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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Pierangelo Metrangolo' Nanoscience Center,
'S Biella' of Chemistry,
'Manu Lahtinen' of Jyvaskyla,
'Rosalba Liantonio' O. Box
'Giuseppe Resnati' 40014 Jyv\"askyl\"a,
;
K.Rissanen
;
;
'Biella Serena'
;
NFMLab
'Luca Russo' G. Natta,

_publ_contact_author_name        'Pierangelo Metrangolo'
_publ_contact_author_address     
;
Dipartimento di Chimica,
Materiali ed Ingegneria Chimica "G. Natta"
Politecnico di Milano
Via L. Mancinelli 7
Milano
I-20131
ITALY
;

_publ_contact_author_email       PIERANGELO.METRANGOLO@POLIMI.IT

_publ_section_title              
;
Solution stoichiometry determines crystal
stoichiometry in halogenbonded
supramolecular complexes
;

data_lrs007
_database_code_depnum_ccdc_archive 'CCDC 630671'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2,C7 H7 O2'
_chemical_formula_sum            'C13 H7 F4 I2 N O2'
_chemical_formula_weight         539.00

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4055(13)
_cell_length_b                   9.589(2)
_cell_length_c                   13.479(5)
_cell_angle_alpha                78.22(3)
_cell_angle_beta                 86.37(3)
_cell_angle_gamma                73.407(15)
_cell_volume                     776.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2428
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    4.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1925
_exptl_absorpt_correction_T_max  0.8214
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_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  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\f and \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            11047
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.59
_reflns_number_total             3558
_reflns_number_gt                2970
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       EvalCCD
_computing_data_reduction        EvalCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 1.4, Diamond 3'
_computing_publication_material  ?

_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^)+(0.0121P)^2^+0.1306P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3558
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0459
_refine_ls_wR_factor_gt          0.0415
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.002
_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 0.3009(5) 0.5606(4) 0.7199(3) 0.0325(8) Uani 1 1 d . . .
H1B H 0.4519 0.5239 0.7351 0.039 Uiso 1 1 calc R . .
C2 C 0.1793(5) 0.6806(3) 0.7600(2) 0.0285(7) Uani 1 1 d . . .
H2A H 0.2455 0.7257 0.8009 0.034 Uiso 1 1 calc R . .
C3 C -0.0437(5) 0.7340(3) 0.7389(2) 0.0218(7) Uani 1 1 d . . .
C4 C -0.1320(5) 0.6638(3) 0.6784(2) 0.0278(7) Uani 1 1 d . . .
H4A H -0.2831 0.6967 0.6631 0.033 Uiso 1 1 calc R . .
C5 C 0.0043(5) 0.5449(4) 0.6406(3) 0.0316(8) Uani 1 1 d . . .
H5A H -0.0570 0.4985 0.5987 0.038 Uiso 1 1 calc R . .
C6 C -0.1791(5) 0.8636(3) 0.7833(2) 0.0244(7) Uani 1 1 d . . .
C7 C -0.5390(5) 0.9928(4) 0.8265(3) 0.0356(9) Uani 1 1 d . . .
H7A H -0.6888 0.9870 0.8239 0.053 Uiso 1 1 calc R . .
H7B H -0.5279 1.0881 0.7867 0.053 Uiso 1 1 calc R . .
H7C H -0.4996 0.9842 0.8970 0.053 Uiso 1 1 calc R . .
C8 C -0.0432(5) 1.3943(3) 0.9499(2) 0.0232(7) Uani 1 1 d . . .
C9 C -0.2007(5) 1.5257(3) 0.9582(2) 0.0233(7) Uani 1 1 d . . .
C10 C 0.1599(5) 1.3727(3) 0.9917(2) 0.0225(7) Uani 1 1 d . . .
C11 C 0.8245(5) 0.1142(3) 0.5271(2) 0.0210(7) Uani 1 1 d . . .
C12 C 1.0301(5) 0.0795(3) 0.5696(2) 0.0226(7) Uani 1 1 d . . .
C13 C 0.7992(5) 0.0332(3) 0.4567(2) 0.0226(7) Uani 1 1 d . . .
N1 N 0.2178(4) 0.4928(3) 0.6605(2) 0.0312(7) Uani 1 1 d . . .
O1 O -0.1010(4) 0.9472(3) 0.8153(2) 0.0430(7) Uani 1 1 d . . .
O2 O -0.3905(3) 0.8718(2) 0.78428(17) 0.0309(5) Uani 1 1 d . . .
I1 I 0.56191(3) 0.27823(2) 0.573814(16) 0.02538(7) Uani 1 1 d . . .
I2 I -0.10652(4) 1.23284(2) 0.882348(17) 0.03442(7) Uani 1 1 d . . .
F1 F -0.3995(3) 1.5564(2) 0.91567(14) 0.0332(4) Uani 1 1 d . . .
F2 F 0.3220(3) 1.24808(19) 0.98488(14) 0.0347(5) Uani 1 1 d . . .
F3 F 1.0674(3) 0.1554(2) 0.63782(14) 0.0332(5) Uani 1 1 d . . .
F4 F 0.6030(3) 0.0646(2) 0.41125(14) 0.0318(4) 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 0.0199(17) 0.0337(19) 0.042(2) -0.0104(17) -0.0005(15) -0.0021(15)
C2 0.0278(18) 0.0297(18) 0.0315(19) -0.0114(15) -0.0029(14) -0.0088(15)
C3 0.0246(16) 0.0213(16) 0.0200(16) -0.0062(13) 0.0020(13) -0.0063(13)
C4 0.0202(16) 0.0319(18) 0.0321(19) -0.0120(15) -0.0021(14) -0.0041(14)
C5 0.0291(19) 0.0372(19) 0.034(2) -0.0196(16) 0.0012(15) -0.0099(16)
C6 0.0243(17) 0.0240(17) 0.0225(17) -0.0041(14) -0.0002(13) -0.0033(14)
C7 0.0299(19) 0.0298(18) 0.040(2) -0.0114(16) 0.0050(16) 0.0051(15)
C8 0.0305(18) 0.0221(16) 0.0184(16) -0.0061(13) 0.0000(13) -0.0081(14)
C9 0.0199(16) 0.0282(17) 0.0217(17) -0.0051(14) -0.0023(13) -0.0059(14)
C10 0.0235(16) 0.0194(15) 0.0224(17) -0.0061(13) 0.0031(13) -0.0017(13)
C11 0.0207(16) 0.0176(15) 0.0230(17) -0.0047(13) 0.0013(13) -0.0027(13)
C12 0.0275(18) 0.0218(16) 0.0214(17) -0.0107(13) 0.0011(13) -0.0070(14)
C13 0.0188(16) 0.0234(16) 0.0240(17) -0.0036(13) -0.0031(13) -0.0036(13)
N1 0.0277(15) 0.0294(15) 0.0371(17) -0.0137(13) 0.0071(13) -0.0054(13)
O1 0.0364(14) 0.0372(14) 0.0661(19) -0.0323(14) 0.0035(12) -0.0127(12)
O2 0.0231(12) 0.0320(13) 0.0389(14) -0.0195(11) 0.0007(10) -0.0011(10)
I1 0.02221(11) 0.02108(11) 0.03107(13) -0.00957(9) 0.00303(9) -0.00075(9)
I2 0.03731(14) 0.03289(13) 0.04023(15) -0.02058(11) 0.00173(10) -0.01210(11)
F1 0.0235(10) 0.0379(11) 0.0376(11) -0.0104(9) -0.0080(8) -0.0038(8)
F2 0.0291(10) 0.0257(10) 0.0435(12) -0.0140(9) -0.0018(9) 0.0068(8)
F3 0.0285(10) 0.0387(11) 0.0377(11) -0.0247(9) -0.0018(8) -0.0053(9)
F4 0.0207(9) 0.0377(11) 0.0357(11) -0.0146(9) -0.0067(8) 0.0003(8)

_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 H1B 0.9500 . ?
C1 C2 1.383(4) . ?
C1 N1 1.346(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.399(4) . ?
C3 C4 1.392(4) . ?
C3 C6 1.509(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.391(4) . ?
C5 H5A 0.9500 . ?
C5 N1 1.339(4) . ?
C6 O1 1.216(4) . ?
C6 O2 1.333(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 O2 1.464(4) . ?
C8 C9 1.391(4) . ?
C8 C10 1.394(4) . ?
C8 I2 2.091(3) . ?
C9 C10 1.382(4) 2_587 ?
C9 F1 1.359(3) . ?
C10 C9 1.382(4) 2_587 ?
C10 F2 1.356(3) . ?
C11 C12 1.393(4) . ?
C11 C13 1.386(4) . ?
C11 I1 2.112(3) . ?
C12 C13 1.386(4) 2_756 ?
C12 F3 1.354(3) . ?
C13 C12 1.386(4) 2_756 ?
C13 F4 1.361(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
H1B C1 C2 118.1 . . ?
H1B C1 N1 118.1 . . ?
C2 C1 N1 123.8(3) . . ?
C1 C2 H2A 120.8 . . ?
C1 C2 C3 118.4(3) . . ?
H2A C2 C3 120.8 . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 C6 119.0(3) . . ?
C4 C3 C6 122.7(3) . . ?
C3 C4 H4A 120.5 . . ?
C3 C4 C5 119.0(3) . . ?
H4A C4 C5 120.5 . . ?
C4 C5 H5A 118.4 . . ?
C4 C5 N1 123.1(3) . . ?
H5A C5 N1 118.4 . . ?
C3 C6 O1 123.1(3) . . ?
C3 C6 O2 111.6(3) . . ?
O1 C6 O2 125.2(3) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7A C7 O2 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7B C7 O2 109.5 . . ?
H7C C7 O2 109.5 . . ?
C9 C8 C10 116.6(3) . . ?
C9 C8 I2 122.4(2) . . ?
C10 C8 I2 121.0(2) . . ?
C8 C9 C10 121.6(3) . 2_587 ?
C8 C9 F1 119.7(3) . . ?
C10 C9 F1 118.7(3) 2_587 . ?
C8 C10 C9 121.7(3) . 2_587 ?
C8 C10 F2 119.7(3) . . ?
C9 C10 F2 118.5(3) 2_587 . ?
C12 C11 C13 117.3(3) . . ?
C12 C11 I1 120.5(2) . . ?
C13 C11 I1 122.1(2) . . ?
C11 C12 C13 121.0(3) . 2_756 ?
C11 C12 F3 120.5(3) . . ?
C13 C12 F3 118.5(3) 2_756 . ?
C11 C13 C12 121.7(3) . 2_756 ?
C11 C13 F4 119.8(3) . . ?
C12 C13 F4 118.5(3) 2_756 . ?
C1 N1 C5 117.3(3) . . ?
C6 O2 C7 116.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C1 C2 C3 C6 179.2(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C6 C3 C4 C5 -179.9(3) . . . . ?
C3 C4 C5 N1 0.8(5) . . . . ?
C2 C3 C6 O1 18.6(5) . . . . ?
C2 C3 C6 O2 -160.2(3) . . . . ?
C4 C3 C6 O1 -162.1(3) . . . . ?
C4 C3 C6 O2 19.0(4) . . . . ?
C10 C8 C9 C10 -2.1(5) . . . 2_587 ?
C10 C8 C9 F1 177.5(3) . . . . ?
I2 C8 C9 C10 176.2(2) . . . 2_587 ?
I2 C8 C9 F1 -4.3(4) . . . . ?
C9 C8 C10 C9 2.1(5) . . . 2_587 ?
C9 C8 C10 F2 -178.9(3) . . . . ?
I2 C8 C10 C9 -176.2(2) . . . 2_587 ?
I2 C8 C10 F2 2.8(4) . . . . ?
C13 C11 C12 C13 -0.9(5) . . . 2_756 ?
C13 C11 C12 F3 179.2(3) . . . . ?
I1 C11 C12 C13 176.6(2) . . . 2_756 ?
I1 C11 C12 F3 -3.2(4) . . . . ?
C12 C11 C13 C12 1.0(5) . . . 2_756 ?
C12 C11 C13 F4 -178.6(3) . . . . ?
I1 C11 C13 C12 -176.6(2) . . . 2_756 ?
I1 C11 C13 F4 3.9(4) . . . . ?
C4 C5 N1 C1 -0.1(5) . . . . ?
C2 C1 N1 C5 -0.7(5) . . . . ?
C3 C6 O2 C7 179.6(3) . . . . ?
O1 C6 O2 C7 0.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.110

# Attachment '3b_CIF.cif'

data_lrs031
_database_code_depnum_ccdc_archive 'CCDC 630672'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2 C7 H7 O2 N,C6 F4 I2'
_chemical_formula_sum            'C20 H14 F4 I2 N2 O4'
_chemical_formula_weight         676.13

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.1581(4)
_cell_length_b                   10.7974(8)
_cell_length_c                   12.7958(19)
_cell_angle_alpha                91.102(11)
_cell_angle_beta                 97.913(12)
_cell_angle_gamma                90.912(8)
_cell_volume                     568.81(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2343
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             322
_exptl_absorpt_coefficient_mu    2.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2819
_exptl_absorpt_correction_T_max  0.6765
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_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  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\f and \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            6429
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1924
_reflns_number_gt                1785
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       EvalCCD
_computing_data_reduction        EvalCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 1.3, Diamond 3'
_computing_publication_material  ?

_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^)+(0.0000P)^2^+0.3199P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1924
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0163
_refine_ls_wR_factor_ref         0.0404
_refine_ls_wR_factor_gt          0.0365
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.001
_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
I1 I 0.74502(4) 0.417214(16) 0.241908(12) 0.02916(8) Uani 1 1 d . . .
F1 F 0.9982(5) 0.25628(14) 0.05427(13) 0.0481(5) Uani 1 1 d . . .
F2 F 0.7971(5) 0.68019(15) 0.12705(12) 0.0476(5) Uani 1 1 d . . .
C8 C 0.8907(6) 0.4660(2) 0.09631(18) 0.0250(6) Uani 1 1 d . . .
O1 O 0.5759(5) 0.11900(18) 0.78213(14) 0.0410(5) Uani 1 1 d . . .
N1 N 0.5707(6) 0.3299(2) 0.43841(17) 0.0334(5) Uani 1 1 d . . .
O2 O 0.1981(6) 0.00451(19) 0.67729(16) 0.0508(6) Uani 1 1 d . . .
C4 C 0.3878(7) 0.2254(2) 0.4211(2) 0.0328(6) Uani 1 1 d . . .
H4A H 0.2967 0.2044 0.3506 0.039 Uiso 1 1 calc R . .
C1 C 0.4607(6) 0.1760(2) 0.6043(2) 0.0267(6) Uani 1 1 d . . .
C10 C 0.8986(6) 0.5897(2) 0.06535(19) 0.0277(6) Uani 1 1 d . . .
C5 C 0.3255(7) 0.1467(2) 0.5009(2) 0.0333(6) Uani 1 1 d . . .
H5A H 0.1934 0.0744 0.4852 0.040 Uiso 1 1 calc R . .
C2 C 0.6511(7) 0.2839(2) 0.6236(2) 0.0326(6) Uani 1 1 d . . .
H2A H 0.7475 0.3065 0.6932 0.039 Uiso 1 1 calc R . .
C9 C 0.9953(6) 0.3786(2) 0.0286(2) 0.0279(6) Uani 1 1 d . . .
C6 C 0.3933(7) 0.0896(2) 0.6900(2) 0.0318(6) Uani 1 1 d . . .
C3 C 0.6963(7) 0.3577(3) 0.5382(2) 0.0360(7) Uani 1 1 d . . .
H3A H 0.8231 0.4317 0.5516 0.043 Uiso 1 1 calc R . .
C7 C 0.5243(9) 0.0398(3) 0.8697(2) 0.0551(9) Uani 1 1 d . . .
H7A H 0.6672 0.0677 0.9335 0.083 Uiso 1 1 calc R . .
H7B H 0.5737 -0.0460 0.8524 0.083 Uiso 1 1 calc R . .
H7C H 0.2975 0.0445 0.8822 0.083 Uiso 1 1 calc R . .

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
I1 0.02153(11) 0.04758(13) 0.01842(10) 0.00734(7) 0.00222(7) -0.00101(8)
F1 0.0784(14) 0.0336(9) 0.0340(9) 0.0082(7) 0.0130(9) 0.0023(9)
F2 0.0745(13) 0.0422(9) 0.0296(9) -0.0002(7) 0.0180(9) 0.0143(9)
C8 0.0187(13) 0.0416(15) 0.0139(12) 0.0052(11) -0.0010(10) -0.0015(11)
O1 0.0513(13) 0.0491(12) 0.0241(10) 0.0112(9) 0.0094(10) -0.0006(10)
N1 0.0352(14) 0.0390(13) 0.0277(13) 0.0095(10) 0.0087(11) 0.0031(11)
O2 0.0712(17) 0.0420(12) 0.0393(12) 0.0108(9) 0.0088(11) -0.0161(12)
C4 0.0384(17) 0.0378(16) 0.0224(14) 0.0025(11) 0.0035(12) 0.0068(13)
C1 0.0306(15) 0.0270(13) 0.0245(13) 0.0032(10) 0.0100(12) 0.0066(11)
C10 0.0258(15) 0.0362(15) 0.0207(13) -0.0032(11) 0.0014(11) 0.0036(12)
C5 0.0397(17) 0.0328(15) 0.0282(15) 0.0017(11) 0.0081(13) -0.0013(13)
C2 0.0332(16) 0.0412(16) 0.0234(14) 0.0023(12) 0.0036(12) 0.0020(13)
C9 0.0298(15) 0.0298(14) 0.0230(13) 0.0064(11) -0.0013(12) -0.0012(12)
C6 0.0389(17) 0.0324(15) 0.0263(15) 0.0044(11) 0.0114(13) 0.0093(13)
C3 0.0392(17) 0.0374(16) 0.0315(16) 0.0061(12) 0.0049(13) -0.0060(13)
C7 0.074(3) 0.065(2) 0.0286(17) 0.0250(15) 0.0112(17) -0.0003(19)

_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
I1 C8 2.111(2) . ?
F1 C9 1.368(3) . ?
F2 C10 1.354(3) . ?
C8 C10 1.401(4) . ?
C8 C9 1.384(4) . ?
O1 C6 1.342(3) . ?
O1 C7 1.460(3) . ?
N1 C4 1.349(4) . ?
N1 C3 1.337(4) . ?
O2 C6 1.210(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.389(4) . ?
C1 C5 1.393(4) . ?
C1 C2 1.396(4) . ?
C1 C6 1.506(3) . ?
C10 C9 1.383(4) 2_765 ?
C5 H5A 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.397(4) . ?
C9 C10 1.383(4) 2_765 ?
C3 H3A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
I1 C8 C10 121.42(18) . . ?
I1 C8 C9 121.94(18) . . ?
C10 C8 C9 116.6(2) . . ?
C6 O1 C7 115.0(2) . . ?
C4 N1 C3 117.3(2) . . ?
N1 C4 H4A 118.3 . . ?
N1 C4 C5 123.4(3) . . ?
H4A C4 C5 118.3 . . ?
C5 C1 C2 118.6(2) . . ?
C5 C1 C6 118.2(2) . . ?
C2 C1 C6 123.2(2) . . ?
F2 C10 C8 120.0(2) . . ?
F2 C10 C9 118.9(2) . 2_765 ?
C8 C10 C9 121.1(2) . 2_765 ?
C4 C5 C1 118.7(3) . . ?
C4 C5 H5A 120.7 . . ?
C1 C5 H5A 120.7 . . ?
C1 C2 H2A 120.8 . . ?
C1 C2 C3 118.3(3) . . ?
H2A C2 C3 120.8 . . ?
F1 C9 C8 119.8(2) . . ?
F1 C9 C10 117.8(2) . 2_765 ?
C8 C9 C10 122.3(2) . 2_765 ?
O1 C6 O2 124.3(2) . . ?
O1 C6 C1 111.6(2) . . ?
O2 C6 C1 124.2(3) . . ?
N1 C3 C2 123.6(3) . . ?
N1 C3 H3A 118.2 . . ?
C2 C3 H3A 118.2 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C4 C5 -0.1(4) . . . . ?
I1 C8 C10 F2 -3.1(3) . . . . ?
I1 C8 C10 C9 177.8(2) . . . 2_765 ?
C9 C8 C10 F2 179.4(2) . . . . ?
C9 C8 C10 C9 0.3(4) . . . 2_765 ?
N1 C4 C5 C1 -0.6(4) . . . . ?
C2 C1 C5 C4 0.5(4) . . . . ?
C6 C1 C5 C4 -179.6(2) . . . . ?
C5 C1 C2 C3 0.2(4) . . . . ?
C6 C1 C2 C3 -179.7(2) . . . . ?
I1 C8 C9 F1 1.7(3) . . . . ?
I1 C8 C9 C10 -177.8(2) . . . 2_765 ?
C10 C8 C9 F1 179.2(2) . . . . ?
C10 C8 C9 C10 -0.3(4) . . . 2_765 ?
C7 O1 C6 O2 0.0(4) . . . . ?
C7 O1 C6 C1 179.8(2) . . . . ?
C5 C1 C6 O1 170.8(2) . . . . ?
C5 C1 C6 O2 -9.4(4) . . . . ?
C2 C1 C6 O1 -9.4(4) . . . . ?
C2 C1 C6 O2 170.4(3) . . . . ?
C4 N1 C3 C2 0.9(4) . . . . ?
C1 C2 C3 N1 -1.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.119


