#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/48/1514809.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_1514809
loop_
_publ_author_name
'Böttcher, Tobias'
'Bassil, Bassem S.'
'Zhechkov, Lyuben'
'Heine, Thomas'
'Röschenthaler, Gerd-Volker'
_publ_section_title
;
 (NHCMe)SiCl4: a versatile carbene transfer reagent -- synthesis from
 silicochloroform
;
_journal_issue                   1
_journal_name_full               'Chemical Science'
_journal_page_first              77
_journal_paper_doi               10.1039/c2sc21214e
_journal_volume                  4
_journal_year                    2013
_chemical_formula_sum            'C11 H15 Cl2 N2 P'
_chemical_formula_weight         277.12
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 128.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.240(3)
_cell_length_b                   11.531(3)
_cell_length_c                   15.038(3)
_cell_measurement_reflns_used    51
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.51
_cell_measurement_theta_min      2.70
_cell_volume                     2605.2(14)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω 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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6638
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.9
_exptl_crystal_size_min          0.7
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0305
_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)+(0.0750P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                2680
_reflns_number_total             2974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc21214e.txt
_cod_data_source_block           try3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        2605.4(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1514809
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'
'-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
C1 C 0.13809(8) 0.69851(12) 0.08585(11) 0.0218(3) Uani 1 1 d
C2 C 0.04179(11) 0.77552(18) -0.09504(13) 0.0372(4) Uani 1 1 d
H22 H -0.0194(16) 0.736(2) -0.153(2) 0.053(6) Uiso 1 1 d
H21 H 0.0619(14) 0.8132(18) -0.1338(17) 0.040(5) Uiso 1 1 d
C3 C 0.04533(11) 0.85550(15) -0.01203(15) 0.0333(3) Uani 1 1 d
H32 H -0.0143(14) 0.8618(18) -0.0337(17) 0.037(5) Uiso 1 1 d
H31 H 0.0691(15) 0.934(2) -0.0039(19) 0.050(6) Uiso 1 1 d
C4 C 0.12343(11) 0.59351(16) -0.07096(13) 0.0315(3) Uani 1 1 d
H43 H 0.0631(14) 0.5537(19) -0.1337(18) 0.045(6) Uiso 1 1 d
H42 H 0.1642(15) 0.5383(19) -0.0154(19) 0.042(5) Uiso 1 1 d
H41 H 0.1468(14) 0.6307(19) -0.1045(17) 0.041(5) Uiso 1 1 d
C5 C 0.11516(11) 0.83602(16) 0.19551(14) 0.0322(3) Uani 1 1 d
H53 H 0.0568(16) 0.850(2) 0.1704(19) 0.047(6) Uiso 1 1 d
H52 H 0.1369(14) 0.775(2) 0.2479(19) 0.043(6) Uiso 1 1 d
H51 H 0.146(2) 0.901(3) 0.215(2) 0.075(8) Uiso 1 1 d
C6 C 0.27642(9) 0.65417(13) 0.33286(11) 0.0243(3) Uani 1 1 d
C7 C 0.28671(10) 0.59141(15) 0.41996(13) 0.0306(3) Uani 1 1 d
H71 H 0.2559(13) 0.5199(19) 0.3989(16) 0.036(5) Uiso 1 1 d
C8 C 0.34026(12) 0.63407(17) 0.53091(13) 0.0375(4) Uani 1 1 d
H81 H 0.3519(15) 0.587(2) 0.5892(19) 0.048(6) Uiso 1 1 d
C9 C 0.38384(11) 0.73910(17) 0.55564(13) 0.0388(4) Uani 1 1 d
H91 H 0.4210(16) 0.769(2) 0.631(2) 0.056(6) Uiso 1 1 d
C10 C 0.37531(10) 0.80129(15) 0.47007(14) 0.0335(4) Uani 1 1 d
H101 H 0.4094(14) 0.8685(19) 0.4869(17) 0.038(5) Uiso 1 1 d
C11 C 0.32194(9) 0.75894(13) 0.35910(12) 0.0276(3) Uani 1 1 d
H111 H 0.3158(13) 0.8034(18) 0.2978(17) 0.035(5) Uiso 1 1 d
N1 N 0.10445(8) 0.68313(12) -0.02151(10) 0.0266(3) Uani 1 1 d
N2 N 0.10787(8) 0.79578(12) 0.09829(11) 0.0281(3) Uani 1 1 d
P1 P 0.21125(2) 0.58291(3) 0.19201(3) 0.02316(13) Uani 1 1 d
Cl1 Cl 0.32093(2) 0.64158(3) 0.17114(3) 0.03140(13) Uani 1 1 d
Cl2 Cl 0.09147(2) 0.54132(4) 0.18859(3) 0.03276(13) 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'
P P 0.1023 0.0942 '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
N1 C1 N2 111.17(13)
N1 C1 P1 118.66(11)
N2 C1 P1 130.03(11)
N1 C2 C3 103.18(12)
N2 C3 C2 103.12(13)
C11 C6 C7 119.10(13)
C11 C6 P1 124.41(11)
C7 C6 P1 116.18(12)
C8 C7 C6 120.36(15)
C7 C8 C9 120.08(16)
C10 C9 C8 120.05(15)
C9 C10 C11 120.06(16)
C6 C11 C10 120.34(14)
C1 N1 C4 129.39(13)
C1 N1 C2 111.60(13)
C4 N1 C2 118.97(13)
C1 N2 C5 129.38(13)
C1 N2 C3 110.88(13)
C5 N2 C3 118.67(13)
C6 P1 C1 105.75(7)
C6 P1 Cl1 90.12(5)
C1 P1 Cl1 86.69(4)
C6 P1 Cl2 94.05(5)
C1 P1 Cl2 85.47(5)
Cl2 P1 Cl1 171.88(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3234(18)
C1 N2 1.3293(19)
C1 P1 1.8707(15)
C2 N1 1.465(2)
C2 C3 1.519(3)
C3 N2 1.477(2)
C4 N1 1.447(2)
C5 N2 1.455(2)
C6 C11 1.397(2)
C6 C7 1.398(2)
C6 P1 1.8482(15)
C7 C8 1.393(2)
C8 C9 1.385(3)
C9 C10 1.390(3)
C10 C11 1.392(2)
P1 Cl1 2.4161(6)
P1 Cl2 2.3227(5)
