# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# 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.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
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data_2a
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C30 H55 N3 S2 Si2'
_chemical_formula_sum 'C30 H55 N3 S2 Si2'
_chemical_formula_weight 578.07
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.985(5)
_cell_length_b 11.898(7)
_cell_length_c 20.220(11)
_cell_angle_alpha 73.605(12)
_cell_angle_beta 78.698(12)
_cell_angle_gamma 74.512(12)
_cell_volume 1760.7(17)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 3065
_cell_measurement_theta_min 2.74
_cell_measurement_theta_max 23.32
_exptl_crystal_description Plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.08
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.090
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 632
_exptl_absorpt_coefficient_mu 0.241
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9810
_exptl_absorpt_correction_T_max 0.9928
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 17351
_diffrn_reflns_av_R_equivalents 0.0372
_diffrn_reflns_av_sigmaI/netI 0.0491
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 1.83
_diffrn_reflns_theta_max 26.44
_reflns_number_total 7112
_reflns_number_gt 4681
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement 'SAINT (Bruker, 2001)'
_computing_data_reduction 'SAINT (Bruker, 2001)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_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^)+(0.0593P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7112
_refine_ls_number_parameters 334
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0792
_refine_ls_R_factor_gt 0.0463
_refine_ls_wR_factor_ref 0.1236
_refine_ls_wR_factor_gt 0.1110
_refine_ls_goodness_of_fit_ref 1.009
_refine_ls_restrained_S_all 1.009
_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
Si2 Si 0.65559(7) 0.79309(5) 0.40271(3) 0.04340(16) Uani 1 1 d . . .
N3 N 1.5012(2) 0.54696(16) 0.19792(9) 0.0471(4) Uani 1 1 d . . .
Si1 Si 1.77346(7) 0.34180(5) 0.18526(3) 0.04513(17) Uani 1 1 d . . .
N2 N 0.9569(2) 0.76526(15) 0.30214(9) 0.0453(4) Uani 1 1 d . . .
S3 S 0.95284(8) 0.55673(5) 0.38880(3) 0.05518(18) Uani 1 1 d . . .
N1 N 1.2365(2) 0.69720(15) 0.23015(9) 0.0460(4) Uani 1 1 d . . .
S4 S 1.43237(8) 0.36609(5) 0.29856(3) 0.05513(18) Uani 1 1 d . . .
C4 C 1.5646(3) 0.4314(2) 0.22445(11) 0.0486(5) Uani 1 1 d . . .
C5 C 1.2844(3) 0.50204(18) 0.29327(11) 0.0447(5) Uani 1 1 d . . .
C6 C 1.1264(3) 0.56590(18) 0.32378(10) 0.0440(5) Uani 1 1 d . . .
C7 C 1.3472(3) 0.58431(18) 0.23667(11) 0.0434(5) Uani 1 1 d . . .
C8 C 0.8618(3) 0.71167(18) 0.35731(11) 0.0463(5) Uani 1 1 d . . .
C9 C 1.1016(3) 0.68334(18) 0.28423(10) 0.0433(5) Uani 1 1 d . . .
C10 C 0.5582(3) 0.9238(2) 0.33325(11) 0.0519(6) Uani 1 1 d . . .
H10A H 0.6500 0.9687 0.3125 0.062 Uiso 1 1 calc R . .
C11 C 0.7230(3) 0.8496(2) 0.46984(11) 0.0549(6) Uani 1 1 d . . .
H11A H 0.6157 0.8905 0.4942 0.066 Uiso 1 1 calc R . .
C13 C 1.7136(3) 0.2794(2) 0.11899(13) 0.0650(7) Uani 1 1 d . . .
H13A H 1.8229 0.2371 0.0965 0.078 Uiso 1 1 calc R . .
C14 C 1.2570(3) 0.80428(19) 0.17529(11) 0.0522(6) Uani 1 1 d . . .
H14A H 1.3804 0.8053 0.1639 0.063 Uiso 1 1 calc R . .
H14B H 1.1970 0.8749 0.1924 0.063 Uiso 1 1 calc R . .
C16 C 0.4027(4) 1.0121(3) 0.36223(16) 0.0948(10) Uani 1 1 d . . .
H16A H 0.3591 1.0769 0.3247 0.142 Uiso 1 1 calc R . .
H16B H 0.4403 1.0436 0.3942 0.142 Uiso 1 1 calc R . .
H16C H 0.3114 0.9710 0.3860 0.142 Uiso 1 1 calc R . .
C17 C 1.1860(3) 0.8111(2) 0.11009(12) 0.0657(7) Uani 1 1 d . . .
H17A H 1.2316 0.8707 0.0724 0.079 Uiso 1 1 calc R . .
H17B H 1.2294 0.7341 0.0982 0.079 Uiso 1 1 calc R . .
C18 C 1.9147(3) 0.4519(2) 0.14102(14) 0.0694(7) Uani 1 1 d . . .
H18A H 1.8441 0.5148 0.1082 0.083 Uiso 1 1 calc R . .
C20 C 0.5105(4) 0.8878(3) 0.27366(14) 0.0789(8) Uani 1 1 d . . .
H20A H 0.4628 0.9589 0.2403 0.118 Uiso 1 1 calc R . .
H20B H 0.4251 0.8396 0.2916 0.118 Uiso 1 1 calc R . .
H20C H 0.6137 0.8426 0.2517 0.118 Uiso 1 1 calc R . .
C21 C 0.9908(3) 0.8424(2) 0.11513(13) 0.0695(7) Uani 1 1 d . . .
H21A H 0.9482 0.9241 0.1205 0.083 Uiso 1 1 calc R . .
H21B H 0.9441 0.7896 0.1566 0.083 Uiso 1 1 calc R . .
C26 C 0.8362(4) 0.9415(3) 0.43656(16) 0.0899(9) Uani 1 1 d . . .
H26A H 0.8664 0.9686 0.4722 0.135 Uiso 1 1 calc R . .
H26B H 0.7720 1.0089 0.4055 0.135 Uiso 1 1 calc R . .
H26C H 0.9413 0.9049 0.4111 0.135 Uiso 1 1 calc R . .
C27 C 1.5990(4) 0.1878(3) 0.15257(17) 0.0962(10) Uani 1 1 d . . .
H27A H 1.5730 0.1580 0.1172 0.144 Uiso 1 1 calc R . .
H27B H 1.4917 0.2260 0.1761 0.144 Uiso 1 1 calc R . .
H27C H 1.6606 0.1222 0.1854 0.144 Uiso 1 1 calc R . .
C28 C 0.9201(4) 0.8325(3) 0.05248(16) 0.0903(9) Uani 1 1 d . . .
H28A H 0.9625 0.8880 0.0114 0.108 Uiso 1 1 calc R . .
H28B H 0.9676 0.7519 0.0458 0.108 Uiso 1 1 calc R . .
C30 C 0.6582(5) 0.8426(4) -0.0025(2) 0.1443(17) Uani 1 1 d . . .
H30A H 0.5325 0.8600 0.0054 0.216 Uiso 1 1 calc R . .
H30B H 0.7021 0.7614 -0.0071 0.216 Uiso 1 1 calc R . .
H30C H 0.6962 0.8970 -0.0444 0.216 Uiso 1 1 calc R . .
C31 C 0.7274(4) 0.8576(4) 0.0582(2) 0.1219(14) Uani 1 1 d . . .
H31A H 0.6801 0.9394 0.0629 0.146 Uiso 1 1 calc R . .
H31B H 0.6845 0.8044 0.1004 0.146 Uiso 1 1 calc R . .
C32 C 1.9555(5) 0.5162(3) 0.1889(2) 0.1244(14) Uani 1 1 d . . .
H32A H 2.0260 0.5719 0.1625 0.187 Uiso 1 1 calc R . .
H32B H 2.0182 0.4584 0.2246 0.187 Uiso 1 1 calc R . .
H32C H 1.8481 0.5591 0.2098 0.187 Uiso 1 1 calc R . .
C34 C 1.6233(4) 0.3793(3) 0.06186(15) 0.0946(10) Uani 1 1 d . . .
H34A H 1.5962 0.3442 0.0291 0.142 Uiso 1 1 calc R . .
H34B H 1.7002 0.4322 0.0384 0.142 Uiso 1 1 calc R . .
H34C H 1.5170 0.4241 0.0824 0.142 Uiso 1 1 calc R . .
C1 C 2.0782(5) 0.3996(4) 0.0965(3) 0.1583(19) Uani 1 1 d . . .
H1A H 2.1441 0.4601 0.0748 0.237 Uiso 1 1 calc R . .
H1B H 2.0444 0.3731 0.0615 0.237 Uiso 1 1 calc R . .
H1C H 2.1491 0.3326 0.1254 0.237 Uiso 1 1 calc R . .
C19 C 1.8635(3) 0.2137(2) 0.25805(12) 0.0570(6) Uani 1 1 d . . .
H19A H 1.7664 0.1746 0.2808 0.068 Uiso 1 1 calc R . .
C2 C 0.5183(3) 0.6797(2) 0.44797(12) 0.0611(6) Uani 1 1 d . . .
H2B H 0.5971 0.6122 0.4752 0.073 Uiso 1 1 calc R . .
C15 C 0.8175(4) 0.7475(3) 0.52439(13) 0.0768(8) Uani 1 1 d . . .
H15A H 0.8481 0.7804 0.5574 0.115 Uiso 1 1 calc R . .
H15B H 0.9220 0.7041 0.5020 0.115 Uiso 1 1 calc R . .
H15C H 0.7417 0.6939 0.5480 0.115 Uiso 1 1 calc R . .
C22 C 1.9211(4) 0.2517(3) 0.31519(14) 0.0815(8) Uani 1 1 d . . .
H22A H 1.9638 0.1815 0.3501 0.122 Uiso 1 1 calc R . .
H22B H 1.8229 0.3028 0.3359 0.122 Uiso 1 1 calc R . .
H22C H 2.0125 0.2945 0.2952 0.122 Uiso 1 1 calc R . .
C23 C 2.0099(4) 0.1163(3) 0.23173(17) 0.0982(11) Uani 1 1 d . . .
H23A H 2.0498 0.0532 0.2707 0.147 Uiso 1 1 calc R . .
H23B H 2.1058 0.1512 0.2060 0.147 Uiso 1 1 calc R . .
H23C H 1.9653 0.0838 0.2022 0.147 Uiso 1 1 calc R . .
C12 C 0.3686(4) 0.7233(3) 0.50128(17) 0.1004(11) Uani 1 1 d . . .
H12A H 0.3060 0.6611 0.5233 0.151 Uiso 1 1 calc R . .
H12B H 0.2902 0.7936 0.4783 0.151 Uiso 1 1 calc R . .
H12C H 0.4157 0.7428 0.5358 0.151 Uiso 1 1 calc R . .
C3 C 0.4546(5) 0.6257(3) 0.39955(17) 0.0971(10) Uani 1 1 d . . .
H3B H 0.3882 0.5681 0.4268 0.146 Uiso 1 1 calc R . .
H3C H 0.5538 0.5867 0.3724 0.146 Uiso 1 1 calc R . .
H3D H 0.3819 0.6886 0.3692 0.146 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
Si2 0.0389(3) 0.0441(3) 0.0423(3) -0.0132(3) -0.0036(3) 0.0005(3)
N3 0.0428(10) 0.0449(11) 0.0472(10) -0.0122(8) -0.0009(8) -0.0016(8)
Si1 0.0380(3) 0.0452(3) 0.0478(4) -0.0155(3) -0.0018(3) -0.0004(3)
N2 0.0423(10) 0.0430(10) 0.0456(10) -0.0146(8) -0.0038(8) 0.0010(8)
S3 0.0542(4) 0.0446(3) 0.0492(3) -0.0067(3) 0.0074(3) 0.0029(3)
N1 0.0429(10) 0.0374(10) 0.0468(10) -0.0068(8) 0.0023(8) -0.0003(8)
S4 0.0518(3) 0.0416(3) 0.0552(4) -0.0082(3) 0.0044(3) 0.0055(3)
C4 0.0433(12) 0.0482(13) 0.0483(13) -0.0135(10) -0.0014(10) -0.0014(10)
C5 0.0437(12) 0.0409(12) 0.0417(12) -0.0103(9) -0.0019(9) 0.0012(10)
C6 0.0419(12) 0.0406(12) 0.0432(12) -0.0105(9) -0.0029(9) -0.0003(10)
C7 0.0420(12) 0.0411(12) 0.0431(12) -0.0130(10) -0.0029(9) -0.0014(10)
C8 0.0475(12) 0.0411(12) 0.0450(12) -0.0122(10) -0.0044(10) -0.0001(10)
C9 0.0414(12) 0.0409(12) 0.0438(12) -0.0140(9) -0.0048(10) 0.0004(10)
C10 0.0513(13) 0.0486(13) 0.0511(13) -0.0105(10) -0.0122(11) -0.0009(11)
C11 0.0513(13) 0.0620(15) 0.0489(13) -0.0218(11) -0.0072(11) 0.0005(12)
C13 0.0624(15) 0.0732(17) 0.0594(15) -0.0274(13) -0.0085(12) -0.0032(14)
C14 0.0526(13) 0.0423(13) 0.0550(14) -0.0070(10) -0.0031(11) -0.0076(11)
C16 0.094(2) 0.079(2) 0.086(2) -0.0239(17) -0.0265(17) 0.0382(17)
C17 0.0722(17) 0.0635(16) 0.0512(14) -0.0037(12) -0.0025(13) -0.0128(14)
C18 0.0531(15) 0.0692(17) 0.0779(18) -0.0094(14) 0.0004(13) -0.0159(13)
C20 0.100(2) 0.0764(19) 0.0610(17) -0.0084(14) -0.0345(16) -0.0132(16)
C21 0.0739(18) 0.0662(17) 0.0648(17) -0.0116(13) -0.0182(14) -0.0074(14)
C26 0.106(2) 0.093(2) 0.091(2) -0.0321(18) -0.0263(19) -0.035(2)
C27 0.118(3) 0.089(2) 0.106(3) -0.035(2) -0.032(2) -0.040(2)
C28 0.089(2) 0.106(2) 0.074(2) -0.0237(18) -0.0183(17) -0.0121(19)
C30 0.106(3) 0.193(5) 0.164(4) -0.099(4) -0.057(3) 0.001(3)
C31 0.085(2) 0.180(4) 0.110(3) -0.061(3) -0.030(2) -0.005(2)
C32 0.153(4) 0.109(3) 0.139(3) -0.008(2) -0.042(3) -0.083(3)
C34 0.109(2) 0.112(3) 0.0648(19) -0.0143(17) -0.0308(18) -0.022(2)
C1 0.089(3) 0.146(4) 0.207(5) -0.042(3) 0.077(3) -0.043(3)
C19 0.0505(13) 0.0533(14) 0.0620(15) -0.0157(12) -0.0116(11) 0.0020(11)
C2 0.0536(14) 0.0663(16) 0.0567(15) -0.0071(12) -0.0053(12) -0.0119(13)
C15 0.0753(18) 0.096(2) 0.0558(16) -0.0213(15) -0.0223(14) -0.0010(16)
C22 0.090(2) 0.083(2) 0.0675(18) -0.0079(15) -0.0284(16) -0.0095(17)
C23 0.089(2) 0.074(2) 0.107(2) -0.0253(18) -0.0263(19) 0.0364(17)
C12 0.0671(19) 0.112(3) 0.105(2) -0.020(2) 0.0273(17) -0.0273(18)
C3 0.115(3) 0.091(2) 0.098(2) -0.0026(18) -0.031(2) -0.054(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
Si2 C10 1.883(2) . ?
Si2 C8 1.884(2) . ?
Si2 C2 1.886(3) . ?
Si2 C11 1.892(2) . ?
N3 C4 1.324(3) . ?
N3 C7 1.361(3) . ?
Si1 C18 1.876(3) . ?
Si1 C4 1.886(2) . ?
Si1 C19 1.889(2) . ?
Si1 C13 1.892(3) . ?
N2 C8 1.324(3) . ?
N2 C9 1.360(2) . ?
S3 C6 1.716(2) . ?
S3 C8 1.771(2) . ?
N1 C7 1.383(3) . ?
N1 C9 1.384(3) . ?
N1 C14 1.457(3) . ?
S4 C5 1.719(2) . ?
S4 C4 1.768(2) . ?
C5 C7 1.387(3) . ?
C5 C6 1.413(3) . ?
C6 C9 1.384(3) . ?
C10 C16 1.534(3) . ?
C10 C20 1.529(3) . ?
C10 H10A 0.9800 . ?
C11 C26 1.530(4) . ?
C11 C15 1.531(3) . ?
C11 H11A 0.9800 . ?
C13 C34 1.537(4) . ?
C13 C27 1.535(4) . ?
C13 H13A 0.9800 . ?
C14 C17 1.508(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C21 1.492(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C32 1.518(4) . ?
C18 C1 1.524(4) . ?
C18 H18A 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C28 1.529(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C31 1.475(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 C31 1.513(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C19 C23 1.541(3) . ?
C19 C22 1.538(3) . ?
C19 H19A 0.9800 . ?
C2 C12 1.529(4) . ?
C2 C3 1.535(4) . ?
C2 H2B 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 H3D 0.9600 . ?
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
C10 Si2 C8 105.45(10) . . ?
C10 Si2 C2 116.90(11) . . ?
C8 Si2 C2 107.29(11) . . ?
C10 Si2 C11 110.04(11) . . ?
C8 Si2 C11 107.30(11) . . ?
C2 Si2 C11 109.37(11) . . ?
C4 N3 C7 109.11(18) . . ?
C18 Si1 C4 105.81(12) . . ?
C18 Si1 C19 116.51(12) . . ?
C4 Si1 C19 107.00(11) . . ?
C18 Si1 C13 110.19(13) . . ?
C4 Si1 C13 107.41(11) . . ?
C19 Si1 C13 109.45(12) . . ?
C8 N2 C9 109.28(18) . . ?
C6 S3 C8 89.96(10) . . ?
C7 N1 C9 105.07(17) . . ?
C7 N1 C14 126.23(17) . . ?
C9 N1 C14 128.64(17) . . ?
C5 S4 C4 90.02(11) . . ?
N3 C4 S4 114.21(15) . . ?
N3 C4 Si1 123.32(17) . . ?
S4 C4 Si1 122.44(13) . . ?
C7 C5 C6 106.42(18) . . ?
C7 C5 S4 107.68(15) . . ?
C6 C5 S4 145.88(17) . . ?
C9 C6 C5 106.40(18) . . ?
C9 C6 S3 107.95(15) . . ?
C5 C6 S3 145.64(17) . . ?
N3 C7 N1 130.03(19) . . ?
N3 C7 C5 118.98(18) . . ?
N1 C7 C5 110.98(18) . . ?
N2 C8 S3 113.97(15) . . ?
N2 C8 Si2 123.70(15) . . ?
S3 C8 Si2 122.21(12) . . ?
N2 C9 C6 118.84(19) . . ?
N2 C9 N1 130.02(19) . . ?
C6 C9 N1 111.14(17) . . ?
C16 C10 C20 110.6(2) . . ?
C16 C10 Si2 113.15(17) . . ?
C20 C10 Si2 114.25(17) . . ?
C16 C10 H10A 106.0 . . ?
C20 C10 H10A 106.0 . . ?
Si2 C10 H10A 106.0 . . ?
C26 C11 C15 109.8(2) . . ?
C26 C11 Si2 112.10(17) . . ?
C15 C11 Si2 112.49(18) . . ?
C26 C11 H11A 107.4 . . ?
C15 C11 H11A 107.4 . . ?
Si2 C11 H11A 107.4 . . ?
C34 C13 C27 110.0(2) . . ?
C34 C13 Si1 112.0(2) . . ?
C27 C13 Si1 112.34(18) . . ?
C34 C13 H13A 107.4 . . ?
C27 C13 H13A 107.4 . . ?
Si1 C13 H13A 107.4 . . ?
N1 C14 C17 113.21(19) . . ?
N1 C14 H14A 108.9 . . ?
C17 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C17 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C17 C14 114.8(2) . . ?
C21 C17 H17A 108.6 . . ?
C14 C17 H17A 108.6 . . ?
C21 C17 H17B 108.6 . . ?
C14 C17 H17B 108.6 . . ?
H17A C17 H17B 107.5 . . ?
C32 C18 C1 112.5(3) . . ?
C32 C18 Si1 114.3(2) . . ?
C1 C18 Si1 113.2(2) . . ?
C32 C18 H18A 105.3 . . ?
C1 C18 H18A 105.3 . . ?
Si1 C18 H18A 105.3 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 C28 114.3(2) . . ?
C17 C21 H21A 108.7 . . ?
C28 C21 H21A 108.7 . . ?
C17 C21 H21B 108.7 . . ?
C28 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C11 C26 H26A 109.5 . . ?
C11 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C11 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C13 C27 H27A 109.5 . . ?
C13 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C13 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C31 C28 C21 114.8(3) . . ?
C31 C28 H28A 108.6 . . ?
C21 C28 H28A 108.6 . . ?
C31 C28 H28B 108.6 . . ?
C21 C28 H28B 108.6 . . ?
H28A C28 H28B 107.5 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 C30 114.7(3) . . ?
C28 C31 H31A 108.6 . . ?
C30 C31 H31A 108.6 . . ?
C28 C31 H31B 108.6 . . ?
C30 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C18 C32 H32A 109.5 . . ?
C18 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C18 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C13 C34 H34A 109.5 . . ?
C13 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C13 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 C1 H1A 109.5 . . ?
C18 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C18 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C23 C19 C22 110.5(2) . . ?
C23 C19 Si1 112.95(18) . . ?
C22 C19 Si1 114.97(17) . . ?
C23 C19 H19A 105.9 . . ?
C22 C19 H19A 105.9 . . ?
Si1 C19 H19A 105.9 . . ?
C12 C2 C3 111.6(2) . . ?
C12 C2 Si2 113.6(2) . . ?
C3 C2 Si2 115.04(18) . . ?
C12 C2 H2B 105.2 . . ?
C3 C2 H2B 105.2 . . ?
Si2 C2 H2B 105.2 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C3 H3D 109.5 . . ?
H3B C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full 26.44
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max 0.291
_refine_diff_density_min -0.206
_refine_diff_density_rms 0.040
_database_code_depnum_ccdc_archive 'CCDC 957527'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# 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.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_3a
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H13 Br2 N3 S2'
_chemical_formula_sum 'C12 H13 Br2 N3 S2'
_chemical_formula_weight 423.19
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'
S S 0.1246 0.1234 '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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
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 8.3182(6)
_cell_length_b 19.0237(12)
_cell_length_c 10.5572(7)
_cell_angle_alpha 90.00
_cell_angle_beta 108.0300(10)
_cell_angle_gamma 90.00
_cell_volume 1588.57(19)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 5777
_cell_measurement_theta_min 2.29
_cell_measurement_theta_max 26.90
_exptl_crystal_description Prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.769
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 832
_exptl_absorpt_coefficient_mu 5.355
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.2964
_exptl_absorpt_correction_T_max 0.6165
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 16405
_diffrn_reflns_av_R_equivalents 0.0261
_diffrn_reflns_av_sigmaI/netI 0.0195
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_k_max 24
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.14
_diffrn_reflns_theta_max 27.00
_reflns_number_total 3483
_reflns_number_gt 2786
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement 'SAINT (Bruker, 2001)'
_computing_data_reduction 'SAINT (Bruker, 2001)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_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^)+(0.0343P)^2^+0.3964P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3483
_refine_ls_number_parameters 172
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0374
_refine_ls_R_factor_gt 0.0261
_refine_ls_wR_factor_ref 0.0675
_refine_ls_wR_factor_gt 0.0643
_refine_ls_goodness_of_fit_ref 1.027
_refine_ls_restrained_S_all 1.027
_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
Br2 Br 0.12701(4) 0.138911(14) 0.16797(3) 0.06674(10) Uani 1 1 d . . .
S1 S 0.08442(8) 0.39029(3) -0.34751(6) 0.05673(16) Uani 1 1 d . . .
Br1 Br 0.27509(4) 0.516400(15) -0.42312(3) 0.07228(10) Uani 1 1 d . . .
C2 C 0.1716(3) 0.34764(11) -0.19770(19) 0.0452(5) Uani 1 1 d . . .
S2 S 0.02257(7) 0.22636(3) -0.09292(5) 0.05222(14) Uani 1 1 d . . .
N3 N 0.4000(2) 0.34914(10) -0.01161(16) 0.0479(4) Uani 1 1 d . . .
C4 C 0.1711(3) 0.20991(11) 0.0609(2) 0.0476(5) Uani 1 1 d . . .
C5 C 0.3226(3) 0.38084(11) -0.13155(19) 0.0430(4) Uani 1 1 d . . .
N2 N 0.3070(2) 0.24802(10) 0.09760(16) 0.0472(4) Uani 1 1 d . . .
C7 C 0.2581(3) 0.44638(11) -0.3030(2) 0.0496(5) Uani 1 1 d . . .
C8 C 0.2939(3) 0.29537(11) -0.00278(19) 0.0441(4) Uani 1 1 d . . .
C9 C 0.1523(3) 0.29291(11) -0.1145(2) 0.0445(5) Uani 1 1 d . . .
N1 N 0.3730(2) 0.43690(9) -0.19007(17) 0.0474(4) Uani 1 1 d . . .
C11 C 0.5635(3) 0.36692(12) 0.0839(2) 0.0516(5) Uani 1 1 d . . .
H11A H 0.5513 0.3706 0.1722 0.062 Uiso 1 1 calc R . .
H11B H 0.5997 0.4123 0.0610 0.062 Uiso 1 1 calc R . .
C12 C 0.6970(3) 0.31270(14) 0.0862(3) 0.0653(6) Uani 1 1 d . . .
H12A H 0.7106 0.3098 -0.0016 0.078 Uiso 1 1 calc R . .
H12B H 0.6592 0.2671 0.1068 0.078 Uiso 1 1 calc R . .
C13 C 0.8661(4) 0.32940(17) 0.1869(3) 0.0812(8) Uani 1 1 d . . .
H13A H 0.8499 0.3399 0.2721 0.097 Uiso 1 1 calc R . .
H13B H 0.9389 0.2885 0.1986 0.097 Uiso 1 1 calc R . .
C14 C 0.9520(4) 0.39151(19) 0.1441(4) 0.0957(10) Uani 1 1 d . . .
H14A H 0.8840 0.4332 0.1419 0.115 Uiso 1 1 calc R . .
H14B H 0.9544 0.3831 0.0541 0.115 Uiso 1 1 calc R . .
C21 C 1.1279(5) 0.4060(2) 0.2308(5) 0.1298(17) Uani 1 1 d . . .
H21A H 1.1964 0.3643 0.2345 0.156 Uiso 1 1 calc R . .
H21B H 1.1261 0.4160 0.3204 0.156 Uiso 1 1 calc R . .
C20 C 1.2077(5) 0.4666(3) 0.1822(6) 0.155(2) Uani 1 1 d . . .
H20A H 1.3199 0.4739 0.2416 0.232 Uiso 1 1 calc R . .
H20B H 1.1414 0.5082 0.1796 0.232 Uiso 1 1 calc R . .
H20C H 1.2129 0.4565 0.0945 0.232 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
Br2 0.0875(2) 0.05469(15) 0.06125(16) 0.01228(11) 0.02779(14) -0.00930(12)
S1 0.0565(3) 0.0581(4) 0.0447(3) 0.0127(2) -0.0003(2) -0.0021(3)
Br1 0.0881(2) 0.06079(17) 0.06105(16) 0.02416(12) 0.01297(14) -0.00415(13)
C2 0.0479(12) 0.0461(12) 0.0370(10) 0.0043(9) 0.0065(9) 0.0012(9)
S2 0.0521(3) 0.0522(3) 0.0478(3) 0.0022(2) 0.0087(2) -0.0108(2)
N3 0.0481(10) 0.0495(10) 0.0390(9) 0.0050(7) 0.0030(7) -0.0067(8)
C4 0.0578(13) 0.0452(12) 0.0402(10) 0.0017(9) 0.0158(9) -0.0002(10)
C5 0.0456(11) 0.0417(11) 0.0381(10) 0.0007(8) 0.0078(8) -0.0014(9)
N2 0.0547(10) 0.0457(10) 0.0382(9) 0.0036(7) 0.0100(8) -0.0016(8)
C7 0.0576(13) 0.0441(12) 0.0460(11) 0.0078(9) 0.0144(10) 0.0041(10)
C8 0.0494(11) 0.0435(11) 0.0361(10) 0.0023(8) 0.0087(8) -0.0030(9)
C9 0.0474(11) 0.0449(11) 0.0387(10) -0.0002(9) 0.0095(8) -0.0044(9)
N1 0.0521(10) 0.0441(10) 0.0448(10) 0.0040(8) 0.0132(8) 0.0003(8)
C11 0.0486(12) 0.0519(13) 0.0448(11) 0.0005(9) 0.0005(9) -0.0070(10)
C12 0.0576(15) 0.0638(16) 0.0681(16) -0.0006(13) 0.0101(12) 0.0026(12)
C13 0.0565(16) 0.082(2) 0.090(2) -0.0027(17) 0.0020(14) 0.0126(14)
C14 0.0642(18) 0.094(2) 0.120(3) -0.026(2) 0.0149(18) -0.0068(17)
C21 0.070(2) 0.135(4) 0.172(4) -0.065(3) 0.018(2) -0.006(2)
C20 0.090(3) 0.134(4) 0.253(7) -0.095(4) 0.072(4) -0.049(3)
_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
Br2 C4 1.869(2) . ?
S1 C2 1.725(2) . ?
S1 C7 1.740(2) . ?
Br1 C7 1.874(2) . ?
C2 C5 1.386(3) . ?
C2 C9 1.403(3) . ?
S2 C9 1.724(2) . ?
S2 C4 1.738(2) . ?
N3 C5 1.370(3) . ?
N3 C8 1.373(3) . ?
N3 C11 1.460(3) . ?
C4 N2 1.297(3) . ?
C5 N1 1.362(3) . ?
N2 C8 1.369(3) . ?
C7 N1 1.289(3) . ?
C8 C9 1.386(3) . ?
C11 C12 1.511(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.511(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.520(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C21 1.492(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C21 C20 1.497(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C7 87.85(10) . . ?
C5 C2 C9 106.52(17) . . ?
C5 C2 S1 107.82(15) . . ?
C9 C2 S1 145.66(17) . . ?
C9 S2 C4 87.87(10) . . ?
C5 N3 C8 105.23(16) . . ?
C5 N3 C11 127.40(18) . . ?
C8 N3 C11 127.33(17) . . ?
N2 C4 S2 118.70(16) . . ?
N2 C4 Br2 122.63(16) . . ?
S2 C4 Br2 118.67(13) . . ?
N1 C5 N3 129.89(18) . . ?
N1 C5 C2 119.10(18) . . ?
N3 C5 C2 111.01(18) . . ?
C4 N2 C8 106.46(17) . . ?
N1 C7 S1 118.68(16) . . ?
N1 C7 Br1 122.38(17) . . ?
S1 C7 Br1 118.91(12) . . ?
N2 C8 N3 130.09(18) . . ?
N2 C8 C9 118.64(18) . . ?
N3 C8 C9 111.24(17) . . ?
C8 C9 C2 106.00(18) . . ?
C8 C9 S2 108.31(15) . . ?
C2 C9 S2 145.65(17) . . ?
C7 N1 C5 106.55(18) . . ?
N3 C11 C12 112.08(19) . . ?
N3 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 112.8(2) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 112.0(3) . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C21 115.0(4) . . ?
C13 C14 H14A 108.5 . . ?
C21 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C21 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C21 C20 112.8(4) . . ?
C14 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C14 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.433
_refine_diff_density_min -0.378
_refine_diff_density_rms 0.052
_database_code_depnum_ccdc_archive 'CCDC 957528'