#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:39:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178575 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/85/4068555.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_4068555
loop_
_publ_author_name
'O, Wylie W. N.'
'Lough, Alan J.'
'Morris, Robert H.'
_publ_section_title
;
 Synthesis and Characterization of Nitrile-Functionalized N-Heterocyclic
 Carbenes and Their Complexes of Silver(I) and Rhodium(I)
;
_journal_issue                   3
_journal_name_full               Organometallics
_journal_page_first              853
_journal_paper_doi               10.1021/om8009377
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C11 H10 N3, B F4'
_chemical_formula_sum            'C11 H10 B F4 N3'
_chemical_formula_weight         271.03
_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                 111.308(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8385(5)
_cell_length_b                   10.2371(6)
_cell_length_c                   9.7995(6)
_cell_measurement_reflns_used    8249
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1199.90(11)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0883
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8249
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.001
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0532
_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)+(0.0779P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                1355
_reflns_number_total             2739
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om8009377_si_001.cif
_cod_data_source_block           m-CN-BF4
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4068555
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
N1 N 0.27941(16) 0.5046(2) 0.1965(2) 0.0269(5) Uani 1 1 d .
N2 N 0.41934(16) 0.6011(2) 0.1674(2) 0.0280(5) Uani 1 1 d .
N3 N 0.30551(19) 0.2234(2) 0.0040(2) 0.0418(6) Uani 1 1 d .
C1 C 0.3211(2) 0.5460(3) 0.0971(3) 0.0293(6) Uani 1 1 d .
H1A H 0.2862 0.5374 -0.0062 0.035 Uiso 1 1 calc R
C2 C 0.3537(2) 0.5366(3) 0.3345(3) 0.0301(6) Uani 1 1 d .
H2A H 0.3447 0.5200 0.4250 0.036 Uiso 1 1 calc R
C3 C 0.4410(2) 0.5957(3) 0.3162(3) 0.0304(6) Uani 1 1 d .
H3A H 0.5058 0.6280 0.3917 0.037 Uiso 1 1 calc R
C4 C 0.4916(2) 0.6626(3) 0.0996(3) 0.0380(7) Uani 1 1 d .
H4A H 0.4608 0.6473 -0.0064 0.057 Uiso 1 1 calc R
H4B H 0.5668 0.6248 0.1410 0.057 Uiso 1 1 calc R
H4C H 0.4956 0.7567 0.1187 0.057 Uiso 1 1 calc R
C5 C 0.17381(19) 0.4383(3) 0.1653(3) 0.0268(6) Uani 1 1 d .
C6 C 0.15370(19) 0.3202(3) 0.0896(3) 0.0295(6) Uani 1 1 d .
C7 C 0.0517(2) 0.2570(3) 0.0621(3) 0.0346(7) Uani 1 1 d .
H7A H 0.0361 0.1767 0.0100 0.041 Uiso 1 1 calc R
C8 C -0.0268(2) 0.3122(3) 0.1113(3) 0.0369(7) Uani 1 1 d .
H8A H -0.0963 0.2696 0.0927 0.044 Uiso 1 1 calc R
C9 C -0.0045(2) 0.4292(3) 0.1874(3) 0.0360(7) Uani 1 1 d .
H9A H -0.0585 0.4658 0.2216 0.043 Uiso 1 1 calc R
C10 C 0.0959(2) 0.4933(3) 0.2141(3) 0.0324(6) Uani 1 1 d .
H10A H 0.1109 0.5741 0.2653 0.039 Uiso 1 1 calc R
C11 C 0.2379(2) 0.2637(3) 0.0420(3) 0.0316(6) Uani 1 1 d .
F1 F 0.24813(13) 1.02140(16) 0.26836(16) 0.0453(5) Uani 1 1 d .
F2 F 0.22830(14) 0.80266(17) 0.24377(19) 0.0559(5) Uani 1 1 d .
F3 F 0.18440(18) 0.9327(2) 0.04415(18) 0.0763(7) Uani 1 1 d .
F4 F 0.36517(14) 0.90611(18) 0.1903(2) 0.0705(6) Uani 1 1 d .
B1 B 0.2559(3) 0.9143(3) 0.1854(3) 0.0346(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
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'
B B 0.0013 0.0007 '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
C1 N1 C2 108.7(2)
C1 N1 C5 125.9(2)
C2 N1 C5 125.41(18)
C1 N2 C3 108.7(2)
C1 N2 C4 126.0(2)
C3 N2 C4 125.3(2)
N2 C1 N1 108.2(2)
C3 C2 N1 106.8(2)
C2 C3 N2 107.6(2)
C10 C5 C6 121.5(2)
C10 C5 N1 118.6(2)
C6 C5 N1 119.9(2)
C5 C6 C7 119.0(2)
C5 C6 C11 120.2(2)
C7 C6 C11 120.7(2)
C8 C7 C6 119.5(3)
C9 C8 C7 120.4(2)
C10 C9 C8 120.5(2)
C5 C10 C9 119.0(3)
N3 C11 C6 177.7(3)
F3 B1 F2 110.8(2)
F3 B1 F4 110.0(2)
F2 B1 F4 110.1(3)
F3 B1 F1 108.5(3)
F2 B1 F1 109.0(2)
F4 B1 F1 108.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.340(3)
N1 C2 1.382(3)
N1 C5 1.446(3)
N2 C1 1.324(3)
N2 C3 1.383(3)
N2 C4 1.465(3)
N3 C11 1.139(3)
C2 C3 1.342(3)
C5 C10 1.376(3)
C5 C6 1.392(4)
C6 C7 1.397(3)
C6 C11 1.445(3)
C7 C8 1.385(3)
C8 C9 1.385(4)
C9 C10 1.384(4)
F1 B1 1.391(3)
F2 B1 1.381(3)
F3 B1 1.368(4)
F4 B1 1.388(3)
