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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/1/57/07/1570772.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_1570772
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     direct
_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                 93.949(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0639(4)
_cell_length_b                   11.4369(3)
_cell_length_c                   19.0593(5)
_cell_measurement_reflns_used    5383
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.6430
_cell_measurement_theta_min      3.9690
_cell_volume                     2840.90(14)
_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
_computing_publication_material  publCIF
_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 0.999
_diffrn_measured_fraction_theta_max 0.973
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11862
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.814
_diffrn_reflns_theta_min         4.511
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.595
_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            yellow
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0458
_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)+(0.0719P)²+1.1395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4370
_reflns_number_total             5511
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05672d2.cif
_cod_data_source_block           RM2364b_a
_cod_depositor_comments
'Adding full bibliography for 1570770--1570774.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570772
_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   0.702
_shelx_estimated_absorpt_t_max   0.798
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
F1 F 0.94106(10) 0.46313(12) 0.57876(8) 0.0515(3) Uani 1 1 d . . . . .
F3 F 0.85333(16) 0.14122(15) 0.43545(8) 0.0730(5) Uani 1 1 d . . . . .
F4 F 0.67945(14) 0.11149(14) 0.50433(8) 0.0667(4) Uani 1 1 d . . . . .
F5 F 0.63865(10) 0.24814(12) 0.60981(7) 0.0498(3) Uani 1 1 d . . . . .
F6 F 0.57917(11) 0.51014(13) 0.56848(7) 0.0521(3) Uani 1 1 d . . . . .
F7 F 0.53760(14) 0.69640(17) 0.48829(9) 0.0720(5) Uani 1 1 d . . . . .
F8 F 0.68101(17) 0.86637(14) 0.47673(9) 0.0768(5) Uani 1 1 d . . . . .
F9 F 0.86145(15) 0.85340(13) 0.55483(9) 0.0666(4) Uani 1 1 d . . . . .
F10 F 0.90115(10) 0.67533(12) 0.64267(7) 0.0497(3) Uani 1 1 d . . . . .
F11 F 0.96103(10) 0.32856(12) 0.70006(8) 0.0503(3) Uani 1 1 d . . . . .
F12 F 1.10530(12) 0.39708(16) 0.79538(10) 0.0699(5) Uani 1 1 d . . . . .
F13 F 1.07023(17) 0.57813(18) 0.88332(11) 0.0904(7) Uani 1 1 d . . . . .
F14 F 0.88760(16) 0.69505(16) 0.86916(9) 0.0758(5) Uani 1 1 d . . . . .
F15 F 0.75119(12) 0.64247(14) 0.76428(8) 0.0598(4) Uani 1 1 d . . . . .
O1 O 0.65992(11) 0.44550(13) 0.69139(7) 0.0364(3) Uani 1 1 d . . . . .
N1 N 0.65074(13) 0.36492(15) 0.74354(9) 0.0349(4) Uani 1 1 d . . . . .
C1 C 0.71498(16) 0.27980(19) 0.75465(11) 0.0362(4) Uani 1 1 d . . . . .
H1 H 0.768741 0.277295 0.723558 0.043 Uiso 1 1 calc R U . . .
F2 F 0.98455(14) 0.31889(16) 0.47597(9) 0.0731(5) Uani 1 1 d . . . . .
C2 C 0.71811(16) 0.18734(19) 0.80707(11) 0.0376(4) Uani 1 1 d . . . . .
C11 C 0.4005(2) 0.4566(2) 0.85623(15) 0.0586(7) Uani 1 1 d . . . . .
H11 H 0.343526 0.479422 0.881434 0.070 Uiso 1 1 calc R U . . .
C12 C 0.3827(2) 0.3938(3) 0.79634(15) 0.0578(6) Uani 1 1 d . . . . .
H12 H 0.314413 0.373237 0.780750 0.069 Uiso 1 1 calc R U . . .
C13 C 0.46592(19) 0.3584(2) 0.75662(14) 0.0513(6) Uani 1 1 d . . . . .
C14 C 0.4499(2) 0.2921(4) 0.69125(18) 0.0757(9) Uani 1 1 d . . . . .
H01C H 0.376165 0.282141 0.679660 0.114 Uiso 1 1 calc R U . . .
H14 H 0.482447 0.215194 0.697111 0.114 Uiso 1 1 calc R U . . .
H01F H 0.480353 0.334485 0.653148 0.114 Uiso 1 1 calc R U . . .
C15 C 0.78827(16) 0.36366(18) 0.60103(10) 0.0343(4) Uani 1 1 d . . . . .
C16 C 0.87502(17) 0.37526(19) 0.56279(11) 0.0403(5) Uani 1 1 d . . . . .
C17 C 0.8985(2) 0.3026(2) 0.50878(12) 0.0485(6) Uani 1 1 d . . . . .
C18 C 0.8328(2) 0.2128(2) 0.48858(12) 0.0501(6) Uani 1 1 d . . . . .
C19 C 0.7454(2) 0.1981(2) 0.52333(12) 0.0453(5) Uani 1 1 d . . . . .
C20 C 0.72555(17) 0.27181(19) 0.57812(11) 0.0381(4) Uani 1 1 d . . . . .
C21 C 0.74039(16) 0.58404(19) 0.61209(11) 0.0371(4) Uani 1 1 d . . . . .
C22 C 0.65004(18) 0.5955(2) 0.56994(11) 0.0416(5) Uani 1 1 d . . . . .
C23 C 0.6275(2) 0.6898(2) 0.52620(12) 0.0502(6) Uani 1 1 d . . . . .
C24 C 0.7000(2) 0.7758(2) 0.52057(13) 0.0537(6) Uani 1 1 d . . . . .
C25 C 0.7912(2) 0.7692(2) 0.55990(13) 0.0485(6) Uani 1 1 d . . . . .
C26 C 0.80989(17) 0.67494(19) 0.60527(11) 0.0402(5) Uani 1 1 d . . . . .
C27 C 0.85001(17) 0.48534(19) 0.72441(11) 0.0385(5) Uani 1 1 d . . . . .
C28 C 0.94074(18) 0.4243(2) 0.73811(12) 0.0421(5) Uani 1 1 d . . . . .
C29 C 1.0159(2) 0.4551(2) 0.78960(14) 0.0523(6) Uani 1 1 d . . . . .
C30 C 0.9988(2) 0.5469(2) 0.83378(14) 0.0591(7) Uani 1 1 d . . . . .
C31 C 0.9073(2) 0.6067(2) 0.82585(13) 0.0551(6) Uani 1 1 d . . . . .
C32 C 0.83645(19) 0.5763(2) 0.77168(12) 0.0449(5) Uani 1 1 d . . . . .
B1 B 0.76299(18) 0.4652(2) 0.65899(12) 0.0348(5) Uani 1 1 d . . . . .
C3 C 0.80784(18) 0.1223(2) 0.81070(13) 0.0483(6) Uani 1 1 d . . . . .
H3 H 0.859962 0.140505 0.780070 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8228(2) 0.0312(3) 0.85816(15) 0.0584(7) Uani 1 1 d . . . . .
H4 H 0.884628 -0.012799 0.859927 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7477(2) 0.0051(3) 0.90271(15) 0.0575(7) Uani 1 1 d . . . . .
H5 H 0.757393 -0.057694 0.935147 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6587(2) 0.0691(3) 0.90054(15) 0.0586(7) Uani 1 1 d . . . . .
H6 H 0.607744 0.050992 0.932071 0.070 Uiso 1 1 calc R U . . .
C7 C 0.64224(19) 0.1595(2) 0.85321(14) 0.0521(6) Uani 1 1 d . . . . .
H7 H 0.580021 0.202719 0.851786 0.063 Uiso 1 1 calc R U . . .
C8 C 0.56187(17) 0.39196(19) 0.78290(12) 0.0423(5) Uani 1 1 d . . . . .
C9 C 0.5798(2) 0.4562(2) 0.84489(13) 0.0550(6) Uani 1 1 d . . . . .
H9 H 0.647554 0.477495 0.861329 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4962(2) 0.4884(3) 0.88193(15) 0.0625(7) Uani 1 1 d . . . . .
H10 H 0.505683 0.531736 0.924396 0.075 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 0.0181 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 120.95(15) . . ?
C1 N1 O1 122.56(16) . . ?
C1 N1 C8 127.30(18) . . ?
O1 N1 C8 110.12(16) . . ?
N1 C1 C2 130.35(19) . . ?
C3 C2 C7 118.5(2) . . ?
C3 C2 C1 114.11(19) . . ?
C7 C2 C1 127.4(2) . . ?
C12 C11 C10 123.1(3) . . ?
C11 C12 C13 120.3(3) . . ?
C8 C13 C12 116.0(2) . . ?
C8 C13 C14 122.0(2) . . ?
C12 C13 C14 122.0(2) . . ?
C20 C15 C16 113.06(19) . . ?
C20 C15 B1 127.10(18) . . ?
C16 C15 B1 119.31(18) . . ?
F1 C16 C17 116.63(19) . . ?
F1 C16 C15 118.95(19) . . ?
C17 C16 C15 124.4(2) . . ?
F2 C17 C16 120.3(2) . . ?
F2 C17 C18 120.1(2) . . ?
C16 C17 C18 119.6(2) . . ?
F3 C18 C19 120.4(2) . . ?
F3 C18 C17 120.8(2) . . ?
C19 C18 C17 118.8(2) . . ?
F4 C19 C18 120.0(2) . . ?
F4 C19 C20 120.2(2) . . ?
C18 C19 C20 119.8(2) . . ?
F5 C20 C19 115.1(2) . . ?
F5 C20 C15 120.59(18) . . ?
C19 C20 C15 124.3(2) . . ?
C22 C21 C26 114.2(2) . . ?
C22 C21 B1 120.49(19) . . ?
C26 C21 B1 125.1(2) . . ?
F6 C22 C23 115.8(2) . . ?
F6 C22 C21 120.0(2) . . ?
C23 C22 C21 124.1(2) . . ?
F7 C23 C24 120.1(2) . . ?
F7 C23 C22 120.9(2) . . ?
C24 C23 C22 119.1(2) . . ?
F8 C24 C25 120.0(3) . . ?
F8 C24 C23 120.1(3) . . ?
C25 C24 C23 119.8(2) . . ?
F9 C25 C24 119.8(2) . . ?
F9 C25 C26 120.7(2) . . ?
C24 C25 C26 119.5(2) . . ?
F10 C26 C21 120.8(2) . . ?
F10 C26 C25 115.9(2) . . ?
C21 C26 C25 123.3(2) . . ?
C28 C27 C32 113.5(2) . . ?
C28 C27 B1 127.6(2) . . ?
C32 C27 B1 118.8(2) . . ?
F11 C28 C29 115.6(2) . . ?
F11 C28 C27 120.3(2) . . ?
C29 C28 C27 124.1(2) . . ?
F12 C29 C30 120.3(2) . . ?
F12 C29 C28 120.2(2) . . ?
C30 C29 C28 119.5(3) . . ?
F13 C30 C29 120.3(3) . . ?
F13 C30 C31 120.4(3) . . ?
C29 C30 C31 119.3(2) . . ?
F14 C31 C30 120.6(2) . . ?
F14 C31 C32 120.2(3) . . ?
C30 C31 C32 119.2(2) . . ?
F15 C32 C31 116.3(2) . . ?
F15 C32 C27 119.5(2) . . ?
C31 C32 C27 124.2(2) . . ?
O1 B1 C21 102.14(16) . . ?
O1 B1 C27 107.16(16) . . ?
C21 B1 C27 112.67(18) . . ?
O1 B1 C15 112.78(17) . . ?
C21 B1 C15 104.74(16) . . ?
C27 B1 C15 116.49(17) . . ?
C4 C3 C2 121.2(2) . . ?
C5 C4 C3 119.5(2) . . ?
C6 C5 C4 120.3(2) . . ?
C5 C6 C7 120.9(2) . . ?
C6 C7 C2 119.6(2) . . ?
C13 C8 C9 123.5(2) . . ?
C13 C8 N1 119.5(2) . . ?
C9 C8 N1 117.0(2) . . ?
C10 C9 C8 118.5(3) . . ?
C11 C10 C9 118.7(3) . . ?
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
F1 C16 1.346(3) . ?
F3 C18 1.344(3) . ?
F4 C19 1.346(3) . ?
F5 C20 1.350(2) . ?
F6 C22 1.345(3) . ?
F7 C23 1.338(3) . ?
F8 C24 1.343(3) . ?
F9 C25 1.338(3) . ?
F10 C26 1.346(3) . ?
F11 C28 1.350(3) . ?
F12 C29 1.342(3) . ?
F13 C30 1.330(3) . ?
F14 C31 1.341(3) . ?
F15 C32 1.346(3) . ?
O1 N1 1.367(2) . ?
O1 B1 1.536(3) . ?
N1 C1 1.293(3) . ?
N1 C8 1.458(3) . ?
C1 C2 1.453(3) . ?
F2 C17 1.336(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.406(3) . ?
C11 C12 1.355(4) . ?
C11 C10 1.360(4) . ?
C12 C13 1.426(4) . ?
C13 C8 1.372(4) . ?
C13 C14 1.461(4) . ?
C15 C20 1.384(3) . ?
C15 C16 1.395(3) . ?
C15 B1 1.651(3) . ?
C16 C17 1.374(3) . ?
C17 C18 1.376(4) . ?
C18 C19 1.369(4) . ?
C19 C20 1.381(3) . ?
C21 C22 1.388(3) . ?
C21 C26 1.392(3) . ?
C21 B1 1.643(3) . ?
C22 C23 1.382(3) . ?
C23 C24 1.375(4) . ?
C24 C25 1.366(4) . ?
C25 C26 1.393(3) . ?
C27 C28 1.385(3) . ?
C27 C32 1.395(3) . ?
C27 B1 1.645(3) . ?
C28 C29 1.385(3) . ?
C29 C30 1.373(4) . ?
C30 C31 1.377(4) . ?
C31 C32 1.382(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.375(4) . ?
C5 C6 1.373(4) . ?
C6 C7 1.379(4) . ?
C8 C9 1.397(4) . ?
C9 C10 1.390(4) . ?
