#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:57:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180162 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/58/7105809.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_7105809
loop_
_publ_author_name
'Manuel Alcarazo'
'Karin Radkowski'
'Richard Goddard'
'Alois Furstner'
_publ_section_title
;
 Metal complexes with carbene ligands stabilized by lateral enamines
;
_journal_name_full               Chem.Commun.
_journal_page_first              776
_journal_paper_doi               10.1039/c0cc03128c
_journal_volume                  47
_journal_year                    2011
_chemical_compound_source        acetonitrile/diethylether
_chemical_formula_moiety         'C11 H18 Cl N2 1+, B F4 1-'
_chemical_formula_sum            'C11 H18 B Cl F4 N2'
_chemical_formula_weight         300.53
_chemical_name_systematic
;
1-chloro-2-(dimethyl-amino-methylidenyl)-cyclopent-5-en-5-yl-
methylidenyl-dimethylammonium tetrafluoroborate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                AVM-AB-172-01
_audit_creation_date             2010-07-28
_cell_angle_alpha                106.620(2)
_cell_angle_beta                 91.767(2)
_cell_angle_gamma                102.890(2)
_cell_formula_units_Z            4
_cell_length_a                   7.6530(7)
_cell_length_b                   12.1577(11)
_cell_length_c                   16.2528(14)
_cell_measurement_reflns_used    40482
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.62
_cell_volume                     1405.2(2)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40280
_diffrn_reflns_theta_full        30.70
_diffrn_reflns_theta_max         30.70
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Bruker AXS (2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.242
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.772
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         8635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.772
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0845
_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)+(0.0724P)²+0.4124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2333
_refine_ls_wR_factor_ref         0.2497
_reflns_number_gt                6051
_reflns_number_total             8635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03128C.TXT
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105809
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.9955(3) 0.5033(2) 0.25394(16) 0.0287(5) Uani 1 1 d . . .
C2 C 0.9032(4) 0.4168(2) 0.28806(17) 0.0314(5) Uani 1 1 d . . .
C3 C 0.9556(4) 0.4606(3) 0.38521(18) 0.0381(6) Uani 1 1 d . . .
H3A H 1.0212 0.4082 0.4030 0.046 Uiso 1 1 calc R . .
H3B H 0.8472 0.4629 0.4168 0.046 Uiso 1 1 calc R . .
C4 C 1.0771(4) 0.5854(3) 0.40334(17) 0.0358(6) Uani 1 1 d . . .
H4A H 1.0198 0.6451 0.4395 0.043 Uiso 1 1 calc R . .
H4B H 1.1950 0.5916 0.4335 0.043 Uiso 1 1 calc R . .
C5 C 1.1010(3) 0.6036(2) 0.31517(16) 0.0297(5) Uani 1 1 d . . .
C6 C 0.7849(4) 0.3149(2) 0.23622(19) 0.0344(6) Uani 1 1 d . . .
H6 H 0.7730 0.3084 0.1765 0.041 Uiso 1 1 calc R . .
C7 C 0.5669(5) 0.1264(3) 0.1919(3) 0.0534(9) Uani 1 1 d . . .
H7A H 0.5697 0.1433 0.1364 0.080 Uiso 1 1 calc R . .
H7B H 0.4435 0.1158 0.2083 0.080 Uiso 1 1 calc R . .
H7C H 0.6076 0.0541 0.1867 0.080 Uiso 1 1 calc R . .
C8 C 0.6853(6) 0.2152(4) 0.3454(3) 0.0629(11) Uani 1 1 d . . .
H8A H 0.8060 0.2511 0.3761 0.094 Uiso 1 1 calc R . .
H8B H 0.6507 0.1315 0.3426 0.094 Uiso 1 1 calc R . .
H8C H 0.5989 0.2562 0.3761 0.094 Uiso 1 1 calc R . .
C9 C 1.1991(3) 0.6982(2) 0.29195(17) 0.0311(5) Uani 1 1 d . . .
H9 H 1.1912 0.6885 0.2317 0.037 Uiso 1 1 calc R . .
C10 C 1.3374(5) 0.8346(3) 0.4346(2) 0.0552(9) Uani 1 1 d . . .
H10A H 1.2309 0.7995 0.4587 0.083 Uiso 1 1 calc R . .
H10B H 1.3642 0.9210 0.4580 0.083 Uiso 1 1 calc R . .
H10C H 1.4406 0.8065 0.4500 0.083 Uiso 1 1 calc R . .
C11 C 1.3918(4) 0.8881(3) 0.3012(2) 0.0446(7) Uani 1 1 d . . .
H11A H 1.3690 0.8558 0.2382 0.067 Uiso 1 1 calc R . .
H11B H 1.5218 0.9089 0.3182 0.067 Uiso 1 1 calc R . .
H11C H 1.3449 0.9590 0.3207 0.067 Uiso 1 1 calc R . .
N1 N 0.6859(3) 0.2253(2) 0.25793(17) 0.0400(6) Uani 1 1 d . . .
N2 N 1.3024(3) 0.8002(2) 0.34048(16) 0.0372(5) Uani 1 1 d . . .
Cl1 Cl 0.97970(10) 0.48787(6) 0.14534(4) 0.03709(19) Uani 1 1 d . . .
C21 C 0.5005(4) 0.5087(3) 0.24715(17) 0.0346(6) Uani 1 1 d . . .
C22 C 0.4080(4) 0.4226(3) 0.17402(18) 0.0385(6) Uani 1 1 d . . .
C23 C 0.4578(4) 0.4661(3) 0.09680(19) 0.0447(7) Uani 1 1 d . . .
H23A H 0.3484 0.4668 0.0630 0.054 Uiso 1 1 calc R . .
H23B H 0.5248 0.4146 0.0586 0.054 Uiso 1 1 calc R . .
C24 C 0.5764(5) 0.5916(3) 0.13501(19) 0.0443(7) Uani 1 1 d . . .
H24A H 0.6931 0.5994 0.1099 0.053 Uiso 1 1 calc R . .
H24B H 0.5156 0.6503 0.1234 0.053 Uiso 1 1 calc R . .
C25 C 0.6050(4) 0.6104(3) 0.23145(18) 0.0369(6) Uani 1 1 d . . .
C26 C 0.2890(4) 0.3201(3) 0.17876(19) 0.0392(6) Uani 1 1 d . . .
H26 H 0.2750 0.3149 0.2355 0.047 Uiso 1 1 calc R . .
C27 C 0.0669(5) 0.1341(3) 0.1372(3) 0.0542(8) Uani 1 1 d . . .
H27A H 0.0601 0.1550 0.1997 0.081 Uiso 1 1 calc R . .
H27B H 0.1085 0.0611 0.1178 0.081 Uiso 1 1 calc R . .
H27C H -0.0526 0.1221 0.1078 0.081 Uiso 1 1 calc R . .
C28 C 0.2015(6) 0.2130(4) 0.0244(2) 0.0740(13) Uani 1 1 d . . .
H28A H 0.1115 0.2473 0.0033 0.111 Uiso 1 1 calc R . .
H28B H 0.1766 0.1283 -0.0066 0.111 Uiso 1 1 calc R . .
H28C H 0.3219 0.2523 0.0144 0.111 Uiso 1 1 calc R . .
C29 C 0.7049(4) 0.7042(3) 0.2972(2) 0.0396(6) Uani 1 1 d . . .
H29 H 0.6972 0.6951 0.3532 0.048 Uiso 1 1 calc R . .
C30 C 0.8499(5) 0.8365(4) 0.2155(3) 0.0606(10) Uani 1 1 d . . .
H30A H 0.9246 0.7867 0.1831 0.091 Uiso 1 1 calc R . .
H30B H 0.9150 0.9198 0.2305 0.091 Uiso 1 1 calc R . .
H30C H 0.7371 0.8239 0.1801 0.091 Uiso 1 1 calc R . .
C31 C 0.8959(5) 0.8958(4) 0.3738(3) 0.0568(9) Uani 1 1 d . . .
H31A H 0.8775 0.8638 0.4227 0.085 Uiso 1 1 calc R . .
H31B H 0.8428 0.9641 0.3829 0.085 Uiso 1 1 calc R . .
H31C H 1.0253 0.9205 0.3693 0.085 Uiso 1 1 calc R . .
N3 N 0.1933(4) 0.2297(3) 0.11691(18) 0.0460(6) Uani 1 1 d . . .
N4 N 0.8098(4) 0.8051(3) 0.29456(18) 0.0440(6) Uani 1 1 d . . .
Cl2 Cl 0.48695(11) 0.49393(7) 0.34883(4) 0.0434(2) Uani 1 1 d . . .
B1 B 0.2985(5) 0.8092(4) 0.0550(2) 0.0440(8) Uani 1 1 d . . .
B2 B 0.7890(6) 0.7957(4) 0.5786(2) 0.0462(8) Uani 1 1 d . . .
F1A F 0.4782(9) 0.8517(6) 0.0970(4) 0.0492(16) Uiso 0.50 1 d P A 1
F2A F 0.2069(8) 0.7012(6) 0.0690(4) 0.0736(15) Uiso 0.50 1 d P A 1
F3A F 0.2705(7) 0.7955(5) -0.0298(4) 0.0718(14) Uiso 0.50 1 d P A 1
F4A F 0.2137(7) 0.8934(5) 0.0997(4) 0.0728(13) Uiso 0.50 1 d P A 1
F5A F 0.9531(9) 0.8092(6) 0.5440(5) 0.0629(18) Uiso 0.50 1 d P B 2
F6A F 0.7715(11) 0.7875(7) 0.6597(5) 0.089(2) Uiso 0.50 1 d P B 2
F7A F 0.7202(8) 0.8895(6) 0.5675(4) 0.0570(15) Uiso 0.50 1 d P B 2
F8A F 0.7169(11) 0.6764(7) 0.5379(6) 0.094(2) Uiso 0.50 1 d P B 2
F1B F 0.4649(11) 0.8252(7) 0.0923(5) 0.067(2) Uiso 0.50 1 d P A 3
F2B F 0.1818(10) 0.7552(7) 0.0947(5) 0.102(2) Uiso 0.50 1 d P A 3
F3B F 0.3256(8) 0.7519(5) -0.0304(4) 0.0746(14) Uiso 0.50 1 d P A 3
F4B F 0.2566(10) 0.9119(7) 0.0492(5) 0.105(2) Uiso 0.50 1 d P A 3
F5B F 0.9690(11) 0.8163(7) 0.5665(5) 0.077(2) Uiso 0.50 1 d P B 4
F6B F 0.8028(11) 0.8308(8) 0.6660(5) 0.094(2) Uiso 0.50 1 d P B 4
F7B F 0.6964(10) 0.8610(7) 0.5484(5) 0.077(2) Uiso 0.50 1 d P B 4
F8B F 0.6698(12) 0.6952(8) 0.5260(6) 0.107(3) Uiso 0.50 1 d P B 4
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'
B B 0.0013 0.0007 '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'
Cl Cl 0.1484 0.1585 '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 C1 C5 114.5(2) . . y
C2 C1 Cl1 122.7(2) . . y
C5 C1 Cl1 122.8(2) . . y
C6 C2 C1 121.5(2) . . y
C6 C2 C3 131.2(2) . . y
C1 C2 C3 107.2(2) . . y
C2 C3 C4 105.4(2) . . y
C5 C4 C3 105.4(2) . . y
C9 C5 C1 121.7(2) . . y
C9 C5 C4 131.0(2) . . y
C1 C5 C4 107.3(2) . . y
N1 C6 C2 129.3(3) . . y
N2 C9 C5 130.1(3) . . y
C6 N1 C8 124.8(3) . . y
C6 N1 C7 120.0(3) . . y
C8 N1 C7 115.2(3) . . y
C9 N2 C11 120.3(2) . . y
C9 N2 C10 124.9(2) . . y
C11 N2 C10 114.8(3) . . y
C22 C21 C25 114.5(3) . . y
C22 C21 Cl2 122.8(2) . . y
C25 C21 Cl2 122.7(2) . . y
C21 C22 C26 121.8(3) . . y
C21 C22 C23 107.4(3) . . y
C26 C22 C23 130.7(3) . . y
C22 C23 C24 105.4(2) . . y
C25 C24 C23 105.6(2) . . y
C29 C25 C21 121.8(3) . . y
C29 C25 C24 131.4(3) . . y
C21 C25 C24 106.8(3) . . y
N3 C26 C22 129.9(3) . . y
N4 C29 C25 130.0(3) . . y
C26 N3 C27 120.6(3) . . y
C26 N3 C28 125.3(3) . . y
C27 N3 C28 114.2(3) . . y
C29 N4 C31 120.6(3) . . y
C29 N4 C30 124.9(3) . . y
C31 N4 C30 114.5(3) . . y
F2B B1 F1B 109.5(5) . . y
F2B B1 F3A 121.9(5) . . y
F1B B1 F3A 120.7(5) . . y
F2B B1 F4A 74.8(5) . . y
F1B B1 F4A 111.7(5) . . y
F3A B1 F4A 108.6(4) . . y
F2B B1 F4B 110.9(6) . . y
F1B B1 F4B 114.3(5) . . y
F3A B1 F4B 74.0(5) . . y
F2B B1 F3B 120.0(5) . . y
F1B B1 F3B 98.4(5) . . y
F4A B1 F3B 140.0(4) . . y
F4B B1 F3B 103.3(5) . . y
F1B B1 F2A 101.7(5) . . y
F3A B1 F2A 107.3(4) . . y
F4A B1 F2A 105.6(4) . . y
F4B B1 F2A 137.3(5) . . y
F3B B1 F2A 92.9(4) . . y
F2B B1 F1A 115.6(5) . . y
F3A B1 F1A 119.5(4) . . y
F4A B1 F1A 102.6(4) . . y
F4B B1 F1A 102.4(5) . . y
F3B B1 F1A 102.5(4) . . y
F2A B1 F1A 112.3(4) . . y
F7B B2 F6B 109.6(6) . . y
F7B B2 F6A 119.7(5) . . y
F7B B2 F5B 115.1(6) . . y
F6B B2 F5B 99.3(5) . . y
F6A B2 F5B 108.4(5) . . y
F7B B2 F8B 88.3(5) . . y
F6B B2 F8B 125.0(6) . . y
F6A B2 F8B 104.6(6) . . y
F5B B2 F8B 119.8(6) . . y
F7B B2 F8A 110.1(6) . . y
F6B B2 F8A 116.4(6) . . y
F6A B2 F8A 95.0(6) . . y
F5B B2 F8A 106.0(6) . . y
F7B B2 F5A 106.1(5) . . y
F6B B2 F5A 114.2(5) . . y
F6A B2 F5A 123.0(5) . . y
F8B B2 F5A 109.1(5) . . y
F8A B2 F5A 99.6(5) . . y
F6B B2 F7A 96.6(5) . . y
F6A B2 F7A 110.5(5) . . y
F5B B2 F7A 109.4(5) . . y
F8B B2 F7A 104.0(5) . . y
F8A B2 F7A 125.9(5) . . y
F5A B2 F7A 104.3(5) . . y
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
C1 C2 1.392(4) . y
C1 C5 1.395(4) . y
C1 Cl1 1.718(3) . y
C2 C6 1.386(4) . y
C2 C3 1.524(4) . y
C3 C4 1.533(4) . y
C4 C5 1.522(3) . y
C5 C9 1.382(4) . y
C6 N1 1.324(4) . y
C7 N1 1.463(4) . y
C8 N1 1.461(4) . y
C9 N2 1.322(4) . y
C10 N2 1.464(4) . y
C11 N2 1.453(4) . y
C21 C22 1.384(4) . y
C21 C25 1.408(4) . y
C21 Cl2 1.717(3) . y
C22 C26 1.394(5) . y
C22 C23 1.523(4) . y
C23 C24 1.531(5) . y
C24 C25 1.520(4) . y
C25 C29 1.375(4) . y
C26 N3 1.311(4) . y
C27 N3 1.460(5) . y
C28 N3 1.464(5) . y
C29 N4 1.320(4) . y
C30 N4 1.464(4) . y
C31 N4 1.456(5) . y
B1 F2B 1.289(8) . y
B1 F1B 1.342(9) . y
B1 F3A 1.343(6) . y
B1 F4A 1.378(7) . y
B1 F4B 1.384(8) . y
B1 F3B 1.407(7) . y
B1 F2A 1.427(7) . y
B1 F1A 1.431(7) . y
B2 F7B 1.352(9) . y
B2 F6B 1.355(9) . y
B2 F6A 1.358(9) . y
B2 F5B 1.375(9) . y
B2 F8B 1.383(10) . y
B2 F8A 1.384(9) . y
B2 F5A 1.388(8) . y
B2 F7A 1.410(8) . y
