#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:38:02 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179539 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/08/4500840.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_4500840
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         'C18 H17 La N2 O9, H2 O'
_chemical_formula_sum            'C18 H19 La N2 O10'
_chemical_formula_weight         562.26
_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                78.1625(16)
_cell_angle_beta                 89.430(2)
_cell_angle_gamma                65.239(3)
_cell_formula_units_Z            2
_cell_length_a                   10.1340(4)
_cell_length_b                   10.3552(4)
_cell_length_c                   10.7436(6)
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.94
_cell_volume                     998.34(8)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16375
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.200
_exptl_absorpt_correction_T_max  0.8100
_exptl_absorpt_correction_T_min  0.6093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.160
_refine_diff_density_min         -1.756
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0365
_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)+(0.0465P)²+0.7846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                4122
_reflns_number_total             4744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200350j_si_001.cif
_cod_data_source_block           4
_cod_database_code               4500840
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
La1 La 0.96661(2) -0.20630(2) -0.000512(19) 0.01729(8) Uani 1 1 d .
O2 O 0.8916(3) 0.0534(3) 0.0885(2) 0.0204(5) Uani 1 1 d .
O3 O 0.7417(3) -0.0538(3) 0.1075(3) 0.0244(6) Uani 1 1 d .
C4 C 0.7652(4) 0.0573(4) 0.1041(3) 0.0187(7) Uani 1 1 d .
C5 C 0.6416(4) 0.1963(4) 0.1159(3) 0.0180(7) Uani 1 1 d .
C6 C 0.4995(4) 0.2344(4) 0.0682(3) 0.0182(7) Uani 1 1 d .
H6 H 0.4783 0.1692 0.0304 0.022 Uiso 1 1 calc R
C7 C 0.3896(4) 0.3677(4) 0.0764(3) 0.0181(7) Uani 1 1 d .
C8 C 0.2347(4) 0.4148(4) 0.0228(3) 0.0178(7) Uani 1 1 d .
O9 O 0.1480(3) 0.5472(3) 0.0091(3) 0.0238(6) Uani 1 1 d .
O10 O 0.2032(3) 0.3181(3) -0.0060(2) 0.0207(5) Uani 1 1 d .
C11 C 0.4183(4) 0.4621(4) 0.1354(3) 0.0184(7) Uani 1 1 d .
H11 H 0.3431 0.5541 0.1401 0.022 Uiso 1 1 calc R
C12 C 0.5590(4) 0.4192(4) 0.1871(3) 0.0176(7) Uani 1 1 d .
C13 C 0.6712(4) 0.2904(4) 0.1752(3) 0.0189(7) Uani 1 1 d .
H13 H 0.7678 0.2656 0.2070 0.023 Uiso 1 1 calc R
O14 O 0.5845(3) 0.5150(3) 0.2466(2) 0.0209(5) Uani 1 1 d .
C15 C 0.6567(4) 0.4558(4) 0.3684(3) 0.0196(7) Uani 1 1 d .
C16 C 0.6321(4) 0.3523(4) 0.4569(4) 0.0238(8) Uani 1 1 d .
H16 H 0.5662 0.3154 0.4348 0.029 Uiso 1 1 calc R
C17 C 0.7045(4) 0.3028(4) 0.5784(4) 0.0231(8) Uani 1 1 d .
H17 H 0.6879 0.2321 0.6398 0.028 Uiso 1 1 calc R
C18 C 0.8010(4) 0.3569(4) 0.6097(3) 0.0206(7) Uani 1 1 d .
C19 C 0.8813(4) 0.3040(4) 0.7395(3) 0.0208(7) Uani 1 1 d .
O20 O 0.8415(3) 0.2309(3) 0.8283(2) 0.0202(5) Uani 1 1 d .
O21 O 0.9848(3) 0.3359(3) 0.7592(2) 0.0270(6) Uani 1 1 d .
C22 C 0.8242(4) 0.4613(4) 0.5196(3) 0.0214(7) Uani 1 1 d .
H22 H 0.8907 0.4975 0.5416 0.026 Uiso 1 1 calc R
C23 C 0.7516(4) 0.5137(4) 0.3977(4) 0.0219(8) Uani 1 1 d .
N24 N 0.7631(4) 0.6252(4) 0.3078(3) 0.0264(7) Uani 1 1 d .
H24A H 0.7500 0.6144 0.2190 0.032 Uiso 1 1 d R
H24B H 0.8558 0.6353 0.3192 0.032 Uiso 1 1 d R
O25 O 0.7781(3) 0.0057(3) -0.1628(2) 0.0253(6) Uani 1 1 d .
H25A H 0.6849 0.0372 -0.1916 0.030 Uiso 1 1 d R
H25B H 0.8053 0.0813 -0.1808 0.030 Uiso 1 1 d R
O26 O 0.9918(3) -0.2529(3) -0.2265(3) 0.0300(6) Uani 1 1 d .
C27 C 0.9638(5) -0.1935(5) -0.3427(4) 0.0334(9) Uani 1 1 d .
H27 H 1.0341 -0.1657 -0.3842 0.040 Uiso 1 1 calc R
N28 N 0.8455(4) -0.1664(4) -0.4124(3) 0.0331(8) Uani 1 1 d .
C29 C 0.7295(6) -0.2008(7) -0.3567(5) 0.0534(14) Uani 1 1 d .
H29A H 0.7664 -0.2686 -0.2736 0.080 Uiso 1 1 calc R
H29B H 0.6960 -0.2460 -0.4135 0.080 Uiso 1 1 calc R
H29C H 0.6480 -0.1111 -0.3457 0.080 Uiso 1 1 calc R
C30 C 0.8207(6) -0.0916(6) -0.5473(5) 0.0505(13) Uani 1 1 d .
H30A H 0.7380 0.0044 -0.5587 0.076 Uiso 1 1 calc R
H30B H 0.7992 -0.1496 -0.5987 0.076 Uiso 1 1 calc R
H30C H 0.9082 -0.0797 -0.5747 0.076 Uiso 1 1 calc R
O31 O 0.5108(3) 0.9099(3) 0.2342(3) 0.0359(7) Uani 1 1 d .
H31A H 0.5626 0.8259 0.2910 0.054 Uiso 1 1 d R
H31B H 0.5676 0.9430 0.1852 0.054 Uiso 1 1 d 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'
La La -0.2871 2.4523 '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'
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
O9 La1 O10 83.32(8) 1_645 2_655
O9 La1 O25 138.69(9) 1_645 .
O10 La1 O25 85.91(8) 2_655 .
O9 La1 O26 70.98(9) 1_645 .
O10 La1 O26 82.79(9) 2_655 .
O25 La1 O26 68.15(9) . .
O9 La1 O3 142.81(9) 1_645 .
O10 La1 O3 72.80(8) 2_655 .
O25 La1 O3 68.56(9) . .
O26 La1 O3 131.23(9) . .
O9 La1 O20 78.97(8) 1_645 2_756
O10 La1 O20 131.07(8) 2_655 2_756
O25 La1 O20 134.75(8) . 2_756
O26 La1 O20 131.35(9) . 2_756
O3 La1 O20 95.46(8) . 2_756
O9 La1 O2 101.96(8) 1_645 2_755
O10 La1 O2 160.11(8) 2_655 2_755
O25 La1 O2 77.47(8) . 2_755
O26 La1 O2 80.93(9) . 2_755
O3 La1 O2 110.22(8) . 2_755
O20 La1 O2 68.78(8) 2_756 2_755
O9 La1 O21 74.40(9) 1_645 2_756
O10 La1 O21 81.52(8) 2_655 2_756
O25 La1 O21 142.72(9) . 2_756
O26 La1 O21 143.32(9) . 2_756
O3 La1 O21 74.20(9) . 2_756
O20 La1 O21 49.86(8) 2_756 2_756
O2 La1 O21 118.36(8) 2_755 2_756
O9 La1 O2 146.11(8) 1_645 .
O10 La1 O2 120.52(8) 2_655 .
O25 La1 O2 71.45(8) . .
O26 La1 O2 131.19(8) . .
O3 La1 O2 47.81(7) . .
O20 La1 O2 67.21(7) 2_756 .
O2 La1 O2 64.38(9) 2_755 .
O21 La1 O2 85.10(8) 2_756 .
O9 La1 C19 75.21(9) 1_645 2_756
O10 La1 C19 106.23(9) 2_655 2_756
O25 La1 C19 145.87(9) . 2_756
O26 La1 C19 143.70(9) . 2_756
O3 La1 C19 84.43(9) . 2_756
O20 La1 C19 25.01(9) 2_756 2_756
O2 La1 C19 93.66(9) 2_755 2_756
O21 La1 C19 24.85(9) 2_756 2_756
O2 La1 C19 74.99(9) . 2_756
O9 La1 C4 156.69(9) 1_645 .
O10 La1 C4 96.10(9) 2_655 .
O25 La1 C4 64.12(9) . .
O26 La1 C4 132.20(9) . .
O3 La1 C4 23.90(9) . .
O20 La1 C4 84.12(8) 2_756 .
O2 La1 C4 86.50(9) 2_755 .
O21 La1 C4 82.45(9) 2_756 .
O2 La1 C4 24.51(8) . .
C19 La1 C4 82.67(9) 2_756 .
C4 O2 La1 144.7(2) . 2_755
C4 O2 La1 88.0(2) . .
La1 O2 La1 115.62(9) 2_755 .
C4 O3 La1 99.8(2) . .
O3 C4 O2 121.4(3) . .
O3 C4 C5 119.0(3) . .
O2 C4 C5 119.6(3) . .
O3 C4 La1 56.33(18) . .
O2 C4 La1 67.48(18) . .
C5 C4 La1 162.1(2) . .
C6 C5 C13 119.9(3) . .
C6 C5 C4 121.8(3) . .
C13 C5 C4 118.2(3) . .
C7 C6 C5 119.6(3) . .
C7 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
C6 C7 C11 120.7(3) . .
C6 C7 C8 121.2(3) . .
C11 C7 C8 118.1(3) . .
O9 C8 O10 125.1(3) . .
O9 C8 C7 117.6(3) . .
O10 C8 C7 117.3(3) . .
C8 O9 La1 174.0(2) . 1_465
C8 O10 La1 148.5(2) . 2_655
C12 C11 C7 118.7(3) . .
C12 C11 H11 120.7 . .
C7 C11 H11 120.7 . .
C13 C12 C11 121.6(3) . .
C13 C12 O14 120.8(3) . .
C11 C12 O14 117.5(3) . .
C12 C13 C5 119.3(3) . .
C12 C13 H13 120.4 . .
C5 C13 H13 120.4 . .
C12 O14 C15 116.0(3) . .
C16 C15 O14 123.0(3) . .
C16 C15 C23 121.9(3) . .
O14 C15 C23 115.0(3) . .
C15 C16 C17 119.5(3) . .
C15 C16 H16 120.2 . .
C17 C16 H16 120.2 . .
C18 C17 C16 119.9(4) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C17 C18 C22 119.8(3) . .
C17 C18 C19 120.8(3) . .
C22 C18 C19 119.3(3) . .
O21 C19 O20 121.1(3) . .
O21 C19 C18 119.5(3) . .
O20 C19 C18 119.4(3) . .
O21 C19 La1 60.86(19) . 2_756
O20 C19 La1 60.20(18) . 2_756
C18 C19 La1 178.2(3) . 2_756
C19 O20 La1 94.8(2) . 2_756
C19 O21 La1 94.3(2) . 2_756
C23 C22 C18 121.3(3) . .
C23 C22 H22 119.4 . .
C18 C22 H22 119.4 . .
N24 C23 C22 123.3(3) . .
N24 C23 C15 119.0(3) . .
C22 C23 C15 117.6(3) . .
C23 N24 H24A 111.3 . .
C23 N24 H24B 114.3 . .
H24A N24 H24B 109.6 . .
La1 O25 H25A 138.2 . .
La1 O25 H25B 109.7 . .
H25A O25 H25B 109.8 . .
C27 O26 La1 144.5(3) . .
O26 C27 N28 125.6(4) . .
O26 C27 H27 117.2 . .
N28 C27 H27 117.2 . .
C27 N28 C29 121.3(4) . .
C27 N28 C30 121.4(4) . .
C29 N28 C30 117.2(4) . .
N28 C29 H29A 109.5 . .
N28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
N28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
N28 C30 H30A 109.5 . .
N28 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
N28 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
H31A O31 H31B 112.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
La1 O9 2.423(3) 1_645
La1 O10 2.438(2) 2_655
La1 O25 2.548(2) .
La1 O26 2.561(3) .
La1 O3 2.592(3) .
La1 O20 2.595(2) 2_756
La1 O2 2.595(3) 2_755
La1 O21 2.610(3) 2_756
La1 O2 2.838(3) .
La1 C19 2.979(4) 2_756
La1 C4 3.070(3) .
O2 C4 1.274(4) .
O2 La1 2.595(3) 2_755
O3 C4 1.262(4) .
C4 C5 1.490(5) .
C5 C6 1.396(5) .
C5 C13 1.396(5) .
C6 C7 1.383(5) .
C6 H6 0.9500 .
C7 C11 1.392(5) .
C7 C8 1.515(5) .
C8 O9 1.259(4) .
C8 O10 1.263(4) .
O9 La1 2.423(3) 1_465
O10 La1 2.438(2) 2_655
C11 C12 1.386(5) .
C11 H11 0.9500 .
C12 C13 1.373(5) .
C12 O14 1.392(4) .
C13 H13 0.9500 .
O14 C15 1.393(4) .
C15 C16 1.384(5) .
C15 C23 1.397(5) .
C16 C17 1.391(5) .
C16 H16 0.9500 .
C17 C18 1.388(5) .
C17 H17 0.9500 .
C18 C22 1.394(5) .
C18 C19 1.498(5) .
C19 O21 1.256(5) .
C19 O20 1.264(5) .
C19 La1 2.979(4) 2_756
O20 La1 2.595(2) 2_756
O21 La1 2.610(3) 2_756
C22 C23 1.394(5) .
C22 H22 0.9500 .
C23 N24 1.389(5) .
N24 H24A 0.9992 .
N24 H24B 0.9991 .
O25 H25A 0.8942 .
O25 H25B 0.9195 .
O26 C27 1.250(5) .
C27 N28 1.314(5) .
C27 H27 0.9500 .
N28 C29 1.455(6) .
N28 C30 1.465(6) .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
O31 H31A 0.9002 .
O31 H31B 0.9002 .
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
N24 H24A O10 1.00 2.36 3.216(4) 144 2_665
N24 H24B O21 1.00 1.92 2.813(4) 148 2_766
O25 H25A O31 0.89 1.86 2.748(4) 174 2_665
O25 H25B O20 0.92 1.76 2.651(4) 164 1_554
O31 H31A N24 0.90 2.19 2.936(4) 140 .
O31 H31B O3 0.90 1.95 2.816(4) 160 1_565
