Effect of Fluorination on Molecular Conformation in the Solid State: Tuning the Conformation of Cocrystal Formers
Friščić, Tomislav; Reid, David G.; Day, Graeme M.; Duer, Melinda J.; Jones, William; Crystal Growth & Design 11 (2011) 972–; doi:10.1021/cg1016388

data_4500521
_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 &amp; Design'
_journal_page_first              972
_journal_paper_doi               10.1021/cg1016388
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         '2(C8 H10 N4 O2) (C6 H2 F8 O4)'
_chemical_formula_sum            'C22 H22 F8 N8 O8'
_chemical_formula_weight         678.48
_chemical_name_common            (caf)2.(Hfad)
_chemical_name_systematic
;
 caffeine:octafluoroadipic acid 2/1
;
_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                 112.6920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8232(2)
_cell_length_b                   13.2644(3)
_cell_length_c                   11.2546(3)
_cell_measurement_reflns_used    8920
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      1.00
_cell_volume                     1352.95(6)
_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      180(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12309
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.894
_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    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0819P)^2^+0.2910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                3472
_reflns_number_total             4272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1016388_si_003.cif
_cod_data_source_block           caf-Hfad
_cod_original_cell_volume        1352.95(5)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4500521