#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/68/4116820.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_4116820
loop_
_publ_author_name
'Venkat R. Thalladi'
'Hans-Christoph Weiss'
'Dieter Bl\"aser'
'Roland Boese'
'Ashwini Nangia'
'Gautam R. Desiraju'
_publ_section_title
;
 C-H...F Interactions in the Crystal Structures of Some Fluorobenzenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8702
_journal_page_last               8710
_journal_paper_doi               10.1021/ja981198e
_journal_volume                  120
_journal_year                    1998
_chemical_compound_source        Aldrich
_chemical_formula_moiety         'C6 H4 F2'
_chemical_formula_sum            'C6 H4 F2'
_chemical_formula_weight         114.09
_chemical_melting_point          239
_chemical_name_common            1,2-difluorobenzene
_chemical_name_systematic        1,2-difluorobenzene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 103.815(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4806(11)
_cell_length_b                   5.9608(9)
_cell_length_c                   11.725(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     507.70(14)
_computing_cell_refinement       'Siemens P3-PC diffractometer program V.4.24'
_computing_data_collection       'Siemens P3-PC diffractometer program V.4.24'
_computing_data_reduction        'Siemens XDISK V.4.20.2 PC'
_computing_molecular_graphics    'SHELXL-93 (Sheldrick, 1993)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device       'Nicolet R3m/V four circle diffractometer'
_diffrn_measurement_method       'Wyckoff scan mode'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2395
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    none
_exptl_crystal_description       cylindric
_exptl_crystal_F_000             232
_exptl_crystal_size_max          '0.3 mm diameter'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0520(101)
_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_all   1.055
_refine_ls_goodness_of_fit_obs   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_restrained_S_obs      1.074
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_obs          0.0344
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.1078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1086
_refine_ls_wR_factor_obs         0.1051
_reflns_number_observed          1119
_reflns_number_total             1231
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja981198e_2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.1078P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.1078P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        507.68(13)
_cod_database_code               4116820
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
F1 0.0411(5) 0.0289(4) 0.0393(4) -0.0144(3) 0.0101(4) -0.0015(3)
C1 0.0238(6) 0.0205(4) 0.0254(5) -0.0036(3) 0.0075(5) -0.0020(4)
F2 0.0364(5) 0.0455(4) 0.0222(3) 0.0050(3) -0.0026(3) 0.0017(3)
C2 0.0206(6) 0.0258(4) 0.0197(4) 0.0034(3) 0.0021(4) -0.0016(4)
C3 0.0247(6) 0.0203(4) 0.0317(5) 0.0019(3) 0.0083(5) 0.0012(4)
C4 0.0261(6) 0.0291(5) 0.0279(5) -0.0079(4) 0.0076(5) -0.0042(4)
C5 0.0222(6) 0.0386(6) 0.0217(4) 0.0010(4) 0.0019(5) -0.0025(4)
C6 0.0222(6) 0.0254(4) 0.0300(5) 0.0056(4) 0.0052(5) 0.0032(4)
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
F1 F 0.98361(11) 0.15838(11) 0.58836(6) 0.0363(2) Uani 1 d
C1 C 0.9903(2) 0.3221(2) 0.66835(9) 0.0229(2) Uani 1 d
F2 F 0.78362(12) 0.52637(13) 0.52350(6) 0.0363(2) Uani 1 d
C2 C 0.8868(2) 0.5127(2) 0.63487(9) 0.0225(2) Uani 1 d
C3 C 0.8862(2) 0.6839(2) 0.71347(10) 0.0253(3) Uani 1 d
H3 H 0.8106(22) 0.8159(25) 0.6887(13) 0.032(4) Uiso 1 d
C4 C 0.9913(2) 0.6605(2) 0.82770(10) 0.0275(3) Uani 1 d
H4 H 0.9856(25) 0.7751(32) 0.8806(16) 0.050(5) Uiso 1 d
C5 C 1.0959(2) 0.4694(2) 0.86130(10) 0.0281(3) Uani 1 d
H5 H 1.1574(26) 0.4505(29) 0.9358(16) 0.042(4) Uiso 1 d
C6 C 1.0958(2) 0.2978(2) 0.78114(10) 0.0260(3) Uani 1 d
H6 H 1.1680(22) 0.1624(25) 0.7992(13) 0.034(4) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
F1 C1 C6 120.73(9)
F1 C1 C2 118.31(10)
C6 C1 C2 120.95(9)
F2 C2 C3 120.67(10)
F2 C2 C1 118.51(9)
C3 C2 C1 120.82(10)
C2 C3 C4 118.67(10)
C5 C4 C3 120.56(9)
C4 C5 C6 120.28(11)
C1 C6 C5 118.72(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.3459(11)
C1 C6 1.376(2)
C1 C2 1.3784(15)
F2 C2 1.3513(12)
C2 C3 1.3757(14)
C3 C4 1.389(2)
C4 C5 1.384(2)
C5 C6 1.389(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9325
2 PubChem 9706
