Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
M.Gdaniec

_publ_contact_author_name        'Maria Gdaniec'
_publ_contact_author_address     
;
Department of Crystallography
Adam Mickiewicz University
Faculty of Chemistry
Grunwaldzka 6
Poznan
60-780
POLAND
;

_publ_contact_author_email       MAGDAN@AMU.EDU.PL

_publ_requested_journal          'Cryst Eng. Comm.'

_publ_section_title              
;
On the polymorphs of pentafluorophenol and its 2:1
co-crystal with pentafluoroaniline
;

data_cocryst
_database_code_depnum_ccdc_archive 'CCDC 632638'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,3,4,5,6-pentafluorophenol 2,3,4,5,6-pentafluoroaniline 2:1 adduct
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2C6F5OH, C6F5NH2'
_chemical_formula_sum            'C18 H4 F15 N O2'
_chemical_formula_weight         551.22

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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'

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

_cell_length_a                   21.1635(16)
_cell_length_b                   5.6554(4)
_cell_length_c                   16.5577(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.797(7)
_cell_angle_gamma                90.00
_cell_volume                     1799.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2644
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6745
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         27.10
_reflns_number_total             1975
_reflns_number_gt                1625
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_cell_refinement       
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_data_reduction        
;
CrysAlis RED
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Bruno et al., 2002)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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^)+(0.0350P)^2^] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1975
_refine_ls_number_parameters     341
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_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
O1A O 0.56149(13) 0.9079(4) 0.46573(19) 0.0213(6) Uani 1 1 d . . .
H1A H 0.554(2) 0.916(8) 0.411(3) 0.058(14) Uiso 1 1 d . . .
F2A F 0.56938(11) 0.8382(3) 0.63027(15) 0.0244(5) Uani 1 1 d . . .
F3A F 0.51307(11) 0.4533(4) 0.67157(15) 0.0270(6) Uani 1 1 d . . .
F4A F 0.44144(11) 0.1290(4) 0.54291(16) 0.0303(6) Uani 1 1 d . . .
F5A F 0.43034(11) 0.1930(4) 0.37390(17) 0.0274(6) Uani 1 1 d . . .
F6A F 0.48683(10) 0.5785(4) 0.33319(14) 0.0229(5) Uani 1 1 d . . .
C1A C 0.52978(18) 0.7162(6) 0.4814(3) 0.0170(8) Uani 1 1 d . . .
C2A C 0.53455(19) 0.6773(7) 0.5666(3) 0.0190(9) Uani 1 1 d . . .
C3A C 0.50530(19) 0.4835(6) 0.5870(3) 0.0191(8) Uani 1 1 d . . .
C4A C 0.46967(19) 0.3205(6) 0.5230(3) 0.0204(9) Uani 1 1 d . . .
C5A C 0.46394(19) 0.3519(6) 0.4378(3) 0.0202(9) Uani 1 1 d . . .
C6A C 0.49328(18) 0.5476(6) 0.4175(3) 0.0174(8) Uani 1 1 d . . .
O1B O 0.64107(13) 1.2521(5) 0.58357(18) 0.0223(6) Uani 1 1 d . . .
H1B H 0.622(2) 1.115(9) 0.554(3) 0.069(15) Uiso 1 1 d . . .
F2B F 0.70606(11) 1.6347(4) 0.68067(16) 0.0276(6) Uani 1 1 d . . .
F3B F 0.84425(11) 1.7026(4) 0.73586(15) 0.0337(6) Uani 1 1 d . . .
F4B F 0.92226(11) 1.3835(4) 0.69226(17) 0.0373(7) Uani 1 1 d . . .
F5B F 0.85938(12) 0.9907(4) 0.59556(17) 0.0340(6) Uani 1 1 d . . .
F6B F 0.72109(11) 0.9223(3) 0.54248(15) 0.0261(6) Uani 1 1 d . . .
C1B C 0.71063(18) 1.2762(6) 0.6102(3) 0.0167(8) Uani 1 1 d . . .
C2B C 0.7440(2) 1.4736(6) 0.6601(3) 0.0221(10) Uani 1 1 d . . .
C3B C 0.8140(2) 1.5096(6) 0.6874(3) 0.0237(9) Uani 1 1 d . . .
C4B C 0.85334(19) 1.3485(7) 0.6661(3) 0.0245(9) Uani 1 1 d . . .
C5B C 0.8223(2) 1.1506(7) 0.6182(3) 0.0222(9) Uani 1 1 d . . .
C6B C 0.75159(19) 1.1170(6) 0.5909(3) 0.0188(9) Uani 1 1 d . . .
N1C N 0.56934(16) 1.0483(6) 0.3114(2) 0.0231(7) Uani 1 1 d . . .
H2C H 0.5525(19) 0.932(6) 0.271(2) 0.035(11) Uiso 1 1 d . . .
H1C H 0.540(2) 1.173(7) 0.288(3) 0.045(12) Uiso 1 1 d . . .
F2C F 0.65843(12) 0.7561(4) 0.27249(16) 0.0280(5) Uani 1 1 d . . .
F3C F 0.79531(12) 0.8555(4) 0.32815(17) 0.0287(6) Uani 1 1 d . . .
F4C F 0.84932(10) 1.2595(4) 0.42088(15) 0.0287(6) Uani 1 1 d . . .
F5C F 0.76447(12) 1.5650(4) 0.45587(16) 0.0263(6) Uani 1 1 d . . .
F6C F 0.62755(12) 1.4668(4) 0.39942(18) 0.0286(6) Uani 1 1 d . . .
C1C C 0.63949(19) 1.1082(6) 0.3345(3) 0.0176(8) Uani 1 1 d . . .
C2C C 0.6840(2) 0.9582(6) 0.3175(3) 0.0180(9) Uani 1 1 d . . .
C3C C 0.75423(19) 1.0072(6) 0.3460(3) 0.0167(8) Uani 1 1 d . . .
C4C C 0.78117(18) 1.2103(6) 0.3916(3) 0.0197(9) Uani 1 1 d . . .
C5C C 0.7379(2) 1.3669(6) 0.4096(3) 0.0193(9) Uani 1 1 d . . .
C6C C 0.6687(2) 1.3133(6) 0.3813(3) 0.0204(9) 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
O1A 0.0249(14) 0.0239(13) 0.0157(15) 0.0003(11) 0.0091(12) -0.0019(11)
F2A 0.0239(12) 0.0297(11) 0.0176(13) -0.0049(10) 0.0069(10) 0.0000(9)
F3A 0.0313(12) 0.0334(12) 0.0197(15) 0.0050(10) 0.0140(11) 0.0036(10)
F4A 0.0302(13) 0.0242(11) 0.0414(17) 0.0035(10) 0.0199(12) -0.0033(9)
F5A 0.0224(11) 0.0279(11) 0.0291(15) -0.0106(11) 0.0081(10) -0.0024(10)
F6A 0.0202(11) 0.0345(12) 0.0140(13) -0.0032(10) 0.0072(10) 0.0011(9)
C1A 0.0110(17) 0.0206(18) 0.020(2) -0.0024(15) 0.0069(16) 0.0045(13)
C2A 0.018(2) 0.0227(18) 0.018(2) -0.0077(16) 0.0090(17) 0.0020(14)
C3A 0.0179(18) 0.0241(18) 0.017(2) -0.0006(16) 0.0095(17) 0.0066(15)
C4A 0.0184(19) 0.0190(17) 0.026(2) 0.0027(17) 0.0111(18) 0.0014(14)
C5A 0.0091(17) 0.0239(18) 0.022(2) -0.0075(17) 0.0014(16) 0.0027(14)
C6A 0.0123(17) 0.0296(19) 0.010(2) 0.0029(16) 0.0041(15) 0.0057(15)
O1B 0.0149(13) 0.0247(13) 0.0256(18) -0.0025(12) 0.0069(12) -0.0006(11)
F2B 0.0325(14) 0.0232(12) 0.0284(15) -0.0064(10) 0.0142(12) 0.0008(9)
F3B 0.0352(13) 0.0327(12) 0.0269(16) -0.0042(11) 0.0068(12) -0.0170(10)
F4B 0.0148(11) 0.0589(16) 0.0342(15) 0.0125(12) 0.0064(10) -0.0049(11)
F5B 0.0294(13) 0.0415(14) 0.0366(16) 0.0079(12) 0.0193(12) 0.0152(11)
F6B 0.0334(13) 0.0213(10) 0.0255(14) -0.0025(10) 0.0142(11) 0.0034(9)
C1B 0.0140(18) 0.0237(18) 0.012(2) 0.0011(16) 0.0049(16) -0.0002(14)
C2B 0.025(2) 0.0201(18) 0.021(3) 0.0036(16) 0.0092(19) 0.0071(15)
C3B 0.028(2) 0.0207(18) 0.017(2) 0.0008(16) 0.0040(18) -0.0088(15)
C4B 0.0146(19) 0.037(2) 0.019(2) 0.0108(18) 0.0038(16) 0.0022(16)
C5B 0.023(2) 0.0303(19) 0.015(2) 0.0073(16) 0.0090(16) 0.0107(16)
C6B 0.021(2) 0.0189(18) 0.015(2) 0.0036(15) 0.0053(17) 0.0011(15)
N1C 0.0159(16) 0.0327(17) 0.0179(18) 0.0032(15) 0.0046(13) 0.0001(14)
F2C 0.0315(11) 0.0238(11) 0.0255(14) -0.0049(10) 0.0089(10) -0.0035(9)
F3C 0.0252(12) 0.0292(12) 0.0341(16) -0.0047(11) 0.0148(11) 0.0090(9)
F4C 0.0187(12) 0.0343(12) 0.0329(16) -0.0047(11) 0.0104(11) -0.0018(10)
F5C 0.0295(12) 0.0193(11) 0.0308(15) -0.0047(10) 0.0135(10) -0.0015(9)
F6C 0.0282(12) 0.0297(12) 0.0342(15) 0.0012(11) 0.0192(11) 0.0126(10)
C1C 0.0171(18) 0.0255(18) 0.012(2) 0.0057(15) 0.0075(15) 0.0009(14)
C2C 0.026(2) 0.0166(17) 0.012(2) 0.0006(15) 0.0087(17) -0.0013(15)
C3C 0.0193(19) 0.0190(17) 0.014(2) 0.0049(15) 0.0097(17) 0.0070(14)
C4C 0.0136(19) 0.0248(19) 0.021(2) 0.0071(17) 0.0076(17) 0.0015(15)
C5C 0.028(2) 0.0161(18) 0.015(2) -0.0002(15) 0.0097(17) 0.0009(15)
C6C 0.020(2) 0.0240(18) 0.022(2) 0.0083(17) 0.0141(17) 0.0121(15)

_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
O1A C1A 1.356(4) . ?
O1A H1A 0.85(4) . ?
F2A C2A 1.353(4) . ?
F3A C3A 1.351(4) . ?
F4A C4A 1.343(4) . ?
F5A C5A 1.342(4) . ?
F6A C6A 1.356(4) . ?
C1A C2A 1.388(5) . ?
C1A C6A 1.393(5) . ?
C2A C3A 1.369(5) . ?
C3A C4A 1.368(6) . ?
C4A C5A 1.376(6) . ?
C5A C6A 1.377(6) . ?
O1B C1B 1.355(4) . ?
O1B H1B 0.92(5) . ?
F2B C2B 1.349(4) . ?
F3B C3B 1.347(4) . ?
F4B C4B 1.351(4) . ?
F5B C5B 1.350(4) . ?
F6B C6B 1.356(4) . ?
C1B C6B 1.376(5) . ?
C1B C2B 1.393(5) . ?
C2B C3B 1.371(5) . ?
C3B C4B 1.375(6) . ?
C4B C5B 1.370(5) . ?
C5B C6B 1.382(5) . ?
N1C C1C 1.410(5) . ?
N1C H2C 0.90(4) . ?
N1C H1C 0.91(4) . ?
F2C C2C 1.347(4) . ?
F3C C3C 1.340(4) . ?
F4C C4C 1.344(4) . ?
F5C C5C 1.341(4) . ?
F6C C6C 1.350(4) . ?
C1C C2C 1.381(5) . ?
C1C C6C 1.388(5) . ?
C2C C3C 1.386(5) . ?
C3C C4C 1.361(5) . ?
C4C C5C 1.392(5) . ?
C5C C6C 1.372(5) . ?

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
C1A O1A H1A 111(3) . . ?
O1A C1A C2A 119.4(3) . . ?
O1A C1A C6A 124.2(4) . . ?
C2A C1A C6A 116.4(3) . . ?
F2A C2A C3A 120.1(4) . . ?
F2A C2A C1A 118.0(3) . . ?
C3A C2A C1A 122.0(3) . . ?
F3A C3A C4A 120.4(3) . . ?
F3A C3A C2A 119.1(3) . . ?
C4A C3A C2A 120.5(4) . . ?
F4A C4A C3A 120.7(4) . . ?
F4A C4A C5A 119.9(4) . . ?
C3A C4A C5A 119.4(3) . . ?
F5A C5A C4A 120.7(4) . . ?
F5A C5A C6A 119.4(4) . . ?
C4A C5A C6A 119.9(4) . . ?
F6A C6A C5A 119.6(3) . . ?
F6A C6A C1A 118.6(3) . . ?
C5A C6A C1A 121.9(4) . . ?
C1B O1B H1B 116(3) . . ?
O1B C1B C6B 124.3(3) . . ?
O1B C1B C2B 119.0(3) . . ?
C6B C1B C2B 116.7(3) . . ?
F2B C2B C3B 119.5(3) . . ?
F2B C2B C1B 119.0(3) . . ?
C3B C2B C1B 121.5(3) . . ?
F3B C3B C2B 119.6(4) . . ?
F3B C3B C4B 120.1(4) . . ?
C2B C3B C4B 120.3(4) . . ?
F4B C4B C5B 119.8(4) . . ?
F4B C4B C3B 120.6(4) . . ?
C5B C4B C3B 119.6(4) . . ?
F5B C5B C4B 120.9(4) . . ?
F5B C5B C6B 119.5(4) . . ?
C4B C5B C6B 119.5(4) . . ?
F6B C6B C1B 118.6(3) . . ?
F6B C6B C5B 119.1(3) . . ?
C1B C6B C5B 122.3(3) . . ?
C1C N1C H2C 115(2) . . ?
C1C N1C H1C 112(3) . . ?
H2C N1C H1C 106(3) . . ?
C2C C1C C6C 116.4(3) . . ?
C2C C1C N1C 121.8(3) . . ?
C6C C1C N1C 121.6(3) . . ?
F2C C2C C1C 118.9(3) . . ?
F2C C2C C3C 118.8(3) . . ?
C1C C2C C3C 122.2(3) . . ?
F3C C3C C4C 120.2(3) . . ?
F3C C3C C2C 120.0(3) . . ?
C4C C3C C2C 119.8(3) . . ?
F4C C4C C3C 120.7(3) . . ?
F4C C4C C5C 119.6(3) . . ?
C3C C4C C5C 119.7(3) . . ?
F5C C5C C6C 120.7(3) . . ?
F5C C5C C4C 119.9(3) . . ?
C6C C5C C4C 119.3(3) . . ?
F6C C6C C5C 118.6(3) . . ?
F6C C6C C1C 118.9(3) . . ?
C5C C6C C1C 122.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1A N1C 0.85(4) 1.96(4) 2.747(5) 153(4) .
O1B H1B O1A 0.92(5) 1.88(5) 2.771(4) 161(4) .
O1B H1B F2A 0.92(5) 2.54(5) 3.060(3) 116(3) .
N1C H1C F4B 0.91(4) 2.35(4) 2.929(3) 121(3) 4_474
N1C H2C F2C 0.90(4) 2.44(4) 2.778(4) 102(3) .
N1C H2C F3A 0.90(4) 2.65(4) 3.537(4) 172(3) 2_564

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045

#===END

data_H1
_database_code_depnum_ccdc_archive 'CCDC 632639'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,3,4,5,6-pentafluorophenol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H F5 O'
_chemical_formula_sum            'C6 H F5 O'
_chemical_formula_weight         184.07

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'
O O 0.0106 0.0060 '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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   5.1398(9)
_cell_length_b                   19.0901(16)
_cell_length_c                   19.1520(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1879.2(4)
_cell_formula_units_Z            12
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3588
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(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  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9704
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1946
_reflns_number_gt                1547
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_cell_refinement       
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_data_reduction        
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; 'Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989)'
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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^)+(0.0514P)^2^] 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
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1946
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1A O 0.6676(7) 0.30583(17) 0.18317(17) 0.0306(8) Uani 1 1 d . . .
H1A H 0.5740 0.3377 0.2131 0.037 Uiso 1 1 d R . .
F2A F 0.2861(6) 0.40206(16) 0.14725(15) 0.0385(8) Uani 1 1 d . . .
F3A F 0.2705(6) 0.45782(17) 0.01658(17) 0.0478(9) Uani 1 1 d . . .
F4A F 0.6280(7) 0.41707(17) -0.08131(14) 0.0509(10) Uani 1 1 d . . .
F5A F 0.9984(6) 0.32159(16) -0.04664(16) 0.0470(9) Uani 1 1 d . . .
F6A F 1.0158(6) 0.26748(15) 0.08399(15) 0.0389(8) Uani 1 1 d . . .
C1A C 0.6520(9) 0.3353(2) 0.1176(2) 0.0266(12) Uani 1 1 d . . .
C2A C 0.4640(10) 0.3822(3) 0.0995(3) 0.0289(12) Uani 1 1 d . . .
C3A C 0.4548(10) 0.4110(3) 0.0331(3) 0.0310(13) Uani 1 1 d . . .
C4A C 0.6337(11) 0.3899(3) -0.0158(3) 0.0360(14) Uani 1 1 d . . .
C5A C 0.8215(11) 0.3425(3) 0.0015(3) 0.0321(13) Uani 1 1 d . . .
C6A C 0.8296(10) 0.3150(3) 0.0675(3) 0.0290(12) Uani 1 1 d . . .
O1B O 1.0671(7) 0.23291(18) 0.23918(17) 0.0367(9) Uani 1 1 d . . .
H1B H 0.9408 0.2501 0.2115 0.044 Uiso 1 1 d R . .
F2B F 0.7162(6) 0.14058(15) 0.17920(16) 0.0397(8) Uani 1 1 d . . .
F3B F 0.7573(7) 0.00046(16) 0.20329(17) 0.0460(8) Uani 1 1 d . . .
F4B F 1.1465(6) -0.04939(15) 0.28769(16) 0.0421(8) Uani 1 1 d . . .
F5B F 1.4848(6) 0.04160(15) 0.34751(15) 0.0430(9) Uani 1 1 d . . .
F6B F 1.4462(6) 0.18107(15) 0.32193(16) 0.0416(8) Uani 1 1 d . . .
C1B C 1.0801(10) 0.1628(3) 0.2503(2) 0.0291(12) Uani 1 1 d . . .
C2B C 0.9085(10) 0.1153(3) 0.2210(3) 0.0297(12) Uani 1 1 d . . .
C3B C 0.9281(10) 0.0444(3) 0.2331(3) 0.0303(12) Uani 1 1 d . . .
C4B C 1.1230(11) 0.0193(3) 0.2755(3) 0.0329(13) Uani 1 1 d . . .
C5B C 1.2962(10) 0.0663(3) 0.3051(3) 0.0293(12) Uani 1 1 d . . .
C6B C 1.2747(10) 0.1362(3) 0.2930(2) 0.0290(12) Uani 1 1 d . . .
O1C O 0.3564(7) 0.33624(18) 0.29755(16) 0.0329(9) Uani 1 1 d . . .
H1C H 0.2517 0.2989 0.2916 0.039 Uiso 1 1 d R . .
F2C F 0.0015(6) 0.27669(16) 0.38961(14) 0.0382(8) Uani 1 1 d . . .
F3C F 0.0265(6) 0.30438(17) 0.52814(14) 0.0464(9) Uani 1 1 d . . .
F4C F 0.4057(6) 0.39026(17) 0.57947(14) 0.0461(9) Uani 1 1 d . . .
F5C F 0.7571(6) 0.44838(17) 0.49034(16) 0.0448(8) Uani 1 1 d . . .
F6C F 0.7320(6) 0.42077(17) 0.35152(16) 0.0433(8) Uani 1 1 d . . .
C1C C 0.3661(10) 0.3487(3) 0.3683(2) 0.0266(12) Uani 1 1 d . . .
C2C C 0.1885(10) 0.3200(2) 0.4140(3) 0.0266(12) Uani 1 1 d . . .
C3C C 0.2013(10) 0.3340(3) 0.4851(2) 0.0278(12) Uani 1 1 d . . .
C4C C 0.3918(11) 0.3765(3) 0.5100(3) 0.0304(12) Uani 1 1 d . . .
C5C C 0.5699(10) 0.4063(3) 0.4659(3) 0.0308(13) Uani 1 1 d . . .
C6C C 0.5531(10) 0.3924(3) 0.3942(3) 0.0280(12) 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
O1A 0.039(2) 0.0331(19) 0.0198(17) -0.0004(16) 0.0041(16) 0.0041(17)
F2A 0.0334(17) 0.0429(18) 0.0391(18) -0.0008(15) 0.0045(16) 0.0043(15)
F3A 0.0434(19) 0.053(2) 0.047(2) 0.0082(17) -0.0140(18) 0.0037(17)
F4A 0.076(3) 0.056(2) 0.0211(17) 0.0060(15) -0.0084(18) -0.0085(19)
F5A 0.057(2) 0.056(2) 0.0283(16) -0.0069(15) 0.0142(17) -0.0016(19)
F6A 0.0413(19) 0.0399(18) 0.0353(17) -0.0030(15) 0.0042(16) 0.0090(17)
C1A 0.031(3) 0.027(3) 0.022(3) -0.002(2) -0.003(2) -0.002(3)
C2A 0.028(3) 0.029(3) 0.030(3) -0.010(2) 0.000(3) 0.001(3)
C3A 0.031(3) 0.027(3) 0.035(3) 0.000(2) -0.016(3) 0.007(3)
C4A 0.048(4) 0.038(3) 0.022(3) -0.001(3) -0.007(3) -0.011(3)
C5A 0.039(3) 0.035(3) 0.023(3) -0.009(2) 0.010(2) -0.005(3)
C6A 0.027(3) 0.033(3) 0.027(3) -0.006(2) -0.003(2) 0.001(3)
O1B 0.046(2) 0.035(2) 0.029(2) 0.0020(17) -0.0160(18) 0.0035(18)
F2B 0.0425(18) 0.0428(18) 0.0340(17) 0.0020(15) -0.0155(16) 0.0017(15)
F3B 0.0447(18) 0.0442(19) 0.049(2) -0.0019(17) -0.0079(17) -0.0092(16)
F4B 0.050(2) 0.0390(18) 0.0371(18) 0.0088(15) 0.0072(16) 0.0030(16)
F5B 0.046(2) 0.0480(19) 0.0355(18) 0.0090(15) -0.0056(17) 0.0131(17)
F6B 0.047(2) 0.0400(18) 0.0372(17) -0.0033(15) -0.0161(16) 0.0009(16)
C1B 0.036(3) 0.030(3) 0.021(3) 0.000(2) 0.000(2) 0.003(3)
C2B 0.033(3) 0.035(3) 0.021(3) -0.002(2) -0.001(2) 0.006(3)
C3B 0.033(3) 0.033(3) 0.025(3) -0.008(2) 0.003(3) 0.000(3)
C4B 0.041(3) 0.033(3) 0.025(3) 0.006(2) 0.011(3) 0.005(3)
C5B 0.029(3) 0.039(3) 0.020(3) 0.002(2) 0.001(2) 0.012(3)
C6B 0.032(3) 0.036(3) 0.020(3) 0.001(2) -0.003(2) 0.000(2)
O1C 0.043(2) 0.036(2) 0.0193(17) -0.0029(16) 0.0017(16) -0.0081(18)
F2C 0.0391(18) 0.0476(18) 0.0280(16) -0.0012(15) -0.0013(16) -0.0148(17)
F3C 0.047(2) 0.064(2) 0.0272(17) 0.0052(16) 0.0111(16) -0.0105(19)
F4C 0.055(2) 0.063(2) 0.0201(16) -0.0062(15) -0.0032(16) 0.0004(19)
F5C 0.0445(19) 0.0465(19) 0.0433(19) -0.0083(16) -0.0079(17) -0.0154(17)
F6C 0.0396(18) 0.054(2) 0.0368(18) 0.0064(16) 0.0044(16) -0.0150(16)
C1C 0.035(3) 0.028(3) 0.016(2) 0.003(2) 0.002(2) 0.005(3)
C2C 0.030(3) 0.023(3) 0.027(3) 0.000(2) -0.001(2) -0.004(2)
C3C 0.032(3) 0.033(3) 0.019(3) 0.002(2) 0.008(2) -0.002(3)
C4C 0.039(3) 0.036(3) 0.017(3) -0.003(2) 0.001(3) 0.007(3)
C5C 0.032(3) 0.028(3) 0.033(3) -0.001(2) -0.005(3) 0.000(3)
C6C 0.030(3) 0.028(3) 0.027(3) 0.008(2) 0.006(3) -0.004(3)

_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
O1A C1A 1.379(6) . ?
O1A H1A 0.9642 . ?
F2A C2A 1.347(6) . ?
F3A C3A 1.340(6) . ?
F4A C4A 1.357(6) . ?
F5A C5A 1.354(6) . ?
F6A C6A 1.356(6) . ?
C1A C2A 1.362(7) . ?
C1A C6A 1.380(7) . ?
C2A C3A 1.387(7) . ?
C3A C4A 1.374(7) . ?
C4A C5A 1.364(7) . ?
C5A C6A 1.370(7) . ?
O1B C1B 1.358(6) . ?
O1B H1B 0.9000 . ?
F2B C2B 1.361(6) . ?
F3B C3B 1.342(6) . ?
F4B C4B 1.337(6) . ?
F5B C5B 1.351(5) . ?
F6B C6B 1.348(5) . ?
C1B C2B 1.383(7) . ?
C1B C6B 1.388(7) . ?
C2B C3B 1.377(7) . ?
C3B C4B 1.376(7) . ?
C4B C5B 1.386(7) . ?
C5B C6B 1.358(7) . ?
O1C C1C 1.377(6) . ?
O1C H1C 0.9001 . ?
F2C C2C 1.351(5) . ?
F3C C3C 1.344(5) . ?
F4C C4C 1.357(5) . ?
F5C C5C 1.338(6) . ?
F6C C6C 1.345(5) . ?
C1C C6C 1.365(7) . ?
C1C C2C 1.378(7) . ?
C2C C3C 1.389(7) . ?
C3C C4C 1.359(7) . ?
C4C C5C 1.370(7) . ?
C5C C6C 1.400(7) . ?

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
C1A O1A H1A 104.7 . . ?
C2A C1A O1A 122.7(4) . . ?
C2A C1A C6A 118.5(5) . . ?
O1A C1A C6A 118.7(4) . . ?
F2A C2A C1A 119.6(5) . . ?
F2A C2A C3A 119.2(5) . . ?
C1A C2A C3A 121.2(5) . . ?
F3A C3A C4A 120.6(5) . . ?
F3A C3A C2A 120.3(5) . . ?
C4A C3A C2A 119.1(5) . . ?
F4A C4A C5A 119.6(5) . . ?
F4A C4A C3A 120.2(5) . . ?
C5A C4A C3A 120.2(5) . . ?
F5A C5A C4A 120.3(5) . . ?
F5A C5A C6A 119.7(5) . . ?
C4A C5A C6A 120.0(5) . . ?
F6A C6A C5A 119.5(5) . . ?
F6A C6A C1A 119.5(4) . . ?
C5A C6A C1A 120.9(5) . . ?
C1B O1B H1B 119.2 . . ?
O1B C1B C2B 123.4(5) . . ?
O1B C1B C6B 119.2(5) . . ?
C2B C1B C6B 117.4(5) . . ?
F2B C2B C3B 120.0(5) . . ?
F2B C2B C1B 118.0(4) . . ?
C3B C2B C1B 122.0(5) . . ?
F3B C3B C2B 119.7(5) . . ?
F3B C3B C4B 120.6(5) . . ?
C2B C3B C4B 119.6(5) . . ?
F4B C4B C3B 120.7(5) . . ?
F4B C4B C5B 120.4(5) . . ?
C3B C4B C5B 118.9(5) . . ?
F5B C5B C6B 120.3(5) . . ?
F5B C5B C4B 118.7(4) . . ?
C6B C5B C4B 121.0(5) . . ?
F6B C6B C5B 120.0(5) . . ?
F6B C6B C1B 118.8(4) . . ?
C5B C6B C1B 121.2(5) . . ?
C1C O1C H1C 106.4 . . ?
C6C C1C O1C 119.3(4) . . ?
C6C C1C C2C 118.6(4) . . ?
O1C C1C C2C 122.1(5) . . ?
F2C C2C C1C 119.7(4) . . ?
F2C C2C C3C 119.3(4) . . ?
C1C C2C C3C 121.0(5) . . ?
F3C C3C C4C 121.2(4) . . ?
F3C C3C C2C 119.3(5) . . ?
C4C C3C C2C 119.5(5) . . ?
F4C C4C C3C 119.8(5) . . ?
F4C C4C C5C 119.3(5) . . ?
C3C C4C C5C 120.9(5) . . ?
F5C C5C C4C 120.9(5) . . ?
F5C C5C C6C 120.1(5) . . ?
C4C C5C C6C 119.0(5) . . ?
F6C C6C C1C 120.4(4) . . ?
F6C C6C C5C 118.5(5) . . ?
C1C C6C C5C 121.0(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1A O1C 0.96 1.97 2.774(5) 140 .
O1B H1B O1A 0.90 1.84 2.703(5) 159 .
O1C H1C O1B 0.90 1.87 2.711(5) 155 1_455

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.061

#===END

data_L
_database_code_depnum_ccdc_archive 'CCDC 632640'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,3,4,5,6-pentafluorophenol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H F5 O'
_chemical_formula_sum            'C6 H F5 O'
_chemical_formula_weight         184.07

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'
O O 0.0106 0.0060 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   12.938(3)
_cell_length_b                   4.8572(13)
_cell_length_c                   10.010(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.55(2)
_cell_angle_gamma                90.00
_cell_volume                     603.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    1655
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(1)
_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  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2925
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1223
_reflns_number_gt                867
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_cell_refinement       
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_data_reduction        
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; 'Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989)'
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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^)+(0.0921P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   refall
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1223
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
O1 O 0.95707(12) 0.5158(4) 0.68758(17) 0.0340(4) Uani 1 1 d . . .
H1 H 0.979(3) 0.374(8) 0.730(4) 0.081(13) Uiso 1 1 d . . .
F2 F 0.81649(11) 0.1238(3) 0.73728(14) 0.0376(4) Uani 1 1 d . . .
F3 F 0.60917(10) 0.1061(3) 0.57916(16) 0.0423(4) Uani 1 1 d . . .
F4 F 0.53647(10) 0.4711(3) 0.36679(14) 0.0453(5) Uani 1 1 d . . .
F5 F 0.67360(11) 0.8580(3) 0.31716(14) 0.0436(4) Uani 1 1 d . . .
F6 F 0.88115(11) 0.8723(3) 0.47493(15) 0.0398(4) Uani 1 1 d . . .
C1 C 0.85216(16) 0.4987(4) 0.6094(2) 0.0264(5) Uani 1 1 d . . .
C2 C 0.78125(17) 0.3059(4) 0.6331(2) 0.0267(5) Uani 1 1 d . . .
C3 C 0.67575(17) 0.2956(4) 0.5535(2) 0.0302(5) Uani 1 1 d . . .
C4 C 0.63841(17) 0.4825(5) 0.4461(2) 0.0307(5) Uani 1 1 d . . .
C5 C 0.70854(18) 0.6752(5) 0.4214(2) 0.0316(5) Uani 1 1 d . . .
C6 C 0.81356(18) 0.6824(5) 0.5016(2) 0.0298(5) 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
O1 0.0266(9) 0.0319(10) 0.0374(9) 0.0026(7) -0.0006(7) -0.0014(7)
F2 0.0359(8) 0.0379(8) 0.0374(8) 0.0122(6) 0.0078(6) 0.0013(5)
F3 0.0302(8) 0.0406(9) 0.0569(10) 0.0005(6) 0.0138(6) -0.0073(5)
F4 0.0274(8) 0.0592(10) 0.0413(8) -0.0065(7) -0.0034(6) 0.0024(6)
F5 0.0474(9) 0.0482(8) 0.0312(8) 0.0111(6) 0.0047(6) 0.0076(6)
F6 0.0410(8) 0.0349(8) 0.0447(8) 0.0079(6) 0.0143(6) -0.0045(6)
C1 0.0267(10) 0.0266(12) 0.0239(10) -0.0039(8) 0.0040(8) -0.0005(9)
C2 0.0289(11) 0.0270(11) 0.0244(10) -0.0002(8) 0.0081(8) 0.0015(9)
C3 0.0273(11) 0.0300(12) 0.0347(12) -0.0048(9) 0.0111(9) -0.0046(9)
C4 0.0270(11) 0.0323(13) 0.0301(12) -0.0068(9) 0.0034(8) 0.0035(9)
C5 0.0367(12) 0.0361(12) 0.0218(10) 0.0008(9) 0.0077(9) 0.0071(10)
C6 0.0338(12) 0.0308(12) 0.0265(11) -0.0023(9) 0.0112(9) -0.0028(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
O1 C1 1.363(2) . ?
O1 H1 0.81(4) . ?
F2 C2 1.344(2) . ?
F3 C3 1.335(2) . ?
F4 C4 1.333(2) . ?
F5 C5 1.346(2) . ?
F6 C6 1.349(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.380(3) . ?
C2 C3 1.372(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.374(3) . ?
C5 C6 1.368(3) . ?

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
C1 O1 H1 113(3) . . ?
O1 C1 C2 123.05(19) . . ?
O1 C1 C6 119.30(19) . . ?
C2 C1 C6 117.64(19) . . ?
F2 C2 C3 119.26(19) . . ?
F2 C2 C1 119.04(19) . . ?
C3 C2 C1 121.7(2) . . ?
F3 C3 C2 120.2(2) . . ?
F3 C3 C4 120.01(19) . . ?
C2 C3 C4 119.8(2) . . ?
F4 C4 C5 120.9(2) . . ?
F4 C4 C3 120.2(2) . . ?
C5 C4 C3 119.0(2) . . ?
F5 C5 C6 119.7(2) . . ?
F5 C5 C4 119.7(2) . . ?
C6 C5 C4 120.5(2) . . ?
F6 C6 C5 119.5(2) . . ?
F6 C6 C1 119.09(19) . . ?
C5 C6 C1 121.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.81(4) 2.00(4) 2.8112(16) 172(4) 2_746

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.075

#===END