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(1991) A47, 655-685. # # # ############################################################################ data_2949 ############################################################################ # # _publ_requested_journal 'Physical Chemistry Chemical Physics' _publ_section_title ; The Structure of N-Aminopyrazole in the Solid State and in Solution: An Experimental and Computational Study ; loop_ _publ_author_name _publ_author_address 'Jos\'e Antonio Jim\'enez' ; Departamento de Qu\'imica Org\'anica y Biolog\'ia Facultad de Ciencias UNED Senda del Rey 9 E-28040 Madrid Spain ; 'Rosa Mar\'ia Claramunt' ; Departamento de Qu\'imica Org\'anica y Biolog\'ia Facultad de Ciencias UNED Senda del Rey 9 E-28040 Madrid Spain ; 'Otilia M\'o' ; Departamento de Qu\'imica Facultad de Ciencias C-9 Universidad Aut\'onoma de Madrid E-28040 Cantoblanco (Madrid) Spain ; 'Manuel Y\'a\~nez' ; Departamento de Qu\'imica C-9 Facultad de Ciencias Universidad Aut\'onoma de Madrid E-28040 Cantoblanco (Madrid) Spain ; 'Frank Wehrmann' ; Institut f\"ur Chemie Freie Universit\"at Berlin Takustrasse 3 D-14195 Berlin Germany ; 'Gerd Buntkowsky' ; Institut f\"ur Chemie Freie Universit\"at Berlin Takustrasse 3 D-14195 Berlin Germany ; 'Hans-Heinrich Limbach' ; Institut f\"ur Chemie Freie Universit\"at Berlin Takustrasse 3 D-14195 Berlin Germany ; 'Richard Goddard' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Jos\'e Elguero' ; Instituto de Qu\'imica M\'edica CSIC Juan de la Cierva 3 E-28006 Madrid Spain ; loop_ _publ_contact_author_name _publ_contact_author_address 'Richard Goddard' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; # # ############################################################################ _chemical_name_systematic ; 1-aminopyrazole ; _chemical_name_common N-aminopyrazole _chemical_formula_sum 'C3 H5 N3' _chemical_formula_weight 83.10 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c n' _symmetry_Int_Tables_number 56 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 10.468(7) _cell_length_b 13.484(3) _cell_length_c 5.7549(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 812.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 23.17 _cell_measurement_theta_max 27.07 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method none _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_special_details ; The crystal was grown by zone crystallization directly on the diffractometer in a 0.5 mm diameter glass capillary (glass No. 50, Hilgenberg) under argon. ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w-2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_time 30 _diffrn_standards_decay_% 13.04 _diffrn_reflns_number 3420 _diffrn_reflns_av_R_equivalents 0.1166 _diffrn_reflns_av_sigmaI/netI 0.0782 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.50 _reflns_number_total 935 _reflns_number_gt 797 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'EXPRESS / CAD4 software (Enraf-Nonius, 1995)' _computing_cell_refinement 'EXPRESS / CAD4 software (Enraf-Nonius, 1995)' _computing_data_reduction 'DATAP (Coppens,Leiserowitz & Rabinovich, 1965)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _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 w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.1663P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.069(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 935 _refine_ls_number_parameters 76 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_obs 0.1327 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.55609(13) 0.07629(9) -0.7266(2) 0.0202(4) Uani 1 d . . . H1 H -0.5731(17) 0.0386(14) -0.869(3) 0.032(5) Uiso 1 d . . . C2 C -0.63151(15) 0.10208(10) -0.5393(2) 0.0228(4) Uani 1 d . . . H2 H -0.720(2) 0.0841(13) -0.512(3) 0.026(4) Uiso 1 d . . . C3 C -0.55274(14) 0.16226(10) -0.4017(2) 0.0206(4) Uani 1 d . . . H3 H -0.5722(19) 0.1977(16) -0.265(4) 0.040(6) Uiso 1 d . . . N1 N -0.43711(12) 0.17411(8) -0.49574(18) 0.0196(4) Uani 1 d . . . N2 N -0.44277(11) 0.12023(7) -0.6943(2) 0.0172(4) Uani 1 d . . . N3 N -0.34097(12) 0.11751(8) -0.8528(2) 0.0213(4) Uani 1 d . . . H3A H -0.269(2) 0.1085(15) -0.784(4) 0.038(5) Uiso 1 d . . . H3B H -0.3345(17) 0.1827(14) -0.917(4) 0.031(5) Uiso 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 C1 0.0254(8) 0.0203(6) 0.0149(7) -0.0020(5) -0.0021(5) -0.0012(5) C2 0.0261(8) 0.0245(6) 0.0177(7) 0.0001(5) 0.0022(5) -0.0024(5) C3 0.0300(8) 0.0208(6) 0.0110(7) -0.0007(5) 0.0020(5) 0.0001(5) N1 0.0298(8) 0.0188(6) 0.0102(6) -0.0023(4) -0.0015(4) -0.0004(4) N2 0.0234(7) 0.0175(6) 0.0105(6) -0.0015(4) 0.0003(4) 0.0008(4) N3 0.0238(7) 0.0237(6) 0.0163(6) -0.0017(4) 0.0036(5) 0.0011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.3389(19) . y C1 C2 1.380(2) . y C2 C3 1.402(2) . y C3 N1 1.335(2) . y N1 N2 1.3552(15) . y N2 N3 1.4032(17) . y 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 N2 C1 C2 106.67(12) . . y C1 C2 C3 104.50(13) . . y N1 C3 C2 111.93(12) . . y C3 N1 N2 103.75(11) . . y C1 N2 N1 113.15(11) . . y C1 N2 N3 124.82(12) . . y N1 N2 N3 121.92(11) . . y _diffrn_measured_fraction_theta_max 0.836 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.836 _refine_diff_density_max 0.439 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.093