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#$Date: 2022-09-03 04:01:47 +0200 (Sat 03 de Sep de 2022) $
#$Revision: 277611 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/26/2022660.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_2022660
loop_
_publ_author_name
'van Terwingen, Steven'
'Englert, Ulli'
_publ_section_title
;
 Trimethylpyrazole: a simple heterocycle reflecting Kitaigorodskii's
 packing principle
;
_journal_coeditor_code           DJ2050
_journal_issue                   10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S205698902200860X
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C6 H10 N2'
_chemical_formula_moiety         'C6 H10 N2'
_chemical_formula_sum            'C6 H10 N2'
_chemical_formula_weight         110.16
_chemical_name_common            'Compound 1 (s20_07)'
_chemical_name_systematic
;
1,3,5-Trimethyl-1H-pyrazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/2
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.205(19)
_cell_length_b                   6.687(11)
_cell_length_c                   8.373(15)
_cell_measurement_reflns_used    263
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.70
_cell_measurement_theta_min      3.04
_cell_volume                     627.4(19)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al., 2020)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1377
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6665
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.845
_diffrn_reflns_theta_min         3.037
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.232
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2019/2 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     50
_refine_ls_number_reflns         648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0467
_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)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                366
_reflns_number_total             648
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2050sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        627.3(19)
_cod_database_code               2022660
_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   0.985
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4912(2) 0.250000 0.6988(3) 0.0289(7) Uani d 1 . .
N N2 0.5279(2) 0.250000 0.5442(3) 0.0249(6) Uani d 1 . .
C C1 0.6481(3) 0.250000 0.5301(4) 0.0236(7) Uani d 1 . .
C C2 0.6912(3) 0.250000 0.6820(3) 0.0260(8) Uani d 1 . .
H H2 0.772711 0.250000 0.713077 0.031 Uiso calc 1 . .
C C3 0.5924(3) 0.250000 0.7829(4) 0.0265(7) Uani d 1 . .
C C4 0.4409(3) 0.250000 0.4164(3) 0.0327(9) Uani d 1 . .
H H4A 0.360267 0.250000 0.461847 0.049 Uiso d 1 . .
H H4B 0.451701 0.130335 0.350369 0.049 Uiso d 1 . .
C C5 0.7079(3) 0.250000 0.3728(4) 0.0342(8) Uani d 1 . .
H H5A 0.794608 0.250000 0.388049 0.051 Uiso d 1 . .
H H5B 0.684366 0.369665 0.312985 0.051 Uiso d 1 . .
C C6 0.5878(3) 0.250000 0.9617(4) 0.0380(9) Uani d 1 . .
H H6A 0.504403 0.250000 0.996905 0.057 Uiso d 1 . .
H H6B 0.628021 0.369665 1.002625 0.057 Uiso d 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
C3 N1 N2 . . 104.2(3) ?
C1 N2 N1 . . 112.7(2) ?
C1 N2 C4 . . 127.3(3) ?
N1 N2 C4 . . 120.0(3) ?
N2 C1 C2 . . 105.8(3) ?
N2 C1 C5 . . 122.0(3) ?
C2 C1 C5 . . 132.2(3) ?
C1 C2 C3 . . 106.6(3) ?
C1 C2 H2 . . 126.7 ?
C3 C2 H2 . . 126.7 ?
N1 C3 C2 . . 110.8(3) ?
N1 C3 C6 . . 119.9(3) ?
C2 C3 C6 . . 129.4(3) ?
N2 C4 H4A . . 109.5 ?
N2 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N2 C4 H4B . 7_565 109.47(10) ?
H4A C4 H4B . 7_565 109.5 ?
H4B C4 H4B . 7_565 109.5 ?
C1 C5 H5A . . 109.5 ?
C1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C1 C5 H5B . 7_565 109.47(11) ?
H5A C5 H5B . 7_565 109.5 ?
H5B C5 H5B . 7_565 109.5 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6B . 7_565 109.47(10) ?
H6A C6 H6B . 7_565 109.5 ?
H6B C6 H6B . 7_565 109.5 ?
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
N1 C3 . 1.336(4) ?
N1 N2 . 1.358(4) ?
N2 C1 . 1.351(4) ?
N2 C4 . 1.448(4) ?
C1 C2 . 1.360(5) ?
C1 C5 . 1.478(4) ?
C2 C3 . 1.392(4) ?
C2 H2 . 0.9500 ?
C3 C6 . 1.498(5) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4B 7_565 0.9800 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5B 7_565 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6B 7_565 0.9800 ?

_cod_database_fobs_code 2022660
