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#$Date: 2023-06-02 11:31:47 +0300 (Fri, 02 Jun 2023) $
#$Revision: 284148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107292.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107292
loop_
_publ_author_name
'Fujisawa, Kiyoshi'
'Ageishi, Keigo'
'Okano, Mitsuki'
'Tiekink, Edward R. T.'
_publ_section_title
;
 The crystal structure of 3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C9H17N3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1055
_journal_page_last               1057
_journal_paper_doi               10.1515/ncrs-2022-0362
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C9 H17 N3'
_chemical_formula_sum            'C9 H17 N3'
_chemical_formula_weight         167.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.564(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5601(3)
_cell_length_b                   9.5210(3)
_cell_length_c                   10.7651(3)
_cell_measurement_reflns_used    7367
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     976.75(5)
_computing_cell_refinement       'CrysAlisPRO [1]'
_computing_data_collection       'CrysAlisPRO [1]'
_computing_data_reduction        'CrysAlisPRO [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SIR2014 [2]'
_diffrn_ambient_temperature      178(2)
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.837
_diffrn_reflns_theta_min         2.860
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPRO [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0617P)²+0.2901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2127
_reflns_number_total             2582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0362_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107292
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.47275(10) 0.17033(10) 0.68661(9) 0.0249(2) Uani 1 1 d D . . . .
H1N H 0.5387(12) 0.1081(12) 0.6726(12) 0.030 Uiso 1 1 d D U . . .
N2 N 0.34837(10) 0.17139(10) 0.61700(9) 0.0273(2) Uani 1 1 d . . . . .
N3 N 0.31020(9) 0.44672(10) 0.84709(8) 0.0222(2) Uani 1 1 d D . . . .
H2N H 0.3173(13) 0.4205(14) 0.9260(8) 0.027 Uiso 1 1 d D U . . .
H3N H 0.2224(10) 0.4731(13) 0.8267(12) 0.027 Uiso 1 1 d D U . . .
C1 C 0.27106(11) 0.27139(12) 0.66664(10) 0.0238(2) Uani 1 1 d . . . . .
C2 C 0.34845(11) 0.33464(10) 0.76847(9) 0.0198(2) Uani 1 1 d . . . . .
C3 C 0.47736(11) 0.26740(11) 0.77825(9) 0.0212(2) Uani 1 1 d . . . . .
C4 C 0.12207(11) 0.29831(14) 0.61499(11) 0.0301(3) Uani 1 1 d . . . . .
H4 H 0.081467 0.372650 0.667019 0.036 Uiso 1 1 calc R U . . .
C5 C 0.03294(14) 0.16496(17) 0.62323(13) 0.0431(3) Uani 1 1 d . . . . .
H5A H 0.070151 0.091008 0.571784 0.065 Uiso 1 1 calc R U . . .
H5B H -0.064370 0.185392 0.593106 0.065 Uiso 1 1 calc R U . . .
H5C H 0.036147 0.133383 0.710054 0.065 Uiso 1 1 calc R U . . .
C6 C 0.11468(14) 0.35035(14) 0.48039(12) 0.0366(3) Uani 1 1 d . . . . .
H6A H 0.170408 0.436328 0.475910 0.055 Uiso 1 1 calc R U . . .
H6B H 0.016829 0.370069 0.451578 0.055 Uiso 1 1 calc R U . . .
H6C H 0.152060 0.278028 0.427345 0.055 Uiso 1 1 calc R U . . .
C7 C 0.60226(11) 0.28694(12) 0.87017(10) 0.0257(2) Uani 1 1 d . . . . .
H7 H 0.581459 0.367367 0.925529 0.031 Uiso 1 1 calc R U . . .
C8 C 0.73342(13) 0.32456(17) 0.80541(13) 0.0414(3) Uani 1 1 d . . . . .
H8A H 0.756801 0.247188 0.750701 0.062 Uiso 1 1 calc R U . . .
H8B H 0.811805 0.340683 0.868127 0.062 Uiso 1 1 calc R U . . .
H8C H 0.715946 0.409972 0.755792 0.062 Uiso 1 1 calc R U . . .
C9 C 0.62567(17) 0.15707(14) 0.95224(13) 0.0421(3) Uani 1 1 d . . . . .
H9A H 0.541606 0.139126 0.996286 0.063 Uiso 1 1 calc R U . . .
H9B H 0.706024 0.172837 1.012992 0.063 Uiso 1 1 calc R U . . .
H9C H 0.644398 0.075841 0.900173 0.063 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 N1 N2 112.06(9) . .
C3 N1 H1N 126.8(9) . .
N2 N1 H1N 121.0(9) . .
C1 N2 N1 105.79(8) . .
C2 N3 H2N 110.8(9) . .
C2 N3 H3N 110.3(9) . .
H2N N3 H3N 108.5(12) . .
N2 C1 C2 109.97(9) . .
N2 C1 C4 120.48(9) . .
C2 C1 C4 129.51(10) . .
C3 C2 C1 105.71(9) . .
C3 C2 N3 124.65(9) . .
C1 C2 N3 129.62(9) . .
N1 C3 C2 106.48(9) . .
N1 C3 C7 123.01(9) . .
C2 C3 C7 130.49(9) . .
C1 C4 C6 112.06(10) . .
C1 C4 C5 110.50(11) . .
C6 C4 C5 109.81(10) . .
C1 C4 H4 108.1 . .
C6 C4 H4 108.1 . .
C5 C4 H4 108.1 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C3 C7 C8 111.58(9) . .
C3 C7 C9 110.71(10) . .
C8 C7 C9 111.53(11) . .
C3 C7 H7 107.6 . .
C8 C7 H7 107.6 . .
C9 C7 H7 107.6 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.3499(13) .
N1 N2 1.3541(13) .
N1 H1N 0.887(8) .
N2 C1 1.3421(14) .
N3 C2 1.4276(13) .
N3 H2N 0.883(8) .
N3 H3N 0.887(8) .
C1 C2 1.4080(14) .
C1 C4 1.5091(15) .
C2 C3 1.3853(14) .
C3 C7 1.5005(14) .
C4 C6 1.5277(18) .
C4 C5 1.5355(19) .
C4 H4 1.0000 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.5250(17) .
C7 C9 1.5258(17) .
C7 H7 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
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
C3 N1 N2 C1 -0.56(13) . . . .
N1 N2 C1 C2 0.38(12) . . . .
N1 N2 C1 C4 -177.64(10) . . . .
N2 C1 C2 C3 -0.08(12) . . . .
C4 C1 C2 C3 177.71(11) . . . .
N2 C1 C2 N3 178.55(10) . . . .
C4 C1 C2 N3 -3.67(19) . . . .
N2 N1 C3 C2 0.52(13) . . . .
N2 N1 C3 C7 179.01(10) . . . .
C1 C2 C3 N1 -0.26(12) . . . .
N3 C2 C3 N1 -178.97(9) . . . .
C1 C2 C3 C7 -178.60(11) . . . .
N3 C2 C3 C7 2.68(18) . . . .
N2 C1 C4 C6 -63.79(15) . . . .
C2 C1 C4 C6 118.63(13) . . . .
N2 C1 C4 C5 59.02(15) . . . .
C2 C1 C4 C5 -118.56(13) . . . .
N1 C3 C7 C8 59.70(15) . . . .
C2 C3 C7 C8 -122.19(13) . . . .
N1 C3 C7 C9 -65.16(14) . . . .
C2 C3 C7 C9 112.95(13) . . . .
