#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:46:54 +0300 (Sat, 06 May 2023) $
#$Revision: 283587 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244226.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244226
loop_
_publ_author_name
'Wark, Stephen'
'Lyons, Megan J.'
'Slawin, Alexandra M. Z.'
'Harrison, William T. A.'
_publ_section_title
;
 Consistent zincophosphite 4-ring 'ladder' chain structural motif with
 isomeric ligands.
;
_journal_coeditor_code           PK2681
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              272
_journal_page_last               279
_journal_paper_doi               10.1107/S2056989023002062
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '[Zn (H P O3) (C6 H8 N2)]'
_chemical_formula_moiety         'C6 H9 N2 O3 P Zn'
_chemical_formula_sum            'C6 H9 N2 O3 P Zn'
_chemical_formula_weight         253.49
_chemical_name_systematic
;
Poly[(2-amino-4-methylpyridine)-μ₃-phosphonato-zinc]
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 128.954(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.873(6)
_cell_length_b                   12.307(3)
_cell_length_c                   16.633(4)
_cell_measurement_reflns_used    5932
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.0
_cell_volume                     3641.1(16)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL-2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Pilatus 200K CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            50824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.317
_diffrn_reflns_theta_min         2.012
_exptl_absorpt_coefficient_mu    2.848
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear (Rigaku, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_description       rod
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0171
_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)+(0.0301P)²+3.9697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0492
_reflns_number_gt                3177
_reflns_number_total             3308
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2681sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2244225--2244229.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2244226
_cod_database_fobs_code          2244226
_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   0.764
_shelx_estimated_absorpt_t_max   0.919
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.13481(2) 0.28075(2) 0.46631(2) 0.01035(6) Uani d 1 . .
Zn Zn2 0.38505(2) 0.50195(2) 0.68663(2) 0.01038(7) Uani d 1 . .
P P1 0.30317(2) 0.28259(3) 0.65170(3) 0.01005(9) Uani d 1 . .
H H1 0.342771 0.281106 0.753047 0.012 Uiso calc 1 . .
P P2 0.46680(2) 0.44040(3) 0.59502(3) 0.01048(9) Uani d 1 . .
H H2 0.443210 0.462953 0.501255 0.013 Uiso calc 1 . .
O O1 0.22394(6) 0.24425(9) 0.60565(8) 0.0126(2) Uani d 1 . .
O O2 0.30176(6) 0.40043(9) 0.62249(8) 0.0142(2) Uani d 1 . .
O O3 0.34276(6) 0.20612(9) 0.62797(8) 0.0133(2) Uani d 1 . .
O O4 0.42559(6) 0.51766(9) 0.61527(9) 0.0151(2) Uani d 1 . .
O O5 0.55137(6) 0.45868(9) 0.66790(8) 0.0141(2) Uani d 1 . .
O O6 0.44751(6) 0.32169(9) 0.59323(9) 0.0192(3) Uani d 1 . .
C C1 0.02104(9) 0.45553(13) 0.39669(12) 0.0139(3) Uani d 1 . .
C C2 -0.00238(9) 0.56244(13) 0.39473(12) 0.0159(3) Uani d 1 . .
H H2A -0.051858 0.585125 0.338516 0.019 Uiso calc 1 . .
C C3 0.04591(9) 0.63392(13) 0.47361(12) 0.0145(3) Uani d 1 . .
C C4 0.11895(9) 0.59656(13) 0.55592(12) 0.0144(3) Uani d 1 . .
H H4 0.153296 0.642415 0.613212 0.017 Uiso calc 1 . .
C C5 0.13951(9) 0.49351(12) 0.55196(12) 0.0127(3) Uani d 1 . .
H H5 0.189116 0.470022 0.606940 0.015 Uiso calc 1 . .
C C6 0.02238(10) 0.74823(14) 0.47273(14) 0.0213(4) Uani d 1 . .
H H6A 0.063327 0.785428 0.536348 0.032 Uiso calc 1 . .
H H6B -0.022360 0.746660 0.468422 0.032 Uiso calc 1 . .
H H6C 0.010814 0.787141 0.412832 0.032 Uiso calc 1 . .
N N1 0.09243(7) 0.42276(10) 0.47310(10) 0.0120(3) Uani d 1 . .
N N2 -0.02674(9) 0.38312(13) 0.32253(12) 0.0209(3) Uani d 1 . .
H H1N -0.0668(13) 0.4006(18) 0.2726(17) 0.025 Uiso d 1 . .
H H2N -0.0154(12) 0.318(2) 0.3279(16) 0.025 Uiso d 1 . .
C C7 0.32300(8) 0.68978(13) 0.72502(11) 0.0113(3) Uani d 1 . .
C C8 0.29315(9) 0.79476(12) 0.70867(12) 0.0127(3) Uani d 1 . .
H H8 0.272479 0.816001 0.741065 0.015 Uiso calc 1 . .
C C9 0.29372(8) 0.86715(13) 0.64575(12) 0.0133(3) Uani d 1 . .
C C10 0.32631(9) 0.83349(13) 0.60142(13) 0.0168(3) Uani d 1 . .
H H10 0.329589 0.881946 0.559930 0.020 Uiso calc 1 . .
C C11 0.35344(10) 0.72937(13) 0.61886(13) 0.0160(3) Uani d 1 . .
H H11 0.374707 0.706960 0.587550 0.019 Uiso calc 1 . .
C C12 0.26058(10) 0.97887(14) 0.62570(14) 0.0187(3) Uani d 1 . .
H H12A 0.274259 1.022946 0.590688 0.028 Uiso calc 1 . .
H H12B 0.280148 1.013133 0.691512 0.028 Uiso calc 1 . .
H H12C 0.205714 0.973379 0.581816 0.028 Uiso calc 1 . .
N N3 0.35144(7) 0.65672(10) 0.67863(10) 0.0118(3) Uani d 1 . .
N N4 0.32235(8) 0.61703(11) 0.78641(11) 0.0151(3) Uani d 1 . .
H H3N 0.3081(11) 0.6407(16) 0.8213(15) 0.018 Uiso d 1 . .
H H4N 0.3543(12) 0.5680(17) 0.8129(15) 0.018 Uiso d 1 . .
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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 Zn1 O6 7_556 7_556 107.84(5) ?
O3 Zn1 O1 7_556 . 111.75(5) ?
O6 Zn1 O1 7_556 . 114.29(5) ?
O3 Zn1 N1 7_556 . 110.52(5) ?
O6 Zn1 N1 7_556 . 104.06(5) ?
O1 Zn1 N1 . . 108.11(5) ?
O4 Zn2 O2 . . 114.40(5) ?
O4 Zn2 O5 . 2_656 121.28(5) ?
O2 Zn2 O5 . 2_656 102.36(5) ?
O4 Zn2 N3 . . 100.10(5) ?
O2 Zn2 N3 . . 111.58(5) ?
O5 Zn2 N3 2_656 . 107.05(5) ?
O3 P1 O2 . . 113.78(6) ?
O3 P1 O1 . . 112.94(7) ?
O2 P1 O1 . . 110.64(6) ?
O3 P1 H1 . . 106.3 ?
O2 P1 H1 . . 106.3 ?
O1 P1 H1 . . 106.3 ?
O4 P2 O6 . . 113.14(7) ?
O4 P2 O5 . . 112.73(7) ?
O6 P2 O5 . . 111.44(6) ?
O4 P2 H2 . . 106.3 ?
O6 P2 H2 . . 106.3 ?
O5 P2 H2 . . 106.3 ?
P1 O1 Zn1 . . 123.26(6) ?
P1 O2 Zn2 . . 128.34(7) ?
P1 O3 Zn1 . 7_556 131.45(7) ?
P2 O4 Zn2 . . 133.02(7) ?
P2 O5 Zn2 . 2_656 127.58(7) ?
P2 O6 Zn1 . 7_556 144.09(8) ?
N2 C1 N1 . . 117.88(15) ?
N2 C1 C2 . . 121.14(15) ?
N1 C1 C2 . . 120.97(14) ?
C3 C2 C1 . . 120.52(15) ?
C3 C2 H2A . . 119.7 ?
C1 C2 H2A . . 119.7 ?
C2 C3 C4 . . 117.82(15) ?
C2 C3 C6 . . 121.41(15) ?
C4 C3 C6 . . 120.77(15) ?
C5 C4 C3 . . 119.16(14) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
N1 C5 C4 . . 123.38(15) ?
N1 C5 H5 . . 118.3 ?
C4 C5 H5 . . 118.3 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C1 N1 C5 . . 117.98(13) ?
C1 N1 Zn1 . . 122.59(11) ?
C5 N1 Zn1 . . 119.05(10) ?
C1 N2 H1N . . 121.4(16) ?
C1 N2 H2N . . 121.4(15) ?
H1N N2 H2N . . 117(2) ?
N3 C7 N4 . . 117.81(14) ?
N3 C7 C8 . . 121.16(14) ?
N4 C7 C8 . . 121.02(14) ?
C9 C8 C7 . . 120.32(14) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 118.03(14) ?
C8 C9 C12 . . 120.98(14) ?
C10 C9 C12 . . 120.99(14) ?
C11 C10 C9 . . 118.96(15) ?
C11 C10 H10 . . 120.5 ?
C9 C10 H10 . . 120.5 ?
N3 C11 C10 . . 123.37(15) ?
N3 C11 H11 . . 118.3 ?
C10 C11 H11 . . 118.3 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C7 N3 C11 . . 118.08(14) ?
C7 N3 Zn2 . . 123.09(10) ?
C11 N3 Zn2 . . 118.72(11) ?
C7 N4 H3N . . 117.5(13) ?
C7 N4 H4N . . 117.1(14) ?
H3N N4 H4N . . 117.4(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O3 7_556 1.9391(12) ?
Zn1 O6 7_556 1.9419(12) ?
Zn1 O1 . 1.9463(11) ?
Zn1 N1 . 2.0358(13) ?
Zn2 O4 . 1.9210(12) ?
Zn2 O2 . 1.9423(11) ?
Zn2 O5 2_656 1.9567(12) ?
Zn2 N3 . 2.0269(14) ?
P1 O3 . 1.5202(11) ?
P1 O2 . 1.5234(12) ?
P1 O1 . 1.5324(12) ?
P1 H1 . 1.3200 ?
P2 O4 . 1.5182(12) ?
P2 O6 . 1.5209(12) ?
P2 O5 . 1.5211(12) ?
P2 H2 . 1.3200 ?
C1 N2 . 1.347(2) ?
C1 N1 . 1.355(2) ?
C1 C2 . 1.413(2) ?
C2 C3 . 1.376(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.415(2) ?
C3 C6 . 1.503(2) ?
C4 C5 . 1.368(2) ?
C4 H4 . 0.9500 ?
C5 N1 . 1.365(2) ?
C5 H5 . 0.9500 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
N2 H1N . 0.79(2) ?
N2 H2N . 0.82(2) ?
C7 N3 . 1.347(2) ?
C7 N4 . 1.365(2) ?
C7 C8 . 1.406(2) ?
C8 C9 . 1.381(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.401(2) ?
C9 C12 . 1.503(2) ?
C10 C11 . 1.373(2) ?
C10 H10 . 0.9500 ?
C11 N3 . 1.359(2) ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
N4 H3N . 0.88(2) ?
N4 H4N . 0.83(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H1N O3 8_455 0.79(2) 2.35(2) 2.9056(19) 128(2) yes
N2 H2N O6 7_556 0.82(2) 2.13(2) 2.900(2) 155(2) yes
N4 H3N O1 4_556 0.88(2) 2.18(2) 3.0310(18) 163.7(18) yes
N4 H4N O5 2_656 0.83(2) 2.39(2) 3.1555(19) 154.3(18) yes
C5 H5 O2 . 0.95 2.57 3.315(2) 136 yes
C8 H8 O1 4_556 0.95 2.65 3.405(2) 137 yes
C11 H11 O4 . 0.95 2.51 3.105(2) 120 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 P1 O1 Zn1 . . . . -87.69(9) ?
O2 P1 O1 Zn1 . . . . 41.16(9) ?
O3 P1 O2 Zn2 . . . . -69.80(10) ?
O1 P1 O2 Zn2 . . . . 161.80(7) ?
O2 P1 O3 Zn1 . . . 7_556 -20.85(11) ?
O1 P1 O3 Zn1 . . . 7_556 106.36(9) ?
O6 P2 O4 Zn2 . . . . 26.92(12) ?
O5 P2 O4 Zn2 . . . . -100.68(10) ?
O4 P2 O5 Zn2 . . . 2_656 35.10(11) ?
O6 P2 O5 Zn2 . . . 2_656 -93.38(9) ?
O4 P2 O6 Zn1 . . . 7_556 51.37(15) ?
O5 P2 O6 Zn1 . . . 7_556 179.64(11) ?
N2 C1 C2 C3 . . . . 176.82(15) ?
N1 C1 C2 C3 . . . . -3.5(2) ?
C1 C2 C3 C4 . . . . -0.2(2) ?
C1 C2 C3 C6 . . . . 179.55(15) ?
C2 C3 C4 C5 . . . . 2.6(2) ?
C6 C3 C4 C5 . . . . -177.19(15) ?
C3 C4 C5 N1 . . . . -1.5(2) ?
N2 C1 N1 C5 . . . . -175.71(14) ?
C2 C1 N1 C5 . . . . 4.6(2) ?
N2 C1 N1 Zn1 . . . . 11.4(2) ?
C2 C1 N1 Zn1 . . . . -168.38(11) ?
C4 C5 N1 C1 . . . . -2.1(2) ?
C4 C5 N1 Zn1 . . . . 171.05(12) ?
N3 C7 C8 C9 . . . . -1.2(2) ?
N4 C7 C8 C9 . . . . -179.53(15) ?
C7 C8 C9 C10 . . . . -1.5(2) ?
C7 C8 C9 C12 . . . . 178.71(14) ?
C8 C9 C10 C11 . . . . 2.5(2) ?
C12 C9 C10 C11 . . . . -177.66(15) ?
C9 C10 C11 N3 . . . . -1.0(3) ?
N4 C7 N3 C11 . . . . -178.87(14) ?
C8 C7 N3 C11 . . . . 2.8(2) ?
N4 C7 N3 Zn2 . . . . 5.08(19) ?
C8 C7 N3 Zn2 . . . . -173.28(11) ?
C10 C11 N3 C7 . . . . -1.7(2) ?
C10 C11 N3 Zn2 . . . . 174.54(13) ?
