#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:34:15 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179536 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/05/4500522.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_4500522
loop_
_publ_author_name
'Friščić, Tomislav'
'Reid, David G.'
'Day, Graeme M.'
'Duer, Melinda J.'
'Jones, William'
_publ_section_title
;
 Effect of Fluorination on Molecular Conformation in the Solid State:
 Tuning the Conformation of Cocrystal Formers
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              972
_journal_paper_doi               10.1021/cg1016388
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         '2(C4 H2 F4 O4), 2(H2 O)'
_chemical_formula_sum            'C4 H4 F4 O5'
_chemical_formula_weight         208.07
_chemical_name_common            Hfsu.H2O
_chemical_name_systematic
;
 tetrafluorosuccinic acid monohydrate
;
_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            16
_cell_length_a                   10.6924(2)
_cell_length_b                   11.6169(2)
_cell_length_c                   22.4410(3)
_cell_measurement_reflns_used    23201
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      1.00
_cell_volume                     2787.45(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            23437
_diffrn_reflns_theta_full        33.13
_diffrn_reflns_theta_max         33.13
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0661P)²+0.2025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                4032
_reflns_number_total             5248
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1016388_si_003.cif
_cod_data_source_block           Hfsu.H2O
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4500522
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
C1 C 0.58934(10) 0.33358(10) 0.60218(5) 0.0155(2) Uani 1 1 d .
C2 C 0.48890(10) 0.25338(10) 0.62945(5) 0.0159(2) Uani 1 1 d .
C3 C 0.50813(10) 0.12579(10) 0.61263(5) 0.0156(2) Uani 1 1 d .
C4 C 0.40998(10) 0.04573(10) 0.64125(5) 0.0159(2) Uani 1 1 d .
C5 C 0.09514(11) 0.11032(10) 0.69511(5) 0.0159(2) Uani 1 1 d .
C6 C -0.01096(10) 0.17793(11) 0.66380(5) 0.0165(2) Uani 1 1 d .
C7 C 0.00800(10) 0.18625(10) 0.59585(6) 0.0160(2) Uani 1 1 d .
C8 C -0.09444(11) 0.25693(10) 0.56369(5) 0.0156(2) Uani 1 1 d .
F1 F 0.37370(7) 0.28523(7) 0.61136(4) 0.02475(18) Uani 1 1 d .
F2 F 0.49342(8) 0.26200(7) 0.68929(3) 0.02341(17) Uani 1 1 d .
F3 F 0.50109(8) 0.11562(7) 0.55287(3) 0.02252(17) Uani 1 1 d .
F4 F 0.62480(6) 0.09551(7) 0.62966(4) 0.02292(17) Uani 1 1 d .
F5 F -0.01392(8) 0.28582(7) 0.68585(4) 0.02575(18) Uani 1 1 d .
F6 F -0.12294(7) 0.12848(8) 0.67395(4) 0.02565(18) Uani 1 1 d .
F7 F 0.00782(8) 0.07810(7) 0.57373(3) 0.02255(17) Uani 1 1 d .
F8 F 0.12188(7) 0.23248(8) 0.58559(4) 0.02437(18) Uani 1 1 d .
O1 O 0.56845(8) 0.35071(8) 0.54565(4) 0.01940(18) Uani 1 1 d .
H1 H 0.6245 0.3935 0.5316 0.029 Uiso 1 1 calc R
O2 O 0.67459(8) 0.37092(9) 0.63163(4) 0.02049(18) Uani 1 1 d .
O3 O 0.43862(9) 0.02311(9) 0.69630(4) 0.02140(19) Uani 1 1 d .
H3 H 0.3828 -0.0185 0.7114 0.032 Uiso 1 1 calc R
O4 O 0.31890(8) 0.01344(8) 0.61388(4) 0.02053(19) Uani 1 1 d .
O5 O 0.07631(8) -0.00039(8) 0.69306(4) 0.01933(18) Uani 1 1 d .
H5 H 0.1342 -0.0344 0.7112 0.029 Uiso 1 1 calc R
O6 O 0.18354(8) 0.16003(8) 0.71692(4) 0.02153(19) Uani 1 1 d .
O7 O -0.07256(8) 0.36740(8) 0.56754(4) 0.01925(18) Uani 1 1 d .
H7 H -0.1286 0.4037 0.5492 0.029 Uiso 1 1 calc R
O8 O -0.18214(8) 0.21064(8) 0.53978(4) 0.02043(18) Uani 1 1 d .
O9 O -0.24847(8) 0.48434(8) 0.50683(4) 0.01764(17) Uani 1 1 d .
O10 O 0.23145(8) 0.38972(8) 0.74580(4) 0.01854(17) Uani 1 1 d .
H30 H -0.2722 0.5554 0.5129 0.030 Uiso 1 1 d .
H40 H -0.2272 0.4872 0.4724 0.030 Uiso 1 1 d .
H1O H 0.2290 0.3870 0.7822 0.030 Uiso 1 1 d .
H2O H 0.2250 0.3206 0.7368 0.030 Uiso 1 1 d .
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
O2 C1 O1 127.42(11)
O2 C1 C2 121.61(11)
O1 C1 C2 110.96(10)
F2 C2 F1 108.19(9)
F2 C2 C3 108.07(10)
F1 C2 C3 108.16(10)
F2 C2 C1 108.93(9)
F1 C2 C1 110.47(10)
C3 C2 C1 112.89(9)
F3 C3 F4 108.06(9)
F3 C3 C4 108.87(9)
F4 C3 C4 110.70(10)
F3 C3 C2 108.66(10)
F4 C3 C2 107.69(9)
C4 C3 C2 112.75(9)
O4 C4 O3 127.53(11)
O4 C4 C3 121.51(11)
O3 C4 C3 110.94(10)
O6 C5 O5 127.28(11)
O6 C5 C6 120.88(11)
O5 C5 C6 111.82(10)
F6 C6 F5 108.27(10)
F6 C6 C7 108.11(9)
F5 C6 C7 107.95(10)
F6 C6 C5 110.97(10)
F5 C6 C5 108.80(10)
C7 C6 C5 112.60(9)
F8 C7 F7 107.96(9)
F8 C7 C6 108.20(10)
F7 C7 C6 107.76(10)
F8 C7 C8 110.34(10)
F7 C7 C8 108.73(9)
C6 C7 C8 113.67(9)
O8 C8 O7 127.29(11)
O8 C8 C7 121.39(11)
O7 C8 C7 111.31(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2065(14)
C1 O1 1.3035(15)
C1 C2 1.5478(16)
C2 F2 1.3476(14)
C2 F1 1.3487(13)
C2 C3 1.5433(17)
C3 F3 1.3484(14)
C3 F4 1.3512(13)
C3 C4 1.5424(16)
C4 O4 1.2110(14)
C4 O3 1.2997(15)
C5 O6 1.2110(15)
C5 O5 1.3025(15)
C5 C6 1.5484(16)
C6 F6 1.3474(13)
C6 F5 1.3478(14)
C6 C7 1.5412(18)
C7 F8 1.3506(13)
C7 F7 1.3508(14)
C7 C8 1.5476(16)
C8 O8 1.2069(14)
C8 O7 1.3073(15)
