#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:00:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178544 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/51/4065104.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_4065104
loop_
_publ_author_name
'Schreiber, Dominique F.'
'Ortin, Yannick'
'Müller-Bunz, Helge'
'Phillips, Andrew D.'
_publ_section_title
;
 Application of Electron-Withdrawing Coordinatively Unsaturated η6-Arene
 β-Diketiminato--Ruthenium Complexes in Lewis Acid Catalyzed Diels--Alder
 Reactions
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5381
_journal_paper_doi               10.1021/om200566a
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C21 H8 F18 N2'
_chemical_formula_sum            'C21 H8 F18 N2'
_chemical_formula_weight         630.29
_chemical_name_common            MegaFluorus
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 92.344(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.1409(10)
_cell_length_b                   7.9853(4)
_cell_length_c                   15.7083(8)
_cell_measurement_reflns_used    5526
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.2418
_cell_measurement_theta_min      3.0448
_cell_volume                     2273.6(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    'ORTEP-3 for windows 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX 1.80.05 (Farrugia, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.2812
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω and π scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8000
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0399
_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)+(0.0456P)²+3.9030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                1912
_reflns_number_total             2229
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            om200566a_si_002.cif
_cod_data_source_block           adp422
_cod_database_code               4065104
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.90043(10) 0.2090(2) 0.62858(11) 0.0232(4) Uani 1 1 d . . .
H1 H 0.973(2) 0.242(6) 0.720(3) 0.035 Uiso 0.50 1 d P . .
C2 C 0.91844(10) 0.1859(2) 0.54444(11) 0.0260(4) Uani 1 1 d . . .
H2 H 0.9621 0.2340 0.5236 0.031 Uiso 1 1 calc R . .
C3 C 0.87180(10) 0.0916(2) 0.49090(11) 0.0260(4) Uani 1 1 d . . .
C4 C 0.80772(10) 0.0209(2) 0.52044(11) 0.0252(4) Uani 1 1 d . . .
H4 H 0.7758 -0.0421 0.4832 0.030 Uiso 1 1 calc R . .
C5 C 0.79092(10) 0.0435(2) 0.60488(11) 0.0236(4) Uani 1 1 d . A .
C6 C 0.83695(10) 0.1365(2) 0.65937(11) 0.0236(4) Uani 1 1 d . . .
H6 H 0.8253 0.1507 0.7173 0.028 Uiso 1 1 calc R . .
C7 C 0.89017(12) 0.0630(3) 0.40002(12) 0.0356(5) Uani 1 1 d . . .
C8 C 0.72268(11) -0.0361(3) 0.63698(12) 0.0309(4) Uani 1 1 d . . .
C9 C 0.95318(9) 0.4652(2) 0.69106(10) 0.0215(4) Uani 1 1 d . . .
C10 C 1.0000 0.5481(3) 0.7500 0.0211(5) Uani 1 2 d S . .
H10 H 1.0000 0.6671 0.7500 0.025 Uiso 1 2 calc SR . .
C11 C 0.90834(10) 0.5751(2) 0.62880(12) 0.0257(4) Uani 1 1 d . . .
N1 N 0.94803(9) 0.3009(2) 0.68613(10) 0.0251(3) Uani 1 1 d . . .
F1 F 0.94515(10) 0.1569(3) 0.37530(9) 0.0817(7) Uani 1 1 d . . .
F2 F 0.90996(8) -0.0955(2) 0.38563(9) 0.0559(4) Uani 1 1 d . . .
F3 F 0.83217(9) 0.0897(2) 0.34673(8) 0.0612(5) Uani 1 1 d . . .
F4 F 0.66329(9) -0.0029(4) 0.58871(12) 0.0670(8) Uani 0.886(5) 1 d P A 1
F5 F 0.70644(10) 0.0135(3) 0.71482(10) 0.0565(7) Uani 0.886(5) 1 d P A 1
F6 F 0.72912(11) -0.2011(2) 0.6423(2) 0.0753(10) Uani 0.886(5) 1 d P A 1
F6B F 0.6984(7) -0.1587(18) 0.5790(8) 0.044(4) Uani 0.114(5) 1 d P A 2
F4B F 0.7333(8) -0.113(3) 0.7019(10) 0.061(5) Uani 0.114(5) 1 d PU A 2
F5B F 0.6704(9) 0.063(2) 0.6392(16) 0.073(5) Uani 0.114(5) 1 d PU A 2
F7 F 0.83908(6) 0.52141(14) 0.61557(7) 0.0339(3) Uani 1 1 d . . .
F8 F 0.93933(7) 0.57746(16) 0.55275(7) 0.0386(3) Uani 1 1 d . . .
F9 F 0.90449(7) 0.73327(14) 0.65495(8) 0.0381(3) 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'
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
C2 C1 C6 120.42(16) . .
C2 C1 N1 120.78(16) . .
C6 C1 N1 118.75(16) . .
C1 C2 C3 119.15(16) . .
C1 C2 H2 120.4 . .
C3 C2 H2 120.4 . .
C4 C3 C2 121.02(17) . .
C4 C3 C7 118.60(16) . .
C2 C3 C7 120.39(16) . .
C5 C4 C3 119.14(16) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 120.69(17) . .
C4 C5 C8 118.99(16) . .
C6 C5 C8 120.32(16) . .
C5 C6 C1 119.58(16) . .
C5 C6 H6 120.2 . .
C1 C6 H6 120.2 . .
F1 C7 F3 108.13(19) . .
F1 C7 F2 106.05(19) . .
F3 C7 F2 104.78(17) . .
F1 C7 C3 113.25(16) . .
F3 C7 C3 111.93(17) . .
F2 C7 C3 112.17(18) . .
F4B C8 F5B 113.6(14) . .
F4B C8 F4 133.7(7) . .
F4B C8 F6 54.9(10) . .
F5B C8 F6 134.4(8) . .
F4 C8 F6 107.7(2) . .
F4B C8 F5 53.5(10) . .
F5B C8 F5 65.5(12) . .
F4 C8 F5 105.20(19) . .
F6 C8 F5 105.1(2) . .
F4B C8 F6B 103.3(11) . .
F5B C8 F6B 104.1(12) . .
F4 C8 F6B 62.4(7) . .
F6 C8 F6B 50.9(6) . .
F5 C8 F6B 137.2(5) . .
F4B C8 C5 113.4(7) . .
F5B C8 C5 112.6(8) . .
F4 C8 C5 112.83(17) . .
F6 C8 C5 111.82(17) . .
F5 C8 C5 113.59(17) . .
F6B C8 C5 108.7(5) . .
N1 C9 C10 123.42(17) . .
N1 C9 C11 120.09(16) . .
C10 C9 C11 116.47(17) . .
C9 C10 C9 123.4(2) . 2_756
C9 C10 H10 118.3 . .
C9 C10 H10 118.3 2_756 .
F9 C11 F7 106.97(15) . .
F9 C11 F8 106.93(15) . .
F7 C11 F8 106.97(14) . .
F9 C11 C9 112.45(15) . .
F7 C11 C9 112.86(15) . .
F8 C11 C9 110.32(15) . .
C9 N1 C1 126.08(16) . .
C9 N1 H1 119(3) . .
C1 N1 H1 115(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.387(3) .
C1 C6 1.393(2) .
C1 N1 1.427(2) .
C2 C3 1.390(3) .
C2 H2 0.9500 .
C3 C4 1.389(3) .
C3 C7 1.497(3) .
C4 C5 1.385(3) .
C4 H4 0.9500 .
C5 C6 1.387(3) .
C5 C8 1.497(3) .
C6 H6 0.9500 .
C7 F1 1.319(2) .
C7 F3 1.335(2) .
C7 F2 1.337(3) .
C8 F4B 1.200(13) .
C8 F5B 1.235(16) .
C8 F4 1.319(3) .
C8 F6 1.325(3) .
C8 F5 1.330(3) .
C8 F6B 1.396(11) .
C9 N1 1.317(2) .
C9 C10 1.398(2) .
C9 C11 1.525(2) .
C10 C9 1.398(2) 2_756
C10 H10 0.9500 .
C11 F9 1.331(2) .
C11 F7 1.336(2) .
C11 F8 1.341(2) .
N1 H1 0.84(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
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.9(3) .
N1 C1 C2 C3 178.15(17) .
C1 C2 C3 C4 0.1(3) .
C1 C2 C3 C7 -179.35(18) .
C2 C3 C4 C5 -0.8(3) .
C7 C3 C4 C5 178.66(18) .
C3 C4 C5 C6 0.5(3) .
C3 C4 C5 C8 -178.64(17) .
C4 C5 C6 C1 0.5(3) .
C8 C5 C6 C1 179.64(16) .
C2 C1 C6 C5 -1.2(3) .
N1 C1 C6 C5 -178.52(16) .
C4 C3 C7 F1 169.7(2) .
C2 C3 C7 F1 -10.8(3) .
C4 C3 C7 F3 47.2(3) .
C2 C3 C7 F3 -133.3(2) .
C4 C3 C7 F2 -70.3(2) .
C2 C3 C7 F2 109.2(2) .
C4 C5 C8 F4B 130.4(12) .
C6 C5 C8 F4B -48.7(12) .
C4 C5 C8 F5B -98.8(13) .
C6 C5 C8 F5B 82.1(13) .
C4 C5 C8 F4 -51.1(3) .
C6 C5 C8 F4 129.7(2) .
C4 C5 C8 F6 70.5(3) .
C6 C5 C8 F6 -108.7(2) .
C4 C5 C8 F5 -170.76(19) .
C6 C5 C8 F5 10.1(3) .
C4 C5 C8 F6B 16.1(8) .
C6 C5 C8 F6B -163.1(8) .
N1 C9 C10 C9 0.87(13) 2_756
C11 C9 C10 C9 -177.35(16) 2_756
N1 C9 C11 F9 163.64(16) .
C10 C9 C11 F9 -18.1(2) .
N1 C9 C11 F7 42.5(2) .
C10 C9 C11 F7 -139.20(14) .
N1 C9 C11 F8 -77.1(2) .
C10 C9 C11 F8 101.21(16) .
C10 C9 N1 C1 178.77(14) .
C11 C9 N1 C1 -3.1(3) .
C2 C1 N1 C9 79.0(2) .
C6 C1 N1 C9 -103.7(2) .
