#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:10:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178711 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/22/4082206.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_4082206
loop_
_publ_author_name
'Kaplan, Peter T.'
'Xu, Long'
'Chen, Bo'
'McGarry, Katherine R.'
'Yu, Siqi'
'Wang, Huan'
'Vicic, David A.'
_publ_section_title
;
 Mild, Safe, and Versatile Reagents for (CF2)nTransfer and the
 Construction of Fluoroalkyl-Containing Rings
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7552
_journal_paper_doi               10.1021/om401016k
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C8 H6 F8 N2 Ni'
_chemical_formula_weight         340.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   13.142(3)
_cell_length_b                   10.518(2)
_cell_length_c                   17.372(3)
_cell_measurement_temperature    100(2)
_cell_volume                     2401.3(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17572
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_T_max  0.6468
_exptl_absorpt_correction_T_min  0.4037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.965
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0623
_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)+(0.0116P)²+17.3871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2032
_reflns_number_total             2416
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om401016k_si_002.cif
_cod_data_source_block           Compound10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2401.2(8)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4082206
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
Ni1 Ni 0.10470(5) 0.59566(6) 0.92930(4) 0.02448(19) Uani 1 1 d
N1 N 0.1229(3) 0.4281(4) 0.8904(3) 0.0316(10) Uani 1 1 d
N2 N 0.1666(3) 0.5480(4) 1.0237(3) 0.0299(10) Uani 1 1 d
F1 F -0.0442(2) 0.5932(3) 0.81947(19) 0.0400(8) Uani 1 1 d
F2 F 0.1070(3) 0.6220(3) 0.77096(17) 0.0388(8) Uani 1 1 d
F3 F 0.1194(3) 0.8539(3) 0.8117(2) 0.0500(9) Uani 1 1 d
F4 F -0.0409(3) 0.8336(3) 0.7825(2) 0.0491(9) Uani 1 1 d
F5 F -0.0904(2) 0.7938(3) 0.9303(2) 0.0467(9) Uani 1 1 d
F6 F 0.0081(3) 0.9618(3) 0.9221(2) 0.0463(9) Uani 1 1 d
F7 F 0.0435(3) 0.7702(3) 1.03966(19) 0.0392(8) Uani 1 1 d
F8 F 0.1696(2) 0.8329(3) 0.9692(2) 0.0415(8) Uani 1 1 d
C1 C 0.0484(4) 0.6505(5) 0.8347(3) 0.0300(11) Uani 1 1 d
C2 C 0.0301(5) 0.7945(5) 0.8325(3) 0.0379(13) Uani 1 1 d
C3 C 0.0071(5) 0.8342(5) 0.9145(4) 0.0399(14) Uani 1 1 d
C4 C 0.0819(4) 0.7625(5) 0.9654(3) 0.0295(11) Uani 1 1 d
C5 C 0.1349(4) 0.3234(5) 0.8752(3) 0.0297(11) Uani 1 1 d
C6 C 0.1497(5) 0.1895(6) 0.8566(4) 0.0385(14) Uani 1 1 d
C7 C 0.2093(4) 0.5104(5) 1.0762(3) 0.0323(12) Uani 1 1 d
C8 C 0.2645(5) 0.4617(9) 1.1421(4) 0.0465(17) Uani 1 1 d
H6 H 0.321(6) 0.459(7) 1.142(4) 0.05(2) Uiso 1 1 d
H3 H 0.149(5) 0.142(6) 0.904(4) 0.040(17) Uiso 1 1 d
H2 H 0.084(7) 0.161(9) 0.834(5) 0.09(3) Uiso 1 1 d
H5 H 0.240(9) 0.376(11) 1.154(6) 0.14(4) Uiso 1 1 d
H4 H 0.254(6) 0.532(8) 1.176(4) 0.07(2) Uiso 1 1 d
H1 H 0.202(8) 0.186(9) 0.835(5) 0.10(4) Uiso 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'
F F 0.0171 0.0103 '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
C4 Ni1 C1 86.7(2)
C4 Ni1 N2 91.5(2)
C1 Ni1 N2 176.8(2)
C4 Ni1 N1 177.7(2)
C1 Ni1 N1 91.3(2)
N2 Ni1 N1 90.49(19)
C5 N1 Ni1 172.5(5)
C7 N2 Ni1 173.0(5)
F2 C1 F1 104.0(4)
F2 C1 C2 106.4(4)
F1 C1 C2 106.7(4)
F2 C1 Ni1 114.3(4)
F1 C1 Ni1 112.2(3)
C2 C1 Ni1 112.6(4)
F4 C2 F3 106.5(5)
F4 C2 C3 112.8(5)
F3 C2 C3 106.9(5)
F4 C2 C1 115.4(5)
F3 C2 C1 108.7(5)
C3 C2 C1 106.2(5)
F6 C3 F5 107.2(5)
F6 C3 C2 111.3(5)
F5 C3 C2 106.7(5)
F6 C3 C4 115.5(5)
F5 C3 C4 109.4(5)
C2 C3 C4 106.4(5)
F8 C4 F7 103.2(4)
F8 C4 C3 107.6(4)
F7 C4 C3 106.1(4)
F8 C4 Ni1 112.6(3)
F7 C4 Ni1 114.9(4)
C3 C4 Ni1 111.7(4)
N1 C5 C6 179.5(7)
C5 C6 H3 109(4)
C5 C6 H2 105(5)
H3 C6 H2 100(6)
C5 C6 H1 105(7)
H3 C6 H1 112(8)
H2 C6 H1 124(8)
N2 C7 C8 179.2(7)
C7 C8 H6 121(6)
C7 C8 H5 109(7)
H6 C8 H5 107(9)
C7 C8 H4 98(5)
H6 C8 H4 99(7)
H5 C8 H4 122(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 C4 1.887(5)
Ni1 C1 1.893(5)
Ni1 N2 1.898(5)
Ni1 N1 1.903(5)
N1 C5 1.143(7)
N2 C7 1.143(7)
F1 C1 1.383(6)
F2 C1 1.381(6)
F3 C2 1.378(7)
F4 C2 1.339(7)
F5 C3 1.378(7)
F6 C3 1.349(6)
F7 C4 1.387(6)
F8 C4 1.372(6)
C1 C2 1.534(8)
C2 C3 1.515(8)
C3 C4 1.522(8)
C5 C6 1.459(8)
C6 H3 0.96(7)
C6 H2 1.00(10)
C6 H1 0.79(10)
C7 C8 1.448(8)
C8 H6 0.75(8)
C8 H5 0.97(12)
C8 H4 0.96(8)
