#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:38:02 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179539 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/08/4500841.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_4500841
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         'C33 H37 N3 Nd2 O22'
_chemical_formula_sum            'C33 H37 N3 Nd2 O22'
_chemical_formula_weight         1116.14
_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                96.342(2)
_cell_angle_beta                 97.063(2)
_cell_angle_gamma                111.7635(19)
_cell_formula_units_Z            1
_cell_length_a                   9.5211(4)
_cell_length_b                   9.9835(4)
_cell_length_c                   11.4843(5)
_cell_measurement_reflns_used    4297
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.62
_cell_volume                     991.60(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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. φ and 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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16434
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.680
_exptl_absorpt_correction_T_max  0.7754
_exptl_absorpt_correction_T_min  0.5539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.711
_refine_diff_density_min         -1.831
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+3.1958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                4162
_reflns_number_total             4698
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200350j_si_001.cif
_cod_data_source_block           5
_cod_database_code               4500841
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
Nd Nd 0.71371(2) 0.95488(2) 0.009210(19) 0.01402(9) Uani 1 1 d .
O8 O 0.5446(4) 0.7609(4) 0.1104(3) 0.0190(6) Uani 1 1 d .
O19 O 0.1196(4) 0.9873(4) 0.7850(3) 0.0198(7) Uani 1 1 d .
O1 O 0.1852(4) 0.2277(3) -0.0123(3) 0.0210(7) Uani 1 1 d .
O2 O -0.0544(4) 0.1588(3) 0.0188(3) 0.0209(7) Uani 1 1 d .
C3 C 0.0776(5) 0.2524(5) 0.0253(4) 0.0149(8) Uani 1 1 d .
C4 C 0.1117(5) 0.4072(5) 0.0817(4) 0.0150(8) Uani 1 1 d .
C5 C 0.2476(5) 0.5184(5) 0.0698(4) 0.0160(8) Uani 1 1 d .
H5 H 0.3191 0.4961 0.0287 0.019 Uiso 1 1 calc R
C6 C 0.2782(5) 0.6630(5) 0.1185(4) 0.0142(8) Uani 1 1 d .
C7 C 0.4224(5) 0.7827(5) 0.1012(4) 0.0150(8) Uani 1 1 d .
O9 O 0.4165(3) 0.9023(3) 0.0768(3) 0.0164(6) Uani 1 1 d .
C10 C 0.1762(5) 0.6950(5) 0.1824(4) 0.0161(8) Uani 1 1 d .
H10 H 0.1943 0.7933 0.2134 0.019 Uiso 1 1 calc R
C11 C 0.0484(5) 0.5810(5) 0.1999(4) 0.0152(8) Uani 1 1 d .
C12 C 0.0124(5) 0.4382(5) 0.1477(4) 0.0156(8) Uani 1 1 d .
H12 H -0.0796 0.3622 0.1571 0.019 Uiso 1 1 calc R
O13 O -0.0533(4) 0.6097(4) 0.2679(3) 0.0189(6) Uani 1 1 d .
C14 C 0.0074(5) 0.6759(5) 0.3855(4) 0.0169(8) Uani 1 1 d .
C15 C 0.1259(6) 0.6530(5) 0.4534(4) 0.0218(9) Uani 1 1 d .
H15 H 0.1712 0.5913 0.4195 0.026 Uiso 1 1 calc R
C16 C 0.1765(5) 0.7220(5) 0.5714(4) 0.0210(9) Uani 1 1 d .
H16 H 0.2569 0.7069 0.6186 0.025 Uiso 1 1 calc R
C17 C 0.1111(5) 0.8127(5) 0.6211(4) 0.0175(9) Uani 1 1 d .
C18 C 0.1718(5) 0.8942(5) 0.7446(4) 0.0172(8) Uani 1 1 d .
O20 O 0.2774(3) 0.8737(4) 0.8097(3) 0.0178(6) Uani 1 1 d .
C21 C -0.0082(5) 0.8332(6) 0.5522(4) 0.0217(9) Uani 1 1 d .
H21 H -0.0533 0.8949 0.5862 0.026 Uiso 1 1 calc R
C22 C -0.0617(5) 0.7642(5) 0.4343(4) 0.0203(9) Uani 1 1 d .
N23 N -0.1883(6) 0.7760(6) 0.3647(4) 0.0372(11) 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 0.8061(4) 0.9413(4) -0.1889(3) 0.0246(7) Uani 1 1 d .
H24A H 0.7518 0.9133 -0.2638 0.037 Uiso 1 1 d .
H24B H 0.9024 0.9557 -0.1963 0.037 Uiso 1 1 d .
O25 O 0.5045(4) 0.7757(3) -0.1480(3) 0.0211(7) Uani 1 1 d .
H25A H 0.4849 0.6788 -0.1717 0.032 Uiso 1 1 d .
H25B H 0.4283 0.8085 -0.1624 0.032 Uiso 1 1 d .
O26 O 0.5762(6) 0.5188(5) 0.2048(5) 0.0611(16) Uani 1 1 d .
H26A H 0.5656 0.5951 0.1759 0.092 Uiso 1 1 d .
H26B H 0.5678 0.5301 0.2880 0.092 Uiso 1 1 d .
N27 N 0.5000 0.0000 0.5000 0.058(2) Uani 1 2 d S
C28 C 0.4986(16) -0.0664(18) 0.3854(11) 0.049(4) Uani 0.50 1 d P
H28A H 0.4039 -0.0797 0.3324 0.08(7) Uiso 0.50 1 d PR
H28B H 0.5030 -0.1621 0.3909 0.08(9) Uiso 0.50 1 d PR
H28C H 0.5876 -0.0060 0.3536 0.09(5) Uiso 0.50 1 d PR
C29 C 0.5748(16) -0.0447(18) 0.5982(11) 0.046(3) Uani 0.50 1 d P
H29A H 0.6468 0.0427 0.6535 0.09(16) Uiso 0.50 1 d PR
H29B H 0.6310 -0.1010 0.5666 0.10(19) Uiso 0.50 1 d PR
H29C H 0.4977 -0.1052 0.6404 0.10(5) Uiso 0.50 1 d PR
C30 C 0.4343(19) 0.096(2) 0.5228(19) 0.070(5) Uani 0.50 1 d P
H30 H 0.4340 0.1327 0.6026 0.11(9) Uiso 0.50 1 d PR
O31 O 0.3618(12) 0.1458(18) 0.4205(9) 0.059(3) Uani 0.50 1 d P
O32 O 0.3280(14) 0.3434(13) 0.3351(9) 0.067(3) Uani 0.50 1 d P
H32A H 0.2939 0.3152 0.4013 0.10 Uiso 0.50 1 d P
H32B H 0.2480 0.3053 0.2685 0.10 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'
Nd Nd -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 Nd O2 98.50(11) 2_665 1_665
O1 Nd O9 156.99(12) 2_665 2_675
O2 Nd O9 86.86(11) 1_665 2_675
O1 Nd O25 85.72(11) 2_665 .
O2 Nd O25 137.36(12) 1_665 .
O9 Nd O25 75.52(10) 2_675 .
O1 Nd O20 124.44(11) 2_665 2_676
O2 Nd O20 76.58(11) 1_665 2_676
O9 Nd O20 78.56(10) 2_675 2_676
O25 Nd O20 134.48(10) . 2_676
O1 Nd O8 73.00(11) 2_665 .
O2 Nd O8 148.97(11) 1_665 .
O9 Nd O8 112.82(10) 2_675 .
O25 Nd O8 72.85(11) . .
O20 Nd O8 83.88(11) 2_676 .
O1 Nd O24 75.87(12) 2_665 .
O2 Nd O24 70.78(11) 1_665 .
O9 Nd O24 84.98(11) 2_675 .
O25 Nd O24 69.26(11) . .
O20 Nd O24 144.08(11) 2_676 .
O8 Nd O24 132.04(11) . .
O1 Nd O19 74.48(11) 2_665 2_676
O2 Nd O19 69.98(11) 1_665 2_676
O9 Nd O19 127.98(10) 2_675 2_676
O25 Nd O19 149.33(11) . 2_676
O20 Nd O19 51.50(10) 2_676 2_676
O8 Nd O19 79.00(11) . 2_676
O24 Nd O19 125.70(11) . 2_676
O1 Nd O9 119.68(10) 2_665 .
O2 Nd O9 136.89(10) 1_665 .
O9 Nd O9 66.14(11) 2_675 .
O25 Nd O9 69.56(10) . .
O20 Nd O9 65.89(9) 2_676 .
O8 Nd O9 47.63(9) . .
O24 Nd O9 134.24(10) . .
O19 Nd O9 99.99(9) 2_676 .
O1 Nd C18 99.82(12) 2_665 2_676
O2 Nd C18 70.61(12) 1_665 2_676
O9 Nd C18 103.06(11) 2_675 2_676
O25 Nd C18 150.77(12) . 2_676
O20 Nd C18 25.65(11) 2_676 2_676
O8 Nd C18 81.32(11) . 2_676
O24 Nd C18 139.96(12) . 2_676
O19 Nd C18 25.87(11) 2_676 2_676
O9 Nd C18 83.04(10) . 2_676
O1 Nd C7 95.19(11) 2_665 .
O2 Nd C7 153.55(11) 1_665 .
O9 Nd C7 89.32(11) 2_675 .
O25 Nd C7 66.01(11) . .
O20 Nd C7 77.00(11) 2_676 .
O8 Nd C7 23.54(11) . .
O24 Nd C7 134.91(11) . .
O19 Nd C7 92.28(11) 2_676 .
O9 Nd C7 24.55(10) . .
C18 Nd C7 84.85(12) 2_676 .
C7 O8 Nd 103.2(3) . .
C18 O19 Nd 93.2(3) . 2_676
C3 O1 Nd 137.0(3) . 2_665
C3 O2 Nd 171.1(3) . 1_445
O2 C3 O1 124.8(4) . .
O2 C3 C4 118.2(4) . .
O1 C3 C4 117.1(4) . .
C12 C4 C5 120.2(4) . .
C12 C4 C3 120.7(4) . .
C5 C4 C3 119.0(4) . .
C4 C5 C6 119.6(4) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C10 C6 C5 120.2(4) . .
C10 C6 C7 120.7(4) . .
C5 C6 C7 119.1(4) . .
O8 C7 O9 122.2(4) . .
O8 C7 C6 118.7(4) . .
O9 C7 C6 119.1(4) . .
O8 C7 Nd 53.3(2) . .
O9 C7 Nd 70.8(2) . .
C6 C7 Nd 163.0(3) . .
C7 O9 Nd 153.0(3) . 2_675
C7 O9 Nd 84.6(2) . .
Nd O9 Nd 113.86(11) 2_675 .
C11 C10 C6 118.6(4) . .
C11 C10 H10 120.7 . .
C6 C10 H10 120.7 . .
C10 C11 C12 121.9(4) . .
C10 C11 O13 119.8(4) . .
C12 C11 O13 118.2(4) . .
C4 C12 C11 119.2(4) . .
C4 C12 H12 120.4 . .
C11 C12 H12 120.4 . .
C14 O13 C11 116.4(3) . .
O13 C14 C22 115.4(4) . .
O13 C14 C15 123.3(4) . .
C22 C14 C15 121.3(4) . .
C16 C15 C14 118.9(4) . .
C16 C15 H15 120.5 . .
C14 C15 H15 120.5 . .
C15 C16 C17 120.7(4) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C16 C17 C21 119.6(4) . .
C16 C17 C18 120.8(4) . .
C21 C17 C18 119.5(4) . .
O20 C18 O19 119.8(4) . .
O20 C18 C17 120.3(4) . .
O19 C18 C17 119.9(4) . .
O20 C18 Nd 59.0(2) . 2_676
O19 C18 Nd 60.9(2) . 2_676
C17 C18 Nd 178.0(3) . 2_676
C18 O20 Nd 95.3(3) . 2_676
C22 C21 C17 120.7(4) . .
C22 C21 H21 119.6 . .
C17 C21 H21 119.6 . .
C21 C22 C14 118.8(4) . .
C21 C22 N23 121.9(4) . .
C14 C22 N23 119.3(4) . .
C22 N23 H23A 117.4 . .
C22 N23 H23B 120.9 . .
H23A N23 H23B 103.5 . .
Nd O24 H24A 129.8 . .
Nd O24 H24B 124.4 . .
H24A O24 H24B 105.5 . .
Nd O25 H25A 127.9 . .
Nd O25 H25B 109.5 . .
H25A O25 H25B 119.5 . .
H26A O26 H26B 107.7 . .
C30 N27 C28 124.3(11) . .
C30 N27 C28 124.3(11) 2_656 2_656
C30 N27 C29 119.9(11) 2_656 2_656
C28 N27 C29 115.8(9) 2_656 2_656
C30 N27 C29 119.9(11) . .
C28 N27 C29 115.8(9) . .
C30 C28 C29 119.5(13) 2_656 2_656
N27 C28 H28A 109.9 . .
N27 C28 H28B 108.1 . .
H28A C28 H28B 109.5 . .
C30 C28 H28C 100.8 2_656 .
N27 C28 H28C 110.4 . .
C29 C28 H28C 97.8 2_656 .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O31 C29 N27 122.0(10) 2_656 .
C30 C29 C28 112.0(12) 2_656 2_656
O31 C29 H29A 111.0 2_656 .
C30 C29 H29A 132.7 2_656 .
N27 C29 H29A 109.2 . .
N27 C29 H29B 109.2 . .
O31 C29 H29C 93.9 2_656 .
C30 C29 H29C 117.8 2_656 .
N27 C29 H29C 110.1 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C28 C30 C29 128.4(15) 2_656 2_656
N27 C30 O31 119.6(15) . .
N27 C30 H30 120.2 . .
O31 C30 H30 120.2 . .
H32A O32 H32B 111.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Nd O1 2.358(3) 2_665
Nd O2 2.364(3) 1_665
Nd O9 2.422(3) 2_675
Nd O25 2.487(3) .
Nd O20 2.515(3) 2_676
Nd O8 2.518(3) .
Nd O24 2.546(3) .
Nd O19 2.556(3) 2_676
Nd O9 2.901(3) .
Nd C18 2.921(4) 2_676
Nd C7 3.058(4) .
O8 C7 1.255(5) .
O19 C18 1.277(5) .
O19 Nd 2.556(3) 2_676
O1 C3 1.252(5) .
O1 Nd 2.358(3) 2_665
O2 C3 1.244(5) .
O2 Nd 2.364(3) 1_445
C3 C4 1.506(6) .
C4 C12 1.380(6) .
C4 C5 1.393(6) .
C5 C6 1.396(6) .
C5 H5 0.9500 .
C6 C10 1.393(6) .
C6 C7 1.502(6) .
C7 O9 1.276(5) .
O9 Nd 2.422(3) 2_675
C10 C11 1.378(6) .
C10 H10 0.9500 .
C11 C12 1.382(6) .
C11 O13 1.404(5) .
C12 H12 0.9500 .
O13 C14 1.386(5) .
C14 C22 1.391(6) .
C14 C15 1.396(6) .
C15 C16 1.389(7) .
C15 H15 0.9500 .
C16 C17 1.388(6) .
C16 H16 0.9500 .
C17 C21 1.394(6) .
C17 C18 1.485(6) .
C18 O20 1.270(5) .
C18 Nd 2.921(4) 2_676
O20 Nd 2.515(3) 2_676
C21 C22 1.390(6) .
C21 H21 0.9500 .
C22 N23 1.412(6) .
N23 H23A 0.9119 .
N23 H23B 0.9153 .
O24 H24A 0.9033 .
O24 H24B 0.8898 .
O25 H25A 0.9171 .
O25 H25B 0.9047 .
O26 H26A 0.8968 .
O26 H26B 0.9664 .
N27 C30 1.344(16) 2_656
N27 C30 1.344(16) .
N27 C28 1.403(13) .
N27 C28 1.403(13) 2_656
N27 C29 1.458(14) 2_656
N27 C29 1.458(14) .
C28 C30 1.28(2) 2_656
C28 C29 1.52(2) 2_656
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 O31 1.37(2) 2_656
C29 C30 1.41(2) 2_656
C29 C28 1.52(2) 2_656
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 C28 1.28(2) 2_656
C30 C29 1.41(2) 2_656
C30 O31 1.51(2) .
C30 H30 0.9500 .
O31 C29 1.37(2) 2_656
O32 H32A 0.8961 .
O32 H32B 0.9416 .
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 0.91 2.09 2.999(6) 179 2_576
N23 H23B O26 0.92 2.03 2.945(7) 179 1_455
O24 H24A O31 0.90 1.89 2.792(11) 180 2_665
O24 H24B O19 0.89 2.02 2.905(5) 179 1_654
O25 H25A O26 0.92 1.82 2.728(5) 171 2_665
O25 H25B O20 0.90 1.79 2.698(4) 180 1_554
O26 H26A O8 0.90 1.96 2.854(5) 179 .
O26 H26B O32 0.97 2.52 3.044(12) 114 .
O32 H32B O24 0.94 2.37 2.873(11) 113 2_665
