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#$Date: 2016-03-22 09:28:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178870 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/46/7224681.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_7224681
loop_
_publ_author_name
'He, Xiang-Hong'
'Yang, Lei'
'Huang, Wei'
'Zhao, Qian'
'Pan, Xiao-Li'
'Jiang, Dao-Feng'
'Yang, Ming-Cheng'
'Peng, Cheng'
'Han, Bo'
_publ_section_title
;
 Catalytic cross-benzoin/Michael/acetalization cascade for asymmetric
 synthesis of trifluoromethylated γ-butyrolactones
;
_journal_issue                   34
_journal_name_full               'RSC Adv.'
_journal_page_first              28960
_journal_paper_doi               10.1039/C6RA03571J
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H12 Cl F3 O3'
_chemical_formula_sum            'C18 H12 Cl F3 O3'
_chemical_formula_weight         368.73
_chemical_melting_point          350
_chemical_name_common            'chiral (trifluoromethyl)dihydrofuranone'
_chemical_name_systematic
(4S,5S)-5-benzoyl-4-phenyl-5-(trifluoromethyl)dihydrofuran-2(3H)-one
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-12-06 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.997(3)
_cell_length_b                   11.806(4)
_cell_length_c                   17.950(5)
_cell_measurement_reflns_used    7813
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      3.08
_cell_volume                     1694.7(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28499
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/n-hexane'
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0442
_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)+(0.0550P)²+0.0411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.745
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     0.998
_reflns_number_gt                2551
_reflns_number_total             3893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra03571j2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1694.7(9)
_cod_database_code               7224681
_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   0.913
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-4
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
Cl1 Cl 0.54344(14) -0.24049(9) -0.06281(5) 0.0883(4) Uani 1 1 d . .
O2 O 0.0415(3) 0.06671(16) 0.13153(10) 0.0510(5) Uani 1 1 d . .
O1 O -0.1357(3) -0.0468(2) 0.19023(14) 0.0770(7) Uani 1 1 d . .
O3 O 0.4078(4) 0.2346(2) 0.12772(13) 0.0842(9) Uani 1 1 d . .
F2 F 0.0384(4) 0.2464(2) 0.03258(13) 0.1206(10) Uani 1 1 d . .
F1 F -0.1198(4) 0.2687(2) 0.12835(17) 0.1203(10) Uani 1 1 d . .
F3 F 0.1057(5) 0.36333(18) 0.11831(15) 0.1246(11) Uani 1 1 d . .
C3 C 0.1327(4) 0.1845(2) 0.23155(16) 0.0488(7) Uani 1 1 d . .
H3 H 0.1174 0.2650 0.2432 0.059 Uiso 1 1 calc R U
C1 C -0.0512(4) 0.0361(3) 0.19222(17) 0.0535(7) Uani 1 1 d . .
C4 C 0.1349(4) 0.1681(2) 0.14542(16) 0.0512(7) Uani 1 1 d . .
C2 C -0.0243(4) 0.1192(3) 0.25325(18) 0.0620(9) Uani 1 1 d . .
H2A H -0.0085 0.0807 0.3005 0.074 Uiso 1 1 calc R U
H2B H -0.1193 0.1699 0.2576 0.074 Uiso 1 1 calc R U
C5 C 0.0396(7) 0.2628(3) 0.1056(2) 0.0847(12) Uani 1 1 d . .
C7 C 0.3641(4) 0.0601(3) 0.06805(15) 0.0497(7) Uani 1 1 d . .
C10 C 0.4787(5) -0.1216(3) -0.01369(17) 0.0595(9) Uani 1 1 d . .
C9 C 0.3231(4) -0.0784(3) -0.02820(16) 0.0569(8) Uani 1 1 d . .
H9 H 0.2574 -0.1095 -0.0658 0.068 Uiso 1 1 calc R U
C6 C 0.3124(5) 0.1593(3) 0.11288(14) 0.0560(8) Uani 1 1 d . .
C12 C 0.5229(5) 0.0175(3) 0.07926(19) 0.0675(10) Uani 1 1 d . .
H12 H 0.5921 0.0513 0.1145 0.081 Uiso 1 1 calc R U
C11 C 0.5803(5) -0.0738(4) 0.0394(2) 0.0726(10) Uani 1 1 d . .
H11 H 0.6866 -0.1028 0.0481 0.087 Uiso 1 1 calc R U
C8 C 0.2647(4) 0.0115(3) 0.01335(17) 0.0536(8) Uani 1 1 d . .
H8 H 0.1579 0.0397 0.0046 0.064 Uiso 1 1 calc R U
C13 C 0.2876(4) 0.1412(2) 0.27031(14) 0.0441(7) Uani 1 1 d . .
C18 C 0.3950(4) 0.2165(3) 0.30537(16) 0.0528(7) Uani 1 1 d . .
H18 H 0.3737 0.2939 0.3027 0.063 Uiso 1 1 calc R U
C14 C 0.3239(5) 0.0268(3) 0.27421(19) 0.0622(9) Uani 1 1 d . .
H14 H 0.2542 -0.0254 0.2510 0.075 Uiso 1 1 calc R U
C17 C 0.5320(4) 0.1787(3) 0.3438(2) 0.0708(10) Uani 1 1 d . .
H17 H 0.6016 0.2305 0.3674 0.085 Uiso 1 1 calc R U
C15 C 0.4633(6) -0.0102(3) 0.3125(2) 0.0810(12) Uani 1 1 d . .
H15 H 0.4874 -0.0872 0.3145 0.097 Uiso 1 1 calc R U
C16 C 0.5671(5) 0.0663(4) 0.3478(2) 0.0802(11) Uani 1 1 d . .
H16 H 0.6603 0.0411 0.3740 0.096 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C1 O2 C4 111.4(2)
C13 C3 C2 112.7(2)
C13 C3 C4 113.9(2)
C2 C3 C4 101.5(2)
C13 C3 H3 109.4
C2 C3 H3 109.4
C4 C3 H3 109.4
O1 C1 O2 120.1(3)
O1 C1 C2 130.3(3)
O2 C1 C2 109.5(3)
O2 C4 C5 105.7(3)
O2 C4 C6 111.0(2)
C5 C4 C6 109.4(3)
O2 C4 C3 105.7(2)
C5 C4 C3 111.5(3)
C6 C4 C3 113.3(3)
C1 C2 C3 105.4(3)
C1 C2 H2A 110.7
C3 C2 H2A 110.7
C1 C2 H2B 110.7
C3 C2 H2B 110.7
H2A C2 H2B 108.8
F3 C5 F2 107.8(4)
F3 C5 F1 106.4(4)
F2 C5 F1 107.5(4)
F3 C5 C4 112.2(3)
F2 C5 C4 111.0(4)
F1 C5 C4 111.7(3)
C12 C7 C8 118.6(3)
C12 C7 C6 117.8(3)
C8 C7 C6 123.5(3)
C9 C10 C11 121.1(3)
C9 C10 Cl1 118.4(3)
C11 C10 Cl1 120.5(3)
C10 C9 C8 119.4(3)
C10 C9 H9 120.3
C8 C9 H9 120.3
O3 C6 C7 121.9(3)
O3 C6 C4 116.8(3)
C7 C6 C4 121.2(2)
C11 C12 C7 121.2(3)
C11 C12 H12 119.4
C7 C12 H12 119.4
C10 C11 C12 119.1(3)
C10 C11 H11 120.4
C12 C11 H11 120.4
C9 C8 C7 120.5(3)
C9 C8 H8 119.8
C7 C8 H8 119.8
C14 C13 C18 118.3(3)
C14 C13 C3 121.8(3)
C18 C13 C3 119.9(2)
C17 C18 C13 120.9(3)
C17 C18 H18 119.5
C13 C18 H18 119.5
C15 C14 C13 120.2(3)
C15 C14 H14 119.9
C13 C14 H14 119.9
C16 C17 C18 120.7(4)
C16 C17 H17 119.6
C18 C17 H17 119.6
C14 C15 C16 120.5(3)
C14 C15 H15 119.8
C16 C15 H15 119.8
C17 C16 C15 119.4(3)
C17 C16 H16 120.3
C15 C16 H16 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C10 1.736(4)
O2 C1 1.366(3)
O2 C4 1.433(3)
O1 C1 1.190(4)
O3 C6 1.201(4)
F2 C5 1.326(5)
F1 C5 1.341(6)
F3 C5 1.318(5)
C3 C13 1.510(4)
C3 C2 1.524(5)
C3 C4 1.558(4)
C3 H3 0.9800
C1 C2 1.486(5)
C4 C5 1.530(5)
C4 C6 1.539(5)
C2 H2A 0.9700
C2 H2B 0.9700
C7 C12 1.380(5)
C7 C8 1.388(4)
C7 C6 1.479(5)
C10 C9 1.370(5)
C10 C11 1.373(5)
C9 C8 1.379(5)
C9 H9 0.9300
C12 C11 1.374(5)
C12 H12 0.9300
C11 H11 0.9300
C8 H8 0.9300
C13 C14 1.383(4)
C13 C18 1.388(4)
C18 C17 1.369(5)
C18 H18 0.9300
C14 C15 1.380(5)
C14 H14 0.9300
C17 C16 1.358(5)
C17 H17 0.9300
C15 C16 1.380(6)
C15 H15 0.9300
C16 H16 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O1 0.98 2.53 3.469(4) 161.0 3
C3 H3 O1 0.98 2.53 3.469(4) 161.0 3
C3 H3 O1 0.98 2.53 3.469(4) 161.0 3
C3 H3 O1 0.98 2.53 3.469(4) 161.0 3
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
C4 O2 C1 O1 -179.6(3)
C4 O2 C1 C2 0.1(3)
C1 O2 C4 C5 -102.7(3)
C1 O2 C4 C6 138.8(2)
C1 O2 C4 C3 15.6(3)
C13 C3 C4 O2 97.5(3)
C2 C3 C4 O2 -24.0(3)
C13 C3 C4 C5 -148.2(3)
C2 C3 C4 C5 90.3(3)
C13 C3 C4 C6 -24.2(3)
C2 C3 C4 C6 -145.7(2)
O1 C1 C2 C3 163.6(3)
O2 C1 C2 C3 -16.1(3)
C13 C3 C2 C1 -98.5(3)
C4 C3 C2 C1 23.8(3)
O2 C4 C5 F3 175.4(3)
C6 C4 C5 F3 -65.1(4)
C3 C4 C5 F3 61.0(5)
O2 C4 C5 F2 -63.9(4)
C6 C4 C5 F2 55.6(4)
C3 C4 C5 F2 -178.3(4)
O2 C4 C5 F1 56.1(4)
C6 C4 C5 F1 175.6(3)
C3 C4 C5 F1 -58.3(4)
C11 C10 C9 C8 -2.8(5)
Cl1 C10 C9 C8 175.9(2)
C12 C7 C6 O3 37.8(4)
C8 C7 C6 O3 -139.1(3)
C12 C7 C6 C4 -139.6(3)
C8 C7 C6 C4 43.4(4)
O2 C4 C6 O3 -172.6(2)
C5 C4 C6 O3 71.2(3)
C3 C4 C6 O3 -53.9(3)
O2 C4 C6 C7 5.0(3)
C5 C4 C6 C7 -111.2(3)
C3 C4 C6 C7 123.7(3)
C8 C7 C12 C11 -2.4(4)
C6 C7 C12 C11 -179.5(3)
C9 C10 C11 C12 1.2(5)
Cl1 C10 C11 C12 -177.5(3)
C7 C12 C11 C10 1.4(5)
C10 C9 C8 C7 1.8(5)
C12 C7 C8 C9 0.8(4)
C6 C7 C8 C9 177.7(3)
C2 C3 C13 C14 46.7(4)
C4 C3 C13 C14 -68.3(4)
C2 C3 C13 C18 -131.1(3)
C4 C3 C13 C18 113.8(3)
C14 C13 C18 C17 -1.0(4)
C3 C13 C18 C17 176.9(3)
C18 C13 C14 C15 0.3(5)
C3 C13 C14 C15 -177.6(3)
C13 C18 C17 C16 0.8(5)
C13 C14 C15 C16 0.5(5)
C18 C17 C16 C15 0.1(6)
C14 C15 C16 C17 -0.7(6)
