Highly fluorinated naphthalenes and bifurcated C‒H⋯F‒C hydrogen bonding
Loader, Jason R.; Libri, Stefano; Meijer, Anthony J. H. M.; Perutz, Robin N.; Brammer, Lee; CrystEngComm 16 (2014) 9711–; doi:10.1039/C4CE01322K

data_7218149
_publ_section_title
;
 Highly fluorinated naphthalenes and bifurcated C--H&#x22EF;F--C hydrogen
 bonding
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              9711
_journal_paper_doi               10.1039/C4CE01322K
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C10 H3 F5'
_chemical_formula_sum            'C10 H3 F5'
_chemical_formula_weight         218.12
_chemical_name_systematic        pentafluoronaphthalene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-03-01
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.08(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5748(17)
_cell_length_b                   3.6622(7)
_cell_length_c                   12.423(3)
_cell_measurement_reflns_used    630
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.63
_cell_measurement_theta_min      5.80
_cell_volume                     389.55(14)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.773
_diffrn_measured_fraction_theta_max 0.773
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1884
_diffrn_reflns_theta_full        32.20
_diffrn_reflns_theta_max         32.20
_diffrn_reflns_theta_min         5.64
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   twinabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0820
_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^)+(0.0676P)^2^+0.7948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2234
_reflns_number_gt                1322
_reflns_number_total             1884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01322k2.cif
_cod_data_source_block           twin5
_cod_depositor_comments
'Adding full bibliography for 7218148--7218149.cif.'
_cod_original_cell_volume        389.56(13)
_cod_database_code               7218149