# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _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_section_title ; How reliable is the hydrogen-bonded amide 'ladder' motif? ; loop_ _publ_author_name 'C. Aakeroy' 'John Desper' 'Benjamin M. T. Scott' data_7 _database_code_depnum_ccdc_archive 'CCDC 653212' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-[(1-pyrazolyl)methyl]benzamide ; _chemical_name_common 4-((1-pyrazolyl)methyl)benzamide _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O' _chemical_formula_sum 'C11 H11 N3 O' _chemical_formula_weight 201.23 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 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 21.660(4) _cell_length_b 4.7544(9) _cell_length_c 9.9321(19) _cell_angle_alpha 90.00 _cell_angle_beta 93.912(3) _cell_angle_gamma 90.00 _cell_volume 1020.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1681 _cell_measurement_theta_min 3.75 _cell_measurement_theta_max 27.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 7149 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.40 _reflns_number_total 2429 _reflns_number_gt 1474 _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^)+(0.0700P)^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 2429 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 0.14044(9) 0.1101(4) 0.05239(19) 0.0216(4) Uani 1 1 d . . . C17 C 0.08126(9) 0.2693(4) 0.0278(2) 0.0233(4) Uani 1 1 d . . . N17 N 0.04533(8) 0.2983(4) 0.12991(18) 0.0267(4) Uani 1 1 d . . . H17A H 0.0067(10) 0.402(4) 0.116(2) 0.032 Uiso 1 1 d . . . H17B H 0.0569(10) 0.236(4) 0.209(2) 0.032 Uiso 1 1 d . . . O17 O 0.06682(6) 0.3717(3) -0.08636(13) 0.0283(4) Uani 1 1 d . . . C12 C 0.14736(9) -0.0999(4) 0.14942(19) 0.0239(5) Uani 1 1 d . . . H12 H 0.1138 -0.1461 0.2023 0.029 Uiso 1 1 calc R . . C13 C 0.20308(9) -0.2422(4) 0.1693(2) 0.0258(5) Uani 1 1 d . . . H13 H 0.2072 -0.3864 0.2356 0.031 Uiso 1 1 calc R . . C14 C 0.25311(9) -0.1781(4) 0.0943(2) 0.0245(5) Uani 1 1 d . . . C15 C 0.24574(9) 0.0339(4) -0.0026(2) 0.0249(5) Uani 1 1 d . . . H15 H 0.2795 0.0822 -0.0545 0.030 Uiso 1 1 calc R . . C16 C 0.19000(9) 0.1751(4) -0.0244(2) 0.0238(4) Uani 1 1 d . . . H16 H 0.1856 0.3167 -0.0918 0.029 Uiso 1 1 calc R . . C18 C 0.31295(9) -0.3390(4) 0.1138(2) 0.0278(5) Uani 1 1 d . . . H18A H 0.3091 -0.4814 0.1855 0.033 Uiso 1 1 calc R . . H18B H 0.3205 -0.4398 0.0292 0.033 Uiso 1 1 calc R . . N21 N 0.36570(7) -0.1578(3) 0.15047(17) 0.0239(4) Uani 1 1 d . . . N22 N 0.37338(8) -0.0441(4) 0.27564(17) 0.0315(4) Uani 1 1 d . . . C23 C 0.42307(10) 0.1202(4) 0.2694(2) 0.0321(5) Uani 1 1 d . . . H23 H 0.4404 0.2280 0.3432 0.039 Uiso 1 1 calc R . . C24 C 0.44642(9) 0.1154(4) 0.1432(2) 0.0324(5) Uani 1 1 d . . . H24 H 0.4811 0.2155 0.1145 0.039 Uiso 1 1 calc R . . C25 C 0.40846(9) -0.0655(4) 0.0687(2) 0.0294(5) Uani 1 1 d . . . H25 H 0.4117 -0.1160 -0.0231 0.035 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 0.0279(10) 0.0230(9) 0.0140(11) -0.0061(8) 0.0020(8) -0.0030(8) C17 0.0300(10) 0.0233(9) 0.0168(11) -0.0012(8) 0.0021(9) -0.0039(8) N17 0.0297(9) 0.0356(9) 0.0153(10) 0.0031(8) 0.0045(8) 0.0053(8) O17 0.0334(8) 0.0363(8) 0.0154(8) 0.0012(6) 0.0041(6) 0.0048(6) C12 0.0292(10) 0.0257(9) 0.0174(11) -0.0020(8) 0.0054(8) -0.0041(8) C13 0.0365(11) 0.0228(9) 0.0184(11) 0.0015(8) 0.0031(9) -0.0022(8) C14 0.0313(11) 0.0217(9) 0.0207(11) -0.0039(8) 0.0019(9) -0.0016(8) C15 0.0286(11) 0.0263(10) 0.0202(12) -0.0021(8) 0.0054(9) -0.0034(8) C16 0.0322(11) 0.0231(9) 0.0161(11) 0.0002(8) 0.0024(8) -0.0018(8) C18 0.0313(11) 0.0242(10) 0.0281(13) -0.0003(9) 0.0033(9) -0.0004(8) N21 0.0281(9) 0.0242(8) 0.0194(10) 0.0006(7) 0.0004(7) 0.0008(7) N22 0.0395(10) 0.0367(10) 0.0180(10) -0.0035(8) 0.0014(8) 0.0017(8) C23 0.0343(11) 0.0327(11) 0.0282(13) -0.0073(9) -0.0067(9) 0.0021(9) C24 0.0297(11) 0.0320(11) 0.0356(14) -0.0004(10) 0.0039(10) -0.0031(9) C25 0.0318(11) 0.0331(11) 0.0241(12) 0.0000(9) 0.0075(9) 0.0009(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C12 1.389(3) . ? C11 C16 1.393(2) . ? C11 C17 1.494(3) . ? C17 O17 1.254(2) . ? C17 N17 1.327(2) . ? N17 H17A 0.97(2) . ? N17 H17B 0.86(2) . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(2) . ? C13 H13 0.9500 . ? C14 C15 1.395(3) . ? C14 C18 1.506(3) . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C18 N21 1.457(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N21 C25 1.346(2) . ? N21 N22 1.355(2) . ? N22 C23 1.335(3) . ? C23 C24 1.383(3) . ? C23 H23 0.9500 . ? C24 C25 1.371(3) . ? C24 H24 0.9500 . ? C25 H25 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 C12 C11 C16 119.24(18) . . ? C12 C11 C17 121.90(16) . . ? C16 C11 C17 118.86(17) . . ? O17 C17 N17 121.84(18) . . ? O17 C17 C11 120.19(16) . . ? N17 C17 C11 117.97(18) . . ? C17 N17 H17A 119.0(12) . . ? C17 N17 H17B 120.8(14) . . ? H17A N17 H17B 120.0(18) . . ? C13 C12 C11 120.11(17) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 121.29(19) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 118.14(18) . . ? C13 C14 C18 120.99(18) . . ? C15 C14 C18 120.85(17) . . ? C16 C15 C14 121.00(17) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 120.21(18) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? N21 C18 C14 112.63(15) . . ? N21 C18 H18A 109.1 . . ? C14 C18 H18A 109.1 . . ? N21 C18 H18B 109.1 . . ? C14 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C25 N21 N22 112.15(16) . . ? C25 N21 C18 126.98(17) . . ? N22 N21 C18 120.68(15) . . ? C23 N22 N21 103.88(16) . . ? N22 C23 C24 112.22(19) . . ? N22 C23 H23 123.9 . . ? C24 C23 H23 123.9 . . ? C25 C24 C23 104.87(18) . . ? C25 C24 H24 127.6 . . ? C23 C24 H24 127.6 . . ? N21 C25 C24 106.88(18) . . ? N21 C25 H25 126.6 . . ? C24 C25 H25 126.6 . . ? 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 C12 C11 C17 O17 -152.27(18) . . . . ? C16 C11 C17 O17 27.8(3) . . . . ? C12 C11 C17 N17 27.9(3) . . . . ? C16 C11 C17 N17 -151.98(18) . . . . ? C16 C11 C12 C13 0.1(3) . . . . ? C17 C11 C12 C13 -179.83(17) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C12 C13 C14 C18 -178.29(18) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C18 C14 C15 C16 177.53(18) . . . . ? C14 C15 C16 C11 1.1(3) . . . . ? C12 C11 C16 C15 -0.8(3) . . . . ? C17 C11 C16 C15 179.08(17) . . . . ? C13 C14 C18 N21 -122.39(19) . . . . ? C15 C14 C18 N21 59.6(2) . . . . ? C14 C18 N21 C25 -101.5(2) . . . . ? C14 C18 N21 N22 73.1(2) . . . . ? C25 N21 N22 C23 -0.7(2) . . . . ? C18 N21 N22 C23 -176.10(17) . . . . ? N21 N22 C23 C24 0.7(2) . . . . ? N22 C23 C24 C25 -0.4(2) . . . . ? N22 N21 C25 C24 0.5(2) . . . . ? C18 N21 C25 C24 175.51(17) . . . . ? C23 C24 C25 N21 -0.1(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 O17 0.97(2) 1.93(2) 2.899(2) 176.4(17) 3_565 N17 H17B O17 0.86(2) 2.09(2) 2.938(2) 167(2) 4_566 _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.302 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.052 #END data_8 _database_code_depnum_ccdc_archive 'CCDC 653213' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-[(3,5-dimethylpyrazol-1-yl)methyl]benzamide ; _chemical_name_common 4-((3,5-dimethylpyrazol-1-yl)methyl)benzamide _chemical_melting_point ? _chemical_formula_moiety ; (C13 H15 N3 O) ; _chemical_formula_sum 'C13 H15 N3 O' _chemical_formula_weight 229.28 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)/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 8.4005(7) _cell_length_b 8.0671(7) _cell_length_c 18.0477(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.621(6) _cell_angle_gamma 90.00 _cell_volume 1193.50(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2149 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.35 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.084 _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 8390 _diffrn_reflns_av_R_equivalents 0.0919 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2789 _reflns_number_gt 1646 _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^)+(0.0650P)^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 2789 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _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 0.21703(18) 0.6793(2) 0.11285(9) 0.0310(4) Uani 1 1 d . . . C12 C 0.3110(2) 0.7028(2) 0.18532(10) 0.0360(4) Uani 1 1 d . . . H12 H 0.3089 0.8063 0.2101 0.043 Uiso 1 1 calc R . . C13 C 0.4078(2) 0.5754(2) 0.22152(9) 0.0353(4) Uani 1 1 d . . . H13 H 0.4700 0.5915 0.2717 0.042 Uiso 1 1 calc R . . C14 C 0.41517(19) 0.4260(2) 0.18609(9) 0.0320(4) Uani 1 1 d . . . C15 C 0.3196(2) 0.4029(2) 0.11392(10) 0.0401(5) Uani 1 1 d . . . H15 H 0.3231 0.2999 0.0889 0.048 Uiso 1 1 calc R . . C16 C 0.2199(2) 0.5269(2) 0.07806(10) 0.0382(5) Uani 1 1 d . . . H16 H 0.1526 0.5080 0.0292 0.046 Uiso 1 1 calc R . . C17 C 0.11795(19) 0.8153(2) 0.06987(10) 0.0356(4) Uani 1 1 d . . . N17 N 0.1721(2) 0.9681(2) 0.08575(9) 0.0401(4) Uani 1 1 d . . . H17A H 0.119(2) 1.046(3) 0.0601(11) 0.048 Uiso 1 1 d . . . H17B H 0.273(2) 0.991(2) 0.1149(11) 0.048 Uiso 1 1 d . . . O17 O -0.00548(14) 0.78419(17) 0.02102(7) 0.0462(4) Uani 1 1 d . . . C18 C 0.5249(2) 0.2908(2) 0.22583(10) 0.0410(5) Uani 1 1 d . . . H18A H 0.6115 0.3414 0.2655 0.049 Uiso 1 1 calc R . . H18B H 0.4604 0.2161 0.2515 0.049 Uiso 1 1 calc R . . N21 N 0.60028(17) 0.19388(19) 0.17564(8) 0.0354(4) Uani 1 1 d . . . N22 N 0.53928(17) 0.04067(19) 0.15246(8) 0.0367(4) Uani 1 1 d . . . C23 C 0.6341(2) -0.0150(2) 0.10780(9) 0.0350(4) Uani 1 1 d . . . C24 C 0.7526(2) 0.1018(3) 0.10208(10) 0.0389(5) Uani 1 1 d . . . H24 H 0.8346 0.0914 0.0735 0.047 Uiso 1 1 calc R . . C25 C 0.7285(2) 0.2339(2) 0.14533(9) 0.0367(5) Uani 1 1 d . . . C26 C 0.6058(2) -0.1797(3) 0.07050(11) 0.0458(5) Uani 1 1 d . . . H26A H 0.5623 -0.2562 0.1033 0.069 Uiso 1 1 calc R . . H26B H 0.7091 -0.2231 0.0617 0.069 Uiso 1 1 calc R . . H26C H 0.5275 -0.1685 0.0218 0.069 Uiso 1 1 calc R . . C27 C 0.8155(2) 0.3951(3) 0.16104(12) 0.0558(6) Uani 1 1 d . . . H27A H 0.8579 0.4071 0.2158 0.084 Uiso 1 1 calc R . . H27B H 0.7397 0.4860 0.1427 0.084 Uiso 1 1 calc R . . H27C H 0.9062 0.3985 0.1349 0.084 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 0.0256(8) 0.0348(10) 0.0342(9) -0.0010(7) 0.0098(6) -0.0007(7) C12 0.0366(9) 0.0339(11) 0.0379(9) -0.0076(8) 0.0089(7) 0.0001(8) C13 0.0368(9) 0.0371(11) 0.0302(8) -0.0041(8) 0.0033(7) 0.0009(8) C14 0.0327(9) 0.0327(10) 0.0317(9) -0.0001(7) 0.0096(7) -0.0012(8) C15 0.0465(10) 0.0314(11) 0.0399(10) -0.0074(8) 0.0038(8) 0.0038(9) C16 0.0353(9) 0.0396(11) 0.0360(9) -0.0069(8) -0.0004(7) 0.0021(8) C17 0.0288(9) 0.0383(12) 0.0406(10) 0.0004(8) 0.0097(7) 0.0036(8) N17 0.0385(9) 0.0332(10) 0.0464(9) 0.0006(7) 0.0042(7) 0.0076(8) O17 0.0319(7) 0.0467(9) 0.0548(8) 0.0025(6) -0.0019(6) 0.0031(6) C18 0.0478(11) 0.0434(12) 0.0312(9) -0.0003(8) 0.0076(8) 0.0078(9) N21 0.0360(8) 0.0344(9) 0.0351(8) 0.0018(6) 0.0061(6) 0.0034(7) N22 0.0377(8) 0.0338(9) 0.0380(8) 0.0009(7) 0.0068(6) 0.0013(7) C23 0.0319(9) 0.0420(11) 0.0292(8) 0.0028(8) 0.0023(7) 0.0072(8) C24 0.0282(9) 0.0553(13) 0.0330(9) 0.0027(9) 0.0062(7) 0.0049(9) C25 0.0295(9) 0.0435(12) 0.0343(9) 0.0066(8) 0.0005(7) 0.0013(8) C26 0.0452(11) 0.0462(13) 0.0449(11) -0.0053(9) 0.0078(8) 0.0059(9) C27 0.0500(12) 0.0532(15) 0.0603(13) 0.0026(11) 0.0037(10) -0.0086(11) _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 1.383(2) . ? C11 C12 1.385(2) . ? C11 C17 1.488(2) . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.372(2) . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 C18 1.504(2) . ? C15 C16 1.373(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.2311(19) . ? C17 N17 1.324(2) . ? N17 H17A 0.85(2) . ? N17 H17B 0.91(2) . ? C18 N21 1.443(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N21 C25 1.349(2) . ? N21 N22 1.368(2) . ? N22 C23 1.329(2) . ? C23 C24 1.390(3) . ? C23 C26 1.485(3) . ? C24 C25 1.362(3) . ? C24 H24 0.9500 . ? C25 C27 1.489(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 119.16(16) . . ? C16 C11 C17 118.79(15) . . ? C12 C11 C17 122.00(16) . . ? C13 C12 C11 119.98(17) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.96(15) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 118.69(16) . . ? C13 C14 C18 119.97(14) . . ? C15 C14 C18 121.34(16) . . ? C16 C15 C14 120.95(17) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 120.20(16) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O17 C17 N17 122.71(17) . . ? O17 C17 C11 120.72(17) . . ? N17 C17 C11 116.55(15) . . ? C17 N17 H17A 117.4(14) . . ? C17 N17 H17B 123.2(12) . . ? H17A N17 H17B 118.1(19) . . ? N21 C18 C14 113.61(14) . . ? N21 C18 H18A 108.8 . . ? C14 C18 H18A 108.8 . . ? N21 C18 H18B 108.8 . . ? C14 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C25 N21 N22 111.77(15) . . ? C25 N21 C18 128.54(17) . . ? N22 N21 C18 119.68(15) . . ? C23 N22 N21 104.86(14) . . ? N22 C23 C24 110.49(17) . . ? N22 C23 C26 121.28(17) . . ? C24 C23 C26 128.22(18) . . ? C25 C24 C23 106.81(16) . . ? C25 C24 H24 126.6 . . ? C23 C24 H24 126.6 . . ? N21 C25 C24 106.07(16) . . ? N21 C25 C27 122.28(18) . . ? C24 C25 C27 131.65(18) . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 0.9(3) . . . . ? C17 C11 C12 C13 -176.60(16) . . . . ? C11 C12 C13 C14 1.4(3) . . . . ? C12 C13 C14 C15 -2.0(3) . . . . ? C12 C13 C14 C18 178.31(16) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C18 C14 C15 C16 -179.96(18) . . . . ? C14 C15 C16 C11 1.9(3) . . . . ? C12 C11 C16 C15 -2.5(3) . . . . ? C17 C11 C16 C15 175.05(17) . . . . ? C16 C11 C17 O17 29.4(3) . . . . ? C12 C11 C17 O17 -153.13(18) . . . . ? C16 C11 C17 N17 -148.97(17) . . . . ? C12 C11 C17 N17 28.5(2) . . . . ? C13 C14 C18 N21 -143.63(17) . . . . ? C15 C14 C18 N21 36.7(2) . . . . ? C14 C18 N21 C25 77.4(2) . . . . ? C14 C18 N21 N22 -101.65(18) . . . . ? C25 N21 N22 C23 0.88(17) . . . . ? C18 N21 N22 C23 -179.88(14) . . . . ? N21 N22 C23 C24 -0.58(18) . . . . ? N21 N22 C23 C26 -179.55(14) . . . . ? N22 C23 C24 C25 0.09(19) . . . . ? C26 C23 C24 C25 178.97(16) . . . . ? N22 N21 C25 C24 -0.84(18) . . . . ? C18 N21 C25 C24 -179.98(15) . . . . ? N22 N21 C25 C27 179.29(15) . . . . ? C18 N21 C25 C27 0.1(3) . . . . ? C23 C24 C25 N21 0.44(18) . . . . ? C23 C24 C25 C27 -179.70(18) . . . . ? 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 O17 0.85(2) 2.08(2) 2.913(2) 168.3(19) 3_575 N17 H17B N22 0.91(2) 2.23(2) 3.112(2) 162.7(17) 1_565 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.168 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.048 #END data_9 _database_code_depnum_ccdc_archive 'CCDC 653214' _audit_creation_method SHELXL-97 _chemical_name_systematic ; BS-3-93-3G 3-[(4-bromo-3,5-dimethylpyrazol-1-yl)methyl]benzamide, succinic acid ; _chemical_name_common ;BS-3-93-3G 3-((4-bromo-3,5-dimethylpyrazol-1- yl)methyl)benzamide, succinic acid ; _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 Br N3 O' _chemical_formula_sum 'C13 H14 Br N3 O' _chemical_formula_weight 308.18 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' Br Br -0.2901 2.4595 '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 12.437(3) _cell_length_b 8.8195(17) _cell_length_c 12.468(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.488(6) _cell_angle_gamma 90.00 _cell_volume 1244.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3973 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 36.42 _exptl_crystal_description prism _exptl_crystal_colour clear _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 3.294 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6378 _exptl_absorpt_correction_T_max 0.6378 _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 58663 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 33.14 _reflns_number_total 4624 _reflns_number_gt 3856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.6000P] 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 4624 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.302476(10) 0.496716(13) 0.982680(10) 0.01678(4) Uani 1 1 d . . . N11 N 0.44558(9) 0.51371(11) 0.74885(9) 0.01489(18) Uani 1 1 d . . . N12 N 0.45061(9) 0.66478(11) 0.77202(8) 0.01621(18) Uani 1 1 d . . . C13 C 0.40620(10) 0.68105(13) 0.85248(10) 0.0150(2) Uani 1 1 d . . . C14 C 0.37236(10) 0.53854(13) 0.87865(10) 0.01378(19) Uani 1 1 d . . . C15 C 0.39866(10) 0.43278(12) 0.81107(10) 0.01370(19) Uiso 1 1 d . . . C16 C 0.39957(11) 0.83416(14) 0.90041(11) 0.0207(2) Uani 1 1 d . . . H16A H 0.3549 0.9028 0.8353 0.031 Uiso 1 1 calc R . . H16B H 0.4796 0.8740 0.9438 0.031 Uiso 1 1 calc R . . H16C H 0.3599 0.8262 0.9536 0.031 Uiso 1 1 calc R . . C17 C 0.38786(11) 0.26454(14) 0.80398(11) 0.0188(2) Uiso 1 1 d . . . H17A H 0.3468 0.2338 0.7213 0.028 Uiso 1 1 calc R . . H17B H 0.3428 0.2302 0.8479 0.028 Uiso 1 1 calc R . . H17C H 0.4668 0.2190 0.8380 0.028 Uiso 1 1 calc R . . C21 C 0.18945(10) 0.47081(13) 0.30734(10) 0.0133(2) Uani 1 1 d . . . C22 C 0.21148(10) 0.59583(13) 0.38251(10) 0.0161(2) Uani 1 1 d . . . H22 H 0.1644 0.6846 0.3566 0.019 Uiso 1 1 calc R . . C23 C 0.30206(10) 0.59044(14) 0.49504(10) 0.0166(2) Uani 1 1 d . . . H23 H 0.3173 0.6764 0.5451 0.020 Uiso 1 1 calc R . . C24 C 0.37089(10) 0.46053(13) 0.53536(10) 0.01403(19) Uani 1 1 d . . . C25 C 0.34541(10) 0.33365(13) 0.46242(10) 0.0155(2) Uani 1 1 d . . . H25 H 0.3892 0.2428 0.4904 0.019 Uiso 1 1 calc R . . C26 C 0.25611(10) 0.33916(13) 0.34872(10) 0.0152(2) Uani 1 1 d . . . H26 H 0.2405 0.2528 0.2990 0.018 Uiso 1 1 calc R . . C27 C 0.10265(11) 0.47616(13) 0.18049(10) 0.0154(2) Uani 1 1 d . . . N27 N 0.01778(9) 0.58025(12) 0.14823(9) 0.01691(19) Uani 1 1 d . . . H27A H -0.0251(14) 0.5863(19) 0.0778(15) 0.020 Uiso 1 1 d . . . H27B H 0.0105(14) 0.6408(19) 0.1934(15) 0.020 Uiso 1 1 d . . . O27 O 0.11278(9) 0.38593(12) 0.10901(8) 0.0263(2) Uani 1 1 d . . . C28 C 0.47569(11) 0.45888(15) 0.65447(10) 0.0171(2) Uani 1 1 d . . . H28A H 0.5063 0.3540 0.6728 0.021 Uiso 1 1 calc R . . H28B H 0.5393 0.5231 0.6507 0.021 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 Br1 0.01604(6) 0.01972(6) 0.01511(6) 0.00191(4) 0.00700(5) -0.00008(4) N11 0.0165(4) 0.0164(4) 0.0103(4) -0.0004(3) 0.0041(4) -0.0020(3) N12 0.0177(4) 0.0154(4) 0.0124(4) 0.0008(3) 0.0031(3) -0.0036(3) C13 0.0140(5) 0.0150(5) 0.0118(5) 0.0006(4) 0.0012(4) -0.0013(4) C14 0.0126(5) 0.0161(5) 0.0113(4) 0.0011(4) 0.0036(4) -0.0008(4) C16 0.0233(6) 0.0152(5) 0.0194(5) -0.0023(4) 0.0046(5) -0.0018(4) C21 0.0136(5) 0.0152(5) 0.0103(4) 0.0001(4) 0.0043(4) -0.0006(4) C22 0.0192(5) 0.0140(5) 0.0133(5) -0.0003(4) 0.0049(4) 0.0017(4) C23 0.0203(5) 0.0146(5) 0.0127(5) -0.0019(4) 0.0046(4) -0.0009(4) C24 0.0143(5) 0.0172(5) 0.0109(4) 0.0005(4) 0.0056(4) -0.0010(4) C25 0.0166(5) 0.0154(5) 0.0141(5) 0.0008(4) 0.0060(4) 0.0025(4) C26 0.0173(5) 0.0140(5) 0.0136(5) -0.0013(4) 0.0056(4) 0.0002(4) C27 0.0154(5) 0.0163(5) 0.0126(5) -0.0005(4) 0.0040(4) -0.0014(4) N27 0.0169(4) 0.0189(5) 0.0105(4) -0.0014(4) 0.0013(4) 0.0023(4) O27 0.0297(5) 0.0286(5) 0.0135(4) -0.0062(4) 0.0018(4) 0.0104(4) C28 0.0150(5) 0.0232(5) 0.0119(5) -0.0001(4) 0.0043(4) 0.0008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.8730(12) . ? N11 C15 1.3517(15) . ? N11 N12 1.3593(14) . ? N11 C28 1.4573(16) . ? N12 C13 1.3384(16) . ? C13 C14 1.4062(16) . ? C13 C16 1.4927(17) . ? C14 C15 1.3841(16) . ? C15 C17 1.4892(17) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 C26 1.3954(16) . ? C21 C22 1.3987(16) . ? C21 C27 1.5013(16) . ? C22 C23 1.3892(16) . ? C22 H22 0.9500 . ? C23 C24 1.3934(17) . ? C23 H23 0.9500 . ? C24 C25 1.3931(16) . ? C24 C28 1.5166(16) . ? C25 C26 1.3929(16) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O27 1.2396(15) . ? C27 N27 1.3292(16) . ? N27 H27A 0.819(17) . ? N27 H27B 0.808(17) . ? C28 H28A 0.9900 . ? C28 H28B 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 C15 N11 N12 112.85(10) . . ? C15 N11 C28 127.21(10) . . ? N12 N11 C28 119.50(10) . . ? C13 N12 N11 105.52(9) . . ? N12 C13 C14 109.53(10) . . ? N12 C13 C16 120.36(10) . . ? C14 C13 C16 130.10(11) . . ? C15 C14 C13 106.98(10) . . ? C15 C14 Br1 125.70(9) . . ? C13 C14 Br1 127.31(9) . . ? N11 C15 C14 105.12(10) . . ? N11 C15 C17 122.81(10) . . ? C14 C15 C17 132.01(11) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 C21 C22 119.14(10) . . ? C26 C21 C27 118.25(10) . . ? C22 C21 C27 122.46(10) . . ? C23 C22 C21 120.09(11) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.82(11) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C25 C24 C23 119.04(10) . . ? C25 C24 C28 120.14(11) . . ? C23 C24 C28 120.75(11) . . ? C26 C25 C24 120.40(10) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C21 120.41(10) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? O27 C27 N27 122.04(11) . . ? O27 C27 C21 119.62(11) . . ? N27 C27 C21 118.33(10) . . ? C27 N27 H27A 116.9(11) . . ? C27 N27 H27B 123.4(12) . . ? H27A N27 H27B 119.5(16) . . ? N11 C28 C24 112.54(10) . . ? N11 C28 H28A 109.1 . . ? C24 C28 H28A 109.1 . . ? N11 C28 H28B 109.1 . . ? C24 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? 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 0.46(13) . . . . ? C28 N11 N12 C13 173.33(10) . . . . ? N11 N12 C13 C14 -0.51(12) . . . . ? N11 N12 C13 C16 179.12(10) . . . . ? N12 C13 C14 C15 0.40(13) . . . . ? C16 C13 C14 C15 -179.19(11) . . . . ? N12 C13 C14 Br1 -178.64(8) . . . . ? C16 C13 C14 Br1 1.77(18) . . . . ? N12 N11 C15 C14 -0.22(13) . . . . ? C28 N11 C15 C14 -172.41(11) . . . . ? N12 N11 C15 C17 -177.77(10) . . . . ? C28 N11 C15 C17 10.04(18) . . . . ? C13 C14 C15 N11 -0.11(12) . . . . ? Br1 C14 C15 N11 178.96(8) . . . . ? C13 C14 C15 C17 177.12(12) . . . . ? Br1 C14 C15 C17 -3.82(19) . . . . ? C26 C21 C22 C23 2.73(17) . . . . ? C27 C21 C22 C23 -172.67(11) . . . . ? C21 C22 C23 C24 -0.97(18) . . . . ? C22 C23 C24 C25 -1.94(17) . . . . ? C22 C23 C24 C28 175.22(11) . . . . ? C23 C24 C25 C26 3.09(17) . . . . ? C28 C24 C25 C26 -174.09(11) . . . . ? C24 C25 C26 C21 -1.33(18) . . . . ? C22 C21 C26 C25 -1.59(17) . . . . ? C27 C21 C26 C25 174.00(11) . . . . ? C26 C21 C27 O27 -18.97(17) . . . . ? C22 C21 C27 O27 156.47(12) . . . . ? C26 C21 C27 N27 162.03(11) . . . . ? C22 C21 C27 N27 -22.53(17) . . . . ? C15 N11 C28 C24 84.93(14) . . . . ? N12 N11 C28 C24 -86.80(13) . . . . ? C25 C24 C28 N11 -132.16(11) . . . . ? C23 C24 C28 N11 50.71(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 N27 H27A O27 0.819(17) 2.137(17) 2.9488(15) 171.0(16) 3_565 N27 H27B N12 0.808(17) 2.249(17) 3.0341(15) 163.9(16) 4_575 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.681 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.066 #END data_10 _database_code_depnum_ccdc_archive 'CCDC 653215' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-[(1-pyrazolyl)methyl]benzamide ; _chemical_name_common 3-((1-pyrazolyl)methyl)benzamide _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O' _chemical_formula_sum 'C11 H11 N3 O' _chemical_formula_weight 201.23 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 7.7873(5) _cell_length_b 8.1130(6) _cell_length_c 8.8400(6) _cell_angle_alpha 77.6614(13) _cell_angle_beta 74.4604(13) _cell_angle_gamma 68.3976(12) _cell_volume 496.14(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3132 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.798 _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 5729 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2838 _reflns_number_gt 2546 _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^)+(0.0800P)^2^+0.1000P] 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 2838 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.63028(11) 0.79687(11) 0.07330(10) 0.01443(19) Uani 1 1 d . . . N12 N 0.63016(12) 0.87465(11) 0.19455(10) 0.01618(19) Uani 1 1 d . . . C13 C 0.80201(14) 0.88974(13) 0.16156(12) 0.0173(2) Uani 1 1 d . . . H13 H 0.8447 0.9400 0.2261 0.021 Uiso 1 1 calc R . . C14 C 0.91169(14) 0.82242(14) 0.02010(12) 0.0178(2) Uani 1 1 d . . . H14 H 1.0374 0.8187 -0.0285 0.021 Uiso 1 1 calc R . . C15 C 0.79642(14) 0.76294(13) -0.03264(12) 0.0167(2) Uani 1 1 d . . . H15 H 0.8278 0.7084 -0.1258 0.020 Uiso 1 1 calc R . . C16 C 0.27884(14) 0.56132(14) 0.25507(12) 0.0174(2) Uani 1 1 d . . . H16 H 0.1717 0.6451 0.2176 0.021 Uiso 1 1 calc R . . C21 C 0.59045(13) 0.31908(12) 0.37033(11) 0.01314(19) Uani 1 1 d . . . C22 C 0.60941(13) 0.46527(13) 0.25869(11) 0.0141(2) Uani 1 1 d . . . H22 H 0.7291 0.4818 0.2222 0.017 Uiso 1 1 calc R . . C23 C 0.45373(13) 0.58698(13) 0.20064(11) 0.0144(2) Uani 1 1 d . . . C24 C 0.41574(14) 0.29260(13) 0.42127(11) 0.0155(2) Uani 1 1 d . . . H24 H 0.4030 0.1918 0.4952 0.019 Uiso 1 1 calc R . . C25 C 0.25996(14) 0.41410(14) 0.36365(12) 0.0175(2) Uani 1 1 d . . . H25 H 0.1408 0.3964 0.3985 0.021 Uiso 1 1 calc R . . C27 C 0.76343(13) 0.19173(12) 0.42796(11) 0.0141(2) Uani 1 1 d . . . N27 N 0.73786(12) 0.07483(11) 0.55703(11) 0.01674(19) Uani 1 1 d . . . H27A H 0.842(2) -0.006(2) 0.5875(17) 0.020 Uiso 1 1 d . . . H27B H 0.629(2) 0.0879(19) 0.6184(17) 0.020 Uiso 1 1 d . . . O27 O 0.92206(10) 0.19376(10) 0.35393(9) 0.01995(19) Uani 1 1 d . . . C28 C 0.46905(14) 0.74526(13) 0.07695(12) 0.0170(2) Uani 1 1 d . . . H28A H 0.4795 0.7149 -0.0286 0.020 Uiso 1 1 calc R . . H28B H 0.3521 0.8483 0.0990 0.020 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 N11 0.0158(4) 0.0132(4) 0.0141(4) 0.0009(3) -0.0042(3) -0.0052(3) N12 0.0177(4) 0.0157(4) 0.0147(4) -0.0011(3) -0.0032(3) -0.0056(3) C13 0.0187(4) 0.0176(5) 0.0168(5) 0.0000(4) -0.0054(4) -0.0073(4) C14 0.0165(4) 0.0187(5) 0.0170(5) 0.0004(4) -0.0028(3) -0.0066(3) C15 0.0184(4) 0.0159(4) 0.0140(4) -0.0002(3) -0.0022(3) -0.0054(3) C16 0.0141(4) 0.0183(5) 0.0193(5) -0.0003(4) -0.0059(3) -0.0043(3) C21 0.0130(4) 0.0124(4) 0.0131(4) -0.0017(3) -0.0028(3) -0.0030(3) C22 0.0131(4) 0.0139(4) 0.0153(4) -0.0008(3) -0.0030(3) -0.0048(3) C23 0.0158(4) 0.0131(4) 0.0151(4) 0.0001(3) -0.0051(3) -0.0053(3) C24 0.0163(4) 0.0160(4) 0.0146(4) -0.0003(3) -0.0029(3) -0.0067(3) C25 0.0139(4) 0.0214(5) 0.0179(5) -0.0010(4) -0.0033(3) -0.0077(4) C27 0.0145(4) 0.0121(4) 0.0141(4) -0.0011(3) -0.0028(3) -0.0031(3) N27 0.0134(4) 0.0153(4) 0.0166(4) 0.0030(3) -0.0019(3) -0.0028(3) O27 0.0132(3) 0.0208(4) 0.0195(4) 0.0047(3) -0.0016(3) -0.0036(3) C28 0.0165(4) 0.0156(4) 0.0199(5) 0.0035(4) -0.0083(3) -0.0066(3) _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 C15 1.3511(12) . ? N11 N12 1.3547(12) . ? N11 C28 1.4533(12) . ? N12 C13 1.3368(13) . ? C13 C14 1.4027(14) . ? C13 H13 0.9500 . ? C14 C15 1.3767(14) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C25 1.3904(14) . ? C16 C23 1.3945(13) . ? C16 H16 0.9500 . ? C21 C24 1.3948(13) . ? C21 C22 1.3975(13) . ? C21 C27 1.5032(13) . ? C22 C23 1.3941(13) . ? C22 H22 0.9500 . ? C23 C28 1.5171(13) . ? C24 C25 1.3924(13) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C27 O27 1.2376(11) . ? C27 N27 1.3400(12) . ? N27 H27A 0.901(15) . ? N27 H27B 0.857(15) . ? C28 H28A 0.9900 . ? C28 H28B 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 C15 N11 N12 112.34(8) . . ? C15 N11 C28 127.80(9) . . ? N12 N11 C28 119.59(8) . . ? C13 N12 N11 104.30(8) . . ? N12 C13 C14 111.80(9) . . ? N12 C13 H13 124.1 . . ? C14 C13 H13 124.1 . . ? C15 C14 C13 104.58(9) . . ? C15 C14 H14 127.7 . . ? C13 C14 H14 127.7 . . ? N11 C15 C14 106.98(9) . . ? N11 C15 H15 126.5 . . ? C14 C15 H15 126.5 . . ? C25 C16 C23 120.58(9) . . ? C25 C16 H16 119.7 . . ? C23 C16 H16 119.7 . . ? C24 C21 C22 119.81(9) . . ? C24 C21 C27 122.17(9) . . ? C22 C21 C27 118.00(8) . . ? C23 C22 C21 120.36(9) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C16 119.31(9) . . ? C22 C23 C28 122.04(9) . . ? C16 C23 C28 118.64(8) . . ? C25 C24 C21 119.93(9) . . ? C25 C24 H24 120.0 . . ? C21 C24 H24 120.0 . . ? C16 C25 C24 119.98(9) . . ? C16 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? O27 C27 N27 122.52(9) . . ? O27 C27 C21 120.02(8) . . ? N27 C27 C21 117.42(8) . . ? C27 N27 H27A 117.3(9) . . ? C27 N27 H27B 121.7(10) . . ? H27A N27 H27B 120.0(13) . . ? N11 C28 C23 112.93(8) . . ? N11 C28 H28A 109.0 . . ? C23 C28 H28A 109.0 . . ? N11 C28 H28B 109.0 . . ? C23 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? 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 0.27(11) . . . . ? C28 N11 N12 C13 174.67(8) . . . . ? N11 N12 C13 C14 0.08(11) . . . . ? N12 C13 C14 C15 -0.38(12) . . . . ? N12 N11 C15 C14 -0.52(11) . . . . ? C28 N11 C15 C14 -174.35(9) . . . . ? C13 C14 C15 N11 0.52(11) . . . . ? C24 C21 C22 C23 1.46(14) . . . . ? C27 C21 C22 C23 179.66(8) . . . . ? C21 C22 C23 C16 -0.03(15) . . . . ? C21 C22 C23 C28 -178.72(9) . . . . ? C25 C16 C23 C22 -1.31(15) . . . . ? C25 C16 C23 C28 177.42(9) . . . . ? C22 C21 C24 C25 -1.54(15) . . . . ? C27 C21 C24 C25 -179.67(9) . . . . ? C23 C16 C25 C24 1.23(16) . . . . ? C21 C24 C25 C16 0.21(15) . . . . ? C24 C21 C27 O27 162.37(10) . . . . ? C22 C21 C27 O27 -15.79(14) . . . . ? C24 C21 C27 N27 -15.39(14) . . . . ? C22 C21 C27 N27 166.45(9) . . . . ? C15 N11 C28 C23 102.91(11) . . . . ? N12 N11 C28 C23 -70.53(11) . . . . ? C22 C23 C28 N11 -22.99(13) . . . . ? C16 C23 C28 N11 158.31(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N27 H27A O27 0.901(15) 2.018(15) 2.9182(11) 177.2(13) 2_756 N27 H27B N12 0.857(15) 2.208(15) 3.0580(12) 170.9(14) 2_666 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.476 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.061 #END data_11 _database_code_depnum_ccdc_archive 'CCDC 653216' _audit_creation_method SHELXL-97 _chemical_name_systematic ; BS-3-92-4 3-[(3,5-dimethylpyrazol-1-yl)methyl]benzamide ; _chemical_name_common 'BS-3-92-4 3-((3,5-dimethylpyrazol-1-yl)methyl)benzamide' _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N3 O' _chemical_formula_sum 'C13 H15 N3 O' _chemical_formula_weight 229.28 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0162(4) _cell_length_b 8.0603(4) _cell_length_c 10.4542(5) _cell_angle_alpha 97.253(2) _cell_angle_beta 106.060(2) _cell_angle_gamma 109.335(2) _cell_volume 594.57(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9065 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 31.45 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9875 _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 21375 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 31.00 _reflns_number_total 3757 _reflns_number_gt 3010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.1000P] 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 3757 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.50776(13) 0.29422(13) 0.41569(9) 0.01634(19) Uani 1 1 d . . . C17 C 0.71498(14) 0.36120(14) 0.44063(10) 0.0191(2) Uani 1 1 d . . . N17 N 0.82663(12) 0.35198(13) 0.55890(9) 0.02161(19) Uani 1 1 d . . . H17A H 0.953(2) 0.4118(18) 0.5791(14) 0.026 Uiso 1 1 d . . . H17B H 0.7841(19) 0.3334(18) 0.6313(14) 0.026 Uiso 1 1 d . . . O17 O 0.77660(11) 0.41894(13) 0.35158(8) 0.0295(2) Uani 1 1 d . . . C12 C 0.39548(13) 0.33393(13) 0.30537(10) 0.01725(19) Uani 1 1 d . . . H12 H 0.4519 0.4025 0.2502 0.021 Uiso 1 1 calc R . . C13 C 0.20265(13) 0.27440(13) 0.27557(10) 0.0182(2) Uani 1 1 d . . . C14 C 0.12146(14) 0.17611(15) 0.35817(12) 0.0247(2) Uani 1 1 d . . . H14 H -0.0102 0.1368 0.3396 0.030 Uiso 1 1 calc R . . C15 C 0.23191(15) 0.13530(16) 0.46732(12) 0.0283(2) Uani 1 1 d . . . H15 H 0.1753 0.0668 0.5225 0.034 Uiso 1 1 calc R . . C16 C 0.42479(14) 0.19408(14) 0.49639(11) 0.0214(2) Uani 1 1 d . . . H16 H 0.5000 0.1659 0.5713 0.026 Uiso 1 1 calc R . . C18 C 0.07558(14) 0.31228(14) 0.15578(11) 0.0230(2) Uani 1 1 d . . . H18A H 0.0060 0.1997 0.0819 0.028 Uiso 1 1 calc R . . H18B H -0.0178 0.3467 0.1857 0.028 Uiso 1 1 calc R . . N21 N 0.17553(12) 0.45476(11) 0.10082(9) 0.01901(18) Uani 1 1 d . . . N22 N 0.24208(12) 0.62969(11) 0.17277(8) 0.01890(18) Uani 1 1 d . . . C23 C 0.33358(14) 0.72696(14) 0.10142(10) 0.0188(2) Uani 1 1 d . . . C24 C 0.32662(14) 0.61432(14) -0.01569(10) 0.0209(2) Uani 1 1 d . . . H24 H 0.3811 0.6506 -0.0826 0.025 Uiso 1 1 calc R . . C25 C 0.22440(14) 0.44036(14) -0.01330(10) 0.0202(2) Uani 1 1 d . . . C26 C 0.16725(17) 0.26514(16) -0.11215(13) 0.0306(3) Uani 1 1 d . . . H26A H 0.2161 0.1848 -0.0647 0.046 Uiso 1 1 calc R . . H26B H 0.2182 0.2870 -0.1863 0.046 Uiso 1 1 calc R . . H26C H 0.0298 0.2082 -0.1506 0.046 Uiso 1 1 calc R . . C27 C 0.42308(17) 0.92828(15) 0.14995(12) 0.0280(2) Uani 1 1 d . . . H27A H 0.3811 0.9678 0.2236 0.042 Uiso 1 1 calc R . . H27B H 0.3868 0.9829 0.0736 0.042 Uiso 1 1 calc R . . H27C H 0.5601 0.9664 0.1845 0.042 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 0.0183(4) 0.0171(4) 0.0145(4) 0.0032(3) 0.0063(3) 0.0075(3) C17 0.0203(4) 0.0253(5) 0.0146(5) 0.0050(4) 0.0081(3) 0.0105(4) N17 0.0197(4) 0.0327(5) 0.0158(4) 0.0095(4) 0.0072(3) 0.0118(3) O17 0.0213(4) 0.0535(5) 0.0165(4) 0.0144(4) 0.0098(3) 0.0129(3) C12 0.0201(4) 0.0184(4) 0.0145(4) 0.0055(3) 0.0069(3) 0.0076(3) C13 0.0192(4) 0.0170(4) 0.0174(5) 0.0047(4) 0.0050(3) 0.0063(3) C14 0.0181(4) 0.0280(5) 0.0259(6) 0.0109(4) 0.0072(4) 0.0048(4) C15 0.0236(5) 0.0333(6) 0.0272(6) 0.0174(5) 0.0100(4) 0.0053(4) C16 0.0231(5) 0.0235(5) 0.0178(5) 0.0094(4) 0.0060(4) 0.0084(4) C18 0.0184(4) 0.0232(5) 0.0241(5) 0.0102(4) 0.0033(4) 0.0055(4) N21 0.0208(4) 0.0200(4) 0.0163(4) 0.0062(3) 0.0048(3) 0.0086(3) N22 0.0230(4) 0.0209(4) 0.0144(4) 0.0057(3) 0.0066(3) 0.0097(3) C23 0.0229(4) 0.0215(5) 0.0152(5) 0.0069(4) 0.0077(4) 0.0107(4) C24 0.0245(5) 0.0273(5) 0.0152(5) 0.0067(4) 0.0089(4) 0.0130(4) C25 0.0215(4) 0.0247(5) 0.0159(5) 0.0037(4) 0.0044(3) 0.0129(4) C26 0.0320(6) 0.0290(6) 0.0280(6) -0.0024(5) 0.0061(5) 0.0151(5) C27 0.0398(6) 0.0219(5) 0.0240(6) 0.0074(4) 0.0139(5) 0.0106(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 1.3902(13) . ? C11 C12 1.3973(13) . ? C11 C17 1.4999(13) . ? C17 O17 1.2406(12) . ? C17 N17 1.3380(13) . ? N17 H17A 0.914(15) . ? N17 H17B 0.921(14) . ? C12 C13 1.3861(13) . ? C12 H12 0.9500 . ? C13 C14 1.3926(14) . ? C13 C18 1.5152(13) . ? C14 C15 1.3867(15) . ? C14 H14 0.9500 . ? C15 C16 1.3878(15) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C18 N21 1.4501(13) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N21 C25 1.3580(13) . ? N21 N22 1.3604(12) . ? N22 C23 1.3336(12) . ? C23 C24 1.4051(14) . ? C23 C27 1.4917(15) . ? C24 C25 1.3775(15) . ? C24 H24 0.9500 . ? C25 C26 1.4878(15) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 119.50(9) . . ? C16 C11 C17 122.77(8) . . ? C12 C11 C17 117.73(8) . . ? O17 C17 N17 122.39(9) . . ? O17 C17 C11 119.81(9) . . ? N17 C17 C11 117.78(9) . . ? C17 N17 H17A 116.3(8) . . ? C17 N17 H17B 121.1(9) . . ? H17A N17 H17B 117.4(12) . . ? C13 C12 C11 120.74(9) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.23(9) . . ? C12 C13 C18 122.40(9) . . ? C14 C13 C18 118.37(9) . . ? C15 C14 C13 120.33(9) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.31(10) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 119.89(9) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? N21 C18 C13 113.60(8) . . ? N21 C18 H18A 108.8 . . ? C13 C18 H18A 108.8 . . ? N21 C18 H18B 108.8 . . ? C13 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C25 N21 N22 112.15(8) . . ? C25 N21 C18 129.00(9) . . ? N22 N21 C18 118.75(8) . . ? C23 N22 N21 105.03(8) . . ? N22 C23 C24 110.89(9) . . ? N22 C23 C27 119.76(9) . . ? C24 C23 C27 129.35(10) . . ? C25 C24 C23 105.73(9) . . ? C25 C24 H24 127.1 . . ? C23 C24 H24 127.1 . . ? N21 C25 C24 106.19(9) . . ? N21 C25 C26 123.53(10) . . ? C24 C25 C26 130.26(10) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 166.24(10) . . . . ? C12 C11 C17 O17 -13.09(15) . . . . ? C16 C11 C17 N17 -12.26(15) . . . . ? C12 C11 C17 N17 168.41(9) . . . . ? C16 C11 C12 C13 -0.08(15) . . . . ? C17 C11 C12 C13 179.27(9) . . . . ? C11 C12 C13 C14 0.87(15) . . . . ? C11 C12 C13 C18 -179.14(9) . . . . ? C12 C13 C14 C15 -1.25(16) . . . . ? C18 C13 C14 C15 178.76(10) . . . . ? C13 C14 C15 C16 0.85(18) . . . . ? C14 C15 C16 C11 -0.05(18) . . . . ? C12 C11 C16 C15 -0.33(15) . . . . ? C17 C11 C16 C15 -179.65(10) . . . . ? C12 C13 C18 N21 -16.25(14) . . . . ? C14 C13 C18 N21 163.75(9) . . . . ? C13 C18 N21 C25 101.40(12) . . . . ? C13 C18 N21 N22 -74.61(11) . . . . ? C25 N21 N22 C23 0.42(10) . . . . ? C18 N21 N22 C23 177.07(8) . . . . ? N21 N22 C23 C24 -0.36(10) . . . . ? N21 N22 C23 C27 178.87(9) . . . . ? N22 C23 C24 C25 0.18(11) . . . . ? C27 C23 C24 C25 -178.95(10) . . . . ? N22 N21 C25 C24 -0.31(11) . . . . ? C18 N21 C25 C24 -176.54(9) . . . . ? N22 N21 C25 C26 -178.80(9) . . . . ? C18 N21 C25 C26 4.98(15) . . . . ? C23 C24 C25 N21 0.08(10) . . . . ? C23 C24 C25 C26 178.43(10) . . . . ? 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 O17 0.914(15) 2.002(15) 2.9033(12) 168.4(12) 2_766 N17 H17B N22 0.921(14) 2.110(14) 2.9997(12) 161.9(12) 2_666 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.478 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.050 #END data_12 _database_code_depnum_ccdc_archive 'CCDC 653217' _audit_creation_method SHELXL-97 _chemical_name_systematic ; BS-3-93-4f 3-[(3-bromo-2,4-dimethylpyrazol-1-yl)methyl]benzamide ; _chemical_name_common ;BS-3-93-4f 3-((3-bromo-2,4-dimethylpyrazol-1- yl)methyl)benzamide ; _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N3 O Br' _chemical_formula_sum 'C13 H14 Br N3 O' _chemical_formula_weight 308.18 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' Br Br -0.2901 2.4595 '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 8.9062(12) _cell_length_b 11.6933(18) _cell_length_c 14.146(2) _cell_angle_alpha 73.396(10) _cell_angle_beta 74.274(9) _cell_angle_gamma 70.553(9) _cell_volume 1305.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2898 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 23.90 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 3.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.551 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _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 15893 _diffrn_reflns_av_R_equivalents 0.0720 _diffrn_reflns_av_sigmaI/netI 0.0948 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.33 _reflns_number_total 5718 _reflns_number_gt 2902 _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^)+(0.1300P)^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 5718 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1450 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.2376 _refine_ls_wR_factor_gt 0.1928 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Br1 Br 1.18777(9) -0.10315(7) 0.81976(6) 0.0574(3) Uani 1 1 d . . . Br2 Br -0.46019(10) 0.39459(8) 0.32423(7) 0.0683(3) Uani 1 1 d . . . N11 N 0.7565(6) -0.0993(4) 0.7846(3) 0.0343(12) Uani 1 1 d . . . N12 N 0.7278(6) -0.1246(4) 0.8870(3) 0.0343(12) Uani 1 1 d . . . C13 C 0.8637(7) -0.1290(5) 0.9115(4) 0.0325(13) Uani 1 1 d . . . C14 C 0.9779(7) -0.1061(5) 0.8258(4) 0.0336(14) Uani 1 1 d . . . C15 C 0.9082(7) -0.0867(5) 0.7451(4) 0.0303(13) Uani 1 1 d . . . C16 C 0.8764(9) -0.1546(6) 1.0189(4) 0.0473(17) Uani 1 1 d . . . H16A H 0.7674 -0.1407 1.0610 0.071 Uiso 1 1 calc R . . H16B H 0.9313 -0.0989 1.0269 0.071 Uiso 1 1 calc R . . H16C H 0.9389 -0.2410 1.0394 0.071 Uiso 1 1 calc R . . C17 C 0.9700(9) -0.0521(6) 0.6347(5) 0.0468(17) Uani 1 1 d . . . H17A H 0.9216 0.0366 0.6100 0.070 Uiso 1 1 calc R . . H17B H 0.9405 -0.1007 0.6000 0.070 Uiso 1 1 calc R . . H17C H 1.0884 -0.0695 0.6216 0.070 Uiso 1 1 calc R . . C21 C 0.3545(7) 0.1998(5) 0.6001(4) 0.0331(13) Uani 1 1 d . . . C27 C 0.2570(8) 0.2262(6) 0.5210(4) 0.0383(15) Uani 1 1 d . . . N27 N 0.1767(6) 0.3422(4) 0.4954(3) 0.0325(11) Uani 1 1 d . . . H27A H 0.1126 0.3644 0.4518 0.039 Uiso 1 1 calc R . . H27B H 0.1864 0.3984 0.5218 0.039 Uiso 1 1 calc R . . O27 O 0.2485(7) 0.1457(5) 0.4875(4) 0.0691(17) Uani 1 1 d . . . C22 C 0.4470(7) 0.0785(5) 0.6283(4) 0.0344(14) Uani 1 1 d . . . H22 H 0.4522 0.0164 0.5955 0.041 Uiso 1 1 calc R . . C23 C 0.5312(7) 0.0494(5) 0.7043(4) 0.0318(13) Uani 1 1 d . . . C24 C 0.5254(8) 0.1395(6) 0.7509(4) 0.0393(15) Uani 1 1 d . . . H24 H 0.5829 0.1182 0.8038 0.047 Uiso 1 1 calc R . . C25 C 0.4368(8) 0.2607(6) 0.7212(5) 0.0440(16) Uani 1 1 d . . . H25 H 0.4334 0.3228 0.7533 0.053 Uiso 1 1 calc R . . C26 C 0.3530(7) 0.2907(6) 0.6445(5) 0.0388(15) Uani 1 1 d . . . H26 H 0.2943 0.3744 0.6222 0.047 Uiso 1 1 calc R . . C28 C 0.6296(8) -0.0853(5) 0.7342(5) 0.0401(15) Uani 1 1 d . . . H28A H 0.5555 -0.1342 0.7789 0.048 Uiso 1 1 calc R . . H28B H 0.6782 -0.1198 0.6730 0.048 Uiso 1 1 calc R . . N31 N 0.0020(6) 0.3974(4) 0.2684(4) 0.0383(12) Uani 1 1 d . . . N32 N -0.0242(6) 0.3683(4) 0.3724(4) 0.0392(13) Uani 1 1 d . . . C33 C -0.1756(8) 0.3639(5) 0.4014(5) 0.0396(15) Uani 1 1 d . . . C34 C -0.2490(8) 0.3891(5) 0.3202(5) 0.0383(14) Uani 1 1 d . . . C35 C -0.1302(8) 0.4123(5) 0.2348(5) 0.0378(15) Uani 1 1 d . . . C36 C -0.2479(10) 0.3332(7) 0.5114(5) 0.058(2) Uani 1 1 d . . . H36A H -0.2179 0.2429 0.5361 0.087 Uiso 1 1 calc R . . H36B H -0.3664 0.3654 0.5213 0.087 Uiso 1 1 calc R . . H36C H -0.2065 0.3713 0.5487 0.087 Uiso 1 1 calc R . . C37 C -0.1416(11) 0.4460(7) 0.1269(5) 0.062(2) Uani 1 1 d . . . H37A H -0.1433 0.5334 0.0996 0.093 Uiso 1 1 calc R . . H37B H -0.2415 0.4334 0.1204 0.093 Uiso 1 1 calc R . . H37C H -0.0476 0.3935 0.0896 0.093 Uiso 1 1 calc R . . C41 C 0.3016(7) 0.7033(5) 0.0965(4) 0.0310(13) Uani 1 1 d . . . C47 C 0.4354(8) 0.7382(6) 0.0160(5) 0.0388(15) Uani 1 1 d . . . N47 N 0.4496(5) 0.8464(4) 0.0088(3) 0.0251(10) Uani 1 1 d . . . H47A H 0.5266 0.8732 -0.0370 0.030 Uiso 1 1 calc R . . H47B H 0.3824 0.8937 0.0498 0.030 Uiso 1 1 calc R . . O47 O 0.5250(8) 0.6707(5) -0.0387(5) 0.088(2) Uani 1 1 d . . . C42 C 0.2864(7) 0.5840(5) 0.1152(5) 0.0371(14) Uani 1 1 d . . . H42 H 0.3582 0.5276 0.0750 0.045 Uiso 1 1 calc R . . C43 C 0.1669(7) 0.5472(5) 0.1921(4) 0.0349(14) Uani 1 1 d . . . C44 C 0.0641(8) 0.6289(6) 0.2505(5) 0.0429(16) Uani 1 1 d . . . H44 H -0.0155 0.6031 0.3050 0.051 Uiso 1 1 calc R . . C45 C 0.0767(8) 0.7493(6) 0.2297(4) 0.0383(14) Uani 1 1 d . . . H45 H 0.0029 0.8066 0.2685 0.046 Uiso 1 1 calc R . . C46 C 0.1959(7) 0.7860(5) 0.1529(4) 0.0338(13) Uani 1 1 d . . . H46 H 0.2048 0.8682 0.1391 0.041 Uiso 1 1 calc R . . C48 C 0.1603(8) 0.4142(6) 0.2126(5) 0.0496(18) Uani 1 1 d . . . H48A H 0.1853 0.3888 0.1478 0.060 Uiso 1 1 calc R . . H48B H 0.2447 0.3593 0.2514 0.060 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 Br1 0.0313(4) 0.0751(6) 0.0710(6) -0.0180(4) -0.0113(3) -0.0182(4) Br2 0.0363(5) 0.0770(6) 0.0972(7) -0.0212(5) -0.0191(4) -0.0161(4) N11 0.032(3) 0.036(3) 0.034(3) 0.002(2) -0.014(2) -0.009(2) N12 0.034(3) 0.037(3) 0.031(3) -0.002(2) -0.008(2) -0.011(2) C13 0.030(3) 0.038(3) 0.031(3) -0.002(2) -0.013(3) -0.010(3) C14 0.030(3) 0.031(3) 0.039(3) -0.006(3) -0.012(3) -0.004(3) C15 0.032(3) 0.024(3) 0.030(3) -0.005(2) -0.005(2) -0.003(2) C16 0.049(4) 0.065(5) 0.032(4) -0.010(3) -0.009(3) -0.020(4) C17 0.050(4) 0.049(4) 0.038(4) -0.009(3) -0.003(3) -0.014(3) C21 0.030(3) 0.039(3) 0.027(3) -0.004(3) -0.005(2) -0.009(3) C27 0.033(3) 0.043(4) 0.032(3) -0.006(3) -0.010(3) -0.001(3) N27 0.033(3) 0.023(2) 0.041(3) 0.000(2) -0.021(2) -0.002(2) O27 0.083(4) 0.058(3) 0.073(4) -0.024(3) -0.056(3) 0.013(3) C22 0.034(3) 0.040(3) 0.028(3) -0.008(2) -0.004(2) -0.010(3) C23 0.027(3) 0.035(3) 0.028(3) 0.001(2) -0.007(2) -0.006(2) C24 0.040(4) 0.046(4) 0.035(3) -0.004(3) -0.015(3) -0.012(3) C25 0.047(4) 0.046(4) 0.045(4) -0.019(3) -0.013(3) -0.011(3) C26 0.028(3) 0.037(3) 0.047(4) -0.007(3) -0.011(3) -0.002(3) C28 0.037(4) 0.034(3) 0.051(4) -0.003(3) -0.020(3) -0.007(3) N31 0.034(3) 0.030(3) 0.038(3) -0.005(2) 0.007(2) -0.007(2) N32 0.033(3) 0.035(3) 0.041(3) 0.004(2) -0.010(2) -0.006(2) C33 0.033(3) 0.032(3) 0.047(4) 0.000(3) -0.007(3) -0.008(3) C34 0.040(4) 0.032(3) 0.041(4) -0.006(3) -0.004(3) -0.011(3) C35 0.041(4) 0.030(3) 0.038(4) -0.006(3) -0.009(3) -0.005(3) C36 0.056(5) 0.075(5) 0.031(4) 0.004(3) 0.001(3) -0.024(4) C37 0.082(6) 0.065(5) 0.040(4) -0.010(4) -0.020(4) -0.015(4) C41 0.025(3) 0.036(3) 0.029(3) -0.003(2) -0.003(2) -0.011(3) C47 0.033(4) 0.039(4) 0.039(4) -0.009(3) 0.003(3) -0.010(3) N47 0.022(2) 0.026(2) 0.025(2) -0.0086(18) 0.0083(18) -0.0106(19) O47 0.083(5) 0.058(4) 0.108(5) -0.042(3) 0.060(4) -0.042(3) C42 0.030(3) 0.037(3) 0.042(4) -0.013(3) 0.001(3) -0.008(3) C43 0.032(3) 0.027(3) 0.039(3) -0.001(3) -0.001(3) -0.008(3) C44 0.032(4) 0.038(4) 0.047(4) -0.007(3) 0.005(3) -0.007(3) C45 0.033(3) 0.037(4) 0.038(4) -0.009(3) 0.004(3) -0.009(3) C46 0.031(3) 0.038(3) 0.033(3) -0.011(3) -0.005(2) -0.010(3) C48 0.038(4) 0.039(4) 0.061(5) -0.009(3) 0.009(3) -0.013(3) _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 Br1 C14 1.859(6) . ? Br2 C34 1.846(7) . ? N11 C15 1.356(8) . ? N11 N12 1.362(6) . ? N11 C28 1.434(7) . ? N12 C13 1.328(7) . ? C13 C14 1.379(8) . ? C13 C16 1.490(8) . ? C14 C15 1.373(8) . ? C15 C17 1.492(8) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 C26 1.375(8) . ? C21 C22 1.389(8) . ? C21 C27 1.501(8) . ? C27 O27 1.199(8) . ? C27 N27 1.302(7) . ? N27 H27A 0.8800 . ? N27 H27B 0.8800 . ? C22 C23 1.376(8) . ? C22 H22 0.9500 . ? C23 C24 1.374(8) . ? C23 C28 1.526(8) . ? C24 C25 1.378(8) . ? C24 H24 0.9500 . ? C25 C26 1.380(8) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? N31 C35 1.328(8) . ? N31 N32 1.383(7) . ? N31 C48 1.463(8) . ? N32 C33 1.313(8) . ? C33 C34 1.385(9) . ? C33 C36 1.503(9) . ? C34 C35 1.402(9) . ? C35 C37 1.486(9) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C41 C46 1.374(8) . ? C41 C42 1.389(8) . ? C41 C47 1.485(8) . ? C47 O47 1.205(7) . ? C47 N47 1.287(7) . ? N47 H47A 0.8800 . ? N47 H47B 0.8800 . ? C42 C43 1.383(8) . ? C42 H42 0.9500 . ? C43 C44 1.375(8) . ? C43 C48 1.517(8) . ? C44 C45 1.390(9) . ? C44 H44 0.9500 . ? C45 C46 1.379(8) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C48 H48A 0.9900 . ? C48 H48B 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 C15 N11 N12 111.1(4) . . ? C15 N11 C28 129.3(5) . . ? N12 N11 C28 119.5(5) . . ? C13 N12 N11 105.9(5) . . ? N12 C13 C14 110.1(5) . . ? N12 C13 C16 120.8(6) . . ? C14 C13 C16 129.1(6) . . ? C15 C14 C13 107.2(5) . . ? C15 C14 Br1 126.0(5) . . ? C13 C14 Br1 126.8(4) . . ? N11 C15 C14 105.7(5) . . ? N11 C15 C17 122.9(5) . . ? C14 C15 C17 131.3(6) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 C21 C22 120.4(5) . . ? C26 C21 C27 122.2(5) . . ? C22 C21 C27 117.4(5) . . ? O27 C27 N27 123.0(5) . . ? O27 C27 C21 122.3(5) . . ? N27 C27 C21 114.6(6) . . ? C27 N27 H27A 120.0 . . ? C27 N27 H27B 120.0 . . ? H27A N27 H27B 120.0 . . ? C23 C22 C21 119.1(5) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 120.5(5) . . ? C24 C23 C28 122.0(5) . . ? C22 C23 C28 117.6(5) . . ? C23 C24 C25 120.5(5) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C26 119.4(6) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C21 C26 C25 120.1(6) . . ? C21 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? N11 C28 C23 113.4(5) . . ? N11 C28 H28A 108.9 . . ? C23 C28 H28A 108.9 . . ? N11 C28 H28B 108.9 . . ? C23 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C35 N31 N32 111.9(5) . . ? C35 N31 C48 129.7(6) . . ? N32 N31 C48 118.4(5) . . ? C33 N32 N31 104.9(5) . . ? N32 C33 C34 111.7(6) . . ? N32 C33 C36 120.2(6) . . ? C34 C33 C36 128.1(6) . . ? C33 C34 C35 105.4(6) . . ? C33 C34 Br2 127.2(5) . . ? C35 C34 Br2 127.5(5) . . ? N31 C35 C34 106.1(5) . . ? N31 C35 C37 124.8(6) . . ? C34 C35 C37 129.1(7) . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C46 C41 C42 120.2(5) . . ? C46 C41 C47 121.1(6) . . ? C42 C41 C47 118.7(5) . . ? O47 C47 N47 122.0(6) . . ? O47 C47 C41 123.1(6) . . ? N47 C47 C41 114.9(5) . . ? C47 N47 H47A 120.0 . . ? C47 N47 H47B 120.0 . . ? H47A N47 H47B 120.0 . . ? C43 C42 C41 120.1(6) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C44 C43 C42 119.7(6) . . ? C44 C43 C48 122.2(6) . . ? C42 C43 C48 118.1(5) . . ? C43 C44 C45 120.0(6) . . ? C43 C44 H44 120.0 . . ? C45 C44 H44 120.0 . . ? C46 C45 C44 120.3(6) . . ? C46 C45 H45 119.9 . . ? C44 C45 H45 119.9 . . ? C41 C46 C45 119.7(6) . . ? C41 C46 H46 120.1 . . ? C45 C46 H46 120.1 . . ? N31 C48 C43 112.8(5) . . ? N31 C48 H48A 109.0 . . ? C43 C48 H48A 109.0 . . ? N31 C48 H48B 109.0 . . ? C43 C48 H48B 109.0 . . ? H48A C48 H48B 107.8 . . ? 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 -0.7(6) . . . . ? C28 N11 N12 C13 -178.4(5) . . . . ? N11 N12 C13 C14 0.4(7) . . . . ? N11 N12 C13 C16 179.8(5) . . . . ? N12 C13 C14 C15 0.0(7) . . . . ? C16 C13 C14 C15 -179.3(6) . . . . ? N12 C13 C14 Br1 -179.5(4) . . . . ? C16 C13 C14 Br1 1.1(10) . . . . ? N12 N11 C15 C14 0.7(6) . . . . ? C28 N11 C15 C14 178.1(6) . . . . ? N12 N11 C15 C17 -176.6(5) . . . . ? C28 N11 C15 C17 0.8(10) . . . . ? C13 C14 C15 N11 -0.4(6) . . . . ? Br1 C14 C15 N11 179.1(4) . . . . ? C13 C14 C15 C17 176.6(6) . . . . ? Br1 C14 C15 C17 -3.9(9) . . . . ? C26 C21 C27 O27 -174.4(7) . . . . ? C22 C21 C27 O27 5.2(9) . . . . ? C26 C21 C27 N27 2.5(9) . . . . ? C22 C21 C27 N27 -178.0(6) . . . . ? C26 C21 C22 C23 3.0(9) . . . . ? C27 C21 C22 C23 -176.6(6) . . . . ? C21 C22 C23 C24 -0.8(9) . . . . ? C21 C22 C23 C28 179.2(6) . . . . ? C22 C23 C24 C25 -0.8(10) . . . . ? C28 C23 C24 C25 179.2(6) . . . . ? C23 C24 C25 C26 0.3(10) . . . . ? C22 C21 C26 C25 -3.5(10) . . . . ? C27 C21 C26 C25 176.1(6) . . . . ? C24 C25 C26 C21 1.9(10) . . . . ? C15 N11 C28 C23 -83.0(8) . . . . ? N12 N11 C28 C23 94.2(6) . . . . ? C24 C23 C28 N11 -21.7(9) . . . . ? C22 C23 C28 N11 158.3(6) . . . . ? C35 N31 N32 C33 0.9(7) . . . . ? C48 N31 N32 C33 177.6(5) . . . . ? N31 N32 C33 C34 0.0(7) . . . . ? N31 N32 C33 C36 179.5(6) . . . . ? N32 C33 C34 C35 -0.8(7) . . . . ? C36 C33 C34 C35 179.7(7) . . . . ? N32 C33 C34 Br2 -179.5(5) . . . . ? C36 C33 C34 Br2 1.0(10) . . . . ? N32 N31 C35 C34 -1.4(7) . . . . ? C48 N31 C35 C34 -177.6(6) . . . . ? N32 N31 C35 C37 178.9(6) . . . . ? C48 N31 C35 C37 2.8(10) . . . . ? C33 C34 C35 N31 1.3(7) . . . . ? Br2 C34 C35 N31 180.0(4) . . . . ? C33 C34 C35 C37 -179.1(7) . . . . ? Br2 C34 C35 C37 -0.4(10) . . . . ? C46 C41 C47 O47 -175.8(7) . . . . ? C42 C41 C47 O47 5.1(10) . . . . ? C46 C41 C47 N47 4.5(8) . . . . ? C42 C41 C47 N47 -174.5(5) . . . . ? C46 C41 C42 C43 -1.5(9) . . . . ? C47 C41 C42 C43 177.6(6) . . . . ? C41 C42 C43 C44 -0.5(9) . . . . ? C41 C42 C43 C48 -177.2(6) . . . . ? C42 C43 C44 C45 2.4(10) . . . . ? C48 C43 C44 C45 179.0(6) . . . . ? C43 C44 C45 C46 -2.4(10) . . . . ? C42 C41 C46 C45 1.5(8) . . . . ? C47 C41 C46 C45 -177.6(5) . . . . ? C44 C45 C46 C41 0.4(9) . . . . ? C35 N31 C48 C43 86.4(8) . . . . ? N32 N31 C48 C43 -89.5(7) . . . . ? C44 C43 C48 N31 23.5(9) . . . . ? C42 C43 C48 N31 -159.8(6) . . . . ? 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 N32 0.88 1.85 2.710(7) 164.9 . N47 H47A N12 0.88 1.83 2.671(7) 160.0 1_564 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.33 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.302 _refine_diff_density_min -0.975 _refine_diff_density_rms 0.135 #END