# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Gautam Desiraju'
_publ_contact_author_email       'GAUTAM DESIRAJU@YAHOO.COM'

_publ_section_title              
;
C-H***F-C Hydrogen Bonding in 1,2,3,5-Tetrafluorobenzene
and other Fluoroaromatic Compounds and the Crystal
Structure of Alloxan Revisited
;
loop_
_publ_author_name
'Gautam Desiraju'
'Dieter Blaser'
'Roland Boese'
'Michael Kirchner'
'Tejender Thakur'

data_tetrafluorbe
_database_code_depnum_ccdc_archive 'CCDC 753706'

_ccdc_compound_id                1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1.2.3.5-Tetrafluorobenzene
;
_chemical_name_common            1.2.3.5-Tetrafluorobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H2 F4'
_chemical_formula_weight         150.08

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.703(4)
_cell_length_b                   14.572(17)
_cell_length_c                   10.573(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.340(19)
_cell_angle_gamma                90.00
_cell_volume                     567.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    715
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      25.19

_exptl_crystal_description       cylindric
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
The crystallization was performed
on the diffractometer at a temperature of
180 K with a miniature zone melting procedure
using focused infrared-laser-radiation
according to:
R. Boese, M.Nussbaumer,
"In Situ crystallisation Techniques", in:
"Organic Crystal Chemistry", Ed. D.W. Jones,
Oxford University Press,
Oxford,England, (1994) 20-37
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Siemens SMART three axis goniometer with APEX II area detector system
Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
Data collection strategy APEX 2 / COSMO
with chi = 0
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            2280
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         28.71
_reflns_number_total             1309
_reflns_number_gt                736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0979P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    
;
Riding model on idealized geometrics
with the 1.2 fold isotropic displacement
parameters of the equivalent Uij of the
corresponding carbon atom
;
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1309
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1767
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5806(9) 0.70098(18) 0.7986(3) 0.0362(7) Uani 1 1 d . . .
C2 C 0.4036(9) 0.69211(18) 0.6772(3) 0.0377(7) Uani 1 1 d . . .
C3 C 0.3339(8) 0.60500(19) 0.6289(2) 0.0354(7) Uani 1 1 d . . .
C4 C 0.4356(8) 0.52799(17) 0.6999(3) 0.0363(7) Uani 1 1 d . . .
H4 H 0.3845 0.4674 0.6661 0.044 Uiso 1 1 d R . .
C5 C 0.6085(8) 0.54136(17) 0.8200(3) 0.0357(7) Uani 1 1 d . . .
C6 C 0.6841(8) 0.6265(2) 0.8721(3) 0.0379(7) Uani 1 1 d . . .
H6 H 0.8101 0.6343 0.9557 0.045 Uiso 1 1 d R . .
F1 F 0.6472(7) 0.78597(12) 0.8433(2) 0.0637(7) Uani 1 1 d . . .
F2 F 0.3008(7) 0.76601(13) 0.6071(2) 0.0613(7) Uani 1 1 d . . .
F3 F 0.1611(6) 0.59731(13) 0.51132(16) 0.0554(6) Uani 1 1 d . . .
F5 F 0.7113(6) 0.46655(12) 0.89014(18) 0.0569(6) Uani 1 1 d . . .

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
C1 0.0340(18) 0.0328(14) 0.0423(17) -0.0058(10) 0.0060(13) -0.0042(11)
C2 0.0394(19) 0.0353(14) 0.0391(16) 0.0072(11) 0.0075(13) 0.0017(12)
C3 0.0313(18) 0.0483(17) 0.0266(13) 0.0012(11) 0.0031(12) -0.0005(11)
C4 0.0356(18) 0.0331(14) 0.0403(16) -0.0047(10) 0.0056(13) 0.0000(11)
C5 0.0331(17) 0.0363(15) 0.0373(15) 0.0082(11) 0.0020(12) 0.0068(11)
C6 0.0316(18) 0.0475(17) 0.0343(15) -0.0030(11) 0.0023(13) 0.0002(12)
F1 0.0833(17) 0.0374(10) 0.0688(15) -0.0116(9) 0.0012(12) -0.0101(10)
F2 0.0804(17) 0.0437(11) 0.0584(13) 0.0172(8) 0.0018(11) 0.0088(9)
F3 0.0590(14) 0.0699(13) 0.0342(10) -0.0009(8) -0.0085(9) -0.0054(10)
F5 0.0697(15) 0.0451(11) 0.0537(12) 0.0140(8) -0.0038(10) 0.0140(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.339(3) . ?
C1 C6 1.366(4) . ?
C1 C2 1.381(5) . ?
C2 F2 1.339(3) . ?
C2 C3 1.382(4) . ?
C3 F3 1.339(3) . ?
C3 C4 1.379(4) . ?
C4 C5 1.372(5) . ?
C5 F5 1.349(3) . ?
C5 C6 1.373(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C6 120.4(3) . . ?
F1 C1 C2 117.7(2) . . ?
C6 C1 C2 121.9(2) . . ?
F2 C2 C1 121.1(2) . . ?
F2 C2 C3 120.3(3) . . ?
C1 C2 C3 118.7(2) . . ?
F3 C3 C4 120.7(2) . . ?
F3 C3 C2 118.1(2) . . ?
C4 C3 C2 121.2(3) . . ?
C5 C4 C3 117.4(2) . . ?
F5 C5 C4 117.9(2) . . ?
F5 C5 C6 118.5(3) . . ?
C4 C5 C6 123.6(2) . . ?
C1 C6 C5 117.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        28.71
_diffrn_measured_fraction_theta_full 0.900
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.077

_vrf_PLAT029_tetrafluorbe        
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.90
RESPONSE:
The compounds are liquids at RT. The single crystals
are formed by an in-situ zone melting process inside a quartz capillary
using an IR-laser. The experimental setup does only allow for a
omega scan of the single crystal. This limits the completeness
to 75% to 95% depending on the crystal system.
;