# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global #TrackingRef 'CIF-pyrazoles-mongin.cif' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name "Floris Chevallier Florence Mongin Yury S. Halauko'" _publ_contact_author_email ;FLORIS.CHEVALLIER@UNIV-RENNES1.FR FLORENCE.MONGIN@UNIV- RENNES1.FR HYS@TUT.BY ; _publ_section_title ; N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides ; _publ_requested_category FO loop_ _publ_author_name 'Floris Chevallier' 'Yury S. Halauko' 'Christelle Pecceu' 'Sidaty Cheikh Sid Ely' 'Ibrahim F. Nassar' ; T.U.Dam ; 'Thierry Roisnel' 'Vadim E. Matulis' 'Oleg A. Ivashkevich' 'Florence Mongin' data_1n _database_code_depnum_ccdc_archive 'CCDC 800823' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-09-07T18:31:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H7 N3' _chemical_formula_sum 'C8 H7 N3' _chemical_formula_weight 145.17 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.2414(9) _cell_length_b 5.4302(2) _cell_length_c 14.7271(7) _cell_angle_alpha 90 _cell_angle_beta 105.429(2) _cell_angle_gamma 90 _cell_volume 1406.21(11) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2000 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.787 _exptl_absorpt_correction_T_max 0.990 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_unetI/netI 0.0318 _diffrn_reflns_number 4606 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 1599 _reflns_number_gt 1382 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0601P)^2^+0.7057P] 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_number_reflns 1599 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 0.245 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.35094(7) 0.3620(2) 0.65263(9) 0.0261(3) Uani 1 1 d . . . H1 H 0.3415 0.5216 0.6735 0.031 Uiso 1 1 calc R . . C2 C 0.41899(7) 0.2735(2) 0.64560(9) 0.0293(3) Uani 1 1 d . . . H2 H 0.4664 0.3572 0.6602 0.035 Uiso 1 1 calc R . . C3 C 0.40394(7) 0.0318(2) 0.61217(9) 0.0299(3) Uani 1 1 d . . . H3 H 0.4414 -0.0761 0.6004 0.036 Uiso 1 1 calc R . . N4 N 0.33139(6) -0.02849(19) 0.59886(8) 0.0275(3) Uani 1 1 d . . . N5 N 0.29892(5) 0.17838(16) 0.62411(7) 0.0201(2) Uani 1 1 d . . . C6 C 0.22075(6) 0.17956(19) 0.62010(8) 0.0193(3) Uani 1 1 d . . . C7 C 0.17386(6) -0.0119(2) 0.57675(8) 0.0234(3) Uani 1 1 d . . . H7 H 0.1934 -0.1458 0.5488 0.028 Uiso 1 1 calc R . . C8 C 0.09776(7) -0.0015(2) 0.57552(9) 0.0274(3) Uani 1 1 d . . . H8 H 0.0659 -0.1324 0.5454 0.033 Uiso 1 1 calc R . . N9 N 0.06580(6) 0.17943(19) 0.61357(7) 0.0283(3) Uani 1 1 d . . . C10 C 0.11256(7) 0.3608(2) 0.65492(9) 0.0276(3) Uani 1 1 d . . . H10 H 0.0916 0.4918 0.6826 0.033 Uiso 1 1 calc R . . C11 C 0.18942(7) 0.3705(2) 0.66009(8) 0.0239(3) Uani 1 1 d . . . H11 H 0.2199 0.5043 0.6902 0.029 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 C1 0.0253(6) 0.0222(6) 0.0307(6) 0.0000(5) 0.0073(5) -0.0043(4) C2 0.0226(6) 0.0348(7) 0.0306(6) 0.0038(5) 0.0075(5) -0.0045(5) C3 0.0223(6) 0.0359(7) 0.0327(7) -0.0009(5) 0.0092(5) 0.0042(5) N4 0.0230(5) 0.0249(5) 0.0353(6) -0.0063(4) 0.0088(4) 0.0042(4) N5 0.0197(5) 0.0182(5) 0.0226(5) -0.0008(4) 0.0062(4) 0.0006(3) C6 0.0197(5) 0.0199(5) 0.0181(5) 0.0029(4) 0.0047(4) 0.0018(4) C7 0.0231(6) 0.0206(6) 0.0264(6) -0.0032(4) 0.0062(5) 0.0015(4) C8 0.0226(6) 0.0266(6) 0.0317(6) -0.0031(5) 0.0050(5) -0.0021(5) N9 0.0217(5) 0.0316(6) 0.0324(6) -0.0002(4) 0.0085(4) 0.0022(4) C10 0.0277(6) 0.0278(6) 0.0285(6) -0.0022(5) 0.0097(5) 0.0061(5) C11 0.0253(6) 0.0215(6) 0.0245(6) -0.0032(5) 0.0060(5) 0.0003(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3604(17) . ? C1 N5 1.3637(14) . ? C1 H1 0.95 . ? C2 C3 1.4029(19) . ? C2 H2 0.95 . ? C3 N4 1.3264(16) . ? C3 H3 0.95 . ? N4 N5 1.3667(13) . ? N5 C6 1.4114(14) . ? C6 C7 1.3891(15) . ? C6 C11 1.3884(16) . ? C7 C8 1.3846(16) . ? C7 H7 0.95 . ? C8 N9 1.3390(16) . ? C8 H8 0.95 . ? N9 C10 1.3386(16) . ? C10 C11 1.3848(16) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N5 107.00(11) . . ? C2 C1 H1 126.5 . . ? N5 C1 H1 126.5 . . ? C1 C2 C3 105.07(11) . . ? C1 C2 H2 127.5 . . ? C3 C2 H2 127.5 . . ? N4 C3 C2 112.17(11) . . ? N4 C3 H3 123.9 . . ? C2 C3 H3 123.9 . . ? C3 N4 N5 104.14(10) . . ? C1 N5 N4 111.62(9) . . ? C1 N5 C6 128.47(10) . . ? N4 N5 C6 119.90(9) . . ? C7 C6 C11 118.77(11) . . ? C7 C6 N5 120.50(10) . . ? C11 C6 N5 120.73(10) . . ? C8 C7 C6 117.91(11) . . ? C8 C7 H7 121 . . ? C6 C7 H7 121 . . ? N9 C8 C7 124.82(11) . . ? N9 C8 H8 117.6 . . ? C7 C8 H8 117.6 . . ? C10 N9 C8 115.76(11) . . ? N9 C10 C11 124.50(11) . . ? N9 C10 H10 117.8 . . ? C11 C10 H10 117.8 . . ? C10 C11 C6 118.24(11) . . ? C10 C11 H11 120.9 . . ? C6 C11 H11 120.9 . . ? 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 N5 C1 C2 C3 -0.14(14) . . . . ? C1 C2 C3 N4 0.05(15) . . . . ? C2 C3 N4 N5 0.06(14) . . . . ? C2 C1 N5 N4 0.19(14) . . . . ? C2 C1 N5 C6 178.96(11) . . . . ? C3 N4 N5 C1 -0.15(13) . . . . ? C3 N4 N5 C6 -179.04(10) . . . . ? C1 N5 C6 C7 170.94(11) . . . . ? N4 N5 C6 C7 -10.38(16) . . . . ? C1 N5 C6 C11 -9.66(17) . . . . ? N4 N5 C6 C11 169.02(10) . . . . ? C11 C6 C7 C8 0.18(17) . . . . ? N5 C6 C7 C8 179.60(10) . . . . ? C6 C7 C8 N9 -0.37(19) . . . . ? C7 C8 N9 C10 0.26(18) . . . . ? C8 N9 C10 C11 0.04(18) . . . . ? N9 C10 C11 C6 -0.20(19) . . . . ? C7 C6 C11 C10 0.08(17) . . . . ? N5 C6 C11 C10 -179.33(10) . . . . ? data_8l _database_code_depnum_ccdc_archive 'CCDC 800824' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-02-22T18:00:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H4 I2 N2 S1' _chemical_formula_sum 'C7 H4 I2 N2 S' _chemical_formula_weight 401.98 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 7.0510(2) _cell_length_b 20.8154(6) _cell_length_c 7.2666(2) _cell_angle_alpha 90 _cell_angle_beta 100.688(2) _cell_angle_gamma 90 _cell_volume 1048.01(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6987 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 27.46 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 2.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.149 _exptl_absorpt_correction_T_max 0.275 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0266 _diffrn_reflns_number 9087 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 2381 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0000P)^2^+5.4910P] 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_number_reflns 2381 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0619 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.201 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.351 _refine_diff_density_min -1.256 _refine_diff_density_rms 0.131 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 I1 I 0.83599(4) 0.158027(13) 1.16666(4) 0.01972(9) Uani 1 1 d . . . C1 C 0.8472(6) 0.1797(2) 0.8916(6) 0.0169(8) Uani 1 1 d . . . C2 C 0.9113(7) 0.2353(2) 0.8186(6) 0.0212(9) Uani 1 1 d . . . H2 H 0.9644 0.2726 0.8844 0.025 Uiso 1 1 calc R . . C3 C 0.8797(7) 0.2240(2) 0.6252(7) 0.0231(10) Uani 1 1 d . . . H3 H 0.909 0.2543 0.5367 0.028 Uiso 1 1 calc R . . N4 N 0.8043(6) 0.16620(19) 0.5784(5) 0.0214(8) Uani 1 1 d . . . N5 N 0.7867(5) 0.13913(17) 0.7461(5) 0.0159(7) Uani 1 1 d . . . C7 C 0.7080(7) 0.0760(2) 0.7520(6) 0.0180(9) Uani 1 1 d . . . C8 C 0.8208(7) 0.0163(3) 0.7749(6) 0.0283(11) Uani 1 1 d . . . H8 H 0.9574 0.0145 0.7895 0.034 Uiso 1 1 calc R . . C9 C 0.7108(9) -0.0333(2) 0.7726(7) 0.0358(13) Uani 1 1 d . . . H9 H 0.759 -0.0761 0.7849 0.043 Uiso 1 1 calc R . . S10 S 0.4667(2) -0.01511(6) 0.74482(18) 0.0284(3) Uani 1 1 d . . . C11 C 0.5165(7) 0.0651(2) 0.7361(6) 0.0188(9) Uani 1 1 d . . . I12 I 0.29761(5) 0.132744(16) 0.70633(6) 0.03256(10) 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 I1 0.02997(17) 0.01791(15) 0.01206(14) -0.00019(10) 0.00595(11) -0.00238(11) C1 0.020(2) 0.020(2) 0.0111(19) -0.0019(16) 0.0033(16) -0.0008(17) C2 0.027(2) 0.019(2) 0.018(2) 0.0008(17) 0.0037(19) -0.0045(18) C3 0.030(3) 0.022(2) 0.019(2) 0.0026(18) 0.0076(19) -0.0052(19) N4 0.029(2) 0.0230(19) 0.0120(17) 0.0030(15) 0.0039(15) -0.0034(16) N5 0.0181(18) 0.0178(18) 0.0120(16) -0.0006(14) 0.0034(14) -0.0024(14) C7 0.027(2) 0.014(2) 0.013(2) -0.0015(16) 0.0062(17) -0.0026(17) C8 0.018(2) 0.049(3) 0.016(2) -0.007(2) -0.0001(18) -0.002(2) C9 0.060(4) 0.017(2) 0.029(3) 0.003(2) 0.006(3) 0.016(2) S10 0.0402(7) 0.0178(5) 0.0272(6) 0.0000(5) 0.0064(5) -0.0102(5) C11 0.024(2) 0.016(2) 0.017(2) -0.0007(16) 0.0046(18) -0.0030(17) I12 0.02277(17) 0.02792(18) 0.0495(2) 0.00204(15) 0.01331(15) 0.00279(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 I1 C1 2.065(4) . ? C1 N5 1.359(5) . ? C1 C2 1.383(6) . ? C2 C3 1.402(6) . ? C2 H2 0.95 . ? C3 N4 1.334(6) . ? C3 H3 0.95 . ? N4 N5 1.369(5) . ? N5 C7 1.430(5) . ? C7 C11 1.353(6) . ? C7 C8 1.468(7) . ? C8 C9 1.291(8) . ? C8 H8 0.95 . ? C9 S10 1.737(6) . ? C9 H9 0.95 . ? S10 C11 1.710(4) . ? C11 I12 2.070(5) . ? 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 N5 C1 C2 107.5(4) . . ? N5 C1 I1 123.6(3) . . ? C2 C1 I1 128.9(3) . . ? C1 C2 C3 103.9(4) . . ? C1 C2 H2 128 . . ? C3 C2 H2 128 . . ? N4 C3 C2 112.9(4) . . ? N4 C3 H3 123.5 . . ? C2 C3 H3 123.5 . . ? C3 N4 N5 104.0(4) . . ? C1 N5 N4 111.7(3) . . ? C1 N5 C7 128.0(4) . . ? N4 N5 C7 120.3(3) . . ? C11 C7 N5 122.6(4) . . ? C11 C7 C8 112.3(4) . . ? N5 C7 C8 125.1(4) . . ? C9 C8 C7 111.4(5) . . ? C9 C8 H8 124.3 . . ? C7 C8 H8 124.3 . . ? C8 C9 S10 114.0(4) . . ? C8 C9 H9 123 . . ? S10 C9 H9 123 . . ? C11 S10 C9 90.7(2) . . ? C7 C11 S10 111.7(3) . . ? C7 C11 I12 127.4(3) . . ? S10 C11 I12 120.9(2) . . ? 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 N5 C1 C2 C3 1.1(5) . . . . ? I1 C1 C2 C3 -178.1(4) . . . . ? C1 C2 C3 N4 -0.6(6) . . . . ? C2 C3 N4 N5 -0.1(6) . . . . ? C2 C1 N5 N4 -1.3(5) . . . . ? I1 C1 N5 N4 178.0(3) . . . . ? C2 C1 N5 C7 -179.8(4) . . . . ? I1 C1 N5 C7 -0.4(6) . . . . ? C3 N4 N5 C1 0.9(5) . . . . ? C3 N4 N5 C7 179.5(4) . . . . ? C1 N5 C7 C11 90.3(6) . . . . ? N4 N5 C7 C11 -88.0(5) . . . . ? C1 N5 C7 C8 -89.9(6) . . . . ? N4 N5 C7 C8 91.8(5) . . . . ? C11 C7 C8 C9 0.7(6) . . . . ? N5 C7 C8 C9 -179.1(4) . . . . ? C7 C8 C9 S10 -0.3(6) . . . . ? C8 C9 S10 C11 -0.1(4) . . . . ? N5 C7 C11 S10 179.1(3) . . . . ? C8 C7 C11 S10 -0.7(5) . . . . ? N5 C7 C11 I12 -1.4(6) . . . . ? C8 C7 C11 I12 178.8(3) . . . . ? C9 S10 C11 C7 0.5(4) . . . . ? C9 S10 C11 I12 -179.1(3) . . . . ? data_8o _database_code_depnum_ccdc_archive 'CCDC 800825' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2009-05-04T14:17:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H5 I2 N3' _chemical_formula_sum 'C8 H5 I2 N3' _chemical_formula_weight 396.95 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 6.8316(4) _cell_length_b 13.4938(7) _cell_length_c 12.1649(7) _cell_angle_alpha 90 _cell_angle_beta 101.594(2) _cell_angle_gamma 90 _cell_volume 1098.53(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4772 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 2.4 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.153 _exptl_absorpt_correction_T_max 0.321 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_number 8550 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.4 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 2499 _reflns_number_gt 2315 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0182P)^2^+5.5676P] 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_number_reflns 2499 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.069 _refine_ls_wR_factor_gt 0.0675 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.643 _refine_diff_density_min -1.71 _refine_diff_density_rms 0.174 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.23875(4) -0.108266(18) 0.21082(2) 0.01308(9) Uani 1 d . . . I2 I -0.26692(4) 0.12499(2) 0.21420(2) 0.02253(10) Uani 1 d . . . C1 C 0.2233(5) 0.0365(3) 0.1496(3) 0.0113(7) Uani 1 d . . . C2 C 0.2368(6) 0.0734(3) 0.0464(3) 0.0154(8) Uani 1 d . . . H2 H 0.25 0.0372 -0.0187 0.018 Uiso 1 calc R . . C3 C 0.2265(6) 0.1774(3) 0.0584(3) 0.0144(8) Uani 1 d . . . H3 H 0.2329 0.2234 0.0002 0.017 Uiso 1 calc R . . N4 N 0.2067(5) 0.2028(2) 0.1615(3) 0.0128(7) Uani 1 d . . . N5 N 0.2054(5) 0.1148(2) 0.2174(3) 0.0092(6) Uani 1 d . . . C6 C 0.1735(6) 0.1154(3) 0.3296(3) 0.0109(8) Uani 1 d . . . C7 C 0.3318(6) 0.1127(3) 0.4207(4) 0.0168(9) Uani 1 d . . . H7 H 0.4654 0.1078 0.4101 0.02 Uiso 1 calc R . . C8 C 0.2910(7) 0.1174(3) 0.5286(4) 0.0219(10) Uani 1 d . . . H8 H 0.3959 0.1158 0.593 0.026 Uiso 1 calc R . . C9 C 0.0921(8) 0.1246(3) 0.5392(4) 0.0223(10) Uani 1 d . . . H9 H 0.0643 0.1284 0.6125 0.027 Uiso 1 calc R . . N10 N -0.0616(6) 0.1264(3) 0.4516(3) 0.0184(8) Uani 1 d . . . C11 C -0.0201(6) 0.1219(3) 0.3502(3) 0.0129(8) Uani 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 I1 0.01630(14) 0.00705(14) 0.01543(14) -0.00170(9) 0.00214(10) 0.00036(9) I2 0.00999(14) 0.03643(19) 0.02114(16) -0.00315(12) 0.00308(11) 0.00233(11) C1 0.0106(17) 0.0076(18) 0.0144(18) 0.0004(15) -0.0004(14) 0.0006(14) C2 0.0182(19) 0.015(2) 0.0122(18) -0.0029(16) 0.0020(15) -0.0037(16) C3 0.0158(18) 0.014(2) 0.0142(18) 0.0047(15) 0.0040(15) -0.0014(15) N4 0.0162(16) 0.0073(16) 0.0150(16) 0.0041(13) 0.0036(13) 0.0002(13) N5 0.0110(15) 0.0065(16) 0.0112(16) 0.0010(12) 0.0052(12) 0.0001(11) C6 0.0161(19) 0.0046(18) 0.0131(18) -0.0025(14) 0.0053(15) 0.0013(14) C7 0.0166(19) 0.018(2) 0.016(2) -0.0013(16) 0.0033(16) -0.0012(16) C8 0.029(2) 0.024(2) 0.0117(19) -0.0011(17) 0.0009(18) 0.0002(19) C9 0.038(3) 0.017(2) 0.015(2) -0.0030(16) 0.0113(19) 0.0009(19) N10 0.0256(19) 0.0147(18) 0.0181(18) -0.0031(14) 0.0123(15) 0.0009(14) C11 0.0149(18) 0.0091(19) 0.0152(19) -0.0024(15) 0.0044(15) 0.0018(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 I1 C1 2.086(4) . ? I2 C11 2.112(4) . ? C1 N5 1.362(5) . ? C1 C2 1.371(6) . ? C2 C3 1.413(6) . ? C2 H2 0.95 . ? C3 N4 1.334(5) . ? C3 H3 0.95 . ? N4 N5 1.369(4) . ? N5 C6 1.425(5) . ? C6 C7 1.384(6) . ? C6 C11 1.397(6) . ? C7 C8 1.396(6) . ? C7 H7 0.95 . ? C8 C9 1.393(7) . ? C8 H8 0.95 . ? C9 N10 1.338(6) . ? C9 H9 0.95 . ? N10 C11 1.322(5) . ? 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 N5 C1 C2 107.6(3) . . ? N5 C1 I1 121.0(3) . . ? C2 C1 I1 131.3(3) . . ? C1 C2 C3 104.6(4) . . ? C1 C2 H2 127.7 . . ? C3 C2 H2 127.7 . . ? N4 C3 C2 111.7(4) . . ? N4 C3 H3 124.2 . . ? C2 C3 H3 124.2 . . ? C3 N4 N5 104.8(3) . . ? C1 N5 N4 111.2(3) . . ? C1 N5 C6 129.3(3) . . ? N4 N5 C6 119.3(3) . . ? C7 C6 C11 118.3(4) . . ? C7 C6 N5 121.4(4) . . ? C11 C6 N5 120.3(3) . . ? C6 C7 C8 118.6(4) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C9 C8 C7 118.2(4) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? N10 C9 C8 123.5(4) . . ? N10 C9 H9 118.3 . . ? C8 C9 H9 118.3 . . ? C11 N10 C9 117.5(4) . . ? N10 C11 C6 123.9(4) . . ? N10 C11 I2 116.3(3) . . ? C6 C11 I2 119.8(3) . . ? 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 N5 C1 C2 C3 0.3(4) . . . . ? I1 C1 C2 C3 -176.8(3) . . . . ? C1 C2 C3 N4 -0.4(4) . . . . ? C2 C3 N4 N5 0.4(4) . . . . ? C2 C1 N5 N4 0.0(4) . . . . ? I1 C1 N5 N4 177.4(2) . . . . ? C2 C1 N5 C6 175.3(4) . . . . ? I1 C1 N5 C6 -7.3(5) . . . . ? C3 N4 N5 C1 -0.3(4) . . . . ? C3 N4 N5 C6 -176.1(3) . . . . ? C1 N5 C6 C7 88.5(5) . . . . ? N4 N5 C6 C7 -96.4(4) . . . . ? C1 N5 C6 C11 -93.5(5) . . . . ? N4 N5 C6 C11 81.5(4) . . . . ? C11 C6 C7 C8 -0.5(6) . . . . ? N5 C6 C7 C8 177.5(4) . . . . ? C6 C7 C8 C9 0.0(6) . . . . ? C7 C8 C9 N10 0.6(7) . . . . ? C8 C9 N10 C11 -0.6(6) . . . . ? C9 N10 C11 C6 0.0(6) . . . . ? C9 N10 C11 I2 -180.0(3) . . . . ? C7 C6 C11 N10 0.5(6) . . . . ? N5 C6 C11 N10 -177.5(4) . . . . ? C7 C6 C11 I2 -179.5(3) . . . . ? N5 C6 C11 I2 2.5(5) . . . . ? data_7n _database_code_depnum_ccdc_archive 'CCDC 800826' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-09-07T16:51:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H6 I N3' _chemical_formula_sum 'C8 H6 I N3' _chemical_formula_weight 271.06 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.1532(3) _cell_length_b 14.7450(6) _cell_length_c 8.1035(4) _cell_angle_alpha 90 _cell_angle_beta 91.8830(10) _cell_angle_gamma 90 _cell_volume 854.25(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5060 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 27.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 2.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.692 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.302 _exptl_absorpt_correction_T_max 0.397 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_number 7483 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 1957 _reflns_number_gt 1824 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0192P)^2^+0.5368P] 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_number_reflns 1957 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0515 _refine_ls_wR_factor_gt 0.0504 _refine_ls_goodness_of_fit_ref 1.12 _refine_ls_restrained_S_all 1.12 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.449 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.102 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 I1 I 0.27784(2) 0.391259(10) 0.646280(19) 0.01955(7) Uani 1 1 d . . . C2 C 0.0795(3) 0.30376(17) 0.5382(3) 0.0184(5) Uani 1 1 d . . . C3 C -0.0858(3) 0.33039(19) 0.4609(3) 0.0219(5) Uani 1 1 d . . . H3 H -0.1288 0.3905 0.4412 0.026 Uiso 1 1 calc R . . C4 C -0.1764(4) 0.24926(19) 0.4178(3) 0.0246(6) Uani 1 1 d . . . H4 H -0.2943 0.2467 0.3606 0.03 Uiso 1 1 calc R . . N5 N -0.0809(3) 0.17657(15) 0.4648(3) 0.0230(5) Uani 1 1 d . . . N6 N 0.0786(3) 0.21064(14) 0.5396(2) 0.0165(4) Uani 1 1 d . . . C7 C 0.2121(3) 0.14730(16) 0.6010(3) 0.0166(5) Uani 1 1 d . . . C8 C 0.1521(4) 0.06219(17) 0.6539(3) 0.0202(5) Uani 1 1 d . . . H8 H 0.0228 0.0473 0.6514 0.024 Uiso 1 1 calc R . . C9 C 0.2841(4) 0.00042(18) 0.7098(3) 0.0231(5) Uani 1 1 d . . . H9 H 0.242 -0.057 0.7465 0.028 Uiso 1 1 calc R . . N10 N 0.4689(3) 0.01671(15) 0.7154(3) 0.0228(5) Uani 1 1 d . . . C11 C 0.5239(4) 0.09753(17) 0.6617(3) 0.0224(5) Uani 1 1 d . . . H11 H 0.6542 0.1101 0.6635 0.027 Uiso 1 1 calc R . . C12 C 0.4030(3) 0.16422(17) 0.6036(3) 0.0197(5) Uani 1 1 d . . . H12 H 0.4498 0.2206 0.5661 0.024 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 I1 0.02326(11) 0.01413(11) 0.02101(10) 0.00061(5) -0.00315(7) -0.00162(6) C2 0.0195(12) 0.0181(13) 0.0175(11) 0.0016(9) 0.0011(9) -0.0020(10) C3 0.0211(13) 0.0215(13) 0.0230(13) 0.0025(10) 0.0003(10) 0.0051(11) C4 0.0150(12) 0.0323(16) 0.0264(14) 0.0037(11) -0.0030(10) -0.0011(11) N5 0.0157(10) 0.0251(12) 0.0280(12) -0.0007(9) -0.0049(8) -0.0051(9) N6 0.0123(9) 0.0153(10) 0.0219(10) -0.0018(8) -0.0010(7) -0.0021(8) C7 0.0179(11) 0.0153(12) 0.0166(11) -0.0032(9) -0.0015(9) -0.0013(10) C8 0.0201(12) 0.0175(13) 0.0229(13) -0.0014(9) 0.0004(10) -0.0041(10) C9 0.0308(14) 0.0159(13) 0.0224(13) 0.0001(10) -0.0021(10) -0.0021(11) N10 0.0257(12) 0.0182(11) 0.0242(11) -0.0015(8) -0.0047(9) 0.0039(9) C11 0.0176(12) 0.0217(14) 0.0275(14) -0.0047(10) -0.0043(10) 0.0004(10) C12 0.0172(12) 0.0150(13) 0.0268(13) -0.0008(9) 0.0003(9) -0.0015(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 I1 C2 2.089(2) . ? C2 N6 1.373(3) . ? C2 C3 1.377(3) . ? C3 C4 1.399(4) . ? C3 H3 0.95 . ? C4 N5 1.320(3) . ? C4 H4 0.95 . ? N5 N6 1.370(3) . ? N6 C7 1.414(3) . ? C7 C12 1.388(3) . ? C7 C8 1.399(4) . ? C8 C9 1.378(4) . ? C8 H8 0.95 . ? C9 N10 1.342(3) . ? C9 H9 0.95 . ? N10 C11 1.332(3) . ? C11 C12 1.382(4) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? 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 N6 C2 C3 106.6(2) . . ? N6 C2 I1 128.10(17) . . ? C3 C2 I1 125.16(19) . . ? C2 C3 C4 104.7(2) . . ? C2 C3 H3 127.7 . . ? C4 C3 H3 127.7 . . ? N5 C4 C3 113.0(2) . . ? N5 C4 H4 123.5 . . ? C3 C4 H4 123.5 . . ? C4 N5 N6 104.2(2) . . ? N5 N6 C2 111.5(2) . . ? N5 N6 C7 117.2(2) . . ? C2 N6 C7 131.3(2) . . ? C12 C7 C8 118.0(2) . . ? C12 C7 N6 122.6(2) . . ? C8 C7 N6 119.3(2) . . ? C9 C8 C7 118.7(2) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? N10 C9 C8 123.8(2) . . ? N10 C9 H9 118.1 . . ? C8 C9 H9 118.1 . . ? C11 N10 C9 116.8(2) . . ? N10 C11 C12 124.0(2) . . ? N10 C11 H11 118 . . ? C12 C11 H11 118 . . ? C11 C12 C7 118.8(2) . . ? C11 C12 H12 120.6 . . ? C7 C12 H12 120.6 . . ? 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 N6 C2 C3 C4 -0.8(3) . . . . ? I1 C2 C3 C4 -176.50(17) . . . . ? C2 C3 C4 N5 1.0(3) . . . . ? C3 C4 N5 N6 -0.7(3) . . . . ? C4 N5 N6 C2 0.1(3) . . . . ? C4 N5 N6 C7 -178.9(2) . . . . ? C3 C2 N6 N5 0.4(3) . . . . ? I1 C2 N6 N5 175.98(16) . . . . ? C3 C2 N6 C7 179.3(2) . . . . ? I1 C2 N6 C7 -5.2(4) . . . . ? N5 N6 C7 C12 147.4(2) . . . . ? C2 N6 C7 C12 -31.4(4) . . . . ? N5 N6 C7 C8 -29.2(3) . . . . ? C2 N6 C7 C8 152.0(2) . . . . ? C12 C7 C8 C9 1.7(3) . . . . ? N6 C7 C8 C9 178.5(2) . . . . ? C7 C8 C9 N10 -0.6(4) . . . . ? C8 C9 N10 C11 -0.6(4) . . . . ? C9 N10 C11 C12 0.7(4) . . . . ? N10 C11 C12 C7 0.4(4) . . . . ? C8 C7 C12 C11 -1.6(3) . . . . ? N6 C7 C12 C11 -178.3(2) . . . . ? data_8n _database_code_depnum_ccdc_archive 'CCDC 800827' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-09-06T17:44:36-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H5 I2 N3' _chemical_formula_sum 'C8 H5 I2 N3' _chemical_formula_weight 396.95 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.1322(2) _cell_length_b 10.9173(3) _cell_length_c 13.3983(4) _cell_angle_alpha 90 _cell_angle_beta 99.7590(10) _cell_angle_gamma 90 _cell_volume 1028.15(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6201 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.46 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 2.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.404 _exptl_absorpt_correction_T_max 0.545 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_number 9081 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2357 _reflns_number_gt 2220 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0161P)^2^+0.0450P] 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_number_reflns 2357 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0195 _refine_ls_R_factor_gt 0.018 _refine_ls_wR_factor_ref 0.0451 _refine_ls_wR_factor_gt 0.0445 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.468 _refine_diff_density_min -0.831 _refine_diff_density_rms 0.137 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 I1 I 0.71094(2) 0.067282(16) 0.214935(13) 0.02603(6) Uani 1 1 d . . . I2 I 0.19169(2) 0.226328(14) 0.141979(11) 0.01857(6) Uani 1 1 d . . . C1 C 0.4856(3) -0.0463(2) 0.15934(18) 0.0176(5) Uani 1 1 d . . . C2 C 0.4594(4) -0.1218(2) 0.07639(18) 0.0215(5) Uani 1 1 d . . . H2 H 0.5435 -0.1352 0.0296 0.026 Uiso 1 1 calc R . . C3 C 0.2812(4) -0.1743(2) 0.07643(18) 0.0244(5) Uani 1 1 d . . . H3 H 0.224 -0.231 0.0267 0.029 Uiso 1 1 calc R . . N4 N 0.1994(3) -0.13679(19) 0.15327(15) 0.0212(5) Uani 1 1 d . . . N5 N 0.3296(3) -0.05705(16) 0.20429(15) 0.0162(4) Uani 1 1 d . . . C6 C 0.2805(3) 0.0081(2) 0.28862(16) 0.0157(5) Uani 1 1 d . . . C7 C 0.2908(4) -0.0514(2) 0.38036(19) 0.0212(5) Uani 1 1 d . . . H7 H 0.3332 -0.1339 0.3885 0.025 Uiso 1 1 calc R . . C8 C 0.2373(4) 0.0131(2) 0.46012(19) 0.0237(5) Uani 1 1 d . . . H8 H 0.2433 -0.0276 0.5233 0.028 Uiso 1 1 calc R . . N9 N 0.1777(3) 0.12944(19) 0.45320(16) 0.0223(5) Uani 1 1 d . . . C10 C 0.1693(3) 0.1857(2) 0.36407(18) 0.0195(5) Uani 1 1 d . . . H10 H 0.1272 0.2684 0.3584 0.023 Uiso 1 1 calc R . . C11 C 0.2190(3) 0.1294(2) 0.27880(17) 0.0156(5) 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 I1 0.01915(10) 0.03036(12) 0.02836(11) 0.00392(7) 0.00336(7) -0.00669(6) I2 0.02158(9) 0.01897(10) 0.01568(10) 0.00243(6) 0.00467(6) 0.00218(5) C1 0.0165(11) 0.0199(12) 0.0172(12) 0.0036(10) 0.0047(9) 0.0006(9) C2 0.0282(13) 0.0226(13) 0.0150(11) -0.0010(10) 0.0076(10) 0.0046(10) C3 0.0340(14) 0.0214(13) 0.0170(12) -0.0045(11) 0.0019(10) -0.0037(11) N4 0.0241(11) 0.0181(11) 0.0213(11) -0.0049(9) 0.0037(8) -0.0045(8) N5 0.0198(10) 0.0128(10) 0.0168(10) -0.0029(8) 0.0051(8) -0.0024(7) C6 0.0151(11) 0.0165(12) 0.0162(11) -0.0022(9) 0.0047(9) -0.0024(8) C7 0.0270(13) 0.0169(12) 0.0206(12) 0.0020(10) 0.0069(10) -0.0010(9) C8 0.0313(14) 0.0254(14) 0.0162(11) 0.0029(11) 0.0091(10) -0.0011(11) N9 0.0255(11) 0.0252(12) 0.0173(10) -0.0026(9) 0.0067(8) -0.0017(8) C10 0.0194(12) 0.0199(12) 0.0194(12) -0.0008(11) 0.0041(9) 0.0015(9) C11 0.0159(11) 0.0162(12) 0.0150(11) 0.0027(9) 0.0036(8) -0.0015(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 I1 C1 2.066(2) . ? I2 C11 2.097(2) . ? C1 N5 1.357(3) . ? C1 C2 1.371(3) . ? C2 C3 1.394(4) . ? C2 H2 0.95 . ? C3 N4 1.331(3) . ? C3 H3 0.95 . ? N4 N5 1.369(3) . ? N5 C6 1.428(3) . ? C6 C7 1.381(3) . ? C6 C11 1.394(3) . ? C7 C8 1.387(3) . ? C7 H7 0.95 . ? C8 N9 1.337(3) . ? C8 H8 0.95 . ? N9 C10 1.335(3) . ? C10 C11 1.395(3) . ? C10 H10 0.95 . ? 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 N5 C1 C2 107.4(2) . . ? N5 C1 I1 122.56(17) . . ? C2 C1 I1 130.07(17) . . ? C1 C2 C3 104.2(2) . . ? C1 C2 H2 127.9 . . ? C3 C2 H2 127.9 . . ? N4 C3 C2 113.1(2) . . ? N4 C3 H3 123.4 . . ? C2 C3 H3 123.4 . . ? C3 N4 N5 103.44(19) . . ? C1 N5 N4 111.82(19) . . ? C1 N5 C6 129.6(2) . . ? N4 N5 C6 118.38(18) . . ? C7 C6 C11 119.9(2) . . ? C7 C6 N5 119.1(2) . . ? C11 C6 N5 120.9(2) . . ? C6 C7 C8 117.8(2) . . ? C6 C7 H7 121.1 . . ? C8 C7 H7 121.1 . . ? N9 C8 C7 123.7(2) . . ? N9 C8 H8 118.1 . . ? C7 C8 H8 118.1 . . ? C10 N9 C8 117.7(2) . . ? N9 C10 C11 123.4(2) . . ? N9 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C10 C11 C6 117.5(2) . . ? C10 C11 I2 119.64(17) . . ? C6 C11 I2 122.88(16) . . ? 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 N5 C1 C2 C3 0.6(3) . . . . ? I1 C1 C2 C3 -179.51(19) . . . . ? C1 C2 C3 N4 -0.5(3) . . . . ? C2 C3 N4 N5 0.1(3) . . . . ? C2 C1 N5 N4 -0.5(3) . . . . ? I1 C1 N5 N4 179.55(15) . . . . ? C2 C1 N5 C6 -175.2(2) . . . . ? I1 C1 N5 C6 4.9(3) . . . . ? C3 N4 N5 C1 0.2(3) . . . . ? C3 N4 N5 C6 175.5(2) . . . . ? C1 N5 C6 C7 -107.4(3) . . . . ? N4 N5 C6 C7 78.2(3) . . . . ? C1 N5 C6 C11 73.9(3) . . . . ? N4 N5 C6 C11 -100.4(3) . . . . ? C11 C6 C7 C8 0.4(4) . . . . ? N5 C6 C7 C8 -178.2(2) . . . . ? C6 C7 C8 N9 -0.4(4) . . . . ? C7 C8 N9 C10 0.2(4) . . . . ? C8 N9 C10 C11 0.1(4) . . . . ? N9 C10 C11 C6 -0.1(4) . . . . ? N9 C10 C11 I2 178.18(18) . . . . ? C7 C6 C11 C10 -0.2(3) . . . . ? N5 C6 C11 C10 178.4(2) . . . . ? C7 C6 C11 I2 -178.38(17) . . . . ? N5 C6 C11 I2 0.3(3) . . . . ? data_9m _database_code_depnum_ccdc_archive 'CCDC 800828' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-02-24T15:25:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H3 Cl I3 N3' _chemical_formula_sum 'C8 H3 Cl I3 N3' _chemical_formula_weight 557.28 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 11.8807(5) _cell_length_b 7.3931(3) _cell_length_c 14.3980(6) _cell_angle_alpha 90 _cell_angle_beta 92.696(2) _cell_angle_gamma 90 _cell_volume 1263.25(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5293 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.42 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 2.93 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.606 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.029 _exptl_absorpt_correction_T_max 0.088 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_number 10351 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 2882 _reflns_number_gt 2561 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0362P)^2^+4.4298P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0063(3) _refine_ls_number_reflns 2882 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.04 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.963 _refine_diff_density_min -1.499 _refine_diff_density_rms 0.256 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 I1 I 0.31531(4) 0.54047(5) -0.06178(3) 0.02239(15) Uani 1 1 d . . . C1 C 0.3078(5) 0.2746(8) -0.1042(4) 0.0146(7) Uani 1 1 d . . . C2 C 0.3537(5) 0.1915(8) -0.1780(4) 0.0146(7) Uani 1 1 d . . . H2 H 0.4009 0.2434 -0.2224 0.018 Uiso 1 1 calc R . . C3 C 0.3155(5) 0.0111(8) -0.1737(4) 0.0146(7) Uani 1 1 d . . . H3 H 0.3332 -0.0791 -0.2177 0.018 Uiso 1 1 calc R . . N4 N 0.2527(4) -0.0189(7) -0.1024(4) 0.0149(10) Uani 1 1 d . . . N5 N 0.2489(4) 0.1467(6) -0.0596(3) 0.0119(10) Uani 1 1 d . . . C6 C 0.1839(5) 0.1630(7) 0.0199(4) 0.0130(5) Uani 1 1 d . . . C7 C 0.2300(5) 0.1176(8) 0.1078(4) 0.0130(5) Uani 1 1 d . . . I7 I 0.39852(3) 0.03854(6) 0.12271(3) 0.02098(15) Uani 1 1 d . . . C8 C 0.1597(4) 0.1271(8) 0.1827(4) 0.0130(5) Uani 1 1 d . . . Cl8 Cl 0.20685(14) 0.0644(2) 0.29294(11) 0.0236(4) Uani 1 1 d . . . N9 N 0.0534(4) 0.1788(7) 0.1752(4) 0.0173(11) Uani 1 1 d . . . C10 C 0.0092(5) 0.2233(7) 0.0902(4) 0.0130(5) Uani 1 1 d . . . H10 H -0.0674 0.2602 0.0844 0.016 Uiso 1 1 calc R . . C11 C 0.0708(5) 0.2172(8) 0.0117(4) 0.0130(5) Uani 1 1 d . . . I11 I -0.00557(3) 0.28908(5) -0.11672(3) 0.01871(15) 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 I1 0.0278(2) 0.0114(2) 0.0291(3) -0.00155(17) 0.01275(19) -0.00620(15) C1 0.0163(15) 0.0131(16) 0.0152(16) -0.0024(14) 0.0096(14) 0.0027(13) C2 0.0163(15) 0.0131(16) 0.0152(16) -0.0024(14) 0.0096(14) 0.0027(13) C3 0.0163(15) 0.0131(16) 0.0152(16) -0.0024(14) 0.0096(14) 0.0027(13) N4 0.018(2) 0.010(2) 0.018(3) -0.005(2) 0.009(2) -0.0021(19) N5 0.015(2) 0.006(2) 0.015(2) -0.0010(19) 0.0109(19) 0.0023(18) C6 0.0124(11) 0.0077(12) 0.0195(14) 0.0008(10) 0.0063(10) -0.0004(9) C7 0.0124(11) 0.0077(12) 0.0195(14) 0.0008(10) 0.0063(10) -0.0004(9) I7 0.0125(2) 0.0267(3) 0.0242(3) 0.00329(18) 0.00637(16) 0.00573(15) C8 0.0124(11) 0.0077(12) 0.0195(14) 0.0008(10) 0.0063(10) -0.0004(9) Cl8 0.0293(8) 0.0278(9) 0.0144(7) 0.0039(6) 0.0071(6) 0.0044(6) N9 0.021(3) 0.013(3) 0.019(3) 0.002(2) 0.011(2) 0.001(2) C10 0.0124(11) 0.0077(12) 0.0195(14) 0.0008(10) 0.0063(10) -0.0004(9) C11 0.0124(11) 0.0077(12) 0.0195(14) 0.0008(10) 0.0063(10) -0.0004(9) I11 0.0190(2) 0.0141(2) 0.0229(3) 0.00267(16) -0.00023(17) -0.00053(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 I1 C1 2.059(6) . ? C1 N5 1.356(8) . ? C1 C2 1.364(8) . ? C2 C3 1.411(8) . ? C2 H2 0.95 . ? C3 N4 1.316(8) . ? C3 H3 0.95 . ? N4 N5 1.373(7) . ? N5 C6 1.415(8) . ? C6 C7 1.396(8) . ? C6 C11 1.402(7) . ? C7 C8 1.397(9) . ? C7 I7 2.087(5) . ? C8 N9 1.319(7) . ? C8 Cl8 1.721(6) . ? N9 C10 1.349(8) . ? C10 C11 1.376(9) . ? C10 H10 0.95 . ? C11 I11 2.089(6) . ? 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 N5 C1 C2 106.8(5) . . ? N5 C1 I1 122.8(4) . . ? C2 C1 I1 130.4(5) . . ? C1 C2 C3 104.5(5) . . ? C1 C2 H2 127.8 . . ? C3 C2 H2 127.8 . . ? N4 C3 C2 112.9(5) . . ? N4 C3 H3 123.5 . . ? C2 C3 H3 123.5 . . ? C3 N4 N5 103.4(5) . . ? C1 N5 N4 112.3(5) . . ? C1 N5 C6 129.6(5) . . ? N4 N5 C6 118.0(5) . . ? C7 C6 C11 118.6(6) . . ? C7 C6 N5 120.4(5) . . ? C11 C6 N5 120.9(5) . . ? C6 C7 C8 117.7(5) . . ? C6 C7 I7 119.7(4) . . ? C8 C7 I7 122.7(4) . . ? N9 C8 C7 123.8(6) . . ? N9 C8 Cl8 115.0(4) . . ? C7 C8 Cl8 121.2(4) . . ? C8 N9 C10 118.4(5) . . ? N9 C10 C11 122.5(5) . . ? N9 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C10 C11 C6 119.0(6) . . ? C10 C11 I11 119.5(4) . . ? C6 C11 I11 121.5(4) . . ? 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 N5 C1 C2 C3 1.2(6) . . . . ? I1 C1 C2 C3 -177.3(5) . . . . ? C1 C2 C3 N4 -1.2(7) . . . . ? C2 C3 N4 N5 0.7(7) . . . . ? C2 C1 N5 N4 -0.9(7) . . . . ? I1 C1 N5 N4 177.7(4) . . . . ? C2 C1 N5 C6 -178.6(5) . . . . ? I1 C1 N5 C6 0.0(9) . . . . ? C3 N4 N5 C1 0.2(7) . . . . ? C3 N4 N5 C6 178.2(5) . . . . ? C1 N5 C6 C7 -97.3(7) . . . . ? N4 N5 C6 C7 85.1(7) . . . . ? C1 N5 C6 C11 85.5(8) . . . . ? N4 N5 C6 C11 -92.1(7) . . . . ? C11 C6 C7 C8 0.7(8) . . . . ? N5 C6 C7 C8 -176.6(5) . . . . ? C11 C6 C7 I7 -179.5(4) . . . . ? N5 C6 C7 I7 3.3(7) . . . . ? C6 C7 C8 N9 -1.0(9) . . . . ? I7 C7 C8 N9 179.1(4) . . . . ? C6 C7 C8 Cl8 177.1(4) . . . . ? I7 C7 C8 Cl8 -2.8(7) . . . . ? C7 C8 N9 C10 0.8(9) . . . . ? Cl8 C8 N9 C10 -177.4(4) . . . . ? C8 N9 C10 C11 -0.2(9) . . . . ? N9 C10 C11 C6 -0.1(9) . . . . ? N9 C10 C11 I11 -179.9(4) . . . . ? C7 C6 C11 C10 -0.2(8) . . . . ? N5 C6 C11 C10 177.1(5) . . . . ? C7 C6 C11 I11 179.7(4) . . . . ? N5 C6 C11 I11 -3.1(7) . . . . ? data_2b _database_code_depnum_ccdc_archive 'CCDC 800829' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-02-24T10:53:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H12 I N3' _chemical_formula_sum 'C11 H12 I N3' _chemical_formula_weight 313.14 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 7.3777(3) _cell_length_b 19.1576(9) _cell_length_c 8.7098(4) _cell_angle_alpha 90 _cell_angle_beta 111.017(2) _cell_angle_gamma 90 _cell_volume 1149.14(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6782 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 27.43 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.81 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.758 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.257 _exptl_absorpt_correction_T_max 0.437 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_number 9641 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 2611 _reflns_number_gt 2432 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0154P)^2^+1.7898P] 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_number_reflns 2611 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0596 _refine_ls_wR_factor_gt 0.0509 _refine_ls_goodness_of_fit_ref 1.21 _refine_ls_restrained_S_all 1.21 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.427 _refine_diff_density_min -0.8 _refine_diff_density_rms 0.101 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 I1 I 0.31639(3) 0.167336(10) 0.03136(2) 0.01987(7) Uani 1 1 d . . . C1 C 0.0569(4) 0.18045(15) 0.0701(4) 0.0190(6) Uani 1 1 d . . . C2 C 0.0231(5) 0.21787(16) 0.1926(4) 0.0240(6) Uani 1 1 d . . . H2 H 0.1123 0.2457 0.276 0.029 Uiso 1 1 calc R . . C3 C -0.1721(5) 0.20553(16) 0.1657(4) 0.0251(7) Uani 1 1 d . . . H3 H -0.238 0.2251 0.2313 0.03 Uiso 1 1 calc R . . N4 N -0.2569(4) 0.16323(13) 0.0377(3) 0.0234(5) Uani 1 1 d . . . N5 N -0.1119(3) 0.14798(13) -0.0211(3) 0.0184(5) Uani 1 1 d . . . C6 C -0.1512(4) 0.10413(14) -0.1628(3) 0.0164(5) Uani 1 1 d . . . C7 C -0.2048(4) 0.03517(15) -0.1578(3) 0.0181(6) Uani 1 1 d . . . H7 H -0.2144 0.0167 -0.0598 0.022 Uiso 1 1 calc R . . C8 C -0.2444(4) -0.00696(15) -0.2951(3) 0.0186(6) Uani 1 1 d . . . H8 H -0.2814 -0.0542 -0.2903 0.022 Uiso 1 1 calc R . . C9 C -0.2308(4) 0.01907(15) -0.4418(3) 0.0171(6) Uani 1 1 d . . . C10 C -0.1767(4) 0.08924(15) -0.4444(3) 0.0190(6) Uani 1 1 d . . . H10 H -0.167 0.1082 -0.5419 0.023 Uiso 1 1 calc R . . C11 C -0.1373(4) 0.13098(15) -0.3068(3) 0.0192(6) Uani 1 1 d . . . H11 H -0.1005 0.1783 -0.3105 0.023 Uiso 1 1 calc R . . N12 N -0.2652(4) -0.02345(13) -0.5764(3) 0.0215(5) Uani 1 1 d . . . C13 C -0.3124(5) -0.09629(16) -0.5700(4) 0.0245(6) Uani 1 1 d . . . H13A H -0.2123 -0.1186 -0.4766 0.037 Uiso 1 1 calc R . . H13B H -0.3186 -0.1193 -0.6723 0.037 Uiso 1 1 calc R . . H13C H -0.4385 -0.1003 -0.5569 0.037 Uiso 1 1 calc R . . C14 C -0.2760(5) 0.00600(17) -0.7333(4) 0.0253(6) Uani 1 1 d . . . H14A H -0.3673 0.0452 -0.7614 0.038 Uiso 1 1 calc R . . H14B H -0.3208 -0.0298 -0.819 0.038 Uiso 1 1 calc R . . H14C H -0.1471 0.0225 -0.7253 0.038 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 I1 0.02040(11) 0.01879(11) 0.02199(11) -0.00203(7) 0.00951(8) -0.00218(7) C1 0.0202(14) 0.0157(14) 0.0207(14) -0.0004(11) 0.0071(11) -0.0014(11) C2 0.0268(16) 0.0223(16) 0.0240(15) -0.0059(12) 0.0104(13) -0.0049(12) C3 0.0290(16) 0.0254(16) 0.0245(16) -0.0062(12) 0.0142(13) 0.0006(13) N4 0.0225(13) 0.0266(14) 0.0240(13) -0.0041(11) 0.0118(11) 0.0007(11) N5 0.0196(12) 0.0175(12) 0.0193(12) -0.0022(9) 0.0086(10) -0.0013(9) C6 0.0166(13) 0.0169(14) 0.0159(13) -0.0017(10) 0.0060(10) 0.0008(10) C7 0.0197(14) 0.0203(15) 0.0149(13) 0.0039(11) 0.0070(11) -0.0003(11) C8 0.0202(13) 0.0149(14) 0.0214(14) 0.0012(11) 0.0084(11) -0.0011(11) C9 0.0159(13) 0.0196(14) 0.0179(14) -0.0001(10) 0.0087(11) 0.0043(11) C10 0.0206(14) 0.0201(15) 0.0178(13) 0.0035(11) 0.0088(11) 0.0009(11) C11 0.0200(14) 0.0162(14) 0.0215(14) 0.0021(11) 0.0074(11) -0.0010(11) N12 0.0315(14) 0.0173(12) 0.0171(12) -0.0021(9) 0.0103(10) -0.0014(10) C13 0.0297(16) 0.0204(16) 0.0251(15) -0.0047(12) 0.0118(13) -0.0019(12) C14 0.0300(16) 0.0291(17) 0.0172(14) 0.0003(12) 0.0090(12) 0.0020(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 I1 C1 2.075(3) . ? C1 N5 1.364(4) . ? C1 C2 1.380(4) . ? C2 C3 1.394(4) . ? C2 H2 0.95 . ? C3 N4 1.338(4) . ? C3 H3 0.95 . ? N4 N5 1.373(3) . ? N5 C6 1.434(3) . ? C6 C7 1.384(4) . ? C6 C11 1.393(4) . ? C7 C8 1.384(4) . ? C7 H7 0.95 . ? C8 C9 1.409(4) . ? C8 H8 0.95 . ? C9 N12 1.374(4) . ? C9 C10 1.405(4) . ? C10 C11 1.382(4) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? N12 C13 1.444(4) . ? N12 C14 1.454(4) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? 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 N5 C1 C2 107.8(3) . . ? N5 C1 I1 123.6(2) . . ? C2 C1 I1 128.5(2) . . ? C1 C2 C3 104.2(3) . . ? C1 C2 H2 127.9 . . ? C3 C2 H2 127.9 . . ? N4 C3 C2 112.9(3) . . ? N4 C3 H3 123.6 . . ? C2 C3 H3 123.6 . . ? C3 N4 N5 104.2(2) . . ? C1 N5 N4 110.9(2) . . ? C1 N5 C6 129.0(2) . . ? N4 N5 C6 120.1(2) . . ? C7 C6 C11 119.6(3) . . ? C7 C6 N5 120.3(2) . . ? C11 C6 N5 120.1(3) . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 121.0(3) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? N12 C9 C10 121.4(3) . . ? N12 C9 C8 120.8(3) . . ? C10 C9 C8 117.8(3) . . ? C11 C10 C9 120.8(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C6 120.4(3) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C9 N12 C13 120.9(2) . . ? C9 N12 C14 120.2(2) . . ? C13 N12 C14 118.6(2) . . ? N12 C13 H13A 109.5 . . ? N12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N12 C14 H14A 109.5 . . ? N12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 N5 C1 C2 C3 -0.4(3) . . . . ? I1 C1 C2 C3 -176.6(2) . . . . ? C1 C2 C3 N4 0.5(4) . . . . ? C2 C3 N4 N5 -0.4(4) . . . . ? C2 C1 N5 N4 0.2(3) . . . . ? I1 C1 N5 N4 176.61(19) . . . . ? C2 C1 N5 C6 179.0(3) . . . . ? I1 C1 N5 C6 -4.6(4) . . . . ? C3 N4 N5 C1 0.1(3) . . . . ? C3 N4 N5 C6 -178.8(3) . . . . ? C1 N5 C6 C7 117.6(3) . . . . ? N4 N5 C6 C7 -63.7(4) . . . . ? C1 N5 C6 C11 -62.9(4) . . . . ? N4 N5 C6 C11 115.7(3) . . . . ? C11 C6 C7 C8 0.0(4) . . . . ? N5 C6 C7 C8 179.4(3) . . . . ? C6 C7 C8 C9 0.2(4) . . . . ? C7 C8 C9 N12 178.2(3) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ? N12 C9 C10 C11 -178.2(3) . . . . ? C8 C9 C10 C11 0.3(4) . . . . ? C9 C10 C11 C6 -0.2(4) . . . . ? C7 C6 C11 C10 0.0(4) . . . . ? N5 C6 C11 C10 -179.4(3) . . . . ? C10 C9 N12 C13 177.3(3) . . . . ? C8 C9 N12 C13 -1.3(4) . . . . ? C10 C9 N12 C14 -9.6(4) . . . . ? C8 C9 N12 C14 171.8(3) . . . . ? data_3b _database_code_depnum_ccdc_archive 'CCDC 800830' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-02-25T15:06:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H11 I2 N3' _chemical_formula_sum 'C11 H11 I2 N3' _chemical_formula_weight 439.03 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 6.9744(3) _cell_length_b 26.4537(12) _cell_length_c 7.2619(3) _cell_angle_alpha 90 _cell_angle_beta 90.717(2) _cell_angle_gamma 90 _cell_volume 1339.71(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7863 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.39 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 2.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.673 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.428 _exptl_absorpt_correction_T_max 0.571 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_unetI/netI 0.0212 _diffrn_reflns_number 11715 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.4 _diffrn_reflns_theta_full 27.4 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 3018 _reflns_number_gt 2908 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0000P)^2^+5.2295P] 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_number_reflns 3018 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 1.288 _refine_ls_restrained_S_all 1.288 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.907 _refine_diff_density_min -0.896 _refine_diff_density_rms 0.112 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9133(7) 0.19129(17) 0.2971(6) 0.0201(9) Uani 1 1 d . . . I1 I 0.89444(5) 0.175098(11) 0.57406(4) 0.02154(8) Uani 1 1 d . . . C2 C 0.9737(7) 0.23432(19) 0.2117(7) 0.0266(10) Uani 1 1 d . . . H2 H 1.0162 0.2648 0.2682 0.032 Uiso 1 1 calc R . . C3 C 0.9598(8) 0.22393(19) 0.0239(7) 0.0296(11) Uani 1 1 d . . . H3 H 0.9921 0.2474 -0.0699 0.036 Uiso 1 1 calc R . . N4 N 0.8958(6) 0.17721(15) -0.0088(6) 0.0256(8) Uani 1 1 d . . . N5 N 0.8678(5) 0.15727(14) 0.1613(5) 0.0195(8) Uani 1 1 d . . . C6 C 0.7934(6) 0.10706(16) 0.1822(6) 0.0185(9) Uani 1 1 d . . . C7 C 0.5973(7) 0.09784(16) 0.1902(6) 0.0199(9) Uani 1 1 d . . . I7 I 0.40215(5) 0.158173(12) 0.16292(5) 0.03005(9) Uani 1 1 d . . . C8 C 0.5265(7) 0.04946(18) 0.2167(6) 0.0218(9) Uani 1 1 d . . . H8 H 0.3918 0.0442 0.2198 0.026 Uiso 1 1 calc R . . C9 C 0.6503(7) 0.00808(17) 0.2392(6) 0.0225(9) Uani 1 1 d . . . C10 C 0.8499(7) 0.01778(18) 0.2282(7) 0.0266(10) Uani 1 1 d . . . H10 H 0.9382 -0.0094 0.2396 0.032 Uiso 1 1 calc R . . C11 C 0.9173(7) 0.06623(18) 0.2010(7) 0.0254(10) Uani 1 1 d . . . H11 H 1.0516 0.0718 0.1951 0.031 Uiso 1 1 calc R . . N12 N 0.5821(7) -0.03979(16) 0.2696(7) 0.0334(10) Uani 1 1 d . . . C13 C 0.7138(9) -0.08102(19) 0.3115(8) 0.0358(13) Uani 1 1 d . . . H13A H 0.7933 -0.0878 0.204 0.054 Uiso 1 1 calc R . . H13B H 0.6406 -0.1114 0.3424 0.054 Uiso 1 1 calc R . . H13C H 0.7961 -0.0716 0.4162 0.054 Uiso 1 1 calc R . . C14 C 0.3770(8) -0.0491(2) 0.2735(8) 0.0350(12) Uani 1 1 d . . . H14A H 0.3226 -0.033 0.3824 0.053 Uiso 1 1 calc R . . H14B H 0.3536 -0.0856 0.2785 0.053 Uiso 1 1 calc R . . H14C H 0.3165 -0.0351 0.1622 0.053 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 C1 0.019(2) 0.020(2) 0.022(2) -0.0007(17) 0.0006(17) -0.0018(18) I1 0.02632(16) 0.02006(14) 0.01829(13) 0.00081(11) 0.00221(11) -0.00102(12) C2 0.033(3) 0.022(2) 0.025(2) -0.0023(19) 0.001(2) -0.006(2) C3 0.041(3) 0.026(3) 0.022(2) 0.0051(19) 0.003(2) -0.009(2) N4 0.029(2) 0.025(2) 0.0229(19) 0.0003(16) 0.0005(17) -0.0061(18) N5 0.0170(19) 0.0196(19) 0.0218(19) 0.0047(15) 0.0056(15) -0.0041(14) C6 0.020(2) 0.018(2) 0.017(2) -0.0032(16) 0.0008(17) -0.0030(17) C7 0.020(2) 0.018(2) 0.022(2) -0.0021(16) -0.0001(18) 0.0019(17) I7 0.02070(16) 0.02004(15) 0.0493(2) -0.00124(13) -0.00192(14) 0.00228(12) C8 0.019(2) 0.023(2) 0.024(2) 0.0003(18) -0.0004(18) -0.0024(18) C9 0.024(2) 0.019(2) 0.024(2) 0.0028(18) -0.0026(18) -0.0014(18) C10 0.026(3) 0.023(2) 0.031(3) 0.0005(19) -0.003(2) 0.0062(19) C11 0.017(2) 0.028(2) 0.032(3) 0.0003(19) 0.002(2) -0.0013(19) N12 0.031(2) 0.022(2) 0.047(3) 0.0082(19) -0.009(2) -0.0042(18) C13 0.043(3) 0.021(2) 0.043(3) 0.004(2) -0.003(3) 0.001(2) C14 0.039(3) 0.027(3) 0.039(3) 0.006(2) 0.005(2) -0.015(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.365(6) . ? C1 N5 1.369(6) . ? C1 I1 2.062(4) . ? C2 C3 1.394(7) . ? C2 H2 0.95 . ? C3 N4 1.334(6) . ? C3 H3 0.95 . ? N4 N5 1.359(5) . ? N5 C6 1.435(6) . ? C6 C11 1.389(7) . ? C6 C7 1.391(6) . ? C7 C8 1.386(6) . ? C7 I7 2.105(4) . ? C8 C9 1.403(6) . ? C8 H8 0.95 . ? C9 N12 1.372(6) . ? C9 C10 1.419(7) . ? C10 C11 1.380(7) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? N12 C14 1.452(7) . ? N12 C13 1.456(7) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N5 106.9(4) . . ? C2 C1 I1 129.8(3) . . ? N5 C1 I1 123.3(3) . . ? C1 C2 C3 105.2(4) . . ? C1 C2 H2 127.4 . . ? C3 C2 H2 127.4 . . ? N4 C3 C2 112.1(4) . . ? N4 C3 H3 124 . . ? C2 C3 H3 124 . . ? C3 N4 N5 104.4(4) . . ? N4 N5 C1 111.4(4) . . ? N4 N5 C6 120.8(4) . . ? C1 N5 C6 127.8(4) . . ? C11 C6 C7 118.1(4) . . ? C11 C6 N5 120.3(4) . . ? C7 C6 N5 121.6(4) . . ? C8 C7 C6 121.3(4) . . ? C8 C7 I7 118.8(3) . . ? C6 C7 I7 119.9(3) . . ? C7 C8 C9 121.1(4) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? N12 C9 C8 121.7(4) . . ? N12 C9 C10 121.3(4) . . ? C8 C9 C10 117.1(4) . . ? C11 C10 C9 120.8(4) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C6 121.6(4) . . ? C10 C11 H11 119.2 . . ? C6 C11 H11 119.2 . . ? C9 N12 C14 120.3(4) . . ? C9 N12 C13 120.4(4) . . ? C14 N12 C13 119.1(4) . . ? N12 C13 H13A 109.5 . . ? N12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N12 C14 H14A 109.5 . . ? N12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 N5 C1 C2 C3 0.5(6) . . . . ? I1 C1 C2 C3 178.9(4) . . . . ? C1 C2 C3 N4 -0.4(6) . . . . ? C2 C3 N4 N5 0.1(6) . . . . ? C3 N4 N5 C1 0.2(5) . . . . ? C3 N4 N5 C6 178.3(4) . . . . ? C2 C1 N5 N4 -0.4(5) . . . . ? I1 C1 N5 N4 -179.0(3) . . . . ? C2 C1 N5 C6 -178.4(4) . . . . ? I1 C1 N5 C6 3.0(6) . . . . ? N4 N5 C6 C11 92.8(5) . . . . ? C1 N5 C6 C11 -89.4(6) . . . . ? N4 N5 C6 C7 -89.3(5) . . . . ? C1 N5 C6 C7 88.6(6) . . . . ? C11 C6 C7 C8 0.2(7) . . . . ? N5 C6 C7 C8 -177.7(4) . . . . ? C11 C6 C7 I7 179.9(3) . . . . ? N5 C6 C7 I7 1.9(6) . . . . ? C6 C7 C8 C9 0.9(7) . . . . ? I7 C7 C8 C9 -178.8(4) . . . . ? C7 C8 C9 N12 178.6(5) . . . . ? C7 C8 C9 C10 -1.8(7) . . . . ? N12 C9 C10 C11 -178.8(5) . . . . ? C8 C9 C10 C11 1.6(7) . . . . ? C9 C10 C11 C6 -0.5(8) . . . . ? C7 C6 C11 C10 -0.4(7) . . . . ? N5 C6 C11 C10 177.6(4) . . . . ? C8 C9 N12 C14 2.0(8) . . . . ? C10 C9 N12 C14 -177.7(5) . . . . ? C8 C9 N12 C13 -173.6(5) . . . . ? C10 C9 N12 C13 6.8(8) . . . . ? data_6j _database_code_depnum_ccdc_archive 'CCDC 800831' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-02-23T18:47:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H8 I2 N4' _chemical_formula_sum 'C12 H8 I2 N4' _chemical_formula_weight 462.02 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a b' _symmetry_space_group_name_Hall '-P 2bc 2n' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x-1/2, -y, z' _cell_length_a 8.3852(3) _cell_length_b 10.2090(3) _cell_length_c 16.0643(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1375.18(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3489 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.35 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 2.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.222 _exptl_absorpt_correction_T_max 0.367 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_unetI/netI 0.0221 _diffrn_reflns_number 6058 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 1568 _reflns_number_gt 1406 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0110P)^2^+0.8343P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00404(17) _refine_ls_number_reflns 1568 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0203 _refine_ls_R_factor_gt 0.017 _refine_ls_wR_factor_ref 0.037 _refine_ls_wR_factor_gt 0.0359 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.375 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 I1 I 0.916232(17) 0.225390(14) 0.778256(9) 0.02009(7) Uani 1 1 d . . . C1 C 0.7430(3) 0.3119(2) 0.85141(12) 0.0151(4) Uani 1 1 d . . . C2 C 0.6747(3) 0.4327(2) 0.84160(13) 0.0188(4) Uani 1 1 d . . . H2 H 0.6939 0.4947 0.7986 0.023 Uiso 1 1 calc R . . C3 C 0.5697(3) 0.4446(2) 0.90929(14) 0.0211(5) Uani 1 1 d . . . H3 H 0.5051 0.5194 0.9192 0.025 Uiso 1 1 calc R . . N4 N 0.5712(2) 0.33980(18) 0.95766(11) 0.0198(4) Uani 1 1 d . . . N5 N 0.6786(2) 0.25696(16) 0.92085(11) 0.0143(4) Uani 1 1 d . . . C6 C 0.7156(2) 0.13575(19) 0.96050(12) 0.0155(4) Uani 1 1 d . . . C7 C 0.6813(3) 0.0185(2) 0.92151(14) 0.0224(5) Uani 1 1 d . . . H7 H 0.634 0.0185 0.8678 0.027 Uiso 1 1 calc R . . C8 C 0.7157(3) -0.0992(2) 0.96084(14) 0.0264(5) Uani 1 1 d . . . H8 H 0.6922 -0.1798 0.9339 0.032 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 I1 0.01804(9) 0.02471(11) 0.01752(9) -0.00091(6) 0.00401(5) 0.00138(6) C1 0.0151(10) 0.0186(10) 0.0117(10) -0.0026(8) -0.0010(8) -0.0026(9) C2 0.0218(11) 0.0178(11) 0.0167(11) 0.0022(9) -0.0035(9) 0.0004(9) C3 0.0235(12) 0.0180(11) 0.0218(12) -0.0002(9) -0.0028(9) 0.0070(9) N4 0.0211(10) 0.0202(10) 0.0182(10) -0.0027(8) 0.0031(8) 0.0071(8) N5 0.0153(9) 0.0140(8) 0.0136(9) -0.0016(7) 0.0005(7) 0.0023(7) C6 0.0163(10) 0.0157(10) 0.0144(10) 0.0015(8) 0.0033(8) 0.0005(8) C7 0.0283(13) 0.0222(11) 0.0166(11) -0.0026(9) -0.0021(9) -0.0004(10) C8 0.0367(14) 0.0151(10) 0.0275(13) -0.0044(9) 0.0005(11) -0.0018(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 I1 C1 2.067(2) . ? C1 N5 1.361(3) . ? C1 C2 1.369(3) . ? C2 C3 1.404(3) . ? C2 H2 0.95 . ? C3 N4 1.323(3) . ? C3 H3 0.95 . ? N4 N5 1.369(2) . ? N5 C6 1.426(3) . ? C6 C7 1.381(3) . ? C6 C6 1.394(4) 4_657 ? C7 C8 1.389(3) . ? C7 H7 0.95 . ? C8 C8 1.383(5) 4_657 ? C8 H8 0.95 . ? 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 N5 C1 C2 107.42(18) . . ? N5 C1 I1 124.70(15) . . ? C2 C1 I1 127.87(16) . . ? C1 C2 C3 104.54(19) . . ? C1 C2 H2 127.7 . . ? C3 C2 H2 127.7 . . ? N4 C3 C2 112.3(2) . . ? N4 C3 H3 123.9 . . ? C2 C3 H3 123.9 . . ? C3 N4 N5 104.62(18) . . ? C1 N5 N4 111.13(16) . . ? C1 N5 C6 129.59(17) . . ? N4 N5 C6 119.11(17) . . ? C7 C6 C6 119.95(13) . 4_657 ? C7 C6 N5 120.25(19) . . ? C6 C6 N5 119.79(11) 4_657 . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C8 C8 C7 120.02(13) 4_657 . ? C8 C8 H8 120 4_657 . ? C7 C8 H8 120 . . ? 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 N5 C1 C2 C3 0.7(2) . . . . ? I1 C1 C2 C3 -177.94(16) . . . . ? C1 C2 C3 N4 -0.2(3) . . . . ? C2 C3 N4 N5 -0.3(3) . . . . ? C2 C1 N5 N4 -1.0(2) . . . . ? I1 C1 N5 N4 177.73(14) . . . . ? C2 C1 N5 C6 -176.1(2) . . . . ? I1 C1 N5 C6 2.6(3) . . . . ? C3 N4 N5 C1 0.8(2) . . . . ? C3 N4 N5 C6 176.50(19) . . . . ? C1 N5 C6 C7 -67.7(3) . . . . ? N4 N5 C6 C7 117.5(2) . . . . ? C1 N5 C6 C6 113.4(3) . . . 4_657 ? N4 N5 C6 C6 -61.4(3) . . . 4_657 ? C6 C6 C7 C8 -0.3(4) 4_657 . . . ? N5 C6 C7 C8 -179.2(2) . . . . ? C6 C7 C8 C8 0.1(4) . . . 4_657 ? data_4b _database_code_depnum_ccdc_archive 'CCDC 800832' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2010-11-05T17:26:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H17 N3' _chemical_formula_sum 'C17 H17 N3' _chemical_formula_weight 263.34 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 6.3843(5) _cell_length_b 30.629(2) _cell_length_c 7.1492(6) _cell_angle_alpha 90 _cell_angle_beta 94.735(3) _cell_angle_gamma 90 _cell_volume 1393.22(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3561 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 27.03 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.805 _exptl_absorpt_correction_T_max 0.977 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_unetI/netI 0.0375 _diffrn_reflns_number 10133 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 3171 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0209P)^2^+1.5977P] 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_number_reflns 3171 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.077 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1473 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 1.188 _refine_ls_restrained_S_all 1.188 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.23 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3655(4) 0.15763(7) 0.0287(3) 0.0271(5) Uani 1 1 d . . . H1 H 0.2277 0.1457 0.0156 0.033 Uiso 1 1 calc R . . C2 C 0.4914(4) 0.15523(8) -0.1192(4) 0.0330(5) Uani 1 1 d . . . H2 H 0.4399 0.1416 -0.2333 0.04 Uiso 1 1 calc R . . C3 C 0.6929(4) 0.17261(8) -0.1017(4) 0.0402(6) Uani 1 1 d . . . H3 H 0.7797 0.1709 -0.2031 0.048 Uiso 1 1 calc R . . C4 C 0.7662(4) 0.19249(8) 0.0646(4) 0.0408(6) Uani 1 1 d . . . H4 H 0.9039 0.2045 0.0769 0.049 Uiso 1 1 calc R . . C5 C 0.6415(4) 0.19515(7) 0.2131(4) 0.0330(5) Uani 1 1 d . . . H5 H 0.6934 0.2091 0.3262 0.04 Uiso 1 1 calc R . . C6 C 0.4394(4) 0.17744(7) 0.1974(3) 0.0251(5) Uani 1 1 d . . . C7 C 0.3050(4) 0.18232(7) 0.3536(3) 0.0263(5) Uani 1 1 d . . . C8 C 0.2747(4) 0.21848(8) 0.4641(3) 0.0345(6) Uani 1 1 d . . . H8 H 0.3441 0.2459 0.4611 0.041 Uiso 1 1 calc R . . C9 C 0.1207(4) 0.20617(8) 0.5807(4) 0.0372(6) Uani 1 1 d . . . H9 H 0.0673 0.225 0.6711 0.045 Uiso 1 1 calc R . . N10 N 0.0568(3) 0.16528(7) 0.5516(3) 0.0319(5) Uani 1 1 d . . . N11 N 0.1716(3) 0.15097(6) 0.4108(3) 0.0247(4) Uani 1 1 d . . . C12 C 0.1517(3) 0.10616(7) 0.3553(3) 0.0225(4) Uani 1 1 d . . . C13 C -0.0460(4) 0.08841(7) 0.3151(3) 0.0267(5) Uani 1 1 d . . . H13 H -0.1669 0.1064 0.3172 0.032 Uiso 1 1 calc R . . C14 C -0.0687(4) 0.04453(7) 0.2718(3) 0.0275(5) Uani 1 1 d . . . H14 H -0.2057 0.0327 0.2464 0.033 Uiso 1 1 calc R . . C15 C 0.1069(4) 0.01707(7) 0.2648(3) 0.0234(4) Uani 1 1 d . . . C16 C 0.3062(3) 0.03609(7) 0.3045(3) 0.0247(5) Uani 1 1 d . . . H16 H 0.4283 0.0185 0.3005 0.03 Uiso 1 1 calc R . . C17 C 0.3279(3) 0.07987(7) 0.3494(3) 0.0231(4) Uani 1 1 d . . . H17 H 0.464 0.092 0.3764 0.028 Uiso 1 1 calc R . . N18 N 0.0845(3) -0.02626(6) 0.2170(3) 0.0324(5) Uani 1 1 d . . . C19 C 0.2660(5) -0.05413(8) 0.2173(5) 0.0475(7) Uani 1 1 d . . . H19A H 0.3652 -0.0419 0.1338 0.071 Uiso 1 1 calc R . . H19B H 0.2224 -0.0833 0.1732 0.071 Uiso 1 1 calc R . . H19C H 0.3339 -0.0562 0.345 0.071 Uiso 1 1 calc R . . C20 C -0.1218(4) -0.04638(8) 0.2025(4) 0.0374(6) Uani 1 1 d . . . H20A H -0.1898 -0.0412 0.3184 0.056 Uiso 1 1 calc R . . H20B H -0.1075 -0.0779 0.183 0.056 Uiso 1 1 calc R . . H20C H -0.2076 -0.0337 0.0961 0.056 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 C1 0.0278(11) 0.0228(10) 0.0303(12) 0.0028(9) 0.0002(9) -0.0016(9) C2 0.0400(14) 0.0269(12) 0.0322(13) 0.0022(10) 0.0042(10) 0.0042(10) C3 0.0441(15) 0.0272(12) 0.0522(17) 0.0072(11) 0.0207(13) 0.0049(11) C4 0.0292(13) 0.0284(12) 0.0654(19) 0.0054(12) 0.0069(12) -0.0046(10) C5 0.0327(13) 0.0216(11) 0.0437(14) 0.0013(10) -0.0039(11) -0.0031(9) C6 0.0291(11) 0.0169(9) 0.0285(11) 0.0052(8) -0.0016(9) 0.0003(8) C7 0.0309(12) 0.0223(10) 0.0248(11) 0.0010(8) -0.0035(9) 0.0005(9) C8 0.0478(15) 0.0218(11) 0.0322(13) -0.0022(10) -0.0075(11) 0.0001(10) C9 0.0497(16) 0.0307(12) 0.0301(13) -0.0065(10) -0.0037(11) 0.0090(11) N10 0.0385(11) 0.0327(11) 0.0250(10) -0.0030(8) 0.0058(8) 0.0069(9) N11 0.0285(10) 0.0230(9) 0.0227(9) -0.0008(7) 0.0023(8) 0.0005(7) C12 0.0283(11) 0.0208(10) 0.0187(10) 0.0028(8) 0.0048(8) -0.0022(8) C13 0.0237(11) 0.0270(11) 0.0298(12) 0.0024(9) 0.0044(9) 0.0000(9) C14 0.0224(11) 0.0308(12) 0.0294(12) 0.0019(9) 0.0033(9) -0.0064(9) C15 0.0298(11) 0.0219(10) 0.0185(10) 0.0025(8) 0.0025(8) -0.0032(8) C16 0.0253(11) 0.0236(10) 0.0252(11) 0.0052(8) 0.0018(9) 0.0024(8) C17 0.0208(10) 0.0251(10) 0.0231(11) 0.0045(8) -0.0001(8) -0.0033(8) N18 0.0357(11) 0.0223(9) 0.0387(12) -0.0033(8) -0.0010(9) -0.0024(8) C19 0.0546(18) 0.0250(13) 0.0597(19) -0.0055(12) -0.0140(15) 0.0091(12) C20 0.0480(15) 0.0314(13) 0.0330(13) -0.0028(10) 0.0051(11) -0.0158(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(3) . ? C1 C6 1.397(3) . ? C1 H1 0.95 . ? C2 C3 1.388(4) . ? C2 H2 0.95 . ? C3 C4 1.383(4) . ? C3 H3 0.95 . ? C4 C5 1.380(4) . ? C4 H4 0.95 . ? C5 C6 1.396(3) . ? C5 H5 0.95 . ? C6 C7 1.471(3) . ? C7 N11 1.368(3) . ? C7 C8 1.383(3) . ? C8 C9 1.392(4) . ? C8 H8 0.95 . ? C9 N10 1.328(3) . ? C9 H9 0.95 . ? N10 N11 1.366(3) . ? N11 C12 1.431(3) . ? C12 C13 1.383(3) . ? C12 C17 1.387(3) . ? C13 C14 1.384(3) . ? C13 H13 0.95 . ? C14 C15 1.406(3) . ? C14 H14 0.95 . ? C15 N18 1.375(3) . ? C15 C16 1.407(3) . ? C16 C17 1.383(3) . ? C16 H16 0.95 . ? C17 H17 0.95 . ? N18 C19 1.439(3) . ? N18 C20 1.450(3) . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.5(2) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C1 C2 C3 120.3(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.8(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 118.8(2) . . ? C5 C6 C7 119.5(2) . . ? C1 C6 C7 121.5(2) . . ? N11 C7 C8 105.7(2) . . ? N11 C7 C6 124.89(19) . . ? C8 C7 C6 129.3(2) . . ? C7 C8 C9 105.3(2) . . ? C7 C8 H8 127.3 . . ? C9 C8 H8 127.3 . . ? N10 C9 C8 112.7(2) . . ? N10 C9 H9 123.7 . . ? C8 C9 H9 123.7 . . ? C9 N10 N11 103.9(2) . . ? N10 N11 C7 112.36(18) . . ? N10 N11 C12 118.13(18) . . ? C7 N11 C12 129.28(19) . . ? C13 C12 C17 119.6(2) . . ? C13 C12 N11 119.6(2) . . ? C17 C12 N11 120.77(19) . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.3(2) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? N18 C15 C14 121.3(2) . . ? N18 C15 C16 121.6(2) . . ? C14 C15 C16 117.10(19) . . ? C17 C16 C15 121.3(2) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C12 120.3(2) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? C15 N18 C19 120.3(2) . . ? C15 N18 C20 120.2(2) . . ? C19 N18 C20 118.3(2) . . ? N18 C19 H19A 109.5 . . ? N18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N18 C20 H20A 109.5 . . ? N18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? C4 C5 C6 C7 -177.2(2) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C2 C1 C6 C7 177.0(2) . . . . ? C5 C6 C7 N11 -141.8(2) . . . . ? C1 C6 C7 N11 41.9(3) . . . . ? C5 C6 C7 C8 42.5(3) . . . . ? C1 C6 C7 C8 -133.8(3) . . . . ? N11 C7 C8 C9 -0.6(3) . . . . ? C6 C7 C8 C9 175.7(2) . . . . ? C7 C8 C9 N10 0.8(3) . . . . ? C8 C9 N10 N11 -0.6(3) . . . . ? C9 N10 N11 C7 0.2(3) . . . . ? C9 N10 N11 C12 175.1(2) . . . . ? C8 C7 N11 N10 0.3(3) . . . . ? C6 C7 N11 N10 -176.3(2) . . . . ? C8 C7 N11 C12 -174.0(2) . . . . ? C6 C7 N11 C12 9.5(4) . . . . ? N10 N11 C12 C13 50.3(3) . . . . ? C7 N11 C12 C13 -135.7(2) . . . . ? N10 N11 C12 C17 -126.8(2) . . . . ? C7 N11 C12 C17 47.2(3) . . . . ? C17 C12 C13 C14 0.9(3) . . . . ? N11 C12 C13 C14 -176.2(2) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C13 C14 C15 N18 -178.3(2) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? N18 C15 C16 C17 178.9(2) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C15 C16 C17 C12 -0.3(3) . . . . ? C13 C12 C17 C16 -0.3(3) . . . . ? N11 C12 C17 C16 176.81(19) . . . . ? C14 C15 N18 C19 -177.7(2) . . . . ? C16 C15 N18 C19 3.7(3) . . . . ? C14 C15 N18 C20 -10.1(3) . . . . ? C16 C15 N18 C20 171.4(2) . . . . ? data_1o _database_code_depnum_ccdc_archive 'CCDC 813448' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2011-02-16T11:16:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H7 N3' _chemical_formula_sum 'C8 H7 N3' _chemical_formula_weight 145.17 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.299(3) _cell_length_b 4.2309(9) _cell_length_c 14.743(3) _cell_angle_alpha 90 _cell_angle_beta 90.229(8) _cell_angle_gamma 90 _cell_volume 704.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2131 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 27.57 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.45 _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.616 _exptl_absorpt_correction_T_max 0.961 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_unetI/netI 0.0407 _diffrn_reflns_number 5605 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 1606 _reflns_number_gt 1174 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0632P)^2^+0.4046P] 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_number_reflns 1606 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.204 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.06691(17) 0.1212(5) 0.34996(13) 0.0291(5) Uani 1 1 d . . . H1 H -0.016 0.1488 0.3422 0.035 Uiso 1 1 calc R . . C2 C 0.12128(18) -0.0563(6) 0.41548(14) 0.0325(5) Uani 1 1 d . . . H2 H 0.0851 -0.1764 0.4622 0.039 Uiso 1 1 calc R . . C3 C 0.24284(17) -0.0209(6) 0.39816(13) 0.0316(5) Uani 1 1 d . . . H3 H 0.3033 -0.1188 0.4332 0.038 Uiso 1 1 calc R . . N4 N 0.26350(13) 0.1643(5) 0.32753(11) 0.0290(4) Uani 1 1 d . . . N5 N 0.15328(13) 0.2510(4) 0.29784(10) 0.0235(4) Uani 1 1 d . . . C6 C 0.14162(15) 0.4494(5) 0.22105(12) 0.0210(4) Uani 1 1 d . . . C7 C 0.02939(15) 0.5301(5) 0.18775(13) 0.0274(5) Uani 1 1 d . . . H7 H -0.0383 0.4533 0.2188 0.033 Uiso 1 1 calc R . . N8 N 0.01322(13) 0.7098(5) 0.11449(11) 0.0326(5) Uani 1 1 d . . . C9 C 0.10957(16) 0.8168(5) 0.07168(13) 0.0286(5) Uani 1 1 d . . . H9 H 0.0993 0.9419 0.0187 0.034 Uiso 1 1 calc R . . C10 C 0.22377(15) 0.7527(5) 0.10138(13) 0.0258(5) Uani 1 1 d . . . H10 H 0.2899 0.837 0.07 0.031 Uiso 1 1 calc R . . C11 C 0.24003(14) 0.5663(5) 0.17650(12) 0.0242(5) Uani 1 1 d . . . H11 H 0.3175 0.5182 0.1976 0.029 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 C1 0.0205(9) 0.0318(14) 0.0352(10) -0.0016(9) 0.0068(7) -0.0027(8) C2 0.0331(11) 0.0311(14) 0.0335(10) 0.0002(9) 0.0067(8) -0.0008(9) C3 0.0281(10) 0.0333(14) 0.0335(10) -0.0004(9) -0.0026(8) 0.0031(9) N4 0.0164(7) 0.0361(12) 0.0346(9) 0.0005(8) -0.0024(6) 0.0034(7) N5 0.0138(7) 0.0257(10) 0.0308(8) -0.0025(7) 0.0018(6) 0.0009(7) C6 0.0140(8) 0.0219(11) 0.0273(9) -0.0041(8) 0.0016(6) 0.0019(7) C7 0.0115(8) 0.0326(13) 0.0382(10) 0.0019(9) 0.0035(7) -0.0023(8) N8 0.0122(7) 0.0456(13) 0.0400(10) 0.0067(8) 0.0012(6) 0.0010(7) C9 0.0159(9) 0.0374(14) 0.0326(10) 0.0034(9) 0.0015(7) 0.0020(8) C10 0.0126(8) 0.0314(13) 0.0335(10) -0.0012(8) 0.0051(7) 0.0002(8) C11 0.0099(7) 0.0278(12) 0.0349(10) -0.0029(8) 0.0009(7) 0.0006(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.360(2) . ? C1 C2 1.367(3) . ? C1 H1 0.95 . ? C2 C3 1.406(3) . ? C2 H2 0.95 . ? C3 N4 1.325(3) . ? C3 H3 0.95 . ? N4 N5 1.368(2) . ? N5 C6 1.415(2) . ? C6 C11 1.385(2) . ? C6 C7 1.400(2) . ? C7 N8 1.333(3) . ? C7 H7 0.95 . ? N8 C9 1.339(2) . ? C9 C10 1.388(2) . ? C9 H9 0.95 . ? C10 C11 1.371(3) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? 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 N5 C1 C2 107.42(17) . . ? N5 C1 H1 126.3 . . ? C2 C1 H1 126.3 . . ? C1 C2 C3 104.46(18) . . ? C1 C2 H2 127.8 . . ? C3 C2 H2 127.8 . . ? N4 C3 C2 112.40(18) . . ? N4 C3 H3 123.8 . . ? C2 C3 H3 123.8 . . ? C3 N4 N5 104.29(15) . . ? C1 N5 N4 111.42(16) . . ? C1 N5 C6 128.81(16) . . ? N4 N5 C6 119.77(14) . . ? C11 C6 C7 118.31(18) . . ? C11 C6 N5 121.26(16) . . ? C7 C6 N5 120.43(16) . . ? N8 C7 C6 122.98(17) . . ? N8 C7 H7 118.5 . . ? C6 C7 H7 118.5 . . ? C7 N8 C9 117.74(16) . . ? N8 C9 C10 122.81(19) . . ? N8 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C11 C10 C9 119.25(17) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C6 118.89(16) . . ? C10 C11 H11 120.6 . . ? C6 C11 H11 120.6 . . ? 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 N5 C1 C2 C3 0.1(2) . . . . ? C1 C2 C3 N4 0.1(3) . . . . ? C2 C3 N4 N5 -0.2(2) . . . . ? C2 C1 N5 N4 -0.2(2) . . . . ? C2 C1 N5 C6 179.13(19) . . . . ? C3 N4 N5 C1 0.2(2) . . . . ? C3 N4 N5 C6 -179.14(17) . . . . ? C1 N5 C6 C11 178.80(19) . . . . ? N4 N5 C6 C11 -1.9(3) . . . . ? C1 N5 C6 C7 -1.8(3) . . . . ? N4 N5 C6 C7 177.52(17) . . . . ? C11 C6 C7 N8 1.1(3) . . . . ? N5 C6 C7 N8 -178.37(18) . . . . ? C6 C7 N8 C9 -0.2(3) . . . . ? C7 N8 C9 C10 -1.1(3) . . . . ? N8 C9 C10 C11 1.5(3) . . . . ? C9 C10 C11 C6 -0.5(3) . . . . ? C7 C6 C11 C10 -0.7(3) . . . . ? N5 C6 C11 C10 178.76(18) . . . . ? data_1j _database_code_depnum_ccdc_archive 'CCDC 813449' #TrackingRef 'CIF-pyrazoles-mongin.cif' _audit_creation_date 2011-02-16T11:29:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H10 N4' _chemical_formula_sum 'C12 H10 N4' _chemical_formula_weight 210.24 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.745(4) _cell_length_b 12.472(6) _cell_length_c 10.787(5) _cell_angle_alpha 90 _cell_angle_beta 92.060(14) _cell_angle_gamma 90 _cell_volume 1041.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 710 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.45 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.159 _exptl_absorpt_correction_T_max 0.997 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_av_unetI/netI 0.1707 _diffrn_reflns_number 2360 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 2360 _reflns_number_gt 1062 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0797P)^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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.055(6) _refine_ls_number_reflns 2360 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1551 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1724 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.312 _refine_diff_density_min -0.4 _refine_diff_density_rms 0.09 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2220(4) 0.2900(3) 0.4313(3) 0.0286(8) Uani 1 1 d . . . H1 H 0.2268 0.2464 0.3593 0.034 Uiso 1 1 calc R . . C2 C 0.2405(4) 0.3988(3) 0.4362(3) 0.0330(9) Uani 1 1 d . . . H2 H 0.2604 0.4463 0.3693 0.04 Uiso 1 1 calc R . . C3 C 0.2238(4) 0.4249(2) 0.5619(3) 0.0289(8) Uani 1 1 d . . . H3 H 0.2318 0.4958 0.5937 0.035 Uiso 1 1 calc R . . N4 N 0.1956(3) 0.33880(19) 0.6313(2) 0.0255(7) Uani 1 1 d . . . N5 N 0.1954(3) 0.25578(19) 0.5481(2) 0.0237(6) Uani 1 1 d . . . C6 C 0.1659(4) 0.1483(2) 0.5887(3) 0.0231(7) Uani 1 1 d . . . C7 C 0.3003(4) 0.0749(2) 0.5802(3) 0.0256(8) Uani 1 1 d . . . H7 H 0.4081 0.0969 0.5492 0.031 Uiso 1 1 calc R . . C8 C 0.2767(4) -0.0305(3) 0.6169(3) 0.0290(8) Uani 1 1 d . . . H8 H 0.368 -0.0809 0.6111 0.035 Uiso 1 1 calc R . . C9 C 0.1204(4) -0.0617(3) 0.6618(3) 0.0276(8) Uani 1 1 d . . . H9 H 0.1049 -0.1336 0.6884 0.033 Uiso 1 1 calc R . . C10 C -0.0148(4) 0.0109(3) 0.6687(3) 0.0264(8) Uani 1 1 d . . . H10 H -0.1225 -0.0116 0.6992 0.032 Uiso 1 1 calc R . . C11 C 0.0070(4) 0.1163(2) 0.6314(3) 0.0228(7) Uani 1 1 d . . . N12 N -0.1360(3) 0.18716(19) 0.6393(2) 0.0244(7) Uani 1 1 d . . . N13 N -0.2515(3) 0.1692(2) 0.7303(2) 0.0310(7) Uani 1 1 d . . . C14 C -0.3785(4) 0.2377(3) 0.7038(3) 0.0343(9) Uani 1 1 d . . . H14 H -0.4785 0.2448 0.7515 0.041 Uiso 1 1 calc R . . C15 C -0.3486(4) 0.2986(3) 0.5974(3) 0.0323(9) Uani 1 1 d . . . H15 H -0.4211 0.3521 0.5604 0.039 Uiso 1 1 calc R . . C16 C -0.1937(4) 0.2642(2) 0.5591(3) 0.0284(8) Uani 1 1 d . . . H16 H -0.1356 0.2895 0.4887 0.034 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 C1 0.025(2) 0.032(2) 0.029(2) 0.0015(14) 0.0062(14) -0.0025(16) C2 0.028(2) 0.031(2) 0.040(2) 0.0070(15) 0.0047(15) -0.0047(16) C3 0.029(2) 0.0215(18) 0.037(2) 0.0013(15) 0.0077(15) 0.0013(15) N4 0.0287(16) 0.0209(15) 0.0271(15) -0.0035(11) 0.0043(11) -0.0027(12) N5 0.0195(15) 0.0237(16) 0.0284(16) 0.0018(11) 0.0062(11) -0.0026(12) C6 0.0222(19) 0.0244(19) 0.0230(17) -0.0005(13) 0.0065(13) -0.0026(14) C7 0.0213(18) 0.031(2) 0.0254(18) -0.0014(14) 0.0065(13) -0.0001(15) C8 0.026(2) 0.029(2) 0.032(2) -0.0048(14) 0.0026(14) 0.0067(15) C9 0.028(2) 0.0253(19) 0.0293(19) 0.0006(13) 0.0000(14) -0.0011(16) C10 0.0230(19) 0.032(2) 0.0239(18) 0.0003(13) 0.0041(13) -0.0029(15) C11 0.0223(19) 0.0245(19) 0.0217(18) -0.0018(13) 0.0023(13) 0.0030(14) N12 0.0195(16) 0.0230(16) 0.0308(16) 0.0002(11) 0.0043(12) 0.0019(12) N13 0.0194(16) 0.0380(17) 0.0361(17) -0.0037(12) 0.0096(12) -0.0007(13) C14 0.0149(19) 0.034(2) 0.054(2) -0.0089(16) 0.0055(16) -0.0015(16) C15 0.0189(19) 0.029(2) 0.049(2) -0.0070(15) -0.0033(15) 0.0005(15) C16 0.026(2) 0.028(2) 0.0306(19) 0.0017(14) 0.0022(14) -0.0021(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.353(4) . ? C1 C2 1.366(4) . ? C1 H1 0.95 . ? C2 C3 1.405(4) . ? C2 H2 0.95 . ? C3 N4 1.331(4) . ? C3 H3 0.95 . ? N4 N5 1.370(3) . ? N5 C6 1.431(4) . ? C6 C11 1.388(4) . ? C6 C7 1.392(4) . ? C7 C8 1.387(4) . ? C7 H7 0.95 . ? C8 C9 1.376(4) . ? C8 H8 0.95 . ? C9 C10 1.389(4) . ? C9 H9 0.95 . ? C10 C11 1.387(4) . ? C10 H10 0.95 . ? C11 N12 1.422(4) . ? N12 C16 1.358(4) . ? N12 N13 1.370(3) . ? N13 C14 1.326(4) . ? C14 C15 1.402(4) . ? C14 H14 0.95 . ? C15 C16 1.353(4) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? 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 N5 C1 C2 107.3(3) . . ? N5 C1 H1 126.4 . . ? C2 C1 H1 126.4 . . ? C1 C2 C3 104.7(3) . . ? C1 C2 H2 127.7 . . ? C3 C2 H2 127.7 . . ? N4 C3 C2 112.3(3) . . ? N4 C3 H3 123.9 . . ? C2 C3 H3 123.9 . . ? C3 N4 N5 103.8(3) . . ? C1 N5 N4 112.0(2) . . ? C1 N5 C6 127.7(3) . . ? N4 N5 C6 120.3(2) . . ? C11 C6 C7 120.5(3) . . ? C11 C6 N5 121.6(3) . . ? C7 C6 N5 117.9(3) . . ? C8 C7 C6 119.8(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 119.7(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.6(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C6 119.2(3) . . ? C10 C11 N12 117.9(3) . . ? C6 C11 N12 122.9(3) . . ? C16 N12 N13 111.3(2) . . ? C16 N12 C11 129.8(3) . . ? N13 N12 C11 118.1(2) . . ? C14 N13 N12 103.8(3) . . ? N13 C14 C15 112.5(3) . . ? N13 C14 H14 123.7 . . ? C15 C14 H14 123.7 . . ? C16 C15 C14 104.6(3) . . ? C16 C15 H15 127.7 . . ? C14 C15 H15 127.7 . . ? C15 C16 N12 107.8(3) . . ? C15 C16 H16 126.1 . . ? N12 C16 H16 126.1 . . ? 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 N5 C1 C2 C3 0.2(3) . . . . ? C1 C2 C3 N4 -0.4(4) . . . . ? C2 C3 N4 N5 0.4(4) . . . . ? C2 C1 N5 N4 0.0(3) . . . . ? C2 C1 N5 C6 178.8(3) . . . . ? C3 N4 N5 C1 -0.3(4) . . . . ? C3 N4 N5 C6 -179.1(3) . . . . ? C1 N5 C6 C11 -111.4(4) . . . . ? N4 N5 C6 C11 67.3(4) . . . . ? C1 N5 C6 C7 66.5(4) . . . . ? N4 N5 C6 C7 -114.9(3) . . . . ? C11 C6 C7 C8 -1.3(4) . . . . ? N5 C6 C7 C8 -179.2(3) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 C10 1.1(5) . . . . ? C8 C9 C10 C11 -0.6(4) . . . . ? C9 C10 C11 C6 -0.8(4) . . . . ? C9 C10 C11 N12 179.4(3) . . . . ? C7 C6 C11 C10 1.8(4) . . . . ? N5 C6 C11 C10 179.6(3) . . . . ? C7 C6 C11 N12 -178.5(3) . . . . ? N5 C6 C11 N12 -0.7(4) . . . . ? C10 C11 N12 C16 -139.4(3) . . . . ? C6 C11 N12 C16 40.9(5) . . . . ? C10 C11 N12 N13 30.2(4) . . . . ? C6 C11 N12 N13 -149.5(3) . . . . ? C16 N12 N13 C14 -0.6(3) . . . . ? C11 N12 N13 C14 -172.1(3) . . . . ? N12 N13 C14 C15 0.6(3) . . . . ? N13 C14 C15 C16 -0.4(4) . . . . ? C14 C15 C16 N12 -0.1(4) . . . . ? N13 N12 C16 C15 0.4(3) . . . . ? C11 N12 C16 C15 170.6(3) . . . . ?