#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/34/2213469.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213469
loop_
_publ_author_name
'Linden, Anthony'
'Wolstenholme, David'
'Basu Baul, Tushar S.'
'Rynjah, Wandondor'
_publ_section_title
Bis{μ-2-hydroxy-5-[(E)-2-(2-methoxyphenyl)diazenyl]benzoato}bis(di-n-butyl{2-hydroxy-5-[(E)-2-(2-methoxyphenyl)diazenyl]benzoato}tin(IV))
_journal_coeditor_code           LH2373
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1547
_journal_page_last               m1548
_journal_paper_doi               10.1107/S1600536807020302
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Sn2 (C14 H11 N2 O4)4 (C4 H9)4]'
_chemical_formula_moiety         'C72 H80 N8 O16 Sn2'
_chemical_formula_sum            'C72 H80 N8 O16 Sn2'
_chemical_formula_weight         1550.66
_chemical_melting_point          353
_chemical_name_systematic
;
Bis{μ-2-hydroxy-5-[(E)-2-(2-methoxyphenyl)diazenyl]benzoato}bis(di-n-
butyl{2-hydroxy-5-[(E)-2-(2-methoxyphenyl)diazenyl]benzoato}tin(IV))
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.0634(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   35.6311(7)
_cell_length_b                   10.6333(2)
_cell_length_c                   19.5551(4)
_cell_measurement_reflns_used    84575
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     7186.9(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            70128
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            orange--red
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3184
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.726
_refine_diff_density_min         -1.124
_refine_ls_extinction_coef       0.00054(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6347
_refine_ls_number_restraints     147
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0562P)²+33.1175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                4601
_reflns_number_total             6348
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2373.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2213469
_cod_database_fobs_code          2213469
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn1 0.440621(10) 0.23007(4) 0.50793(3) 0.0626(2) Uani d D 1 . .
O O1 0.38955(10) 0.1216(3) 0.4884(2) 0.0622(11) Uani d . 1 A .
O O2 0.43609(12) -0.0038(4) 0.5434(3) 0.0775(13) Uani d . 1 A .
O O3 0.42002(13) -0.2343(4) 0.5729(3) 0.0739(12) Uani d . 1 A .
H H3 0.4325 -0.1672 0.5840 0.089 Uiso calc R 1 . .
O O4 0.21361(11) 0.1554(3) 0.4502(2) 0.0595(10) Uani d . 1 . .
O O5 0.40166(9) 0.3689(3) 0.4550(2) 0.0546(10) Uani d . 1 A .
O O6 0.45967(11) 0.4485(4) 0.4800(3) 0.0801(14) Uani d . 1 A .
O O7 0.47184(11) 0.6766(5) 0.4421(4) 0.104(2) Uani d . 1 A .
H H7 0.4759 0.6295 0.4776 0.124 Uiso calc R 1 . .
O O8 0.28023(12) 0.9501(4) 0.1671(2) 0.0615(10) Uani d . 1 . .
N N1 0.26745(13) -0.1497(4) 0.4320(2) 0.0515(11) Uani d . 1 . .
N N2 0.25529(13) -0.0380(4) 0.4257(2) 0.0518(11) Uani d . 1 . .
N N3 0.31623(12) 0.6859(4) 0.3049(2) 0.0478(10) Uani d . 1 . .
N N4 0.30688(12) 0.7685(4) 0.2575(2) 0.0462(10) Uani d . 1 . .
C C1 0.40120(16) 0.0127(6) 0.5147(3) 0.0614(16) Uani d . 1 . .
C C2 0.37205(16) -0.0880(5) 0.5096(3) 0.0541(14) Uani d . 1 A .
C C3 0.38338(17) -0.2071(6) 0.5400(3) 0.0589(15) Uani d . 1 . .
C C4 0.35504(19) -0.2998(5) 0.5339(3) 0.0611(16) Uani d . 1 A .
H H4 0.3622 -0.3799 0.5545 0.073 Uiso calc R 1 . .
C C5 0.31803(17) -0.2796(5) 0.4998(3) 0.0556(14) Uani d . 1 . .
H H5 0.2995 -0.3451 0.4967 0.067 Uiso calc R 1 A .
C C6 0.30644(16) -0.1620(5) 0.4686(3) 0.0499(13) Uani d . 1 A .
C C7 0.33387(15) -0.0672(5) 0.4743(3) 0.0507(13) Uani d . 1 . .
H H71 0.3264 0.0127 0.4537 0.061 Uiso calc R 1 A .
C C8 0.21665(16) -0.0261(5) 0.3836(3) 0.0513(13) Uani d . 1 . .
C C9 0.20017(18) -0.1081(5) 0.3296(3) 0.0598(15) Uani d . 1 . .
H H9 0.2145 -0.1785 0.3201 0.072 Uiso calc R 1 . .
C C10 0.16311(18) -0.0885(7) 0.2896(3) 0.0700(18) Uani d . 1 . .
H H10 0.1520 -0.1452 0.2527 0.084 Uiso calc R 1 . .
C C11 0.14208(19) 0.0138(6) 0.3031(4) 0.0701(17) Uani d . 1 . .
H H11 0.1165 0.0271 0.2757 0.084 Uiso calc R 1 . .
C C12 0.15840(17) 0.0967(6) 0.3567(3) 0.0608(15) Uani d . 1 . .
H H12 0.1439 0.1668 0.3661 0.073 Uiso calc R 1 . .
C C13 0.19547(16) 0.0780(5) 0.3962(3) 0.0525(14) Uani d . 1 . .
C C14 0.42436(14) 0.4608(5) 0.4515(3) 0.0551(14) Uani d . 1 . .
C C15 0.40969(14) 0.5758(5) 0.4136(3) 0.0476(13) Uani d . 1 A .
C C16 0.43376(16) 0.6769(6) 0.4106(4) 0.0676(18) Uani d . 1 . .
C C17 0.41870(17) 0.7851(6) 0.3733(4) 0.0729(19) Uani d . 1 A .
H H17 0.4351 0.8550 0.3721 0.087 Uiso calc R 1 . .
C C18 0.38074(16) 0.7911(5) 0.3388(3) 0.0573(15) Uani d . 1 . .
H H18 0.3709 0.8647 0.3131 0.069 Uiso calc R 1 A .
C C19 0.35611(14) 0.6903(5) 0.3410(3) 0.0425(11) Uani d . 1 A .
C C20 0.37058(14) 0.5844(5) 0.3788(3) 0.0457(12) Uani d . 1 . .
H H20 0.3537 0.5162 0.3813 0.055 Uiso calc R 1 A .
C C21 0.26767(15) 0.7612(5) 0.2192(3) 0.0457(12) Uani d . 1 . .
C C22 0.24313(15) 0.6617(5) 0.2244(3) 0.0516(13) Uani d . 1 . .
H H22 0.2525 0.5938 0.2555 0.062 Uiso calc R 1 . .
C C23 0.20544(17) 0.6604(6) 0.1849(3) 0.0596(15) Uani d . 1 . .
H H23 0.1886 0.5930 0.1891 0.072 Uiso calc R 1 . .
C C24 0.19255(19) 0.7583(7) 0.1393(3) 0.0735(19) Uani d . 1 . .
H H24 0.1665 0.7585 0.1124 0.088 Uiso calc R 1 . .
C C25 0.21640(19) 0.8555(6) 0.1317(3) 0.0660(17) Uani d . 1 . .
H H25 0.2068 0.9212 0.0992 0.079 Uiso calc R 1 . .
C C26 0.25438(17) 0.8588(5) 0.1710(3) 0.0531(14) Uani d . 1 . .
C C27 0.19379(19) 0.2689(5) 0.4603(4) 0.0676(17) Uani d . 1 . .
H H271 0.1876 0.3172 0.4163 0.101 Uiso calc R 1 . .
H H272 0.2104 0.3193 0.4976 0.101 Uiso calc R 1 . .
H H273 0.1698 0.2477 0.4738 0.101 Uiso calc R 1 . .
C C28 0.2687(2) 1.0449(6) 0.1137(3) 0.081(2) Uani d . 1 . .
H H281 0.2592 1.0045 0.0677 0.121 Uiso calc R 1 . .
H H282 0.2909 1.0983 0.1125 0.121 Uiso calc R 1 . .
H H283 0.2481 1.0965 0.1244 0.121 Uiso calc R 1 . .
C C29A 0.4745(7) 0.151(3) 0.4441(9) 0.104(5) Uani d PDU 0.401(8) A 1
H H291 0.5022 0.1578 0.4687 0.125 Uiso calc PR 0.401(8) A 1
H H292 0.4682 0.0605 0.4367 0.125 Uiso calc PR 0.401(8) A 1
C C30A 0.4676(6) 0.217(2) 0.3722(10) 0.123(4) Uani d PDU 0.401(8) A 1
H H301 0.4757 0.3057 0.3814 0.147 Uiso calc PR 0.401(8) A 1
H H302 0.4854 0.1786 0.3464 0.147 Uiso calc PR 0.401(8) A 1
C C31A 0.4272(6) 0.219(3) 0.3217(12) 0.147(4) Uani d PDU 0.401(8) A 1
H H311 0.4082 0.2621 0.3430 0.176 Uiso calc PR 0.401(8) A 1
H H312 0.4179 0.1323 0.3081 0.176 Uiso calc PR 0.401(8) A 1
C C32A 0.4340(9) 0.292(3) 0.2580(13) 0.166(7) Uani d PDU 0.401(8) A 1
H H321 0.4400 0.3800 0.2714 0.249 Uiso calc PR 0.401(8) A 1
H H322 0.4107 0.2883 0.2193 0.249 Uiso calc PR 0.401(8) A 1
H H323 0.4558 0.2547 0.2428 0.249 Uiso calc PR 0.401(8) A 1
C C29B 0.4633(5) 0.1640(18) 0.4227(7) 0.110(4) Uani d PDU 0.599(8) A 2
H H293 0.4836 0.2228 0.4158 0.132 Uiso calc PR 0.599(8) A 2
H H294 0.4755 0.0809 0.4353 0.132 Uiso calc PR 0.599(8) A 2
C C30B 0.4318(5) 0.1520(17) 0.3524(8) 0.135(4) Uani d PDU 0.599(8) A 2
H H303 0.4102 0.1032 0.3631 0.161 Uiso calc PR 0.599(8) A 2
H H304 0.4217 0.2379 0.3396 0.161 Uiso calc PR 0.599(8) A 2
C C31B 0.4400(6) 0.0947(19) 0.2865(9) 0.171(5) Uani d PDU 0.599(8) A 2
H H313 0.4490 0.0067 0.2948 0.205 Uiso calc PR 0.599(8) A 2
H H314 0.4595 0.1442 0.2699 0.205 Uiso calc PR 0.599(8) A 2
C C32B 0.3996(6) 0.101(2) 0.2330(11) 0.188(6) Uani d PDU 0.599(8) A 2
H H324 0.3816 0.1488 0.2539 0.282 Uiso calc PR 0.599(8) A 2
H H325 0.3897 0.0160 0.2217 0.282 Uiso calc PR 0.599(8) A 2
H H326 0.4023 0.1434 0.1898 0.282 Uiso calc PR 0.599(8) A 2
C C33A 0.4517(10) 0.2667(15) 0.6180(5) 0.096(4) Uani d PDU 0.50 A 1
H H331 0.4307 0.2293 0.6366 0.115 Uiso calc PR 0.50 A 1
H H332 0.4763 0.2255 0.6421 0.115 Uiso calc PR 0.50 A 1
C C34A 0.4544(5) 0.4080(13) 0.6348(6) 0.098(3) Uani d PDU 0.50 A 1
H H341 0.4752 0.4474 0.6165 0.118 Uiso calc PR 0.50 A 1
H H342 0.4297 0.4503 0.6131 0.118 Uiso calc PR 0.50 A 1
C C35A 0.4636(6) 0.4189(14) 0.7155(7) 0.123(4) Uani d PDU 0.50 A 1
H H351 0.4431 0.3766 0.7333 0.147 Uiso calc PR 0.50 A 1
H H352 0.4885 0.3767 0.7365 0.147 Uiso calc PR 0.50 A 1
C C36A 0.4660(6) 0.5578(15) 0.7375(10) 0.134(5) Uani d PDU 0.50 A 1
H H361 0.4558 0.6104 0.6960 0.200 Uiso calc PR 0.50 A 1
H H362 0.4931 0.5803 0.7581 0.200 Uiso calc PR 0.50 A 1
H H363 0.4508 0.5715 0.7724 0.200 Uiso calc PR 0.50 A 1
C C33B 0.4473(9) 0.2926(16) 0.6133(6) 0.098(4) Uani d PDU 0.50 A 2
H H333 0.4732 0.3318 0.6275 0.118 Uiso calc PR 0.50 A 2
H H334 0.4283 0.3612 0.6114 0.118 Uiso calc PR 0.50 A 2
C C34B 0.4437(5) 0.2066(16) 0.6743(9) 0.109(4) Uani d PDU 0.50 A 2
H H343 0.4216 0.1481 0.6591 0.131 Uiso calc PR 0.50 A 2
H H344 0.4397 0.2569 0.7146 0.131 Uiso calc PR 0.50 A 2
C C35B 0.4821(5) 0.1337(17) 0.6950(10) 0.130(5) Uani d PDU 0.50 A 2
H H353 0.4877 0.0947 0.6526 0.156 Uiso calc PR 0.50 A 2
H H354 0.5034 0.1921 0.7157 0.156 Uiso calc PR 0.50 A 2
C C36B 0.4791(6) 0.0312(18) 0.7489(11) 0.149(6) Uani d PDU 0.50 A 2
H H364 0.4785 0.0706 0.7939 0.223 Uiso calc PR 0.50 A 2
H H365 0.5016 -0.0245 0.7558 0.223 Uiso calc PR 0.50 A 2
H H366 0.4554 -0.0177 0.7314 0.223 Uiso calc PR 0.50 A 2
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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Sn Sn -0.6537 1.4246
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Sn1 C29A . . 105.5(9) ?
O1 Sn1 O5 . . 81.84(14) ?
C29A Sn1 O5 . . 113.0(5) ?
O1 Sn1 C33B . . 103.6(8) ?
O5 Sn1 C33B . . 99.3(6) ?
O1 Sn1 C33A . . 102.9(8) ?
C29A Sn1 C33A . . 132.7(11) yes
O5 Sn1 C33A . . 107.8(6) ?
O1 Sn1 C29B . . 98.8(6) ?
O5 Sn1 C29B . . 100.1(4) ?
C33B Sn1 C29B . . 152.2(10) ?
O1 Sn1 O6 . . 137.01(13) ?
C29A Sn1 O6 . . 90.9(8) ?
O5 Sn1 O6 . . 55.23(12) yes
C33B Sn1 O6 . . 87.1(6) ?
C33A Sn1 O6 . . 93.3(5) ?
C29B Sn1 O6 . . 87.7(6) ?
O1 Sn1 O2 . . 54.41(13) yes
C29A Sn1 O2 . . 81.8(8) ?
O5 Sn1 O2 . . 136.25(13) ?
C33B Sn1 O2 . . 92.3(5) ?
C33A Sn1 O2 . . 85.0(5) ?
C29B Sn1 O2 . . 87.3(6) ?
O6 Sn1 O2 . . 168.28(13) yes
O1 Sn1 O5 . . 81.86(13) yes
O1 Sn1 O7 . 5_666 164.01(13) ?
C29A Sn1 O7 . 5_666 69.4(9) ?
O5 Sn1 O7 . 5_666 114.15(12) ?
C33B Sn1 O7 . 5_666 74.6(9) ?
C33A Sn1 O7 . 5_666 72.9(9) ?
C29B Sn1 O7 . 5_666 79.3(6) ?
O6 Sn1 O7 . 5_666 58.97(12) ?
O2 Sn1 O7 . 5_666 109.60(12) ?
C1 O1 Sn1 . . 103.8(3) ?
C1 O2 Sn1 . . 82.2(3) ?
C3 O3 H3 . . 109.5 ?
C13 O4 C27 . . 117.1(5) ?
C14 O5 Sn1 . . 102.2(3) ?
C14 O6 Sn1 . . 84.2(3) ?
C16 O7 Sn1 . 5_666 160.1(4) ?
C16 O7 H7 . . 109.5 ?
Sn1 O7 H7 5_666 . 88.4 ?
C26 O8 C28 . . 117.7(5) ?
N2 N1 C6 . . 114.3(4) ?
N1 N2 C8 . . 113.6(4) ?
N4 N3 C19 . . 113.2(4) ?
N3 N4 C21 . . 113.6(4) ?
O2 C1 O1 . . 119.6(5) ?
O2 C1 C2 . . 122.4(5) ?
O1 C1 C2 . . 118.0(5) ?
C7 C2 C3 . . 119.8(5) ?
C7 C2 C1 . . 120.4(5) ?
C3 C2 C1 . . 119.7(5) ?
O3 C3 C4 . . 119.3(5) ?
O3 C3 C2 . . 122.7(5) ?
C4 C3 C2 . . 118.0(6) ?
C5 C4 C3 . . 122.2(6) ?
C5 C4 H4 . . 118.9 ?
C3 C4 H4 . . 118.9 ?
C4 C5 C6 . . 120.4(5) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C7 C6 N1 . . 124.2(5) ?
C7 C6 C5 . . 118.9(5) ?
N1 C6 C5 . . 116.9(5) ?
C2 C7 C6 . . 120.7(5) ?
C2 C7 H71 . . 119.7 ?
C6 C7 H71 . . 119.7 ?
C9 C8 C13 . . 119.1(5) ?
C9 C8 N2 . . 123.7(5) ?
C13 C8 N2 . . 117.1(5) ?
C10 C9 C8 . . 120.5(6) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.0(6) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 119.9(6) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C13 C12 C11 . . 120.2(6) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
O4 C13 C12 . . 123.8(5) ?
O4 C13 C8 . . 116.0(5) ?
C12 C13 C8 . . 120.2(5) ?
O6 C14 O5 . . 118.4(5) ?
O6 C14 C15 . . 120.7(5) ?
O5 C14 C15 . . 120.9(4) ?
C16 C15 C20 . . 118.9(5) ?
C16 C15 C14 . . 121.5(5) ?
C20 C15 C14 . . 119.6(4) ?
O7 C16 C15 . . 123.0(5) ?
O7 C16 C17 . . 117.2(5) ?
C15 C16 C17 . . 119.8(5) ?
C18 C17 C16 . . 120.5(5) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C17 C18 C19 . . 120.5(5) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C20 C19 C18 . . 119.3(5) ?
C20 C19 N3 . . 115.9(4) ?
C18 C19 N3 . . 124.7(5) ?
C19 C20 C15 . . 120.9(5) ?
C19 C20 H20 . . 119.5 ?
C15 C20 H20 . . 119.5 ?
C22 C21 C26 . . 119.7(5) ?
C22 C21 N4 . . 124.0(5) ?
C26 C21 N4 . . 116.3(5) ?
C23 C22 C21 . . 120.8(5) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C24 C23 C22 . . 118.8(6) ?
C24 C23 H23 . . 120.6 ?
C22 C23 H23 . . 120.6 ?
C25 C24 C23 . . 121.6(6) ?
C25 C24 H24 . . 119.2 ?
C23 C24 H24 . . 119.2 ?
C24 C25 C26 . . 120.5(6) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
O8 C26 C25 . . 125.0(5) ?
O8 C26 C21 . . 116.4(5) ?
C25 C26 C21 . . 118.6(6) ?
O4 C27 H271 . . 109.5 ?
O4 C27 H272 . . 109.5 ?
H271 C27 H272 . . 109.5 ?
O4 C27 H273 . . 109.5 ?
H271 C27 H273 . . 109.5 ?
H272 C27 H273 . . 109.5 ?
O8 C28 H281 . . 109.5 ?
O8 C28 H282 . . 109.5 ?
H281 C28 H282 . . 109.5 ?
O8 C28 H283 . . 109.5 ?
H281 C28 H283 . . 109.5 ?
H282 C28 H283 . . 109.5 ?
C30A C29A Sn1 . . 111.7(12) ?
C30A C29A H291 . . 109.3 ?
Sn1 C29A H291 . . 109.3 ?
C30A C29A H292 . . 109.3 ?
Sn1 C29A H292 . . 109.3 ?
H291 C29A H292 . . 107.9 ?
C31A C30A C29A . . 120.7(14) ?
C31A C30A H301 . . 107.1 ?
C29A C30A H301 . . 107.1 ?
C31A C30A H302 . . 107.1 ?
C29A C30A H302 . . 107.1 ?
H301 C30A H302 . . 106.8 ?
C30A C31A C32A . . 102.6(14) ?
C30A C31A H311 . . 111.3 ?
C32A C31A H311 . . 111.3 ?
C30A C31A H312 . . 111.3 ?
C32A C31A H312 . . 111.3 ?
H311 C31A H312 . . 109.2 ?
C30B C29B Sn1 . . 112.7(10) ?
C30B C29B H293 . . 109.0 ?
Sn1 C29B H293 . . 109.0 ?
C30B C29B H294 . . 109.0 ?
Sn1 C29B H294 . . 109.0 ?
H293 C29B H294 . . 107.8 ?
C31B C30B C29B . . 122.5(12) ?
C31B C30B H303 . . 106.7 ?
C29B C30B H303 . . 106.7 ?
C31B C30B H304 . . 106.7 ?
C29B C30B H304 . . 106.7 ?
H303 C30B H304 . . 106.6 ?
C30B C31B C32B . . 102.4(14) ?
C30B C31B H313 . . 111.3 ?
C32B C31B H313 . . 111.3 ?
C30B C31B H314 . . 111.3 ?
C32B C31B H314 . . 111.3 ?
H313 C31B H314 . . 109.2 ?
C31B C32B H324 . . 109.5 ?
C31B C32B H325 . . 109.5 ?
H324 C32B H325 . . 109.5 ?
C31B C32B H326 . . 109.5 ?
H324 C32B H326 . . 109.5 ?
H325 C32B H326 . . 109.5 ?
C34A C33A Sn1 . . 112.5(9) ?
C34A C33A H331 . . 109.1 ?
Sn1 C33A H331 . . 109.1 ?
C34A C33A H332 . . 109.1 ?
Sn1 C33A H332 . . 109.1 ?
H331 C33A H332 . . 107.8 ?
C35A C34A C33A . . 106.3(10) ?
C35A C34A H341 . . 110.5 ?
C33A C34A H341 . . 110.5 ?
C35A C34A H342 . . 110.5 ?
C33A C34A H342 . . 110.5 ?
H341 C34A H342 . . 108.7 ?
C36A C35A C34A . . 110.1(12) ?
C36A C35A H351 . . 109.6 ?
C34A C35A H351 . . 109.6 ?
C36A C35A H352 . . 109.6 ?
C34A C35A H352 . . 109.6 ?
H351 C35A H352 . . 108.2 ?
C34B C33B Sn1 . . 123.9(13) ?
C34B C33B H333 . . 106.4 ?
Sn1 C33B H333 . . 106.4 ?
C34B C33B H334 . . 106.4 ?
Sn1 C33B H334 . . 106.4 ?
H333 C33B H334 . . 106.4 ?
C33B C34B C35B . . 105.6(12) ?
C33B C34B H343 . . 110.6 ?
C35B C34B H343 . . 110.6 ?
C33B C34B H344 . . 110.6 ?
C35B C34B H344 . . 110.6 ?
H343 C34B H344 . . 108.8 ?
C36B C35B C34B . . 109.5(12) ?
C36B C35B H353 . . 109.8 ?
C34B C35B H353 . . 109.8 ?
C36B C35B H354 . . 109.8 ?
C34B C35B H354 . . 109.8 ?
H353 C35B H354 . . 108.2 ?
C35B C36B H364 . . 109.5 ?
C35B C36B H365 . . 109.5 ?
H364 C36B H365 . . 109.5 ?
C35B C36B H366 . . 109.5 ?
H364 C36B H366 . . 109.5 ?
H365 C36B H366 . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 O1 . 2.109(3) yes
Sn1 C29A . 2.112(11) yes
Sn1 O5 . 2.116(3) yes
Sn1 C33B . 2.122(10) yes
Sn1 C33A . 2.127(10) yes
Sn1 C29B . 2.139(10) yes
Sn1 O6 . 2.517(4) yes
Sn1 O2 . 2.597(4) yes
Sn1 O7 5_666 3.192(4) yes
O1 C1 . 1.294(7) ?
O2 C1 . 1.246(7) ?
O3 C3 . 1.339(7) ?
O3 H3 . 0.8400 ?
O4 C13 . 1.371(6) ?
O4 C27 . 1.436(7) ?
O5 C14 . 1.281(6) ?
O6 C14 . 1.253(6) ?
O7 C16 . 1.347(7) ?
O7 H7 . 0.8400 ?
O8 C26 . 1.353(7) ?
O8 C28 . 1.439(7) ?
N1 N2 . 1.261(6) ?
N1 C6 . 1.406(7) ?
N2 C8 . 1.427(7) ?
N3 N4 . 1.261(6) ?
N3 C19 . 1.426(6) ?
N4 C21 . 1.418(6) ?
C1 C2 . 1.478(8) ?
C2 C7 . 1.386(8) ?
C2 C3 . 1.415(8) ?
C3 C4 . 1.395(8) ?
C4 C5 . 1.342(8) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.409(8) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.390(7) ?
C7 H71 . 0.9500 ?
C8 C9 . 1.385(7) ?
C8 C13 . 1.395(8) ?
C9 C10 . 1.378(8) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.382(9) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.384(9) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.373(8) ?
C12 H12 . 0.9500 ?
C14 C15 . 1.459(7) ?
C15 C16 . 1.386(7) ?
C15 C20 . 1.397(7) ?
C16 C17 . 1.397(8) ?
C17 C18 . 1.358(8) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.393(7) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.377(7) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.392(8) ?
C21 C26 . 1.405(7) ?
C22 C23 . 1.377(7) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.375(9) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.369(9) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.385(8) ?
C25 H25 . 0.9500 ?
C27 H271 . 0.9800 ?
C27 H272 . 0.9800 ?
C27 H273 . 0.9800 ?
C28 H281 . 0.9800 ?
C28 H282 . 0.9800 ?
C28 H283 . 0.9800 ?
C29A C30A . 1.538(8) ?
C29A H291 . 0.9900 ?
C29A H292 . 0.9900 ?
C30A C31A . 1.535(8) ?
C30A H301 . 0.9900 ?
C30A H302 . 0.9900 ?
C31A C32A . 1.539(9) ?
C31A H311 . 0.9900 ?
C31A H312 . 0.9900 ?
C32A H321 . 0.9800 ?
C32A H322 . 0.9800 ?
C32A H323 . 0.9800 ?
C29B C30B . 1.556(12) ?
C29B H293 . 0.9900 ?
C29B H294 . 0.9900 ?
C30B C31B . 1.517(12) ?
C30B H303 . 0.9900 ?
C30B H304 . 0.9900 ?
C31B C32B . 1.560(12) ?
C31B H313 . 0.9900 ?
C31B H314 . 0.9900 ?
C32B H324 . 0.9800 ?
C32B H325 . 0.9800 ?
C32B H326 . 0.9800 ?
C33A C34A . 1.536(9) ?
C33A H331 . 0.9900 ?
C33A H332 . 0.9900 ?
C34A C35A . 1.536(8) ?
C34A H341 . 0.9900 ?
C34A H342 . 0.9900 ?
C35A C36A . 1.535(8) ?
C35A H351 . 0.9900 ?
C35A H352 . 0.9900 ?
C36A H361 . 0.9800 ?
C36A H362 . 0.9800 ?
C36A H363 . 0.9800 ?
C33B C34B . 1.533(12) ?
C33B H333 . 0.9900 ?
C33B H334 . 0.9900 ?
C34B C35B . 1.538(12) ?
C34B H343 . 0.9900 ?
C34B H344 . 0.9900 ?
C35B C36B . 1.537(12) ?
C35B H353 . 0.9900 ?
C35B H354 . 0.9900 ?
C36B H364 . 0.9800 ?
C36B H365 . 0.9800 ?
C36B H366 . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O2 . 0.84 1.93 2.613(6) 138 yes
O7 H7 O6 . 0.84 2.01 2.603(6) 127 yes
O7 H7 O6 5_666 0.84 2.39 2.871(6) 117 yes
C22 H22 O8 4_545 0.95 2.62 3.334(7) 134 yes
C27 H271 O8 4_545 0.98 2.62 3.449(8) 142 yes
C27 H272 O4 7_556 0.98 2.67 3.434(8) 136 yes
C32B H326 O3 6_555 0.98 2.69 3.67(2) 170 yes
C33B H333 O7 5_666 0.99 2.64 3.33(3) 127 yes
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
C29A Sn1 O1 C1 67.4(7)
O5 Sn1 O1 C1 179.1(4)
C33B Sn1 O1 C1 -83.3(7)
C33A Sn1 O1 C1 -74.4(7)
C29B Sn1 O1 C1 80.0(6)
O6 Sn1 O1 C1 176.2(4)
O2 Sn1 O1 C1 -0.3(4)
O1 Sn1 O2 C1 0.3(4)
C29A Sn1 O2 C1 -115.5(8)
O5 Sn1 O2 C1 -0.6(5)
C33B Sn1 O2 C1 105.4(9)
C33A Sn1 O2 C1 110.0(10)
C29B Sn1 O2 C1 -102.5(6)
O6 Sn1 O2 C1 -167.8(8)
O1 Sn1 O5 C14 -176.0(4)
C29A Sn1 O5 C14 -72.5(11)
C33B Sn1 O5 C14 81.4(9)
C33A Sn1 O5 C14 83.0(9)
C29B Sn1 O5 C14 -78.5(7)
O6 Sn1 O5 C14 1.6(4)
O2 Sn1 O5 C14 -175.3(3)
O1 Sn1 O6 C14 1.9(5)
C29A Sn1 O6 C14 116.1(7)
O5 Sn1 O6 C14 -1.6(4)
C33B Sn1 O6 C14 -105.0(9)
C33A Sn1 O6 C14 -111.0(10)
C29B Sn1 O6 C14 102.4(6)
O2 Sn1 O6 C14 167.6(7)
C6 N1 N2 C8 175.3(4)
C19 N3 N4 C21 177.3(4)
Sn1 O2 C1 O1 -0.4(6)
Sn1 O2 C1 C2 179.9(6)
Sn1 O1 C1 O2 0.5(7)
Sn1 O1 C1 C2 -179.8(5)
O2 C1 C2 C7 -176.9(6)
O1 C1 C2 C7 3.4(9)
O2 C1 C2 C3 1.9(10)
O1 C1 C2 C3 -177.7(6)
C7 C2 C3 O3 177.9(6)
C1 C2 C3 O3 -1.0(9)
C7 C2 C3 C4 -0.9(9)
C1 C2 C3 C4 -179.8(5)
O3 C3 C4 C5 -178.1(6)
C2 C3 C4 C5 0.7(9)
C3 C4 C5 C6 0.0(9)
N2 N1 C6 C7 -24.0(7)
N2 N1 C6 C5 157.5(5)
C4 C5 C6 C7 -0.5(8)
C4 C5 C6 N1 178.0(5)
C3 C2 C7 C6 0.3(8)
C1 C2 C7 C6 179.2(5)
N1 C6 C7 C2 -178.1(5)
C5 C6 C7 C2 0.4(8)
N1 N2 C8 C9 -28.8(7)
N1 N2 C8 C13 154.5(5)
C13 C8 C9 C10 -1.1(8)
N2 C8 C9 C10 -177.8(5)
C8 C9 C10 C11 0.1(9)
C9 C10 C11 C12 0.3(10)
C10 C11 C12 C13 0.3(9)
C27 O4 C13 C12 -6.8(8)
C27 O4 C13 C8 174.7(5)
C11 C12 C13 O4 -179.7(5)
C11 C12 C13 C8 -1.3(8)
C9 C8 C13 O4 -179.7(5)
N2 C8 C13 O4 -2.9(7)
C9 C8 C13 C12 1.7(8)
N2 C8 C13 C12 178.6(5)
Sn1 O6 C14 O5 2.5(5)
Sn1 O6 C14 C15 -176.0(6)
Sn1 O5 C14 O6 -3.0(7)
Sn1 O5 C14 C15 175.5(5)
O6 C14 C15 C16 -3.0(10)
O5 C14 C15 C16 178.6(6)
O6 C14 C15 C20 176.3(6)
O5 C14 C15 C20 -2.1(9)
C20 C15 C16 O7 -179.5(6)
C14 C15 C16 O7 -0.2(11)
C20 C15 C16 C17 0.2(10)
C14 C15 C16 C17 179.4(6)
O7 C16 C17 C18 178.5(7)
C15 C16 C17 C18 -1.3(11)
C16 C17 C18 C19 1.0(11)
C17 C18 C19 C20 0.4(9)
C17 C18 C19 N3 -178.0(6)
N4 N3 C19 C20 -162.8(5)
N4 N3 C19 C18 15.6(7)
C18 C19 C20 C15 -1.5(8)
N3 C19 C20 C15 177.0(5)
C16 C15 C20 C19 1.2(9)
C14 C15 C20 C19 -178.1(5)
N3 N4 C21 C22 -10.1(7)
N3 N4 C21 C26 173.3(4)
C26 C21 C22 C23 -2.8(8)
N4 C21 C22 C23 -179.3(5)
C21 C22 C23 C24 1.1(8)
C22 C23 C24 C25 0.9(9)
C23 C24 C25 C26 -1.0(10)
C28 O8 C26 C25 -6.1(8)
C28 O8 C26 C21 174.2(5)
C24 C25 C26 O8 179.6(6)
C24 C25 C26 C21 -0.7(9)
C22 C21 C26 O8 -177.7(5)
N4 C21 C26 O8 -0.9(7)
C22 C21 C26 C25 2.5(8)
N4 C21 C26 C25 179.3(5)
O1 Sn1 C29A C30A 92.9(18)
O5 Sn1 C29A C30A 5(2)
C33A Sn1 C29A C30A -142.2(13)
O6 Sn1 C29A C30A -46.9(18)
O2 Sn1 C29A C30A 142.3(18)
Sn1 C29A C30A C31A -60(3)
C29A C30A C31A C32A -179(2)
O1 Sn1 C29B C30B 42.7(14)
O5 Sn1 C29B C30B -40.5(14)
C33B Sn1 C29B C30B -174.0(13)
O6 Sn1 C29B C30B -94.6(13)
O2 Sn1 C29B C30B 96.1(14)
Sn1 C29B C30B C31B -173.6(15)
C29B C30B C31B C32B 178.5(18)
O1 Sn1 C33A C34A -123.3(19)
C29A Sn1 C33A C34A 111(2)
O5 Sn1 C33A C34A -38(2)
O6 Sn1 C33A C34A 17(2)
O2 Sn1 C33A C34A -175(2)
Sn1 C33A C34A C35A -178.5(15)
C33A C34A C35A C36A -179(2)
O1 Sn1 C33B C34B 47.2(19)
O5 Sn1 C33B C34B 131.0(17)
C29B Sn1 C33B C34B -95(3)
O6 Sn1 C33B C34B -175.0(19)
O2 Sn1 C33B C34B -6.7(19)
Sn1 C33B C34B C35B 78(2)
C33B C34B C35B C36B -172.0(17)
