#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/40/1504079.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_1504079
loop_
_publ_author_name
'Kang, Sung Ok'
'Day, Victor W.'
'Bowman-James, Kristin'
_publ_section_title
;
 The influence of amine functionalities on anion binding in
 polyamide-containing macrocycles.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3654
_journal_page_last               3657
_journal_paper_doi               10.1021/ol9014249
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C26 H54 N8 O18 P2'
_chemical_formula_weight         828.71
_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                108.885(2)
_cell_angle_beta                 93.062(2)
_cell_angle_gamma                107.523(2)
_cell_formula_units_Z            1
_cell_length_a                   8.1169(11)
_cell_length_b                   11.2001(15)
_cell_length_c                   11.4236(15)
_cell_measurement_reflns_used    4690
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.67
_cell_volume                     923.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5212
_diffrn_reflns_theta_full        21.50
_diffrn_reflns_theta_max         21.50
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular plate'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0107P)²+15.6331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                1958
_reflns_number_total             2117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9014249_si_002.cif
_cod_data_source_block           k97f_(Compnd_B)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P_-1
_cod_database_code               1504079
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.3771(7) 0.3985(5) -0.2760(5) 0.0198(14) Uani 1 1 d .
O2 O 0.1594(7) 0.5842(6) 0.3310(5) 0.0251(14) Uani 1 1 d .
N1 N 0.1946(9) -0.1714(7) -0.4940(6) 0.0204(17) Uani 1 1 d .
H1N1 H 0.189(10) -0.126(8) -0.562(8) 0.025 Uiso 1 1 d .
H1N2 H 0.227(11) -0.236(9) -0.533(8) 0.025 Uiso 1 1 d .
C2 C 0.3225(10) -0.0637(8) -0.3844(7) 0.0175(19) Uani 1 1 d .
H2A H 0.4331 -0.0269 -0.4131 0.021 Uiso 1 1 calc R
H2B H 0.3488 -0.1031 -0.3226 0.021 Uiso 1 1 calc R
C3 C 0.2547(10) 0.0497(8) -0.3205(7) 0.0167(19) Uani 1 1 d .
H3A H 0.1622 0.0196 -0.2731 0.020 Uiso 1 1 calc R
H3B H 0.2035 0.0767 -0.3843 0.020 Uiso 1 1 calc R
C4 C 0.4075(10) 0.1687(8) -0.2311(7) 0.0192(19) Uani 1 1 d .
H4A H 0.4712 0.1368 -0.1781 0.023 Uiso 1 1 calc R
H4B H 0.4900 0.2070 -0.2808 0.023 Uiso 1 1 calc R
N5 N 0.3496(8) 0.2725(7) -0.1512(6) 0.0186(16) Uani 1 1 d .
H5N H 0.3201 0.2661 -0.0799 0.022 Uiso 1 1 calc R
C6 C 0.3381(9) 0.3767(8) -0.1782(7) 0.0150(19) Uani 1 1 d .
C7 C 0.2788(10) 0.4721(8) -0.0801(7) 0.0154(19) Uani 1 1 d .
N8 N 0.2586(8) 0.4480(7) 0.0278(6) 0.0182(16) Uani 1 1 d .
C9 C 0.2448(10) 0.5804(8) -0.0987(8) 0.019(2) Uani 1 1 d .
H9 H 0.2593 0.5956 -0.1752 0.023 Uiso 1 1 calc R
C10 C 0.1892(10) 0.6658(8) -0.0034(8) 0.021(2) Uani 1 1 d .
H10 H 0.1620 0.7386 -0.0146 0.025 Uiso 1 1 calc R
C11 C 0.1746(10) 0.6426(8) 0.1065(7) 0.0179(19) Uani 1 1 d .
H11 H 0.1428 0.7019 0.1745 0.021 Uiso 1 1 calc R
C12 C 0.2072(10) 0.5302(8) 0.1179(7) 0.0155(19) Uani 1 1 d .
C13 C 0.1826(10) 0.5023(8) 0.2379(7) 0.0154(19) Uani 1 1 d .
N14 N 0.1836(8) 0.3807(7) 0.2315(6) 0.0181(16) Uani 1 1 d .
H14N H 0.1926 0.3240 0.1600 0.022 Uiso 1 1 calc R
C15 C 0.1700(11) 0.3410(8) 0.3415(7) 0.022(2) Uani 1 1 d .
H15A H 0.2381 0.4192 0.4166 0.026 Uiso 1 1 calc R
H15B H 0.2238 0.2705 0.3315 0.026 Uiso 1 1 calc R
C16 C -0.0165(10) 0.2888(8) 0.3634(7) 0.0191(19) Uani 1 1 d .
H16A H -0.0903 0.2185 0.2852 0.023 Uiso 1 1 calc R
H16B H -0.0655 0.3626 0.3880 0.023 Uiso 1 1 calc R
C17 C -0.0165(10) 0.2307(9) 0.4675(7) 0.022(2) Uani 1 1 d .
H17A H 0.0390 0.1607 0.4435 0.026 Uiso 1 1 calc R
H17B H 0.0558 0.3027 0.5453 0.026 Uiso 1 1 calc R
P P -0.2656(3) -0.0477(2) -0.04400(19) 0.0143(6) Uani 1 1 d .
O11 O -0.2798(8) 0.0549(6) 0.0838(5) 0.0183(13) Uani 1 1 d .
H11O H -0.361(14) 0.082(10) 0.078(9) 0.05(3) Uiso 1 1 d .
O12 O -0.1383(8) 0.0383(6) -0.1085(5) 0.0192(14) Uani 1 1 d .
H12O H -0.043(13) 0.071(10) -0.056(9) 0.04(3) Uiso 1 1 d .
O13 O -0.4411(7) -0.1147(5) -0.1286(5) 0.0229(14) Uani 1 1 d .
O14 O -0.1816(6) -0.1394(5) -0.0144(5) 0.0173(13) Uani 1 1 d .
O1W O -0.2141(8) 0.0118(6) -0.3611(5) 0.0284(15) Uani 1 1 d .
H1W1 H -0.2058 0.0183 -0.2641 0.11(5) Uiso 1 1 d R
H1W2 H -0.3086 -0.0945 -0.4116 0.07(3) Uiso 1 1 d R
O2W O -0.4537(7) -0.2383(6) -0.5026(5) 0.0257(15) Uani 1 1 d .
H2W1 H -0.4092 -0.3036 -0.5832 0.12(5) Uiso 1 1 d R
H2W2 H -0.4986 -0.2922 -0.4622 0.02(2) Uiso 1 1 d R
O3W O -0.5761(7) -0.3553(6) -0.3338(5) 0.0259(15) Uani 1 1 d .
H3W1 H -0.5205 -0.2788 -0.2602 0.03(2) Uiso 1 1 d R
H3W2 H -0.5877 -0.4440 -0.3119 0.04(3) Uiso 1 1 d 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'
P P 0.1023 0.0942 '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
C17 N1 C2 115.6(6) 2
C17 N1 H1N1 111(4) 2
C2 N1 H1N1 105(4) .
C17 N1 H1N2 107(6) 2
C2 N1 H1N2 116(6) .
H1N1 N1 H1N2 102(7) .
N1 C2 C3 112.6(6) .
N1 C2 H2A 109.1 .
C3 C2 H2A 109.1 .
N1 C2 H2B 109.1 .
C3 C2 H2B 109.1 .
H2A C2 H2B 107.8 .
C2 C3 C4 108.8(6) .
C2 C3 H3A 109.9 .
C4 C3 H3A 109.9 .
C2 C3 H3B 109.9 .
C4 C3 H3B 109.9 .
H3A C3 H3B 108.3 .
N5 C4 C3 112.3(6) .
N5 C4 H4A 109.1 .
C3 C4 H4A 109.1 .
N5 C4 H4B 109.1 .
C3 C4 H4B 109.1 .
H4A C4 H4B 107.9 .
C6 N5 C4 124.3(7) .
C6 N5 H5N 117.8 .
C4 N5 H5N 117.8 .
O1 C6 N5 124.5(7) .
O1 C6 C7 120.8(7) .
N5 C6 C7 114.7(7) .
N8 C7 C9 121.7(7) .
N8 C7 C6 116.5(7) .
C9 C7 C6 121.9(7) .
C12 N8 C7 118.8(7) .
C10 C9 C7 119.1(7) .
C10 C9 H9 120.5 .
C7 C9 H9 120.5 .
C11 C10 C9 118.6(8) .
C11 C10 H10 120.7 .
C9 C10 H10 120.7 .
C10 C11 C12 119.3(8) .
C10 C11 H11 120.3 .
C12 C11 H11 120.3 .
N8 C12 C11 122.5(7) .
N8 C12 C13 118.7(7) .
C11 C12 C13 118.8(7) .
O2 C13 N14 124.0(7) .
O2 C13 C12 121.6(7) .
N14 C13 C12 114.4(7) .
C13 N14 C15 121.0(7) .
C13 N14 H14N 119.5 .
C15 N14 H14N 119.5 .
N14 C15 C16 113.9(6) .
N14 C15 H15A 108.8 .
C16 C15 H15A 108.8 .
N14 C15 H15B 108.8 .
C16 C15 H15B 108.8 .
H15A C15 H15B 107.7 .
C15 C16 C17 109.0(6) .
C15 C16 H16A 109.9 .
C17 C16 H16A 109.9 .
C15 C16 H16B 109.9 .
C17 C16 H16B 109.9 .
H16A C16 H16B 108.3 .
N1 C17 C16 113.8(7) 2
N1 C17 H17A 108.8 2
C16 C17 H17A 108.8 .
N1 C17 H17B 108.8 2
C16 C17 H17B 108.8 .
H17A C17 H17B 107.7 .
O14 P O13 116.1(3) .
O14 P O11 108.0(3) .
O13 P O11 110.3(3) .
O14 P O12 108.6(3) .
O13 P O12 107.6(3) .
O11 P O12 105.8(3) .
P O11 H11O 113(7) .
P O12 H12O 101(6) .
H1W1 O1W H1W2 101.7 .
H2W1 O2W H2W2 103.3 .
H3W1 O3W H3W2 108.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.255(9) .
O2 C13 1.226(9) .
N1 C17 1.490(11) 2
N1 C2 1.493(10) .
N1 H1N1 1.06(9) .
N1 H1N2 0.84(9) .
C2 C3 1.521(11) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.532(11) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 N5 1.446(10) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
N5 C6 1.327(10) .
N5 H5N 0.8800 .
C6 C7 1.491(11) .
C7 N8 1.353(10) .
C7 C9 1.398(11) .
N8 C12 1.321(10) .
C9 C10 1.393(11) .
C9 H9 0.9500 .
C10 C11 1.366(11) .
C10 H10 0.9500 .
C11 C12 1.406(11) .
C11 H11 0.9500 .
C12 C13 1.512(11) .
C13 N14 1.343(10) .
N14 C15 1.461(10) .
N14 H14N 0.8800 .
C15 C16 1.516(11) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.529(11) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 N1 1.490(11) 2
C17 H17A 0.9900 .
C17 H17B 0.9900 .
P O14 1.501(6) .
P O13 1.505(6) .
P O11 1.574(6) .
P O12 1.575(6) .
O11 H11O 0.81(10) .
O12 H12O 0.86(10) .
O1W H1W1 1.0837 .
O1W H1W2 1.1380 .
O2W H2W1 1.1269 .
O2W H2W2 0.8806 .
O3W H3W1 0.9515 .
O3W H3W2 1.0805 .
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 H1N1 O1W 1.06(9) 1.74(9) 2.781(9) 164(7) 2_554
N1 H1N2 O2 0.84(9) 2.00(9) 2.738(9) 146(8) 1_544
N1 H1N2 O2W 0.84(9) 2.60(9) 3.161(9) 125(7) 1_655
N5 H5N O14 0.88 2.14 2.922(8) 147.1 2
N14 H14N O14 0.88 2.17 3.014(8) 161.4 2
O11 H11O O13 0.81(10) 1.83(11) 2.580(8) 152(10) 2_455
O12 H12O O14 0.86(10) 1.78(10) 2.609(8) 163(9) 2
O1W H1W1 O12 1.08 1.75 2.818(8) 166.2 .
O1W H1W2 O2W 1.14 1.65 2.774(8) 170.4 .
O2W H2W1 O1 1.13 1.70 2.812(8) 167.5 2_554
O2W H2W2 O3W 0.88 1.88 2.734(8) 161.9 .
O3W H3W1 O13 0.95 1.86 2.796(8) 168.5 .
O3W H3W2 O1 1.08 1.88 2.960(8) 176.5 1_445
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_4
C17 N1 C2 C3 -54.8(9) 2 .
N1 C2 C3 C4 -166.7(7) . .
C2 C3 C4 N5 -170.3(7) . .
C3 C4 N5 C6 -92.4(9) . .
C4 N5 C6 O1 -0.5(12) . .
C4 N5 C6 C7 -178.8(7) . .
O1 C6 C7 N8 -172.8(6) . .
N5 C6 C7 N8 5.5(10) . .
O1 C6 C7 C9 7.5(11) . .
N5 C6 C7 C9 -174.2(7) . .
C9 C7 N8 C12 -0.7(11) . .
C6 C7 N8 C12 179.6(6) . .
N8 C7 C9 C10 0.2(11) . .
C6 C7 C9 C10 179.8(7) . .
C7 C9 C10 C11 1.8(11) . .
C9 C10 C11 C12 -3.2(11) . .
C7 N8 C12 C11 -0.8(11) . .
C7 N8 C12 C13 179.3(6) . .
C10 C11 C12 N8 2.8(12) . .
C10 C11 C12 C13 -177.2(7) . .
N8 C12 C13 O2 169.6(7) . .
C11 C12 C13 O2 -10.4(11) . .
N8 C12 C13 N14 -12.2(10) . .
C11 C12 C13 N14 167.8(7) . .
O2 C13 N14 C15 -4.8(12) . .
C12 C13 N14 C15 177.0(6) . .
C13 N14 C15 C16 83.2(9) . .
N14 C15 C16 C17 171.3(7) . .
C15 C16 C17 N1 -177.8(7) . 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038381
