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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/4/10/64/4106444.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_4106444
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, C10 H10 Fe'
_chemical_formula_sum            'C50 H40 Fe N4 Ni2 O9'
_chemical_formula_weight         1014.09
_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                   15.417(3)
_cell_length_b                   23.492(5)
_cell_length_c                   32.648(7)
_cell_measurement_reflns_used    9202
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.4662
_cell_measurement_theta_min      3.0393
_cell_volume                     11824(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  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            8769
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  0.7698
_exptl_absorpt_correction_T_min  0.6082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Jacobson, R. (1998) Private communication to Rigaku Company, Tokyo, Japan.'
_exptl_crystal_colour            Yellow-Green
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       Block
_exptl_crystal_F_000             4176
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0890
_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)+(0.1824P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2303
_refine_ls_wR_factor_ref         0.2408
_reflns_number_gt                3399
_reflns_number_total             3859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203053y_si_002_1.cif
_cod_data_source_block           6
_cod_database_code               4106444
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 0.36176(6) 0.24030(4) 0.51297(3) 0.0434(3) Uani 1 1 d .
N1 N 0.3913(4) 0.1645(3) 0.4825(2) 0.0465(15) Uani 1 1 d .
N2 N 0.2272(5) 0.0119(3) 0.2973(2) 0.0509(16) Uani 1 1 d .
O1 O 0.3064(3) 0.1938(2) 0.55974(17) 0.0491(12) Uani 1 1 d .
O2 O 0.1667(4) 0.1838(2) 0.54097(17) 0.0498(13) Uani 1 1 d .
O3 O 0.4181(4) 0.0710(3) 0.6777(2) 0.0657(18) Uani 1 1 d .
O4 O 0.3171(4) 0.0332(2) 0.71931(19) 0.0528(13) Uani 1 1 d .
O5 O 0.2500 0.2500 0.4767(3) 0.0484(18) Uani 1 2 d SDU
H1W H 0.221(5) 0.225(3) 0.467(3) 0.048(3) Uiso 1 1 d DU
C1 C 0.4691(5) 0.1572(4) 0.4647(3) 0.056(2) Uani 1 1 d .
H1 H 0.5098 0.1868 0.4673 0.067 Uiso 1 1 calc R
C2 C 0.4932(5) 0.1094(4) 0.4431(3) 0.0543(19) Uani 1 1 d .
H2 H 0.5487 0.1066 0.4313 0.065 Uiso 1 1 calc R
C3 C 0.4329(5) 0.0651(3) 0.4391(2) 0.0484(17) Uani 1 1 d .
C4 C 0.3521(5) 0.0705(4) 0.4575(3) 0.057(2) Uani 1 1 d .
H4 H 0.3105 0.0414 0.4558 0.068 Uiso 1 1 calc R
C5 C 0.3352(5) 0.1215(4) 0.4787(3) 0.056(2) Uani 1 1 d .
H5 H 0.2805 0.1255 0.4911 0.067 Uiso 1 1 calc R
C6 C 0.4545(5) 0.0133(3) 0.4131(3) 0.0497(18) Uani 1 1 d .
H6 H 0.4104 -0.0167 0.4176 0.060 Uiso 1 1 calc R
C7 C 0.4657(5) 0.0240(3) 0.3664(3) 0.0518(19) Uani 1 1 d .
H7 H 0.4937 0.0613 0.3616 0.062 Uiso 1 1 calc R
C8 C 0.3834(5) 0.0183(4) 0.3398(3) 0.0498(19) Uani 1 1 d .
C9 C 0.3261(6) 0.0654(4) 0.3387(3) 0.067(2) Uani 1 1 d .
H9 H 0.3410 0.0998 0.3517 0.080 Uiso 1 1 calc R
C10 C 0.2477(6) 0.0602(4) 0.3182(4) 0.068(3) Uani 1 1 d .
H10 H 0.2080 0.0905 0.3188 0.082 Uiso 1 1 calc R
C11 C 0.2842(6) -0.0294(4) 0.2951(3) 0.064(2) Uani 1 1 d .
H11 H 0.2721 -0.0611 0.2786 0.077 Uiso 1 1 calc R
C12 C 0.3632(6) -0.0276(4) 0.3169(4) 0.066(3) Uani 1 1 d .
H12 H 0.4019 -0.0584 0.3155 0.079 Uiso 1 1 calc R
C13 C 0.2146(5) 0.1335(4) 0.5999(3) 0.0524(18) Uani 1 1 d .
C14 C 0.1313(6) 0.1127(5) 0.6070(3) 0.071(3) Uani 1 1 d .
H14 H 0.0857 0.1224 0.5892 0.085 Uiso 1 1 calc R
C15 C 0.1155(6) 0.0778(7) 0.6401(4) 0.093(5) Uani 1 1 d .
H15 H 0.0584 0.0660 0.6454 0.111 Uiso 1 1 calc R
C16 C 0.1813(6) 0.0597(5) 0.6657(4) 0.077(3) Uani 1 1 d .
H16 H 0.1698 0.0345 0.6874 0.092 Uiso 1 1 calc R
C17 C 0.2676(5) 0.0801(4) 0.6584(3) 0.0519(18) Uani 1 1 d .
C18 C 0.2837(5) 0.1149(3) 0.6255(3) 0.0494(18) Uani 1 1 d .
H18 H 0.3408 0.1266 0.6198 0.059 Uiso 1 1 calc R
C19 C 0.2317(5) 0.1743(3) 0.5644(3) 0.0474(17) Uani 1 1 d .
C20 C 0.3415(6) 0.0602(4) 0.6866(3) 0.0534(19) Uani 1 1 d .
Fe1 Fe 0.2500 0.2500 0.73486(12) 0.1059(10) Uani 1 2 d SU
C21 C 0.1350(11) 0.2901(10) 0.7468(8) 0.129(4) Uani 1 1 d U
H21 H 0.1316 0.3294 0.7577 0.155 Uiso 1 1 calc R
C22 C 0.1421(11) 0.2452(10) 0.7705(10) 0.135(4) Uani 1 1 d U
H22 H 0.1420 0.2461 0.8008 0.162 Uiso 1 1 calc R
C23 C 0.1506(11) 0.1983(10) 0.7478(7) 0.133(4) Uani 1 1 d U
H23 H 0.1545 0.1587 0.7580 0.159 Uiso 1 1 calc R
C24 C 0.1450(11) 0.2167(9) 0.7039(8) 0.130(4) Uani 1 1 d U
H24 H 0.1434 0.1934 0.6786 0.157 Uiso 1 1 calc R
C25 C 0.1388(11) 0.2789(9) 0.7087(8) 0.127(4) Uani 1 1 d U
H25 H 0.1350 0.3070 0.6862 0.152 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'
Fe Fe 0.3463 0.8444 '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
O2 Ni1 O4 89.8(2) 14 12_554
O2 Ni1 O1 92.4(2) 14 .
O4 Ni1 O1 172.3(2) 12_554 .
O2 Ni1 N1 178.0(3) 14 .
O4 Ni1 N1 88.4(3) 12_554 .
O1 Ni1 N1 89.5(3) . .
O2 Ni1 O5 89.0(2) 14 .
O4 Ni1 O5 89.6(2) 12_554 .
O1 Ni1 O5 97.8(2) . .
N1 Ni1 O5 90.1(2) . .
O2 Ni1 N2 88.0(2) 14 3
O4 Ni1 N2 86.0(3) 12_554 3
O1 Ni1 N2 86.7(2) . 3
N1 Ni1 N2 92.7(3) . 3
O5 Ni1 N2 174.7(2) . 3
C5 N1 C1 116.2(7) . .
C5 N1 Ni1 123.2(5) . .
C1 N1 Ni1 120.5(6) . .
C11 N2 C10 119.1(8) . .
C11 N2 Ni1 121.4(6) . 11_454
C10 N2 Ni1 119.0(6) . 11_454
C19 O1 Ni1 131.8(5) . .
C19 O2 Ni1 125.9(5) . 14
C20 O4 Ni1 130.8(6) . 16_545
Ni1 O5 Ni1 111.5(4) 14 .
Ni1 O5 H1W 82(7) 14 .
Ni1 O5 H1W 127(7) . .
N1 C1 C2 124.5(8) . .
N1 C1 H1 117.8 . .
C2 C1 H1 117.8 . .
C1 C2 C3 118.3(7) . .
C1 C2 H2 120.9 . .
C3 C2 H2 120.9 . .
C4 C3 C2 119.1(7) . .
C4 C3 C6 120.7(7) . .
C2 C3 C6 120.1(7) . .
C3 C4 C5 117.2(8) . .
C3 C4 H4 121.4 . .
C5 C4 H4 121.4 . .
N1 C5 C4 124.7(7) . .
N1 C5 H5 117.7 . .
C4 C5 H5 117.7 . .
C3 C6 C6 121.7(7) . 2_655
C3 C6 C7 116.2(7) . .
C6 C6 C7 88.0(4) 2_655 .
C3 C6 H6 109.7 . .
C6 C6 H6 109.7 2_655 .
C7 C6 H6 109.7 . .
C8 C7 C7 119.9(7) . 2_655
C8 C7 C6 116.6(7) . .
C7 C7 C6 87.6(4) 2_655 .
C8 C7 H7 110.3 . .
C7 C7 H7 110.3 2_655 .
C6 C7 H7 110.3 . .
C12 C8 C9 117.9(8) . .
C12 C8 C7 124.8(7) . .
C9 C8 C7 117.2(8) . .
C10 C9 C8 119.0(9) . .
C10 C9 H9 120.5 . .
C8 C9 H9 120.5 . .
N2 C10 C9 121.3(8) . .
N2 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
N2 C11 C12 122.0(8) . .
N2 C11 H11 119.0 . .
C12 C11 H11 119.0 . .
C8 C12 C11 120.2(8) . .
C8 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C14 C13 C18 118.9(7) . .
C14 C13 C19 120.5(7) . .
C18 C13 C19 120.6(7) . .
C15 C14 C13 120.2(8) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C14 C15 C16 121.9(8) . .
C14 C15 H15 119.0 . .
C16 C15 H15 119.0 . .
C15 C16 C17 118.5(8) . .
C15 C16 H16 120.7 . .
C17 C16 H16 120.7 . .
C18 C17 C16 119.8(8) . .
C18 C17 C20 121.1(7) . .
C16 C17 C20 119.1(8) . .
C17 C18 C13 120.5(7) . .
C17 C18 H18 119.8 . .
C13 C18 H18 119.8 . .
O1 C19 O2 125.8(7) . .
O1 C19 C13 118.8(7) . .
O2 C19 C13 115.3(7) . .
O3 C20 O4 124.6(8) . .
O3 C20 C17 120.1(8) . .
O4 C20 C17 115.3(8) . .
C23 Fe1 C23 155.6(14) 14 .
C23 Fe1 C25 69.2(8) 14 14
C23 Fe1 C25 122.2(9) . 14
C23 Fe1 C25 122.2(9) 14 .
C23 Fe1 C25 69.2(8) . .
C25 Fe1 C25 130.3(14) 14 .
C23 Fe1 C22 122.6(10) 14 .
C23 Fe1 C22 38.6(8) . .
C25 Fe1 C22 155.8(9) 14 .
C25 Fe1 C22 64.4(10) . .
C23 Fe1 C22 38.6(8) 14 14
C23 Fe1 C22 122.6(10) . 14
C25 Fe1 C22 64.5(10) 14 14
C25 Fe1 C22 155.8(9) . 14
C22 Fe1 C22 110.2(16) . 14
C23 Fe1 C21 64.9(9) 14 14
C23 Fe1 C21 110.1(9) . 14
C25 Fe1 C21 36.4(8) 14 14
C25 Fe1 C21 164.9(12) . 14
C22 Fe1 C21 125.0(10) . 14
C22 Fe1 C21 37.5(8) 14 14
C23 Fe1 C21 110.1(9) 14 .
C23 Fe1 C21 64.9(9) . .
C25 Fe1 C21 164.9(12) 14 .
C25 Fe1 C21 36.4(8) . .
C22 Fe1 C21 37.5(8) . .
C22 Fe1 C21 125.0(10) 14 .
C21 Fe1 C21 158.0(14) 14 .
C23 Fe1 C24 159.2(11) 14 .
C23 Fe1 C24 43.3(8) . .
C25 Fe1 C24 109.2(10) 14 .
C25 Fe1 C24 42.1(8) . .
C22 Fe1 C24 67.5(11) . .
C22 Fe1 C24 160.7(9) 14 .
C21 Fe1 C24 126.8(9) 14 .
C21 Fe1 C24 65.7(9) . .
C23 Fe1 C24 43.3(8) 14 14
C23 Fe1 C24 159.2(11) . 14
C25 Fe1 C24 42.1(8) 14 14
C25 Fe1 C24 109.2(10) . 14
C22 Fe1 C24 160.7(9) . 14
C22 Fe1 C24 67.5(11) 14 14
C21 Fe1 C24 65.7(9) 14 14
C21 Fe1 C24 126.8(9) . 14
C24 Fe1 C24 121.3(14) . 14
C25 C21 C22 114(3) . .
C25 C21 Fe1 71.2(13) . .
C22 C21 Fe1 70.7(12) . .
C25 C21 H21 123.0 . .
C22 C21 H21 123.0 . .
Fe1 C21 H21 123.0 . .
C21 C22 C23 110(3) . .
C21 C22 Fe1 71.7(13) . .
C23 C22 Fe1 69.3(14) . .
C21 C22 H22 124.9 . .
C23 C22 H22 124.9 . .
Fe1 C22 H22 124.9 . .
C22 C23 C24 107(2) . .
C22 C23 Fe1 72.0(13) . .
C24 C23 Fe1 70.6(11) . .
C22 C23 H23 126.5 . .
C24 C23 H23 126.5 . .
Fe1 C23 H23 126.5 . .
C25 C24 C23 100.8(19) . .
C25 C24 Fe1 67.8(11) . .
C23 C24 Fe1 66.1(11) . .
C25 C24 H24 129.6 . .
C23 C24 H24 129.6 . .
Fe1 C24 H24 129.6 . .
C21 C25 C24 108(2) . .
C21 C25 Fe1 72.4(13) . .
C24 C25 Fe1 70.1(10) . .
C21 C25 H25 125.8 . .
C24 C25 H25 125.8 . .
Fe1 C25 H25 125.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O2 2.051(5) 14
Ni1 O4 2.062(6) 12_554
Ni1 O1 2.063(5) .
Ni1 N1 2.090(6) .
Ni1 O5 2.103(5) .
Ni1 N2 2.103(7) 3
N1 C5 1.336(11) .
N1 C1 1.343(11) .
N2 C11 1.311(11) .
N2 C10 1.360(12) .
N2 Ni1 2.103(7) 11_454
O1 C19 1.249(10) .
O2 C19 1.281(10) .
O2 Ni1 2.051(5) 14
O3 C20 1.243(11) .
O4 C20 1.297(11) .
O4 Ni1 2.062(6) 16_545
O5 Ni1 2.103(5) 14
O5 H1W 0.80(2) .
C1 C2 1.378(13) .
C1 H1 0.9400 .
C2 C3 1.402(11) .
C2 H2 0.9400 .
C3 C4 1.388(12) .
C3 C6 1.520(11) .
C4 C5 1.408(13) .
C4 H4 0.9400 .
C5 H5 0.9400 .
C6 C6 1.536(14) 2_655
C6 C7 1.554(13) .
C6 H6 0.9900 .
C7 C8 1.544(11) .
C7 C7 1.547(15) 2_655
C7 H7 0.9900 .
C8 C12 1.347(14) .
C8 C9 1.416(13) .
C9 C10 1.388(13) .
C9 H9 0.9400 .
C10 H10 0.9400 .
C11 C12 1.411(13) .
C11 H11 0.9400 .
C12 H12 0.9400 .
C13 C14 1.394(13) .
C13 C18 1.424(12) .
C13 C19 1.525(11) .
C14 C15 1.377(15) .
C14 H14 0.9400 .
C15 C16 1.381(14) .
C15 H15 0.9400 .
C16 C17 1.435(11) .
C16 H16 0.9400 .
C17 C18 1.374(12) .
C17 C20 1.537(12) .
C18 H18 0.9400 .
Fe1 C23 2.000(19) 14
Fe1 C23 2.000(19) .
Fe1 C25 2.031(19) 14
Fe1 C25 2.031(19) .
Fe1 C22 2.03(2) .
Fe1 C22 2.03(2) 14
Fe1 C21 2.046(17) 14
Fe1 C21 2.046(17) .
Fe1 C24 2.06(2) .
Fe1 C24 2.06(2) 14
C21 C25 1.27(3) .
C21 C22 1.31(3) .
C21 H21 0.9900 .
C22 C23 1.33(3) .
C22 H22 0.9900 .
C23 C24 1.50(3) .
C23 H23 0.9900 .
C24 C25 1.47(3) .
C24 H24 0.9900 .
C25 H25 0.9900 .
