# Supplementary Material (ESI) for Chemical Science
# This journal is (c) The Royal Society of Chemistry 2011

data_global

_journal_coden_Cambridge         1475

loop_
_publ_author_name
'David MacMillan'

_publ_contact_author_name        'David MacMillan'
_publ_contact_author_address     
;
rick Laboratory
Washington Rd
Princeton
New Jersey
United States
NJ08544
;

_publ_contact_author_email       dmacmill@princeton.edu

data_k08308
_database_code_depnum_ccdc_archive 'CCDC 805599'
#TrackingRef 'diazonamide-int-11a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H59 Cl3 N4 O8 Si, CH Cl3'
_chemical_formula_sum            'C47 H59 Cl3 N4 O8 Si'
_chemical_formula_weight         942.42
_chemical_absolute_configuration unk

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  C2y

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

_cell_length_a                   19.546(4)
_cell_length_b                   17.360(4)
_cell_length_c                   19.889(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.63(3)
_cell_angle_gamma                90.00
_cell_volume                     6499(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    8612
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      24.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.963
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    0.201
# Absorption correction

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_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  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8612
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         24.38
_reflns_number_total             5228
_reflns_number_gt                3121
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        Denzo-SMN
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'

_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
#_refine_ls_abs_structure_details
# 'Flack H D (1983), Acta Cryst. A39, 876-881'
#_refine_ls_abs_structure_Flack 0.0(3)
_refine_ls_number_reflns         5228
_refine_ls_number_parameters     568
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.1136
_refine_ls_wR_factor_ref         0.3174
_refine_ls_wR_factor_gt          0.2908
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.18451(15) 0.3815(2) 0.31172(15) 0.0860(9) Uani 1 1 d . . .
O1 O 0.5341(4) 0.6479(4) 0.8038(3) 0.0843(18) Uani 1 1 d . . .
O2 O 0.4264(3) 0.4519(4) 0.7182(3) 0.0741(16) Uani 1 1 d . . .
O3 O 0.4873(4) 0.3366(4) 0.9303(4) 0.095(2) Uani 1 1 d . . .
H3 H 0.4976 0.3425 0.9738 0.143 Uiso 0.50 1 calc PR . .
O4 O 0.4828(4) 0.4640(4) 0.9345(3) 0.090(2) Uani 1 1 d . . .
H4 H 0.4938 0.4543 0.9775 0.135 Uiso 0.50 1 calc PR . .
O5 O 0.3925(4) 0.6989(4) 0.9838(3) 0.0840(19) Uani 1 1 d . . .
O6 O 0.3075(4) 0.4378(4) 0.5698(3) 0.089(2) Uani 1 1 d . . .
O7 O 0.4400(4) 0.4544(5) 0.4089(3) 0.096(2) Uani 1 1 d . . .
O8 O 0.2523(4) 0.4450(4) 0.3373(3) 0.0844(18) Uani 1 1 d . . .
N1 N 0.4737(4) 0.6468(5) 0.8959(4) 0.077(2) Uani 1 1 d . . .
H1A H 0.4971 0.6823 0.9246 0.092 Uiso 1 1 calc R . .
N2 N 0.4535(4) 0.3426(5) 0.7809(4) 0.072(2) Uani 1 1 d . . .
N3 N 0.4217(4) 0.3991(5) 0.5953(4) 0.078(2) Uani 1 1 d . . .
H3B H 0.4628 0.4051 0.5858 0.094 Uiso 1 1 calc R . .
N4 N 0.3459(4) 0.4850(6) 0.4450(4) 0.082(2) Uani 1 1 d . . .
H4B H 0.2993 0.4888 0.4328 0.099 Uiso 1 1 calc R . .
C1 C 0.4347(5) 0.5596(6) 0.7972(5) 0.068(2) Uani 1 1 d . . .
C2 C 0.3777(3) 0.5765(4) 0.8318(3) 0.082(3) Uani 1 1 d G . .
C3 C 0.3073(4) 0.5524(4) 0.8153(3) 0.084(3) Uani 1 1 d G . .
H3A H 0.2894 0.5191 0.7766 0.101 Uiso 1 1 calc R . .
C4 C 0.2631(3) 0.5770(5) 0.8553(4) 0.115(4) Uani 1 1 d G . .
H4A H 0.2150 0.5605 0.8440 0.139 Uiso 1 1 calc R . .
C5 C 0.2893(3) 0.6257(5) 0.9119(4) 0.103(4) Uani 1 1 d G . .
H5A H 0.2592 0.6425 0.9392 0.123 Uiso 1 1 calc R . .
C6 C 0.3597(3) 0.6498(4) 0.9284(3) 0.083(3) Uani 1 1 d G . .
C7 C 0.4039(3) 0.6252(4) 0.8883(3) 0.074(3) Uani 1 1 d G . .
C8 C 0.5021(5) 0.6000(6) 0.8474(5) 0.075(3) Uani 1 1 d . . .
H8A H 0.5367 0.5608 0.8735 0.091 Uiso 1 1 calc R . .
C9 C 0.4915(3) 0.6467(4) 0.7393(3) 0.080(3) Uani 1 1 d G . .
C10 C 0.5075(3) 0.6780(4) 0.6811(4) 0.087(3) Uani 1 1 d G . .
H10A H 0.5487 0.7091 0.6866 0.105 Uiso 1 1 calc R . .
C11 C 0.4634(4) 0.6639(4) 0.6147(3) 0.088(3) Uani 1 1 d G . .
H11A H 0.4744 0.6853 0.5749 0.106 Uiso 1 1 calc R . .
C12 C 0.4031(3) 0.6185(4) 0.6066(2) 0.086(3) Uani 1 1 d G . .
C13 C 0.3871(3) 0.5872(4) 0.6649(3) 0.069(2) Uani 1 1 d G . .
H13A H 0.3459 0.5562 0.6593 0.082 Uiso 1 1 calc R . .
C14 C 0.4312(3) 0.6013(4) 0.7312(3) 0.082(3) Uani 1 1 d G . .
C15 C 0.4431(5) 0.4739(5) 0.7877(4) 0.068(2) Uani 1 1 d . . .
C16 C 0.4599(5) 0.4081(6) 0.8251(5) 0.080(3) Uani 1 1 d . . .
C17 C 0.4785(6) 0.4019(7) 0.9008(6) 0.087(3) Uani 1 1 d . . .
C18 C 0.4330(5) 0.3747(6) 0.7175(6) 0.081(3) Uani 1 1 d . . .
C19 C 0.4144(6) 0.3381(6) 0.6452(5) 0.078(3) Uani 1 1 d . . .
H19A H 0.3625 0.3261 0.6338 0.093 Uiso 1 1 calc R . .
C20 C 0.4505(6) 0.2632(6) 0.6395(6) 0.085(3) Uani 1 1 d . . .
H20A H 0.4426 0.2270 0.6758 0.102 Uiso 1 1 calc R . .
C21 C 0.4205(10) 0.2282(10) 0.5696(8) 0.142(6) Uani 1 1 d . . .
H21A H 0.4455 0.1800 0.5663 0.213 Uiso 1 1 calc R . .
H21B H 0.4265 0.2640 0.5334 0.213 Uiso 1 1 calc R . .
H21C H 0.3699 0.2177 0.5629 0.213 Uiso 1 1 calc R . .
C22 C 0.5294(7) 0.2748(7) 0.6515(6) 0.100(4) Uani 1 1 d . . .
H22A H 0.5521 0.2251 0.6482 0.150 Uiso 1 1 calc R . .
H22B H 0.5495 0.2969 0.6979 0.150 Uiso 1 1 calc R . .
H22C H 0.5379 0.3100 0.6160 0.150 Uiso 1 1 calc R . .
C23 C 0.3676(5) 0.4452(6) 0.5644(5) 0.069(2) Uani 1 1 d . . .
C24 C 0.3845(6) 0.5069(6) 0.5170(5) 0.079(3) Uani 1 1 d . . .
H24A H 0.4366 0.5053 0.5212 0.094 Uiso 1 1 calc R . .
C25 C 0.3649(7) 0.5894(7) 0.5352(5) 0.091(3) Uani 1 1 d . . .
H25A H 0.3745 0.6254 0.5002 0.109 Uiso 1 1 calc R . .
H25B H 0.3132 0.5910 0.5306 0.109 Uiso 1 1 calc R . .
C26 C 0.3766(5) 0.4603(5) 0.3983(4) 0.063(2) Uani 1 1 d . . .
C27 C 0.3207(5) 0.4388(5) 0.3273(5) 0.077(3) Uani 1 1 d . . .
H27A H 0.3287 0.3842 0.3153 0.093 Uiso 1 1 calc R . .
C28 C 0.3303(6) 0.4908(7) 0.2691(5) 0.079(3) Uani 1 1 d . . .
H28A H 0.2898 0.4791 0.2275 0.095 Uiso 1 1 calc R . .
C29 C 0.3230(8) 0.5764(9) 0.2859(8) 0.120(4) Uani 1 1 d . . .
H29A H 0.2791 0.5841 0.3000 0.180 Uiso 1 1 calc R . .
H29B H 0.3214 0.6075 0.2444 0.180 Uiso 1 1 calc R . .
H29C H 0.3638 0.5921 0.3241 0.180 Uiso 1 1 calc R . .
C30 C 0.3945(8) 0.4778(9) 0.2474(8) 0.123(4) Uani 1 1 d . . .
H30A H 0.4014 0.4223 0.2427 0.184 Uiso 1 1 calc R . .
H30B H 0.4354 0.4992 0.2823 0.184 Uiso 1 1 calc R . .
H30C H 0.3902 0.5030 0.2023 0.184 Uiso 1 1 calc R . .
C31 C 0.1501(6) 0.3781(5) 0.2157(5) 0.100(4) Uani 1 1 d D . .
H31A H 0.1908 0.3591 0.1987 0.120 Uiso 1 1 calc R . .
C32 C 0.1296(6) 0.4541(6) 0.1791(7) 0.104(4) Uani 1 1 d D . .
H32A H 0.1133 0.4456 0.1286 0.156 Uiso 1 1 calc R . .
H32B H 0.1708 0.4885 0.1897 0.156 Uiso 1 1 calc R . .
H32C H 0.0912 0.4775 0.1952 0.156 Uiso 1 1 calc R . .
C33 C 0.0918(8) 0.3193(10) 0.1901(8) 0.145(6) Uani 1 1 d D . .
H33A H 0.0775 0.3189 0.1389 0.218 Uiso 1 1 calc R . .
H33B H 0.0509 0.3328 0.2073 0.218 Uiso 1 1 calc R . .
H33C H 0.1093 0.2682 0.2074 0.218 Uiso 1 1 calc R . .
C34 C 0.2145(8) 0.2839(9) 0.3485(7) 0.141(7) Uani 1 1 d D . .
H34A H 0.1708 0.2516 0.3413 0.169 Uiso 1 1 calc R . .
C35 C 0.2535(15) 0.2780(13) 0.4250(9) 0.219(13) Uani 1 1 d D . .
H35A H 0.2650 0.2239 0.4371 0.329 Uiso 1 1 calc R . .
H35B H 0.2233 0.2980 0.4531 0.329 Uiso 1 1 calc R . .
H35C H 0.2974 0.3081 0.4344 0.329 Uiso 1 1 calc R . .
C36 C 0.2648(15) 0.2402(11) 0.3171(17) 0.227(14) Uani 1 1 d D . .
H36A H 0.2753 0.1899 0.3401 0.340 Uiso 1 1 calc R . .
H36B H 0.3090 0.2695 0.3237 0.340 Uiso 1 1 calc R . .
H36C H 0.2429 0.2326 0.2671 0.340 Uiso 1 1 calc R . .
C37 C 0.1160(8) 0.4262(11) 0.3478(11) 0.164(8) Uani 1 1 d D . .
H37A H 0.0913 0.4468 0.3006 0.197 Uiso 1 1 calc R . .
C38 C 0.0476(10) 0.3899(14) 0.3531(14) 0.208(11) Uani 1 1 d D . .
H38A H 0.0194 0.4282 0.3701 0.312 Uiso 1 1 calc R . .
H38B H 0.0583 0.3465 0.3857 0.312 Uiso 1 1 calc R . .
H38C H 0.0207 0.3716 0.3069 0.312 Uiso 1 1 calc R . .
C39 C 0.1327(16) 0.5070(12) 0.3745(14) 0.212(12) Uani 1 1 d D . .
H39A H 0.0922 0.5280 0.3888 0.318 Uiso 1 1 calc R . .
H39B H 0.1420 0.5392 0.3375 0.318 Uiso 1 1 calc R . .
H39C H 0.1748 0.5065 0.4147 0.318 Uiso 1 1 calc R . .
C40 C 0.3560(7) 0.7265(10) 1.0317(8) 0.126(5) Uani 1 1 d . . .
H40A H 0.3589 0.6866 1.0680 0.152 Uiso 1 1 calc R . .
H40B H 0.3053 0.7329 1.0065 0.152 Uiso 1 1 calc R . .
C41 C 0.3812(5) 0.7972(4) 1.0655(4) 0.095(3) Uani 1 1 d G . .
C42 C 0.4089(5) 0.8546(6) 1.0317(4) 0.118(4) Uani 1 1 d G . .
H42A H 0.4150 0.8454 0.9866 0.142 Uiso 1 1 calc R . .
C43 C 0.4276(5) 0.9254(5) 1.0640(7) 0.138(6) Uani 1 1 d G . .
H43A H 0.4465 0.9647 1.0409 0.165 Uiso 1 1 calc R . .
C44 C 0.4187(5) 0.9389(5) 1.1300(7) 0.142(6) Uani 1 1 d G . .
H44A H 0.4315 0.9873 1.1521 0.171 Uiso 1 1 calc R . .
C45 C 0.3910(6) 0.8815(7) 1.1638(4) 0.134(5) Uani 1 1 d G . .
H45A H 0.3849 0.8906 1.2089 0.161 Uiso 1 1 calc R . .
C46 C 0.3723(5) 0.8106(6) 1.1315(4) 0.110(4) Uani 1 1 d G . .
H46A H 0.3534 0.7714 1.1546 0.133 Uiso 1 1 calc R . .
Cl1 Cl 0.2755(5) 0.3628(4) 0.0878(3) 0.133(3) Uani 0.50 1 d PD . .
Cl2 Cl 0.2424(5) 0.5208(5) 0.0639(4) 0.141(3) Uani 0.50 1 d PD . .
Cl3 Cl 0.3492(4) 0.4592(6) 0.0157(7) 0.172(4) Uani 0.50 1 d PD . .
C1S C 0.2698(7) 0.4385(6) 0.0316(8) 0.125(11) Uani 0.50 1 d PD . .
H1S H 0.2346 0.4254 -0.0136 0.150 Uiso 0.50 1 calc PR . .
Cl4 Cl 0.1845(5) 0.5304(7) 0.5786(6) 0.164(4) Uani 0.50 1 d PD . .
Cl5 Cl 0.1064(6) 0.5554(7) 0.6790(5) 0.165(3) Uani 0.50 1 d PD . .
Cl6 Cl 0.0346(4) 0.5406(7) 0.5310(5) 0.152(3) Uani 0.50 1 d PD . .
C2S C 0.1091(6) 0.5649(15) 0.5944(6) 0.174(17) Uani 0.50 1 d PD . .
H2S H 0.1129 0.6218 0.5886 0.209 Uiso 0.50 1 calc PR . .

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
Si1 0.0806(17) 0.086(2) 0.0919(18) -0.0044(15) 0.0240(14) -0.0094(15)
O1 0.090(4) 0.082(4) 0.081(4) -0.008(4) 0.022(4) -0.006(4)
O2 0.091(4) 0.055(4) 0.074(4) 0.002(3) 0.019(3) 0.006(3)
O3 0.134(6) 0.058(4) 0.094(5) 0.009(4) 0.031(4) 0.004(4)
O4 0.134(6) 0.061(4) 0.070(4) 0.001(3) 0.019(4) 0.009(4)
O5 0.090(4) 0.090(5) 0.080(4) -0.022(4) 0.038(4) 0.002(4)
O6 0.101(5) 0.078(4) 0.087(4) 0.000(4) 0.022(4) 0.001(4)
O7 0.081(5) 0.126(6) 0.086(4) -0.007(4) 0.031(3) -0.002(4)
O8 0.077(4) 0.079(4) 0.096(4) -0.018(4) 0.021(3) -0.008(3)
N1 0.071(5) 0.080(5) 0.077(5) -0.012(4) 0.017(4) -0.006(4)
N2 0.078(5) 0.065(5) 0.080(5) -0.004(4) 0.032(4) -0.006(4)
N3 0.077(5) 0.076(5) 0.084(5) -0.002(4) 0.024(4) 0.003(4)
N4 0.079(5) 0.098(6) 0.071(5) 0.008(4) 0.021(4) -0.007(5)
C1 0.073(5) 0.070(6) 0.063(5) 0.004(4) 0.021(4) 0.014(5)
C2 0.086(7) 0.077(7) 0.077(6) 0.002(5) 0.011(5) -0.004(6)
C3 0.085(7) 0.085(7) 0.087(6) -0.003(6) 0.030(6) 0.007(6)
C4 0.073(7) 0.123(11) 0.143(10) -0.049(9) 0.016(7) -0.028(7)
C5 0.081(7) 0.128(10) 0.096(7) 0.000(8) 0.018(6) -0.004(7)
C6 0.069(6) 0.096(8) 0.078(6) -0.007(6) 0.010(5) 0.014(6)
C7 0.074(6) 0.070(6) 0.075(6) 0.019(5) 0.016(5) 0.016(5)
C8 0.086(6) 0.076(6) 0.066(5) -0.001(5) 0.023(5) -0.004(5)
C9 0.099(7) 0.074(6) 0.074(6) -0.005(5) 0.032(6) 0.009(6)
C10 0.096(7) 0.053(6) 0.118(8) 0.001(5) 0.040(7) -0.015(5)
C11 0.096(8) 0.074(7) 0.096(8) 0.009(6) 0.028(6) 0.011(6)
C12 0.083(7) 0.074(6) 0.096(7) -0.004(6) 0.018(6) 0.006(6)
C13 0.076(6) 0.068(6) 0.063(5) 0.004(4) 0.021(5) 0.005(5)
C14 0.083(7) 0.087(7) 0.076(7) -0.007(5) 0.022(5) 0.009(6)
C15 0.083(6) 0.062(6) 0.063(5) -0.013(4) 0.027(4) -0.004(5)
C16 0.089(7) 0.078(7) 0.071(6) 0.014(6) 0.018(5) 0.005(5)
C17 0.106(8) 0.073(8) 0.086(7) 0.000(6) 0.033(6) 0.007(6)
C18 0.090(7) 0.062(6) 0.088(7) -0.005(5) 0.017(5) 0.003(5)
C19 0.098(7) 0.068(6) 0.063(5) 0.008(5) 0.015(5) 0.000(5)
C20 0.103(8) 0.067(6) 0.087(7) 0.003(5) 0.030(6) 0.015(6)
C21 0.170(14) 0.127(12) 0.109(9) -0.048(9) 0.005(9) 0.033(10)
C22 0.117(10) 0.084(8) 0.107(8) 0.004(6) 0.044(7) 0.022(7)
C23 0.042(5) 0.071(6) 0.097(6) -0.023(5) 0.024(4) -0.011(5)
C24 0.093(7) 0.076(7) 0.066(6) 0.003(5) 0.021(5) -0.005(5)
C25 0.117(8) 0.093(8) 0.057(5) 0.005(5) 0.014(5) -0.006(7)
C26 0.072(6) 0.061(5) 0.065(5) 0.005(4) 0.034(4) 0.008(5)
C27 0.088(7) 0.047(5) 0.097(7) -0.007(5) 0.025(5) -0.028(5)
C28 0.090(7) 0.091(7) 0.061(5) 0.017(5) 0.027(5) 0.007(5)
C29 0.132(11) 0.101(10) 0.138(11) 0.038(8) 0.054(9) 0.010(8)
C30 0.142(11) 0.103(9) 0.141(11) 0.008(8) 0.068(9) -0.016(9)
C31 0.119(9) 0.084(7) 0.083(6) -0.030(6) 0.003(6) 0.016(7)
C32 0.081(7) 0.092(8) 0.127(9) 0.019(7) 0.009(6) 0.002(6)
C33 0.124(11) 0.159(15) 0.128(11) 0.012(11) -0.009(9) -0.051(11)
C34 0.115(10) 0.129(13) 0.151(13) 0.047(11) -0.013(10) -0.038(10)
C35 0.28(3) 0.132(17) 0.189(19) -0.001(15) -0.039(19) -0.086(18)
C36 0.23(2) 0.091(12) 0.41(4) 0.046(18) 0.17(3) 0.064(14)
C37 0.093(9) 0.22(2) 0.178(14) -0.007(15) 0.040(9) -0.056(12)
C38 0.18(2) 0.129(15) 0.28(3) 0.009(18) 0.008(18) -0.058(15)
C39 0.29(3) 0.153(18) 0.26(2) -0.100(18) 0.19(2) -0.051(19)
C40 0.092(8) 0.146(13) 0.128(10) -0.045(10) 0.008(7) 0.037(8)
C41 0.096(8) 0.075(7) 0.115(9) -0.006(7) 0.032(7) 0.017(6)
C42 0.114(9) 0.131(13) 0.102(8) 0.005(9) 0.016(7) -0.024(9)
C43 0.102(10) 0.077(10) 0.226(19) 0.001(11) 0.029(11) -0.012(7)
C44 0.126(12) 0.092(11) 0.191(17) -0.065(12) 0.013(11) 0.013(9)
C45 0.117(10) 0.158(16) 0.118(10) -0.024(12) 0.015(8) 0.023(11)
C46 0.116(9) 0.107(10) 0.105(9) -0.014(8) 0.025(7) 0.002(8)
Cl1 0.193(7) 0.094(5) 0.096(4) 0.002(3) 0.009(4) -0.040(5)
Cl2 0.173(7) 0.119(6) 0.134(5) 0.001(5) 0.049(5) 0.005(5)
Cl3 0.110(5) 0.146(8) 0.286(12) 0.046(8) 0.099(7) 0.026(5)
C1S 0.101(16) 0.20(3) 0.067(11) -0.022(16) 0.014(11) -0.08(2)
Cl4 0.132(6) 0.144(7) 0.220(9) -0.050(7) 0.054(6) -0.005(6)
Cl5 0.180(8) 0.179(9) 0.137(6) -0.020(6) 0.041(6) -0.018(7)
Cl6 0.107(5) 0.177(8) 0.171(7) 0.011(7) 0.036(4) 0.003(5)
C2S 0.18(3) 0.13(3) 0.26(4) -0.09(3) 0.14(3) -0.04(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
Si1 O8 1.694(8) . ?
Si1 C31 1.847(10) . ?
Si1 C37 1.852(18) . ?
Si1 C34 1.875(16) . ?
O1 C9 1.328(8) . ?
O1 C8 1.458(12) . ?
O2 C18 1.347(13) . ?
O2 C15 1.387(11) . ?
O3 C17 1.266(13) . ?
O4 C17 1.260(13) . ?
O5 C6 1.404(8) . ?
O5 C40 1.419(15) . ?
O6 C23 1.215(10) . ?
O7 C26 1.205(11) . ?
O8 C27 1.407(12) . ?
N1 C7 1.383(9) . ?
N1 C8 1.479(12) . ?
N2 C18 1.336(13) . ?
N2 C16 1.423(13) . ?
N3 C23 1.337(13) . ?
N3 C19 1.485(13) . ?
N4 C26 1.306(12) . ?
N4 C24 1.477(13) . ?
C1 C14 1.485(10) . ?
C1 C2 1.488(10) . ?
C1 C15 1.515(14) . ?
C1 C8 1.585(14) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C12 C25 1.503(11) . ?
C13 C14 1.3900 . ?
C15 C16 1.354(14) . ?
C16 C17 1.454(14) . ?
C18 C19 1.523(15) . ?
C19 C20 1.499(15) . ?
C20 C21 1.485(17) . ?
C20 C22 1.509(17) . ?
C23 C24 1.521(14) . ?
C24 C25 1.551(16) . ?
C26 C27 1.580(13) . ?
C27 C28 1.520(13) . ?
C28 C30 1.451(17) . ?
C28 C29 1.54(2) . ?
C31 C32 1.508(10) . ?
C31 C33 1.512(10) . ?
C34 C36 1.506(11) . ?
C34 C35 1.511(11) . ?
C37 C38 1.505(11) . ?
C37 C39 1.505(11) . ?
C40 C41 1.422(17) . ?
C41 C42 1.3900 . ?
C41 C46 1.3900 . ?
C42 C43 1.3900 . ?
C43 C44 1.3900 . ?
C44 C45 1.3900 . ?
C45 C46 1.3900 . ?
Cl1 C1S 1.711(9) . ?
Cl2 C1S 1.711(10) . ?
Cl3 C1S 1.704(10) . ?
Cl4 C2S 1.696(10) . ?
Cl5 C2S 1.706(10) . ?
Cl6 Cl6 1.564(18) 2_556 ?
Cl6 C2S 1.704(10) . ?

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
O8 Si1 C31 111.6(4) . . ?
O8 Si1 C37 101.5(5) . . ?
C31 Si1 C37 108.3(7) . . ?
O8 Si1 C34 109.5(5) . . ?
C31 Si1 C34 111.3(6) . . ?
C37 Si1 C34 114.2(8) . . ?
C9 O1 C8 108.0(7) . . ?
C18 O2 C15 106.6(7) . . ?
C6 O5 C40 121.7(8) . . ?
C27 O8 Si1 127.1(6) . . ?
C7 N1 C8 108.2(7) . . ?
C18 N2 C16 101.8(8) . . ?
C23 N3 C19 121.8(8) . . ?
C26 N4 C24 124.2(9) . . ?
C14 C1 C2 116.8(7) . . ?
C14 C1 C15 110.4(7) . . ?
C2 C1 C15 111.7(8) . . ?
C14 C1 C8 100.0(7) . . ?
C2 C1 C8 102.8(7) . . ?
C15 C1 C8 114.4(8) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 130.4(6) . . ?
C7 C2 C1 109.5(6) . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 O5 114.4(5) . . ?
C5 C6 O5 125.6(5) . . ?
N1 C7 C6 127.0(5) . . ?
N1 C7 C2 113.0(5) . . ?
C6 C7 C2 120.0 . . ?
O1 C8 N1 111.8(8) . . ?
O1 C8 C1 107.1(7) . . ?
N1 C8 C1 105.0(7) . . ?
O1 C9 C10 125.1(5) . . ?
O1 C9 C14 114.3(5) . . ?
C10 C9 C14 120.0 . . ?
C9 C10 C11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 C25 119.3(6) . . ?
C13 C12 C25 119.3(6) . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 C1 128.5(6) . . ?
C9 C14 C1 109.8(5) . . ?
C16 C15 O2 105.8(8) . . ?
C16 C15 C1 141.1(8) . . ?
O2 C15 C1 113.0(8) . . ?
C15 C16 N2 111.5(7) . . ?
C15 C16 C17 126.0(10) . . ?
N2 C16 C17 122.5(9) . . ?
O4 C17 O3 122.5(9) . . ?
O4 C17 C16 116.7(10) . . ?
O3 C17 C16 120.7(10) . . ?
N2 C18 O2 114.2(9) . . ?
N2 C18 C19 130.6(10) . . ?
O2 C18 C19 115.1(9) . . ?
N3 C19 C20 115.8(9) . . ?
N3 C19 C18 107.0(8) . . ?
C20 C19 C18 115.8(9) . . ?
C21 C20 C19 110.5(10) . . ?
C21 C20 C22 109.3(11) . . ?
C19 C20 C22 110.8(10) . . ?
O6 C23 N3 124.1(10) . . ?
O6 C23 C24 120.4(9) . . ?
N3 C23 C24 115.4(8) . . ?
N4 C24 C23 106.3(8) . . ?
N4 C24 C25 111.7(8) . . ?
C23 C24 C25 113.4(8) . . ?
C12 C25 C24 116.1(9) . . ?
O7 C26 N4 123.5(9) . . ?
O7 C26 C27 124.5(8) . . ?
N4 C26 C27 112.0(9) . . ?
O8 C27 C28 112.3(8) . . ?
O8 C27 C26 108.0(8) . . ?
C28 C27 C26 110.0(7) . . ?
C30 C28 C27 115.4(10) . . ?
C30 C28 C29 110.7(11) . . ?
C27 C28 C29 111.7(9) . . ?
C32 C31 C33 110.4(10) . . ?
C32 C31 Si1 116.5(7) . . ?
C33 C31 Si1 113.6(9) . . ?
C36 C34 C35 100(2) . . ?
C36 C34 Si1 117.7(11) . . ?
C35 C34 Si1 118.3(13) . . ?
C38 C37 C39 118.5(19) . . ?
C38 C37 Si1 126.9(16) . . ?
C39 C37 Si1 114.6(11) . . ?
O5 C40 C41 115.8(13) . . ?
C42 C41 C46 120.0 . . ?
C42 C41 C40 121.4(10) . . ?
C46 C41 C40 118.4(10) . . ?
C43 C42 C41 120.0 . . ?
C42 C43 C44 120.0 . . ?
C45 C44 C43 120.0 . . ?
C44 C45 C46 120.0 . . ?
C45 C46 C41 120.0 . . ?
Cl3 C1S Cl2 106.7(8) . . ?
Cl3 C1S Cl1 112.4(9) . . ?
Cl2 C1S Cl1 111.6(8) . . ?
Cl6 Cl6 C2S 165.6(9) 2_556 . ?
Cl4 C2S Cl6 112.8(9) . . ?
Cl4 C2S Cl5 114.1(11) . . ?
Cl6 C2S Cl5 117.3(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O3 0.84 1.85 2.681(15) 168.8 2_657
O4 H4 O4 0.84 1.69 2.507(13) 162.8 2_657
N1 H1A O5 0.88 2.44 3.164(10) 140.3 2_657
N3 H3B O7 0.88 2.06 2.891(12) 157.1 2_656
N4 H4B O8 0.88 2.02 2.511(10) 113.9 .

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        24.38
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.085

_vrf_PLAT061_k08308              
;
PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.56
RESPONSE: ...
This Alert is generated when the predicted transmission coefficients
are different from the calculated ones. Since the multi-scan correction
uses redundant data it corrects for more than just absorption: slight
crystal alignment, poor crystal quality and maybe even sometimes
partial twinning. When there are many kappa data sets within one
collection, we have found the transmission factors appear larger than
they should and this is sometimes to do with inter-set scaling. You
would expect this Alert to appear more for low absorbers (organics)
where the absorption is minimal but the multi-scan absorption
correction has been used.
In this case the effect maybe explained by the crystals being of
poor quality because of the rapid loss of solvent.
;
# end Validation Reply Form

_vrf_PLAT029_k08308              
;
PROBLEM: diffrn_measured_fraction_theta_full Low ....... 0.94
RESPONSE: ...
The crystals diffracted very weakly and higher angle reflections
are not included in the refinement. These theoretical relections
were simply the reslut of noise.
;
# end Validation Reply Form

_vrf_PLAT220_k08308              
;
PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.60 Ratio
RESPONSE: ...
Some terminal C atoms, namley those of the isopropyl groups have
higher than normal displacement parameters. This may be the result
of borderline disorder which in this case was not modelled as this
did not improve the refinement.
;
# end Validation Reply Form

_vrf_PLAT222_k08308              
;
PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ...4.15 Ratio

RESPONSE: ...
... see above
;
# end Validation Reply Form

_vrf_PLAT230_k08308              
;
PROBLEM: Hirshfeld Test Diff for O6 -- C23 .. 8.95 su

RESPONSE: ...
The physical description of and anisotropic displacement
paprameters [ADPs] at these atoms relies on the availability of
high angle data. In the case of this crystal where diffraction drops
off rapidly at two-theta angles above 40 degrees this high angle data
is not available therfore the ADP description may not be ideal.
;
# end Validation Reply Form

_vrf_PLAT241_k08308              
;
PROBLEM: Check High Ueq as Compared to Neighbors for C40

RESPONSE: ...
see PLAT220 above
;
# end Validation Reply Form

_vrf_PLAT242_k08308              
;
PROBLEM: Check Low Ueq as Compared to Neighbors for Si1

RESPONSE: ...
see PLAT220 above
;
# end Validation Reply Form

_vrf_PLAT049_k08308              
;
PROBLEM: Calculated Density less than 1.0 gcm-3 ......... 0.96

RESPONSE: ...
The crystal might be expected to have a low density as the lattice
appears to contain substantial solvent. The calcluated density will
be lowred by the treatment used to deal with the disordered solvent
in the lattice (see PLAT602 below)
;
# end Validation Reply Form

_vrf_PLAT602_k08308              
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure !
RESPONSE: ...
During the
refinement of the structure, electron density peaks were located
that were believed to be highly disordered
solvent molecules (likely additional chloroform). Attempts
made to model the solvent molecule were not successful.
The SQUEEZE option in PLATON (Spek, 2003) indicated there was a
solvent cavity of volume 1644 \%A^3^ containing approximately 270
electrons. In the final cycles of refinement, this contribution to the
electron density was removed from the observed data. The
density, the F(000) value, the molecular weight and the formula are
given without taking into account the results obtained with the
SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered
solvent molecules were carried out by St\"ahler et al. (2001),
Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005).
References:

Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13

Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005).
Acta Cryst. E61, m2014-m2017.

Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M.
(2003). Acta Cryst. E59, o975-o977.

Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M.
(2003). Acta Cryst. C59, m84-m86.

St\"ahler, R., N\"ather, C. & Bensch, W. (2001). Acta Cryst.
C57, 26-27.

;
# end Validation Reply Form