#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:29:24 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179751 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/47/7004790.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_7004790
loop_
_publ_author_name
'Camadanli, Sebnem'
'Beck, Robert'
'Flörke, Ulrich'
'Klein, Hans-Friedrich'
_publ_section_title
;
 First regioselective cyclometalation reactions of cobalt in
 arylketones: C--H versus C--F activation
;
_journal_issue                   42
_journal_name_full               'Dalton Transactions'
_journal_page_first              5701
_journal_page_last               5704
_journal_paper_doi               10.1039/B813419g
_journal_year                    2008
_chemical_formula_sum            'C22 H36 Co F O P3'
_chemical_formula_weight         487.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(12)
_cell_angle_beta                 101.030(12)
_cell_angle_gamma                90.000(12)
_cell_formula_units_Z            4
_cell_length_a                   9.7220(12)
_cell_length_b                   17.1350(13)
_cell_length_c                   15.4390(11)
_cell_measurement_temperature    150(2)
_cell_volume                     2524.4(4)
_computing_cell_refinement       'Stoe X-Area'
_computing_data_collection       'Stoe X-Area'
_computing_data_reduction        'Stoe X-RED'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       '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  0.1130
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            30970
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.16
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  0.9324
_exptl_absorpt_correction_T_min  0.9010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bloc
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.717
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0450
_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)+(0.0684P)²+1.0226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                4494
_reflns_number_total             5112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B813419g.txt
_cod_data_source_block           c:\structures\4
_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      P21/n
_cod_database_code               7004790
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6744(2) 0.25560(12) 0.43596(15) 0.0202(5) Uani 1 1 d . . .
C2 C 0.7325(2) 0.33230(13) 0.41066(15) 0.0219(5) Uani 1 1 d . . .
C3 C 0.7365(3) 0.35772(14) 0.32521(16) 0.0263(5) Uani 1 1 d . . .
C4 C 0.7842(3) 0.43049(15) 0.3060(2) 0.0369(6) Uani 1 1 d . . .
H5A H 0.7840 0.4449 0.2479 0.044 Uiso 1 1 calc R . .
C5 C 0.8322(3) 0.48182(15) 0.3749(2) 0.0433(8) Uani 1 1 d . . .
H11A H 0.8655 0.5309 0.3632 0.052 Uiso 1 1 calc R . .
C6 C 0.8305(3) 0.45954(16) 0.4612(2) 0.0400(7) Uani 1 1 d . . .
H7A H 0.8620 0.4938 0.5075 0.048 Uiso 1 1 calc R . .
C7 C 0.7816(3) 0.38605(15) 0.47835(18) 0.0299(5) Uani 1 1 d . . .
H6A H 0.7813 0.3719 0.5365 0.036 Uiso 1 1 calc R . .
C8 C 0.7479(2) 0.18072(13) 0.42123(15) 0.0219(5) Uani 1 1 d . . .
C9 C 0.8181(2) 0.16742(14) 0.35140(17) 0.0258(5) Uani 1 1 d . . .
H2A H 0.8251 0.2076 0.3119 0.031 Uiso 1 1 calc R . .
C10 C 0.8777(3) 0.09502(15) 0.34002(18) 0.0318(6) Uani 1 1 d . . .
H4A H 0.9199 0.0868 0.2916 0.038 Uiso 1 1 calc R . .
C11 C 0.8749(3) 0.03517(15) 0.3998(2) 0.0377(6) Uani 1 1 d . . .
H9A H 0.9152 -0.0129 0.3922 0.045 Uiso 1 1 calc R . .
C12 C 0.8106(3) 0.04846(16) 0.4714(2) 0.0399(7) Uani 1 1 d . . .
H12A H 0.8103 0.0092 0.5130 0.048 Uiso 1 1 calc R . .
C13 C 0.7466(3) 0.11936(15) 0.48196(18) 0.0311(6) Uani 1 1 d . . .
H10A H 0.7024 0.1265 0.5297 0.037 Uiso 1 1 calc R . .
C14 C 0.4211(3) 0.44723(15) 0.3960(2) 0.0402(7) Uani 1 1 d . . .
H15A H 0.5194 0.4521 0.3956 0.048 Uiso 1 1 calc R . .
H15B H 0.4061 0.4509 0.4555 0.048 Uiso 1 1 calc R . .
H15C H 0.3709 0.4883 0.3612 0.048 Uiso 1 1 calc R . .
C15 C 0.3604(3) 0.37029(19) 0.23147(19) 0.0440(7) Uani 1 1 d . . .
H18C H 0.3102 0.4175 0.2128 0.053 Uiso 1 1 calc R . .
H18B H 0.3166 0.3273 0.1969 0.053 Uiso 1 1 calc R . .
H18A H 0.4556 0.3753 0.2236 0.053 Uiso 1 1 calc R . .
C16 C 0.1692(3) 0.36438(17) 0.3458(2) 0.0385(6) Uani 1 1 d . . .
H13A H 0.1521 0.3684 0.4049 0.046 Uiso 1 1 calc R . .
H13B H 0.1199 0.3200 0.3172 0.046 Uiso 1 1 calc R . .
H13C H 0.1368 0.4109 0.3136 0.046 Uiso 1 1 calc R . .
C17 C 0.3356(3) 0.31548(17) 0.59481(19) 0.0398(7) Uani 1 1 d . . .
H21A H 0.3002 0.3601 0.5599 0.048 Uiso 1 1 calc R . .
H21B H 0.4300 0.3255 0.6246 0.048 Uiso 1 1 calc R . .
H21C H 0.2779 0.3055 0.6376 0.048 Uiso 1 1 calc R . .
C18 C 0.4153(3) 0.15790(17) 0.60325(19) 0.0398(7) Uani 1 1 d . . .
H14A H 0.5066 0.1758 0.6311 0.048 Uiso 1 1 calc R . .
H14B H 0.4238 0.1093 0.5738 0.048 Uiso 1 1 calc R . .
H14C H 0.3586 0.1505 0.6471 0.048 Uiso 1 1 calc R . .
C19 C 0.1494(3) 0.20093(19) 0.5079(2) 0.0415(7) Uani 1 1 d . . .
H22C H 0.1219 0.1982 0.5644 0.050 Uiso 1 1 calc R . .
H22B H 0.1376 0.1507 0.4800 0.050 Uiso 1 1 calc R . .
H22A H 0.0921 0.2385 0.4715 0.050 Uiso 1 1 calc R . .
C20 C 0.4727(3) 0.1550(2) 0.2213(2) 0.0460(8) Uani 1 1 d . . .
H16A H 0.5718 0.1466 0.2387 0.055 Uiso 1 1 calc R . .
H16B H 0.4562 0.2035 0.1898 0.055 Uiso 1 1 calc R . .
H16C H 0.4318 0.1130 0.1839 0.055 Uiso 1 1 calc R . .
C21 C 0.4200(5) 0.05707(17) 0.3567(3) 0.0606(10) Uani 1 1 d . . .
H19A H 0.3696 0.0476 0.4034 0.073 Uiso 1 1 calc R . .
H19B H 0.5181 0.0479 0.3779 0.073 Uiso 1 1 calc R . .
H19C H 0.3863 0.0226 0.3083 0.073 Uiso 1 1 calc R . .
C22 C 0.2077(3) 0.1565(2) 0.2656(2) 0.0530(9) Uani 1 1 d . . .
H17C H 0.1927 0.1150 0.2232 0.064 Uiso 1 1 calc R . .
H17B H 0.1827 0.2054 0.2363 0.064 Uiso 1 1 calc R . .
H17A H 0.1508 0.1481 0.3092 0.064 Uiso 1 1 calc R . .
Co1 Co 0.46365(3) 0.247968(15) 0.421370(19) 0.01735(11) Uani 1 1 d . . .
F1 F 0.68442(17) 0.30984(9) 0.25483(9) 0.0354(4) Uani 1 1 d . . .
O1 O 0.62480(18) 0.25929(9) 0.51126(11) 0.0225(3) Uani 1 1 d . . .
P1 P 0.39335(7) 0.15879(4) 0.31962(4) 0.02638(16) Uani 1 1 d . . .
P2 P 0.33318(7) 0.23020(4) 0.52297(4) 0.02321(15) Uani 1 1 d . . .
P3 P 0.35815(7) 0.35246(4) 0.34931(4) 0.02582(16) 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'
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'
O O 0.0106 0.0060 '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
O1 C1 C8 115.47(19) . . ?
O1 C1 C2 113.38(18) . . ?
C8 C1 C2 119.35(19) . . ?
O1 C1 Co1 64.87(12) . . ?
C8 C1 Co1 115.33(15) . . ?
C2 C1 Co1 116.63(15) . . ?
C3 C2 C7 115.5(2) . . ?
C3 C2 C1 126.5(2) . . ?
C7 C2 C1 117.9(2) . . ?
F1 C3 C4 117.1(2) . . ?
F1 C3 C2 119.1(2) . . ?
C4 C3 C2 123.7(2) . . ?
C3 C4 C5 119.0(3) . . ?
C6 C5 C4 119.7(2) . . ?
C7 C6 C5 119.9(3) . . ?
C6 C7 C2 122.1(3) . . ?
C9 C8 C13 117.2(2) . . ?
C9 C8 C1 124.7(2) . . ?
C13 C8 C1 118.0(2) . . ?
C10 C9 C8 121.1(2) . . ?
C11 C10 C9 120.9(3) . . ?
C10 C11 C12 118.6(2) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C8 120.9(2) . . ?
O1 Co1 C1 39.93(8) . . ?
O1 Co1 P1 133.91(5) . . ?
C1 Co1 P1 107.07(7) . . ?
O1 Co1 P2 90.04(5) . . ?
C1 Co1 P2 129.36(7) . . ?
P1 Co1 P2 105.51(3) . . ?
O1 Co1 P3 121.06(5) . . ?
C1 Co1 P3 111.11(7) . . ?
P1 Co1 P3 98.60(3) . . ?
P2 Co1 P3 100.99(3) . . ?
C1 O1 Co1 75.20(13) . . ?
C20 P1 C21 99.70(18) . . ?
C20 P1 C22 98.99(16) . . ?
C21 P1 C22 100.90(18) . . ?
C20 P1 Co1 119.53(10) . . ?
C21 P1 Co1 115.43(11) . . ?
C22 P1 Co1 118.78(10) . . ?
C18 P2 C19 100.95(14) . . ?
C18 P2 C17 100.20(15) . . ?
C19 P2 C17 101.23(14) . . ?
C18 P2 Co1 109.79(9) . . ?
C19 P2 Co1 128.69(10) . . ?
C17 P2 Co1 112.07(10) . . ?
C14 P3 C16 99.78(14) . . ?
C14 P3 C15 100.03(16) . . ?
C16 P3 C15 98.80(14) . . ?
C14 P3 Co1 115.10(10) . . ?
C16 P3 Co1 117.47(10) . . ?
C15 P3 Co1 121.87(10) . . ?
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
C1 O1 1.343(3) . ?
C1 C8 1.507(3) . ?
C1 C2 1.511(3) . ?
C1 Co1 2.022(2) . ?
C2 C3 1.397(3) . ?
C2 C7 1.406(3) . ?
C3 F1 1.378(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.390(4) . ?
C5 C6 1.390(5) . ?
C6 C7 1.389(4) . ?
C8 C9 1.401(3) . ?
C8 C13 1.410(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.383(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.388(4) . ?
C14 P3 1.834(3) . ?
C15 P3 1.849(3) . ?
C16 P3 1.839(3) . ?
C17 P2 1.832(3) . ?
C18 P2 1.825(3) . ?
C19 P2 1.828(3) . ?
C20 P1 1.831(3) . ?
C21 P1 1.838(3) . ?
C22 P1 1.838(3) . ?
Co1 O1 1.8938(17) . ?
Co1 P1 2.2043(7) . ?
Co1 P2 2.2189(7) . ?
Co1 P3 2.2492(7) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -151.2(2) . . . . ?
C8 C1 C2 C3 67.5(3) . . . . ?
Co1 C1 C2 C3 -78.7(3) . . . . ?
O1 C1 C2 C7 25.4(3) . . . . ?
C8 C1 C2 C7 -115.9(2) . . . . ?
Co1 C1 C2 C7 97.9(2) . . . . ?
C7 C2 C3 F1 -177.1(2) . . . . ?
C1 C2 C3 F1 -0.5(4) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 176.3(2) . . . . ?
F1 C3 C4 C5 177.4(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C3 C2 C7 C6 0.2(4) . . . . ?
C1 C2 C7 C6 -176.8(2) . . . . ?
O1 C1 C8 C9 -174.0(2) . . . . ?
C2 C1 C8 C9 -33.4(3) . . . . ?
Co1 C1 C8 C9 113.2(2) . . . . ?
O1 C1 C8 C13 5.9(3) . . . . ?
C2 C1 C8 C13 146.5(2) . . . . ?
Co1 C1 C8 C13 -66.9(3) . . . . ?
C13 C8 C9 C10 3.3(3) . . . . ?
C1 C8 C9 C10 -176.8(2) . . . . ?
C8 C9 C10 C11 -3.0(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C11 C12 C13 C8 -1.5(4) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C1 C8 C13 C12 179.0(2) . . . . ?
C8 C1 Co1 O1 107.7(2) . . . . ?
C2 C1 Co1 O1 -104.8(2) . . . . ?
O1 C1 Co1 P1 -139.76(10) . . . . ?
C8 C1 Co1 P1 -32.09(18) . . . . ?
C2 C1 Co1 P1 115.46(16) . . . . ?
O1 C1 Co1 P2 -11.90(14) . . . . ?
C8 C1 Co1 P2 95.77(17) . . . . ?
C2 C1 Co1 P2 -116.68(15) . . . . ?
O1 C1 Co1 P3 113.61(10) . . . . ?
C8 C1 Co1 P3 -138.72(15) . . . . ?
C2 C1 Co1 P3 8.83(18) . . . . ?
C8 C1 O1 Co1 -107.45(18) . . . . ?
C2 C1 O1 Co1 109.66(18) . . . . ?
P1 Co1 O1 C1 59.00(13) . . . . ?
P2 Co1 O1 C1 170.83(11) . . . . ?
P3 Co1 O1 C1 -86.29(12) . . . . ?
O1 Co1 P1 C20 -76.02(15) . . . . ?
C1 Co1 P1 C20 -40.89(15) . . . . ?
P2 Co1 P1 C20 178.42(13) . . . . ?
P3 Co1 P1 C20 74.42(13) . . . . ?
O1 Co1 P1 C21 42.90(18) . . . . ?
C1 Co1 P1 C21 78.04(17) . . . . ?
P2 Co1 P1 C21 -62.65(16) . . . . ?
P3 Co1 P1 C21 -166.66(16) . . . . ?
O1 Co1 P1 C22 162.91(17) . . . . ?
C1 Co1 P1 C22 -161.95(17) . . . . ?
P2 Co1 P1 C22 57.36(15) . . . . ?
P3 Co1 P1 C22 -46.65(15) . . . . ?
O1 Co1 P2 C18 -48.67(12) . . . . ?
C1 Co1 P2 C18 -41.06(14) . . . . ?
P1 Co1 P2 C18 87.38(12) . . . . ?
P3 Co1 P2 C18 -170.39(11) . . . . ?
O1 Co1 P2 C19 -171.81(15) . . . . ?
C1 Co1 P2 C19 -164.20(16) . . . . ?
P1 Co1 P2 C19 -35.76(14) . . . . ?
P3 Co1 P2 C19 66.47(14) . . . . ?
O1 Co1 P2 C17 61.75(12) . . . . ?
C1 Co1 P2 C17 69.36(14) . . . . ?
P1 Co1 P2 C17 -162.20(11) . . . . ?
P3 Co1 P2 C17 -59.97(12) . . . . ?
O1 Co1 P3 C14 -9.60(13) . . . . ?
C1 Co1 P3 C14 -52.96(13) . . . . ?
P1 Co1 P3 C14 -165.08(11) . . . . ?
P2 Co1 P3 C14 87.17(12) . . . . ?
O1 Co1 P3 C16 -126.66(12) . . . . ?
C1 Co1 P3 C16 -170.02(13) . . . . ?
P1 Co1 P3 C16 77.86(11) . . . . ?
P2 Co1 P3 C16 -29.90(11) . . . . ?
O1 Co1 P3 C15 111.59(15) . . . . ?
C1 Co1 P3 C15 68.23(16) . . . . ?
P1 Co1 P3 C15 -43.89(14) . . . . ?
P2 Co1 P3 C15 -151.64(14) . . . . ?
