#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/01/7120180.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_7120180
loop_
_publ_author_name
'Liu, Zhicheng'
'Bai, Yihui'
'Zhang, Jian'
'Yu, Yongqi'
'Tan, Ze'
'Zhu, Gangguo'
_publ_section_title
;
 Copper-catalyzed acyltrifluoromethylation of alkenes: rapid access to
 trifluoroethyl indanones and related compounds
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02537H
_journal_year                    2017
_chemical_formula_sum            'C14 H13 F3 O3'
_chemical_formula_weight         286.24
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-25 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2998(10)
_cell_length_b                   10.3533(6)
_cell_length_c                   7.8903(5)
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1331.54(14)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20606
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                2102
_reflns_number_total             3066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc02537h2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               7120180
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.14567(15) 0.2479(2) 0.3465(4) 0.0440(6) Uani 1 1 d .
H1A H 0.0914 0.2675 0.3722 0.053 Uiso 1 1 calc R
F1 F 0.02023(10) -0.24336(18) 0.2268(3) 0.0845(7) Uani 1 1 d .
O3 O 0.31579(11) -0.0813(2) 0.1156(3) 0.0681(6) Uani 1 1 d .
C8 C 0.16596(14) -0.0758(2) 0.1296(3) 0.0406(5) Uani 1 1 d .
H8A H 0.1529 -0.0697 0.0087 0.049 Uiso 1 1 calc R
C7 C 0.25332(15) -0.0243(2) 0.1556(3) 0.0441(6) Uani 1 1 d .
O2 O 0.11495(15) 0.46711(19) 0.5306(3) 0.0669(6) Uani 1 1 d .
O1 O 0.23839(16) 0.5493(2) 0.4723(4) 0.0831(8) Uani 1 1 d .
F3 F 0.08864(12) -0.41225(17) 0.1624(4) 0.0926(8) Uani 1 1 d .
C4 C 0.31009(15) 0.1915(3) 0.2721(3) 0.0498(7) Uani 1 1 d .
H4A H 0.3645 0.1718 0.2476 0.060 Uiso 1 1 calc R
C5 C 0.24738(14) 0.1037(2) 0.2336(3) 0.0398(5) Uani 1 1 d .
C2 C 0.20774(16) 0.3356(3) 0.3829(3) 0.0468(6) Uani 1 1 d .
C12 C 0.16230(15) -0.2178(2) 0.1807(4) 0.0495(7) Uani 1 1 d .
H12A H 0.2074 -0.2629 0.1266 0.059 Uiso 1 1 calc R
H12B H 0.1703 -0.2239 0.3022 0.059 Uiso 1 1 calc R
C3 C 0.28993(16) 0.3068(3) 0.3463(4) 0.0518(7) Uani 1 1 d .
H3A H 0.3308 0.3662 0.3724 0.062 Uiso 1 1 calc R
C9 C 0.10946(13) 0.0198(2) 0.2265(3) 0.0394(6) Uani 1 1 d .
H9A H 0.0916 -0.0218 0.3318 0.047 Uiso 1 1 calc R
C6 C 0.16552(15) 0.1311(2) 0.2717(3) 0.0386(5) Uani 1 1 d .
F2 F 0.06360(13) -0.2689(2) -0.0247(3) 0.0899(7) Uani 1 1 d .
C13 C 0.1904(2) 0.4622(3) 0.4653(4) 0.0555(7) Uani 1 1 d .
C10 C 0.03333(15) 0.0623(3) 0.1286(5) 0.0583(7) Uani 1 1 d .
H10A H 0.0018 0.1207 0.1969 0.087 Uiso 1 1 calc R
H10B H 0.0006 -0.0120 0.1014 0.087 Uiso 1 1 calc R
H10C H 0.0497 0.1048 0.0259 0.087 Uiso 1 1 calc R
C11 C 0.08473(17) -0.2843(3) 0.1362(5) 0.0572(7) Uani 1 1 d .
C14 C 0.0942(3) 0.5832(3) 0.6220(6) 0.0885(12) Uani 1 1 d .
H14A H 0.0391 0.5765 0.6642 0.133 Uiso 1 1 calc R
H14B H 0.0982 0.6562 0.5475 0.133 Uiso 1 1 calc R
H14C H 0.1314 0.5941 0.7152 0.133 Uiso 1 1 calc R
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
C6 C1 C2 119.3(2)
C6 C1 H1A 120.4
C2 C1 H1A 120.4
C12 C8 C7 109.6(2)
C12 C8 C9 117.5(2)
C7 C8 C9 105.30(19)
C12 C8 H8A 108.0
C7 C8 H8A 108.0
C9 C8 H8A 108.0
O3 C7 C5 127.0(2)
O3 C7 C8 125.0(2)
C5 C7 C8 107.99(19)
C13 O2 C14 116.2(3)
C3 C4 C5 118.9(2)
C3 C4 H4A 120.6
C5 C4 H4A 120.6
C4 C5 C6 121.3(2)
C4 C5 C7 129.0(2)
C6 C5 C7 109.7(2)
C1 C2 C3 121.0(3)
C1 C2 C13 121.8(2)
C3 C2 C13 117.3(2)
C11 C12 C8 114.7(2)
C11 C12 H12A 108.6
C8 C12 H12A 108.6
C11 C12 H12B 108.6
C8 C12 H12B 108.6
H12A C12 H12B 107.6
C4 C3 C2 120.1(2)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
C6 C9 C10 113.0(2)
C6 C9 C8 104.07(18)
C10 C9 C8 114.6(2)
C6 C9 H9A 108.3
C10 C9 H9A 108.3
C8 C9 H9A 108.3
C1 C6 C5 119.5(2)
C1 C6 C9 128.7(2)
C5 C6 C9 111.8(2)
O1 C13 O2 123.8(3)
O1 C13 C2 124.0(3)
O2 C13 C2 112.2(2)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
F2 C11 F1 105.6(3)
F2 C11 F3 106.1(3)
F1 C11 F3 105.5(3)
F2 C11 C12 113.1(3)
F1 C11 C12 113.4(3)
F3 C11 C12 112.4(2)
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.384(3)
C1 C2 1.389(4)
C1 H1A 0.9300
F1 C11 1.340(4)
O3 C7 1.218(3)
C8 C12 1.526(3)
C8 C7 1.534(3)
C8 C9 1.552(3)
C8 H8A 0.9800
C7 C5 1.465(3)
O2 C13 1.334(4)
O2 C14 1.442(4)
O1 C13 1.196(4)
F3 C11 1.343(3)
C4 C3 1.370(4)
C4 C5 1.401(4)
C4 H4A 0.9300
C5 C6 1.397(3)
C2 C3 1.402(4)
C2 C13 1.490(4)
C12 C11 1.482(4)
C12 H12A 0.9700
C12 H12B 0.9700
C3 H3A 0.9300
C9 C6 1.514(3)
C9 C10 1.526(3)
C9 H9A 0.9800
F2 C11 1.325(4)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 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
C12 C8 C7 O3 43.7(4)
C9 C8 C7 O3 170.9(3)
C12 C8 C7 C5 -137.0(2)
C9 C8 C7 C5 -9.7(3)
C3 C4 C5 C6 -0.9(4)
C3 C4 C5 C7 -179.8(3)
O3 C7 C5 C4 3.5(5)
C8 C7 C5 C4 -175.8(3)
O3 C7 C5 C6 -175.5(3)
C8 C7 C5 C6 5.1(3)
C6 C1 C2 C3 -0.5(4)
C6 C1 C2 C13 -179.2(3)
C7 C8 C12 C11 -170.8(2)
C9 C8 C12 C11 69.2(3)
C5 C4 C3 C2 0.1(4)
C1 C2 C3 C4 0.6(4)
C13 C2 C3 C4 179.3(3)
C12 C8 C9 C6 132.6(2)
C7 C8 C9 C6 10.3(2)
C12 C8 C9 C10 -103.4(3)
C7 C8 C9 C10 134.3(2)
C2 C1 C6 C5 -0.2(4)
C2 C1 C6 C9 177.6(3)
C4 C5 C6 C1 1.0(4)
C7 C5 C6 C1 -179.9(2)
C4 C5 C6 C9 -177.2(2)
C7 C5 C6 C9 1.9(3)
C10 C9 C6 C1 49.1(3)
C8 C9 C6 C1 174.1(2)
C10 C9 C6 C5 -132.8(2)
C8 C9 C6 C5 -7.9(3)
C14 O2 C13 O1 -3.6(5)
C14 O2 C13 C2 176.4(3)
C1 C2 C13 O1 -166.3(3)
C3 C2 C13 O1 15.0(5)
C1 C2 C13 O2 13.7(4)
C3 C2 C13 O2 -165.1(3)
C8 C12 C11 F2 51.3(3)
C8 C12 C11 F1 -69.0(4)
C8 C12 C11 F3 171.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139187748
