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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/15/1551533.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_1551533
loop_
_publ_author_name
'MITSUHASHI, Ryoji'
'MIKURIYA, Masahiro'
_publ_section_title
;
 Synthesis and Crystal Structure of
 Bis[2-(1,4,5,6-tetrahydropyrimidin-2-yl)phenolato]zinc(II)
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              37
_journal_paper_doi               10.2116/xraystruct.35.37
_journal_volume                  35
_journal_year                    2019
_chemical_formula_moiety         'C20 H22 N4 O2 Zn'
_chemical_formula_sum            'C20 H22 N4 O2 Zn'
_chemical_formula_weight         415.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.242(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7667(14)
_cell_length_b                   11.4666(11)
_cell_length_c                   12.2213(12)
_cell_measurement_reflns_used    1991
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.42
_cell_volume                     1730.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2104
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.501
_diffrn_reflns_theta_min         2.424
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   TWINABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0652P)²+0.2665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1833
_reflns_number_total             2104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            35_37_1.txt
_cod_data_source_block           twin4
_cod_database_code               1551533
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.688
_shelx_estimated_absorpt_t_max   0.802
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.5000 0.57879(3) 0.2500 0.01179(15) Uani 1 2 d S T P
O1 O 0.37646(13) 0.47902(14) 0.20879(15) 0.0138(4) Uani 1 1 d . . .
C1 C 0.31051(18) 0.4888(2) 0.2605(2) 0.0121(5) Uani 1 1 d . . .
C2 C 0.21738(19) 0.4170(2) 0.2139(2) 0.0138(5) Uani 1 1 d . . .
H2 H 0.2076 0.3634 0.1506 0.017 Uiso 1 1 calc R U .
C3 C 0.14041(19) 0.4221(2) 0.2570(2) 0.0151(5) Uani 1 1 d . . .
H3 H 0.0798 0.3711 0.2248 0.018 Uiso 1 1 calc R U .
C4 C 0.15118(18) 0.5018(2) 0.3476(2) 0.0160(5) Uani 1 1 d . . .
H4 H 0.0965 0.5086 0.3747 0.019 Uiso 1 1 calc R U .
C5 C 0.24223(19) 0.5703(2) 0.3972(2) 0.0142(5) Uani 1 1 d . . .
H5 H 0.2491 0.6247 0.4589 0.017 Uiso 1 1 calc R U .
C6 C 0.32671(18) 0.5635(2) 0.3605(2) 0.0120(5) Uani 1 1 d . . .
C7 C 0.42734(18) 0.6318(2) 0.4333(2) 0.0113(5) Uani 1 1 d . . .
N1 N 0.44229(16) 0.66623(18) 0.54489(19) 0.0146(4) Uani 1 1 d . . .
H1 H 0.405(3) 0.630(3) 0.577(3) 0.032(9) Uiso 1 1 d . . .
C8 C 0.52346(19) 0.7507(2) 0.6211(2) 0.0152(5) Uani 1 1 d . . .
H8 H 0.5805 0.7104 0.6921 0.018 Uiso 1 1 calc R U .
H8A H 0.4891 0.8097 0.6519 0.018 Uiso 1 1 calc R U .
C9 C 0.57376(19) 0.8103(2) 0.5480(2) 0.0156(5) Uani 1 1 d . . .
H9 H 0.6419 0.8495 0.6036 0.019 Uiso 1 1 calc R U .
H9A H 0.5236 0.8701 0.4938 0.019 Uiso 1 1 calc R U .
C10 C 0.59663(19) 0.7189(2) 0.4726(2) 0.0142(5) Uani 1 1 d . . .
H10 H 0.6295 0.7569 0.4242 0.017 Uiso 1 1 calc R U .
H10A H 0.6492 0.6615 0.5277 0.017 Uiso 1 1 calc R U .
N2 N 0.49698(15) 0.65804(17) 0.38988(18) 0.0114(4) 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'
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 O1 106.98(10) 2_655 .
O1 Zn1 N2 98.48(7) 2_655 2_655
O1 Zn1 N2 113.97(7) . 2_655
O1 Zn1 N2 113.97(7) 2_655 .
O1 Zn1 N2 98.48(7) . .
N2 Zn1 N2 124.53(11) 2_655 .
C1 O1 Zn1 122.68(15) . .
O1 C1 C2 116.8(2) . .
O1 C1 C6 125.5(2) . .
C2 C1 C6 117.7(2) . .
C3 C2 C1 122.4(2) . .
C3 C2 H2 118.8 . .
C1 C2 H2 118.8 . .
C2 C3 C4 120.2(2) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 118.8(2) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
C4 C5 C6 122.9(2) . .
C4 C5 H5 118.5 . .
C6 C5 H5 118.5 . .
C5 C6 C1 117.6(2) . .
C5 C6 C7 117.1(2) . .
C1 C6 C7 125.3(2) . .
N2 C7 N1 121.9(2) . .
N2 C7 C6 121.8(2) . .
N1 C7 C6 116.3(2) . .
C7 N1 C8 124.9(2) . .
C7 N1 H1 117(2) . .
C8 N1 H1 118(2) . .
N1 C8 C9 110.1(2) . .
N1 C8 H8 109.6 . .
C9 C8 H8 109.6 . .
N1 C8 H8A 109.6 . .
C9 C8 H8A 109.6 . .
H8 C8 H8A 108.1 . .
C8 C9 C10 108.54(19) . .
C8 C9 H9 110.0 . .
C10 C9 H9 110.0 . .
C8 C9 H9A 110.0 . .
C10 C9 H9A 110.0 . .
H9 C9 H9A 108.4 . .
N2 C10 C9 111.36(19) . .
N2 C10 H10 109.4 . .
C9 C10 H10 109.4 . .
N2 C10 H10A 109.4 . .
C9 C10 H10A 109.4 . .
H10 C10 H10A 108.0 . .
C7 N2 C10 117.02(19) . .
C7 N2 Zn1 123.13(16) . .
C10 N2 Zn1 116.62(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.9229(16) 2_655
Zn1 O1 1.9229(16) .
Zn1 N2 1.953(2) 2_655
Zn1 N2 1.9526(19) .
O1 C1 1.320(3) .
C1 C2 1.414(3) .
C1 C6 1.427(3) .
C2 C3 1.377(3) .
C2 H2 0.9500 .
C3 C4 1.392(4) .
C3 H3 0.9500 .
C4 C5 1.373(3) .
C4 H4 0.9500 .
C5 C6 1.422(3) .
C5 H5 0.9500 .
C6 C7 1.495(3) .
C7 N2 1.320(3) .
C7 N1 1.345(3) .
N1 C8 1.461(3) .
N1 H1 0.88(4) .
C8 C9 1.514(3) .
C8 H8 0.9900 .
C8 H8A 0.9900 .
C9 C10 1.518(3) .
C9 H9 0.9900 .
C9 H9A 0.9900 .
C10 N2 1.471(3) .
C10 H10 0.9900 .
C10 H10A 0.9900 .
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
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88(4) 2.20(4) 3.035(3) 157(3) 6_566
C8 H8 O1 0.99 2.43 3.260(3) 141.1 5_666
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
Zn1 O1 C1 C2 174.41(15)
Zn1 O1 C1 C6 -7.1(3)
O1 C1 C2 C3 -177.6(2)
C6 C1 C2 C3 3.8(3)
C1 C2 C3 C4 1.6(4)
C2 C3 C4 C5 -3.4(4)
C3 C4 C5 C6 -0.2(4)
C4 C5 C6 C1 5.5(4)
C4 C5 C6 C7 -172.2(2)
O1 C1 C6 C5 174.5(2)
C2 C1 C6 C5 -7.0(3)
O1 C1 C6 C7 -8.1(4)
C2 C1 C6 C7 170.4(2)
C5 C6 C7 N2 -161.0(2)
C1 C6 C7 N2 21.5(4)
C5 C6 C7 N1 18.2(3)
C1 C6 C7 N1 -159.3(2)
N2 C7 N1 C8 11.0(4)
C6 C7 N1 C8 -168.2(2)
C7 N1 C8 C9 10.5(3)
N1 C8 C9 C10 -43.2(3)
C8 C9 C10 N2 58.9(3)
N1 C7 N2 C10 4.7(3)
C6 C7 N2 C10 -176.10(19)
N1 C7 N2 Zn1 163.70(17)
C6 C7 N2 Zn1 -17.1(3)
C9 C10 N2 C7 -40.1(3)
C9 C10 N2 Zn1 159.58(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168302930
