#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:21:57 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301837 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/99/4319965.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_4319965
loop_
_publ_author_name
'Krystyna Brandt'
'Piotr Seliger'
'Andrzej Grzejdziak'
'Tadeusz J. Bartczak'
'Rafat Kruszynski'
'Dariusz Lach'
'Jerzy Silberring'
_publ_section_title
;
 Structure-Property Relationships of a Tetrapyrrolidinyl PNP-Lariat Ether
 and Its Complexes with Potassium, Sodium, and Silver Cations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3704
_journal_page_last               3710
_journal_paper_doi               10.1021/ic000430q
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C24 H48 N7 O5 P3'
_chemical_formula_weight         607.60
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.730(10)
_cell_angle_beta                 75.540(10)
_cell_angle_gamma                82.720(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2510(10)
_cell_length_b                   9.6780(10)
_cell_length_c                   17.994(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1542.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6277
_diffrn_reflns_theta_full        80.91
_diffrn_reflns_theta_max         80.91
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_T_max  0.5651
_exptl_absorpt_correction_T_min  0.5651
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.0062(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6086
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.2186
_refine_ls_R_factor_gt           0.0810
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1850P)²+0.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2306
_refine_ls_wR_factor_ref         0.3349
_reflns_number_gt                1975
_reflns_number_total             6086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic000430q_2.cif
_cod_data_source_block           ligand
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1850P)^2^+0.1626P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1850P)^2^+0.1626P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4319965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4559(6) -0.1544(6) 0.2970(4) 0.1238(18) Uani 1 d . . .
P1 P 0.2862(2) -0.11345(16) 0.31754(13) 0.1175(8) Uani 1 d . . .
N4 N 0.2072(7) -0.2501(5) 0.3606(4) 0.143(2) Uani 1 d . . .
C9 C 0.0456(9) -0.2384(9) 0.3965(6) 0.177(4) Uani 1 d . . .
H9A H 0.0285 -0.2200 0.4495 0.265 Uiso 1 d R . .
H9B H -0.0069 -0.1642 0.3706 0.265 Uiso 1 d R . .
C10 C -0.0003(15) -0.3703(14) 0.3918(10) 0.269(8) Uani 1 d . . .
H10A H -0.0504 -0.4076 0.4420 0.403 Uiso 1 d R . .
H10B H -0.0708 -0.3571 0.3599 0.403 Uiso 1 d R . .
C11 C 0.1171(15) -0.4625(11) 0.3619(9) 0.234(6) Uani 1 d . . .
H11A H 0.0970 -0.5020 0.3193 0.351 Uiso 1 d R . .
H11B H 0.1318 -0.5372 0.3999 0.351 Uiso 1 d R . .
C12 C 0.2533(10) -0.3871(7) 0.3327(6) 0.164(3) Uani 1 d . . .
H12A H 0.3329 -0.4334 0.3546 0.245 Uiso 1 d R . .
H12B H 0.2870 -0.3818 0.2776 0.245 Uiso 1 d R . .
P2 P 0.29907(17) -0.00613(13) 0.16634(13) 0.1076(8) Uani 1 d . . .
N5 N 0.2858(5) 0.1592(4) 0.1394(4) 0.124(2) Uani 1 d . . .
C13 C 0.3918(7) 0.2541(5) 0.1404(6) 0.146(3) Uani 1 d . . .
H13A H 0.4831 0.2358 0.1019 0.219 Uiso 1 d R . .
H13B H 0.4150 0.2448 0.1899 0.219 Uiso 1 d R . .
C14 C 0.3202(10) 0.3938(6) 0.1256(7) 0.189(4) Uani 1 d . . .
H14A H 0.3378 0.4566 0.1594 0.284 Uiso 1 d R . .
H14B H 0.3599 0.4286 0.0734 0.284 Uiso 1 d R . .
C15 C 0.1622(10) 0.3821(7) 0.1387(8) 0.225(6) Uani 1 d . . .
H15A H 0.1248 0.4325 0.0972 0.338 Uiso 1 d R . .
H15B H 0.1096 0.4225 0.1856 0.338 Uiso 1 d R . .
C16 C 0.1351(7) 0.2373(6) 0.1445(6) 0.170(4) Uani 1 d . . .
H16A H 0.0942 0.2190 0.1030 0.255 Uiso 1 d R . .
H16B H 0.0671 0.2121 0.1925 0.255 Uiso 1 d R . .
N6 N 0.2082(5) -0.0676(4) 0.1106(4) 0.1129(18) Uani 1 d . . .
C17 C 0.2587(10) -0.0491(9) 0.0255(6) 0.163(3) Uani 1 d . . .
H17A H 0.3663 -0.0594 0.0095 0.245 Uiso 1 d R . .
H17B H 0.2219 0.0422 0.0071 0.245 Uiso 1 d R . .
C18 C 0.1935(11) -0.1595(11) -0.0035(6) 0.181(4) Uani 1 d . . .
H18A H 0.1398 -0.1190 -0.0412 0.271 Uiso 1 d R . .
H18B H 0.2722 -0.2269 -0.0271 0.271 Uiso 1 d R . .
C19 C 0.0929(11) -0.2250(8) 0.0628(6) 0.165(3) Uani 1 d . . .
H19A H 0.1004 -0.3238 0.0583 0.247 Uiso 1 d R . .
H19B H -0.0090 -0.1867 0.0654 0.247 Uiso 1 d R . .
C20 C 0.1402(8) -0.1983(6) 0.1313(5) 0.129(2) Uani 1 d . . .
H20A H 0.0549 -0.1881 0.1742 0.194 Uiso 1 d R . .
H20B H 0.2105 -0.2728 0.1446 0.194 Uiso 1 d R . .
N2 N 0.2087(5) -0.0389(5) 0.2526(4) 0.1129(17) Uani 1 d . . .
P3 P 0.55001(19) -0.14648(15) 0.21036(16) 0.1213(9) Uani 1 d . . .
N7 N 0.6002(7) -0.3036(5) 0.1827(5) 0.133(2) Uani 1 d . . .
C21 C 0.6472(9) -0.3322(7) 0.1049(6) 0.146(3) Uani 1 d . . .
H21A H 0.7151 -0.2673 0.0764 0.218 Uiso 1 d R . .
H21B H 0.5625 -0.3256 0.0824 0.218 Uiso 1 d R . .
C22 C 0.7250(11) -0.4813(9) 0.1042(8) 0.180(4) Uani 1 d . . .
H22A H 0.6728 -0.5419 0.0837 0.270 Uiso 1 d R . .
H22B H 0.8267 -0.4831 0.0741 0.270 Uiso 1 d R . .
C23 C 0.7191(15) -0.5227(11) 0.1845(9) 0.229(6) Uani 1 d . . .
H23A H 0.8169 -0.5645 0.1887 0.344 Uiso 1 d R . .
H23B H 0.6505 -0.5924 0.2026 0.344 Uiso 1 d R . .
C24 C 0.6765(11) -0.4098(7) 0.2324(7) 0.183(4) Uani 1 d . . .
H24A H 0.7619 -0.3755 0.2427 0.275 Uiso 1 d R . .
H24B H 0.6094 -0.4370 0.2803 0.275 Uiso 1 d R . .
N3 N 0.4732(5) -0.0549(4) 0.1491(3) 0.1102(17) Uani 1 d . . .
O1 O 0.2436(6) -0.0198(5) 0.3883(3) 0.1502(19) Uani 1 d D . .
C1 C 0.2601(13) 0.1198(9) 0.3809(7) 0.193(4) Uani 1 d D . .
H1A H 0.1635 0.1657 0.4038 0.290 Uiso 1 d R . .
H1B H 0.2808 0.1479 0.3267 0.290 Uiso 1 d R . .
C2 C 0.3580(18) 0.176(2) 0.4179(12) 0.301(12) Uani 1 d D . .
H2A H 0.4551 0.1259 0.4004 0.452 Uiso 1 d R . .
H2B H 0.3644 0.2732 0.4018 0.452 Uiso 1 d R . .
O2 O 0.3376(16) 0.1630(11) 0.4915(9) 0.330(9) Uani 1 d D . .
C3 C 0.3733(17) 0.2910(15) 0.5028(16) 0.45(2) Uani 1 d D . .
H3A H 0.3301 0.3809 0.4861 0.676 Uiso 1 d R . .
H3B H 0.3353 0.2782 0.5575 0.676 Uiso 1 d R . .
C4 C 0.528(2) 0.2847(18) 0.5049(8) 0.245(7) Uani 1 d D . .
H4A H 0.5445 0.3475 0.5390 0.367 Uiso 1 d R . .
H4B H 0.5720 0.1936 0.5191 0.367 Uiso 1 d R . .
O3 O 0.6116(12) 0.3280(9) 0.4320(7) 0.206(3) Uani 1 d D . .
C5 C 0.7673(18) 0.3110(15) 0.4072(9) 0.234(6) Uani 1 d D . .
H5A H 0.7925 0.3835 0.3667 0.350 Uiso 1 d R . .
H5B H 0.8126 0.3264 0.4477 0.350 Uiso 1 d R . .
C6 C 0.8259(14) 0.1829(15) 0.3747(9) 0.230(6) Uani 1 d D . .
H6A H 0.9335 0.1780 0.3624 0.346 Uiso 1 d R . .
H6B H 0.7948 0.1076 0.4125 0.346 Uiso 1 d R . .
O4 O 0.7826(7) 0.1761(6) 0.3041(5) 0.169(2) Uani 1 d D . .
C7 C 0.7883(9) 0.0414(8) 0.2857(6) 0.147(3) Uani 1 d D . .
H7A H 0.8917 0.0065 0.2677 0.221 Uiso 1 d R . .
H7B H 0.7439 -0.0196 0.3287 0.221 Uiso 1 d R . .
C8 C 0.7152(9) 0.0420(7) 0.2256(6) 0.157(3) Uani 1 d D . .
H8A H 0.6153 0.0875 0.2414 0.235 Uiso 1 d R . .
H8B H 0.7670 0.0939 0.1803 0.235 Uiso 1 d R . .
O5 O 0.7070(5) -0.0926(5) 0.2063(4) 0.152(2) Uani 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
P1 N1 P3 121.2(4) . . ?
N1 P1 O1 109.4(3) . . ?
N1 P1 N2 118.9(4) . . ?
O1 P1 N2 108.6(3) . . ?
N1 P1 N4 107.5(3) . . ?
O1 P1 N4 98.0(3) . . ?
N2 P1 N4 112.4(3) . . ?
C12 N4 C9 109.2(6) . . ?
C12 N4 P1 121.9(6) . . ?
C9 N4 P1 120.1(5) . . ?
C10 C9 N4 105.2(8) . . ?
C11 C10 C9 111.9(10) . . ?
C10 C11 C12 108.9(9) . . ?
N4 C12 C11 103.9(8) . . ?
N3 P2 N2 115.3(3) . . ?
N3 P2 N5 105.5(2) . . ?
N2 P2 N5 112.4(3) . . ?
N3 P2 N6 114.8(3) . . ?
N2 P2 N6 106.6(3) . . ?
N5 P2 N6 101.5(3) . . ?
C13 N5 C16 109.6(5) . . ?
C13 N5 P2 126.0(4) . . ?
C16 N5 P2 119.5(4) . . ?
N5 C13 C14 106.3(6) . . ?
C15 C14 C13 106.9(6) . . ?
C16 C15 C14 110.4(6) . . ?
C15 C16 N5 104.2(6) . . ?
C20 N6 C17 108.2(6) . . ?
C20 N6 P2 122.2(6) . . ?
C17 N6 P2 121.0(4) . . ?
N6 C17 C18 105.4(7) . . ?
C19 C18 C17 106.8(8) . . ?
C18 C19 C20 107.1(7) . . ?
N6 C20 C19 104.9(7) . . ?
P1 N2 P2 122.8(3) . . ?
N1 P3 O5 109.0(3) . . ?
N1 P3 N3 116.8(3) . . ?
O5 P3 N3 109.2(3) . . ?
N1 P3 N7 109.7(4) . . ?
O5 P3 N7 102.0(3) . . ?
N3 P3 N7 109.0(3) . . ?
C21 N7 C24 111.0(6) . . ?
C21 N7 P3 123.2(5) . . ?
C24 N7 P3 118.4(6) . . ?
N7 C21 C22 106.0(8) . . ?
C23 C22 C21 103.8(9) . . ?
C24 C23 C22 113.6(9) . . ?
C23 C24 N7 100.9(8) . . ?
P2 N3 P3 122.7(4) . . ?
C1 O1 P1 123.1(7) . . ?
O1 C1 C2 121.8(12) . . ?
O2 C2 C1 121.2(17) . . ?
C2 O2 C3 99.6(16) . . ?
O2 C3 C4 111.1(13) . . ?
O3 C4 C3 109.0(14) . . ?
C5 O3 C4 125.8(12) . . ?
O3 C5 C6 114.3(10) . . ?
C5 C6 O4 111.0(10) . . ?
C7 O4 C6 112.5(9) . . ?
O4 C7 C8 108.8(7) . . ?
O5 C8 C7 112.7(7) . . ?
C8 O5 P3 121.0(5) . . ?
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
N1 P1 1.531(5) . ?
N1 P3 1.584(6) . ?
P1 O1 1.584(6) . ?
P1 N2 1.582(6) . ?
P1 N4 1.619(6) . ?
N4 C12 1.445(9) . ?
N4 C9 1.468(9) . ?
C9 C10 1.413(14) . ?
C10 C11 1.355(14) . ?
C11 C12 1.488(12) . ?
P2 N3 1.582(4) . ?
P2 N2 1.587(6) . ?
P2 N5 1.619(4) . ?
P2 N6 1.656(6) . ?
N5 C13 1.431(7) . ?
N5 C16 1.486(7) . ?
C13 C14 1.456(9) . ?
C14 C15 1.438(10) . ?
C15 C16 1.442(9) . ?
N6 C20 1.455(7) . ?
N6 C17 1.483(10) . ?
C17 C18 1.491(11) . ?
C18 C19 1.457(11) . ?
C19 C20 1.464(10) . ?
P3 O5 1.586(5) . ?
P3 N3 1.589(5) . ?
P3 N7 1.627(6) . ?
N7 C21 1.405(10) . ?
N7 C24 1.513(9) . ?
C21 C22 1.529(10) . ?
C22 C23 1.446(14) . ?
C23 C24 1.421(12) . ?
O1 C1 1.367(9) . ?
C1 C2 1.437(12) . ?
C2 O2 1.284(15) . ?
O2 C3 1.370(15) . ?
C3 C4 1.432(15) . ?
C4 O3 1.398(12) . ?
O3 C5 1.391(12) . ?
C5 C6 1.415(12) . ?
C6 O4 1.435(11) . ?
O4 C7 1.371(8) . ?
C7 C8 1.411(9) . ?
C8 O5 1.400(7) . ?
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
P3 N1 P1 O1 -135.6(4) . . . . ?
N1 P1 O1 C1 80.3(8) . . . . ?
P1 O1 C1 C2 -118.4(13) . . . . ?
O1 C1 C2 O2 -60(2) . . . . ?
C1 C2 O2 C3 -141.8(18) . . . . ?
C2 O2 C3 C4 -94(2) . . . . ?
O2 C3 C4 O3 96(2) . . . . ?
C3 C4 O3 C5 -166.7(12) . . . . ?
C4 O3 C5 C6 88.4(17) . . . . ?
O3 C5 C6 O4 66.2(16) . . . . ?
C5 C6 O4 C7 -157.9(11) . . . . ?
C6 O4 C7 C8 167.8(9) . . . . ?
O4 C7 C8 O5 -176.1(6) . . . . ?
C7 C8 O5 P3 122.1(7) . . . . ?
C8 O5 P3 N1 -64.5(7) . . . . ?
O5 P3 N1 P1 141.7(4) . . . . ?
P3 N1 P1 O1 -135.6(4) . . . . ?
N1 P1 N2 P2 0.8(5) . . . . ?
P1 N2 P2 N3 0.7(5) . . . . ?
N2 P2 N3 P3 7.2(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139133742
