#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:51:24 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179158 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/19/4311952.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_4311952
loop_
_publ_author_name
'Andrew C. Warden'
'Mark Warren'
'Milton T. W. Hearn'
'Leone Spiccia'
_publ_contact_author             'Spiccia, Leone'
_publ_contact_author_email       leone.spiccia@sci.monash.edu.au
_publ_section_title
;
 Binding of Inorganic Oxoanions to Macrocyclic Ligands: Effect of the
 Degree of Protonation on Supramolecular Assemblies Formed by Phosphate
 and [18]aneN6
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6936
_journal_page_last               6943
_journal_paper_doi               10.1021/ic049633v
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C12 H48 N6 O24 P6'
_chemical_formula_weight         846.38
_chemical_name_systematic
;
 1,4,7,10,13,16-hexaazoniacyclooctadecane-hexa-dihydrogen phosphate
;
_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_date             2003-12-14T00:32:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.8940(10)
_cell_angle_beta                 105.4840(10)
_cell_angle_gamma                97.4440(10)
_cell_formula_units_Z            1
_cell_length_a                   8.48260(10)
_cell_length_b                   8.8353(2)
_cell_length_c                   11.9115(3)
_cell_measurement_temperature    123(2)
_cell_volume                     807.41(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9125
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                3007
_reflns_number_total             3938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic049633vsi20040319_083424_2.cif
_cod_data_source_block           b81b1
_cod_database_code               4311952
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
P1 P -0.29401(7) -0.54985(6) 0.15532(5) 0.01345(15) Uani 1 1 d . . .
N1 N -0.5486(2) -0.1944(2) 0.19446(18) 0.0144(4) Uani 1 1 d . . .
C6 C -0.4586(3) -0.0541(3) 0.1694(2) 0.0169(5) Uani 1 1 d . . .
H8 H -0.181(3) 0.406(3) 0.569(2) 0.011(5) Uiso 1 1 d . . .
P2 P -0.15544(7) -0.23163(6) 0.91899(5) 0.01370(15) Uani 1 1 d . . .
N2 N -0.2474(2) 0.2074(2) 0.61371(16) 0.0134(4) Uani 1 1 d . . .
C1 C -0.2734(3) 0.1867(3) 0.8122(2) 0.0162(5) Uani 1 1 d . . .
H10 H -0.241(3) 0.394(2) 0.7595(19) 0.008(5) Uiso 1 1 d . . .
P3 P -0.28288(6) -0.20462(6) 0.53117(5) 0.01273(14) Uani 1 1 d . . .
N3 N -0.2051(2) 0.0592(2) 0.36360(17) 0.0140(4) Uani 1 1 d . . .
C2 C -0.2014(3) 0.2939(3) 0.74977(19) 0.0151(4) Uani 1 1 d . . .
H2A H -0.256(3) -0.008(3) 0.393(2) 0.006(5) Uiso 1 1 d . . .
C3 C -0.1644(3) 0.2994(3) 0.5487(2) 0.0157(4) Uani 1 1 d . . .
H5 H -0.186(3) 0.291(3) 0.372(2) 0.017(6) Uiso 1 1 d . . .
C4 C -0.2335(3) 0.2251(3) 0.4104(2) 0.0169(5) Uani 1 1 d . . .
H4 H -0.226(3) -0.113(3) 0.210(2) 0.021(6) Uiso 1 1 d . . .
C5 C -0.2706(3) -0.0174(3) 0.2254(2) 0.0160(4) Uani 1 1 d . . .
H2 H -0.500(3) 0.043(3) 0.201(2) 0.015(5) Uiso 1 1 d . . .
H12 H -0.280(3) 0.076(3) 0.774(2) 0.010(5) Uiso 1 1 d . . .
H1B H -0.557(3) -0.284(3) 0.143(2) 0.019(6) Uiso 1 1 d . . .
H6 H -0.352(3) 0.219(3) 0.384(2) 0.018(6) Uiso 1 1 d . . .
H3 H -0.216(2) 0.064(2) 0.1943(19) 0.006(5) Uiso 1 1 d . . .
H9 H -0.081(3) 0.310(3) 0.780(2) 0.019(6) Uiso 1 1 d . . .
H1 H -0.489(3) -0.080(2) 0.081(2) 0.011(5) Uiso 1 1 d . . .
H7 H -0.044(3) 0.309(3) 0.586(2) 0.014(5) Uiso 1 1 d . . .
H3A H -0.215(3) 0.107(4) 0.608(3) 0.042(8) Uiso 1 1 d . . .
H11 H -0.209(3) 0.226(3) 0.903(2) 0.014(5) Uiso 1 1 d . . .
H3B H -0.359(3) 0.188(3) 0.580(2) 0.017(6) Uiso 1 1 d . . .
H1A H -0.489(3) -0.202(3) 0.276(2) 0.027(7) Uiso 1 1 d . . .
H2B H -0.091(4) 0.067(3) 0.390(3) 0.036(8) Uiso 1 1 d . . .
H1P H -0.199(5) -0.387(5) 1.018(4) 0.094(14) Uiso 1 1 d . . .
H2P H -0.142(4) 0.014(4) 1.012(3) 0.043(8) Uiso 1 1 d . . .
H3P H -0.328(4) -0.270(4) 0.683(3) 0.054(10) Uiso 1 1 d . . .
H5P H -0.088(4) -0.659(4) 0.178(3) 0.056(10) Uiso 1 1 d . . .
H6P H -0.507(4) -0.672(4) 0.163(3) 0.052(10) Uiso 1 1 d . . .
O1P1 O -0.31180(18) -0.54834(17) 0.02632(13) 0.0184(3) Uani 1 1 d . . .
O2P1 O -0.11974(18) -0.58273(18) 0.21697(14) 0.0179(3) Uani 1 1 d . . .
O3P1 O -0.42327(19) -0.69804(18) 0.14950(15) 0.0198(4) Uani 1 1 d . . .
O4P1 O -0.30911(19) -0.39603(16) 0.24153(14) 0.0185(3) Uani 1 1 d . . .
O1P2 O 0.00951(18) -0.18462(17) 0.89738(14) 0.0185(3) Uani 1 1 d . . .
O2P2 O -0.29377(17) -0.34179(16) 0.80550(13) 0.0154(3) Uani 1 1 d . . .
O3P2 O -0.1215(2) -0.3098(2) 1.02206(16) 0.0277(4) Uani 1 1 d . . .
O4P2 O -0.22069(19) -0.07616(19) 0.96608(15) 0.0202(4) Uani 1 1 d . . .
O1P3 O -0.40806(17) -0.15024(16) 0.44045(13) 0.0147(3) Uani 1 1 d . . .
O2P3 O -0.12631(17) -0.07153(17) 0.59837(14) 0.0177(3) Uani 1 1 d . . .
O3P3 O -0.37482(19) -0.23983(19) 0.62095(15) 0.0202(4) Uani 1 1 d . . .
O4P3 O -0.23918(19) -0.36276(17) 0.46592(14) 0.0193(3) Uani 1 1 d . . .
H4P H -0.2678 -0.3783 0.3898 0.023 Uiso 1 1 calc 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 0 '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 0.006 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4P1 P1 O1P1 114.92(8) . . ?
O4P1 P1 O2P1 106.41(9) . . ?
O1P1 P1 O2P1 111.15(8) . . ?
O4P1 P1 O3P1 111.00(8) . . ?
O1P1 P1 O3P1 109.07(9) . . ?
O2P1 P1 O3P1 103.69(8) . . ?
C1 N1 C6 112.77(16) 2_456 . ?
C5 C6 N1 113.88(18) . . ?
O2P2 P2 O1P2 114.46(9) . . ?
O2P2 P2 O3P2 110.88(9) . . ?
O1P2 P2 O3P2 107.81(9) . . ?
O2P2 P2 O4P2 106.51(8) . . ?
O1P2 P2 O4P2 109.26(8) . . ?
O3P2 P2 O4P2 107.73(9) . . ?
C3 N2 C2 113.29(17) . . ?
N1 C1 C2 112.45(17) 2_456 . ?
O2P3 P3 O1P3 109.66(8) . . ?
O2P3 P3 O4P3 110.90(8) . . ?
O1P3 P3 O4P3 111.52(8) . . ?
O2P3 P3 O3P3 111.46(9) . . ?
O1P3 P3 O3P3 105.30(8) . . ?
O4P3 P3 O3P3 107.87(9) . . ?
C4 N3 C5 114.90(17) . . ?
N2 C2 C1 110.56(18) . . ?
N2 C3 C4 112.52(18) . . ?
N3 C4 C3 113.71(18) . . ?
C6 C5 N3 115.27(17) . . ?
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
P1 O4P1 1.5062(14) . ?
P1 O1P1 1.5073(16) . ?
P1 O2P1 1.5676(15) . ?
P1 O3P1 1.5682(16) . ?
N1 C1 1.503(3) 2_456 ?
N1 C6 1.512(3) . ?
C6 C5 1.507(3) . ?
P2 O2P2 1.5126(15) . ?
P2 O1P2 1.5155(15) . ?
P2 O3P2 1.5473(17) . ?
P2 O4P2 1.5648(14) . ?
N2 C3 1.499(3) . ?
N2 C2 1.507(3) . ?
C1 N1 1.503(3) 2_456 ?
C1 C2 1.518(3) . ?
P3 O2P3 1.5164(15) . ?
P3 O1P3 1.5264(15) . ?
P3 O4P3 1.5450(14) . ?
P3 O3P3 1.5536(16) . ?
N3 C4 1.494(3) . ?
N3 C5 1.510(3) . ?
C3 C4 1.510(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
N1 H1B O1P1 0.84(2) 2.06(3) 2.802(2) 147(2) 2_445
N2 H3B O1P3 0.89(3) 1.90(3) 2.765(2) 163(2) 2_456
N3 H2B O2P3 0.92(3) 1.80(3) 2.708(2) 166(3) 2_556
O3P2 H1P O1P1 0.86(4) 1.66(4) 2.504(2) 167(4) 1_556
O4P2 H2P O1P2 0.90(3) 1.65(3) 2.547(2) 174(3) 2_557
O2P1 H5P O1P2 0.83(3) 1.74(3) 2.569(2) 177(3) 2_546
O3P1 H6P O2P2 0.82(3) 1.84(3) 2.641(2) 167(3) 2_446
N2 H3A O2P3 0.95(3) 1.82(3) 2.769(2) 172(2) .
N3 H2A O1P3 0.89(2) 1.98(2) 2.858(2) 169.5(19) .
N1 H1A O1P3 0.99(3) 1.80(3) 2.747(2) 159(2) .
O3P3 H3P O2P2 0.87(3) 1.71(3) 2.560(2) 164(3) .
O4P3 H4P O4P1 0.84 1.66 2.502(2) 174.7 .
C4 H6 O3P3 0.96(2) 2.33(2) 3.267(3) 164.1(19) 2_456
C2 H10 O2P2 0.97(2) 2.38(2) 3.343(2) 171.0(17) 1_565
