# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'C. Aakeroy' 'John Desper' 'Benjamin M. T. Scott' _publ_contact_author_name 'C. Aakeroy' _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Kansas 66506-3701 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Balancing supramolecular reagents for reliable formation of co-crystals ; # Attachment 'all.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 292716' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-[(1-pyrazolyl)methyl]benzamide)2, oxalic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H11 N3 O)2 (C2 H2 O4) ; _chemical_formula_sum 'C24 H24 N6 O6' _chemical_formula_weight 492.49 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 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 4.2359(8) _cell_length_b 49.029(9) _cell_length_c 5.5087(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.780(4) _cell_angle_gamma 90.00 _cell_volume 1142.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2346 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 28.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.106 _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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8069 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -63 _diffrn_reflns_limit_k_max 64 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.39 _reflns_number_total 2638 _reflns_number_gt 2435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0400P)^2^+1.4000P] 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 2638 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1489 _refine_ls_goodness_of_fit_ref 1.253 _refine_ls_restrained_S_all 1.253 _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 N11 N 0.6417(5) 0.18976(4) 0.6722(4) 0.0171(4) Uani 1 1 d . . . N12 N 0.5162(5) 0.19404(4) 0.8895(4) 0.0201(5) Uani 1 1 d . . . C13 C 0.3382(6) 0.21633(5) 0.8550(5) 0.0227(5) Uani 1 1 d . . . H13 H 0.2188 0.2245 0.9772 0.027 Uiso 1 1 calc R . . C14 C 0.3488(6) 0.22618(5) 0.6182(5) 0.0259(6) Uani 1 1 d . . . H14 H 0.2426 0.2416 0.5500 0.031 Uiso 1 1 calc R . . C15 C 0.5458(6) 0.20866(5) 0.5061(5) 0.0219(5) Uani 1 1 d . . . H15 H 0.6044 0.2096 0.3420 0.026 Uiso 1 1 calc R . . C21 C 0.3143(5) 0.09348(4) 0.4322(4) 0.0150(5) Uani 1 1 d . . . C22 C 0.4766(6) 0.09530(5) 0.6580(5) 0.0202(5) Uani 1 1 d . . . H22 H 0.4720 0.0805 0.7685 0.024 Uiso 1 1 calc R . . C23 C 0.6453(6) 0.11879(5) 0.7219(5) 0.0202(5) Uani 1 1 d . . . H23 H 0.7554 0.1198 0.8760 0.024 Uiso 1 1 calc R . . C24 C 0.6553(5) 0.14072(5) 0.5648(5) 0.0178(5) Uani 1 1 d . . . C25 C 0.4926(6) 0.13901(5) 0.3383(5) 0.0185(5) Uani 1 1 d . . . H25 H 0.4975 0.1539 0.2283 0.022 Uiso 1 1 calc R . . C26 C 0.3240(5) 0.11565(5) 0.2737(4) 0.0172(5) Uani 1 1 d . . . H26 H 0.2137 0.1147 0.1196 0.021 Uiso 1 1 calc R . . C27 C 0.1313(5) 0.06882(5) 0.3496(4) 0.0172(5) Uani 1 1 d . . . N27 N 0.1488(6) 0.04666(4) 0.4859(4) 0.0238(5) Uani 1 1 d . . . H27A H 0.040(7) 0.0316(6) 0.438(6) 0.029 Uiso 1 1 d . . . H27B H 0.262(8) 0.0454(6) 0.611(6) 0.029 Uiso 1 1 d . . . O27 O -0.0317(4) 0.06981(3) 0.1545(3) 0.0211(4) Uani 1 1 d . . . C28 C 0.8416(6) 0.16611(5) 0.6354(5) 0.0212(5) Uani 1 1 d . . . H28A H 0.9697 0.1625 0.7870 0.025 Uiso 1 1 calc R . . H28B H 0.9888 0.1703 0.5063 0.025 Uiso 1 1 calc R . . C31 C -0.3832(6) 0.01008(5) 0.0647(5) 0.0183(5) Uani 1 1 d . . . O31 O -0.3951(4) 0.03429(3) -0.0340(3) 0.0214(4) Uani 1 1 d . . . H31 H -0.256(7) 0.0455(6) 0.040(6) 0.026 Uiso 1 1 d . . . O32 O -0.2151(5) 0.00311(3) 0.2379(3) 0.0255(4) 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 N11 0.0164(9) 0.0166(9) 0.0182(11) -0.0019(8) -0.0002(8) -0.0025(7) N12 0.0217(10) 0.0197(10) 0.0186(11) -0.0023(8) -0.0004(8) -0.0029(8) C13 0.0198(12) 0.0184(11) 0.0300(15) -0.0090(10) 0.0009(10) -0.0001(9) C14 0.0220(12) 0.0176(11) 0.0372(16) 0.0031(11) -0.0082(11) -0.0024(9) C15 0.0241(12) 0.0215(12) 0.0195(13) 0.0035(10) -0.0041(10) -0.0049(10) C21 0.0148(10) 0.0141(10) 0.0162(12) -0.0014(9) 0.0010(9) 0.0018(8) C22 0.0239(12) 0.0182(11) 0.0181(13) 0.0040(9) -0.0021(10) 0.0021(9) C23 0.0199(12) 0.0232(12) 0.0170(13) -0.0020(10) -0.0053(10) 0.0009(9) C24 0.0137(10) 0.0181(11) 0.0217(13) -0.0049(10) 0.0018(9) 0.0021(8) C25 0.0196(11) 0.0149(10) 0.0207(13) 0.0024(9) -0.0004(10) -0.0006(9) C26 0.0182(11) 0.0176(11) 0.0157(12) -0.0008(9) -0.0021(9) 0.0005(9) C27 0.0182(11) 0.0148(11) 0.0186(12) 0.0000(9) 0.0012(9) 0.0023(8) N27 0.0326(12) 0.0164(10) 0.0214(12) 0.0045(9) -0.0084(10) -0.0049(9) O27 0.0275(9) 0.0154(8) 0.0196(9) 0.0039(7) -0.0074(7) -0.0032(7) C28 0.0155(11) 0.0218(12) 0.0263(14) -0.0050(10) -0.0009(10) 0.0006(9) C31 0.0214(11) 0.0148(10) 0.0185(12) 0.0000(9) -0.0006(9) 0.0001(9) O31 0.0272(9) 0.0136(8) 0.0226(10) 0.0030(7) -0.0088(8) -0.0032(7) O32 0.0339(10) 0.0162(8) 0.0251(10) 0.0052(7) -0.0124(8) -0.0024(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 N11 N12 1.349(3) . ? N11 C15 1.351(3) . ? N11 C28 1.455(3) . ? N12 C13 1.336(3) . ? C13 C14 1.394(4) . ? C13 H13 0.9500 . ? C14 C15 1.366(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C21 C22 1.395(3) . ? C21 C26 1.396(3) . ? C21 C27 1.495(3) . ? C22 C23 1.391(3) . ? C22 H22 0.9500 . ? C23 C24 1.382(3) . ? C23 H23 0.9500 . ? C24 C25 1.399(3) . ? C24 C28 1.514(3) . ? C25 C26 1.387(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O27 1.250(3) . ? C27 N27 1.321(3) . ? N27 H27A 0.91(3) . ? N27 H27B 0.82(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C31 O32 1.212(3) . ? C31 O31 1.305(3) . ? C31 C31 1.548(5) 3_455 ? O31 H31 0.89(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 N12 N11 C15 112.1(2) . . ? N12 N11 C28 120.3(2) . . ? C15 N11 C28 127.6(2) . . ? C13 N12 N11 104.2(2) . . ? N12 C13 C14 111.9(2) . . ? N12 C13 H13 124.0 . . ? C14 C13 H13 124.0 . . ? C15 C14 C13 104.7(2) . . ? C15 C14 H14 127.7 . . ? C13 C14 H14 127.7 . . ? N11 C15 C14 107.2(2) . . ? N11 C15 H15 126.4 . . ? C14 C15 H15 126.4 . . ? C22 C21 C26 118.7(2) . . ? C22 C21 C27 123.3(2) . . ? C26 C21 C27 118.0(2) . . ? C23 C22 C21 120.3(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 121.1(2) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 118.9(2) . . ? C23 C24 C28 120.7(2) . . ? C25 C24 C28 120.4(2) . . ? C26 C25 C24 120.3(2) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 120.9(2) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? O27 C27 N27 122.3(2) . . ? O27 C27 C21 119.1(2) . . ? N27 C27 C21 118.6(2) . . ? C27 N27 H27A 120(2) . . ? C27 N27 H27B 124(2) . . ? H27A N27 H27B 117(3) . . ? N11 C28 C24 113.01(19) . . ? N11 C28 H28A 109.0 . . ? C24 C28 H28A 109.0 . . ? N11 C28 H28B 109.0 . . ? C24 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? O32 C31 O31 126.4(2) . . ? O32 C31 C31 121.4(3) . 3_455 ? O31 C31 C31 112.2(3) . 3_455 ? C31 O31 H31 111.0(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 N12 C13 -0.1(3) . . . . ? C28 N11 N12 C13 -177.2(2) . . . . ? N11 N12 C13 C14 0.1(3) . . . . ? N12 C13 C14 C15 -0.1(3) . . . . ? N12 N11 C15 C14 0.0(3) . . . . ? C28 N11 C15 C14 176.9(2) . . . . ? C13 C14 C15 N11 0.1(3) . . . . ? C26 C21 C22 C23 -0.3(4) . . . . ? C27 C21 C22 C23 179.3(2) . . . . ? C21 C22 C23 C24 0.2(4) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C22 C23 C24 C28 -179.5(2) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C28 C24 C25 C26 179.6(2) . . . . ? C24 C25 C26 C21 -0.2(4) . . . . ? C22 C21 C26 C25 0.3(3) . . . . ? C27 C21 C26 C25 -179.3(2) . . . . ? C22 C21 C27 O27 173.3(2) . . . . ? C26 C21 C27 O27 -7.2(3) . . . . ? C22 C21 C27 N27 -6.9(4) . . . . ? C26 C21 C27 N27 172.6(2) . . . . ? N12 N11 C28 C24 85.4(3) . . . . ? C15 N11 C28 C24 -91.3(3) . . . . ? C23 C24 C28 N11 -112.1(3) . . . . ? C25 C24 C28 N11 68.5(3) . . . . ? 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 N27 H27A O32 0.91(3) 2.05(3) 2.932(3) 164(3) . O31 H31 O27 0.89(3) 1.63(3) 2.515(2) 171(3) . _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.434 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.063 #END data_2 _database_code_depnum_ccdc_archive 'CCDC 292717' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-[(1-pyrazolyl)methyl]benzamide, succinic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H11 N3 O)2 (C4 H6 O4) ; _chemical_formula_sum 'C26 H28 N6 O6' _chemical_formula_weight 520.54 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 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 9.5363(9) _cell_length_b 7.3143(6) _cell_length_c 17.6580(15) _cell_angle_alpha 90.00 _cell_angle_beta 96.130(7) _cell_angle_gamma 90.00 _cell_volume 1224.63(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3296 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 280.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.103 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8075 _diffrn_reflns_av_R_equivalents 0.1114 _diffrn_reflns_av_sigmaI/netI 0.0851 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.85 _reflns_number_total 2790 _reflns_number_gt 2042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1000P)^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 SHELXL _refine_ls_extinction_coef 0.079(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2790 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.1686 _refine_ls_wR_factor_gt 0.1527 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C11 C 0.69892(17) 0.6422(2) 0.11394(10) 0.0253(4) Uani 1 1 d . . . C12 C 0.77524(18) 0.5043(3) 0.15386(10) 0.0276(4) Uani 1 1 d . . . H12 H 0.8718 0.5230 0.1714 0.033 Uiso 1 1 calc R . . C13 C 0.71129(19) 0.3402(3) 0.16813(10) 0.0290(4) Uani 1 1 d . . . H13 H 0.7646 0.2465 0.1951 0.035 Uiso 1 1 calc R . . C14 C 0.57028(17) 0.3109(3) 0.14353(10) 0.0261(4) Uani 1 1 d . . . C15 C 0.49377(18) 0.4504(3) 0.10582(11) 0.0322(5) Uani 1 1 d . . . H15 H 0.3963 0.4329 0.0901 0.039 Uiso 1 1 calc R . . C16 C 0.55639(18) 0.6141(3) 0.09062(11) 0.0303(5) Uani 1 1 d . . . H16 H 0.5023 0.7079 0.0642 0.036 Uiso 1 1 calc R . . C17 C 0.76314(17) 0.8158(3) 0.09078(10) 0.0251(4) Uani 1 1 d . . . N17 N 0.88870(16) 0.8634(2) 0.12459(10) 0.0308(4) Uani 1 1 d . . . H17A H 0.926(2) 0.968(3) 0.1097(12) 0.037 Uiso 1 1 d . . . H17B H 0.942(2) 0.791(3) 0.1616(12) 0.037 Uiso 1 1 d . . . O17 O 0.69900(12) 0.91043(19) 0.03984(7) 0.0322(4) Uani 1 1 d . . . C18 C 0.50140(18) 0.1281(3) 0.15472(11) 0.0293(4) Uani 1 1 d . . . H18A H 0.4744 0.0714 0.1044 0.035 Uiso 1 1 calc R . . H18B H 0.5703 0.0464 0.1838 0.035 Uiso 1 1 calc R . . N21 N 0.37771(14) 0.1451(2) 0.19488(8) 0.0246(4) Uani 1 1 d . . . N22 N 0.39218(15) 0.1750(2) 0.27057(8) 0.0271(4) Uani 1 1 d . . . C23 C 0.26112(18) 0.1968(3) 0.28798(11) 0.0304(4) Uani 1 1 d . . . H23 H 0.2369 0.2186 0.3380 0.037 Uiso 1 1 calc R . . C24 C 0.16387(18) 0.1836(3) 0.22381(11) 0.0324(5) Uani 1 1 d . . . H24 H 0.0642 0.1943 0.2214 0.039 Uiso 1 1 calc R . . C25 C 0.24191(18) 0.1522(3) 0.16544(11) 0.0310(5) Uani 1 1 d . . . H25 H 0.2071 0.1378 0.1133 0.037 Uiso 1 1 calc R . . C31 C 0.89715(17) 1.2786(3) 0.01090(10) 0.0255(4) Uani 1 1 d . . . O31 O 0.77253(13) 1.2171(2) -0.01719(8) 0.0322(4) Uani 1 1 d . . . H31 H 0.754(2) 1.114(3) 0.0057(13) 0.039 Uiso 1 1 d . . . O32 O 0.97582(13) 1.1949(2) 0.05651(8) 0.0377(4) Uani 1 1 d . . . C32 C 0.93136(17) 1.4630(2) -0.01942(9) 0.0261(4) Uani 1 1 d . . . H32A H 0.8541 1.5492 -0.0117 0.039 Uiso 1 1 calc R . . H32B H 0.9380 1.4536 -0.0749 0.039 Uiso 1 1 calc 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 C11 0.0265(8) 0.0252(10) 0.0247(9) -0.0001(7) 0.0045(7) -0.0014(7) C12 0.0246(8) 0.0311(10) 0.0267(9) 0.0013(8) 0.0002(7) -0.0016(7) C13 0.0277(8) 0.0295(11) 0.0299(10) 0.0036(8) 0.0031(7) 0.0021(7) C14 0.0258(8) 0.0267(10) 0.0267(9) -0.0007(7) 0.0069(7) -0.0009(7) C15 0.0231(8) 0.0344(12) 0.0385(10) 0.0044(9) 0.0005(7) -0.0018(7) C16 0.0258(9) 0.0297(11) 0.0350(10) 0.0047(8) 0.0009(7) 0.0009(7) C17 0.0258(8) 0.0259(10) 0.0238(9) 0.0009(7) 0.0034(7) 0.0006(7) N17 0.0285(8) 0.0286(10) 0.0338(9) 0.0085(7) -0.0041(7) -0.0047(7) O17 0.0273(6) 0.0302(8) 0.0377(8) 0.0098(6) -0.0035(5) -0.0038(5) C18 0.0292(8) 0.0274(11) 0.0322(10) -0.0006(8) 0.0078(7) -0.0008(7) N21 0.0235(7) 0.0240(8) 0.0262(8) 0.0001(6) 0.0020(6) -0.0035(6) N22 0.0269(7) 0.0273(9) 0.0264(8) -0.0005(7) -0.0009(6) -0.0009(6) C23 0.0311(9) 0.0310(11) 0.0295(10) -0.0008(8) 0.0047(7) 0.0012(8) C24 0.0234(8) 0.0322(11) 0.0406(11) 0.0003(8) -0.0005(8) -0.0008(7) C25 0.0271(9) 0.0330(11) 0.0310(10) 0.0003(8) -0.0053(7) -0.0045(7) C31 0.0245(8) 0.0288(10) 0.0234(9) -0.0002(7) 0.0035(7) -0.0001(7) O31 0.0287(6) 0.0317(8) 0.0343(7) 0.0077(6) -0.0052(5) -0.0088(6) O32 0.0283(7) 0.0346(8) 0.0477(9) 0.0145(7) -0.0077(6) -0.0055(6) C32 0.0270(8) 0.0254(10) 0.0256(9) 0.0013(7) 0.0014(7) -0.0020(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 C11 C12 1.391(2) . ? C11 C16 1.393(2) . ? C11 C17 1.486(3) . ? C12 C13 1.382(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(3) . ? C14 C18 1.512(3) . ? C15 C16 1.378(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.243(2) . ? C17 N17 1.326(2) . ? N17 H17A 0.89(2) . ? N17 H17B 0.94(2) . ? C18 N21 1.445(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N21 C25 1.344(2) . ? N21 N22 1.347(2) . ? N22 C23 1.328(2) . ? C23 C24 1.389(3) . ? C23 H23 0.9500 . ? C24 C25 1.354(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C31 O32 1.207(2) . ? C31 O31 1.317(2) . ? C31 C32 1.500(3) . ? O31 H31 0.88(3) . ? C32 C32 1.512(3) 3_785 ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? 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 C12 C11 C16 118.98(17) . . ? C12 C11 C17 123.40(15) . . ? C16 C11 C17 117.54(16) . . ? C13 C12 C11 120.34(16) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.64(17) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 118.82(17) . . ? C15 C14 C18 120.06(15) . . ? C13 C14 C18 121.09(16) . . ? C16 C15 C14 121.18(16) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 120.01(17) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? O17 C17 N17 122.06(18) . . ? O17 C17 C11 119.31(15) . . ? N17 C17 C11 118.63(16) . . ? C17 N17 H17A 117.6(13) . . ? C17 N17 H17B 123.9(13) . . ? H17A N17 H17B 118.5(18) . . ? N21 C18 C14 112.14(15) . . ? N21 C18 H18A 109.2 . . ? C14 C18 H18A 109.2 . . ? N21 C18 H18B 109.2 . . ? C14 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C25 N21 N22 111.70(15) . . ? C25 N21 C18 128.09(16) . . ? N22 N21 C18 119.90(14) . . ? C23 N22 N21 104.48(14) . . ? N22 C23 C24 111.45(17) . . ? N22 C23 H23 124.3 . . ? C24 C23 H23 124.3 . . ? C25 C24 C23 105.04(15) . . ? C25 C24 H24 127.5 . . ? C23 C24 H24 127.5 . . ? N21 C25 C24 107.31(16) . . ? N21 C25 H25 126.3 . . ? C24 C25 H25 126.3 . . ? O32 C31 O31 123.32(18) . . ? O32 C31 C32 123.44(16) . . ? O31 C31 C32 113.24(15) . . ? C31 O31 H31 109.5(13) . . ? C31 C32 C32 111.77(17) . 3_785 ? C31 C32 H32A 109.3 . . ? C32 C32 H32A 109.3 3_785 . ? C31 C32 H32B 109.3 . . ? C32 C32 H32B 109.3 3_785 . ? H32A C32 H32B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 C13 1.8(3) . . . . ? C17 C11 C12 C13 -174.67(17) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C12 C13 C14 C18 176.35(17) . . . . ? C13 C14 C15 C16 1.9(3) . . . . ? C18 C14 C15 C16 -175.81(18) . . . . ? C14 C15 C16 C11 -0.6(3) . . . . ? C12 C11 C16 C15 -1.3(3) . . . . ? C17 C11 C16 C15 175.43(17) . . . . ? C12 C11 C17 O17 161.81(17) . . . . ? C16 C11 C17 O17 -14.8(3) . . . . ? C12 C11 C17 N17 -17.2(3) . . . . ? C16 C11 C17 N17 166.28(17) . . . . ? C15 C14 C18 N21 -57.4(2) . . . . ? C13 C14 C18 N21 124.95(18) . . . . ? C14 C18 N21 C25 97.6(2) . . . . ? C14 C18 N21 N22 -75.4(2) . . . . ? C25 N21 N22 C23 1.4(2) . . . . ? C18 N21 N22 C23 175.56(16) . . . . ? N21 N22 C23 C24 -0.9(2) . . . . ? N22 C23 C24 C25 0.1(2) . . . . ? N22 N21 C25 C24 -1.4(2) . . . . ? C18 N21 C25 C24 -174.97(17) . . . . ? C23 C24 C25 N21 0.8(2) . . . . ? O32 C31 C32 C32 -5.3(3) . . . 3_785 ? O31 C31 C32 C32 174.63(18) . . . 3_785 ? 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 N17 H17A O32 0.89(2) 1.99(3) 2.868(2) 166.9(18) . N17 H17B N22 0.94(2) 2.06(2) 2.978(2) 162.6(18) 2_655 O31 H31 O17 0.88(3) 1.71(3) 2.586(2) 172(2) . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.496 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.124 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 292718' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(pyrazol-1-yl)benzamide, benzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H11 N3 O) (C7 H6 O2) ; _chemical_formula_sum 'C18 H17 N3 O3' _chemical_formula_weight 323.35 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0434(8) _cell_length_b 10.5552(9) _cell_length_c 17.4323(15) _cell_angle_alpha 101.8070(10) _cell_angle_beta 102.1260(10) _cell_angle_gamma 94.3700(10) _cell_volume 1580.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7691 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.15 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.095 _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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14134 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.27 _reflns_number_total 7283 _reflns_number_gt 5988 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0600P)^2^+0.2000P] 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 7283 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C11 C -0.16027(14) 0.23119(12) 0.40463(7) 0.0166(3) Uani 1 1 d . . . C12 C -0.27682(15) 0.14274(12) 0.41113(8) 0.0205(3) Uani 1 1 d . . . H12 H -0.3203 0.0707 0.3675 0.025 Uiso 1 1 calc R . . C13 C -0.32958(15) 0.15991(13) 0.48160(8) 0.0213(3) Uani 1 1 d . . . H13 H -0.4088 0.0990 0.4858 0.026 Uiso 1 1 calc R . . C14 C -0.26810(14) 0.26482(12) 0.54592(8) 0.0183(3) Uani 1 1 d . . . C15 C -0.15119(15) 0.35297(12) 0.53908(8) 0.0203(3) Uani 1 1 d . . . H15 H -0.1076 0.4251 0.5826 0.024 Uiso 1 1 calc R . . C16 C -0.09848(15) 0.33581(12) 0.46915(8) 0.0196(3) Uani 1 1 d . . . H16 H -0.0188 0.3965 0.4652 0.023 Uiso 1 1 calc R . . C17 C -0.09672(14) 0.22021(12) 0.33109(7) 0.0176(3) Uani 1 1 d . . . N17 N -0.12735(14) 0.10855(11) 0.27619(7) 0.0216(2) Uani 1 1 d . . . H17A H -0.0829(17) 0.1076(15) 0.2338(10) 0.026 Uiso 1 1 d . . . H17B H -0.1813(18) 0.0396(15) 0.2797(9) 0.026 Uiso 1 1 d . . . O17 O -0.01545(11) 0.31588(9) 0.32349(5) 0.0224(2) Uani 1 1 d . . . C18 C -0.32794(15) 0.28523(13) 0.62194(8) 0.0219(3) Uani 1 1 d . . . H18A H -0.3557 0.3749 0.6339 0.026 Uiso 1 1 calc R . . H18B H -0.4217 0.2238 0.6124 0.026 Uiso 1 1 calc R . . N21 N -0.21807(12) 0.26599(10) 0.69180(6) 0.0176(2) Uani 1 1 d . . . N22 N -0.19815(13) 0.14393(10) 0.70159(6) 0.0202(2) Uani 1 1 d . . . C23 C -0.09651(15) 0.16250(13) 0.77194(8) 0.0221(3) Uani 1 1 d . . . H23 H -0.0598 0.0939 0.7954 0.026 Uiso 1 1 calc R . . C24 C -0.05107(15) 0.29411(13) 0.80651(8) 0.0224(3) Uani 1 1 d . . . H24 H 0.0200 0.3317 0.8560 0.027 Uiso 1 1 calc R . . C25 C -0.13169(15) 0.35815(12) 0.75337(8) 0.0208(3) Uani 1 1 d . . . H25 H -0.1272 0.4499 0.7591 0.025 Uiso 1 1 calc R . . C31 C 0.18203(14) 0.25038(12) 0.08514(8) 0.0184(3) Uani 1 1 d . . . C37 C 0.10818(14) 0.22296(12) 0.15002(8) 0.0184(3) Uani 1 1 d . . . O31 O 0.12829(11) 0.32376(9) 0.21180(6) 0.0225(2) Uani 1 1 d . . . H31 H 0.0755(18) 0.3092(15) 0.2481(10) 0.027 Uiso 1 1 d . . . O32 O 0.03610(11) 0.11798(9) 0.14578(5) 0.0235(2) Uani 1 1 d . . . C32 C 0.26324(15) 0.37151(12) 0.09275(8) 0.0210(3) Uani 1 1 d . . . H32 H 0.2738 0.4377 0.1402 0.025 Uiso 1 1 calc R . . C33 C 0.32887(16) 0.39591(13) 0.03126(8) 0.0246(3) Uani 1 1 d . . . H33 H 0.3846 0.4785 0.0367 0.030 Uiso 1 1 calc R . . C34 C 0.31294(16) 0.29941(14) -0.03815(8) 0.0264(3) Uani 1 1 d . . . H34 H 0.3574 0.3161 -0.0804 0.032 Uiso 1 1 calc R . . C35 C 0.23237(16) 0.17865(14) -0.04601(8) 0.0260(3) Uani 1 1 d . . . H35 H 0.2221 0.1126 -0.0935 0.031 Uiso 1 1 calc R . . C36 C 0.16659(15) 0.15410(13) 0.01545(8) 0.0224(3) Uani 1 1 d . . . H36 H 0.1110 0.0714 0.0099 0.027 Uiso 1 1 calc R . . C41 C 0.30622(14) 0.25279(12) 0.44430(7) 0.0179(3) Uani 1 1 d . . . C42 C 0.23524(15) 0.14561(13) 0.46408(8) 0.0211(3) Uani 1 1 d . . . H42 H 0.2155 0.0630 0.4273 0.025 Uiso 1 1 calc R . . C43 C 0.19365(15) 0.15964(13) 0.53715(8) 0.0211(3) Uani 1 1 d . . . H43 H 0.1458 0.0863 0.5503 0.025 Uiso 1 1 calc R . . C44 C 0.22130(14) 0.28006(13) 0.59154(8) 0.0193(3) Uani 1 1 d . . . C45 C 0.28916(14) 0.38740(12) 0.57103(8) 0.0199(3) Uani 1 1 d . . . H45 H 0.3066 0.4704 0.6073 0.024 Uiso 1 1 calc R . . C46 C 0.33142(14) 0.37383(12) 0.49811(8) 0.0195(3) Uani 1 1 d . . . H46 H 0.3779 0.4476 0.4847 0.023 Uiso 1 1 calc R . . C47 C 0.36076(14) 0.24375(12) 0.36826(8) 0.0191(3) Uani 1 1 d . . . N47 N 0.33724(14) 0.12917(11) 0.31630(7) 0.0222(2) Uani 1 1 d . . . H47A H 0.3778(17) 0.1264(14) 0.2721(10) 0.027 Uiso 1 1 d . . . H47B H 0.2988(18) 0.0607(15) 0.3256(9) 0.027 Uiso 1 1 d . . . O47 O 0.42849(11) 0.34274(9) 0.35603(5) 0.0237(2) Uani 1 1 d . . . C48 C 0.18287(15) 0.29342(13) 0.67262(8) 0.0220(3) Uani 1 1 d . . . H48A H 0.1586 0.3829 0.6910 0.026 Uiso 1 1 calc R . . H48B H 0.0917 0.2315 0.6678 0.026 Uiso 1 1 calc R . . N51 N 0.31022(12) 0.26713(10) 0.73192(6) 0.0180(2) Uani 1 1 d . . . N52 N 0.32057(13) 0.14391(10) 0.74195(7) 0.0233(2) Uani 1 1 d . . . C53 C 0.45832(16) 0.15033(13) 0.78953(8) 0.0231(3) Uani 1 1 d . . . H53 H 0.4980 0.0782 0.8078 0.028 Uiso 1 1 calc R . . C54 C 0.53713(15) 0.27558(13) 0.80937(8) 0.0210(3) Uani 1 1 d . . . H54 H 0.6367 0.3045 0.8423 0.025 Uiso 1 1 calc R . . C55 C 0.43905(15) 0.34796(12) 0.77084(7) 0.0194(3) Uani 1 1 d . . . H55 H 0.4582 0.4379 0.7714 0.023 Uiso 1 1 calc R . . C61 C 0.64969(15) 0.25227(12) 0.12688(7) 0.0191(3) Uani 1 1 d . . . C67 C 0.56311(15) 0.24113(12) 0.18952(8) 0.0187(3) Uani 1 1 d . . . O61 O 0.58394(11) 0.34601(9) 0.24865(6) 0.0229(2) Uani 1 1 d . . . H61 H 0.5238(18) 0.3369(15) 0.2825(10) 0.027 Uiso 1 1 d . . . O62 O 0.47885(11) 0.14259(9) 0.18562(6) 0.0232(2) Uani 1 1 d . . . C62 C 0.74911(15) 0.36266(13) 0.13211(8) 0.0226(3) Uani 1 1 d . . . H62 H 0.7660 0.4337 0.1776 0.027 Uiso 1 1 calc R . . C63 C 0.82336(16) 0.36846(13) 0.07070(9) 0.0259(3) Uani 1 1 d . . . H63 H 0.8916 0.4436 0.0743 0.031 Uiso 1 1 calc R . . C64 C 0.79871(16) 0.26541(14) 0.00416(8) 0.0256(3) Uani 1 1 d . . . H64 H 0.8495 0.2703 -0.0378 0.031 Uiso 1 1 calc R . . C65 C 0.70016(16) 0.15515(14) -0.00129(8) 0.0261(3) Uani 1 1 d . . . H65 H 0.6829 0.0845 -0.0470 0.031 Uiso 1 1 calc R . . C66 C 0.62677(16) 0.14859(13) 0.06047(8) 0.0234(3) Uani 1 1 d . . . H66 H 0.5603 0.0725 0.0572 0.028 Uiso 1 1 calc 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 C11 0.0182(6) 0.0158(6) 0.0173(6) 0.0062(5) 0.0043(5) 0.0031(5) C12 0.0221(7) 0.0176(6) 0.0207(6) 0.0025(5) 0.0053(5) -0.0011(5) C13 0.0198(6) 0.0203(6) 0.0259(7) 0.0074(5) 0.0085(5) -0.0003(5) C14 0.0174(6) 0.0214(6) 0.0196(6) 0.0087(5) 0.0066(5) 0.0071(5) C15 0.0242(7) 0.0191(6) 0.0171(6) 0.0027(5) 0.0056(5) 0.0010(5) C16 0.0213(6) 0.0185(6) 0.0192(6) 0.0051(5) 0.0055(5) -0.0005(5) C17 0.0182(6) 0.0171(6) 0.0174(6) 0.0055(5) 0.0028(5) 0.0013(5) N17 0.0280(6) 0.0170(5) 0.0200(6) 0.0026(5) 0.0100(5) -0.0032(5) O17 0.0296(5) 0.0189(5) 0.0187(5) 0.0025(4) 0.0098(4) -0.0046(4) C18 0.0209(7) 0.0270(7) 0.0216(7) 0.0088(5) 0.0087(5) 0.0060(5) N21 0.0219(5) 0.0157(5) 0.0179(5) 0.0044(4) 0.0098(4) 0.0029(4) N22 0.0263(6) 0.0155(5) 0.0207(6) 0.0045(4) 0.0094(5) 0.0021(4) C23 0.0264(7) 0.0226(7) 0.0209(7) 0.0078(5) 0.0097(5) 0.0057(5) C24 0.0234(7) 0.0246(7) 0.0186(6) 0.0020(5) 0.0080(5) -0.0010(5) C25 0.0265(7) 0.0157(6) 0.0215(7) 0.0008(5) 0.0128(5) -0.0004(5) C31 0.0180(6) 0.0196(6) 0.0191(6) 0.0071(5) 0.0049(5) 0.0030(5) C37 0.0201(6) 0.0164(6) 0.0187(6) 0.0050(5) 0.0034(5) 0.0021(5) O31 0.0316(5) 0.0182(5) 0.0184(5) 0.0027(4) 0.0105(4) -0.0027(4) O32 0.0305(5) 0.0175(5) 0.0226(5) 0.0044(4) 0.0087(4) -0.0023(4) C32 0.0237(7) 0.0187(6) 0.0213(7) 0.0039(5) 0.0076(5) 0.0023(5) C33 0.0261(7) 0.0220(7) 0.0290(7) 0.0087(6) 0.0114(6) 0.0014(5) C34 0.0273(7) 0.0331(8) 0.0243(7) 0.0107(6) 0.0128(6) 0.0073(6) C35 0.0283(7) 0.0284(7) 0.0204(7) 0.0010(6) 0.0075(6) 0.0052(6) C36 0.0225(7) 0.0203(6) 0.0233(7) 0.0029(5) 0.0056(5) 0.0010(5) C41 0.0164(6) 0.0184(6) 0.0183(6) 0.0039(5) 0.0035(5) 0.0014(5) C42 0.0232(7) 0.0180(6) 0.0216(7) 0.0030(5) 0.0060(5) 0.0009(5) C43 0.0233(7) 0.0189(6) 0.0228(7) 0.0070(5) 0.0076(5) 0.0011(5) C44 0.0151(6) 0.0235(6) 0.0195(6) 0.0046(5) 0.0043(5) 0.0036(5) C45 0.0200(6) 0.0189(6) 0.0188(6) 0.0004(5) 0.0038(5) 0.0022(5) C46 0.0182(6) 0.0179(6) 0.0223(6) 0.0057(5) 0.0039(5) 0.0005(5) C47 0.0194(6) 0.0175(6) 0.0198(6) 0.0052(5) 0.0034(5) 0.0000(5) N47 0.0304(6) 0.0172(6) 0.0194(6) 0.0037(5) 0.0090(5) -0.0029(5) O47 0.0318(5) 0.0178(5) 0.0223(5) 0.0039(4) 0.0108(4) -0.0022(4) C48 0.0193(6) 0.0265(7) 0.0207(7) 0.0038(5) 0.0074(5) 0.0032(5) N51 0.0215(5) 0.0156(5) 0.0175(5) 0.0034(4) 0.0070(4) 0.0001(4) N52 0.0325(6) 0.0150(5) 0.0224(6) 0.0035(4) 0.0085(5) -0.0004(5) C53 0.0329(8) 0.0188(6) 0.0194(6) 0.0047(5) 0.0089(6) 0.0064(5) C54 0.0221(7) 0.0240(7) 0.0181(6) 0.0049(5) 0.0076(5) 0.0019(5) C55 0.0243(7) 0.0161(6) 0.0184(6) 0.0024(5) 0.0088(5) -0.0007(5) C61 0.0213(6) 0.0195(6) 0.0172(6) 0.0065(5) 0.0031(5) 0.0044(5) C67 0.0237(7) 0.0144(6) 0.0178(6) 0.0049(5) 0.0031(5) 0.0031(5) O61 0.0317(5) 0.0177(5) 0.0197(5) 0.0020(4) 0.0108(4) -0.0014(4) O62 0.0309(5) 0.0164(5) 0.0222(5) 0.0034(4) 0.0083(4) -0.0003(4) C62 0.0264(7) 0.0178(6) 0.0229(7) 0.0026(5) 0.0066(5) 0.0020(5) C63 0.0265(7) 0.0236(7) 0.0302(8) 0.0091(6) 0.0094(6) 0.0021(6) C64 0.0267(7) 0.0330(8) 0.0207(7) 0.0109(6) 0.0075(5) 0.0081(6) C65 0.0317(8) 0.0278(7) 0.0169(6) 0.0018(5) 0.0042(5) 0.0046(6) C66 0.0282(7) 0.0208(7) 0.0197(7) 0.0032(5) 0.0043(5) 0.0000(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 C11 C16 1.3893(18) . ? C11 C12 1.3924(17) . ? C11 C17 1.4987(17) . ? C12 C13 1.3922(18) . ? C12 H12 0.9500 . ? C13 C14 1.3887(18) . ? C13 H13 0.9500 . ? C14 C15 1.3950(18) . ? C14 C18 1.5157(17) . ? C15 C16 1.3833(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.2490(14) . ? C17 N17 1.3263(17) . ? N17 H17A 0.911(16) . ? N17 H17B 0.865(16) . ? C18 N21 1.4613(16) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N21 C25 1.3465(16) . ? N21 N22 1.3542(14) . ? N22 C23 1.3371(17) . ? C23 C24 1.3886(19) . ? C23 H23 0.9500 . ? C24 C25 1.3763(19) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C31 C36 1.3892(18) . ? C31 C32 1.3922(17) . ? C31 C37 1.4937(17) . ? C37 O32 1.2224(15) . ? C37 O31 1.3207(15) . ? O31 H31 0.899(16) . ? C32 C33 1.3873(18) . ? C32 H32 0.9500 . ? C33 C34 1.386(2) . ? C33 H33 0.9500 . ? C34 C35 1.3854(19) . ? C34 H34 0.9500 . ? C35 C36 1.3881(19) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C46 1.3926(18) . ? C41 C42 1.3974(17) . ? C41 C47 1.4965(18) . ? C42 C43 1.3852(18) . ? C42 H42 0.9500 . ? C43 C44 1.3913(18) . ? C43 H43 0.9500 . ? C44 C45 1.3928(18) . ? C44 C48 1.5069(17) . ? C45 C46 1.3859(18) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 O47 1.2493(14) . ? C47 N47 1.3266(17) . ? N47 H47A 0.917(16) . ? N47 H47B 0.839(16) . ? C48 N51 1.4621(16) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? N51 C55 1.3510(16) . ? N51 N52 1.3549(14) . ? N52 C53 1.3321(18) . ? C53 C54 1.3933(19) . ? C53 H53 0.9500 . ? C54 C55 1.3727(18) . ? C54 H54 0.9500 . ? C55 H55 0.9500 . ? C61 C66 1.3881(18) . ? C61 C62 1.3917(18) . ? C61 C67 1.4889(18) . ? C67 O62 1.2230(15) . ? C67 O61 1.3203(15) . ? O61 H61 0.896(16) . ? C62 C63 1.3867(19) . ? C62 H62 0.9500 . ? C63 C64 1.384(2) . ? C63 H63 0.9500 . ? C64 C65 1.3852(19) . ? C64 H64 0.9500 . ? C65 C66 1.3887(19) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? 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 C16 C11 C12 119.04(12) . . ? C16 C11 C17 117.49(11) . . ? C12 C11 C17 123.47(11) . . ? C13 C12 C11 119.94(12) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.95(12) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 118.84(11) . . ? C13 C14 C18 120.96(11) . . ? C15 C14 C18 120.19(12) . . ? C16 C15 C14 120.24(12) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.99(12) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? O17 C17 N17 121.84(12) . . ? O17 C17 C11 119.20(11) . . ? N17 C17 C11 118.96(11) . . ? C17 N17 H17A 114.5(10) . . ? C17 N17 H17B 124.7(10) . . ? H17A N17 H17B 120.7(14) . . ? N21 C18 C14 113.16(10) . . ? N21 C18 H18A 108.9 . . ? C14 C18 H18A 108.9 . . ? N21 C18 H18B 108.9 . . ? C14 C18 H18B 108.9 . . ? H18A C18 H18B 107.8 . . ? C25 N21 N22 112.09(10) . . ? C25 N21 C18 127.68(11) . . ? N22 N21 C18 120.19(10) . . ? C23 N22 N21 104.29(10) . . ? N22 C23 C24 111.84(12) . . ? N22 C23 H23 124.1 . . ? C24 C23 H23 124.1 . . ? C25 C24 C23 104.83(12) . . ? C25 C24 H24 127.6 . . ? C23 C24 H24 127.6 . . ? N21 C25 C24 106.95(11) . . ? N21 C25 H25 126.5 . . ? C24 C25 H25 126.5 . . ? C36 C31 C32 119.62(12) . . ? C36 C31 C37 119.30(11) . . ? C32 C31 C37 121.07(12) . . ? O32 C37 O31 123.82(12) . . ? O32 C37 C31 123.14(12) . . ? O31 C37 C31 113.04(11) . . ? C37 O31 H31 112.4(10) . . ? C33 C32 C31 120.25(12) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 119.83(12) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 120.16(12) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C34 C35 C36 120.08(13) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C31 120.06(12) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? C46 C41 C42 119.19(12) . . ? C46 C41 C47 117.68(11) . . ? C42 C41 C47 123.12(12) . . ? C43 C42 C41 120.12(12) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C42 C43 C44 120.69(12) . . ? C42 C43 H43 119.7 . . ? C44 C43 H43 119.7 . . ? C43 C44 C45 119.13(12) . . ? C43 C44 C48 120.48(12) . . ? C45 C44 C48 120.37(12) . . ? C46 C45 C44 120.41(12) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C45 C46 C41 120.44(12) . . ? C45 C46 H46 119.8 . . ? C41 C46 H46 119.8 . . ? O47 C47 N47 122.05(12) . . ? O47 C47 C41 119.55(11) . . ? N47 C47 C41 118.39(11) . . ? C47 N47 H47A 115.7(10) . . ? C47 N47 H47B 122.9(11) . . ? H47A N47 H47B 120.8(14) . . ? N51 C48 C44 110.90(10) . . ? N51 C48 H48A 109.5 . . ? C44 C48 H48A 109.5 . . ? N51 C48 H48B 109.5 . . ? C44 C48 H48B 109.5 . . ? H48A C48 H48B 108.0 . . ? C55 N51 N52 111.76(10) . . ? C55 N51 C48 127.30(11) . . ? N52 N51 C48 119.92(10) . . ? C53 N52 N51 104.53(10) . . ? N52 C53 C54 111.86(11) . . ? N52 C53 H53 124.1 . . ? C54 C53 H53 124.1 . . ? C55 C54 C53 104.72(12) . . ? C55 C54 H54 127.6 . . ? C53 C54 H54 127.6 . . ? N51 C55 C54 107.11(11) . . ? N51 C55 H55 126.4 . . ? C54 C55 H55 126.4 . . ? C66 C61 C62 119.61(12) . . ? C66 C61 C67 117.88(11) . . ? C62 C61 C67 122.50(12) . . ? O62 C67 O61 123.16(12) . . ? O62 C67 C61 122.20(12) . . ? O61 C67 C61 114.64(11) . . ? C67 O61 H61 111.2(10) . . ? C63 C62 C61 119.73(13) . . ? C63 C62 H62 120.1 . . ? C61 C62 H62 120.1 . . ? C64 C63 C62 120.41(13) . . ? C64 C63 H63 119.8 . . ? C62 C63 H63 119.8 . . ? C63 C64 C65 120.12(13) . . ? C63 C64 H64 119.9 . . ? C65 C64 H64 119.9 . . ? C64 C65 C66 119.58(13) . . ? C64 C65 H65 120.2 . . ? C66 C65 H65 120.2 . . ? C61 C66 C65 120.53(12) . . ? C61 C66 H66 119.7 . . ? C65 C66 H66 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 C13 -0.05(19) . . . . ? C17 C11 C12 C13 -179.97(11) . . . . ? C11 C12 C13 C14 0.30(19) . . . . ? C12 C13 C14 C15 -0.41(19) . . . . ? C12 C13 C14 C18 178.61(11) . . . . ? C13 C14 C15 C16 0.26(18) . . . . ? C18 C14 C15 C16 -178.77(11) . . . . ? C14 C15 C16 C11 -0.01(19) . . . . ? C12 C11 C16 C15 -0.09(19) . . . . ? C17 C11 C16 C15 179.83(11) . . . . ? C16 C11 C17 O17 -14.30(17) . . . . ? C12 C11 C17 O17 165.61(12) . . . . ? C16 C11 C17 N17 165.09(12) . . . . ? C12 C11 C17 N17 -14.99(18) . . . . ? C13 C14 C18 N21 112.09(13) . . . . ? C15 C14 C18 N21 -68.90(15) . . . . ? C14 C18 N21 C25 103.21(14) . . . . ? C14 C18 N21 N22 -79.40(14) . . . . ? C25 N21 N22 C23 0.35(13) . . . . ? C18 N21 N22 C23 -177.43(10) . . . . ? N21 N22 C23 C24 -0.42(14) . . . . ? N22 C23 C24 C25 0.34(15) . . . . ? N22 N21 C25 C24 -0.15(14) . . . . ? C18 N21 C25 C24 177.42(11) . . . . ? C23 C24 C25 N21 -0.11(14) . . . . ? C36 C31 C37 O32 1.42(19) . . . . ? C32 C31 C37 O32 -179.89(12) . . . . ? C36 C31 C37 O31 -178.25(11) . . . . ? C32 C31 C37 O31 0.44(17) . . . . ? C36 C31 C32 C33 -0.22(19) . . . . ? C37 C31 C32 C33 -178.90(12) . . . . ? C31 C32 C33 C34 0.3(2) . . . . ? C32 C33 C34 C35 -0.3(2) . . . . ? C33 C34 C35 C36 0.3(2) . . . . ? C34 C35 C36 C31 -0.3(2) . . . . ? C32 C31 C36 C35 0.24(19) . . . . ? C37 C31 C36 C35 178.95(12) . . . . ? C46 C41 C42 C43 -1.36(19) . . . . ? C47 C41 C42 C43 177.10(12) . . . . ? C41 C42 C43 C44 0.2(2) . . . . ? C42 C43 C44 C45 1.12(19) . . . . ? C42 C43 C44 C48 -176.99(12) . . . . ? C43 C44 C45 C46 -1.32(19) . . . . ? C48 C44 C45 C46 176.80(11) . . . . ? C44 C45 C46 C41 0.18(19) . . . . ? C42 C41 C46 C45 1.16(19) . . . . ? C47 C41 C46 C45 -177.38(11) . . . . ? C46 C41 C47 O47 1.20(18) . . . . ? C42 C41 C47 O47 -177.28(12) . . . . ? C46 C41 C47 N47 -179.83(11) . . . . ? C42 C41 C47 N47 1.69(19) . . . . ? C43 C44 C48 N51 87.98(14) . . . . ? C45 C44 C48 N51 -90.11(14) . . . . ? C44 C48 N51 C55 77.85(16) . . . . ? C44 C48 N51 N52 -89.61(13) . . . . ? C55 N51 N52 C53 1.18(14) . . . . ? C48 N51 N52 C53 170.46(11) . . . . ? N51 N52 C53 C54 -0.71(15) . . . . ? N52 C53 C54 C55 0.02(15) . . . . ? N52 N51 C55 C54 -1.20(14) . . . . ? C48 N51 C55 C54 -169.51(12) . . . . ? C53 C54 C55 N51 0.69(14) . . . . ? C66 C61 C67 O62 3.09(19) . . . . ? C62 C61 C67 O62 -178.11(12) . . . . ? C66 C61 C67 O61 -176.39(11) . . . . ? C62 C61 C67 O61 2.41(18) . . . . ? C66 C61 C62 C63 0.50(19) . . . . ? C67 C61 C62 C63 -178.28(12) . . . . ? C61 C62 C63 C64 0.3(2) . . . . ? C62 C63 C64 C65 -0.4(2) . . . . ? C63 C64 C65 C66 -0.2(2) . . . . ? C62 C61 C66 C65 -1.1(2) . . . . ? C67 C61 C66 C65 177.73(12) . . . . ? C64 C65 C66 C61 1.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N17 H17A O32 0.911(16) 2.066(17) 2.9740(15) 174.2(14) . N17 H17B N52 0.865(16) 2.147(16) 2.9946(16) 166.4(14) 2_556 O31 H31 O17 0.899(16) 1.683(17) 2.5692(13) 168.0(15) . N47 H47A O62 0.917(16) 1.948(17) 2.8599(15) 172.5(14) . N47 H47B N22 0.839(16) 2.195(16) 2.9840(15) 156.8(14) 2_556 O61 H61 O47 0.896(16) 1.682(17) 2.5702(13) 170.4(15) . _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.260 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.055 #END data_4 _database_code_depnum_ccdc_archive 'CCDC 292719' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(pyrazol-1-yl)benzamide, 4-fluorobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H11 N3 O) (C7 H5 O2 F) ; _chemical_formula_sum 'C18 H16 F N3 O3' _chemical_formula_weight 341.34 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' F F 0.0171 0.0103 '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 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 4.3453(7) _cell_length_b 10.8147(17) _cell_length_c 34.003(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.541(2) _cell_angle_gamma 90.00 _cell_volume 1597.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5694 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9978 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2909 _reflns_number_gt 2486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0500P)^2^+0.7000P] 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 2909 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C11 C 0.1501(4) 0.27596(14) 0.52906(5) 0.0209(4) Uani 1 1 d . . . C17 C 0.3260(4) 0.30326(15) 0.56578(5) 0.0229(4) Uani 1 1 d . . . N17 N 0.3653(4) 0.21420(14) 0.59206(5) 0.0270(3) Uani 1 1 d . . . H17A H 0.481(5) 0.2347(18) 0.6146(6) 0.032 Uiso 1 1 d . . . H17B H 0.293(4) 0.1378(19) 0.5892(6) 0.032 Uiso 1 1 d . . . O17 O 0.4347(3) 0.40946(10) 0.57113(4) 0.0303(3) Uani 1 1 d . . . C12 C -0.0264(4) 0.16905(15) 0.52427(5) 0.0234(4) Uani 1 1 d . . . H12 H -0.0356 0.1098 0.5449 0.028 Uiso 1 1 calc R . . C13 C -0.1875(4) 0.14941(15) 0.48969(5) 0.0234(4) Uani 1 1 d . . . H13 H -0.3070 0.0764 0.4867 0.028 Uiso 1 1 calc R . . C14 C -0.1781(4) 0.23451(15) 0.45914(5) 0.0205(4) Uani 1 1 d . . . C15 C -0.0008(4) 0.34077(15) 0.46389(5) 0.0225(4) Uani 1 1 d . . . H15 H 0.0083 0.3999 0.4433 0.027 Uiso 1 1 calc R . . C16 C 0.1621(4) 0.36067(15) 0.49845(5) 0.0219(4) Uani 1 1 d . . . H16 H 0.2836 0.4332 0.5013 0.026 Uiso 1 1 calc R . . C18 C -0.3540(4) 0.21170(16) 0.42146(5) 0.0237(4) Uani 1 1 d . . . H18A H -0.5305 0.1565 0.4269 0.028 Uiso 1 1 calc R . . H18B H -0.4367 0.2912 0.4115 0.028 Uiso 1 1 calc R . . N21 N -0.1620(3) 0.15565(12) 0.39141(4) 0.0197(3) Uani 1 1 d . . . N22 N -0.1033(3) 0.03290(12) 0.39242(4) 0.0239(3) Uani 1 1 d . . . C23 C 0.0890(4) 0.01445(16) 0.36274(5) 0.0253(4) Uani 1 1 d . . . H23 H 0.1696 -0.0641 0.3557 0.030 Uiso 1 1 calc R . . C24 C 0.1574(4) 0.12376(16) 0.34329(5) 0.0254(4) Uani 1 1 d . . . H24 H 0.2900 0.1347 0.3215 0.031 Uiso 1 1 calc R . . C25 C -0.0085(4) 0.21224(15) 0.36248(5) 0.0228(4) Uani 1 1 d . . . H25 H -0.0141 0.2980 0.3564 0.027 Uiso 1 1 calc R . . C31 C 0.8695(4) 0.46564(15) 0.69908(5) 0.0228(4) Uani 1 1 d . . . C37 C 0.7476(4) 0.41178(15) 0.66183(5) 0.0254(4) Uani 1 1 d . A . O31 O 0.6640(3) 0.49208(11) 0.63494(4) 0.0331(3) Uani 1 1 d . . . H31 H 0.571(5) 0.4542(19) 0.6110(6) 0.040 Uiso 1 1 d . . . O32 O 0.7292(3) 0.30005(11) 0.65779(4) 0.0397(4) Uani 1 1 d . . . C32A C 0.7749(4) 0.57756(15) 0.71485(5) 0.0250(4) Uani 0.844(3) 1 d P A 1 F32 F 0.5621(3) 0.64427(11) 0.69648(3) 0.0286(4) Uiso 0.844(3) 1 d P A 1 C32B C 0.7749(4) 0.57756(15) 0.71485(5) 0.0250(4) Uani 0.156(3) 1 d P A 2 H32 H 0.6316 0.6266 0.7005 0.030 Uiso 0.156(3) 1 calc PR A 2 C33 C 0.8813(4) 0.62004(16) 0.75060(5) 0.0293(4) Uani 1 1 d . . . H33 H 0.8114 0.6968 0.7607 0.035 Uiso 1 1 calc R A 1 C34 C 1.0911(4) 0.54974(17) 0.77161(5) 0.0312(4) Uani 1 1 d . A . H34 H 1.1667 0.5784 0.7963 0.037 Uiso 1 1 calc R . . C35 C 1.1913(4) 0.43783(17) 0.75688(5) 0.0299(4) Uani 1 1 d . . . H35 H 1.3354 0.3894 0.7713 0.036 Uiso 1 1 calc R A 1 C36A C 1.0805(4) 0.39704(16) 0.72109(5) 0.0256(4) Uani 0.844(3) 1 d P A 1 H36 H 1.1500 0.3200 0.7111 0.031 Uiso 0.844(3) 1 calc PR A 1 C36B C 1.0805(4) 0.39704(16) 0.72109(5) 0.0256(4) Uani 0.156(3) 1 d P A 2 F36 F 1.1947(16) 0.3055(7) 0.7068(2) 0.038(2) Uiso 0.156(3) 1 d P A 2 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 C11 0.0222(8) 0.0175(8) 0.0229(9) -0.0019(7) 0.0035(7) 0.0039(6) C17 0.0274(9) 0.0180(9) 0.0234(9) -0.0016(7) 0.0029(7) 0.0027(7) N17 0.0379(9) 0.0172(7) 0.0260(8) 0.0013(6) -0.0051(7) -0.0028(6) O17 0.0437(8) 0.0171(6) 0.0298(7) 0.0010(5) -0.0076(6) -0.0041(5) C12 0.0259(9) 0.0197(8) 0.0245(9) 0.0038(7) 0.0041(7) -0.0001(7) C13 0.0227(8) 0.0204(8) 0.0271(9) -0.0007(7) 0.0037(7) -0.0039(7) C14 0.0186(8) 0.0197(8) 0.0232(9) -0.0013(7) 0.0045(6) 0.0048(6) C15 0.0269(9) 0.0165(8) 0.0241(9) 0.0025(7) 0.0047(7) 0.0042(7) C16 0.0247(8) 0.0155(8) 0.0254(9) -0.0024(7) 0.0025(7) 0.0010(7) C18 0.0204(8) 0.0234(9) 0.0273(9) 0.0000(7) 0.0030(7) 0.0028(7) N21 0.0223(7) 0.0156(7) 0.0212(7) 0.0011(6) -0.0012(6) 0.0008(5) N22 0.0282(7) 0.0172(7) 0.0263(8) 0.0022(6) -0.0012(6) 0.0016(6) C23 0.0282(9) 0.0221(9) 0.0255(9) -0.0034(7) -0.0035(7) 0.0047(7) C24 0.0279(9) 0.0272(9) 0.0212(9) -0.0020(7) 0.0022(7) -0.0021(7) C25 0.0272(8) 0.0191(8) 0.0221(8) 0.0022(7) -0.0022(7) -0.0034(7) C31 0.0222(8) 0.0201(8) 0.0262(9) 0.0011(7) 0.0050(7) -0.0048(7) C37 0.0291(9) 0.0188(9) 0.0284(9) 0.0000(7) 0.0013(7) -0.0005(7) O31 0.0520(8) 0.0188(6) 0.0284(7) 0.0027(5) -0.0093(6) -0.0060(6) O32 0.0620(9) 0.0190(7) 0.0379(8) -0.0024(6) -0.0160(7) 0.0018(6) C32A 0.0233(8) 0.0203(9) 0.0315(10) 0.0032(7) 0.0039(7) -0.0032(7) C32B 0.0233(8) 0.0203(9) 0.0315(10) 0.0032(7) 0.0039(7) -0.0032(7) C33 0.0327(10) 0.0218(9) 0.0338(10) -0.0062(8) 0.0116(8) -0.0089(7) C34 0.0317(10) 0.0359(10) 0.0261(10) -0.0017(8) 0.0031(8) -0.0137(8) C35 0.0268(9) 0.0333(10) 0.0298(10) 0.0052(8) 0.0004(8) -0.0055(8) C36A 0.0252(9) 0.0228(9) 0.0288(9) 0.0004(7) 0.0045(7) -0.0028(7) C36B 0.0252(9) 0.0228(9) 0.0288(9) 0.0004(7) 0.0045(7) -0.0028(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 C11 C16 1.388(2) . ? C11 C12 1.396(2) . ? C11 C17 1.488(2) . ? C17 O17 1.254(2) . ? C17 N17 1.324(2) . ? N17 H17A 0.94(2) . ? N17 H17B 0.89(2) . ? C12 C13 1.379(2) . ? C12 H12 0.9500 . ? C13 C14 1.389(2) . ? C13 H13 0.9500 . ? C14 C15 1.392(2) . ? C14 C18 1.506(2) . ? C15 C16 1.383(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C18 N21 1.457(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N21 C25 1.341(2) . ? N21 N22 1.3522(19) . ? N22 C23 1.331(2) . ? C23 C24 1.388(2) . ? C23 H23 0.9500 . ? C24 C25 1.368(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C31 C32A 1.388(2) . ? C31 C36A 1.392(2) . ? C31 C37 1.487(2) . ? C37 O32 1.219(2) . ? C37 O31 1.310(2) . ? O31 H31 1.00(2) . ? C32A F32 1.325(2) . ? C32A C33 1.376(3) . ? C33 C34 1.381(3) . ? C33 H33 0.9500 . ? C34 C35 1.382(3) . ? C34 H34 0.9500 . ? C35 C36A 1.377(2) . ? C35 H35 0.9500 . ? C36A H36 0.9500 . ? 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 C16 C11 C12 118.92(15) . . ? C16 C11 C17 118.42(15) . . ? C12 C11 C17 122.65(15) . . ? O17 C17 N17 121.49(16) . . ? O17 C17 C11 119.55(15) . . ? N17 C17 C11 118.96(15) . . ? C17 N17 H17A 116.3(12) . . ? C17 N17 H17B 123.9(13) . . ? H17A N17 H17B 119.7(17) . . ? C13 C12 C11 120.05(15) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 121.16(15) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 118.71(15) . . ? C13 C14 C18 120.63(15) . . ? C15 C14 C18 120.65(15) . . ? C16 C15 C14 120.35(15) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 120.80(15) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? N21 C18 C14 112.03(13) . . ? N21 C18 H18A 109.2 . . ? C14 C18 H18A 109.2 . . ? N21 C18 H18B 109.2 . . ? C14 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C25 N21 N22 111.82(14) . . ? C25 N21 C18 128.05(14) . . ? N22 N21 C18 119.98(13) . . ? C23 N22 N21 104.32(13) . . ? N22 C23 C24 111.87(15) . . ? N22 C23 H23 124.1 . . ? C24 C23 H23 124.1 . . ? C25 C24 C23 104.59(15) . . ? C25 C24 H24 127.7 . . ? C23 C24 H24 127.7 . . ? N21 C25 C24 107.39(15) . . ? N21 C25 H25 126.3 . . ? C24 C25 H25 126.3 . . ? C32A C31 C36A 116.95(16) . . ? C32A C31 C37 124.48(15) . . ? C36A C31 C37 118.47(15) . . ? O32 C37 O31 124.14(16) . . ? O32 C37 C31 120.45(16) . . ? O31 C37 C31 115.41(15) . . ? C37 O31 H31 114.0(12) . . ? F32 C32A C33 117.54(16) . . ? F32 C32A C31 120.06(15) . . ? C33 C32A C31 122.30(16) . . ? C32A C33 C34 119.22(17) . . ? C32A C33 H33 120.4 . . ? C34 C33 H33 120.4 . . ? C33 C34 C35 120.23(17) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C36A C35 C34 119.48(17) . . ? C36A C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? C35 C36A C31 121.83(17) . . ? C35 C36A H36 119.1 . . ? C31 C36A H36 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C17 O17 12.4(2) . . . . ? C12 C11 C17 O17 -167.38(16) . . . . ? C16 C11 C17 N17 -167.24(15) . . . . ? C12 C11 C17 N17 12.9(2) . . . . ? C16 C11 C12 C13 -0.6(2) . . . . ? C17 C11 C12 C13 179.26(15) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C12 C13 C14 C18 179.75(15) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C18 C14 C15 C16 -179.50(14) . . . . ? C14 C15 C16 C11 -0.5(2) . . . . ? C12 C11 C16 C15 0.8(2) . . . . ? C17 C11 C16 C15 -179.01(15) . . . . ? C13 C14 C18 N21 -95.67(18) . . . . ? C15 C14 C18 N21 83.79(18) . . . . ? C14 C18 N21 C25 -95.19(19) . . . . ? C14 C18 N21 N22 79.79(18) . . . . ? C25 N21 N22 C23 -0.85(18) . . . . ? C18 N21 N22 C23 -176.59(14) . . . . ? N21 N22 C23 C24 0.99(18) . . . . ? N22 C23 C24 C25 -0.77(19) . . . . ? N22 N21 C25 C24 0.39(18) . . . . ? C18 N21 C25 C24 175.71(15) . . . . ? C23 C24 C25 N21 0.21(18) . . . . ? C32A C31 C37 O32 -147.92(18) . . . . ? C36A C31 C37 O32 28.3(2) . . . . ? C32A C31 C37 O31 31.8(2) . . . . ? C36A C31 C37 O31 -151.96(16) . . . . ? C36A C31 C32A F32 -176.34(15) . . . . ? C37 C31 C32A F32 -0.1(3) . . . . ? C36A C31 C32A C33 -0.2(2) . . . . ? C37 C31 C32A C33 176.05(16) . . . . ? F32 C32A C33 C34 176.59(15) . . . . ? C31 C32A C33 C34 0.4(3) . . . . ? C32A C33 C34 C35 -0.3(3) . . . . ? C33 C34 C35 C36A 0.0(3) . . . . ? C34 C35 C36A C31 0.1(3) . . . . ? C32A C31 C36A C35 0.0(2) . . . . ? C37 C31 C36A C35 -176.53(15) . . . . ? 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 O31 H31 O17 1.00(2) 1.55(2) 2.5415(17) 173.4(19) . N17 H17A O32 0.94(2) 1.95(2) 2.879(2) 171.8(18) . N17 H17B N22 0.89(2) 2.12(2) 2.954(2) 156.3(18) 3_556 _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.297 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.044 #END