#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:56:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180523 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/92/7219222.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_7219222
loop_
_publ_author_name
'Cui, Yanhui'
'Wu, Jiang'
'Kirillov, Alexander M.'
'Gu, Jinzhong'
'dou, wei'
_publ_section_title
;
 Exploring 5-fluoronicotinic acid as a versatile building block for the
 generation of topologically diverse metal-organic and supramolecular Ni,
 Co, and Cd networks
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA14534H
_journal_year                    2015
_chemical_formula_sum            'C18 H12 Co F2 N6 O4'
_chemical_formula_weight         473.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.8197(4)
_cell_length_b                   17.8112(9)
_cell_length_c                   26.5942(14)
_cell_measurement_temperature    296(2)
_cell_volume                     3704.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17808
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.7974
_exptl_absorpt_correction_T_min  0.7559
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0278
_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)+(0.0328P)²+1.8561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0692
_reflns_number_gt                2795
_reflns_number_total             3307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra14534h2.cif
_cod_data_source_block           pbcn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7219222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
Co1 Co -0.01709(3) 0.040753(15) 0.381106(10) 0.02316(9) Uani 1 1 d .
O1 O 0.25868(18) 0.03325(9) 0.37203(5) 0.0344(4) Uani 1 1 d .
O2 O 0.15100(17) 0.06417(9) 0.44511(5) 0.0341(4) Uani 1 1 d .
O3 O 0.0980(3) -0.30953(10) 0.30960(7) 0.0588(5) Uani 1 1 d .
O4 O 0.2014(2) -0.20405(9) 0.27530(6) 0.0482(4) Uani 1 1 d .
N1 N 0.7561(2) 0.05594(9) 0.42647(6) 0.0258(4) Uani 1 1 d .
N2 N -0.0122(2) -0.07839(10) 0.39025(6) 0.0257(4) Uani 1 1 d .
N3 N -0.1402(2) 0.02982(9) 0.31189(6) 0.0276(4) Uani 1 1 d .
N4 N -0.2682(2) 0.08802(11) 0.24934(7) 0.0329(4) Uani 1 1 d .
N5 N -0.0360(2) 0.15556(10) 0.35980(7) 0.0314(4) Uani 1 1 d .
F1 F 0.66809(17) 0.13930(10) 0.54559(5) 0.0602(5) Uani 1 1 d .
F2 F -0.1660(3) -0.22383(8) 0.47001(6) 0.0788(6) Uani 1 1 d .
C1 C 0.2766(2) 0.05338(11) 0.41666(7) 0.0256(4) Uani 1 1 d .
C2 C 0.4535(2) 0.06554(11) 0.43702(7) 0.0236(4) Uani 1 1 d .
C3 C 0.5965(2) 0.04544(11) 0.40971(7) 0.0262(4) Uani 1 1 d .
H3 H 0.5812 0.0236 0.3783 0.031 Uiso 1 1 calc R
C4 C 0.7767(3) 0.08733(12) 0.47167(8) 0.0319(5) Uani 1 1 d .
H4 H 0.8866 0.0951 0.4840 0.038 Uiso 1 1 calc R
C5 C 0.6395(3) 0.10818(13) 0.50014(8) 0.0325(5) Uani 1 1 d .
C6 C 0.4763(2) 0.09836(12) 0.48361(8) 0.0302(5) Uani 1 1 d .
H6 H 0.3833 0.1132 0.5030 0.036 Uiso 1 1 calc R
C7 C 0.1234(3) -0.24035(14) 0.30809(9) 0.0389(6) Uani 1 1 d .
C8 C 0.0489(3) -0.19699(12) 0.35173(8) 0.0310(5) Uani 1 1 d .
C9 C 0.0549(2) -0.11969(12) 0.35306(8) 0.0282(5) Uani 1 1 d .
H9 H 0.1085 -0.0948 0.3267 0.034 Uiso 1 1 calc R
C10 C -0.0832(3) -0.11421(12) 0.42870(8) 0.0306(5) Uani 1 1 d .
H10 H -0.1285 -0.0867 0.4553 0.037 Uiso 1 1 calc R
C11 C -0.0910(3) -0.19075(13) 0.42983(8) 0.0409(6) Uani 1 1 d .
C12 C -0.0279(3) -0.23361(13) 0.39149(9) 0.0430(6) Uani 1 1 d .
H12 H -0.0363 -0.2857 0.3922 0.052 Uiso 1 1 calc R
C13 C -0.2105(3) -0.02260(12) 0.28005(8) 0.0309(5) Uani 1 1 d .
H13 H -0.2048 -0.0744 0.2843 0.037 Uiso 1 1 calc R
C14 C -0.2889(3) 0.01291(13) 0.24173(8) 0.0333(5) Uani 1 1 d .
H14 H -0.3464 -0.0096 0.2151 0.040 Uiso 1 1 calc R
C15 C -0.1786(2) 0.09594(12) 0.29173(7) 0.0276(5) Uani 1 1 d .
C16 C -0.1208(3) 0.16314(12) 0.31696(8) 0.0298(5) Uani 1 1 d .
C17 C -0.0584(3) 0.27646(13) 0.34034(9) 0.0447(6) Uani 1 1 d .
H17 H -0.0486 0.3285 0.3415 0.054 Uiso 1 1 calc R
C18 C 0.0030(3) 0.22715(13) 0.37470(9) 0.0391(5) Uani 1 1 d .
H18 H 0.0623 0.2399 0.4038 0.047 Uiso 1 1 calc R
H1 H -0.306(3) 0.1244(16) 0.2302(10) 0.055(8) Uiso 1 1 d .
H2 H -0.199(4) 0.2555(17) 0.2751(11) 0.076(9) Uiso 1 1 d .
N6 N -0.1378(2) 0.23532(11) 0.30359(7) 0.0378(5) Uani 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'
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'
Co Co 0.3494 0.9721 '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
N3 Co1 N5 79.79(7) . .
N3 Co1 N2 90.92(6) . .
N5 Co1 N2 170.58(6) . .
N3 Co1 N1 97.22(6) . 1_455
N5 Co1 N1 88.36(6) . 1_455
N2 Co1 N1 94.33(6) . 1_455
N3 Co1 O1 110.72(6) . .
N5 Co1 O1 95.64(6) . .
N2 Co1 O1 86.20(6) . .
N1 Co1 O1 152.05(6) 1_455 .
N3 Co1 O2 168.56(6) . .
N5 Co1 O2 93.76(6) . .
N2 Co1 O2 95.16(6) . .
N1 Co1 O2 91.99(5) 1_455 .
O1 Co1 O2 60.19(5) . .
C1 O1 Co1 89.33(12) . .
C1 O2 Co1 88.39(11) . .
C4 N1 C3 118.09(17) . .
C4 N1 Co1 117.11(13) . 1_655
C3 N1 Co1 124.17(13) . 1_655
C10 N2 C9 117.96(18) . .
C10 N2 Co1 123.89(14) . .
C9 N2 Co1 117.93(14) . .
C15 N3 C13 105.25(16) . .
C15 N3 Co1 112.19(13) . .
C13 N3 Co1 142.29(14) . .
C15 N4 C14 106.95(18) . .
C15 N4 H1 126.2(18) . .
C14 N4 H1 126.8(18) . .
C16 N5 C18 105.38(18) . .
C16 N5 Co1 111.21(14) . .
C18 N5 Co1 143.37(15) . .
O1 C1 O2 121.98(18) . .
O1 C1 C2 119.22(17) . .
O2 C1 C2 118.80(17) . .
C3 C2 C6 118.50(18) . .
C3 C2 C1 121.28(17) . .
C6 C2 C1 120.22(17) . .
N1 C3 C2 122.94(18) . .
N1 C3 H3 118.5 . .
C2 C3 H3 118.5 . .
N1 C4 C5 121.21(18) . .
N1 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
F1 C5 C6 119.87(18) . .
F1 C5 C4 118.59(18) . .
C6 C5 C4 121.54(19) . .
C5 C6 C2 117.70(18) . .
C5 C6 H6 121.1 . .
C2 C6 H6 121.1 . .
O4 C7 O3 127.8(2) . .
O4 C7 C8 117.5(2) . .
O3 C7 C8 114.7(2) . .
C9 C8 C12 117.88(19) . .
C9 C8 C7 121.1(2) . .
C12 C8 C7 121.0(2) . .
N2 C9 C8 123.6(2) . .
N2 C9 H9 118.2 . .
C8 C9 H9 118.2 . .
N2 C10 C11 121.04(19) . .
N2 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
F2 C11 C10 118.1(2) . .
F2 C11 C12 120.2(2) . .
C10 C11 C12 121.7(2) . .
C11 C12 C8 117.7(2) . .
C11 C12 H12 121.1 . .
C8 C12 H12 121.1 . .
C14 C13 N3 109.22(19) . .
C14 C13 H13 125.4 . .
N3 C13 H13 125.4 . .
C13 C14 N4 107.11(19) . .
C13 C14 H14 126.4 . .
N4 C14 H14 126.4 . .
N3 C15 N4 111.46(18) . .
N3 C15 C16 118.45(18) . .
N4 C15 C16 130.09(19) . .
N5 C16 N6 112.06(19) . .
N5 C16 C15 118.12(19) . .
N6 C16 C15 129.82(19) . .
C18 C17 N6 107.2(2) . .
C18 C17 H17 126.4 . .
N6 C17 H17 126.4 . .
C17 C18 N5 109.2(2) . .
C17 C18 H18 125.4 . .
N5 C18 H18 125.4 . .
C16 N6 C17 106.18(19) . .
C16 N6 H2 127.9(18) . .
C17 N6 H2 125.8(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 N3 2.0863(16) .
Co1 N5 2.1271(18) .
Co1 N2 2.1363(17) .
Co1 N1 2.1620(16) 1_455
Co1 O1 2.1740(14) .
Co1 O2 2.1907(14) .
O1 C1 1.248(2) .
O2 C1 1.255(2) .
O3 C7 1.249(3) .
O4 C7 1.245(3) .
N1 C4 1.335(2) .
N1 C3 1.339(2) .
N1 Co1 2.1620(16) 1_655
N2 C10 1.327(3) .
N2 C9 1.340(3) .
N3 C15 1.328(3) .
N3 C13 1.375(3) .
N4 C15 1.335(3) .
N4 C14 1.363(3) .
N4 H1 0.87(3) .
N5 C16 1.325(3) .
N5 C18 1.370(3) .
F1 C5 1.348(2) .
F2 C11 1.354(3) .
C1 C2 1.501(3) .
C2 C3 1.380(3) .
C2 C6 1.382(3) .
C3 H3 0.9300 .
C4 C5 1.365(3) .
C4 H4 0.9300 .
C5 C6 1.361(3) .
C6 H6 0.9300 .
C7 C8 1.511(3) .
C8 C9 1.378(3) .
C8 C12 1.380(3) .
C9 H9 0.9300 .
C10 C11 1.365(3) .
C10 H10 0.9300 .
C11 C12 1.366(3) .
C12 H12 0.9300 .
C13 C14 1.347(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.445(3) .
C16 N6 1.341(3) .
C17 C18 1.355(3) .
C17 N6 1.370(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
N6 H2 0.97(3) .
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
N6 H2 O4 0.97(3) 1.71(3) 2.673(2) 176(3) 6_566
N4 H1 O3 0.87(3) 1.75(3) 2.623(2) 173(3) 6_566
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
N3 Co1 O1 C1 170.39(12) .
N5 Co1 O1 C1 89.20(12) .
N2 Co1 O1 C1 -100.07(12) .
N1 Co1 O1 C1 -8.0(2) 1_455
O2 Co1 O1 C1 -1.91(11) .
N3 Co1 O2 C1 -37.3(4) .
N5 Co1 O2 C1 -92.45(13) .
N2 Co1 O2 C1 84.52(12) .
N1 Co1 O2 C1 179.06(12) 1_455
O1 Co1 O2 C1 1.90(11) .
N3 Co1 N2 C10 -121.43(16) .
N5 Co1 N2 C10 -130.5(4) .
N1 Co1 N2 C10 -24.12(16) 1_455
O1 Co1 N2 C10 127.86(16) .
O2 Co1 N2 C10 68.27(16) .
N3 Co1 N2 C9 53.17(15) .
N5 Co1 N2 C9 44.1(5) .
N1 Co1 N2 C9 150.48(14) 1_455
O1 Co1 N2 C9 -57.54(14) .
O2 Co1 N2 C9 -117.13(14) .
N5 Co1 N3 C15 -4.45(13) .
N2 Co1 N3 C15 177.05(14) .
N1 Co1 N3 C15 82.57(14) 1_455
O1 Co1 N3 C15 -96.66(14) .
O2 Co1 N3 C15 -60.8(4) .
N5 Co1 N3 C13 -177.1(2) .
N2 Co1 N3 C13 4.4(2) .
N1 Co1 N3 C13 -90.1(2) 1_455
O1 Co1 N3 C13 90.7(2) .
O2 Co1 N3 C13 126.6(3) .
N3 Co1 N5 C16 3.54(14) .
N2 Co1 N5 C16 12.7(5) .
N1 Co1 N5 C16 -94.10(14) 1_455
O1 Co1 N5 C16 113.62(14) .
O2 Co1 N5 C16 174.01(14) .
N3 Co1 N5 C18 -179.4(3) .
N2 Co1 N5 C18 -170.1(3) .
N1 Co1 N5 C18 83.0(3) 1_455
O1 Co1 N5 C18 -69.3(3) .
O2 Co1 N5 C18 -8.9(3) .
Co1 O1 C1 O2 3.4(2) .
Co1 O1 C1 C2 -176.25(16) .
Co1 O2 C1 O1 -3.4(2) .
Co1 O2 C1 C2 176.27(16) .
O1 C1 C2 C3 -8.7(3) .
O2 C1 C2 C3 171.60(19) .
O1 C1 C2 C6 170.35(19) .
O2 C1 C2 C6 -9.3(3) .
C4 N1 C3 C2 0.0(3) .
Co1 N1 C3 C2 -170.59(15) 1_655
C6 C2 C3 N1 0.4(3) .
C1 C2 C3 N1 179.48(18) .
C3 N1 C4 C5 0.0(3) .
Co1 N1 C4 C5 171.28(17) 1_655
N1 C4 C5 F1 179.7(2) .
N1 C4 C5 C6 -0.4(4) .
F1 C5 C6 C2 -179.4(2) .
C4 C5 C6 C2 0.8(3) .
C3 C2 C6 C5 -0.7(3) .
C1 C2 C6 C5 -179.85(19) .
O4 C7 C8 C9 5.2(3) .
O3 C7 C8 C9 -174.7(2) .
O4 C7 C8 C12 -175.0(2) .
O3 C7 C8 C12 5.1(3) .
C10 N2 C9 C8 2.3(3) .
Co1 N2 C9 C8 -172.60(16) .
C12 C8 C9 N2 -1.3(3) .
C7 C8 C9 N2 178.57(19) .
C9 N2 C10 C11 -1.4(3) .
Co1 N2 C10 C11 173.25(17) .
N2 C10 C11 F2 -179.6(2) .
N2 C10 C11 C12 -0.6(4) .
F2 C11 C12 C8 -179.3(2) .
C10 C11 C12 C8 1.7(4) .
C9 C8 C12 C11 -0.7(3) .
C7 C8 C12 C11 179.4(2) .
C15 N3 C13 C14 0.1(2) .
Co1 N3 C13 C14 173.02(17) .
N3 C13 C14 N4 0.0(2) .
C15 N4 C14 C13 0.0(2) .
C13 N3 C15 N4 -0.1(2) .
Co1 N3 C15 N4 -175.44(13) .
C13 N3 C15 C16 -179.85(18) .
Co1 N3 C15 C16 4.8(2) .
C14 N4 C15 N3 0.1(2) .
C14 N4 C15 C16 179.8(2) .
C18 N5 C16 N6 0.2(2) .
Co1 N5 C16 N6 178.38(14) .
C18 N5 C16 C15 179.61(18) .
Co1 N5 C16 C15 -2.2(2) .
N3 C15 C16 N5 -1.8(3) .
N4 C15 C16 N5 178.5(2) .
N3 C15 C16 N6 177.6(2) .
N4 C15 C16 N6 -2.2(4) .
N6 C17 C18 N5 0.4(3) .
C16 N5 C18 C17 -0.3(3) .
Co1 N5 C18 C17 -177.53(19) .
N5 C16 N6 C17 0.1(3) .
C15 C16 N6 C17 -179.3(2) .
C18 C17 N6 C16 -0.3(3) .
