#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023251.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_4023251
loop_
_publ_author_name
'Pierre-Loïc Saaidi'
'Mathieu Guyonnet'
'Erwann Jeanneau'
'Paul Fleurat-Lessard'
'Jens Hasserodt'
_publ_contact_author_address
;Centre de Diffractométrie Henri Longchambon
Université Claude Bernard Lyon1
43 boulevard du 11 novembre 1918
F-69622 Villeurbanne cedex
France
;
_publ_contact_author_email       erwann.jeanneau@univ-lyon1.fr
_publ_contact_author_fax         '+33 472 431 160'
_publ_contact_author_name        'Erwann Jeanneau'
_publ_contact_author_phone       '+33 472 431 859'
_publ_section_title
;
 Trimerization Products of Trifluoroacetone: Critical Solvent Effect
 on Position and Kinetics of Anomeric Equilibria
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1209
_journal_page_last               1216
_journal_paper_doi               10.1021/jo701669p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C9 H9 F9 O3'
_chemical_formula_sum            'C9 H9 F9 O3'
_chemical_formula_weight         336.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-04-24
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 97.628(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9014(2)
_cell_length_b                   9.5107(3)
_cell_length_c                   16.5051(5)
_cell_measurement_reflns_used    2527
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.679
_cell_volume                     1229.35(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5047
_diffrn_reflns_theta_full        25.933
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_min         2.477
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1379
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000500
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.658 0.275 0.277 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0448
_refine_ls_wR_factor_gt          0.0384
_refine_ls_wR_factor_ref         0.0384
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2411
_reflns_number_total             2912
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0353
_oxford_refine_ls_scale          1.0231(17)
_oxford_reflns_number_all        2905
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo701669p-File004.cif
_cod_data_source_block
;
;
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023251
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
F1 F 0.37635(12) 0.26991(8) 0.65582(5) 0.0365 1.0000 Uani . . . . . . .
F2 F 0.16571(12) 0.33936(9) 0.56863(5) 0.0376 1.0000 Uani . . . . . . .
F3 F 0.42360(12) 0.36227(9) 0.54160(5) 0.0383 1.0000 Uani . . . . . . .
F4 F 0.07319(13) 0.86746(11) 0.52269(7) 0.0521 1.0000 Uani . . . . . . .
F5 F 0.26131(14) 1.01367(9) 0.57923(7) 0.0495 1.0000 Uani . . . . . . .
F6 F 0.32305(15) 0.87418(11) 0.48449(6) 0.0494 1.0000 Uani . . . . . . .
F7 F 0.83477(12) 0.78515(12) 0.70862(7) 0.0503 1.0000 Uani . . . . . . .
F8 F 0.78974(11) 0.62887(12) 0.61379(6) 0.0478 1.0000 Uani . . . . . . .
F9 F 0.83913(12) 0.56521(12) 0.73919(6) 0.0496 1.0000 Uani . . . . . . .
C1 C 0.32501(18) 0.37016(14) 0.60145(8) 0.0275 1.0000 Uani . . . . . . .
C2 C 0.33305(15) 0.51646(13) 0.64100(7) 0.0222 1.0000 Uani . . . . . . .
C3 C 0.26035(16) 0.62717(13) 0.57945(8) 0.0237 1.0000 Uani . . . . . . .
C4 C 0.30016(16) 0.77375(13) 0.61468(8) 0.0243 1.0000 Uani . . . . . . .
C5 C 0.2388(2) 0.88313(15) 0.54970(9) 0.0354 1.0000 Uani . . . . . . .
C6 C 0.49176(16) 0.78989(13) 0.64048(8) 0.0244 1.0000 Uani . . . . . . .
C7 C 0.56808(16) 0.67090(14) 0.69668(8) 0.0251 1.0000 Uani . . . . . . .
C8 C 0.75908(18) 0.66151(17) 0.68927(9) 0.0349 1.0000 Uani . . . . . . .
C9 C 0.54890(19) 0.69136(16) 0.78675(8) 0.0327 1.0000 Uani . . . . . . .
O1 O 0.50837(11) 0.53394(9) 0.66797(5) 0.0253 1.0000 Uani . . . . . . .
O3 O 0.20528(12) 0.80377(11) 0.68015(6) 0.0314 1.0000 Uani . . . . . . .
O2 O 0.23200(12) 0.51737(10) 0.70463(6) 0.0274 1.0000 Uani . . . . . . .
H31 H 0.1368 0.6140 0.5664 0.0277 1.0000 Uiso R . . . . . .
H32 H 0.3131 0.6167 0.5305 0.0282 1.0000 Uiso R . . . . . .
H61 H 0.5463 0.7895 0.5911 0.0309 1.0000 Uiso R . . . . . .
H62 H 0.5129 0.8788 0.6677 0.0293 1.0000 Uiso R . . . . . .
H91 H 0.5965 0.6099 0.8177 0.0477 1.0000 Uiso R . . . . . .
H92 H 0.4285 0.7014 0.7928 0.0460 1.0000 Uiso R . . . . . .
H93 H 0.6109 0.7747 0.8064 0.0494 1.0000 Uiso R . . . . . .
H1 H 0.2653 0.4559 0.7382 0.0431 1.0000 Uiso R . . . . . .
H2 H 0.1734 0.7331 0.6990 0.0482 1.0000 Uiso R . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F3 . C1 . F2 . 107.33(11) yes
F3 . C1 . F1 . 107.53(11) yes
F2 . C1 . F1 . 107.57(11) yes
F3 . C1 . C2 . 111.68(10) yes
F2 . C1 . C2 . 110.80(11) yes
F1 . C1 . C2 . 111.71(10) yes
C1 . C2 . C3 . 110.65(10) yes
C1 . C2 . O1 . 103.00(10) yes
C3 . C2 . O1 . 113.44(10) yes
C1 . C2 . O2 . 109.21(10) yes
C3 . C2 . O2 . 107.10(10) yes
O1 . C2 . O2 . 113.39(10) yes
C2 . C3 . C4 . 109.70(10) yes
C2 . C3 . H31 . 109.6 no
C4 . C3 . H31 . 110.4 no
C2 . C3 . H32 . 108.8 no
C4 . C3 . H32 . 108.9 no
H31 . C3 . H32 . 109.4 no
C3 . C4 . C5 . 108.93(10) yes
C3 . C4 . C6 . 110.17(10) yes
C5 . C4 . C6 . 109.79(11) yes
C3 . C4 . O3 . 111.69(11) yes
C5 . C4 . O3 . 104.28(11) yes
C6 . C4 . O3 . 111.79(10) yes
C4 . C5 . F6 . 112.05(12) yes
C4 . C5 . F5 . 111.23(12) yes
F6 . C5 . F5 . 107.18(13) yes
C4 . C5 . F4 . 111.40(12) yes
F6 . C5 . F4 . 107.11(12) yes
F5 . C5 . F4 . 107.62(12) yes
C4 . C6 . C7 . 112.98(10) yes
C4 . C6 . H61 . 107.4 no
C7 . C6 . H61 . 108.8 no
C4 . C6 . H62 . 108.8 no
C7 . C6 . H62 . 109.7 no
H61 . C6 . H62 . 109.1 no
C6 . C7 . C8 . 107.86(11) yes
C6 . C7 . C9 . 114.37(11) yes
C8 . C7 . C9 . 108.14(11) yes
C6 . C7 . O1 . 112.44(10) yes
C8 . C7 . O1 . 101.74(10) yes
C9 . C7 . O1 . 111.36(11) yes
C7 . C8 . F7 . 110.07(12) yes
C7 . C8 . F8 . 112.96(11) yes
F7 . C8 . F8 . 107.21(13) yes
C7 . C8 . F9 . 112.44(12) yes
F7 . C8 . F9 . 107.19(12) yes
F8 . C8 . F9 . 106.65(13) yes
C7 . C9 . H91 . 109.1 no
C7 . C9 . H92 . 109.7 no
H91 . C9 . H92 . 109.8 no
C7 . C9 . H93 . 108.7 no
H91 . C9 . H93 . 109.4 no
H92 . C9 . H93 . 110.2 no
C7 . O1 . C2 . 118.38(9) yes
C4 . O3 . H2 . 110.7 no
C2 . O2 . H1 . 109.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C1 . 1.3351(16) yes
F2 . C1 . 1.3351(16) yes
F3 . C1 . 1.3389(15) yes
F4 . C5 . 1.3336(18) yes
F5 . C5 . 1.3371(17) yes
F6 . C5 . 1.3412(19) yes
F7 . C8 . 1.3386(18) yes
F8 . C8 . 1.3368(18) yes
F9 . C8 . 1.3340(18) yes
C1 . C2 . 1.5346(18) yes
C2 . C3 . 1.5218(17) yes
C2 . O1 . 1.4075(15) yes
C2 . O2 . 1.4011(15) yes
C3 . C4 . 1.5271(17) yes
C3 . H31 . 0.979 no
C3 . H32 . 0.962 no
C4 . C5 . 1.5263(19) yes
C4 . C6 . 1.5250(17) yes
C4 . O3 . 1.4235(15) yes
C6 . C7 . 1.5350(17) yes
C6 . H61 . 0.971 no
C6 . H62 . 0.961 no
C7 . C8 . 1.5328(19) yes
C7 . C9 . 1.5266(18) yes
C7 . O1 . 1.4439(15) yes
C9 . H91 . 0.975 no
C9 . H92 . 0.974 no
C9 . H93 . 0.965 no
O3 . H2 . 0.796 no
O2 . H1 . 0.824 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H92 . O3 . 123 0.97 2.58 3.2159(19) yes
O2 . H1 . O3 3_546 168 0.82 1.97 2.7819(19) yes
O3 . H2 . O2 . 140 0.80 2.10 2.7576(19) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10322575
