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#$Date: 2025-01-23 04:17:41 +0200 (Thu, 23 Jan 2025) $
#$Revision: 297434 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/98/7249825.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_7249825
loop_
_publ_author_name
'Cifuentes, Carlos'
'Bravo, Nestor'
'Restrepo, Daniel'
'Macías, Mario'
'Portilla, Jaime'
_publ_section_title
;
 Isomerization of pirazolopyrimidines to pyrazolopyridines by
 ring-opening/closing reaction in aqueous NaOH
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              2078
_journal_page_last               2085
_journal_paper_doi               10.1039/D4RA06345G
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C14 H10 Cl N3 O'
_chemical_formula_sum            'C14 H10 Cl N3 O'
_chemical_formula_weight         271.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-27 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                89.961(7)
_cell_angle_beta                 81.987(6)
_cell_angle_gamma                79.955(7)
_cell_formula_units_Z            2
_cell_length_a                   6.1624(4)
_cell_length_b                   9.2368(9)
_cell_length_c                   11.2678(9)
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.0580
_cell_measurement_theta_min      3.8120
_cell_volume                     625.19(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6224
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.324
_diffrn_reflns_theta_min         3.963
_diffrn_source
'SuperNova (Cu) micro-focus sealed X-ray Source'
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0469
_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)+(0.0763P)²+0.1270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2295
_reflns_number_total             2574
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra06345g2.cif
_cod_data_source_block           Compound_2b
_cod_database_code               7249825
_shelx_shelxl_version_number     2018/3
_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   0.605
_shelx_estimated_absorpt_t_max   0.646
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl19 Cl -0.23795(9) 0.49140(6) 0.75937(4) 0.0663(2) Uani 1 1 d . . . . .
N5 N 0.4266(2) -0.25968(17) -0.02682(13) 0.0482(4) Uani 1 1 d . . . . .
N6 N 0.2477(2) -0.14743(17) -0.00246(13) 0.0470(3) Uani 1 1 d . . . . .
H6 H 0.138397 -0.131362 -0.043391 0.056 Uiso 1 1 calc R U . . .
N8 N 0.1193(2) 0.05279(17) 0.14056(13) 0.0453(3) Uani 1 1 d . . . . .
C1 C 0.3762(3) 0.06335(18) 0.28461(14) 0.0414(3) Uani 1 1 d . . . . .
O11 O 0.6351(2) 0.1370(2) 0.39545(17) 0.0799(6) Uani 1 1 d . . . . .
C3 C 0.4654(3) -0.12744(18) 0.13529(14) 0.0395(3) Uani 1 1 d . . . . .
C2 C 0.5239(3) -0.05857(19) 0.23266(14) 0.0416(3) Uani 1 1 d . . . . .
H2 H 0.656862 -0.092686 0.261997 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0586(3) 0.19166(19) 0.50842(16) 0.0459(4) Uani 1 1 d . . . . .
H14 H 0.021212 0.112693 0.469468 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2647(3) -0.06552(18) 0.09369(14) 0.0396(3) Uani 1 1 d . . . . .
C13 C 0.2660(3) 0.23059(18) 0.47593(14) 0.0414(3) Uani 1 1 d . . . . .
C9 C 0.1781(3) 0.11327(19) 0.23589(15) 0.0443(4) Uani 1 1 d . . . . .
H9 H 0.081521 0.194278 0.273045 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4399(3) 0.1439(2) 0.38536(16) 0.0477(4) Uani 1 1 d . . . . .
C4 C 0.5569(3) -0.2495(2) 0.05524(14) 0.0445(4) Uani 1 1 d . . . . .
C17 C 0.1633(3) 0.4323(2) 0.62121(16) 0.0494(4) Uani 1 1 d . . . . .
H17 H 0.197067 0.513861 0.658282 0.059 Uiso 1 1 calc R U . . .
C15 C -0.0929(3) 0.2691(2) 0.59808(16) 0.0498(4) Uani 1 1 d . . . . .
H15 H -0.229081 0.239900 0.621776 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3167(3) 0.3511(2) 0.53407(16) 0.0457(4) Uani 1 1 d . . . . .
H18 H 0.455951 0.377286 0.513950 0.055 Uiso 1 1 calc R U . . .
C16 C -0.0411(3) 0.3898(2) 0.65210(15) 0.0473(4) Uani 1 1 d . . . . .
C12 C 0.7660(3) -0.3569(3) 0.05766(19) 0.0613(5) Uani 1 1 d . . . . .
H12A H 0.842387 -0.375873 -0.022520 0.092 Uiso 1 1 calc R U . . .
H12B H 0.731080 -0.446924 0.091337 0.092 Uiso 1 1 calc R U . . .
H12C H 0.859528 -0.317116 0.105730 0.092 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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
C4 N5 N6 106.61(14) . . ?
C7 N6 N5 111.49(13) . . ?
C7 N6 H6 124.3 . . ?
N5 N6 H6 124.3 . . ?
C9 N8 C7 114.04(13) . . ?
C2 C1 C9 119.47(14) . . ?
C2 C1 C10 118.60(14) . . ?
C9 C1 C10 121.79(15) . . ?
C2 C3 C7 117.66(15) . . ?
C2 C3 C4 137.91(15) . . ?
C7 C3 C4 104.39(14) . . ?
C3 C2 C1 117.48(14) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C15 C14 C13 120.63(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N8 C7 N6 126.65(14) . . ?
N8 C7 C3 126.52(14) . . ?
N6 C7 C3 106.84(14) . . ?
C14 C13 C18 118.63(16) . . ?
C14 C13 C10 122.31(15) . . ?
C18 C13 C10 118.99(15) . . ?
N8 C9 C1 124.80(15) . . ?
N8 C9 H9 117.6 . . ?
C1 C9 H9 117.6 . . ?
O11 C10 C1 119.87(16) . . ?
O11 C10 C13 119.40(16) . . ?
C1 C10 C13 120.71(14) . . ?
N5 C4 C3 110.67(15) . . ?
N5 C4 C12 121.24(16) . . ?
C3 C4 C12 128.09(16) . . ?
C16 C17 C18 118.71(16) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C16 C15 C14 119.62(17) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C18 C13 121.15(16) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C15 C16 C17 121.20(17) . . ?
C15 C16 Cl19 119.18(14) . . ?
C17 C16 Cl19 119.61(14) . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
Cl19 C16 1.7347(18) . ?
N5 C4 1.320(2) . ?
N5 N6 1.373(2) . ?
N6 C7 1.348(2) . ?
N6 H6 0.8600 . ?
N8 C9 1.333(2) . ?
N8 C7 1.343(2) . ?
C1 C2 1.391(2) . ?
C1 C9 1.412(2) . ?
C1 C10 1.491(2) . ?
O11 C10 1.215(2) . ?
C3 C2 1.389(2) . ?
C3 C7 1.411(2) . ?
C3 C4 1.428(2) . ?
C2 H2 0.9300 . ?
C14 C15 1.382(3) . ?
C14 C13 1.388(3) . ?
C14 H14 0.9300 . ?
C13 C18 1.394(2) . ?
C13 C10 1.492(2) . ?
C9 H9 0.9300 . ?
C4 C12 1.486(2) . ?
C17 C16 1.383(3) . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N5 N6 C7 0.6(2) . . . . ?
C7 C3 C2 C1 2.2(2) . . . . ?
C4 C3 C2 C1 179.64(19) . . . . ?
C9 C1 C2 C3 -1.2(2) . . . . ?
C10 C1 C2 C3 -176.98(15) . . . . ?
C9 N8 C7 N6 -179.81(17) . . . . ?
C9 N8 C7 C3 -0.2(3) . . . . ?
N5 N6 C7 N8 179.43(16) . . . . ?
N5 N6 C7 C3 -0.2(2) . . . . ?
C2 C3 C7 N8 -1.6(3) . . . . ?
C4 C3 C7 N8 -179.83(16) . . . . ?
C2 C3 C7 N6 178.01(15) . . . . ?
C4 C3 C7 N6 -0.19(18) . . . . ?
C15 C14 C13 C18 -1.2(3) . . . . ?
C15 C14 C13 C10 175.87(16) . . . . ?
C7 N8 C9 C1 1.5(3) . . . . ?
C2 C1 C9 N8 -0.8(3) . . . . ?
C10 C1 C9 N8 174.88(17) . . . . ?
C2 C1 C10 O11 24.2(3) . . . . ?
C9 C1 C10 O11 -151.5(2) . . . . ?
C2 C1 C10 C13 -154.44(17) . . . . ?
C9 C1 C10 C13 29.9(3) . . . . ?
C14 C13 C10 O11 -147.8(2) . . . . ?
C18 C13 C10 O11 29.2(3) . . . . ?
C14 C13 C10 C1 30.8(3) . . . . ?
C18 C13 C10 C1 -152.18(17) . . . . ?
N6 N5 C4 C3 -0.7(2) . . . . ?
N6 N5 C4 C12 178.65(18) . . . . ?
C2 C3 C4 N5 -177.07(19) . . . . ?
C7 C3 C4 N5 0.6(2) . . . . ?
C2 C3 C4 C12 3.7(4) . . . . ?
C7 C3 C4 C12 -178.72(19) . . . . ?
C13 C14 C15 C16 2.8(3) . . . . ?
C16 C17 C18 C13 1.5(3) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C10 C13 C18 C17 -178.12(15) . . . . ?
C14 C15 C16 C17 -2.2(3) . . . . ?
C14 C15 C16 Cl19 176.88(14) . . . . ?
C18 C17 C16 C15 0.1(3) . . . . ?
C18 C17 C16 Cl19 -178.99(13) . . . . ?
