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#$Date: 2024-03-04 22:03:30 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/07/1570770.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_1570770
loop_
_publ_author_name
'Guerzoni, Michael G.'
'van Ingen, Yara'
'Babaahmadi, Rasool'
'Wirth, Thomas'
'Richards, Emma'
'Melen, Rebecca L.'
_publ_section_title
;
 An un-forgotten classic: the nitro-Mannich reaction between nitrones and
 silyl nitronates catalysed by B(C₆F₅)₃.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              2648
_journal_page_last               2654
_journal_paper_doi               10.1039/d3sc05672d
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H26 N2 O4 Si'
_chemical_formula_sum            'C21 H26 N2 O4 Si'
_chemical_formula_weight         398.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-10-16 deposited with the CCDC.	2023-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9467(4)
_cell_length_b                   10.7574(6)
_cell_length_c                   19.8365(9)
_cell_measurement_reflns_used    5764
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.3100
_cell_measurement_theta_min      4.0940
_cell_volume                     2122.52(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'ORTEP, Mercury'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'micro-focus sealed X-ray tube'
_diffrn_measurement_method       'w/ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9161
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.823
_diffrn_reflns_theta_min         3.464
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       blocks
_exptl_crystal_F_000             848
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.439
_exptl_crystal_size_min          0.173
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0357P)²+0.5160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                4488
_reflns_number_total             4976
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05672d2.cif
_cod_data_source_block           RM2339_a
_cod_depositor_comments
'Adding full bibliography for 1570770--1570774.cif.'
_cod_database_code               1570770
_shelx_shelxl_version_number     2018/3
_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   0.874
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_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
O1 O 0.40627(14) 0.51103(14) 0.66307(7) 0.0281(3) Uani 1 1 d . . . . .
N1 N 0.30589(17) 0.60862(17) 0.66881(9) 0.0263(4) Uani 1 1 d . . . . .
C1 C 0.1762(2) 0.5474(2) 0.68605(10) 0.0274(4) Uani 1 1 d . . . . .
H1 H 0.104121 0.611438 0.680461 0.033 Uiso 1 1 calc R U . . .
O2 O -0.05278(17) 0.4955(2) 0.76703(10) 0.0525(5) Uani 1 1 d . . . . .
N2 N 0.0540(2) 0.4448(2) 0.77937(9) 0.0364(4) Uani 1 1 d . . . . .
C2 C 0.1814(2) 0.5144(2) 0.76145(11) 0.0305(5) Uani 1 1 d . . . . .
H2 H 0.260757 0.459593 0.770038 0.037 Uiso 1 1 calc R U . . .
O3 O 0.0650(2) 0.34313(19) 0.80637(10) 0.0559(5) Uani 1 1 d . . . . .
C3 C 0.1901(3) 0.6281(3) 0.80679(12) 0.0411(6) Uani 1 1 d . . . . .
H00A H 0.107275 0.678144 0.801427 0.049 Uiso 1 1 calc R U . . .
H00D H 0.267086 0.679996 0.792332 0.049 Uiso 1 1 calc R U . . .
O4 O 0.03652(17) 0.16215(16) 0.50747(8) 0.0376(4) Uani 1 1 d . . . . .
C4 C 0.2073(3) 0.5946(3) 0.88087(13) 0.0534(8) Uani 1 1 d . . . . .
H00X H 0.125920 0.552954 0.897152 0.080 Uiso 1 1 calc R U . . .
H00Y H 0.222657 0.670391 0.907139 0.080 Uiso 1 1 calc R U . . .
H00Z H 0.284517 0.538717 0.885985 0.080 Uiso 1 1 calc R U . . .
Si1 Si 0.55621(6) 0.55410(6) 0.69492(3) 0.03164(15) Uani 1 1 d . . . . .
C5 C 0.5583(3) 0.5481(3) 0.78838(13) 0.0601(8) Uani 1 1 d . . . . .
H00U H 0.528876 0.465777 0.803479 0.090 Uiso 1 1 calc R U . . .
H00V H 0.497460 0.611579 0.806401 0.090 Uiso 1 1 calc R U . . .
H00W H 0.649812 0.563871 0.804631 0.090 Uiso 1 1 calc R U . . .
C6 C 0.6030(3) 0.7133(3) 0.67000(14) 0.0467(6) Uani 1 1 d . . . . .
H00H H 0.593927 0.722171 0.621047 0.070 Uiso 1 1 calc R U . . .
H6 H 0.696419 0.729421 0.683111 0.070 Uiso 1 1 calc R U . . .
H00O H 0.543713 0.772883 0.692590 0.070 Uiso 1 1 calc R U . . .
C7 C 0.6680(3) 0.4359(3) 0.65781(17) 0.0549(7) Uani 1 1 d . . . . .
H00R H 0.665829 0.442761 0.608554 0.082 Uiso 1 1 calc R U . . .
H00S H 0.637562 0.352926 0.671279 0.082 Uiso 1 1 calc R U . . .
H00T H 0.760064 0.449253 0.673850 0.082 Uiso 1 1 calc R U . . .
C8 C 0.2980(2) 0.6770(2) 0.60646(11) 0.0276(4) Uani 1 1 d . . . . .
C9 C 0.3603(3) 0.6399(2) 0.54757(11) 0.0383(5) Uani 1 1 d . . . . .
H9 H 0.408128 0.563558 0.545896 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3522(3) 0.7153(3) 0.49075(13) 0.0503(7) Uani 1 1 d . . . . .
H00P H 0.396312 0.690716 0.450396 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2815(3) 0.8245(3) 0.49230(15) 0.0501(7) Uani 1 1 d . . . . .
H00Q H 0.276095 0.875105 0.453143 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2181(3) 0.8608(3) 0.55108(15) 0.0469(6) Uani 1 1 d . . . . .
H12 H 0.167874 0.935907 0.552126 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2275(2) 0.7882(2) 0.60827(13) 0.0372(5) Uani 1 1 d . . . . .
H13 H 0.185587 0.814466 0.648898 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1397(2) 0.4391(2) 0.64042(10) 0.0262(4) Uani 1 1 d . . . . .
C15 C 0.1834(2) 0.3178(2) 0.65366(11) 0.0296(5) Uani 1 1 d . . . . .
H15 H 0.236320 0.302900 0.692698 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1523(2) 0.2191(2) 0.61198(11) 0.0321(5) Uani 1 1 d . . . . .
H16 H 0.180819 0.136771 0.621876 0.038 Uiso 1 1 calc R U . . .
C17 C 0.0777(2) 0.2461(2) 0.55526(10) 0.0297(5) Uani 1 1 d . . . . .
C18 C 0.0312(2) 0.3648(2) 0.54020(11) 0.0310(5) Uani 1 1 d . . . . .
C19 C 0.0627(2) 0.4625(2) 0.58357(10) 0.0312(5) Uani 1 1 d . . . . .
H19 H 0.031766 0.544242 0.574259 0.037 Uiso 1 1 calc R U . . .
C20 C -0.0450(3) 0.3503(3) 0.47908(12) 0.0422(6) Uani 1 1 d . . . . .
H20 H -0.090754 0.413963 0.455119 0.051 Uiso 1 1 calc R U . . .
C21 C -0.0391(3) 0.2304(3) 0.46248(12) 0.0433(6) Uani 1 1 d . . . . .
H21 H -0.082008 0.195876 0.424016 0.052 Uiso 1 1 calc R U . . .
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
N1 O1 Si1 112.35(11) . . ?
C8 N1 O1 109.81(16) . . ?
C8 N1 C1 112.07(16) . . ?
O1 N1 C1 107.11(15) . . ?
N1 C1 C14 114.16(16) . . ?
N1 C1 C2 107.22(16) . . ?
C14 C1 C2 114.24(18) . . ?
N1 C1 H1 106.9 . . ?
C14 C1 H1 106.9 . . ?
C2 C1 H1 106.9 . . ?
O2 N2 O3 124.5(2) . . ?
O2 N2 C2 117.4(2) . . ?
O3 N2 C2 118.1(2) . . ?
N2 C2 C3 107.87(18) . . ?
N2 C2 C1 108.31(17) . . ?
C3 C2 C1 113.0(2) . . ?
N2 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C2 C3 C4 112.7(2) . . ?
C2 C3 H00A 109.0 . . ?
C4 C3 H00A 109.0 . . ?
C2 C3 H00D 109.0 . . ?
C4 C3 H00D 109.0 . . ?
H00A C3 H00D 107.8 . . ?
C17 O4 C21 105.03(18) . . ?
C3 C4 H00X 109.5 . . ?
C3 C4 H00Y 109.5 . . ?
H00X C4 H00Y 109.5 . . ?
C3 C4 H00Z 109.5 . . ?
H00X C4 H00Z 109.5 . . ?
H00Y C4 H00Z 109.5 . . ?
O1 Si1 C6 112.27(10) . . ?
O1 Si1 C7 101.23(11) . . ?
C6 Si1 C7 112.43(14) . . ?
O1 Si1 C5 112.04(12) . . ?
C6 Si1 C5 107.31(14) . . ?
C7 Si1 C5 111.62(16) . . ?
Si1 C5 H00U 109.5 . . ?
Si1 C5 H00V 109.5 . . ?
H00U C5 H00V 109.5 . . ?
Si1 C5 H00W 109.5 . . ?
H00U C5 H00W 109.5 . . ?
H00V C5 H00W 109.5 . . ?
Si1 C6 H00H 109.5 . . ?
Si1 C6 H6 109.5 . . ?
H00H C6 H6 109.5 . . ?
Si1 C6 H00O 109.5 . . ?
H00H C6 H00O 109.5 . . ?
H6 C6 H00O 109.5 . . ?
Si1 C7 H00R 109.5 . . ?
Si1 C7 H00S 109.5 . . ?
H00R C7 H00S 109.5 . . ?
Si1 C7 H00T 109.5 . . ?
H00R C7 H00T 109.5 . . ?
H00S C7 H00T 109.5 . . ?
C9 C8 C13 119.9(2) . . ?
C9 C8 N1 123.6(2) . . ?
C13 C8 N1 116.5(2) . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H00P 119.6 . . ?
C9 C10 H00P 119.6 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H00Q 120.1 . . ?
C12 C11 H00Q 120.1 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C19 C14 C15 119.6(2) . . ?
C19 C14 C1 118.5(2) . . ?
C15 C14 C1 121.92(18) . . ?
C16 C15 C14 122.34(19) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C17 C16 C15 116.5(2) . . ?
C17 C16 H16 121.7 . . ?
C15 C16 H16 121.7 . . ?
O4 C17 C16 125.8(2) . . ?
O4 C17 C18 110.91(18) . . ?
C16 C17 C18 123.3(2) . . ?
C17 C18 C19 119.0(2) . . ?
C17 C18 C20 104.9(2) . . ?
C19 C18 C20 136.1(2) . . ?
C14 C19 C18 119.3(2) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C18 106.9(2) . . ?
C21 C20 H20 126.6 . . ?
C18 C20 H20 126.6 . . ?
C20 C21 O4 112.3(2) . . ?
C20 C21 H21 123.8 . . ?
O4 C21 H21 123.8 . . ?
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
O1 N1 1.453(2) . ?
O1 Si1 1.6846(15) . ?
N1 C8 1.441(3) . ?
N1 C1 1.489(3) . ?
C1 C14 1.519(3) . ?
C1 C2 1.538(3) . ?
C1 H1 1.0000 . ?
O2 N2 1.220(3) . ?
N2 O3 1.222(3) . ?
N2 C2 1.514(3) . ?
C2 C3 1.521(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.523(4) . ?
C3 H00A 0.9900 . ?
C3 H00D 0.9900 . ?
O4 C17 1.372(3) . ?
O4 C21 1.379(3) . ?
C4 H00X 0.9800 . ?
C4 H00Y 0.9800 . ?
C4 H00Z 0.9800 . ?
Si1 C6 1.842(3) . ?
Si1 C7 1.842(3) . ?
Si1 C5 1.855(3) . ?
C5 H00U 0.9800 . ?
C5 H00V 0.9800 . ?
C5 H00W 0.9800 . ?
C6 H00H 0.9800 . ?
C6 H6 0.9800 . ?
C6 H00O 0.9800 . ?
C7 H00R 0.9800 . ?
C7 H00S 0.9800 . ?
C7 H00T 0.9800 . ?
C8 C9 1.381(3) . ?
C8 C13 1.388(3) . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.370(4) . ?
C10 H00P 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H00Q 0.9500 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.386(3) . ?
C14 C15 1.400(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C18 C19 1.394(3) . ?
C18 C20 1.438(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.332(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
