Nanoporous organic layered crystals of double-headed bis(trifluorolactate)s. Hydrogen-bonded systematic crystal structures controlled by the symmetries of molecular components
Takahashi, Satoshi; Katagiri, Toshimasa; Uneyama, Kenji; CrystEngComm 8 (2006) 132–; doi:10.1039/b512051a

data_7203132
_publ_section_title
;
 Nanoporous organic layered crystals of double-headed
 bis(trifluorolactate)s. Hydrogen-bonded systematic crystal structures
 controlled by the symmetries of molecular components
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              132
_journal_paper_doi               10.1039/b512051a
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H22 F6 O6, (C8 H18)0.28'
_chemical_formula_sum            'C17.24 H27.04 F6 O6'
_chemical_formula_weight         444.51
_chemical_melting_point          322
_chemical_name_common
;(S,S)-(-)-nonamethylene bis(3,3,3-trifluorolactate) octane
solvate
;
_chemical_optical_rotation       '[\a]^25^~D~= -3.93 (c = 1.1, acetone)'
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 95.942(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   27.753(11)
_cell_length_b                   4.9906(10)
_cell_length_c                   7.992(3)
_cell_measurement_reflns_used    4015
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.7
_cell_volume                     1101.0(6)
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2928
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(HIGASHI, T. (1995). Abscor - Empirical Absorption Correction
based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             465
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_platon_squeeze_details
;
Although there were four peaks within the void from Fourier difference map,
the highly disordered solvents within the void were not crystallographically
well defined.

The SQUEEZE routine of the program PLATON was used
in order to eliminate the contribution of disordered solvents molecules,
thereby a final model based only on the ordered part of the crystal structure
was obtained.

The SQUEEZE routine suggested that
a total potential solvent area volume of 184.2 Ang^3^[16.7% of cell volume],
and a void electron population 37 per cell.

Refinement after the SQUEEZE routine gave significantly improved R values.
[R values before SQUEEZE]
R1 = 0.103 for >2sigma(I) data
R1 = 0.117 , wR2 = 0.322 , GooF = S = 1.62 for all data
( 1072 data and 0 restraint / 125 parameters)

_platon_squeeze_details
;
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Friedel pairs were merged before refinement.
;
_refine_ls_extinction_coef       0.014(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1068
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0496
_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/[\s^2^(Fo^2^)+(0.1104P)^2^+0.2214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                992
_reflns_number_total             1068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b512051a.txt
_cod_data_source_block           3f_octane_solvate
_cod_database_code               7203132