 16.5326(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.209(2) _cell_angle_gamma 90.00 _cell_volume 1290.80(9) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7038 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.837 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8351 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2884 _reflns_number_gt 1678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material '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^)+(0.0599P)^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_number_reflns 2884 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.893 _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 0.26928(9) 1.3640(4) 0.33104(9) 0.0379(4) Uani 1 1 d . . . H1 H 0.2424 1.5047 0.2950 0.045 Uiso 1 1 calc R . . C2 C 0.22411(9) 1.2155(4) 0.37661(9) 0.0350(4) Uani 1 1 d . . . H2 H 0.1664 1.2524 0.3721 0.042 Uiso 1 1 calc R . . C3 C 0.26390(9) 1.0135(3) 0.42852(9) 0.0300(4) Uani 1 1 d . . . C4 C 0.25038(9) 0.6689(4) 0.53074(9) 0.0350(4) Uani 1 1 d . . . C5 C 0.33940(8) 0.6029(3) 0.53907(8) 0.0287(4) Uani 1 1 d . . . C6 C 0.38397(9) 0.7392(3) 0.49276(9) 0.0305(4) Uani 1 1 d . . . H6 H 0.4412 0.6924 0.4979 0.037 Uiso 1 1 calc R . . C7 C 0.34836(9) 0.9512(3) 0.43629(8) 0.0289(4) Uani 1 1 d . . . C8 C 0.39286(9) 1.1037(3) 0.38848(9) 0.0331(4) Uani 1 1 d . . . H8 H 0.4502 1.0638 0.3916 0.040 Uiso 1 1 calc R . . C9 C 0.35432(10) 1.3096(4) 0.33736(9) 0.0372(4) Uani 1 1 d . . . H9 H 0.3852 1.4148 0.3064 0.045 Uiso 1 1 calc R . . C10 C 0.38181(9) 0.3855(4) 0.59759(9) 0.0324(4) Uani 1 1 d . . . C11 C 0.64582(10) 0.2600(4) 0.22395(10) 0.0460(5) Uani 1 1 d . . . H11 H 0.7039 0.2671 0.2497 0.055 Uiso 1 1 calc R . . C12 C 0.61622(10) 0.4218(4) 0.15542(10) 0.0443(5) Uani 1 1 d . . . H12 H 0.6536 0.5371 0.1350 0.053 Uiso 1 1 calc R . . C13 C 0.53232(9) 0.4166(3) 0.11638(8) 0.0323(4) Uani 1 1 d . . . C14 C 0.48161(10) 0.2437(4) 0.15024(10) 0.0405(4) Uani 1 1 d . . . H14 H 0.4233 0.2333 0.1260 0.049 Uiso 1 1 calc R . . C15 C 0.51574(9) 0.0880(4) 0.21862(9) 0.0412(4) Uani 1 1 d . . . H15 H 0.4799 -0.0294 0.2405 0.049 Uiso 1 1 calc R . . C16 C 0.49875(9) 0.5823(4) 0.03930(8) 0.0375(4) Uani 1 1 d . . . H16B H 0.5326 0.7505 0.0408 0.045 Uiso 1 1 calc R . . H16A H 0.4403 0.6373 0.0377 0.045 Uiso 1 1 calc R . . N1 N 0.59697(8) 0.0943(3) 0.25578(7) 0.0372(4) Uani 1 1 d . . . O1 O 0.45777(6) 0.3618(3) 0.61362(7) 0.0488(4) Uani 1 1 d . . . O2 O 0.33176(6) 0.2294(3) 0.62800(7) 0.0421(3) Uani 1 1 d . . . H2A H 0.3601 0.1300 0.6655 0.104(9) Uiso 1 1 calc R . . O3 O 0.20228(7) 0.5708(3) 0.56743(8) 0.0545(4) Uani 1 1 d . . . O4 O 0.21702(6) 0.8704(2) 0.47363(6) 0.0340(3) 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 0.0519(10) 0.0310(11) 0.0273(8) 0.0006(8) 0.0018(7) 0.0022(8) C2 0.0349(8) 0.0346(11) 0.0329(9) -0.0007(8) 0.0022(7) 0.0054(7) C3 0.0337(8) 0.0280(10) 0.0280(8) -0.0030(7) 0.0066(6) -0.0018(7) C4 0.0395(9) 0.0313(11) 0.0343(8) 0.0015(8) 0.0089(7) 0.0063(8) C5 0.0305(7) 0.0281(10) 0.0267(7) -0.0023(7) 0.0050(6) 0.0027(7) C6 0.0283(7) 0.0327(11) 0.0289(8) -0.0057(7) 0.0034(6) 0.0023(7) C7 0.0334(8) 0.0261(9) 0.0262(8) -0.0037(7) 0.0045(6) -0.0006(7) C8 0.0370(8) 0.0329(11) 0.0296(8) -0.0059(8) 0.0081(6) -0.0015(7) C9 0.0488(10) 0.0342(11) 0.0286(8) -0.0031(8) 0.0090(7) -0.0061(8) C10 0.0378(9) 0.0316(11) 0.0278(8) -0.0018(8) 0.0076(7) 0.0031(7) C11 0.0371(9) 0.0587(14) 0.0391(10) 0.0114(9) 0.0021(7) 0.0011(9) C12 0.0417(9) 0.0512(13) 0.0410(9) 0.0127(9) 0.0115(7) -0.0034(8) C13 0.0393(8) 0.0323(10) 0.0259(8) 0.0004(7) 0.0087(6) 0.0037(7) C14 0.0337(8) 0.0474(13) 0.0386(9) 0.0068(9) 0.0047(7) 0.0015(8) C15 0.0442(10) 0.0441(12) 0.0369(9) 0.0086(9) 0.0124(7) -0.0005(8) C16 0.0438(9) 0.0369(11) 0.0318(8) 0.0040(8) 0.0087(7) 0.0038(8) N1 0.0439(8) 0.0391(9) 0.0286(7) 0.0039(7) 0.0084(6) 0.0036(7) O1 0.0345(6) 0.0547(9) 0.0557(8) 0.0185(7) 0.0072(5) 0.0104(6) O2 0.0408(6) 0.0448(9) 0.0386(7) 0.0145(6) 0.0049(5) 0.0053(6) O3 0.0458(7) 0.0563(9) 0.0703(8) 0.0249(7) 0.0320(6) 0.0129(6) O4 0.0306(5) 0.0344(7) 0.0369(6) 0.0067(5) 0.0073(4) 0.0048(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 C1 C2 1.378(2) . ? C1 C9 1.399(2) . ? C1 H1 0.9500 . ? C2 C3 1.372(2) . ? C2 H2 0.9500 . ? C3 O4 1.3780(17) . ? C3 C7 1.395(2) . ? C4 O3 1.1995(18) . ? C4 O4 1.3878(19) . ? C4 C5 1.470(2) . ? C5 C6 1.349(2) . ? C5 C10 1.498(2) . ? C6 C7 1.428(2) . ? C6 H6 0.9500 . ? C7 C8 1.406(2) . ? C8 C9 1.373(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 O1 1.2180(16) . ? C10 O2 1.3026(18) . ? C11 N1 1.330(2) . ? C11 C12 1.376(2) . ? C11 H11 0.9500 . ? C12 C13 1.380(2) . ? C12 H12 0.9500 . ? C13 C14 1.390(2) . ? C13 C16 1.505(2) . ? C14 C15 1.372(2) . ? C14 H14 0.9500 . ? C15 N1 1.3334(19) . ? C15 H15 0.9500 . ? C16 C16 1.537(3) 3_665 ? C16 H16B 0.9900 . ? C16 H16A 0.9900 . ? O2 H2A 0.8400 . ? 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 120.63(15) . . ? C2 C1 H1 119.7 . . ? C9 C1 H1 119.7 . . ? C3 C2 C1 118.92(14) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 O4 117.39(12) . . ? C2 C3 C7 122.34(14) . . ? O4 C3 C7 120.27(14) . . ? O3 C4 O4 115.21(13) . . ? O3 C4 C5 128.16(15) . . ? O4 C4 C5 116.63(13) . . ? C6 C5 C4 119.54(14) . . ? C6 C5 C10 119.07(13) . . ? C4 C5 C10 121.38(13) . . ? C5 C6 C7 122.44(13) . . ? C5 C6 H6 118.8 . . ? C7 C6 H6 118.8 . . ? C3 C7 C8 117.65(14) . . ? C3 C7 C6 117.90(13) . . ? C8 C7 C6 124.45(13) . . ? C9 C8 C7 120.70(14) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C1 119.74(15) . . ? C8 C9 H9 120.1 . . ? C1 C9 H9 120.1 . . ? O1 C10 O2 124.27(15) . . ? O1 C10 C5 120.57(14) . . ? O2 C10 C5 115.16(13) . . ? N1 C11 C12 123.06(15) . . ? N1 C11 H11 118.5 . . ? C12 C11 H11 118.5 . . ? C11 C12 C13 120.06(15) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 116.53(14) . . ? C12 C13 C16 121.26(14) . . ? C14 C13 C16 122.17(14) . . ? C15 C14 C13 120.06(14) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? N1 C15 C14 122.89(15) . . ? N1 C15 H15 118.6 . . ? C14 C15 H15 118.6 . . ? C13 C16 C16 111.00(17) . 3_665 ? C13 C16 H16B 109.4 . . ? C16 C16 H16B 109.4 3_665 . ? C13 C16 H16A 109.4 . . ? C16 C16 H16A 109.4 3_665 . ? H16B C16 H16A 108.0 . . ? C11 N1 C15 117.40(14) . . ? C10 O2 H2A 109.5 . . ? C3 O4 C4 123.17(11) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.185 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.046 # Attachment 'coumarin-3-carboxylic acid+4,4-bipyridylethene.cif' data_wj1108 _database_code_depnum_ccdc_archive 'CCDC 851666' #TrackingRef 'coumarin-3-carboxylic acid+4,4-bipyridylethene.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic "coumarin-3-carboxylic acid+4,4'-bipyridylethene" _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2, 2(C10 H6 O4)' _chemical_formula_sum 'C32 H22 N2 O8' _chemical_formula_weight 562.52 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 P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.2227(4) _cell_length_b 5.02570(10) _cell_length_c 16.3150(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.9180(10) _cell_angle_gamma 90.00 _cell_volume 1306.09(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5288 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8761 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2288 _reflns_number_gt 1884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material '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^)+(0.0502P)^2^+0.4609P] 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_number_reflns 2288 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.001 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 0.60677(11) -0.0909(3) 0.61484(10) 0.0352(4) Uani 1 1 d . . . H1 H 0.5487 -0.0589 0.6126 0.042 Uiso 1 1 calc R . . C2 C 0.64708(12) -0.2891(3) 0.66576(10) 0.0398(4) Uani 1 1 d . . . H2 H 0.6165 -0.3956 0.6977 0.048 Uiso 1 1 calc R . . C3 C 0.73227(12) -0.3328(3) 0.67037(10) 0.0426(5) Uani 1 1 d . . . H3 H 0.7597 -0.4686 0.7060 0.051 Uiso 1 1 calc R . . C4 C 0.77779(11) -0.1821(3) 0.62404(10) 0.0396(4) Uani 1 1 d . . . H4 H 0.8362 -0.2114 0.6278 0.048 Uiso 1 1 calc R . . C5 C 0.73637(10) 0.0130(3) 0.57175(9) 0.0312(4) Uani 1 1 d . . . C6 C 0.74781(10) 0.3399(3) 0.46568(11) 0.0372(4) Uani 1 1 d . . . C7 C 0.65944(9) 0.4043(3) 0.46232(9) 0.0293(4) Uani 1 1 d . . . C8 C 0.61480(9) 0.2698(3) 0.51010(9) 0.0294(4) Uani 1 1 d . . . H8 H 0.5572 0.3124 0.5066 0.035 Uiso 1 1 calc R . . C9 C 0.65140(9) 0.0635(3) 0.56637(9) 0.0293(4) Uani 1 1 d . . . C10 C 0.61727(10) 0.6174(3) 0.40485(9) 0.0317(4) Uani 1 1 d . . . C1' C 0.0229(7) 0.486(2) 0.7177(5) 0.0592(18) Uani 0.65 1 d P A 1 H1' H -0.0074 0.6086 0.7449 0.071 Uiso 0.65 1 calc PR A 1 C2' C -0.0165(2) 0.3969(7) 0.6391(2) 0.0460(11) Uani 0.65 1 d P A 1 H2' H -0.0691 0.4668 0.6120 0.055 Uiso 0.65 1 calc PR A 1 C3' C 0.02504(19) 0.1996(7) 0.60211(18) 0.0317(7) Uani 0.65 1 d P A 1 C4' C 0.1017(2) 0.1176(7) 0.6464(2) 0.0374(8) Uani 0.65 1 d P A 1 H4' H 0.1327 -0.0169 0.6247 0.045 Uiso 0.65 1 calc PR A 1 C5' C 0.1334(3) 0.2349(14) 0.7238(4) 0.0406(11) Uani 0.65 1 d P A 1 H5' H 0.1861 0.1737 0.7534 0.049 Uiso 0.65 1 calc PR A 1 C6' C -0.01399(16) 0.1009(6) 0.51975(16) 0.0363(6) Uani 0.65 1 d P . 1 H6' H -0.0634 0.1883 0.4922 0.044 Uiso 0.65 1 calc PR . 1 C1" C 0.0211(11) 0.487(3) 0.7045(11) 0.0338(7) Uiso 0.35 1 d P B 2 H1" H -0.0134 0.6310 0.7153 0.041 Uiso 0.35 1 calc PR B 2 C2" C 0.0013(5) 0.3178(16) 0.6321(5) 0.0338(7) Uiso 0.35 1 d P B 2 H2" H -0.0516 0.3448 0.5964 0.041 Uiso 0.35 1 calc PR B 2 C3" C 0.0517(5) 0.1205(13) 0.6096(5) 0.0338(7) Uiso 0.35 1 d P B 2 C4" C 0.1256(5) 0.0693(15) 0.6639(5) 0.0338(7) Uiso 0.35 1 d P B 2 H4" H 0.1607 -0.0705 0.6515 0.041 Uiso 0.35 1 calc PR B 2 C5" C 0.1500(8) 0.212(3) 0.7345(8) 0.0338(7) Uiso 0.35 1 d P B 2 H5" H 0.2027 0.1767 0.7694 0.041 Uiso 0.35 1 calc PR B 2 C6" C 0.0303(3) -0.0285(11) 0.5321(3) 0.0338(7) Uiso 0.35 1 d P . 2 H6" H 0.0631 -0.1821 0.5269 0.041 Uiso 0.35 1 calc PR . 2 N1' N 0.09669(9) 0.4180(3) 0.75737(8) 0.0422(7) Uani 0.65 1 d P A 1 N1" N 0.09669(9) 0.4180(3) 0.75737(8) 0.0338(7) Uiso 0.35 1 d P B 2 O1 O 0.54102(7) 0.6273(3) 0.38632(8) 0.0496(4) Uani 1 1 d . . . O2 O 0.66798(7) 0.7843(2) 0.37870(7) 0.0387(3) Uani 1 1 d . . . H2A H 0.6407 0.8803 0.3409 0.046 Uiso 1 1 calc R . . O3 O 0.79399(8) 0.4248(3) 0.42265(10) 0.0639(5) Uani 1 1 d . . . O4 O 0.78305(7) 0.1545(2) 0.52526(7) 0.0373(3) 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 0.0417(9) 0.0323(9) 0.0317(8) -0.0024(7) 0.0070(7) -0.0021(7) C2 0.0594(12) 0.0299(9) 0.0297(9) 0.0004(7) 0.0074(8) -0.0043(8) C3 0.0633(12) 0.0302(9) 0.0306(9) 0.0015(7) -0.0004(8) 0.0085(8) C4 0.0423(10) 0.0356(9) 0.0376(9) 0.0005(8) -0.0010(7) 0.0096(8) C5 0.0352(8) 0.0274(8) 0.0301(8) -0.0012(7) 0.0037(6) 0.0020(7) C6 0.0350(9) 0.0333(9) 0.0446(10) 0.0075(8) 0.0113(7) 0.0067(7) C7 0.0317(8) 0.0274(8) 0.0290(8) -0.0009(6) 0.0065(6) 0.0041(6) C8 0.0281(8) 0.0290(8) 0.0308(8) -0.0013(7) 0.0046(6) 0.0044(6) C9 0.0337(8) 0.0262(8) 0.0276(8) -0.0030(6) 0.0047(6) 0.0008(6) C10 0.0359(9) 0.0322(9) 0.0280(8) 0.0005(7) 0.0089(7) 0.0063(7) C1' 0.063(2) 0.071(2) 0.039(4) -0.013(3) -0.002(3) -0.0016(18) C2' 0.0383(18) 0.049(2) 0.0476(19) -0.0217(16) 0.0006(14) 0.0127(14) C3' 0.0319(17) 0.0344(17) 0.0301(14) -0.0070(14) 0.0091(13) -0.0008(12) C4' 0.039(2) 0.0403(19) 0.0336(19) -0.0103(14) 0.0093(17) 0.0061(14) C5' 0.035(3) 0.047(2) 0.038(2) -0.0011(17) 0.0019(18) 0.004(2) C6' 0.0288(14) 0.0466(15) 0.0322(15) -0.0054(12) 0.0027(10) 0.0044(12) N1' 0.0543(15) 0.0401(14) 0.0318(12) -0.0103(10) 0.0066(11) -0.0095(11) O1 0.0324(7) 0.0586(8) 0.0583(8) 0.0245(7) 0.0103(6) 0.0128(6) O2 0.0404(7) 0.0370(7) 0.0364(6) 0.0120(5) 0.0016(5) 0.0022(5) O3 0.0453(8) 0.0663(9) 0.0893(11) 0.0382(8) 0.0360(8) 0.0205(7) O4 0.0299(6) 0.0369(6) 0.0450(7) 0.0086(5) 0.0070(5) 0.0078(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 C1 C2 1.380(2) . ? C1 C9 1.403(2) . ? C1 H1 0.9500 . ? C2 C3 1.387(3) . ? C2 H2 0.9500 . ? C3 C4 1.379(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(2) . ? C4 H4 0.9500 . ? C5 O4 1.3681(19) . ? C5 C9 1.388(2) . ? C6 O3 1.198(2) . ? C6 O4 1.389(2) . ? C6 C7 1.460(2) . ? C7 C8 1.343(2) . ? C7 C10 1.501(2) . ? C8 C9 1.437(2) . ? C8 H8 0.9500 . ? C10 O1 1.2175(19) . ? C10 O2 1.3019(19) . ? C1' N1' 1.294(10) . ? C1' C2' 1.393(10) . ? C1' H1' 0.9500 . ? C2' C3' 1.399(4) . ? C2' H2' 0.9500 . ? C3' C4' 1.377(4) . ? C3' C6' 1.460(4) . ? C4' C5' 1.400(7) . ? C4' H4' 0.9500 . ? C5' N1' 1.275(7) . ? C5' H5' 0.9500 . ? C6' C6' 1.327(5) 3_556 ? C6' H6' 0.9500 . ? C1" C2" 1.44(2) . ? C1" H1" 0.9500 . ? C2" C3" 1.378(9) . ? C2" H2" 0.9500 . ? C3" C4" 1.374(9) . ? C3" C6" 1.455(10) . ? C4" C5" 1.351(17) . ? C4" H4" 0.9500 . ? C5" H5" 0.9500 . ? C6" C6" 1.325(10) 3_556 ? C6" H6" 0.9500 . ? O2 H2A 0.8400 . ? 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 120.15(16) . . ? C2 C1 H1 119.9 . . ? C9 C1 H1 119.9 . . ? C1 C2 C3 120.05(16) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.97(16) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.56(16) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? O4 C5 C4 116.99(14) . . ? O4 C5 C9 121.16(14) . . ? C4 C5 C9 121.86(15) . . ? O3 C6 O4 115.38(14) . . ? O3 C6 C7 128.13(16) . . ? O4 C6 C7 116.48(14) . . ? C8 C7 C6 120.01(14) . . ? C8 C7 C10 119.34(14) . . ? C6 C7 C10 120.65(14) . . ? C7 C8 C9 122.09(14) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C5 C9 C1 118.41(14) . . ? C5 C9 C8 117.24(14) . . ? C1 C9 C8 124.35(14) . . ? O1 C10 O2 124.60(15) . . ? O1 C10 C7 120.37(15) . . ? O2 C10 C7 115.02(13) . . ? N1' C1' C2' 126.6(8) . . ? N1' C1' H1' 116.7 . . ? C2' C1' H1' 116.7 . . ? C1' C2' C3' 116.7(5) . . ? C1' C2' H2' 121.7 . . ? C3' C2' H2' 121.6 . . ? C4' C3' C2' 116.5(3) . . ? C4' C3' C6' 124.9(3) . . ? C2' C3' C6' 118.5(3) . . ? C3' C4' C5' 119.2(3) . . ? C3' C4' H4' 120.4 . . ? C5' C4' H4' 120.4 . . ? N1' C5' C4' 124.7(3) . . ? N1' C5' H5' 117.6 . . ? C4' C5' H5' 117.6 . . ? C6' C6' C3' 125.3(3) 3_556 . ? C6' C6' H6' 117.3 3_556 . ? C3' C6' H6' 117.3 . . ? C2" C1" H1" 123.5 . . ? C3" C2" C1" 126.2(9) . . ? C3" C2" H2" 116.9 . . ? C1" C2" H2" 116.9 . . ? C4" C3" C2" 116.9(7) . . ? C4" C3" C6" 120.0(7) . . ? C2" C3" C6" 123.1(8) . . ? C5" C4" C3" 121.9(8) . . ? C5" C4" H4" 119.1 . . ? C3" C4" H4" 119.1 . . ? C4" C5" H5" 119.7 . . ? C6" C6" C3" 126.5(7) 3_556 . ? C6" C6" H6" 116.7 3_556 . ? C3" C6" H6" 116.7 . . ? C5' N1' C1' 116.0(5) . . ? C10 O2 H2A 109.5 . . ? C5 O4 C6 122.60(12) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.146 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.039 # Attachment 'coumarin-3-carboxylic acid+pyridine-2,6-diamine.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 851667' #TrackingRef 'coumarin-3-carboxylic acid+pyridine-2,6-diamine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'coumarin-3-carboxylic acid+pyridine-2,6-diamine' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H5 O4, C5 H8 N3' _chemical_formula_sum 'C15 H13 N3 O4' _chemical_formula_weight 299.28 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8797(2) _cell_length_b 12.9776(5) _cell_length_c 7.3847(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.383(2) _cell_angle_gamma 90.00 _cell_volume 1330.14(12) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3814 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.885 _exptl_absorpt_correction_T_max 1.008 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7181 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.23 _reflns_number_total 2398 _reflns_number_gt 1614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material '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^)+(0.0312P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2398 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0726 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _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 0.03855(12) 0.01870(13) 0.2609(2) 0.0412(4) Uani 1 1 d . . . C2 C -0.01905(12) 0.09887(13) 0.1991(2) 0.0393(4) Uani 1 1 d . . . C3 C 0.01196(11) 0.19945(13) 0.2111(2) 0.0348(4) Uani 1 1 d . . . C4 C 0.10170(10) 0.21908(10) 0.28602(18) 0.0263(3) Uani 1 1 d . . . C5 C 0.21910(10) 0.35013(11) 0.36815(17) 0.0274(3) Uani 1 1 d . . . C6 C 0.28232(10) 0.26853(10) 0.43388(17) 0.0236(3) Uani 1 1 d . . . C7 C 0.25329(10) 0.16960(11) 0.42134(17) 0.0257(3) Uani 1 1 d . . . C8 C 0.16156(10) 0.14094(10) 0.34819(17) 0.0257(3) Uani 1 1 d . . . C9 C 0.12791(12) 0.03947(12) 0.33475(19) 0.0355(4) Uani 1 1 d . . . C10 C 0.38045(11) 0.29296(11) 0.51509(17) 0.0278(4) Uani 1 1 d . . . C11 C 0.22730(11) 0.75109(13) 0.61041(19) 0.0335(4) Uani 1 1 d . . . C12 C 0.27050(11) 0.65692(12) 0.63876(18) 0.0326(4) Uani 1 1 d . . . C13 C 0.35940(11) 0.65483(11) 0.72514(18) 0.0285(4) Uani 1 1 d . . . C14 C 0.35898(10) 0.83849(11) 0.74815(17) 0.0258(3) Uani 1 1 d . . . C15 C 0.26912(11) 0.84207(12) 0.66438(18) 0.0313(4) Uani 1 1 d . . . H1 H 0.0144(11) -0.0533(12) 0.2554(17) 0.054(5) Uiso 1 1 d . . . H2 H -0.0812(11) 0.0817(10) 0.1453(18) 0.044(4) Uiso 1 1 d . . . H3 H -0.0252(11) 0.2556(11) 0.1665(18) 0.041(4) Uiso 1 1 d . . . H7 H 0.2979(9) 0.1186(9) 0.4642(16) 0.025(4) Uiso 1 1 d . . . H9 H 0.1688(10) -0.0157(11) 0.3780(17) 0.041(4) Uiso 1 1 d . . . H11 H 0.1649(11) 0.7533(11) 0.5482(18) 0.039(4) Uiso 1 1 d . . . H12 H 0.2424(10) 0.5948(10) 0.5973(16) 0.031(4) Uiso 1 1 d . . . H15 H 0.2390(11) 0.9050(11) 0.6470(18) 0.041(4) Uiso 1 1 d . . . H1A H 0.3897(11) 0.5101(13) 0.705(2) 0.063(6) Uiso 1 1 d . . . H2A H 0.4641(12) 0.9097(11) 0.8673(19) 0.047(5) Uiso 1 1 d . . . H3A H 0.4641(12) 0.7414(10) 0.8361(19) 0.041(4) Uiso 1 1 d . . . H1B H 0.4646(12) 0.5714(11) 0.814(2) 0.042(5) Uiso 1 1 d . . . H2B H 0.3751(11) 0.9780(12) 0.8237(19) 0.056(6) Uiso 1 1 d . . . N1 N 0.40711(11) 0.56735(10) 0.76848(19) 0.0382(4) Uani 1 1 d . . . N2 N 0.40870(10) 0.92161(10) 0.80378(16) 0.0317(3) Uani 1 1 d . . . N3 N 0.40111(9) 0.74515(8) 0.77470(15) 0.0258(3) Uani 1 1 d . . . O1 O 0.42941(7) 0.21649(8) 0.56471(13) 0.0377(3) Uani 1 1 d . . . O2 O 0.40584(7) 0.38504(7) 0.52893(12) 0.0390(3) Uani 1 1 d . . . O3 O 0.23312(7) 0.44203(7) 0.36553(14) 0.0418(3) Uani 1 1 d . . . O4 O 0.13015(7) 0.32033(7) 0.29702(12) 0.0300(3) 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 0.0427(11) 0.0343(10) 0.0466(10) -0.0024(8) -0.0042(8) -0.0127(9) C2 0.0278(10) 0.0471(11) 0.0429(10) -0.0078(8) -0.0042(7) -0.0070(9) C3 0.0270(9) 0.0362(10) 0.0410(9) -0.0046(8) -0.0051(7) 0.0010(8) C4 0.0269(9) 0.0256(8) 0.0263(7) -0.0024(7) 0.0017(6) -0.0036(7) C5 0.0255(9) 0.0285(9) 0.0282(8) -0.0012(7) -0.0007(6) -0.0036(7) C6 0.0234(8) 0.0244(8) 0.0231(7) 0.0013(6) 0.0005(6) 0.0012(7) C7 0.0260(9) 0.0260(9) 0.0250(8) 0.0007(7) -0.0018(6) 0.0024(7) C8 0.0258(8) 0.0273(8) 0.0239(7) -0.0018(6) 0.0007(6) -0.0025(7) C9 0.0402(11) 0.0283(9) 0.0380(9) -0.0005(7) -0.0052(7) -0.0024(8) C10 0.0289(9) 0.0270(9) 0.0276(8) -0.0009(7) -0.0002(6) -0.0013(8) C11 0.0243(9) 0.0487(11) 0.0274(8) -0.0048(7) -0.0021(7) -0.0003(8) C12 0.0301(10) 0.0358(10) 0.0319(8) -0.0087(8) 0.0013(7) -0.0078(8) C13 0.0311(9) 0.0276(8) 0.0268(7) -0.0058(7) 0.0044(6) -0.0022(7) C14 0.0266(9) 0.0273(8) 0.0236(7) -0.0009(7) 0.0019(6) 0.0003(7) C15 0.0285(10) 0.0361(10) 0.0294(8) -0.0014(8) -0.0029(6) 0.0049(8) N1 0.0384(10) 0.0279(8) 0.0483(9) -0.0057(7) -0.0047(7) 0.0023(7) N2 0.0279(8) 0.0281(8) 0.0391(8) -0.0015(6) -0.0049(6) 0.0018(7) N3 0.0219(7) 0.0268(7) 0.0288(7) -0.0024(6) -0.0024(5) 0.0003(6) O1 0.0310(7) 0.0277(6) 0.0543(7) 0.0009(5) -0.0132(5) -0.0003(5) O2 0.0362(7) 0.0256(6) 0.0550(7) -0.0009(5) -0.0138(5) -0.0044(5) O3 0.0374(7) 0.0234(6) 0.0646(7) 0.0041(5) -0.0099(5) -0.0022(5) O4 0.0247(6) 0.0262(6) 0.0390(6) -0.0008(4) -0.0048(4) -0.0003(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 C1 C9 1.378(2) . ? C1 C2 1.388(2) . ? C1 H1 0.994(15) . ? C2 C3 1.377(2) . ? C2 H2 0.973(15) . ? C3 C4 1.383(2) . ? C3 H3 0.950(14) . ? C4 O4 1.3743(15) . ? C4 C8 1.3871(19) . ? C5 O3 1.2086(15) . ? C5 O4 1.3931(16) . ? C5 C6 1.4565(19) . ? C6 C7 1.3487(18) . ? C6 C10 1.5179(19) . ? C7 C8 1.4290(19) . ? C7 H7 0.959(13) . ? C8 C9 1.4005(19) . ? C9 H9 0.966(14) . ? C10 O2 1.2498(15) . ? C10 O1 1.2560(16) . ? C11 C15 1.374(2) . ? C11 C12 1.377(2) . ? C11 H11 0.978(15) . ? C12 C13 1.385(2) . ? C12 H12 0.946(13) . ? C13 N1 1.3517(18) . ? C13 N3 1.3565(17) . ? C14 N2 1.3434(17) . ? C14 N3 1.3587(16) . ? C14 C15 1.3893(19) . ? C15 H15 0.926(14) . ? N1 H1A 0.909(16) . ? N1 H1B 0.867(15) . ? N2 H2A 0.911(16) . ? N2 H2B 0.881(16) . ? N3 H3A 0.984(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 C9 C1 C2 119.91(16) . . ? C9 C1 H1 120.2(9) . . ? C2 C1 H1 119.9(9) . . ? C3 C2 C1 120.68(16) . . ? C3 C2 H2 121.3(8) . . ? C1 C2 H2 118.0(9) . . ? C2 C3 C4 118.72(16) . . ? C2 C3 H3 122.4(9) . . ? C4 C3 H3 118.9(9) . . ? O4 C4 C3 117.21(13) . . ? O4 C4 C8 120.54(12) . . ? C3 C4 C8 122.24(14) . . ? O3 C5 O4 114.23(12) . . ? O3 C5 C6 128.76(13) . . ? O4 C5 C6 117.01(12) . . ? C7 C6 C5 119.35(13) . . ? C7 C6 C10 119.53(12) . . ? C5 C6 C10 121.12(12) . . ? C6 C7 C8 122.60(13) . . ? C6 C7 H7 116.3(7) . . ? C8 C7 H7 121.1(7) . . ? C4 C8 C9 117.73(13) . . ? C4 C8 C7 117.71(13) . . ? C9 C8 C7 124.57(14) . . ? C1 C9 C8 120.72(16) . . ? C1 C9 H9 120.7(8) . . ? C8 C9 H9 118.5(8) . . ? O2 C10 O1 125.43(13) . . ? O2 C10 C6 118.94(13) . . ? O1 C10 C6 115.63(12) . . ? C15 C11 C12 122.42(15) . . ? C15 C11 H11 118.8(9) . . ? C12 C11 H11 118.8(9) . . ? C11 C12 C13 118.23(15) . . ? C11 C12 H12 121.9(8) . . ? C13 C12 H12 119.8(8) . . ? N1 C13 N3 117.02(14) . . ? N1 C13 C12 123.97(15) . . ? N3 C13 C12 118.98(14) . . ? N2 C14 N3 116.87(13) . . ? N2 C14 C15 124.55(14) . . ? N3 C14 C15 118.57(14) . . ? C11 C15 C14 118.48(15) . . ? C11 C15 H15 121.9(9) . . ? C14 C15 H15 119.6(9) . . ? C13 N1 H1A 115.9(10) . . ? C13 N1 H1B 119.3(10) . . ? H1A N1 H1B 119.4(14) . . ? C14 N2 H2A 116.8(9) . . ? C14 N2 H2B 116.5(10) . . ? H2A N2 H2B 120.0(14) . . ? C13 N3 C14 123.29(13) . . ? C13 N3 H3A 117.3(8) . . ? C14 N3 H3A 119.4(8) . . ? C4 O4 C5 122.77(11) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.148 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.039