#------------------------------------------------------------------------------
#$Date: 2022-05-10 03:31:15 +0300 (Tue, 10 May 2022) $
#$Revision: 275286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158682.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_7158682
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         'C18 H16 F4 O3'
_chemical_formula_sum            'C18 H16 F4 O3'
_chemical_formula_weight         356.31
_chemical_name_systematic
ethyl(2S,3S)-3-(4-fluorophenyl)-3-hydroxy-2-methyl-2-(2,4,6-trifluorophenyl)propanoate
_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   mixed
_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                113.593(6)
_cell_angle_beta                 103.792(7)
_cell_angle_gamma                90.918(7)
_cell_formula_units_Z            2
_cell_length_a                   8.0494(7)
_cell_length_b                   9.9716(7)
_cell_length_c                   11.4118(7)
_cell_measurement_reflns_used    2857
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.6970
_cell_measurement_theta_min      4.0870
_cell_volume                     808.79(12)
_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 shelxle'
_computing_publication_material  'XCIF and publCIF'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6366
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.594
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.250
_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    1.463
_exptl_crystal_description       Block
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Pentane'
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0383
_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)+(0.0353P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2279
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00643j2.cif
_cod_data_source_block           RM2205_auto
_cod_original_cell_volume        808.80(11)
_cod_database_code               7158682
_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   0.954
_shelx_estimated_absorpt_t_max   0.967
_publcif_funding_html
;
;
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
F1 F 0.40911(14) 1.07132(10) 0.82930(10) 0.0331(3) Uani 1 1 d . . . . .
F3 F 0.25227(16) 0.56642(10) 0.54771(11) 0.0415(3) Uani 1 1 d . . . . .
F4 F 0.68459(17) 0.33867(12) 0.80544(12) 0.0520(4) Uani 1 1 d . . . . .
F2 F 0.68054(17) 0.83899(14) 0.49524(13) 0.0541(4) Uani 1 1 d . . . . .
O3 O 0.05802(16) 1.01163(12) 0.71485(11) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.09753(17) 1.03800(12) 0.92426(12) 0.0310(3) Uani 1 1 d . . . . .
O1 O 0.1468(2) 0.77262(15) 0.95676(14) 0.0417(4) Uani 1 1 d D . . . .
H1 H 0.101(3) 0.850(2) 0.984(2) 0.063 Uiso 1 1 d D U . . .
C6 C 0.3128(2) 0.82067(17) 0.69104(16) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.1101(2) 0.96937(17) 0.81297(17) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.2709(3) 0.79972(18) 0.89642(17) 0.0274(4) Uani 1 1 d . . . . .
H12 H 0.346607 0.893288 0.960510 0.033 Uiso 1 1 calc R U . . .
C17 C 0.4160(3) 0.41929(19) 0.82168(19) 0.0348(5) Uani 1 1 d . . . . .
H17 H 0.369844 0.322023 0.801832 0.042 Uiso 1 1 calc R U . . .
C1 C 0.4218(2) 0.94721(17) 0.72453(17) 0.0252(4) Uani 1 1 d . . . . .
C14 C 0.5530(3) 0.70123(18) 0.87955(17) 0.0290(4) Uani 1 1 d . . . . .
H14 H 0.600632 0.798329 0.900221 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4653(3) 0.7012(2) 0.52103(18) 0.0330(5) Uani 1 1 d . . . . .
H4 H 0.480852 0.614648 0.450685 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3809(2) 0.67464(17) 0.87199(16) 0.0248(4) Uani 1 1 d . . . . .
C7 C 0.1810(2) 0.81980(17) 0.76748(16) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.5443(3) 0.9594(2) 0.66261(19) 0.0334(5) Uani 1 1 d . . . . .
H2 H 0.612877 1.050346 0.689192 0.040 Uiso 1 1 calc R U . . .
C10 C 0.0001(3) 1.15776(18) 0.75389(18) 0.0292(4) Uani 1 1 d . . . . .
H10A H 0.092652 1.233284 0.824260 0.035 Uiso 1 1 calc R U . . .
H10B H -0.102243 1.159519 0.788191 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3131(3) 0.53265(18) 0.84446(18) 0.0298(4) Uani 1 1 d . . . . .
H18 H 0.195824 0.513211 0.841240 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5623(3) 0.8333(2) 0.56037(19) 0.0349(5) Uani 1 1 d . . . . .
C5 C 0.3442(2) 0.69908(17) 0.58754(17) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.0200(3) 0.70521(19) 0.68331(19) 0.0325(4) Uani 1 1 d . . . . .
H8A H -0.020714 0.709318 0.596884 0.049 Uiso 1 1 calc R U . . .
H8B H -0.071231 0.727369 0.729364 0.049 Uiso 1 1 calc R U . . .
H8C H 0.049798 0.606263 0.670294 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6582(3) 0.5889(2) 0.85754(18) 0.0329(5) Uani 1 1 d . . . . .
H15 H 0.776438 0.607304 0.862509 0.039 Uiso 1 1 calc R U . . .
C11 C -0.0444(3) 1.1882(2) 0.6324(2) 0.0374(5) Uani 1 1 d . . . . .
H11A H 0.057321 1.184379 0.598558 0.056 Uiso 1 1 calc R U . . .
H11B H -0.081933 1.286374 0.654906 0.056 Uiso 1 1 calc R U . . .
H11C H -0.137609 1.113832 0.564197 0.056 Uiso 1 1 calc R U . . .
C16 C 0.5838(3) 0.45016(19) 0.82834(18) 0.0340(5) 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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C9 O3 C10 114.98(13) . . ?
C12 O1 H1 106.9(17) . . ?
C1 C6 C5 112.59(16) . . ?
C1 C6 C7 121.62(14) . . ?
C5 C6 C7 125.73(15) . . ?
O2 C9 O3 123.83(14) . . ?
O2 C9 C7 123.69(15) . . ?
O3 C9 C7 112.43(14) . . ?
O1 C12 C13 107.73(13) . . ?
O1 C12 C7 110.80(15) . . ?
C13 C12 C7 113.50(13) . . ?
O1 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
C7 C12 H12 108.2 . . ?
C16 C17 C18 118.72(17) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
F1 C1 C2 116.08(15) . . ?
F1 C1 C6 117.79(15) . . ?
C2 C1 C6 126.13(15) . . ?
C13 C14 C15 121.52(17) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C3 C4 C5 117.24(16) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C14 C13 C18 118.83(15) . . ?
C14 C13 C12 119.89(15) . . ?
C18 C13 C12 121.27(17) . . ?
C6 C7 C9 109.95(13) . . ?
C6 C7 C8 113.72(14) . . ?
C9 C7 C8 104.67(14) . . ?
C6 C7 C12 109.77(14) . . ?
C9 C7 C12 106.68(13) . . ?
C8 C7 C12 111.71(14) . . ?
C3 C2 C1 116.31(17) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
O3 C10 C11 106.98(14) . . ?
O3 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O3 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C17 C18 C13 120.38(19) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
F2 C3 C4 118.46(17) . . ?
F2 C3 C2 118.87(18) . . ?
C4 C3 C2 122.68(18) . . ?
F3 C5 C4 115.81(15) . . ?
F3 C5 C6 119.16(16) . . ?
C4 C5 C6 125.02(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C16 C15 C14 117.21(19) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
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 . . ?
C17 C16 F4 118.69(17) . . ?
C17 C16 C15 123.31(16) . . ?
F4 C16 C15 117.99(19) . . ?
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 C1 1.3599(18) . ?
F3 C5 1.353(2) . ?
F4 C16 1.3636(19) . ?
F2 C3 1.353(2) . ?
O3 C9 1.329(2) . ?
O3 C10 1.4631(18) . ?
O2 C9 1.208(2) . ?
O1 C12 1.419(2) . ?
O1 H1 0.837(16) . ?
C6 C1 1.388(2) . ?
C6 C5 1.391(2) . ?
C6 C7 1.528(2) . ?
C9 C7 1.539(2) . ?
C12 C13 1.514(2) . ?
C12 C7 1.569(2) . ?
C12 H12 1.0000 . ?
C17 C16 1.358(3) . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C1 C2 1.373(3) . ?
C14 C13 1.381(3) . ?
C14 C15 1.394(2) . ?
C14 H14 0.9500 . ?
C4 C3 1.368(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C13 C18 1.392(2) . ?
C7 C8 1.545(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9500 . ?
C10 C11 1.499(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C18 H18 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
