#------------------------------------------------------------------------------
#$Date: 2022-05-10 03:31:15 +0300 (Tue, 10 May 2022) $
#$Revision: 275286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158680.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_7158680
loop_
_publ_author_name
'Kaehler, Tanja'
'Lorenz, Jonas'
'Ould, Darren'
'Engl, Dorothea'
'Santi, Micol'
'Gierlichs, Lukas'
'Wirth, Thomas'
'Melen, Rebecca'
_publ_section_title
;
 Borane promoted aryl transfer reaction for the synthesis of α-aryl
 functionalised β-hydroxy and β-keto esters
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00643J
_journal_year                    2022
_chemical_formula_moiety         'C23 H10 B F11 O3'
_chemical_formula_sum            'C23 H10 B F11 O3'
_chemical_formula_weight         554.12
_chemical_name_systematic
4-ethoxy-6-(4-fluorophenyl)-2,2-bis(perfluorophenyl)-2H-1,3λ³,2λ⁴-dioxaborinine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-24 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.148(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1068(3)
_cell_length_b                   13.2125(4)
_cell_length_c                   18.2143(7)
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.5820
_cell_measurement_theta_min      4.0770
_cell_volume                     2188.30(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'XSHELL and Shellxle'
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELLXS
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8687
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.900
_diffrn_reflns_theta_min         4.136
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.555
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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    1.682
_exptl_crystal_description       rod
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Pentane'
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0410
_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)+(0.0620P)²+0.2963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3145
_reflns_number_total             4222
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00643j2.cif
_cod_data_source_block           rm2146b_auto
_cod_original_cell_volume        2188.32(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158680
_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   0.515
_shelx_estimated_absorpt_t_max   0.895
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C7 C -0.0144(2) 0.82245(13) 0.23602(11) 0.0339(4) Uani 1 1 d . . . . .
C12 C 0.0210(2) 0.56516(14) 0.15741(11) 0.0384(4) Uani 1 1 d . . . . .
C23 C 0.2191(2) 0.71479(13) 0.13155(10) 0.0345(4) Uani 1 1 d . . . . .
C9 C 0.1738(2) 0.73369(14) 0.30482(10) 0.0355(4) Uani 1 1 d . . . . .
C8 C 0.0907(2) 0.82255(14) 0.29211(11) 0.0378(4) Uani 1 1 d . . . . .
H8 H 0.107537 0.880901 0.321865 0.045 Uiso 1 1 calc R U . . .
C6 C -0.1195(2) 0.90479(13) 0.21889(11) 0.0357(4) Uani 1 1 d . . . . .
C21 C 0.3412(3) 0.84043(15) 0.05841(12) 0.0446(5) Uani 1 1 d . . . . .
C17 C -0.0652(2) 0.56337(15) 0.09297(12) 0.0426(5) Uani 1 1 d . . . . .
C18 C 0.3368(2) 0.65298(15) 0.11766(12) 0.0412(4) Uani 1 1 d . . . . .
C1 C -0.1250(2) 0.99152(15) 0.26251(13) 0.0426(5) Uani 1 1 d . . . . .
H1 H -0.066444 0.995276 0.307243 0.051 Uiso 1 1 calc R U . . .
C20 C 0.4548(2) 0.77587(18) 0.04662(13) 0.0484(5) Uani 1 1 d . . . . .
C22 C 0.2264(2) 0.80991(14) 0.09967(11) 0.0380(4) Uani 1 1 d . . . . .
C5 C -0.2106(2) 0.89876(16) 0.15533(12) 0.0444(5) Uani 1 1 d . . . . .
H5 H -0.209634 0.839417 0.125906 0.053 Uiso 1 1 calc R U . . .
C3 C -0.3003(2) 1.06365(15) 0.17778(14) 0.0472(5) Uani 1 1 d . . . . .
C14 C -0.0461(3) 0.38803(15) 0.17070(16) 0.0571(6) Uani 1 1 d . . . . .
C19 C 0.4527(2) 0.68013(17) 0.07698(13) 0.0475(5) Uani 1 1 d . . . . .
C13 C 0.0295(2) 0.47400(15) 0.19524(13) 0.0442(5) Uani 1 1 d . . . . .
C16 C -0.1420(2) 0.47958(17) 0.06680(14) 0.0515(6) Uani 1 1 d . . . . .
C15 C -0.1322(3) 0.39140(17) 0.10708(17) 0.0580(6) Uani 1 1 d . . . . .
C2 C -0.2146(2) 1.07193(15) 0.24128(14) 0.0494(5) Uani 1 1 d . . . . .
H2 H -0.216458 1.131644 0.270270 0.059 Uiso 1 1 calc R U . . .
C4 C -0.3029(3) 0.97839(17) 0.13430(13) 0.0491(5) Uani 1 1 d . . . . .
H4 H -0.366079 0.974183 0.091142 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3398(3) 0.63065(15) 0.37608(13) 0.0488(5) Uani 1 1 d . . . . .
H10A H 0.408473 0.621184 0.336361 0.059 Uiso 1 1 calc R U . . .
H10B H 0.271536 0.572304 0.375647 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4227(3) 0.63793(18) 0.44843(14) 0.0557(6) Uani 1 1 d . . . . .
H11A H 0.479692 0.575826 0.457450 0.084 Uiso 1 1 calc R U . . .
H11B H 0.353541 0.646694 0.487313 0.084 Uiso 1 1 calc R U . . .
H11C H 0.489502 0.696055 0.448262 0.084 Uiso 1 1 calc R U . . .
F11 F 0.11947(14) 0.87935(8) 0.10782(7) 0.0513(3) Uani 1 1 d . . . . .
F7 F 0.33952(14) 0.55803(9) 0.14599(8) 0.0531(3) Uani 1 1 d . . . . .
F6 F -0.07844(15) 0.64814(10) 0.05149(7) 0.0520(3) Uani 1 1 d . . . . .
F10 F 0.34308(17) 0.93491(10) 0.03030(8) 0.0638(4) Uani 1 1 d . . . . .
F2 F 0.11146(16) 0.46425(9) 0.25834(8) 0.0569(4) Uani 1 1 d . . . . .
F3 F -0.03624(19) 0.30225(10) 0.21051(11) 0.0758(5) Uani 1 1 d . . . . .
F9 F 0.56607(16) 0.80468(13) 0.00655(9) 0.0680(4) Uani 1 1 d . . . . .
F1 F -0.38764(16) 1.14213(10) 0.15610(9) 0.0650(4) Uani 1 1 d . . . . .
F8 F 0.56294(16) 0.61536(12) 0.06639(10) 0.0741(5) Uani 1 1 d . . . . .
F5 F -0.22434(17) 0.48338(12) 0.00369(9) 0.0709(4) Uani 1 1 d . . . . .
F4 F -0.20818(19) 0.30936(11) 0.08362(12) 0.0847(6) Uani 1 1 d . . . . .
O2 O 0.16988(15) 0.65886(9) 0.26014(7) 0.0387(3) Uani 1 1 d . . . . .
O3 O -0.02950(14) 0.74427(9) 0.19089(7) 0.0364(3) Uani 1 1 d . . . . .
O1 O 0.25686(16) 0.72566(10) 0.36483(8) 0.0415(3) Uani 1 1 d . . . . .
B1 B 0.0934(2) 0.67256(15) 0.18479(12) 0.0356(4) 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'
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'
B B 0.0090 0.0039 '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
O3 C7 C8 120.82(17) . . ?
O3 C7 C6 113.66(16) . . ?
C8 C7 C6 125.52(17) . . ?
C17 C12 C13 114.97(19) . . ?
C17 C12 B1 118.55(17) . . ?
C13 C12 B1 126.35(19) . . ?
C18 C23 C22 113.78(18) . . ?
C18 C23 B1 118.76(16) . . ?
C22 C23 B1 127.40(17) . . ?
O2 C9 O1 117.83(17) . . ?
O2 C9 C8 122.89(17) . . ?
O1 C9 C8 119.27(16) . . ?
C7 C8 C9 118.15(17) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C5 C6 C1 118.87(18) . . ?
C5 C6 C7 119.09(17) . . ?
C1 C6 C7 121.95(18) . . ?
F10 C21 C20 119.47(19) . . ?
F10 C21 C22 120.2(2) . . ?
C20 C21 C22 120.37(19) . . ?
F6 C17 C12 119.45(17) . . ?
F6 C17 C16 116.3(2) . . ?
C12 C17 C16 124.3(2) . . ?
F7 C18 C19 116.72(18) . . ?
F7 C18 C23 118.36(18) . . ?
C19 C18 C23 124.92(19) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
F9 C20 C21 120.8(2) . . ?
F9 C20 C19 120.5(2) . . ?
C21 C20 C19 118.8(2) . . ?
F11 C22 C21 115.66(17) . . ?
F11 C22 C23 121.16(17) . . ?
C21 C22 C23 123.18(18) . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
F1 C3 C2 119.1(2) . . ?
F1 C3 C4 117.9(2) . . ?
C2 C3 C4 123.00(19) . . ?
F3 C14 C15 120.2(2) . . ?
F3 C14 C13 119.9(3) . . ?
C15 C14 C13 119.9(2) . . ?
F8 C19 C18 121.0(2) . . ?
F8 C19 C20 120.0(2) . . ?
C18 C19 C20 118.99(19) . . ?
F2 C13 C12 121.45(18) . . ?
F2 C13 C14 116.1(2) . . ?
C12 C13 C14 122.5(2) . . ?
F5 C16 C15 120.4(2) . . ?
F5 C16 C17 121.1(2) . . ?
C15 C16 C17 118.5(2) . . ?
F4 C15 C14 120.4(2) . . ?
F4 C15 C16 119.8(3) . . ?
C14 C15 C16 119.8(2) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
O1 C10 C11 107.45(18) . . ?
O1 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O1 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 O2 B1 118.63(14) . . ?
C7 O3 B1 119.65(15) . . ?
C9 O1 C10 117.18(15) . . ?
O3 B1 O2 108.74(15) . . ?
O3 B1 C12 106.61(16) . . ?
O2 B1 C12 109.33(15) . . ?
O3 B1 C23 112.55(15) . . ?
O2 B1 C23 106.01(15) . . ?
C12 B1 C23 113.52(16) . . ?
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
C7 O3 1.323(2) . ?
C7 C8 1.361(3) . ?
C7 C6 1.471(3) . ?
C12 C17 1.376(3) . ?
C12 C13 1.388(3) . ?
C12 B1 1.631(3) . ?
C23 C18 1.382(3) . ?
C23 C22 1.388(3) . ?
C23 B1 1.638(3) . ?
C9 O2 1.280(2) . ?
C9 O1 1.299(2) . ?
C9 C8 1.409(3) . ?
C8 H8 0.9500 . ?
C6 C5 1.389(3) . ?
C6 C1 1.397(3) . ?
C21 F10 1.350(2) . ?
C21 C20 1.367(3) . ?
C21 C22 1.381(3) . ?
C17 F6 1.353(3) . ?
C17 C16 1.381(3) . ?
C18 F7 1.356(2) . ?
C18 C19 1.370(3) . ?
C1 C2 1.382(3) . ?
C1 H1 0.9500 . ?
C20 F9 1.336(3) . ?
C20 C19 1.381(3) . ?
C22 F11 1.352(2) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9500 . ?
C3 F1 1.353(2) . ?
C3 C2 1.364(3) . ?
C3 C4 1.377(3) . ?
C14 F3 1.346(3) . ?
C14 C15 1.364(4) . ?
C14 C13 1.389(3) . ?
C19 F8 1.341(2) . ?
C13 F2 1.342(3) . ?
C16 F5 1.338(3) . ?
C16 C15 1.377(4) . ?
C15 F4 1.343(3) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C10 O1 1.473(2) . ?
C10 C11 1.485(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O2 B1 1.515(3) . ?
O3 B1 1.476(2) . ?
