#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:41:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180515 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218465.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_7218465
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         'C9 H7 F3 O3'
_chemical_formula_sum            'C9 H7 F3 O3'
_chemical_formula_weight         220.15
_chemical_name_systematic
;
 ?
;
_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                   9.8173(5)
_cell_length_b                   9.6920(5)
_cell_length_c                   19.9217(14)
_cell_measurement_reflns_used    16778
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1895.54(19)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_molecular_graphics
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30644
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1612
_refine_ls_R_factor_gt           0.0832
_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)+(0.0285P)²+0.7024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                1123
_reflns_number_total             2173
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce01832j2.cif
_cod_data_source_block           2012jms0013a-RS-4F3MeMA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7218452--7218470.cif.
;
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               7218465
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_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
C4 C 0.6212(4) -0.3175(4) -0.23458(19) 0.0802(9) Uani 1 1 d . A .
C7 C 0.6285(3) -0.2776(3) -0.44837(14) 0.0571(7) Uani 1 1 d . . .
H2 H 0.6808 -0.1947 -0.4597 0.069 Uiso 1 1 calc R . .
C8 C 0.4864(3) -0.2613(3) -0.47696(13) 0.0549(7) Uani 1 1 d . . .
C5 C 0.6932(4) -0.2155(4) -0.2640(2) 0.0994(11) Uani 1 1 d . . .
H6 H 0.7425 -0.1543 -0.2375 0.119 Uiso 1 1 calc R . .
C1 C 0.6240(3) -0.2900(3) -0.37276(15) 0.0569(7) Uani 1 1 d . . .
C2 C 0.5521(3) -0.3942(3) -0.34260(18) 0.0852(10) Uani 1 1 d . . .
H4 H 0.5043 -0.4570 -0.3689 0.102 Uiso 1 1 calc R . .
C6 C 0.6946(3) -0.2010(3) -0.33288(19) 0.0867(10) Uani 1 1 d . . .
H7 H 0.7442 -0.1297 -0.3523 0.104 Uiso 1 1 calc R . .
C3 C 0.5500(4) -0.4068(4) -0.2740(2) 0.0959(11) Uani 1 1 d . . .
H5 H 0.4995 -0.4771 -0.2542 0.115 Uiso 1 1 calc R . .
F1A F 0.4975(6) -0.375(2) -0.1351(4) 0.144(5) Uani 0.69(2) 1 d P A 1
F2A F 0.7016(8) -0.4323(13) -0.1397(5) 0.133(4) Uani 0.69(2) 1 d P A 1
F3A F 0.655(3) -0.2211(12) -0.1270(4) 0.185(7) Uani 0.69(2) 1 d P A 1
F1B F 0.598(10) -0.447(4) -0.1456(9) 0.30(3) Uani 0.31(2) 1 d P A 2
F2B F 0.733(3) -0.301(8) -0.1332(10) 0.25(2) Uani 0.31(2) 1 d P A 2
F3B F 0.542(5) -0.248(5) -0.1367(9) 0.178(13) Uani 0.31(2) 1 d P A 2
C9 C 0.6192(7) -0.3329(8) -0.1606(3) 0.1150(15) Uani 1 1 d . . .
O3 O 0.69423(16) -0.39298(17) -0.47823(11) 0.0677(6) Uani 1 1 d . . .
H3 H 0.6382 -0.4540 -0.4852 0.101 Uiso 1 1 calc R . .
O1 O 0.43893(18) -0.13729(17) -0.46677(10) 0.0734(6) Uani 1 1 d . . .
H1 H 0.3622 -0.1312 -0.4828 0.110 Uiso 1 1 calc R . .
O2 O 0.42537(17) -0.35242(17) -0.50436(10) 0.0707(6) Uani 1 1 d . . .
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
C4 0.080(2) 0.088(2) 0.073(3) 0.000(2) -0.005(2) 0.016(2)
C7 0.0475(14) 0.0493(15) 0.075(2) -0.0050(14) 0.0025(15) -0.0056(12)
C8 0.0572(16) 0.0483(15) 0.0591(18) 0.0027(14) 0.0040(14) -0.0039(13)
C5 0.109(3) 0.103(3) 0.085(3) -0.016(2) -0.023(2) -0.017(2)
C1 0.0455(14) 0.0560(16) 0.069(2) -0.0022(16) -0.0016(15) 0.0016(13)
C2 0.094(2) 0.083(2) 0.079(3) 0.0041(19) -0.008(2) -0.0287(19)
C6 0.090(2) 0.087(2) 0.083(3) -0.004(2) -0.0098(19) -0.0269(19)
C3 0.107(3) 0.098(2) 0.082(3) 0.018(2) 0.000(2) -0.020(2)
F1A 0.116(5) 0.229(14) 0.087(3) 0.025(5) 0.026(2) 0.031(5)
F2A 0.126(5) 0.176(9) 0.096(5) 0.032(4) -0.017(3) 0.044(4)
F3A 0.31(2) 0.162(7) 0.082(3) -0.019(4) -0.026(7) -0.024(9)
F1B 0.60(9) 0.23(3) 0.076(9) 0.051(12) 0.02(3) -0.07(5)
F2B 0.211(18) 0.42(6) 0.118(10) -0.06(2) -0.097(10) 0.05(3)
F3B 0.23(2) 0.23(3) 0.076(8) -0.024(12) 0.026(11) 0.09(2)
C9 0.130(5) 0.133(5) 0.081(4) 0.008(4) -0.008(4) 0.022(5)
O3 0.0494(10) 0.0598(11) 0.0938(15) -0.0150(11) 0.0050(10) -0.0052(9)
O1 0.0672(12) 0.0548(11) 0.0981(16) -0.0131(11) -0.0178(11) 0.0045(9)
O2 0.0637(12) 0.0515(10) 0.0971(16) -0.0099(10) -0.0146(11) -0.0043(9)
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
C5 C4 C3 118.9(3)
C5 C4 C9 120.9(5)
C3 C4 C9 120.2(5)
O3 C7 C1 111.6(2)
O3 C7 C8 110.1(2)
C1 C7 C8 110.9(2)
O3 C7 H2 108.1
C1 C7 H2 108.1
C8 C7 H2 108.1
O2 C8 O1 124.8(2)
O2 C8 C7 123.7(2)
O1 C8 C7 111.5(2)
C4 C5 C6 120.8(3)
C4 C5 H6 119.6
C6 C5 H6 119.6
C6 C1 C2 118.2(3)
C6 C1 C7 121.1(3)
C2 C1 C7 120.7(3)
C1 C2 C3 120.6(3)
C1 C2 H4 119.7
C3 C2 H4 119.7
C1 C6 C5 120.7(3)
C1 C6 H7 119.7
C5 C6 H7 119.7
C4 C3 C2 120.7(3)
C4 C3 H5 119.7
C2 C3 H5 119.7
F1B C9 F3B 116(3)
F1B C9 F2B 106(2)
F3B C9 F2B 102.2(16)
F1B C9 F3A 134.2(14)
F3B C9 F3A 54.1(18)
F2B C9 F3A 50(2)
F1B C9 F2A 49(5)
F3B C9 F2A 138.6(11)
F2B C9 F2A 61(3)
F3A C9 F2A 105.8(9)
F1B C9 F1A 57(4)
F3B C9 F1A 61(2)
F2B C9 F1A 132.8(14)
F3A C9 F1A 107.1(9)
F2A C9 F1A 101.5(9)
F1B C9 C4 110.6(12)
F3B C9 C4 109.2(11)
F2B C9 C4 112.8(14)
F3A C9 C4 114.7(7)
F2A C9 C4 112.2(6)
F1A C9 C4 114.4(6)
C7 O3 H3 109.5
C8 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C4 C5 1.349(4)
C4 C3 1.362(4)
C4 C9 1.482(6)
C7 O3 1.421(3)
C7 C1 1.512(4)
C7 C8 1.515(4)
C7 H2 0.9800
C8 O2 1.198(3)
C8 O1 1.305(3)
C5 C6 1.379(4)
C5 H6 0.9300
C1 C6 1.362(4)
C1 C2 1.371(4)
C2 C3 1.372(4)
C2 H4 0.9300
C6 H7 0.9300
C3 H5 0.9300
F1A C9 1.362(11)
F2A C9 1.325(11)
F3A C9 1.322(11)
F1B C9 1.17(2)
F2B C9 1.28(3)
F3B C9 1.216(17)
O3 H3 0.8200
O1 H1 0.8200
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
O3 C7 C8 O2 20.3(4)
C1 C7 C8 O2 -103.7(3)
O3 C7 C8 O1 -160.9(2)
C1 C7 C8 O1 75.2(3)
C3 C4 C5 C6 0.4(5)
C9 C4 C5 C6 -179.8(4)
O3 C7 C1 C6 113.8(3)
C8 C7 C1 C6 -123.2(3)
O3 C7 C1 C2 -64.0(3)
C8 C7 C1 C2 59.0(3)
C6 C1 C2 C3 1.0(5)
C7 C1 C2 C3 178.8(3)
C2 C1 C6 C5 -0.2(5)
C7 C1 C6 C5 -178.0(3)
C4 C5 C6 C1 -0.5(5)
C5 C4 C3 C2 0.4(5)
C9 C4 C3 C2 -179.4(4)
C1 C2 C3 C4 -1.1(5)
C5 C4 C9 F1B -154(5)
C3 C4 C9 F1B 26(6)
C5 C4 C9 F3B 78(3)
C3 C4 C9 F3B -102(3)
C5 C4 C9 F2B -35(4)
C3 C4 C9 F2B 145(4)
C5 C4 C9 F3A 19.5(17)
C3 C4 C9 F3A -160.6(15)
C5 C4 C9 F2A -101.3(10)
C3 C4 C9 F2A 78.6(9)
C5 C4 C9 F1A 143.8(10)
C3 C4 C9 F1A -36.3(12)
