#------------------------------------------------------------------------------
#$Date: 2023-04-20 14:53:48 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567734.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_1567734
loop_
_publ_author_name
'Sungnoi, Wanna'
'Harmata, Michael'
_publ_section_title
;
 Oxidative bridgehead functionalization of (4 + 3) cycloadducts obtained
 from oxidopyridinium ions
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              28572
_journal_page_last               28575
_journal_paper_doi               10.1039/D2RA05189C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C26 H39 F6 N O4 Si'
_chemical_formula_sum            'C26 H39 F6 N O4 Si'
_chemical_formula_weight         571.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-10 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                105.3326(16)
_cell_angle_beta                 99.3403(19)
_cell_angle_gamma                101.6075(17)
_cell_formula_units_Z            2
_cell_length_a                   7.2552(2)
_cell_length_b                   13.8552(4)
_cell_length_c                   15.7314(5)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      73.55
_cell_measurement_theta_min      2.99
_cell_volume                     1454.49(8)
_computing_cell_refinement       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51591
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.291
_diffrn_reflns_theta_min         2.992
_diffrn_source                   'Incoatec IMuS microfocus Cu tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8764.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       needle
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol/water'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+0.6809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5225
_reflns_number_total             5717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05189c2.cif
_cod_data_source_block           8a
_cod_database_code               1567734
_shelx_shelxl_version_number     2017/1
_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_max   0.961
_shelx_estimated_absorpt_t_min   0.598
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C10(H10), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C21(H21A,H21B), C22(H22A,H22B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C15(H15A,H15B,
 H15C), C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.20219(6) 0.99409(3) 0.34658(2) 0.02330(10) Uani 1 1 d . . . . .
O1 O 0.37910(13) 0.71888(7) 0.04418(6) 0.0242(2) Uani 1 1 d . . . . .
F2 F 0.30032(13) 0.93516(7) -0.12688(7) 0.0398(2) Uani 1 1 d . . . . .
O2 O 0.17625(13) 0.85638(6) 0.00894(6) 0.01980(19) Uani 1 1 d . . . . .
F4 F -0.08279(13) 0.88474(7) -0.12308(7) 0.0405(2) Uani 1 1 d . . . . .
F6 F -0.19352(13) 0.73148(7) -0.11868(6) 0.0419(2) Uani 1 1 d . . . . .
F1 F 0.48257(13) 0.85878(9) -0.06392(7) 0.0453(3) Uani 1 1 d . . . . .
F5 F -0.05920(15) 0.75400(9) -0.22627(6) 0.0495(3) Uani 1 1 d . . . . .
O4 O -0.34817(14) 0.51497(7) 0.10658(7) 0.0287(2) Uani 1 1 d . . . . .
O3 O -0.07994(15) 0.45917(7) 0.13460(7) 0.0316(2) Uani 1 1 d . . . . .
N1 N -0.06355(15) 0.77895(8) 0.07267(7) 0.0196(2) Uani 1 1 d . . . . .
F3 F 0.31647(18) 0.78390(9) -0.19869(7) 0.0554(3) Uani 1 1 d . . . . .
C3 C 0.22047(18) 0.87776(10) 0.25471(8) 0.0200(3) Uani 1 1 d . . . . .
C6 C 0.16296(18) 0.64427(9) 0.12238(8) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.200825 0.578794 0.097361 0.023 Uiso 1 1 calc R . . . .
C7 C -0.05394(18) 0.61955(9) 0.10487(8) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.23777(18) 0.71976(9) 0.07560(8) 0.0184(2) Uani 1 1 d . . . . .
C26 C -0.1676(2) 0.85989(10) 0.08058(10) 0.0257(3) Uani 1 1 d . . . . .
H26A H -0.306262 0.828015 0.056105 0.039 Uiso 1 1 calc GR . . . .
H26B H -0.121029 0.905850 0.046485 0.039 Uiso 1 1 calc GR . . . .
H26C H -0.145351 0.900018 0.144449 0.039 Uiso 1 1 calc GR . . . .
C4 C 0.22105(18) 0.78996(10) 0.27554(9) 0.0204(3) Uani 1 1 d . . . . .
H4 H 0.192301 0.791591 0.332625 0.024 Uiso 1 1 calc R . . . .
C2 C 0.25207(19) 0.89689(9) 0.16645(8) 0.0204(3) Uani 1 1 d . . . . .
H2A H 0.392058 0.909587 0.168140 0.024 Uiso 1 1 calc R . . . .
H2B H 0.214201 0.961012 0.163878 0.024 Uiso 1 1 calc R . . . .
C11 C 0.3134(2) 0.84376(11) -0.11783(9) 0.0272(3) Uani 1 1 d . . . . .
C8 C -0.14802(19) 0.68883(10) 0.08565(8) 0.0199(3) Uani 1 1 d . . . . .
H8 H -0.283657 0.673243 0.080864 0.024 Uiso 1 1 calc R . . . .
C10 C 0.1469(2) 0.79432(10) -0.08162(9) 0.0222(3) Uani 1 1 d . . . . .
H10 H 0.153024 0.722420 -0.083168 0.027 Uiso 1 1 calc R . . . .
C16 C 0.47745(19) 0.69720(11) 0.24489(9) 0.0233(3) Uani 1 1 d . . . . .
H16A H 0.501511 0.636528 0.202651 0.028 Uiso 1 1 calc R . . . .
H16B H 0.544778 0.760003 0.232701 0.028 Uiso 1 1 calc R . . . .
C24 C -0.1567(2) 0.52392(10) 0.11651(9) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.14231(18) 0.80961(9) 0.07815(8) 0.0184(2) Uani 1 1 d . . . . .
C5 C 0.25857(19) 0.68871(10) 0.22587(8) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.200756 0.636440 0.253825 0.024 Uiso 1 1 calc R . . . .
C12 C -0.0482(2) 0.79127(11) -0.13792(10) 0.0295(3) Uani 1 1 d . . . . .
C17 C 0.5632(2) 0.70257(12) 0.34193(9) 0.0273(3) Uani 1 1 d . . . . .
H17A H 0.563157 0.770081 0.383584 0.033 Uiso 1 1 calc R . . . .
H17B H 0.480685 0.647402 0.358380 0.033 Uiso 1 1 calc R . . . .
C18 C 0.7685(2) 0.68997(12) 0.35404(10) 0.0287(3) Uani 1 1 d . . . . .
H18A H 0.851603 0.747835 0.341058 0.034 Uiso 1 1 calc R . . . .
H18B H 0.768899 0.624887 0.308933 0.034 Uiso 1 1 calc R . . . .
C14 C 0.2232(2) 0.96469(12) 0.45664(10) 0.0340(3) Uani 1 1 d . . . . .
H14A H 0.107811 0.911990 0.453761 0.051 Uiso 1 1 calc GR . . . .
H14B H 0.234854 1.027875 0.505662 0.051 Uiso 1 1 calc GR . . . .
H14C H 0.337978 0.938798 0.468141 0.051 Uiso 1 1 calc GR . . . .
C19 C 0.8568(2) 0.68752(12) 0.44840(10) 0.0289(3) Uani 1 1 d . . . . .
H19A H 0.879480 0.756967 0.492474 0.035 Uiso 1 1 calc R . . . .
H19B H 0.763838 0.638040 0.466210 0.035 Uiso 1 1 calc R . . . .
C21 C 1.1398(2) 0.64823(12) 0.54381(10) 0.0297(3) Uani 1 1 d . . . . .
H21A H 1.174464 0.717409 0.589621 0.036 Uiso 1 1 calc R . . . .
H21B H 1.044907 0.601077 0.562871 0.036 Uiso 1 1 calc R . . . .
C22 C 1.3198(2) 0.60843(12) 0.54050(10) 0.0330(3) Uani 1 1 d . . . . .
H22A H 1.413441 0.655285 0.520598 0.040 Uiso 1 1 calc R . . . .
H22B H 1.284271 0.539157 0.494788 0.040 Uiso 1 1 calc R . . . .
C25 C -0.4594(2) 0.43017(11) 0.12820(11) 0.0327(3) Uani 1 1 d . . . . .
H25A H -0.461764 0.364691 0.084194 0.049 Uiso 1 1 calc GR . . . .
H25B H -0.591813 0.437034 0.126014 0.049 Uiso 1 1 calc GR . . . .
H25C H -0.400592 0.430969 0.189111 0.049 Uiso 1 1 calc GR . . . .
C20 C 1.0468(2) 0.65606(12) 0.45248(10) 0.0312(3) Uani 1 1 d . . . . .
H20A H 1.139703 0.707042 0.436127 0.037 Uiso 1 1 calc R . . . .
H20B H 1.023786 0.588083 0.406163 0.037 Uiso 1 1 calc R . . . .
C15 C -0.0329(3) 1.02653(14) 0.32094(11) 0.0418(4) Uani 1 1 d . . . . .
H15A H -0.042765 1.048443 0.266386 0.063 Uiso 1 1 calc GR . . . .
H15B H -0.041111 1.082838 0.372018 0.063 Uiso 1 1 calc GR . . . .
H15C H -0.138835 0.965422 0.310899 0.063 Uiso 1 1 calc GR . . . .
C13 C 0.4035(3) 1.10471(13) 0.35475(12) 0.0472(4) Uani 1 1 d . . . . .
H13A H 0.526610 1.086434 0.367152 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.402754 1.165150 0.403926 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.387640 1.121043 0.297496 0.071 Uiso 1 1 calc GR . . . .
C23 C 1.4172(3) 0.60056(14) 0.63086(11) 0.0420(4) Uani 1 1 d . . . . .
H23A H 1.527007 0.570517 0.623224 0.063 Uiso 1 1 calc GR . . . .
H23B H 1.324195 0.556326 0.652234 0.063 Uiso 1 1 calc GR . . . .
H23C H 1.463117 0.669787 0.675263 0.063 Uiso 1 1 calc GR . . . .
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'
F F 0.0727 0.0534 '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
_geom_angle_publ_flag
C14 Si1 C3 109.43(6) . . ?
C15 Si1 C3 111.99(7) . . ?
C15 Si1 C14 107.67(8) . . ?
C13 Si1 C3 107.31(7) . . ?
C13 Si1 C14 110.40(8) . . ?
C13 Si1 C15 110.06(9) . . ?
C10 O2 C1 120.45(9) . . ?
C24 O4 C25 117.13(11) . . ?
C8 N1 C26 118.42(11) . . ?
C8 N1 C1 121.75(10) . . ?
C1 N1 C26 117.28(10) . . ?
C4 C3 Si1 117.80(10) . . ?
C4 C3 C2 125.97(11) . . ?
C2 C3 Si1 115.97(9) . . ?
C7 C6 C5 111.70(10) . . ?
C9 C6 C7 110.69(10) . . ?
C9 C6 C5 109.53(10) . . ?
C8 C7 C6 120.12(11) . . ?
C8 C7 C24 121.36(12) . . ?
C24 C7 C6 118.33(11) . . ?
O1 C9 C6 123.30(11) . . ?
O1 C9 C1 119.08(11) . . ?
C6 C9 C1 117.22(10) . . ?
C3 C4 C5 132.60(12) . . ?
C3 C2 C1 116.44(10) . . ?
F2 C11 C10 112.33(11) . . ?
F1 C11 F2 107.15(12) . . ?
F1 C11 F3 107.07(12) . . ?
F1 C11 C10 111.72(11) . . ?
F3 C11 F2 107.00(12) . . ?
F3 C11 C10 111.27(12) . . ?
C7 C8 N1 125.03(12) . . ?
O2 C10 C11 105.87(10) . . ?
O2 C10 C12 111.08(11) . . ?
C12 C10 C11 110.78(11) . . ?
C17 C16 C5 113.45(11) . . ?
O4 C24 C7 112.65(11) . . ?
O3 C24 O4 122.97(12) . . ?
O3 C24 C7 124.37(13) . . ?
O2 C1 N1 109.69(10) . . ?
O2 C1 C9 112.63(10) . . ?
O2 C1 C2 103.04(9) . . ?
N1 C1 C9 112.42(10) . . ?
N1 C1 C2 112.55(10) . . ?
C9 C1 C2 106.12(10) . . ?
C4 C5 C6 115.99(10) . . ?
C4 C5 C16 109.99(10) . . ?
C16 C5 C6 111.82(10) . . ?
F4 C12 C10 112.57(11) . . ?
F6 C12 F4 106.49(13) . . ?
F6 C12 C10 111.36(11) . . ?
F5 C12 F4 107.14(12) . . ?
F5 C12 F6 107.34(12) . . ?
F5 C12 C10 111.62(13) . . ?
C18 C17 C16 112.29(11) . . ?
C17 C18 C19 114.54(12) . . ?
C20 C19 C18 112.48(12) . . ?
C22 C21 C20 112.26(12) . . ?
C21 C22 C23 113.61(13) . . ?
C19 C20 C21 115.40(12) . . ?
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 C3 1.9028(13) . ?
Si1 C14 1.8705(15) . ?
Si1 C15 1.8589(17) . ?
Si1 C13 1.8528(18) . ?
O1 C9 1.2092(16) . ?
F2 C11 1.3312(16) . ?
O2 C10 1.4123(15) . ?
O2 C1 1.4359(14) . ?
F4 C12 1.3357(18) . ?
F6 C12 1.3319(17) . ?
F1 C11 1.3173(18) . ?
F5 C12 1.3314(17) . ?
O4 C24 1.3488(17) . ?
O4 C25 1.4375(16) . ?
O3 C24 1.2169(16) . ?
N1 C26 1.4633(16) . ?
N1 C8 1.3579(16) . ?
N1 C1 1.4499(16) . ?
F3 C11 1.3286(17) . ?
C3 C4 1.3415(18) . ?
C3 C2 1.5245(17) . ?
C6 C7 1.5040(18) . ?
C6 C9 1.4961(17) . ?
C6 C5 1.5627(17) . ?
C7 C8 1.3522(18) . ?
C7 C24 1.4561(18) . ?
C9 C1 1.5364(17) . ?
C4 C5 1.5151(17) . ?
C2 C1 1.5463(17) . ?
C11 C10 1.5326(19) . ?
C10 C12 1.530(2) . ?
C16 C5 1.5418(18) . ?
C16 C17 1.5283(18) . ?
C17 C18 1.522(2) . ?
C18 C19 1.5303(19) . ?
C19 C20 1.524(2) . ?
C21 C22 1.520(2) . ?
C21 C20 1.5259(19) . ?
C22 C23 1.523(2) . ?
