#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:39:25 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266184 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/31/1563169.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_1563169
loop_
_publ_author_name
'MITSUHASHI, Ryoji'
_publ_section_title
;
 Synthesis and Crystal Structure of
 Bis[2-(2-imidazolinyl)-6-methoxyphenolato]zinc(II)
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              25
_journal_page_last               26
_journal_paper_doi               10.2116/xraystruct.37.25
_journal_volume                  37
_journal_year                    2021
_chemical_formula_moiety         'C20 H22 N4 O4 Zn, C H4 O'
_chemical_formula_sum            'C21 H26 N4 O5 Zn'
_chemical_formula_weight         479.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 104.253(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6485(5)
_cell_length_b                   19.2428(6)
_cell_length_c                   7.5851(3)
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0490
_cell_measurement_theta_min      2.5350
_cell_volume                     2072.26(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14475
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.557
_exptl_absorpt_coefficient_mu    1.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0428P)²+0.7182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3799
_reflns_number_total             4597
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            37_25_1.txt
_cod_data_source_block           RMI67_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1563169
_shelx_shelxl_version_number     2018/1
_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   0.809
_shelx_estimated_absorpt_t_max   0.919
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.69755(2) 0.49876(2) 0.42830(3) 0.01588(8) Uani 1 1 d . . . . .
O1 O 0.74456(8) 0.44673(6) 0.65107(18) 0.0190(3) Uani 1 1 d . . . . .
C1 C 0.81665(11) 0.40395(9) 0.6793(2) 0.0153(4) Uani 1 1 d . . . . .
C2 C 0.83144(12) 0.36041(9) 0.8360(2) 0.0166(4) Uani 1 1 d . . . . .
C3 C 0.90342(12) 0.31283(9) 0.8779(3) 0.0198(4) Uani 1 1 d . . . . .
H3 H 0.910295 0.283933 0.981906 0.024 Uiso 1 1 calc R U . . .
C4 C 0.96638(12) 0.30700(9) 0.7677(3) 0.0212(4) Uani 1 1 d . . . . .
H4 H 1.016195 0.274098 0.796351 0.025 Uiso 1 1 calc R U . . .
C5 C 0.95636(12) 0.34871(9) 0.6181(3) 0.0183(4) Uani 1 1 d . . . . .
H5 H 1.000012 0.344708 0.544460 0.022 Uiso 1 1 calc R U . . .
C6 C 0.88231(11) 0.39768(9) 0.5708(2) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.87762(12) 0.44152(9) 0.4099(3) 0.0164(4) Uani 1 1 d . . . . .
N1 N 0.94892(11) 0.44381(9) 0.3275(2) 0.0258(4) Uani 1 1 d D . . . .
H1N H 1.0006(11) 0.4265(10) 0.363(3) 0.021(5) Uiso 1 1 d D . . . .
C8 C 0.92760(13) 0.49037(9) 0.1720(3) 0.0192(4) Uani 1 1 d . . . . .
H8A H 0.925278 0.465143 0.057193 0.023 Uiso 1 1 calc R U . . .
H8B H 0.974230 0.528484 0.185872 0.023 Uiso 1 1 calc R U . . .
C9 C 0.83001(14) 0.51775(11) 0.1785(3) 0.0240(4) Uani 1 1 d . . . . .
H9A H 0.832046 0.568510 0.200367 0.029 Uiso 1 1 calc R U . . .
H9B H 0.783140 0.507935 0.062799 0.029 Uiso 1 1 calc R U . . .
N2 N 0.80614(10) 0.48035(8) 0.3304(2) 0.0174(3) Uani 1 1 d . . . . .
O2 O 0.76721(8) 0.37103(7) 0.93832(18) 0.0206(3) Uani 1 1 d . . . . .
C10 C 0.77123(14) 0.32432(10) 1.0864(3) 0.0244(4) Uani 1 1 d . . . . .
H10A H 0.761354 0.276655 1.040132 0.037 Uiso 1 1 calc R U . . .
H10B H 0.722015 0.336459 1.148209 0.037 Uiso 1 1 calc R U . . .
H10C H 0.833080 0.327798 1.172498 0.037 Uiso 1 1 calc R U . . .
O3 O 0.69033(8) 0.59715(6) 0.47319(19) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.61300(12) 0.63422(9) 0.4447(2) 0.0156(4) Uani 1 1 d . . . . .
C12 C 0.62286(12) 0.70439(9) 0.5068(3) 0.0182(4) Uani 1 1 d . . . . .
C13 C 0.54755(13) 0.74842(10) 0.4862(3) 0.0229(4) Uani 1 1 d . . . . .
H13 H 0.556182 0.794697 0.530832 0.028 Uiso 1 1 calc R U . . .
C14 C 0.45758(13) 0.72433(10) 0.3984(3) 0.0261(5) Uani 1 1 d . . . . .
H14 H 0.404910 0.754554 0.382768 0.031 Uiso 1 1 calc R U . . .
C15 C 0.44511(12) 0.65780(10) 0.3352(3) 0.0218(4) Uani 1 1 d . . . . .
H15 H 0.383699 0.642603 0.274558 0.026 Uiso 1 1 calc R U . . .
C16 C 0.52128(12) 0.61094(9) 0.3576(2) 0.0158(4) Uani 1 1 d . . . . .
C17 C 0.50218(12) 0.53974(9) 0.2886(2) 0.0150(4) Uani 1 1 d . . . . .
N3 N 0.41426(11) 0.52068(9) 0.1969(2) 0.0196(3) Uani 1 1 d D . . . .
H3N H 0.3696(13) 0.5409(11) 0.214(3) 0.024(6) Uiso 1 1 d D . . . .
C18 C 0.41229(12) 0.44684(10) 0.1532(3) 0.0194(4) Uani 1 1 d . . . . .
H18A H 0.385471 0.438745 0.021749 0.023 Uiso 1 1 calc R U . . .
H18B H 0.375446 0.420289 0.223680 0.023 Uiso 1 1 calc R U . . .
C19 C 0.51740(12) 0.42713(9) 0.2097(3) 0.0184(4) Uani 1 1 d . . . . .
H19A H 0.527817 0.387026 0.294068 0.022 Uiso 1 1 calc R U . . .
H19B H 0.541062 0.415258 0.101955 0.022 Uiso 1 1 calc R U . . .
N4 N 0.56463(10) 0.49004(7) 0.3008(2) 0.0159(3) Uani 1 1 d . . . . .
O4 O 0.71407(9) 0.72204(7) 0.5881(2) 0.0262(3) Uani 1 1 d . . . . .
C20 C 0.73499(14) 0.79331(10) 0.6234(3) 0.0271(4) Uani 1 1 d . . . . .
H20A H 0.715027 0.819767 0.509973 0.041 Uiso 1 1 calc R U . . .
H20B H 0.802956 0.799036 0.672863 0.041 Uiso 1 1 calc R U . . .
H20C H 0.701444 0.810445 0.711621 0.041 Uiso 1 1 calc R U . . .
O5 O 0.87655(9) 0.62737(8) 0.62781(19) 0.0250(3) Uani 1 1 d . . . . .
H5A H 0.8217(17) 0.6281(13) 0.563(2) 0.038 Uiso 1 1 calc R U . . .
C21 C 0.87443(15) 0.62611(15) 0.8113(3) 0.0406(6) Uani 1 1 d . . . . .
H21A H 0.851017 0.670748 0.844306 0.061 Uiso 1 1 calc R U . . .
H21B H 0.938137 0.617980 0.886894 0.061 Uiso 1 1 calc R U . . .
H21C H 0.832671 0.588710 0.831230 0.061 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
O3 Zn1 O1 112.07(6) . . ?
O3 Zn1 N2 109.33(6) . . ?
O1 Zn1 N2 95.17(6) . . ?
O3 Zn1 N4 94.60(5) . . ?
O1 Zn1 N4 118.89(6) . . ?
N2 Zn1 N4 127.11(7) . . ?
C1 O1 Zn1 124.36(12) . . ?
O1 C1 C6 126.27(16) . . ?
O1 C1 C2 117.06(16) . . ?
C6 C1 C2 116.66(15) . . ?
C3 C2 O2 124.20(17) . . ?
C3 C2 C1 122.33(17) . . ?
O2 C2 C1 113.48(15) . . ?
C2 C3 C4 119.92(18) . . ?
C5 C4 C3 119.92(17) . . ?
C4 C5 C6 121.35(18) . . ?
C5 C6 C1 119.80(17) . . ?
C5 C6 C7 117.96(16) . . ?
C1 C6 C7 122.23(15) . . ?
N2 C7 N1 113.13(17) . . ?
N2 C7 C6 125.41(16) . . ?
N1 C7 C6 121.45(16) . . ?
C7 N1 C8 111.21(15) . . ?
N1 C8 C9 101.61(15) . . ?
N2 C9 C8 105.06(15) . . ?
C7 N2 C9 108.86(15) . . ?
C7 N2 Zn1 124.42(13) . . ?
C9 N2 Zn1 125.70(12) . . ?
C2 O2 C10 116.68(14) . . ?
C11 O3 Zn1 125.95(11) . . ?
O3 C11 C16 125.94(16) . . ?
O3 C11 C12 116.60(15) . . ?
C16 C11 C12 117.46(15) . . ?
C13 C12 O4 124.58(17) . . ?
C13 C12 C11 122.34(16) . . ?
O4 C12 C11 113.08(15) . . ?
C12 C13 C14 119.13(18) . . ?
C15 C14 C13 120.44(17) . . ?
C14 C15 C16 121.59(17) . . ?
C15 C16 C11 119.02(16) . . ?
C15 C16 C17 118.50(15) . . ?
C11 C16 C17 122.48(15) . . ?
N4 C17 N3 113.41(16) . . ?
N4 C17 C16 125.95(16) . . ?
N3 C17 C16 120.60(16) . . ?
C17 N3 C18 110.10(15) . . ?
N3 C18 C19 102.37(14) . . ?
N4 C19 C18 104.43(14) . . ?
C17 N4 C19 109.04(14) . . ?
C17 N4 Zn1 124.37(12) . . ?
C19 N4 Zn1 126.55(11) . . ?
C12 O4 C20 117.83(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.9312(13) . ?
Zn1 O1 1.9388(13) . ?
Zn1 N2 1.9464(15) . ?
Zn1 N4 1.9563(15) . ?
O1 C1 1.314(2) . ?
C1 C6 1.417(3) . ?
C1 C2 1.426(2) . ?
C2 C3 1.373(2) . ?
C2 O2 1.374(2) . ?
C3 C4 1.394(3) . ?
C4 C5 1.368(3) . ?
C5 C6 1.415(2) . ?
C6 C7 1.471(3) . ?
C7 N2 1.307(2) . ?
C7 N1 1.344(2) . ?
N1 C8 1.453(2) . ?
C8 C9 1.536(3) . ?
C9 N2 1.472(3) . ?
O2 C10 1.429(2) . ?
O3 C11 1.311(2) . ?
C11 C16 1.416(2) . ?
C11 C12 1.426(2) . ?
C12 C13 1.369(2) . ?
C12 O4 1.369(2) . ?
C13 C14 1.401(3) . ?
C14 C15 1.364(3) . ?
C15 C16 1.412(2) . ?
C16 C17 1.469(2) . ?
C17 N4 1.311(2) . ?
C17 N3 1.355(2) . ?
N3 C18 1.458(2) . ?
C18 C19 1.540(2) . ?
C19 N4 1.479(2) . ?
O4 C20 1.416(2) . ?
O5 C21 1.400(3) . ?
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
_geom_hbond_publ_flag
N1 H1N O5 0.810(15) 2.063(16) 2.846(2) 162(2) 3_766 yes
N3 H3N O1 0.799(15) 2.178(18) 2.908(2) 152(2) 3_666 yes
O5 H5A O3 0.83 1.97 2.7530(18) 156.7 . yes
O5 H5A O4 0.83 2.44 2.9530(18) 121.0 . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 C6 12.4(2) . . . . ?
Zn1 O1 C1 C2 -168.84(11) . . . . ?
O1 C1 C2 C3 178.86(16) . . . . ?
C6 C1 C2 C3 -2.2(2) . . . . ?
O1 C1 C2 O2 -1.1(2) . . . . ?
C6 C1 C2 O2 177.78(14) . . . . ?
O2 C2 C3 C4 -178.54(16) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 178.79(16) . . . . ?
O1 C1 C6 C5 -179.64(16) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
O1 C1 C6 C7 1.4(3) . . . . ?
C2 C1 C6 C7 -177.37(15) . . . . ?
C5 C6 C7 N2 167.73(17) . . . . ?
C1 C6 C7 N2 -13.3(3) . . . . ?
C5 C6 C7 N1 -10.9(3) . . . . ?
C1 C6 C7 N1 168.06(17) . . . . ?
N2 C7 N1 C8 1.0(2) . . . . ?
C6 C7 N1 C8 179.73(16) . . . . ?
C7 N1 C8 C9 1.5(2) . . . . ?
N1 C8 C9 N2 -3.1(2) . . . . ?
N1 C7 N2 C9 -3.1(2) . . . . ?
C6 C7 N2 C9 178.19(17) . . . . ?
N1 C7 N2 Zn1 -172.10(13) . . . . ?
C6 C7 N2 Zn1 9.2(3) . . . . ?
C8 C9 N2 C7 3.8(2) . . . . ?
C8 C9 N2 Zn1 172.65(12) . . . . ?
C3 C2 O2 C10 -6.5(2) . . . . ?
C1 C2 O2 C10 173.51(15) . . . . ?
Zn1 O3 C11 C16 -7.3(3) . . . . ?
Zn1 O3 C11 C12 172.98(12) . . . . ?
O3 C11 C12 C13 -179.67(18) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
O3 C11 C12 O4 0.1(2) . . . . ?
C16 C11 C12 O4 -179.67(16) . . . . ?
O4 C12 C13 C14 179.20(18) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C14 C15 C16 C17 178.99(18) . . . . ?
O3 C11 C16 C15 -179.14(17) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
O3 C11 C16 C17 0.5(3) . . . . ?
C12 C11 C16 C17 -179.70(16) . . . . ?
C15 C16 C17 N4 -179.08(18) . . . . ?
C11 C16 C17 N4 1.2(3) . . . . ?
C15 C16 C17 N3 3.5(3) . . . . ?
C11 C16 C17 N3 -176.18(17) . . . . ?
N4 C17 N3 C18 5.9(2) . . . . ?
C16 C17 N3 C18 -176.40(16) . . . . ?
C17 N3 C18 C19 -8.0(2) . . . . ?
N3 C18 C19 N4 7.24(19) . . . . ?
N3 C17 N4 C19 -0.7(2) . . . . ?
C16 C17 N4 C19 -178.24(17) . . . . ?
N3 C17 N4 Zn1 -178.59(12) . . . . ?
C16 C17 N4 Zn1 3.8(3) . . . . ?
C18 C19 N4 C17 -4.4(2) . . . . ?
C18 C19 N4 Zn1 173.48(12) . . . . ?
C13 C12 O4 C20 -12.1(3) . . . . ?
C11 C12 O4 C20 168.11(17) . . . . ?
