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#$Date: 2024-08-07 01:04:42 +0300 (Wed, 07 Aug 2024) $
#$Revision: 293991 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023182.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_2023182
loop_
_publ_author_name
'Hayward, Emily R.'
'Zeller, Matthias'
'Mezei, Gellert'
_publ_section_title
;
 Chiral versus achiral crystal structures of
 4-benzyl-1H-pyrazole and its 3,5-di-amino derivative.
;
_journal_coeditor_code           VM2305
_journal_issue                   'Pt 7'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              800
_journal_page_last               805
_journal_paper_doi               10.1107/S2056989024006182
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C10 H10 N2'
_chemical_formula_moiety         'C10 H10 N2'
_chemical_formula_sum            'C10 H10 N2'
_chemical_formula_weight         158.20
_chemical_name_systematic
;
4-Benzyl-1H-pyrazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 101.732(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6651(5)
_cell_length_b                   5.7566(6)
_cell_length_c                   13.2321(9)
_cell_measurement_reflns_used    3320
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.8105
_cell_measurement_theta_min      3.4101
_cell_volume                     422.51(6)
_computing_cell_refinement
;
SAINT V8.40B (Bruker, 2020)
;
_computing_data_collection
;
APEX5 v2023.9-2 (Bruker, 2023)
;
_computing_data_reduction
;
SAINT V8.40B (Bruker, 2020)
;
_computing_molecular_graphics
'CrystalMaker (CrystalMaker Software, 2003)'
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b),
ShelXle Rev1613 (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'HELIOS multilayer Montel optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4021
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.980
_diffrn_reflns_theta_min         3.411
_diffrn_source                   'I-mu-S 3.0 microsource X-ray tube'
_diffrn_source_current           '1.1 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       plate
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.158
_refine_ls_abs_structure_details
;
Flack x determined using 605 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1612
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0320
_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)+(0.0261P)²+0.0328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                1549
_reflns_number_total             1612
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2305.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2023182--2023183.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2023182
_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   0.922
_shelx_estimated_absorpt_t_max   0.949
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.2067(3) 0.1035(3) 0.57682(11) 0.0298(3) Uani d 1 . .
H H1N 0.097(4) -0.009(4) 0.5558(18) 0.045 Uiso d 1 . .
N N2 0.1810(3) 0.3078(3) 0.52511(10) 0.0304(3) Uani d 1 . .
C C1 0.4146(3) 0.0962(3) 0.64801(12) 0.0296(4) Uani d 1 . .
H H1 0.469928 -0.030094 0.692813 0.036 Uiso calc 1 . .
C C2 0.5319(3) 0.3046(3) 0.64400(12) 0.0281(4) Uani d 1 . .
C C3 0.3770(3) 0.4290(3) 0.56670(13) 0.0294(4) Uani d 1 . .
H H3 0.408236 0.582314 0.546294 0.035 Uiso calc 1 . .
C C4 0.7775(3) 0.3749(3) 0.70179(14) 0.0333(4) Uani d 1 . .
H H4A 0.872243 0.428501 0.651089 0.040 Uiso calc 1 . .
H H4B 0.858928 0.235376 0.736236 0.040 Uiso calc 1 . .
C C5 0.7846(3) 0.5626(3) 0.78212(12) 0.0285(4) Uani d 1 . .
C C6 0.9684(3) 0.7272(3) 0.79620(14) 0.0342(4) Uani d 1 . .
H H6 1.083272 0.724351 0.752955 0.041 Uiso calc 1 . .
C C7 0.9862(4) 0.8950(4) 0.87229(15) 0.0413(5) Uani d 1 . .
H H7 1.113464 1.005361 0.881061 0.050 Uiso calc 1 . .
C C8 0.8206(4) 0.9031(4) 0.93542(15) 0.0433(5) Uani d 1 . .
H H8 0.833562 1.017860 0.987870 0.052 Uiso calc 1 . .
C C9 0.6349(3) 0.7423(4) 0.92160(14) 0.0389(5) Uani d 1 . .
H H9 0.518731 0.748123 0.964163 0.047 Uiso calc 1 . .
C C10 0.6177(3) 0.5727(3) 0.84595(13) 0.0329(4) Uani d 1 . .
H H10 0.490632 0.462217 0.837655 0.039 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
C1 N1 N2 . . 111.63(14) ?
C1 N1 H1N . . 130.0(15) ?
N2 N1 H1N . . 118.0(15) ?
C3 N2 N1 . . 104.56(13) ?
N1 C1 C2 . . 107.75(15) ?
N1 C1 H1 . . 126.1 ?
C2 C1 H1 . . 126.1 ?
C1 C2 C3 . . 103.75(15) ?
C1 C2 C4 . . 128.29(16) ?
C3 C2 C4 . . 127.76(17) ?
N2 C3 C2 . . 112.30(15) ?
N2 C3 H3 . . 123.8 ?
C2 C3 H3 . . 123.8 ?
C2 C4 C5 . . 116.15(15) ?
C2 C4 H4A . . 108.2 ?
C5 C4 H4A . . 108.2 ?
C2 C4 H4B . . 108.2 ?
C5 C4 H4B . . 108.2 ?
H4A C4 H4B . . 107.4 ?
C10 C5 C6 . . 118.22(16) ?
C10 C5 C4 . . 122.19(15) ?
C6 C5 C4 . . 119.55(16) ?
C7 C6 C5 . . 120.94(18) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C8 C7 C6 . . 120.44(19) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C9 . . 119.31(18) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
C8 C9 C10 . . 120.38(18) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C9 C10 C5 . . 120.69(17) ?
C9 C10 H10 . . 119.7 ?
C5 C10 H10 . . 119.7 ?
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 C1 . 1.351(2) ?
N1 N2 . 1.353(2) ?
N1 H1N . 0.90(2) ?
N2 C3 . 1.332(2) ?
C1 C2 . 1.378(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.401(2) ?
C2 C4 . 1.500(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.511(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C10 . 1.391(3) ?
C5 C6 . 1.392(2) ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.378(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.385(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.388(3) ?
C9 H9 . 0.9500 ?
C10 H10 . 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
_geom_hbond_publ_flag
N1 H1N N2 2_546 0.90(2) 2.01(2) 2.887(2) 163(2) yes
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
C1 N1 N2 C3 . . . . -0.69(18) ?
N2 N1 C1 C2 . . . . 0.29(19) ?
N1 C1 C2 C3 . . . . 0.21(18) ?
N1 C1 C2 C4 . . . . -174.91(16) ?
N1 N2 C3 C2 . . . . 0.84(18) ?
C1 C2 C3 N2 . . . . -0.67(19) ?
C4 C2 C3 N2 . . . . 174.49(15) ?
C1 C2 C4 C5 . . . . -112.26(19) ?
C3 C2 C4 C5 . . . . 73.7(2) ?
C2 C4 C5 C10 . . . . 39.2(2) ?
C2 C4 C5 C6 . . . . -143.18(17) ?
C10 C5 C6 C7 . . . . 0.6(3) ?
C4 C5 C6 C7 . . . . -177.05(16) ?
C5 C6 C7 C8 . . . . -0.4(3) ?
C6 C7 C8 C9 . . . . -0.4(3) ?
C7 C8 C9 C10 . . . . 0.9(3) ?
C8 C9 C10 C5 . . . . -0.7(3) ?
C6 C5 C10 C9 . . . . -0.1(3) ?
C4 C5 C10 C9 . . . . 177.52(16) ?
