#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:41:59 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180515 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218453.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_7218453
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 92.709(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1888(12)
_cell_length_b                   10.1998(14)
_cell_length_c                   9.2654(12)
_cell_measurement_reflns_used    7074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     773.02(18)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b5 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b5 (Rigaku, 2012)
;
_computing_molecular_graphics
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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, VHF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9704
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b5 (Rigaku, 2012)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0602
_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)+(0.0916P)²+0.4411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1743
_reflns_number_gt                1268
_reflns_number_total             1752
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce01832j2.cif
_cod_data_source_block           2012gjt0004a
_cod_depositor_comments
'Adding full bibliography for 7218452--7218470.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7218453
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.3374(2) 0.96674(18) 0.09770(17) 0.0466(5) Uani 1 1 d .
O2 O 0.0711(2) 0.89246(16) 0.37748(17) 0.0287(4) Uani 1 1 d .
H2 H 0.0328 0.8164 0.3681 0.043 Uiso 1 1 calc R
O3 O 0.0708(2) 1.16460(15) 0.13413(17) 0.0263(4) Uani 1 1 d .
H3A H 0.0631 1.1110 0.0653 0.039 Uiso 1 1 calc R
O1 O -0.0247(2) 0.91361(16) 0.14893(17) 0.0322(5) Uani 1 1 d .
C1 C 0.2973(3) 1.0993(2) 0.2982(2) 0.0235(5) Uani 1 1 d .
C7 C 0.1149(3) 1.0964(2) 0.2646(2) 0.0217(5) Uani 1 1 d .
H7 H 0.0612 1.1423 0.3452 0.026 Uiso 1 1 calc R
C8 C 0.0463(3) 0.9572(2) 0.2558(2) 0.0233(5) Uani 1 1 d .
C2 C 0.4040(3) 1.0336(2) 0.2118(3) 0.0282(5) Uani 1 1 d .
C6 C 0.3660(3) 1.1687(2) 0.4155(3) 0.0300(6) Uani 1 1 d .
H6 H 0.2969 1.2152 0.4772 0.036 Uiso 1 1 calc R
C5 C 0.5338(3) 1.1708(3) 0.4435(3) 0.0346(6) Uani 1 1 d .
H5 H 0.5789 1.2185 0.5239 0.042 Uiso 1 1 calc R
C3 C 0.5707(3) 1.0337(3) 0.2360(3) 0.0372(6) Uani 1 1 d .
H3 H 0.6396 0.9874 0.1739 0.045 Uiso 1 1 calc R
C4 C 0.6356(3) 1.1034(3) 0.3543(3) 0.0382(6) Uani 1 1 d .
H4 H 0.7505 1.1049 0.3740 0.046 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
F1 0.0438(10) 0.0557(11) 0.0404(10) -0.0154(8) 0.0029(7) 0.0079(8)
O2 0.0395(10) 0.0231(8) 0.0229(9) 0.0021(7) -0.0034(7) -0.0070(7)
O3 0.0382(10) 0.0204(8) 0.0200(8) -0.0016(6) -0.0021(7) 0.0042(7)
O1 0.0446(11) 0.0295(9) 0.0221(9) -0.0020(7) -0.0048(7) -0.0101(8)
C1 0.0288(12) 0.0201(10) 0.0217(11) 0.0039(9) 0.0012(9) -0.0014(9)
C7 0.0274(12) 0.0200(10) 0.0176(11) 0.0000(8) 0.0013(9) 0.0019(9)
C8 0.0255(11) 0.0243(11) 0.0203(12) -0.0010(9) 0.0035(9) 0.0007(9)
C2 0.0285(13) 0.0344(13) 0.0218(12) -0.0007(10) 0.0008(9) 0.0005(10)
C6 0.0371(14) 0.0230(11) 0.0297(13) 0.0000(9) 0.0002(11) -0.0025(10)
C5 0.0356(14) 0.0316(13) 0.0361(14) 0.0000(11) -0.0043(11) -0.0067(11)
C3 0.0307(14) 0.0493(16) 0.0320(14) 0.0033(12) 0.0065(11) 0.0046(12)
C4 0.0265(13) 0.0468(15) 0.0410(15) 0.0094(12) -0.0013(11) -0.0050(12)
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
C8 O2 H2 109.5
C7 O3 H3A 109.5
C2 C1 C6 117.0(2)
C2 C1 C7 121.0(2)
C6 C1 C7 122.0(2)
O3 C7 C1 111.92(18)
O3 C7 C8 109.27(17)
C1 C7 C8 112.74(18)
O3 C7 H7 107.6
C1 C7 H7 107.6
C8 C7 H7 107.6
O1 C8 O2 124.5(2)
O1 C8 C7 123.2(2)
O2 C8 C7 112.30(18)
F1 C2 C3 119.3(2)
F1 C2 C1 117.0(2)
C3 C2 C1 123.7(2)
C5 C6 C1 120.9(2)
C5 C6 H6 119.5
C1 C6 H6 119.5
C4 C5 C6 120.0(2)
C4 C5 H5 120.0
C6 C5 H5 120.0
C2 C3 C4 118.0(2)
C2 C3 H3 121.0
C4 C3 H3 121.0
C5 C4 C3 120.4(2)
C5 C4 H4 119.8
C3 C4 H4 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.351(3)
O2 C8 1.315(3)
O2 H2 0.8400
O3 C7 1.426(3)
O3 H3A 0.8400
O1 C8 1.209(3)
C1 C2 1.386(3)
C1 C6 1.393(3)
C1 C7 1.511(3)
C7 C8 1.527(3)
C7 H7 1.0000
C2 C3 1.373(4)
C6 C5 1.387(4)
C6 H6 0.9500
C5 C4 1.384(4)
C5 H5 0.9500
C3 C4 1.391(4)
C3 H3 0.9500
C4 H4 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.84 1.76 2.598(2) 171.3 2_545
O3 H3A O1 0.84 2.01 2.750(2) 146.5 3_575
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
C2 C1 C7 O3 -67.4(3)
C6 C1 C7 O3 111.8(2)
C2 C1 C7 C8 56.2(3)
C6 C1 C7 C8 -124.5(2)
O3 C7 C8 O1 4.2(3)
C1 C7 C8 O1 -120.9(2)
O3 C7 C8 O2 -174.73(18)
C1 C7 C8 O2 60.1(2)
C6 C1 C2 F1 -179.8(2)
C7 C1 C2 F1 -0.5(3)
C6 C1 C2 C3 0.1(4)
C7 C1 C2 C3 179.4(2)
C2 C1 C6 C5 -0.2(3)
C7 C1 C6 C5 -179.5(2)
C1 C6 C5 C4 0.0(4)
F1 C2 C3 C4 180.0(2)
C1 C2 C3 C4 0.1(4)
C6 C5 C4 C3 0.2(4)
C2 C3 C4 C5 -0.3(4)
