#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:22:36 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178810 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/64/4106449.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_4106449
loop_
_publ_author_name
'Dong Liu'
'Jian-Ping Lang'
'Brendan F. Abrahams'
_publ_contact_author_address
;
 School of Chemistry and Chemical Engineering
 Suzhou University
 Suzhou 215123, Jiangsu
 P.R.China
;
_publ_contact_author_email       jplang@suda.edu.cn
_publ_contact_author_fax         86-512-65880089
_publ_contact_author_name        'Jian-Ping Lang'
_publ_contact_author_phone       86-512-65882865
_publ_section_title
;
 Highly Efficient Separation of a Solid Mixture of Naphthalene and
 Anthracene by a Reusable Porous Metal-Organic Framework through a
 Single-Crystal-to-Single-Crystal Transformation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11042
_journal_page_last               11045
_journal_paper_doi               10.1021/ja203053y
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C40 H28 N4 Ni2 O9, 4(C6 H6)'
_chemical_formula_sum            'C64 H52 N4 Ni2 O9'
_chemical_formula_weight         1138.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.477(3)
_cell_length_b                   23.392(5)
_cell_length_c                   32.321(7)
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.4894
_cell_measurement_theta_min      3.0642
_cell_volume                     11701(4)
_computing_cell_refinement       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_data_collection       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_data_reduction
'CrystalStructure, Ver. 3.60 (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku MercuryCCD area detector'
_diffrn_measurement_method       ω
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            9470
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.8722
_exptl_absorpt_correction_T_min  0.7910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Jacobson, R. (1998) Private communication to Rigaku Company, Tokyo, Japan.'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       Block
_exptl_crystal_F_000             4736
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0687
_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)+(0.1165P)²+38.4255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1821
_reflns_number_gt                3569
_reflns_number_total             3630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203053y_si_002_6.cif
_cod_data_source_block           5
_cod_database_code               4106449
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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 0.11111(5) 0.00946(3) -0.09753(3) 0.0165(2) Uani 1 1 d .
O1 O 0.0823(3) -0.0662(2) -0.06860(15) 0.0247(11) Uani 1 1 d .
N1 N 0.1406(4) 0.0866(3) -0.1271(2) 0.0255(13) Uani 1 1 d .
C1 C 0.0841(4) 0.1296(3) -0.1326(2) 0.0286(16) Uani 1 1 d .
H1 H 0.0285 0.1259 -0.1212 0.034 Uiso 1 1 calc R
C2 C 0.1036(5) 0.1781(3) -0.1536(3) 0.0290(17) Uani 1 1 d .
H2 H 0.0620 0.2072 -0.1557 0.035 Uiso 1 1 calc R
N2 N -0.0219(4) 0.2372(3) -0.31399(19) 0.0233(13) Uani 1 1 d .
O2 O -0.0563(3) -0.0561(2) -0.05045(15) 0.0239(10) Uani 1 1 d .
C3 C 0.1842(4) 0.1853(3) -0.1723(2) 0.0230(14) Uani 1 1 d .
O3 O -0.1694(3) -0.1747(3) 0.06893(18) 0.0396(15) Uani 1 1 d .
C4 C 0.2413(5) 0.1416(3) -0.1665(2) 0.0287(16) Uani 1 1 d .
H4 H 0.2970 0.1443 -0.1779 0.034 Uiso 1 1 calc R
O4 O -0.0679(3) -0.2187(2) 0.10750(14) 0.0227(10) Uani 1 1 d .
O5 O 0.0000 0.0000 -0.1341(2) 0.0187(14) Uani 1 2 d S
C5 C 0.2189(5) 0.0939(3) -0.1443(2) 0.0300(17) Uani 1 1 d .
H5 H 0.2603 0.0649 -0.1411 0.036 Uiso 1 1 calc R
C6 C 0.2039(4) 0.2365(3) -0.1984(2) 0.0236(15) Uani 1 1 d .
H6 H 0.1601 0.2665 -0.1935 0.028 Uiso 1 1 calc R
C7 C 0.2146(4) 0.2266(3) -0.2449(2) 0.0195(14) Uani 1 1 d .
H7 H 0.2419 0.1889 -0.2495 0.023 Uiso 1 1 calc R
C8 C 0.1346(4) 0.2309(3) -0.2709(2) 0.0212(14) Uani 1 1 d .
C9 C 0.0723(5) 0.1870(3) -0.2683(3) 0.0321(18) Uani 1 1 d .
H9 H 0.0828 0.1542 -0.2523 0.039 Uiso 1 1 calc R
C10 C -0.0035(5) 0.1931(4) -0.2895(3) 0.0347(18) Uani 1 1 d .
H10 H -0.0454 0.1642 -0.2867 0.042 Uiso 1 1 calc R
C11 C 0.0355(6) 0.2790(4) -0.3172(3) 0.0383(19) Uani 1 1 d .
H11 H 0.0230 0.3106 -0.3341 0.046 Uiso 1 1 calc R
C12 C 0.1144(5) 0.2773(4) -0.2960(3) 0.036(2) Uani 1 1 d .
H12 H 0.1538 0.3077 -0.2988 0.043 Uiso 1 1 calc R
C13 C 0.0307(3) -0.1178(3) -0.0111(2) 0.0526(19) Uani 1 1 d GU
C14 C 0.1114(3) -0.1431(4) -0.0067(2) 0.075(2) Uani 1 1 d GU
H14 H 0.1563 -0.1338 -0.0251 0.090 Uiso 1 1 calc R
C15 C 0.1257(3) -0.1821(4) 0.0250(3) 0.085(2) Uani 1 1 d GU
H15 H 0.1803 -0.1992 0.0281 0.101 Uiso 1 1 calc R
C16 C 0.0594(4) -0.1958(4) 0.0522(2) 0.077(2) Uani 1 1 d GU
H16 H 0.0691 -0.2222 0.0737 0.092 Uiso 1 1 calc R
C17 C -0.0214(3) -0.1705(3) 0.0478(2) 0.0573(19) Uani 1 1 d GU
C18 C -0.0357(3) -0.1315(3) 0.0161(2) 0.0450(18) Uani 1 1 d GU
H18 H -0.0903 -0.1144 0.0130 0.054 Uiso 1 1 calc R
C19 C 0.0183(4) -0.0760(3) -0.0463(2) 0.0212(14) Uani 1 1 d .
C20 C -0.0923(5) -0.1894(3) 0.0768(2) 0.0261(16) Uani 1 1 d .
C21 C 0.3133(14) -0.0310(14) 0.2386(7) 0.250(8) Uani 1 1 d GU
H21 H 0.2647 -0.0235 0.2552 0.300 Uiso 1 1 calc R
C22 C 0.3936(16) -0.0394(12) 0.2568(5) 0.254(8) Uani 1 1 d GU
H22 H 0.3994 -0.0376 0.2857 0.305 Uiso 1 1 calc R
C23 C 0.4654(13) -0.0506(6) 0.2322(7) 0.258(8) Uani 1 1 d GDU
H23 H 0.5198 -0.0562 0.2445 0.310 Uiso 1 1 calc R
C24 C 0.4569(13) -0.0534(12) 0.1895(7) 0.254(8) Uani 1 1 d GU
H24 H 0.5054 -0.0609 0.1729 0.305 Uiso 1 1 calc R
C25 C 0.3765(16) -0.0450(15) 0.1712(5) 0.248(9) Uani 1 1 d GU
H25 H 0.3707 -0.0468 0.1423 0.298 Uiso 1 1 calc R
C26 C 0.3047(13) -0.0338(11) 0.1958(7) 0.244(8) Uani 1 1 d GU
H26 H 0.2504 -0.0282 0.1835 0.293 Uiso 1 1 calc R
C27 C 0.2539(19) -0.1429(15) 0.1098(7) 0.278(13) Uani 1 1 d GU
H27 H 0.2342 -0.1451 0.1373 0.334 Uiso 1 1 calc R
C28 C 0.301(2) -0.1878(11) 0.0929(10) 0.276(12) Uani 1 1 d GU
H28 H 0.3131 -0.2203 0.1089 0.332 Uiso 1 1 calc R
C29 C 0.3302(18) -0.1844(12) 0.0523(10) 0.275(12) Uani 1 1 d GU
H29 H 0.3621 -0.2148 0.0408 0.330 Uiso 1 1 calc R
C30 C 0.3123(19) -0.1362(14) 0.0286(7) 0.272(12) Uani 1 1 d GU
H30 H 0.3321 -0.1340 0.0012 0.327 Uiso 1 1 calc R
C31 C 0.2652(18) -0.0914(10) 0.0456(9) 0.273(12) Uani 1 1 d GU
H31 H 0.2531 -0.0588 0.0295 0.327 Uiso 1 1 calc R
C32 C 0.2360(17) -0.0947(12) 0.0861(10) 0.274(12) Uani 1 1 d GU
H32 H 0.2042 -0.0644 0.0976 0.329 Uiso 1 1 calc 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'
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'
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
O1 Ni1 O2 91.8(2) . 2
O1 Ni1 O4 92.2(2) . 7_544
O2 Ni1 O4 171.78(19) 2 7_544
O1 Ni1 N1 179.9(3) . .
O2 Ni1 N1 88.3(2) 2 .
O4 Ni1 N1 87.8(2) 7_544 .
O1 Ni1 O5 89.29(16) . .
O2 Ni1 O5 97.72(18) 2 .
O4 Ni1 O5 89.52(18) 7_544 .
N1 Ni1 O5 90.77(19) . .
O1 Ni1 N2 89.1(2) . 3
O2 Ni1 N2 87.4(2) 2 3
O4 Ni1 N2 85.5(2) 7_544 3
N1 Ni1 N2 90.9(2) . 3
O5 Ni1 N2 174.7(2) . 3
C19 O1 Ni1 126.6(5) . .
C5 N1 C1 115.8(6) . .
C5 N1 Ni1 119.7(5) . .
C1 N1 Ni1 124.3(5) . .
N1 C1 C2 123.2(6) . .
N1 C1 H1 118.4 . .
C2 C1 H1 118.4 . .
C1 C2 C3 121.1(7) . .
C1 C2 H2 119.4 . .
C3 C2 H2 119.4 . .
C11 N2 C10 118.3(7) . .
C11 N2 Ni1 120.6(5) . 11_454
C10 N2 Ni1 121.1(5) . 11_454
C19 O2 Ni1 131.0(4) . 2
C4 C3 C2 115.3(6) . .
C4 C3 C6 123.1(6) . .
C2 C3 C6 121.5(6) . .
C3 C4 C5 121.3(7) . .
C3 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
C20 O4 Ni1 130.2(4) . 15_445
Ni1 O5 Ni1 111.5(3) 2 .
N1 C5 C4 123.2(7) . .
N1 C5 H5 118.4 . .
C4 C5 H5 118.4 . .
C3 C6 C7 117.1(6) . .
C3 C6 C6 120.7(6) . 14
C7 C6 C6 87.8(3) . 14
C3 C6 H6 109.8 . .
C7 C6 H6 109.8 . .
C6 C6 H6 109.8 14 .
C8 C7 C6 116.8(6) . .
C8 C7 C7 122.5(6) . 14
C6 C7 C7 88.3(3) . 14
C8 C7 H7 109.2 . .
C6 C7 H7 109.2 . .
C7 C7 H7 109.2 14 .
C12 C8 C9 116.7(6) . .
C12 C8 C7 124.3(6) . .
C9 C8 C7 118.9(6) . .
C10 C9 C8 118.8(7) . .
C10 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
N2 C10 C9 124.2(7) . .
N2 C10 H10 117.9 . .
C9 C10 H10 117.9 . .
N2 C11 C12 121.8(8) . .
N2 C11 H11 119.1 . .
C12 C11 H11 119.1 . .
C8 C12 C11 120.2(7) . .
C8 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C14 C13 C18 120.0 . .
C14 C13 C19 117.9(4) . .
C18 C13 C19 122.1(4) . .
C15 C14 C13 120.0 . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C16 120.0 . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C15 C16 C17 120.0 . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C18 C17 C16 120.0 . .
C18 C17 C20 122.2(4) . .
C16 C17 C20 117.7(4) . .
C17 C18 C13 120.0 . .
C17 C18 H18 120.0 . .
C13 C18 H18 120.0 . .
O1 C19 O2 127.1(6) . .
O1 C19 C13 116.9(6) . .
O2 C19 C13 115.9(5) . .
O4 C20 O3 125.9(6) . .
O4 C20 C17 115.3(6) . .
O3 C20 C17 118.8(6) . .
C22 C21 C26 120.0 . .
C22 C21 H21 120.0 . .
C26 C21 H21 120.0 . .
C23 C22 C21 120.0 . .
C23 C22 H22 120.0 . .
C21 C22 H22 120.0 . .
C22 C23 C24 120.0 . .
C22 C23 H23 120.0 . .
C24 C23 H23 120.0 . .
C25 C24 C23 120.0 . .
C25 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
C26 C25 C24 120.0 . .
C26 C25 H25 120.0 . .
C24 C25 H25 120.0 . .
C25 C26 C21 120.0 . .
C25 C26 H26 120.0 . .
C21 C26 H26 120.0 . .
C28 C27 C32 120.0 . .
C28 C27 H27 120.0 . .
C32 C27 H27 120.0 . .
C27 C28 C29 120.0 . .
C27 C28 H28 120.0 . .
C29 C28 H28 120.0 . .
C30 C29 C28 120.0 . .
C30 C29 H29 120.0 . .
C28 C29 H29 120.0 . .
C31 C30 C29 120.0 . .
C31 C30 H30 120.0 . .
C29 C30 H30 120.0 . .
C32 C31 C30 120.0 . .
C32 C31 H31 120.0 . .
C30 C31 H31 120.0 . .
C31 C32 C27 120.0 . .
C31 C32 H32 120.0 . .
C27 C32 H32 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.050(5) .
Ni1 O2 2.056(5) 2
Ni1 O4 2.057(5) 7_544
Ni1 N1 2.092(6) .
Ni1 O5 2.097(4) .
Ni1 N2 2.111(6) 3
O1 C19 1.247(8) .
N1 C5 1.344(9) .
N1 C1 1.345(10) .
C1 C2 1.356(11) .
C1 H1 0.9400 .
C2 C3 1.398(10) .
C2 H2 0.9400 .
N2 C11 1.325(10) .
N2 C10 1.332(10) .
N2 Ni1 2.111(6) 11_454
O2 C19 1.252(8) .
O2 Ni1 2.056(5) 2
C3 C4 1.364(10) .
C3 C6 1.495(10) .
O3 C20 1.267(9) .
C4 C5 1.370(11) .
C4 H4 0.9400 .
O4 C20 1.265(9) .
O4 Ni1 2.057(5) 15_445
O5 Ni1 2.097(4) 2
C5 H5 0.9400 .
C6 C7 1.531(10) .
C6 C6 1.561(12) 14
C6 H6 0.9900 .
C7 C8 1.500(9) .
C7 C7 1.549(12) 14
C7 H7 0.9900 .
C8 C12 1.392(11) .
C8 C9 1.410(10) .
C9 C10 1.367(10) .
C9 H9 0.9400 .
C10 H10 0.9400 .
C11 C12 1.399(11) .
C11 H11 0.9400 .
C12 H12 0.9400 .
C13 C14 1.3900 .
C13 C18 1.3900 .
C13 C19 1.512(8) .
C14 C15 1.3900 .
C14 H14 0.9400 .
C15 C16 1.3900 .
C15 H15 0.9400 .
C16 C17 1.3900 .
C16 H16 0.9400 .
C17 C18 1.3900 .
C17 C20 1.510(8) .
C18 H18 0.9400 .
C21 C22 1.3900 .
C21 C26 1.3900 .
C21 H21 0.9400 .
C22 C23 1.3900 .
C22 H22 0.9400 .
C23 C24 1.3900 .
C23 H23 0.9400 .
C24 C25 1.3900 .
C24 H24 0.9400 .
C25 C26 1.3900 .
C25 H25 0.9400 .
C26 H26 0.9400 .
C27 C28 1.3900 .
C27 C32 1.3900 .
C27 H27 0.9400 .
C28 C29 1.3900 .
C28 H28 0.9400 .
C29 C30 1.3900 .
C29 H29 0.9400 .
C30 C31 1.3900 .
C30 H30 0.9400 .
C31 C32 1.3900 .
C31 H31 0.9400 .
C32 H32 0.9400 .
