#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:10:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178711 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/22/4082208.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_4082208
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            'C22 H18 F8 N2 Ni'
_chemical_formula_weight         521.09
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.792(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7462(17)
_cell_length_b                   17.523(4)
_cell_length_c                   15.835(3)
_cell_measurement_temperature    100(2)
_cell_volume                     2144.7(8)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26534
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.010
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.260
_refine_diff_density_max         1.368
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0544P)²+9.9585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3792
_reflns_number_total             4338
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om401016k_si_002.cif
_cod_data_source_block           Compound11
_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        2144.6(8)
_cod_database_code               4082208
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.737
_shelx_estimated_absorpt_t_max   0.784
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ni1 Ni 0.88205(7) 0.02391(3) 0.67017(3) 0.02151(19) Uani 1 1 d . U
F1 F 0.8664(4) 0.13747(17) 0.78963(17) 0.0396(7) Uani 1 1 d . U
F2 F 1.1317(4) 0.1114(2) 0.76172(18) 0.0448(8) Uani 1 1 d . U
F3 F 0.9991(6) 0.0637(2) 0.92212(18) 0.0583(11) Uani 1 1 d . U
F4 F 1.1473(5) -0.0120(2) 0.8468(2) 0.0612(10) Uani 1 1 d . U
F5 F 0.6990(5) 0.0044(2) 0.8518(2) 0.0538(9) Uani 1 1 d . U
F6 F 0.8693(5) -0.08893(18) 0.89601(18) 0.0493(9) Uani 1 1 d . U
F7 F 0.6842(5) -0.0955(2) 0.7331(2) 0.0530(9) Uani 1 1 d . U
F8 F 0.9605(5) -0.11703(18) 0.7410(2) 0.0520(9) Uani 1 1 d . U
C5 C 0.7900(6) -0.0349(3) 0.5795(3) 0.0237(9) Uani 1 1 d . U
C14 C 0.9209(5) 0.1126(3) 0.6086(2) 0.0206(8) Uani 1 1 d . U
C1 C 0.9738(6) 0.0782(3) 0.7699(3) 0.0263(9) Uani 1 1 d . U
C2 C 0.9927(8) 0.0266(3) 0.8482(3) 0.0412(12) Uani 1 1 d . U
C3 C 0.8535(9) -0.0323(3) 0.8388(3) 0.0414(12) Uani 1 1 d . U
C4 C 0.8415(6) -0.0596(3) 0.7462(3) 0.0268(9) Uani 1 1 d . U
N1 N 0.7257(5) -0.0726(2) 0.5262(2) 0.0233(8) Uani 1 1 d . U
C6 C 0.6375(6) -0.1172(3) 0.4629(3) 0.0245(9) Uani 1 1 d . U
C7 C 0.5942(6) -0.1922(3) 0.4831(3) 0.0300(10) Uani 1 1 d . U
C8 C 0.5036(7) -0.2337(3) 0.4195(4) 0.0374(11) Uani 1 1 d . U
H8A H 0.4721 -0.2851 0.4299 0.045 Uiso 1 1 calc R U
C9 C 0.4586(6) -0.2015(3) 0.3412(4) 0.0373(12) Uani 1 1 d . U
H9A H 0.3952 -0.2307 0.2991 0.045 Uiso 1 1 calc R U
C10 C 0.5047(6) -0.1274(3) 0.3236(3) 0.0317(10) Uani 1 1 d . U
H10A H 0.4732 -0.1064 0.2695 0.038 Uiso 1 1 calc R U
C11 C 0.5970(5) -0.0830(3) 0.3842(3) 0.0246(9) Uani 1 1 d . U
C12 C 0.6445(7) -0.2269(3) 0.5686(4) 0.0412(12) Uani 1 1 d . U
H12A H 0.5905 -0.2772 0.5726 0.062 Uiso 1 1 calc R U
H12B H 0.6050 -0.1937 0.6132 0.062 Uiso 1 1 calc R U
H12C H 0.7705 -0.2322 0.5755 0.062 Uiso 1 1 calc R U
C13 C 0.6514(6) -0.0028(3) 0.3663(3) 0.0286(10) Uani 1 1 d . U
H13A H 0.6016 0.0321 0.4066 0.043 Uiso 1 1 calc R U
H13B H 0.6102 0.0112 0.3085 0.043 Uiso 1 1 calc R U
H13C H 0.7779 0.0008 0.3721 0.043 Uiso 1 1 calc R U
N2 N 0.9393(5) 0.1711(2) 0.5767(2) 0.0217(7) Uani 1 1 d . U
C15 C 0.9535(5) 0.2428(2) 0.5387(3) 0.0221(8) Uani 1 1 d . U
C16 C 0.8852(6) 0.2504(3) 0.4544(3) 0.0269(9) Uani 1 1 d . U
C17 C 0.8985(7) 0.3225(3) 0.4186(3) 0.0389(12) Uani 1 1 d . U
H17A H 0.8537 0.3309 0.3621 0.047 Uiso 1 1 calc R U
C18 C 0.9756(8) 0.3822(3) 0.4639(4) 0.0465(14) Uani 1 1 d . U
H18A H 0.9839 0.4307 0.4377 0.056 Uiso 1 1 calc R U
C19 C 1.0415(7) 0.3725(3) 0.5470(4) 0.0426(13) Uani 1 1 d . U
H19A H 1.0939 0.4144 0.5770 0.051 Uiso 1 1 calc R U
C20 C 1.0312(6) 0.3020(3) 0.5865(3) 0.0316(10) Uani 1 1 d . U
C21 C 0.8072(7) 0.1836(3) 0.4073(3) 0.0343(11) Uani 1 1 d . U
H21A H 0.7646 0.1997 0.3505 0.051 Uiso 1 1 calc R U
H21B H 0.7108 0.1634 0.4377 0.051 Uiso 1 1 calc R U
H21C H 0.8950 0.1437 0.4030 0.051 Uiso 1 1 calc R U
C22 C 1.0988(7) 0.2906(3) 0.6772(3) 0.0388(12) Uani 1 1 d . U
H22A H 1.1814 0.2481 0.6803 0.058 Uiso 1 1 calc R U
H22B H 1.0022 0.2789 0.7120 0.058 Uiso 1 1 calc R U
H22C H 1.1568 0.3372 0.6981 0.058 Uiso 1 1 calc R 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'
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
C5 Ni1 C14 97.13(18)
C5 Ni1 C4 89.52(19)
C14 Ni1 C4 172.79(18)
C5 Ni1 C1 175.51(19)
C14 Ni1 C1 87.36(19)
C4 Ni1 C1 86.0(2)
N1 C5 Ni1 176.1(4)
N2 C14 Ni1 173.7(4)
F2 C1 F1 104.9(4)
F2 C1 C2 106.8(4)
F1 C1 C2 106.7(4)
F2 C1 Ni1 114.5(3)
F1 C1 Ni1 111.1(3)
C2 C1 Ni1 112.3(3)
F3 C2 F4 105.7(4)
F3 C2 C3 114.1(5)
F4 C2 C3 106.4(5)
F3 C2 C1 114.7(4)
F4 C2 C1 108.2(5)
C3 C2 C1 107.3(4)
F6 C3 F5 106.5(4)
F6 C3 C2 114.2(5)
F5 C3 C2 106.8(5)
F6 C3 C4 114.2(4)
F5 C3 C4 106.7(4)
C2 C3 C4 107.9(4)
F8 C4 F7 104.3(4)
F8 C4 C3 106.7(4)
F7 C4 C3 106.4(4)
F8 C4 Ni1 112.4(3)
F7 C4 Ni1 115.6(3)
C3 C4 Ni1 110.9(3)
C5 N1 C6 176.5(4)
C11 C6 C7 124.3(4)
C11 C6 N1 117.7(4)
C7 C6 N1 118.0(4)
C8 C7 C6 116.2(5)
C8 C7 C12 121.8(5)
C6 C7 C12 122.1(5)
C9 C8 C7 121.3(5)
C10 C9 C8 120.7(5)
C9 C10 C11 121.0(5)
C10 C11 C6 116.6(4)
C10 C11 C13 122.0(4)
C6 C11 C13 121.4(4)
C14 N2 C15 177.3(4)
C20 C15 N2 118.4(4)
C20 C15 C16 124.4(4)
N2 C15 C16 117.2(4)
C17 C16 C15 115.9(5)
C17 C16 C21 123.2(4)
C15 C16 C21 120.9(4)
C18 C17 C16 121.2(5)
C17 C18 C19 121.2(5)
C20 C19 C18 120.4(5)
C19 C20 C15 116.9(5)
C19 C20 C22 121.3(5)
C15 C20 C22 121.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 C5 1.870(5)
Ni1 C14 1.870(4)
Ni1 C4 1.933(5)
Ni1 C1 1.937(4)
F1 C1 1.380(5)
F2 C1 1.368(6)
F3 C2 1.337(6)
F4 C2 1.377(7)
F5 C3 1.386(7)
F6 C3 1.344(6)
F7 C4 1.374(6)
F8 C4 1.371(5)
C5 N1 1.158(6)
C14 N2 1.155(6)
C1 C2 1.534(6)
C2 C3 1.493(9)
C3 C4 1.539(7)
N1 C6 1.412(5)
C6 C11 1.399(6)
C6 C7 1.400(7)
C7 C8 1.393(7)
C7 C12 1.511(7)
C8 C9 1.386(8)
C9 C10 1.378(8)
C10 C11 1.396(6)
C11 C13 1.499(7)
N2 C15 1.401(6)
C15 C20 1.398(6)
C15 C16 1.409(6)
C16 C17 1.393(7)
C16 C21 1.494(7)
C17 C18 1.381(9)
C18 C19 1.391(8)
C19 C20 1.389(7)
C20 C22 1.509(7)
