#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:41:59 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180515 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218470.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_7218470
loop_
_publ_author_name
'Coles, S. J.'
'Ellis, A. L.'
'Leung, K.'
'Sarson, J.'
'Threlfall, T. L.'
'Tizzard, G. J.'
_publ_section_title
;
 Relationships between the racemic structures of substituted mandelic
 acids containing 8- and 10-membered hydrogen bonded dimer rings
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              10816
_journal_paper_doi               10.1039/C4CE01832J
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H7 F O3'
_chemical_formula_sum            'C8 H7 F O3'
_chemical_formula_weight         170.14
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.142(7)
_cell_angle_beta                 92.370(7)
_cell_angle_gamma                111.420(8)
_cell_formula_units_Z            2
_cell_length_a                   5.0748(10)
_cell_length_b                   5.2814(10)
_cell_length_c                   15.032(4)
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      4.1
_cell_volume                     374.47(14)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_computing_molecular_graphics
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3166
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         4.07
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2012)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0616
_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)+(0.0535P)²+0.4486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                1128
_reflns_number_total             1677
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce01832j2.cif
_cod_data_source_block           2012tsb0006a-RS-3FMA-2
_cod_depositor_comments
'Adding full bibliography for 7218452--7218470.cif.'
_cod_database_code               7218470
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2544(5) 0.7633(5) 0.2310(2) 0.0168(6) Uani 1 1 d . . .
C2 C 0.1128(6) 0.9025(6) 0.2773(2) 0.0217(7) Uani 1 1 d . C .
H2 H 0.0181 1.0018 0.2460 0.026 Uiso 1 1 calc R . .
C3 C 0.1114(6) 0.8949(6) 0.3682(2) 0.0243(7) Uani 1 1 d . . .
H3A H 0.0146 0.9900 0.3992 0.029 Uiso 0.50 1 calc PR A 2
C4 C 0.2483(6) 0.7511(6) 0.4167(2) 0.0251(7) Uani 1 1 d . C .
H4 H 0.2462 0.7476 0.4798 0.030 Uiso 1 1 calc R . .
C5 C 0.3863(6) 0.6150(6) 0.3697(2) 0.0243(7) Uani 1 1 d . . .
H5 H 0.4801 0.5155 0.4014 0.029 Uiso 0.50 1 calc PR B 1
C6 C 0.3925(6) 0.6185(5) 0.2777(2) 0.0223(7) Uani 1 1 d . C .
H6 H 0.4898 0.5234 0.2468 0.027 Uiso 1 1 calc R . .
C7 C 0.2601(5) 0.7741(5) 0.1305(2) 0.0173(6) Uani 1 1 d . . .
H7 H 0.3619 0.6563 0.1088 0.021 Uiso 1 1 calc R . .
C8 C 0.4128(5) 1.0614(5) 0.10041(19) 0.0163(6) Uani 1 1 d . . .
F1A F -0.0182(7) 1.0433(7) 0.4130(3) 0.0311(9) Uani 0.50 1 d P C 1
F1B F 0.5372(8) 0.4836(7) 0.4131(3) 0.0324(9) Uani 0.50 1 d P C 2
O1 O 0.3041(4) 1.1739(4) 0.04910(14) 0.0210(5) Uani 1 1 d . . .
O2 O 0.6749(4) 1.1702(4) 0.13557(15) 0.0216(5) Uani 1 1 d . . .
H2A H 0.7557 1.3244 0.1148 0.032 Uiso 1 1 calc R . .
O3 O -0.0225(4) 0.6699(4) 0.09262(15) 0.0244(5) Uani 1 1 d . . .
H3 H -0.0376 0.7676 0.0508 0.037 Uiso 1 1 calc R . .
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 0.0148(12) 0.0131(12) 0.0191(16) 0.0012(11) 0.0002(11) 0.0010(9)
C2 0.0193(13) 0.0211(13) 0.0247(18) 0.0017(13) 0.0020(12) 0.0074(11)
C3 0.0234(14) 0.0252(15) 0.0234(18) -0.0015(13) 0.0040(13) 0.0078(12)
C4 0.0233(14) 0.0278(15) 0.0185(17) 0.0021(13) -0.0008(12) 0.0026(12)
C5 0.0232(14) 0.0217(14) 0.0258(18) 0.0047(13) -0.0041(13) 0.0062(11)
C6 0.0234(14) 0.0164(13) 0.0274(19) 0.0014(13) 0.0020(13) 0.0074(11)
C7 0.0167(12) 0.0150(12) 0.0191(16) 0.0002(11) -0.0003(11) 0.0045(10)
C8 0.0132(12) 0.0174(12) 0.0159(15) -0.0021(11) 0.0037(11) 0.0027(10)
F1A 0.034(2) 0.036(2) 0.026(2) -0.0028(17) 0.0088(16) 0.0151(16)
F1B 0.035(2) 0.034(2) 0.030(2) 0.0096(18) -0.0063(17) 0.0143(16)
O1 0.0196(10) 0.0174(9) 0.0229(12) 0.0036(9) -0.0033(8) 0.0032(7)
O2 0.0160(9) 0.0172(9) 0.0272(13) 0.0049(9) -0.0022(8) 0.0009(7)
O3 0.0214(10) 0.0192(10) 0.0251(13) 0.0058(9) -0.0069(9) -0.0008(8)
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
C6 C1 C2 119.7(3)
C6 C1 C7 120.5(3)
C2 C1 C7 119.7(2)
C3 C2 C1 119.5(3)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 F1A 118.7(3)
C2 C3 C4 122.0(3)
F1A C3 C4 119.3(3)
C2 C3 H3A 119.0
C4 C3 H3A 119.0
C5 C4 C3 117.6(3)
C5 C4 H4 121.2
C3 C4 H4 121.2
F1B C5 C4 120.7(3)
F1B C5 C6 117.2(3)
C4 C5 C6 122.0(3)
C4 C5 H5 119.0
C6 C5 H5 119.0
C5 C6 C1 119.2(3)
C5 C6 H6 120.4
C1 C6 H6 120.4
O3 C7 C1 109.4(2)
O3 C7 C8 109.9(2)
C1 C7 C8 111.8(2)
O3 C7 H7 108.5
C1 C7 H7 108.5
C8 C7 H7 108.5
O1 C8 O2 124.7(2)
O1 C8 C7 123.0(2)
O2 C8 C7 112.3(2)
C8 O2 H2A 109.5
C7 O3 H3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.393(4)
C1 C2 1.396(4)
C1 C7 1.514(4)
C2 C3 1.367(4)
C2 H2 0.9500
C3 F1A 1.376(4)
C3 C4 1.399(4)
C3 H3A 0.9500
C4 C5 1.376(4)
C4 H4 0.9500
C5 F1B 1.363(4)
C5 C6 1.386(4)
C5 H5 0.9500
C6 H6 0.9500
C7 O3 1.424(3)
C7 C8 1.518(3)
C7 H7 1.0000
C8 O1 1.215(3)
C8 O2 1.323(3)
O2 H2A 0.8400
O3 H3 0.8400
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 0.0(4)
C7 C1 C2 C3 -179.2(2)
C1 C2 C3 F1A 177.1(3)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 -0.1(4)
F1A C3 C4 C5 -177.2(3)
C3 C4 C5 F1B 176.3(3)
C3 C4 C5 C6 0.2(4)
F1B C5 C6 C1 -176.4(3)
C4 C5 C6 C1 -0.2(4)
C2 C1 C6 C5 0.1(4)
C7 C1 C6 C5 179.3(2)
C6 C1 C7 O3 121.9(3)
C2 C1 C7 O3 -59.0(3)
C6 C1 C7 C8 -116.1(3)
C2 C1 C7 C8 63.0(3)
O3 C7 C8 O1 -2.3(4)
C1 C7 C8 O1 -124.0(3)
O3 C7 C8 O2 178.5(2)
C1 C7 C8 O2 56.7(3)
