#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:58:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178414 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/35/4023502.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_4023502
loop_
_publ_author_name
'Ivan V. Korendovych'
'Mimi Cho'
'Olga V. Makhlynets'
'Phillip L. Butler'
'Richard J. Staples'
'Elena V. Rybak-Akimova'
_publ_section_title
;
 Anion and Carboxylic Acid Binding to Monotopic and Ditopic
 Amidopyridine Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4771
_journal_page_last               4782
_journal_paper_doi               10.1021/jo800128r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C26 H38 N10 O4, 2(C H4 O)'
_chemical_formula_sum            'C28 H46 N10 O6'
_chemical_formula_weight         618.75
_chemical_name_systematic
;
?
;
_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                102.0700(10)
_cell_angle_beta                 115.0170(10)
_cell_angle_gamma                92.1090(10)
_cell_formula_units_Z            1
_cell_length_a                   9.1721(7)
_cell_length_b                   9.4004(7)
_cell_length_c                   10.7902(8)
_cell_measurement_reflns_used    3540
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.48
_cell_volume                     816.15(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6268
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.133(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0489
_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)+(0.0897P)²+0.0653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                2982
_reflns_number_total             3751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800128r-File010.cif
_cod_data_source_block           III
_cod_database_code               4023502
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.45347(12) 0.67111(11) 0.16979(10) 0.0388(2) Uani 1 1 d . . .
O1S O 0.69097(14) -0.00565(12) 0.30526(12) 0.0619(3) Uani 1 1 d . . .
H1S4 H 0.715(2) 0.073(2) 0.374(2) 0.075(6) Uiso 1 1 d . . .
C1 C 0.21590(15) 0.79245(15) 0.07301(14) 0.0493(3) Uani 1 1 d . . .
O1 O 0.06877(13) 0.78355(14) 0.00659(16) 0.0857(4) Uani 1 1 d . . .
C1S C 0.7263(3) 0.0310(3) 0.2009(2) 0.0792(5) Uani 1 1 d . . .
H1S1 H 0.758(4) 0.131(4) 0.211(3) 0.151(12) Uiso 1 1 d . . .
H1S2 H 0.653(4) -0.018(3) 0.117(4) 0.132(10) Uiso 1 1 d . . .
H1S3 H 0.818(6) -0.002(5) 0.203(4) 0.194(18) Uiso 1 1 d . . .
O2 O 0.76364(12) 0.45851(11) 0.31804(12) 0.0580(3) Uani 1 1 d . . .
N2 N 0.31538(14) 0.91876(12) 0.14503(12) 0.0515(3) Uani 1 1 d . . .
H2 H 0.414(2) 0.9154(18) 0.1970(18) 0.055(4) Uiso 1 1 d . . .
C2 C 0.29614(14) 0.65581(14) 0.08061(12) 0.0416(3) Uani 1 1 d . . .
N3 N 0.77327(13) 0.70451(13) 0.34707(11) 0.0464(3) Uani 1 1 d . . .
H3 H 0.7245(19) 0.7757(19) 0.3248(16) 0.051(4) Uiso 1 1 d . . .
C3 C 0.20313(16) 0.51972(16) 0.00264(14) 0.0491(3) Uani 1 1 d . . .
H3A H 0.091(2) 0.514(2) -0.0607(19) 0.068(5) Uiso 1 1 d . . .
N4 N 1.22614(12) 0.73789(12) 0.49339(10) 0.0405(3) Uani 1 1 d . . .
H4 H 1.2352(18) 0.6797(17) 0.5516(16) 0.048(4) Uiso 1 1 d . . .
C4 C 0.27575(18) 0.39505(16) 0.01815(15) 0.0530(3) Uani 1 1 d . . .
H4A H 0.212(2) 0.296(2) -0.0309(19) 0.073(5) Uiso 1 1 d . . .
C5 C 0.43815(17) 0.40871(15) 0.11054(14) 0.0473(3) Uani 1 1 d . . .
H5A H 0.493(2) 0.322(2) 0.1259(17) 0.063(5) Uiso 1 1 d . . .
N5 N 1.58474(15) 0.86778(13) 0.58057(14) 0.0542(3) Uani 1 1 d . . .
H5 H 1.584(2) 0.894(2) 0.503(2) 0.076(5) Uiso 1 1 d . . .
C6 C 0.52248(14) 0.54900(13) 0.18451(12) 0.0390(3) Uani 1 1 d . . .
C7 C 0.69794(15) 0.56655(14) 0.28905(13) 0.0421(3) Uani 1 1 d . . .
C8 C 0.94245(16) 0.73814(17) 0.45201(14) 0.0491(3) Uani 1 1 d . . .
H8A H 0.966(2) 0.674(2) 0.5191(18) 0.060(4) Uiso 1 1 d . . .
H8B H 0.961(2) 0.839(2) 0.501(2) 0.075(5) Uiso 1 1 d . . .
C9 C 1.05741(16) 0.71295(18) 0.38534(14) 0.0487(3) Uani 1 1 d . . .
H9B H 1.046(2) 0.778(2) 0.324(2) 0.073(5) Uiso 1 1 d . . .
H9A H 1.025(2) 0.609(2) 0.323(2) 0.078(5) Uiso 1 1 d . . .
C10 C 1.33565(17) 0.69391(18) 0.42983(14) 0.0521(3) Uani 1 1 d . . .
H10B H 1.326(2) 0.757(2) 0.3626(18) 0.062(4) Uiso 1 1 d . . .
H10A H 1.302(2) 0.591(2) 0.374(2) 0.072(5) Uiso 1 1 d . . .
C11 C 1.51112(16) 0.71509(15) 0.53752(15) 0.0494(3) Uani 1 1 d . . .
H11B H 1.5165(18) 0.6820(17) 0.6184(16) 0.047(4) Uiso 1 1 d . . .
H11A H 1.570(2) 0.650(2) 0.4963(19) 0.069(5) Uiso 1 1 d . . .
C12 C 1.74837(18) 0.89617(19) 0.6961(2) 0.0649(4) Uani 1 1 d . . .
H12B H 1.805(3) 0.812(2) 0.696(2) 0.086(6) Uiso 1 1 d . . .
H12A H 1.811(2) 0.977(2) 0.6843(19) 0.077(5) Uiso 1 1 d . . .
C13 C 0.25566(19) 1.05857(17) 0.16276(18) 0.0610(4) Uani 1 1 d . . .
H13A H 0.332(2) 1.133(2) 0.1558(19) 0.071(5) Uiso 1 1 d . . .
H13B H 0.154(3) 1.048(2) 0.087(2) 0.081(6) Uiso 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'
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
C2 N1 C6 117.73(10) . . ?
C1S O1S H1S4 108.7(13) . . ?
O1 C1 N2 124.14(13) . . ?
O1 C1 C2 120.34(12) . . ?
N2 C1 C2 115.51(11) . . ?
O1S C1S H1S1 118(2) . . ?
O1S C1S H1S2 109.5(19) . . ?
H1S1 C1S H1S2 117(3) . . ?
O1S C1S H1S3 111(3) . . ?
H1S1 C1S H1S3 97(3) . . ?
H1S2 C1S H1S3 102(3) . . ?
C1 N2 C13 122.33(12) . . ?
C1 N2 H2 118.4(12) . . ?
C13 N2 H2 117.8(12) . . ?
N1 C2 C3 122.92(12) . . ?
N1 C2 C1 117.51(11) . . ?
C3 C2 C1 119.44(11) . . ?
C7 N3 C8 121.65(11) . . ?
C7 N3 H3 121.1(11) . . ?
C8 N3 H3 117.2(11) . . ?
C4 C3 C2 118.78(12) . . ?
C4 C3 H3A 121.4(11) . . ?
C2 C3 H3A 119.9(11) . . ?
C9 N4 C10 110.79(10) . . ?
C9 N4 H4 108.4(10) . . ?
C10 N4 H4 106.2(10) . . ?
C3 C4 C5 119.11(12) . . ?
C3 C4 H4A 121.1(11) . . ?
C5 C4 H4A 119.6(11) . . ?
C4 C5 C6 118.48(13) . . ?
C4 C5 H5A 121.3(10) . . ?
C6 C5 H5A 120.2(10) . . ?
C11 N5 C12 113.29(12) . . ?
C11 N5 H5 108.2(12) . . ?
C12 N5 H5 111.3(12) . . ?
N1 C6 C5 122.98(11) . . ?
N1 C6 C7 117.51(10) . . ?
C5 C6 C7 119.49(11) . . ?
O2 C7 N3 123.73(12) . . ?
O2 C7 C6 120.60(11) . . ?
N3 C7 C6 115.67(11) . . ?
N3 C8 C9 111.90(11) . . ?
N3 C8 H8A 110.6(10) . . ?
C9 C8 H8A 107.0(10) . . ?
N3 C8 H8B 107.7(12) . . ?
C9 C8 H8B 109.4(12) . . ?
H8A C8 H8B 110.2(15) . . ?
N4 C9 C8 110.86(10) . . ?
N4 C9 H9B 108.6(11) . . ?
C8 C9 H9B 110.8(12) . . ?
N4 C9 H9A 112.0(11) . . ?
C8 C9 H9A 107.8(11) . . ?
H9B C9 H9A 106.7(16) . . ?
N4 C10 C11 112.80(11) . . ?
N4 C10 H10B 107.7(10) . . ?
C11 C10 H10B 108.1(10) . . ?
N4 C10 H10A 110.5(11) . . ?
C11 C10 H10A 110.1(11) . . ?
H10B C10 H10A 107.4(14) . . ?
N5 C11 C10 111.55(12) . . ?
N5 C11 H11B 110.5(9) . . ?
C10 C11 H11B 108.8(9) . . ?
N5 C11 H11A 111.5(11) . . ?
C10 C11 H11A 108.1(11) . . ?
H11B C11 H11A 106.2(14) . . ?
N5 C12 C13 111.04(12) . 2_776 ?
N5 C12 H12B 112.6(12) . . ?
C13 C12 H12B 108.1(12) 2_776 . ?
N5 C12 H12A 107.8(11) . . ?
C13 C12 H12A 109.4(11) 2_776 . ?
H12B C12 H12A 107.8(18) . . ?
N2 C13 C12 111.49(13) . 2_776 ?
N2 C13 H13A 106.8(12) . . ?
C12 C13 H13A 110.0(11) 2_776 . ?
N2 C13 H13B 106.3(13) . . ?
C12 C13 H13B 113.1(13) 2_776 . ?
H13A C13 H13B 109.0(16) . . ?
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 C2 1.3347(15) . ?
N1 C6 1.3372(16) . ?
O1S C1S 1.398(2) . ?
O1S H1S4 0.88(2) . ?
C1 O1 1.2208(16) . ?
C1 N2 1.3346(17) . ?
C1 C2 1.5036(19) . ?
C1S H1S1 0.95(4) . ?
C1S H1S2 0.88(3) . ?
C1S H1S3 0.90(5) . ?
O2 C7 1.2293(15) . ?
N2 C13 1.4493(19) . ?
N2 H2 0.845(18) . ?
C2 C3 1.3909(18) . ?
N3 C7 1.3341(17) . ?
N3 C8 1.4554(16) . ?
N3 H3 0.839(17) . ?
C3 C4 1.375(2) . ?
C3 H3A 0.954(19) . ?
N4 C9 1.4637(16) . ?
N4 C10 1.4645(17) . ?
N4 H4 0.897(16) . ?
C4 C5 1.380(2) . ?
C4 H4A 0.991(19) . ?
C5 C6 1.3918(18) . ?
C5 H5A 0.978(19) . ?
N5 C11 1.4548(18) . ?
N5 C12 1.458(2) . ?
N5 H5 0.92(2) . ?
C6 C7 1.5022(16) . ?
C8 C9 1.508(2) . ?
C8 H8A 0.997(18) . ?
C8 H8B 0.95(2) . ?
C9 H9B 0.97(2) . ?
C9 H9A 1.01(2) . ?
C10 C11 1.5094(19) . ?
C10 H10B 1.009(18) . ?
C10 H10A 0.99(2) . ?
C11 H11B 0.969(15) . ?
C11 H11A 0.99(2) . ?
C12 C13 1.510(3) 2_776 ?
C12 H12B 0.96(2) . ?
C12 H12A 1.00(2) . ?
C13 C12 1.510(3) 2_776 ?
C13 H13A 1.01(2) . ?
C13 H13B 0.93(2) . ?
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
O1S H1S4 N4 0.88(2) 1.93(2) 2.7944(15) 171.6(18) 2_766
N2 H2 O1S 0.845(18) 2.314(18) 3.1033(16) 155.4(15) 1_565
N3 H3 O1S 0.839(17) 2.130(18) 2.9282(16) 158.8(15) 1_565
N4 H4 O2 0.897(16) 2.102(16) 2.9966(14) 175.5(14) 2_766
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
O1 C1 N2 C13 6.2(2) . . . . ?
C2 C1 N2 C13 -172.31(13) . . . . ?
C6 N1 C2 C3 -0.61(17) . . . . ?
C6 N1 C2 C1 175.26(10) . . . . ?
O1 C1 C2 N1 -171.14(13) . . . . ?
N2 C1 C2 N1 7.43(18) . . . . ?
O1 C1 C2 C3 4.9(2) . . . . ?
N2 C1 C2 C3 -176.54(11) . . . . ?
N1 C2 C3 C4 0.27(19) . . . . ?
C1 C2 C3 C4 -175.53(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C2 N1 C6 C5 0.59(17) . . . . ?
C2 N1 C6 C7 -177.75(9) . . . . ?
C4 C5 C6 N1 -0.22(18) . . . . ?
C4 C5 C6 C7 178.09(10) . . . . ?
C8 N3 C7 O2 -0.37(19) . . . . ?
C8 N3 C7 C6 178.82(10) . . . . ?
N1 C6 C7 O2 172.51(11) . . . . ?
C5 C6 C7 O2 -5.89(17) . . . . ?
N1 C6 C7 N3 -6.71(15) . . . . ?
C5 C6 C7 N3 174.89(11) . . . . ?
C7 N3 C8 C9 78.75(16) . . . . ?
C10 N4 C9 C8 172.15(12) . . . . ?
N3 C8 C9 N4 -176.17(11) . . . . ?
C9 N4 C10 C11 -179.00(11) . . . . ?
C12 N5 C11 C10 173.41(12) . . . . ?
N4 C10 C11 N5 -79.42(15) . . . . ?
C11 N5 C12 C13 -91.43(15) . . . 2_776 ?
C1 N2 C13 C12 98.16(16) . . . 2_776 ?
