# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


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#
#                 Cambridge Crystallographic Data Centre
#                                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_a20905a
_database_code_depnum_ccdc_archive 'CCDC 901494'
#TrackingRef 'a20905a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 Cl2 I N3 O3 P'
_chemical_formula_weight         608.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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                   17.266(14)
_cell_length_b                   8.920(7)
_cell_length_c                   16.576(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.576(10)
_cell_angle_gamma                90.00
_cell_volume                     2531(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    855
_cell_measurement_theta_min      2.575
_cell_measurement_theta_max      21.842

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    1.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7444
_exptl_absorpt_correction_T_max  0.9257
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10089
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4452
_reflns_number_gt                3034
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0889P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4452
_refine_ls_number_parameters     299
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
P1 P 0.12605(11) -0.1234(2) 0.30303(11) 0.0800(5) Uani 1 1 d . . .
O1 O 0.1504(3) -0.1519(6) 0.2189(3) 0.1212(19) Uani 1 1 d . A .
O2 O 0.1296(3) -0.2865(6) 0.3361(4) 0.1182(18) Uani 1 1 d . . .
O3 O 0.0571(3) -0.0407(6) 0.3085(4) 0.1158(19) Uani 1 1 d . . .
C1 C 0.4315(3) 0.0785(7) 0.5654(3) 0.0614(13) Uani 1 1 d . . .
C2 C 0.3999(4) -0.0531(7) 0.5861(4) 0.0715(16) Uani 1 1 d . . .
H2 H 0.4218 -0.1059 0.6319 0.086 Uiso 1 1 calc R . .
C3 C 0.3355(3) -0.1064(7) 0.5384(3) 0.0702(15) Uani 1 1 d . . .
H3 H 0.3128 -0.1954 0.5528 0.084 Uiso 1 1 calc R . .
C4 C 0.3028(3) -0.0312(6) 0.4689(3) 0.0563(13) Uani 1 1 d . . .
C5 C 0.2123(3) -0.0333(6) 0.3569(4) 0.0591(13) Uani 1 1 d . . .
C6 C 0.0980(7) -0.3332(14) 0.4016(8) 0.183(5) Uani 1 1 d . . .
H6A H 0.1325 -0.3024 0.4497 0.220 Uiso 1 1 calc R . .
H6B H 0.0490 -0.2801 0.4023 0.220 Uiso 1 1 calc R . .
C7 C 0.0839(12) -0.4783(11) 0.4085(10) 0.238(10) Uani 1 1 d . . .
H7A H 0.0601 -0.4958 0.4568 0.357 Uiso 1 1 calc R . .
H7B H 0.1322 -0.5329 0.4118 0.357 Uiso 1 1 calc R . .
H7C H 0.0493 -0.5115 0.3618 0.357 Uiso 1 1 calc R . .
C8 C 0.1232(11) -0.2463(19) 0.1610(9) 0.242(7) Uani 1 1 d DU . .
H8A H 0.1343 -0.3437 0.1858 0.290 Uiso 0.527(19) 1 calc PR A 1
H8B H 0.1595 -0.2360 0.1214 0.290 Uiso 0.527(19) 1 calc PR A 1
H8C H 0.0736 -0.2001 0.1405 0.290 Uiso 0.473(19) 1 d PR A 2
H8D H 0.1093 -0.3297 0.1938 0.290 Uiso 0.473(19) 1 d PR A 2
C9 C 0.0482(14) -0.269(3) 0.1106(15) 0.248(12) Uani 0.527(19) 1 d PDU A 1
H9A H 0.0471 -0.3665 0.0863 0.372 Uiso 0.527(19) 1 calc PR A 1
H9B H 0.0415 -0.1939 0.0687 0.372 Uiso 0.527(19) 1 calc PR A 1
H9C H 0.0069 -0.2606 0.1438 0.372 Uiso 0.527(19) 1 calc PR A 1
C9' C 0.140(2) -0.332(4) 0.0895(15) 0.258(14) Uani 0.473(19) 1 d PDU A 2
H9'D H 0.1016 -0.4090 0.0771 0.387 Uiso 0.473(19) 1 calc PR A 2
H9'E H 0.1910 -0.3781 0.1013 0.387 Uiso 0.473(19) 1 calc PR A 2
H9'F H 0.1400 -0.2664 0.0437 0.387 Uiso 0.473(19) 1 calc PR A 2
C10 C 0.2465(2) 0.1365(6) 0.1840(3) 0.0516(12) Uani 1 1 d . . .
C11 C 0.2175(3) 0.1956(6) 0.1100(3) 0.0593(13) Uani 1 1 d . . .
H11 H 0.2436 0.1808 0.0650 0.071 Uiso 1 1 calc R . .
C12 C 0.1500(3) 0.2764(6) 0.1030(3) 0.0610(14) Uani 1 1 d . . .
C13 C 0.1112(3) 0.2974(6) 0.1687(4) 0.0651(15) Uani 1 1 d . . .
H13 H 0.0645 0.3506 0.1632 0.078 Uiso 1 1 calc R . .
C14 C 0.1416(3) 0.2393(6) 0.2431(3) 0.0587(13) Uani 1 1 d . . .
H14 H 0.1161 0.2565 0.2883 0.070 Uiso 1 1 calc R . .
C15 C 0.2085(2) 0.1573(5) 0.2515(3) 0.0493(11) Uani 1 1 d . . .
C16 C 0.2996(2) 0.1848(6) 0.3758(3) 0.0477(11) Uani 1 1 d . . .
C17 C 0.3617(3) 0.4358(6) 0.3613(3) 0.0587(13) Uani 1 1 d . . .
C18 C 0.3304(4) 0.5518(7) 0.2959(4) 0.089(2) Uani 1 1 d . . .
H18A H 0.2778 0.5786 0.3027 0.133 Uiso 1 1 calc R . .
H18B H 0.3312 0.5093 0.2428 0.133 Uiso 1 1 calc R . .
H18C H 0.3628 0.6397 0.3015 0.133 Uiso 1 1 calc R . .
C19 C 0.4437(3) 0.3964(8) 0.3508(4) 0.0830(18) Uani 1 1 d . . .
H19A H 0.4445 0.3505 0.2985 0.125 Uiso 1 1 calc R . .
H19B H 0.4644 0.3278 0.3927 0.125 Uiso 1 1 calc R . .
H19C H 0.4750 0.4858 0.3542 0.125 Uiso 1 1 calc R . .
C20 C 0.3546(4) 0.5083(6) 0.4424(4) 0.0763(17) Uani 1 1 d . . .
H20A H 0.3008 0.5315 0.4456 0.115 Uiso 1 1 calc R . .
H20B H 0.3848 0.5990 0.4475 0.115 Uiso 1 1 calc R . .
H20C H 0.3737 0.4407 0.4855 0.115 Uiso 1 1 calc R . .
C21 C 0.3350(3) 0.1042(6) 0.4487(3) 0.0487(11) Uani 1 1 d . . .
C22 C 0.4007(3) 0.1567(6) 0.4993(3) 0.0563(12) Uani 1 1 d . . .
H22 H 0.4234 0.2470 0.4871 0.068 Uiso 1 1 calc R . .
Cl1 Cl 0.51362(9) 0.1468(2) 0.62430(10) 0.0885(5) Uani 1 1 d . . .
Cl2 Cl 0.11255(10) 0.3486(2) 0.00926(10) 0.0936(5) Uani 1 1 d . . .
I1 I 0.35042(2) 0.01618(5) 0.19351(2) 0.0798(2) Uani 1 1 d . . .
N1 N 0.2399(3) -0.0979(5) 0.4236(3) 0.0622(11) Uani 1 1 d . . .
N2 N 0.2396(2) 0.0969(4) 0.3290(2) 0.0495(9) Uani 1 1 d . . .
N3 N 0.3092(2) 0.3097(5) 0.3434(2) 0.0544(10) 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
P1 0.0771(11) 0.0772(12) 0.0820(12) 0.0014(9) -0.0036(9) -0.0366(9)
O1 0.152(5) 0.111(4) 0.097(4) -0.038(3) 0.002(3) -0.068(4)
O2 0.126(4) 0.100(4) 0.124(4) 0.002(3) -0.002(3) -0.062(3)
O3 0.061(3) 0.125(4) 0.158(5) 0.006(4) 0.003(3) -0.031(3)
C1 0.058(3) 0.070(4) 0.054(3) -0.002(3) 0.001(2) 0.003(3)
C2 0.077(4) 0.078(4) 0.057(3) 0.003(3) 0.000(3) 0.014(3)
C3 0.083(4) 0.064(4) 0.064(4) 0.011(3) 0.010(3) -0.006(3)
C4 0.062(3) 0.052(3) 0.056(3) -0.001(2) 0.013(2) -0.002(2)
C5 0.055(3) 0.057(3) 0.066(4) -0.009(3) 0.012(3) -0.014(2)
C6 0.167(10) 0.166(11) 0.219(13) 0.075(10) 0.032(9) -0.049(8)
C7 0.41(3) 0.085(7) 0.256(18) 0.025(8) 0.159(19) -0.057(10)
C8 0.32(2) 0.234(16) 0.155(12) -0.015(12) -0.011(13) -0.046(15)
C9 0.39(3) 0.20(2) 0.153(18) -0.071(16) 0.01(2) -0.04(2)
C9' 0.33(3) 0.26(3) 0.17(2) 0.03(2) -0.04(2) -0.08(2)
C10 0.036(2) 0.058(3) 0.060(3) -0.003(2) 0.004(2) 0.004(2)
C11 0.052(3) 0.073(4) 0.052(3) -0.003(3) 0.000(2) 0.007(3)
C12 0.055(3) 0.055(3) 0.068(4) -0.006(3) -0.011(3) -0.003(2)
C13 0.044(3) 0.060(3) 0.089(4) -0.006(3) -0.003(3) 0.004(2)
C14 0.045(3) 0.057(3) 0.076(4) -0.010(3) 0.015(2) -0.001(2)
C15 0.039(2) 0.052(3) 0.056(3) -0.007(2) 0.004(2) -0.006(2)
C16 0.042(2) 0.052(3) 0.049(3) -0.007(2) 0.009(2) -0.003(2)
C17 0.058(3) 0.059(3) 0.058(3) -0.001(3) 0.005(2) -0.021(3)
C18 0.098(5) 0.069(4) 0.093(5) 0.023(4) -0.010(4) -0.028(4)
C19 0.061(3) 0.106(5) 0.085(4) -0.005(4) 0.019(3) -0.023(3)
C20 0.088(4) 0.064(4) 0.076(4) -0.011(3) 0.007(3) -0.010(3)
C21 0.047(2) 0.054(3) 0.046(3) -0.004(2) 0.007(2) 0.001(2)
C22 0.053(3) 0.054(3) 0.060(3) -0.003(3) 0.003(2) -0.005(2)
Cl1 0.0725(9) 0.1078(13) 0.0771(10) -0.0024(9) -0.0199(8) -0.0031(9)
Cl2 0.0975(11) 0.0889(12) 0.0858(11) 0.0192(9) -0.0196(9) 0.0126(9)
I1 0.0606(3) 0.1070(4) 0.0716(3) -0.0026(2) 0.00744(19) 0.0316(2)
N1 0.067(3) 0.058(3) 0.061(3) 0.001(2) 0.007(2) -0.014(2)
N2 0.047(2) 0.048(2) 0.052(2) -0.0020(19) 0.0027(17) -0.0096(18)
N3 0.054(2) 0.054(3) 0.054(2) -0.002(2) 0.0045(18) -0.010(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
P1 O3 1.414(6) . ?
P1 O1 1.530(6) . ?
P1 O2 1.553(6) . ?
P1 C5 1.819(5) . ?
O1 C8 1.317(15) . ?
O2 C6 1.344(11) . ?
C1 C22 1.348(7) . ?
C1 C2 1.358(9) . ?
C1 Cl1 1.723(6) . ?
C2 C3 1.364(8) . ?
C3 C4 1.387(8) . ?
C4 N1 1.372(7) . ?
C4 C21 1.388(7) . ?
C5 N1 1.281(7) . ?
C5 N2 1.357(6) . ?
C6 C7 1.325(12) . ?
C8 C9 1.458(10) . ?
C8 C9' 1.475(10) . ?
C10 C11 1.368(7) . ?
C10 C15 1.381(6) . ?
C10 I1 2.079(4) . ?
C11 C12 1.362(7) . ?
C12 C13 1.365(8) . ?
C12 Cl2 1.727(6) . ?
C13 C14 1.377(8) . ?
C14 C15 1.359(6) . ?
C15 N2 1.431(6) . ?
C16 N3 1.257(6) . ?
C16 N2 1.441(6) . ?
C16 C21 1.469(7) . ?
C17 N3 1.450(6) . ?
C17 C19 1.492(8) . ?
C17 C20 1.510(9) . ?
C17 C18 1.545(8) . ?
C21 C22 1.400(6) . ?

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
O3 P1 O1 118.7(4) . . ?
O3 P1 O2 117.4(3) . . ?
O1 P1 O2 99.4(3) . . ?
O3 P1 C5 112.3(3) . . ?
O1 P1 C5 102.5(3) . . ?
O2 P1 C5 104.4(3) . . ?
C8 O1 P1 131.1(9) . . ?
C6 O2 P1 125.0(7) . . ?
C22 C1 C2 121.7(5) . . ?
C22 C1 Cl1 119.0(5) . . ?
C2 C1 Cl1 119.3(4) . . ?
C1 C2 C3 118.6(5) . . ?
C2 C3 C4 121.7(6) . . ?
N1 C4 C3 116.8(5) . . ?
N1 C4 C21 123.9(5) . . ?
C3 C4 C21 119.3(5) . . ?
N1 C5 N2 124.9(5) . . ?
N1 C5 P1 114.3(4) . . ?
N2 C5 P1 120.6(4) . . ?
C7 C6 O2 118.1(13) . . ?
O1 C8 C9 135.2(19) . . ?
O1 C8 C9' 146(2) . . ?
C9 C8 C9' 74.2(18) . . ?
C11 C10 C15 121.2(4) . . ?
C11 C10 I1 118.5(4) . . ?
C15 C10 I1 120.3(4) . . ?
C12 C11 C10 119.2(5) . . ?
C11 C12 C13 120.6(5) . . ?
C11 C12 Cl2 119.3(4) . . ?
C13 C12 Cl2 120.1(4) . . ?
C12 C13 C14 119.6(5) . . ?
C15 C14 C13 120.9(5) . . ?
C14 C15 C10 118.5(5) . . ?
C14 C15 N2 120.5(4) . . ?
C10 C15 N2 120.9(4) . . ?
N3 C16 N2 112.2(4) . . ?
N3 C16 C21 136.1(4) . . ?
N2 C16 C21 111.6(4) . . ?
N3 C17 C19 111.8(5) . . ?
N3 C17 C20 113.1(4) . . ?
C19 C17 C20 113.2(5) . . ?
N3 C17 C18 103.0(4) . . ?
C19 C17 C18 108.9(5) . . ?
C20 C17 C18 106.0(5) . . ?
C4 C21 C22 117.8(5) . . ?
C4 C21 C16 119.2(4) . . ?
C22 C21 C16 123.0(5) . . ?
C1 C22 C21 121.0(5) . . ?
C5 N1 C4 117.1(4) . . ?
C5 N2 C15 121.5(4) . . ?
C5 N2 C16 122.6(4) . . ?
C15 N2 C16 115.9(4) . . ?
C16 N3 C17 135.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.115