# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 ---------- X-Sun-Data-Type: default X-Sun-Data-Name: 161111-2 X-Sun-Charset: us-ascii X-Sun-Content-Lines: 646 # 1. SUBMISSION DETAILS data_global _publ_contact_author # Name and address of author for correspondence ; Pinilla, Elena Departamento de Qummica Inorganica I Laboratorio de Difraccisn de Rayos X Facultad de Ciencias Qummicas Universidad Complutense de Madrid 28040 Madrid (Spain) ; _publ_contact_author_phone '+34 91 3944285' _publ_contact_author_fax '+34 91 3944284' _publ_contact_author_email elena@rx3.quim.ucm.es _publ_requested_journal 'New Journal of Chemistry' _journal_coden_Cambridge 440 _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication as a Regular Structure Paper in New Journal of Chemistry. ; #============================================================================ # 3. TITLE AND AUTHOR LIST _publ_section_title ; The structure of halogeno-1,2,4-triazoles in the solid state and in solution. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Claramunt, Rosa M.' ; Departamento de Qummica Organica y Biologia Facultad de Ciencias Universidad Nacional de Educacion a Distancia Senda del Rey s/n E-28040 Madrid (Spain) ; 'Lopez, Concepcion' ; Departamento de Qummica Organica y Biologia Facultad de Ciencias Universidad Nacional de Educacion a Distancia Senda del Rey s/n E-28040 Madrid (Spain) ; 'Garcia, M. Angeles' ; Departamento de Qummica Organica y Biologia Facultad de Ciencias Universidad Nacional de Educacion a Distancia Senda del Rey s/n E-28040 Madrid (Spain) ; 'Otero, M. Dolores' ; Departamento de Qummica Organica y Biologia Facultad de Ciencias Universidad Nacional de Educacion a Distancia Senda del Rey s/n E-28040 Madrid (Spain) ; 'Torres, M. Rosario' ; Laboratorio de Difraccisn de Rayos X Facultad de Ciencias Qummicas Universidad Complutense de Madrid E-28040 Madrid (Spain) ; 'Pinilla, Elena' ; Depto. de Qummica Inorganica I and Lab. de Difraccisn de Rayos X Facultad de Ciencias Qummicas Universidad Complutense de Madrid E-28040 Madrid (Spain) ; 'Alarcon, Sergio H.' ; Departamento de Quimica Analitica Facultad de Ciencias Bioquimicas y Farmaceuticas Universidad Nacional de Rosario Suipacha 531 Rosario 2000 (Argentina) ; 'AlKorta, Ibon' ; Instituto de Quimica Medica, CSIC Juan de la Cierva, 3 E-28006 Madrid (Spain) ; 'Elguero, Jose' ; Instituto de Quimica Medica, CSIC Juan de la Cierva, 3 E-28006 Madrid (Spain) ; #============================================================================ data_1a _database_code_CSD 161111 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H2 Br N3' _chemical_formula_weight 147.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.3740 2.4560 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.2101(8) _cell_length_b 9.9396(10) _cell_length_c 10.6382(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 868.13(15) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 82 _cell_measurement_theta_min 9 _cell_measurement_theta_max 15 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 9.292 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3352 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 22.98 _reflns_number_total 600 _reflns_number_gt 493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment riding on their atom bonded _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0085(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 600 _refine_ls_number_parameters 58 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0607 _refine_ls_wR_factor_gt 0.0584 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.03181(6) 0.29103(5) 0.26263(4) 0.0497(3) Uani 1 1 d . . . N1 N 0.2324(4) 0.5578(3) 0.4791(3) 0.0381(8) Uani 1 1 d . . . H1 H 0.2623 0.6345 0.4898 0.047(13) Uiso 1 1 d R . . N2 N 0.1458(3) 0.5273(3) 0.3745(3) 0.0376(8) Uani 1 1 d . . . C3 C 0.1385(4) 0.3962(3) 0.3826(3) 0.0307(8) Uani 1 1 d . . . N4 N 0.2130(4) 0.3406(3) 0.4826(3) 0.0373(8) Uani 1 1 d . . . C5 C 0.2712(5) 0.4476(4) 0.5414(4) 0.0401(10) Uani 1 1 d . . . H5 H 0.3299 0.4458 0.6146 0.049(11) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0565(4) 0.0545(4) 0.0381(3) -0.00877(17) -0.00496(17) -0.0117(2) N1 0.052(2) 0.0198(18) 0.043(2) -0.0017(14) -0.0005(15) -0.0037(13) N2 0.0478(18) 0.0293(17) 0.0356(18) 0.0032(13) -0.0040(15) 0.0016(14) C3 0.038(2) 0.030(2) 0.0239(18) -0.0020(14) 0.0063(16) -0.0002(15) N4 0.059(2) 0.0211(18) 0.0318(18) -0.0008(14) -0.0047(14) -0.0014(13) C5 0.056(2) 0.031(2) 0.033(2) 0.0003(18) -0.0073(18) 0.0038(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C3 1.868(3) . ? N1 C5 1.319(6) . ? N1 N2 1.356(4) . ? N1 H1 0.8093 . ? N2 C3 1.308(4) . ? C3 N4 1.346(4) . ? N4 C5 1.323(5) . ? C5 H5 0.9167 . ? 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 C5 N1 N2 110.7(3) . . ? C5 N1 H1 129.7 . . ? N2 N1 H1 119.0 . . ? C3 N2 N1 101.1(3) . . ? N2 C3 N4 116.1(3) . . ? N2 C3 Br1 122.3(2) . . ? N4 C3 Br1 121.6(2) . . ? C5 N4 C3 102.0(3) . . ? N4 C5 N1 110.0(4) . . ? N4 C5 H5 125.2 . . ? N1 C5 H5 124.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 C3 0.2(4) . . . . ? N1 N2 C3 N4 -0.2(4) . . . . ? N1 N2 C3 Br1 180.0(2) . . . . ? N2 C3 N4 C5 0.0(4) . . . . ? Br1 C3 N4 C5 179.9(3) . . . . ? C3 N4 C5 N1 0.1(4) . . . . ? N2 N1 C5 N4 -0.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N4 0.81 2.06 2.847(4) 164.1 8_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.660 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.076 #============================================================================= data_2a _database_code_CSD 161112 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H2 Cl N3' _chemical_formula_weight 103.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1320 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 10.849(2) _cell_length_b 3.7618(9) _cell_length_c 9.863(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 402.50(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 72 _cell_measurement_theta_min 12 _cell_measurement_theta_max 19 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.756 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1804 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 24.91 _reflns_number_total 667 _reflns_number_gt 617 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment riding on their atom bonded _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.23(8) _refine_ls_number_reflns 667 _refine_ls_number_parameters 57 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0479 _refine_ls_wR_factor_gt 0.0474 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.388 _refine_ls_shift/su_mean 0.057 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 Cl1 Cl 0.53383(4) 0.89004(13) 0.94051(5) 0.04671(18) Uani 1 1 d . . . N1 N 0.70244(17) 0.6045(6) 0.62978(19) 0.0402(5) Uani 1 1 d . . . H1 H 0.7152 0.5861 0.5398 0.064(9) Uiso 1 1 d R . . N2 N 0.59922(14) 0.7466(5) 0.68796(17) 0.0404(4) Uani 1 1 d . . . C3 C 0.62993(17) 0.7365(6) 0.8167(2) 0.0326(5) Uani 1 1 d . . . N4 N 0.74242(17) 0.6032(5) 0.84567(18) 0.0380(5) Uani 1 1 d . . . C5 C 0.7845(2) 0.5226(7) 0.7229(2) 0.0408(6) Uani 1 1 d . . . H5 H 0.8616 0.4319 0.7107 0.046(7) Uiso 1 1 d 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 Cl1 0.0427(3) 0.0583(3) 0.0391(3) -0.0047(4) 0.0114(3) 0.0071(2) N1 0.0381(11) 0.0593(14) 0.0234(11) -0.0009(8) 0.0029(8) -0.0012(9) N2 0.0340(9) 0.0577(12) 0.0297(11) 0.0040(9) -0.0024(9) 0.0030(9) C3 0.0319(11) 0.0404(13) 0.0256(11) -0.0005(10) 0.0031(9) -0.0015(9) N4 0.0321(9) 0.0552(13) 0.0266(10) -0.0014(9) 0.0006(8) 0.0038(8) C5 0.0333(14) 0.0599(14) 0.0291(13) 0.0012(11) 0.0012(9) 0.0045(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.706(2) . ? N1 C5 1.316(3) . ? N1 N2 1.367(3) . ? N1 H1 0.9005 . ? N2 C3 1.313(2) . ? C3 N4 1.350(3) . ? N4 C5 1.329(3) . ? C5 H5 0.9109 . ? 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 C5 N1 N2 110.68(18) . . ? C5 N1 H1 124.4 . . ? N2 N1 H1 124.7 . . ? C3 N2 N1 100.76(16) . . ? N2 C3 N4 116.41(17) . . ? N2 C3 Cl1 121.81(15) . . ? N4 C3 Cl1 121.77(15) . . ? C5 N4 C3 101.68(18) . . ? N4 C5 N1 110.47(19) . . ? N4 C5 H5 121.4 . . ? N1 C5 H5 128.1 . . ? 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 C5 N1 N2 C3 -0.1(2) . . . . ? N1 N2 C3 N4 0.2(3) . . . . ? N1 N2 C3 Cl1 179.19(16) . . . . ? N2 C3 N4 C5 -0.2(3) . . . . ? Cl1 C3 N4 C5 -179.24(17) . . . . ? C3 N4 C5 N1 0.2(3) . . . . ? N2 N1 C5 N4 -0.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N4 0.90 1.97 2.865(3) 172.2 4_654 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.91 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.116 _refine_diff_density_min -0.111 _refine_diff_density_rms 0.029