#------------------------------------------------------------------------------
#$Date: 2024-08-02 02:59:23 +0300 (Fri, 02 Aug 2024) $
#$Revision: 293627 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/91/7249173.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_7249173
loop_
_publ_author_name
'Kocek, Hugo'
'Chalupská, Dominika'
'Dejmek, Milan'
'Dvořáková, Alexandra'
'Zgarbová, Michala'
'Šála, Michal'
'Chalupský, Karel'
'Krafčíková, Petra'
'Otava, Tomáš'
'Drexler, Matus'
'Procházková, Eliška'
'Klepetářová, Blanka'
'Štefek, Milan'
'Kozic, Ján'
'Mertlíková-Kaiserová, Helena'
'Boura, Evzen'
'Weber, Jan'
'Nencka, Radim'
_publ_section_title
;
 Discovery of highly potent SARS-CoV-2 nsp14 methyltransferase inhibitors
 based on adenosine 5′-carboxamides
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00422A
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H50 N8 O5 Si2, C2 H3 N'
_chemical_formula_sum            'C41 H53 N9 O5 Si2'
_chemical_formula_weight         808.10
_chemical_name_systematic
(2S,3R,4R,5R)-5-(4-amino-5-(pyrimidin-5-ylethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)tetrahydrofuran-2-carboxamide
_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   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2024-06-05 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.3520(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5790(4)
_cell_length_b                   11.3344(3)
_cell_length_c                   14.3892(4)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.1644
_cell_measurement_theta_min      3.2985
_cell_volume                     2185.20(11)
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.046
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49727
_diffrn_reflns_theta_full        72.211
_diffrn_reflns_theta_max         72.211
_diffrn_reflns_theta_min         3.112
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.166
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.06
_refine_diff_density_min         -0.04
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 3455 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.035(4)
_refine_ls_extinction_coef       60(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         8393
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.0004770
_refine_ls_shift/su_mean         0.0000287
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method = Chebychev polynomial, (Carruthers & Watkin, 1979) 
 W = 1.0/[A[0]*T[0]'(X)+A[1]*T[1]'(X) ... +A[NP-1]*T[NP-1]'(X)] 
 0.119 0.147 0.299E-01 -0.107E-02 0.245E-02 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0343
_refine_ls_wR_factor_gt          0.0323
_refine_ls_wR_factor_ref         0.0323
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                8393
_reflns_number_total             8550
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      28.79
_oxford_refine_ls_scale          0.18860(17)
_cod_data_source_file            d4md00422a2.cif
_cod_data_source_block           I_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249173
_oxford_refine_reflns_threshold_expression I>2.0\s(I)
_refine_ls_r_factor_ref          0.0249
_reflns_number_all               8550
_oxford_hooft_y                  0.042(6)
_oxford_bijvoet_difference       0.035(4)
_oxford_refined_flack_x          0.037(12)
loop_
_symmetry_equiv_pos_as_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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Si1 Si 0.08075(3) -0.02788(4) 0.33452(3) 0.0267 1.0000 Uani . . . . . .
O2 O 0.15668(6) 0.06543(8) 0.29212(7) 0.0253 1.0000 Uani . . . . . .
C3 C 0.12888(9) 0.18001(11) 0.26135(9) 0.0219 1.0000 Uani . . . . . .
C4 C 0.11326(9) 0.18614(11) 0.15224(9) 0.0224 1.0000 Uani . . . . . .
O5 O 0.19819(6) 0.24516(9) 0.12650(6) 0.0236 1.0000 Uani . . . . . .
C6 C 0.27344(9) 0.24786(11) 0.20662(9) 0.0220 1.0000 Uani . . . . . .
C7 C 0.21696(9) 0.26566(11) 0.28849(8) 0.0218 1.0000 Uani . . . . . .
O8 O 0.27792(7) 0.24221(9) 0.37462(6) 0.0276 1.0000 Uani . . . . . .
Si9 Si 0.30183(3) 0.33578(4) 0.46420(2) 0.0269 1.0000 Uani . . . . . .
C10 C 0.42254(11) 0.28392(14) 0.53575(10) 0.0330 1.0000 Uani . . . . . .
C11 C 0.40860(14) 0.17035(17) 0.58878(14) 0.0500 1.0000 Uani . . . . . .
C12 C 0.46427(16) 0.37951(18) 0.60672(15) 0.0608 1.0000 Uani . . . . . .
C13 C 0.49863(13) 0.2587(2) 0.46969(14) 0.0590 1.0000 Uani . . . . . .
C14 C 0.31588(15) 0.48735(14) 0.41834(13) 0.0481 1.0000 Uani . . . . . .
C15 C 0.19578(13) 0.3312(2) 0.53064(13) 0.0520 1.0000 Uani . . . . . .
N16 N 0.34419(7) 0.33967(10) 0.19376(7) 0.0236 1.0000 Uani . . . . . .
C17 C 0.44643(9) 0.32459(13) 0.21368(9) 0.0255 1.0000 Uani . . . . . .
C18 C 0.49325(9) 0.42933(12) 0.20190(9) 0.0257 1.0000 Uani . . . . . .
C19 C 0.59902(10) 0.44616(12) 0.21931(9) 0.0267 1.0000 Uani . . . . . .
C20 C 0.68744(10) 0.45705(13) 0.23765(10) 0.0285 1.0000 Uani . . . . . .
C21 C 0.79249(9) 0.47284(13) 0.26679(9) 0.0264 1.0000 Uani . . . . . .
C22 C 0.83232(10) 0.58383(13) 0.29051(10) 0.0309 1.0000 Uani . . . . . .
N23 N 0.92885(9) 0.60139(13) 0.32125(10) 0.0378 1.0000 Uani . . . . . .
C24 C 0.98577(10) 0.50615(15) 0.32735(11) 0.0367 1.0000 Uani . . . . . .
N25 N 0.95787(9) 0.39617(13) 0.30558(10) 0.0381 1.0000 Uani . . . . . .
C26 C 0.86048(11) 0.38039(14) 0.27546(11) 0.0350 1.0000 Uani . . . . . .
C27 C 0.41555(9) 0.51353(12) 0.17223(9) 0.0235 1.0000 Uani . . . . . .
C28 C 0.32445(9) 0.45495(12) 0.16788(9) 0.0228 1.0000 Uani . . . . . .
N29 N 0.23286(8) 0.50309(11) 0.14148(9) 0.0288 1.0000 Uani . . . . . .
C30 C 0.23908(10) 0.61607(13) 0.11884(11) 0.0318 1.0000 Uani . . . . . .
N31 N 0.32016(8) 0.68450(11) 0.12041(9) 0.0295 1.0000 Uani . . . . . .
C32 C 0.41050(9) 0.63496(12) 0.14929(9) 0.0243 1.0000 Uani . . . . . .
N33 N 0.49155(8) 0.70326(11) 0.15463(9) 0.0295 1.0000 Uani . . . . . .
C34 C 0.01730(9) 0.24829(12) 0.11217(9) 0.0253 1.0000 Uani . . . . . .
O35 O -0.06155(7) 0.19469(10) 0.10656(8) 0.0369 1.0000 Uani . . . . . .
N36 N 0.02645(8) 0.36355(10) 0.08868(8) 0.0252 1.0000 Uani . . . . . .
C37 C -0.05577(9) 0.43998(12) 0.06540(9) 0.0237 1.0000 Uani . . . . . .
C38 C -0.04594(10) 0.55865(12) 0.09347(9) 0.0262 1.0000 Uani . . . . . .
C39 C -0.12735(10) 0.63212(12) 0.07871(9) 0.0262 1.0000 Uani . . . . . .
C40 C -0.22167(9) 0.59179(12) 0.03491(9) 0.0239 1.0000 Uani . . . . . .
C41 C -0.31118(10) 0.66333(12) 0.01961(9) 0.0264 1.0000 Uani . . . . . .
C42 C -0.39737(10) 0.61568(13) -0.02456(10) 0.0288 1.0000 Uani . . . . . .
C43 C -0.40494(10) 0.49503(13) -0.05869(10) 0.0291 1.0000 Uani . . . . . .
O44 O -0.48370(7) 0.44948(10) -0.09931(8) 0.0404 1.0000 Uani . . . . . .
N45 N -0.31840(8) 0.43153(10) -0.04354(8) 0.0277 1.0000 Uani . . . . . .
C46 C -0.22830(9) 0.47464(12) 0.00301(9) 0.0236 1.0000 Uani . . . . . .
C47 C -0.14592(9) 0.39935(12) 0.01774(9) 0.0257 1.0000 Uani . . . . . .
C48 C -0.30664(11) 0.78903(13) 0.05293(11) 0.0331 1.0000 Uani . . . . . .
C49 C 0.16865(11) -0.13732(12) 0.40180(10) 0.0331 1.0000 Uani . . . . . .
C50 C 0.11237(14) -0.22164(16) 0.45806(13) 0.0492 1.0000 Uani . . . . . .
C51 C 0.24662(13) -0.06930(16) 0.47097(13) 0.0461 1.0000 Uani . . . . . .
C52 C 0.22090(16) -0.20670(16) 0.33337(15) 0.0543 1.0000 Uani . . . . . .
C53 C 0.00637(14) 0.05419(17) 0.41115(15) 0.0516 1.0000 Uani . . . . . .
C54 C -0.00469(15) -0.09772(17) 0.23496(14) 0.0574 1.0000 Uani . . . . . .
C55 C -0.30346(19) 0.1202(3) 0.1242(2) 0.0798 1.0000 Uani . . . . . .
C1 C -0.3004(3) 0.1096(3) 0.2230(3) 0.1083 1.0000 Uani . . . . . .
N4 N -0.2981(4) 0.1040(5) 0.3020(3) 0.2002 1.0000 Uani . . . . . .
H31 H 0.0683 0.2053 0.2843 0.0242 1.0000 Uiso R . . . . .
H41 H 0.1076 0.1057 0.1269 0.0259 1.0000 Uiso R . . . . .
H61 H 0.3108 0.1747 0.2145 0.0247 1.0000 Uiso R . . . . .
H71 H 0.1886 0.3440 0.2834 0.0229 1.0000 Uiso R . . . . .
H113 H 0.4708 0.1452 0.6290 0.0742 1.0000 Uiso R . . . . .
H112 H 0.3599 0.1832 0.6295 0.0734 1.0000 Uiso R . . . . .
H111 H 0.3865 0.1093 0.5427 0.0749 1.0000 Uiso R . . . . .
H123 H 0.5241 0.3517 0.6453 0.0904 1.0000 Uiso R . . . . .
H122 H 0.4146 0.3940 0.6474 0.0865 1.0000 Uiso R . . . . .
H121 H 0.4788 0.4520 0.5731 0.0915 1.0000 Uiso R . . . . .
H133 H 0.5613 0.2366 0.5097 0.0864 1.0000 Uiso R . . . . .
H132 H 0.5099 0.3323 0.4352 0.0875 1.0000 Uiso R . . . . .
H131 H 0.4733 0.1932 0.4233 0.0879 1.0000 Uiso R . . . . .
H141 H 0.3275 0.5392 0.4711 0.0721 1.0000 Uiso R . . . . .
H143 H 0.3732 0.4913 0.3874 0.0722 1.0000 Uiso R . . . . .
H142 H 0.2595 0.5101 0.3754 0.0719 1.0000 Uiso R . . . . .
H151 H 0.2099 0.3843 0.5834 0.0783 1.0000 Uiso R . . . . .
H153 H 0.1856 0.2519 0.5513 0.0769 1.0000 Uiso R . . . . .
H152 H 0.1343 0.3557 0.4908 0.0769 1.0000 Uiso R . . . . .
H171 H 0.4767 0.2511 0.2320 0.0289 1.0000 Uiso R . . . . .
H221 H 0.7897 0.6488 0.2854 0.0368 1.0000 Uiso R . . . . .
H241 H 1.0545 0.5177 0.3522 0.0463 1.0000 Uiso R . . . . .
H261 H 0.8387 0.3033 0.2587 0.0427 1.0000 Uiso R . . . . .
H301 H 0.1757 0.6539 0.0961 0.0366 1.0000 Uiso R . . . . .
H381 H 0.0153 0.5875 0.1247 0.0324 1.0000 Uiso R . . . . .
H391 H -0.1177 0.7134 0.1006 0.0313 1.0000 Uiso R . . . . .
H421 H -0.4573 0.6620 -0.0356 0.0348 1.0000 Uiso R . . . . .
H471 H -0.1524 0.3223 -0.0033 0.0281 1.0000 Uiso R . . . . .
H481 H -0.3716 0.8252 0.0347 0.0498 1.0000 Uiso R . . . . .
H482 H -0.2551 0.8311 0.0244 0.0472 1.0000 Uiso R . . . . .
H483 H -0.2896 0.7931 0.1218 0.0489 1.0000 Uiso R . . . . .
H501 H 0.1614 -0.2827 0.4885 0.0734 1.0000 Uiso R . . . . .
H502 H 0.0864 -0.1806 0.5078 0.0726 1.0000 Uiso R . . . . .
H503 H 0.0572 -0.2631 0.4184 0.0717 1.0000 Uiso R . . . . .
H511 H 0.2896 -0.1225 0.5107 0.0695 1.0000 Uiso R . . . . .
H512 H 0.2108 -0.0187 0.5101 0.0694 1.0000 Uiso R . . . . .
H513 H 0.2860 -0.0191 0.4346 0.0680 1.0000 Uiso R . . . . .
H522 H 0.2712 -0.2613 0.3680 0.0817 1.0000 Uiso R . . . . .
H521 H 0.2560 -0.1529 0.2973 0.0808 1.0000 Uiso R . . . . .
H523 H 0.1714 -0.2520 0.2891 0.0788 1.0000 Uiso R . . . . .
H532 H -0.0293 0.0011 0.4436 0.0779 1.0000 Uiso R . . . . .
H531 H 0.0494 0.1027 0.4561 0.0776 1.0000 Uiso R . . . . .
H533 H -0.0410 0.1066 0.3734 0.0782 1.0000 Uiso R . . . . .
H542 H -0.0432 -0.1593 0.2613 0.0857 1.0000 Uiso R . . . . .
H541 H 0.0347 -0.1326 0.1899 0.0864 1.0000 Uiso R . . . . .
H543 H -0.0521 -0.0414 0.2011 0.0845 1.0000 Uiso R . . . . .
H552 H -0.2403 0.1019 0.1069 0.1202 1.0000 Uiso R . . . . .
H551 H -0.3551 0.0639 0.0945 0.1202 1.0000 Uiso R . . . . .
H553 H -0.3244 0.2005 0.1087 0.1214 1.0000 Uiso R . . . . .
H361 H 0.0845 0.3935 0.1018 0.0303 1.0000 Uiso R . . . . .
H451 H -0.3203 0.3595 -0.0648 0.0317 1.0000 Uiso R . . . . .
H331 H 0.4859 0.7775 0.1392 0.0369 1.0000 Uiso R . . . . .
H332 H 0.5509 0.6741 0.1781 0.0376 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . Si1 . C49 . 103.27(6) yes
O2 . Si1 . C53 . 109.18(7) yes
C49 . Si1 . C53 . 112.68(8) yes
O2 . Si1 . C54 . 109.49(7) yes
C49 . Si1 . C54 . 112.29(8) yes
C53 . Si1 . C54 . 109.70(10) yes
Si1 . O2 . C3 . 123.63(8) yes
O2 . C3 . C4 . 110.25(10) yes
O2 . C3 . C7 . 110.18(9) yes
C4 . C3 . C7 . 101.60(9) yes
O2 . C3 . H31 . 111.3 no
C4 . C3 . H31 . 110.1 no
C7 . C3 . H31 . 113.0 no
C3 . C4 . O5 . 107.40(9) yes
C3 . C4 . C34 . 112.00(10) yes
O5 . C4 . C34 . 111.36(10) yes
C3 . C4 . H41 . 108.9 no
O5 . C4 . H41 . 110.8 no
C34 . C4 . H41 . 106.3 no
C4 . O5 . C6 . 107.78(9) yes
O5 . C6 . C7 . 104.27(9) yes
O5 . C6 . N16 . 108.57(10) yes
C7 . C6 . N16 . 115.61(10) yes
O5 . C6 . H61 . 111.9 no
C7 . C6 . H61 . 110.1 no
N16 . C6 . H61 . 106.5 no
C3 . C7 . C6 . 100.87(9) yes
C3 . C7 . O8 . 115.33(10) yes
C6 . C7 . O8 . 111.15(10) yes
C3 . C7 . H71 . 106.0 no
C6 . C7 . H71 . 107.9 no
O8 . C7 . H71 . 114.4 no
C7 . O8 . Si9 . 125.40(8) yes
O8 . Si9 . C10 . 105.56(6) yes
O8 . Si9 . C14 . 109.43(7) yes
C10 . Si9 . C14 . 110.60(7) yes
O8 . Si9 . C15 . 108.19(8) yes
C10 . Si9 . C15 . 112.92(8) yes
C14 . Si9 . C15 . 109.98(10) yes
Si9 . C10 . C11 . 111.70(10) yes
Si9 . C10 . C12 . 109.78(11) yes
C11 . C10 . C12 . 109.02(14) yes
Si9 . C10 . C13 . 109.41(11) yes
C11 . C10 . C13 . 107.60(16) yes
C12 . C10 . C13 . 109.27(15) yes
C10 . C11 . H113 . 112.0 no
C10 . C11 . H112 . 109.3 no
H113 . C11 . H112 . 107.1 no
C10 . C11 . H111 . 108.0 no
H113 . C11 . H111 . 109.6 no
H112 . C11 . H111 . 110.9 no
C10 . C12 . H123 . 109.8 no
C10 . C12 . H122 . 107.6 no
H123 . C12 . H122 . 108.1 no
C10 . C12 . H121 . 110.0 no
H123 . C12 . H121 . 109.8 no
H122 . C12 . H121 . 111.5 no
C10 . C13 . H133 . 106.9 no
C10 . C13 . H132 . 109.0 no
H133 . C13 . H132 . 108.6 no
C10 . C13 . H131 . 110.6 no
H133 . C13 . H131 . 111.5 no
H132 . C13 . H131 . 110.3 no
Si9 . C14 . H141 . 107.5 no
Si9 . C14 . H143 . 110.2 no
H141 . C14 . H143 . 107.5 no
Si9 . C14 . H142 . 111.6 no
H141 . C14 . H142 . 111.5 no
H143 . C14 . H142 . 108.5 no
Si9 . C15 . H151 . 108.5 no
Si9 . C15 . H153 . 110.3 no
H151 . C15 . H153 . 111.1 no
Si9 . C15 . H152 . 110.6 no
H151 . C15 . H152 . 109.1 no
H153 . C15 . H152 . 107.2 no
C6 . N16 . C17 . 123.34(11) yes
C6 . N16 . C28 . 127.88(10) yes
C17 . N16 . C28 . 108.61(10) yes
N16 . C17 . C18 . 109.75(12) yes
N16 . C17 . H171 . 122.8 no
C18 . C17 . H171 . 127.4 no
C17 . C18 . C19 . 124.53(12) yes
C17 . C18 . C27 . 106.23(11) yes
C19 . C18 . C27 . 129.22(12) yes
C18 . C19 . C20 . 176.88(14) yes
C19 . C20 . C21 . 175.58(15) yes
C20 . C21 . C22 . 120.98(13) yes
C20 . C21 . C26 . 123.26(13) yes
C22 . C21 . C26 . 115.75(12) yes
C21 . C22 . N23 . 122.74(13) yes
C21 . C22 . H221 . 118.9 no
N23 . C22 . H221 . 118.3 no
C22 . N23 . C24 . 115.74(13) yes
N23 . C24 . N25 . 127.62(13) yes
N23 . C24 . H241 . 116.1 no
N25 . C24 . H241 . 116.3 no
C24 . N25 . C26 . 115.64(13) yes
C21 . C26 . N25 . 122.49(14) yes
C21 . C26 . H261 . 120.1 no
N25 . C26 . H261 . 117.5 no
C18 . C27 . C28 . 107.48(11) yes
C18 . C27 . C32 . 136.20(12) yes
C28 . C27 . C32 . 116.31(12) yes
C27 . C28 . N16 . 107.93(11) yes
C27 . C28 . N29 . 125.97(12) yes
N16 . C28 . N29 . 126.09(11) yes
C28 . N29 . C30 . 111.42(11) yes
N29 . C30 . N31 . 129.58(13) yes
N29 . C30 . H301 . 114.9 no
N31 . C30 . H301 . 115.5 no
C30 . N31 . C32 . 117.74(12) yes
C27 . C32 . N31 . 118.89(12) yes
C27 . C32 . N33 . 122.79(12) yes
N31 . C32 . N33 . 118.32(12) yes
C32 . N33 . H331 . 120.5 no
C32 . N33 . H332 . 119.7 no
H331 . N33 . H332 . 119.6 no
C4 . C34 . O35 . 119.04(12) yes
C4 . C34 . N36 . 115.76(11) yes
O35 . C34 . N36 . 125.13(12) yes
C34 . N36 . C37 . 123.26(11) yes
C34 . N36 . H361 . 116.5 no
C37 . N36 . H361 . 118.5 no
N36 . C37 . C38 . 119.05(11) yes
N36 . C37 . C47 . 121.12(12) yes
C38 . C37 . C47 . 119.81(12) yes
C37 . C38 . C39 . 120.00(12) yes
C37 . C38 . H381 . 120.5 no
C39 . C38 . H381 . 119.5 no
C38 . C39 . C40 . 121.54(12) yes
C38 . C39 . H391 . 117.4 no
C40 . C39 . H391 . 121.0 no
C39 . C40 . C41 . 124.48(12) yes
C39 . C40 . C46 . 117.31(12) yes
C41 . C40 . C46 . 118.21(12) yes
C40 . C41 . C42 . 119.31(12) yes
C40 . C41 . C48 . 119.54(12) yes
C42 . C41 . C48 . 121.16(13) yes
C41 . C42 . C43 . 123.00(12) yes
C41 . C42 . H421 . 120.4 no
C43 . C42 . H421 . 116.6 no
C42 . C43 . O44 . 123.93(12) yes
C42 . C43 . N45 . 115.53(12) yes
O44 . C43 . N45 . 120.53(13) yes
C43 . N45 . C46 . 124.14(12) yes
C43 . N45 . H451 . 117.5 no
C46 . N45 . H451 . 118.3 no
C40 . C46 . N45 . 119.78(11) yes
C40 . C46 . C47 . 121.46(12) yes
N45 . C46 . C47 . 118.76(12) yes
C46 . C47 . C37 . 119.70(12) yes
C46 . C47 . H471 . 119.8 no
C37 . C47 . H471 . 120.5 no
C41 . C48 . H481 . 109.1 no
C41 . C48 . H482 . 108.7 no
H481 . C48 . H482 . 110.9 no
C41 . C48 . H483 . 111.0 no
H481 . C48 . H483 . 108.0 no
H482 . C48 . H483 . 109.3 no
Si1 . C49 . C50 . 110.75(11) yes
Si1 . C49 . C51 . 108.40(10) yes
C50 . C49 . C51 . 108.69(13) yes
Si1 . C49 . C52 . 109.38(11) yes
C50 . C49 . C52 . 110.11(14) yes
C51 . C49 . C52 . 109.47(15) yes
C49 . C50 . H501 . 107.8 no
C49 . C50 . H502 . 111.3 no
H501 . C50 . H502 . 107.6 no
C49 . C50 . H503 . 112.9 no
H501 . C50 . H503 . 108.1 no
H502 . C50 . H503 . 108.9 no
C49 . C51 . H511 . 111.0 no
C49 . C51 . H512 . 108.0 no
H511 . C51 . H512 . 109.5 no
C49 . C51 . H513 . 108.7 no
H511 . C51 . H513 . 110.4 no
H512 . C51 . H513 . 109.1 no
C49 . C52 . H522 . 110.6 no
C49 . C52 . H521 . 110.0 no
H522 . C52 . H521 . 107.5 no
C49 . C52 . H523 . 110.1 no
H522 . C52 . H523 . 109.8 no
H521 . C52 . H523 . 108.7 no
Si1 . C53 . H532 . 110.3 no
Si1 . C53 . H531 . 110.6 no
H532 . C53 . H531 . 109.5 no
Si1 . C53 . H533 . 110.4 no
H532 . C53 . H533 . 108.7 no
H531 . C53 . H533 . 107.3 no
Si1 . C54 . H542 . 107.9 no
Si1 . C54 . H541 . 109.8 no
H542 . C54 . H541 . 110.3 no
Si1 . C54 . H543 . 112.5 no
H542 . C54 . H543 . 107.9 no
H541 . C54 . H543 . 108.4 no
C1 . C55 . H552 . 111.2 no
C1 . C55 . H551 . 106.2 no
H552 . C55 . H551 . 110.5 no
C1 . C55 . H553 . 105.7 no
H552 . C55 . H553 . 112.8 no
H551 . C55 . H553 . 110.2 no
C55 . C1 . N4 . 178.3(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Si1 . O2 . 1.6608(9) yes
Si1 . C49 . 1.8774(15) yes
Si1 . C53 . 1.8609(18) yes
Si1 . C54 . 1.8668(18) yes
O2 . C3 . 1.4039(15) yes
C3 . C4 . 1.5514(17) yes
C3 . C7 . 1.5407(16) yes
C3 . H31 . 0.978 no
C4 . O5 . 1.4329(14) yes
C4 . C34 . 1.5108(17) yes
C4 . H41 . 0.980 no
O5 . C6 . 1.4111(15) yes
C6 . C7 . 1.5199(17) yes
C6 . N16 . 1.4484(15) yes
C6 . H61 . 0.970 no
C7 . O8 . 1.3994(14) yes
C7 . H71 . 0.966 no
O8 . Si9 . 1.6601(10) yes
Si9 . C10 . 1.8824(14) yes
Si9 . C14 . 1.8613(16) yes
Si9 . C15 . 1.8541(17) yes
C10 . C11 . 1.524(2) yes
C10 . C12 . 1.533(2) yes
C10 . C13 . 1.540(2) yes
C11 . H113 . 0.985 no
C11 . H112 . 0.963 no
C11 . H111 . 0.972 no
C12 . H123 . 0.960 no
C12 . H122 . 0.976 no
C12 . H121 . 0.990 no
C13 . H133 . 0.979 no
C13 . H132 . 0.996 no
C13 . H131 . 1.020 no
C14 . H141 . 0.953 no
C14 . H143 . 0.958 no
C14 . H142 . 0.939 no
C15 . H151 . 0.964 no
C15 . H153 . 0.963 no
C15 . H152 . 0.973 no
N16 . C17 . 1.3819(15) yes
N16 . C28 . 1.3731(17) yes
C17 . C18 . 1.3702(19) yes
C17 . H171 . 0.947 no
C18 . C19 . 1.4300(18) yes
C18 . C27 . 1.4352(18) yes
C19 . C20 . 1.1931(19) yes
C20 . C21 . 1.4311(17) yes
C21 . C22 . 1.390(2) yes
C21 . C26 . 1.389(2) yes
C22 . N23 . 1.3286(18) yes
C22 . H221 . 0.933 no
N23 . C24 . 1.322(2) yes
C24 . N25 . 1.326(2) yes
C24 . H241 . 0.953 no
N25 . C26 . 1.3351(18) yes
C26 . H261 . 0.941 no
C27 . C28 . 1.3963(17) yes
C27 . C32 . 1.4144(19) yes
C28 . N29 . 1.3547(16) yes
N29 . C30 . 1.3274(18) yes
C30 . N31 . 1.3440(17) yes
C30 . H301 . 0.970 no
N31 . C32 . 1.3517(17) yes
C32 . N33 . 1.3376(17) yes
N33 . H331 . 0.870 no
N33 . H332 . 0.886 no
C34 . O35 . 1.2223(16) yes
C34 . N36 . 1.3602(18) yes
N36 . C37 . 1.4098(16) yes
N36 . H361 . 0.850 no
C37 . C38 . 1.4045(19) yes
C37 . C47 . 1.3813(18) yes
C38 . C39 . 1.3727(19) yes
C38 . H381 . 0.938 no
C39 . C40 . 1.4087(18) yes
C39 . H391 . 0.975 no
C40 . C41 . 1.4479(18) yes
C40 . C46 . 1.4031(19) yes
C41 . C42 . 1.350(2) yes
C41 . C48 . 1.501(2) yes
C42 . C43 . 1.451(2) yes
C42 . H421 . 0.960 no
C43 . O44 . 1.2445(17) yes
C43 . N45 . 1.3650(17) yes
N45 . C46 . 1.3849(16) yes
N45 . H451 . 0.871 no
C46 . C47 . 1.3954(18) yes
C47 . H471 . 0.924 no
C48 . H481 . 0.969 no
C48 . H482 . 0.990 no
C48 . H483 . 0.981 no
C49 . C50 . 1.534(2) yes
C49 . C51 . 1.537(2) yes
C49 . C52 . 1.523(2) yes
C50 . H501 . 1.010 no
C50 . H502 . 0.968 no
C50 . H503 . 0.985 no
C51 . H511 . 0.960 no
C51 . H512 . 0.985 no
C51 . H513 . 0.987 no
C52 . H522 . 0.994 no
C52 . H521 . 0.974 no
C52 . H523 . 0.991 no
C53 . H532 . 0.943 no
C53 . H531 . 0.969 no
C53 . H533 . 0.974 no
C54 . H542 . 0.984 no
C54 . H541 . 0.988 no
C54 . H543 . 0.978 no
C55 . C1 . 1.421(5) yes
C55 . H552 . 0.954 no
C55 . H551 . 0.992 no
C55 . H553 . 0.968 no
C1 . N4 . 1.134(5) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C50 . H503 . N23 1_445 172 0.98 2.56 3.538(2) yes
C55 . H551 . O44 2_445 150 0.99 2.56 3.448(2) yes
N36 . H361 . N29 . 171 0.85 2.36 3.200(2) yes
N45 . H451 . N31 2_545 178 0.87 2.14 3.009(2) yes
N33 . H331 . O44 2_555 175 0.87 2.03 2.899(2) yes
