#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/52/7055215.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_7055215
loop_
_publ_author_name
'Bustos, Carlos'
'Molins, Elies'
'Cárcamo, Juan-Guillermo'
'Aguilar, Marcelo N.'
'Sánchez, Christian'
'Moreno-Villoslada, Ignacio'
'Nishide, Hiroyuki'
'Zarate, Ximena'
'Schott, Eduardo'
_publ_section_title
;
 A family of substituted hydrazonoisoxazolones with potential biological
 properties
;
_journal_issue                   3
_journal_name_full               'New J. Chem.'
_journal_page_first              2156
_journal_paper_doi               10.1039/C5NJ02604K
_journal_volume                  40
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H8 Cl1 N3 O2'
_chemical_formula_sum            'C10 H8 Cl N3 O2'
_chemical_formula_weight         237.64
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-06-18T19:38:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-04-29 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.90(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.577(3)
_cell_length_b                   8.509(8)
_cell_length_c                   20.565(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      16
_cell_measurement_wavelength     0.71073
_cell_volume                     2145(2)
_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    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.060892
_diffrn_orient_matrix_UB_12      -0.007576
_diffrn_orient_matrix_UB_13      -0.040534
_diffrn_orient_matrix_UB_21      -0.054047
_diffrn_orient_matrix_UB_22      0.018197
_diffrn_orient_matrix_UB_23      0.028236
_diffrn_orient_matrix_UB_31      0.004607
_diffrn_orient_matrix_UB_32      0.11584
_diffrn_orient_matrix_UB_33      -0.00708
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4213
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.66
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.9497
_exptl_absorpt_correction_T_min  0.8455
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0594P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2147
_reflns_number_total             4213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj02604k2.cif
_cod_data_source_block           xv1
_cod_depositor_comments
'Adding full bibliography for 7055215--7055216.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7055215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C11 C 0.9809(3) 1.3861(4) -0.08287(17) 0.0509(8) Uani 1 1 d .
C12 C 0.8187(3) 1.2710(4) -0.13605(17) 0.0547(9) Uani 1 1 d .
C13 C 0.8998(3) 1.2701(3) -0.07558(15) 0.0457(8) Uani 1 1 d .
C14 C 0.9610(3) 1.0933(4) 0.08525(16) 0.0517(9) Uani 1 1 d .
C15 C 0.8779(3) 0.9850(4) 0.08004(17) 0.0562(9) Uani 1 1 d .
H15 H 0.8285 0.968 0.0397 0.067 Uiso 1 1 calc R
C16 C 0.8705(3) 0.9028(4) 0.1365(2) 0.0654(10) Uani 1 1 d .
C17 C 0.9440(4) 0.9238(4) 0.1966(2) 0.0762(12) Uani 1 1 d .
H17 H 0.9378 0.8659 0.2339 0.091 Uiso 1 1 calc R
C18 C 1.0259(3) 1.0308(4) 0.20039(18) 0.0709(11) Uani 1 1 d .
H18 H 1.0758 1.0465 0.2406 0.085 Uiso 1 1 calc R
C19 C 1.0350(3) 1.1159(4) 0.14484(17) 0.0599(9) Uani 1 1 d .
H19 H 1.0911 1.1884 0.1476 0.072 Uiso 1 1 calc R
C22 C 0.7209(3) 1.1697(4) -0.15359(19) 0.0782(11) Uani 1 1 d .
H22A H 0.6783 1.1996 -0.1966 0.117 Uiso 1 1 calc R
H22B H 0.6781 1.1817 -0.1207 0.117 Uiso 1 1 calc R
H22C H 0.7431 1.062 -0.1549 0.117 Uiso 1 1 calc R
Cl16 Cl 0.76320(10) 0.77122(12) 0.13202(6) 0.0993(5) Uani 1 1 d .
N11 N 0.8400(2) 1.3731(4) -0.17794(14) 0.0714(9) Uani 1 1 d .
N13 N 0.8934(2) 1.1808(3) -0.02471(14) 0.0506(7) Uani 1 1 d .
N14 N 0.9704(2) 1.1857(3) 0.02960(13) 0.0521(7) Uani 1 1 d .
H14 H 1.0266 1.2447 0.0315 0.062 Uiso 1 1 calc R
O10 O 1.06408(19) 1.4258(3) -0.04523(12) 0.0643(7) Uani 1 1 d .
O11 O 0.9452(2) 1.4503(3) -0.14434(12) 0.0690(7) Uani 1 1 d .
C1 C 0.7136(3) 0.6564(4) -0.11221(19) 0.0635(10) Uani 1 1 d .
C2 C 0.5556(3) 0.5390(4) -0.17095(18) 0.0621(9) Uani 1 1 d .
C3 C 0.6299(3) 0.5441(4) -0.10670(17) 0.0539(9) Uani 1 1 d .
C4 C 0.6841(3) 0.3604(3) 0.05198(16) 0.0477(8) Uani 1 1 d .
C5 C 0.5937(3) 0.2635(4) 0.04601(17) 0.0589(9) Uani 1 1 d .
H5 H 0.5388 0.2634 0.0073 0.071 Uiso 1 1 calc R
C6 C 0.5875(3) 0.1677(4) 0.0990(2) 0.0621(10) Uani 1 1 d .
C7 C 0.6677(3) 0.1643(4) 0.15650(18) 0.0643(10) Uani 1 1 d .
H7 H 0.662 0.0981 0.1916 0.077 Uiso 1 1 calc R
C8 C 0.7562(3) 0.2607(4) 0.16105(18) 0.0614(9) Uani 1 1 d .
H8 H 0.8112 0.2599 0.1997 0.074 Uiso 1 1 calc R
C9 C 0.7652(3) 0.3591(4) 0.10915(16) 0.0528(8) Uani 1 1 d .
H9 H 0.8258 0.424 0.1129 0.063 Uiso 1 1 calc R
C21 C 0.4562(3) 0.4418(5) -0.18867(19) 0.0894(13) Uani 1 1 d .
H21A H 0.4031 0.4798 -0.1654 0.134 Uiso 1 1 calc R
H21B H 0.474 0.3346 -0.1762 0.134 Uiso 1 1 calc R
H21C H 0.427 0.4476 -0.2359 0.134 Uiso 1 1 calc R
Cl6 Cl 0.47417(10) 0.04679(13) 0.09162(6) 0.1038(4) Uani 1 1 d .
N1 N 0.5845(3) 0.6294(4) -0.21354(16) 0.0942(11) Uani 1 1 d .
N3 N 0.6201(2) 0.4560(3) -0.05679(14) 0.0516(7) Uani 1 1 d .
N4 N 0.6939(2) 0.4614(3) -0.00083(13) 0.0537(7) Uani 1 1 d .
H4 H 0.7478 0.5257 0.0037 0.064 Uiso 1 1 calc R
O0 O 0.7919(2) 0.6986(3) -0.07018(13) 0.0867(9) Uani 1 1 d .
O1 O 0.6919(2) 0.7124(3) -0.17485(13) 0.0912(9) Uani 1 1 d .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 -3 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O10 C11 O11 123.0(3)
O10 C11 C13 131.0(3)
O11 C11 C13 106.0(3)
N11 C12 C13 111.9(3)
N11 C12 C22 120.9(3)
C13 C12 C22 127.2(3)
N13 C13 C12 122.9(3)
N13 C13 C11 130.3(3)
C12 C13 C11 106.8(3)
C19 C14 C15 120.8(3)
C19 C14 N14 118.7(3)
C15 C14 N14 120.5(3)
C16 C15 C14 117.8(3)
C15 C16 C17 122.1(3)
C15 C16 Cl16 118.7(3)
C17 C16 Cl16 119.2(3)
C18 C17 C16 119.0(3)
C17 C18 C19 120.3(4)
C14 C19 C18 120.0(3)
C12 N11 O11 106.2(3)
N14 N13 C13 119.9(3)
N13 N14 C14 119.6(3)
C11 O11 N11 109.1(2)
O0 C1 O1 122.6(4)
O0 C1 C3 129.1(3)
O1 C1 C3 108.3(3)
N1 C2 C3 112.7(4)
N1 C2 C21 121.6(4)
C3 C2 C21 125.7(4)
N3 C3 C2 123.5(3)
N3 C3 C1 130.0(3)
C2 C3 C1 106.4(3)
C9 C4 C5 120.5(3)
C9 C4 N4 119.2(3)
C5 C4 N4 120.2(3)
C6 C5 C4 118.2(3)
C7 C6 C5 122.2(3)
C7 C6 Cl6 119.6(3)
C5 C6 Cl6 118.2(3)
C8 C7 C6 118.4(3)
C7 C8 C9 121.1(4)
C4 C9 C8 119.6(3)
C2 N1 O1 105.5(3)
C3 N3 N4 120.1(3)
N3 N4 C4 119.3(3)
C1 O1 N1 107.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 O10 1.202(4)
C11 O11 1.358(4)
C11 C13 1.451(4)
C12 N11 1.293(4)
C12 C13 1.421(4)
C12 C22 1.479(4)
C13 N13 1.310(4)
C14 C19 1.377(4)
C14 C15 1.379(4)
C14 N14 1.416(4)
C15 C16 1.377(4)
C16 C17 1.379(5)
C16 Cl16 1.739(4)
C17 C18 1.364(5)
C18 C19 1.378(4)
N11 O11 1.500(3)
N13 N14 1.306(3)
C1 O0 1.210(4)
C1 O1 1.343(4)
C1 C3 1.445(5)
C2 N1 1.278(4)
C2 C3 1.438(5)
C2 C21 1.475(5)
C3 N3 1.299(4)
C4 C9 1.374(4)
C4 C5 1.388(4)
C4 N4 1.411(4)
C5 C6 1.377(4)
C6 C7 1.373(4)
C6 Cl6 1.737(3)
C7 C8 1.369(4)
C8 C9 1.381(4)
N1 O1 1.573(4)
N3 N4 1.308(3)
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
N11 C12 C13 N13 177.2(3)
C22 C12 C13 N13 -4.1(5)
N11 C12 C13 C11 -0.8(4)
C22 C12 C13 C11 178.0(3)
O10 C11 C13 N13 2.7(6)
O11 C11 C13 N13 -176.8(3)
O10 C11 C13 C12 -179.5(3)
O11 C11 C13 C12 1.0(3)
C19 C14 C15 C16 1.2(5)
N14 C14 C15 C16 -177.6(3)
C14 C15 C16 C17 -1.3(5)
C14 C15 C16 Cl16 177.5(2)
C15 C16 C17 C18 0.9(5)
Cl16 C16 C17 C18 -177.9(3)
C16 C17 C18 C19 -0.3(5)
C15 C14 C19 C18 -0.7(5)
N14 C14 C19 C18 178.1(3)
C17 C18 C19 C14 0.2(5)
C13 C12 N11 O11 0.3(4)
C22 C12 N11 O11 -178.6(3)
C12 C13 N13 N14 -179.8(3)
C11 C13 N13 N14 -2.3(5)
C13 N13 N14 C14 177.6(3)
C19 C14 N14 N13 -171.2(3)
C15 C14 N14 N13 7.6(4)
O10 C11 O11 N11 179.6(3)
C13 C11 O11 N11 -0.9(3)
C12 N11 O11 C11 0.4(3)
N1 C2 C3 N3 -176.3(3)
C21 C2 C3 N3 3.4(5)
N1 C2 C3 C1 1.2(4)
C21 C2 C3 C1 -179.1(3)
O0 C1 C3 N3 -3.4(6)
O1 C1 C3 N3 176.6(3)
O0 C1 C3 C2 179.3(4)
O1 C1 C3 C2 -0.7(4)
C9 C4 C5 C6 0.5(5)
N4 C4 C5 C6 -179.6(3)
C4 C5 C6 C7 -0.6(5)
C4 C5 C6 Cl6 179.9(2)
C5 C6 C7 C8 0.4(5)
Cl6 C6 C7 C8 180.0(2)
C6 C7 C8 C9 -0.1(5)
C5 C4 C9 C8 -0.1(5)
N4 C4 C9 C8 179.9(3)
C7 C8 C9 C4 0.0(5)
C3 C2 N1 O1 -1.2(4)
C21 C2 N1 O1 179.2(3)
C2 C3 N3 N4 176.5(3)
C1 C3 N3 N4 -0.4(5)
C3 N3 N4 C4 -177.5(3)
C9 C4 N4 N3 175.9(3)
C5 C4 N4 N3 -4.0(4)
O0 C1 O1 N1 -180.0(3)
C3 C1 O1 N1 0.0(4)
C2 N1 O1 C1 0.7(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139063207
