# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Kari Rissanen'
_publ_contact_author_email       KARI.RISSANEN@JYU.FI

_publ_section_title              
;
Halogen bonding drives the self-assembly
of piperazine cyclophanes into porous structures
;
loop_
_publ_author_name
'Kari Rissanen'
'Juhani Huuskonen'
'Manu Lahtinen'
'Pierangelo Metrangolo'
'Kari Raatikainen'

# Attachment '1_F4DIB.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 717658'

_audit_creation_date             2009-02-10T11:07:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         '2(C36 H48 N6), C6 F4 I2, C H CL3'
_chemical_formula_sum            'C79 H97 Cl3 F4 I2 N12'
_chemical_formula_weight         1650.84
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   24.6450(7)
_cell_length_b                   5.8927(2)
_cell_length_c                   27.7544(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.404(2)
_cell_angle_gamma                90
_cell_volume                     3976.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    113303
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      28.283
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.329665E-1
_diffrn_orient_matrix_ub_12      0.694885E-1
_diffrn_orient_matrix_ub_13      0.109166E-1
_diffrn_orient_matrix_ub_21      0.16511E-2
_diffrn_orient_matrix_ub_22      0.12964
_diffrn_orient_matrix_ub_23      -0.229658E-1
_diffrn_orient_matrix_ub_31      -0.24537E-1
_diffrn_orient_matrix_ub_32      -0.84637E-1
_diffrn_orient_matrix_ub_33      -0.262143E-1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_number            12399
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_reflns_number_total             6878
_reflns_number_gt                5395
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0681P)^2^+40.8870P] 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_number_reflns         6878
_refine_ls_number_parameters     478
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1578
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.946
_refine_diff_density_min         -2.177
_refine_diff_density_rms         0.148

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
Cl Cl 0.1484 0.1585 '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'

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 0.8180(3) 0.7614(12) 0.6785(2) 0.0216(15) Uani 1 1 d . . .
C2 C 0.8487(3) 0.5646(13) 0.6776(2) 0.0231(16) Uani 1 1 d . . .
H2 H 0.8364 0.4488 0.6546 0.028 Uiso 1 1 calc R . .
C3 C 0.8981(3) 0.5350(13) 0.7105(3) 0.0279(17) Uani 1 1 d . . .
H3 H 0.9186 0.3987 0.7098 0.033 Uiso 1 1 calc R . .
C4 C 0.9171(3) 0.7037(12) 0.7440(2) 0.0221(16) Uani 1 1 d . . .
C5 C 0.8869(3) 0.9039(13) 0.7435(2) 0.0236(16) Uani 1 1 d . . .
H5 H 0.8999 1.0224 0.7656 0.028 Uiso 1 1 calc R . .
C6 C 0.8383(3) 0.9329(13) 0.7114(3) 0.0248(16) Uani 1 1 d . . .
H6 H 0.8184 1.0709 0.7117 0.03 Uiso 1 1 calc R . .
C7 C 0.7630(3) 0.7915(12) 0.6467(2) 0.0220(15) Uani 1 1 d . . .
H7A H 0.7597 0.9492 0.6342 0.026 Uiso 1 1 calc R . .
H7B H 0.7604 0.688 0.6183 0.026 Uiso 1 1 calc R . .
N8 N 0.7172(2) 0.7436(10) 0.67389(19) 0.0189(12) Uani 1 1 d . . .
C9 C 0.6658(3) 0.8441(12) 0.6491(2) 0.0194(14) Uani 1 1 d . . .
H9A H 0.6554 0.7745 0.6164 0.023 Uiso 1 1 calc R . .
H9B H 0.6709 1.009 0.6446 0.023 Uiso 1 1 calc R . .
C10 C 0.6200(3) 0.8047(11) 0.6794(2) 0.0182(14) Uani 1 1 d . . .
H10A H 0.6301 0.8766 0.7119 0.022 Uiso 1 1 calc R . .
H10B H 0.5854 0.8747 0.6628 0.022 Uiso 1 1 calc R . .
N11 N 0.6119(2) 0.5613(10) 0.68525(19) 0.0181(12) Uani 1 1 d . . .
C12 C 0.6632(3) 0.4562(11) 0.7089(2) 0.0198(15) Uani 1 1 d . . .
H12A H 0.6578 0.2905 0.7116 0.024 Uiso 1 1 calc R . .
H12B H 0.6735 0.5182 0.7423 0.024 Uiso 1 1 calc R . .
C13 C 0.7094(3) 0.5013(12) 0.6798(3) 0.0221(15) Uani 1 1 d . . .
H13A H 0.7439 0.4331 0.697 0.026 Uiso 1 1 calc R . .
H13B H 0.7004 0.4289 0.6473 0.026 Uiso 1 1 calc R . .
C14 C 0.5647(3) 0.5156(13) 0.7115(2) 0.0224(15) Uani 1 1 d . . .
H14A H 0.5552 0.3526 0.7078 0.027 Uiso 1 1 calc R . .
H14B H 0.5325 0.6033 0.6954 0.027 Uiso 1 1 calc R . .
C15 C 0.5747(3) 0.5735(12) 0.7657(2) 0.0214(15) Uani 1 1 d . . .
C16 C 0.5638(3) 0.7901(12) 0.7821(2) 0.0213(15) Uani 1 1 d . . .
H16 H 0.5481 0.9024 0.7594 0.026 Uiso 1 1 calc R . .
C17 C 0.5759(3) 0.8423(12) 0.8320(2) 0.0219(15) Uani 1 1 d . . .
H17 H 0.5682 0.9899 0.8429 0.026 Uiso 1 1 calc R . .
C18 C 0.5989(3) 0.6803(12) 0.8656(2) 0.0200(14) Uani 1 1 d . . .
C19 C 0.6077(3) 0.4647(12) 0.8493(2) 0.0238(16) Uani 1 1 d . . .
H19 H 0.6218 0.3506 0.8722 0.029 Uiso 1 1 calc R . .
C20 C 0.5963(3) 0.4117(12) 0.7997(2) 0.0253(16) Uani 1 1 d . . .
H20 H 0.6035 0.263 0.7891 0.03 Uiso 1 1 calc R . .
C21 C 0.6136(3) 0.7464(13) 0.9193(2) 0.0232(15) Uani 1 1 d . . .
H21A H 0.6318 0.8966 0.9217 0.028 Uiso 1 1 calc R . .
H21B H 0.5794 0.7601 0.9335 0.028 Uiso 1 1 calc R . .
N22 N 0.6497(2) 0.5822(10) 0.94749(19) 0.0198(12) Uani 1 1 d . . .
C23 C 0.6546(3) 0.6157(13) 1.0004(2) 0.0251(16) Uani 1 1 d . . .
H23A H 0.6176 0.6167 1.0099 0.03 Uiso 1 1 calc R . .
H23B H 0.6724 0.7633 1.0098 0.03 Uiso 1 1 calc R . .
C24 C 0.6885(3) 0.4252(13) 1.0262(2) 0.0226(15) Uani 1 1 d . . .
H24A H 0.6913 0.4458 1.0619 0.027 Uiso 1 1 calc R . .
H24B H 0.6696 0.2792 1.0174 0.027 Uiso 1 1 calc R . .
N25 N 0.7440(2) 0.4158(11) 1.0135(2) 0.0237(13) Uani 1 1 d . . .
C26 C 0.7383(3) 0.3912(13) 0.9602(2) 0.0272(17) Uani 1 1 d . . .
H26A H 0.7197 0.2459 0.9501 0.033 Uiso 1 1 calc R . .
H26B H 0.7752 0.3884 0.9505 0.033 Uiso 1 1 calc R . .
C27 C 0.7054(3) 0.5852(13) 0.9352(2) 0.0242(16) Uani 1 1 d . . .
H27A H 0.7237 0.7307 0.9457 0.029 Uiso 1 1 calc R . .
H27B H 0.7034 0.5717 0.8994 0.029 Uiso 1 1 calc R . .
C28 C 0.7750(3) 0.2269(14) 1.0394(3) 0.0276(17) Uani 1 1 d . . .
H28A H 0.7526 0.0867 1.0343 0.033 Uiso 1 1 calc R . .
H28B H 0.7821 0.2597 1.0748 0.033 Uiso 1 1 calc R . .
C29 C 0.8293(3) 0.1891(13) 1.0215(2) 0.0248(16) Uani 1 1 d . . .
C30 C 0.8689(3) 0.3560(14) 1.0262(3) 0.0277(16) Uani 1 1 d . . .
H30 H 0.8647 0.4871 1.0451 0.033 Uiso 1 1 calc R . .
C31 C 0.9153(3) 0.3356(14) 1.0035(3) 0.0291(16) Uani 1 1 d . . .
H31 H 0.9425 0.4514 1.0073 0.035 Uiso 1 1 calc R . .
C32 C 0.9215(3) 0.1439(13) 0.9752(2) 0.0258(16) Uani 1 1 d . . .
C33 C 0.8834(3) -0.0303(13) 0.9731(3) 0.0288(17) Uani 1 1 d . . .
H33 H 0.8884 -0.1654 0.9557 0.035 Uiso 1 1 calc R . .
C34 C 0.8377(3) -0.0077(13) 0.9964(3) 0.0282(17) Uani 1 1 d . . .
H34 H 0.812 -0.1286 0.995 0.034 Uiso 1 1 calc R . .
C35 C 0.9696(3) 0.1269(14) 0.9476(3) 0.0295(18) Uani 1 1 d . . .
H35A H 1.0044 0.1338 0.971 0.035 Uiso 1 1 calc R . .
H35B H 0.9682 -0.0213 0.9306 0.035 Uiso 1 1 calc R . .
N36 N 0.9689(2) 0.3096(11) 0.9117(2) 0.0245(13) Uani 1 1 d . . .
C37 C 1.0162(3) 0.2864(13) 0.8861(3) 0.0260(17) Uani 1 1 d . . .
H37A H 1.0137 0.1402 0.8682 0.031 Uiso 1 1 calc R . .
H37B H 1.0506 0.2859 0.9101 0.031 Uiso 1 1 calc R . .
C38 C 1.0176(3) 0.4793(14) 0.8505(3) 0.0265(16) Uani 1 1 d . . .
H38A H 1.0216 0.6251 0.8684 0.032 Uiso 1 1 calc R . .
H38B H 1.0498 0.4612 0.8336 0.032 Uiso 1 1 calc R . .
N39 N 0.9666(2) 0.4826(11) 0.8141(2) 0.0237(13) Uani 1 1 d . . .
C40 C 0.9195(3) 0.5013(14) 0.8399(3) 0.0254(16) Uani 1 1 d . . .
H40A H 0.8851 0.5007 0.8159 0.031 Uiso 1 1 calc R . .
H40B H 0.9216 0.647 0.8578 0.031 Uiso 1 1 calc R . .
C41 C 0.9185(3) 0.3083(13) 0.8752(3) 0.0258(16) Uani 1 1 d . . .
H41A H 0.886 0.3231 0.8917 0.031 Uiso 1 1 calc R . .
H41B H 0.9156 0.1624 0.8572 0.031 Uiso 1 1 calc R . .
C42 C 0.9696(3) 0.6743(13) 0.7806(2) 0.0238(15) Uani 1 1 d . . .
H42A H 1.0008 0.6495 0.7627 0.029 Uiso 1 1 calc R . .
H42B H 0.977 0.8155 0.7998 0.029 Uiso 1 1 calc R . .
C43A C 0.7727(4) 0.9841(16) 0.8150(3) 0.024(4) Uani 0.35 1 d PDU A 1
H43A H 0.8091 1.0554 0.813 0.029 Uiso 0.35 1 calc PR A 1
C43B C 0.7275(5) 0.8955(16) 0.8174(2) 0.014(9) Uani 0.15 1 d PDU A 2
H43B H 0.6911 0.8242 0.8194 0.017 Uiso 0.15 1 calc PR A 2
Cl44 Cl 0.7268(2) 1.0267(10) 0.75999(19) 0.0642(14) Uani 0.5 1 d PD . .
Cl45 Cl 0.7802(5) 0.6890(16) 0.8239(4) 0.201(7) Uani 0.5 1 d PD . .
Cl46 Cl 0.7431(6) 1.1098(19) 0.8621(4) 0.276(12) Uani 0.5 1 d PD . .
I47 I 0.566430(18) 0.33630(7) 0.596874(14) 0.01916(16) Uani 1 1 d . . .
C48 C 0.5267(3) 0.1368(12) 0.5389(2) 0.0205(15) Uani 1 1 d . . .
C49 C 0.4992(3) -0.0641(12) 0.5475(2) 0.0183(14) Uani 1 1 d . . .
F50 F 0.49759(17) -0.1276(7) 0.59376(13) 0.0244(9) Uani 1 1 d . . .
C51 C 0.5264(3) 0.1946(12) 0.4903(2) 0.0203(15) Uani 1 1 d . . .
F52 F 0.55234(17) 0.3859(7) 0.47982(14) 0.0245(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
C1 0.020(4) 0.026(4) 0.020(3) 0.006(3) 0.005(3) -0.001(3)
C2 0.020(4) 0.026(4) 0.022(3) -0.002(3) 0.002(3) -0.002(3)
C3 0.025(4) 0.024(4) 0.036(4) 0.001(3) 0.010(3) 0.001(3)
C4 0.025(4) 0.025(4) 0.016(3) 0.002(3) 0.004(3) -0.007(3)
C5 0.025(4) 0.027(4) 0.018(3) -0.001(3) 0.004(3) -0.002(3)
C6 0.029(4) 0.021(4) 0.025(4) 0.004(3) 0.007(3) 0.002(3)
C7 0.023(4) 0.025(4) 0.019(3) 0.004(3) 0.007(3) 0.001(3)
N8 0.022(3) 0.021(3) 0.014(3) 0.002(2) 0.004(2) 0.001(2)
C9 0.021(4) 0.022(4) 0.015(3) 0.000(3) 0.003(3) 0.000(3)
C10 0.021(4) 0.018(4) 0.015(3) 0.001(3) 0.000(3) 0.001(3)
N11 0.020(3) 0.019(3) 0.014(3) 0.003(2) -0.001(2) -0.002(2)
C12 0.024(4) 0.013(4) 0.023(3) 0.001(3) 0.006(3) -0.001(3)
C13 0.023(4) 0.018(3) 0.026(4) 0.000(3) 0.006(3) 0.003(3)
C14 0.020(4) 0.021(4) 0.026(4) -0.001(3) 0.003(3) -0.004(3)
C15 0.017(4) 0.028(4) 0.020(3) 0.000(3) 0.004(3) -0.005(3)
C16 0.020(4) 0.021(4) 0.024(3) 0.004(3) 0.005(3) 0.002(3)
C17 0.019(4) 0.019(4) 0.028(4) -0.004(3) 0.008(3) 0.001(3)
C18 0.019(3) 0.018(4) 0.023(3) 0.002(3) 0.006(3) -0.006(3)
C19 0.033(4) 0.018(4) 0.021(3) 0.001(3) 0.007(3) -0.001(3)
C20 0.041(5) 0.016(3) 0.022(3) -0.001(3) 0.011(3) -0.001(3)
C21 0.026(4) 0.026(4) 0.018(3) -0.005(3) 0.007(3) -0.003(3)
N22 0.018(3) 0.027(3) 0.015(3) -0.001(2) 0.004(2) -0.002(2)
C23 0.025(4) 0.034(4) 0.017(3) -0.005(3) 0.006(3) -0.004(3)
C24 0.021(4) 0.032(4) 0.015(3) -0.003(3) 0.007(3) -0.005(3)
N25 0.021(3) 0.034(3) 0.015(3) 0.001(2) 0.000(2) 0.001(3)
C26 0.030(4) 0.037(5) 0.017(3) 0.001(3) 0.011(3) 0.000(3)
C27 0.029(4) 0.031(4) 0.014(3) -0.002(3) 0.007(3) -0.002(3)
C28 0.025(4) 0.033(4) 0.025(4) 0.003(3) 0.005(3) 0.000(3)
C29 0.027(4) 0.027(4) 0.020(3) 0.006(3) 0.003(3) 0.003(3)
C30 0.028(4) 0.031(4) 0.025(4) -0.006(3) 0.005(3) -0.003(3)
C31 0.030(4) 0.027(4) 0.029(4) 0.001(3) 0.000(3) -0.001(4)
C32 0.028(4) 0.028(4) 0.021(3) 0.005(3) 0.001(3) 0.007(3)
C33 0.038(5) 0.021(4) 0.026(4) -0.004(3) 0.003(3) 0.003(3)
C34 0.032(4) 0.025(4) 0.028(4) 0.000(3) 0.006(3) -0.006(3)
C35 0.028(4) 0.033(5) 0.028(4) 0.008(3) 0.008(3) 0.009(3)
N36 0.022(3) 0.030(4) 0.021(3) 0.002(3) 0.002(2) 0.007(3)
C37 0.017(4) 0.038(5) 0.022(3) -0.005(3) 0.001(3) 0.006(3)
C38 0.021(4) 0.036(4) 0.023(3) -0.001(3) 0.004(3) 0.004(3)
N39 0.019(3) 0.032(3) 0.020(3) 0.001(3) 0.004(2) 0.002(3)
C40 0.019(4) 0.035(4) 0.024(4) 0.002(3) 0.008(3) -0.003(3)
C41 0.021(4) 0.030(4) 0.026(4) 0.006(3) 0.001(3) 0.000(3)
C42 0.017(3) 0.030(4) 0.024(3) 0.001(3) 0.003(3) -0.004(3)
C43A 0.025(5) 0.024(5) 0.024(5) 0.000(2) 0.007(2) 0.002(2)
C43B 0.014(9) 0.014(9) 0.014(9) -0.001(2) 0.001(2) 0.000(2)
Cl44 0.072(4) 0.060(3) 0.061(3) -0.003(3) 0.010(3) 0.006(3)
Cl45 0.197(14) 0.210(15) 0.221(15) -0.076(12) 0.110(12) -0.051(12)
Cl46 0.148(12) 0.114(10) 0.57(4) 0.037(16) 0.083(17) 0.018(9)
I47 0.0222(3) 0.0175(2) 0.0171(2) -0.00194(18) 0.00109(16) 0.0006(2)
C48 0.022(4) 0.021(4) 0.018(3) -0.003(3) 0.002(3) 0.004(3)
C49 0.024(4) 0.019(4) 0.014(3) 0.003(3) 0.010(3) 0.007(3)
F50 0.035(2) 0.024(2) 0.0134(18) 0.0013(16) 0.0044(17) 0.0002(18)
C51 0.025(4) 0.017(4) 0.020(3) -0.002(3) 0.007(3) 0.000(3)
F52 0.032(2) 0.020(2) 0.022(2) 0.0017(16) 0.0043(17) -0.0058(18)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C2 1.388(10) . ?
C1 C6 1.398(10) . ?
C1 C7 1.503(10) . ?
C2 C3 1.408(10) . ?
C2 H2 0.95 . ?
C3 C4 1.388(10) . ?
C3 H3 0.95 . ?
C4 C5 1.394(10) . ?
C4 C42 1.519(10) . ?
C5 C6 1.381(10) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N8 1.484(8) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
N8 C13 1.454(9) . ?
N8 C9 1.465(9) . ?
C9 C10 1.532(9) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N11 1.461(9) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
N11 C12 1.465(9) . ?
N11 C14 1.493(8) . ?
C12 C13 1.522(9) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.523(9) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C20 1.386(10) . ?
C15 C16 1.395(10) . ?
C16 C17 1.403(10) . ?
C16 H16 0.95 . ?
C17 C18 1.389(10) . ?
C17 H17 0.95 . ?
C18 C19 1.378(10) . ?
C18 C21 1.526(9) . ?
C19 C20 1.395(10) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 N22 1.454(9) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
N22 C23 1.467(8) . ?
N22 C27 1.468(9) . ?
C23 C24 1.509(10) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 N25 1.469(9) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
N25 C28 1.468(10) . ?
N25 C26 1.470(8) . ?
C26 C27 1.504(10) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C28 C29 1.519(10) . ?
C28 H28A 0.99 . ?
C28 H28B 0.99 . ?
C29 C30 1.377(11) . ?
C29 C34 1.386(11) . ?
C30 C31 1.397(10) . ?
C30 H30 0.95 . ?
C31 C32 1.397(11) . ?
C31 H31 0.95 . ?
C32 C33 1.387(11) . ?
C32 C35 1.517(10) . ?
C33 C34 1.392(10) . ?
C33 H33 0.95 . ?
C34 H34 0.95 . ?
C35 N36 1.464(9) . ?
C35 H35A 0.99 . ?
C35 H35B 0.99 . ?
N36 C37 1.468(9) . ?
N36 C41 1.469(9) . ?
C37 C38 1.510(11) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C38 N39 1.478(9) . ?
C38 H38A 0.99 . ?
C38 H38B 0.99 . ?
N39 C40 1.463(8) . ?
N39 C42 1.473(9) . ?
C40 C41 1.504(10) . ?
C40 H40A 0.99 . ?
C40 H40B 0.99 . ?
C41 H41A 0.99 . ?
C41 H41B 0.99 . ?
C42 H42A 0.99 . ?
C42 H42B 0.99 . ?
C43A Cl45 1.762(3) . ?
C43A Cl46 1.762(3) . ?
C43A Cl44 1.764(2) . ?
C43A H43A 1 . ?
C43B Cl45 1.768(3) . ?
C43B Cl46 1.768(3) . ?
C43B Cl44 1.769(2) . ?
C43B H43B 1 . ?
I47 C48 2.101(7) . ?
C48 C51 1.390(9) . ?
C48 C49 1.404(10) . ?
C49 F50 1.345(7) . ?
C49 C51 1.368(10) 3_656 ?
C51 F52 1.351(8) . ?
C51 C49 1.368(10) 3_656 ?

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
C2 C1 C6 118.6(7) . . ?
C2 C1 C7 122.1(7) . . ?
C6 C1 C7 119.3(7) . . ?
C1 C2 C3 120.6(7) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.5(7) . . ?
C3 C4 C42 121.5(7) . . ?
C5 C4 C42 120.0(6) . . ?
C6 C5 C4 121.2(7) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.7(7) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N8 C7 C1 111.4(5) . . ?
N8 C7 H7A 109.3 . . ?
C1 C7 H7A 109.3 . . ?
N8 C7 H7B 109.3 . . ?
C1 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?
C13 N8 C9 109.2(6) . . ?
C13 N8 C7 111.8(5) . . ?
C9 N8 C7 110.8(5) . . ?
N8 C9 C10 109.8(5) . . ?
N8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N11 C10 C9 109.7(6) . . ?
N11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C10 N11 C12 109.9(5) . . ?
C10 N11 C14 111.3(5) . . ?
C12 N11 C14 112.9(5) . . ?
N11 C12 C13 110.8(5) . . ?
N11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N8 C13 C12 110.9(6) . . ?
N8 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
N11 C14 C15 115.4(6) . . ?
N11 C14 H14A 108.4 . . ?
C15 C14 H14A 108.4 . . ?
N11 C14 H14B 108.4 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C20 C15 C16 118.7(6) . . ?
C20 C15 C14 120.0(6) . . ?
C16 C15 C14 121.2(6) . . ?
C15 C16 C17 120.0(6) . . ?
C15 C16 H16 120 . . ?
C17 C16 H16 120 . . ?
C18 C17 C16 120.7(7) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 118.8(6) . . ?
C19 C18 C21 122.0(6) . . ?
C17 C18 C21 119.1(6) . . ?
C18 C19 C20 120.9(7) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 120.7(7) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N22 C21 C18 112.5(6) . . ?
N22 C21 H21A 109.1 . . ?
C18 C21 H21A 109.1 . . ?
N22 C21 H21B 109.1 . . ?
C18 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C21 N22 C23 113.0(5) . . ?
C21 N22 C27 112.4(5) . . ?
C23 N22 C27 107.8(5) . . ?
N22 C23 C24 108.8(6) . . ?
N22 C23 H23A 109.9 . . ?
C24 C23 H23A 109.9 . . ?
N22 C23 H23B 109.9 . . ?
C24 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
N25 C24 C23 112.3(6) . . ?
N25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
N25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
C28 N25 C24 110.0(6) . . ?
C28 N25 C26 111.9(6) . . ?
C24 N25 C26 107.8(5) . . ?
N25 C26 C27 110.2(6) . . ?
N25 C26 H26A 109.6 . . ?
C27 C26 H26A 109.6 . . ?
N25 C26 H26B 109.6 . . ?
C27 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
N22 C27 C26 109.7(6) . . ?
N22 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
N22 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
N25 C28 C29 111.6(6) . . ?
N25 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
N25 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 108 . . ?
C30 C29 C34 118.8(7) . . ?
C30 C29 C28 121.0(7) . . ?
C34 C29 C28 120.0(7) . . ?
C29 C30 C31 121.1(7) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C30 C31 C32 119.6(7) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C33 C32 C31 119.2(7) . . ?
C33 C32 C35 120.6(7) . . ?
C31 C32 C35 120.2(7) . . ?
C32 C33 C34 120.2(7) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C29 C34 C33 120.8(7) . . ?
C29 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
N36 C35 C32 111.8(6) . . ?
N36 C35 H35A 109.2 . . ?
C32 C35 H35A 109.2 . . ?
N36 C35 H35B 109.2 . . ?
C32 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
C35 N36 C37 109.8(6) . . ?
C35 N36 C41 112.3(6) . . ?
C37 N36 C41 108.3(5) . . ?
N36 C37 C38 110.6(6) . . ?
N36 C37 H37A 109.5 . . ?
C38 C37 H37A 109.5 . . ?
N36 C37 H37B 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
N39 C38 C37 110.4(6) . . ?
N39 C38 H38A 109.6 . . ?
C37 C38 H38A 109.6 . . ?
N39 C38 H38B 109.6 . . ?
C37 C38 H38B 109.6 . . ?
H38A C38 H38B 108.1 . . ?
C40 N39 C42 112.2(6) . . ?
C40 N39 C38 108.7(5) . . ?
C42 N39 C38 108.5(6) . . ?
N39 C40 C41 111.1(6) . . ?
N39 C40 H40A 109.4 . . ?
C41 C40 H40A 109.4 . . ?
N39 C40 H40B 109.4 . . ?
C41 C40 H40B 109.4 . . ?
H40A C40 H40B 108 . . ?
N36 C41 C40 110.1(6) . . ?
N36 C41 H41A 109.6 . . ?
C40 C41 H41A 109.6 . . ?
N36 C41 H41B 109.6 . . ?
C40 C41 H41B 109.6 . . ?
H41A C41 H41B 108.2 . . ?
N39 C42 C4 112.6(6) . . ?
N39 C42 H42A 109.1 . . ?
C4 C42 H42A 109.1 . . ?
N39 C42 H42B 109.1 . . ?
C4 C42 H42B 109.1 . . ?
H42A C42 H42B 107.8 . . ?
Cl45 C43A Cl46 110.9(5) . . ?
Cl45 C43A Cl44 107.4(5) . . ?
Cl46 C43A Cl44 107.3(5) . . ?
Cl45 C43A H43A 110.4 . . ?
Cl46 C43A H43A 110.4 . . ?
Cl44 C43A H43A 110.4 . . ?
Cl45 C43B Cl46 110.3(6) . . ?
Cl45 C43B Cl44 107.0(5) . . ?
Cl46 C43B Cl44 106.8(5) . . ?
Cl45 C43B H43B 110.9 . . ?
Cl46 C43B H43B 110.9 . . ?
Cl44 C43B H43B 110.9 . . ?
C51 C48 C49 116.4(6) . . ?
C51 C48 I47 122.3(5) . . ?
C49 C48 I47 121.3(5) . . ?
F50 C49 C51 119.6(6) . 3_656 ?
F50 C49 C48 119.1(6) . . ?
C51 C49 C48 121.3(6) 3_656 . ?
F52 C51 C49 118.6(6) . 3_656 ?
F52 C51 C48 119.1(6) . . ?
C49 C51 C48 122.3(6) 3_656 . ?

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
C6 C1 C2 C3 2.6(10) . . . . ?
C7 C1 C2 C3 -175.2(6) . . . . ?
C1 C2 C3 C4 -0.8(10) . . . . ?
C2 C3 C4 C5 -1.3(10) . . . . ?
C2 C3 C4 C42 178.7(6) . . . . ?
C3 C4 C5 C6 1.7(10) . . . . ?
C42 C4 C5 C6 -178.4(6) . . . . ?
C4 C5 C6 C1 0.1(10) . . . . ?
C2 C1 C6 C5 -2.3(10) . . . . ?
C7 C1 C6 C5 175.6(6) . . . . ?
C2 C1 C7 N8 98.7(7) . . . . ?
C6 C1 C7 N8 -79.1(8) . . . . ?
C1 C7 N8 C13 -77.0(7) . . . . ?
C1 C7 N8 C9 160.9(6) . . . . ?
C13 N8 C9 C10 59.8(7) . . . . ?
C7 N8 C9 C10 -176.6(5) . . . . ?
N8 C9 C10 N11 -60.3(7) . . . . ?
C9 C10 N11 C12 58.3(7) . . . . ?
C9 C10 N11 C14 -175.8(5) . . . . ?
C10 N11 C12 C13 -57.0(7) . . . . ?
C14 N11 C12 C13 178.1(5) . . . . ?
C9 N8 C13 C12 -58.4(7) . . . . ?
C7 N8 C13 C12 178.6(5) . . . . ?
N11 C12 C13 N8 57.3(7) . . . . ?
C10 N11 C14 C15 -71.4(7) . . . . ?
C12 N11 C14 C15 52.8(8) . . . . ?
N11 C14 C15 C20 -89.9(8) . . . . ?
N11 C14 C15 C16 88.4(8) . . . . ?
C20 C15 C16 C17 1.4(10) . . . . ?
C14 C15 C16 C17 -176.8(6) . . . . ?
C15 C16 C17 C18 0.2(10) . . . . ?
C16 C17 C18 C19 -2.5(10) . . . . ?
C16 C17 C18 C21 177.6(6) . . . . ?
C17 C18 C19 C20 3.1(10) . . . . ?
C21 C18 C19 C20 -177.0(7) . . . . ?
C16 C15 C20 C19 -0.8(11) . . . . ?
C14 C15 C20 C19 177.4(7) . . . . ?
C18 C19 C20 C15 -1.5(11) . . . . ?
C19 C18 C21 N22 15.1(9) . . . . ?
C17 C18 C21 N22 -164.9(6) . . . . ?
C18 C21 N22 C23 -167.4(6) . . . . ?
C18 C21 N22 C27 70.3(7) . . . . ?
C21 N22 C23 C24 174.8(6) . . . . ?
C27 N22 C23 C24 -60.3(7) . . . . ?
N22 C23 C24 N25 59.7(8) . . . . ?
C23 C24 N25 C28 -179.6(6) . . . . ?
C23 C24 N25 C26 -57.4(8) . . . . ?
C28 N25 C26 C27 178.8(6) . . . . ?
C24 N25 C26 C27 57.8(8) . . . . ?
C21 N22 C27 C26 -172.2(6) . . . . ?
C23 N22 C27 C26 62.6(7) . . . . ?
N25 C26 C27 N22 -62.3(8) . . . . ?
C24 N25 C28 C29 171.4(6) . . . . ?
C26 N25 C28 C29 51.6(8) . . . . ?
N25 C28 C29 C30 61.5(9) . . . . ?
N25 C28 C29 C34 -112.9(8) . . . . ?
C34 C29 C30 C31 4.0(11) . . . . ?
C28 C29 C30 C31 -170.4(7) . . . . ?
C29 C30 C31 C32 0.6(11) . . . . ?
C30 C31 C32 C33 -4.6(11) . . . . ?
C30 C31 C32 C35 175.8(7) . . . . ?
C31 C32 C33 C34 3.9(11) . . . . ?
C35 C32 C33 C34 -176.4(7) . . . . ?
C30 C29 C34 C33 -4.7(11) . . . . ?
C28 C29 C34 C33 169.8(7) . . . . ?
C32 C33 C34 C29 0.7(11) . . . . ?
C33 C32 C35 N36 119.5(8) . . . . ?
C31 C32 C35 N36 -60.9(9) . . . . ?
C32 C35 N36 C37 179.8(6) . . . . ?
C32 C35 N36 C41 -59.7(8) . . . . ?
C35 N36 C37 C38 -177.5(6) . . . . ?
C41 N36 C37 C38 59.5(8) . . . . ?
N36 C37 C38 N39 -59.4(8) . . . . ?
C37 C38 N39 C40 57.2(8) . . . . ?
C37 C38 N39 C42 179.5(6) . . . . ?
C42 N39 C40 C41 -177.9(6) . . . . ?
C38 N39 C40 C41 -58.0(8) . . . . ?
C35 N36 C41 C40 179.0(6) . . . . ?
C37 N36 C41 C40 -59.5(8) . . . . ?
N39 C40 C41 N36 60.3(8) . . . . ?
C40 N39 C42 C4 -55.5(8) . . . . ?
C38 N39 C42 C4 -175.6(6) . . . . ?
C3 C4 C42 N39 -61.6(8) . . . . ?
C5 C4 C42 N39 118.4(7) . . . . ?
Cl45 C43A Cl44 C43B 59.6(5) . . . . ?
Cl46 C43A Cl44 C43B -59.7(5) . . . . ?
Cl45 C43B Cl44 C43A -59.0(5) . . . . ?
Cl46 C43B Cl44 C43A 59.1(5) . . . . ?
Cl46 C43A Cl45 C43B 57.4(5) . . . . ?
Cl44 C43A Cl45 C43B -59.6(5) . . . . ?
Cl46 C43B Cl45 C43A -56.8(5) . . . . ?
Cl44 C43B Cl45 C43A 59.1(5) . . . . ?
Cl45 C43A Cl46 C43B -57.4(5) . . . . ?
Cl44 C43A Cl46 C43B 59.7(5) . . . . ?
Cl45 C43B Cl46 C43A 56.8(5) . . . . ?
Cl44 C43B Cl46 C43A -59.2(5) . . . . ?
C51 C48 C49 F50 -179.4(6) . . . . ?
I47 C48 C49 F50 1.0(8) . . . . ?
C51 C48 C49 C51 0.0(11) . . . 3_656 ?
I47 C48 C49 C51 -179.6(5) . . . 3_656 ?
C49 C48 C51 F52 -179.8(6) . . . . ?
I47 C48 C51 F52 -0.2(9) . . . . ?
C49 C48 C51 C49 0.0(11) . . . 3_656 ?
I47 C48 C51 C49 179.6(5) . . . 3_656 ?

# Attachment '2_F4DIB.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 717659'

_audit_creation_date             2009-02-10T11:54:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         '2(C37 H42 N6), 2(C6 F4 I2), C H Cl3'
_chemical_formula_sum            'C87 H85 Cl3 F8 I4 N12'
_chemical_formula_weight         2064.62
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   5.9855(2)
_cell_length_b                   33.6650(10)
_cell_length_c                   22.8345(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.906(2)
_cell_angle_gamma                90
_cell_volume                     4576.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10143
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      63.48
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2052
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    12.037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing et al., 1995)'
_exptl_absorpt_correction_T_min  0.068
_exptl_absorpt_correction_T_max  0.299

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.449388E-1
_diffrn_orient_matrix_ub_12      -0.247923E-1
_diffrn_orient_matrix_ub_13      0.198727E-1
_diffrn_orient_matrix_ub_21      0.146815
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      0.252323E-1
_diffrn_orient_matrix_ub_31      -0.680955E-1
_diffrn_orient_matrix_ub_32      0.163614E-1
_diffrn_orient_matrix_ub_33      0.301129E-1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_number            13440
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         63.48
_diffrn_reflns_theta_full        63.48
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_reflns_number_total             7310
_reflns_number_gt                6224
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0951P)^2^+12.1523P] 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_number_reflns         7310
_refine_ls_number_parameters     528
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.17
_refine_ls_wR_factor_gt          0.1613
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.502
_refine_diff_density_min         -1.515
_refine_diff_density_rms         0.177

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_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 0.554(3) 0.7934(3) 0.7561(4) 0.084(4) Uani 1 1 d . . .
H1A H 0.7111 0.8029 0.7567 0.101 Uiso 1 1 calc R . .
H1B H 0.458 0.8169 0.7604 0.101 Uiso 1 1 calc R . .
C2 C 0.5388(17) 0.7662(2) 0.8088(4) 0.053(2) Uani 1 1 d . . .
C3 C 0.6907(16) 0.7363(3) 0.8208(4) 0.060(2) Uani 1 1 d . . .
H3 H 0.8012 0.7317 0.7945 0.072 Uiso 1 1 calc R . .
C4 C 0.6885(15) 0.7125(3) 0.8699(4) 0.054(2) Uani 1 1 d . . .
H4 H 0.7981 0.6922 0.877 0.065 Uiso 1 1 calc R . .
C5 C 0.5284(13) 0.7178(2) 0.9092(3) 0.0377(16) Uani 1 1 d . . .
C6 C 0.3720(15) 0.7474(2) 0.8969(4) 0.050(2) Uani 1 1 d . . .
H6 H 0.2582 0.7515 0.9223 0.06 Uiso 1 1 calc R . .
C7 C 0.3789(18) 0.7714(2) 0.8473(4) 0.060(3) Uani 1 1 d . . .
H7 H 0.2706 0.792 0.84 0.072 Uiso 1 1 calc R . .
C8 C 0.5409(14) 0.6932(2) 0.9640(3) 0.0434(18) Uani 1 1 d . . .
H8A H 0.6986 0.6924 0.982 0.052 Uiso 1 1 calc R . .
H8B H 0.45 0.7061 0.9925 0.052 Uiso 1 1 calc R . .
N9 N 0.4607(10) 0.65253(16) 0.9535(2) 0.0305(12) Uani 1 1 d . . .
C10 C 0.5445(12) 0.6265(2) 1.0016(3) 0.0334(15) Uani 1 1 d . . .
H10A H 0.4867 0.6354 1.0385 0.04 Uiso 1 1 calc R . .
H10B H 0.7106 0.6277 1.0072 0.04 Uiso 1 1 calc R . .
C11 C 0.4687(12) 0.5841(2) 0.9877(3) 0.0333(15) Uani 1 1 d . . .
H11A H 0.5254 0.5753 0.9506 0.04 Uiso 1 1 calc R . .
H11B H 0.5311 0.5662 1.0197 0.04 Uiso 1 1 calc R . .
N12 N 0.2235(9) 0.58200(16) 0.9819(2) 0.0273(11) Uani 1 1 d . . .
C13 C 0.1332(11) 0.6095(2) 0.9353(3) 0.0332(15) Uani 1 1 d . . .
H13A H -0.0329 0.6092 0.9326 0.04 Uiso 1 1 calc R . .
H13B H 0.1788 0.6005 0.897 0.04 Uiso 1 1 calc R . .
C14 C 0.2165(12) 0.6513(2) 0.9473(3) 0.0371(16) Uani 1 1 d . . .
H14A H 0.1575 0.6689 0.9145 0.044 Uiso 1 1 calc R . .
H14B H 0.1603 0.6613 0.9838 0.044 Uiso 1 1 calc R . .
C15 C 0.1324(12) 0.5413(2) 0.9738(3) 0.0341(15) Uani 1 1 d . . .
H15A H -0.0269 0.5416 0.9819 0.041 Uiso 1 1 calc R . .
H15B H 0.2151 0.5237 1.0032 0.041 Uiso 1 1 calc R . .
C16 C 0.1459(12) 0.5239(2) 0.9130(3) 0.0318(15) Uani 1 1 d . . .
C17 C 0.3426(12) 0.5075(2) 0.8965(3) 0.0317(14) Uani 1 1 d . . .
H17 H 0.463 0.5022 0.9259 0.038 Uiso 1 1 calc R . .
C18 C 0.3689(12) 0.49852(19) 0.8385(3) 0.0313(14) Uani 1 1 d . . .
H18 H 0.5048 0.4873 0.828 0.038 Uiso 1 1 calc R . .
C19 C 0.1903(12) 0.5064(2) 0.7959(3) 0.0312(14) Uani 1 1 d . . .
C20 C -0.0150(11) 0.5191(2) 0.8125(3) 0.0334(15) Uani 1 1 d . . .
H20 H -0.1416 0.5213 0.784 0.04 Uiso 1 1 calc R . .
C21 C -0.0343(12) 0.5285(2) 0.8709(3) 0.0341(15) Uani 1 1 d . . .
H21 H -0.173 0.5382 0.8819 0.041 Uiso 1 1 calc R . .
N22 N 0.2031(10) 0.50597(18) 0.7334(3) 0.0350(13) Uani 1 1 d . . .
N23 N 0.4004(10) 0.50716(17) 0.7207(2) 0.0323(12) Uani 1 1 d . . .
C24 C 0.4179(12) 0.5133(2) 0.6590(3) 0.0323(15) Uani 1 1 d . . .
C25 C 0.6281(12) 0.5253(2) 0.6461(3) 0.0355(16) Uani 1 1 d . . .
H25 H 0.7527 0.5241 0.6754 0.043 Uiso 1 1 calc R . .
C26 C 0.6553(12) 0.5390(2) 0.5901(3) 0.0376(16) Uani 1 1 d . . .
H26 H 0.8 0.5472 0.5813 0.045 Uiso 1 1 calc R . .
C27 C 0.4756(12) 0.5410(2) 0.5463(3) 0.0306(14) Uani 1 1 d . . .
C28 C 0.2691(12) 0.5265(2) 0.5599(3) 0.0326(15) Uani 1 1 d . . .
H28 H 0.1459 0.5261 0.5301 0.039 Uiso 1 1 calc R . .
C29 C 0.2387(12) 0.5129(2) 0.6153(3) 0.0329(15) Uani 1 1 d . . .
H29 H 0.0962 0.5032 0.6236 0.039 Uiso 1 1 calc R . .
C30 C 0.5104(13) 0.5605(2) 0.4882(3) 0.0358(16) Uani 1 1 d . . .
H30A H 0.6669 0.5556 0.4797 0.043 Uiso 1 1 calc R . .
H30B H 0.4097 0.5476 0.4567 0.043 Uiso 1 1 calc R . .
N31 N 0.4689(10) 0.60335(17) 0.4858(2) 0.0319(13) Uani 1 1 d . . .
C32 C 0.6025(11) 0.6251(2) 0.5327(3) 0.0332(15) Uani 1 1 d . . .
H32A H 0.7637 0.6191 0.5313 0.04 Uiso 1 1 calc R . .
H32B H 0.56 0.6163 0.5714 0.04 Uiso 1 1 calc R . .
C33 C 0.5659(12) 0.6696(2) 0.5265(3) 0.0383(16) Uani 1 1 d . . .
H33A H 0.6543 0.6835 0.5593 0.046 Uiso 1 1 calc R . .
H33B H 0.6179 0.6788 0.4891 0.046 Uiso 1 1 calc R . .
N34 N 0.3277(10) 0.67876(17) 0.5272(3) 0.0361(13) Uani 1 1 d . . .
C35 C 0.2018(12) 0.6586(2) 0.4779(3) 0.0371(16) Uani 1 1 d . . .
H35A H 0.2566 0.6673 0.4405 0.045 Uiso 1 1 calc R . .
H35B H 0.0407 0.6655 0.4766 0.045 Uiso 1 1 calc R . .
C36 C 0.2307(11) 0.6141(2) 0.4848(3) 0.0350(16) Uani 1 1 d . . .
H36A H 0.1733 0.6054 0.5219 0.042 Uiso 1 1 calc R . .
H36B H 0.1427 0.6004 0.4517 0.042 Uiso 1 1 calc R . .
C37 C 0.2877(15) 0.7217(2) 0.5265(4) 0.047(2) Uani 1 1 d . . .
H37A H 0.1255 0.7268 0.5162 0.056 Uiso 1 1 calc R . .
H37B H 0.3704 0.7341 0.4958 0.056 Uiso 1 1 calc R . .
C38 C 0.3614(14) 0.7407(2) 0.5852(3) 0.0420(18) Uani 1 1 d . . .
C39 C 0.5464(18) 0.7635(3) 0.5955(4) 0.061(2) Uani 1 1 d . . .
H39 H 0.636 0.7683 0.5643 0.073 Uiso 1 1 calc R . .
C40 C 0.6108(19) 0.7803(3) 0.6505(5) 0.070(3) Uani 1 1 d . . .
H40 H 0.7434 0.7959 0.6561 0.084 Uiso 1 1 calc R . .
C41 C 0.4850(18) 0.7743(2) 0.6964(4) 0.054(2) Uani 1 1 d . . .
C42 C 0.2969(18) 0.7518(4) 0.6862(4) 0.069(3) Uani 1 1 d . . .
H42 H 0.207 0.7474 0.7175 0.082 Uiso 1 1 calc R . .
C43 C 0.2327(16) 0.7354(3) 0.6325(4) 0.064(3) Uani 1 1 d . . .
H43 H 0.0989 0.7201 0.6271 0.077 Uiso 1 1 calc R . .
I44 I 0.63667(7) 0.611576(13) 0.372590(17) 0.03301(16) Uani 1 1 d . . .
C45 C 0.7778(11) 0.6061(2) 0.2927(3) 0.0310(15) Uani 1 1 d . . .
C46 C 0.6736(12) 0.6226(2) 0.2411(3) 0.0341(15) Uani 1 1 d . . .
F47 F 0.4809(7) 0.64340(15) 0.24219(18) 0.0496(12) Uani 1 1 d . . .
C48 C 0.7666(12) 0.6200(2) 0.1893(3) 0.0326(15) Uani 1 1 d . . .
F49 F 0.6609(7) 0.63785(15) 0.14085(17) 0.0500(12) Uani 1 1 d . . .
C50 C 0.9626(12) 0.5998(2) 0.1844(3) 0.0282(14) Uani 1 1 d . . .
I51 I 1.09360(7) 0.594653(13) 0.103109(18) 0.03365(17) Uani 1 1 d . . .
C52 C 1.0683(11) 0.5831(2) 0.2356(3) 0.0292(14) Uani 1 1 d . . .
F53 F 1.2623(7) 0.56302(13) 0.23472(18) 0.0407(10) Uani 1 1 d . . .
C54 C 0.9751(11) 0.5862(2) 0.2884(3) 0.0278(14) Uani 1 1 d . . .
F55 F 1.0822(7) 0.56904(13) 0.33618(16) 0.0388(9) Uani 1 1 d . . .
C56 C -0.103(4) 0.6309(7) 0.7269(8) 0.15(4) Uiso 0.2 1 d PD A 1
H56 H -0.1953 0.6109 0.746 0.186 Uiso 0.2 1 calc PR A 1
Cl57 Cl -0.285(4) 0.6667(8) 0.6904(11) 0.146(9) Uiso 0.2 1 d PD A 1
Cl58 Cl 0.083(5) 0.6542(9) 0.7821(9) 0.161(11) Uiso 0.2 1 d PD A 1
Cl59 Cl 0.053(4) 0.6061(6) 0.6757(8) 0.108(6) Uiso 0.2 1 d PD A 1
C64 C 0.112(3) 0.6588(5) 0.6997(6) 0.14(2) Uiso 0.3 1 d PD B 2
H64 H 0.199 0.679 0.6794 0.165 Uiso 0.3 1 calc PR B 2
Cl65 Cl -0.175(2) 0.6703(4) 0.6839(6) 0.111(4) Uiso 0.3 1 d PD B 2
Cl62 Cl 0.197(3) 0.6624(5) 0.7759(6) 0.141(6) Uiso 0.3 1 d PD B 2
Cl63 Cl 0.177(3) 0.6118(5) 0.6720(8) 0.165(7) Uiso 0.3 1 d PD B 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
C1 0.163(12) 0.029(5) 0.054(6) 0.005(4) -0.017(7) -0.012(6)
C2 0.084(6) 0.028(4) 0.045(5) 0.002(3) -0.005(4) -0.013(4)
C3 0.066(6) 0.058(6) 0.060(6) 0.021(5) 0.019(5) 0.001(5)
C4 0.047(5) 0.055(5) 0.061(5) 0.018(4) 0.009(4) 0.017(4)
C5 0.044(4) 0.019(3) 0.049(4) -0.004(3) -0.001(3) -0.011(3)
C6 0.065(5) 0.034(4) 0.051(5) -0.004(3) 0.003(4) 0.006(4)
C7 0.087(7) 0.027(4) 0.060(5) -0.005(4) -0.016(5) 0.020(4)
C8 0.057(5) 0.037(4) 0.035(4) -0.003(3) -0.004(3) -0.015(4)
N9 0.038(3) 0.022(3) 0.031(3) 0.000(2) -0.003(2) -0.008(2)
C10 0.035(4) 0.035(4) 0.029(3) 0.003(3) -0.004(3) -0.007(3)
C11 0.035(4) 0.032(4) 0.033(4) 0.006(3) 0.001(3) 0.000(3)
N12 0.031(3) 0.025(3) 0.026(3) -0.001(2) 0.005(2) -0.007(2)
C13 0.025(3) 0.032(4) 0.040(4) -0.001(3) -0.005(3) -0.002(3)
C14 0.042(4) 0.028(4) 0.040(4) -0.002(3) 0.000(3) 0.001(3)
C15 0.038(4) 0.029(4) 0.036(4) -0.001(3) 0.010(3) -0.006(3)
C16 0.039(4) 0.025(3) 0.032(3) 0.001(3) 0.009(3) -0.014(3)
C17 0.039(4) 0.023(3) 0.033(4) 0.004(3) 0.003(3) 0.002(3)
C18 0.036(4) 0.022(3) 0.037(4) 0.003(3) 0.010(3) -0.003(3)
C19 0.039(4) 0.025(3) 0.030(3) -0.007(3) 0.006(3) -0.005(3)
C20 0.028(3) 0.038(4) 0.035(4) -0.005(3) 0.008(3) -0.004(3)
C21 0.030(4) 0.035(4) 0.037(4) -0.004(3) 0.007(3) -0.007(3)
N22 0.033(3) 0.034(3) 0.039(3) -0.003(3) 0.010(3) -0.003(3)
N23 0.036(3) 0.030(3) 0.032(3) 0.004(2) 0.007(2) 0.005(2)
C24 0.039(4) 0.026(4) 0.032(4) 0.002(3) 0.009(3) 0.009(3)
C25 0.032(4) 0.041(4) 0.034(4) 0.007(3) 0.004(3) 0.009(3)
C26 0.035(4) 0.039(4) 0.040(4) 0.007(3) 0.011(3) 0.011(3)
C27 0.037(4) 0.029(4) 0.028(3) 0.001(3) 0.012(3) 0.011(3)
C28 0.037(4) 0.027(3) 0.034(4) -0.002(3) 0.004(3) 0.007(3)
C29 0.034(4) 0.027(4) 0.040(4) -0.003(3) 0.013(3) 0.004(3)
C30 0.046(4) 0.033(4) 0.031(4) 0.003(3) 0.015(3) 0.013(3)
N31 0.035(3) 0.032(3) 0.031(3) 0.004(2) 0.009(2) 0.010(2)
C32 0.024(3) 0.037(4) 0.039(4) 0.003(3) 0.004(3) 0.003(3)
C33 0.034(4) 0.035(4) 0.046(4) 0.002(3) 0.002(3) 0.002(3)
N34 0.041(3) 0.024(3) 0.044(3) 0.005(2) 0.006(3) 0.013(3)
C35 0.037(4) 0.039(4) 0.036(4) 0.006(3) 0.004(3) 0.014(3)
C36 0.025(3) 0.043(4) 0.037(4) 0.003(3) 0.005(3) 0.004(3)
C37 0.059(5) 0.029(4) 0.053(5) 0.017(3) 0.005(4) 0.017(4)
C38 0.053(5) 0.033(4) 0.040(4) 0.008(3) 0.006(3) 0.013(4)
C39 0.088(7) 0.035(5) 0.064(6) 0.009(4) 0.027(5) -0.007(5)
C40 0.084(7) 0.045(6) 0.080(7) 0.010(5) 0.008(6) -0.021(5)
C41 0.085(7) 0.022(4) 0.053(5) 0.009(3) -0.002(5) -0.002(4)
C42 0.073(7) 0.090(8) 0.045(5) -0.003(5) 0.018(5) -0.008(6)
C43 0.054(5) 0.082(7) 0.055(6) -0.006(5) 0.005(4) -0.003(5)
I44 0.0340(3) 0.0377(3) 0.0285(3) 0.00117(16) 0.00844(18) 0.00090(17)
C45 0.031(4) 0.034(4) 0.029(3) -0.002(3) 0.007(3) -0.002(3)
C46 0.031(4) 0.039(4) 0.032(4) 0.003(3) 0.002(3) 0.005(3)
F47 0.037(2) 0.072(3) 0.041(2) 0.006(2) 0.0057(18) 0.023(2)
C48 0.032(4) 0.039(4) 0.026(3) -0.001(3) 0.000(3) 0.003(3)
F49 0.048(3) 0.073(3) 0.028(2) 0.013(2) -0.0017(18) 0.015(2)
C50 0.036(4) 0.027(3) 0.023(3) -0.003(2) 0.008(3) -0.006(3)
I51 0.0372(3) 0.0370(3) 0.0277(3) -0.00411(16) 0.00767(18) -0.00385(18)
C52 0.028(3) 0.028(3) 0.031(3) 0.000(3) 0.003(3) 0.001(3)
F53 0.034(2) 0.042(2) 0.047(2) -0.0001(18) 0.0087(18) 0.0110(18)
C54 0.031(3) 0.027(3) 0.025(3) 0.002(3) 0.000(3) -0.004(3)
F55 0.038(2) 0.048(3) 0.030(2) 0.0101(17) 0.0016(17) 0.0075(19)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C2 1.524(12) . ?
C1 C41 1.525(13) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C3 1.365(13) . ?
C2 C7 1.377(14) . ?
C3 C4 1.380(12) . ?
C3 H3 0.95 . ?
C4 C5 1.390(12) . ?
C4 H4 0.95 . ?
C5 C6 1.377(11) . ?
C5 C8 1.496(10) . ?
C6 C7 1.395(13) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N9 1.463(9) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
N9 C10 1.453(9) . ?
N9 C14 1.454(9) . ?
C10 C11 1.522(10) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 N12 1.462(9) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
N12 C13 1.470(9) . ?
N12 C15 1.478(8) . ?
C13 C14 1.509(9) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.517(9) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C21 1.379(10) . ?
C16 C17 1.387(10) . ?
C17 C18 1.382(10) . ?
C17 H17 0.95 . ?
C18 C19 1.396(10) . ?
C18 H18 0.95 . ?
C19 C20 1.390(10) . ?
C19 N22 1.437(9) . ?
C20 C21 1.386(10) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
N22 N23 1.245(8) . ?
N23 C24 1.439(9) . ?
C24 C25 1.380(10) . ?
C24 C29 1.387(10) . ?
C25 C26 1.387(10) . ?
C25 H25 0.95 . ?
C26 C27 1.393(10) . ?
C26 H26 0.95 . ?
C27 C28 1.393(10) . ?
C27 C30 1.514(9) . ?
C28 C29 1.377(10) . ?
C28 H28 0.95 . ?
C29 H29 0.95 . ?
C30 N31 1.462(9) . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
N31 C32 1.467(9) . ?
N31 C36 1.470(9) . ?
N31 I44 2.880(5) . ?
C32 C33 1.516(10) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
C33 N34 1.461(9) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
N34 C35 1.457(10) . ?
N34 C37 1.466(9) . ?
C35 C36 1.512(10) . ?
C35 H35A 0.99 . ?
C35 H35B 0.99 . ?
C36 H36A 0.99 . ?
C36 H36B 0.99 . ?
C37 C38 1.508(12) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C38 C39 1.348(13) . ?
C38 C43 1.401(12) . ?
C39 C40 1.393(14) . ?
C39 H39 0.95 . ?
C40 C41 1.367(14) . ?
C40 H40 0.95 . ?
C41 C42 1.357(14) . ?
C42 C43 1.365(13) . ?
C42 H42 0.95 . ?
C43 H43 0.95 . ?
I44 C45 2.095(7) . ?
C45 C54 1.369(10) . ?
C45 C46 1.393(10) . ?
C46 F47 1.351(8) . ?
C46 C48 1.361(10) . ?
C48 F49 1.357(8) . ?
C48 C50 1.371(10) . ?
C50 C52 1.390(10) . ?
C50 I51 2.095(6) . ?
I51 N12 2.982(5) 1_654 ?
C52 F53 1.346(8) . ?
C52 C54 1.383(9) . ?
C54 F55 1.339(8) . ?
C56 Cl57 1.775(5) . ?
C56 Cl58 1.776(7) . ?
C56 Cl59 1.776(7) . ?
C56 H56 1 . ?
C64 Cl63 1.762(7) . ?
C64 Cl65 1.764(7) . ?
C64 Cl62 1.766(5) . ?
C64 H64 1 . ?

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
C2 C1 C41 114.7(7) . . ?
C2 C1 H1A 108.6 . . ?
C41 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
C41 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C7 117.3(8) . . ?
C3 C2 C1 120.6(10) . . ?
C7 C2 C1 122.0(9) . . ?
C2 C3 C4 122.0(9) . . ?
C2 C3 H3 119 . . ?
C4 C3 H3 119 . . ?
C3 C4 C5 121.0(8) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 117.4(7) . . ?
C6 C5 C8 123.1(8) . . ?
C4 C5 C8 119.4(7) . . ?
C5 C6 C7 120.7(8) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 121.6(8) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N9 C8 C5 113.1(6) . . ?
N9 C8 H8A 109 . . ?
C5 C8 H8A 109 . . ?
N9 C8 H8B 109 . . ?
C5 C8 H8B 109 . . ?
H8A C8 H8B 107.8 . . ?
C10 N9 C14 108.8(5) . . ?
C10 N9 C8 111.0(5) . . ?
C14 N9 C8 110.6(6) . . ?
N9 C10 C11 109.6(5) . . ?
N9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N12 C11 C10 109.8(6) . . ?
N12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 N12 C13 109.1(5) . . ?
C11 N12 C15 114.2(5) . . ?
C13 N12 C15 112.9(5) . . ?
N12 C13 C14 111.5(6) . . ?
N12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108 . . ?
N9 C14 C13 110.7(6) . . ?
N9 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N9 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N12 C15 C16 114.8(5) . . ?
N12 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
N12 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C21 C16 C17 118.7(6) . . ?
C21 C16 C15 118.9(6) . . ?
C17 C16 C15 122.0(6) . . ?
C18 C17 C16 122.0(7) . . ?
C18 C17 H17 119 . . ?
C16 C17 H17 119 . . ?
C17 C18 C19 118.2(6) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 C18 120.2(6) . . ?
C20 C19 N22 114.4(6) . . ?
C18 C19 N22 125.1(6) . . ?
C21 C20 C19 119.8(7) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C16 C21 C20 120.6(7) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
N23 N22 C19 112.3(6) . . ?
N22 N23 C24 113.5(6) . . ?
C25 C24 C29 120.3(6) . . ?
C25 C24 N23 114.2(6) . . ?
C29 C24 N23 125.0(6) . . ?
C24 C25 C26 119.3(7) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 121.6(7) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C28 C27 C26 117.4(6) . . ?
C28 C27 C30 123.6(7) . . ?
C26 C27 C30 119.0(7) . . ?
C29 C28 C27 121.8(7) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C24 119.4(6) . . ?
C28 C29 H29 120.3 . . ?
C24 C29 H29 120.3 . . ?
N31 C30 C27 115.0(5) . . ?
N31 C30 H30A 108.5 . . ?
C27 C30 H30A 108.5 . . ?
N31 C30 H30B 108.5 . . ?
C27 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C30 N31 C32 112.8(6) . . ?
C30 N31 C36 113.9(6) . . ?
C32 N31 C36 110.0(5) . . ?
C30 N31 I44 93.2(4) . . ?
C32 N31 I44 113.2(4) . . ?
C36 N31 I44 113.0(4) . . ?
N31 C32 C33 111.2(6) . . ?
N31 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
N31 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108 . . ?
N34 C33 C32 109.9(6) . . ?
N34 C33 H33A 109.7 . . ?
C32 C33 H33A 109.7 . . ?
N34 C33 H33B 109.7 . . ?
C32 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C35 N34 C33 108.7(6) . . ?
C35 N34 C37 112.4(6) . . ?
C33 N34 C37 111.6(6) . . ?
N34 C35 C36 109.7(6) . . ?
N34 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
N34 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
N31 C36 C35 110.3(6) . . ?
N31 C36 H36A 109.6 . . ?
C35 C36 H36A 109.6 . . ?
N31 C36 H36B 109.6 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
N34 C37 C38 112.1(6) . . ?
N34 C37 H37A 109.2 . . ?
C38 C37 H37A 109.2 . . ?
N34 C37 H37B 109.2 . . ?
C38 C37 H37B 109.2 . . ?
H37A C37 H37B 107.9 . . ?
C39 C38 C43 116.4(8) . . ?
C39 C38 C37 123.9(8) . . ?
C43 C38 C37 119.7(8) . . ?
C38 C39 C40 122.3(9) . . ?
C38 C39 H39 118.8 . . ?
C40 C39 H39 118.8 . . ?
C41 C40 C39 120.6(9) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C42 C41 C40 117.6(9) . . ?
C42 C41 C1 122.2(10) . . ?
C40 C41 C1 120.2(10) . . ?
C41 C42 C43 122.2(9) . . ?
C41 C42 H42 118.9 . . ?
C43 C42 H42 118.9 . . ?
C42 C43 C38 121.0(10) . . ?
C42 C43 H43 119.5 . . ?
C38 C43 H43 119.5 . . ?
C45 I44 N31 168.9(2) . . ?
C54 C45 C46 116.7(6) . . ?
C54 C45 I44 122.3(5) . . ?
C46 C45 I44 121.0(5) . . ?
F47 C46 C48 118.4(6) . . ?
F47 C46 C45 120.0(6) . . ?
C48 C46 C45 121.5(7) . . ?
F49 C48 C46 118.8(6) . . ?
F49 C48 C50 118.9(6) . . ?
C46 C48 C50 122.2(6) . . ?
C48 C50 C52 116.8(6) . . ?
C48 C50 I51 121.0(5) . . ?
C52 C50 I51 122.2(5) . . ?
C50 I51 N12 172.5(2) . 1_654 ?
F53 C52 C54 118.5(6) . . ?
F53 C52 C50 120.6(6) . . ?
C54 C52 C50 120.9(6) . . ?
F55 C54 C45 119.7(6) . . ?
F55 C54 C52 118.4(6) . . ?
C45 C54 C52 121.9(6) . . ?
Cl57 C56 Cl58 110.1(6) . . ?
Cl57 C56 Cl59 110.4(6) . . ?
Cl58 C56 Cl59 109.9(7) . . ?
Cl57 C56 H56 108.8 . . ?
Cl58 C56 H56 108.8 . . ?
Cl59 C56 H56 108.8 . . ?
Cl63 C64 Cl65 111.8(7) . . ?
Cl63 C64 Cl62 111.3(6) . . ?
Cl65 C64 Cl62 111.3(6) . . ?
Cl63 C64 H64 107.4 . . ?
Cl65 C64 H64 107.4 . . ?
Cl62 C64 H64 107.4 . . ?

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
C41 C1 C2 C3 72.9(14) . . . . ?
C41 C1 C2 C7 -109.8(11) . . . . ?
C7 C2 C3 C4 -1.1(15) . . . . ?
C1 C2 C3 C4 176.4(9) . . . . ?
C2 C3 C4 C5 0.7(16) . . . . ?
C3 C4 C5 C6 0.5(13) . . . . ?
C3 C4 C5 C8 -175.9(8) . . . . ?
C4 C5 C6 C7 -1.3(12) . . . . ?
C8 C5 C6 C7 175.0(8) . . . . ?
C3 C2 C7 C6 0.2(14) . . . . ?
C1 C2 C7 C6 -177.2(9) . . . . ?
C5 C6 C7 C2 1.0(14) . . . . ?
C6 C5 C8 N9 107.0(9) . . . . ?
C4 C5 C8 N9 -76.8(10) . . . . ?
C5 C8 N9 C10 160.4(6) . . . . ?
C5 C8 N9 C14 -78.8(8) . . . . ?
C14 N9 C10 C11 61.2(7) . . . . ?
C8 N9 C10 C11 -177.0(6) . . . . ?
N9 C10 C11 N12 -61.7(7) . . . . ?
C10 C11 N12 C13 57.9(7) . . . . ?
C10 C11 N12 C15 -174.7(5) . . . . ?
C11 N12 C13 C14 -56.0(7) . . . . ?
C15 N12 C13 C14 175.8(6) . . . . ?
C10 N9 C14 C13 -58.9(7) . . . . ?
C8 N9 C14 C13 179.0(6) . . . . ?
N12 C13 C14 N9 57.0(8) . . . . ?
C11 N12 C15 C16 -74.8(8) . . . . ?
C13 N12 C15 C16 50.6(8) . . . . ?
N12 C15 C16 C21 -92.3(8) . . . . ?
N12 C15 C16 C17 80.1(8) . . . . ?
C21 C16 C17 C18 5.0(10) . . . . ?
C15 C16 C17 C18 -167.4(6) . . . . ?
C16 C17 C18 C19 0.0(10) . . . . ?
C17 C18 C19 C20 -6.5(10) . . . . ?
C17 C18 C19 N22 167.8(6) . . . . ?
C18 C19 C20 C21 7.8(10) . . . . ?
N22 C19 C20 C21 -167.0(6) . . . . ?
C17 C16 C21 C20 -3.7(10) . . . . ?
C15 C16 C21 C20 169.0(6) . . . . ?
C19 C20 C21 C16 -2.6(11) . . . . ?
C20 C19 N22 N23 158.4(6) . . . . ?
C18 C19 N22 N23 -16.2(10) . . . . ?
C19 N22 N23 C24 -170.4(6) . . . . ?
N22 N23 C24 C25 163.4(6) . . . . ?
N22 N23 C24 C29 -8.2(10) . . . . ?
C29 C24 C25 C26 3.6(11) . . . . ?
N23 C24 C25 C26 -168.4(6) . . . . ?
C24 C25 C26 C27 0.0(11) . . . . ?
C25 C26 C27 C28 -3.6(10) . . . . ?
C25 C26 C27 C30 173.1(7) . . . . ?
C26 C27 C28 C29 3.7(10) . . . . ?
C30 C27 C28 C29 -172.9(6) . . . . ?
C27 C28 C29 C24 -0.2(10) . . . . ?
C25 C24 C29 C28 -3.6(10) . . . . ?
N23 C24 C29 C28 167.6(6) . . . . ?
C28 C27 C30 N31 87.6(9) . . . . ?
C26 C27 C30 N31 -88.9(8) . . . . ?
C27 C30 N31 C32 55.4(8) . . . . ?
C27 C30 N31 C36 -70.9(8) . . . . ?
C27 C30 N31 I44 172.3(6) . . . . ?
C30 N31 C32 C33 176.5(6) . . . . ?
C36 N31 C32 C33 -55.2(7) . . . . ?
I44 N31 C32 C33 72.2(6) . . . . ?
N31 C32 C33 N34 57.7(8) . . . . ?
C32 C33 N34 C35 -60.5(7) . . . . ?
C32 C33 N34 C37 175.0(6) . . . . ?
C33 N34 C35 C36 62.1(7) . . . . ?
C37 N34 C35 C36 -174.0(6) . . . . ?
C30 N31 C36 C35 -176.0(6) . . . . ?
C32 N31 C36 C35 56.3(7) . . . . ?
I44 N31 C36 C35 -71.3(6) . . . . ?
N34 C35 C36 N31 -60.4(8) . . . . ?
C35 N34 C37 C38 163.5(7) . . . . ?
C33 N34 C37 C38 -74.2(8) . . . . ?
N34 C37 C38 C39 106.6(9) . . . . ?
N34 C37 C38 C43 -74.1(10) . . . . ?
C43 C38 C39 C40 1.5(14) . . . . ?
C37 C38 C39 C40 -179.3(8) . . . . ?
C38 C39 C40 C41 -0.7(16) . . . . ?
C39 C40 C41 C42 -0.2(15) . . . . ?
C39 C40 C41 C1 -178.8(9) . . . . ?
C2 C1 C41 C42 45.2(16) . . . . ?
C2 C1 C41 C40 -136.2(11) . . . . ?
C40 C41 C42 C43 0.1(16) . . . . ?
C1 C41 C42 C43 178.7(10) . . . . ?
C41 C42 C43 C38 0.8(17) . . . . ?
C39 C38 C43 C42 -1.5(14) . . . . ?
C37 C38 C43 C42 179.2(9) . . . . ?
C30 N31 I44 C45 -8.1(14) . . . . ?
C32 N31 I44 C45 108.4(12) . . . . ?
C36 N31 I44 C45 -125.7(11) . . . . ?
N31 I44 C45 C54 -40.9(15) . . . . ?
N31 I44 C45 C46 139.1(10) . . . . ?
C54 C45 C46 F47 -178.6(7) . . . . ?
I44 C45 C46 F47 1.4(10) . . . . ?
C54 C45 C46 C48 -1.5(11) . . . . ?
I44 C45 C46 C48 178.4(6) . . . . ?
F47 C46 C48 F49 -0.8(11) . . . . ?
C45 C46 C48 F49 -178.0(7) . . . . ?
F47 C46 C48 C50 179.5(7) . . . . ?
C45 C46 C48 C50 2.4(12) . . . . ?
F49 C48 C50 C52 178.0(6) . . . . ?
C46 C48 C50 C52 -2.4(11) . . . . ?
F49 C48 C50 I51 -2.0(9) . . . . ?
C46 C48 C50 I51 177.6(6) . . . . ?
C48 C50 C52 F53 -179.6(6) . . . . ?
I51 C50 C52 F53 0.4(9) . . . . ?
C48 C50 C52 C54 1.6(10) . . . . ?
I51 C50 C52 C54 -178.4(5) . . . . ?
C46 C45 C54 F55 -179.0(6) . . . . ?
I44 C45 C54 F55 1.0(9) . . . . ?
C46 C45 C54 C52 0.8(10) . . . . ?
I44 C45 C54 C52 -179.2(5) . . . . ?
F53 C52 C54 F55 0.1(9) . . . . ?
C50 C52 C54 F55 178.9(6) . . . . ?
F53 C52 C54 C45 -179.7(6) . . . . ?
C50 C52 C54 C45 -0.9(11) . . . . ?