#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/75/2237586.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237586
loop_
_publ_author_name
'Gerber, Thomas'
'Betz, Richard'
_publ_section_title
;
 rac-3,3,3-Trifluorolactic acid
;
_journal_coeditor_code           ZL2532
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o336
_journal_paper_doi               10.1107/S1600536813003097
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C3 H3 F3 O3'
_chemical_formula_moiety         'C3 H3 F3 O3'
_chemical_formula_sum            'C3 H3 F3 O3'
_chemical_formula_weight         144.05
_chemical_name_common
;
rac-3,3,3-Trifluorolactic acid
;
_chemical_name_systematic
;
rac-3,3,3-Trifluoro-2-hydroxypropanoic acid
;
_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                   10.586(3)
_cell_length_b                   9.248(3)
_cell_length_c                   10.826(3)
_cell_measurement_reflns_used    4117
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      3.47
_cell_volume                     1059.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and
Mercury (Macrae et al., 2008)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9450
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0306
_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)+(0.0349P)²+0.3452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                1133
_reflns_number_total             1309
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL da008_s in P2(1)/c          New: Pbca
CELL  0.71073   10.5860    9.2480   10.8260    90.000    90.000    90.000
ZERR        8    0.0030    0.0030    0.0030     0.000     0.000     0.000
LATT   1
SYMM     0.50000 - X ,            - Y ,    0.50000 + Z
SYMM     0.50000 + X ,    0.50000 - Y ,            - Z
SYMM             - X ,    0.50000 + Y ,    0.50000 - Z
SFAC  C  H  F  O
UNIT    24   24  24  24
ACTA
BOND $H
CONF
HTAB
TEMP -73
OMIT 4 3 0
EQIV $1 -x, -y+1, -z+1
EQIV $2 x-1/2, -y+1/2, -z+1
EQIV $3 -x,-y,1-z
HTAB O3 O2_$1
HTAB O1 O3_$2
HTAB C2 O1_$3
L.S. 10
FMAP 2
PLAN -5
WGHT    0.034900    0.345200
FVAR       0.28265
F1  3    0.074908    0.073344    0.263623    11.00000    0.09555    0.05943 =
         0.05432   -0.02923    0.01429   -0.01456
F2  3    0.240456    0.205426    0.269380    11.00000    0.04510    0.10028 =
         0.05557   -0.01104    0.02264    0.00554
F3  3    0.061212    0.299362    0.225498    11.00000    0.08266    0.08091 =
         0.03478    0.01232    0.00029    0.02239
O3   4    0.160578    0.359067    0.466174    11.00000    0.02117    0.02575 =
         0.05683   -0.00670   -0.00034    0.00242
AFIX   147
H12   2    0.108366    0.426977    0.473094    11.00000   -1.50000
AFIX   0
O1  4   -0.102698    0.120767    0.459656    11.00000    0.02319    0.02507 =
         0.05996   -0.00193    0.00003    0.00083
AFIX   147
H111  2   -0.179028    0.132747    0.478174    11.00000   -1.50000
AFIX   0
O2  4   -0.092030    0.359855    0.487064    11.00000    0.02707    0.02515 =
         0.05228   -0.00343    0.00288    0.00338
C1   1   -0.044105    0.245147    0.463182    11.00000    0.02274    0.02570 =
         0.02846    0.00077   -0.00233    0.00204
C2   1    0.096909    0.231808    0.433895    11.00000    0.02289    0.02374 =
         0.03149   -0.00060   -0.00031    0.00259
AFIX  13
H12A  2    0.132790    0.149880    0.482918    11.00000   -1.20000
AFIX   0
C3   1    0.118351    0.201726    0.296709    11.00000    0.03933    0.04372 =
         0.03624   -0.00295    0.00525    0.00384
HKLF 4 1  1.0000  0.0000  0.0000  0.0000 -1.0000  0.0000  0.0000  0.0000 -1.0000
REM  da008_s in P2(1)/c          New: Pbca
REM R1 =  0.0306 for   1133 Fo > 4sig(Fo)  and  0.0368 for all   1309 data
REM     82 parameters refined using      0 restraints
END
;
_cod_data_source_file            zl2532.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     ' -P 2ac 2ab'
_cod_database_code               2237586
_cod_database_fobs_code          2237586
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
F F1 0.07491(11) 0.07334(11) 0.26362(9) 0.0698(3) Uani d . 1 1
F F2 0.24046(9) 0.20543(13) 0.26938(9) 0.0670(3) Uani d . 1 1
F F3 0.06121(11) 0.29936(12) 0.22550(8) 0.0661(3) Uani d . 1 1
O O3 0.16058(7) 0.35907(8) 0.46617(9) 0.0346(2) Uani d . 1 1
H H12 0.1084 0.4270 0.4731 0.052 Uiso d R 1 1
O O1 -0.10270(7) 0.12077(8) 0.45966(9) 0.0361(2) Uani d . 1 1
H H111 -0.1790 0.1327 0.4782 0.054 Uiso d R 1 1
O O2 -0.09203(7) 0.35985(8) 0.48706(9) 0.0348(2) Uani d . 1 1
C C1 -0.04410(10) 0.24515(11) 0.46318(10) 0.0256(2) Uani d . 1 1
C C2 0.09691(10) 0.23181(11) 0.43390(10) 0.0260(2) Uani d . 1 1
H H12A 0.1328 0.1499 0.4829 0.031 Uiso calc R 1 1
C C3 0.11835(13) 0.20173(15) 0.29671(12) 0.0398(3) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.0956(8) 0.0594(6) 0.0543(6) -0.0146(5) 0.0143(5) -0.0292(5)
F2 0.0451(5) 0.1003(8) 0.0556(5) 0.0055(5) 0.0226(4) -0.0110(5)
F3 0.0827(7) 0.0809(7) 0.0348(5) 0.0224(6) 0.0003(4) 0.0123(4)
O3 0.0212(4) 0.0258(4) 0.0568(5) 0.0024(3) -0.0003(3) -0.0067(4)
O1 0.0232(4) 0.0251(4) 0.0600(6) 0.0008(3) 0.0000(4) -0.0019(4)
O2 0.0271(4) 0.0252(4) 0.0523(5) 0.0034(3) 0.0029(4) -0.0034(3)
C1 0.0227(5) 0.0257(5) 0.0285(5) 0.0020(4) -0.0023(4) 0.0008(4)
C2 0.0229(5) 0.0237(5) 0.0315(5) 0.0026(4) -0.0003(4) -0.0006(4)
C3 0.0393(7) 0.0437(7) 0.0362(6) 0.0038(5) 0.0053(5) -0.0030(5)
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
C2 O3 H12 109.5
C1 O1 H111 109.5
O2 C1 O1 125.56(10)
O2 C1 C2 121.76(10)
O1 C1 C2 112.68(9)
O3 C2 C3 108.91(10)
O3 C2 C1 110.48(8)
C3 C2 C1 111.15(9)
O3 C2 H12A 108.8
C3 C2 H12A 108.8
C1 C2 H12A 108.8
F1 C3 F2 107.55(12)
F1 C3 F3 107.08(12)
F2 C3 F3 107.21(12)
F1 C3 C2 112.03(11)
F2 C3 C2 110.91(11)
F3 C3 C2 111.81(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.3227(17)
F2 C3 1.3265(17)
F3 C3 1.3325(17)
O3 C2 1.4005(13)
O3 H12 0.8400
O1 C1 1.3074(13)
O1 H111 0.8399
O2 C1 1.2040(13)
C1 C2 1.5310(15)
C2 C3 1.5280(17)
C2 H12A 1.0000
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H12 O2 5_566 0.84 2.03 2.7459(13) 143.4
O1 H111 O3 3_456 0.84 1.80 2.6381(13) 172.4
C2 H12A O1 5_556 1.00 2.60 3.4588(16) 144.1
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
O2 C1 C2 O3 13.26(15)
O1 C1 C2 O3 -166.37(9)
O2 C1 C2 C3 -107.76(12)
O1 C1 C2 C3 72.61(12)
O3 C2 C3 F1 171.65(10)
C1 C2 C3 F1 -66.42(14)
O3 C2 C3 F2 51.46(14)
C1 C2 C3 F2 173.40(11)
O3 C2 C3 F3 -68.14(13)
C1 C2 C3 F3 53.80(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 214194
