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#$Date: 2025-08-19 01:15:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/22/1562233.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_1562233
loop_
_publ_author_name
'Bin, Huai-Yu'
'Cheng, Li'
'Wu, Xiong'
'Zhu, Chang-Liang'
'Yang, Xiao-Hui'
'Xie, Jian-Hua'
'Zhou, Qi-Lin'
_publ_section_title
;
 Asymmetric Hydrogenation of Exocyclic γ,δ-Unsaturated β-Ketoesters to
 Functionalized Chiral Allylic Alcohols via Dynamic Kinetic Resolution
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02044G
_journal_year                    2021
_chemical_formula_sum            'C15 H17 F O3'
_chemical_formula_weight         264.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-01-08 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.22580(10)
_cell_length_b                   11.19040(10)
_cell_length_c                   14.72280(10)
_cell_measurement_temperature    291(2)
_cell_volume                     1355.23(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10637
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.405
_diffrn_reflns_theta_min         4.964
_exptl_absorpt_coefficient_mu    0.817
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             560
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_coef       0.0154(12)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0340
_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)+(0.0434P)²+0.1495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                2615
_reflns_number_total             2751
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02044g2.cif
_cod_data_source_block           p21091217a
_cod_database_code               1562233
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.6238(2) 0.38721(12) 0.39779(11) 0.0889(5) Uani 1 1 d . . . . .
O1 O 0.54501(18) 0.63947(12) 0.66212(11) 0.0634(4) Uani 1 1 d . . . . .
H1 H 0.551280 0.572932 0.685189 0.095 Uiso 1 1 calc R U . . .
O2 O 0.4521(2) 0.90303(16) 0.76246(15) 0.0932(6) Uani 1 1 d . . . . .
O3 O 0.2956(3) 0.74669(16) 0.80129(11) 0.0889(6) Uani 1 1 d D . . . .
C1 C 0.3865(2) 0.65561(16) 0.62434(13) 0.0521(4) Uani 1 1 d . . . . .
H1A H 0.310305 0.595354 0.647198 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3281(2) 0.78275(17) 0.64691(14) 0.0567(5) Uani 1 1 d . . . . .
H2 H 0.209627 0.784555 0.640176 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4013(3) 0.85892(17) 0.57148(15) 0.0646(5) Uani 1 1 d . . . . .
H3A H 0.515608 0.874489 0.582572 0.077 Uiso 1 1 calc R U . . .
H3B H 0.344312 0.934413 0.565650 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3780(3) 0.78171(16) 0.48713(15) 0.0623(5) Uani 1 1 d . . . . .
H4A H 0.271818 0.795162 0.460387 0.075 Uiso 1 1 calc R U . . .
H4B H 0.460801 0.798985 0.442077 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3934(2) 0.65479(16) 0.52124(14) 0.0521(4) Uani 1 1 d . . . . .
C6 C 0.3680(3) 0.81943(19) 0.74171(17) 0.0670(6) Uani 1 1 d . . . . .
C7 C 0.3100(9) 0.7605(6) 0.8993(3) 0.0833(17) Uani 0.734(15) 1 d D U P A 1
H7A H 0.211342 0.734065 0.929255 0.100 Uiso 0.734(15) 1 calc R U P A 1
H7B H 0.329258 0.843477 0.914945 0.100 Uiso 0.734(15) 1 calc R U P A 1
C8 C 0.4491(11) 0.6858(10) 0.9271(4) 0.112(3) Uani 0.734(15) 1 d D U P A 1
H8A H 0.430943 0.604799 0.908184 0.167 Uiso 0.734(15) 1 calc R U P A 1
H8B H 0.460278 0.688430 0.992021 0.167 Uiso 0.734(15) 1 calc R U P A 1
H8C H 0.546637 0.715515 0.899360 0.167 Uiso 0.734(15) 1 calc R U P A 1
C9 C 0.4194(3) 0.55592(17) 0.47365(14) 0.0580(5) Uani 1 1 d . . . . .
H9 H 0.425888 0.485252 0.506697 0.070 Uiso 1 1 calc R U . . .
C10 C 0.4392(3) 0.54516(16) 0.37494(14) 0.0563(5) Uani 1 1 d . . . . .
C11 C 0.5445(3) 0.46049(18) 0.33862(15) 0.0627(5) Uani 1 1 d . . . . .
C12 C 0.5757(3) 0.4476(2) 0.24791(18) 0.0728(6) Uani 1 1 d . . . . .
H12 H 0.648551 0.390084 0.227326 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4965(4) 0.5218(2) 0.18772(17) 0.0752(7) Uani 1 1 d . . . . .
H13 H 0.516684 0.515515 0.125750 0.090 Uiso 1 1 calc R U . . .
C14 C 0.3876(3) 0.6051(2) 0.21944(16) 0.0728(6) Uani 1 1 d . . . . .
H14 H 0.332385 0.653970 0.178684 0.087 Uiso 1 1 calc R U . . .
C15 C 0.3599(3) 0.61662(19) 0.31114(15) 0.0632(5) Uani 1 1 d . . . . .
H15 H 0.286124 0.673745 0.331242 0.076 Uiso 1 1 calc R U . . .
C7A C 0.387(3) 0.7832(11) 0.8864(7) 0.085(4) Uani 0.266(15) 1 d D U P A 2
H7AA H 0.501136 0.797548 0.873608 0.102 Uiso 0.266(15) 1 calc R U P A 2
H7AB H 0.340251 0.854365 0.913501 0.102 Uiso 0.266(15) 1 calc R U P A 2
C8A C 0.365(4) 0.6763(18) 0.9466(10) 0.113(7) Uani 0.266(15) 1 d D U P A 2
H8AA H 0.381426 0.604717 0.911879 0.169 Uiso 0.266(15) 1 calc R U P A 2
H8AB H 0.256986 0.676485 0.971279 0.169 Uiso 0.266(15) 1 calc R U P A 2
H8AC H 0.442608 0.679226 0.995319 0.169 Uiso 0.266(15) 1 calc R U P A 2
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'
F F 0.0727 0.0534 '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'
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
C1 O1 H1 109.5 . . ?
C6 O3 C7 123.3(4) . . ?
C6 O3 C7A 99.0(6) . . ?
O1 C1 C5 110.73(16) . . ?
O1 C1 C2 108.52(15) . . ?
C5 C1 C2 103.48(16) . . ?
O1 C1 H1A 111.3 . . ?
C5 C1 H1A 111.3 . . ?
C2 C1 H1A 111.3 . . ?
C6 C2 C3 116.18(18) . . ?
C6 C2 C1 112.84(17) . . ?
C3 C2 C1 103.70(16) . . ?
C6 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C2 C3 C4 103.12(16) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C5 C4 C3 104.55(17) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C9 C5 C4 128.42(18) . . ?
C9 C5 C1 122.59(18) . . ?
C4 C5 C1 108.86(16) . . ?
O2 C6 O3 124.3(2) . . ?
O2 C6 C2 125.3(2) . . ?
O3 C6 C2 110.41(19) . . ?
O3 C7 C8 106.2(4) . . ?
O3 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
O3 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
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 . . ?
C5 C9 C10 127.54(18) . . ?
C5 C9 H9 116.2 . . ?
C10 C9 H9 116.2 . . ?
C11 C10 C15 115.00(19) . . ?
C11 C10 C9 120.39(19) . . ?
C15 C10 C9 124.60(19) . . ?
F1 C11 C12 118.1(2) . . ?
F1 C11 C10 117.53(19) . . ?
C12 C11 C10 124.4(2) . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
C8A C7A O3 102.3(9) . . ?
C8A C7A H7AA 111.3 . . ?
O3 C7A H7AA 111.3 . . ?
C8A C7A H7AB 111.3 . . ?
O3 C7A H7AB 111.3 . . ?
H7AA C7A H7AB 109.2 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 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 C11 1.362(3) . ?
O1 C1 1.429(2) . ?
O1 H1 0.8200 . ?
O2 C6 1.203(3) . ?
O3 C6 1.337(3) . ?
O3 C7 1.456(4) . ?
O3 C7A 1.518(10) . ?
C1 C5 1.519(3) . ?
C1 C2 1.538(2) . ?
C1 H1A 0.9800 . ?
C2 C6 1.491(3) . ?
C2 C3 1.524(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.512(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.327(3) . ?
C7 C8 1.475(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.467(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.368(3) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C7A C8A 1.501(12) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C6 -41.6(2) . . . . ?
C5 C1 C2 C6 -159.28(18) . . . . ?
O1 C1 C2 C3 84.93(19) . . . . ?
C5 C1 C2 C3 -32.7(2) . . . . ?
C6 C2 C3 C4 165.36(18) . . . . ?
C1 C2 C3 C4 41.0(2) . . . . ?
C2 C3 C4 C5 -32.9(2) . . . . ?
C3 C4 C5 C9 -163.2(2) . . . . ?
C3 C4 C5 C1 12.7(2) . . . . ?
O1 C1 C5 C9 72.4(2) . . . . ?
C2 C1 C5 C9 -171.48(19) . . . . ?
O1 C1 C5 C4 -103.71(18) . . . . ?
C2 C1 C5 C4 12.4(2) . . . . ?
C7 O3 C6 O2 0.1(4) . . . . ?
C7A O3 C6 O2 -13.8(8) . . . . ?
C7 O3 C6 C2 -179.3(3) . . . . ?
C7A O3 C6 C2 166.8(8) . . . . ?
C3 C2 C6 O2 0.0(3) . . . . ?
C1 C2 C6 O2 119.5(2) . . . . ?
C3 C2 C6 O3 179.37(19) . . . . ?
C1 C2 C6 O3 -61.1(2) . . . . ?
C6 O3 C7 C8 -92.1(9) . . . . ?
C4 C5 C9 C10 -0.3(4) . . . . ?
C1 C5 C9 C10 -175.7(2) . . . . ?
C5 C9 C10 C11 145.5(2) . . . . ?
C5 C9 C10 C15 -33.6(3) . . . . ?
C15 C10 C11 F1 -179.20(19) . . . . ?
C9 C10 C11 F1 1.7(3) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
C9 C10 C11 C12 -177.1(2) . . . . ?
F1 C11 C12 C13 -179.7(2) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
C9 C10 C15 C14 177.7(2) . . . . ?
C6 O3 C7A C8A -158(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307465
