Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2005

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data_Chisholm1228
_database_code_depnum_ccdc_archive 'CCDC 247157'

_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C46 H58 N2 O8 Sn2'
_chemical_formula_weight 1004.32
_chemical_absolute_configuration ad

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'
Sn Sn -0.6537 1.4246 '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)

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

_cell_length_a 12.2393(10)
_cell_length_b 14.3304(10)
_cell_length_c 13.4490(10)
_cell_angle_alpha 90.00
_cell_angle_beta 96.518(4)
_cell_angle_gamma 90.00
_cell_volume 2343.6(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 200(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?

_exptl_crystal_description 'irregular chunk'
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.423
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1024
_exptl_absorpt_coefficient_mu 1.117
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.662
_exptl_absorpt_correction_T_max 0.809
_exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details
;All work was done at 200 K using an Oxford Cryosystems Cryostream
Cooler. The data collection strategy was set up to measure a
quadrant of reciprocal space with a redundancy factor of 4.1, which
means that 90% of the reflections were measured at least 4.1 times.
A combination of phi and omega scans with a frame width of one
degree was used for data collection.
;

_diffrn_ambient_temperature 203(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 Kappa CCD'
_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 45817
_diffrn_reflns_av_R_equivalents 0.037
_diffrn_reflns_av_sigmaI/netI ?
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.13
_diffrn_reflns_theta_max 27.49
_reflns_number_total 10735
_reflns_number_gt 9401
_reflns_threshold_expression >2sigma(I)

_computing_data_collection 'COLLECT (Nonius, 1999)'
_computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?

_refine_special_details
;For each methyl group, the
hydrogen atoms were included in the model at calculated positions with
U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle which defines the
orientation of the methyl group about the C-C bond was refined. The rest
of the hydrogen atoms were added at calculated positions using a riding
model with U(H) = 1.2 * Ueq(bonded carbon atom).

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
'w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary heavy
_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 0.000(11)
_refine_ls_number_reflns 10735
_refine_ls_number_parameters 534
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0337
_refine_ls_R_factor_gt 0.0247
_refine_ls_wR_factor_ref 0.0504
_refine_ls_wR_factor_gt 0.0480
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_restrained_S_all 1.041
_refine_ls_shift/su_max 0.1
_refine_ls_shift/su_mean 0.008
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.513
_refine_diff_density_min -0.507
_refine_diff_density_rms 0.057


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
Sn1 Sn 0.679935(11) 0.503264(11) 0.293696(9) 0.02534(4) Uani 1 1 d . . .
Sn2 Sn 0.897827(11) 0.496202(11) 0.124110(10) 0.02646(4) Uani 1 1 d . . .
O1 O 0.73979(14) 0.42519(11) 0.18516(11) 0.0296(4) Uani 1 1 d . . .
O2 O 0.51330(18) 0.26647(16) 0.17671(18) 0.0659(7) Uani 1 1 d . . .
O3 O 0.51991(15) 0.52360(12) 0.40894(13) 0.0372(5) Uani 1 1 d . . .
O4 O 0.35952(14) 0.45678(12) 0.43268(13) 0.0401(4) Uani 1 1 d . . .
O5 O 0.83556(14) 0.57385(11) 0.23347(11) 0.0290(4) Uani 1 1 d . . .
O6 O 0.99099(17) 0.77259(12) 0.16661(14) 0.0462(5) Uani 1 1 d . . .
O7 O 1.03087(14) 0.48791(19) -0.00114(13) 0.0475(5) Uani 1 1 d . . .
O8 O 1.17360(18) 0.56078(14) -0.05579(14) 0.0557(6) Uani 1 1 d . . .
N1 N 1.00528(18) 0.61402(14) 0.13857(15) 0.0281(5) Uani 1 1 d . . .
N2 N 0.56716(17) 0.39038(14) 0.27865(15) 0.0297(5) Uani 1 1 d . . .
C1 C 0.5913(2) 0.61968(18) 0.22872(18) 0.0276(6) Uani 1 1 d . . .
C2 C 0.5765(2) 0.70276(18) 0.2772(2) 0.0380(7) Uani 1 1 d . . .
H2 H 0.6034 0.7089 0.3452 0.046 Uiso 1 1 calc R . .
C3 C 0.5229(2) 0.7770(2) 0.2278(2) 0.0468(8) Uani 1 1 d . . .
H3 H 0.5126 0.8327 0.2624 0.056 Uiso 1 1 calc R . .
C4 C 0.4846(2) 0.7694(2) 0.1284(2) 0.0528(8) Uani 1 1 d . . .
H4 H 0.4495 0.8204 0.0944 0.063 Uiso 1 1 calc R . .
C5 C 0.4975(3) 0.6878(2) 0.0789(2) 0.0538(8) Uani 1 1 d . . .
H5 H 0.4710 0.6827 0.0107 0.065 Uiso 1 1 calc R . .
C6 C 0.5494(2) 0.6124(2) 0.12857(19) 0.0426(7) Uani 1 1 d . . .
H6 H 0.5563 0.5560 0.0943 0.051 Uiso 1 1 calc R . .
C7 C 0.77533(19) 0.46774(16) 0.43035(17) 0.0295(6) Uani 1 1 d . . .
C8 C 0.7905(2) 0.52298(19) 0.51413(18) 0.0489(8) Uani 1 1 d . . .
H8 H 0.7620 0.5840 0.5123 0.059 Uiso 1 1 calc R . .
C9 C 0.8482(3) 0.4887(3) 0.60223(19) 0.0641(9) Uani 1 1 d . . .
H9 H 0.8595 0.5276 0.6588 0.077 Uiso 1 1 calc R . .
C10 C 0.8881(3) 0.4006(2) 0.6076(2) 0.0564(9) Uani 1 1 d . . .
H10 H 0.9265 0.3781 0.6673 0.068 Uiso 1 1 calc R . .
C11 C 0.8719(3) 0.3449(2) 0.5251(2) 0.0563(8) Uani 1 1 d . . .
H11 H 0.8987 0.2834 0.5282 0.068 Uiso 1 1 calc R . .
C12 C 0.8162(2) 0.37839(19) 0.4366(2) 0.0466(8) Uani 1 1 d . . .
H12 H 0.8063 0.3394 0.3801 0.056 Uiso 1 1 calc R . .
C13 C 0.7391(2) 0.26351(19) 0.1340(3) 0.0574(9) Uani 1 1 d . . .
H13A H 0.7925 0.2739 0.0871 0.086 Uiso 1 1 calc R . .
H13B H 0.6906 0.2127 0.1102 0.086 Uiso 1 1 calc R . .
H13C H 0.7770 0.2477 0.1991 0.086 Uiso 1 1 calc R . .
C14 C 0.6720(2) 0.35133(18) 0.14248(19) 0.0345(6) Uani 1 1 d . . .
H14 H 0.6417 0.3704 0.0741 0.041 Uiso 1 1 calc R . .
C15 C 0.5761(2) 0.33264(19) 0.2021(2) 0.0374(7) Uani 1 1 d . . .
C16 C 0.4747(2) 0.37312(18) 0.33606(18) 0.0346(6) Uani 1 1 d . . .
H16 H 0.4083 0.3610 0.2887 0.042 Uiso 1 1 calc R . .
C17 C 0.4555(2) 0.45946(18) 0.39524(18) 0.0329(6) Uani 1 1 d . . .
C18 C 0.3297(2) 0.5365(2) 0.4920(2) 0.0500(8) Uani 1 1 d . . .
H18 H 0.3512 0.5951 0.4606 0.060 Uiso 1 1 calc R . .
C19 C 0.2054(3) 0.5321(3) 0.4886(2) 0.0727(11) Uani 1 1 d . . .
H19A H 0.1728 0.5288 0.4195 0.109 Uiso 1 1 calc R . .
H19B H 0.1791 0.5876 0.5198 0.109 Uiso 1 1 calc R . .
H19C H 0.1848 0.4772 0.5243 0.109 Uiso 1 1 calc R . .
C20 C 0.3883(3) 0.5292(2) 0.5966(2) 0.0646(11) Uani 1 1 d . . .
H20A H 0.3674 0.4715 0.6271 0.097 Uiso 1 1 calc R . .
H20B H 0.3680 0.5817 0.6361 0.097 Uiso 1 1 calc R . .
H20C H 0.4671 0.5296 0.5938 0.097 Uiso 1 1 calc R . .
C21 C 0.4954(2) 0.28648(19) 0.4074(2) 0.0472(7) Uani 1 1 d . . .
H21 H 0.5441 0.2433 0.3755 0.057 Uiso 1 1 calc R . .
C22 C 0.3907(3) 0.2341(2) 0.4187(3) 0.0644(10) Uani 1 1 d . . .
H22A H 0.4079 0.1778 0.4572 0.097 Uiso 1 1 calc R . .
H22B H 0.3546 0.2178 0.3531 0.097 Uiso 1 1 calc R . .
H22C H 0.3423 0.2732 0.4531 0.097 Uiso 1 1 calc R . .
C23 C 0.5543(3) 0.3116(2) 0.5102(2) 0.0655(10) Uani 1 1 d . . .
H23A H 0.5066 0.3502 0.5459 0.098 Uiso 1 1 calc R . .
H23B H 0.6212 0.3457 0.5020 0.098 Uiso 1 1 calc R . .
H23C H 0.5726 0.2550 0.5479 0.098 Uiso 1 1 calc R . .
C24 C 0.79350(17) 0.5118(2) -0.01178(16) 0.0312(5) Uani 1 1 d . . .
C25 C 0.7312(2) 0.5904(2) -0.0293(2) 0.0495(8) Uani 1 1 d . . .
H25 H 0.7350 0.6373 0.0199 0.059 Uiso 1 1 calc R . .
C26 C 0.6624(3) 0.6030(3) -0.1178(3) 0.0682(10) Uani 1 1 d . . .
H26 H 0.6203 0.6577 -0.1285 0.082 Uiso 1 1 calc R . .
C27 C 0.6568(3) 0.5340(3) -0.1893(2) 0.0693(12) Uani 1 1 d . . .
H27 H 0.6099 0.5414 -0.2492 0.083 Uiso 1 1 calc R . .
C28 C 0.7177(3) 0.4561(3) -0.1744(3) 0.0644(10) Uani 1 1 d . . .
H28 H 0.7134 0.4096 -0.2240 0.077 Uiso 1 1 calc R . .
C29 C 0.7869(3) 0.4440(2) -0.0863(2) 0.0538(8) Uani 1 1 d . . .
H29 H 0.8297 0.3895 -0.0769 0.065 Uiso 1 1 calc R . .
C30 C 0.9907(2) 0.38105(19) 0.1849(2) 0.0431(8) Uani 1 1 d . . .
C31 C 1.0162(3) 0.3761(2) 0.2885(3) 0.0646(10) Uani 1 1 d . . .
H31 H 0.9922 0.4227 0.3302 0.078 Uiso 1 1 calc R . .
C32 C 1.0779(4) 0.3007(3) 0.3292(4) 0.1099(18) Uani 1 1 d . . .
H32 H 1.0958 0.2966 0.3989 0.132 Uiso 1 1 calc R . .
C33 C 1.1120(4) 0.2343(4) 0.2703(6) 0.144(3) Uani 1 1 d . . .
H33 H 1.1546 0.1846 0.2991 0.173 Uiso 1 1 calc R . .
C34 C 1.0860(4) 0.2374(3) 0.1693(5) 0.119(2) Uani 1 1 d . . .
H34 H 1.1078 0.1886 0.1292 0.143 Uiso 1 1 calc R . .
C35 C 1.0273(2) 0.3126(2) 0.1255(3) 0.0672(10) Uani 1 1 d . . .
H35 H 1.0126 0.3166 0.0554 0.081 Uiso 1 1 calc R . .
C36 C 0.8896(3) 0.7035(2) 0.3421(2) 0.0558(9) Uani 1 1 d . . .
H36A H 0.8240 0.6994 0.3762 0.084 Uiso 1 1 calc R . .
H36B H 0.9146 0.7678 0.3424 0.084 Uiso 1 1 calc R . .
H36C H 0.9468 0.6646 0.3763 0.084 Uiso 1 1 calc R . .
C37 C 0.8635(2) 0.67045(17) 0.23506(18) 0.0337(6) Uani 1 1 d . . .
H37 H 0.7989 0.7058 0.2041 0.040 Uiso 1 1 calc R . .
C38 C 0.9608(2) 0.69091(18) 0.17563(18) 0.0318(6) Uani 1 1 d . . .
C39 C 1.0988(2) 0.62667(17) 0.08305(17) 0.0311(6) Uani 1 1 d . . .
H39 H 1.0921 0.6882 0.0494 0.037 Uiso 1 1 calc R . .
C40 C 1.0952(2) 0.5512(2) 0.0034(2) 0.0371(6) Uani 1 1 d . . .
C41 C 1.1851(3) 0.4840(3) -0.1271(2) 0.0760(11) Uani 1 1 d . . .
H41 H 1.1526 0.4252 -0.1053 0.091 Uiso 1 1 calc R . .
C42 C 1.1312(4) 0.5155(4) -0.2264(3) 0.118(2) Uani 1 1 d . . .
H42A H 1.0532 0.5249 -0.2227 0.177 Uiso 1 1 calc R . .
H42B H 1.1410 0.4684 -0.2764 0.177 Uiso 1 1 calc R . .
H42C H 1.1641 0.5736 -0.2448 0.177 Uiso 1 1 calc R . .
C43 C 1.3062(4) 0.4754(5) -0.1302(4) 0.158(3) Uani 1 1 d . . .
H43A H 1.3203 0.4313 -0.1820 0.238 Uiso 1 1 calc R . .
H43B H 1.3405 0.4534 -0.0660 0.238 Uiso 1 1 calc R . .
H43C H 1.3363 0.5358 -0.1449 0.238 Uiso 1 1 calc R . .
C44 C 1.2136(2) 0.6214(2) 0.1470(2) 0.0426(7) Uani 1 1 d . . .
H44 H 1.2692 0.6397 0.1027 0.051 Uiso 1 1 calc R . .
C45 C 1.2426(2) 0.5235(2) 0.1845(2) 0.0577(9) Uani 1 1 d . . .
H45A H 1.3163 0.5233 0.2197 0.086 Uiso 1 1 calc R . .
H45B H 1.2395 0.4810 0.1280 0.086 Uiso 1 1 calc R . .
H45C H 1.1906 0.5036 0.2295 0.086 Uiso 1 1 calc R . .
C46 C 1.2226(3) 0.6909(2) 0.2337(2) 0.0604(9) Uani 1 1 d . . .
H46A H 1.1696 0.6748 0.2794 0.091 Uiso 1 1 calc R . .
H46B H 1.2076 0.7534 0.2079 0.091 Uiso 1 1 calc R . .
H46C H 1.2962 0.6887 0.2689 0.091 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
Sn1 0.02903(8) 0.02327(8) 0.02345(7) -0.00091(9) 0.00186(6) -0.00164(12)
Sn2 0.02577(8) 0.02367(8) 0.02986(8) -0.00306(10) 0.00289(6) 0.00038(10)
O1 0.0325(10) 0.0242(9) 0.0325(9) -0.0059(7) 0.0058(8) -0.0075(8)
O2 0.0543(15) 0.0671(16) 0.0807(17) -0.0403(13) 0.0276(13) -0.0371(12)
O3 0.0431(10) 0.0350(13) 0.0349(9) 0.0002(8) 0.0103(8) -0.0080(9)
O4 0.0383(11) 0.0433(11) 0.0412(10) 0.0029(8) 0.0152(9) 0.0015(8)
O5 0.0314(10) 0.0257(9) 0.0312(9) -0.0071(7) 0.0092(8) -0.0047(8)
O6 0.0550(13) 0.0261(11) 0.0619(12) -0.0018(9) 0.0260(10) -0.0063(9)
O7 0.0387(10) 0.0558(14) 0.0514(10) -0.0205(12) 0.0201(8) -0.0081(12)
O8 0.0715(15) 0.0488(13) 0.0539(12) -0.0020(10) 0.0380(11) 0.0025(11)
N1 0.0270(12) 0.0247(11) 0.0331(12) -0.0003(9) 0.0052(10) -0.0015(9)
N2 0.0284(12) 0.0299(12) 0.0316(12) -0.0019(10) 0.0063(10) -0.0043(9)
C1 0.0251(14) 0.0283(15) 0.0299(14) 0.0017(12) 0.0054(11) -0.0005(11)
C2 0.0424(17) 0.0369(17) 0.0344(15) 0.0013(12) 0.0032(12) 0.0043(13)
C3 0.053(2) 0.0324(16) 0.0556(19) 0.0045(14) 0.0081(15) 0.0120(14)
C4 0.0475(19) 0.055(2) 0.0568(19) 0.0253(16) 0.0092(16) 0.0217(16)
C5 0.053(2) 0.072(2) 0.0348(15) 0.0084(16) -0.0032(14) 0.0185(17)
C6 0.0424(17) 0.0496(18) 0.0344(15) -0.0043(13) -0.0020(12) 0.0094(14)
C7 0.0285(13) 0.0331(15) 0.0264(12) 0.0018(10) 0.0016(10) -0.0018(10)
C8 0.0668(19) 0.0381(19) 0.0393(15) -0.0054(12) -0.0046(13) 0.0123(14)
C9 0.093(2) 0.058(2) 0.0350(14) -0.0095(18) -0.0211(14) 0.006(2)
C10 0.064(2) 0.058(2) 0.0429(17) 0.0081(16) -0.0146(15) 0.0131(17)
C11 0.072(2) 0.0438(18) 0.0499(18) 0.0043(15) -0.0062(16) 0.0158(16)
C12 0.059(2) 0.0327(16) 0.0447(16) -0.0033(13) -0.0098(14) 0.0087(14)
C13 0.0446(18) 0.0379(17) 0.092(2) -0.0277(16) 0.0183(17) -0.0122(15)
C14 0.0355(15) 0.0344(14) 0.0336(14) -0.0097(11) 0.0042(12) -0.0103(12)
C15 0.0351(16) 0.0386(17) 0.0387(16) -0.0077(13) 0.0052(12) -0.0088(13)
C16 0.0295(14) 0.0361(16) 0.0391(15) -0.0008(12) 0.0071(12) -0.0037(12)
C17 0.0385(16) 0.0361(15) 0.0238(13) 0.0065(11) 0.0016(12) 0.0048(13)
C18 0.059(2) 0.0478(18) 0.0481(17) 0.0009(14) 0.0269(15) 0.0069(14)
C19 0.066(2) 0.091(3) 0.066(2) -0.0040(18) 0.0277(17) 0.0193(19)
C20 0.079(2) 0.074(3) 0.0436(16) -0.0113(16) 0.0171(15) 0.0009(18)
C21 0.0480(18) 0.0317(15) 0.066(2) 0.0119(14) 0.0232(16) 0.0023(13)
C22 0.074(3) 0.046(2) 0.077(2) 0.0066(18) 0.0243(19) -0.0197(18)
C23 0.063(2) 0.062(2) 0.070(2) 0.0418(19) -0.0005(18) -0.0073(18)
C24 0.0267(11) 0.0352(16) 0.0319(11) 0.0020(13) 0.0040(9) -0.0024(13)
C25 0.0452(18) 0.060(2) 0.0430(17) -0.0003(14) 0.0055(14) 0.0136(15)
C26 0.047(2) 0.086(3) 0.072(2) 0.019(2) 0.0069(18) 0.0277(18)
C27 0.052(2) 0.109(4) 0.0437(18) 0.019(2) -0.0088(16) -0.007(2)
C28 0.080(3) 0.067(2) 0.0417(18) -0.0003(17) -0.0135(17) -0.013(2)
C29 0.077(2) 0.0456(18) 0.0349(16) 0.0043(14) -0.0099(15) -0.0008(16)
C30 0.0221(15) 0.0288(16) 0.077(2) 0.0084(15) -0.0023(15) -0.0020(12)
C31 0.044(2) 0.058(2) 0.087(2) 0.0295(19) -0.0113(18) -0.0029(16)
C32 0.077(3) 0.081(3) 0.159(4) 0.066(3) -0.040(3) 0.004(3)
C33 0.073(4) 0.048(3) 0.297(10) 0.058(5) -0.041(5) 0.004(2)
C34 0.054(3) 0.044(3) 0.253(7) -0.027(4) -0.009(4) 0.014(2)
C35 0.0368(18) 0.0354(19) 0.128(3) -0.019(2) 0.003(2) 0.0041(15)
C36 0.066(2) 0.0498(19) 0.0567(19) -0.0257(15) 0.0282(16) -0.0252(16)
C37 0.0339(15) 0.0236(13) 0.0451(15) -0.0085(11) 0.0113(12) -0.0048(11)
C38 0.0336(15) 0.0278(15) 0.0339(14) -0.0022(11) 0.0039(11) -0.0044(12)
C39 0.0334(14) 0.0293(14) 0.0319(13) 0.0047(11) 0.0091(11) -0.0025(11)
C40 0.0359(16) 0.0427(17) 0.0347(14) 0.0071(13) 0.0133(13) 0.0067(13)
C41 0.098(3) 0.068(3) 0.072(2) -0.020(2) 0.056(2) -0.008(2)
C42 0.111(3) 0.143(5) 0.098(3) -0.077(4) 0.005(3) -0.004(4)
C43 0.138(4) 0.215(7) 0.129(4) -0.052(5) 0.048(3) 0.090(5)
C44 0.0331(15) 0.0523(18) 0.0431(16) 0.0111(14) 0.0078(12) -0.0052(13)
C45 0.0414(16) 0.066(2) 0.0632(18) 0.0150(16) -0.0042(14) 0.0028(15)
C46 0.051(2) 0.067(2) 0.061(2) -0.0025(17) -0.0060(16) -0.0209(17)

_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
Sn1 O1 2.0401(15) . ?
Sn1 N2 2.121(2) . ?
Sn1 C1 2.123(3) . ?
Sn1 C7 2.124(2) . ?
Sn1 O5 2.3785(16) . ?
Sn2 O5 2.0583(15) . ?
Sn2 C30 2.115(3) . ?
Sn2 C24 2.119(2) . ?
Sn2 N1 2.135(2) . ?
Sn2 O1 2.4108(16) . ?
Sn2 O7 2.4750(16) . ?
O1 C14 1.425(3) . ?
O2 C15 1.244(3) . ?
O3 C17 1.212(3) . ?
O4 C17 1.330(3) . ?
O4 C18 1.463(3) . ?
O5 C37 1.425(3) . ?
O6 C38 1.238(3) . ?
O7 C40 1.198(3) . ?
O8 C40 1.322(3) . ?
O8 C41 1.476(4) . ?
N1 C38 1.349(3) . ?
N1 C39 1.447(3) . ?
N2 C15 1.335(3) . ?
N2 C16 1.461(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.390(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.363(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.372(3) . ?
C7 C12 1.374(3) . ?
C8 C9 1.398(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.353(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.514(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.518(4) . ?
C14 H14 0.9900 . ?
C16 C17 1.504(4) . ?
C16 C21 1.572(3) . ?
C16 H16 0.9900 . ?
C18 C20 1.507(4) . ?
C18 C19 1.518(4) . ?
C18 H18 0.9900 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.508(4) . ?
C21 C23 1.528(4) . ?
C21 H21 0.9900 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 C25 1.365(4) . ?
C24 C29 1.392(4) . ?
C25 C26 1.390(4) . ?
C25 H25 0.9400 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9400 . ?
C27 C28 1.345(5) . ?
C27 H27 0.9400 . ?
C28 C29 1.387(4) . ?
C28 H28 0.9400 . ?
C29 H29 0.9400 . ?
C30 C35 1.371(4) . ?
C30 C31 1.395(4) . ?
C31 C32 1.394(5) . ?
C31 H31 0.9400 . ?
C32 C33 1.335(8) . ?
C32 H32 0.9400 . ?
C33 C34 1.359(8) . ?
C33 H33 0.9400 . ?
C34 C35 1.390(5) . ?
C34 H34 0.9400 . ?
C35 H35 0.9400 . ?
C36 C37 1.515(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 H36C 0.9700 . ?
C37 C38 1.536(4) . ?
C37 H37 0.9900 . ?
C39 C40 1.519(4) . ?
C39 C44 1.564(3) . ?
C39 H39 0.9900 . ?
C41 C42 1.492(5) . ?
C41 C43 1.492(5) . ?
C41 H41 0.9900 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 H42C 0.9700 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 H43C 0.9700 . ?
C44 C45 1.520(4) . ?
C44 C46 1.528(4) . ?
C44 H44 0.9900 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C45 H45C 0.9700 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 H46C 0.9700 . ?

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
O1 Sn1 N2 78.24(7) . . ?
O1 Sn1 C1 110.16(8) . . ?
N2 Sn1 C1 105.27(8) . . ?
O1 Sn1 C7 106.31(8) . . ?
N2 Sn1 C7 100.81(8) . . ?
C1 Sn1 C7 138.53(9) . . ?
O1 Sn1 O5 67.86(6) . . ?
N2 Sn1 O5 146.04(7) . . ?
C1 Sn1 O5 85.25(8) . . ?
C7 Sn1 O5 90.79(8) . . ?
O5 Sn2 C30 111.85(10) . . ?
O5 Sn2 C24 108.87(8) . . ?
C30 Sn2 C24 131.34(12) . . ?
O5 Sn2 N1 77.39(7) . . ?
C30 Sn2 N1 106.45(8) . . ?
C24 Sn2 N1 107.44(9) . . ?
O5 Sn2 O1 66.94(6) . . ?
C30 Sn2 O1 87.48(9) . . ?
C24 Sn2 O1 84.84(7) . . ?
N1 Sn2 O1 144.33(7) . . ?
O5 Sn2 O7 146.91(8) . . ?
C30 Sn2 O7 81.90(11) . . ?
C24 Sn2 O7 78.27(7) . . ?
N1 Sn2 O7 69.75(8) . . ?
O1 Sn2 O7 145.77(6) . . ?
C14 O1 Sn1 117.12(14) . . ?
C14 O1 Sn2 129.00(13) . . ?
Sn1 O1 Sn2 112.29(7) . . ?
C17 O4 C18 118.0(2) . . ?
C37 O5 Sn2 115.35(14) . . ?
C37 O5 Sn1 127.42(14) . . ?
Sn2 O5 Sn1 112.90(7) . . ?
C40 O7 Sn2 114.07(17) . . ?
C40 O8 C41 116.3(2) . . ?
C38 N1 C39 117.7(2) . . ?
C38 N1 Sn2 114.15(17) . . ?
C39 N1 Sn2 124.55(16) . . ?
C15 N2 C16 116.0(2) . . ?
C15 N2 Sn1 115.89(17) . . ?
C16 N2 Sn1 127.81(16) . . ?
C2 C1 C6 118.0(2) . . ?
C2 C1 Sn1 124.90(19) . . ?
C6 C1 Sn1 117.08(19) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C12 118.3(2) . . ?
C8 C7 Sn1 125.59(18) . . ?
C12 C7 Sn1 115.88(18) . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.9(3) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 C13 110.6(2) . . ?
O1 C14 C15 111.6(2) . . ?
C13 C14 C15 110.6(2) . . ?
O1 C14 H14 108.0 . . ?
C13 C14 H14 108.0 . . ?
C15 C14 H14 108.0 . . ?
O2 C15 N2 125.6(3) . . ?
O2 C15 C14 118.7(2) . . ?
N2 C15 C14 115.7(2) . . ?
N2 C16 C17 108.5(2) . . ?
N2 C16 C21 112.0(2) . . ?
C17 C16 C21 110.5(2) . . ?
N2 C16 H16 108.5 . . ?
C17 C16 H16 108.5 . . ?
C21 C16 H16 108.5 . . ?
O3 C17 O4 123.5(2) . . ?
O3 C17 C16 124.5(2) . . ?
O4 C17 C16 112.0(2) . . ?
O4 C18 C20 109.5(2) . . ?
O4 C18 C19 105.2(2) . . ?
C20 C18 C19 113.2(2) . . ?
O4 C18 H18 109.6 . . ?
C20 C18 H18 109.6 . . ?
C19 C18 H18 109.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C23 110.2(3) . . ?
C22 C21 C16 112.0(2) . . ?
C23 C21 C16 113.1(2) . . ?
C22 C21 H21 107.1 . . ?
C23 C21 H21 107.1 . . ?
C16 C21 H21 107.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 117.8(2) . . ?
C25 C24 Sn2 120.4(2) . . ?
C29 C24 Sn2 121.8(2) . . ?
C24 C25 C26 121.8(3) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C27 C26 C25 118.9(3) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C28 C27 C26 120.6(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 120.4(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C24 120.5(3) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
C35 C30 C31 119.7(3) . . ?
C35 C30 Sn2 122.0(3) . . ?
C31 C30 Sn2 118.4(2) . . ?
C30 C31 C32 118.8(4) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 H31 120.6 . . ?
C33 C32 C31 120.8(5) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 121.1(5) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C33 C34 C35 120.0(5) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 119.6(4) . . ?
C30 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C37 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O5 C37 C36 110.0(2) . . ?
O5 C37 C38 112.09(19) . . ?
C36 C37 C38 110.0(2) . . ?
O5 C37 H37 108.2 . . ?
C36 C37 H37 108.2 . . ?
C38 C37 H37 108.2 . . ?
O6 C38 N1 126.8(2) . . ?
O6 C38 C37 119.3(2) . . ?
N1 C38 C37 113.9(2) . . ?
N1 C39 C40 108.2(2) . . ?
N1 C39 C44 115.1(2) . . ?
C40 C39 C44 107.9(2) . . ?
N1 C39 H39 108.5 . . ?
C40 C39 H39 108.5 . . ?
C44 C39 H39 108.5 . . ?
O7 C40 O8 124.4(3) . . ?
O7 C40 C39 122.8(2) . . ?
O8 C40 C39 112.7(2) . . ?
O8 C41 C42 107.0(3) . . ?
O8 C41 C43 104.4(3) . . ?
C42 C41 C43 109.9(3) . . ?
O8 C41 H41 111.8 . . ?
C42 C41 H41 111.8 . . ?
C43 C41 H41 111.8 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 C46 110.8(2) . . ?
C45 C44 C39 112.9(2) . . ?
C46 C44 C39 111.8(2) . . ?
C45 C44 H44 107.0 . . ?
C46 C44 H44 107.0 . . ?
C39 C44 H44 107.0 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C44 C46 H46A 109.5 . . ?
C44 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C44 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

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
N2 Sn1 O1 C14 11.17(16) . . . . ?
C1 Sn1 O1 C14 -90.95(17) . . . . ?
C7 Sn1 O1 C14 109.15(17) . . . . ?
O5 Sn1 O1 C14 -166.80(17) . . . . ?
N2 Sn1 O1 Sn2 178.11(9) . . . . ?
C1 Sn1 O1 Sn2 75.99(10) . . . . ?
C7 Sn1 O1 Sn2 -83.91(9) . . . . ?
O5 Sn1 O1 Sn2 0.14(7) . . . . ?
O5 Sn2 O1 C14 164.8(2) . . . . ?
C30 Sn2 O1 C14 -80.1(2) . . . . ?
C24 Sn2 O1 C14 51.8(2) . . . . ?
N1 Sn2 O1 C14 164.76(18) . . . . ?
O7 Sn2 O1 C14 -8.5(2) . . . . ?
O5 Sn2 O1 Sn1 -0.16(8) . . . . ?
C30 Sn2 O1 Sn1 114.90(11) . . . . ?
C24 Sn2 O1 Sn1 -113.21(10) . . . . ?
N1 Sn2 O1 Sn1 -0.24(16) . . . . ?
O7 Sn2 O1 Sn1 -173.50(9) . . . . ?
C30 Sn2 O5 C37 124.51(17) . . . . ?
C24 Sn2 O5 C37 -82.73(17) . . . . ?
N1 Sn2 O5 C37 21.63(16) . . . . ?
O1 Sn2 O5 C37 -158.32(17) . . . . ?
O7 Sn2 O5 C37 14.8(2) . . . . ?
C30 Sn2 O5 Sn1 -77.02(11) . . . . ?
C24 Sn2 O5 Sn1 75.73(10) . . . . ?
N1 Sn2 O5 Sn1 -179.90(9) . . . . ?
O1 Sn2 O5 Sn1 0.14(7) . . . . ?
O7 Sn2 O5 Sn1 173.27(9) . . . . ?
O1 Sn1 O5 C37 155.15(19) . . . . ?
N2 Sn1 O5 C37 151.59(18) . . . . ?
C1 Sn1 O5 C37 41.12(19) . . . . ?
C7 Sn1 O5 C37 -97.54(18) . . . . ?
O1 Sn1 O5 Sn2 -0.17(8) . . . . ?
N2 Sn1 O5 Sn2 -3.72(16) . . . . ?
C1 Sn1 O5 Sn2 -114.19(10) . . . . ?
C7 Sn1 O5 Sn2 107.15(9) . . . . ?
O5 Sn2 O7 C40 8.1(3) . . . . ?
C30 Sn2 O7 C40 -109.9(2) . . . . ?
C24 Sn2 O7 C40 114.8(2) . . . . ?
N1 Sn2 O7 C40 1.0(2) . . . . ?
O1 Sn2 O7 C40 176.86(17) . . . . ?
O5 Sn2 N1 C38 -23.96(17) . . . . ?
C30 Sn2 N1 C38 -133.32(18) . . . . ?
C24 Sn2 N1 C38 82.13(18) . . . . ?
O1 Sn2 N1 C38 -23.9(2) . . . . ?
O7 Sn2 N1 C38 152.08(19) . . . . ?
O5 Sn2 N1 C39 178.2(2) . . . . ?
C30 Sn2 N1 C39 68.8(2) . . . . ?
C24 Sn2 N1 C39 -75.7(2) . . . . ?
O1 Sn2 N1 C39 178.25(15) . . . . ?
O7 Sn2 N1 C39 -5.79(17) . . . . ?
O1 Sn1 N2 C15 -8.83(19) . . . . ?
C1 Sn1 N2 C15 99.1(2) . . . . ?
C7 Sn1 N2 C15 -113.44(19) . . . . ?
O5 Sn1 N2 C15 -5.5(3) . . . . ?
O1 Sn1 N2 C16 177.3(2) . . . . ?
C1 Sn1 N2 C16 -74.7(2) . . . . ?
C7 Sn1 N2 C16 72.7(2) . . . . ?
O5 Sn1 N2 C16 -179.29(16) . . . . ?
O1 Sn1 C1 C2 -153.9(2) . . . . ?
N2 Sn1 C1 C2 123.2(2) . . . . ?
C7 Sn1 C1 C2 -3.8(3) . . . . ?
O5 Sn1 C1 C2 -89.6(2) . . . . ?
O1 Sn1 C1 C6 23.2(2) . . . . ?
N2 Sn1 C1 C6 -59.7(2) . . . . ?
C7 Sn1 C1 C6 173.28(18) . . . . ?
O5 Sn1 C1 C6 87.5(2) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
Sn1 C1 C2 C3 176.3(2) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C1 -1.6(5) . . . . ?
C2 C1 C6 C5 2.0(4) . . . . ?
Sn1 C1 C6 C5 -175.3(2) . . . . ?
O1 Sn1 C7 C8 156.2(2) . . . . ?
N2 Sn1 C7 C8 -123.0(2) . . . . ?
C1 Sn1 C7 C8 5.4(3) . . . . ?
O5 Sn1 C7 C8 89.1(2) . . . . ?
O1 Sn1 C7 C12 -30.0(2) . . . . ?
N2 Sn1 C7 C12 50.8(2) . . . . ?
C1 Sn1 C7 C12 179.18(19) . . . . ?
O5 Sn1 C7 C12 -97.1(2) . . . . ?
C12 C7 C8 C9 1.3(4) . . . . ?
Sn1 C7 C8 C9 175.0(2) . . . . ?
C7 C8 C9 C10 -1.3(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C8 C7 C12 C11 -0.4(4) . . . . ?
Sn1 C7 C12 C11 -174.6(2) . . . . ?
C10 C11 C12 C7 -0.6(5) . . . . ?
Sn1 O1 C14 C13 -135.2(2) . . . . ?
Sn2 O1 C14 C13 60.4(3) . . . . ?
Sn1 O1 C14 C15 -11.7(3) . . . . ?
Sn2 O1 C14 C15 -176.05(15) . . . . ?
C16 N2 C15 O2 -0.3(4) . . . . ?
Sn1 N2 C15 O2 -174.8(2) . . . . ?
C16 N2 C15 C14 179.7(2) . . . . ?
Sn1 N2 C15 C14 5.1(3) . . . . ?
O1 C14 C15 O2 -176.1(3) . . . . ?
C13 C14 C15 O2 -52.5(4) . . . . ?
O1 C14 C15 N2 3.9(3) . . . . ?
C13 C14 C15 N2 127.5(3) . . . . ?
C15 N2 C16 C17 -161.9(2) . . . . ?
Sn1 N2 C16 C17 11.9(3) . . . . ?
C15 N2 C16 C21 75.7(3) . . . . ?
Sn1 N2 C16 C21 -110.5(2) . . . . ?
C18 O4 C17 O3 1.1(3) . . . . ?
C18 O4 C17 C16 -179.9(2) . . . . ?
N2 C16 C17 O3 -14.3(3) . . . . ?
C21 C16 C17 O3 109.0(3) . . . . ?
N2 C16 C17 O4 166.8(2) . . . . ?
C21 C16 C17 O4 -70.0(3) . . . . ?
C17 O4 C18 C20 -79.7(3) . . . . ?
C17 O4 C18 C19 158.3(2) . . . . ?
N2 C16 C21 C22 -146.3(2) . . . . ?
C17 C16 C21 C22 92.5(3) . . . . ?
N2 C16 C21 C23 88.4(3) . . . . ?
C17 C16 C21 C23 -32.8(3) . . . . ?
O5 Sn2 C24 C25 26.4(2) . . . . ?
C30 Sn2 C24 C25 172.0(2) . . . . ?
N1 Sn2 C24 C25 -55.9(2) . . . . ?
O1 Sn2 C24 C25 89.9(2) . . . . ?
O7 Sn2 C24 C25 -120.0(2) . . . . ?
O5 Sn2 C24 C29 -154.5(2) . . . . ?
C30 Sn2 C24 C29 -9.0(3) . . . . ?
N1 Sn2 C24 C29 123.2(2) . . . . ?
O1 Sn2 C24 C29 -91.0(2) . . . . ?
O7 Sn2 C24 C29 59.1(2) . . . . ?
C29 C24 C25 C26 0.6(4) . . . . ?
Sn2 C24 C25 C26 179.7(2) . . . . ?
C24 C25 C26 C27 0.3(5) . . . . ?
C25 C26 C27 C28 -0.7(5) . . . . ?
C26 C27 C28 C29 0.3(5) . . . . ?
C27 C28 C29 C24 0.6(5) . . . . ?
C25 C24 C29 C28 -1.0(4) . . . . ?
Sn2 C24 C29 C28 179.9(2) . . . . ?
O5 Sn2 C30 C35 170.8(2) . . . . ?
C24 Sn2 C30 C35 26.1(3) . . . . ?
N1 Sn2 C30 C35 -106.4(2) . . . . ?
O1 Sn2 C30 C35 106.9(3) . . . . ?
O7 Sn2 C30 C35 -40.4(2) . . . . ?
O5 Sn2 C30 C31 -10.0(3) . . . . ?
C24 Sn2 C30 C31 -154.8(2) . . . . ?
N1 Sn2 C30 C31 72.7(3) . . . . ?
O1 Sn2 C30 C31 -73.9(2) . . . . ?
O7 Sn2 C30 C31 138.7(2) . . . . ?
C35 C30 C31 C32 -0.5(5) . . . . ?
Sn2 C30 C31 C32 -179.6(3) . . . . ?
C30 C31 C32 C33 -0.1(6) . . . . ?
C31 C32 C33 C34 -1.1(8) . . . . ?
C32 C33 C34 C35 2.9(9) . . . . ?
C31 C30 C35 C34 2.2(5) . . . . ?
Sn2 C30 C35 C34 -178.6(3) . . . . ?
C33 C34 C35 C30 -3.4(7) . . . . ?
Sn2 O5 C37 C36 -139.58(18) . . . . ?
Sn1 O5 C37 C36 65.6(3) . . . . ?
Sn2 O5 C37 C38 -16.8(3) . . . . ?
Sn1 O5 C37 C38 -171.61(14) . . . . ?
C39 N1 C38 O6 0.6(4) . . . . ?
Sn2 N1 C38 O6 -158.9(2) . . . . ?
C39 N1 C38 C37 -178.9(2) . . . . ?
Sn2 N1 C38 C37 21.6(3) . . . . ?
O5 C37 C38 O6 176.7(2) . . . . ?
C36 C37 C38 O6 -60.5(3) . . . . ?
O5 C37 C38 N1 -3.7(3) . . . . ?
C36 C37 C38 N1 119.1(2) . . . . ?
C38 N1 C39 C40 -148.3(2) . . . . ?
Sn2 N1 C39 C40 8.9(3) . . . . ?
C38 N1 C39 C44 91.0(3) . . . . ?
Sn2 N1 C39 C44 -111.8(2) . . . . ?
Sn2 O7 C40 O8 179.7(2) . . . . ?
Sn2 O7 C40 C39 3.5(3) . . . . ?
C41 O8 C40 O7 -4.1(4) . . . . ?
C41 O8 C40 C39 172.5(3) . . . . ?
N1 C39 C40 O7 -7.6(4) . . . . ?
C44 C39 C40 O7 117.5(3) . . . . ?
N1 C39 C40 O8 175.8(2) . . . . ?
C44 C39 C40 O8 -59.2(3) . . . . ?
C40 O8 C41 C42 101.0(3) . . . . ?
C40 O8 C41 C43 -142.6(3) . . . . ?
N1 C39 C44 C45 70.2(3) . . . . ?
C40 C39 C44 C45 -50.7(3) . . . . ?
N1 C39 C44 C46 -55.5(3) . . . . ?
C40 C39 C44 C46 -176.4(2) . . . . ?


data_Chisholm1234
_database_code_depnum_ccdc_archive 'CCDC 247158'

_audit_creation_method SHELXL-93
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_formula_moiety 'C6 H9 N O3'
_chemical_formula_structural ?
_chemical_formula_analytical ?
_chemical_formula_sum 'C6 H9 N O3'
_chemical_formula_weight 143.14
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration syn

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'

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

_cell_length_a 5.0120(10)
_cell_length_b 7.4610(10)
_cell_length_c 18.660(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 697.8(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 200(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?

_exptl_crystal_description rod
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.363
_exptl_crystal_density_method ?
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.110
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?

_exptl_special_details
;All work was done at 200 K using an Oxford Cryosystems Cryostream
Cooler. The data collection strategy was set up to measure an
octant of reciprocal space with a redundancy factor of 5, which
means that 90% of the reflections were measured at least 5 times.

The correct enantiomer was chosen based on known chiral centers
in the molecule.
;

_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 'Nonius Kappa CCD'
_diffrn_measurement_method 'phi and omega scans with kappa offsets'
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10691
_diffrn_reflns_av_R_equivalents 0.032
_diffrn_reflns_av_sigmaI/netI ?
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 2.18
_diffrn_reflns_theta_max 27.46
_reflns_number_total 1603
_reflns_number_gt 1368
_reflns_threshold_expression >2sigma(I)

_computing_data_collection 'COLLECT (Nonius, 1999)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics ?
_computing_publication_material ?

_refine_special_details
;The hydrogen atom bonded to the nitrogen atom was refined isotropically.
The methyl group
hydrogen atoms were included in the model at calculated positions with
U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle which defines the
orientation of the methyl group about the C-C bond was refined. The rest
of the hydrogen atoms were added at calculated positions using a riding
model with U(H) = 1.2 * Ueq(bonded carbon atom).

Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors. Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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
'w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.1107P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
_refine_ls_number_reflns 1603
_refine_ls_number_parameters 97
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0487
_refine_ls_R_factor_obs 0.0361
_refine_ls_wR_factor_all 0.1191
_refine_ls_wR_factor_obs 0.0875
_refine_ls_goodness_of_fit_all 1.156
_refine_ls_goodness_of_fit_obs 0.925
_refine_ls_restrained_S_all 1.156
_refine_ls_restrained_S_obs 0.925
_refine_ls_shift/esd_max 0.022
_refine_ls_shift/esd_mean 0.002

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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.0601(3) 0.7290(2) 0.90909(6) 0.0305(3) Uani 1 d . .
O2 O 0.0359(3) 0.9446(2) 0.98882(7) 0.0381(4) Uani 1 d . .
O3 O 0.3968(3) 0.7211(2) 0.74323(6) 0.0349(4) Uani 1 d . .
N N 0.4387(3) 0.9129(2) 0.83633(8) 0.0264(4) Uani 1 d . .
H1N H 0.5145(45) 0.9955(31) 0.8066(12) 0.040(6) Uiso 1 d . .
C1 C 0.1598(4) 0.8751(3) 0.94117(9) 0.0268(4) Uani 1 d . .
C2 C 0.4250(4) 0.9426(2) 0.91377(9) 0.0246(4) Uani 1 d . .
H2 H 0.5699 0.8712 0.93704 0.030 Uiso 1 calc R .
C3 C 0.3633(4) 0.7589(2) 0.80689(9) 0.0247(4) Uani 1 d . .
C4 C 0.2281(4) 0.6311(3) 0.85840(10) 0.0263(4) Uani 1 d . .
H4 H 0.3680 0.5643 0.88570 0.032 Uiso 1 calc R .
C5 C 0.4689(5) 1.1380(3) 0.93133(11) 0.0384(5) Uani 1 d . .
H5A H 0.4624 1.1547 0.9834 0.058 Uiso 1 calc R .
H5B H 0.3291 1.2102 0.9087 0.058 Uiso 1 calc R .
H5C H 0.6438 1.1757 0.9133 0.058 Uiso 1 calc R .
C6 C 0.0479(5) 0.4981(3) 0.82173(12) 0.0415(6) Uani 1 d . .
H6A H 0.1555 0.4161 0.7926 0.062 Uiso 1 calc R .
H6B H -0.0782 0.5621 0.7908 0.062 Uiso 1 calc R .
H6C H -0.0508 0.4297 0.8579 0.062 Uiso 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
O1 0.0271(7) 0.0321(7) 0.0323(7) -0.0020(6) 0.0051(6) -0.0047(6)
O2 0.0373(8) 0.0443(9) 0.0328(7) -0.0057(7) 0.0116(7) 0.0028(8)
O3 0.0511(9) 0.0293(8) 0.0242(7) -0.0040(6) 0.0042(6) 0.0056(7)
N 0.0372(9) 0.0222(8) 0.0197(7) 0.0015(6) 0.0055(7) -0.0035(8)
C1 0.0294(9) 0.0293(10) 0.0217(9) 0.0035(8) 0.0007(8) 0.0012(9)
C2 0.0283(9) 0.0260(9) 0.0197(8) 0.0008(7) 0.0015(8) -0.0013(8)
C3 0.0283(9) 0.0212(9) 0.0246(8) 0.0003(7) 0.0002(8) 0.0045(8)
C4 0.0288(10) 0.0234(10) 0.0267(9) 0.0009(8) -0.0007(8) 0.0004(8)
C5 0.0512(13) 0.0308(11) 0.0333(10) -0.0082(9) 0.0039(10) -0.0069(11)
C6 0.0433(12) 0.0331(11) 0.0482(12) -0.0052(10) -0.0036(11) -0.0108(11)

_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
O1 C1 1.340(2) . ?
O1 C4 1.462(2) . ?
O2 C1 1.202(2) . ?
O3 C3 1.232(2) . ?
N C3 1.329(2) . ?
N C2 1.464(2) . ?
N H1N 0.91(2) . ?
C1 C2 1.511(3) . ?
C2 C5 1.510(3) . ?
C2 H2 1.00 . ?
C3 C4 1.514(3) . ?
C4 C6 1.506(3) . ?
C4 H4 1.00 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?

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
C1 O1 C4 118.7(2) . . ?
C3 N C2 121.7(2) . . ?
C3 N H1N 116.9(14) . . ?
C2 N H1N 121.1(14) . . ?
O2 C1 O1 119.2(2) . . ?
O2 C1 C2 124.1(2) . . ?
O1 C1 C2 116.6(2) . . ?
N C2 C1 109.0(2) . . ?
N C2 C5 110.7(2) . . ?
C1 C2 C5 112.1(2) . . ?
N C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C5 C2 H2 108.3 . . ?
O3 C3 N 123.9(2) . . ?
O3 C3 C4 121.9(2) . . ?
N C3 C4 114.2(2) . . ?
O1 C4 C6 106.1(2) . . ?
O1 C4 C3 110.8(2) . . ?
C6 C4 C3 113.3(2) . . ?
O1 C4 H4 108.9 . . ?
C6 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
C4 O1 C1 O2 -171.5(2) . . . . ?
C4 O1 C1 C2 8.9(2) . . . . ?
C3 N C2 C1 -44.9(2) . . . . ?
C3 N C2 C5 -168.7(2) . . . . ?
O2 C1 C2 N -144.5(2) . . . . ?
O1 C1 C2 N 35.0(2) . . . . ?
O2 C1 C2 C5 -21.6(3) . . . . ?
O1 C1 C2 C5 158.0(2) . . . . ?
C2 N C3 O3 -172.2(2) . . . . ?
C2 N C3 C4 8.3(3) . . . . ?
C1 O1 C4 C6 -169.7(2) . . . . ?
C1 O1 C4 C3 -46.4(2) . . . . ?
O3 C3 C4 O1 -142.4(2) . . . . ?
N C3 C4 O1 37.0(2) . . . . ?
O3 C3 C4 C6 -23.4(3) . . . . ?
N C3 C4 C6 156.1(2) . . . . ?

_refine_diff_density_max 0.198
_refine_diff_density_min -0.225
_refine_diff_density_rms 0.058


data_Chisholm1239
_database_code_depnum_ccdc_archive 'CCDC 247159'

_audit_creation_method SHELXL-93
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_formula_moiety 'C8 H13 N O3'
_chemical_formula_structural ?
_chemical_formula_analytical ?
_chemical_formula_sum 'C8 H13 N O3'
_chemical_formula_weight 171.19
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration syn

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'

_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21'

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

_cell_length_a 8.905(2)
_cell_length_b 5.2560(10)
_cell_length_c 9.185(3)
_cell_angle_alpha 90.00
_cell_angle_beta 99.110(10)
_cell_angle_gamma 90.00
_cell_volume 424.5(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 200(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?

_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.31
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.339
_exptl_crystal_density_method ?
_exptl_crystal_F_000 184
_exptl_absorpt_coefficient_mu 0.102
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?

_exptl_special_details
; All work was done at 200 K using an Oxford Cryosystems Cryostream
Cooler. The data collection strategy was set up to measure a
quadrant of reciprocal space with a redundancy factor of 4.1, which
means that 90% of the reflections were measured at least 4.1 times.
A combination of phi and omega scans with a frame width of 2 degrees
was used for data collection.

The correct enantiomer was chosen based on the known chiral centers.
;

_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 'Nonius Kappa CCD'
_diffrn_measurement_method 'phi and omega scans with kappa offsets'
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8429
_diffrn_reflns_av_R_equivalents 0.036
_diffrn_reflns_av_sigmaI/netI ?
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 2.25
_diffrn_reflns_theta_max 27.45
_reflns_number_total 1924
_reflns_number_gt 1747
_reflns_threshold_expression >2sigma(I)

_computing_data_collection 'COLLECT (Nonius, 1999) '
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics ?
_computing_publication_material ?

_refine_special_details
;The hydrogen atom bonded to the nitrogen atom was refined isotropically.
The methyl group
hydrogen atoms were included in the model at calculated positions with
U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle which defines the
orientation of the methyl group about the C-C bond was refined. The rest
of the hydrogen atoms were added at calculated positions using a riding
model with U(H) = 1.2 * Ueq(bonded carbon atom).

Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors. Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.0221P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
_refine_ls_number_reflns 1924
_refine_ls_number_parameters 116
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0388
_refine_ls_R_factor_obs 0.0338
_refine_ls_wR_factor_all 0.0832
_refine_ls_wR_factor_obs 0.0809
_refine_ls_goodness_of_fit_all 1.083
_refine_ls_goodness_of_fit_obs 1.108
_refine_ls_restrained_S_all 1.083
_refine_ls_restrained_S_obs 1.108
_refine_ls_shift/esd_max 0.002
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 1.00373(11) -0.1412(2) 0.65504(10) 0.0298(2) Uani 1 d . .
O2 O 1.21376(12) -0.1066(2) 0.56233(11) 0.0381(3) Uani 1 d . .
O3 O 0.87188(11) 0.1842(2) 0.94975(9) 0.0323(3) Uani 1 d . .
N N 1.07343(13) 0.2679(2) 0.83618(12) 0.0260(3) Uani 1 d . .
H1N H 1.1030(16) 0.3794(32) 0.9011(16) 0.024(4) Uiso 1 d . .
C1 C 1.1298(2) -0.0129(3) 0.63808(13) 0.0259(3) Uani 1 d . .
C2 C 1.16131(14) 0.2409(3) 0.71565(12) 0.0234(3) Uani 1 d . .
H2 H 1.12960 0.3791 0.64241 0.028 Uiso 1 calc R .
C3 C 0.94336(15) 0.1514(2) 0.84614(13) 0.0245(3) Uani 1 d . .
C4 C 0.8818(2) -0.0189(3) 0.71758(14) 0.0274(3) Uani 1 d . .
H4 H 0.8220 0.0889 0.63930 0.033 Uiso 1 calc R .
C5 C 1.3310(2) 0.2789(3) 0.77799(14) 0.0283(3) Uani 1 d . .
H5 H 1.3372 0.4337 0.84198 0.034 Uiso 1 calc R .
C6 C 1.3947(2) 0.0586(3) 0.8778(2) 0.0381(4) Uani 1 d . .
H6A H 1.3279 0.0268 0.9510 0.057 Uiso 1 calc R .
H6B H 1.4967 0.1025 0.9283 0.057 Uiso 1 calc R .
H6C H 1.4002 -0.0946 0.8181 0.057 Uiso 1 calc R .
C7 C 1.4295(2) 0.3324(3) 0.6604(2) 0.0410(4) Uani 1 d . .
H7A H 1.3862 0.4749 0.5988 0.062 Uiso 1 calc R .
H7B H 1.4329 0.1809 0.5989 0.062 Uiso 1 calc R .
H7C H 1.5327 0.3759 0.7078 0.062 Uiso 1 calc R .
C8 C 0.7800(2) -0.2270(3) 0.7567(2) 0.0359(3) Uani 1 d . .
H8A H 0.6908 -0.1521 0.7905 0.054 Uiso 1 calc R .
H8B H 0.8357 -0.3320 0.8355 0.054 Uiso 1 calc R .
H8C H 0.7470 -0.3330 0.6697 0.054 Uiso 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
O1 0.0336(5) 0.0273(5) 0.0307(5) -0.0080(4) 0.0115(4) -0.0072(4)
O2 0.0406(6) 0.0398(6) 0.0376(5) -0.0173(5) 0.0170(5) -0.0053(5)
O3 0.0420(6) 0.0297(5) 0.0288(5) 0.0040(4) 0.0164(4) 0.0058(4)
N 0.0333(6) 0.0247(6) 0.0211(5) -0.0061(5) 0.0078(4) -0.0020(5)
C1 0.0327(7) 0.0254(7) 0.0203(6) -0.0021(5) 0.0060(5) -0.0021(5)
C2 0.0299(6) 0.0218(6) 0.0197(5) -0.0011(5) 0.0074(5) -0.0013(5)
C3 0.0311(7) 0.0199(6) 0.0230(6) 0.0050(5) 0.0057(5) 0.0071(5)
C4 0.0272(7) 0.0289(7) 0.0264(6) 0.0015(6) 0.0056(5) 0.0027(5)
C5 0.0310(7) 0.0253(7) 0.0289(6) -0.0038(5) 0.0052(5) -0.0034(6)
C6 0.0359(8) 0.0407(9) 0.0364(8) 0.0032(7) 0.0016(6) 0.0047(7)
C7 0.0360(8) 0.0422(9) 0.0471(8) 0.0011(7) 0.0136(7) -0.0082(7)
C8 0.0358(8) 0.0345(8) 0.0388(7) -0.0030(6) 0.0104(6) -0.0066(7)

_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
O1 C1 1.339(2) . ?
O1 C4 1.456(2) . ?
O2 C1 1.205(2) . ?
O3 C3 1.2378(15) . ?
N C3 1.326(2) . ?
N C2 1.460(2) . ?
N H1N 0.85(2) . ?
C1 C2 1.517(2) . ?
C2 C5 1.542(2) . ?
C2 H2 1.00 . ?
C3 C4 1.513(2) . ?
C4 C8 1.501(2) . ?
C4 H4 1.00 . ?
C5 C7 1.521(2) . ?
C5 C6 1.529(2) . ?
C5 H5 1.00 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?

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
C1 O1 C4 120.97(10) . . ?
C3 N C2 125.90(11) . . ?
C3 N H1N 116.6(9) . . ?
C2 N H1N 117.1(9) . . ?
O2 C1 O1 118.01(12) . . ?
O2 C1 C2 123.02(13) . . ?
O1 C1 C2 118.96(11) . . ?
N C2 C1 111.08(11) . . ?
N C2 C5 108.50(10) . . ?
C1 C2 C5 112.70(11) . . ?
N C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C5 C2 H2 108.1 . . ?
O3 C3 N 123.36(12) . . ?
O3 C3 C4 121.02(12) . . ?
N C3 C4 115.56(11) . . ?
O1 C4 C8 106.81(11) . . ?
O1 C4 C3 111.62(11) . . ?
C8 C4 C3 113.70(11) . . ?
O1 C4 H4 108.2 . . ?
C8 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C7 C5 C6 111.43(13) . . ?
C7 C5 C2 113.67(11) . . ?
C6 C5 C2 111.89(11) . . ?
C7 C5 H5 106.4 . . ?
C6 C5 H5 106.4 . . ?
C2 C5 H5 106.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C4 O1 C1 O2 -166.76(12) . . . . ?
C4 O1 C1 C2 13.8(2) . . . . ?
C3 N C2 C1 -25.3(2) . . . . ?
C3 N C2 C5 -149.76(12) . . . . ?
O2 C1 C2 N -160.59(13) . . . . ?
O1 C1 C2 N 18.8(2) . . . . ?
O2 C1 C2 C5 -38.6(2) . . . . ?
O1 C1 C2 C5 140.78(12) . . . . ?
C2 N C3 O3 -178.74(12) . . . . ?
C2 N C3 C4 -1.4(2) . . . . ?
C1 O1 C4 C8 -165.69(11) . . . . ?
C1 O1 C4 C3 -40.84(15) . . . . ?
O3 C3 C4 O1 -148.78(11) . . . . ?
N C3 C4 O1 33.9(2) . . . . ?
O3 C3 C4 C8 -27.9(2) . . . . ?
N C3 C4 C8 154.77(12) . . . . ?
N C2 C5 C7 -163.14(12) . . . . ?
C1 C2 C5 C7 73.42(15) . . . . ?
N C2 C5 C6 69.56(14) . . . . ?
C1 C2 C5 C6 -53.88(14) . . . . ?

_refine_diff_density_max 0.123
_refine_diff_density_min -0.231
_refine_diff_density_rms 0.042

#END OF CIF



data_Chisholm1284
_database_code_depnum_ccdc_archive 'CCDC 263405'

_audit_creation_date 2005-02-10T14:51:38-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_audit_conform_dict_name cif_core.dic
_audit_conform_dict_version 2.2
_audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic
;
?
;
_chemical_name_common 'Chisholm 1284'
_chemical_formula_moiety 'C32 H64 N4 O6 Sn2'
_chemical_formula_sum 'C32 H64 N4 O6 Sn2'
_chemical_formula_weight 838.29
_chemical_compound_source 'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting trigonal
_symmetry_space_group_name_H-M 'P 32 2 1'
_symmetry_space_group_name_Hall ?
_symmetry_Int_Tables_number 154
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'y, x, -z'
'-x+y, -x, z+1/3'
'-x, -x+y, -z+2/3'
'x-y, -y, -z+1/3'

_cell_length_a 17.406(1)
_cell_length_b 17.406(1)
_cell_length_c 11.737(1)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 3079.6(4)
_cell_formula_units_Z 3
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 4718
_cell_measurement_theta_min 2.037
_cell_measurement_theta_max 27.485
_cell_measurement_wavelength 0.71073

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

_exptl_crystal_description rod
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.23
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.08
_exptl_crystal_density_diffrn 1.356
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1296
_exptl_special_details
;The data collection strategy was set up to measure a
hemisphere of reciprocal space with a redundancy
factor of 1.8, which means that 90% of the reflections
were measured at least 1.8 times. A combination of
phi and omega scans with a frame width of one
degree was used.
;

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

_exptl_absorpt_coefficient_mu 1.257
_exptl_absorpt_correction_type none

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

_diffrn_source 'Enraf Nonius FR590'
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_detector 'CCD plate'
_diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11 0.284911E-1
_diffrn_orient_matrix_ub_12 0.60773E-1
_diffrn_orient_matrix_ub_13 -0.340466E-1
_diffrn_orient_matrix_ub_21 0.389923E-1
_diffrn_orient_matrix_ub_22 0.243959E-1
_diffrn_orient_matrix_ub_23 0.68544E-1
_diffrn_orient_matrix_ub_31 0.454841E-1
_diffrn_orient_matrix_ub_32 -0.106031E-1
_diffrn_orient_matrix_ub_33 -0.374342E-1
_diffrn_measurement_device '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type KappaCCD
_diffrn_measurement_method 'phi and omega scans'
_diffrn_reflns_av_R_equivalents 0.048
_diffrn_reflns_av_unetI/netI ?
_diffrn_reflns_number 9356
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.2
_diffrn_reflns_theta_max 27.49
_diffrn_reflns_theta_full 27.49
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total 4718
_reflns_number_gt 4057
_reflns_threshold_expression >2sigma(I)

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

_computing_data_collection 'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'

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

_refine_special_details
;The molecule is a dimer and contains a crystallographic inversion
center.

One of the n-butyl groups is disordered, while the other one is ordered.
This disorder was modeled with two sets of atoms, C(14A), C(15A),
C(16A) and C(14B), C(15B), C(16B), and with C(13) common to both
sets. These sets of atoms were refined isotropically, their occupancy
factors were fixed to 0.6 for set A and 0.4 for set B, and the C-C bond
lengths were restrained to 1.54 Ang. with the DFIX command.

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
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary heavy
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_number_reflns 4718
_refine_ls_number_parameters 194
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0411
_refine_ls_R_factor_gt 0.0306
_refine_ls_wR_factor_ref 0.074
_refine_ls_wR_factor_gt 0.0704
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_refine_ls_shift/su_max 0.095
_refine_ls_shift/su_mean 0.007
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.01(2)
_refine_diff_density_max 0.84
_refine_diff_density_min -0.408
_refine_diff_density_rms 0.071

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn 0.353290(16) 0.958999(15) 0.014691(17) 0.03582(8) Uani 1 1 d . . .
O1 O 0.33823(18) 0.91895(15) -0.18688(17) 0.0459(6) Uani 1 1 d . . .
O2 O 0.24400(17) 0.68909(16) 0.09559(19) 0.0447(6) Uani 1 1 d . . .
O3 O 0.41345(16) 1.08461(15) 0.15205(16) 0.0385(5) Uani 1 1 d . . .
N1 N 0.3316(2) 0.8155(2) -0.3078(2) 0.0439(7) Uani 1 1 d . . .
N2 N 0.29210(19) 0.81868(17) -0.0043(2) 0.0331(6) Uani 1 1 d . . .
C1 C 0.3175(2) 0.8406(2) -0.2054(3) 0.0370(8) Uani 1 1 d . . .
C2 C 0.2716(2) 0.7713(2) -0.1130(2) 0.0363(8) Uani 1 1 d . . .
H2 H 0.2961 0.7301 -0.1126 0.044 Uiso 1 1 calc R . .
C3 C 0.1728(3) 0.7188(3) -0.1378(3) 0.0529(10) Uani 1 1 d . . .
H3A H 0.1424 0.6767 -0.0757 0.079 Uiso 1 1 calc R . .
H3B H 0.1628 0.6862 -0.2095 0.079 Uiso 1 1 calc R . .
H3C H 0.1495 0.7595 -0.1444 0.079 Uiso 1 1 calc R . .
C4 C 0.2745(2) 0.7705(2) 0.0913(3) 0.0360(8) Uani 1 1 d . . .
C5 C 0.2988(2) 0.8241(2) 0.2018(3) 0.0382(8) Uani 1 1 d . . .
H5 H 0.3478 0.8195 0.2395 0.046 Uiso 1 1 calc R . .
C6 C 0.2191(3) 0.7845(3) 0.2813(3) 0.0546(11) Uani 1 1 d . . .
H6A H 0.236 0.8158 0.3544 0.082 Uiso 1 1 calc R . .
H6B H 0.199 0.7215 0.2937 0.082 Uiso 1 1 calc R . .
H6C H 0.1711 0.7905 0.247 0.082 Uiso 1 1 calc R . .
C7 C 0.3129(3) 0.7275(3) -0.3374(3) 0.0544(10) Uani 1 1 d . . .
H7A H 0.3292 0.7266 -0.4171 0.082 Uiso 1 1 calc R . .
H7B H 0.2495 0.6856 -0.3271 0.082 Uiso 1 1 calc R . .
H7C H 0.3473 0.7104 -0.2881 0.082 Uiso 1 1 calc R . .
C8 C 0.3686(4) 0.8807(3) -0.3996(3) 0.0666(13) Uani 1 1 d . . .
H8A H 0.3749 0.8523 -0.4683 0.1 Uiso 1 1 calc R . .
H8B H 0.4269 0.9294 -0.3767 0.1 Uiso 1 1 calc R . .
H8C H 0.3288 0.904 -0.4154 0.1 Uiso 1 1 calc R . .
C9 C 0.4916(2) 1.0084(2) -0.0106(3) 0.0372(8) Uani 1 1 d . . .
H9A H 0.5176 1.0692 -0.0419 0.045 Uiso 1 1 calc R . .
H9B H 0.5188 1.0137 0.0652 0.045 Uiso 1 1 calc R . .
C10 C 0.5206(2) 0.9569(2) -0.0870(3) 0.0429(9) Uani 1 1 d . . .
H10A H 0.4888 0.8938 -0.0638 0.051 Uiso 1 1 calc R . .
H10B H 0.5035 0.9601 -0.1666 0.051 Uiso 1 1 calc R . .
C11 C 0.6190(3) 0.9916(3) -0.0820(4) 0.0649(12) Uani 1 1 d . . .
H11A H 0.6364 0.9888 -0.0025 0.078 Uiso 1 1 calc R . .
H11B H 0.651 1.0546 -0.1061 0.078 Uiso 1 1 calc R . .
C12 C 0.6463(4) 0.9382(5) -0.1590(6) 0.117(3) Uani 1 1 d . . .
H12A H 0.6112 0.8751 -0.1395 0.175 Uiso 1 1 calc R . .
H12B H 0.7095 0.9585 -0.1479 0.175 Uiso 1 1 calc R . .
H12C H 0.6358 0.9467 -0.2388 0.175 Uiso 1 1 calc R . .
C13 C 0.2583(3) 0.9978(3) -0.0243(4) 0.0603(10) Uiso 1 1 d D . .
H13A H 0.2743 1.054 0.0157 0.072 Uiso 0.6 1 calc PR A 1
H13B H 0.2591 1.0086 -0.1072 0.072 Uiso 0.6 1 calc PR A 1
H13C H 0.2445 1.0183 0.0475 0.072 Uiso 0.4 1 calc PR A 2
H13D H 0.2874 1.05 -0.0753 0.072 Uiso 0.4 1 calc PR A 2
C14A C 0.1635(7) 0.9257(8) 0.0118(10) 0.105(3) Uiso 0.6 1 d PD B 1
H14A H 0.1635 0.9112 0.0933 0.126 Uiso 0.6 1 calc PR B 1
H14B H 0.1451 0.8711 -0.0331 0.126 Uiso 0.6 1 calc PR B 1
C15A C 0.0966(10) 0.9589(10) -0.0081(13) 0.140(5) Uiso 0.6 1 d PD B 1
H15A H 0.1145 1.0138 0.0359 0.167 Uiso 0.6 1 calc PR B 1
H15B H 0.0944 0.9716 -0.0899 0.167 Uiso 0.6 1 calc PR B 1
C16A C 0.0057(15) 0.8845(19) 0.032(2) 0.287(15) Uiso 0.6 1 d PD B 1
H16A H -0.0386 0.9031 0.0219 0.431 Uiso 0.6 1 calc PR B 1
H16B H 0.009 0.8722 0.1129 0.431 Uiso 0.6 1 calc PR B 1
H16C H -0.0115 0.8308 -0.0127 0.431 Uiso 0.6 1 calc PR B 1
C14B C 0.1717(11) 0.9327(13) -0.0782(18) 0.121(6) Uiso 0.4 1 d PD B 2
H14C H 0.1844 0.8972 -0.1328 0.145 Uiso 0.4 1 calc PR B 2
H14D H 0.1518 0.9675 -0.1237 0.145 Uiso 0.4 1 calc PR B 2
C15B C 0.0923(19) 0.867(4) -0.006(3) 0.35(3) Uiso 0.4 1 d PD B 2
H15C H 0.0916 0.8954 0.0671 0.414 Uiso 0.4 1 calc PR B 2
H15D H 0.0974 0.8142 0.0114 0.414 Uiso 0.4 1 calc PR B 2
C16B C 0.004(2) 0.839(2) -0.073(2) 0.195(12) Uiso 0.4 1 d PD B 2
H16D H -0.0467 0.7975 -0.0273 0.292 Uiso 0.4 1 calc PR B 2
H16E H 0.0049 0.8102 -0.1449 0.292 Uiso 0.4 1 calc PR B 2
H16F H -0.0004 0.8917 -0.0902 0.292 Uiso 0.4 1 calc PR B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn 0.04346(14) 0.03615(13) 0.02457(10) 0.00172(9) -0.00262(9) 0.01744(10)
O1 0.0680(16) 0.0327(12) 0.0244(10) 0.0006(9) -0.0074(11) 0.0157(12)
O2 0.0587(16) 0.0359(14) 0.0274(11) 0.0046(10) 0.0072(11) 0.0144(12)
O3 0.0525(13) 0.0364(11) 0.0240(10) 0.0007(9) -0.0035(10) 0.0203(11)
N1 0.057(2) 0.0386(16) 0.0226(13) -0.0002(12) 0.0046(13) 0.0137(15)
N2 0.0387(15) 0.0348(14) 0.0200(12) 0.0022(11) 0.0035(11) 0.0140(13)
C1 0.0407(19) 0.039(2) 0.0216(14) -0.0005(13) -0.0040(14) 0.0131(16)
C2 0.042(2) 0.0364(18) 0.0247(15) 0.0000(13) -0.0007(14) 0.0147(16)
C3 0.046(2) 0.062(3) 0.0289(17) -0.0039(17) 0.0007(16) 0.0108(19)
C4 0.0368(19) 0.042(2) 0.0258(15) 0.0026(14) 0.0027(13) 0.0169(16)
C5 0.044(2) 0.0405(18) 0.0236(14) 0.0027(13) 0.0018(14) 0.0166(16)
C6 0.062(3) 0.051(2) 0.0343(18) -0.0004(17) 0.0130(18) 0.016(2)
C7 0.059(3) 0.051(2) 0.043(2) -0.0056(19) 0.0087(19) 0.020(2)
C8 0.105(4) 0.045(2) 0.0233(16) 0.0064(16) 0.011(2) 0.018(2)
C9 0.0430(19) 0.0360(19) 0.0237(14) -0.0013(13) -0.0005(13) 0.0130(15)
C10 0.047(2) 0.040(2) 0.0366(18) -0.0066(15) -0.0004(15) 0.0177(18)
C11 0.063(3) 0.063(3) 0.060(3) -0.021(2) 0.008(2) 0.025(2)
C12 0.073(4) 0.121(5) 0.154(6) -0.081(5) -0.004(4) 0.047(4)


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

_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn O3 2.063(2) 6_675 ?
Sn C13 2.126(4) . ?
Sn N2 2.133(3) . ?
Sn C9 2.134(4) . ?
Sn O1 2.443(2) . ?
Sn O3 2.487(2) . ?
O1 C1 1.243(4) . ?
O2 C4 1.241(4) . ?
O3 C5 1.423(4) 6_675 ?
O3 Sn 2.063(2) 6_675 ?
N1 C1 1.343(4) . ?
N1 C7 1.441(5) . ?
N1 C8 1.460(4) . ?
N2 C4 1.341(4) . ?
N2 C2 1.463(4) . ?
C1 C2 1.518(4) . ?
C2 C3 1.518(5) . ?
C2 H2 1 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 C5 1.528(5) . ?
C5 O3 1.423(4) 6_675 ?
C5 C6 1.521(5) . ?
C5 H5 1 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C10 1.521(5) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.507(6) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.533(7) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14B 1.499(14) . ?
C13 C14A 1.550(11) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C13 H13C 0.99 . ?
C13 H13D 0.99 . ?
C14A C15A 1.555(14) . ?
C14A H14A 0.99 . ?
C14A H14B 0.99 . ?
C15A C16A 1.534(17) . ?
C15A H15A 0.99 . ?
C15A H15B 0.99 . ?
C16A H16A 0.98 . ?
C16A H16B 0.98 . ?
C16A H16C 0.98 . ?
C14B C15B 1.534(19) . ?
C14B H14C 0.99 . ?
C14B H14D 0.99 . ?
C15B C16B 1.571(19) . ?
C15B H15C 0.99 . ?
C15B H15D 0.99 . ?
C16B H16D 0.98 . ?
C16B H16E 0.98 . ?
C16B H16F 0.98 . ?

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 Sn C13 105.70(14) 6_675 . ?
O3 Sn N2 77.55(9) 6_675 . ?
C13 Sn N2 108.62(15) . . ?
O3 Sn C9 105.28(11) 6_675 . ?
C13 Sn C9 137.94(14) . . ?
N2 Sn C9 105.28(11) . . ?
O3 Sn O1 147.11(9) 6_675 . ?
C13 Sn O1 83.85(14) . . ?
N2 Sn O1 69.59(8) . . ?
C9 Sn O1 85.34(11) . . ?
O3 Sn O3 68.16(10) 6_675 . ?
C13 Sn O3 84.98(13) . . ?
N2 Sn O3 145.49(8) . . ?
C9 Sn O3 80.89(10) . . ?
O1 Sn O3 144.73(7) . . ?
C1 O1 Sn 114.38(19) . . ?
C5 O3 Sn 117.65(17) 6_675 6_675 ?
C5 O3 Sn 128.53(17) 6_675 . ?
Sn O3 Sn 111.79(10) 6_675 . ?
C1 N1 C7 125.5(3) . . ?
C1 N1 C8 119.3(3) . . ?
C7 N1 C8 115.2(3) . . ?
C4 N2 C2 117.5(3) . . ?
C4 N2 Sn 117.1(2) . . ?
C2 N2 Sn 125.29(19) . . ?
O1 C1 N1 120.8(3) . . ?
O1 C1 C2 119.7(3) . . ?
N1 C1 C2 119.4(3) . . ?
N2 C2 C1 107.0(3) . . ?
N2 C2 C3 113.0(3) . . ?
C1 C2 C3 109.2(3) . . ?
N2 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N2 125.5(3) . . ?
O2 C4 C5 119.5(3) . . ?
N2 C4 C5 114.9(3) . . ?
O3 C5 C6 110.7(3) 6_675 . ?
O3 C5 C4 111.9(2) 6_675 . ?
C6 C5 C4 109.4(3) . . ?
O3 C5 H5 108.2 6_675 . ?
C6 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 Sn 119.0(2) . . ?
C10 C9 H9A 107.6 . . ?
Sn C9 H9A 107.6 . . ?
C10 C9 H9B 107.6 . . ?
Sn C9 H9B 107.6 . . ?
H9A C9 H9B 107 . . ?
C11 C10 C9 112.7(3) . . ?
C11 C10 H10A 109 . . ?
C9 C10 H10A 109 . . ?
C11 C10 H10B 109 . . ?
C9 C10 H10B 109 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 111.7(4) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14B C13 Sn 119.9(9) . . ?
C14A C13 Sn 111.4(5) . . ?
C14A C13 H13A 109.3 . . ?
Sn C13 H13A 109.3 . . ?
C14A C13 H13B 109.3 . . ?
Sn C13 H13B 109.3 . . ?
H13A C13 H13B 108 . . ?
C14B C13 H13C 107.3 . . ?
Sn C13 H13C 107.4 . . ?
C14B C13 H13D 107.4 . . ?
Sn C13 H13D 107.4 . . ?
H13C C13 H13D 106.9 . . ?
C13 C14A C15A 110.5(10) . . ?
C13 C14A H14A 109.6 . . ?
C15A C14A H14A 109.6 . . ?
C13 C14A H14B 109.5 . . ?
C15A C14A H14B 109.6 . . ?
H14A C14A H14B 108.1 . . ?
C16A C15A C14A 106.8(14) . . ?
C16A C15A H15A 110.5 . . ?
C14A C15A H15A 110.4 . . ?
C16A C15A H15B 110.3 . . ?
C14A C15A H15B 110.4 . . ?
H15A C15A H15B 108.6 . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.4 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.6 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C13 C14B C15B 121(2) . . ?
C13 C14B H14C 107 . . ?
C15B C14B H14C 107 . . ?
C13 C14B H14D 107 . . ?
C15B C14B H14D 107 . . ?
H14C C14B H14D 106.7 . . ?
C14B C15B C16B 109(3) . . ?
C14B C15B H15C 109.9 . . ?
C16B C15B H15C 109.9 . . ?
C14B C15B H15D 109.8 . . ?
C16B C15B H15D 109.8 . . ?
H15C C15B H15D 108.3 . . ?
C15B C16B H16D 109.4 . . ?
C15B C16B H16E 109.6 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.4 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?

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
O3 Sn O1 C1 -14.7(4) 6_675 . . . ?
C13 Sn O1 C1 -124.3(3) . . . . ?
N2 Sn O1 C1 -11.8(2) . . . . ?
C9 Sn O1 C1 96.4(3) . . . . ?
O3 Sn O1 C1 163.5(2) . . . . ?
O3 Sn O3 C5 166.0(2) 6_675 . . 6_675 ?
C13 Sn O3 C5 -84.9(3) . . . 6_675 ?
N2 Sn O3 C5 159.1(3) . . . 6_675 ?
C9 Sn O3 C5 55.4(3) . . . 6_675 ?
O1 Sn O3 C5 -13.0(3) . . . 6_675 ?
O3 Sn O3 Sn 2.75(15) 6_675 . . 6_675 ?
C13 Sn O3 Sn 111.90(15) . . . 6_675 ?
N2 Sn O3 Sn -4.1(2) . . . 6_675 ?
C9 Sn O3 Sn -107.85(14) . . . 6_675 ?
O1 Sn O3 Sn -176.19(12) . . . 6_675 ?
O3 Sn N2 C4 -5.5(2) 6_675 . . . ?
C13 Sn N2 C4 -108.1(3) . . . . ?
C9 Sn N2 C4 97.2(3) . . . . ?
O1 Sn N2 C4 176.1(3) . . . . ?
O3 Sn N2 C4 1.0(4) . . . . ?
O3 Sn N2 C2 177.4(3) 6_675 . . . ?
C13 Sn N2 C2 74.8(3) . . . . ?
C9 Sn N2 C2 -79.9(3) . . . . ?
O1 Sn N2 C2 -0.9(3) . . . . ?
O3 Sn N2 C2 -176.1(2) . . . . ?
Sn O1 C1 N1 -160.4(3) . . . . ?
Sn O1 C1 C2 22.4(4) . . . . ?
C7 N1 C1 O1 177.9(4) . . . . ?
C8 N1 C1 O1 -2.5(6) . . . . ?
C7 N1 C1 C2 -5.0(5) . . . . ?
C8 N1 C1 C2 174.6(4) . . . . ?
C4 N2 C2 C1 -166.3(3) . . . . ?
Sn N2 C2 C1 10.7(4) . . . . ?
C4 N2 C2 C3 73.5(4) . . . . ?
Sn N2 C2 C3 -109.5(3) . . . . ?
O1 C1 C2 N2 -21.9(4) . . . . ?
N1 C1 C2 N2 160.9(3) . . . . ?
O1 C1 C2 C3 100.7(4) . . . . ?
N1 C1 C2 C3 -76.5(4) . . . . ?
C2 N2 C4 O2 1.7(5) . . . . ?
Sn N2 C4 O2 -175.6(3) . . . . ?
C2 N2 C4 C5 179.1(3) . . . . ?
Sn N2 C4 C5 1.8(4) . . . . ?
O2 C4 C5 O3 -177.3(3) . . . 6_675 ?
N2 C4 C5 O3 5.1(4) . . . 6_675 ?
O2 C4 C5 C6 -54.3(5) . . . . ?
N2 C4 C5 C6 128.1(3) . . . . ?
O3 Sn C9 C10 109.6(3) 6_675 . . . ?
C13 Sn C9 C10 -114.3(3) . . . . ?
N2 Sn C9 C10 28.6(3) . . . . ?
O1 Sn C9 C10 -38.8(3) . . . . ?
O3 Sn C9 C10 173.8(3) . . . . ?
Sn C9 C10 C11 -171.0(3) . . . . ?
C9 C10 C11 C12 179.5(5) . . . . ?
O3 Sn C13 C14B -92.9(10) 6_675 . . . ?
N2 Sn C13 C14B -11.1(10) . . . . ?
C9 Sn C13 C14B 131.0(10) . . . . ?
O1 Sn C13 C14B 55.0(10) . . . . ?
O3 Sn C13 C14B -158.5(10) . . . . ?
O3 Sn C13 C14A -48.4(6) 6_675 . . . ?
N2 Sn C13 C14A 33.5(6) . . . . ?
C9 Sn C13 C14A 175.6(5) . . . . ?
O1 Sn C13 C14A 99.5(6) . . . . ?
O3 Sn C13 C14A -114.0(6) . . . . ?
Sn C13 C14A C15A 175.2(9) . . . . ?
C13 C14A C15A C16A -178.8(15) . . . . ?
C14A C13 C14B C15B -3(3) . . . . ?
Sn C13 C14B C15B 85(3) . . . . ?
C13 C14B C15B C16B 155(3) . . . . ?

#END OF CIF