#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/26/2102641.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_2102641
loop_
_publ_author_name
'Sobolev, Alexandre N.'
'White, Allan H.'
_publ_section_title
;
 Temperature dependence of the crystal structure of
 3,5-di-tert-butylpyrazole from 10K
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              621
_journal_page_last               625
_journal_paper_doi               10.1107/S0108768104017380
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C11 H20 N2'
_chemical_formula_sum            'C11 H20 N2'
_chemical_formula_weight         180.29
_chemical_name_common            3,5-di-tert-butylpyrazole
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.356(2)
_cell_length_b                   20.637(4)
_cell_length_c                   9.850(2)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      16.77
_cell_measurement_theta_min      15.99
_cell_volume                     2308.4(8)
_computing_cell_refinement       'Local diffractometer control software'
_computing_data_collection       'Local diffractometer control software'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_molecular_graphics    'SHELXTL (Bruker,1997)'
_computing_publication_material  'SHELXTL (Bruker,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Huber 512 goniometer'
_diffrn_measurement_method       'ω-2θ scan'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2043
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'XTAL 3.7 (Hall, du Boulay & Olthof-Hazekamp, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.038
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.191
_refine_ls_extinction_coef       0.0044(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0634
_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)+(0.0721P)²+0.8688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                1419
_reflns_number_total             2043
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ta5008.cif
_cod_data_source_block           120k
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2102641
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'
loop_
_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
_atom_site_type_symbol
N1 0.40361(16) 0.04686(10) 0.45044(18) 0.0281(5) Uani d . 1 . . N
H1 0.423(2) 0.0043(14) 0.427(3) 0.051(8) Uiso d . 1 . . H
N2 0.47649(16) 0.07557(9) 0.54291(18) 0.0285(5) Uani d . 1 . . N
C3 0.4297(2) 0.13456(11) 0.5618(2) 0.0289(6) Uani d . 1 . . C
C31 0.4888(2) 0.18188(12) 0.6582(2) 0.0339(6) Uani d . 1 . . C
C32 0.4166(2) 0.24437(13) 0.6679(3) 0.0455(7) Uani d . 1 . . C
H31 0.3337(14) 0.2337(2) 0.6992(18) 0.068 Uiso calc R 1 . . H
H32 0.4132(13) 0.2659(6) 0.5754(15) 0.068 Uiso calc R 1 . . H
H33 0.4550(11) 0.2749(6) 0.7354(17) 0.068 Uiso calc R 1 . . H
C33 0.4977(3) 0.15159(15) 0.7997(3) 0.0600(9) Uani d . 1 . . C
H34 0.4152(14) 0.1400(9) 0.8337(11) 0.090 Uiso calc R 1 . . H
H35 0.5358(18) 0.1840(7) 0.8649(13) 0.090 Uiso calc R 1 . . H
H36 0.5480(18) 0.1105(9) 0.7949(5) 0.090 Uiso calc R 1 . . H
C34 0.6125(2) 0.19827(13) 0.6054(3) 0.0473(8) Uani d . 1 . . C
H37 0.6061(3) 0.2182(9) 0.5102(17) 0.071 Uiso calc R 1 . . H
H38 0.6621(9) 0.1568(7) 0.6009(17) 0.071 Uiso calc R 1 . . H
H39 0.6518(9) 0.2308(8) 0.6697(14) 0.071 Uiso calc R 1 . . H
C4 0.3292(2) 0.14253(11) 0.4817(2) 0.0315(6) Uani d . 1 . . C
H4 0.2806 0.1799 0.4765 0.038 Uiso calc R 1 . . H
C5 0.3146(2) 0.08515(11) 0.4114(2) 0.0291(6) Uani d . 1 A . C
C51 0.2233(2) 0.06334(12) 0.3090(2) 0.0345(6) Uani d . 1 . . C
C52 0.2482(5) -0.0090(2) 0.2657(5) 0.0561(13) Uani d P 0.67 A 1 C
H51 0.331(3) -0.0121(4) 0.222(3) 0.084 Uiso calc PR 0.67 A 1 H
H52 0.185(2) -0.0239(7) 0.196(3) 0.084 Uiso calc PR 0.67 A 1 H
H53 0.245(3) -0.0387(9) 0.351(2) 0.084 Uiso calc PR 0.67 A 1 H
C53 0.1025(4) 0.0669(3) 0.3730(5) 0.0678(16) Uani d P 0.67 A 1 C
H54 0.0989(11) 0.0362(15) 0.454(3) 0.102 Uiso calc PR 0.67 A 1 H
H55 0.0403(19) 0.0536(18) 0.303(2) 0.102 Uiso calc PR 0.67 A 1 H
H56 0.0865(15) 0.1132(15) 0.405(3) 0.102 Uiso calc PR 0.67 A 1 H
C54 0.2313(5) 0.1043(2) 0.1842(4) 0.0543(12) Uani d P 0.67 A 1 C
H57 0.3129(9) 0.0981(4) 0.1396(8) 0.081 Uiso calc PR 0.67 A 1 H
H58 0.2202(8) 0.1525(3) 0.2102(4) 0.081 Uiso calc PR 0.67 A 1 H
H59 0.1661(7) 0.0907(3) 0.1165(7) 0.081 Uiso calc PR 0.67 A 1 H
C52' 0.1272(8) 0.1217(3) 0.2928(7) 0.053(2) Uani d PR 0.33 A 2 C
H51' 0.0971(10) 0.1322(3) 0.3770(11) 0.080 Uiso calc PR 0.33 A 2 H
H52' 0.0668(9) 0.1082(4) 0.2367(6) 0.080 Uiso calc PR 0.33 A 2 H
H53' 0.1634(8) 0.1576(3) 0.2554(5) 0.080 Uiso calc PR 0.33 A 2 H
C53' 0.2803(8) 0.0602(6) 0.1691(9) 0.064(3) Uani d P 0.33 A 2 C
H54' 0.344(6) 0.028(3) 0.170(2) 0.095 Uiso calc PR 0.33 A 2 H
H55' 0.313(6) 0.103(3) 0.146(3) 0.095 Uiso calc PR 0.33 A 2 H
H56' 0.221(4) 0.048(3) 0.101(4) 0.095 Uiso calc PR 0.33 A 2 H
C54' 0.1618(10) 0.0049(5) 0.3503(12) 0.067(4) Uani d P 0.33 A 2 C
H57' 0.211(4) -0.026(3) 0.361(9) 0.100 Uiso calc PR 0.33 A 2 H
H58' 0.112(7) -0.006(3) 0.289(6) 0.100 Uiso calc PR 0.33 A 2 H
H59' 0.126(7) 0.0118(15) 0.425(7) 0.100 Uiso calc PR 0.33 A 2 H
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
C5 N1 N2 113.12(19)
C3 N2 N1 104.27(18)
N2 C3 C4 110.6(2)
N2 C3 C31 119.7(2)
C4 C3 C31 129.7(2)
C3 C31 C32 110.1(2)
C3 C31 C33 109.6(2)
C3 C31 C34 109.5(2)
C32 C31 C33 108.8(2)
C32 C31 C34 109.0(2)
C33 C31 C34 109.7(2)
C3 C4 C5 106.3(2)
N1 C5 C4 105.75(19)
N1 C5 C51 122.2(2)
C4 C5 C51 132.1(2)
C5 C51 C52 109.8(2)
C5 C51 C53 109.2(2)
C5 C51 C54 109.8(2)
C52 C51 C53 108.7(4)
C52 C51 C54 107.6(3)
C53 C51 C54 111.8(3)
C5 C51 C52' 107.7(3)
C5 C51 C53' 108.9(4)
C5 C51 C54' 112.9(4)
C52' C51 C53' 103.1(5)
C52' C51 C54' 108.6(6)
C53' C51 C54' 115.0(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.366(3)
N1 C5 1.339(3)
N2 C3 1.341(3)
C3 C4 1.398(3)
C3 C31 1.518(3)
C31 C32 1.531(3)
C31 C33 1.531(3)
C31 C34 1.536(4)
C4 C5 1.382(3)
C5 C51 1.515(3)
C51 C52 1.578(5)
C51 C53 1.512(5)
C51 C54 1.494(4)
C51 C52' 1.633(7)
C51 C54' 1.451(9)
C51 C53' 1.524(9)
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
N1 H1 N2 5_656 0.94(3) 2.03(3) 2.871(3) 149(2)
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
C5 N1 N2 C3 0.1(2)
N1 N2 C3 C31 -179.08(18)
N1 N2 C3 C4 -0.2(2)
N2 C3 C31 C32 -177.4(2)
N2 C3 C31 C33 -57.7(3)
N2 C3 C31 C34 62.7(3)
C4 C3 C31 C32 4.0(3)
C4 C3 C31 C33 123.7(3)
C4 C3 C31 C34 -115.9(3)
N2 C3 C4 C5 0.3(3)
C31 C3 C4 C5 179.0(2)
N2 N1 C5 C4 0.1(3)
N2 N1 C5 C51 179.71(19)
C3 C4 C5 N1 -0.2(2)
C3 C4 C5 C51 -179.8(2)
N1 C5 C51 C52 2.5(4)
N1 C5 C51 C53 121.6(3)
N1 C5 C51 C54 -115.6(3)
C4 C5 C51 C52 -178.0(3)
C4 C5 C51 C53 -58.9(4)
C4 C5 C51 C54 63.9(4)
N1 C5 C51 C52' 177.7(3)
N1 C5 C51 C53' -71.1(6)
N1 C5 C51 C54' 57.9(6)
C4 C5 C51 C52' -2.8(4)
C4 C5 C51 C53' 108.4(6)
C4 C5 C51 C54' -122.6(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136912
