# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_name 'Ignasi Mata' _publ_contact_author_email imata@icmab.es loop_ _publ_author_name J.J.L.Gonzalez A.M.J.Ramon I.Mata E.Molins R.Claramunt C.Lopez I.Alkorta J.Elguero data_c7n2h6 _database_code_depnum_ccdc_archive 'CCDC 827788' #TrackingRef 'web_deposit_cif_file_0_IgnasiMata_1306829698.archive-indazole.cif' _audit_creation_date 2011-04-26T11:15:53-00:00 _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_sum 'C7 H6 N2' _chemical_formula_weight 118.14 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.4285(4) _cell_length_b 5.7480(2) _cell_length_c 7.6305(4) _cell_angle_alpha 90 _cell_angle_beta 118.462(6) _cell_angle_gamma 90 _cell_volume 286.43(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 7231 _cell_measurement_theta_min 6.5936 _cell_measurement_theta_max 76.2575 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.37 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 124 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.684 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.6236 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4508 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_number 7284 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 6.6 _diffrn_reflns_theta_max 76.45 _diffrn_reflns_theta_full 76.45 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 1122 _reflns_number_gt 1116 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury CCDC' _computing_publication_material WINGX #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.0305P)^2^+0.4813P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refxyz _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 0.017(3) _refine_ls_number_reflns 1122 _refine_ls_number_parameters 101 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1297 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(11) _refine_diff_density_max 0.28 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # 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 0.0181 0.0091 '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 0.0311 0.018 '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 N1 N 0.9015(4) 0.9295(5) 0.7954(4) 0.0213(6) Uani 1 1 d D . . H1 H 0.903(5) 1.032(5) 0.884(4) 0.026 Uiso 1 1 d D . . N2 N 1.0187(4) 0.7330(5) 0.8650(4) 0.0234(6) Uani 1 1 d . . . C1 C 0.9720(5) 0.6017(6) 0.7068(5) 0.0230(7) Uani 1 1 d D . . H1A H 1.049(5) 0.462(5) 0.728(5) 0.028 Uiso 1 1 d D . . C2 C 0.7060(4) 0.6428(5) 0.3274(4) 0.0209(7) Uani 1 1 d D . . H2 H 0.708(5) 0.503(4) 0.261(5) 0.025 Uiso 1 1 d D . . C3 C 0.5559(5) 0.7907(6) 0.2010(4) 0.0228(7) Uani 1 1 d D . . H3 H 0.472(5) 0.750(7) 0.062(3) 0.027 Uiso 1 1 d D . . C4 C 0.5200(5) 1.0062(6) 0.2698(4) 0.0218(7) Uani 1 1 d D . . H4 H 0.424(4) 1.102(6) 0.168(4) 0.026 Uiso 1 1 d D . . C5 C 0.6303(4) 1.0740(5) 0.4630(4) 0.0211(7) Uani 1 1 d D . . H5 H 0.602(5) 1.220(4) 0.507(5) 0.025 Uiso 1 1 d D . . C6 C 0.7797(4) 0.9203(6) 0.5954(4) 0.0184(6) Uani 1 1 d . . . C7 C 0.8209(4) 0.7076(5) 0.5315(4) 0.0192(6) 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 N1 0.0267(13) 0.0170(13) 0.0190(12) -0.0022(10) 0.0099(10) 0.0004(11) N2 0.0246(12) 0.0220(15) 0.0227(12) 0.0025(11) 0.0104(10) 0.0019(11) C1 0.0230(14) 0.0213(16) 0.0266(15) 0.0022(14) 0.0134(12) 0.0013(13) C2 0.0247(14) 0.0210(18) 0.0207(14) -0.0006(12) 0.0138(12) -0.0007(12) C3 0.0237(15) 0.0268(19) 0.0202(14) -0.0010(12) 0.0122(12) -0.0027(13) C4 0.0207(14) 0.0238(17) 0.0240(14) 0.0084(12) 0.0132(12) 0.0038(12) C5 0.0225(14) 0.0184(16) 0.0269(15) 0.0031(13) 0.0154(12) 0.0014(12) C6 0.0202(14) 0.0177(16) 0.0204(13) -0.0009(12) 0.0122(11) -0.0028(11) C7 0.0210(13) 0.0176(15) 0.0226(14) -0.0010(13) 0.0133(11) -0.0009(12) #----------------------------------------------------------------------------# # 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 N1 C6 1.355(4) . ? N1 N2 1.369(4) . ? N1 H1 0.890(18) . ? N2 C1 1.322(4) . ? C1 C7 1.411(4) . ? C1 H1A 0.954(19) . ? C2 C3 1.368(4) . ? C2 C7 1.423(4) . ? C2 H2 0.956(18) . ? C3 C4 1.420(5) . ? C3 H3 0.969(18) . ? C4 C5 1.358(4) . ? C4 H4 0.944(18) . ? C5 C6 1.402(4) . ? C5 H5 0.960(18) . ? C6 C7 1.403(4) . ? 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 C6 N1 N2 111.3(2) . . ? C6 N1 H1 130(2) . . ? N2 N1 H1 118(2) . . ? C1 N2 N1 106.0(2) . . ? N2 C1 C7 111.3(3) . . ? N2 C1 H1A 117(2) . . ? C7 C1 H1A 132(2) . . ? C3 C2 C7 118.1(3) . . ? C3 C2 H2 111(2) . . ? C7 C2 H2 131(2) . . ? C2 C3 C4 121.0(3) . . ? C2 C3 H3 120(2) . . ? C4 C3 H3 119(2) . . ? C5 C4 C3 121.9(3) . . ? C5 C4 H4 124(2) . . ? C3 C4 H4 114(2) . . ? C4 C5 C6 117.6(3) . . ? C4 C5 H5 120(2) . . ? C6 C5 H5 122(2) . . ? N1 C6 C7 106.7(2) . . ? N1 C6 C5 131.4(3) . . ? C7 C6 C5 121.8(3) . . ? C6 C7 C1 104.6(3) . . ? C6 C7 C2 119.5(3) . . ? C1 C7 C2 135.8(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 C6 N1 N2 C1 0.9(3) . . . . ? N1 N2 C1 C7 -1.1(3) . . . . ? C7 C2 C3 C4 2.0(4) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 -1.5(4) . . . . ? N2 N1 C6 C7 -0.4(3) . . . . ? N2 N1 C6 C5 176.8(3) . . . . ? C4 C5 C6 N1 -174.5(3) . . . . ? C4 C5 C6 C7 2.4(4) . . . . ? N1 C6 C7 C1 -0.2(3) . . . . ? C5 C6 C7 C1 -177.8(3) . . . . ? N1 C6 C7 C2 176.4(3) . . . . ? C5 C6 C7 C2 -1.1(4) . . . . ? N2 C1 C7 C6 0.8(3) . . . . ? N2 C1 C7 C2 -175.0(3) . . . . ? C3 C2 C7 C6 -1.1(4) . . . . ? C3 C2 C7 C1 174.2(3) . . . . ? # END of CIF