#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:57:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180162 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/58/7105802.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_7105802
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_absolute_configuration unk
_chemical_compound_source        dichloromethane/diethylether
_chemical_formula_moiety         'C15 H18 Cl N2 1+, B F4 1-'
_chemical_formula_sum            'C15 H18 B Cl F4 N2'
_chemical_formula_weight         348.57
_chemical_name_systematic
;
2-chloro-3-(dimethylamino-methylidenyl)-ind-1-en-1-yl-methylidenyl-
dimethylammoniumium tetrafluoroborate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                RKI-RE-185-03
_audit_creation_date             2009-02-06
_cell_angle_alpha                90.00
_cell_angle_beta                 96.479(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1625(5)
_cell_length_b                   17.6971(7)
_cell_length_c                   7.3078(3)
_cell_measurement_reflns_used    130950
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      2.91
_cell_volume                     1562.89(11)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_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 18.18
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23107
_diffrn_reflns_theta_full        33.90
_diffrn_reflns_theta_max         33.90
_diffrn_reflns_theta_min         3.31
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Bruker AXS (2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.326
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         5992
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0344
_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)+(0.0626P)²+0.0229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                5742
_reflns_number_total             5992
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            C0CC03128C.TXT
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (33
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (36
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (23
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (18 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7105802
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'
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 -0.04111(8) 0.54972(6) 0.60445(13) 0.01600(16) Uani 1 1 d . . .
C2 C 0.00904(7) 0.47914(6) 0.65371(13) 0.01610(16) Uani 1 1 d . . .
C3 C -0.07544(8) 0.42214(6) 0.59249(14) 0.01673(16) Uani 1 1 d . . .
C4 C -0.07901(10) 0.34336(6) 0.61459(16) 0.02110(18) Uani 1 1 d . . .
H4 H -0.0208 0.3184 0.6826 0.025 Uiso 1 1 calc R . .
C5 C -0.17016(10) 0.30276(7) 0.53418(17) 0.0244(2) Uani 1 1 d . . .
H5 H -0.1721 0.2505 0.5475 0.029 Uiso 1 1 calc R . .
C6 C -0.25858(10) 0.33996(7) 0.43383(17) 0.0252(2) Uani 1 1 d . . .
H6 H -0.3173 0.3121 0.3758 0.030 Uiso 1 1 calc R . .
C7 C -0.25948(9) 0.41842(7) 0.41998(15) 0.02071(19) Uani 1 1 d . . .
H7 H -0.3192 0.4428 0.3545 0.025 Uiso 1 1 calc R . .
C8 C -0.17036(8) 0.46064(6) 0.50463(13) 0.01673(16) Uani 1 1 d . . .
C9 C -0.14978(8) 0.54223(6) 0.51693(13) 0.01654(16) Uani 1 1 d . . .
C10 C 0.11715(8) 0.47919(6) 0.74703(14) 0.01796(17) Uani 1 1 d . . .
H10 H 0.1398 0.5257 0.7968 0.022 Uiso 1 1 calc R . .
C11 C 0.29559(11) 0.44004(8) 0.8937(2) 0.0302(3) Uani 1 1 d . . .
H11A H 0.2996 0.4083 1.0008 0.045 Uiso 1 1 calc R . .
H11B H 0.2981 0.4921 0.9310 0.045 Uiso 1 1 calc R . .
H11C H 0.3570 0.4293 0.8261 0.045 Uiso 1 1 calc R . .
C12 C 0.18213(11) 0.34984(7) 0.6964(2) 0.0278(2) Uani 1 1 d . . .
H12A H 0.1356 0.3516 0.5813 0.042 Uiso 1 1 calc R . .
H12B H 0.1503 0.3163 0.7793 0.042 Uiso 1 1 calc R . .
H12C H 0.2542 0.3318 0.6761 0.042 Uiso 1 1 calc R . .
C13 C -0.21108(8) 0.60878(6) 0.46600(14) 0.01788(17) Uani 1 1 d . . .
H13 H -0.1680 0.6517 0.4571 0.021 Uiso 1 1 calc R . .
C14 C -0.36031(10) 0.69508(7) 0.37034(18) 0.0267(2) Uani 1 1 d . . .
H14A H -0.2993 0.7284 0.3575 0.040 Uiso 1 1 calc R . .
H14B H -0.4039 0.7151 0.4607 0.040 Uiso 1 1 calc R . .
H14C H -0.4054 0.6907 0.2542 0.040 Uiso 1 1 calc R . .
C15 C -0.40465(9) 0.56494(7) 0.45517(17) 0.0247(2) Uani 1 1 d . . .
H15A H -0.3730 0.5233 0.5270 0.037 Uiso 1 1 calc R . .
H15B H -0.4369 0.5469 0.3373 0.037 Uiso 1 1 calc R . .
H15C H -0.4608 0.5885 0.5181 0.037 Uiso 1 1 calc R . .
B1 B -0.58672(11) 0.64721(8) 0.89924(19) 0.0239(2) Uani 1 1 d . . .
N1 N 0.19169(8) 0.42537(6) 0.77642(14) 0.02048(17) Uani 1 1 d . . .
N2 N -0.31795(8) 0.62019(6) 0.42931(14) 0.02044(17) Uani 1 1 d . . .
F1 F -0.69540(8) 0.62833(5) 0.82722(14) 0.03433(19) Uani 1 1 d . . .
F2 F -0.54065(8) 0.58821(5) 1.00816(15) 0.0407(2) Uani 1 1 d . . .
F3 F -0.52388(8) 0.66158(7) 0.75434(13) 0.0417(2) Uani 1 1 d . . .
F4 F -0.59067(8) 0.71224(5) 1.00515(14) 0.0381(2) Uani 1 1 d . . .
Cl1 Cl 0.02506(2) 0.635254(13) 0.64380(3) 0.02118(6) 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'
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
C9 C1 C2 112.77(8) . . y
C9 C1 Cl1 123.73(8) . . y
C2 C1 Cl1 123.49(7) . . y
C10 C2 C1 118.21(9) . . y
C10 C2 C3 136.64(10) . . y
C1 C2 C3 105.11(8) . . y
C4 C3 C8 119.40(10) . . y
C4 C3 C2 132.41(10) . . y
C8 C3 C2 108.08(9) . . y
C5 C4 C3 119.77(10) . . y
C5 C4 H4 120.1 . . n
C3 C4 H4 120.1 . . n
C4 C5 C6 120.47(11) . . y
C4 C5 H5 119.8 . . n
C6 C5 H5 119.8 . . n
C7 C6 C5 120.51(10) . . y
C7 C6 H6 119.7 . . n
C5 C6 H6 119.7 . . n
C6 C7 C8 120.02(10) . . y
C6 C7 H7 120.0 . . n
C8 C7 H7 120.0 . . n
C7 C8 C3 119.30(10) . . y
C7 C8 C9 132.07(10) . . y
C3 C8 C9 108.56(9) . . y
C1 C9 C13 118.61(9) . . y
C1 C9 C8 105.40(8) . . y
C13 C9 C8 135.99(9) . . y
N1 C10 C2 131.74(11) . . y
N1 C10 H10 114.1 . . n
C2 C10 H10 114.1 . . n
N1 C11 H11A 109.5 . . n
N1 C11 H11B 109.5 . . n
H11A C11 H11B 109.5 . . n
N1 C11 H11C 109.5 . . n
H11A C11 H11C 109.5 . . n
H11B C11 H11C 109.5 . . n
N1 C12 H12A 109.5 . . n
N1 C12 H12B 109.5 . . n
H12A C12 H12B 109.5 . . n
N1 C12 H12C 109.5 . . n
H12A C12 H12C 109.5 . . n
H12B C12 H12C 109.5 . . n
N2 C13 C9 131.23(10) . . y
N2 C13 H13 114.4 . . n
C9 C13 H13 114.4 . . n
N2 C14 H14A 109.5 . . n
N2 C14 H14B 109.5 . . n
H14A C14 H14B 109.5 . . n
N2 C14 H14C 109.5 . . n
H14A C14 H14C 109.5 . . n
H14B C14 H14C 109.5 . . n
N2 C15 H15A 109.5 . . n
N2 C15 H15B 109.5 . . n
H15A C15 H15B 109.5 . . n
N2 C15 H15C 109.5 . . n
H15A C15 H15C 109.5 . . n
H15B C15 H15C 109.5 . . n
F4 B1 F2 109.84(11) . . y
F4 B1 F3 109.11(12) . . y
F2 B1 F3 110.52(11) . . y
F4 B1 F1 108.34(11) . . y
F2 B1 F1 109.67(11) . . y
F3 B1 F1 109.32(11) . . y
C10 N1 C12 125.15(10) . . y
C10 N1 C11 119.96(11) . . y
C12 N1 C11 114.87(10) . . y
C13 N2 C15 125.53(10) . . y
C13 N2 C14 120.34(10) . . y
C15 N2 C14 113.96(9) . . 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 C9 1.4081(14) . y
C1 C2 1.4184(13) . y
C1 Cl1 1.7232(10) . y
C2 C10 1.4113(13) . y
C2 C3 1.4730(14) . y
C3 C4 1.4047(15) . y
C3 C8 1.4290(14) . y
C4 C5 1.3941(15) . y
C4 H4 0.9300 . n
C5 C6 1.3963(17) . y
C5 H5 0.9300 . n
C6 C7 1.3921(16) . y
C6 H6 0.9300 . n
C7 C8 1.4016(15) . y
C7 H7 0.9300 . n
C8 C9 1.4664(15) . y
C9 C13 1.4210(14) . y
C10 N1 1.3156(13) . y
C10 H10 0.9300 . n
C11 N1 1.4680(16) . y
C11 H11A 0.9600 . n
C11 H11B 0.9600 . n
C11 H11C 0.9600 . n
C12 N1 1.4583(16) . y
C12 H12A 0.9600 . n
C12 H12B 0.9600 . n
C12 H12C 0.9600 . n
C13 N2 1.3128(14) . y
C13 H13 0.9300 . n
C14 N2 1.4688(15) . y
C14 H14A 0.9600 . n
C14 H14B 0.9600 . n
C14 H14C 0.9600 . n
C15 N2 1.4658(15) . y
C15 H15A 0.9600 . n
C15 H15B 0.9600 . n
C15 H15C 0.9600 . n
B1 F4 1.3908(16) . y
B1 F2 1.3917(16) . y
B1 F3 1.3974(18) . y
B1 F1 1.4067(16) . y
