#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:04:03 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180058 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/04/7050442.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_7050442
loop_
_publ_author_name
'Sladek, Marianna I.'
'Braun, Thomas'
'Neumann, Beate'
'Stammler, Hans-Georg'
_publ_section_title
;
 3-Fluoropyridyl nickel complexes as useful tools for the selective
 synthesis of new 2,4,5,6-tetrafluoropyridines: a route complementing
 the established methods to access fluorinated pyridines
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              313
_journal_paper_doi               10.1039/b207943g
_journal_volume                  27
_journal_year                    2003
_chemical_formula_moiety         'C17 H30 Cl F4 N Ni P2'
_chemical_formula_sum            'C17 H30 Cl F4 N Ni P2'
_chemical_formula_weight         480.52
_chemical_name_systematic        ?
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   23.36300(10)
_cell_length_b                   8.55400(10)
_cell_length_c                   10.9840(2)
_cell_measurement_reflns_used    3628
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.910
_cell_volume                     2195.12(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'KappaCCD '
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images'
_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  0.038
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            43259
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    1.19
_exptl_absorpt_correction_T_max  0.8422
_exptl_absorpt_correction_T_min  0.7174
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.499(6)
_refine_ls_extinction_coef       0.0029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0226P)²+0.7712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0513
_reflns_number_gt                5943
_reflns_number_total             6102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b207943g.txt
_cod_data_source_block           compound1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               7050442
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, 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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.151038(7) 0.367091(18) 0.974608(18) 0.01283(4) Uani 1 1 d . . .
Cl1 Cl 0.176420(15) 0.45390(5) 1.15446(3) 0.02299(8) Uani 1 1 d . . .
P1 P 0.060071(15) 0.38862(4) 1.02905(3) 0.01551(7) Uani 1 1 d . . .
P2 P 0.240776(15) 0.39404(4) 0.91120(3) 0.01390(7) Uani 1 1 d . . .
F1 F 0.13987(4) 0.01559(11) 0.91514(9) 0.02412(19) Uani 1 1 d . . .
F2 F 0.10818(5) -0.12745(10) 0.70568(10) 0.0281(2) Uani 1 1 d . . .
F3 F 0.08407(4) 0.05203(13) 0.50652(9) 0.0303(2) Uani 1 1 d . . .
F4 F 0.11451(4) 0.49621(10) 0.71565(9) 0.02240(18) Uani 1 1 d . . .
N1 N 0.10046(5) 0.27355(16) 0.61379(12) 0.0207(2) Uani 1 1 d . . .
C1 C 0.13030(6) 0.26654(16) 0.82741(13) 0.0146(2) Uani 1 1 d . . .
C2 C 0.12760(6) 0.10507(16) 0.81805(14) 0.0167(3) Uani 1 1 d . . .
C3 C 0.11182(6) 0.02815(16) 0.71169(15) 0.0195(3) Uani 1 1 d . . .
C4 C 0.09929(6) 0.12037(19) 0.61271(14) 0.0219(3) Uani 1 1 d . . .
C5 C 0.11527(6) 0.33832(16) 0.71852(13) 0.0162(2) Uani 1 1 d . . .
C6 C 0.00582(6) 0.33712(19) 0.91502(14) 0.0217(3) Uani 1 1 d . . .
H6A H 0.0142 0.3963 0.8397 0.026 Uiso 1 1 calc R . .
H6B H 0.0101 0.2247 0.8956 0.026 Uiso 1 1 calc R . .
C7 C -0.05668(6) 0.3669(2) 0.94948(15) 0.0258(3) Uani 1 1 d . . .
H7A H -0.0664 0.3057 1.0220 0.039 Uiso 1 1 calc R . .
H7B H -0.0816 0.3358 0.8819 0.039 Uiso 1 1 calc R . .
H7C H -0.0621 0.4784 0.9666 0.039 Uiso 1 1 calc R . .
C8 C 0.03940(7) 0.28285(19) 1.16693(15) 0.0244(3) Uani 1 1 d . . .
H8A H 0.0648 0.3157 1.2344 0.029 Uiso 1 1 calc R . .
H8B H -0.0002 0.3128 1.1890 0.029 Uiso 1 1 calc R . .
C9 C 0.04236(8) 0.1056(2) 1.1546(2) 0.0335(4) Uani 1 1 d . . .
H9A H 0.0147 0.0709 1.0932 0.050 Uiso 1 1 calc R . .
H9B H 0.0332 0.0571 1.2331 0.050 Uiso 1 1 calc R . .
H9C H 0.0810 0.0749 1.1297 0.050 Uiso 1 1 calc R . .
C10 C 0.04350(7) 0.59112(19) 1.07025(14) 0.0217(3) Uani 1 1 d . . .
H10A H 0.0040 0.5955 1.1029 0.026 Uiso 1 1 calc R . .
H10B H 0.0698 0.6245 1.1360 0.026 Uiso 1 1 calc R . .
C11 C 0.04845(8) 0.70571(18) 0.9648(2) 0.0325(4) Uani 1 1 d . . .
H11A H 0.0865 0.6968 0.9280 0.049 Uiso 1 1 calc R . .
H11B H 0.0428 0.8125 0.9949 0.049 Uiso 1 1 calc R . .
H11C H 0.0192 0.6817 0.9037 0.049 Uiso 1 1 calc R . .
C12 C 0.25716(6) 0.34498(17) 0.75239(13) 0.0175(3) Uani 1 1 d . . .
H12A H 0.2515 0.2312 0.7413 0.021 Uiso 1 1 calc R . .
H12B H 0.2292 0.3991 0.6994 0.021 Uiso 1 1 calc R . .
C13 C 0.31750(7) 0.3870(2) 0.70886(17) 0.0261(3) Uani 1 1 d . . .
H13A H 0.3227 0.5006 0.7126 0.039 Uiso 1 1 calc R . .
H13B H 0.3226 0.3513 0.6248 0.039 Uiso 1 1 calc R . .
H13C H 0.3458 0.3359 0.7613 0.039 Uiso 1 1 calc R . .
C14 C 0.29355(6) 0.28506(17) 0.99934(13) 0.0186(3) Uani 1 1 d . . .
H14A H 0.3324 0.3176 0.9738 0.022 Uiso 1 1 calc R . .
H14B H 0.2891 0.3116 1.0866 0.022 Uiso 1 1 calc R . .
C15 C 0.28787(7) 0.10790(17) 0.98374(18) 0.0246(3) Uani 1 1 d . . .
H15A H 0.2488 0.0757 1.0041 0.037 Uiso 1 1 calc R . .
H15B H 0.3149 0.0550 1.0380 0.037 Uiso 1 1 calc R . .
H15C H 0.2963 0.0796 0.8992 0.037 Uiso 1 1 calc R . .
C16 C 0.26364(7) 0.59740(17) 0.92850(16) 0.0226(3) Uani 1 1 d . . .
H16A H 0.2624 0.6262 1.0158 0.027 Uiso 1 1 calc R . .
H16B H 0.3037 0.6077 0.9004 0.027 Uiso 1 1 calc R . .
C17 C 0.22592(8) 0.70994(19) 0.8565(2) 0.0333(4) Uani 1 1 d . . .
H17A H 0.2270 0.6820 0.7700 0.050 Uiso 1 1 calc R . .
H17B H 0.2401 0.8170 0.8670 0.050 Uiso 1 1 calc R . .
H17C H 0.1864 0.7031 0.8862 0.050 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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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'
P P 0.1023 0.0942 '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
C1 Ni1 Cl1 172.80(4) . . ?
C1 Ni1 P1 91.31(4) . . ?
Cl1 Ni1 P1 89.318(15) . . ?
C1 Ni1 P2 91.20(4) . . ?
Cl1 Ni1 P2 89.545(14) . . ?
P1 Ni1 P2 168.951(14) . . ?
C8 P1 C10 101.97(8) . . ?
C8 P1 C6 105.31(8) . . ?
C10 P1 C6 104.45(7) . . ?
C8 P1 Ni1 115.83(5) . . ?
C10 P1 Ni1 110.37(5) . . ?
C6 P1 Ni1 117.27(5) . . ?
C14 P2 C16 103.50(7) . . ?
C14 P2 C12 104.28(7) . . ?
C16 P2 C12 104.79(7) . . ?
C14 P2 Ni1 114.75(5) . . ?
C16 P2 Ni1 109.98(5) . . ?
C12 P2 Ni1 118.12(5) . . ?
C4 N1 C5 115.59(13) . . ?
C2 C1 C5 111.39(13) . . ?
C2 C1 Ni1 121.82(11) . . ?
C5 C1 Ni1 126.77(10) . . ?
F1 C2 C1 119.92(13) . . ?
F1 C2 C3 116.99(12) . . ?
C1 C2 C3 123.08(13) . . ?
F2 C3 C4 121.29(14) . . ?
F2 C3 C2 122.01(14) . . ?
C4 C3 C2 116.70(13) . . ?
N1 C4 F3 116.45(14) . . ?
N1 C4 C3 124.20(14) . . ?
F3 C4 C3 119.35(14) . . ?
N1 C5 F4 113.26(12) . . ?
N1 C5 C1 129.02(13) . . ?
F4 C5 C1 117.72(12) . . ?
C7 C6 P1 116.76(11) . . ?
C9 C8 P1 114.00(12) . . ?
C11 C10 P1 113.90(11) . . ?
C13 C12 P2 115.81(11) . . ?
C15 C14 P2 112.83(10) . . ?
C17 C16 P2 112.17(11) . . ?
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
Ni1 C1 1.8943(14) . ?
Ni1 Cl1 2.1921(4) . ?
Ni1 P1 2.2155(4) . ?
Ni1 P2 2.2212(4) . ?
P1 C8 1.8290(16) . ?
P1 C10 1.8318(16) . ?
P1 C6 1.8355(15) . ?
P2 C14 1.8238(14) . ?
P2 C16 1.8296(15) . ?
P2 C12 1.8345(15) . ?
F1 C2 1.3436(17) . ?
F2 C3 1.3353(16) . ?
F3 C4 1.3524(17) . ?
F4 C5 1.3511(15) . ?
N1 C4 1.311(2) . ?
N1 C5 1.3228(19) . ?
C1 C2 1.3865(19) . ?
C1 C5 1.3896(19) . ?
C2 C3 1.391(2) . ?
C3 C4 1.375(2) . ?
C6 C7 1.530(2) . ?
C8 C9 1.523(2) . ?
C10 C11 1.521(3) . ?
C12 C13 1.531(2) . ?
C14 C15 1.531(2) . ?
C16 C17 1.526(2) . ?
