#------------------------------------------------------------------------------
#$Date: 2019-11-25 05:37:32 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240110 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/93/4129396.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_4129396
loop_
_publ_author_name
'Ahmad, Syed Usman'
'Szilvási, Tibor'
'Irran, Elisabeth'
'Inoue, Shigeyoshi'
_publ_section_title
;
 An NHC-Stabilized Silicon Analogue of Acylium Ion: Synthesis, Structure,
 Reactivity, and Theoretical Studies.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5828
_journal_page_last               5836
_journal_paper_doi               10.1021/jacs.5b01853
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C48 H50 O4 Si2, 2(C7 H13 N2), 2(C2 H3 N)'
_chemical_formula_sum            'C66 H82 N6 O4 Si2'
_chemical_formula_weight         1079.56
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.877(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.4980(6)
_cell_length_b                   13.8363(7)
_cell_length_c                   18.2313(8)
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.9420
_cell_measurement_theta_min      4.0260
_cell_volume                     3130.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12398
_diffrn_reflns_theta_full        67.49
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         4.02
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  0.8798
_exptl_absorpt_correction_T_min  0.8304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5634
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0785P)²+2.1850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1731
_refine_ls_wR_factor_ref         0.1925
_reflns_number_gt                4080
_reflns_number_total             5634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b01853_si_003.cif
_cod_data_source_block           cu-398
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4129396
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Si1 Si 0.49730(6) 0.55578(6) 0.55047(4) 0.0296(2) Uani 1 1 d . . .
O1 O 0.58920(15) 0.47957(16) 0.52196(11) 0.0314(5) Uani 1 1 d . . .
O2 O 0.52507(18) 0.66513(17) 0.55921(12) 0.0400(5) Uani 1 1 d . . .
N1 N 0.7007(2) 0.8235(2) 0.44596(15) 0.0404(7) Uani 1 1 d . . .
N2 N 0.7155(2) 0.8525(2) 0.56226(15) 0.0413(7) Uani 1 1 d . . .
C1 C 0.4495(2) 0.5011(2) 0.63612(16) 0.0310(7) Uani 1 1 d . . .
C2 C 0.3389(2) 0.5045(2) 0.64718(16) 0.0331(7) Uani 1 1 d . . .
C3 C 0.3022(3) 0.4523(3) 0.70472(17) 0.0400(8) Uani 1 1 d . . .
H3 H 0.2280 0.4545 0.7113 0.048 Uiso 1 1 calc R . .
C4 C 0.3721(3) 0.3975(3) 0.75225(17) 0.0420(8) Uani 1 1 d . . .
H4 H 0.3455 0.3596 0.7896 0.050 Uiso 1 1 calc R . .
C5 C 0.4816(3) 0.3981(3) 0.74504(17) 0.0382(7) Uani 1 1 d . . .
H5 H 0.5301 0.3622 0.7787 0.046 Uiso 1 1 calc R . .
C6 C 0.5207(2) 0.4510(2) 0.68879(16) 0.0330(7) Uani 1 1 d . . .
C7 C 0.6412(2) 0.4602(2) 0.69018(16) 0.0345(7) Uani 1 1 d . . .
C8 C 0.6908(3) 0.5443(3) 0.71977(17) 0.0388(7) Uani 1 1 d . . .
C9 C 0.8032(3) 0.5526(3) 0.72431(19) 0.0468(9) Uani 1 1 d . . .
H9 H 0.8371 0.6099 0.7443 0.056 Uiso 1 1 calc R . .
C10 C 0.8662(3) 0.4789(3) 0.7003(2) 0.0499(9) Uani 1 1 d . . .
C11 C 0.8154(3) 0.3966(3) 0.67163(18) 0.0450(9) Uani 1 1 d . . .
H11 H 0.8578 0.3457 0.6554 0.054 Uiso 1 1 calc R . .
C12 C 0.7030(3) 0.3852(3) 0.66549(17) 0.0384(8) Uani 1 1 d . . .
C13 C 0.6519(3) 0.2962(3) 0.63078(19) 0.0451(8) Uani 1 1 d . . .
H13A H 0.6049 0.3137 0.5858 0.068 Uiso 1 1 calc R . .
H13B H 0.6092 0.2645 0.6656 0.068 Uiso 1 1 calc R . .
H13C H 0.7081 0.2519 0.6181 0.068 Uiso 1 1 calc R . .
C14 C 0.9878(3) 0.4900(4) 0.7059(3) 0.0731(14) Uani 1 1 d . . .
H14A H 1.0196 0.4302 0.6896 0.110 Uiso 1 1 calc R . .
H14B H 1.0165 0.5033 0.7574 0.110 Uiso 1 1 calc R . .
H14C H 1.0056 0.5437 0.6746 0.110 Uiso 1 1 calc R . .
C15 C 0.6257(3) 0.6267(3) 0.74632(19) 0.0448(8) Uani 1 1 d . . .
H15A H 0.5779 0.6019 0.7808 0.067 Uiso 1 1 calc R . .
H15B H 0.5826 0.6567 0.7039 0.067 Uiso 1 1 calc R . .
H15C H 0.6746 0.6749 0.7714 0.067 Uiso 1 1 calc R . .
C16 C 0.2599(2) 0.5688(3) 0.60153(17) 0.0363(7) Uani 1 1 d . . .
C17 C 0.1876(2) 0.5313(2) 0.54367(18) 0.0361(7) Uani 1 1 d . . .
C18 C 0.1113(3) 0.5940(3) 0.5057(2) 0.0421(8) Uani 1 1 d . . .
H18 H 0.0617 0.5688 0.4668 0.051 Uiso 1 1 calc R . .
C19 C 0.1064(3) 0.6900(3) 0.5230(2) 0.0454(9) Uani 1 1 d . . .
C20 C 0.1790(3) 0.7259(3) 0.58041(19) 0.0441(8) Uani 1 1 d . . .
H20 H 0.1759 0.7923 0.5932 0.053 Uiso 1 1 calc R . .
C21 C 0.2563(2) 0.6665(3) 0.61967(18) 0.0396(8) Uani 1 1 d . . .
C22 C 0.3349(3) 0.7098(3) 0.6801(2) 0.0499(9) Uani 1 1 d . . .
H22A H 0.3320 0.6737 0.7261 0.075 Uiso 1 1 calc R . .
H22B H 0.3159 0.7775 0.6876 0.075 Uiso 1 1 calc R . .
H22C H 0.4080 0.7064 0.6659 0.075 Uiso 1 1 calc R . .
C23 C 0.0249(3) 0.7567(3) 0.4805(3) 0.0639(12) Uani 1 1 d . . .
H23A H -0.0222 0.7191 0.4443 0.096 Uiso 1 1 calc R . .
H23B H 0.0628 0.8060 0.4549 0.096 Uiso 1 1 calc R . .
H23C H -0.0186 0.7881 0.5150 0.096 Uiso 1 1 calc R . .
C24 C 0.1924(3) 0.4283(3) 0.5205(2) 0.0433(8) Uani 1 1 d . . .
H24A H 0.1333 0.4150 0.4814 0.065 Uiso 1 1 calc R . .
H24B H 0.1857 0.3863 0.5630 0.065 Uiso 1 1 calc R . .
H24C H 0.2615 0.4159 0.5018 0.065 Uiso 1 1 calc R . .
C25 C 0.6706(3) 0.7941(2) 0.50999(18) 0.0391(7) Uani 1 1 d . . .
H25 H 0.6250 0.7408 0.5169 0.047 Uiso 1 1 calc R . .
C26 C 0.7678(3) 0.9037(3) 0.45841(19) 0.0410(8) Uani 1 1 d . . .
C27 C 0.7768(3) 0.9214(3) 0.53175(19) 0.0420(8) Uani 1 1 d . . .
C28 C 0.8375(4) 0.9977(3) 0.5772(2) 0.0618(11) Uani 1 1 d . . .
H28A H 0.8684 1.0436 0.5446 0.093 Uiso 1 1 calc R . .
H28B H 0.8956 0.9677 0.6104 0.093 Uiso 1 1 calc R . .
H28C H 0.7885 1.0319 0.6064 0.093 Uiso 1 1 calc R . .
C29 C 0.8139(4) 0.9529(3) 0.3971(2) 0.0609(11) Uani 1 1 d . . .
H29A H 0.8559 1.0092 0.4164 0.091 Uiso 1 1 calc R . .
H29B H 0.7555 0.9741 0.3599 0.091 Uiso 1 1 calc R . .
H29C H 0.8610 0.9080 0.3744 0.091 Uiso 1 1 calc R . .
C30 C 0.6631(4) 0.7810(3) 0.3743(2) 0.0575(10) Uani 1 1 d . . .
H30A H 0.6235 0.7213 0.3816 0.086 Uiso 1 1 calc R . .
H30B H 0.7251 0.7664 0.3480 0.086 Uiso 1 1 calc R . .
H30C H 0.6154 0.8268 0.3453 0.086 Uiso 1 1 calc R . .
C31 C 0.6990(4) 0.8436(3) 0.6403(2) 0.0592(11) Uani 1 1 d . . .
H31A H 0.6447 0.7938 0.6455 0.089 Uiso 1 1 calc R . .
H31B H 0.6742 0.9056 0.6580 0.089 Uiso 1 1 calc R . .
H31C H 0.7670 0.8254 0.6694 0.089 Uiso 1 1 calc R . .
N3 N 0.5323(4) 0.0630(4) 0.5901(3) 0.0619(12) Uani 0.70 1 d PU A 1
C32 C 0.5624(5) 0.0959(4) 0.5389(3) 0.0524(12) Uani 0.70 1 d PU A 1
C33 C 0.6002(19) 0.1364(12) 0.4733(9) 0.054(3) Uani 0.70 1 d PU A 1
H33A H 0.5691 0.2008 0.4639 0.081 Uiso 0.70 1 calc PR A 1
H33B H 0.5782 0.0944 0.4309 0.081 Uiso 0.70 1 calc PR A 1
H33C H 0.6790 0.1412 0.4808 0.081 Uiso 0.70 1 calc PR A 1
N3A N 0.4764(11) -0.0029(10) 0.6042(7) 0.066(2) Uani 0.30 1 d PU B 2
C32A C 0.4420(13) -0.0647(11) 0.5675(8) 0.061(3) Uani 0.30 1 d PU B 2
C33A C 0.402(5) -0.146(4) 0.517(2) 0.059(4) Uani 0.30 1 d PU B 2
H33D H 0.4065 -0.1279 0.4657 0.089 Uiso 0.30 1 calc PR B 2
H33E H 0.3269 -0.1609 0.5236 0.089 Uiso 0.30 1 calc PR B 2
H33F H 0.4465 -0.2039 0.5293 0.089 Uiso 0.30 1 calc PR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
O2 Si1 O1 118.64(12) . 3_666
O2 Si1 O1 119.18(12) . .
O1 Si1 O1 88.49(10) 3_666 .
O2 Si1 C1 113.09(13) . .
O1 Si1 C1 107.18(12) 3_666 .
O1 Si1 C1 107.34(12) . .
O2 Si1 Si1 132.44(10) . 3_666
O1 Si1 Si1 44.41(7) 3_666 3_666
O1 Si1 Si1 44.07(7) . 3_666
C1 Si1 Si1 114.47(11) . 3_666
Si1 O1 Si1 91.51(10) 3_666 .
C25 N1 C26 109.2(3) . .
C25 N1 C30 124.6(3) . .
C26 N1 C30 126.2(3) . .
C25 N2 C27 109.9(3) . .
C25 N2 C31 123.4(3) . .
C27 N2 C31 126.7(3) . .
C6 C1 C2 117.7(3) . .
C6 C1 Si1 121.4(2) . .
C2 C1 Si1 120.8(2) . .
C3 C2 C1 120.2(3) . .
C3 C2 C16 118.0(3) . .
C1 C2 C16 121.7(3) . .
C4 C3 C2 121.1(3) . .
C3 C4 C5 119.5(3) . .
C4 C5 C6 120.6(3) . .
C5 C6 C1 120.6(3) . .
C5 C6 C7 118.0(3) . .
C1 C6 C7 121.1(3) . .
C8 C7 C12 120.4(3) . .
C8 C7 C6 118.3(3) . .
C12 C7 C6 121.3(3) . .
C7 C8 C9 119.2(3) . .
C7 C8 C15 121.4(3) . .
C9 C8 C15 119.5(3) . .
C10 C9 C8 121.5(4) . .
C11 C10 C9 118.2(3) . .
C11 C10 C14 121.5(4) . .
C9 C10 C14 120.3(4) . .
C10 C11 C12 122.4(3) . .
C7 C12 C11 118.4(3) . .
C7 C12 C13 121.6(3) . .
C11 C12 C13 120.0(3) . .
C21 C16 C17 120.0(3) . .
C21 C16 C2 118.7(3) . .
C17 C16 C2 121.2(3) . .
C16 C17 C18 118.6(3) . .
C16 C17 C24 121.5(3) . .
C18 C17 C24 119.8(3) . .
C19 C18 C17 122.1(3) . .
C18 C19 C20 118.5(3) . .
C18 C19 C23 121.3(4) . .
C20 C19 C23 120.2(4) . .
C19 C20 C21 121.5(3) . .
C16 C21 C20 119.3(3) . .
C16 C21 C22 121.4(3) . .
C20 C21 C22 119.3(3) . .
N2 C25 N1 107.7(3) . .
C27 C26 N1 106.4(3) . .
C27 C26 C29 132.0(4) . .
N1 C26 C29 121.6(3) . .
C26 C27 N2 106.8(3) . .
C26 C27 C28 130.9(3) . .
N2 C27 C28 122.3(3) . .
N3 C32 C33 179.1(9) . .
N3A C32A C33A 177(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 O2 1.556(3) .
Si1 O1 1.676(2) 3_666
Si1 O1 1.687(2) .
Si1 C1 1.895(3) .
Si1 Si1 2.4091(16) 3_666
O1 Si1 1.676(2) 3_666
N1 C25 1.332(4) .
N1 C26 1.393(5) .
N1 C30 1.458(4) .
N2 C25 1.322(4) .
N2 C27 1.381(4) .
N2 C31 1.467(4) .
C1 C6 1.411(4) .
C1 C2 1.421(4) .
C2 C3 1.395(4) .
C2 C16 1.504(5) .
C3 C4 1.381(5) .
C4 C5 1.391(5) .
C5 C6 1.395(4) .
C6 C7 1.509(4) .
C7 C8 1.395(5) .
C7 C12 1.400(5) .
C8 C9 1.402(5) .
C8 C15 1.514(5) .
C9 C10 1.391(6) .
C10 C11 1.376(6) .
C10 C14 1.517(5) .
C11 C12 1.405(5) .
C12 C13 1.493(5) .
C16 C21 1.393(5) .
C16 C17 1.404(5) .
C17 C18 1.408(5) .
C17 C24 1.490(5) .
C18 C19 1.369(5) .
C19 C20 1.392(5) .
C19 C23 1.517(5) .
C20 C21 1.399(5) .
C21 C22 1.510(5) .
C26 C27 1.351(5) .
C26 C29 1.484(5) .
C27 C28 1.492(5) .
N3 C32 1.141(8) .
C32 C33 1.451(18) .
N3A C32A 1.138(19) .
C32A C33A 1.50(5) .
