#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/87/4118723.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_4118723
loop_
_publ_author_name
'Petr Novák'
'Anton Lishchynskyi'
'Vladimir V. Grushin'
_publ_section_title
;
 Trifluoromethylation of α-Haloketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16167
_journal_page_last               16170
_journal_paper_doi               10.1021/ja307783w
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C9 H6 Cl F3 O'
_chemical_formula_weight         222.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8625(9)
_cell_length_b                   5.8223(3)
_cell_length_c                   20.7554(11)
_cell_measurement_reflns_used    2783
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.30
_cell_measurement_theta_min      3.37
_cell_volume                     1796.05(17)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support whith MicroMount'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            4276
_diffrn_reflns_theta_full        36.49
_diffrn_reflns_theta_max         36.49
_diffrn_reflns_theta_min         1.96
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.8458
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 TWINABS Version 2008/0 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0704P)²+0.5316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                3536
_reflns_number_total             4276
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja307783w_si_004.cif
_cod_data_source_block           pnb-268-04t
_cod_database_code               4118723
loop_
_symmetry_equiv_pos_as_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'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.11253(7) 0.35771(19) 1.03645(6) 0.01972(19) Uani 1 1 d .
C2 C 0.15363(7) 0.5713(2) 1.04072(5) 0.02033(19) Uani 1 1 d .
H2 H 0.1737 0.6289 1.0811 0.024 Uiso 1 1 calc R
C3 C 0.16484(7) 0.69899(18) 0.98486(5) 0.01811(18) Uani 1 1 d .
H3 H 0.1934 0.8448 0.9869 0.022 Uiso 1 1 calc R
C4 C 0.13446(6) 0.61496(17) 0.92560(5) 0.01590(17) Uani 1 1 d .
C5 C 0.09295(7) 0.40073(18) 0.92283(5) 0.01833(18) Uani 1 1 d .
H5 H 0.0722 0.3431 0.8827 0.022 Uiso 1 1 calc R
C6 C 0.08166(8) 0.27093(19) 0.97833(6) 0.02064(19) Uani 1 1 d .
H6 H 0.0532 0.1249 0.9765 0.025 Uiso 1 1 calc R
C7 C 0.15034(7) 0.75728(18) 0.86715(5) 0.01655(17) Uani 1 1 d .
C8 C 0.11683(8) 0.6632(2) 0.80335(5) 0.02000(19) Uani 1 1 d .
H8A H 0.1503 0.5207 0.7932 0.024 Uiso 1 1 calc R
H8B H 0.0525 0.6224 0.8078 0.024 Uiso 1 1 calc R
C9 C 0.12715(8) 0.8289(2) 0.74779(6) 0.0225(2) Uani 1 1 d .
Cl1 Cl 0.10071(2) 0.19114(6) 1.105261(15) 0.02819(9) Uani 1 1 d .
F1 F 0.21278(5) 0.87328(15) 0.73342(4) 0.02991(18) Uani 1 1 d .
F2 F 0.08654(6) 1.03056(16) 0.75907(4) 0.03270(19) Uani 1 1 d .
F3 F 0.08908(7) 0.74243(19) 0.69436(4) 0.0354(2) Uani 1 1 d .
O1 O 0.18808(6) 0.94183(14) 0.86997(4) 0.02251(17) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0178(4) 0.0217(4) 0.0197(5) 0.0023(3) 0.0028(3) 0.0049(3)
C2 0.0187(4) 0.0238(5) 0.0184(5) -0.0018(3) -0.0006(3) 0.0031(3)
C3 0.0158(4) 0.0187(4) 0.0198(5) -0.0017(3) -0.0019(3) 0.0010(3)
C4 0.0131(4) 0.0162(4) 0.0184(4) -0.0014(3) -0.0002(3) 0.0003(3)
C5 0.0170(4) 0.0170(4) 0.0211(5) -0.0018(3) 0.0004(3) -0.0012(3)
C6 0.0192(4) 0.0183(4) 0.0244(5) 0.0007(3) 0.0027(3) -0.0002(3)
C7 0.0133(4) 0.0177(4) 0.0186(4) -0.0011(3) -0.0008(3) 0.0006(3)
C8 0.0202(4) 0.0226(4) 0.0172(5) -0.0020(3) -0.0002(3) -0.0037(3)
C9 0.0206(5) 0.0260(5) 0.0209(5) -0.0023(4) -0.0013(4) -0.0006(4)
Cl1 0.03213(16) 0.02939(15) 0.02306(16) 0.00756(10) 0.00556(10) 0.00627(10)
F1 0.0260(4) 0.0340(4) 0.0298(4) 0.0036(3) 0.0071(3) -0.0055(3)
F2 0.0370(4) 0.0328(4) 0.0283(4) 0.0027(3) -0.0064(3) 0.0128(3)
F3 0.0435(5) 0.0452(5) 0.0175(4) -0.0012(3) -0.0042(3) -0.0134(4)
O1 0.0239(4) 0.0188(3) 0.0248(4) 0.0008(3) -0.0037(3) -0.0048(3)
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
C6 C1 C2 121.85(11)
C6 C1 Cl1 118.63(9)
C2 C1 Cl1 119.52(9)
C3 C2 C1 118.65(10)
C2 C3 C4 120.58(10)
C5 C4 C3 119.52(10)
C5 C4 C7 122.36(9)
C3 C4 C7 118.10(9)
C6 C5 C4 120.46(10)
C1 C6 C5 118.94(10)
O1 C7 C4 121.80(9)
O1 C7 C8 120.91(10)
C4 C7 C8 117.29(9)
C9 C8 C7 113.71(9)
F1 C9 F2 107.42(10)
F1 C9 F3 106.87(10)
F2 C9 F3 106.44(10)
F1 C9 C8 113.05(10)
F2 C9 C8 112.34(10)
F3 C9 C8 110.35(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3861(17)
C1 C2 1.3886(17)
C1 Cl1 1.7352(12)
C2 C3 1.3871(16)
C3 C4 1.3987(15)
C4 C5 1.3927(14)
C4 C7 1.4881(15)
C5 C6 1.3879(16)
C7 O1 1.2135(13)
C7 C8 1.5170(15)
C8 C9 1.5115(17)
C9 F1 1.3325(14)
C9 F2 1.3405(15)
C9 F3 1.3430(14)
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
C6 C1 C2 C3 -0.83(16)
Cl1 C1 C2 C3 178.11(8)
C1 C2 C3 C4 0.68(16)
C2 C3 C4 C5 -0.28(15)
C2 C3 C4 C7 -178.58(9)
C3 C4 C5 C6 0.01(15)
C7 C4 C5 C6 178.24(9)
C2 C1 C6 C5 0.57(16)
Cl1 C1 C6 C5 -178.38(8)
C4 C5 C6 C1 -0.15(16)
C5 C4 C7 O1 -178.60(10)
C3 C4 C7 O1 -0.35(15)
C5 C4 C7 C8 1.78(14)
C3 C4 C7 C8 -179.97(9)
O1 C7 C8 C9 -5.57(15)
C4 C7 C8 C9 174.05(9)
C7 C8 C9 F1 65.79(13)
C7 C8 C9 F2 -55.99(13)
C7 C8 C9 F3 -174.60(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9206643
