#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:16:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178556 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/64/4066433.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_4066433
loop_
_publ_author_name
'Enk, Barbara'
'Eisenstecken, Daniela'
'Kopacka, Holger'
'Wurst, Klaus'
'Müller, Thomas'
'Pevny, Florian'
'Winter, Rainer F.'
'Bildstein, Benno'
_publ_section_title
;
 Doubly N-Functionalized Pentafulvenes and Redox-Responsive [N,N]- and
 [N,C,N]-Pincer Bis(imidoyl)pentamethylruthenocene Metalloligands
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3169
_journal_paper_doi               10.1021/om100458h
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C21 H14 F6 N2'
_chemical_formula_weight         408.34
_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                90.00
_cell_angle_beta                 92.188(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0834(4)
_cell_length_b                   10.4979(2)
_cell_length_c                   14.0277(4)
_cell_measurement_reflns_used    13237
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.0
_cell_volume                     1925.28(9)
_computing_data_collection       COLLECT
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10293
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0387
_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)+(0.0475P)²+0.5858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                2838
_reflns_number_total             3383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100458h_si_002.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4066433
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
N1 N 0.00264(10) 0.37695(13) 0.65694(9) 0.0375(3) Uani 1 1 d
H1N H -0.0568(15) 0.3648(17) 0.6815(13) 0.049(5) Uiso 1 1 d
N2 N 0.36663(10) 0.18550(13) 0.31378(9) 0.0361(3) Uani 1 1 d
C1 C 0.10996(11) 0.31366(14) 0.52548(10) 0.0328(3) Uani 1 1 d
C2 C 0.13001(12) 0.22768(15) 0.44863(10) 0.0349(4) Uani 1 1 d
H2 H 0.0850 0.1645 0.4247 0.042 Uiso 1 1 calc
C3 C 0.22536(11) 0.25261(14) 0.41585(10) 0.0306(3) Uani 1 1 d
C4 C 0.26711(11) 0.35922(15) 0.47075(11) 0.0354(4) Uani 1 1 d
H4 H 0.3313 0.3970 0.4627 0.043 Uiso 1 1 calc
C5 C 0.19890(12) 0.39512(14) 0.53513(11) 0.0357(4) Uani 1 1 d
H5 H 0.2077 0.4621 0.5791 0.043 Uiso 1 1 calc
C6 C 0.02268(11) 0.31166(14) 0.57787(10) 0.0332(4) Uani 1 1 d
C7 C -0.06503(13) 0.22592(18) 0.54489(12) 0.0467(4) Uani 1 1 d
C8 C 0.07312(12) 0.45043(15) 0.71521(10) 0.0366(4) Uani 1 1 d
C9 C 0.04982(15) 0.57540(18) 0.73353(14) 0.0552(5) Uani 1 1 d
H9 H -0.0087 0.6133 0.7047 0.066 Uiso 1 1 calc
C10 C 0.1136(2) 0.6448(2) 0.79492(18) 0.0756(7) Uani 1 1 d
H10 H 0.0981 0.7304 0.8078 0.091 Uiso 1 1 calc
C11 C 0.1983(2) 0.5906(3) 0.83684(15) 0.0734(7) Uani 1 1 d
H11 H 0.2412 0.6387 0.8783 0.088 Uiso 1 1 calc
C12 C 0.22111(16) 0.4655(2) 0.81853(14) 0.0637(6) Uani 1 1 d
H12 H 0.2798 0.4283 0.8475 0.076 Uiso 1 1 calc
C13 C 0.15835(14) 0.39393(17) 0.75778(12) 0.0474(4) Uani 1 1 d
H13 H 0.1736 0.3081 0.7457 0.057 Uiso 1 1 calc
C14 C 0.27346(11) 0.18746(14) 0.33726(10) 0.0320(3) Uani 1 1 d
C15 C 0.20381(13) 0.11024(17) 0.27048(11) 0.0436(4) Uani 1 1 d
C16 C 0.44661(11) 0.23941(15) 0.37211(11) 0.0351(4) Uani 1 1 d
C17 C 0.49844(13) 0.34526(16) 0.34130(12) 0.0430(4) Uani 1 1 d
H17 H 0.4775 0.3858 0.2841 0.052 Uiso 1 1 calc
C18 C 0.58107(14) 0.39135(18) 0.39478(15) 0.0540(5) Uani 1 1 d
H18 H 0.6150 0.4650 0.3748 0.065 Uiso 1 1 calc
C19 C 0.61410(15) 0.3306(2) 0.47686(15) 0.0591(5) Uani 1 1 d
H19 H 0.6712 0.3615 0.5124 0.071 Uiso 1 1 calc
C20 C 0.56317(16) 0.2245(2) 0.50681(14) 0.0583(5) Uani 1 1 d
H20 H 0.5858 0.1826 0.5630 0.070 Uiso 1 1 calc
C21 C 0.47906(14) 0.17862(17) 0.45519(12) 0.0477(4) Uani 1 1 d
H21 H 0.4441 0.1064 0.4765 0.057 Uiso 1 1 calc
F1 F -0.09361(9) 0.24716(15) 0.45454(8) 0.0840(5) Uani 1 1 d
F2 F -0.03926(9) 0.10437(11) 0.55169(10) 0.0779(4) Uani 1 1 d
F3 F -0.14794(7) 0.24029(11) 0.59551(8) 0.0595(3) Uani 1 1 d
F4 F 0.12457(10) 0.17610(15) 0.23628(9) 0.0885(5) Uani 1 1 d
F5 F 0.16516(12) 0.01090(13) 0.31530(9) 0.0865(5) Uani 1 1 d
F6 F 0.25020(8) 0.06382(12) 0.19616(7) 0.0636(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1N N1 C6 117.3(12)
H1N N1 C8 114.7(12)
C6 N1 C8 127.29(13)
C14 N2 C16 122.35(12)
C6 C1 C2 124.58(14)
C6 C1 C5 129.61(14)
C2 C1 C5 105.79(13)
C3 C2 C1 109.03(13)
C2 C3 C4 107.31(12)
C2 C3 C14 125.99(13)
C4 C3 C14 126.64(13)
C5 C4 C3 108.99(13)
C4 C5 C1 108.84(13)
N1 C6 C1 128.70(14)
N1 C6 C7 112.75(13)
C1 C6 C7 118.55(13)
F2 C7 F1 107.03(15)
F2 C7 F3 106.40(14)
F1 C7 F3 106.60(15)
F2 C7 C6 111.28(15)
F1 C7 C6 111.97(14)
F3 C7 C6 113.18(13)
C9 C8 C13 120.77(16)
C9 C8 N1 118.56(16)
C13 C8 N1 120.49(14)
C8 C9 C10 119.1(2)
C11 C10 C9 120.7(2)
C10 C11 C12 119.93(19)
C11 C12 C13 120.5(2)
C8 C13 C12 118.99(18)
N2 C14 C3 130.28(14)
N2 C14 C15 112.93(13)
C3 C14 C15 116.78(13)
F6 C15 F4 106.54(14)
F6 C15 F5 106.21(15)
F4 C15 F5 105.98(15)
F6 C15 C14 113.69(13)
F4 C15 C14 112.90(15)
F5 C15 C14 110.98(13)
C17 C16 C21 119.83(15)
C17 C16 N2 120.02(14)
C21 C16 N2 119.85(14)
C16 C17 C18 119.77(16)
C19 C18 C17 120.58(17)
C18 C19 C20 119.55(17)
C19 C20 C21 120.62(18)
C20 C21 C16 119.63(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 H1N 0.87(2)
N1 C6 1.3383(19)
N1 C8 1.434(2)
N2 C14 1.2751(19)
N2 C16 1.4210(19)
C1 C6 1.381(2)
C1 C2 1.438(2)
C1 C5 1.446(2)
C2 C3 1.371(2)
C3 C4 1.453(2)
C3 C14 1.460(2)
C4 C5 1.347(2)
C6 C7 1.517(2)
C7 F2 1.322(2)
C7 F1 1.327(2)
C7 F3 1.3276(19)
C8 C9 1.373(2)
C8 C13 1.379(2)
C9 C10 1.383(3)
C10 C11 1.360(4)
C11 C12 1.373(3)
C12 C13 1.383(3)
C14 C15 1.517(2)
C15 F6 1.3195(18)
C15 F4 1.321(2)
C15 F5 1.328(2)
C16 C17 1.380(2)
C16 C21 1.381(2)
C17 C18 1.380(2)
C18 C19 1.371(3)
C19 C20 1.372(3)
C20 C21 1.381(3)
