#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/59/7025989.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_7025989
loop_
_publ_author_name
'You, Wei'
'Zhu, Hao-Yu'
'Huang, Wei'
'Hu, Bin'
'Fan, Ying'
'You, Xiao-Zeng'
_publ_section_title
;
 The first observation of azo-hydrazone and cis-trans tautomerisms for
 disperse yellow dyes and their nickel(II) and copper(II) complexes.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7876
_journal_page_last               7880
_journal_paper_doi               10.1039/c0dt00101e
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C14 H10 Cl2 N4 O2'
_chemical_formula_sum            'C14 H10 Cl2 N4 O2'
_chemical_formula_weight         337.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.756(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5409(12)
_cell_length_b                   11.9685(16)
_cell_length_c                   14.529(2)
_cell_measurement_reflns_used    1082
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      21.534
_cell_measurement_theta_min      2.278
_cell_volume                     1448.5(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (BRUKER 2000)'
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7116
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0635
_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)+(0.0999P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1877
_reflns_number_gt                1337
_reflns_number_total             2539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00101e.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7025989
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.3354(5) 0.6525(3) 0.9068(3) 0.0431(10) Uani 1 1 d .
C2 C 0.3982(5) 0.6049(4) 0.8295(3) 0.0448(11) Uani 1 1 d .
C3 C 0.4314(5) 0.7928(4) 0.7717(3) 0.0551(12) Uani 1 1 d .
C4 C 0.3805(5) 0.8377(3) 0.8544(3) 0.0484(11) Uani 1 1 d .
C5 C 0.3315(5) 0.7716(3) 0.9187(3) 0.0458(11) Uani 1 1 d .
C6 C 0.5046(6) 0.6310(4) 0.6887(3) 0.0647(14) Uani 1 1 d .
H6A H 0.5621 0.5633 0.7091 0.097 Uiso 1 1 calc R
H6B H 0.5756 0.6839 0.6694 0.097 Uiso 1 1 calc R
H6C H 0.4169 0.6151 0.6364 0.097 Uiso 1 1 calc R
C7 C 0.3815(5) 0.9574(4) 0.8622(3) 0.0565(13) Uani 1 1 d .
C8 C 0.2691(6) 0.8191(4) 0.9992(3) 0.0602(13) Uani 1 1 d .
H8A H 0.3576 0.8373 1.0503 0.090 Uiso 1 1 calc R
H8B H 0.2016 0.7650 1.0202 0.090 Uiso 1 1 calc R
H8C H 0.2081 0.8854 0.9787 0.090 Uiso 1 1 calc R
C9 C 0.2219(5) 0.4190(4) 1.0303(3) 0.0469(11) Uani 1 1 d .
C10 C 0.2339(5) 0.3060(4) 1.0233(3) 0.0513(12) Uani 1 1 d .
H10 H 0.2779 0.2740 0.9764 0.062 Uiso 1 1 calc R
C11 C 0.1775(5) 0.2383(3) 1.0893(3) 0.0494(12) Uani 1 1 d .
C12 C 0.1159(5) 0.2884(4) 1.1591(3) 0.0536(12) Uani 1 1 d .
C13 C 0.1043(6) 0.3996(4) 1.1654(3) 0.0583(13) Uani 1 1 d .
H13 H 0.0617 0.4312 1.2130 0.070 Uiso 1 1 calc R
C14 C 0.1561(5) 0.4676(4) 1.1005(3) 0.0548(12) Uani 1 1 d .
H14 H 0.1470 0.5448 1.1038 0.066 Uiso 1 1 calc R
Cl1 Cl 0.19264(17) 0.09542(10) 1.07928(9) 0.0734(5) Uani 1 1 d .
Cl2 Cl 0.04973(17) 0.20257(11) 1.23998(9) 0.0735(5) Uani 1 1 d .
N1 N 0.4423(4) 0.6778(3) 0.7664(2) 0.0478(9) Uani 1 1 d .
N2 N 0.3840(5) 1.0527(4) 0.8703(3) 0.0782(14) Uani 1 1 d .
N3 N 0.2834(4) 0.5916(3) 0.9697(2) 0.0453(9) Uani 1 1 d .
N4 N 0.2809(4) 0.4838(3) 0.9641(2) 0.0490(10) Uani 1 1 d .
H4 H 0.3155 0.4512 0.9197 0.059 Uiso 1 1 calc R
O1 O 0.4106(4) 0.5030(3) 0.8208(2) 0.0602(9) Uani 1 1 d .
O2 O 0.4636(4) 0.8524(3) 0.7100(2) 0.0768(11) 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 0.0000 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'
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
N3 C1 C5 116.3(4)
N3 C1 C2 123.6(4)
C5 C1 C2 120.1(4)
O1 C2 N1 121.1(4)
O1 C2 C1 121.2(4)
N1 C2 C1 117.7(4)
O2 C3 N1 120.7(5)
O2 C3 C4 122.8(4)
N1 C3 C4 116.5(4)
C5 C4 C7 121.6(4)
C5 C4 C3 122.8(4)
C7 C4 C3 115.6(4)
C4 C5 C1 118.4(4)
C4 C5 C8 122.1(4)
C1 C5 C8 119.4(4)
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N2 C7 C4 178.6(5)
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C14 121.2(4)
C10 C9 N4 116.7(4)
C14 C9 N4 122.1(4)
C9 C10 C11 118.3(4)
C9 C10 H10 120.8
C11 C10 H10 120.8
C12 C11 C10 119.4(4)
C12 C11 Cl1 122.8(4)
C10 C11 Cl1 117.8(4)
C13 C12 C11 121.9(4)
C13 C12 Cl2 119.9(4)
C11 C12 Cl2 118.1(4)
C12 C13 C14 119.7(5)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C9 119.5(4)
C13 C14 H14 120.3
C9 C14 H14 120.3
C2 N1 C3 124.2(4)
C2 N1 C6 118.1(4)
C3 N1 C6 117.7(4)
N4 N3 C1 120.7(4)
N3 N4 C9 120.5(4)
N3 N4 H4 119.7
C9 N4 H4 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.320(5)
C1 C5 1.438(6)
C1 C2 1.463(6)
C2 O1 1.233(5)
C2 N1 1.376(5)
C3 O2 1.223(5)
C3 N1 1.383(5)
C3 C4 1.467(6)
C4 C5 1.359(6)
C4 C7 1.437(6)
C5 C8 1.500(6)
C6 N1 1.463(5)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 N2 1.146(6)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.363(5)
C9 C14 1.395(6)
C9 N4 1.412(5)
C10 C11 1.418(6)
C10 H10 0.9300
C11 C12 1.379(6)
C11 Cl1 1.723(4)
C12 C13 1.339(6)
C12 Cl2 1.746(5)
C13 C14 1.390(6)
C13 H13 0.9300
C14 H14 0.9300
N3 N4 1.294(4)
N4 H4 0.8600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 163361
