#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:01:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178416 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023790.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_4023790
loop_
_publ_author_name
'Yajun Ma'
'Siping Wei'
'Jingbo Lan'
'Jingzhi Wang'
'Rugang Xie'
'Jingsong You'
_publ_section_title
;
 Pyrido[1,2-a][1,2,4]triazol-3-ylidenes as a New Family of Stable
 Annulated N-Heterocyclic Carbenes: Synthesis, Reactivity, and Their
 Application in Coordination Chemistry and Organocatalysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8256
_journal_page_last               8264
_journal_paper_doi               10.1021/jo801349d
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         C8H10BF4N3
_chemical_formula_sum            'C8 H10 B F4 N3'
_chemical_formula_weight         234.99
_chemical_name_common
;
2-ethyl-pyrido[1,2-a][1,2,4]-triazol-2-ium hexafluorophosphate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.08(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.439(3)
_cell_length_b                   7.1401(16)
_cell_length_c                   13.216(4)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      9.69
_cell_measurement_theta_min      4.60
_cell_volume                     1031.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       Omega\2-Theta
_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  0.0080
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2068
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        5.029
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                895
_reflns_number_total             1887
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801349d_si_001.cif
_cod_data_source_block           cd12b
_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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023790
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B B 0.6684(3) 0.6802(7) 0.2805(3) 0.0500(10) Uani 1 d . . .
F1 F 0.56120(18) 0.5806(3) 0.25663(18) 0.0751(7) Uani 1 d . . .
F2 F 0.6634(2) 0.8085(4) 0.20104(19) 0.0836(8) Uani 1 d . . .
F3 F 0.76642(18) 0.5623(3) 0.29054(18) 0.0739(7) Uani 1 d . . .
F4 F 0.6851(2) 0.7738(4) 0.37506(18) 0.0846(8) Uani 1 d . . .
N1 N 0.8358(2) 0.3404(4) -0.1395(2) 0.0430(7) Uani 1 d . . .
N2 N 0.8357(2) 0.1877(4) 0.0076(2) 0.0532(8) Uani 1 d . . .
N3 N 0.7202(2) 0.2319(4) -0.0533(2) 0.0490(7) Uani 1 d . . .
C1 C 0.9061(3) 0.2550(5) -0.0470(3) 0.0451(8) Uani 1 d . . .
C2 C 1.0346(3) 0.2520(6) -0.0266(3) 0.0583(10) Uani 1 d . . .
C3 C 1.0839(4) 0.3272(6) -0.0968(3) 0.0619(11) Uani 1 d . . .
C4 C 1.0089(4) 0.4130(6) -0.1909(3) 0.0634(11) Uani 1 d . . .
C5 C 0.8871(3) 0.4194(6) -0.2116(3) 0.0555(10) Uani 1 d . . .
C6 C 0.7199(3) 0.3212(5) -0.1391(3) 0.0475(9) Uani 1 d . . .
C7 C 0.6155(4) 0.1794(8) -0.0158(4) 0.0670(12) Uani 1 d . . .
C8 C 0.6083(5) 0.3022(10) 0.0712(4) 0.0898(18) Uani 1 d . . .
H2 H 1.082(3) 0.203(4) 0.033(3) 0.042(9) Uiso 1 d . . .
H3 H 1.170(4) 0.320(5) -0.085(3) 0.072(11) Uiso 1 d . . .
H4 H 1.050(3) 0.466(6) -0.247(3) 0.069(11) Uiso 1 d . . .
H5 H 0.832(3) 0.469(6) -0.269(3) 0.068(12) Uiso 1 d . . .
H6 H 0.660(3) 0.356(4) -0.191(2) 0.031(8) Uiso 1 d . . .
H71 H 0.631(4) 0.040(7) 0.007(3) 0.085(14) Uiso 1 d . . .
H72 H 0.552(3) 0.195(5) -0.075(3) 0.065(11) Uiso 1 d . . .
H81 H 0.537(4) 0.287(6) 0.098(3) 0.093(14) Uiso 1 d . . .
H82 H 0.682(5) 0.300(7) 0.140(4) 0.114(17) Uiso 1 d . . .
H83 H 0.587(5) 0.428(8) 0.045(4) 0.12(2) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B F3 110.6(4) . . ?
F1 B F4 109.6(3) . . ?
F3 B F4 108.5(3) . . ?
F1 B F2 109.5(3) . . ?
F3 B F2 109.2(3) . . ?
F4 B F2 109.4(4) . . ?
C6 N1 C5 132.1(3) . . ?
C6 N1 C1 105.6(3) . . ?
C5 N1 C1 122.3(3) . . ?
C1 N2 N3 103.5(3) . . ?
C6 N3 N2 112.4(3) . . ?
C6 N3 C7 128.6(3) . . ?
N2 N3 C7 119.0(3) . . ?
N2 C1 N1 110.7(3) . . ?
N2 C1 C2 131.0(3) . . ?
N1 C1 C2 118.3(3) . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 121(2) . . ?
C1 C2 H2 120(2) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 120(2) . . ?
C4 C3 H3 119(2) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 120(2) . . ?
C3 C4 H4 119(2) . . ?
C4 C5 N1 118.3(4) . . ?
C4 C5 H5 127(2) . . ?
N1 C5 H5 114(2) . . ?
N3 C6 N1 107.8(3) . . ?
N3 C6 H6 129.6(19) . . ?
N1 C6 H6 122.4(19) . . ?
C8 C7 N3 110.5(4) . . ?
C8 C7 H71 113(2) . . ?
N3 C7 H71 105(2) . . ?
C8 C7 H72 113(2) . . ?
N3 C7 H72 102(2) . . ?
H71 C7 H72 113(3) . . ?
C7 C8 H81 117(3) . . ?
C7 C8 H82 117(3) . . ?
H81 C8 H82 104(3) . . ?
C7 C8 H83 110(3) . . ?
H81 C8 H83 95(4) . . ?
H82 C8 H83 112(4) . . ?
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
B F1 1.372(4) . ?
B F3 1.377(5) . ?
B F4 1.380(5) . ?
B F2 1.382(5) . ?
N1 C6 1.335(4) . ?
N1 C5 1.378(4) . ?
N1 C1 1.391(4) . ?
N2 C1 1.319(4) . ?
N2 N3 1.367(4) . ?
N3 C6 1.300(4) . ?
N3 C7 1.472(5) . ?
C1 C2 1.415(5) . ?
C2 C3 1.331(5) . ?
C2 H2 0.89(3) . ?
C3 C4 1.426(6) . ?
C3 H3 0.96(4) . ?
C4 C5 1.340(5) . ?
C4 H4 1.06(4) . ?
C5 H5 0.90(4) . ?
C6 H6 0.85(3) . ?
C7 C8 1.468(7) . ?
C7 H71 1.04(4) . ?
C7 H72 0.91(4) . ?
C8 H81 0.99(5) . ?
C8 H82 1.04(5) . ?
C8 H83 0.97(5) . ?
