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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/24/1542483.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_1542483
loop_
_publ_author_name
'Cunha, Anna C.'
'Jordão, Alessandro K.'
'de Souza, Maria C. B. V.'
'Ferreira, Vitor F.'
'de Almeida, Maria C. B.'
'Wardell, James L.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 [1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanol
;
_journal_coeditor_code           HB4004
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x152447
_journal_paper_doi               10.1107/S2414314615024475
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C10 H10 Cl2 N4 O'
_chemical_formula_moiety         'C10 H10 Cl2 N4 O'
_chemical_formula_sum            'C10 H10 Cl2 N4 O'
_chemical_formula_weight         273.12
_chemical_name_systematic
'[1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanol'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 112.276(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1802(5)
_cell_length_b                   7.3646(4)
_cell_length_c                   13.9001(8)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1153.82(11)
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_collection
;
COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12461
_diffrn_reflns_theta_full        27.487
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.993
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.767664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.395
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0431
_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)+(0.0528P)²+0.5445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                1963
_reflns_number_total             2645
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4004sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1542483.cif.'
_cod_original_cell_volume        1153.81(11)
_cod_database_code               1542483
_cod_database_fobs_code          1542483
_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   0.870
_shelx_estimated_absorpt_t_max   0.917
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_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
Cl Cl1 0.37932(5) 0.38765(8) 0.87969(5) 0.02943(19) Uani d 1
Cl Cl2 0.68215(5) 0.39438(8) 0.60698(4) 0.02549(18) Uani d 1
O O1 1.07381(14) 0.3879(2) 1.25648(13) 0.0289(4) Uani d 1
H H1O 1.098(2) 0.319(3) 1.3086(16) 0.043 Uiso d 1
N N1 0.78023(15) 0.4396(3) 0.83509(14) 0.0188(4) Uani d 1
H H1N 0.8125(19) 0.503(3) 0.8004(17) 0.023 Uiso d 1
N N2 0.82967(15) 0.4789(2) 0.94015(13) 0.0163(4) Uani d 1
N N3 0.83152(15) 0.6498(2) 0.97786(14) 0.0190(4) Uani d 1
N N4 0.87624(15) 0.6334(2) 1.07929(14) 0.0190(4) Uani d 1
C C1 0.90092(17) 0.4551(3) 1.10644(16) 0.0177(5) Uani d 1
C C2 0.87186(17) 0.3534(3) 1.01696(17) 0.0175(5) Uani d 1
C C3 0.8799(2) 0.1582(3) 0.99578(19) 0.0249(5) Uani d 1
H H3A 0.8016 0.1136 0.9502 0.037 Uiso calc 1
H H3B 0.9070 0.0906 1.0614 0.037 Uiso calc 1
H H3C 0.9364 0.1410 0.9617 0.037 Uiso calc 1
C C4 0.65537(18) 0.4209(3) 0.79153(16) 0.0164(4) Uani d 1
C C5 0.58710(19) 0.4161(3) 0.85238(17) 0.0190(5) Uani d 1
H H5 0.6234 0.4282 0.9258 0.023 Uiso calc 1
C C6 0.46531(19) 0.3934(3) 0.80412(18) 0.0195(5) Uani d 1
C C7 0.40899(19) 0.3747(3) 0.69811(18) 0.0227(5) Uani d 1
H H7 0.3252 0.3615 0.6670 0.027 Uiso calc 1
C C8 0.4772(2) 0.3757(3) 0.63790(18) 0.0231(5) Uani d 1
H H8 0.4404 0.3614 0.5647 0.028 Uiso calc 1
C C9 0.59873(19) 0.3976(3) 0.68423(17) 0.0185(5) Uani d 1
C C10 0.94792(19) 0.3937(3) 1.21697(17) 0.0211(5) Uani d 1
H H10A 0.9215 0.4782 1.2592 0.025 Uiso calc 1
H H10B 0.9164 0.2715 1.2216 0.025 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C10 O1 H1O 109(2)
N2 N1 C4 116.08(16)
N2 N1 H1N 111.5(16)
C4 N1 H1N 117.1(16)
C2 N2 N3 112.40(17)
C2 N2 N1 124.87(18)
N3 N2 N1 122.50(17)
N4 N3 N2 105.56(16)
N3 N4 C1 110.12(17)
N4 C1 C2 108.56(19)
N4 C1 C10 122.24(19)
C2 C1 C10 129.2(2)
N2 C2 C1 103.36(18)
N2 C2 C3 122.65(19)
C1 C2 C3 134.0(2)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C5 C4 C9 118.58(19)
C5 C4 N1 122.34(19)
C9 C4 N1 119.01(18)
C6 C5 C4 119.0(2)
C6 C5 H5 120.5
C4 C5 H5 120.5
C7 C6 C5 122.5(2)
C7 C6 Cl1 118.26(16)
C5 C6 Cl1 119.24(17)
C6 C7 C8 118.48(19)
C6 C7 H7 120.8
C8 C7 H7 120.8
C9 C8 C7 120.1(2)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C4 121.3(2)
C8 C9 Cl2 119.02(17)
C4 C9 Cl2 119.63(16)
O1 C10 C1 110.11(17)
O1 C10 H10A 109.6
C1 C10 H10A 109.6
O1 C10 H10B 109.6
C1 C10 H10B 109.6
H10A C10 H10B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C6 1.742(2)
Cl2 C9 1.736(2)
O1 C10 1.420(3)
O1 H1O 0.839(10)
N1 N2 1.383(2)
N1 C4 1.414(3)
N1 H1N 0.866(10)
N2 C2 1.357(3)
N2 N3 1.361(3)
N3 N4 1.310(3)
N4 C1 1.368(3)
C1 C2 1.378(3)
C1 C10 1.492(3)
C2 C3 1.478(3)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 C5 1.393(3)
C4 C9 1.396(3)
C5 C6 1.387(3)
C5 H5 0.9500
C6 C7 1.376(3)
C7 C8 1.385(3)
C7 H7 0.9500
C8 C9 1.382(3)
C8 H8 0.9500
C10 H10A 0.9900
C10 H10B 0.9900
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 H1N Cl2 . 0.87(2) 2.67(2) 2.9530(19) 100.2(17)
O1 H1O N4 2_747 0.84(2) 2.01(2) 2.836(2) 169(2)
N1 H1N O1 3_767 0.87(2) 2.01(2) 2.848(3) 165(2)
C6 Cl1 Cg1 3_667 1.742(2) 3.7326(12) 5.411(3) 161.12(8)
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
C4 N1 N2 C2 93.4(2)
C4 N1 N2 N3 -80.6(2)
C2 N2 N3 N4 0.6(2)
N1 N2 N3 N4 175.36(16)
N2 N3 N4 C1 -1.0(2)
N3 N4 C1 C2 1.0(2)
N3 N4 C1 C10 -177.30(18)
N3 N2 C2 C1 0.0(2)
N1 N2 C2 C1 -174.61(17)
N3 N2 C2 C3 -179.43(18)
N1 N2 C2 C3 6.0(3)
N4 C1 C2 N2 -0.6(2)
C10 C1 C2 N2 177.57(19)
N4 C1 C2 C3 178.7(2)
C10 C1 C2 C3 -3.1(4)
N2 N1 C4 C5 -8.9(3)
N2 N1 C4 C9 174.27(18)
C9 C4 C5 C6 -1.7(3)
N1 C4 C5 C6 -178.6(2)
C4 C5 C6 C7 0.2(3)
C4 C5 C6 Cl1 -179.89(16)
C5 C6 C7 C8 1.1(3)
Cl1 C6 C7 C8 -178.78(17)
C6 C7 C8 C9 -0.9(3)
C7 C8 C9 C4 -0.7(3)
C7 C8 C9 Cl2 178.92(17)
C5 C4 C9 C8 2.0(3)
N1 C4 C9 C8 178.94(19)
C5 C4 C9 Cl2 -177.60(16)
N1 C4 C9 Cl2 -0.6(3)
N4 C1 C10 O1 -93.2(2)
C2 C1 C10 O1 88.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139048065
