#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/71/2017152.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_2017152
loop_
_publ_author_name
'Castillo, Juan C.'
'Abonía, Rodrigo'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Seven 5-benzylamino-3-tert-butyl-1-phenyl-1H-pyrazoles:
 unexpected isomorphisms, and hydrogen-bonded supramolecular structures
 in zero, one and two dimensions
;
_journal_coeditor_code           SK3324
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o303
_journal_page_last               o310
_journal_paper_doi               10.1107/S0108270109018964
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H22 F3 N3'
_chemical_formula_moiety         'C21 H22 F3 N3'
_chemical_formula_sum            'C21 H22 F3 N3'
_chemical_formula_weight         373.42
_chemical_name_systematic
;
3-tert-butyl-1-phenyl-5-[4-(trifluoromethyl)benzyl]-1H-pyrazole
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.275(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.824(3)
_cell_length_b                   7.3429(11)
_cell_length_c                   24.225(4)
_cell_measurement_reflns_used    4218
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.94
_cell_volume                     3674.4(10)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1508
_diffrn_reflns_av_sigmaI/netI    0.1460
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21869
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.474
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1933
_refine_ls_R_factor_gt           0.0825
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0791P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1961
_reflns_number_gt                2014
_reflns_number_total             4218
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3324.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_original_cell_volume        3674.3(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017152
_cod_database_fobs_code          2017152
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.80598(14) 0.5223(4) 0.26474(12) 0.0208(7) Uani d . 1 . .
N N2 0.84366(14) 0.5000(4) 0.31528(11) 0.0214(7) Uani d . 1 . .
C C3 0.80213(17) 0.4853(4) 0.35142(14) 0.0202(8) Uani d . 1 . .
C C4 0.73816(17) 0.5000(5) 0.32628(14) 0.0224(8) Uani d . 1 . .
H H4 0.6999 0.4927 0.3438 0.027 Uiso calc R 1 . .
C C5 0.74238(17) 0.5270(5) 0.27133(14) 0.0204(8) Uani d . 1 . .
C C11 0.83698(18) 0.5484(4) 0.21710(14) 0.0211(8) Uani d . 1 . .
C C12 0.80881(17) 0.4881(5) 0.16545(14) 0.0231(8) Uani d . 1 . .
H H12 0.7684 0.4266 0.1619 0.028 Uiso calc R 1 . .
C C13 0.83955(19) 0.5176(5) 0.11938(15) 0.0280(9) Uani d . 1 . .
H H13 0.8198 0.4790 0.0838 0.034 Uiso calc R 1 . .
C C14 0.8991(2) 0.6031(5) 0.12449(17) 0.0313(10) Uani d . 1 . .
H H14 0.9202 0.6252 0.0926 0.038 Uiso calc R 1 . .
C C15 0.92733(19) 0.6554(5) 0.17605(17) 0.0296(10) Uani d . 1 . .
H H15 0.9687 0.7120 0.1799 0.036 Uiso calc R 1 . .
C C16 0.89719(18) 0.6278(5) 0.22198(16) 0.0260(9) Uani d . 1 . .
H H16 0.9178 0.6636 0.2576 0.031 Uiso calc R 1 . .
C C31 0.82464(17) 0.4647(5) 0.41273(14) 0.0230(8) Uani d . 1 . .
C C32 0.89773(17) 0.4476(5) 0.42395(15) 0.0264(9) Uani d . 1 . .
H H32A 0.9114 0.3355 0.4069 0.040 Uiso calc R 1 . .
H H32B 0.9111 0.4435 0.4642 0.040 Uiso calc R 1 . .
H H32C 0.9178 0.5527 0.4080 0.040 Uiso calc R 1 . .
C C33 0.80282(19) 0.6331(5) 0.44218(16) 0.0303(10) Uani d . 1 . .
H H33A 0.8228 0.7418 0.4282 0.045 Uiso calc R 1 . .
H H33B 0.8160 0.6219 0.4823 0.045 Uiso calc R 1 . .
H H33C 0.7556 0.6439 0.4349 0.045 Uiso calc R 1 . .
C C34 0.7936(2) 0.2971(5) 0.43503(17) 0.0360(11) Uani d . 1 . .
H H34A 0.7464 0.3087 0.4283 0.054 Uiso calc R 1 . .
H H34B 0.8074 0.2862 0.4751 0.054 Uiso calc R 1 . .
H H34C 0.8070 0.1883 0.4160 0.054 Uiso calc R 1 . .
N N51 0.69471(13) 0.5515(4) 0.22687(12) 0.0229(7) Uani d . 1 . .
H H51 0.7091 0.6275 0.2032 0.027 Uiso d R 1 . .
C C51 0.57982(17) 0.5726(5) 0.19126(14) 0.0197(8) Uani d . 1 . .
C C52 0.52900(18) 0.6943(5) 0.18628(16) 0.0256(9) Uani d . 1 . .
H H52 0.5278 0.7873 0.2134 0.031 Uiso calc R 1 . .
C C53 0.48006(18) 0.6831(5) 0.14272(16) 0.0271(9) Uani d . 1 . .
H H53 0.4444 0.7645 0.1406 0.033 Uiso calc R 1 . .
C C54 0.48295(17) 0.5532(5) 0.10209(15) 0.0230(8) Uani d . 1 . .
C C55 0.53430(17) 0.4343(5) 0.10571(15) 0.0231(8) Uani d . 1 . .
H H55 0.5368 0.3466 0.0772 0.028 Uiso calc R 1 . .
C C56 0.58201(17) 0.4420(5) 0.15044(14) 0.0217(8) Uani d . 1 . .
H H56 0.6167 0.3571 0.1533 0.026 Uiso calc R 1 . .
C C57 0.63008(16) 0.5817(5) 0.24123(14) 0.0207(8) Uani d . 1 . .
H H571 0.6283 0.7027 0.2590 0.025 Uiso calc R 1 . .
H H572 0.6204 0.4886 0.2686 0.025 Uiso calc R 1 . .
C C58 0.43125(19) 0.5515(5) 0.05461(16) 0.0298(9) Uani d . 1 . .
F F1 0.37230(10) 0.5426(4) 0.07037(10) 0.0488(7) Uani d . 1 . .
F F2 0.43146(12) 0.7029(3) 0.02396(10) 0.0433(7) Uani d . 1 . .
F F3 0.43564(11) 0.4136(3) 0.02004(9) 0.0388(6) Uani 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'
F F 0.0171 0.0103 '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
C5 N1 N2 . . 110.7(3) ?
C5 N1 C11 . . 130.6(3) ?
N2 N1 C11 . . 118.5(3) ?
C3 N2 N1 . . 104.7(3) ?
N2 C3 C4 . . 112.1(3) ?
N2 C3 C31 . . 121.1(3) ?
C4 C3 C31 . . 126.7(3) ?
C5 C4 C3 . . 105.2(3) ?
C5 C4 H4 . . 127.4 ?
C3 C4 H4 . . 127.4 ?
N1 C5 C4 . . 107.3(3) ?
N1 C5 N51 . . 121.9(3) ?
C4 C5 N51 . . 130.8(3) ?
C16 C11 C12 . . 119.4(3) ?
C16 C11 N1 . . 119.8(3) ?
C12 C11 N1 . . 120.8(3) ?
C13 C12 C11 . . 119.8(4) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.3(4) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.1(4) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C16 C15 C14 . . 121.1(4) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C11 . . 120.2(4) ?
C15 C16 H16 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
C3 C31 C32 . . 111.4(3) ?
C3 C31 C34 . . 109.7(3) ?
C32 C31 C34 . . 109.3(3) ?
C3 C31 C33 . . 107.8(3) ?
C32 C31 C33 . . 109.6(3) ?
C34 C31 C33 . . 108.9(3) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 C33 H33A . . 109.5 ?
C31 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C31 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C31 C34 H34A . . 109.5 ?
C31 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C31 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C5 N51 C57 . . 115.5(3) ?
C5 N51 H51 . . 108.7 ?
C57 N51 H51 . . 117.6 ?
N51 C57 C51 . . 112.0(3) ?
N51 C57 H571 . . 109.2 ?
C51 C57 H571 . . 109.2 ?
N51 C57 H572 . . 109.2 ?
C51 C57 H572 . . 109.2 ?
H571 C57 H572 . . 107.9 ?
C52 C51 C56 . . 118.8(3) ?
C52 C51 C57 . . 119.5(3) ?
C56 C51 C57 . . 121.7(3) ?
C53 C52 C51 . . 121.0(4) ?
C53 C52 H52 . . 119.5 ?
C51 C52 H52 . . 119.5 ?
C52 C53 C54 . . 119.7(3) ?
C52 C53 H53 . . 120.2 ?
C54 C53 H53 . . 120.2 ?
C55 C54 C53 . . 119.9(3) ?
C55 C54 C58 . . 122.0(3) ?
C53 C54 C58 . . 118.0(3) ?
C54 C55 C56 . . 120.2(3) ?
C54 C55 H55 . . 119.9 ?
C56 C55 H55 . . 119.9 ?
C55 C56 C51 . . 120.4(3) ?
C55 C56 H56 . . 119.8 ?
C51 C56 H56 . . 119.8 ?
F3 C58 F1 . . 106.5(3) ?
F3 C58 F2 . . 106.2(3) ?
F1 C58 F2 . . 105.5(3) ?
F3 C58 C54 . . 113.5(3) ?
F1 C58 C54 . . 112.7(3) ?
F2 C58 C54 . . 111.9(3) ?
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 C5 . 1.354(4) ?
N1 N2 . 1.378(4) ?
N1 C11 . 1.405(4) ?
N2 C3 . 1.311(4) ?
C3 C4 . 1.397(5) ?
C3 C31 . 1.507(5) ?
C4 C5 . 1.360(5) ?
C4 H4 . 0.9500 ?
C5 N51 . 1.381(4) ?
C11 C16 . 1.374(5) ?
C11 C12 . 1.386(5) ?
C12 C13 . 1.372(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.382(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.366(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.360(5) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C31 C32 . 1.517(5) ?
C31 C34 . 1.521(5) ?
C31 C33 . 1.525(5) ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 H33A . 0.9800 ?
C33 H33B . 0.9800 ?
C33 H33C . 0.9800 ?
C34 H34A . 0.9800 ?
C34 H34B . 0.9800 ?
C34 H34C . 0.9800 ?
N51 C57 . 1.449(4) ?
N51 H51 . 0.8797 ?
C57 C51 . 1.498(5) ?
C57 H571 . 0.9900 ?
C57 H572 . 0.9900 ?
C51 C52 . 1.378(5) ?
C51 C56 . 1.382(5) ?
C52 C53 . 1.373(5) ?
C52 H52 . 0.9500 ?
C53 C54 . 1.377(5) ?
C53 H53 . 0.9500 ?
C54 C55 . 1.375(5) ?
C54 C58 . 1.473(5) ?
C55 C56 . 1.375(5) ?
C55 H55 . 0.9500 ?
C56 H56 . 0.9500 ?
C58 F3 . 1.324(4) ?
C58 F1 . 1.332(4) ?
C58 F2 . 1.337(4) ?
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
_geom_hbond_publ_flag
C12 H12 N51 . 0.95 2.51 2.995(5) 112 no
N51 H51 <i>Cg</i>1 4_655 0.88 2.80 3.470(3) 134 no
C53 H53 <i>Cg</i>2 3_455 0.95 2.91 3.809(4) 157 no
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
C5 N1 N2 C3 . . . . 2.1(3) ?
C11 N1 N2 C3 . . . . 177.9(3) ?
N1 N2 C3 C4 . . . . -0.9(4) ?
N1 N2 C3 C31 . . . . -178.0(3) ?
N2 C3 C4 C5 . . . . -0.6(4) ?
C31 C3 C4 C5 . . . . 176.4(3) ?
N2 N1 C5 C4 . . . . -2.5(4) ?
C11 N1 C5 C4 . . . . -177.6(3) ?
N2 N1 C5 N51 . . . . 178.8(3) ?
C11 N1 C5 N51 . . . . 3.7(5) ?
C3 C4 C5 N1 . . . . 1.8(4) ?
C3 C4 C5 N51 . . . . -179.7(3) ?
C5 N1 C11 C16 . . . . 146.7(3) ?
N2 N1 C11 C16 . . . . -28.1(4) ?
C5 N1 C11 C12 . . . . -36.0(5) ?
N2 N1 C11 C12 . . . . 149.2(3) ?
C16 C11 C12 C13 . . . . -3.7(5) ?
N1 C11 C12 C13 . . . . 179.0(3) ?
C11 C12 C13 C14 . . . . 1.6(5) ?
C12 C13 C14 C15 . . . . 0.9(5) ?
C13 C14 C15 C16 . . . . -1.3(6) ?
C14 C15 C16 C11 . . . . -0.9(6) ?
C12 C11 C16 C15 . . . . 3.4(5) ?
N1 C11 C16 C15 . . . . -179.3(3) ?
N2 C3 C31 C32 . . . . -4.9(4) ?
C4 C3 C31 C32 . . . . 178.4(3) ?
N2 C3 C31 C34 . . . . -126.2(3) ?
C4 C3 C31 C34 . . . . 57.2(5) ?
N2 C3 C31 C33 . . . . 115.3(3) ?
C4 C3 C31 C33 . . . . -61.4(4) ?
N1 C5 N51 C57 . . . . -170.8(3) ?
C4 C5 N51 C57 . . . . 10.9(5) ?
C5 N51 C57 C51 . . . . -169.5(3) ?
N51 C57 C51 C52 . . . . -140.2(3) ?
N51 C57 C51 C56 . . . . 41.6(5) ?
C56 C51 C52 C53 . . . . 2.2(5) ?
C57 C51 C52 C53 . . . . -176.1(3) ?
C51 C52 C53 C54 . . . . -2.7(6) ?
C52 C53 C54 C55 . . . . 0.8(6) ?
C52 C53 C54 C58 . . . . -177.0(3) ?
C53 C54 C55 C56 . . . . 1.5(5) ?
C58 C54 C55 C56 . . . . 179.2(3) ?
C54 C55 C56 C51 . . . . -1.9(5) ?
C52 C51 C56 C55 . . . . 0.1(5) ?
C57 C51 C56 C55 . . . . 178.4(3) ?
C55 C54 C58 F3 . . . . 7.1(5) ?
C53 C54 C58 F3 . . . . -175.2(3) ?
C55 C54 C58 F1 . . . . 128.2(4) ?
C53 C54 C58 F1 . . . . -54.1(5) ?
C55 C54 C58 F2 . . . . -113.1(4) ?
C53 C54 C58 F2 . . . . 64.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654166
2 PubChem 139060680
