#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:55:38 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179496 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/93/4339312.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_4339312
loop_
_publ_author_name
'Matloka, Kornelia'
'Sah, Ajay K.'
'Peters, Matthew W.'
'Srinivasan, Priya'
'Gelis, Artem V.'
'Regalbuto, Monica'
'Scott, Michael J.'
_publ_section_title
;
 CMPO-functionalized C3-symmetric tripodal ligands in liquid/liquid
 extractions: efficient, selective recognition of Pu(IV) with low affinity
 for 3+ metal ions.
;
_journal_issue                   25
_journal_name_full               'Inorganic chemistry'
_journal_page_first              10549
_journal_page_last               10563
_journal_paper_doi               10.1021/ic700800a
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C95 H122 N3 O10 P3'
_chemical_formula_weight         1558.87
_chemical_name_common            'Compoun 12b'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   18.674(2)
_cell_length_b                   18.674(2)
_cell_length_c                   43.801(3)
_cell_measurement_temperature    173(2)
_cell_volume                     13228(2)
_computing_cell_refinement       'Bruker AXS SMART'
_computing_data_collection       'Bruker AXS SMART'
_computing_data_reduction        'Bruker AXS SAINT'
_computing_molecular_graphics    XP
_computing_publication_material  'Microsoft Word'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1023
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            24103
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.645969
_exptl_absorpt_correction_type   'Corrected by SADABS'
_exptl_absorpt_process_details   'Corrected by SADABS'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5028
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0816
_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)+(0.0513P)²+56.7569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                3938
_reflns_number_total             5195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic700800a-file002.cif
_cod_data_source_block           12bMeOH
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      r3bar
_cod_database_code               4339312
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
P1 P 0.49405(7) 0.83782(6) 0.02361(2) 0.0420(3) Uani 1 1 d .
O1 O 0.24053(15) 0.72206(14) -0.11847(5) 0.0324(6) Uani 1 1 d .
O2 O 0.47786(17) 0.92937(16) -0.03910(6) 0.0472(7) Uani 1 1 d .
O3 O 0.4703(2) 0.75562(18) 0.01093(7) 0.0645(9) Uani 1 1 d .
N1 N 0.3586(2) 0.8079(2) -0.03487(7) 0.0427(8) Uani 1 1 d .
H1A H 0.3191 0.7734 -0.0225 0.051 Uiso 1 1 calc R
C1 C 0.3333 0.6667 -0.15474(12) 0.0302(13) Uani 1 3 d S
H1B H 0.3333 0.6667 -0.1319 0.036 Uiso 1 3 calc SR
C2 C 0.2529(2) 0.6632(2) -0.16548(7) 0.0308(8) Uani 1 1 d .
C3 C 0.2091(2) 0.6888(2) -0.14712(7) 0.0320(8) Uani 1 1 d .
C4 C 0.1320(2) 0.6772(2) -0.15588(8) 0.0361(8) Uani 1 1 d .
C5 C 0.0738(2) 0.6894(3) -0.13400(8) 0.0433(9) Uani 1 1 d .
C6 C 0.1081(3) 0.7802(3) -0.12583(11) 0.0586(12) Uani 1 1 d .
H6A H 0.1583 0.7996 -0.1136 0.088 Uiso 1 1 calc R
H6B H 0.0667 0.7862 -0.1141 0.088 Uiso 1 1 calc R
H6C H 0.1212 0.8130 -0.1446 0.088 Uiso 1 1 calc R
C7 C 0.0610(3) 0.6394(3) -0.10470(10) 0.0600(12) Uani 1 1 d .
H7A H 0.1126 0.6642 -0.0930 0.090 Uiso 1 1 calc R
H7B H 0.0449 0.5823 -0.1100 0.090 Uiso 1 1 calc R
H7C H 0.0173 0.6396 -0.0924 0.090 Uiso 1 1 calc R
C8 C -0.0118(3) 0.6578(4) -0.14837(11) 0.0675(14) Uani 1 1 d .
H8A H -0.0494 0.6595 -0.1332 0.101 Uiso 1 1 calc R
H8B H -0.0336 0.6007 -0.1553 0.101 Uiso 1 1 calc R
H8C H -0.0071 0.6928 -0.1658 0.101 Uiso 1 1 calc R
C9 C 0.1061(2) 0.6489(2) -0.18550(8) 0.0387(9) Uani 1 1 d .
H9A H 0.0552 0.6432 -0.1924 0.046 Uiso 1 1 calc R
C10 C 0.1506(2) 0.6288(2) -0.20536(8) 0.0367(8) Uani 1 1 d .
C11 C 0.1231(3) 0.6062(2) -0.23883(8) 0.0430(10) Uani 1 1 d .
C12 C 0.1404(5) 0.6860(3) -0.25484(11) 0.090(2) Uani 1 1 d .
H12A H 0.1051 0.7057 -0.2461 0.135 Uiso 1 1 calc R
H12B H 0.1287 0.6753 -0.2767 0.135 Uiso 1 1 calc R
H12C H 0.1986 0.7281 -0.2520 0.135 Uiso 1 1 calc R
C13 C 0.1734(3) 0.5745(4) -0.25570(11) 0.0759(16) Uani 1 1 d .
H13A H 0.2323 0.6160 -0.2546 0.114 Uiso 1 1 calc R
H13B H 0.1561 0.5643 -0.2771 0.114 Uiso 1 1 calc R
H13C H 0.1640 0.5230 -0.2462 0.114 Uiso 1 1 calc R
C14 C 0.0337(3) 0.5417(4) -0.24163(11) 0.0783(17) Uani 1 1 d .
H14A H -0.0004 0.5618 -0.2321 0.117 Uiso 1 1 calc R
H14B H 0.0240 0.4909 -0.2314 0.117 Uiso 1 1 calc R
H14C H 0.0190 0.5300 -0.2633 0.117 Uiso 1 1 calc R
C15 C 0.2215(2) 0.6320(2) -0.19449(8) 0.0344(8) Uani 1 1 d .
H15A H 0.2497 0.6126 -0.2070 0.041 Uiso 1 1 calc R
C16 C 0.3028(2) 0.8079(2) -0.11866(8) 0.0355(8) Uani 1 1 d .
H16A H 0.2839 0.8402 -0.1307 0.043 Uiso 1 1 calc R
H16B H 0.3545 0.8152 -0.1279 0.043 Uiso 1 1 calc R
C17 C 0.3175(3) 0.8364(2) -0.08573(8) 0.0413(9) Uani 1 1 d .
H17A H 0.3572 0.8966 -0.0850 0.050 Uiso 1 1 calc R
H17B H 0.2648 0.8264 -0.0766 0.050 Uiso 1 1 calc R
C18 C 0.3512(3) 0.7912(2) -0.06752(8) 0.0404(9) Uani 1 1 d .
H18A H 0.3147 0.7310 -0.0707 0.048 Uiso 1 1 calc R
H18B H 0.4064 0.8063 -0.0756 0.048 Uiso 1 1 calc R
C19 C 0.4239(2) 0.8743(2) -0.02329(8) 0.0403(9) Uani 1 1 d .
C20 C 0.4280(2) 0.8768(2) 0.01127(8) 0.0370(9) Uani 1 1 d .
H20A H 0.3719 0.8425 0.0199 0.044 Uiso 1 1 calc R
H20B H 0.4503 0.9343 0.0185 0.044 Uiso 1 1 calc R
C21 C 0.4896(2) 0.8358(2) 0.06474(8) 0.0409(9) Uani 1 1 d .
C22 C 0.4794(3) 0.7652(3) 0.07895(10) 0.0575(12) Uani 1 1 d .
H22A H 0.4749 0.7206 0.0670 0.069 Uiso 1 1 calc R
C23 C 0.4757(3) 0.7589(3) 0.11069(11) 0.0715(15) Uani 1 1 d .
H23A H 0.4690 0.7104 0.1204 0.086 Uiso 1 1 calc R
C24 C 0.4819(3) 0.8229(3) 0.12780(10) 0.0642(14) Uani 1 1 d .
H24A H 0.4796 0.8187 0.1494 0.077 Uiso 1 1 calc R
C25 C 0.4913(3) 0.8930(3) 0.11415(10) 0.0580(12) Uani 1 1 d .
H25A H 0.4960 0.9373 0.1263 0.070 Uiso 1 1 calc R
C26 C 0.4942(3) 0.8996(3) 0.08242(9) 0.0452(10) Uani 1 1 d .
H26A H 0.4992 0.9476 0.0729 0.054 Uiso 1 1 calc R
C27 C 0.5962(3) 0.9133(3) 0.01161(8) 0.0450(10) Uani 1 1 d .
C28 C 0.6398(3) 0.9905(3) 0.02360(10) 0.0537(11) Uani 1 1 d .
H28A H 0.6176 1.0044 0.0406 0.064 Uiso 1 1 calc R
C29 C 0.7150(3) 1.0494(3) 0.01200(11) 0.0643(13) Uani 1 1 d .
H29A H 0.7428 1.1034 0.0206 0.077 Uiso 1 1 calc R
C30 C 0.7488(4) 1.0307(5) -0.01145(13) 0.0879(19) Uani 1 1 d .
H30A H 0.8022 1.0698 -0.0188 0.106 Uiso 1 1 calc R
C31 C 0.7057(5) 0.9551(6) -0.02448(18) 0.124(3) Uani 1 1 d .
H31A H 0.7279 0.9424 -0.0418 0.149 Uiso 1 1 calc R
C32 C 0.6301(4) 0.8961(4) -0.01304(16) 0.106(2) Uani 1 1 d .
H32A H 0.6012 0.8432 -0.0224 0.127 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 0.0000 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
_geom_angle_site_symmetry_3
O3 P1 C27 110.8(2) . .
O3 P1 C20 113.41(19) . .
C27 P1 C20 105.60(18) . .
O3 P1 C21 111.57(18) . .
C27 P1 C21 109.21(18) . .
C20 P1 C21 105.95(17) . .
C3 O1 C16 114.8(2) . .
C19 N1 C18 121.3(3) . .
C2 C1 C2 111.2(2) . 3_565
C2 C1 C2 111.2(2) . 2_665
C2 C1 C2 111.2(2) 3_565 2_665
C3 C2 C15 118.2(3) . .
C3 C2 C1 122.4(3) . .
C15 C2 C1 119.4(3) . .
C2 C3 O1 119.0(3) . .
C2 C3 C4 121.7(3) . .
O1 C3 C4 119.2(3) . .
C9 C4 C3 116.7(3) . .
C9 C4 C5 119.7(3) . .
C3 C4 C5 123.5(3) . .
C6 C5 C7 109.4(4) . .
C6 C5 C8 107.6(4) . .
C7 C5 C8 107.1(4) . .
C6 C5 C4 111.9(3) . .
C7 C5 C4 109.5(3) . .
C8 C5 C4 111.2(3) . .
C10 C9 C4 123.3(3) . .
C9 C10 C15 117.8(3) . .
C9 C10 C11 120.8(3) . .
C15 C10 C11 121.4(3) . .
C14 C11 C13 107.6(4) . .
C14 C11 C12 110.8(4) . .
C13 C11 C12 106.5(4) . .
C14 C11 C10 112.5(4) . .
C13 C11 C10 112.5(3) . .
C12 C11 C10 106.9(3) . .
C10 C15 C2 121.7(3) . .
O1 C16 C17 106.9(3) . .
C18 C17 C16 111.0(3) . .
N1 C18 C17 114.9(3) . .
O2 C19 N1 123.4(3) . .
O2 C19 C20 121.9(3) . .
N1 C19 C20 114.7(3) . .
C19 C20 P1 108.8(3) . .
C22 C21 C26 119.2(4) . .
C22 C21 P1 116.9(3) . .
C26 C21 P1 123.9(3) . .
C21 C22 C23 120.4(5) . .
C24 C23 C22 119.7(4) . .
C23 C24 C25 120.8(4) . .
C24 C25 C26 120.0(5) . .
C21 C26 C25 119.9(4) . .
C28 C27 C32 116.9(5) . .
C28 C27 P1 123.9(3) . .
C32 C27 P1 118.8(4) . .
C27 C28 C29 122.4(4) . .
C30 C29 C28 119.9(5) . .
C29 C30 C31 118.9(6) . .
C30 C31 C32 121.1(6) . .
C27 C32 C31 120.6(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O3 1.477(3) .
P1 C27 1.793(4) .
P1 C20 1.800(4) .
P1 C21 1.803(4) .
O1 C3 1.393(4) .
O1 C16 1.434(4) .
O2 C19 1.232(4) .
N1 C19 1.330(5) .
N1 C18 1.456(4) .
C1 C2 1.545(4) .
C1 C2 1.545(4) 3_565
C1 C2 1.545(4) 2_665
C2 C3 1.391(5) .
C2 C15 1.398(5) .
C3 C4 1.398(5) .
C4 C9 1.393(5) .
C4 C5 1.549(5) .
C5 C6 1.524(6) .
C5 C7 1.534(6) .
C5 C8 1.535(6) .
C9 C10 1.378(5) .
C10 C15 1.380(5) .
C10 C11 1.541(5) .
C11 C14 1.498(6) .
C11 C13 1.527(6) .
C11 C12 1.527(6) .
C16 C17 1.514(5) .
C17 C18 1.508(5) .
C19 C20 1.515(5) .
C21 C22 1.383(6) .
C21 C26 1.387(6) .
C22 C23 1.394(6) .
C23 C24 1.366(7) .
C24 C25 1.369(7) .
C25 C26 1.394(5) .
C27 C28 1.358(6) .
C27 C32 1.367(6) .
C28 C29 1.376(6) .
C29 C30 1.341(7) .
C30 C31 1.353(9) .
C31 C32 1.380(9) .
