#------------------------------------------------------------------------------
#$Date: 2023-01-20 12:04:31 +0200 (Fri, 20 Jan 2023) $
#$Revision: 280466 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106509.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_8106509
loop_
_publ_author_name
'Yun, Zhao'
'Lu, Xu'
'Li-Fang, Zhang'
_publ_section_title
;
 Crystal structure of (tris(2-pyridylmethyl)amine-κ4
 N,N′,N′′,N′′′′)-chloranilato-\kO,O′-zinc(II)
 -- methanol (1/1), C25H22Cl2N4O5Zn
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              275
_journal_page_last               277
_journal_paper_doi               10.1515/ncrs-2016-0237
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C24 H18 Cl2 N4 O4 Zn, C H4 O'
_chemical_formula_sum            'C25 H22 Cl2 N4 O5 Zn'
_chemical_formula_weight         594.74
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.302(3)
_cell_length_b                   11.324(2)
_cell_length_c                   14.636(3)
_cell_measurement_reflns_used    1138
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.48
_cell_volume                     2515.1(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II 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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21913
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.234
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.0049(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0511
_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)+(0.0469P)²+2.9961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                4419
_reflns_number_total             4932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0237_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        2515.1(9)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8106509
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.26637(2) 0.81232(3) 0.25800(3) 0.02211(14) Uani 1 1 d . . .
Cl1 Cl 0.02192(5) 0.96845(7) 0.35808(6) 0.0267(2) Uani 1 1 d . . .
Cl2 Cl 0.41477(5) 1.15424(7) 0.47332(6) 0.0273(2) Uani 1 1 d . . .
N4 N 0.20777(17) 0.6530(2) 0.1779(2) 0.0236(6) Uani 1 1 d . . .
N2 N 0.30709(18) 0.6797(2) 0.3777(2) 0.0256(6) Uani 1 1 d . . .
N1 N 0.19251(17) 0.8790(2) 0.1134(2) 0.0244(6) Uani 1 1 d . . .
N3 N 0.37739(17) 0.7465(2) 0.23119(18) 0.0204(6) Uani 1 1 d . . .
O1 O 0.32649(14) 0.95507(19) 0.33964(16) 0.0234(5) Uani 1 1 d . . .
O2 O 0.16452(14) 0.87168(19) 0.29929(17) 0.0253(5) Uani 1 1 d . . .
O3 O 0.27648(15) 1.2438(2) 0.54296(17) 0.0300(5) Uani 1 1 d . . .
O4 O 0.10899(16) 1.1706(2) 0.49166(19) 0.0351(6) Uani 1 1 d . . .
C1 C 0.1204(2) 0.6898(3) 0.1073(3) 0.0281(7) Uani 1 1 d . . .
H1A H 0.0793 0.6973 0.1411 0.034 Uiso 1 1 calc R . .
H1B H 0.0979 0.6301 0.0567 0.034 Uiso 1 1 calc R . .
C5 C 0.1371(3) 1.0267(3) -0.0106(3) 0.0359(9) Uani 1 1 d . . .
H5 H 0.1412 1.1026 -0.0327 0.043 Uiso 1 1 calc R . .
C2 C 0.1275(2) 0.8063(3) 0.0608(2) 0.0255(7) Uani 1 1 d . . .
C6 C 0.1966(2) 0.9871(3) 0.0776(3) 0.0305(8) Uani 1 1 d . . .
H6 H 0.2417 1.0375 0.1140 0.037 Uiso 1 1 calc R . .
C4 C 0.0708(3) 0.9509(3) -0.0656(3) 0.0401(9) Uani 1 1 d . . .
H4 H 0.0298 0.9747 -0.1258 0.048 Uiso 1 1 calc R . .
C3 C 0.0666(2) 0.8395(3) -0.0297(3) 0.0360(9) Uani 1 1 d . . .
H3 H 0.0231 0.7869 -0.0659 0.043 Uiso 1 1 calc R . .
C11 C 0.4102(2) 0.5961(3) 0.5243(3) 0.0346(8) Uani 1 1 d . . .
H11 H 0.4546 0.6073 0.5854 0.041 Uiso 1 1 calc R . .
C7 C 0.2013(2) 0.5642(3) 0.2492(3) 0.0333(8) Uani 1 1 d . . .
H7A H 0.1983 0.4859 0.2213 0.040 Uiso 1 1 calc R . .
H7B H 0.1473 0.5772 0.2613 0.040 Uiso 1 1 calc R . .
C9 C 0.3156(2) 0.4706(3) 0.4002(3) 0.0315(8) Uani 1 1 d . . .
H9 H 0.2962 0.3956 0.3759 0.038 Uiso 1 1 calc R . .
C12 C 0.3720(2) 0.6914(3) 0.4654(3) 0.0298(8) Uani 1 1 d . . .
H12 H 0.3922 0.7668 0.4875 0.036 Uiso 1 1 calc R . .
C10 C 0.3812(2) 0.4836(3) 0.4909(3) 0.0341(8) Uani 1 1 d . . .
H10 H 0.4056 0.4179 0.5293 0.041 Uiso 1 1 calc R . .
C8 C 0.2787(2) 0.5700(3) 0.3453(3) 0.0278(7) Uani 1 1 d . . .
C17 C 0.5319(2) 0.7189(3) 0.2712(3) 0.0302(8) Uani 1 1 d . . .
H17 H 0.5892 0.7458 0.3031 0.036 Uiso 1 1 calc R . .
C14 C 0.3613(2) 0.6459(3) 0.1793(2) 0.0237(7) Uani 1 1 d . . .
C13 C 0.2657(2) 0.6132(3) 0.1265(3) 0.0319(8) Uani 1 1 d . . .
H13A H 0.2452 0.6477 0.0614 0.038 Uiso 1 1 calc R . .
H13B H 0.2611 0.5281 0.1190 0.038 Uiso 1 1 calc R . .
C18 C 0.4610(2) 0.7809(3) 0.2770(2) 0.0250(7) Uani 1 1 d . . .
H18 H 0.4719 0.8496 0.3144 0.030 Uiso 1 1 calc R . .
C15 C 0.4291(2) 0.5789(3) 0.1705(3) 0.0308(8) Uani 1 1 d . . .
H15 H 0.4167 0.5097 0.1338 0.037 Uiso 1 1 calc R . .
C16 C 0.5158(2) 0.6158(3) 0.2170(3) 0.0310(8) Uani 1 1 d . . .
H16 H 0.5620 0.5719 0.2117 0.037 Uiso 1 1 calc R . .
C20 C 0.3073(2) 1.1027(3) 0.4428(2) 0.0199(6) Uani 1 1 d . . .
C24 C 0.1852(2) 0.9620(3) 0.3544(2) 0.0201(7) Uani 1 1 d . . .
C21 C 0.2526(2) 1.1607(3) 0.4842(2) 0.0210(7) Uani 1 1 d . . .
C23 C 0.1296(2) 1.0192(3) 0.3915(2) 0.0196(6) Uani 1 1 d . . .
C22 C 0.1558(2) 1.1174(3) 0.4557(2) 0.0222(7) Uani 1 1 d . . .
C19 C 0.27968(19) 1.0087(3) 0.3797(2) 0.0179(6) Uani 1 1 d . . .
O5 O 0.23853(17) 0.2391(3) 0.7139(2) 0.0408(6) Uani 1 1 d . . .
H5A H 0.2352 0.2423 0.6566 0.061 Uiso 1 1 calc R . .
C25 C 0.1551(2) 0.2592(3) 0.7179(3) 0.0357(9) Uani 1 1 d . . .
H25A H 0.1558 0.2377 0.7816 0.054 Uiso 1 1 calc R . .
H25B H 0.1121 0.2125 0.6687 0.054 Uiso 1 1 calc R . .
H25C H 0.1404 0.3414 0.7061 0.054 Uiso 1 1 calc R . .
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'
Zn Zn 0.2839 1.4301 '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
O1 Zn1 O2 80.60(8) . .
O1 Zn1 N3 97.31(9) . .
O2 Zn1 N3 174.06(10) . .
O1 Zn1 N1 105.95(10) . .
O2 Zn1 N1 87.30(10) . .
N3 Zn1 N1 98.63(10) . .
O1 Zn1 N4 176.43(10) . .
O2 Zn1 N4 100.67(9) . .
N3 Zn1 N4 81.10(10) . .
N1 Zn1 N4 77.49(10) . .
O1 Zn1 N2 97.65(10) . .
O2 Zn1 N2 91.70(10) . .
N3 Zn1 N2 83.05(10) . .
N1 Zn1 N2 155.87(10) . .
N4 Zn1 N2 79.02(10) . .
C13 N4 C7 112.1(3) . .
C13 N4 C1 111.2(3) . .
C7 N4 C1 112.6(3) . .
C13 N4 Zn1 106.93(19) . .
C7 N4 Zn1 108.3(2) . .
C1 N4 Zn1 105.30(19) . .
C12 N2 C8 118.5(3) . .
C12 N2 Zn1 126.5(2) . .
C8 N2 Zn1 112.4(2) . .
C2 N1 C6 118.5(3) . .
C2 N1 Zn1 113.0(2) . .
C6 N1 Zn1 127.9(2) . .
C18 N3 C14 119.0(3) . .
C18 N3 Zn1 125.9(2) . .
C14 N3 Zn1 113.5(2) . .
C19 O1 Zn1 114.08(19) . .
C24 O2 Zn1 112.99(19) . .
N4 C1 C2 110.4(3) . .
N4 C1 H1A 109.6 . .
C2 C1 H1A 109.6 . .
N4 C1 H1B 109.6 . .
C2 C1 H1B 109.6 . .
H1A C1 H1B 108.1 . .
C6 C5 C4 118.5(3) . .
C6 C5 H5 120.8 . .
C4 C5 H5 120.8 . .
N1 C2 C3 121.5(3) . .
N1 C2 C1 116.9(3) . .
C3 C2 C1 121.5(3) . .
N1 C6 C5 123.0(3) . .
N1 C6 H6 118.5 . .
C5 C6 H6 118.5 . .
C3 C4 C5 118.9(4) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C4 C3 C2 119.7(3) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C12 C11 C10 118.7(3) . .
C12 C11 H11 120.6 . .
C10 C11 H11 120.6 . .
N4 C7 C8 112.1(3) . .
N4 C7 H7A 109.2 . .
C8 C7 H7A 109.2 . .
N4 C7 H7B 109.2 . .
C8 C7 H7B 109.2 . .
H7A C7 H7B 107.9 . .
C10 C9 C8 119.5(3) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
N2 C12 C11 122.7(3) . .
N2 C12 H12 118.6 . .
C11 C12 H12 118.6 . .
C9 C10 C11 119.0(3) . .
C9 C10 H10 120.5 . .
C11 C10 H10 120.5 . .
N2 C8 C9 121.5(3) . .
N2 C8 C7 115.5(3) . .
C9 C8 C7 122.9(3) . .
C16 C17 C18 118.5(3) . .
C16 C17 H17 120.8 . .
C18 C17 H17 120.8 . .
N3 C14 C15 121.3(3) . .
N3 C14 C13 116.7(3) . .
C15 C14 C13 121.9(3) . .
N4 C13 C14 113.4(3) . .
N4 C13 H13A 108.9 . .
C14 C13 H13A 108.9 . .
N4 C13 H13B 108.9 . .
C14 C13 H13B 108.9 . .
H13A C13 H13B 107.7 . .
N3 C18 C17 122.9(3) . .
N3 C18 H18 118.6 . .
C17 C18 H18 118.6 . .
C14 C15 C16 119.6(3) . .
C14 C15 H15 120.2 . .
C16 C15 H15 120.2 . .
C17 C16 C15 118.8(3) . .
C17 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
C19 C20 C21 123.1(3) . .
C19 C20 Cl2 118.9(2) . .
C21 C20 Cl2 117.9(2) . .
O2 C24 C23 124.7(3) . .
O2 C24 C19 116.1(3) . .
C23 C24 C19 119.2(3) . .
O3 C21 C20 124.4(3) . .
O3 C21 C22 117.2(3) . .
C20 C21 C22 118.4(3) . .
C24 C23 C22 123.2(3) . .
C24 C23 Cl1 118.4(2) . .
C22 C23 Cl1 118.3(2) . .
O4 C22 C23 125.7(3) . .
O4 C22 C21 117.2(3) . .
C23 C22 C21 117.1(3) . .
O1 C19 C20 125.1(3) . .
O1 C19 C24 116.1(3) . .
C20 C19 C24 118.8(3) . .
C25 O5 H5A 109.5 . .
O5 C25 H25A 109.5 . .
O5 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
O5 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 2.036(2) .
Zn1 O2 2.075(2) .
Zn1 N3 2.122(3) .
Zn1 N1 2.153(3) .
Zn1 N4 2.173(3) .
Zn1 N2 2.217(3) .
Cl1 C23 1.738(3) .
Cl2 C20 1.743(3) .
N4 C13 1.476(4) .
N4 C7 1.480(4) .
N4 C1 1.482(4) .
N2 C12 1.339(4) .
N2 C8 1.350(4) .
N1 C2 1.341(4) .
N1 C6 1.343(4) .
N3 C18 1.339(4) .
N3 C14 1.341(4) .
O1 C19 1.274(4) .
O2 C24 1.269(4) .
O3 C21 1.238(4) .
O4 C22 1.231(4) .
C1 C2 1.508(5) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C5 C6 1.376(5) .
C5 C4 1.385(5) .
C5 H5 0.9300 .
C2 C3 1.385(5) .
C6 H6 0.9300 .
C4 C3 1.378(5) .
C4 H4 0.9300 .
C3 H3 0.9300 .
C11 C12 1.379(5) .
C11 C10 1.385(5) .
C11 H11 0.9300 .
C7 C8 1.509(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C9 C10 1.375(5) .
C9 C8 1.386(5) .
C9 H9 0.9300 .
C12 H12 0.9300 .
C10 H10 0.9300 .
C17 C16 1.382(5) .
C17 C18 1.381(5) .
C17 H17 0.9300 .
C14 C15 1.385(5) .
C14 C13 1.511(5) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C18 H18 0.9300 .
C15 C16 1.389(5) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C20 C19 1.372(4) .
C20 C21 1.411(4) .
C24 C23 1.377(4) .
C24 C19 1.540(4) .
C21 C22 1.556(4) .
C23 C22 1.417(4) .
O5 C25 1.401(4) .
O5 H5A 0.8200 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
