#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:26:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179579 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/44/4504465.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_4504465
loop_
_publ_author_name
'Lill, Daniel T. de'
'Cahill, Christopher L.'
_publ_section_title
;
 Synthesis and Characterization of a Praseodymium--Adipate Framework
 Templated with 1,2-bis(4-Pyridyl)ethane: Host--Guest Interactions and
 Structural Survey
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2390
_journal_paper_doi               10.1021/cg700741v
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C9 H14 O7 Pr, C6 H6 N'
_chemical_formula_sum            'C15 H20 N O7 Pr'
_chemical_formula_weight         467.23
_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                108.6740(10)
_cell_angle_beta                 105.8120(10)
_cell_angle_gamma                104.1080(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8538(5)
_cell_length_b                   11.0219(7)
_cell_length_c                   11.6693(8)
_cell_measurement_reflns_used    2835
_cell_measurement_temperature    296(2)
_cell_volume                     857.90(10)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2005)'
_computing_data_collection       'APEX II (Bruker AXS, 2005)'
_computing_data_reduction        'SAINTPLUS (Bruker AXS, 2005)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Apex CCD'
_diffrn_measurement_method       'omega and Phi 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  0.0844
_diffrn_reflns_av_sigmaI/netI    0.1094
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10754
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    2.875
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0502
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0611
_reflns_number_gt                2680
_reflns_number_total             3512
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg700741v-file002.cif
_cod_data_source_block           GWMOF-11
_cod_original_sg_symbol_H-M      'p -1'
_cod_database_code               4504465
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
Pr1 Pr 0.27462(6) 0.02108(4) 0.06542(4) 0.01623(10) Uani 1 1 d .
O1 O 0.0682(5) 0.1493(4) 0.0183(3) 0.0217(10) Uani 1 1 d .
O2 O 0.1468(6) -0.0399(4) -0.1765(4) 0.0354(13) Uani 1 1 d .
O3 O 0.5405(7) 0.0235(5) 0.2420(4) 0.0257(11) Uani 1 1 d D
O4 O 0.4101(6) -0.1440(4) -0.0478(3) 0.0228(10) Uani 1 1 d .
O5 O 0.1654(6) 0.0895(4) 0.2431(4) 0.0287(11) Uani 1 1 d .
O6 O 0.5001(6) 0.2716(4) 0.1888(4) 0.0310(12) Uani 1 1 d .
O7 O 0.1561(6) -0.1915(4) 0.1044(4) 0.0348(12) Uani 1 1 d .
C1 C -0.0180(10) -0.0811(6) -0.2656(5) 0.0219(15) Uani 1 1 d .
C5 C -0.1682(9) -0.3366(6) 0.0383(6) 0.0378(19) Uani 1 1 d .
H5A H -0.2308 -0.4052 -0.0514 0.045 Uiso 1 1 calc R
H5B H -0.2622 -0.3027 0.0621 0.045 Uiso 1 1 calc R
C6 C -0.1004(9) -0.4062(5) 0.1265(6) 0.0288(17) Uani 1 1 d .
H6A H 0.0121 -0.4228 0.1176 0.035 Uiso 1 1 calc R
H6B H -0.0666 -0.3459 0.2171 0.035 Uiso 1 1 calc R
C2 C -0.0299(9) -0.1149(6) -0.4038(5) 0.0250(16) Uani 1 1 d .
H2A H -0.1543 -0.1827 -0.4642 0.030 Uiso 1 1 calc R
H2B H 0.0643 -0.1545 -0.4175 0.030 Uiso 1 1 calc R
N1 N 0.5279(8) 0.1755(6) 0.6620(5) 0.0412(16) Uani 1 1 d .
C8 C 0.7930(8) 0.3825(5) 0.1767(5) 0.0242(15) Uani 1 1 d .
H8A H 0.8967 0.3532 0.1661 0.029 Uiso 1 1 calc R
H8B H 0.8322 0.4435 0.2679 0.029 Uiso 1 1 calc R
C13 C 0.5216(10) 0.3999(7) 0.6913(6) 0.046(2) Uani 1 1 d .
H13 H 0.4968 0.4754 0.7369 0.055 Uiso 1 1 calc R
C4 C -0.0144(9) -0.2186(6) 0.0441(6) 0.0213(15) Uani 1 1 d .
C11 C 0.6212(10) 0.2850(7) 0.5302(7) 0.047(2) Uani 1 1 d .
H11 H 0.6651 0.2810 0.4632 0.057 Uiso 1 1 calc R
C14 C 0.4958(11) 0.2862(8) 0.7228(6) 0.050(2) Uani 1 1 d .
H14 H 0.4537 0.2887 0.7904 0.061 Uiso 1 1 calc R
C3 C 0.0037(9) 0.0134(6) -0.4320(5) 0.0341(18) Uani 1 1 d .
H3A H 0.1270 0.0813 -0.3698 0.041 Uiso 1 1 calc R
H3B H -0.0916 0.0520 -0.4186 0.041 Uiso 1 1 calc R
C12 C 0.5838(10) 0.3983(6) 0.5924(6) 0.038(2) Uani 1 1 d .
C7 C -0.2553(9) -0.5427(6) 0.0905(6) 0.0338(18) Uani 1 1 d .
H7A H -0.2839 -0.6031 0.0008 0.041 Uiso 1 1 calc R
H7B H -0.3695 -0.5254 0.0938 0.041 Uiso 1 1 calc R
C10 C 0.5933(11) 0.1771(7) 0.5673(7) 0.050(2) Uani 1 1 d .
H10 H 0.6212 0.1019 0.5247 0.060 Uiso 1 1 calc R
C9 C 0.6190(9) 0.2590(6) 0.1375(6) 0.0248(16) Uani 1 1 d .
C15 C 0.5941(10) 0.5118(7) 0.5471(7) 0.049(2) Uani 1 1 d .
H15A H 0.6857 0.5171 0.5057 0.059 Uiso 1 1 calc R
H15B H 0.6371 0.5987 0.6220 0.059 Uiso 1 1 calc R
HW1 H 0.516(9) -0.034(6) 0.270(6) 0.04(2) Uiso 1 1 d D
HW2 H 0.631(18) 0.047(14) 0.221(12) 0.30(8) Uiso 1 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 0.0033 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'
Pr Pr -0.2180 2.8214 '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
O5 Pr1 O1 71.53(13) . .
O5 Pr1 O3 81.34(15) . .
O1 Pr1 O3 143.00(13) . .
O5 Pr1 O4 144.54(12) . .
O1 Pr1 O4 140.70(11) . .
O3 Pr1 O4 73.95(14) . .
O5 Pr1 O2 136.35(14) . .
O1 Pr1 O2 70.47(13) . .
O3 Pr1 O2 142.06(15) . .
O4 Pr1 O2 70.28(13) . .
O5 Pr1 O7 73.61(14) . .
O1 Pr1 O7 121.04(13) . .
O3 Pr1 O7 72.13(15) . .
O4 Pr1 O7 74.82(13) . .
O2 Pr1 O7 109.35(13) . .
O5 Pr1 O6 81.12(13) . .
O1 Pr1 O6 76.61(13) . .
O3 Pr1 O6 74.72(14) . .
O4 Pr1 O6 115.24(14) . .
O2 Pr1 O6 109.74(13) . .
O7 Pr1 O6 140.69(13) . .
O5 Pr1 O1 73.82(12) . 2
O1 Pr1 O1 74.36(12) . 2
O3 Pr1 O1 121.94(14) . 2
O4 Pr1 O1 98.08(12) . 2
O2 Pr1 O1 75.96(12) . 2
O7 Pr1 O1 50.87(12) . 2
O6 Pr1 O1 146.33(13) . 2
O5 Pr1 O4 129.08(12) . 2_655
O1 Pr1 O4 105.27(12) . 2_655
O3 Pr1 O4 72.91(14) . 2_655
O4 Pr1 O4 66.82(13) . 2_655
O2 Pr1 O4 81.69(13) . 2_655
O7 Pr1 O4 133.57(13) . 2_655
O6 Pr1 O4 50.27(12) . 2_655
O1 Pr1 O4 156.40(11) 2 2_655
O5 Pr1 C4 70.73(14) . .
O1 Pr1 C4 97.84(16) . .
O3 Pr1 C4 96.33(17) . .
O4 Pr1 C4 86.96(15) . .
O2 Pr1 C4 94.03(15) . .
O7 Pr1 C4 24.95(14) . .
O6 Pr1 C4 151.52(14) . .
O1 Pr1 C4 25.96(13) 2 .
O4 Pr1 C4 153.40(15) 2_655 .
O5 Pr1 C9 104.67(16) . .
O1 Pr1 C9 91.41(15) . .
O3 Pr1 C9 71.32(16) . .
O4 Pr1 C9 91.19(17) . .
O2 Pr1 C9 96.96(15) . .
O7 Pr1 C9 143.21(15) . .
O6 Pr1 C9 24.77(14) . .
O1 Pr1 C9 165.51(14) 2 .
O4 Pr1 C9 25.51(14) 2_655 .
C4 Pr1 C9 167.52(16) . .
O5 Pr1 Pr1 68.09(10) . 2
O1 Pr1 Pr1 38.21(8) . 2
O3 Pr1 Pr1 146.00(12) . 2
O4 Pr1 Pr1 124.36(9) . 2
O2 Pr1 Pr1 68.86(10) . 2
O7 Pr1 Pr1 84.86(10) . 2
O6 Pr1 Pr1 113.12(10) . 2
O1 Pr1 Pr1 36.15(8) 2 2
O4 Pr1 Pr1 138.59(8) 2_655 2
C4 Pr1 Pr1 60.40(13) . 2
C9 Pr1 Pr1 129.56(13) . 2
C4 O1 Pr1 148.7(4) 2 .
C4 O1 Pr1 92.1(3) 2 2
Pr1 O1 Pr1 105.64(12) . 2
C1 O2 Pr1 135.6(4) . .
Pr1 O3 HW1 117(5) . .
Pr1 O3 HW2 102(9) . .
HW1 O3 HW2 128(10) . .
C9 O4 Pr1 148.5(4) 2_655 .
C9 O4 Pr1 92.8(4) 2_655 2_655
Pr1 O4 Pr1 113.18(13) . 2_655
C1 O5 Pr1 141.9(4) 2 .
C9 O6 Pr1 96.4(3) . .
C4 O7 Pr1 95.4(3) . .
O5 C1 O2 123.6(6) 2 .
O5 C1 C2 119.0(5) 2 .
O2 C1 C2 117.4(6) . .
C4 C5 C6 115.3(5) . .
C4 C5 H5A 108.4 . .
C6 C5 H5A 108.4 . .
C4 C5 H5B 108.4 . .
C6 C5 H5B 108.5 . .
H5A C5 H5B 107.5 . .
C7 C6 C5 110.9(5) . .
C7 C6 H6A 109.5 . .
C5 C6 H6A 109.5 . .
C7 C6 H6B 109.5 . .
C5 C6 H6B 109.4 . .
H6A C6 H6B 108.0 . .
C1 C2 C3 111.2(5) . .
C1 C2 H2A 109.4 . .
C3 C2 H2A 109.4 . .
C1 C2 H2B 109.4 . .
C3 C2 H2B 109.4 . .
H2A C2 H2B 108.0 . .
C14 N1 C10 116.5(6) . .
C9 C8 C7 108.7(5) . 1_665
C9 C8 H8A 110.0 . .
C7 C8 H8A 110.0 1_665 .
C9 C8 H8B 110.0 . .
C7 C8 H8B 110.0 1_665 .
H8A C8 H8B 108.3 . .
C12 C13 C14 119.0(6) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
O7 C4 O1 121.3(5) . 2
O7 C4 C5 121.7(5) . .
O1 C4 C5 116.9(6) 2 .
O7 C4 Pr1 59.6(3) . .
O1 C4 Pr1 61.9(3) 2 .
C5 C4 Pr1 176.4(5) . .
C10 C11 C12 119.9(7) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
N1 C14 C13 123.7(7) . .
N1 C14 H14 118.2 . .
C13 C14 H14 118.2 . .
C2 C3 C3 113.8(6) . 2_554
C2 C3 H3A 108.8 . .
C3 C3 H3A 108.8 2_554 .
C2 C3 H3B 108.8 . .
C3 C3 H3B 108.8 2_554 .
H3A C3 H3B 107.7 . .
C13 C12 C11 117.8(6) . .
C13 C12 C15 120.3(7) . .
C11 C12 C15 121.7(7) . .
C6 C7 C8 115.5(5) . 1_445
C6 C7 H7A 108.4 . .
C8 C7 H7A 108.4 1_445 .
C6 C7 H7B 108.4 . .
C8 C7 H7B 108.4 1_445 .
H7A C7 H7B 107.5 . .
N1 C10 C11 123.1(7) . .
N1 C10 H10 118.5 . .
C11 C10 H10 118.5 . .
O6 C9 O4 120.4(6) . 2_655
O6 C9 C8 119.7(6) . .
O4 C9 C8 119.7(6) 2_655 .
O6 C9 Pr1 58.8(3) . .
O4 C9 Pr1 61.7(3) 2_655 .
C8 C9 Pr1 178.5(5) . .
C12 C15 C15 111.0(7) . 2_666
C12 C15 H15A 109.4 . .
C15 C15 H15A 109.4 2_666 .
C12 C15 H15B 109.4 . .
C15 C15 H15B 109.4 2_666 .
H15A C15 H15B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pr1 O5 2.426(4) .
Pr1 O1 2.461(4) .
Pr1 O3 2.489(4) .
Pr1 O4 2.521(4) .
Pr1 O2 2.518(4) .
Pr1 O7 2.533(4) .
Pr1 O6 2.552(4) .
Pr1 O1 2.580(4) 2
Pr1 O4 2.613(4) 2_655
Pr1 C4 2.923(6) .
Pr1 C9 2.964(6) .
Pr1 Pr1 4.0166(9) 2
O1 C4 1.280(6) 2
O1 Pr1 2.580(4) 2
O2 C1 1.282(7) .
O3 HW1 0.80(6) .
O3 HW2 0.83(12) .
O4 C9 1.278(6) 2_655
O4 Pr1 2.613(4) 2_655
O5 C1 1.244(7) 2
O6 C9 1.250(7) .
O7 C4 1.239(7) .
C1 O5 1.244(7) 2
C1 C2 1.504(7) .
C5 C4 1.512(7) .
C5 C6 1.530(7) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.531(7) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C2 C3 1.530(7) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
N1 C14 1.323(8) .
N1 C10 1.342(8) .
C8 C9 1.511(7) .
C8 C7 1.520(7) 1_665
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C13 C12 1.367(8) .
C13 C14 1.400(8) .
C13 H13 0.9300 .
C4 O1 1.280(6) 2
C11 C10 1.380(8) .
C11 C12 1.373(9) .
C11 H11 0.9300 .
C14 H14 0.9300 .
C3 C3 1.500(10) 2_554
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C12 C15 1.499(8) .
C7 C8 1.520(7) 1_445
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C10 H10 0.9300 .
C9 O4 1.278(6) 2_655
C15 C15 1.485(12) 2_666
C15 H15A 0.9700 .
C15 H15B 0.9700 .
