#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:28:27 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179247 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/67/4316720.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_4316720
loop_
_publ_author_name
'Sinai Aharonovich'
'Mark Botoshansky'
'Robert M. Waymouth'
'Moris S. Eisen'
_publ_section_title
;
 Chemoselectivity Diversity in the Reaction of LiNC6F5SiMe3 with Nitriles
 and the Synthesis, Structure, and Reactivity of Zirconium Mono- and
 Tris[2-(2-pyridyl)tetrafluorobenzimidazolate] Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9217
_journal_page_last               9229
_journal_paper_doi               10.1021/ic100696r
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C23 H24 F9 Li N4 O'
_chemical_formula_weight         550.40
_chemical_name_common            'complex7 (Sinay)'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 114.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.807(2)
_cell_length_b                   16.647(3)
_cell_length_c                   9.424(2)
_cell_measurement_reflns_used    8173
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.38
_cell_volume                     1254.0(5)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'TEXSAN  (MSC, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      240(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       phi-scan
_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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8173
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0817P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                1949
_reflns_number_total             2390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100696r_si_002_2.cif
_cod_data_source_block           complex7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4316720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
F1 F -0.2282(3) 0.18836(14) 0.5576(3) 0.0423(6) Uani 1 1 d . . .
F2 F -0.5158(3) 0.16845(14) 0.3058(3) 0.0491(6) Uani 1 1 d . . .
F3 F -0.4133(3) 0.40426(15) 0.0835(3) 0.0465(6) Uani 1 1 d . . .
F4 F -0.1272(3) 0.42619(14) 0.3320(3) 0.0454(6) Uani 1 1 d . . .
F5 F 0.0959(3) 0.43609(17) 0.8123(3) 0.0542(7) Uani 1 1 d . . .
F6 F 0.3646(3) 0.52403(17) 0.8514(4) 0.0663(8) Uani 1 1 d . . .
F7 F 0.5282(3) 0.49904(18) 0.6645(4) 0.0711(9) Uani 1 1 d . . .
F8 F 0.4102(4) 0.3871(2) 0.4340(4) 0.0680(9) Uani 1 1 d . . .
F9 F 0.1412(3) 0.29886(18) 0.3944(3) 0.0576(7) Uani 1 1 d . . .
O1 O 0.1448(3) 0.1396(2) 0.6510(4) 0.0497(8) Uani 1 1 d . . .
N1 N -0.0235(4) 0.3119(2) 0.5927(4) 0.0353(8) Uani 1 1 d . . .
N2 N 0.2558(4) 0.2586(2) 0.9417(4) 0.0408(8) Uani 1 1 d . . .
N3 N -0.0065(4) 0.1036(2) 0.8984(4) 0.0418(8) Uani 1 1 d . . .
N4 N -0.1449(4) 0.2667(2) 0.8875(4) 0.0417(8) Uani 1 1 d . . .
C1 C -0.1607(4) 0.3073(2) 0.4583(4) 0.0305(8) Uani 1 1 d . . .
C2 C -0.2736(5) 0.2434(2) 0.4407(4) 0.0334(9) Uani 1 1 d . . .
C3 C -0.4194(5) 0.2322(2) 0.3122(5) 0.0321(8) Uani 1 1 d . . .
C4 C -0.4731(5) 0.2853(2) 0.1850(4) 0.0334(8) Uani 1 1 d . . .
C5 C -0.3665(4) 0.3506(2) 0.2009(4) 0.0301(8) Uani 1 1 d . . .
C6 C -0.2196(4) 0.3599(2) 0.3281(4) 0.0310(8) Uani 1 1 d . . .
C7 C 0.1078(5) 0.3619(3) 0.6030(4) 0.0339(9) Uani 1 1 d . . .
C8 C 0.1723(5) 0.4212(2) 0.7183(5) 0.0368(9) Uani 1 1 d . . .
C9 C 0.3108(5) 0.4668(3) 0.7387(5) 0.0453(10) Uani 1 1 d . . .
C10 C 0.3911(5) 0.4554(3) 0.6448(6) 0.0469(11) Uani 1 1 d . . .
C11 C 0.3320(5) 0.3995(3) 0.5275(5) 0.0443(11) Uani 1 1 d . . .
C12 C 0.1945(5) 0.3532(2) 0.5092(5) 0.0373(9) Uani 1 1 d . . .
C13 C -0.0709(8) 0.1336(3) 1.0086(7) 0.0631(14) Uani 1 1 d . . .
H13A H -0.1184 0.0898 1.0426 0.076 Uiso 1 1 d R . .
H13B H 0.0184 0.1573 1.0974 0.076 Uiso 1 1 d R . .
C14 C -0.2031(7) 0.1942(3) 0.9397(7) 0.0612(14) Uani 1 1 d . . .
H14A H -0.2418 0.2081 1.0178 0.073 Uiso 1 1 d R . .
H14B H -0.2928 0.1702 0.8518 0.073 Uiso 1 1 d R . .
C15 C -0.1208(6) 0.0452(3) 0.7886(6) 0.0541(12) Uani 1 1 d . . .
H15A H -0.2274 0.0708 0.7275 0.081 Uiso 1 1 calc R . .
H15B H -0.1376 0.0005 0.8465 0.081 Uiso 1 1 calc R . .
H15C H -0.0730 0.0257 0.7193 0.081 Uiso 1 1 calc R . .
C16 C 0.1539(6) 0.0626(3) 0.9834(6) 0.0588(13) Uani 1 1 d . . .
H16A H 0.1945 0.0419 0.9095 0.088 Uiso 1 1 calc R . .
H16B H 0.1386 0.0185 1.0434 0.088 Uiso 1 1 calc R . .
H16C H 0.2346 0.1002 1.0536 0.088 Uiso 1 1 calc R . .
C17 C -0.0473(7) 0.3191(4) 1.0164(6) 0.0602(13) Uani 1 1 d . . .
H17A H -0.0069 0.3644 0.9774 0.090 Uiso 1 1 calc R . .
H17B H 0.0471 0.2895 1.0917 0.090 Uiso 1 1 calc R . .
H17C H -0.1167 0.3383 1.0665 0.090 Uiso 1 1 calc R . .
C18 C -0.2897(7) 0.3129(4) 0.7832(6) 0.0700(16) Uani 1 1 d . . .
H18A H -0.3574 0.2802 0.6938 0.105 Uiso 1 1 calc R . .
H18B H -0.2520 0.3604 0.7477 0.105 Uiso 1 1 calc R . .
H18C H -0.3558 0.3288 0.8388 0.105 Uiso 1 1 calc R . .
C19 C 0.0671(6) 0.1107(3) 0.4935(5) 0.0504(11) Uani 1 1 d . . .
H19A H 0.0102 0.1547 0.4220 0.060 Uiso 1 1 calc R . .
H19B H -0.0158 0.0693 0.4840 0.060 Uiso 1 1 calc R . .
C20 C 0.2030(6) 0.0759(4) 0.4539(7) 0.0680(15) Uani 1 1 d . . .
H20A H 0.1805 0.0193 0.4238 0.082 Uiso 1 1 calc R . .
H20B H 0.2112 0.1057 0.3676 0.082 Uiso 1 1 calc R . .
C21 C 0.3589(7) 0.0844(5) 0.5988(7) 0.0797(19) Uani 1 1 d . . .
H21A H 0.3921 0.0325 0.6520 0.096 Uiso 1 1 calc R . .
H21B H 0.4501 0.1043 0.5746 0.096 Uiso 1 1 calc R . .
C22 C 0.3207(6) 0.1429(4) 0.6989(6) 0.0658(15) Uani 1 1 d . . .
H22A H 0.3798 0.1283 0.8095 0.079 Uiso 1 1 calc R . .
H22B H 0.3550 0.1972 0.6844 0.079 Uiso 1 1 calc R . .
Li1 Li 0.0223(8) 0.2159(4) 0.7677(8) 0.0401(15) Uani 1 1 d . . .
C23 C -0.6235(4) 0.2723(2) 0.0499(4) 0.0320(8) 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
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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'
Li Li -0.0003 0.0001 '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
C2 F1 Li1 114.3(3) . . ?
C19 O1 C22 109.0(3) . . ?
C19 O1 Li1 125.6(3) . . ?
C22 O1 Li1 120.6(3) . . ?
C1 N1 C7 119.6(3) . . ?
C1 N1 Li1 118.4(3) . . ?
C7 N1 Li1 119.6(3) . . ?
C23 N2 Li1 168.9(4) 1_656 . ?
C16 N3 C13 110.0(4) . . ?
C16 N3 C15 107.1(4) . . ?
C13 N3 C15 111.7(4) . . ?
C16 N3 Li1 111.8(3) . . ?
C13 N3 Li1 105.3(3) . . ?
C15 N3 Li1 110.9(3) . . ?
C14 N4 C18 109.2(4) . . ?
C14 N4 C17 112.3(4) . . ?
C18 N4 C17 106.9(4) . . ?
C14 N4 Li1 103.9(3) . . ?
C18 N4 Li1 114.3(3) . . ?
C17 N4 Li1 110.3(3) . . ?
N1 C1 C6 130.0(4) . . ?
N1 C1 C2 117.7(3) . . ?
C6 C1 C2 112.2(3) . . ?
C3 C2 F1 118.4(3) . . ?
C3 C2 C1 124.2(3) . . ?
F1 C2 C1 117.3(3) . . ?
F2 C3 C2 119.5(3) . . ?
F2 C3 C4 118.6(3) . . ?
C2 C3 C4 121.9(3) . . ?
C5 C4 C3 115.3(3) . . ?
C5 C4 C23 123.1(3) . . ?
C3 C4 C23 121.6(3) . . ?
F3 C5 C6 120.1(3) . . ?
F3 C5 C4 117.8(3) . . ?
C6 C5 C4 122.1(3) . . ?
C5 C6 F4 117.0(3) . . ?
C5 C6 C1 124.2(3) . . ?
F4 C6 C1 118.7(3) . . ?
C8 C7 N1 121.9(3) . . ?
C8 C7 C12 114.4(3) . . ?
N1 C7 C12 123.5(4) . . ?
F5 C8 C9 117.7(4) . . ?
F5 C8 C7 119.4(3) . . ?
C9 C8 C7 122.9(4) . . ?
F6 C9 C10 120.2(4) . . ?
F6 C9 C8 119.6(4) . . ?
C10 C9 C8 120.2(4) . . ?
C9 C10 F7 120.9(5) . . ?
C9 C10 C11 119.7(4) . . ?
F7 C10 C11 119.4(4) . . ?
F8 C11 C12 119.7(4) . . ?
F8 C11 C10 120.5(4) . . ?
C12 C11 C10 119.7(4) . . ?
F9 C12 C11 118.0(4) . . ?
F9 C12 C7 118.9(3) . . ?
C11 C12 C7 123.0(4) . . ?
N3 C13 C14 113.0(4) . . ?
N3 C13 H13A 109.2 . . ?
C14 C13 H13A 107.1 . . ?
N3 C13 H13B 109.8 . . ?
C14 C13 H13B 108.1 . . ?
H13A C13 H13B 109.5 . . ?
N4 C14 C13 112.9(4) . . ?
N4 C14 H14A 110.1 . . ?
C13 C14 H14A 107.3 . . ?
N4 C14 H14B 109.2 . . ?
C13 C14 H14B 107.9 . . ?
H14A C14 H14B 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 107.5(4) . . ?
O1 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O1 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C21 C20 C19 105.1(4) . . ?
C21 C20 H20A 110.7 . . ?
C19 C20 H20A 110.7 . . ?
C21 C20 H20B 110.7 . . ?
C19 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
C22 C21 C20 106.1(5) . . ?
C22 C21 H21A 110.5 . . ?
C20 C21 H21A 110.5 . . ?
C22 C21 H21B 110.5 . . ?
C20 C21 H21B 110.5 . . ?
H21A C21 H21B 108.7 . . ?
O1 C22 C21 106.2(4) . . ?
O1 C22 H22A 110.5 . . ?
C21 C22 H22A 110.5 . . ?
O1 C22 H22B 110.5 . . ?
C21 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
N2 Li1 N1 98.5(3) . . ?
N2 Li1 O1 93.4(3) . . ?
N1 Li1 O1 91.1(3) . . ?
N2 Li1 N3 98.3(3) . . ?
N1 Li1 N3 163.1(4) . . ?
O1 Li1 N3 89.2(3) . . ?
N2 Li1 F1 170.7(4) . . ?
N1 Li1 F1 72.2(2) . . ?
O1 Li1 F1 87.1(3) . . ?
N3 Li1 F1 91.0(3) . . ?
N2 Li1 N4 96.1(3) . . ?
N1 Li1 N4 98.2(3) . . ?
O1 Li1 N4 165.6(4) . . ?
N3 Li1 N4 78.7(2) . . ?
F1 Li1 N4 85.3(2) . . ?
N2 C23 C4 177.3(4) 1_454 . ?
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
F1 C2 1.358(4) . ?
F1 Li1 2.309(7) . ?
F2 C3 1.344(4) . ?
F3 C5 1.345(4) . ?
F4 C6 1.362(4) . ?
F5 C8 1.340(5) . ?
F6 C9 1.355(5) . ?
F7 C10 1.353(5) . ?
F8 C11 1.343(5) . ?
F9 C12 1.335(5) . ?
O1 C19 1.432(6) . ?
O1 C22 1.421(5) . ?
O1 Li1 2.232(8) . ?
N1 C1 1.336(5) . ?
N1 C7 1.395(5) . ?
N1 Li1 2.209(7) . ?
N2 C23 1.146(5) 1_656 ?
N2 Li1 2.142(8) . ?
N3 C16 1.468(6) . ?
N3 C13 1.465(6) . ?
N3 C15 1.468(6) . ?
N3 Li1 2.310(7) . ?
N4 C14 1.474(7) . ?
N4 C18 1.459(6) . ?
N4 C17 1.449(6) . ?
N4 Li1 2.357(8) . ?
C1 C6 1.417(5) . ?
C1 C2 1.417(5) . ?
C2 C3 1.358(5) . ?
C3 C4 1.402(6) . ?
C4 C5 1.403(5) . ?
C4 C23 1.416(5) . ?
C5 C6 1.354(5) . ?
C7 C8 1.400(6) . ?
C7 C12 1.397(6) . ?
C8 C9 1.380(6) . ?
C9 C10 1.359(7) . ?
C10 C11 1.369(7) . ?
C11 C12 1.384(6) . ?
C13 C14 1.470(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 C20 1.511(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C21 1.482(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.490(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 N2 1.146(5) 1_454 ?
