#------------------------------------------------------------------------------
#$Date: 2022-05-10 03:31:15 +0300 (Tue, 10 May 2022) $
#$Revision: 275286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158679.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_7158679
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         'C19 H16 F6 O3'
_chemical_formula_sum            'C19 H16 F6 O3'
_chemical_formula_weight         406.32
_chemical_name_systematic
'Ethyl (2R)-3-hydroxy-2-methyl-3-(4-(trifluoromethyl)phenyl)-2-(3,4,5-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   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                101.608(3)
_cell_angle_beta                 91.454(2)
_cell_angle_gamma                100.640(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1188(2)
_cell_length_b                   10.3636(3)
_cell_length_c                   12.8288(4)
_cell_measurement_reflns_used    13803
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.3320
_cell_measurement_theta_min      4.4010
_cell_volume                     909.24(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_molecular_graphics    'XSHELL and Shelxle'
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    ShelXS
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.087
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.236
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
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    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Pentane'
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.188
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0088(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0555P)²+0.5367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2996
_reflns_number_total             3644
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00643j2.cif
_cod_data_source_block           rm1831h
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Direct' was changed
to 'direct' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7158679
_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   0.551
_shelx_estimated_absorpt_t_max   0.801
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 0.2731(2) 0.36640(15) 0.40657(10) 0.0673(4) Uani 1 1 d . . . . .
F2 F -0.1070(2) 0.26588(15) 0.38495(12) 0.0757(5) Uani 1 1 d . . . . .
F3 F -0.31524(19) 0.29134(19) 0.55828(15) 0.0872(6) Uani 1 1 d . . . . .
C8A C 0.2455(14) 0.3741(8) 0.8589(8) 0.055(3) Uani 0.612(5) 1 d . . P A 1
H8A H 0.108075 0.327901 0.852295 0.065 Uiso 0.612(5) 1 calc R U P A 1
O3A O 0.2893(4) 0.4187(3) 0.9592(2) 0.0649(10) Uani 0.612(5) 1 d . . P A 1
H3A H 0.206(8) 0.460(6) 0.986(2) 0.097 Uiso 0.612(5) 1 calc R U P A 1
C1A C 0.681(2) -0.0265(12) 0.6630(13) 0.068(3) Uani 0.652(9) 1 d . . P B 3
F4A F 0.5762(7) -0.1321(4) 0.6000(6) 0.114(3) Uani 0.652(9) 1 d . . P B 3
F5A F 0.8138(7) 0.0211(4) 0.6076(5) 0.0983(16) Uani 0.652(9) 1 d . . P B 3
F6A F 0.7700(13) -0.0751(7) 0.7350(3) 0.123(3) Uani 0.652(9) 1 d . . P B 3
C10A C 0.1255(15) 0.5787(13) 0.8489(9) 0.0484(19) Uani 0.603(5) 1 d . . P A 5
O1A O -0.0259(4) 0.5446(3) 0.8885(2) 0.0684(10) Uani 0.603(5) 1 d . . P A 5
O2A O 0.1967(6) 0.7108(5) 0.8546(3) 0.0548(10) Uani 0.603(5) 1 d . . P A 5
C8B C 0.250(3) 0.3700(19) 0.8487(15) 0.091(7) Uani 0.388(5) 1 d . . P A 2
H8B H 0.323311 0.413164 0.918308 0.109 Uiso 0.388(5) 1 calc R U P A 2
O3B O 0.0880(5) 0.3170(5) 0.8801(3) 0.0596(14) Uani 0.388(5) 1 d . . P A 2
H3B H 0.054(7) 0.372(7) 0.930(7) 0.089 Uiso 0.388(5) 1 calc R U P A 2
C1B C 0.657(5) -0.032(3) 0.683(3) 0.080(8) Uani 0.348(9) 1 d . . P B 4
F4B F 0.602(3) -0.1338(10) 0.7183(18) 0.178(7) Uani 0.348(9) 1 d . . P B 4
F5B F 0.647(4) -0.071(3) 0.5800(8) 0.213(11) Uani 0.348(9) 1 d . . P B 4
F6B F 0.8422(12) 0.0011(13) 0.710(2) 0.198(10) Uani 0.348(9) 1 d . . P B 4
C10B C 0.174(2) 0.6073(18) 0.8688(14) 0.047(3) Uani 0.397(5) 1 d . . P A 6
O1B O 0.1372(5) 0.6037(4) 0.9574(3) 0.0597(14) Uani 0.397(5) 1 d . . P A 6
O2B O 0.1522(14) 0.6936(10) 0.8128(5) 0.079(3) Uani 0.397(5) 1 d . . P A 6
C18 C 0.2646(3) 0.4294(2) 0.59295(16) 0.0456(5) Uani 1 1 d . . . . .
H18 H 0.398930 0.462614 0.599356 0.055 Uiso 1 1 calc R U . . .
C13 C 0.1599(3) 0.4383(2) 0.68319(16) 0.0463(5) Uani 1 1 d . . . . .
C16 C -0.0204(3) 0.3226(2) 0.48189(19) 0.0544(5) Uani 1 1 d . . . . .
C14 C -0.0386(3) 0.3913(2) 0.66987(19) 0.0556(6) Uani 1 1 d . . . . .
H14 H -0.113923 0.398670 0.730081 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2812(3) 0.1690(2) 0.71922(19) 0.0575(6) Uani 1 1 d . . . . .
H4 H 0.156680 0.166917 0.689682 0.069 Uiso 1 1 calc R U . . .
C17 C 0.1729(3) 0.3723(2) 0.49426(17) 0.0492(5) Uani 1 1 d . . . . .
C9 C 0.2567(3) 0.4914(2) 0.79511(16) 0.0500(5) Uani 1 1 d . . . . .
C12 C 0.4655(3) 0.5630(2) 0.79512(18) 0.0539(5) Uani 1 1 d . . . . .
H12A H 0.540380 0.499540 0.757912 0.081 Uiso 1 1 calc R U . . .
H12B H 0.518807 0.597219 0.868802 0.081 Uiso 1 1 calc R U . . .
H12C H 0.470773 0.637970 0.758653 0.081 Uiso 1 1 calc R U . . .
C15 C -0.1239(3) 0.3349(2) 0.5707(2) 0.0581(6) Uani 1 1 d . . . . .
C5 C 0.3582(3) 0.2683(2) 0.80630(19) 0.0541(5) Uani 1 1 d . . . . .
C7 C 0.6415(3) 0.1725(2) 0.8043(2) 0.0592(6) Uani 1 1 d . . . . .
H7 H 0.765888 0.173771 0.833577 0.071 Uiso 1 1 calc R U . . .
C2 C 0.5628(3) 0.0746(2) 0.7175(2) 0.0574(6) Uani 1 1 d . . . . .
C3 C 0.3827(3) 0.0728(2) 0.6745(2) 0.0605(6) Uani 1 1 d . . . . .
H3 H 0.328570 0.005353 0.614261 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5410(3) 0.2684(2) 0.84889(19) 0.0590(6) Uani 1 1 d . . . . .
H6 H 0.596103 0.335495 0.909163 0.071 Uiso 1 1 calc R U . . .
C11 C 0.0783(5) 0.8077(3) 0.8901(3) 0.0951(10) Uani 1 1 d . . . . .
H11A H 0.008381 0.787385 0.952456 0.114 Uiso 1 1 calc R U . A 5
H11B H -0.015320 0.809839 0.832402 0.114 Uiso 1 1 calc R U . A 5
C19 C 0.2157(6) 0.9342(4) 0.9189(3) 0.1162(14) Uani 1 1 d . . . . .
H19A H 0.281786 0.952407 0.855770 0.174 Uiso 1 1 calc R U . . .
H19B H 0.309529 0.928209 0.974063 0.174 Uiso 1 1 calc R U . . .
H19C H 0.148108 1.007088 0.946124 0.174 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'
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
O3A C8A C5 114.0(6) . . ?
O3A C8A C9 112.4(6) . . ?
C5 C8A C9 111.2(6) . . ?
O3A C8A H8A 106.2 . . ?
C5 C8A H8A 106.2 . . ?
C9 C8A H8A 106.2 . . ?
C8A O3A H3A 109.5 . . ?
F5A C1A F4A 106.7(11) . . ?
F5A C1A F6A 105.2(10) . . ?
F4A C1A F6A 105.1(9) . . ?
F5A C1A C2 115.1(8) . . ?
F4A C1A C2 113.1(10) . . ?
F6A C1A C2 110.9(11) . . ?
O1A C10A O2A 119.9(11) . . ?
O1A C10A C9 128.3(10) . . ?
O2A C10A C9 111.8(8) . . ?
C10A O2A C11 119.2(6) . . ?
O3B C8B C5 111.1(13) . . ?
O3B C8B C9 118.4(14) . . ?
C5 C8B C9 118.9(13) . . ?
O3B C8B H8B 101.5 . . ?
C5 C8B H8B 101.5 . . ?
C9 C8B H8B 101.5 . . ?
C8B O3B H3B 109.5 . . ?
F4B C1B F5B 106(3) . . ?
F4B C1B F6B 105(3) . . ?
F5B C1B F6B 105(2) . . ?
F4B C1B C2 116(2) . . ?
F5B C1B C2 113(3) . . ?
F6B C1B C2 112(3) . . ?
O1B C10B O2B 130.4(17) . . ?
O1B C10B C9 122.0(17) . . ?
O2B C10B C9 107.5(13) . . ?
C10B O2B C11 105.4(9) . . ?
C17 C18 C13 119.69(19) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C18 C13 C14 118.3(2) . . ?
C18 C13 C9 121.71(18) . . ?
C14 C13 C9 119.95(18) . . ?
F2 C16 C15 120.8(2) . . ?
F2 C16 C17 121.0(2) . . ?
C15 C16 C17 118.3(2) . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
F1 C17 C16 118.3(2) . . ?
F1 C17 C18 119.81(19) . . ?
C16 C17 C18 121.85(19) . . ?
C10A C9 C13 102.8(4) . . ?
C10A C9 C12 114.8(4) . . ?
C13 C9 C12 113.11(16) . . ?
C13 C9 C8B 107.3(7) . . ?
C12 C9 C8B 109.3(7) . . ?
C13 C9 C10B 116.2(7) . . ?
C12 C9 C10B 99.8(6) . . ?
C13 C9 C8A 110.8(4) . . ?
C12 C9 C8A 109.9(4) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F3 C15 C14 119.9(2) . . ?
F3 C15 C16 118.4(2) . . ?
C14 C15 C16 121.7(2) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 C8B 119.2(8) . . ?
C6 C5 C8B 122.3(8) . . ?
C4 C5 C8A 121.6(5) . . ?
C6 C5 C8A 119.9(5) . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C7 C2 C3 120.0(2) . . ?
C7 C2 C1B 118.7(18) . . ?
C3 C2 C1B 120.7(18) . . ?
C7 C2 C1A 120.1(6) . . ?
C3 C2 C1A 119.7(6) . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O2A C11 C19 103.3(3) . . ?
C19 C11 O2B 114.5(5) . . ?
O2A C11 H11A 111.1 . . ?
C19 C11 H11A 111.1 . . ?
O2A C11 H11B 111.1 . . ?
C19 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 C17 1.345(2) . ?
F2 C16 1.344(3) . ?
F3 C15 1.348(3) . ?
C8A O3A 1.287(10) . ?
C8A C5 1.535(7) . ?
C8A C9 1.588(8) . ?
C8A H8A 1.0000 . ?
O3A H3A 0.84(6) . ?
C1A F5A 1.282(16) . ?
C1A F4A 1.312(15) . ?
C1A F6A 1.336(16) . ?
C1A C2 1.535(13) . ?
C10A O1A 1.227(12) . ?
C10A O2A 1.355(14) . ?
C10A C9 1.504(14) . ?
O2A C11 1.440(6) . ?
C8B O3B 1.292(18) . ?
C8B C5 1.447(19) . ?
C8B C9 1.545(19) . ?
C8B H8B 1.0000 . ?
O3B H3B 0.84(9) . ?
C1B F4B 1.23(3) . ?
C1B F5B 1.30(4) . ?
C1B F6B 1.32(4) . ?
C1B C2 1.40(3) . ?
C10B O1B 1.18(2) . ?
C10B O2B 1.28(3) . ?
C10B C9 1.587(19) . ?
O2B C11 1.563(9) . ?
C18 C17 1.376(3) . ?
C18 C13 1.390(3) . ?
C18 H18 0.9500 . ?
C13 C14 1.401(3) . ?
C13 C9 1.527(3) . ?
C16 C15 1.370(3) . ?
C16 C17 1.371(3) . ?
C14 C15 1.364(3) . ?
C14 H14 0.9500 . ?
C4 C3 1.379(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C9 C12 1.534(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C5 C6 1.398(3) . ?
C7 C6 1.371(3) . ?
C7 C2 1.374(3) . ?
C7 H7 0.9500 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C11 C19 1.458(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
