#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/48/1514808.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_1514808
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            'C6 H13 Cl2 N2 P'
_chemical_formula_weight         215.05
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.768(2)
_cell_length_b                   12.985(3)
_cell_length_c                   19.423(4)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.52
_cell_measurement_theta_min      2.35
_cell_volume                     1959.1(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5553
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.5784
_exptl_absorpt_correction_T_min  0.5137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.90
_exptl_crystal_size_min          0.80
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    calcall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0316
_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)+(0.0550P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                2033
_reflns_number_total             2243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc21214e.txt
_cod_data_source_block           try2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        1959.2(8)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1514808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.4468(2) 0.08118(11) 0.38122(7) 0.0168(3) Uani 1 1 d
C2 C 0.7244(2) 0.04451(13) 0.41763(10) 0.0249(4) Uani 1 1 d
H22 H 0.793(3) 0.0090(19) 0.3841(13) 0.037(6) Uiso 1 1 d
H21 H 0.763(3) 0.0291(18) 0.4612(13) 0.035(6) Uiso 1 1 d
C3 C 0.7074(2) 0.15971(13) 0.40424(9) 0.0239(3) Uani 1 1 d
H32 H 0.720(3) 0.2031(17) 0.4437(12) 0.032(6) Uiso 1 1 d
H31 H 0.790(3) 0.1869(17) 0.3691(12) 0.034(6) Uiso 1 1 d
C4 C 0.5082(3) -0.10127(13) 0.41444(11) 0.0303(4) Uani 1 1 d
H43 H 0.547(3) -0.1379(18) 0.3740(13) 0.040(6) Uiso 1 1 d
H42 H 0.390(3) -0.1135(19) 0.4177(12) 0.035(6) Uiso 1 1 d
H41 H 0.561(3) -0.1257(19) 0.4547(13) 0.042(7) Uiso 1 1 d
C5 C 0.4650(3) 0.27374(12) 0.36534(10) 0.0261(3) Uani 1 1 d
H53 H 0.506(4) 0.3026(19) 0.3245(14) 0.048(7) Uiso 1 1 d
H52 H 0.505(4) 0.317(2) 0.3977(14) 0.049(7) Uiso 1 1 d
H51 H 0.349(4) 0.274(2) 0.3643(13) 0.042(7) Uiso 1 1 d
C6 C 0.1589(2) 0.14949(14) 0.29417(9) 0.0260(4) Uani 1 1 d
H63 H 0.251(3) 0.1763(19) 0.2675(13) 0.041(6) Uiso 1 1 d
H62 H 0.108(3) 0.2034(19) 0.3168(12) 0.036(6) Uiso 1 1 d
H61 H 0.076(3) 0.1147(19) 0.2620(12) 0.038(6) Uiso 1 1 d
N1 N 0.54568(18) 0.00825(10) 0.40863(7) 0.0215(3) Uani 1 1 d
N2 N 0.53071(17) 0.16979(10) 0.37684(7) 0.0196(3) Uani 1 1 d
P1 P 0.22206(5) 0.04656(3) 0.35446(2) 0.01976(13) Uani 1 1 d
Cl1 Cl 0.13620(5) 0.15180(3) 0.45461(2) 0.02416(12) Uani 1 1 d
Cl2 Cl 0.33885(6) -0.04307(3) 0.26399(2) 0.02942(14) Uani 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0173(7) 0.0172(6) 0.0158(6) -0.0012(5) 0.0006(5) -0.0002(6)
C2 0.0180(8) 0.0259(8) 0.0309(9) -0.0002(6) -0.0042(7) 0.0013(6)
C3 0.0200(8) 0.0243(7) 0.0274(8) -0.0014(6) -0.0029(6) -0.0032(6)
C4 0.0337(10) 0.0158(7) 0.0413(10) 0.0032(7) -0.0100(8) 0.0011(7)
C5 0.0292(9) 0.0154(7) 0.0336(9) 0.0025(6) -0.0027(7) -0.0014(6)
C6 0.0271(9) 0.0292(8) 0.0219(8) 0.0006(6) -0.0058(6) 0.0032(7)
N1 0.0210(7) 0.0158(6) 0.0278(7) 0.0001(5) -0.0044(5) -0.0002(5)
N2 0.0184(6) 0.0171(6) 0.0232(6) 0.0016(5) -0.0006(5) -0.0010(5)
P1 0.0176(2) 0.0188(2) 0.0229(2) -0.00045(14) -0.00206(14) -0.00171(14)
Cl1 0.0245(2) 0.0266(2) 0.0215(2) -0.00178(14) 0.00085(14) 0.00424(15)
Cl2 0.0305(3) 0.0305(2) 0.0272(2) -0.01058(15) 0.00073(16) 0.00017(16)
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
N2 C1 N1 111.11(14)
N2 C1 P1 130.38(11)
N1 C1 P1 118.51(11)
N1 C2 C3 102.22(13)
N2 C3 C2 103.21(13)
C1 N1 C4 127.64(14)
C1 N1 C2 111.29(13)
C4 N1 C2 119.38(14)
C1 N2 C5 129.84(14)
C1 N2 C3 110.89(13)
C5 N2 C3 117.49(13)
C6 P1 C1 104.47(7)
C6 P1 Cl2 89.23(6)
C1 P1 Cl2 88.04(5)
C6 P1 Cl1 91.56(6)
C1 P1 Cl1 84.29(5)
Cl2 P1 Cl1 172.24(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.3250(19)
C1 N1 1.330(2)
C1 P1 1.8764(16)
C2 N1 1.476(2)
C2 C3 1.524(2)
C3 N2 1.478(2)
C4 N1 1.456(2)
C5 N2 1.460(2)
C6 P1 1.8435(18)
P1 Cl2 2.2947(7)
P1 Cl1 2.4691(7)
