#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/25/7112506.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_7112506
loop_
_publ_author_name
'Masciocchi, Daniela'
'Gelain, Arianna'
'Porta, Federica'
'Meneghetti, Fiorella'
'Pedretti, Alessandro'
'Celentano, Giuseppe'
'Barlocco, Daniela'
'Legnani, Laura'
'Toma, Lucio'
'Kwon, Byoung-Mog'
'Asai, Akira'
'Villa, Stefania'
_publ_section_title
;
 Synthesis, structure--activity relationships and stereochemical
 investigations of new tricyclic pyridazinone derivatives as potential
 STAT3 inhibitors
;
_journal_issue                   8
_journal_name_full               MedChemComm
_journal_page_first              1181
_journal_paper_doi               10.1039/c3md00095h
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H15 Cl N2 O'
_chemical_formula_weight         262.73
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-12T14:13:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.929(4)
_cell_length_b                   12.530(4)
_cell_length_c                   12.977(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      9
_cell_volume                     1289.3(11)
_computing_cell_refinement       'SHELXL-97 (Sheldrick, 2008)'
_computing_data_collection       'CAD-4 Software (Enraf Nonius, 1989)'
_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    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1806
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.3057
_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    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         1806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0524P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                1010
_reflns_number_total             1806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3md00095h.txt
_cod_data_source_block           dm5clr
_cod_database_code               7112506
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
Cl1 Cl 0.8552(2) 0.75926(10) 0.47502(12) 0.0847(5) Uani 1 1 d
N2 N 0.9038(5) 0.3961(3) 0.4991(3) 0.0493(12) Uani 1 1 d
O1 O 0.8537(6) 0.5064(3) 0.7479(3) 0.0848(12) Uani 1 1 d
C5 C 0.8836(6) 0.2244(3) 0.4259(4) 0.0385(11) Uani 1 1 d
C3 C 0.9066(5) 0.2503(4) 0.6225(3) 0.0436(12) Uani 1 1 d
N1 N 0.9158(6) 0.4634(3) 0.5842(3) 0.0563(13) Uani 1 1 d
C4 C 0.8954(6) 0.2961(3) 0.5167(4) 0.0418(12) Uani 1 1 d
C2 C 0.8196(8) 0.3249(4) 0.6968(4) 0.0552(15) Uani 1 1 d
H2A H 0.688(6) 0.318(4) 0.682(4) 0.085(17) Uiso 1 1 d
H2B H 0.834(6) 0.306(3) 0.762(3) 0.061(16) Uiso 1 1 d
C8 C 0.8380(7) 0.1376(4) 0.6274(4) 0.0481(13) Uani 1 1 d
H8A H 0.704(5) 0.142(3) 0.613(3) 0.066(14) Uiso 1 1 d
H8B H 0.860(6) 0.105(3) 0.691(3) 0.053(14) Uiso 1 1 d
C9 C 0.8583(7) 0.2663(4) 0.3289(4) 0.0489(12) Uani 1 1 d
H9 H 0.843(5) 0.338(3) 0.318(3) 0.032(11) Uiso 1 1 d
C13 C 0.9558(9) 0.5731(4) 0.5564(5) 0.0706(19) Uani 1 1 d
H13A H 1.050(7) 0.573(4) 0.507(3) 0.09(2) Uiso 1 1 d
H13B H 0.967(7) 0.624(5) 0.630(4) 0.13(2) Uiso 1 1 d
C10 C 0.8520(8) 0.1996(5) 0.2449(4) 0.0632(14) Uani 1 1 d
H10 H 0.830(5) 0.229(3) 0.180(3) 0.056(13) Uiso 1 1 d
C7 C 0.9248(8) 0.0689(4) 0.5463(4) 0.0579(16) Uani 1 1 d
C6 C 0.8998(6) 0.1149(3) 0.4400(4) 0.0463(13) Uani 1 1 d
C1 C 0.8627(8) 0.4387(4) 0.6818(4) 0.0565(14) Uani 1 1 d
C12 C 0.8899(8) 0.0505(4) 0.3535(5) 0.0663(17) Uani 1 1 d
H12 H 0.916(6) -0.022(3) 0.368(3) 0.051(14) Uiso 1 1 d
C11 C 0.8682(9) 0.0912(5) 0.2579(5) 0.0728(17) Uani 1 1 d
H11 H 0.866(7) 0.037(3) 0.205(3) 0.075(15) Uiso 1 1 d
C14 C 0.8102(9) 0.6229(5) 0.5013(6) 0.078(2) Uani 1 1 d
H14A H 0.726(6) 0.610(3) 0.551(3) 0.059(18) Uiso 1 1 d
H14B H 0.754(8) 0.582(4) 0.439(4) 0.13(3) Uiso 1 1 d
H3 H 1.027(5) 0.251(4) 0.638(3) 0.059(13) Uiso 1 1 d
H7A H 1.074(7) 0.068(4) 0.563(4) 0.10(2) Uiso 1 1 d
H7B H 0.861(7) -0.002(4) 0.549(4) 0.096(18) Uiso 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'
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'
Cl Cl 0.1484 0.1585 '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
C4 N2 N1 117.2(4)
C9 C5 C6 120.7(5)
C9 C5 C4 120.2(4)
C6 C5 C4 119.1(4)
C4 C3 C2 108.8(4)
C4 C3 C8 112.1(4)
C2 C3 C8 112.7(4)
C1 N1 N2 125.1(4)
C1 N1 C13 120.6(5)
N2 N1 C13 113.0(4)
N2 C4 C5 117.1(4)
N2 C4 C3 122.7(5)
C5 C4 C3 120.1(4)
C1 C2 C3 114.0(5)
C3 C8 C7 109.6(5)
C10 C9 C5 119.8(5)
N1 C13 C14 110.2(5)
C9 C10 C11 120.1(5)
C6 C7 C8 110.9(4)
C12 C6 C5 117.5(5)
C12 C6 C7 121.8(4)
C5 C6 C7 120.7(5)
O1 C1 N1 121.1(5)
O1 C1 C2 124.7(5)
N1 C1 C2 114.2(5)
C11 C12 C6 122.1(5)
C12 C11 C10 119.8(6)
C13 C14 Cl1 109.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.778(6)
N2 C4 1.276(5)
N2 N1 1.392(5)
O1 C1 1.209(5)
C5 C9 1.379(6)
C5 C6 1.390(6)
C5 C4 1.485(6)
C3 C4 1.490(6)
C3 C2 1.509(7)
C3 C8 1.514(6)
N1 C1 1.370(6)
N1 C13 1.456(6)
C2 C1 1.480(7)
C8 C7 1.525(7)
C9 C10 1.374(6)
C13 C14 1.494(8)
C10 C11 1.374(7)
C7 C6 1.508(7)
C6 C12 1.384(7)
C12 C11 1.352(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184492
