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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102753.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_8102753
loop_
_publ_author_name
'Pascale Lemoine'
'Bernard Viossat'
'Pascal Retailleau'
'Jean Daniel Brion'
'Alain Bekaert'
_publ_section_title
;
 Crystal structure of 3,4-dihydroxy-1,5-dimethyl-2-phenylpyrazolium
 chloride, [C11H13N2O2]Cl
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              689
_journal_volume                  225
_journal_year                    2010
_chemical_formula_moiety         'C11 H13 N2 O2, Cl'
_chemical_formula_sum            'C11 H13 Cl N2 O2'
_chemical_formula_weight         240.68
_chemical_name_systematic
; 
1,5-dihydro-3,4-dihydroxy-1,5-dimethyl-2-phenyl-pyrazol chloride 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                71.80(2)
_cell_angle_beta                 84.05(5)
_cell_angle_gamma                87.47(5)
_cell_formula_units_Z            2
_cell_length_a                   7.150(5)
_cell_length_b                   8.380(2)
_cell_length_c                   10.586(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.49
_cell_measurement_theta_min      2.03
_cell_volume                     599.3(5)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'WinGX - version 1.63.02 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92(Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf-nonius CAD4'
_diffrn_measurement_method       'ω - 2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3691
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0488
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1755
_reflns_number_gt                1804
_reflns_number_total             3471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3048.cff
_cod_data_source_block           shelxl
_cod_database_code               8102753
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.71788(10) 0.39960(8) 0.18326(5) 0.0732(2) Uani 1 1 d . . .
O1 O 0.7266(3) 0.2350(2) 0.46977(17) 0.0718(5) Uani 1 1 d . . .
H1 H 0.745(5) 0.281(5) 0.385(4) 0.116(12) Uiso 1 1 d . . .
N1 N 0.7612(2) 0.31114(19) 0.65575(16) 0.0500(4) Uani 1 1 d . . .
C1 C 0.7631(3) 0.1448(2) 0.74909(17) 0.0494(5) Uani 1 1 d . . .
O2 O 0.7241(3) 0.62920(19) 0.34830(15) 0.0669(5) Uani 1 1 d . . .
H2 H 0.710(4) 0.555(4) 0.296(3) 0.093(9) Uiso 1 1 d . . .
N2 N 0.7741(3) 0.4542(2) 0.68963(17) 0.0521(4) Uani 1 1 d . . .
C2 C 0.9312(4) 0.0741(3) 0.7892(3) 0.0724(7) Uani 1 1 d . . .
H20 H 1.0432 0.1312 0.7560 0.087 Uiso 1 1 calc R . .
C3 C 0.9296(6) -0.0857(4) 0.8810(3) 0.0929(10) Uani 1 1 d . . .
H3 H 1.0420 -0.1360 0.9111 0.112 Uiso 1 1 calc R . .
C4 C 0.7670(6) -0.1691(3) 0.9271(2) 0.0911(11) Uani 1 1 d . . .
H4 H 0.7683 -0.2761 0.9889 0.109 Uiso 1 1 calc R . .
C5 C 0.5999(6) -0.0973(4) 0.8837(3) 0.0947(10) Uani 1 1 d . . .
H5 H 0.4889 -0.1567 0.9148 0.114 Uiso 1 1 calc R . .
C6 C 0.5954(4) 0.0630(3) 0.7939(2) 0.0699(6) Uani 1 1 d . . .
H6 H 0.4826 0.1137 0.7650 0.084 Uiso 1 1 calc R . .
C7 C 0.7412(3) 0.3547(2) 0.52415(18) 0.0477(4) Uani 1 1 d . . .
C8 C 0.7413(3) 0.5292(2) 0.47462(19) 0.0461(4) Uani 1 1 d . . .
C9 C 0.7603(3) 0.5867(2) 0.5804(2) 0.0502(5) Uani 1 1 d . . .
C10 C 0.7658(4) 0.7640(3) 0.5811(3) 0.0705(6) Uani 1 1 d . . .
H10A H 0.7714 0.7657 0.6709 0.106 Uiso 1 1 calc R . .
H10B H 0.6546 0.8228 0.5466 0.106 Uiso 1 1 calc R . .
H10C H 0.8748 0.8177 0.5262 0.106 Uiso 1 1 calc R . .
C11 C 0.7788(4) 0.4506(3) 0.8284(2) 0.0642(6) Uani 1 1 d . . .
H11A H 0.7736 0.3363 0.8856 0.096 Uiso 1 1 calc R . .
H11B H 0.6729 0.5125 0.8532 0.096 Uiso 1 1 calc R . .
H11C H 0.8930 0.5005 0.8372 0.096 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 106(3) . . ?
C7 N1 N2 108.45(16) . . ?
C7 N1 C1 127.45(16) . . ?
N2 N1 C1 124.08(15) . . ?
C2 C1 C6 122.7(2) . . ?
C2 C1 N1 118.8(2) . . ?
C6 C1 N1 118.5(2) . . ?
C8 O2 H2 107(2) . . ?
C9 N2 N1 108.65(15) . . ?
C9 N2 C11 128.97(18) . . ?
N1 N2 C11 121.98(17) . . ?
C1 C2 C3 117.9(3) . . ?
C1 C2 H20 121.1 . . ?
C3 C2 H20 121.1 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
O1 C7 N1 118.68(17) . . ?
O1 C7 C8 133.73(18) . . ?
N1 C7 C8 107.60(18) . . ?
O2 C8 C9 124.43(18) . . ?
O2 C8 C7 128.74(19) . . ?
C9 C8 C7 106.83(17) . . ?
N2 C9 C8 108.47(18) . . ?
N2 C9 C10 123.29(19) . . ?
C8 C9 C10 128.2(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.316(2) . ?
O1 H1 0.85(4) . ?
N1 C7 1.347(2) . ?
N1 N2 1.364(2) . ?
N1 C1 1.436(2) . ?
C1 C2 1.364(3) . ?
C1 C6 1.373(3) . ?
O2 C8 1.353(2) . ?
O2 H2 0.97(3) . ?
N2 C9 1.338(3) . ?
N2 C11 1.463(3) . ?
C2 C3 1.387(4) . ?
C2 H20 0.9300 . ?
C3 C4 1.349(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.391(3) . ?
C8 C9 1.371(3) . ?
C9 C10 1.490(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl1 0.85(4) 2.08(4) 2.9195(19) 166(3) .
O2 H2 Cl1 0.97(3) 2.02(4) 2.980(2) 172(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653991
2 PubChem 139207294
