#------------------------------------------------------------------------------
#$Date: 2017-06-06 07:18:46 +0300 (Tue, 06 Jun 2017) $
#$Revision: 197558 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/56/7155666.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_7155666
loop_
_publ_author_name
'Silvestri, Anthony Paul'
'Dawson, Philip Edward'
_publ_section_title
;
 Base-catalyzed Diastereoselective Trimerization of Trifluoroacetone
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01094J
_journal_year                    2017
_chemical_formula_moiety         'C11 H11 F9 O4'
_chemical_formula_sum            'C11 H11 F9 O4'
_chemical_formula_weight         378.20
_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_date             2016-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-02-08 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2625(4)
_cell_length_b                   9.6405(4)
_cell_length_c                   17.8895(7)
_cell_measurement_reflns_used    8166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.72
_cell_volume                     1424.98(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17826
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.748
_diffrn_reflns_theta_min         2.277
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.6466
_exptl_absorpt_correction_T_min  0.5900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.9125.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0310
_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)+(0.0369P)²+0.3106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2776
_reflns_number_total             3022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob01094j2.cif
_cod_data_source_block           dawson03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' 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_database_code               7155666
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
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
F8 F 0.08475(18) 0.30589(16) 0.79682(8) 0.0294(4) Uani 1 1 d .
F9 F -0.11525(17) 0.32665(16) 0.72164(8) 0.0286(3) Uani 1 1 d .
F6 F 0.02677(19) 0.58373(16) 0.46508(8) 0.0333(4) Uani 1 1 d .
F5 F 0.2790(2) 0.61384(16) 0.43931(8) 0.0312(4) Uani 1 1 d .
F7 F 0.0003(2) 0.50932(15) 0.76511(8) 0.0324(4) Uani 1 1 d .
F1 F 0.6213(2) 0.53382(17) 0.73549(9) 0.0349(4) Uani 1 1 d .
F4 F 0.1671(2) 0.73013(15) 0.52855(9) 0.0344(4) Uani 1 1 d .
F2 F 0.4837(2) 0.69738(15) 0.68343(9) 0.0339(4) Uani 1 1 d .
F3 F 0.67525(19) 0.59711(18) 0.62236(9) 0.0359(4) Uani 1 1 d .
O3 O 0.18296(19) 0.24196(16) 0.65403(9) 0.0178(3) Uani 1 1 d .
O2 O 0.2227(2) 0.36421(16) 0.51158(9) 0.0203(4) Uani 1 1 d .
H2 H 0.2984 0.3668 0.4803 0.030 Uiso 1 1 calc GR
O1 O 0.3688(2) 0.53225(17) 0.57726(9) 0.0209(4) Uani 1 1 d .
O4 O -0.0467(2) 0.20135(17) 0.58867(9) 0.0223(4) Uani 1 1 d .
C10 C 0.0887(3) 0.1677(2) 0.60639(13) 0.0190(5) Uani 1 1 d .
C2 C 0.0879(3) 0.4768(2) 0.61102(13) 0.0185(5) Uani 1 1 d .
H2A H -0.0122 0.4368 0.5896 0.022 Uiso 1 1 calc R
H2B H 0.0619 0.5701 0.6308 0.022 Uiso 1 1 calc R
C9 C 0.0273(3) 0.3803(2) 0.73943(14) 0.0225(5) Uani 1 1 d .
C4 C 0.3087(3) 0.4424(2) 0.70394(14) 0.0204(5) Uani 1 1 d .
H4A H 0.3535 0.3777 0.7416 0.024 Uiso 1 1 calc R
H4B H 0.2879 0.5321 0.7292 0.024 Uiso 1 1 calc R
C1 C 0.2162(3) 0.4893(2) 0.55012(14) 0.0184(5) Uani 1 1 d .
C3 C 0.1483(3) 0.3843(2) 0.67482(13) 0.0179(5) Uani 1 1 d .
C8 C 0.1715(3) 0.6057(2) 0.49541(14) 0.0233(5) Uani 1 1 d .
C6 C 0.5290(3) 0.3341(2) 0.62090(15) 0.0234(5) Uani 1 1 d .
H6A H 0.4542 0.2647 0.6006 0.035 Uiso 1 1 calc GR
H6B H 0.5828 0.2964 0.6653 0.035 Uiso 1 1 calc GR
H6C H 0.6103 0.3574 0.5831 0.035 Uiso 1 1 calc GR
C5 C 0.4347(3) 0.4647(2) 0.64231(14) 0.0209(5) Uani 1 1 d .
C7 C 0.5548(3) 0.5743(3) 0.67066(15) 0.0267(6) Uani 1 1 d .
C11 C 0.1754(3) 0.0407(2) 0.58122(14) 0.0252(5) Uani 1 1 d .
H11A H 0.2572 0.0659 0.5439 0.038 Uiso 1 1 calc GR
H11B H 0.0979 -0.0243 0.5590 0.038 Uiso 1 1 calc GR
H11C H 0.2283 -0.0033 0.6241 0.038 Uiso 1 1 calc GR
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O3 C3 123.09(18)
C1 O2 H2 109.5
C1 O1 C5 118.80(18)
O3 C10 C11 110.3(2)
O4 C10 O3 123.7(2)
O4 C10 C11 126.0(2)
H2A C2 H2B 108.1
C1 C2 H2A 109.5
C1 C2 H2B 109.5
C1 C2 C3 110.62(18)
C3 C2 H2A 109.5
C3 C2 H2B 109.5
F8 C9 F7 106.99(19)
F8 C9 C3 111.2(2)
F9 C9 F8 106.86(19)
F9 C9 F7 107.18(19)
F9 C9 C3 114.2(2)
F7 C9 C3 110.10(19)
H4A C4 H4B 107.7
C3 C4 H4A 108.9
C3 C4 H4B 108.9
C3 C4 C5 113.3(2)
C5 C4 H4A 108.9
C5 C4 H4B 108.9
O2 C1 O1 112.96(19)
O2 C1 C2 108.23(18)
O2 C1 C8 109.11(19)
O1 C1 C2 113.45(19)
O1 C1 C8 102.67(18)
C2 C1 C8 110.27(19)
O3 C3 C2 115.10(18)
O3 C3 C9 107.42(18)
O3 C3 C4 105.23(18)
C9 C3 C2 111.43(19)
C9 C3 C4 108.54(19)
C4 C3 C2 108.79(19)
F6 C8 F5 107.4(2)
F6 C8 F4 107.4(2)
F6 C8 C1 111.09(19)
F5 C8 C1 111.1(2)
F4 C8 F5 107.3(2)
F4 C8 C1 112.3(2)
H6A C6 H6B 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C5 C6 H6A 109.5
C5 C6 H6B 109.5
C5 C6 H6C 109.5
O1 C5 C4 112.9(2)
O1 C5 C6 111.2(2)
O1 C5 C7 101.50(18)
C4 C5 C7 107.3(2)
C6 C5 C4 114.3(2)
C6 C5 C7 108.6(2)
F1 C7 F2 106.8(2)
F1 C7 C5 110.5(2)
F2 C7 C5 112.4(2)
F3 C7 F1 107.6(2)
F3 C7 F2 106.9(2)
F3 C7 C5 112.4(2)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F8 C9 1.339(3)
F9 C9 1.325(3)
F6 C8 1.330(3)
F5 C8 1.342(3)
F7 C9 1.345(3)
F1 C7 1.341(3)
F4 C8 1.338(3)
F2 C7 1.344(3)
F3 C7 1.336(3)
O3 C10 1.359(3)
O3 C3 1.450(3)
O2 H2 0.8400
O2 C1 1.390(3)
O1 C1 1.413(3)
O1 C5 1.440(3)
O4 C10 1.207(3)
C10 C11 1.489(3)
C2 H2A 0.9900
C2 H2B 0.9900
C2 C1 1.525(3)
C2 C3 1.532(3)
C9 C3 1.528(3)
C4 H4A 0.9900
C4 H4B 0.9900
C4 C3 1.531(3)
C4 C5 1.531(4)
C1 C8 1.534(3)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C6 C5 1.529(3)
C5 C7 1.537(3)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
