#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:38:02 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179539 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/08/4500842.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_4500842
loop_
_publ_author_name
'Karmakar, Anirban'
'Titi, Hatem M.'
'Goldberg, Israel'
_publ_section_title
;
 Coordination Polymers of
 5-(2-Amino/Acetamido-4-carboxyphenoxy)-benzene-1,3-dioic Acids with
 Transition Metal Ions: Synthesis, Structure, and Catalytic Activity
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2621
_journal_paper_doi               10.1021/cg200350j
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         '2(C15 H12 Ce N O9), C3 H7 N O, 2(H2 O)'
_chemical_formula_sum            'C33 H37 Ce2 N3 O22'
_chemical_formula_weight         1107.90
_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                96.126(2)
_cell_angle_beta                 97.2065(17)
_cell_angle_gamma                111.8585(19)
_cell_formula_units_Z            1
_cell_length_a                   9.6047(4)
_cell_length_b                   10.0427(4)
_cell_length_c                   11.4589(5)
_cell_measurement_reflns_used    3894
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.22
_cell_volume                     1003.50(7)
_computing_cell_refinement       Denzo
_computing_data_collection       'Collect, Nonius B.V.'
_computing_data_reduction        'Denzo & Scalepack'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. ω 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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12389
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         2.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.329
_exptl_absorpt_correction_T_max  0.8005
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.990
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+4.2459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                3745
_reflns_number_total             4284
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200350j_si_001.cif
_cod_data_source_block           6
_cod_database_code               4500842
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
CE Ce 0.71324(3) 0.95492(3) 0.00822(2) 0.01663(10) Uani 1 1 d .
O8 O 0.5437(4) 0.7573(4) 0.1099(3) 0.0213(8) Uani 1 1 d .
O19 O 0.1182(4) 0.9824(4) 0.7823(3) 0.0235(8) Uani 1 1 d .
O1 O 0.1830(4) 0.2265(4) -0.0169(4) 0.0285(9) Uani 1 1 d .
O2 O -0.0539(4) 0.1594(4) 0.0161(3) 0.0237(8) Uani 1 1 d .
C3 C 0.0782(6) 0.2530(5) 0.0226(4) 0.0189(10) Uani 1 1 d .
C4 C 0.1131(6) 0.4068(5) 0.0795(4) 0.0184(10) Uani 1 1 d .
C5 C 0.2475(6) 0.5170(5) 0.0680(4) 0.0184(10) Uani 1 1 d .
H5 H 0.3177 0.4949 0.0263 0.022 Uiso 1 1 calc R
C6 C 0.2795(5) 0.6603(5) 0.1174(4) 0.0162(10) Uani 1 1 d .
C7 C 0.4220(6) 0.7789(5) 0.1012(4) 0.0175(10) Uani 1 1 d .
O9 O 0.4192(4) 0.8997(4) 0.0777(3) 0.0189(7) Uani 1 1 d .
C10 C 0.1777(6) 0.6918(6) 0.1809(4) 0.0200(10) Uani 1 1 d .
H10 H 0.1960 0.7896 0.2119 0.024 Uiso 1 1 calc R
C11 C 0.0502(6) 0.5789(6) 0.1980(4) 0.0195(10) Uani 1 1 d .
C12 C 0.0137(6) 0.4371(5) 0.1460(4) 0.0181(10) Uani 1 1 d .
H12 H -0.0777 0.3616 0.1554 0.022 Uiso 1 1 calc R
O13 O -0.0506(4) 0.6078(4) 0.2654(3) 0.0221(8) Uani 1 1 d .
C14 C 0.0090(6) 0.6737(6) 0.3826(4) 0.0207(10) Uani 1 1 d .
C15 C 0.1257(6) 0.6515(6) 0.4520(5) 0.0258(12) Uani 1 1 d .
H15 H 0.1710 0.5904 0.4186 0.031 Uiso 1 1 calc R
C16 C 0.1754(6) 0.7189(6) 0.5699(5) 0.0217(11) Uani 1 1 d .
H16 H 0.2542 0.7032 0.6178 0.026 Uiso 1 1 calc R
C17 C 0.1104(6) 0.8092(6) 0.6182(4) 0.0203(10) Uani 1 1 d .
C18 C 0.1704(6) 0.8905(5) 0.7427(4) 0.0191(10) Uani 1 1 d .
O20 O 0.2756(4) 0.8703(4) 0.8079(3) 0.0201(7) Uani 1 1 d .
C21 C -0.0063(6) 0.8305(6) 0.5483(5) 0.0257(11) Uani 1 1 d .
H21 H -0.0502 0.8928 0.5817 0.031 Uiso 1 1 calc R
C22 C -0.0593(6) 0.7619(6) 0.4307(5) 0.0220(11) Uani 1 1 d .
N23 N -0.1821(6) 0.7749(6) 0.3597(5) 0.0376(13) Uani 1 1 d .
H23A H -0.1678 0.8473 0.3185 0.045 Uiso 1 1 d .
H23B H -0.2621 0.6962 0.3154 0.045 Uiso 1 1 d .
O24 O 0.8067(4) 0.9374(5) -0.1919(3) 0.0314(9) Uani 1 1 d .
H24A H 0.7518 0.9133 -0.2638 0.047 Uiso 1 1 d .
H24B H 0.9024 0.9557 -0.1963 0.047 Uiso 1 1 d .
O25 O 0.5020(4) 0.7742(4) -0.1519(3) 0.0234(8) Uani 1 1 d .
H25A H 0.4849 0.6788 -0.1717 0.035 Uiso 1 1 d .
H25B H 0.4283 0.8085 -0.1624 0.035 Uiso 1 1 d .
O26 O 0.5732(6) 0.5184(5) 0.2081(5) 0.0627(17) Uani 1 1 d .
H26A H 0.5656 0.5951 0.1759 0.094 Uiso 1 1 d .
H26B H 0.5678 0.5301 0.2880 0.094 Uiso 1 1 d .
N27 N 0.5000 0.0000 0.5000 0.066(3) Uani 1 2 d S
C28 C 0.4936(17) -0.065(2) 0.3843(12) 0.057(4) Uani 0.50 1 d P
H28A H 0.3988 -0.0785 0.3313 0.100 Uiso 0.50 1 d PR
H28B H 0.4980 -0.1609 0.3898 0.100 Uiso 0.50 1 d PR
H28C H 0.5825 -0.0048 0.3525 0.100 Uiso 0.50 1 d PR
C29 C 0.5804(18) -0.038(2) 0.5983(13) 0.055(4) Uani 0.50 1 d P
H29A H 0.6524 0.0490 0.6535 0.100 Uiso 0.50 1 d PR
H29B H 0.6367 -0.0946 0.5667 0.100 Uiso 0.50 1 d PR
H29C H 0.5034 -0.0989 0.6404 0.100 Uiso 0.50 1 d PR
C30 C 0.436(2) 0.100(2) 0.521(2) 0.084(7) Uani 0.50 1 d P
H30 H 0.4355 0.1366 0.6011 0.100 Uiso 0.50 1 d PR
O31 O 0.3549(14) 0.1451(18) 0.4245(10) 0.080(4) Uani 0.50 1 d P
O32 O 0.3310(16) 0.3522(17) 0.3414(13) 0.087(4) Uani 0.50 1 d P
H32A H 0.3415 0.2787 0.3716 0.100 Uiso 0.50 1 d P
H32B H 0.2480 0.3053 0.2685 0.100 Uiso 0.50 1 d P
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.1943 3.0179 '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'
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
O1 CE O2 97.98(13) 2_665 1_665
O1 CE O9 159.03(13) 2_665 2_675
O2 CE O9 86.96(12) 1_665 2_675
O1 CE O25 86.99(12) 2_665 .
O2 CE O25 136.86(13) 1_665 .
O9 CE O25 75.78(11) 2_675 .
O1 CE O8 72.18(12) 2_665 .
O2 CE O8 149.55(12) 1_665 .
O9 CE O8 112.72(11) 2_675 .
O25 CE O8 72.61(12) . .
O1 CE O20 123.12(13) 2_665 2_676
O2 CE O20 76.58(12) 1_665 2_676
O9 CE O20 77.85(11) 2_675 2_676
O25 CE O20 134.81(11) . 2_676
O8 CE O20 84.87(12) . 2_676
O1 CE O24 75.93(14) 2_665 .
O2 CE O24 70.69(13) 1_665 .
O9 CE O24 86.66(13) 2_675 .
O25 CE O24 69.12(13) . .
O8 CE O24 130.73(13) . .
O20 CE O24 144.39(12) 2_676 .
O1 CE O19 73.96(13) 2_665 2_676
O2 CE O19 69.76(12) 1_665 2_676
O9 CE O19 126.53(11) 2_675 2_676
O25 CE O19 150.25(12) . 2_676
O8 CE O19 79.79(12) . 2_676
O20 CE O19 50.69(11) 2_676 2_676
O24 CE O19 125.39(12) . 2_676
O1 CE O9 118.86(11) 2_665 .
O2 CE O9 137.64(11) 1_665 .
O9 CE O9 66.40(12) 2_675 .
O25 CE O9 69.66(11) . .
O8 CE O9 47.30(10) . .
O20 CE O9 66.32(10) 2_676 .
O24 CE O9 135.02(11) . .
O19 CE O9 99.47(11) 2_676 .
O1 CE C18 98.81(14) 2_665 2_676
O2 CE C18 70.67(13) 1_665 2_676
O9 CE C18 102.05(13) 2_675 2_676
O25 CE C18 151.10(13) . 2_676
O8 CE C18 82.22(13) . 2_676
O20 CE C18 25.30(12) 2_676 2_676
O24 CE C18 139.77(13) . 2_676
O19 CE C18 25.41(13) 2_676 2_676
O9 CE C18 82.94(12) . 2_676
O1 CE C7 94.48(13) 2_665 .
O2 CE C7 154.37(13) 1_665 .
O9 CE C7 89.37(12) 2_675 .
O25 CE C7 65.89(12) . .
O8 CE C7 23.40(12) . .
O20 CE C7 77.85(12) 2_676 .
O24 CE C7 134.40(13) . .
O19 CE C7 92.55(12) 2_676 .
O9 CE C7 24.39(11) . .
C18 CE C7 85.38(13) 2_676 .
C7 O8 CE 103.1(3) . .
C18 O19 CE 93.7(3) . 2_676
C3 O1 CE 136.8(3) . 2_665
C3 O2 CE 171.0(3) . 1_445
O2 C3 O1 123.9(5) . .
O2 C3 C4 118.2(4) . .
O1 C3 C4 117.9(4) . .
C5 C4 C12 120.4(5) . .
C5 C4 C3 119.3(5) . .
C12 C4 C3 120.4(4) . .
C4 C5 C6 120.0(5) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C5 C6 C10 119.8(5) . .
C5 C6 C7 119.7(4) . .
C10 C6 C7 120.5(4) . .
O8 C7 O9 121.0(4) . .
O8 C7 C6 118.9(4) . .
O9 C7 C6 120.1(4) . .
O8 C7 CE 53.5(2) . .
O9 C7 CE 69.4(3) . .
C6 C7 CE 163.0(3) . .
C7 O9 CE 151.7(3) . 2_675
C7 O9 CE 86.2(3) . .
CE O9 CE 113.60(12) 2_675 .
C11 C10 C6 118.9(5) . .
C11 C10 H10 120.5 . .
C6 C10 H10 120.5 . .
C10 C11 C12 121.9(5) . .
C10 C11 O13 119.8(5) . .
C12 C11 O13 118.2(4) . .
C11 C12 C4 118.7(5) . .
C11 C12 H12 120.6 . .
C4 C12 H12 120.6 . .
C14 O13 C11 116.5(4) . .
O13 C14 C22 115.5(4) . .
O13 C14 C15 123.7(5) . .
C22 C14 C15 120.8(5) . .
C16 C15 C14 119.7(5) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
C15 C16 C17 120.1(5) . .
C15 C16 H16 119.9 . .
C17 C16 H16 119.9 . .
C16 C17 C21 119.8(5) . .
C16 C17 C18 120.6(5) . .
C21 C17 C18 119.6(5) . .
O20 C18 O19 120.2(4) . .
O20 C18 C17 120.0(4) . .
O19 C18 C17 119.8(4) . .
O20 C18 CE 59.4(2) . 2_676
O19 C18 CE 60.9(3) . 2_676
C17 C18 CE 178.6(4) . 2_676
C18 O20 CE 95.3(3) . 2_676
C22 C21 C17 120.9(5) . .
C22 C21 H21 119.6 . .
C17 C21 H21 119.6 . .
C21 C22 C14 118.7(5) . .
C21 C22 N23 122.3(5) . .
C14 C22 N23 119.0(5) . .
C22 N23 H23A 121.2 . .
C22 N23 H23B 122.6 . .
H23A N23 H23B 106.4 . .
CE O24 H24A 127.3 . .
CE O24 H24B 122.8 . .
H24A O24 H24B 109.9 . .
CE O25 H25A 125.3 . .
CE O25 H25B 107.1 . .
H25A O25 H25B 123.1 . .
H26A O26 H26B 110.2 . .
C30 N27 C30 180.0(9) . 2_656
C30 N27 C28 121.7(11) . .
C30 N27 C28 58.3(11) 2_656 .
C30 N27 C28 58.3(11) . 2_656
C30 N27 C28 121.7(11) 2_656 2_656
C28 N27 C28 180.0(13) . 2_656
C30 N27 C29 59.6(11) . 2_656
C30 N27 C29 120.4(11) 2_656 2_656
C28 N27 C29 62.2(9) . 2_656
C28 N27 C29 117.8(10) 2_656 2_656
C30 N27 C29 120.4(11) . .
C30 N27 C29 59.6(11) 2_656 .
C28 N27 C29 117.8(9) . .
C28 N27 C29 62.2(10) 2_656 .
C29 N27 C29 179.999(4) 2_656 .
C30 C28 N27 60.0(9) 2_656 .
C30 C28 C29 120.7(13) 2_656 2_656
N27 C28 C29 60.7(9) . 2_656
C30 C28 H28A 149.4 2_656 .
N27 C28 H28A 111.6 . .
C29 C28 H28A 59.2 2_656 .
C30 C28 H28B 54.0 2_656 .
N27 C28 H28B 107.2 . .
C29 C28 H28B 151.0 2_656 .
H28A C28 H28B 109.4 . .
C30 C28 H28C 100.3 2_656 .
N27 C28 H28C 109.3 . .
C29 C28 H28C 99.8 2_656 .
H28A C28 H28C 110.0 . .
H28B C28 H28C 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
CE O1 2.385(4) 2_665
CE O2 2.391(4) 1_665
CE O9 2.469(3) 2_675
CE O25 2.528(4) .
CE O8 2.552(3) .
CE O20 2.559(3) 2_676
CE O24 2.577(4) .
CE O19 2.593(4) 2_676
CE O9 2.900(4) .
CE C18 2.961(5) 2_676
CE C7 3.091(5) .
O8 C7 1.260(6) .
O19 C18 1.273(6) .
O19 CE 2.593(4) 2_676
O1 C3 1.255(6) .
O1 CE 2.385(4) 2_665
O2 C3 1.254(6) .
O2 CE 2.391(3) 1_445
C3 C4 1.507(7) .
C4 C5 1.385(7) .
C4 C12 1.391(7) .
C5 C6 1.392(7) .
C5 H5 0.9500 .
C6 C10 1.396(7) .
C6 C7 1.491(7) .
C7 O9 1.279(6) .
O9 CE 2.469(3) 2_675
C10 C11 1.377(7) .
C10 H10 0.9500 .
C11 C12 1.379(7) .
C11 O13 1.402(6) .
C12 H12 0.9500 .
O13 C14 1.380(6) .
C14 C22 1.393(8) .
C14 C15 1.392(7) .
C15 C16 1.383(7) .
C15 H15 0.9500 .
C16 C17 1.386(7) .
C16 H16 0.9500 .
C17 C21 1.390(7) .
C17 C18 1.493(7) .
C18 O20 1.271(6) .
C18 CE 2.961(5) 2_676
O20 CE 2.559(3) 2_676
C21 C22 1.385(7) .
C21 H21 0.9500 .
C22 N23 1.403(7) .
N23 H23A 0.8859 .
N23 H23B 0.9154 .
O24 H24A 0.8773 .
O24 H24B 0.8763 .
O25 H25A 0.9079 .
O25 H25B 0.8953 .
O26 H26A 0.9112 .
O26 H26B 0.9214 .
N27 C30 1.375(17) .
N27 C30 1.375(17) 2_656
N27 C28 1.398(14) .
N27 C28 1.398(14) 2_656
N27 C29 1.452(15) 2_656
N27 C29 1.452(15) .
C28 C30 1.35(2) 2_656
C28 C29 1.47(2) 2_656
C28 H28A 0.9842 .
C28 H28B 0.9856 .
C28 H28C 0.9850 .
C29 C30 1.41(2) 2_656
C29 O31 1.44(2) 2_656
C29 C28 1.47(2) 2_656
C29 H29A 0.9841 .
C29 H29B 0.9877 .
C29 H29C 0.9836 .
C30 C28 1.35(2) 2_656
C30 C29 1.41(2) 2_656
C30 O31 1.48(2) .
C30 H30 0.9501 .
O31 C29 1.44(2) 2_656
O32 H32A 0.8810 .
O32 H32B 1.0127 .
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
N23 H23A O19 0.89 2.11 2.991(7) 176 2_576
N23 H23B O26 0.92 2.03 2.948(7) 175 1_455
O24 H24A O31 0.88 1.91 2.781(12) 175 2_665
O24 H24B O19 0.88 2.04 2.913(5) 175 1_654
O25 H25A O26 0.91 1.83 2.734(6) 173 2_665
O25 H25B O20 0.90 1.80 2.698(5) 176 1_554
O26 H26A O8 0.91 1.94 2.847(6) 177 .
O26 H26B O32 0.92 2.51 3.013(15) 115 .
O32 H32A O31 0.88 1.57 2.45(2) 178 .
O32 H32B O24 1.01 2.34 2.941(16) 117 2_665
