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#$Date: 2016-03-21 18:22:36 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178810 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/64/4106447.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_4106447
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 H30 N4 Ni2 O9, 2(C10 H8)'
_chemical_formula_sum            'C60 H46 N4 Ni2 O9'
_chemical_formula_weight         1084.39
_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                   15.322(3)
_cell_length_b                   24.083(5)
_cell_length_c                   31.621(6)
_cell_measurement_reflns_used    8291
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.4855
_cell_measurement_theta_min      3.0826
_cell_volume                     11668(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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            8159
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.8610
_exptl_absorpt_correction_T_min  0.7667
_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    1.235
_exptl_crystal_description       Block
_exptl_crystal_F_000             4496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     103
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0547
_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)+(0.0946P)²+3.3271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                3887
_reflns_number_total             4164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203053y_si_002_4.cif
_cod_data_source_block           3
_cod_database_code               4106447
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 0.61149(4) 0.01087(3) 0.407371(19) 0.0210(2) Uani 1 1 d .
N1 N 0.7266(3) 0.01389(19) 0.44221(14) 0.0258(10) Uani 1 1 d .
N2 N 0.8911(3) 0.1635(2) 0.62807(14) 0.0269(10) Uani 1 1 d .
O1 O 0.5866(2) -0.06328(16) 0.43569(11) 0.0268(8) Uani 1 1 d .
O2 O 0.4462(2) -0.05559(16) 0.45541(11) 0.0256(8) Uani 1 1 d .
O3 O 0.3342(3) -0.1828(2) 0.57005(14) 0.0490(13) Uani 1 1 d .
O4 O 0.4347(2) -0.22159(16) 0.61133(11) 0.0304(9) Uani 1 1 d .
O5 O 0.5000 0.0000 0.36958(17) 0.0247(11) Uani 1 2 d S
H1W H 0.482(6) 0.024(3) 0.351(2) 0.06(2) Uiso 1 1 d .
C1 C 0.7838(4) -0.0270(3) 0.44073(19) 0.0368(14) Uani 1 1 d .
H1 H 0.7703 -0.0584 0.4243 0.044 Uiso 1 1 calc R
C2 C 0.8626(4) -0.0260(3) 0.4621(2) 0.0394(15) Uani 1 1 d .
H2 H 0.9019 -0.0558 0.4595 0.047 Uiso 1 1 calc R
C3 C 0.8833(3) 0.0190(2) 0.48731(16) 0.0249(11) Uani 1 1 d .
C4 C 0.8240(4) 0.0626(3) 0.48783(19) 0.0360(14) Uani 1 1 d .
H4 H 0.8366 0.0950 0.5033 0.043 Uiso 1 1 calc R
C5 C 0.7474(4) 0.0588(3) 0.46594(19) 0.0356(14) Uani 1 1 d .
H5 H 0.7077 0.0884 0.4674 0.043 Uiso 1 1 calc R
C6 C 0.9645(3) 0.0229(2) 0.51325(16) 0.0256(11) Uani 1 1 d .
H6 H 0.9925 0.0594 0.5082 0.031 Uiso 1 1 calc R
C7 C 0.9537(3) 0.0138(2) 0.56203(16) 0.0231(11) Uani 1 1 d .
H7 H 0.9084 -0.0147 0.5674 0.028 Uiso 1 1 calc R
C8 C 0.9350(3) 0.0644(2) 0.58726(15) 0.0244(11) Uani 1 1 d .
C9 C 0.8519(4) 0.0732(3) 0.6027(2) 0.0401(15) Uani 1 1 d .
H9 H 0.8083 0.0461 0.5992 0.048 Uiso 1 1 calc R
C10 C 0.8337(4) 0.1228(3) 0.6236(2) 0.0371(13) Uani 1 1 d .
H10 H 0.7776 0.1276 0.6351 0.045 Uiso 1 1 calc R
C11 C 0.9706(4) 0.1548(3) 0.6124(2) 0.0406(15) Uani 1 1 d .
H11 H 1.0128 0.1828 0.6156 0.049 Uiso 1 1 calc R
C12 C 0.9939(4) 0.1069(3) 0.5917(2) 0.0404(15) Uani 1 1 d .
H12 H 1.0505 0.1033 0.5805 0.048 Uiso 1 1 calc R
C13 C 0.5369(4) -0.1181(3) 0.49284(18) 0.0352(12) Uani 1 1 d U
C14 C 0.6186(4) -0.1408(4) 0.4982(2) 0.0543(15) Uani 1 1 d U
H14 H 0.6642 -0.1303 0.4799 0.065 Uiso 1 1 calc R
C15 C 0.6344(5) -0.1783(4) 0.5297(3) 0.0632(16) Uani 1 1 d U
H15 H 0.6907 -0.1933 0.5327 0.076 Uiso 1 1 calc R
C16 C 0.5700(4) -0.1946(3) 0.5568(2) 0.0564(15) Uani 1 1 d U
H16 H 0.5824 -0.2191 0.5791 0.068 Uiso 1 1 calc R
C17 C 0.4847(4) -0.1742(3) 0.55082(19) 0.0391(12) Uani 1 1 d U
C18 C 0.4690(4) -0.1364(3) 0.51825(17) 0.0320(11) Uani 1 1 d U
H18 H 0.4120 -0.1232 0.5135 0.038 Uiso 1 1 calc R
C19 C 0.4110(4) -0.1943(3) 0.57925(17) 0.0310(13) Uani 1 1 d .
C20 C 0.5211(3) -0.0749(2) 0.45878(16) 0.0263(11) Uani 1 1 d .
C21 C 1.0248(13) 0.2195(8) 0.4377(7) 0.170(3) Uani 1 1 d U
H21 H 1.0421 0.2388 0.4621 0.204 Uiso 1 1 calc R
C22 C 0.9681(13) 0.1782(9) 0.4427(7) 0.172(3) Uani 1 1 d U
H22 H 0.9330 0.1759 0.4670 0.207 Uiso 1 1 calc R
C23 C 0.9628(13) 0.1402(8) 0.4121(7) 0.171(3) Uani 1 1 d U
H23 H 0.9335 0.1062 0.4160 0.206 Uiso 1 1 calc R
C24 C 1.0005(12) 0.1530(8) 0.3769(7) 0.169(3) Uani 1 1 d U
H24 H 0.9933 0.1275 0.3547 0.203 Uiso 1 1 calc R
C25 C 1.0819(13) 0.2135(8) 0.3264(6) 0.161(3) Uani 1 1 d U
H25 H 1.0668 0.1912 0.3032 0.193 Uiso 1 1 calc R
C26 C 1.1303(12) 0.2558(8) 0.3198(7) 0.159(3) Uani 1 1 d U
H26 H 1.1550 0.2625 0.2931 0.190 Uiso 1 1 calc R
C27 C 1.1453(12) 0.2915(8) 0.3537(6) 0.157(3) Uani 1 1 d U
H27 H 1.1799 0.3231 0.3486 0.188 Uiso 1 1 calc R
C28 C 1.1142(12) 0.2844(8) 0.3932(6) 0.158(3) Uani 1 1 d U
H28 H 1.1266 0.3090 0.4155 0.190 Uiso 1 1 calc R
C29 C 1.0484(13) 0.1979(8) 0.3682(7) 0.161(3) Uani 1 1 d U
C30 C 1.0618(14) 0.2372(8) 0.3982(7) 0.161(3) Uani 1 1 d U
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 93.08(15) . 2_655
O1 Ni1 O4 90.59(15) . 7_544
O2 Ni1 O4 172.26(15) 2_655 7_544
O1 Ni1 N1 87.52(16) . .
O2 Ni1 N1 87.40(15) 2_655 .
O4 Ni1 N1 85.95(17) 7_544 .
O1 Ni1 N2 178.30(16) . 11_454
O2 Ni1 N2 87.96(17) 2_655 11_454
O4 Ni1 N2 88.22(16) 7_544 11_454
N1 Ni1 N2 91.19(18) . 11_454
O1 Ni1 O5 89.33(13) . .
O2 Ni1 O5 97.80(13) 2_655 .
O4 Ni1 O5 89.05(15) 7_544 .
N1 Ni1 O5 174.05(14) . .
N2 Ni1 O5 91.87(14) 11_454 .
C1 N1 C5 117.3(5) . .
C1 N1 Ni1 121.2(4) . .
C5 N1 Ni1 121.4(4) . .
C10 N2 C11 116.8(5) . .
C10 N2 Ni1 123.2(4) . 3
C11 N2 Ni1 120.0(4) . 3
C20 O1 Ni1 126.4(4) . .
C20 O2 Ni1 130.9(3) . 2_655
C19 O4 Ni1 130.4(4) . 15_445
Ni1 O5 Ni1 110.7(2) . 2_655
Ni1 O5 H1W 124(6) . .
Ni1 O5 H1W 102(5) 2_655 .
N1 C1 C2 123.3(5) . .
N1 C1 H1 118.4 . .
C2 C1 H1 118.4 . .
C3 C2 C1 119.7(5) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
C2 C3 C4 116.7(5) . .
C2 C3 C6 123.9(5) . .
C4 C3 C6 119.4(5) . .
C5 C4 C3 120.3(5) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
N1 C5 C4 122.6(5) . .
N1 C5 H5 118.7 . .
C4 C5 H5 118.7 . .
C3 C6 C6 122.6(5) . 2_755
C3 C6 C7 116.3(4) . .
C6 C6 C7 88.5(3) 2_755 .
C3 C6 H6 109.2 . .
C6 C6 H6 109.2 2_755 .
C7 C6 H6 109.2 . .
C8 C7 C7 121.5(5) . 2_755
C8 C7 C6 115.7(4) . .
C7 C7 C6 87.9(3) 2_755 .
C8 C7 H7 109.9 . .
C7 C7 H7 109.9 2_755 .
C6 C7 H7 109.9 . .
C12 C8 C9 117.2(5) . .
C12 C8 C7 122.7(5) . .
C9 C8 C7 119.6(5) . .
C8 C9 C10 119.0(5) . .
C8 C9 H9 120.5 . .
C10 C9 H9 120.5 . .
N2 C10 C9 123.5(5) . .
N2 C10 H10 118.2 . .
C9 C10 H10 118.2 . .
N2 C11 C12 123.2(6) . .
N2 C11 H11 118.4 . .
C12 C11 H11 118.4 . .
C8 C12 C11 120.2(5) . .
C8 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C14 C13 C18 119.1(6) . .
C14 C13 C20 120.3(5) . .
C18 C13 C20 120.6(5) . .
C15 C14 C13 120.8(6) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C16 C15 C14 121.4(7) . .
C16 C15 H15 119.3 . .
C14 C15 H15 119.3 . .
C15 C16 C17 119.1(6) . .
C15 C16 H16 120.4 . .
C17 C16 H16 120.4 . .
C18 C17 C16 119.1(6) . .
C18 C17 C19 121.0(5) . .
C16 C17 C19 119.9(5) . .
C13 C18 C17 120.3(5) . .
C13 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
O3 C19 O4 125.2(5) . .
O3 C19 C17 119.5(5) . .
O4 C19 C17 115.3(5) . .
O2 C20 O1 126.6(5) . .
O2 C20 C13 117.7(5) . .
O1 C20 C13 115.6(5) . .
C22 C21 C30 126(2) . .
C22 C21 H21 117.1 . .
C30 C21 H21 117.1 . .
C21 C22 C23 118(2) . .
C21 C22 H22 121.1 . .
C23 C22 H22 121.1 . .
C24 C23 C22 116(2) . .
C24 C23 H23 122.2 . .
C22 C23 H23 122.2 . .
C23 C24 C29 128(2) . .
C23 C24 H24 115.9 . .
C29 C24 H24 115.9 . .
C26 C25 C29 124(2) . .
C26 C25 H25 118.1 . .
C29 C25 H25 118.1 . .
C25 C26 C27 118(2) . .
C25 C26 H26 121.2 . .
C27 C26 H26 121.2 . .
C28 C27 C26 125(2) . .
C28 C27 H27 117.4 . .
C26 C27 H27 117.4 . .
C27 C28 C30 114(2) . .
C27 C28 H28 122.9 . .
C30 C28 H28 122.9 . .
C24 C29 C30 120.1(19) . .
C24 C29 C25 126(2) . .
C30 C29 C25 113.5(18) . .
C29 C30 C28 125.1(19) . .
C29 C30 C21 110.0(18) . .
C28 C30 C21 124(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.034(4) .
Ni1 O2 2.061(3) 2_655
Ni1 O4 2.067(4) 7_544
Ni1 N1 2.080(4) .
Ni1 N2 2.093(5) 11_454
Ni1 O5 2.101(3) .
N1 C1 1.320(8) .
N1 C5 1.354(8) .
N2 C10 1.325(8) .
N2 C11 1.332(7) .
N2 Ni1 2.093(5) 3
O1 C20 1.271(6) .
O2 C20 1.244(7) .
O2 Ni1 2.061(3) 2_655
O3 C19 1.243(7) .
O4 C19 1.262(7) .
O4 Ni1 2.067(4) 15_445
O5 Ni1 2.101(3) 2_655
O5 H1W 0.89(8) .
C1 C2 1.385(8) .
C1 H1 0.9400 .
C2 C3 1.382(8) .
C2 H2 0.9400 .
C3 C4 1.391(8) .
C3 C6 1.493(7) .
C4 C5 1.365(8) .
C4 H4 0.9400 .
C5 H5 0.9400 .
C6 C6 1.550(11) 2_755
C6 C7 1.567(7) .
C6 H6 0.9900 .
C7 C8 1.485(7) .
C7 C7 1.567(10) 2_755
C7 H7 0.9900 .
C8 C12 1.373(8) .
C8 C9 1.379(8) .
C9 C10 1.393(9) .
C9 H9 0.9400 .
C10 H10 0.9400 .
C11 C12 1.374(9) .
C11 H11 0.9400 .
C12 H12 0.9400 .
C13 C14 1.376(9) .
C13 C18 1.387(8) .
C13 C20 1.518(8) .
C14 C15 1.368(10) .
C14 H14 0.9400 .
C15 C16 1.363(10) .
C15 H15 0.9400 .
C16 C17 1.409(9) .
C16 H16 0.9400 .
C17 C18 1.396(8) .
C17 C19 1.522(8) .
C18 H18 0.9400 .
C21 C22 1.33(2) .
C21 C30 1.44(2) .
C21 H21 0.9400 .
C22 C23 1.33(3) .
C22 H22 0.9400 .
C23 C24 1.29(2) .
C23 H23 0.9400 .
C24 C29 1.34(2) .
C24 H24 0.9400 .
C25 C26 1.28(2) .
C25 C29 1.47(2) .
C25 H25 0.9400 .
C26 C27 1.39(3) .
C26 H26 0.9400 .
C27 C28 1.35(2) .
C27 H27 0.9400 .
C28 C30 1.40(2) .
C28 H28 0.9400 .
C29 C30 1.36(3) .
