#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:06:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180123 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/21/7102121.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_7102121
loop_
_publ_author_name
'Lindup, Richard J'
'Marder, Todd B'
'Perutz, Robin N'
'Whitwood, Adrian C'
_publ_section_title
;
 Sequential C-F activation and borylation of fluoropyridines via
 intermediate Rh(I) fluoropyridyl complexes: a multinuclear NMR
 investigation.
;
_journal_issue                   35
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3664
_journal_page_last               3666
_journal_paper_doi               10.1039/b707840d
_journal_year                    2007
_chemical_formula_moiety         'C14 H27 F4 N P3 Rh'
_chemical_formula_sum            'C14 H27 F4 N P3 Rh'
_chemical_formula_weight         481.19
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 102.8010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1172(6)
_cell_length_b                   9.2891(5)
_cell_length_c                   18.3352(9)
_cell_measurement_reflns_used    6207
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.47
_cell_volume                     2012.48(18)
_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, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21962
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0207
_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)+(0.0305P)²+0.6064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0527
_refine_ls_wR_factor_ref         0.0540
_reflns_number_gt                5272
_reflns_number_total             5785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b707840d.txt
_cod_data_source_block           Rhfluoropyridyl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7102121
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.26409(12) 0.43022(14) 0.14656(7) 0.0176(2) Uani 1 1 d .
C2 C 0.33449(12) 0.45420(14) 0.09738(8) 0.0192(3) Uani 1 1 d .
C3 C 0.32704(12) 0.37695(15) 0.03242(8) 0.0213(3) Uani 1 1 d .
C4 C 0.18654(12) 0.24551(15) 0.05588(8) 0.0213(3) Uani 1 1 d .
C5 C 0.18887(11) 0.31828(15) 0.12175(8) 0.0195(3) Uani 1 1 d .
C6 C 0.49910(14) 0.3299(2) 0.25437(10) 0.0342(4) Uani 1 1 d .
H6A H 0.5480 0.2572 0.2841 0.051 Uiso 1 1 calc R
H6B H 0.5444 0.4145 0.2481 0.051 Uiso 1 1 calc R
H6C H 0.4643 0.2899 0.2052 0.051 Uiso 1 1 calc R
C7 C 0.32005(14) 0.21007(16) 0.31059(9) 0.0289(3) Uani 1 1 d .
H7A H 0.2794 0.1781 0.2610 0.043 Uiso 1 1 calc R
H7B H 0.2665 0.2212 0.3432 0.043 Uiso 1 1 calc R
H7C H 0.3774 0.1384 0.3321 0.043 Uiso 1 1 calc R
C8 C 0.47557(16) 0.39908(19) 0.39732(9) 0.0336(4) Uani 1 1 d .
H8A H 0.4269 0.4209 0.4320 0.050 Uiso 1 1 calc R
H8B H 0.5306 0.4769 0.3988 0.050 Uiso 1 1 calc R
H8C H 0.5157 0.3084 0.4120 0.050 Uiso 1 1 calc R
C9 C 0.11898(19) 0.6702(2) 0.06230(10) 0.0455(5) Uani 1 1 d .
H9A H 0.0876 0.5737 0.0500 0.068 Uiso 1 1 calc R
H9B H 0.1918 0.6782 0.0477 0.068 Uiso 1 1 calc R
H9C H 0.0664 0.7423 0.0352 0.068 Uiso 1 1 calc R
C10 C -0.00729(14) 0.6942(2) 0.17120(11) 0.0373(4) Uani 1 1 d .
H10A H -0.0122 0.7245 0.2216 0.056 Uiso 1 1 calc R
H10B H -0.0360 0.5957 0.1622 0.056 Uiso 1 1 calc R
H10C H -0.0528 0.7590 0.1342 0.056 Uiso 1 1 calc R
C11 C 0.16886(18) 0.89377(19) 0.16319(12) 0.0431(5) Uani 1 1 d .
H11A H 0.1113 0.9412 0.1247 0.065 Uiso 1 1 calc R
H11B H 0.2438 0.9095 0.1526 0.065 Uiso 1 1 calc R
H11C H 0.1672 0.9341 0.2123 0.065 Uiso 1 1 calc R
C12 C 0.16638(15) 0.83407(18) 0.35006(10) 0.0313(3) Uani 1 1 d .
H12A H 0.0896 0.8168 0.3206 0.047 Uiso 1 1 calc R
H12B H 0.1996 0.9161 0.3290 0.047 Uiso 1 1 calc R
H12C H 0.1634 0.8552 0.4019 0.047 Uiso 1 1 calc R
C13 C 0.38144(14) 0.74599(18) 0.40874(9) 0.0308(3) Uani 1 1 d .
H13A H 0.3645 0.7749 0.4565 0.046 Uiso 1 1 calc R
H13B H 0.4076 0.8298 0.3849 0.046 Uiso 1 1 calc R
H13C H 0.4407 0.6721 0.4177 0.046 Uiso 1 1 calc R
C14 C 0.1944(2) 0.55898(18) 0.41015(11) 0.0393(4) Uani 1 1 d .
H14A H 0.2378 0.4692 0.4193 0.059 Uiso 1 1 calc R
H14B H 0.1153 0.5371 0.3871 0.059 Uiso 1 1 calc R
H14C H 0.1985 0.6092 0.4577 0.059 Uiso 1 1 calc R
F1 F 0.41393(8) 0.56039(9) 0.11145(5) 0.02688(19) Uani 1 1 d .
F2 F 0.39656(8) 0.40778(11) -0.01339(5) 0.0308(2) Uani 1 1 d .
F3 F 0.10985(8) 0.14027(9) 0.03391(5) 0.02814(19) Uani 1 1 d .
F4 F 0.11123(7) 0.27905(10) 0.16135(5) 0.02718(19) Uani 1 1 d .
N1 N 0.25420(11) 0.27243(13) 0.01056(7) 0.0228(2) Uani 1 1 d .
P1 P 0.38865(3) 0.38222(4) 0.302343(19) 0.01845(7) Uani 1 1 d .
P2 P 0.13964(3) 0.70063(4) 0.16301(2) 0.02092(8) Uani 1 1 d .
P3 P 0.25354(3) 0.67330(4) 0.34747(2) 0.01926(7) Uani 1 1 d .
Rh1 Rh 0.264541(8) 0.553895(10) 0.240541(5) 0.01550(4) 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'
F F 0.0171 0.0103 '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'
Rh Rh -1.1178 0.9187 '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
C2 C1 C5 111.07(12)
C2 C1 Rh1 124.22(10)
C5 C1 Rh1 124.59(10)
F1 C2 C3 116.71(12)
F1 C2 C1 120.18(12)
C3 C2 C1 123.09(13)
N1 C3 F2 115.98(12)
N1 C3 C2 124.07(13)
F2 C3 C2 119.94(13)
N1 C4 F3 115.76(12)
N1 C4 C5 124.47(13)
F3 C4 C5 119.76(13)
F4 C5 C4 117.01(12)
F4 C5 C1 120.44(12)
C4 C5 C1 122.52(13)
P1 C6 H6A 109.5
P1 C6 H6B 109.5
H6A C6 H6B 109.5
P1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
P1 C7 H7A 109.5
P1 C7 H7B 109.5
H7A C7 H7B 109.5
P1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
P1 C8 H8A 109.5
P1 C8 H8B 109.5
H8A C8 H8B 109.5
P1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
P2 C9 H9A 109.5
P2 C9 H9B 109.5
H9A C9 H9B 109.5
P2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
P2 C10 H10A 109.5
P2 C10 H10B 109.5
H10A C10 H10B 109.5
P2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
P2 C11 H11A 109.5
P2 C11 H11B 109.5
H11A C11 H11B 109.5
P2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
P3 C12 H12A 109.5
P3 C12 H12B 109.5
H12A C12 H12B 109.5
P3 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
P3 C13 H13A 109.5
P3 C13 H13B 109.5
H13A C13 H13B 109.5
P3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
P3 C14 H14A 109.5
P3 C14 H14B 109.5
H14A C14 H14B 109.5
P3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C3 N1 C4 114.76(12)
C6 P1 C7 101.71(8)
C6 P1 C8 98.78(9)
C7 P1 C8 99.95(8)
C6 P1 Rh1 114.54(5)
C7 P1 Rh1 112.76(5)
C8 P1 Rh1 125.61(5)
C10 P2 C11 102.97(10)
C10 P2 C9 99.24(10)
C11 P2 C9 97.86(10)
C10 P2 Rh1 117.03(6)
C11 P2 Rh1 118.89(7)
C9 P2 Rh1 117.36(6)
C14 P3 C13 103.03(9)
C14 P3 C12 98.56(8)
C13 P3 C12 95.61(8)
C14 P3 Rh1 111.36(6)
C13 P3 Rh1 120.27(6)
C12 P3 Rh1 124.13(6)
C1 Rh1 P3 174.29(4)
C1 Rh1 P2 86.21(4)
P3 Rh1 P2 95.043(14)
C1 Rh1 P1 84.64(4)
P3 Rh1 P1 93.997(13)
P2 Rh1 P1 170.822(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3897(19)
C1 C5 1.3911(19)
C1 Rh1 2.0700(13)
C2 F1 1.3623(15)
C2 C3 1.3763(19)
C3 N1 1.3137(19)
C3 F2 1.3455(16)
C4 N1 1.3141(19)
C4 F3 1.3475(16)
C4 C5 1.379(2)
C5 F4 1.3594(15)
C6 P1 1.8228(16)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 P1 1.8240(16)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 P1 1.8313(16)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 P2 1.8296(18)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 P2 1.8205(17)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 P2 1.8286(18)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 P3 1.8358(16)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 P3 1.8298(16)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 P3 1.8238(17)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
P1 Rh1 2.3094(4)
P2 Rh1 2.2838(4)
P3 Rh1 2.2821(4)
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
C5 C1 C2 F1 179.56(12)
Rh1 C1 C2 F1 3.28(19)
C5 C1 C2 C3 1.1(2)
Rh1 C1 C2 C3 -175.19(11)
F1 C2 C3 N1 -179.26(13)
C1 C2 C3 N1 -0.7(2)
F1 C2 C3 F2 0.2(2)
C1 C2 C3 F2 178.71(13)
N1 C4 C5 F4 178.58(13)
F3 C4 C5 F4 -0.40(19)
N1 C4 C5 C1 0.6(2)
F3 C4 C5 C1 -178.40(12)
C2 C1 C5 F4 -178.94(12)
Rh1 C1 C5 F4 -2.68(18)
C2 C1 C5 C4 -1.00(19)
Rh1 C1 C5 C4 175.26(11)
F2 C3 N1 C4 -179.31(12)
C2 C3 N1 C4 0.2(2)
F3 C4 N1 C3 178.94(12)
C5 C4 N1 C3 -0.1(2)
C2 C1 Rh1 P2 86.88(11)
C5 C1 Rh1 P2 -88.90(11)
C2 C1 Rh1 P1 -93.83(11)
C5 C1 Rh1 P1 90.39(11)
C14 P3 Rh1 P2 116.16(8)
C13 P3 Rh1 P2 -123.27(7)
C12 P3 Rh1 P2 -1.10(7)
C14 P3 Rh1 P1 -62.25(8)
C13 P3 Rh1 P1 58.32(7)
C12 P3 Rh1 P1 -179.51(7)
C10 P2 Rh1 C1 106.90(9)
C11 P2 Rh1 C1 -128.41(9)
C9 P2 Rh1 C1 -10.94(10)
C10 P2 Rh1 P3 -67.52(8)
C11 P2 Rh1 P3 57.18(9)
C9 P2 Rh1 P3 174.65(9)
C6 P1 Rh1 C1 44.68(8)
C7 P1 Rh1 C1 -71.02(7)
C8 P1 Rh1 C1 166.91(9)
C6 P1 Rh1 P3 -140.88(7)
C7 P1 Rh1 P3 103.42(6)
C8 P1 Rh1 P3 -18.66(8)
