#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/22/1542270.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_1542270
loop_
_publ_author_name
'Amiri, Nayereh'
'Rofouei, Mohammad K.'
'Ghasemi, Jahan B.'
_publ_section_title
;
 Multivariate optimization, preconcentration and determination of mercury
 ions with (1-(p-acetyl phenyl)-3-(o-methyl benzoate)) triazene in aqueous
 samples using ICP-AES
;
_journal_issue                   5
_journal_name_full               'Anal. Methods'
_journal_page_first              1111
_journal_paper_doi               10.1039/C5AY03169A
_journal_volume                  8
_journal_year                    2016
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_audit_update_record
;
2015-08-24 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.54(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0689(16)
_cell_length_b                   13.762(3)
_cell_length_c                   14.911(5)
_cell_measurement_reflns_used    3997
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.16
_cell_measurement_theta_min      2.12
_cell_volume                     1494.0(7)
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.0868
_diffrn_reflns_av_sigmaI/netI    0.1324
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10101
_diffrn_reflns_theta_full        29.16
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.1986
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0310P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                1333
_reflns_number_total             3997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ay03169a3.cif
_cod_data_source_block           kh695h
_cod_depositor_comments          'Adding full bibliography for 1542270.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1542270
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
O1 O 0.4039(2) 0.39674(12) 0.58423(13) 0.0719(6) Uani 1 1 d .
O2 O 0.4202(2) 0.30258(12) 0.46720(13) 0.0669(5) Uani 1 1 d .
O3 O 1.0487(3) -0.35567(15) 0.41574(16) 0.0983(7) Uani 1 1 d .
N1 N 0.6206(3) 0.14175(15) 0.52527(16) 0.0513(6) Uani 1 1 d .
N2 N 0.6954(3) 0.06049(13) 0.51042(15) 0.0480(5) Uani 1 1 d .
N3 N 0.6620(2) 0.04774(13) 0.42053(15) 0.0498(5) Uani 1 1 d .
C1 C 0.2838(4) 0.4621(2) 0.5078(2) 0.0922(10) Uani 1 1 d .
H1A H 0.3118 0.4593 0.4515 0.138 Uiso 1 1 calc R
H1B H 0.3014 0.5272 0.5333 0.138 Uiso 1 1 calc R
H1C H 0.1583 0.4431 0.4879 0.138 Uiso 1 1 calc R
C2 C 0.4602(3) 0.31745(18) 0.5543(2) 0.0506(6) Uani 1 1 d .
C3 C 0.5696(3) 0.25288(17) 0.63719(17) 0.0435(5) Uani 1 1 d .
C4 C 0.5959(3) 0.27431(18) 0.73389(18) 0.0528(7) Uani 1 1 d .
H4 H 0.5457 0.3310 0.7456 0.063 Uiso 1 1 calc R
C5 C 0.6938(3) 0.2138(2) 0.81206(19) 0.0626(7) Uani 1 1 d .
H5 H 0.7080 0.2286 0.8758 0.075 Uiso 1 1 calc R
C6 C 0.7709(3) 0.1307(2) 0.7947(2) 0.0659(7) Uani 1 1 d .
H6 H 0.8393 0.0899 0.8475 0.079 Uiso 1 1 calc R
C7 C 0.7484(3) 0.10709(18) 0.70066(19) 0.0568(7) Uani 1 1 d .
H7 H 0.8016 0.0508 0.6903 0.068 Uiso 1 1 calc R
C8 C 0.6463(3) 0.16710(17) 0.62099(18) 0.0441(6) Uani 1 1 d .
C9 C 0.7434(3) -0.03961(16) 0.40635(17) 0.0422(6) Uani 1 1 d .
C10 C 0.8413(3) -0.10425(18) 0.48196(19) 0.0529(6) Uani 1 1 d .
H10 H 0.8603 -0.0910 0.5469 0.063 Uiso 1 1 calc R
C11 C 0.9099(3) -0.18776(18) 0.46085(18) 0.0530(6) Uani 1 1 d .
H11 H 0.9747 -0.2309 0.5121 0.064 Uiso 1 1 calc R
C12 C 0.8851(3) -0.20976(17) 0.36472(18) 0.0452(6) Uani 1 1 d .
C13 C 0.9585(3) -0.30257(19) 0.3469(2) 0.0571(7) Uani 1 1 d .
C14 C 0.9202(4) -0.33144(19) 0.24311(19) 0.0754(8) Uani 1 1 d .
H14A H 0.9838 -0.3908 0.2445 0.113 Uiso 1 1 calc R
H14B H 0.9616 -0.2811 0.2130 0.113 Uiso 1 1 calc R
H14C H 0.7905 -0.3409 0.2051 0.113 Uiso 1 1 calc R
C15 C 0.7888(3) -0.14442(17) 0.29022(18) 0.0520(6) Uani 1 1 d .
H15 H 0.7700 -0.1573 0.2253 0.062 Uiso 1 1 calc R
C16 C 0.7196(3) -0.05969(17) 0.31128(17) 0.0530(7) Uani 1 1 d .
H16 H 0.6564 -0.0159 0.2604 0.064 Uiso 1 1 calc R
H1 H 0.555(3) 0.1806(18) 0.4760(18) 0.072(9) 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 0.0000 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
C2 O1 C1 117.1(2)
N2 N1 C8 120.1(2)
N2 N1 H1 121.7(16)
C8 N1 H1 118.2(16)
N3 N2 N1 112.9(2)
N2 N3 C9 111.93(19)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 O1 121.7(2)
O2 C2 C3 125.8(2)
O1 C2 C3 112.5(2)
C4 C3 C8 118.3(2)
C4 C3 C2 120.7(2)
C8 C3 C2 121.0(2)
C5 C4 C3 121.6(2)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 119.0(2)
C4 C5 H5 120.5
C6 C5 H5 120.5
C7 C6 C5 121.1(3)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 120.1(2)
C6 C7 H7 120.0
C8 C7 H7 120.0
C7 C8 N1 119.9(2)
C7 C8 C3 119.8(2)
N1 C8 C3 120.3(2)
C16 C9 C10 119.2(2)
C16 C9 N3 117.0(2)
C10 C9 N3 123.9(2)
C11 C10 C9 119.8(2)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 121.7(2)
C10 C11 H11 119.1
C12 C11 H11 119.1
C15 C12 C11 117.9(2)
C15 C12 C13 123.3(2)
C11 C12 C13 118.8(2)
O3 C13 C12 120.6(2)
O3 C13 C14 119.8(2)
C12 C13 C14 119.7(2)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 C16 120.5(2)
C12 C15 H15 119.7
C16 C15 H15 119.7
C9 C16 C15 120.8(2)
C9 C16 H16 119.6
C15 C16 H16 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.331(3)
O1 C1 1.447(3)
O2 C2 1.213(3)
O3 C13 1.214(3)
N1 N2 1.334(2)
N1 C8 1.395(3)
N1 H1 0.88(2)
N2 N3 1.260(2)
N3 C9 1.429(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.468(3)
C3 C4 1.396(3)
C3 C8 1.401(3)
C4 C5 1.372(3)
C4 H4 0.9300
C5 C6 1.379(3)
C5 H5 0.9300
C6 C7 1.372(3)
C6 H6 0.9300
C7 C8 1.389(3)
C7 H7 0.9300
C9 C16 1.374(3)
C9 C10 1.385(3)
C10 C11 1.370(3)
C10 H10 0.9300
C11 C12 1.393(3)
C11 H11 0.9300
C12 C15 1.379(3)
C12 C13 1.480(3)
C13 C14 1.495(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 C16 1.386(3)
C15 H15 0.9300
C16 H16 0.9300
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
N1 H1 O2 0.88(2) 1.97(3) 2.656(3) 134(2)
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
C8 N1 N2 N3 -179.3(2)
N1 N2 N3 C9 179.99(17)
C1 O1 C2 O2 3.5(3)
C1 O1 C2 C3 -175.7(2)
O2 C2 C3 C4 -175.4(2)
O1 C2 C3 C4 3.7(3)
O2 C2 C3 C8 3.0(3)
O1 C2 C3 C8 -177.9(2)
C8 C3 C4 C5 0.0(3)
C2 C3 C4 C5 178.4(2)
C3 C4 C5 C6 1.2(4)
C4 C5 C6 C7 -1.1(4)
C5 C6 C7 C8 -0.1(4)
C6 C7 C8 N1 -178.7(2)
C6 C7 C8 C3 1.4(3)
N2 N1 C8 C7 -0.6(3)
N2 N1 C8 C3 179.3(2)
C4 C3 C8 C7 -1.3(3)
C2 C3 C8 C7 -179.7(2)
C4 C3 C8 N1 178.8(2)
C2 C3 C8 N1 0.4(3)
N2 N3 C9 C16 -178.4(2)
N2 N3 C9 C10 2.3(3)
C16 C9 C10 C11 -1.2(3)
N3 C9 C10 C11 178.0(2)
C9 C10 C11 C12 0.4(3)
C10 C11 C12 C15 0.1(3)
C10 C11 C12 C13 -178.3(2)
C15 C12 C13 O3 177.0(2)
C11 C12 C13 O3 -4.6(3)
C15 C12 C13 C14 -3.4(3)
C11 C12 C13 C14 175.0(2)
C11 C12 C15 C16 0.1(3)
C13 C12 C15 C16 178.5(2)
C10 C9 C16 C15 1.4(3)
N3 C9 C16 C15 -177.9(2)
C12 C15 C16 C9 -0.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139047919
