#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:38:02 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179539 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/08/4500843.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_4500843
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         'C25 H21 N3 Ni O9'
_chemical_formula_sum            'C25 H21 N3 Ni O9'
_chemical_formula_weight         566.16
_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                98.1485(16)
_cell_angle_beta                 108.8361(17)
_cell_angle_gamma                105.377(3)
_cell_formula_units_Z            2
_cell_length_a                   9.9873(3)
_cell_length_b                   12.3715(4)
_cell_length_c                   15.2890(7)
_cell_measurement_reflns_used    6158
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      1.45
_cell_volume                     1669.55(11)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19983
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  0.9120
_exptl_absorpt_correction_T_min  0.7880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_platon_squeeze_details
;
;
_refine_diff_density_max         1.244
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1001P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1693
_reflns_number_gt                4490
_reflns_number_total             7834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200350j_si_001.cif
_cod_data_source_block           7
_cod_database_code               4500843
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
Ni1 Ni 0.74427(4) 0.24137(3) 0.74316(2) 0.04045(15) Uani 1 1 d .
O2 O 0.5377(2) 0.11274(17) 0.68842(14) 0.0385(5) Uani 1 1 d .
C3 C 0.4236(4) 0.1077(3) 0.7079(2) 0.0464(8) Uani 1 1 d .
O4 O 0.4229(3) 0.1689(3) 0.78080(18) 0.0725(8) Uani 1 1 d .
C5 C 0.2750(3) 0.0204(3) 0.6390(2) 0.0414(7) Uani 1 1 d .
C6 C 0.2623(3) -0.0414(3) 0.5518(2) 0.0390(7) Uani 1 1 d .
H6 H 0.3476 -0.0281 0.5347 0.047 Uiso 1 1 calc R
C7 C 0.1264(3) -0.1222(3) 0.4892(2) 0.0412(7) Uani 1 1 d .
C8 C 0.1117(4) -0.1895(3) 0.3949(2) 0.0445(7) Uani 1 1 d .
O9 O 0.2156(2) -0.15496(17) 0.36563(13) 0.0397(5) Uani 1 1 d .
O10 O -0.0049(3) -0.2770(2) 0.35057(18) 0.0674(7) Uani 1 1 d .
C11 C 0.0008(3) -0.1422(3) 0.5138(2) 0.0434(7) Uani 1 1 d .
H11 H -0.0921 -0.1987 0.4722 0.052 Uiso 1 1 calc R
C12 C 0.0136(4) -0.0788(3) 0.5997(2) 0.0500(8) Uani 1 1 d .
C13 C 0.1495(3) 0.0024(3) 0.6625(2) 0.0468(8) Uani 1 1 d .
H13 H 0.1561 0.0453 0.7213 0.056 Uiso 1 1 calc R
O14 O -0.1154(2) -0.0935(2) 0.62097(16) 0.0525(6) Uani 1 1 d .
C15 C -0.1263(3) -0.1472(3) 0.6923(2) 0.0446(7) Uani 1 1 d .
C16 C -0.0276(4) -0.2003(3) 0.7368(2) 0.0504(8) Uani 1 1 d .
H16 H 0.0557 -0.1993 0.7194 0.061 Uiso 1 1 calc R
C17 C -0.0484(4) -0.2546(3) 0.8059(3) 0.0576(9) Uani 1 1 d .
H17 H 0.0203 -0.2907 0.8363 0.069 Uiso 1 1 calc R
C18 C -0.1716(4) -0.2563(3) 0.8314(2) 0.0544(8) Uani 1 1 d .
C19 C -0.1893(5) -0.3151(4) 0.9064(3) 0.0766(12) Uani 1 1 d .
O20 O -0.1042(4) -0.3614(3) 0.9465(3) 0.1026(11) Uani 1 1 d .
O21 O -0.3105(4) -0.3143(3) 0.9239(2) 0.0966(10) Uani 1 1 d .
H21 H -0.3025 -0.3453 0.9764 0.145 Uiso 1 1 d .
C22 C -0.2709(4) -0.2008(3) 0.7850(2) 0.0529(8) Uani 1 1 d .
H22 H -0.3552 -0.2024 0.8015 0.063 Uiso 1 1 calc R
C23 C -0.2491(3) -0.1446(3) 0.7165(2) 0.0461(7) Uani 1 1 d .
N24 N -0.3490(3) -0.0943(2) 0.6675(2) 0.0524(7) Uani 1 1 d .
H24A H -0.4281 -0.0969 0.6820 0.063 Uiso 1 1 d .
H24B H -0.3111 -0.0244 0.6587 0.063 Uiso 1 1 d .
N25 N 0.6537(3) 0.3362(2) 0.65258(17) 0.0458(6) Uani 1 1 d .
C26 C 0.5537(4) 0.2856(3) 0.5641(2) 0.0505(8) Uani 1 1 d .
H26 H 0.5239 0.2039 0.5421 0.061 Uiso 1 1 calc R
C27 C 0.4914(4) 0.3470(3) 0.5030(2) 0.0583(10) Uani 1 1 d .
H27 H 0.4199 0.3071 0.4407 0.070 Uiso 1 1 calc R
C28 C 0.5326(4) 0.4655(3) 0.5321(2) 0.0520(9) Uani 1 1 d .
C29 C 0.6387(5) 0.5177(3) 0.6228(3) 0.0839(15) Uani 1 1 d .
H29 H 0.6738 0.5996 0.6453 0.101 Uiso 1 1 calc R
C30 C 0.6944(5) 0.4509(3) 0.6813(2) 0.0738(13) Uani 1 1 d .
H30 H 0.7644 0.4885 0.7445 0.089 Uiso 1 1 calc R
N31 N 0.8360(3) 0.1499(2) 0.83614(16) 0.0379(6) Uani 1 1 d .
C32 C 0.9688(3) 0.1353(3) 0.8447(2) 0.0452(8) Uani 1 1 d .
H32 H 1.0186 0.1660 0.8057 0.054 Uiso 1 1 calc R
C33 C 1.0354(3) 0.0774(3) 0.9080(2) 0.0440(7) Uani 1 1 d .
H33 H 1.1292 0.0698 0.9119 0.053 Uiso 1 1 calc R
C34 C 0.9659(3) 0.0308(2) 0.96539(18) 0.0358(6) Uani 1 1 d .
C35 C 0.8282(3) 0.0455(3) 0.9556(2) 0.0432(7) Uani 1 1 d .
H35 H 0.7751 0.0148 0.9929 0.052 Uiso 1 1 calc R
C36 C 0.7703(4) 0.1043(3) 0.8918(2) 0.0460(8) Uani 1 1 d .
H36 H 0.6768 0.1133 0.8870 0.055 Uiso 1 1 calc R
O37 O 0.9494(3) 0.3737(2) 0.78869(16) 0.0578(6) Uani 1 1 d .
H37A H 0.9853 0.3698 0.8494 0.069 Uiso 1 1 d .
H37B H 0.9696 0.3393 0.7392 0.069 Uiso 1 1 d .
O38 O 0.6909(2) 0.33008(18) 0.84510(14) 0.0490(5) Uani 1 1 d .
H38A H 0.5988 0.2749 0.8232 0.059 Uiso 1 1 d .
H38B H 0.6897 0.4030 0.8617 0.059 Uiso 1 1 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'
O O 0.0106 0.0060 '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'
Ni Ni 0.3393 1.1124 '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 Ni1 O2 85.28(8) 2_656 .
O9 Ni1 O38 175.79(7) 2_656 .
O2 Ni1 O38 92.69(9) . .
O9 Ni1 N31 92.02(8) 2_656 .
O2 Ni1 N31 91.76(9) . .
O38 Ni1 N31 91.72(8) . .
O9 Ni1 N25 89.12(9) 2_656 .
O2 Ni1 N25 88.94(9) . .
O38 Ni1 N25 87.16(9) . .
N31 Ni1 N25 178.70(10) . .
O9 Ni1 O37 92.40(9) 2_656 .
O2 Ni1 O37 175.84(8) . .
O38 Ni1 O37 89.40(9) . .
N31 Ni1 O37 91.78(9) . .
N25 Ni1 O37 87.56(10) . .
C3 O2 Ni1 129.2(2) . .
O2 C3 O4 125.2(3) . .
O2 C3 C5 117.7(3) . .
O4 C3 C5 117.1(3) . .
C13 C5 C6 119.3(3) . .
C13 C5 C3 119.8(3) . .
C6 C5 C3 120.9(3) . .
C5 C6 C7 120.8(3) . .
C5 C6 H6 119.6 . .
C7 C6 H6 119.6 . .
C6 C7 C11 119.9(3) . .
C6 C7 C8 121.2(3) . .
C11 C7 C8 118.9(3) . .
O9 C8 O10 124.7(3) . .
O9 C8 C7 117.8(3) . .
O10 C8 C7 117.5(3) . .
C8 O9 Ni1 128.3(2) . 2_656
C12 C11 C7 118.9(3) . .
C12 C11 H11 120.5 . .
C7 C11 H11 120.5 . .
C11 C12 C13 121.3(3) . .
C11 C12 O14 118.6(3) . .
C13 C12 O14 120.0(3) . .
C5 C13 C12 119.7(3) . .
C5 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C15 O14 C12 118.1(2) . .
O14 C15 C16 124.3(3) . .
O14 C15 C23 113.8(3) . .
C16 C15 C23 121.8(3) . .
C17 C16 C15 120.8(3) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C16 C17 C18 119.5(3) . .
C16 C17 H17 120.2 . .
C18 C17 H17 120.2 . .
C17 C18 C22 118.6(3) . .
C17 C18 C19 117.7(3) . .
C22 C18 C19 123.6(3) . .
O20 C19 O21 123.2(4) . .
O20 C19 C18 123.6(4) . .
O21 C19 C18 113.2(4) . .
C19 O21 H21 104.7 . .
C23 C22 C18 122.0(3) . .
C23 C22 H22 119.0 . .
C18 C22 H22 119.0 . .
C22 C23 N24 122.6(3) . .
C22 C23 C15 117.2(3) . .
N24 C23 C15 120.1(3) . .
C23 N24 H24A 118.4 . .
C23 N24 H24B 117.8 . .
H24A N24 H24B 109.4 . .
C26 N25 C30 117.4(2) . .
C26 N25 Ni1 121.8(2) . .
C30 N25 Ni1 120.8(2) . .
N25 C26 C27 122.7(3) . .
N25 C26 H26 118.6 . .
C27 C26 H26 118.6 . .
C28 C27 C26 120.3(3) . .
C28 C27 H27 119.8 . .
C26 C27 H27 119.8 . .
C27 C28 C29 116.7(3) . .
C27 C28 C28 121.7(3) . 2_666
C29 C28 C28 121.5(4) . 2_666
C28 C29 C30 120.1(3) . .
C28 C29 H29 120.0 . .
C30 C29 H29 120.0 . .
N25 C30 C29 122.7(3) . .
N25 C30 H30 118.6 . .
C29 C30 H30 118.6 . .
C36 N31 C32 116.2(2) . .
C36 N31 Ni1 122.52(18) . .
C32 N31 Ni1 121.28(19) . .
N31 C32 C33 122.8(3) . .
N31 C32 H32 118.6 . .
C33 C32 H32 118.6 . .
C34 C33 C32 120.3(3) . .
C34 C33 H33 119.9 . .
C32 C33 H33 119.9 . .
C33 C34 C35 116.6(2) . .
C33 C34 C34 121.9(3) . 2_757
C35 C34 C34 121.6(3) . 2_757
C36 C35 C34 119.7(3) . .
C36 C35 H35 120.2 . .
C34 C35 H35 120.2 . .
N31 C36 C35 124.5(3) . .
N31 C36 H36 117.7 . .
C35 C36 H36 117.7 . .
Ni1 O37 H37A 98.2 . .
Ni1 O37 H37B 90.2 . .
H37A O37 H37B 126.3 . .
Ni1 O38 H38A 90.0 . .
Ni1 O38 H38B 135.4 . .
H38A O38 H38B 113.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O9 2.055(2) 2_656
Ni1 O2 2.063(2) .
Ni1 O38 2.068(2) .
Ni1 N31 2.075(2) .
Ni1 N25 2.080(2) .
Ni1 O37 2.083(2) .
O2 C3 1.255(4) .
C3 O4 1.259(4) .
C3 C5 1.516(4) .
C5 C13 1.384(4) .
C5 C6 1.389(4) .
C6 C7 1.389(4) .
C6 H6 0.9500 .
C7 C11 1.394(4) .
C7 C8 1.500(4) .
C8 O9 1.257(4) .
C8 O10 1.265(4) .
O9 Ni1 2.055(2) 2_656
C11 C12 1.379(5) .
C11 H11 0.9500 .
C12 C13 1.391(5) .
C12 O14 1.401(4) .
C13 H13 0.9500 .
O14 C15 1.374(4) .
C15 C16 1.380(4) .
C15 C23 1.398(4) .
C16 C17 1.370(5) .
C16 H16 0.9500 .
C17 C18 1.402(5) .
C17 H17 0.9500 .
C18 C22 1.415(5) .
C18 C19 1.475(6) .
C19 O20 1.203(5) .
C19 O21 1.324(5) .
O21 H21 0.9275 .
C22 C23 1.378(5) .
C22 H22 0.9500 .
C23 N24 1.387(4) .
N24 H24A 0.8807 .
N24 H24B 0.8953 .
N25 C26 1.332(4) .
N25 C30 1.332(4) .
C26 C27 1.383(4) .
C26 H26 0.9500 .
C27 C28 1.376(4) .
C27 H27 0.9500 .
C28 C29 1.378(4) .
C28 C28 1.496(5) 2_666
C29 C30 1.387(4) .
C29 H29 0.9500 .
C30 H30 0.9500 .
N31 C36 1.332(4) .
N31 C32 1.353(4) .
C32 C33 1.388(4) .
C32 H32 0.9500 .
C33 C34 1.382(4) .
C33 H33 0.9500 .
C34 C35 1.397(4) .
C34 C34 1.484(5) 2_757
C35 C36 1.369(4) .
C35 H35 0.9500 .
C36 H36 0.9500 .
O37 H37A 0.8943 .
O37 H37B 0.9205 .
O38 H38A 0.9104 .
O38 H38B 0.9063 .
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 H24B O9 0.90 2.30 3.200(3) 179 2_556
O37 H37B O10 0.92 1.66 2.582(3) 180 2_656
O38 H38A O4 0.91 1.74 2.650(4) 180 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.072 0.449 0.428 589 183 ' '
