# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_db061
_database_code_depnum_ccdc_archive 'CCDC 907312'
#TrackingRef 'web_deposit_cif_file_0_DavidBryce_1351030412.db061_compound 2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 Cl F4 I2 P'
_chemical_formula_weight         696.73
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   14.4599(2)
_cell_length_b                   14.9417(2)
_cell_length_c                   15.0638(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.6830(10)
_cell_angle_gamma                90.00
_cell_volume                     2882.06(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      28.28
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_absorpt_coefficient_mu    2.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_T_max  0.7332
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_special_details           
;
Data collection is performed with three batch runs at phi = 0.00 deg
(650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg
(650 frames).
Frame width = 0.30 deg in omega.
Data is merged, corrected for decay (if any), and treated with multi-scan
absorption corrections (if required). All symmetry-equivalent reflections
are merged for centrosymmetric data.
Friedel pairs are not merged for noncentrosymmetric data.
;
_diffrn_ambient_temperature      200(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62401
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0101
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.31
_reflns_number_total             7118
_reflns_number_gt                6216
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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^)+(0.0212P)^2^+2.0621P] 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         7118
_refine_ls_number_parameters     298
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0537
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.023
_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 0.327926(10) 0.724664(10) 0.049933(10) 0.04449(4) Uani 1 1 d . . .
I2 I 0.869825(10) 0.787360(10) 0.321932(11) 0.04675(5) Uani 1 1 d . . .
F1 F 0.48891(11) 0.71027(11) 0.28310(10) 0.0650(4) Uani 1 1 d . . .
F2 F 0.69541(11) 0.72672(11) 0.38541(10) 0.0650(4) Uani 1 1 d . . .
F3 F 0.70623(11) 0.81460(13) 0.08972(11) 0.0706(4) Uani 1 1 d . . .
F4 F 0.50088(11) 0.78987(12) -0.01394(10) 0.0669(4) Uani 1 1 d . . .
Cl1 Cl 0.09772(4) 0.82375(5) 0.43795(4) 0.05618(14) Uani 1 1 d . . .
P1 P 0.09380(5) 0.61918(4) 0.20055(4) 0.04805(13) Uani 1 1 d . . .
C1 C 0.48896(15) 0.74707(14) 0.13108(15) 0.0400(4) Uani 1 1 d . . .
C2 C 0.54190(16) 0.73328(15) 0.23321(16) 0.0439(4) Uani 1 1 d . . .
C3 C 0.64892(17) 0.74273(15) 0.28666(15) 0.0444(4) Uani 1 1 d . . .
C4 C 0.70744(15) 0.76918(14) 0.23983(16) 0.0423(4) Uani 1 1 d . . .
C5 C 0.65407(16) 0.78614(15) 0.13868(16) 0.0458(5) Uani 1 1 d . . .
C6 C 0.54781(17) 0.77418(15) 0.08521(15) 0.0460(5) Uani 1 1 d . . .
C7 C 0.19796(18) 0.56132(16) 0.19065(17) 0.0494(5) Uani 1 1 d . . .
H7A H 0.1753 0.4988 0.1706 0.059 Uiso 1 1 calc R . .
H7B H 0.2068 0.5892 0.1355 0.059 Uiso 1 1 calc R . .
C8 C 0.30558(19) 0.55876(17) 0.28392(18) 0.0548(5) Uani 1 1 d . . .
H8A H 0.3306 0.6207 0.3045 0.066 Uiso 1 1 calc R . .
H8B H 0.2989 0.5298 0.3398 0.066 Uiso 1 1 calc R . .
C9 C 0.3850(2) 0.50803(17) 0.26416(19) 0.0578(6) Uani 1 1 d . . .
H9A H 0.3938 0.5388 0.2104 0.069 Uiso 1 1 calc R . .
H9B H 0.3580 0.4471 0.2401 0.069 Uiso 1 1 calc R . .
C10 C 0.4912(2) 0.5006(2) 0.3572(2) 0.0740(8) Uani 1 1 d . . .
H10A H 0.5393 0.4671 0.3406 0.111 Uiso 1 1 calc R . .
H10B H 0.4832 0.4694 0.4104 0.111 Uiso 1 1 calc R . .
H10C H 0.5193 0.5607 0.3803 0.111 Uiso 1 1 calc R . .
C11 C 0.0982(2) 0.73753(16) 0.1824(2) 0.0623(7) Uani 1 1 d . . .
H11A H 0.0754 0.7489 0.1104 0.075 Uiso 1 1 calc R . .
H11B H 0.0475 0.7672 0.1997 0.075 Uiso 1 1 calc R . .
C12 C 0.2047(2) 0.78041(16) 0.24333(19) 0.0567(6) Uani 1 1 d . B .
H12A H 0.2292 0.7672 0.3152 0.068 Uiso 1 1 calc R . .
H12B H 0.2549 0.7531 0.2237 0.068 Uiso 1 1 calc R . .
C13 C 0.2044(3) 0.8803(2) 0.2297(3) 0.0824(9) Uani 1 1 d DU . .
H13A H 0.1604 0.9091 0.2560 0.099 Uiso 0.50 1 calc PR A 1
H13B H 0.1747 0.8947 0.1575 0.099 Uiso 0.50 1 calc PR A 1
H13C H 0.1704 0.8931 0.1569 0.099 Uiso 0.50 1 calc PR A 2
H13D H 0.1606 0.9075 0.2571 0.099 Uiso 0.50 1 calc PR A 2
C14 C 0.3160(16) 0.916(3) 0.286(3) 0.094(5) Uani 0.50 1 d PDU B 1
H14A H 0.3158 0.9808 0.2775 0.141 Uiso 0.50 1 calc PR B 1
H14B H 0.3589 0.8880 0.2584 0.141 Uiso 0.50 1 calc PR B 1
H14C H 0.3451 0.9011 0.3571 0.141 Uiso 0.50 1 calc PR B 1
C14' C 0.3100(16) 0.926(3) 0.278(3) 0.108(8) Uani 0.50 1 d PDU B 2
H14D H 0.3005 0.9907 0.2647 0.161 Uiso 0.50 1 calc PR B 2
H14E H 0.3535 0.9021 0.2494 0.161 Uiso 0.50 1 calc PR B 2
H14F H 0.3441 0.9157 0.3503 0.161 Uiso 0.50 1 calc PR B 2
C15 C -0.02613(18) 0.57460(17) 0.10401(17) 0.0520(5) Uani 1 1 d . . .
H15A H -0.0286 0.5871 0.0384 0.062 Uiso 1 1 calc R . .
H15B H -0.0246 0.5088 0.1120 0.062 Uiso 1 1 calc R . .
C16 C -0.12697(19) 0.60977(18) 0.10086(18) 0.0574(6) Uani 1 1 d . . .
H16A H -0.1244 0.6007 0.1671 0.069 Uiso 1 1 calc R . .
H16B H -0.1332 0.6748 0.0866 0.069 Uiso 1 1 calc R . .
C17 C -0.2215(2) 0.56187(19) 0.0210(2) 0.0637(6) Uani 1 1 d . . .
H17A H -0.2238 0.5721 -0.0449 0.076 Uiso 1 1 calc R . .
H17B H -0.2130 0.4968 0.0345 0.076 Uiso 1 1 calc R . .
C18 C -0.3249(2) 0.5914(2) 0.0148(3) 0.0780(8) Uani 1 1 d . . .
H18A H -0.3819 0.5568 -0.0372 0.117 Uiso 1 1 calc R . .
H18B H -0.3357 0.6552 -0.0018 0.117 Uiso 1 1 calc R . .
H18C H -0.3238 0.5811 0.0796 0.117 Uiso 1 1 calc R . .
C19 C 0.1027(2) 0.59996(18) 0.32187(17) 0.0587(6) Uani 1 1 d . D .
H19A H 0.1711 0.6223 0.3735 0.070 Uiso 1 1 calc R . .
H19B H 0.0478 0.6354 0.3274 0.070 Uiso 1 1 calc R . .
C20 C 0.0913(2) 0.5032(2) 0.3442(2) 0.0700(7) Uani 1 1 d U . .
H20A H 0.1398 0.4639 0.3325 0.084 Uiso 0.50 1 calc PR C 1
H20B H 0.0189 0.4816 0.3038 0.084 Uiso 0.50 1 calc PR C 1
H20C H 0.0219 0.4838 0.2916 0.084 Uiso 0.50 1 calc PR C 2
H20D H 0.1435 0.4694 0.3324 0.084 Uiso 0.50 1 calc PR C 2
C21 C 0.1223(8) 0.5090(5) 0.4611(7) 0.0676(19) Uani 0.50 1 d PU D 1
H21A H 0.1950 0.5304 0.5003 0.081 Uiso 0.50 1 calc PR D 1
H21B H 0.0752 0.5508 0.4717 0.081 Uiso 0.50 1 calc PR D 1
C22 C 0.1113(6) 0.4150(4) 0.4935(5) 0.0787(17) Uani 0.50 1 d PU D 1
H22A H 0.1280 0.4156 0.5645 0.118 Uiso 0.50 1 calc PR D 1
H22B H 0.1594 0.3747 0.4840 0.118 Uiso 0.50 1 calc PR D 1
H22C H 0.0394 0.3942 0.4531 0.118 Uiso 0.50 1 calc PR D 1
C21' C 0.1001(7) 0.4691(7) 0.4409(7) 0.077(2) Uani 0.50 1 d PU D 2
H21C H 0.0508 0.5018 0.4579 0.092 Uiso 0.50 1 calc PR D 2
H21D H 0.0821 0.4047 0.4347 0.092 Uiso 0.50 1 calc PR D 2
C22' C 0.2082(7) 0.4824(5) 0.5208(5) 0.098(2) Uani 0.50 1 d PU D 2
H22D H 0.2133 0.4633 0.5852 0.147 Uiso 0.50 1 calc PR D 2
H22E H 0.2267 0.5458 0.5244 0.147 Uiso 0.50 1 calc PR D 2
H22F H 0.2561 0.4468 0.5059 0.147 Uiso 0.50 1 calc PR D 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
I1 0.03212(6) 0.05887(9) 0.03825(7) 0.00357(6) 0.01278(5) -0.00060(5)
I2 0.03274(7) 0.05306(8) 0.04831(8) -0.01032(6) 0.01365(6) -0.00195(5)
F1 0.0484(7) 0.1041(12) 0.0431(7) 0.0104(7) 0.0217(6) -0.0157(7)
F2 0.0500(8) 0.0957(12) 0.0359(7) 0.0105(7) 0.0086(6) -0.0075(7)
F3 0.0507(8) 0.1166(13) 0.0514(8) -0.0019(8) 0.0296(7) -0.0228(8)
F4 0.0493(7) 0.1118(13) 0.0347(7) 0.0096(7) 0.0153(6) -0.0121(7)
Cl1 0.0303(2) 0.0721(4) 0.0559(3) -0.0142(3) 0.0114(2) -0.0021(2)
P1 0.0575(3) 0.0464(3) 0.0410(3) -0.0038(2) 0.0236(3) 0.0006(2)
C1 0.0324(9) 0.0479(11) 0.0346(9) -0.0006(8) 0.0113(7) -0.0018(8)
C2 0.0402(10) 0.0523(12) 0.0396(10) 0.0020(9) 0.0189(8) -0.0051(8)
C3 0.0421(10) 0.0502(12) 0.0347(10) 0.0007(8) 0.0126(8) -0.0025(9)
C4 0.0305(9) 0.0484(11) 0.0456(11) -0.0067(9) 0.0155(8) -0.0036(8)
C5 0.0399(10) 0.0583(13) 0.0426(11) -0.0046(9) 0.0221(9) -0.0079(9)
C6 0.0422(10) 0.0595(13) 0.0319(9) 0.0018(9) 0.0134(8) -0.0031(9)
C7 0.0600(13) 0.0481(12) 0.0461(11) -0.0020(9) 0.0296(10) -0.0010(10)
C8 0.0610(14) 0.0554(13) 0.0515(13) -0.0034(10) 0.0291(11) -0.0002(11)
C9 0.0648(15) 0.0496(13) 0.0613(14) -0.0007(11) 0.0313(12) 0.0043(11)
C10 0.0705(18) 0.0647(17) 0.081(2) 0.0028(15) 0.0307(16) 0.0139(14)
C11 0.0725(17) 0.0474(13) 0.0581(15) -0.0021(11) 0.0229(13) 0.0030(12)
C12 0.0752(16) 0.0496(13) 0.0515(13) -0.0047(10) 0.0346(13) -0.0050(11)
C13 0.105(2) 0.0547(16) 0.091(2) -0.0027(15) 0.048(2) -0.0103(16)
C14 0.142(10) 0.061(7) 0.101(9) -0.019(8) 0.074(9) -0.040(8)
C14' 0.127(10) 0.080(13) 0.109(12) -0.006(8) 0.048(9) -0.034(8)
C15 0.0585(13) 0.0537(13) 0.0440(11) -0.0064(10) 0.0239(10) -0.0005(10)
C16 0.0618(14) 0.0596(14) 0.0505(13) -0.0090(11) 0.0258(11) 0.0021(11)
C17 0.0579(14) 0.0648(16) 0.0656(16) -0.0110(13) 0.0263(13) 0.0021(12)
C18 0.0666(17) 0.080(2) 0.091(2) -0.0048(17) 0.0395(16) 0.0025(15)
C19 0.0640(14) 0.0728(16) 0.0425(12) -0.0030(11) 0.0274(11) 0.0102(12)
C20 0.0668(16) 0.092(2) 0.0609(15) 0.0210(14) 0.0378(13) 0.0100(14)
C21 0.082(5) 0.072(5) 0.055(4) 0.009(3) 0.038(3) -0.002(4)
C22 0.103(5) 0.070(4) 0.082(4) 0.030(3) 0.060(4) 0.016(3)
C21' 0.086(5) 0.094(6) 0.065(4) 0.008(4) 0.047(4) 0.004(4)
C22' 0.135(6) 0.082(4) 0.056(3) 0.003(3) 0.027(4) 0.016(4)
_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 C1 2.0937(19) . ?
I2 C4 2.1021(19) . ?
F1 C2 1.344(2) . ?
F2 C3 1.339(2) . ?
F3 C5 1.346(2) . ?
F4 C6 1.343(2) . ?
P1 C11 1.795(3) . ?
P1 C15 1.795(2) . ?
P1 C19 1.795(2) . ?
P1 C7 1.802(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.374(3) . ?
C5 C6 1.375(3) . ?
C7 C8 1.538(3) . ?
C8 C9 1.516(3) . ?
C9 C10 1.528(4) . ?
C11 C12 1.520(4) . ?
C12 C13 1.506(4) . ?
C13 C14' 1.516(12) . ?
C13 C14 1.527(12) . ?
C15 C16 1.530(3) . ?
C16 C17 1.517(3) . ?
C17 C18 1.520(4) . ?
C19 C20 1.511(4) . ?
C20 C21' 1.491(9) . ?
C20 C21 1.605(9) . ?
C21 C22 1.518(9) . ?
C21' C22' 1.477(11) . ?
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
C11 P1 C15 109.36(12) . . ?
C11 P1 C19 108.79(13) . . ?
C15 P1 C19 110.54(12) . . ?
C11 P1 C7 111.70(12) . . ?
C15 P1 C7 106.56(11) . . ?
C19 P1 C7 109.89(11) . . ?
C2 C1 C6 116.73(18) . . ?
C2 C1 I1 121.19(15) . . ?
C6 C1 I1 122.06(14) . . ?
F1 C2 C1 119.81(18) . . ?
F1 C2 C3 118.43(19) . . ?
C1 C2 C3 121.76(19) . . ?
F2 C3 C2 118.55(19) . . ?
F2 C3 C4 120.38(19) . . ?
C2 C3 C4 121.06(19) . . ?
C5 C4 C3 117.08(18) . . ?
C5 C4 I2 121.80(15) . . ?
C3 C4 I2 121.07(15) . . ?
F3 C5 C4 119.79(19) . . ?
F3 C5 C6 118.57(19) . . ?
C4 C5 C6 121.63(19) . . ?
F4 C6 C5 118.58(19) . . ?
F4 C6 C1 119.76(19) . . ?
C5 C6 C1 121.66(19) . . ?
C8 C7 P1 117.79(16) . . ?
C9 C8 C7 111.72(19) . . ?
C8 C9 C10 112.7(2) . . ?
C12 C11 P1 114.89(18) . . ?
C13 C12 C11 113.4(2) . . ?
C14' C13 C12 116.4(18) . . ?
C14' C13 C14 7(3) . . ?
C12 C13 C14 109.5(17) . . ?
C16 C15 P1 116.47(16) . . ?
C17 C16 C15 110.9(2) . . ?
C18 C17 C16 114.2(2) . . ?
C20 C19 P1 114.61(18) . . ?
C21' C20 C19 125.1(4) . . ?
C21' C20 C21 24.9(4) . . ?
C19 C20 C21 100.9(4) . . ?
C22 C21 C20 106.6(6) . . ?
C22' C21' C20 109.2(7) . . ?
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 F1 177.4(2) . . . . ?
I1 C1 C2 F1 -4.1(3) . . . . ?
C6 C1 C2 C3 -2.4(3) . . . . ?
I1 C1 C2 C3 176.14(17) . . . . ?
F1 C2 C3 F2 1.4(3) . . . . ?
C1 C2 C3 F2 -178.8(2) . . . . ?
F1 C2 C3 C4 -177.9(2) . . . . ?
C1 C2 C3 C4 1.9(4) . . . . ?
F2 C3 C4 C5 -178.7(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
F2 C3 C4 I2 -1.2(3) . . . . ?
C2 C3 C4 I2 178.12(17) . . . . ?
C3 C4 C5 F3 178.0(2) . . . . ?
I2 C4 C5 F3 0.5(3) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
I2 C4 C5 C6 -179.98(17) . . . . ?
F3 C5 C6 F4 1.2(3) . . . . ?
C4 C5 C6 F4 -178.4(2) . . . . ?
F3 C5 C6 C1 -178.5(2) . . . . ?
C4 C5 C6 C1 2.0(4) . . . . ?
C2 C1 C6 F4 -179.2(2) . . . . ?
I1 C1 C6 F4 2.3(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
I1 C1 C6 C5 -178.01(17) . . . . ?
C11 P1 C7 C8 82.9(2) . . . . ?
C15 P1 C7 C8 -157.70(18) . . . . ?
C19 P1 C7 C8 -37.9(2) . . . . ?
P1 C7 C8 C9 -179.94(17) . . . . ?
C7 C8 C9 C10 -177.2(2) . . . . ?
C15 P1 C11 C12 -166.56(18) . . . . ?
C19 P1 C11 C12 72.6(2) . . . . ?
C7 P1 C11 C12 -48.9(2) . . . . ?
P1 C11 C12 C13 -177.4(2) . . . . ?
C11 C12 C13 C14' -172.6(16) . . . . ?
C11 C12 C13 C14 -174.7(13) . . . . ?
C11 P1 C15 C16 -62.5(2) . . . . ?
C19 P1 C15 C16 57.3(2) . . . . ?
C7 P1 C15 C16 176.62(18) . . . . ?
P1 C15 C16 C17 -175.91(19) . . . . ?
C15 C16 C17 C18 178.5(2) . . . . ?
C11 P1 C19 C20 175.4(2) . . . . ?
C15 P1 C19 C20 55.3(2) . . . . ?
C7 P1 C19 C20 -62.0(2) . . . . ?
P1 C19 C20 C21' 177.3(5) . . . . ?
P1 C19 C20 C21 170.8(4) . . . . ?
C21' C20 C21 C22 11.3(12) . . . . ?
C19 C20 C21 C22 178.5(5) . . . . ?
C19 C20 C21' C22' -65.7(8) . . . . ?
C21 C20 C21' C22' -50.3(13) . . . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.057


data_db067a
_database_code_depnum_ccdc_archive 'CCDC 907313'
#TrackingRef 'web_deposit_cif_file_1_DavidBryce_1351030412.db067_3_(nBu4NBr)(para-DITFB)_revised.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 Br F4 I2 N'
_chemical_formula_weight         724.23
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'
Br Br -0.2901 2.4595 '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           Orthorhombic
_symmetry_space_group_name_H-M   Pccn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
_cell_length_a                   48.3095(10)
_cell_length_b                   8.7022(2)
_cell_length_c                   13.6477(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5737.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9406
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.19
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2816
_exptl_absorpt_coefficient_mu    3.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5619
_exptl_absorpt_correction_T_max  0.6916
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      200(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58424
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.26
_reflns_number_total             7074
_reflns_number_gt                6176
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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^)+(0.0703P)^2^+56.8396P] 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         7074
_refine_ls_number_parameters     319
_refine_ls_number_restraints     246
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1889
_refine_ls_wR_factor_gt          0.1845
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.118
_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
I1 I 0.066001(9) 0.52952(6) 0.39114(4) 0.03927(15) Uani 1 1 d . . .
I2 I 0.185224(13) 0.43124(9) 0.28479(6) 0.0680(2) Uani 1 1 d . . .
F1 F 0.03693(9) 0.2690(5) 0.5250(4) 0.0493(11) Uani 1 1 d U . .
C2 C 0.01888(15) 0.3857(8) 0.5114(5) 0.0356(14) Uani 1 1 d U . .
C3 C 0.00688(16) 0.6269(8) 0.4456(6) 0.0397(15) Uani 1 1 d U . .
F2 F 0.01296(10) 0.7521(5) 0.3937(4) 0.0516(11) Uani 1 1 d U . .
F3 F 0.2174(5) 0.237(5) 0.440(2) 0.209(13) Uani 0.50 1 d PU A 1
C5 C 0.2323(6) 0.226(5) 0.352(3) 0.113(9) Uani 0.50 1 d PDU . 1
C6 C 0.2435(5) 0.323(5) 0.201(2) 0.107(6) Uani 0.50 1 d PDU . 1
F4 F 0.2363(6) 0.425(5) 0.135(2) 0.31(2) Uani 0.50 1 d PDU B 1
F3' F 0.2327(5) 0.393(4) 0.4472(19) 0.209(15) Uani 0.50 1 d PU . 2
C5' C 0.2404(6) 0.320(4) 0.365(2) 0.102(9) Uani 0.50 1 d PDU . 2
C6' C 0.2322(5) 0.257(5) 0.211(2) 0.107(6) Uani 0.50 1 d PDU . 2
F4' F 0.2203(5) 0.270(4) 0.1224(16) 0.199(14) Uani 0.50 1 d PDU C 2
N1 N 0.11636(14) 0.0429(7) 0.4708(5) 0.0412(14) Uani 1 1 d . . .
Br1 Br 0.124356(16) 0.58594(12) 0.29182(7) 0.0527(2) Uani 1 1 d . . .
C1 C 0.02651(14) 0.5114(8) 0.4563(5) 0.0335(13) Uani 1 1 d U . .
C4 C 0.2242(2) 0.3246(15) 0.2824(9) 0.073(3) Uani 1 1 d DU . .
C7 C 0.10095(17) -0.0878(9) 0.5217(6) 0.0427(16) Uani 1 1 d U . .
H7A H 0.0992 -0.1745 0.4752 0.051 Uiso 1 1 calc R . .
H7B H 0.1122 -0.1238 0.5777 0.051 Uiso 1 1 calc R . .
C8 C 0.07270(18) -0.0463(10) 0.5584(7) 0.0497(19) Uani 1 1 d U . .
H8A H 0.0607 -0.0204 0.5020 0.060 Uiso 1 1 calc R . .
H8B H 0.0741 0.0459 0.6007 0.060 Uiso 1 1 calc R . .
C9 C 0.05958(19) -0.1764(11) 0.6163(6) 0.0519(19) Uani 1 1 d U . .
H9A H 0.0706 -0.1945 0.6764 0.062 Uiso 1 1 calc R . .
H9B H 0.0602 -0.2715 0.5766 0.062 Uiso 1 1 calc R . .
C10 C 0.0298(2) -0.1437(15) 0.6450(7) 0.067(3) Uani 1 1 d U . .
H10A H 0.0223 -0.2316 0.6813 0.100 Uiso 1 1 calc R . .
H10B H 0.0187 -0.1266 0.5858 0.100 Uiso 1 1 calc R . .
H10C H 0.0291 -0.0518 0.6864 0.100 Uiso 1 1 calc R . .
C11 C 0.09892(18) 0.1114(9) 0.3889(6) 0.0459(17) Uani 1 1 d U . .
H11A H 0.0822 0.1586 0.4185 0.055 Uiso 1 1 calc R . .
H11B H 0.1097 0.1948 0.3576 0.055 Uiso 1 1 calc R . .
C12 C 0.0897(2) 0.0009(11) 0.3101(6) 0.052(2) Uani 1 1 d U . .
H12A H 0.0796 -0.0865 0.3398 0.063 Uiso 1 1 calc R . .
H12B H 0.1060 -0.0400 0.2746 0.063 Uiso 1 1 calc R . .
C13 C 0.0706(2) 0.0880(12) 0.2386(6) 0.057(2) Uani 1 1 d U . .
H13A H 0.0700 0.0314 0.1757 0.069 Uiso 1 1 calc R . .
H13B H 0.0786 0.1906 0.2255 0.069 Uiso 1 1 calc R . .
C14 C 0.0411(2) 0.1083(15) 0.2764(8) 0.071(3) Uani 1 1 d U . .
H14A H 0.0303 0.1675 0.2287 0.106 Uiso 1 1 calc R . .
H14B H 0.0415 0.1633 0.3390 0.106 Uiso 1 1 calc R . .
H14C H 0.0326 0.0072 0.2857 0.106 Uiso 1 1 calc R . .
C15 C 0.12224(19) 0.1659(10) 0.5483(7) 0.0520(19) Uani 1 1 d U . .
H15A H 0.1044 0.2110 0.5690 0.062 Uiso 1 1 calc R . .
H15B H 0.1304 0.1149 0.6062 0.062 Uiso 1 1 calc R . .
C16 C 0.1412(2) 0.2954(12) 0.5178(9) 0.073(3) Uani 1 1 d U E .
H16A H 0.1346 0.3405 0.4554 0.087 Uiso 1 1 calc R . .
H16B H 0.1602 0.2557 0.5077 0.087 Uiso 1 1 calc R . .
C17 C 0.1413(3) 0.4176(18) 0.5975(13) 0.109(5) Uani 1 1 d DU . .
H17A H 0.1220 0.4525 0.6068 0.131 Uiso 0.55 1 calc PR D 1
H17B H 0.1471 0.3674 0.6593 0.131 Uiso 0.55 1 calc PR D 1
H17C H 0.1291 0.5041 0.5781 0.131 Uiso 0.45 1 calc PR D 2
H17D H 0.1341 0.3736 0.6593 0.131 Uiso 0.45 1 calc PR D 2
C18 C 0.1570(8) 0.543(3) 0.586(3) 0.123(12) Uani 0.55 1 d PDU E 1
H18A H 0.1552 0.6087 0.6438 0.184 Uiso 0.55 1 calc PR E 1
H18B H 0.1509 0.5990 0.5277 0.184 Uiso 0.55 1 calc PR E 1
H18C H 0.1764 0.5119 0.5780 0.184 Uiso 0.55 1 calc PR E 1
C18' C 0.1668(7) 0.468(6) 0.611(5) 0.164(19) Uani 0.45 1 d PDU E 2
H18D H 0.1669 0.5442 0.6643 0.246 Uiso 0.45 1 calc PR E 2
H18E H 0.1736 0.5161 0.5508 0.246 Uiso 0.45 1 calc PR E 2
H18F H 0.1789 0.3820 0.6288 0.246 Uiso 0.45 1 calc PR E 2
C19 C 0.14305(19) -0.0198(11) 0.4277(7) 0.055(2) Uani 1 1 d U . .
H19A H 0.1383 -0.1062 0.3836 0.067 Uiso 1 1 calc R . .
H19B H 0.1515 0.0616 0.3868 0.067 Uiso 1 1 calc R . .
C20 C 0.1645(2) -0.0749(15) 0.4986(9) 0.077(3) Uani 1 1 d U G .
H20A H 0.1563 -0.1555 0.5409 0.092 Uiso 1 1 calc R . .
H20B H 0.1701 0.0116 0.5412 0.092 Uiso 1 1 calc R . .
C21 C 0.1898(2) -0.139(3) 0.4475(14) 0.133(7) Uani 1 1 d U . .
H21A H 0.1844 -0.2423 0.4233 0.160 Uiso 0.50 1 calc PR F 1
H21B H 0.1926 -0.0747 0.3887 0.160 Uiso 0.50 1 calc PR F 1
H21C H 0.1983 -0.0576 0.4070 0.160 Uiso 0.50 1 calc PR F 2
H21D H 0.1839 -0.2232 0.4030 0.160 Uiso 0.50 1 calc PR F 2
C22 C 0.2108(9) -0.154(10) 0.481(5) 0.20(2) Uani 0.50 1 d PU G 1
H22A H 0.2231 -0.0717 0.4587 0.293 Uiso 0.50 1 calc PR G 1
H22B H 0.2185 -0.2537 0.4622 0.293 Uiso 0.50 1 calc PR G 1
H22C H 0.2092 -0.1495 0.5530 0.293 Uiso 0.50 1 calc PR G 1
C22' C 0.2131(11) -0.206(9) 0.524(4) 0.18(2) Uani 0.50 1 d PU G 2
H22D H 0.2286 -0.2486 0.4866 0.275 Uiso 0.50 1 calc PR G 2
H22E H 0.2048 -0.2866 0.5644 0.275 Uiso 0.50 1 calc PR G 2
H22F H 0.2197 -0.1223 0.5657 0.275 Uiso 0.50 1 calc PR G 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
I1 0.0357(2) 0.0392(3) 0.0429(3) -0.00387(19) 0.0052(2) 0.00366(18)
I2 0.0410(3) 0.0851(5) 0.0780(5) -0.0036(4) 0.0022(3) 0.0210(3)
F1 0.046(2) 0.041(2) 0.060(3) 0.009(2) 0.007(2) 0.020(2)
C2 0.041(3) 0.034(3) 0.032(3) -0.002(3) 0.001(3) 0.012(3)
C3 0.050(4) 0.026(3) 0.043(4) -0.007(3) 0.003(3) 0.007(3)
F2 0.053(3) 0.039(2) 0.063(3) 0.014(2) 0.010(2) 0.008(2)
F3 0.144(19) 0.33(3) 0.153(17) 0.11(2) 0.077(16) 0.12(2)
C5 0.068(16) 0.15(2) 0.121(16) 0.035(15) 0.024(13) 0.041(16)
C6 0.047(12) 0.197(18) 0.078(7) -0.006(8) 0.003(7) 0.072(11)
F4 0.19(3) 0.55(5) 0.18(3) 0.21(3) 0.10(2) 0.25(3)
F3' 0.15(2) 0.34(3) 0.128(15) -0.12(2) -0.071(15) 0.16(2)
C5' 0.054(13) 0.15(2) 0.099(11) -0.042(15) -0.019(10) 0.062(14)
C6' 0.047(12) 0.197(18) 0.078(7) -0.006(8) 0.003(7) 0.072(11)
F4' 0.139(18) 0.35(3) 0.103(12) -0.10(2) -0.058(13) 0.17(2)
N1 0.046(3) 0.037(3) 0.040(3) -0.001(3) 0.007(3) 0.005(3)
Br1 0.0343(4) 0.0671(6) 0.0565(5) -0.0044(4) 0.0047(3) 0.0118(4)
C1 0.032(3) 0.036(3) 0.032(3) -0.004(3) 0.003(3) 0.004(3)
C4 0.043(4) 0.098(8) 0.078(5) -0.008(5) 0.002(4) 0.032(5)
C7 0.055(4) 0.033(3) 0.040(4) 0.005(3) 0.002(3) 0.007(3)
C8 0.048(4) 0.052(5) 0.049(5) 0.010(4) -0.003(3) 0.007(3)
C9 0.063(5) 0.052(5) 0.041(4) -0.003(4) 0.005(4) -0.005(4)
C10 0.053(5) 0.093(8) 0.054(5) -0.006(5) 0.004(4) -0.016(5)
C11 0.059(5) 0.038(4) 0.040(4) 0.002(3) 0.003(3) 0.005(3)
C12 0.069(5) 0.049(5) 0.039(4) -0.002(3) -0.003(4) 0.006(4)
C13 0.073(5) 0.065(6) 0.034(4) 0.004(4) -0.003(4) 0.007(5)
C14 0.061(5) 0.093(8) 0.058(6) 0.003(6) -0.008(4) -0.010(5)
C15 0.058(5) 0.045(4) 0.053(5) -0.013(4) 0.005(4) 0.008(3)
C16 0.079(7) 0.056(5) 0.083(7) -0.017(5) 0.007(6) -0.014(5)
C17 0.099(9) 0.093(9) 0.137(12) -0.064(9) 0.013(9) -0.027(7)
C18 0.18(3) 0.075(17) 0.11(2) -0.022(15) -0.01(2) -0.037(18)
C18' 0.12(2) 0.18(4) 0.20(4) -0.08(3) -0.08(3) -0.01(3)
C19 0.051(4) 0.055(5) 0.061(5) -0.008(4) 0.014(4) 0.007(4)
C20 0.055(5) 0.087(8) 0.088(8) -0.014(6) 0.003(5) 0.026(5)
C21 0.051(6) 0.204(17) 0.145(13) -0.038(13) -0.012(7) 0.054(9)
C22 0.060(14) 0.30(5) 0.23(5) -0.03(4) -0.030(18) 0.07(2)
C22' 0.11(2) 0.25(5) 0.19(4) -0.04(4) -0.04(2) 0.11(2)
_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 C1 2.111(7) . ?
I2 C4 2.101(9) . ?
F1 C2 1.351(8) . ?
C2 C1 1.378(10) . ?
C2 C3 1.380(10) 5_566 ?
C3 F2 1.332(9) . ?
C3 C2 1.381(10) 5_566 ?
C3 C1 1.390(10) . ?
F3 C5 1.41(4) . ?
C5 C4 1.34(4) . ?
C5 C5 1.76(7) 2 ?
C6 C6 1.42(7) 2 ?
C6 C4 1.45(3) . ?
C6 F4 1.31(4) . ?
F3' C5' 1.35(3) . ?
C5' C4 1.37(3) . ?
C5' C5' 1.53(6) 2 ?
C6' C4 1.20(3) . ?
C6' F4' 1.34(3) . ?
C6' C6' 1.73(5) 2 ?
N1 C11 1.521(10) . ?
N1 C7 1.526(10) . ?
N1 C15 1.531(10) . ?
N1 C19 1.519(10) . ?
C7 C8 1.498(11) . ?
C8 C9 1.519(12) . ?
C9 C10 1.519(13) . ?
C11 C12 1.511(12) . ?
C12 C13 1.542(12) . ?
C13 C14 1.524(14) . ?
C15 C16 1.509(13) . ?
C16 C17 1.522(15) . ?
C17 C18' 1.32(3) . ?
C17 C18 1.34(2) . ?
C19 C20 1.496(15) . ?
C20 C21 1.516(16) . ?
C21 C22 1.12(4) . ?
C21 C22' 1.64(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C2 C1 119.9(6) . . ?
F1 C2 C3 117.6(6) . 5_566 ?
C1 C2 C3 122.4(6) . 5_566 ?
F2 C3 C2 119.3(6) . 5_566 ?
F2 C3 C1 119.8(7) . . ?
C2 C3 C1 120.9(7) 5_566 . ?
C4 C5 F3 114(3) . . ?
C4 C5 C5 98(3) . 2 ?
F3 C5 C5 119(2) . 2 ?
C6 C6 C4 107(3) 2 . ?
C6 C6 F4 136.8(19) 2 . ?
C4 C6 F4 110(2) . . ?
C4 C5' F3' 120.9(19) . . ?
C4 C5' C5' 112(2) . 2 ?
F3' C5' C5' 122.9(17) . 2 ?
C4 C6' F4' 124(2) . . ?
C4 C6' C6' 111(2) . 2 ?
F4' C6' C6' 115.8(14) . 2 ?
C11 N1 C7 110.8(6) . . ?
C11 N1 C15 109.6(6) . . ?
C7 N1 C15 107.3(6) . . ?
C11 N1 C19 109.1(6) . . ?
C7 N1 C19 108.8(6) . . ?
C15 N1 C19 111.2(7) . . ?
C2 C1 C3 116.7(6) . . ?
C2 C1 I1 122.1(5) . . ?
C3 C1 I1 121.2(5) . . ?
C6' C4 C5' 118.0(19) . . ?
C6' C4 C5 100(3) . . ?
C5' C4 C5 40(2) . . ?
C6' C4 C6 33(2) . . ?
C5' C4 C6 105.3(18) . . ?
C5 C4 C6 111(2) . . ?
C6' C4 I2 120.9(15) . . ?
C5' C4 I2 120.9(12) . . ?
C5 C4 I2 122.3(15) . . ?
C6 C4 I2 126.2(14) . . ?
C8 C7 N1 114.7(6) . . ?
C7 C8 C9 112.0(7) . . ?
C8 C9 C10 112.9(8) . . ?
C12 C11 N1 115.9(7) . . ?
C11 C12 C13 108.3(7) . . ?
C12 C13 C14 113.7(8) . . ?
C16 C15 N1 116.4(8) . . ?
C15 C16 C17 109.1(10) . . ?
C18' C17 C18 38(3) . . ?
C18' C17 C16 110(3) . . ?
C18 C17 C16 119(2) . . ?
C20 C19 N1 116.8(8) . . ?
C19 C20 C21 112.3(11) . . ?
C22 C21 C20 126(4) . . ?
C22 C21 C22' 23(6) . . ?
C20 C21 C22' 113(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
F1 C2 C1 C3 -179.9(6) . . . . ?
C3 C2 C1 C3 0.0(12) 5_566 . . . ?
F1 C2 C1 I1 -0.1(9) . . . . ?
C3 C2 C1 I1 179.8(5) 5_566 . . . ?
F2 C3 C1 C2 179.6(7) . . . . ?
C2 C3 C1 C2 0.0(12) 5_566 . . . ?
F2 C3 C1 I1 -0.3(10) . . . . ?
C2 C3 C1 I1 -179.9(5) 5_566 . . . ?
F4' C6' C4 C5' -171(3) . . . . ?
C6' C6' C4 C5' -26(5) 2 . . . ?
F4' C6' C4 C5 151(3) . . . . ?
C6' C6' C4 C5 -64(4) 2 . . . ?
F4' C6' C4 C6 -96(6) . . . . ?
C6' C6' C4 C6 48(4) 2 . . . ?
F4' C6' C4 I2 14(5) . . . . ?
C6' C6' C4 I2 158(2) 2 . . . ?
F3' C5' C4 C6' 180(4) . . . . ?
C5' C5' C4 C6' -23(5) 2 . . . ?
F3' C5' C4 C5 -110(6) . . . . ?
C5' C5' C4 C5 47(3) 2 . . . ?
F3' C5' C4 C6 146(4) . . . . ?
C5' C5' C4 C6 -57(4) 2 . . . ?
F3' C5' C4 I2 -5(5) . . . . ?
C5' C5' C4 I2 152(2) 2 . . . ?
F3 C5 C4 C6' -157(3) . . . . ?
C5 C5 C4 C6' 77(3) 2 . . . ?
F3 C5 C4 C5' 81(5) . . . . ?
C5 C5 C4 C5' -45(3) 2 . . . ?
F3 C5 C4 C6 171(3) . . . . ?
C5 C5 C4 C6 44(3) 2 . . . ?
F3 C5 C4 I2 -20(4) . . . . ?
C5 C5 C4 I2 -146.2(15) 2 . . . ?
C6 C6 C4 C6' -51(5) 2 . . . ?
F4 C6 C4 C6' 107(5) . . . . ?
C6 C6 C4 C5' 67(3) 2 . . . ?
F4 C6 C4 C5' -135(3) . . . . ?
C6 C6 C4 C5 25(4) 2 . . . ?
F4 C6 C4 C5 -177(2) . . . . ?
C6 C6 C4 I2 -143.6(16) 2 . . . ?
F4 C6 C4 I2 14(4) . . . . ?
C11 N1 C7 C8 -53.8(9) . . . . ?
C15 N1 C7 C8 65.9(9) . . . . ?
C19 N1 C7 C8 -173.7(7) . . . . ?
N1 C7 C8 C9 -174.7(7) . . . . ?
C7 C8 C9 C10 -173.8(8) . . . . ?
C7 N1 C11 C12 -57.6(9) . . . . ?
C15 N1 C11 C12 -175.9(7) . . . . ?
C19 N1 C11 C12 62.1(9) . . . . ?
N1 C11 C12 C13 175.8(7) . . . . ?
C11 C12 C13 C14 -79.0(11) . . . . ?
C11 N1 C15 C16 -68.6(10) . . . . ?
C7 N1 C15 C16 171.0(8) . . . . ?
C19 N1 C15 C16 52.1(11) . . . . ?
N1 C15 C16 C17 171.8(10) . . . . ?
C15 C16 C17 C18' 138(3) . . . . ?
C15 C16 C17 C18 179(2) . . . . ?
C11 N1 C19 C20 172.8(9) . . . . ?
C7 N1 C19 C20 -66.1(11) . . . . ?
C15 N1 C19 C20 51.8(11) . . . . ?
N1 C19 C20 C21 178.2(12) . . . . ?
C19 C20 C21 C22 160(6) . . . . ?
C19 C20 C21 C22' -178(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.858
_refine_diff_density_min         -1.493
_refine_diff_density_rms         0.138


data_db065_5
_database_code_depnum_ccdc_archive 'CCDC 907314'
#TrackingRef 'web_deposit_cif_file_2_DavidBryce_1351030412.db065_compound 4.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H72 Br2 F8 I4 P2'
_chemical_formula_weight         1482.38
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
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'
'-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                   49.7447(10)
_cell_length_b                   8.4785(2)
_cell_length_c                   14.1541(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.1190(10)
_cell_angle_gamma                90.00
_cell_volume                     5789.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4500
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.29
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2880
_exptl_absorpt_coefficient_mu    3.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5765
_exptl_absorpt_correction_T_max  0.6902
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_special_details           
;
Data collection is performed with three batch runs at phi = 0.00 deg
(650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg
(650 frames).
Frame width = 0.30 deg in omega.
Data is merged, corrected for decay (if any), and treated with multi-scan
absorption corrections (if required). All symmetry-equivalent reflections
are merged for centrosymmetric data.
Friedel pairs are not merged for noncentrosymmetric data.
;
_diffrn_ambient_temperature      200(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -66
_diffrn_reflns_limit_h_max       64
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.33
_reflns_number_total             7049
_reflns_number_gt                5827
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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^)+(0.0589P)^2^+20.2869P] 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         7049
_refine_ls_number_parameters     347
_refine_ls_number_restraints     221
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.005
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 0.184226(9) 0.71256(5) 0.04795(3) 0.05422(11) Uani 1 1 d . . .
I2 I 0.064790(9) 0.81324(6) 0.05198(4) 0.06281(13) Uani 1 1 d . . .
Br1 Br 0.125040(14) 0.65776(10) 0.09199(6) 0.0662(2) Uani 1 1 d . . .
F1 F 0.21358(9) 0.9910(6) -0.0446(4) 0.0786(13) Uani 1 1 d . . .
F2 F 0.23676(9) 0.4821(5) 0.0810(4) 0.0808(13) Uani 1 1 d . . .
C1 C 0.23130(14) 0.8684(8) -0.0226(5) 0.0521(14) Uani 1 1 d . . .
C2 C 0.22360(12) 0.7350(8) 0.0191(5) 0.0501(14) Uani 1 1 d . . .
C3 C 0.24290(14) 0.6186(8) 0.0411(5) 0.0534(14) Uani 1 1 d . . .
C5 C 0.02576(13) 0.9226(9) 0.0224(5) 0.0602(16) Uani 1 1 d U . .
F3 F 0.0332(5) 1.016(4) 0.1786(14) 0.130(10) Uani 0.50 1 d PU A 1
F4 F 0.0155(4) 0.837(3) -0.1402(13) 0.113(9) Uani 0.50 1 d PU B 1
C4 C 0.0186(5) 1.008(4) 0.092(3) 0.066(7) Uani 0.50 1 d PU . 1
C6 C 0.0068(6) 0.903(4) -0.073(3) 0.071(8) Uani 0.50 1 d PU . 1
F3' F 0.0245(6) 0.929(5) 0.1867(18) 0.153(14) Uani 0.50 1 d PU . 2
F4' F 0.0243(5) 0.920(4) -0.1443(18) 0.143(13) Uani 0.50 1 d PU . 2
C4' C 0.0114(5) 0.966(4) 0.090(2) 0.068(7) Uani 0.50 1 d PU . 2
C6' C 0.0128(7) 0.961(4) -0.070(2) 0.069(7) Uani 0.50 1 d PU . 2
P1 P 0.12813(4) 0.7876(3) 0.41076(19) 0.0792(7) Uani 1 1 d . D .
C7 C 0.1492(2) 0.8767(13) 0.5266(8) 0.097(3) Uani 1 1 d DU . .
H7A H 0.1666 0.9194 0.5143 0.117 Uiso 0.67 1 calc PR C 1
H7B H 0.1387 0.9661 0.5450 0.117 Uiso 0.67 1 calc PR C 1
H7C H 0.1599 0.9658 0.5092 0.117 Uiso 0.33 1 calc PR C 2
H7D H 0.1363 0.9209 0.5629 0.117 Uiso 0.33 1 calc PR C 2
C8 C 0.1563(3) 0.7657(17) 0.6091(9) 0.081(3) Uani 0.67 1 d PDU D 1
H8A H 0.1393 0.7312 0.6276 0.097 Uiso 0.67 1 calc PR D 1
H8B H 0.1656 0.6714 0.5905 0.097 Uiso 0.67 1 calc PR D 1
C8' C 0.1682(6) 0.773(3) 0.5910(15) 0.095(7) Uani 0.33 1 d PDU D 2
H8C H 0.1854 0.7598 0.5680 0.113 Uiso 0.33 1 calc PR D 2
H8D H 0.1597 0.6678 0.5927 0.113 Uiso 0.33 1 calc PR D 2
C9 C 0.1750(3) 0.8462(12) 0.6918(8) 0.085(3) Uani 1 1 d DU . .
H9A H 0.172(3) 0.95(2) 0.718(13) 0.102 Uiso 0.67 1 d P E 1
H9B H 0.181(4) 0.80(2) 0.732(14) 0.102 Uiso 0.67 1 d P F 1
H9C H 0.190(6) 0.94(4) 0.76(2) 0.102 Uiso 0.33 1 d P G 2
H9D H 0.170(6) 0.86(4) 0.62(2) 0.102 Uiso 0.33 1 d P H 2
C10 C 0.2059(2) 0.8616(15) 0.7019(9) 0.105(4) Uani 1 1 d U D .
H10A H 0.2149 0.8963 0.7680 0.157 Uiso 1 1 calc R . .
H10B H 0.2093 0.9393 0.6548 0.157 Uiso 1 1 calc R . .
H10C H 0.2135 0.7593 0.6892 0.157 Uiso 1 1 calc R . .
C11 C 0.12314(18) 0.9454(12) 0.3276(6) 0.080(2) Uani 1 1 d U . .
H11A H 0.1414 0.9952 0.3314 0.096 Uiso 1 1 calc R D .
H11B H 0.1165 0.9016 0.2612 0.096 Uiso 1 1 calc R . .
C12 C 0.1034(2) 1.0711(17) 0.3408(12) 0.125(4) Uani 1 1 d U D .
H12A H 0.1099 1.1187 0.4062 0.150 Uiso 1 1 calc R . .
H12B H 0.0849 1.0240 0.3364 0.150 Uiso 1 1 calc R . .
C13 C 0.1010(4) 1.199(2) 0.2635(17) 0.162(7) Uani 1 1 d U . .
H13A H 0.1174 1.2672 0.2870 0.195 Uiso 1 1 calc R D .
H13B H 0.1041 1.1435 0.2053 0.195 Uiso 1 1 calc R . .
C14 C 0.0821(5) 1.287(3) 0.233(2) 0.300(17) Uani 1 1 d U D .
H14A H 0.0863 1.3522 0.1813 0.451 Uiso 1 1 calc R . .
H14B H 0.0794 1.3544 0.2860 0.451 Uiso 1 1 calc R . .
H14C H 0.0652 1.2258 0.2067 0.451 Uiso 1 1 calc R . .
C15 C 0.0971(2) 0.722(2) 0.4387(13) 0.161(7) Uani 1 1 d DU . .
H15A H 0.1017 0.6317 0.4839 0.193 Uiso 1 1 calc R D .
H15B H 0.0902 0.8082 0.4742 0.193 Uiso 1 1 calc R . .
C16 C 0.0756(3) 0.677(2) 0.3607(15) 0.214(9) Uani 1 1 d DU D .
H16A H 0.0842 0.6166 0.3159 0.257 Uiso 0.50 1 calc PR I 1
H16B H 0.0682 0.7753 0.3260 0.257 Uiso 0.50 1 calc PR I 1
H16C H 0.0817 0.5852 0.3284 0.257 Uiso 0.50 1 calc PR I 2
H16D H 0.0718 0.7645 0.3128 0.257 Uiso 0.50 1 calc PR I 2
C17 C 0.0506(6) 0.582(4) 0.372(3) 0.182(11) Uani 0.50 1 d PDU D 1
H17A H 0.0385 0.5643 0.3064 0.218 Uiso 0.50 1 calc PR D 1
H17B H 0.0574 0.4779 0.3992 0.218 Uiso 0.50 1 calc PR D 1
C18 C 0.0332(8) 0.649(5) 0.434(3) 0.222(14) Uani 0.50 1 d PDU D 1
H18A H 0.0139 0.6549 0.3964 0.333 Uiso 0.50 1 calc PR D 1
H18B H 0.0398 0.7552 0.4557 0.333 Uiso 0.50 1 calc PR D 1
H18C H 0.0344 0.5813 0.4911 0.333 Uiso 0.50 1 calc PR D 1
C17' C 0.0485(5) 0.634(5) 0.389(3) 0.193(12) Uani 0.50 1 d PDU D 2
H17C H 0.0521 0.5487 0.4377 0.232 Uiso 0.50 1 calc PR D 2
H17D H 0.0416 0.7271 0.4180 0.232 Uiso 0.50 1 calc PR D 2
C18' C 0.0268(5) 0.581(5) 0.301(4) 0.240(18) Uani 0.50 1 d PDU D 2
H18D H 0.0103 0.5469 0.3212 0.361 Uiso 0.50 1 calc PR D 2
H18E H 0.0340 0.4934 0.2696 0.361 Uiso 0.50 1 calc PR D 2
H18F H 0.0220 0.6691 0.2549 0.361 Uiso 0.50 1 calc PR D 2
C19 C 0.14799(16) 0.6397(11) 0.3698(7) 0.072(2) Uani 1 1 d U . .
H19A H 0.1497 0.5476 0.4139 0.086 Uiso 1 1 calc R D .
H19B H 0.1378 0.6047 0.3041 0.086 Uiso 1 1 calc R . .
C20 C 0.17721(16) 0.6922(10) 0.3650(7) 0.073(2) Uani 1 1 d U D .
H20A H 0.1758 0.7904 0.3263 0.088 Uiso 1 1 calc R . .
H20B H 0.1883 0.7158 0.4317 0.088 Uiso 1 1 calc R . .
C21 C 0.19218(16) 0.5673(11) 0.3197(6) 0.0701(19) Uani 1 1 d U . .
H21A H 0.1819 0.5479 0.2515 0.084 Uiso 1 1 calc R D .
H21B H 0.1929 0.4672 0.3562 0.084 Uiso 1 1 calc R . .
C22 C 0.22146(18) 0.6217(14) 0.3218(7) 0.085(3) Uani 1 1 d U D .
H22A H 0.2307 0.5415 0.2911 0.128 Uiso 1 1 calc R . .
H22B H 0.2318 0.6372 0.3895 0.128 Uiso 1 1 calc R . .
H22C H 0.2207 0.7213 0.2861 0.128 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 0.0503(2) 0.0582(2) 0.0568(2) -0.0063(2) 0.0183(2) 0.00063(19)
I2 0.0488(2) 0.0762(3) 0.0635(3) -0.0060(2) 0.0138(2) 0.01175(19)
Br1 0.0453(3) 0.0777(5) 0.0766(5) -0.0029(4) 0.0167(3) 0.0114(3)
F1 0.076(3) 0.066(3) 0.103(4) 0.030(3) 0.041(3) 0.029(2)
F2 0.083(3) 0.062(2) 0.110(4) 0.026(3) 0.047(3) 0.009(2)
C1 0.060(4) 0.047(3) 0.050(3) 0.008(3) 0.016(3) 0.014(3)
C2 0.044(3) 0.056(4) 0.054(3) -0.008(3) 0.018(3) -0.003(3)
C3 0.058(3) 0.047(3) 0.057(4) 0.001(3) 0.017(3) 0.005(3)
C5 0.047(3) 0.078(4) 0.055(3) -0.005(4) 0.010(3) 0.014(3)
F3 0.085(13) 0.23(3) 0.055(9) -0.046(13) -0.015(8) 0.074(14)
F4 0.083(11) 0.20(2) 0.050(8) -0.048(11) -0.006(7) 0.075(12)
C4 0.028(10) 0.099(17) 0.062(9) -0.020(11) -0.008(8) 0.008(10)
C6 0.043(12) 0.10(2) 0.060(8) -0.017(12) 0.002(8) 0.029(12)
F3' 0.103(17) 0.30(4) 0.066(8) 0.043(17) 0.032(10) 0.078(19)
F4' 0.101(15) 0.26(4) 0.080(10) 0.017(16) 0.054(11) 0.069(16)
C4' 0.049(14) 0.118(19) 0.035(7) -0.004(10) 0.004(9) -0.006(11)
C6' 0.056(13) 0.11(2) 0.047(7) -0.006(12) 0.023(8) 0.018(12)
P1 0.0575(11) 0.1072(18) 0.0747(14) 0.0326(13) 0.0200(10) 0.0104(11)
C7 0.108(7) 0.093(7) 0.097(6) -0.008(5) 0.035(5) -0.010(5)
C8 0.085(8) 0.069(7) 0.104(8) -0.003(6) 0.053(6) -0.015(6)
C8' 0.077(14) 0.093(16) 0.115(13) -0.032(11) 0.027(10) -0.007(12)
C9 0.112(7) 0.059(5) 0.093(6) -0.015(4) 0.040(5) 0.000(5)
C10 0.088(6) 0.111(8) 0.100(8) 0.016(7) -0.009(5) 0.008(6)
C11 0.080(5) 0.094(6) 0.072(5) -0.008(4) 0.031(4) -0.014(4)
C12 0.097(7) 0.112(8) 0.180(12) 0.046(8) 0.061(8) 0.027(6)
C13 0.165(13) 0.131(12) 0.231(18) 0.053(10) 0.125(13) 0.049(9)
C14 0.25(3) 0.26(3) 0.38(4) 0.22(3) 0.05(3) 0.08(2)
C15 0.061(5) 0.172(13) 0.246(17) 0.116(12) 0.031(7) -0.005(6)
C16 0.114(9) 0.118(11) 0.37(2) 0.069(14) -0.027(11) -0.055(8)
C17 0.098(13) 0.11(2) 0.32(3) 0.080(19) 0.025(14) -0.016(13)
C18 0.16(3) 0.13(2) 0.35(4) -0.01(3) 0.01(2) 0.01(2)
C17' 0.078(10) 0.12(2) 0.34(3) 0.08(2) -0.033(13) -0.004(14)
C18' 0.095(14) 0.16(3) 0.41(4) 0.04(3) -0.06(2) -0.031(17)
C19 0.063(4) 0.072(5) 0.077(5) 0.019(4) 0.010(4) -0.013(4)
C20 0.060(4) 0.068(5) 0.094(6) 0.011(4) 0.023(4) -0.008(3)
C21 0.077(5) 0.071(5) 0.060(4) 0.004(3) 0.011(3) 0.002(4)
C22 0.073(5) 0.106(7) 0.079(6) -0.001(5) 0.021(4) 0.001(5)
_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 C2 2.105(6) . ?
I2 C5 2.099(6) . ?
F1 C1 1.349(8) . ?
F2 C3 1.354(8) . ?
C1 C3 1.375(9) 7_565 ?
C1 C2 1.373(10) . ?
C2 C3 1.359(9) . ?
C3 C1 1.376(9) 7_565 ?
C5 C4 1.34(3) . ?
C5 C6' 1.35(3) . ?
C5 C6 1.45(3) . ?
C5 C4' 1.38(3) . ?
F3 C4 1.26(4) . ?
F4 C6 1.27(4) . ?
C4 C6 1.44(4) 5_575 ?
C6 C4 1.44(4) 5_575 ?
F3' C4' 1.40(4) . ?
F4' C6' 1.36(4) . ?
C4' C6' 1.32(5) 5_575 ?
C6' C4' 1.32(5) 5_575 ?
P1 C11 1.758(10) . ?
P1 C19 1.779(10) . ?
P1 C15 1.773(11) . ?
P1 C7 1.875(11) . ?
C7 C8' 1.444(18) . ?
C7 C8 1.475(14) . ?
C8 C9 1.472(15) . ?
C8' C9 1.517(18) . ?
C9 C10 1.512(17) . ?
C11 C12 1.491(15) . ?
C12 C13 1.52(2) . ?
C13 C14 1.20(2) . ?
C15 C16 1.391(15) . ?
C16 C17 1.521(17) . ?
C16 C17' 1.539(19) . ?
C17 C18 1.488(19) . ?
C17' C18' 1.499(19) . ?
C19 C20 1.538(10) . ?
C20 C21 1.524(12) . ?
C21 C22 1.521(12) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C3 118.8(6) . 7_565 ?
F1 C1 C2 119.9(6) . . ?
C3 C1 C2 121.3(6) 7_565 . ?
C3 C2 C1 116.2(6) . . ?
C3 C2 I1 121.9(5) . . ?
C1 C2 I1 121.9(5) . . ?
F2 C3 C2 119.8(6) . . ?
F2 C3 C1 117.6(6) . 7_565 ?
C2 C3 C1 122.5(6) . 7_565 ?
C4 C5 C6' 116(2) . . ?
C4 C5 C6 120.9(17) . . ?
C6' C5 C6 23.0(19) . . ?
C4 C5 C4' 21.2(17) . . ?
C6' C5 C4' 114.0(19) . . ?
C6 C5 C4' 110.3(18) . . ?
C4 C5 I2 119.4(13) . . ?
C6' C5 I2 119.9(15) . . ?
C6 C5 I2 119.7(14) . . ?
C4' C5 I2 126.1(14) . . ?
C5 C4 F3 123(3) . . ?
C5 C4 C6 121(3) . 5_575 ?
F3 C4 C6 115(3) . 5_575 ?
F4 C6 C5 119(2) . . ?
F4 C6 C4 122(3) . 5_575 ?
C5 C6 C4 117(3) . 5_575 ?
F3' C4' C6' 120(3) . 5_575 ?
F3' C4' C5 115(3) . . ?
C6' C4' C5 125(3) 5_575 . ?
F4' C6' C5 120(3) . . ?
F4' C6' C4' 119(3) . 5_575 ?
C5 C6' C4' 121(3) . 5_575 ?
C11 P1 C19 108.5(4) . . ?
C11 P1 C15 113.5(5) . . ?
C19 P1 C15 115.8(7) . . ?
C11 P1 C7 103.7(5) . . ?
C19 P1 C7 109.4(4) . . ?
C15 P1 C7 105.2(7) . . ?
C8' C7 C8 27.8(14) . . ?
C8' C7 P1 116.6(12) . . ?
C8 C7 P1 114.3(8) . . ?
C9 C8 C7 108.5(10) . . ?
C7 C8' C9 107.8(15) . . ?
C8 C9 C10 122.9(11) . . ?
C8 C9 C8' 27.2(13) . . ?
C10 C9 C8' 96.4(15) . . ?
C12 C11 P1 116.7(7) . . ?
C11 C12 C13 110.8(11) . . ?
C14 C13 C12 128.3(18) . . ?
C16 C15 P1 116.8(13) . . ?
C15 C16 C17 123(2) . . ?
C15 C16 C17' 114.5(19) . . ?
C17 C16 C17' 20(2) . . ?
C18 C17 C16 118(2) . . ?
C18' C17' C16 111(2) . . ?
C20 C19 P1 114.6(6) . . ?
C21 C20 C19 112.4(7) . . ?
C20 C21 C22 110.2(7) . . ?
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
F1 C1 C2 C3 -178.4(6) . . . . ?
C3 C1 C2 C3 0.4(11) 7_565 . . . ?
F1 C1 C2 I1 1.3(9) . . . . ?
C3 C1 C2 I1 -180.0(5) 7_565 . . . ?
C1 C2 C3 F2 -178.9(6) . . . . ?
I1 C2 C3 F2 1.4(10) . . . . ?
C1 C2 C3 C1 -0.4(11) . . . 7_565 ?
I1 C2 C3 C1 179.9(5) . . . 7_565 ?
C6' C5 C4 F3 -162(3) . . . . ?
C6 C5 C4 F3 173(3) . . . . ?
C4' C5 C4 F3 108(9) . . . . ?
I2 C5 C4 F3 -6(4) . . . . ?
C6' C5 C4 C6 19(3) . . . 5_575 ?
C6 C5 C4 C6 -6(4) . . . 5_575 ?
C4' C5 C4 C6 -71(6) . . . 5_575 ?
I2 C5 C4 C6 174(2) . . . 5_575 ?
C4 C5 C6 F4 172(3) . . . . ?
C6' C5 C6 F4 88(7) . . . . ?
C4' C5 C6 F4 -168(3) . . . . ?
I2 C5 C6 F4 -9(4) . . . . ?
C4 C5 C6 C4 6(4) . . . 5_575 ?
C6' C5 C6 C4 -77(7) . . . 5_575 ?
C4' C5 C6 C4 26(3) . . . 5_575 ?
I2 C5 C6 C4 -174.6(19) . . . 5_575 ?
C4 C5 C4' F3' -80(7) . . . . ?
C6' C5 C4' F3' -180(3) . . . . ?
C6 C5 C4' F3' 156(3) . . . . ?
I2 C5 C4' F3' -1(3) . . . . ?
C4 C5 C4' C6' 99(9) . . . 5_575 ?
C6' C5 C4' C6' 0(4) . . . 5_575 ?
C6 C5 C4' C6' -25(4) . . . 5_575 ?
I2 C5 C4' C6' 178(2) . . . 5_575 ?
C4 C5 C6' F4' 159(3) . . . . ?
C6 C5 C6' F4' -92(7) . . . . ?
C4' C5 C6' F4' -178(3) . . . . ?
I2 C5 C6' F4' 4(3) . . . . ?
C4 C5 C6' C4' -23(3) . . . 5_575 ?
C6 C5 C6' C4' 86(7) . . . 5_575 ?
C4' C5 C6' C4' 0(4) . . . 5_575 ?
I2 C5 C6' C4' -178(2) . . . 5_575 ?
C11 P1 C7 C8' -149.0(18) . . . . ?
C19 P1 C7 C8' -33.5(19) . . . . ?
C15 P1 C7 C8' 91.6(19) . . . . ?
C11 P1 C7 C8 -179.8(9) . . . . ?
C19 P1 C7 C8 -64.3(10) . . . . ?
C15 P1 C7 C8 60.8(11) . . . . ?
C8' C7 C8 C9 73(2) . . . . ?
P1 C7 C8 C9 174.6(9) . . . . ?
C8 C7 C8' C9 -68(2) . . . . ?
P1 C7 C8' C9 -159.7(14) . . . . ?
C7 C8 C9 C10 -82.0(15) . . . . ?
C7 C8 C9 C8' -69(2) . . . . ?
C7 C8' C9 C8 72(2) . . . . ?
C7 C8' C9 C10 -120(2) . . . . ?
C19 P1 C11 C12 171.1(9) . . . . ?
C15 P1 C11 C12 40.9(12) . . . . ?
C7 P1 C11 C12 -72.7(10) . . . . ?
P1 C11 C12 C13 -179.6(12) . . . . ?
C11 C12 C13 C14 155(3) . . . . ?
C11 P1 C15 C16 56.0(16) . . . . ?
C19 P1 C15 C16 -70.4(14) . . . . ?
C7 P1 C15 C16 168.6(13) . . . . ?
P1 C15 C16 C17 165(2) . . . . ?
P1 C15 C16 C17' -175(2) . . . . ?
C15 C16 C17 C18 58(5) . . . . ?
C17' C16 C17 C18 -10(6) . . . . ?
C15 C16 C17' C18' -178(3) . . . . ?
C17 C16 C17' C18' -56(8) . . . . ?
C11 P1 C19 C20 62.3(8) . . . . ?
C15 P1 C19 C20 -168.8(8) . . . . ?
C7 P1 C19 C20 -50.1(8) . . . . ?
P1 C19 C20 C21 -174.0(6) . . . . ?
C19 C20 C21 C22 -177.0(7) . . . . ?
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         1.007
_refine_diff_density_min         -1.448
_refine_diff_density_rms         0.104


data_db093
_database_code_depnum_ccdc_archive 'CCDC 907315'
#TrackingRef 'web_deposit_cif_file_3_DavidBryce_1351030412.db093_compound 5.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Br F2 I P'
_chemical_formula_weight         572.17
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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
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                   10.8351(3)
_cell_length_b                   11.8074(3)
_cell_length_c                   17.0179(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.3430(10)
_cell_angle_gamma                90.00
_cell_volume                     2175.35(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9053
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.32
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1116
_exptl_absorpt_coefficient_mu    3.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4183
_exptl_absorpt_correction_T_max  0.5639
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_special_details           
;
Data collection is performed with three batch runs at phi = 0.00 deg
(650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg
(650 frames).
Frame width = 0.30 deg in omega.
Data is merged, corrected for decay (if any), and treated with multi-scan
absorption corrections (if required). All symmetry-equivalent reflections
are merged for centrosymmetric data.
Friedel pairs are not merged for noncentrosymmetric data.
;
_diffrn_ambient_temperature      200(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23686
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.33
_reflns_number_total             5372
_reflns_number_gt                5011
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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^)+(0.0260P)^2^+0.6704P] 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     SHELXL
_refine_ls_extinction_coef       0.0066(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5372
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0190
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0464
_refine_ls_wR_factor_gt          0.0452
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.133173(8) 0.026643(8) 0.191541(5) 0.02742(4) Uani 1 1 d . . .
F1 F 0.16345(9) 0.16915(9) 0.03171(6) 0.0399(2) Uani 1 1 d . . .
F2 F -0.06556(9) -0.14712(9) 0.11296(5) 0.0413(2) Uani 1 1 d . . .
Br1 Br 0.225234(16) 0.544806(15) 0.143726(9) 0.03616(5) Uani 1 1 d . . .
P1 P 0.62401(3) 0.10719(3) 0.20642(2) 0.02132(7) Uani 1 1 d . . .
C1 C 0.05187(13) 0.01186(12) 0.07733(8) 0.0246(3) Uani 1 1 d . . .
C2 C 0.08266(13) 0.08421(13) 0.01737(8) 0.0265(3) Uani 1 1 d . . .
C3 C -0.03207(13) -0.07243(13) 0.05761(8) 0.0265(3) Uani 1 1 d . . .
C4 C 0.49508(13) 0.20070(13) 0.22056(9) 0.0279(3) Uani 1 1 d . . .
H4A H 0.4384 0.1647 0.2573 0.034 Uiso 1 1 calc R . .
H4B H 0.5260 0.2718 0.2452 0.034 Uiso 1 1 calc R . .
C5 C 0.42307(15) 0.22937(14) 0.14395(10) 0.0352(3) Uani 1 1 d . . .
H5A H 0.3544 0.2801 0.1552 0.053 Uiso 1 1 calc R . .
H5B H 0.3906 0.1596 0.1198 0.053 Uiso 1 1 calc R . .
H5C H 0.4781 0.2668 0.1078 0.053 Uiso 1 1 calc R . .
C6 C 0.73021(12) 0.17368(12) 0.14271(8) 0.0236(3) Uani 1 1 d . . .
C7 C 0.70739(13) 0.17187(13) 0.06109(8) 0.0282(3) Uani 1 1 d . . .
H7A H 0.6391 0.1306 0.0391 0.034 Uiso 1 1 calc R . .
C8 C 0.78436(14) 0.23026(14) 0.01261(9) 0.0317(3) Uani 1 1 d . . .
H8A H 0.7689 0.2292 -0.0427 0.038 Uiso 1 1 calc R . .
C9 C 0.88440(14) 0.29051(13) 0.04464(9) 0.0321(3) Uani 1 1 d . . .
H9A H 0.9373 0.3303 0.0111 0.038 Uiso 1 1 calc R . .
C10 C 0.90744(14) 0.29283(13) 0.12520(9) 0.0306(3) Uani 1 1 d . . .
H10A H 0.9761 0.3340 0.1467 0.037 Uiso 1 1 calc R . .
C11 C 0.83050(13) 0.23517(12) 0.17454(8) 0.0267(3) Uani 1 1 d . . .
H11A H 0.8459 0.2374 0.2299 0.032 Uiso 1 1 calc R . .
C12 C 0.70112(13) 0.07595(12) 0.29907(8) 0.0238(3) Uani 1 1 d . . .
C13 C 0.64377(14) 0.09482(13) 0.36974(8) 0.0282(3) Uani 1 1 d . . .
H13A H 0.5642 0.1286 0.3699 0.034 Uiso 1 1 calc R . .
C14 C 0.70439(16) 0.06355(14) 0.43994(9) 0.0338(3) Uani 1 1 d . . .
H14A H 0.6661 0.0763 0.4884 0.041 Uiso 1 1 calc R . .
C15 C 0.82012(17) 0.01404(14) 0.43984(10) 0.0351(3) Uani 1 1 d . . .
H15A H 0.8608 -0.0070 0.4882 0.042 Uiso 1 1 calc R . .
C16 C 0.87681(15) -0.00497(14) 0.36961(10) 0.0344(3) Uani 1 1 d . . .
H16A H 0.9566 -0.0384 0.3698 0.041 Uiso 1 1 calc R . .
C17 C 0.81724(14) 0.02475(12) 0.29900(9) 0.0293(3) Uani 1 1 d . . .
H17A H 0.8553 0.0103 0.2507 0.035 Uiso 1 1 calc R . .
C18 C 0.56929(13) -0.02455(11) 0.16531(8) 0.0233(3) Uani 1 1 d . . .
C19 C 0.63583(14) -0.08540(13) 0.11082(9) 0.0308(3) Uani 1 1 d . . .
H19A H 0.7089 -0.0543 0.0905 0.037 Uiso 1 1 calc R . .
C20 C 0.59476(15) -0.19139(14) 0.08650(10) 0.0352(3) Uani 1 1 d . . .
H20A H 0.6398 -0.2330 0.0495 0.042 Uiso 1 1 calc R . .
C21 C 0.48877(15) -0.23668(13) 0.11584(10) 0.0340(3) Uani 1 1 d . . .
H21A H 0.4609 -0.3092 0.0986 0.041 Uiso 1 1 calc R . .
C22 C 0.42291(14) -0.17721(14) 0.17011(10) 0.0330(3) Uani 1 1 d . . .
H22A H 0.3501 -0.2090 0.1902 0.040 Uiso 1 1 calc R . .
C23 C 0.46292(13) -0.07109(13) 0.19529(9) 0.0276(3) Uani 1 1 d . . .
H23A H 0.4179 -0.0304 0.2328 0.033 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 0.02268(6) 0.03775(7) 0.02175(6) 0.00025(3) -0.00023(3) 0.00213(3)
F1 0.0409(5) 0.0427(5) 0.0356(5) 0.0030(4) -0.0051(4) -0.0185(4)
F2 0.0477(5) 0.0451(6) 0.0307(5) 0.0152(4) -0.0034(4) -0.0154(5)
Br1 0.03865(9) 0.05045(10) 0.01941(8) 0.00245(6) 0.00135(6) -0.00401(7)
P1 0.02212(16) 0.02172(17) 0.02007(15) -0.00067(12) 0.00043(12) 0.00058(12)
C1 0.0210(6) 0.0323(7) 0.0204(6) 0.0001(5) -0.0007(5) 0.0043(5)
C2 0.0228(6) 0.0287(7) 0.0279(7) 0.0012(5) 0.0005(5) -0.0025(5)
C3 0.0260(7) 0.0297(7) 0.0238(6) 0.0061(5) 0.0022(5) 0.0000(5)
C4 0.0287(7) 0.0251(7) 0.0300(7) -0.0024(6) 0.0019(5) 0.0054(5)
C5 0.0308(7) 0.0331(8) 0.0412(9) 0.0034(7) -0.0051(6) 0.0048(6)
C6 0.0250(6) 0.0234(6) 0.0225(6) 0.0013(5) 0.0011(5) 0.0014(5)
C7 0.0295(7) 0.0305(7) 0.0243(6) 0.0014(6) -0.0023(5) -0.0004(6)
C8 0.0363(8) 0.0367(8) 0.0220(6) 0.0041(6) 0.0017(6) 0.0030(6)
C9 0.0324(7) 0.0310(8) 0.0333(8) 0.0077(6) 0.0079(6) 0.0005(6)
C10 0.0282(7) 0.0288(7) 0.0347(8) 0.0013(6) 0.0007(6) -0.0030(6)
C11 0.0289(7) 0.0270(7) 0.0241(6) -0.0010(5) -0.0016(5) -0.0008(5)
C12 0.0267(6) 0.0220(6) 0.0226(6) 0.0016(5) -0.0008(5) -0.0014(5)
C13 0.0307(7) 0.0283(7) 0.0257(7) 0.0004(5) 0.0022(5) -0.0009(6)
C14 0.0442(9) 0.0339(8) 0.0232(7) 0.0021(6) 0.0023(6) -0.0042(7)
C15 0.0434(9) 0.0317(8) 0.0295(7) 0.0076(6) -0.0093(7) -0.0065(7)
C16 0.0323(8) 0.0310(8) 0.0394(9) 0.0069(7) -0.0056(7) 0.0020(6)
C17 0.0291(7) 0.0296(8) 0.0291(7) 0.0024(6) 0.0025(6) 0.0023(6)
C18 0.0239(6) 0.0226(7) 0.0233(6) -0.0014(5) -0.0014(5) 0.0014(5)
C19 0.0302(7) 0.0285(7) 0.0339(7) -0.0031(6) 0.0062(6) 0.0019(6)
C20 0.0410(9) 0.0285(7) 0.0362(8) -0.0071(6) 0.0028(6) 0.0060(6)
C21 0.0367(8) 0.0242(7) 0.0400(8) -0.0037(6) -0.0105(6) 0.0010(6)
C22 0.0268(7) 0.0316(8) 0.0402(8) 0.0018(6) -0.0035(6) -0.0038(6)
C23 0.0244(7) 0.0301(7) 0.0284(7) -0.0012(6) 0.0014(5) 0.0007(5)
_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 C1 2.1081(14) . ?
F1 C2 1.3469(17) . ?
F2 C3 1.3508(16) . ?
P1 C12 1.7923(14) . ?
P1 C6 1.7938(14) . ?
P1 C18 1.7964(14) . ?
P1 C4 1.8044(14) . ?
C1 C2 1.382(2) . ?
C1 C3 1.380(2) . ?
C2 C3 1.375(2) 3 ?
C3 C2 1.375(2) 3 ?
C4 C5 1.530(2) . ?
C6 C7 1.4009(18) . ?
C6 C11 1.3977(19) . ?
C7 C8 1.381(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.384(2) . ?
C10 C11 1.386(2) . ?
C12 C17 1.396(2) . ?
C12 C13 1.394(2) . ?
C13 C14 1.390(2) . ?
C14 C15 1.384(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.386(2) . ?
C18 C23 1.392(2) . ?
C18 C19 1.396(2) . ?
C19 C20 1.386(2) . ?
C20 C21 1.379(2) . ?
C21 C22 1.382(2) . ?
C22 C23 1.388(2) . ?
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
C12 P1 C6 109.53(6) . . ?
C12 P1 C18 107.39(6) . . ?
C6 P1 C18 110.68(7) . . ?
C12 P1 C4 110.13(7) . . ?
C6 P1 C4 109.40(7) . . ?
C18 P1 C4 109.68(7) . . ?
C2 C1 C3 116.28(13) . . ?
C2 C1 I1 121.67(10) . . ?
C3 C1 I1 122.02(10) . . ?
F1 C2 C1 120.08(13) . . ?
F1 C2 C3 118.35(13) . 3 ?
C1 C2 C3 121.56(13) . 3 ?
F2 C3 C2 118.21(13) . 3 ?
F2 C3 C1 119.62(12) . . ?
C2 C3 C1 122.16(13) 3 . ?
C5 C4 P1 113.10(11) . . ?
C7 C6 C11 119.68(13) . . ?
C7 C6 P1 120.07(11) . . ?
C11 C6 P1 120.06(10) . . ?
C8 C7 C6 119.88(13) . . ?
C7 C8 C9 120.11(13) . . ?
C10 C9 C8 120.35(14) . . ?
C9 C10 C11 120.12(14) . . ?
C10 C11 C6 119.85(13) . . ?
C17 C12 C13 120.23(13) . . ?
C17 C12 P1 118.44(11) . . ?
C13 C12 P1 121.19(11) . . ?
C14 C13 C12 119.18(14) . . ?
C15 C14 C13 120.52(15) . . ?
C16 C15 C14 120.24(15) . . ?
C17 C16 C15 120.02(15) . . ?
C16 C17 C12 119.79(15) . . ?
C23 C18 C19 119.86(13) . . ?
C23 C18 P1 117.64(11) . . ?
C19 C18 P1 122.21(11) . . ?
C20 C19 C18 119.66(14) . . ?
C21 C20 C19 120.27(15) . . ?
C20 C21 C22 120.37(15) . . ?
C21 C22 C23 120.12(14) . . ?
C18 C23 C22 119.73(14) . . ?
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 C1 C2 F1 179.67(13) . . . . ?
I1 C1 C2 F1 -2.21(19) . . . . ?
C3 C1 C2 C3 0.0(2) . . . 3 ?
I1 C1 C2 C3 178.16(11) . . . 3 ?
C2 C1 C3 F2 179.28(13) . . . . ?
I1 C1 C3 F2 1.16(19) . . . . ?
C2 C1 C3 C2 0.0(2) . . . 3 ?
I1 C1 C3 C2 -178.15(11) . . . 3 ?
C12 P1 C4 C5 -178.89(11) . . . . ?
C6 P1 C4 C5 60.68(13) . . . . ?
C18 P1 C4 C5 -60.90(13) . . . . ?
C12 P1 C6 C7 158.44(12) . . . . ?
C18 P1 C6 C7 40.21(14) . . . . ?
C4 P1 C6 C7 -80.76(13) . . . . ?
C12 P1 C6 C11 -26.73(13) . . . . ?
C18 P1 C6 C11 -144.95(11) . . . . ?
C4 P1 C6 C11 94.07(12) . . . . ?
C11 C6 C7 C8 0.3(2) . . . . ?
P1 C6 C7 C8 175.20(12) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C6 0.6(2) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
P1 C6 C11 C10 -175.59(11) . . . . ?
C6 P1 C12 C17 -46.48(13) . . . . ?
C18 P1 C12 C17 73.77(13) . . . . ?
C4 P1 C12 C17 -166.84(11) . . . . ?
C6 P1 C12 C13 137.87(12) . . . . ?
C18 P1 C12 C13 -101.88(13) . . . . ?
C4 P1 C12 C13 17.51(14) . . . . ?
C17 C12 C13 C14 0.9(2) . . . . ?
P1 C12 C13 C14 176.49(12) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C12 1.3(2) . . . . ?
C13 C12 C17 C16 -1.5(2) . . . . ?
P1 C12 C17 C16 -177.18(12) . . . . ?
C12 P1 C18 C23 77.76(12) . . . . ?
C6 P1 C18 C23 -162.72(11) . . . . ?
C4 P1 C18 C23 -41.91(13) . . . . ?
C12 P1 C18 C19 -95.98(13) . . . . ?
C6 P1 C18 C19 23.54(14) . . . . ?
C4 P1 C18 C19 144.34(12) . . . . ?
C23 C18 C19 C20 0.5(2) . . . . ?
P1 C18 C19 C20 174.16(12) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C19 C18 C23 C22 -0.7(2) . . . . ?
P1 C18 C23 C22 -174.63(11) . . . . ?
C21 C22 C23 C18 0.4(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.056