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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/1/57/07/1570773.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_1570773
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_formula_moiety         ' C32 H13 B F15 N O'
_chemical_formula_sum            'C32 H13 B F15 N O'
_chemical_formula_weight         723.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 107.799(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4252(5)
_cell_length_b                   8.0582(3)
_cell_length_c                   20.1712(6)
_cell_measurement_reflns_used    5020
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.3250
_cell_measurement_theta_min      4.4850
_cell_volume                     2851.55(16)
_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    'Mercury, ORTEP'
_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 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11158
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.786
_diffrn_reflns_theta_min         4.523
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.530
_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    1.685
_exptl_crystal_description       plates
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0514
_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)+(0.0402P)²+2.6583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4493
_reflns_number_total             5518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05672d2.cif
_cod_data_source_block           RM2354_a
_cod_depositor_comments
'Adding full bibliography for 1570770--1570774.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570773
_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   0.595
_shelx_estimated_absorpt_t_max   0.909
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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 0.77901(9) 0.4272(2) 0.62493(8) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.72620(12) 0.3170(3) 0.58786(10) 0.0287(4) Uani 1 1 d . . . . .
C1 C 0.73450(14) 0.2331(3) 0.53628(13) 0.0307(5) Uani 1 1 d . . . . .
H1 H 0.695499 0.154204 0.516725 0.037 Uiso 1 1 calc R U . . .
B1 B 0.76461(16) 0.6154(4) 0.61172(14) 0.0277(6) Uani 1 1 d . . . . .
C2 C 0.79443(15) 0.2409(3) 0.50361(13) 0.0325(6) Uani 1 1 d . . . . .
F3 F 0.48889(10) 0.7888(3) 0.68035(10) 0.0588(6) Uani 1 1 d . . . . .
C3 C 0.86728(16) 0.3008(4) 0.53763(16) 0.0423(7) Uani 1 1 d . . . . .
H3 H 0.878911 0.343955 0.583517 0.051 Uiso 1 1 calc R U . . .
F4 F 0.60319(10) 0.6119(3) 0.77016(9) 0.0512(5) Uani 1 1 d . . . . .
C4 C 0.92260(18) 0.2969(5) 0.50413(19) 0.0572(9) Uani 1 1 d . . . . .
H4 H 0.972551 0.336027 0.527331 0.069 Uiso 1 1 calc R U . . .
F5 F 0.72937(8) 0.5421(2) 0.73833(7) 0.0348(3) Uani 1 1 d . . . . .
C5 C 0.9053(2) 0.2361(6) 0.4370(2) 0.0629(10) Uani 1 1 d . . . . .
H5 H 0.942974 0.236731 0.413739 0.075 Uiso 1 1 calc R U . . .
F6 F 0.78890(10) 0.9603(2) 0.62103(10) 0.0494(4) Uani 1 1 d . . . . .
C6 C 0.8337(2) 0.1749(5) 0.40389(18) 0.0574(9) Uani 1 1 d . . . . .
H6 H 0.822964 0.132477 0.357951 0.069 Uiso 1 1 calc R U . . .
F7 F 0.88561(12) 1.1324(2) 0.72412(13) 0.0644(6) Uani 1 1 d . . . . .
C7 C 0.77703(18) 0.1734(4) 0.43573(15) 0.0420(7) Uani 1 1 d . . . . .
F8 F 0.98507(11) 0.9718(3) 0.83330(11) 0.0583(5) Uani 1 1 d . . . . .
C8 C 0.6998(2) 0.1052(6) 0.39755(18) 0.0609(10) Uani 1 1 d . . . . .
H01A H 0.660937 0.189434 0.395755 0.091 Uiso 1 1 calc R U . . .
H8 H 0.689896 0.006595 0.421866 0.091 Uiso 1 1 calc R U . . .
H01F H 0.698266 0.074938 0.350068 0.091 Uiso 1 1 calc R U . . .
F9 F 0.98528(10) 0.6342(3) 0.83615(9) 0.0522(5) Uani 1 1 d . . . . .
F2 F 0.50590(9) 0.9009(2) 0.55937(9) 0.0460(4) Uani 1 1 d . . . . .
C9 C 0.66533(15) 0.2777(3) 0.61760(14) 0.0329(6) Uani 1 1 d . . . . .
F10 F 0.89043(10) 0.4620(2) 0.73639(9) 0.0457(4) Uani 1 1 d . . . . .
C10 C 0.68629(19) 0.2185(4) 0.68528(15) 0.0425(7) Uani 1 1 d . . . . .
H10 H 0.738416 0.204266 0.711264 0.051 Uiso 1 1 calc R U . . .
F11 F 0.63840(9) 0.5423(2) 0.48370(8) 0.0398(4) Uani 1 1 d . . . . .
F1 F 0.63364(9) 0.8467(2) 0.52851(8) 0.0374(4) Uani 1 1 d . . . . .
C20 C 0.67472(14) 0.6281(3) 0.69116(13) 0.0298(5) Uani 1 1 d . . . . .
C21 C 0.83403(14) 0.7024(3) 0.67209(13) 0.0294(5) Uani 1 1 d . . . . .
C22 C 0.83789(15) 0.8738(4) 0.67410(15) 0.0354(6) Uani 1 1 d . . . . .
C23 C 0.88721(16) 0.9663(4) 0.72626(18) 0.0424(7) Uani 1 1 d . . . . .
C24 C 0.93715(15) 0.8853(4) 0.78108(16) 0.0404(7) Uani 1 1 d . . . . .
C25 C 0.93715(15) 0.7151(4) 0.78234(14) 0.0367(6) Uani 1 1 d . . . . .
C26 C 0.88653(15) 0.6277(3) 0.72885(14) 0.0319(5) Uani 1 1 d . . . . .
C27 C 0.76465(15) 0.6481(4) 0.53103(14) 0.0339(6) Uani 1 1 d . . . . .
C28 C 0.70340(16) 0.6018(4) 0.47410(14) 0.0348(6) Uani 1 1 d . . . . .
C29 C 0.70298(19) 0.6066(4) 0.40556(15) 0.0448(7) Uani 1 1 d . . . . .
C30 C 0.7668(2) 0.6594(5) 0.39085(16) 0.0536(9) Uani 1 1 d . . . . .
C31 C 0.82911(19) 0.7084(5) 0.44420(18) 0.0548(9) Uani 1 1 d . . . . .
C32 C 0.82713(16) 0.7009(4) 0.51233(16) 0.0432(7) Uani 1 1 d . . . . .
C16 C 0.62776(15) 0.7748(3) 0.58751(13) 0.0306(5) Uani 1 1 d . . . . .
C17 C 0.56164(15) 0.8108(4) 0.60302(14) 0.0346(6) Uani 1 1 d . . . . .
C19 C 0.61045(16) 0.6646(4) 0.70907(13) 0.0354(6) Uani 1 1 d . . . . .
C18 C 0.55266(15) 0.7537(4) 0.66412(15) 0.0389(6) Uani 1 1 d . . . . .
C11 C 0.6293(2) 0.1808(5) 0.71368(18) 0.0578(9) Uani 1 1 d . . . . .
H11 H 0.642146 0.138423 0.759772 0.069 Uiso 1 1 calc R U . . .
F12 F 0.64045(12) 0.5585(3) 0.35430(9) 0.0616(6) Uani 1 1 d . . . . .
C14 C 0.59016(17) 0.2984(4) 0.57868(16) 0.0425(7) Uani 1 1 d . . . . .
H14 H 0.577014 0.336855 0.531986 0.051 Uiso 1 1 calc R U . . .
F15 F 0.89197(10) 0.7448(3) 0.56113(10) 0.0600(6) Uani 1 1 d . . . . .
C15 C 0.68588(14) 0.6750(3) 0.62834(12) 0.0273(5) Uani 1 1 d . . . . .
C12 C 0.5538(2) 0.2037(5) 0.67630(19) 0.0590(10) Uani 1 1 d . . . . .
H12 H 0.515080 0.179270 0.696966 0.071 Uiso 1 1 calc R U . . .
F13 F 0.76827(15) 0.6606(4) 0.32464(10) 0.0823(8) Uani 1 1 d . . . . .
C13 C 0.53441(19) 0.2618(5) 0.60911(19) 0.0545(9) Uani 1 1 d . . . . .
H13 H 0.482255 0.276986 0.583412 0.065 Uiso 1 1 calc R U . . .
F14 F 0.89203(12) 0.7581(4) 0.43060(12) 0.0796(8) Uani 1 1 d . . . . .
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'
B B 0.0090 0.0039 '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'
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 B1 119.26(18) . . ?
C1 N1 O1 123.0(2) . . ?
C1 N1 C9 120.9(2) . . ?
O1 N1 C9 115.22(19) . . ?
N1 C1 C2 129.7(3) . . ?
N1 C1 H1 115.1 . . ?
C2 C1 H1 115.1 . . ?
O1 B1 C21 103.8(2) . . ?
O1 B1 C27 105.9(2) . . ?
C21 B1 C27 115.6(2) . . ?
O1 B1 C15 111.3(2) . . ?
C21 B1 C15 105.1(2) . . ?
C27 B1 C15 114.7(2) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 C1 122.9(2) . . ?
C7 C2 C1 116.4(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 117.7(3) . . ?
C6 C7 C8 119.8(3) . . ?
C2 C7 C8 122.4(3) . . ?
C7 C8 H01A 109.5 . . ?
C7 C8 H8 109.5 . . ?
H01A C8 H8 109.5 . . ?
C7 C8 H01F 109.5 . . ?
H01A C8 H01F 109.5 . . ?
H8 C8 H01F 109.5 . . ?
C14 C9 C10 122.2(3) . . ?
C14 C9 N1 120.3(2) . . ?
C10 C9 N1 117.5(2) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
F5 C20 C19 116.3(2) . . ?
F5 C20 C15 119.6(2) . . ?
C19 C20 C15 124.0(2) . . ?
C22 C21 C26 113.0(2) . . ?
C22 C21 B1 118.2(2) . . ?
C26 C21 B1 128.2(2) . . ?
F6 C22 C23 116.5(3) . . ?
F6 C22 C21 118.2(2) . . ?
C23 C22 C21 125.3(3) . . ?
F7 C23 C24 120.3(3) . . ?
F7 C23 C22 120.8(3) . . ?
C24 C23 C22 118.8(3) . . ?
F8 C24 C23 120.3(3) . . ?
F8 C24 C25 120.5(3) . . ?
C23 C24 C25 119.2(3) . . ?
F9 C25 C24 119.8(3) . . ?
F9 C25 C26 120.3(3) . . ?
C24 C25 C26 119.9(3) . . ?
F10 C26 C25 114.7(2) . . ?
F10 C26 C21 121.5(2) . . ?
C25 C26 C21 123.8(3) . . ?
C32 C27 C28 112.9(2) . . ?
C32 C27 B1 124.7(2) . . ?
C28 C27 B1 121.8(2) . . ?
F11 C28 C29 114.7(3) . . ?
F11 C28 C27 120.3(2) . . ?
C29 C28 C27 125.0(3) . . ?
F12 C29 C30 120.9(3) . . ?
F12 C29 C28 120.1(3) . . ?
C30 C29 C28 119.0(3) . . ?
F13 C30 C29 119.9(3) . . ?
F13 C30 C31 120.7(3) . . ?
C29 C30 C31 119.3(3) . . ?
F14 C31 C30 119.9(3) . . ?
F14 C31 C32 120.4(3) . . ?
C30 C31 C32 119.7(3) . . ?
F15 C32 C27 120.6(3) . . ?
F15 C32 C31 115.3(3) . . ?
C27 C32 C31 124.0(3) . . ?
F1 C16 C17 115.0(2) . . ?
F1 C16 C15 120.9(2) . . ?
C17 C16 C15 124.2(2) . . ?
F2 C17 C18 119.5(2) . . ?
F2 C17 C16 121.1(2) . . ?
C18 C17 C16 119.4(2) . . ?
F4 C19 C18 119.7(2) . . ?
F4 C19 C20 120.5(2) . . ?
C18 C19 C20 119.8(2) . . ?
F3 C18 C19 120.6(2) . . ?
F3 C18 C17 120.2(3) . . ?
C19 C18 C17 119.1(2) . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C9 C14 C13 118.4(3) . . ?
C9 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C16 C15 C20 113.2(2) . . ?
C16 C15 B1 127.7(2) . . ?
C20 C15 B1 119.1(2) . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
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 1.360(3) . ?
O1 B1 1.548(3) . ?
N1 C1 1.289(3) . ?
N1 C9 1.459(3) . ?
C1 C2 1.450(4) . ?
C1 H1 0.9500 . ?
B1 C21 1.630(4) . ?
B1 C27 1.649(4) . ?
B1 C15 1.657(4) . ?
C2 C3 1.394(4) . ?
C2 C7 1.416(4) . ?
F3 C18 1.343(3) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
F4 C19 1.348(3) . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
F5 C20 1.347(3) . ?
C5 C6 1.375(6) . ?
C5 H5 0.9500 . ?
F6 C22 1.363(3) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
F7 C23 1.339(4) . ?
C7 C8 1.499(5) . ?
F8 C24 1.344(3) . ?
C8 H01A 0.9800 . ?
C8 H8 0.9800 . ?
C8 H01F 0.9800 . ?
F9 C25 1.342(3) . ?
F2 C17 1.343(3) . ?
C9 C14 1.377(4) . ?
C9 C10 1.385(4) . ?
F10 C26 1.344(3) . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
F11 C28 1.358(3) . ?
F1 C16 1.358(3) . ?
C20 C19 1.372(4) . ?
C20 C15 1.396(3) . ?
C21 C22 1.383(4) . ?
C21 C26 1.390(4) . ?
C22 C23 1.380(4) . ?
C23 C24 1.368(5) . ?
C24 C25 1.372(4) . ?
C25 C26 1.384(4) . ?
C27 C32 1.384(4) . ?
C27 C28 1.393(4) . ?
C28 C29 1.381(4) . ?
C29 F12 1.348(4) . ?
C29 C30 1.365(5) . ?
C30 F13 1.344(3) . ?
C30 C31 1.370(5) . ?
C31 F14 1.332(4) . ?
C31 C32 1.387(4) . ?
C32 F15 1.343(4) . ?
C16 C17 1.378(4) . ?
C16 C15 1.390(4) . ?
C17 C18 1.372(4) . ?
C19 C18 1.371(4) . ?
C11 C12 1.377(5) . ?
C11 H11 0.9500 . ?
C14 C13 1.380(4) . ?
C14 H14 0.9500 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
