#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220430.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220430
loop_
_publ_author_name
'Kerscher, Tobias'
'Pust, Philipp'
'Betz, Richard'
'Klüfers, Peter'
'Mayer, Peter'
_publ_section_title
;
 Trispyrazol-1-ylmethane
;
_journal_coeditor_code           BT2828
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o108
_journal_paper_doi               10.1107/S1600536808041767
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H10 N6'
_chemical_formula_moiety         'C10 H10 N6'
_chemical_formula_sum            'C10 H10 N6'
_chemical_formula_weight         214.24
_chemical_name_common            Tris(pyrazolyl)-methane
_chemical_name_systematic
;
Tripyrazol-1-ylmethane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                99.292(8)
_cell_angle_beta                 100.023(9)
_cell_angle_gamma                107.045(9)
_cell_formula_units_Z            2
_cell_length_a                   7.7216(9)
_cell_length_b                   7.8946(6)
_cell_length_c                   9.4143(10)
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.2460
_cell_measurement_theta_min      3.9197
_cell_volume                     526.36(10)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2005)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2005)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2005)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.1155
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4340
_diffrn_reflns_theta_full        26.31
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         3.92
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.829
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.04P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                1054
_reflns_number_total             2117
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2828.cif
_cod_data_source_block           I
_cod_database_code               2220430
_cod_database_fobs_code          2220430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N5 0.36455(16) 0.27051(16) 0.27731(13) 0.0334(3) Uani d . 1 . .
N N1 0.64066(18) 0.38873(17) 0.19270(15) 0.0379(3) Uani d . 1 . .
N N6 0.28341(18) 0.38479(16) 0.33973(14) 0.0409(4) Uani d . 1 . .
N N3 0.63243(17) 0.18619(16) 0.35571(14) 0.0367(3) Uani d . 1 . .
C C10 0.5661(2) 0.32745(19) 0.31338(16) 0.0334(4) Uani d . 1 . .
H H10 0.6125 0.4332 0.4005 0.040 Uiso calc R 1 . .
N N2 0.78449(19) 0.54772(17) 0.22761(17) 0.0539(4) Uani d . 1 . .
N N4 0.6002(2) 0.02927(18) 0.25599(16) 0.0517(4) Uani d . 1 . .
C C7 0.1030(2) 0.2989(2) 0.28350(19) 0.0491(5) Uani d . 1 . .
H H7 0.0086 0.3453 0.3072 0.059 Uiso calc R 1 . .
C C4 0.7280(2) 0.1888(2) 0.49067(19) 0.0489(5) Uani d . 1 . .
H H4 0.7652 0.2845 0.5766 0.059 Uiso calc R 1 . .
C C9 0.2372(2) 0.1197(2) 0.18445(18) 0.0444(4) Uani d . 1 . .
H H9 0.2619 0.0219 0.1283 0.053 Uiso calc R 1 . .
C C8 0.0671(2) 0.1351(2) 0.18683(18) 0.0497(5) Uani d . 1 . .
H H8 -0.0510 0.0511 0.1335 0.060 Uiso calc R 1 . .
C C6 0.6797(3) -0.0647(2) 0.3351(2) 0.0582(5) Uani d . 1 . .
H H6 0.6807 -0.1830 0.2961 0.070 Uiso calc R 1 . .
C C1 0.5986(3) 0.3080(2) 0.0478(2) 0.0535(5) Uani d . 1 . .
H H1 0.5039 0.1956 -0.0004 0.064 Uiso calc R 1 . .
C C2 0.7163(3) 0.4167(3) -0.0163(2) 0.0641(6) Uani d . 1 . .
H H2 0.7215 0.3975 -0.1175 0.077 Uiso calc R 1 . .
C C3 0.8267(3) 0.5611(3) 0.0972(3) 0.0656(6) Uani d . 1 . .
H H3 0.9231 0.6602 0.0842 0.079 Uiso calc R 1 . .
C C5 0.7606(3) 0.0283(3) 0.4800(2) 0.0599(5) Uani d . 1 . .
H H5 0.8254 -0.0117 0.5560 0.072 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N5 N6 . . 111.92(13) ?
C9 N5 C10 . . 130.33(14) ?
N6 N5 C10 . . 117.71(12) ?
C1 N1 N2 . . 112.14(13) ?
C1 N1 C10 . . 130.61(13) ?
N2 N1 C10 . . 117.11(13) ?
C7 N6 N5 . . 103.53(12) ?
C4 N3 N4 . . 112.51(13) ?
C4 N3 C10 . . 126.82(14) ?
N4 N3 C10 . . 120.67(13) ?
N3 C10 N5 . . 111.58(11) ?
N3 C10 N1 . . 111.25(11) ?
N5 C10 N1 . . 111.28(12) ?
N3 C10 H10 . . 107.5 ?
N5 C10 H10 . . 107.5 ?
N1 C10 H10 . . 107.5 ?
C3 N2 N1 . . 102.69(15) ?
C6 N4 N3 . . 102.95(14) ?
N6 C7 C8 . . 112.73(15) ?
N6 C7 H7 . . 123.6 ?
C8 C7 H7 . . 123.6 ?
N3 C4 C5 . . 106.61(16) ?
N3 C4 H4 . . 126.7 ?
C5 C4 H4 . . 126.7 ?
N5 C9 C8 . . 106.78(15) ?
N5 C9 H9 . . 126.6 ?
C8 C9 H9 . . 126.6 ?
C9 C8 C7 . . 105.04(15) ?
C9 C8 H8 . . 127.5 ?
C7 C8 H8 . . 127.5 ?
N4 C6 C5 . . 112.70(17) ?
N4 C6 H6 . . 123.7 ?
C5 C6 H6 . . 123.7 ?
N1 C1 C2 . . 107.29(16) ?
N1 C1 H1 . . 126.4 ?
C2 C1 H1 . . 126.4 ?
C1 C2 C3 . . 104.79(17) ?
C1 C2 H2 . . 127.6 ?
C3 C2 H2 . . 127.6 ?
N2 C3 C2 . . 113.08(16) ?
N2 C3 H3 . . 123.5 ?
C2 C3 H3 . . 123.5 ?
C4 C5 C6 . . 105.23(17) ?
C4 C5 H5 . . 127.4 ?
C6 C5 H5 . . 127.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N5 C9 . 1.3516(18) ?
N5 N6 . 1.3565(15) ?
N5 C10 . 1.4475(18) ?
N1 C1 . 1.348(2) ?
N1 N2 . 1.3562(16) ?
N1 C10 . 1.4486(17) ?
N6 C7 . 1.3243(19) ?
N3 C4 . 1.3473(19) ?
N3 N4 . 1.3566(16) ?
N3 C10 . 1.4397(18) ?
C10 H10 . 1.0000 ?
N2 C3 . 1.336(2) ?
N4 C6 . 1.330(2) ?
C7 C8 . 1.378(2) ?
C7 H7 . 0.9500 ?
C4 C5 . 1.354(2) ?
C4 H4 . 0.9500 ?
C9 C8 . 1.357(2) ?
C9 H9 . 0.9500 ?
C8 H8 . 0.9500 ?
C6 C5 . 1.378(2) ?
C6 H6 . 0.9500 ?
C1 C2 . 1.351(2) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.373(3) ?
C2 H2 . 0.9500 ?
C3 H3 . 0.9500 ?
C5 H5 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C10 H10 N6 2_666 1.00 2.49 3.451(2) 161
C6 H6 N2 1_545 0.95 2.51 3.432(2) 163
C1 H1 N4 2_655 0.95 2.59 3.353(2) 138
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N5 N6 C7 . . . . 0.54(15) ?
C10 N5 N6 C7 . . . . 178.36(12) ?
C4 N3 C10 N5 . . . . -113.15(16) ?
N4 N3 C10 N5 . . . . 66.40(16) ?
C4 N3 C10 N1 . . . . 121.92(15) ?
N4 N3 C10 N1 . . . . -58.53(17) ?
C9 N5 C10 N3 . . . . -51.4(2) ?
N6 N5 C10 N3 . . . . 131.27(13) ?
C9 N5 C10 N1 . . . . 73.53(18) ?
N6 N5 C10 N1 . . . . -103.82(13) ?
C1 N1 C10 N3 . . . . 73.6(2) ?
N2 N1 C10 N3 . . . . -101.77(14) ?
C1 N1 C10 N5 . . . . -51.5(2) ?
N2 N1 C10 N5 . . . . 133.13(13) ?
C1 N1 N2 C3 . . . . 0.65(17) ?
C10 N1 N2 C3 . . . . 176.88(13) ?
C4 N3 N4 C6 . . . . 0.02(16) ?
C10 N3 N4 C6 . . . . -179.60(13) ?
N5 N6 C7 C8 . . . . -0.47(17) ?
N4 N3 C4 C5 . . . . 0.17(17) ?
C10 N3 C4 C5 . . . . 179.76(13) ?
N6 N5 C9 C8 . . . . -0.41(17) ?
C10 N5 C9 C8 . . . . -177.88(13) ?
N5 C9 C8 C7 . . . . 0.10(17) ?
N6 C7 C8 C9 . . . . 0.24(19) ?
N3 N4 C6 C5 . . . . -0.21(18) ?
N2 N1 C1 C2 . . . . -0.57(19) ?
C10 N1 C1 C2 . . . . -176.15(15) ?
N1 C1 C2 C3 . . . . 0.2(2) ?
N1 N2 C3 C2 . . . . -0.5(2) ?
C1 C2 C3 N2 . . . . 0.2(2) ?
N3 C4 C5 C6 . . . . -0.28(18) ?
N4 C6 C5 C4 . . . . 0.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4412315
2 PubChem 5243808
