#------------------------------------------------------------------------------
#$Date: 2021-06-06 19:14:43 +0300 (Sun, 06 Jun 2021) $
#$Revision: 266200 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022350.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_2022350
loop_
_publ_author_name
'Linden, Anthony'
'Basu Baul, Tushar S.'
_publ_section_title
;
 Structural diversity among some dialkyltin(IV) benzoate and related
 derivatives
;
_journal_coeditor_code           OV3150
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              209
_journal_page_last               220
_journal_paper_doi               10.1107/S2053229621003545
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          '[Sn (C4 H9)2 (C14 H11 N2 O3)2], 0.5C6 H12'
_chemical_formula_moiety         'C36 H40 N4 O6 Sn, 0.5(C6 H12)'
_chemical_formula_sum            'C39 H46 N4 O6 Sn'
_chemical_formula_weight         785.49
_chemical_name_systematic
;
Dibutylbis{(E)-2-hydroxy-5-[(3-methylphenyl)diazenyl]benzoato}tin(IV)
cyclohexane hemisolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.3046(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.40280(10)
_cell_length_b                   25.1718(2)
_cell_length_c                   15.50080(10)
_cell_measurement_reflns_used    84811
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     3662.71(5)
_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
;
SHELXL2018 (Sheldrick, 2015), Mercury (Macrae et al.,
2020) and PLATON
(Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1994)
;
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0657
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            90950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.029
_diffrn_reflns_theta_min         2.632
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SORTAV; Blessing, 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.630
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         10702
_refine_ls_number_restraints     645
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0398
_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)+(0.0545P)²+1.0512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                7109
_reflns_number_total             10708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3150sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2022350--2022354.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022350
_cod_database_fobs_code          2022350
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn1 1.14355(2) 0.40458(2) 0.17524(2) 0.03777(7) Uani d 1 . .
O O1 0.99456(19) 0.45491(7) 0.22890(10) 0.0422(4) Uani d 1 . .
O O2 1.01081(19) 0.48431(7) 0.09670(11) 0.0459(4) Uani d 1 . .
O O3 0.8742(2) 0.57069(8) 0.04591(11) 0.0452(4) Uani d 1 . .
H H3 0.922(4) 0.5455(14) 0.045(2) 0.069(12) Uiso d 1 . .
N N1 0.6414(2) 0.57079(8) 0.36788(13) 0.0389(5) Uani d 1 . .
N N2 0.5572(2) 0.60765(8) 0.38296(13) 0.0385(5) Uani d 1 . .
C C1 0.9573(3) 0.48839(10) 0.16860(14) 0.0375(5) Uani d 1 . .
C C2 0.8560(2) 0.53078(9) 0.18696(14) 0.0354(5) Uani d 1 . .
C C3 0.8204(3) 0.56998(10) 0.12480(15) 0.0364(5) Uani d 1 . .
C C4 0.7271(3) 0.61062(10) 0.14413(16) 0.0414(6) Uani d 1 . .
H H4 0.704542 0.637386 0.102346 0.050 Uiso calc 1 . .
C C5 0.6672(3) 0.61257(10) 0.22263(16) 0.0401(6) Uani d 1 . .
H H5 0.604374 0.640728 0.235119 0.048 Uiso calc 1 . .
C C6 0.6987(3) 0.57297(10) 0.28457(15) 0.0359(5) Uani d 1 . .
C C7 0.7924(3) 0.53284(9) 0.26635(15) 0.0358(5) Uani d 1 . .
H H7 0.814077 0.506154 0.308404 0.043 Uiso calc 1 . .
C C8 0.4993(3) 0.60429(9) 0.46625(15) 0.0370(5) Uani d 1 . .
C C9 0.3989(3) 0.64256(10) 0.48359(16) 0.0404(6) Uani d 1 . .
H H9 0.374403 0.668761 0.441186 0.049 Uiso calc 1 . .
C C10 0.3330(3) 0.64347(11) 0.56202(17) 0.0442(6) Uani d 1 . .
C C11 0.3726(3) 0.60474(11) 0.62258(17) 0.0475(7) Uani d 1 . .
H H11 0.330706 0.604756 0.676913 0.057 Uiso calc 1 . .
C C12 0.4716(3) 0.56619(11) 0.60530(17) 0.0474(6) Uani d 1 . .
H H12 0.495179 0.539636 0.647273 0.057 Uiso calc 1 . .
C C13 0.5368(3) 0.56584(10) 0.52760(16) 0.0419(6) Uani d 1 . .
H H13 0.606252 0.539696 0.516368 0.050 Uiso calc 1 . .
C C27 0.2235(3) 0.68518(13) 0.5788(2) 0.0584(8) Uani d 1 . .
H H271 0.184768 0.678779 0.635272 0.088 Uiso calc 1 . .
H H272 0.146349 0.683583 0.533646 0.088 Uiso calc 1 . .
H H273 0.268068 0.720375 0.578592 0.088 Uiso calc 1 . .
O O4 1.16131(18) 0.37375(7) 0.30096(11) 0.0428(4) Uani d 1 . .
O O5A 1.335(2) 0.3262(13) 0.2380(11) 0.038(3) Uani d 0.437(5) A 1
O O6A 1.4503(15) 0.2495(6) 0.3328(6) 0.0458(18) Uani d 0.437(5) A 1
H H6A 1.426681 0.265078 0.286191 0.069 Uiso calc 0.437(5) A 1
N N3A 1.1171(13) 0.3174(6) 0.5944(7) 0.0364(18) Uani d 0.437(5) A 1
N N4A 1.1244(5) 0.2927(2) 0.6633(3) 0.0403(12) Uani d 0.437(5) A 1
C C14A 1.263(3) 0.3393(10) 0.3002(11) 0.035(2) Uani d 0.437(5) A 1
C C15A 1.276(2) 0.3105(7) 0.3838(9) 0.0336(17) Uani d 0.437(5) A 1
C C16A 1.3711(14) 0.2678(5) 0.3955(6) 0.0361(17) Uani d 0.437(5) A 1
C C17A 1.3879(9) 0.2418(3) 0.4754(5) 0.0358(15) Uani d 0.437(5) A 1
H H171 1.455009 0.213821 0.483992 0.043 Uiso calc 0.437(5) A 1
C C18A 1.3061(8) 0.2576(3) 0.5407(4) 0.0292(13) Uani d 0.437(5) A 1
H H181 1.316526 0.239976 0.594895 0.035 Uiso calc 0.437(5) A 1
C C19A 1.2077(8) 0.2987(3) 0.5299(4) 0.0309(14) Uani d 0.437(5) A 1
C C20A 1.1937(12) 0.3254(4) 0.4520(6) 0.0303(16) Uani d 0.437(5) A 1
H H201 1.128234 0.354046 0.444884 0.036 Uiso calc 0.437(5) A 1
C C21A 1.0284(8) 0.3130(3) 0.7254(5) 0.0394(15) Uani d 0.437(5) A 1
C C22A 0.9380(17) 0.3551(7) 0.7085(9) 0.047(2) Uani d 0.437(5) A 1
H H221 0.938030 0.372809 0.654406 0.057 Uiso calc 0.437(5) A 1
C C23A 0.846(3) 0.3720(12) 0.7709(13) 0.0523(19) Uani d 0.437(5) A 1
C C24A 0.8551(14) 0.3465(5) 0.8502(8) 0.056(2) Uani d 0.437(5) A 1
H H241 0.795821 0.358344 0.893955 0.067 Uiso calc 0.437(5) A 1
C C25A 0.9464(10) 0.3049(4) 0.8683(6) 0.0552(18) Uani d 0.437(5) A 1
H H25A 0.948616 0.288099 0.923288 0.066 Uiso calc 0.437(5) A 1
C C26A 1.0355(8) 0.2874(3) 0.8057(6) 0.0447(16) Uani d 0.437(5) A 1
H H261 1.099738 0.258732 0.817100 0.054 Uiso calc 0.437(5) A 1
C C28A 0.7532(13) 0.4206(5) 0.7581(10) 0.059(2) Uani d 0.437(5) A 1
H H281 0.665835 0.411168 0.724009 0.089 Uiso calc 0.437(5) A 1
H H282 0.804899 0.447936 0.727597 0.089 Uiso calc 0.437(5) A 1
H H283 0.728524 0.434321 0.814542 0.089 Uiso calc 0.437(5) A 1
O O5B 1.3096(18) 0.3282(9) 0.2321(9) 0.038(2) Uani d 0.563(5) A 2
O O6B 1.4630(12) 0.2517(4) 0.3081(5) 0.0430(13) Uani d 0.563(5) A 2
H H6B 1.437641 0.272918 0.268220 0.064 Uiso calc 0.563(5) A 2
N N3B 1.1851(4) 0.28580(16) 0.6084(2) 0.0382(10) Uani d 0.563(5) A 2
N N4B 1.0894(10) 0.3200(5) 0.6092(5) 0.0395(15) Uani d 0.563(5) A 2
C C14B 1.253(2) 0.3355(7) 0.3023(9) 0.034(2) Uani d 0.563(5) A 2
C C15B 1.2916(16) 0.3040(5) 0.3807(7) 0.0325(14) Uani d 0.563(5) A 2
C C16B 1.3935(10) 0.2631(4) 0.3785(5) 0.0335(14) Uani d 0.563(5) A 2
C C17B 1.4235(7) 0.2322(3) 0.4516(4) 0.0376(13) Uani d 0.563(5) A 2
H H172 1.493150 0.204936 0.450500 0.045 Uiso calc 0.563(5) A 2
C C18B 1.3532(6) 0.2410(2) 0.5249(4) 0.0350(11) Uani d 0.563(5) A 2
H H182 1.373890 0.219341 0.574244 0.042 Uiso calc 0.563(5) A 2
C C19B 1.2507(6) 0.2814(3) 0.5287(3) 0.0314(12) Uani d 0.563(5) A 2
C C20B 1.2228(9) 0.3132(3) 0.4569(5) 0.0328(14) Uani d 0.563(5) A 2
H H202 1.156312 0.341497 0.459372 0.039 Uiso calc 0.563(5) A 2
C C21B 1.0245(7) 0.3227(3) 0.6912(4) 0.0404(13) Uani d 0.563(5) A 2
C C22B 0.9174(13) 0.3598(5) 0.6964(7) 0.0474(17) Uani d 0.563(5) A 2
H H222 0.890803 0.380898 0.647321 0.057 Uiso calc 0.563(5) A 2
C C23B 0.847(3) 0.3667(9) 0.7726(10) 0.0531(17) Uani d 0.563(5) A 2
C C24B 0.8824(11) 0.3341(4) 0.8423(6) 0.0554(18) Uani d 0.563(5) A 2
H H242 0.833196 0.337597 0.893834 0.067 Uiso calc 0.563(5) A 2
C C25B 0.9873(8) 0.2969(3) 0.8375(5) 0.0541(15) Uani d 0.563(5) A 2
H H252 1.011694 0.275187 0.886349 0.065 Uiso calc 0.563(5) A 2
C C26B 1.0593(6) 0.2902(2) 0.7617(5) 0.0465(12) Uani d 0.563(5) A 2
H H263 1.131037 0.263793 0.758446 0.056 Uiso calc 0.563(5) A 2
C C28B 0.7288(11) 0.4068(4) 0.7728(8) 0.071(2) Uani d 0.563(5) A 2
H H284 0.754429 0.434989 0.814503 0.107 Uiso calc 0.563(5) A 2
H H285 0.641172 0.389335 0.789138 0.107 Uiso calc 0.563(5) A 2
H H286 0.713613 0.422241 0.714997 0.107 Uiso calc 0.563(5) A 2
C C29 1.0163(3) 0.34748(10) 0.10760(16) 0.0412(6) Uani d 1 . .
H H291 0.978564 0.362721 0.052015 0.049 Uiso calc 1 . .
H H292 1.075319 0.316216 0.094748 0.049 Uiso calc 1 . .
C C30 0.8923(3) 0.32999(11) 0.16058(16) 0.0429(6) Uani d 1 . .
H H301 0.930799 0.315112 0.216247 0.051 Uiso calc 1 . .
H H302 0.834154 0.361491 0.173503 0.051 Uiso calc 1 . .
C C31 0.7970(3) 0.28867(11) 0.11466(17) 0.0444(6) Uani d 1 . .
H H311 0.757029 0.303476 0.059265 0.053 Uiso calc 1 . .
H H312 0.854462 0.257036 0.101545 0.053 Uiso calc 1 . .
C C32 0.6759(3) 0.27222(14) 0.1699(2) 0.0600(8) Uani d 1 . .
H H321 0.715235 0.256159 0.223728 0.090 Uiso calc 1 . .
H H322 0.614986 0.246356 0.138249 0.090 Uiso calc 1 . .
H H323 0.619406 0.303553 0.183397 0.090 Uiso calc 1 . .
C C33 1.3355(3) 0.44608(11) 0.16023(18) 0.0474(6) Uani d 1 . .
H H331 1.312307 0.483083 0.142993 0.057 Uiso calc 1 . .
H H332 1.389692 0.447418 0.216890 0.057 Uiso calc 1 . .
C C34 1.4310(3) 0.42214(11) 0.09390(18) 0.0450(6) Uani d 1 . .
H H341 1.447514 0.384176 0.107854 0.054 Uiso calc 1 . .
H H342 1.380992 0.424035 0.035994 0.054 Uiso calc 1 . .
C C35 1.5724(3) 0.44980(13) 0.0910(2) 0.0536(7) Uani d 1 . .
H H351 1.626598 0.444800 0.147116 0.064 Uiso calc 1 . .
H H352 1.556030 0.488363 0.082824 0.064 Uiso calc 1 . .
C C36 1.6606(3) 0.42936(15) 0.0192(2) 0.0639(8) Uani d 1 . .
H H361 1.679330 0.391364 0.027768 0.096 Uiso calc 1 . .
H H362 1.751182 0.448674 0.020065 0.096 Uiso calc 1 . .
H H363 1.608370 0.434816 -0.036627 0.096 Uiso calc 1 . .
C C37 0.9061(6) 0.5119(2) 0.5726(4) 0.149(3) Uani d 1 . .
H H371 0.948957 0.493958 0.624624 0.179 Uiso calc 1 . .
H H372 0.822029 0.532405 0.589114 0.179 Uiso calc 1 . .
C C38 1.0160(4) 0.54900(15) 0.5328(3) 0.0857(12) Uani d 1 . .
H H381 0.963940 0.572510 0.490655 0.103 Uiso calc 1 . .
H H382 1.057966 0.571923 0.579548 0.103 Uiso calc 1 . .
C C39 1.1321(5) 0.5243(2) 0.4897(3) 0.1039(15) Uani d 1 . .
H H391 1.188027 0.552653 0.463175 0.125 Uiso calc 1 . .
H H392 1.195644 0.506552 0.533944 0.125 Uiso calc 1 . .
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'
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 O2 . . 53.93(5) y
O1 Sn1 O4 . . 82.76(6) y
O1 Sn1 O5A . . 135.8(3) y
O1 Sn1 O5B . . 135.6(2) y
O1 Sn1 C29 . . 103.65(9) y
O1 Sn1 C33 . . 109.89(9) y
O2 Sn1 O4 . . 136.44(6) y
O2 Sn1 O5A . . 167.5(4) y
O2 Sn1 O5B . . 169.5(3) y
O2 Sn1 C29 . . 92.83(8) y
O2 Sn1 C33 . . 87.56(9) y
O4 Sn1 O5A . . 53.3(3) y
O4 Sn1 O5B . . 52.9(2) y
O4 Sn1 C29 . . 102.85(9) y
O4 Sn1 C33 . . 105.25(9) y
O5A Sn1 C29 . . 91.6(6) y
O5A Sn1 C33 . . 81.4(6) y
O5B Sn1 C29 . . 88.7(5) y
O5B Sn1 C33 . . 84.4(5) y
C29 Sn1 C33 . . 138.31(10) y
C1 O1 Sn1 . . 105.49(14) ?
C1 O2 Sn1 . . 81.66(14) ?
C3 O3 H3 . . 105(3) ?
N2 N1 C6 . . 114.6(2) ?
N1 N2 C8 . . 113.7(2) ?
O2 C1 O1 . . 118.9(2) ?
O2 C1 C2 . . 122.0(2) ?
O1 C1 C2 . . 119.07(19) ?
C7 C2 C3 . . 118.7(2) ?
C7 C2 C1 . . 120.8(2) ?
C3 C2 C1 . . 120.6(2) ?
O3 C3 C4 . . 117.3(2) ?
O3 C3 C2 . . 122.9(2) ?
C4 C3 C2 . . 119.8(2) ?
C5 C4 C3 . . 120.9(2) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 120.0(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 119.5(2) ?
C7 C6 N1 . . 115.8(2) ?
C5 C6 N1 . . 124.7(2) ?
C6 C7 C2 . . 121.1(2) ?
C6 C7 H7 . . 119.4 ?
C2 C7 H7 . . 119.4 ?
C9 C8 C13 . . 120.1(2) ?
C9 C8 N2 . . 115.6(2) ?
C13 C8 N2 . . 124.3(2) ?
C8 C9 C10 . . 121.4(2) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C11 C10 C9 . . 117.5(2) ?
C11 C10 C27 . . 122.2(2) ?
C9 C10 C27 . . 120.3(3) ?
C12 C11 C10 . . 121.3(2) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C13 . . 120.7(3) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C8 . . 119.0(2) ?
C12 C13 H13 . . 120.5 ?
C8 C13 H13 . . 120.5 ?
C10 C27 H271 . . 109.5 ?
C10 C27 H272 . . 109.5 ?
H271 C27 H272 . . 109.5 ?
C10 C27 H273 . . 109.5 ?
H271 C27 H273 . . 109.5 ?
H272 C27 H273 . . 109.5 ?
C14B O4 Sn1 . . 108.0(5) ?
C14A O4 Sn1 . . 105.1(6) ?
C14A O5A Sn1 . . 73.6(12) ?
C16A O6A H6A . . 109.5 ?
N4A N3A C19A . . 115.7(9) ?
N3A N4A C21A . . 113.1(7) ?
O5A C14A O4 . . 128.0(15) ?
O5A C14A C15A . . 121.5(13) ?
O4 C14A C15A . . 110.0(9) ?
C20A C15A C16A . . 119.0(9) ?
C20A C15A C14A . . 120.6(9) ?
C16A C15A C14A . . 120.3(8) ?
O6A C16A C17A . . 116.3(8) ?
O6A C16A C15A . . 123.1(9) ?
C17A C16A C15A . . 120.6(8) ?
C18A C17A C16A . . 118.7(7) ?
C18A C17A H171 . . 120.6 ?
C16A C17A H171 . . 120.7 ?
C17A C18A C19A . . 121.8(6) ?
C17A C18A H181 . . 119.1 ?
C19A C18A H181 . . 119.1 ?
C20A C19A C18A . . 119.7(6) ?
C20A C19A N3A . . 114.9(7) ?
C18A C19A N3A . . 125.4(7) ?
C19A C20A C15A . . 120.1(8) ?
C19A C20A H201 . . 119.9 ?
C15A C20A H201 . . 119.9 ?
C22A C21A C26A . . 121.5(8) ?
C22A C21A N4A . . 123.1(8) ?
C26A C21A N4A . . 115.4(7) ?
C21A C22A C23A . . 120.2(11) ?
C21A C22A H221 . . 119.9 ?
C23A C22A H221 . . 119.9 ?
C24A C23A C22A . . 117.5(10) ?
C24A C23A C28A . . 119.9(10) ?
C22A C23A C28A . . 122.1(11) ?
C25A C24A C23A . . 122.8(10) ?
C25A C24A H241 . . 118.6 ?
C23A C24A H241 . . 118.6 ?
C24A C25A C26A . . 119.6(9) ?
C24A C25A H25A . . 120.2 ?
C26A C25A H25A . . 120.2 ?
C25A C26A C21A . . 118.4(8) ?
C25A C26A H261 . . 120.8 ?
C21A C26A H261 . . 120.8 ?
C23A C28A H281 . . 109.5 ?
C23A C28A H282 . . 109.5 ?
H281 C28A H282 . . 109.5 ?
C23A C28A H283 . . 109.5 ?
H281 C28A H283 . . 109.5 ?
H282 C28A H283 . . 109.5 ?
C14B O5B Sn1 . . 84.7(9) ?
C16B O6B H6B . . 109.5 ?
N4B N3B C19B . . 114.4(5) ?
N3B N4B C21B . . 112.5(7) ?
O5B C14B O4 . . 114.3(11) ?
O5B C14B C15B . . 122.5(10) ?
O4 C14B C15B . . 123.1(8) ?
C20B C15B C16B . . 119.4(7) ?
C20B C15B C14B . . 120.1(7) ?
C16B C15B C14B . . 120.5(6) ?
O6B C16B C17B . . 117.4(6) ?
O6B C16B C15B . . 122.8(7) ?
C17B C16B C15B . . 119.7(6) ?
C18B C17B C16B . . 120.2(5) ?
C18B C17B H172 . . 119.9 ?
C16B C17B H172 . . 119.9 ?
C17B C18B C19B . . 121.2(5) ?
C17B C18B H182 . . 119.4 ?
C19B C18B H182 . . 119.4 ?
C20B C19B C18B . . 119.0(5) ?
C20B C19B N3B . . 125.8(6) ?
C18B C19B N3B . . 115.3(5) ?
C19B C20B C15B . . 120.5(6) ?
C19B C20B H202 . . 119.7 ?
C15B C20B H202 . . 119.7 ?
C22B C21B C26B . . 119.6(6) ?
C22B C21B N4B . . 115.5(7) ?
C26B C21B N4B . . 124.9(6) ?
C21B C22B C23B . . 121.1(8) ?
C21B C22B H222 . . 119.5 ?
C23B C22B H222 . . 119.5 ?
C24B C23B C22B . . 118.9(8) ?
C24B C23B C28B . . 122.8(8) ?
C22B C23B C28B . . 118.1(9) ?
C25B C24B C23B . . 120.4(8) ?
C25B C24B H242 . . 119.8 ?
C23B C24B H242 . . 119.8 ?
C24B C25B C26B . . 120.9(7) ?
C24B C25B H252 . . 119.6 ?
C26B C25B H252 . . 119.6 ?
C21B C26B C25B . . 119.1(6) ?
C21B C26B H263 . . 120.5 ?
C25B C26B H263 . . 120.5 ?
C23B C28B H284 . . 109.5 ?
C23B C28B H285 . . 109.5 ?
H284 C28B H285 . . 109.5 ?
C23B C28B H286 . . 109.5 ?
H284 C28B H286 . . 109.5 ?
H285 C28B H286 . . 109.5 ?
C30 C29 Sn1 . . 110.95(16) ?
C30 C29 H291 . . 109.4 ?
Sn1 C29 H291 . . 109.4 ?
C30 C29 H292 . . 109.4 ?
Sn1 C29 H292 . . 109.4 ?
H291 C29 H292 . . 108.0 ?
C31 C30 C29 . . 113.1(2) ?
C31 C30 H301 . . 109.0 ?
C29 C30 H301 . . 109.0 ?
C31 C30 H302 . . 109.0 ?
C29 C30 H302 . . 109.0 ?
H301 C30 H302 . . 107.8 ?
C32 C31 C30 . . 111.2(2) ?
C32 C31 H311 . . 109.4 ?
C30 C31 H311 . . 109.4 ?
C32 C31 H312 . . 109.4 ?
C30 C31 H312 . . 109.4 ?
H311 C31 H312 . . 108.0 ?
C31 C32 H321 . . 109.5 ?
C31 C32 H322 . . 109.5 ?
H321 C32 H322 . . 109.5 ?
C31 C32 H323 . . 109.5 ?
H321 C32 H323 . . 109.5 ?
H322 C32 H323 . . 109.5 ?
C34 C33 Sn1 . . 114.74(18) ?
C34 C33 H331 . . 108.6 ?
Sn1 C33 H331 . . 108.6 ?
C34 C33 H332 . . 108.6 ?
Sn1 C33 H332 . . 108.6 ?
H331 C33 H332 . . 107.6 ?
C35 C34 C33 . . 113.1(2) ?
C35 C34 H341 . . 109.0 ?
C33 C34 H341 . . 109.0 ?
C35 C34 H342 . . 109.0 ?
C33 C34 H342 . . 109.0 ?
H341 C34 H342 . . 107.8 ?
C34 C35 C36 . . 112.8(3) ?
C34 C35 H351 . . 109.0 ?
C36 C35 H351 . . 109.0 ?
C34 C35 H352 . . 109.0 ?
C36 C35 H352 . . 109.0 ?
H351 C35 H352 . . 107.8 ?
C35 C36 H361 . . 109.5 ?
C35 C36 H362 . . 109.5 ?
H361 C36 H362 . . 109.5 ?
C35 C36 H363 . . 109.5 ?
H361 C36 H363 . . 109.5 ?
H362 C36 H363 . . 109.5 ?
C39 C37 C38 3_766 . 106.1(5) ?
C39 C37 H371 3_766 . 110.5 ?
C38 C37 H371 . . 110.5 ?
C39 C37 H372 3_766 . 110.5 ?
C38 C37 H372 . . 110.5 ?
H371 C37 H372 . . 108.7 ?
C39 C38 C37 . . 117.5(4) ?
C39 C38 H381 . . 107.9 ?
C37 C38 H381 . . 107.9 ?
C39 C38 H382 . . 107.9 ?
C37 C38 H382 . . 107.9 ?
H381 C38 H382 . . 107.2 ?
C37 C39 C38 3_766 . 116.0(4) ?
C37 C39 H391 3_766 . 108.3 ?
C38 C39 H391 . . 108.3 ?
C37 C39 H392 3_766 . 108.3 ?
C38 C39 H392 . . 108.3 ?
H391 C39 H392 . . 107.4 ?
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 . 2.0961(16) y
Sn1 O2 . 2.6252(18) y
Sn1 O4 . 2.0954(17) y
Sn1 O5A . 2.81(3) y
Sn1 O5B . 2.60(2) y
Sn1 C29 . 2.110(3) y
Sn1 C33 . 2.110(3) y
Sn1 O3 3_765 3.4786(17) y
O1 C1 . 1.292(3) ?
O2 C1 . 1.253(2) ?
O3 C3 . 1.350(3) ?
O3 H3 . 0.78(3) ?
N1 N2 . 1.250(3) y
N1 C6 . 1.429(3) ?
N2 C8 . 1.433(3) ?
C1 C2 . 1.469(3) ?
C2 C7 . 1.400(3) ?
C2 C3 . 1.406(3) ?
C3 C4 . 1.392(4) ?
C4 C5 . 1.371(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.404(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.380(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.386(3) ?
C8 C13 . 1.388(3) ?
C9 C10 . 1.396(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.389(4) ?
C10 C27 . 1.504(4) ?
C11 C12 . 1.382(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.383(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C27 H271 . 0.9800 ?
C27 H272 . 0.9800 ?
C27 H273 . 0.9800 ?
O4 C14B . 1.291(4) ?
O4 C14A . 1.291(4) ?
O5A C14A . 1.254(4) ?
O6A C16A . 1.340(9) ?
O6A H6A . 0.8400 ?
N3A N4A . 1.233(10) ?
N3A C19A . 1.430(10) ?
N4A C21A . 1.450(8) ?
C14A C15A . 1.485(11) ?
C15A C20A . 1.395(10) ?
C15A C16A . 1.405(10) ?
C16A C17A . 1.401(10) ?
C17A C18A . 1.365(8) ?
C17A H171 . 0.9500 ?
C18A C19A . 1.393(8) ?
C18A H181 . 0.9500 ?
C19A C20A . 1.382(9) ?
C20A H201 . 0.9500 ?
C21A C22A . 1.375(10) ?
C21A C26A . 1.399(9) ?
C22A C23A . 1.401(11) ?
C22A H221 . 0.9500 ?
C23A C24A . 1.386(11) ?
C23A C28A . 1.508(11) ?
C24A C25A . 1.374(11) ?
C24A H241 . 0.9500 ?
C25A C26A . 1.390(9) ?
C25A H25A . 0.9500 ?
C26A H261 . 0.9500 ?
C28A H281 . 0.9800 ?
C28A H282 . 0.9800 ?
C28A H283 . 0.9800 ?
O5B C14B . 1.253(4) ?
O6B C16B . 1.336(6) ?
O6B H6B . 0.8400 ?
N3B N4B . 1.246(8) ?
N3B C19B . 1.418(6) ?
N4B C21B . 1.444(8) ?
C14B C15B . 1.480(8) ?
C15B C20B . 1.398(8) ?
C15B C16B . 1.407(8) ?
C16B C17B . 1.389(8) ?
C17B C18B . 1.366(7) ?
C17B H172 . 0.9500 ?
C18B C19B . 1.405(7) ?
C18B H182 . 0.9500 ?
C19B C20B . 1.383(7) ?
C20B H202 . 0.9500 ?
C21B C22B . 1.377(8) ?
C21B C26B . 1.390(7) ?
C22B C23B . 1.397(9) ?
C22B H222 . 0.9500 ?
C23B C24B . 1.381(9) ?
C23B C28B . 1.503(10) ?
C24B C25B . 1.366(9) ?
C24B H242 . 0.9500 ?
C25B C26B . 1.401(8) ?
C25B H252 . 0.9500 ?
C26B H263 . 0.9500 ?
C28B H284 . 0.9800 ?
C28B H285 . 0.9800 ?
C28B H286 . 0.9800 ?
C29 C30 . 1.529(3) ?
C29 H291 . 0.9900 ?
C29 H292 . 0.9900 ?
C30 C31 . 1.522(4) ?
C30 H301 . 0.9900 ?
C30 H302 . 0.9900 ?
C31 C32 . 1.521(4) ?
C31 H311 . 0.9900 ?
C31 H312 . 0.9900 ?
C32 H321 . 0.9800 ?
C32 H322 . 0.9800 ?
C32 H323 . 0.9800 ?
C33 C34 . 1.527(4) ?
C33 H331 . 0.9900 ?
C33 H332 . 0.9900 ?
C34 C35 . 1.504(4) ?
C34 H341 . 0.9900 ?
C34 H342 . 0.9900 ?
C35 C36 . 1.516(4) ?
C35 H351 . 0.9900 ?
C35 H352 . 0.9900 ?
C36 H361 . 0.9800 ?
C36 H362 . 0.9800 ?
C36 H363 . 0.9800 ?
C37 C39 3_766 1.360(5) ?
C37 C38 . 1.546(6) ?
C37 H371 . 0.9900 ?
C37 H372 . 0.9900 ?
C38 C39 . 1.453(5) ?
C38 H381 . 0.9900 ?
C38 H382 . 0.9900 ?
C39 H391 . 0.9900 ?
C39 H392 . 0.9900 ?
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 . 0.78(3) 1.91(3) 2.623(3) 153(3) yes
O3 H3 O2 3_765 0.78(3) 2.44(3) 2.872(3) 117(3) yes
O6A H6A O5A . 0.84 1.90 2.62(3) 144 yes
O6B H6B O5B . 0.84 1.90 2.64(2) 146 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 N2 C8 . . . . 179.1(2) ?
Sn1 O2 C1 O1 . . . . -0.6(2) ?
Sn1 O2 C1 C2 . . . . 178.0(2) ?
Sn1 O1 C1 O2 . . . . 0.7(3) ?
Sn1 O1 C1 C2 . . . . -177.90(18) ?
O2 C1 C2 C7 . . . . 176.8(2) ?
O1 C1 C2 C7 . . . . -4.6(4) ?
O2 C1 C2 C3 . . . . -2.9(4) ?
O1 C1 C2 C3 . . . . 175.7(2) ?
C7 C2 C3 O3 . . . . -178.8(2) ?
C1 C2 C3 O3 . . . . 0.9(4) ?
C7 C2 C3 C4 . . . . 2.0(4) ?
C1 C2 C3 C4 . . . . -178.3(2) ?
O3 C3 C4 C5 . . . . 179.6(2) ?
C2 C3 C4 C5 . . . . -1.1(4) ?
C3 C4 C5 C6 . . . . -0.6(4) ?
C4 C5 C6 C7 . . . . 1.3(4) ?
C4 C5 C6 N1 . . . . -179.3(2) ?
N2 N1 C6 C7 . . . . 179.8(2) ?
N2 N1 C6 C5 . . . . 0.4(4) ?
C5 C6 C7 C2 . . . . -0.3(4) ?
N1 C6 C7 C2 . . . . -179.8(2) ?
C3 C2 C7 C6 . . . . -1.3(4) ?
C1 C2 C7 C6 . . . . 179.0(2) ?
N1 N2 C8 C9 . . . . -176.3(2) ?
N1 N2 C8 C13 . . . . 3.3(4) ?
C13 C8 C9 C10 . . . . -0.3(4) ?
N2 C8 C9 C10 . . . . 179.3(2) ?
C8 C9 C10 C11 . . . . 0.5(4) ?
C8 C9 C10 C27 . . . . -179.5(3) ?
C9 C10 C11 C12 . . . . -1.1(4) ?
C27 C10 C11 C12 . . . . 178.9(3) ?
C10 C11 C12 C13 . . . . 1.5(4) ?
C11 C12 C13 C8 . . . . -1.2(4) ?
C9 C8 C13 C12 . . . . 0.6(4) ?
N2 C8 C13 C12 . . . . -178.9(2) ?
C19A N3A N4A C21A . . . . -179.0(10) ?
Sn1 O5A C14A O4 . . . . 1(3) ?
Sn1 O5A C14A C15A . . . . 173(3) ?
Sn1 O4 C14A O5A . . . . -1(4) ?
Sn1 O4 C14A C15A . . . . -174.0(19) ?
O5A C14A C15A C20A . . . . -179(3) ?
O4 C14A C15A C20A . . . . -6(4) ?
O5A C14A C15A C16A . . . . 1(4) ?
O4 C14A C15A C16A . . . . 174(2) ?
C20A C15A C16A O6A . . . . 177.7(15) ?
C14A C15A C16A O6A . . . . -3(3) ?
C20A C15A C16A C17A . . . . -2(2) ?
C14A C15A C16A C17A . . . . 177(2) ?
O6A C16A C17A C18A . . . . -177.7(10) ?
C15A C16A C17A C18A . . . . 2.4(18) ?
C16A C17A C18A C19A . . . . -0.4(12) ?
C17A C18A C19A C20A . . . . -1.4(11) ?
C17A C18A C19A N3A . . . . 179.4(11) ?
N4A N3A C19A C20A . . . . 177.4(11) ?
N4A N3A C19A C18A . . . . -3.5(19) ?
C18A C19A C20A C15A . . . . 1.4(16) ?
N3A C19A C20A C15A . . . . -179.4(15) ?
C16A C15A C20A C19A . . . . 1(2) ?
C14A C15A C20A C19A . . . . -179(2) ?
N3A N4A C21A C22A . . . . 0.5(16) ?
N3A N4A C21A C26A . . . . -178.1(10) ?
C26A C21A C22A C23A . . . . -3(3) ?
N4A C21A C22A C23A . . . . 179(2) ?
C21A C22A C23A C24A . . . . 3(5) ?
C21A C22A C23A C28A . . . . 175(2) ?
C22A C23A C24A C25A . . . . -2(4) ?
C28A C23A C24A C25A . . . . -174(2) ?
C23A C24A C25A C26A . . . . 1(2) ?
C24A C25A C26A C21A . . . . -0.3(14) ?
C22A C21A C26A C25A . . . . 1.3(15) ?
N4A C21A C26A C25A . . . . 179.9(7) ?
C19B N3B N4B C21B . . . . 179.3(7) ?
Sn1 O5B C14B O4 . . . . -2.1(19) ?
Sn1 O5B C14B C15B . . . . -180(2) ?
Sn1 O4 C14B O5B . . . . 3(2) ?
Sn1 O4 C14B C15B . . . . -179.5(19) ?
O5B C14B C15B C20B . . . . -179(2) ?
O4 C14B C15B C20B . . . . 4(3) ?
O5B C14B C15B C16B . . . . -2(3) ?
O4 C14B C15B C16B . . . . -179.1(18) ?
C20B C15B C16B O6B . . . . 179.6(12) ?
C14B C15B C16B O6B . . . . 2(2) ?
C20B C15B C16B C17B . . . . 0.6(18) ?
C14B C15B C16B C17B . . . . -176.8(16) ?
O6B C16B C17B C18B . . . . -178.2(8) ?
C15B C16B C17B C18B . . . . 0.8(13) ?
C16B C17B C18B C19B . . . . -0.7(9) ?
C17B C18B C19B C20B . . . . -0.9(9) ?
C17B C18B C19B N3B . . . . 179.5(5) ?
N4B N3B C19B C20B . . . . 4.0(10) ?
N4B N3B C19B C18B . . . . -176.5(8) ?
C18B C19B C20B C15B . . . . 2.3(12) ?
N3B C19B C20B C15B . . . . -178.1(9) ?
C16B C15B C20B C19B . . . . -2.2(17) ?
C14B C15B C20B C19B . . . . 175.2(16) ?
N3B N4B C21B C22B . . . . -179.9(10) ?
N3B N4B C21B C26B . . . . -2.0(14) ?
C26B C21B C22B C23B . . . . 3(2) ?
N4B C21B C22B C23B . . . . -179(2) ?
C21B C22B C23B C24B . . . . -3(4) ?
C21B C22B C23B C28B . . . . -178.4(15) ?
C22B C23B C24B C25B . . . . 2(3) ?
C28B C23B C24B C25B . . . . 177.4(18) ?
C23B C24B C25B C26B . . . . -1.3(19) ?
C22B C21B C26B C25B . . . . -1.8(11) ?
N4B C21B C26B C25B . . . . -179.6(8) ?
C24B C25B C26B C21B . . . . 1.1(11) ?
Sn1 C29 C30 C31 . . . . -179.94(18) ?
C29 C30 C31 C32 . . . . 179.6(2) ?
Sn1 C33 C34 C35 . . . . -174.66(19) ?
C33 C34 C35 C36 . . . . -174.4(2) ?
C39 C37 C38 C39 3_766 . . . -48.3(6) ?
C37 C38 C39 C37 . . . 3_766 53.0(7) ?
