#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:19:42 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179241 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/61/4316146.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_4316146
loop_
_publ_author_name
'Abdul Malik Puthan Peedikakkal'
'Charlene Shi Yun Peh'
'Lip Lin Koh'
'Jagadese J. Vittal'
_publ_contact_author
; 
     Dr. Jagadese J. Vittal
     Department of Chemistry
     National University of Singapore
     3 Science Drive 3
     SINGAPORE 117543 
;
_publ_contact_author_email       chmjjv@nus.edu.sg
_publ_contact_author_fax         '(65) 6779 1691'
_publ_contact_author_phone       '(65) 6516 2677'
_publ_section_title
;
 Metal-Organic Frameworks Containing a Tetrapyridylcyclobutane Ligand
 Derived from Isomerization Reaction
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6775
_journal_page_last               6777
_journal_paper_doi               10.1021/ic100853h
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C16 H12 F6 N2 O4'
_chemical_formula_weight         410.28
_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                96.054(17)
_cell_angle_beta                 93.549(16)
_cell_angle_gamma                104.627(11)
_cell_formula_units_Z            4
_cell_length_a                   10.950(8)
_cell_length_b                   11.556(9)
_cell_length_c                   14.278(10)
_cell_measurement_reflns_used    874
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.30
_cell_volume                     1731(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9846
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         6065
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0842
_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)+(0.1434P)²+0.6442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2382
_refine_ls_wR_factor_ref         0.2659
_reflns_number_gt                3670
_reflns_number_total             6065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100853h_si_002_2.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4316146
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7267(3) -0.2171(3) 0.1291(2) 0.0504(8) Uani 1 1 d . . .
H1 H 0.6863 -0.2913 0.1292 0.060 Uiso 1 1 calc R . .
N2 N 1.2313(3) 0.5621(3) 0.1310(2) 0.0530(8) Uani 1 1 d . . .
H2 H 1.2711 0.6372 0.1368 0.064 Uiso 1 1 calc R . .
N3 N 0.1891(3) 0.1851(3) 0.3713(2) 0.0480(8) Uani 1 1 d . . .
H3 H 0.142(4) 0.098(4) 0.366(3) 0.075(13) Uiso 1 1 d . . .
N4 N 0.6962(3) 0.9661(3) 0.3844(2) 0.0474(8) Uani 1 1 d . . .
H4 H 0.739(4) 1.045(4) 0.385(3) 0.069(13) Uiso 1 1 d . . .
C1 C 0.8517(4) -0.1898(3) 0.1213(3) 0.0500(9) Uani 1 1 d . . .
H1A H 0.8935 -0.2506 0.1161 0.060 Uiso 1 1 calc R . .
C2 C 0.9184(3) -0.0717(3) 0.1208(3) 0.0502(9) Uani 1 1 d . . .
H2A H 1.0051 -0.0528 0.1153 0.060 Uiso 1 1 calc R . .
C3 C 0.8553(3) 0.0203(3) 0.1287(3) 0.0445(9) Uani 1 1 d . . .
C4 C 0.7256(3) -0.0130(3) 0.1372(3) 0.0508(10) Uani 1 1 d . . .
H4A H 0.6811 0.0457 0.1432 0.061 Uiso 1 1 calc R . .
C5 C 0.6626(3) -0.1326(3) 0.1368(3) 0.0522(10) Uani 1 1 d . . .
H5 H 0.5757 -0.1545 0.1419 0.063 Uiso 1 1 calc R . .
C6 C 0.9193(3) 0.1485(3) 0.1281(3) 0.0509(10) Uani 1 1 d . . .
H6 H 0.8693 0.2026 0.1344 0.061 Uiso 1 1 calc R . .
C7 C 1.0392(3) 0.1937(3) 0.1197(3) 0.0487(9) Uani 1 1 d . . .
H7 H 1.0891 0.1396 0.1128 0.058 Uiso 1 1 calc R . .
C8 C 1.2973(3) 0.4797(4) 0.1331(3) 0.0526(10) Uani 1 1 d . . .
H8 H 1.3854 0.5040 0.1390 0.063 Uiso 1 1 calc R . .
C9 C 1.2357(3) 0.3588(3) 0.1267(3) 0.0506(9) Uani 1 1 d . . .
H9 H 1.2820 0.3015 0.1268 0.061 Uiso 1 1 calc R . .
C10 C 1.1034(3) 0.3226(3) 0.1200(3) 0.0446(9) Uani 1 1 d . . .
C11 C 1.0378(4) 0.4113(4) 0.1151(3) 0.0527(10) Uani 1 1 d . . .
H11 H 0.9496 0.3899 0.1085 0.063 Uiso 1 1 calc R . .
C12 C 1.1040(4) 0.5306(4) 0.1202(3) 0.0565(10) Uani 1 1 d . . .
H12 H 1.0603 0.5895 0.1160 0.068 Uiso 1 1 calc R . .
C13 C 0.1240(3) 0.2685(3) 0.3740(3) 0.0501(9) Uani 1 1 d . . .
H13 H 0.0360 0.2454 0.3716 0.060 Uiso 1 1 calc R . .
C14 C 0.1871(3) 0.3887(3) 0.3802(3) 0.0471(9) Uani 1 1 d . . .
H14 H 0.1414 0.4465 0.3825 0.057 Uiso 1 1 calc R . .
C15 C 0.3193(3) 0.4244(3) 0.3831(2) 0.0403(8) Uani 1 1 d . . .
C16 C 0.3835(3) 0.3338(3) 0.3796(3) 0.0445(9) Uani 1 1 d . . .
H16 H 0.4714 0.3539 0.3808 0.053 Uiso 1 1 calc R . .
C17 C 0.3166(3) 0.2149(3) 0.3743(3) 0.0483(9) Uani 1 1 d . . .
H17 H 0.3595 0.1549 0.3728 0.058 Uiso 1 1 calc R . .
C18 C 0.3839(3) 0.5534(3) 0.3890(3) 0.0452(9) Uani 1 1 d . . .
H18 H 0.3372 0.6080 0.4062 0.054 Uiso 1 1 calc R . .
C19 C 0.5014(3) 0.5980(3) 0.3719(3) 0.0456(9) Uani 1 1 d . . .
H19 H 0.5480 0.5434 0.3547 0.055 Uiso 1 1 calc R . .
C20 C 0.5713(3) 0.9374(3) 0.3914(3) 0.0494(9) Uani 1 1 d . . .
H20 H 0.5295 0.9982 0.3984 0.059 Uiso 1 1 calc R . .
C21 C 0.5037(3) 0.8188(3) 0.3885(3) 0.0485(9) Uani 1 1 d . . .
H21 H 0.4168 0.7995 0.3936 0.058 Uiso 1 1 calc R . .
C22 C 0.5667(3) 0.7277(3) 0.3777(2) 0.0405(8) Uani 1 1 d . . .
C23 C 0.6966(3) 0.7609(3) 0.3713(3) 0.0505(9) Uani 1 1 d . . .
H23 H 0.7411 0.7023 0.3646 0.061 Uiso 1 1 calc R . .
C24 C 0.7598(3) 0.8811(3) 0.3751(3) 0.0510(10) Uani 1 1 d . . .
H24 H 0.8469 0.9033 0.3712 0.061 Uiso 1 1 calc R . .
O1 O 0.2548(3) 0.9229(3) 0.3834(3) 0.0758(10) Uani 1 1 d . . .
O2 O 0.0653(3) 0.9587(2) 0.3603(3) 0.0736(10) Uani 1 1 d . . .
O3 O 0.3552(3) 0.7907(2) 0.1527(2) 0.0663(8) Uani 1 1 d . . .
O4 O 0.1680(3) 0.8278(3) 0.1154(3) 0.0908(12) Uani 1 1 d . . .
O5 O 0.6371(3) 0.2390(3) 0.4050(2) 0.0713(9) Uani 1 1 d . . .
O6 O 0.8117(2) 0.1881(2) 0.3621(2) 0.0636(8) Uani 1 1 d . . .
O7 O 0.6092(3) 0.5576(2) 0.1428(2) 0.0675(9) Uani 1 1 d . . .
O8 O 0.7850(3) 0.5128(3) 0.0957(2) 0.0680(8) Uani 1 1 d . . .
C1S C 0.1400(3) 0.8932(3) 0.3701(3) 0.0496(9) Uani 1 1 d D . .
C2S C 0.0726(4) 0.7580(4) 0.3621(3) 0.0542(10) Uani 1 1 d D . .
C3S C 0.2820(4) 0.8559(3) 0.1364(3) 0.0540(10) Uani 1 1 d D . .
C4S C 0.3501(4) 0.9904(4) 0.1442(3) 0.0608(11) Uani 1 1 d D . .
C5S C 0.7443(3) 0.2591(3) 0.3794(3) 0.0461(9) Uani 1 1 d D . .
C6S C 0.8090(3) 0.3905(3) 0.3682(3) 0.0467(9) Uani 1 1 d D . .
C7S C 0.6760(3) 0.4887(3) 0.1164(3) 0.0472(9) Uani 1 1 d D . .
C8S C 0.6032(4) 0.3535(4) 0.1086(3) 0.0574(11) Uani 1 1 d D . .
F1 F -0.0136(3) 0.7193(2) 0.2893(2) 0.0962(10) Uani 1 1 d D . .
F2 F 0.1481(3) 0.6876(3) 0.3582(3) 0.1299(15) Uani 1 1 d D . .
F3 F 0.0053(4) 0.7344(3) 0.4350(2) 0.1131(11) Uani 1 1 d D . .
F4 F 0.4425(3) 1.0288(2) 0.2144(2) 0.0881(9) Uani 1 1 d D . .
F5 F 0.2761(3) 1.0619(3) 0.1559(4) 0.1524(19) Uani 1 1 d D . .
F6 F 0.4110(4) 1.0150(3) 0.0691(3) 0.1362(15) Uani 1 1 d D . .
F7 F 0.8991(3) 0.4393(3) 0.4363(3) 0.1145(12) Uani 1 1 d D . .
F8 F 0.7345(3) 0.4616(3) 0.3680(3) 0.1369(17) Uani 1 1 d D . .
F9 F 0.8678(4) 0.4012(3) 0.2920(3) 0.1330(15) Uani 1 1 d D . .
F10 F 0.5399(3) 0.3276(3) 0.1823(2) 0.1056(11) Uani 1 1 d D . .
F11 F 0.6769(3) 0.2807(3) 0.0985(3) 0.1237(14) Uani 1 1 d D . .
F12 F 0.5174(3) 0.3240(3) 0.0352(2) 0.1077(11) Uani 1 1 d 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'
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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C5 N1 C1 122.1(3) . . ?
C8 N2 C12 121.6(3) . . ?
C13 N3 C17 121.8(3) . . ?
C20 N4 C24 121.4(3) . . ?
N1 C1 C2 120.0(3) . . ?
C1 C2 C3 120.0(3) . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 C6 119.0(3) . . ?
C2 C3 C6 123.4(3) . . ?
C5 C4 C3 120.4(3) . . ?
N1 C5 C4 119.9(3) . . ?
C7 C6 C3 126.3(3) . . ?
C6 C7 C10 126.2(3) . . ?
N2 C8 C9 120.4(3) . . ?
C8 C9 C10 119.8(3) . . ?
C9 C10 C11 118.0(3) . . ?
C9 C10 C7 119.1(3) . . ?
C11 C10 C7 123.0(3) . . ?
C12 C11 C10 119.8(3) . . ?
N2 C12 C11 120.3(4) . . ?
N3 C13 C14 120.0(3) . . ?
C13 C14 C15 120.5(3) . . ?
C14 C15 C16 117.4(3) . . ?
C14 C15 C18 119.2(3) . . ?
C16 C15 C18 123.3(3) . . ?
C17 C16 C15 120.1(3) . . ?
N3 C17 C16 120.2(3) . . ?
C19 C18 C15 125.6(3) . . ?
C18 C19 C22 125.7(3) . . ?
N4 C20 C21 120.7(3) . . ?
C20 C21 C22 119.5(3) . . ?
C23 C22 C21 118.2(3) . . ?
C23 C22 C19 118.7(3) . . ?
C21 C22 C19 123.1(3) . . ?
C24 C23 C22 120.0(3) . . ?
N4 C24 C23 120.3(3) . . ?
O1 C1S O2 128.7(4) . . ?
O1 C1S C2S 117.8(3) . . ?
O2 C1S C2S 113.4(3) . . ?
F2 C2S F1 107.1(4) . . ?
F2 C2S F3 107.2(4) . . ?
F1 C2S F3 102.5(4) . . ?
F2 C2S C1S 114.4(3) . . ?
F1 C2S C1S 114.1(3) . . ?
F3 C2S C1S 110.7(3) . . ?
O4 C3S O3 129.8(4) . . ?
O4 C3S C4S 116.8(4) . . ?
O3 C3S C4S 113.4(3) . . ?
F5 C4S F6 108.3(4) . . ?
F5 C4S F4 105.4(4) . . ?
F6 C4S F4 102.4(4) . . ?
F5 C4S C3S 114.3(4) . . ?
F6 C4S C3S 111.0(4) . . ?
F4 C4S C3S 114.6(3) . . ?
O5 C5S O6 129.5(4) . . ?
O5 C5S C6S 116.6(3) . . ?
O6 C5S C6S 113.8(3) . . ?
F8 C6S F9 106.9(4) . . ?
F8 C6S F7 106.0(3) . . ?
F9 C6S F7 103.5(4) . . ?
F8 C6S C5S 115.0(3) . . ?
F9 C6S C5S 113.0(3) . . ?
F7 C6S C5S 111.6(3) . . ?
O8 C7S O7 129.8(4) . . ?
O8 C7S C8S 117.7(3) . . ?
O7 C7S C8S 112.5(3) . . ?
F11 C8S F10 107.4(4) . . ?
F11 C8S F12 107.0(4) . . ?
F10 C8S F12 105.4(4) . . ?
F11 C8S C7S 113.3(3) . . ?
F10 C8S C7S 112.7(3) . . ?
F12 C8S C7S 110.7(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.338(4) . ?
N1 C1 1.339(5) . ?
N2 C8 1.335(5) . ?
N2 C12 1.344(5) . ?
N3 C13 1.334(5) . ?
N3 C17 1.348(5) . ?
N4 C20 1.336(5) . ?
N4 C24 1.340(5) . ?
C1 C2 1.376(5) . ?
C2 C3 1.405(5) . ?
C3 C4 1.391(5) . ?
C3 C6 1.472(5) . ?
C4 C5 1.379(5) . ?
C6 C7 1.303(5) . ?
C7 C10 1.478(5) . ?
C8 C9 1.381(5) . ?
C9 C10 1.396(5) . ?
C10 C11 1.398(5) . ?
C11 C12 1.378(6) . ?
C13 C14 1.377(5) . ?
C14 C15 1.399(5) . ?
C15 C16 1.399(5) . ?
C15 C18 1.471(5) . ?
C16 C17 1.376(5) . ?
C18 C19 1.308(5) . ?
C19 C22 1.479(5) . ?
C20 C21 1.379(5) . ?
C21 C22 1.398(5) . ?
C22 C23 1.388(5) . ?
C23 C24 1.380(5) . ?
O1 C1S 1.213(4) . ?
O2 C1S 1.259(4) . ?
O3 C3S 1.258(4) . ?
O4 C3S 1.218(5) . ?
O5 C5S 1.225(4) . ?
O6 C5S 1.251(4) . ?
O7 C7S 1.255(4) . ?
O8 C7S 1.218(4) . ?
C1S C2S 1.539(5) . ?
C2S F2 1.298(4) . ?
C2S F1 1.318(5) . ?
C2S F3 1.326(5) . ?
C3S C4S 1.534(6) . ?
C4S F5 1.301(4) . ?
C4S F6 1.315(5) . ?
C4S F4 1.334(5) . ?
C5S C6S 1.535(5) . ?
C6S F8 1.296(4) . ?
C6S F9 1.299(5) . ?
C6S F7 1.312(4) . ?
C7S C8S 1.553(5) . ?
C8S F11 1.308(4) . ?
C8S F10 1.315(5) . ?
C8S F12 1.319(5) . ?
