#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:42:43 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281585 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159084.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_7159084
loop_
_publ_author_name
'Zhang, Yu'
'Yi, Zi-Juan'
'Yang, Ai-Mei'
'Guo, Jia-Ming'
'Li, Xin'
'Wei, Bang-Guo'
_publ_section_title
;
 AgSbF₆-catalyzed C3 aza-Friedel-Crafts alkylation of
 N,O-acetals with indoles for the synthesis of
 N-α indole substituted pyrrolidine and piperidine
 derivatives.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1303
_journal_page_last               1315
_journal_paper_doi               10.1039/d2ob02213c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H44 N2 O3 Si'
_chemical_formula_weight         472.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-05-08 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.937(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2060(5)
_cell_length_b                   11.4624(6)
_cell_length_c                   12.4467(6)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.910
_cell_measurement_theta_min      4.560
_cell_volume                     1392.92(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22950
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.466
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 2235 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       0.025(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5418
_refine_ls_number_restraints     119
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0632P)²+0.2219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5084
_reflns_number_total             5418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02213c2.cif
_cod_data_source_block           mo_ddz21073_0m
_cod_depositor_comments
'Adding full bibliography for 7159083--7159084.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159084
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.36309(10) 0.38403(7) 0.36961(6) 0.0499(3) Uani 1 1 d D . . . .
O1 O 0.27838(18) 0.35681(16) 0.92155(14) 0.0362(4) Uani 1 1 d . . . . .
O2 O 0.08856(17) 0.41850(18) 0.78605(15) 0.0388(5) Uani 1 1 d . . . . .
O3 O 0.3313(2) 0.44736(17) 0.47816(14) 0.0400(5) Uani 1 1 d . . . . .
N1 N 0.6160(3) 0.6315(2) 0.9817(2) 0.0477(6) Uani 1 1 d . . . . .
H1 H 0.6316 0.7040 1.0023 0.057 Uiso 1 1 calc R U . . .
N2 N 0.29173(18) 0.42122(18) 0.75362(16) 0.0288(4) Uani 1 1 d . . . . .
C1 C 0.6789(3) 0.5373(3) 1.0407(2) 0.0428(7) Uani 1 1 d . . . . .
C2 C 0.7769(3) 0.5303(4) 1.1456(3) 0.0598(9) Uani 1 1 d . . . . .
H2 H 0.8123 0.5980 1.1864 0.072 Uiso 1 1 calc R U . . .
C3 C 0.8192(4) 0.4225(4) 1.1867(3) 0.0692(12) Uani 1 1 d . . . . .
H3 H 0.8847 0.4158 1.2573 0.083 Uiso 1 1 calc R U . . .
C4 C 0.7679(4) 0.3212(4) 1.1265(3) 0.0637(10) Uani 1 1 d . . . . .
H4 H 0.8006 0.2482 1.1571 0.076 Uiso 1 1 calc R U . . .
C5 C 0.6701(3) 0.3260(3) 1.0228(2) 0.0446(7) Uani 1 1 d . . . . .
H5 H 0.6355 0.2575 0.9831 0.053 Uiso 1 1 calc R U . . .
C6 C 0.6242(2) 0.4359(3) 0.9788(2) 0.0344(6) Uani 1 1 d . . . . .
C7 C 0.5240(2) 0.4755(2) 0.8781(2) 0.0305(5) Uani 1 1 d . . . . .
C8 C 0.5237(3) 0.5936(3) 0.8840(2) 0.0409(6) Uani 1 1 d . . . . .
H8 H 0.4680 0.6427 0.8289 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4412(2) 0.3995(2) 0.78396(19) 0.0297(5) Uani 1 1 d . . . . .
H9 H 0.4591 0.3166 0.8057 0.036 Uiso 1 1 calc R U . . .
C10 C 0.4711(2) 0.4199(3) 0.6715(2) 0.0365(6) Uani 1 1 d . . . . .
H10A H 0.5002 0.5005 0.6658 0.044 Uiso 1 1 calc R U . . .
H10B H 0.5431 0.3671 0.6634 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3367(2) 0.3949(2) 0.58258(18) 0.0315(5) Uani 1 1 d . . . . .
H11 H 0.3240 0.3095 0.5726 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2276(2) 0.4448(2) 0.63341(19) 0.0281(5) Uani 1 1 d . . . . .
H12 H 0.1423 0.3987 0.6065 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1954(3) 0.5740(2) 0.6086(2) 0.0349(6) Uani 1 1 d . . . . .
H13A H 0.1678 0.6080 0.6709 0.042 Uiso 1 1 calc R U . . .
H13B H 0.2792 0.6138 0.6054 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0831(4) 0.5980(3) 0.4995(3) 0.0520(8) Uani 1 1 d . . . . .
H14 H 0.1011 0.5491 0.4398 0.062 Uiso 1 1 calc R U . . .
C15 C 0.0862(6) 0.7239(4) 0.4660(4) 0.0938(16) Uani 1 1 d . . . . .
H15A H 0.0687 0.7734 0.5235 0.141 Uiso 1 1 calc R U . . .
H15B H 0.0164 0.7372 0.3953 0.141 Uiso 1 1 calc R U . . .
H15C H 0.1755 0.7422 0.4577 0.141 Uiso 1 1 calc R U . . .
C16 C -0.0588(4) 0.5670(4) 0.5088(4) 0.0733(11) Uani 1 1 d . . . . .
H16A H -0.0589 0.4868 0.5338 0.110 Uiso 1 1 calc R U . . .
H16B H -0.1261 0.5760 0.4360 0.110 Uiso 1 1 calc R U . . .
H16C H -0.0816 0.6185 0.5625 0.110 Uiso 1 1 calc R U . . .
C17 C 0.2231(2) 0.3954(2) 0.82834(19) 0.0285(5) Uani 1 1 d . . . . .
C18 C -0.0034(3) 0.4137(3) 0.8585(2) 0.0412(7) Uani 1 1 d . . . . .
C19 C -0.0046(4) 0.2933(4) 0.9063(4) 0.0699(11) Uani 1 1 d . . . . .
H19A H -0.0247 0.2365 0.8459 0.105 Uiso 1 1 calc R U . . .
H19B H -0.0743 0.2892 0.9451 0.105 Uiso 1 1 calc R U . . .
H19C H 0.0843 0.2766 0.9587 0.105 Uiso 1 1 calc R U . . .
C20 C 0.0397(4) 0.5066(4) 0.9481(3) 0.0689(11) Uani 1 1 d . . . . .
H20A H 0.1318 0.4903 0.9952 0.103 Uiso 1 1 calc R U . . .
H20B H -0.0228 0.5067 0.9937 0.103 Uiso 1 1 calc R U . . .
H20C H 0.0379 0.5823 0.9128 0.103 Uiso 1 1 calc R U . . .
C21 C -0.1411(3) 0.4424(4) 0.7772(3) 0.0656(11) Uani 1 1 d . . . . .
H21A H -0.1372 0.5187 0.7446 0.098 Uiso 1 1 calc R U . . .
H21B H -0.2102 0.4427 0.8168 0.098 Uiso 1 1 calc R U . . .
H21C H -0.1645 0.3843 0.7181 0.098 Uiso 1 1 calc R U . . .
C22 C 0.4638(17) 0.2553(12) 0.4015(10) 0.106(5) Uani 0.5 1 d D U P A 1
H22A H 0.5476 0.2717 0.4606 0.159 Uiso 0.5 1 calc R U P A 1
H22B H 0.4862 0.2289 0.3349 0.159 Uiso 0.5 1 calc R U P A 1
H22C H 0.4127 0.1950 0.4264 0.159 Uiso 0.5 1 calc R U P A 1
C23 C 0.1831(11) 0.3282(10) 0.2743(8) 0.103(4) Uani 0.6 1 d D U P A 1
H23A H 0.1338 0.2914 0.3211 0.155 Uiso 0.6 1 calc R U P A 1
H23B H 0.1969 0.2720 0.2203 0.155 Uiso 0.6 1 calc R U P A 1
H23C H 0.1305 0.3937 0.2347 0.155 Uiso 0.6 1 calc R U P A 1
C24 C 0.4106(15) 0.4999(17) 0.2881(15) 0.0542(16) Uani 0.6 1 d D U P A 1
C25 C 0.3214(9) 0.6059(6) 0.2678(7) 0.0642(17) Uani 0.6 1 d D U P A 1
H25A H 0.2343 0.5877 0.2135 0.096 Uiso 0.6 1 calc R U P A 1
H25B H 0.3659 0.6682 0.2390 0.096 Uiso 0.6 1 calc R U P A 1
H25C H 0.3061 0.6304 0.3378 0.096 Uiso 0.6 1 calc R U P A 1
C26 C 0.422(2) 0.4614(12) 0.1735(14) 0.057(3) Uani 0.6 1 d D U P A 1
H26A H 0.3385 0.4216 0.1325 0.085 Uiso 0.6 1 calc R U P A 1
H26B H 0.4991 0.4089 0.1840 0.085 Uiso 0.6 1 calc R U P A 1
H26C H 0.4353 0.5293 0.1314 0.085 Uiso 0.6 1 calc R U P A 1
C27 C 0.5607(11) 0.5317(11) 0.3684(9) 0.078(2) Uani 0.5 1 d D U P A 1
H27A H 0.6020 0.5904 0.3324 0.117 Uiso 0.5 1 calc R U P A 1
H27B H 0.6174 0.4621 0.3819 0.117 Uiso 0.5 1 calc R U P A 1
H27C H 0.5534 0.5617 0.4393 0.117 Uiso 0.5 1 calc R U P A 1
C22' C 0.5516(15) 0.3152(13) 0.4314(10) 0.104(5) Uani 0.5 1 d D U P A 2
H22D H 0.6135 0.3740 0.4741 0.157 Uiso 0.5 1 calc R U P A 2
H22E H 0.5844 0.2885 0.3699 0.157 Uiso 0.5 1 calc R U P A 2
H22F H 0.5478 0.2498 0.4799 0.157 Uiso 0.5 1 calc R U P A 2
C23' C 0.256(2) 0.2609(15) 0.3142(13) 0.105(5) Uani 0.4 1 d D U P A 2
H23D H 0.2516 0.2102 0.3754 0.157 Uiso 0.4 1 calc R U P A 2
H23E H 0.2944 0.2183 0.2631 0.157 Uiso 0.4 1 calc R U P A 2
H23F H 0.1649 0.2878 0.2742 0.157 Uiso 0.4 1 calc R U P A 2
C24' C 0.398(2) 0.503(3) 0.279(2) 0.058(2) Uani 0.4 1 d D U P A 2
C25' C 0.2542(15) 0.5672(13) 0.2425(11) 0.080(3) Uani 0.4 1 d D U P A 2
H25D H 0.2387 0.6058 0.3071 0.120 Uiso 0.4 1 calc R U P A 2
H25E H 0.1824 0.5103 0.2129 0.120 Uiso 0.4 1 calc R U P A 2
H25F H 0.2534 0.6246 0.1851 0.120 Uiso 0.4 1 calc R U P A 2
C26' C 0.424(3) 0.4343(19) 0.178(2) 0.055(3) Uani 0.4 1 d D U P A 2
H26D H 0.4217 0.4882 0.1170 0.083 Uiso 0.4 1 calc R U P A 2
H26E H 0.3529 0.3759 0.1515 0.083 Uiso 0.4 1 calc R U P A 2
H26F H 0.5126 0.3965 0.2018 0.083 Uiso 0.4 1 calc R U P A 2
C27' C 0.5256(13) 0.5781(9) 0.3346(9) 0.075(2) Uani 0.5 1 d D U P A 2
H27D H 0.6077 0.5329 0.3402 0.112 Uiso 0.5 1 calc R U P A 2
H27E H 0.5239 0.6014 0.4091 0.112 Uiso 0.5 1 calc R U P A 2
H27F H 0.5253 0.6470 0.2893 0.112 Uiso 0.5 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
O3 Si1 C22 115.0(4) . . ?
O3 Si1 C23' 114.8(5) . . ?
O3 Si1 C24 106.5(5) . . ?
C22 Si1 C24 120.0(7) . . ?
O3 Si1 C24' 106.8(8) . . ?
C23' Si1 C24' 123.0(9) . . ?
O3 Si1 C23 105.3(4) . . ?
C22 Si1 C23 103.9(7) . . ?
C24 Si1 C23 104.6(5) . . ?
O3 Si1 C22' 104.7(4) . . ?
C23' Si1 C22' 104.2(9) . . ?
C24' Si1 C22' 100.8(8) . . ?
C17 O2 C18 120.70(19) . . ?
C11 O3 Si1 126.89(16) . . ?
C1 N1 C8 108.7(2) . . ?
C1 N1 H1 125.6 . . ?
C8 N1 H1 125.6 . . ?
C17 N2 C12 125.03(18) . . ?
C17 N2 C9 119.32(18) . . ?
C12 N2 C9 114.17(17) . . ?
N1 C1 C2 130.4(3) . . ?
N1 C1 C6 108.0(2) . . ?
C2 C1 C6 121.5(3) . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 134.1(3) . . ?
C1 C6 C7 106.4(3) . . ?
C8 C7 C6 106.2(2) . . ?
C8 C7 C9 127.6(2) . . ?
C6 C7 C9 126.2(2) . . ?
C7 C8 N1 110.6(3) . . ?
C7 C8 H8 124.7 . . ?
N1 C8 H8 124.7 . . ?
N2 C9 C7 113.82(19) . . ?
N2 C9 C10 101.85(18) . . ?
C7 C9 C10 114.0(2) . . ?
N2 C9 H9 109.0 . . ?
C7 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C11 C10 C9 104.99(19) . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
O3 C11 C10 111.9(2) . . ?
O3 C11 C12 112.24(19) . . ?
C10 C11 C12 103.76(18) . . ?
O3 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C12 C11 H11 109.6 . . ?
N2 C12 C13 112.9(2) . . ?
N2 C12 C11 100.86(17) . . ?
C13 C12 C11 114.5(2) . . ?
N2 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C14 C13 C12 114.6(2) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 110.4(4) . . ?
C15 C14 C16 109.9(3) . . ?
C13 C14 C16 112.0(3) . . ?
C15 C14 H14 108.1 . . ?
C13 C14 H14 108.1 . . ?
C16 C14 H14 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 O2 125.5(2) . . ?
O1 C17 N2 123.2(2) . . ?
O2 C17 N2 111.25(19) . . ?
O2 C18 C19 110.8(2) . . ?
O2 C18 C21 102.5(2) . . ?
C19 C18 C21 110.6(3) . . ?
O2 C18 C20 108.9(2) . . ?
C19 C18 C20 112.9(3) . . ?
C21 C18 C20 110.8(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1 C23 H23A 109.5 . . ?
Si1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C26 106.5(15) . . ?
C25 C24 C27 110.1(12) . . ?
C26 C24 C27 109.1(13) . . ?
C25 C24 Si1 116.0(11) . . ?
C26 C24 Si1 114.5(12) . . ?
C27 C24 Si1 100.3(11) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Si1 C22' H22D 109.5 . . ?
Si1 C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
Si1 C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
Si1 C23' H23D 109.5 . . ?
Si1 C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
Si1 C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C27' C24' C26' 109(2) . . ?
C27' C24' C25' 118(2) . . ?
C26' C24' C25' 111(2) . . ?
C27' C24' Si1 114.9(16) . . ?
C26' C24' Si1 102.8(18) . . ?
C25' C24' Si1 100.7(16) . . ?
C24' C25' H25D 109.5 . . ?
C24' C25' H25E 109.5 . . ?
H25D C25' H25E 109.5 . . ?
C24' C25' H25F 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
C24' C26' H26D 109.5 . . ?
C24' C26' H26E 109.5 . . ?
H26D C26' H26E 109.5 . . ?
C24' C26' H26F 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 109.5 . . ?
C24' C27' H27D 109.5 . . ?
C24' C27' H27E 109.5 . . ?
H27D C27' H27E 109.5 . . ?
C24' C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?
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
Si1 O3 1.6470(18) . ?
Si1 C22 1.776(10) . ?
Si1 C23' 1.794(13) . ?
Si1 C24 1.82(2) . ?
Si1 C24' 1.87(4) . ?
Si1 C23 1.980(9) . ?
Si1 C22' 2.014(11) . ?
O1 C17 1.216(3) . ?
O2 C17 1.346(3) . ?
O2 C18 1.480(3) . ?
O3 C11 1.419(3) . ?
N1 C1 1.357(4) . ?
N1 C8 1.374(4) . ?
N1 H1 0.8700 . ?
N2 C17 1.350(3) . ?
N2 C12 1.473(3) . ?
N2 C9 1.482(3) . ?
C1 C2 1.397(4) . ?
C1 C6 1.416(4) . ?
C2 C3 1.359(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.398(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.441(3) . ?
C7 C8 1.356(4) . ?
C7 C9 1.506(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.535(3) . ?
C9 H9 0.9900 . ?
C10 C11 1.518(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.542(3) . ?
C11 H11 0.9900 . ?
C12 C13 1.529(3) . ?
C12 H12 0.9900 . ?
C13 C14 1.524(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.505(6) . ?
C14 C16 1.529(5) . ?
C14 H14 0.9900 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C18 C19 1.505(5) . ?
C18 C21 1.509(4) . ?
C18 C20 1.511(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 C25 1.495(17) . ?
C24 C26 1.529(17) . ?
C24 C27 1.608(14) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C22' H22D 0.9700 . ?
C22' H22E 0.9700 . ?
C22' H22F 0.9700 . ?
C23' H23D 0.9700 . ?
C23' H23E 0.9700 . ?
C23' H23F 0.9700 . ?
C24' C27' 1.54(2) . ?
C24' C26' 1.58(2) . ?
C24' C25' 1.59(2) . ?
C25' H25D 0.9700 . ?
C25' H25E 0.9700 . ?
C25' H25F 0.9700 . ?
C26' H26D 0.9700 . ?
C26' H26E 0.9700 . ?
C26' H26F 0.9700 . ?
C27' H27D 0.9700 . ?
C27' H27E 0.9700 . ?
C27' H27F 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.87 2.07 2.920(3) 163.6 2_657
C19 H19C O1 0.97 2.35 2.931(4) 117.9 .
C20 H20A O1 0.97 2.49 3.075(4) 118.4 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 Si1 O3 C11 -21.2(7) . . . . ?
C23' Si1 O3 C11 58.8(8) . . . . ?
C24 Si1 O3 C11 -156.7(5) . . . . ?
C24' Si1 O3 C11 -161.1(7) . . . . ?
C23 Si1 O3 C11 92.6(4) . . . . ?
C22' Si1 O3 C11 -54.8(5) . . . . ?
C8 N1 C1 C2 -178.0(3) . . . . ?
C8 N1 C1 C6 -0.4(3) . . . . ?
N1 C1 C2 C3 177.8(3) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 -178.1(3) . . . . ?
N1 C1 C6 C5 -178.6(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
N1 C1 C6 C7 0.1(3) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C1 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C9 -3.5(4) . . . . ?
C1 C6 C7 C9 178.0(2) . . . . ?
C6 C7 C8 N1 -0.4(3) . . . . ?
C9 C7 C8 N1 -178.2(2) . . . . ?
C1 N1 C8 C7 0.5(3) . . . . ?
C17 N2 C9 C7 -66.3(3) . . . . ?
C12 N2 C9 C7 126.9(2) . . . . ?
C17 N2 C9 C10 170.6(2) . . . . ?
C12 N2 C9 C10 3.8(3) . . . . ?
C8 C7 C9 N2 -54.8(3) . . . . ?
C6 C7 C9 N2 127.9(2) . . . . ?
C8 C7 C9 C10 61.5(3) . . . . ?
C6 C7 C9 C10 -115.9(3) . . . . ?
N2 C9 C10 C11 -25.7(3) . . . . ?
C7 C9 C10 C11 -148.7(2) . . . . ?
Si1 O3 C11 C10 98.2(3) . . . . ?
Si1 O3 C11 C12 -145.65(19) . . . . ?
C9 C10 C11 O3 159.3(2) . . . . ?
C9 C10 C11 C12 38.1(3) . . . . ?
C17 N2 C12 C13 90.3(3) . . . . ?
C9 N2 C12 C13 -103.8(2) . . . . ?
C17 N2 C12 C11 -147.0(2) . . . . ?
C9 N2 C12 C11 18.9(3) . . . . ?
O3 C11 C12 N2 -155.1(2) . . . . ?
C10 C11 C12 N2 -34.1(2) . . . . ?
O3 C11 C12 C13 -33.5(3) . . . . ?
C10 C11 C12 C13 87.5(2) . . . . ?
N2 C12 C13 C14 -157.1(2) . . . . ?
C11 C12 C13 C14 88.2(3) . . . . ?
C12 C13 C14 C15 -164.0(3) . . . . ?
C12 C13 C14 C16 73.2(3) . . . . ?
C18 O2 C17 O1 8.9(4) . . . . ?
C18 O2 C17 N2 -170.8(2) . . . . ?
C12 N2 C17 O1 166.8(2) . . . . ?
C9 N2 C17 O1 1.5(4) . . . . ?
C12 N2 C17 O2 -13.5(3) . . . . ?
C9 N2 C17 O2 -178.8(2) . . . . ?
C17 O2 C18 C19 -60.9(3) . . . . ?
C17 O2 C18 C21 -178.9(3) . . . . ?
C17 O2 C18 C20 63.8(3) . . . . ?
O3 Si1 C24 C25 -45.9(10) . . . . ?
C22 Si1 C24 C25 -178.7(9) . . . . ?
C23' Si1 C24 C25 93.4(13) . . . . ?
C24' Si1 C24 C25 49(16) . . . . ?
C23 Si1 C24 C25 65.4(11) . . . . ?
C22' Si1 C24 C25 -153.5(10) . . . . ?
O3 Si1 C24 C26 -170.6(11) . . . . ?
C22 Si1 C24 C26 56.6(15) . . . . ?
C23' Si1 C24 C26 -31.4(17) . . . . ?
C24' Si1 C24 C26 -75(16) . . . . ?
C23 Si1 C24 C26 -59.4(13) . . . . ?
C22' Si1 C24 C26 81.8(13) . . . . ?
O3 Si1 C24 C27 72.7(8) . . . . ?
C22 Si1 C24 C27 -60.1(11) . . . . ?
C23' Si1 C24 C27 -148.0(10) . . . . ?
C24' Si1 C24 C27 168(17) . . . . ?
C23 Si1 C24 C27 -176.1(8) . . . . ?
C22' Si1 C24 C27 -34.9(9) . . . . ?
O3 Si1 C24' C27' 63.1(15) . . . . ?
C22 Si1 C24' C27' -72.9(18) . . . . ?
C23' Si1 C24' C27' -160.9(13) . . . . ?
C24 Si1 C24' C27' -23(15) . . . . ?
C23 Si1 C24' C27' 172.8(14) . . . . ?
C22' Si1 C24' C27' -46.0(16) . . . . ?
O3 Si1 C24' C26' -178.8(15) . . . . ?
C22 Si1 C24' C26' 45.2(19) . . . . ?
C23' Si1 C24' C26' -43(2) . . . . ?
C24 Si1 C24' C26' 95(17) . . . . ?
C23 Si1 C24' C26' -69.1(17) . . . . ?
C22' Si1 C24' C26' 72.1(17) . . . . ?
O3 Si1 C24' C25' -64.2(12) . . . . ?
C22 Si1 C24' C25' 159.7(10) . . . . ?
C23' Si1 C24' C25' 71.8(16) . . . . ?
C24 Si1 C24' C25' -150(17) . . . . ?
C23 Si1 C24' C25' 45.5(13) . . . . ?
C22' Si1 C24' C25' -173.4(11) . . . . ?
