# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex1
_database_code_depnum_ccdc_archive 'CCDC 1444872'
_audit_update_record             
;
2015-12-31 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H17 N5 O3 Sn'
_chemical_formula_sum            'C11 H17 N5 O3 Sn'
_chemical_formula_weight         385.99

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   'P 21/c'

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

_cell_length_a                   12.1488(10)
_cell_length_b                   10.8376(8)
_cell_length_c                   12.1250(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.254(3)
_cell_angle_gamma                90.00
_cell_volume                     1524.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2774
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      24.87

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8176
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2837
_reflns_number_gt                1961
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0306P)²+0.1508P] where P=(Fo²+2Fc²)/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_number_reflns         2837
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn01 Sn -0.04726(2) 0.07953(2) 0.69433(2) 0.03974(12) Uani 1 1 d . . .
N3 N 0.3583(3) 0.0161(3) 0.9292(3) 0.0367(8) Uani 1 1 d . . .
O6 O 0.5371(3) 0.1018(2) 0.6981(3) 0.0586(9) Uani 1 1 d . . .
N1 N 0.4552(3) -0.0343(3) 0.7912(3) 0.0376(8) Uani 1 1 d . . .
H1 H 0.4753 -0.0934 0.7540 0.045 Uiso 1 1 calc R . .
C4 C 0.3850(3) 0.1323(3) 0.9068(3) 0.0346(9) Uani 1 1 d . . .
C5 C 0.4447(3) 0.1720(3) 0.8340(3) 0.0379(10) Uani 1 1 d . . .
N9 N 0.3539(2) 0.2370(3) 0.9542(2) 0.0367(8) Uani 1 1 d . . .
N2 N 0.3779(3) -0.1847(3) 0.8793(3) 0.0543(10) Uani 1 1 d . . .
H2A H 0.3411 -0.2085 0.9261 0.065 Uiso 1 1 calc R . .
H2B H 0.4025 -0.2382 0.8399 0.065 Uiso 1 1 calc R . .
C2 C 0.3968(3) -0.0652(3) 0.8679(4) 0.0372(10) Uani 1 1 d . . .
N7 N 0.4534(3) 0.2990(3) 0.8363(3) 0.0455(9) Uani 1 1 d . . .
C10 C 0.1591(3) 0.2128(3) 0.9711(3) 0.0399(10) Uani 1 1 d . . .
H10A H 0.1547 0.1322 0.9353 0.048 Uiso 1 1 calc R . .
H10B H 0.1173 0.2085 1.0279 0.048 Uiso 1 1 calc R . .
C6 C 0.4844(4) 0.0837(4) 0.7690(4) 0.0421(10) Uani 1 1 d . . .
C9 C 0.2842(3) 0.2420(3) 1.0325(3) 0.0412(10) Uani 1 1 d . . .
H9A H 0.2897 0.3237 1.0663 0.049 Uiso 1 1 calc R . .
H9B H 0.3138 0.1833 1.0946 0.049 Uiso 1 1 calc R . .
C8 C 0.3985(3) 0.3333(4) 0.9085(3) 0.0443(11) Uani 1 1 d . . .
H8 H 0.3904 0.4154 0.9272 0.053 Uiso 1 1 calc R . .
C13 C -0.1215(5) 0.0452(4) 0.8279(4) 0.0753(16) Uani 1 1 d . . .
H13A H -0.0628 0.0186 0.8958 0.113 Uiso 1 1 calc R . .
H13B H -0.1790 -0.0181 0.8040 0.113 Uiso 1 1 calc R . .
H13C H -0.1566 0.1194 0.8446 0.113 Uiso 1 1 calc R . .
C14 C 0.1204(4) 0.0288(4) 0.6970(4) 0.0544(12) Uani 1 1 d . . .
H14A H 0.1191 -0.0028 0.6226 0.082 Uiso 1 1 calc R . .
H14B H 0.1488 -0.0337 0.7545 0.082 Uiso 1 1 calc R . .
H14C H 0.1699 0.0997 0.7150 0.082 Uiso 1 1 calc R . .
C12 C -0.1377(4) 0.1931(3) 0.5558(3) 0.0550(12) Uani 1 1 d . . .
H12A H -0.1413 0.2756 0.5834 0.082 Uiso 1 1 calc R . .
H12B H -0.2144 0.1617 0.5234 0.082 Uiso 1 1 calc R . .
H12C H -0.0985 0.1936 0.4977 0.082 Uiso 1 1 calc R . .
O2 O 0.1274(2) 0.4178(2) 0.9060(2) 0.0435(7) Uani 1 1 d . . .
C11 C 0.1009(3) 0.3059(3) 0.8799(4) 0.0378(10) Uani 1 1 d . . .
O1 O 0.0323(2) 0.2725(2) 0.7883(2) 0.0492(8) Uani 1 1 d . . .


_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
Sn01 C14 2.101(4) . ?
Sn01 C13 2.107(4) . ?
Sn01 C12 2.109(4) . ?
Sn01 O2 2.190(2) 2_546 ?
Sn01 O1 2.440(3) . ?
N3 C2 1.325(4) . ?
N3 C4 1.348(5) . ?
O6 C6 1.230(4) . ?
N1 C2 1.368(5) . ?
N1 C6 1.375(4) . ?
N1 H1 0.8600 . ?
C4 C5 1.368(5) . ?
C4 N9 1.374(4) . ?
C5 N7 1.380(4) . ?
C5 C6 1.413(5) . ?
N9 C8 1.367(4) . ?
N9 C9 1.448(4) . ?
N2 C2 1.330(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N7 C8 1.303(4) . ?
C10 C11 1.509(5) . ?
C10 C9 1.515(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O2 C11 1.272(4) . ?
O2 Sn01 2.190(2) 2_556 ?
C11 O1 1.229(4) . ?

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
C14 Sn01 C13 125.2(2) . . ?
C14 Sn01 C12 116.01(17) . . ?
C13 Sn01 C12 118.32(19) . . ?
C14 Sn01 O2 93.93(14) . 2_546 ?
C13 Sn01 O2 93.68(15) . 2_546 ?
C12 Sn01 O2 89.07(14) . 2_546 ?
C14 Sn01 O1 88.23(13) . . ?
C13 Sn01 O1 89.63(14) . . ?
C12 Sn01 O1 84.96(12) . . ?
O2 Sn01 O1 174.00(9) 2_546 . ?
C2 N3 C4 111.2(3) . . ?
C2 N1 C6 125.3(3) . . ?
C2 N1 H1 117.4 . . ?
C6 N1 H1 117.4 . . ?
N3 C4 C5 129.0(3) . . ?
N3 C4 N9 125.1(3) . . ?
C5 C4 N9 105.9(3) . . ?
C4 C5 N7 110.6(3) . . ?
C4 C5 C6 118.8(3) . . ?
N7 C5 C6 130.6(4) . . ?
C8 N9 C4 105.6(3) . . ?
C8 N9 C9 128.1(3) . . ?
C4 N9 C9 126.3(3) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N3 C2 N2 119.3(3) . . ?
N3 C2 N1 124.0(3) . . ?
N2 C2 N1 116.7(3) . . ?
C8 N7 C5 104.3(3) . . ?
C11 C10 C9 113.9(3) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O6 C6 N1 120.3(3) . . ?
O6 C6 C5 128.0(4) . . ?
N1 C6 C5 111.7(3) . . ?
N9 C9 C10 111.5(3) . . ?
N9 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N9 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N7 C8 N9 113.4(3) . . ?
N7 C8 H8 123.3 . . ?
N9 C8 H8 123.3 . . ?
Sn01 C13 H13A 109.5 . . ?
Sn01 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Sn01 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Sn01 C14 H14A 109.5 . . ?
Sn01 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Sn01 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Sn01 C12 H12A 109.5 . . ?
Sn01 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Sn01 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 O2 Sn01 125.9(3) . 2_556 ?
O1 C11 O2 124.0(4) . . ?
O1 C11 C10 120.7(3) . . ?
O2 C11 C10 115.2(4) . . ?
C11 O1 Sn01 137.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.085
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Complex2
_database_code_depnum_ccdc_archive 'CCDC 1444873'
_audit_update_record             
;
2015-12-31 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H35 N5 O3 Sn'
_chemical_formula_weight         512.22

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.030(5)
_cell_length_b                   11.026(5)
_cell_length_c                   17.428(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.716(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2460.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5677
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    1.066
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16872
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4573
_reflns_number_gt                3319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0847P)²+1.9899P] where P=(Fo²+2Fc²)/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_number_reflns         4573
_refine_ls_number_parameters     269
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.71976(3) 0.45910(3) 0.77434(2) 0.05295(17) Uani 1 1 d . . .
O1 O 0.6789(3) 0.3022(3) 0.8409(2) 0.0609(10) Uani 1 1 d . . .
N9 N 0.4847(3) 0.1470(3) 0.8763(2) 0.0444(9) Uani 1 1 d . . .
O2 O 0.7409(3) 0.1519(3) 0.7799(2) 0.0664(11) Uani 1 1 d . . .
N1 N 0.2961(3) -0.1185(4) 0.7883(3) 0.0534(11) Uani 1 1 d . . .
N3 N 0.4528(3) -0.0701(3) 0.8754(2) 0.0474(10) Uani 1 1 d . . .
C5 C 0.3419(4) 0.0846(4) 0.7988(3) 0.0471(11) Uani 1 1 d . . .
N7 N 0.3452(3) 0.2104(3) 0.7913(3) 0.0560(11) Uani 1 1 d . . .
O6 O 0.1866(3) 0.0163(3) 0.7142(3) 0.0762(13) Uani 1 1 d . . .
N2 N 0.3967(4) -0.2669(4) 0.8588(3) 0.0715(14) Uani 1 1 d . . .
H2A H 0.4505 -0.2898 0.8921 0.086 Uiso 1 1 calc R . .
H2B H 0.3520 -0.3196 0.8371 0.086 Uiso 1 1 calc R . .
C6 C 0.2682(4) -0.0013(5) 0.7622(4) 0.0549(13) Uani 1 1 d . . .
C4 C 0.4271(4) 0.0456(4) 0.8512(3) 0.0431(11) Uani 1 1 d . . .
C11 C 0.6985(4) 0.1914(4) 0.8327(3) 0.0487(12) Uani 1 1 d . . .
C10 C 0.6741(4) 0.1059(4) 0.8952(3) 0.0509(12) Uani 1 1 d . . .
H10A H 0.7357 0.0977 0.9357 0.061 Uiso 1 1 calc R . .
H10B H 0.6578 0.0264 0.8722 0.061 Uiso 1 1 calc R . .
C9 C 0.5826(4) 0.1488(5) 0.9322(3) 0.0505(12) Uani 1 1 d . . .
H9A H 0.5767 0.0967 0.9760 0.061 Uiso 1 1 calc R . .
H9B H 0.5963 0.2306 0.9519 0.061 Uiso 1 1 calc R . .
C2 C 0.3825(4) -0.1485(4) 0.8409(3) 0.0472(11) Uani 1 1 d . . .
C8 C 0.4306(4) 0.2426(4) 0.8382(3) 0.0518(13) Uani 1 1 d . . .
H8 H 0.4528 0.3227 0.8451 0.062 Uiso 1 1 calc R . .
C20 C 0.6498(5) 0.5695(5) 0.8514(4) 0.0663(16) Uani 1 1 d . . .
H20A H 0.6467 0.6525 0.8327 0.080 Uiso 1 1 calc R . .
H20B H 0.5787 0.5421 0.8499 0.080 Uiso 1 1 calc R . .
C12 C 0.6257(6) 0.4090(7) 0.6650(4) 0.0845(19) Uani 1 1 d . . .
H12A H 0.6137 0.4819 0.6335 0.101 Uiso 1 1 calc R . .
H12B H 0.6674 0.3552 0.6391 0.101 Uiso 1 1 calc R . .
C16 C 0.8820(5) 0.4232(6) 0.7940(4) 0.0785(17) Uani 1 1 d DU . .
H16A H 0.8939 0.3581 0.7593 0.094 Uiso 1 1 calc R . .
H16B H 0.9168 0.4947 0.7789 0.094 Uiso 1 1 calc R . .
C22 C 0.6582(8) 0.6314(9) 0.9942(5) 0.127(3) Uani 1 1 d . . .
H22A H 0.6858 0.6027 1.0466 0.153 Uiso 1 1 calc R . .
H22B H 0.5832 0.6192 0.9832 0.153 Uiso 1 1 calc R . .
C14 C 0.4641(9) 0.3146(12) 0.5829(6) 0.171(5) Uani 1 1 d . . .
H14A H 0.4362 0.3875 0.5556 0.205 Uiso 1 1 calc R . .
H14B H 0.5116 0.2782 0.5529 0.205 Uiso 1 1 calc R . .
C13 C 0.5280(8) 0.3528(13) 0.6624(5) 0.159(5) Uani 1 1 d . . .
H13A H 0.4851 0.4075 0.6865 0.191 Uiso 1 1 calc R . .
H13B H 0.5393 0.2809 0.6950 0.191 Uiso 1 1 calc R . .
C15 C 0.3779(11) 0.2310(16) 0.5826(8) 0.241(8) Uani 1 1 d . . .
H15A H 0.4049 0.1518 0.5978 0.362 Uiso 1 1 calc R . .
H15B H 0.3363 0.2272 0.5311 0.362 Uiso 1 1 calc R . .
H15C H 0.3356 0.2586 0.6187 0.362 Uiso 1 1 calc R . .
C21 C 0.7085(8) 0.5669(8) 0.9360(5) 0.120(3) Uani 1 1 d . . .
H21A H 0.7185 0.4829 0.9521 0.144 Uiso 1 1 calc R . .
H21B H 0.7771 0.6019 0.9375 0.144 Uiso 1 1 calc R . .
C17 C 0.9329(9) 0.3900(13) 0.8735(6) 0.157(4) Uani 1 1 d DU . .
H17A H 0.8948 0.3231 0.8910 0.189 Uiso 1 1 calc R . .
H17B H 0.9283 0.4582 0.9078 0.189 Uiso 1 1 calc R . .
C18 C 1.0533(10) 0.3515(12) 0.8823(8) 0.170(5) Uani 1 1 d U . .
H18A H 1.0863 0.4015 0.8481 0.204 Uiso 1 1 calc R . .
H18B H 1.0886 0.3664 0.9356 0.204 Uiso 1 1 calc R . .
C23 C 0.6856(11) 0.7673(12) 0.9854(7) 0.192(6) Uani 1 1 d . . .
H23A H 0.7544 0.7832 1.0144 0.288 Uiso 1 1 calc R . .
H23B H 0.6359 0.8171 1.0052 0.288 Uiso 1 1 calc R . .
H23C H 0.6834 0.7856 0.9313 0.288 Uiso 1 1 calc R . .
C19 C 1.0651(13) 0.2285(14) 0.8640(10) 0.228(7) Uani 1 1 d U . .
H19A H 1.0196 0.1798 0.8888 0.341 Uiso 1 1 calc R . .
H19B H 1.1362 0.2042 0.8822 0.341 Uiso 1 1 calc R . .
H19C H 1.0475 0.2177 0.8084 0.341 Uiso 1 1 calc R . .
H1 H 0.253(6) -0.193(7) 0.767(4) 0.11(2) Uiso 1 1 d . . .


_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 C16 2.115(7) . ?
Sn1 C12 2.137(7) . ?
Sn1 C20 2.137(5) . ?
Sn1 O1 2.202(3) . ?
Sn1 O2 2.420(4) 2_656 ?
O1 C11 1.262(5) . ?
N9 C8 1.369(6) . ?
N9 C4 1.373(5) . ?
N9 C9 1.454(6) . ?
O2 C11 1.237(5) . ?
O2 Sn1 2.420(4) 2_646 ?
N1 C2 1.354(6) . ?
N1 C6 1.395(7) . ?
N1 H1 1.02(8) . ?
N3 C2 1.321(6) . ?
N3 C4 1.366(6) . ?
C5 C4 1.369(7) . ?
C5 N7 1.395(6) . ?
C5 C6 1.413(7) . ?
N7 C8 1.302(7) . ?
O6 C6 1.240(7) . ?
N2 C2 1.347(6) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C11 C10 1.518(7) . ?
C10 C9 1.532(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8 0.9300 . ?
C20 C21 1.530(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C12 C13 1.410(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C16 C17 1.467(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C22 C21 1.486(11) . ?
C22 C23 1.555(16) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C14 C15 1.452(15) . ?
C14 C13 1.537(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C17 C18 1.604(15) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.408(17) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Sn1 C12 119.1(3) . . ?
C16 Sn1 C20 122.3(3) . . ?
C12 Sn1 C20 117.8(3) . . ?
C16 Sn1 O1 95.7(2) . . ?
C12 Sn1 O1 96.4(2) . . ?
C20 Sn1 O1 86.75(18) . . ?
C16 Sn1 O2 87.1(2) . 2_656 ?
C12 Sn1 O2 90.4(2) . 2_656 ?
C20 Sn1 O2 83.76(17) . 2_656 ?
O1 Sn1 O2 170.14(12) . 2_656 ?
C11 O1 Sn1 128.8(3) . . ?
C8 N9 C4 105.7(4) . . ?
C8 N9 C9 128.6(4) . . ?
C4 N9 C9 125.8(4) . . ?
C11 O2 Sn1 139.1(3) . 2_646 ?
C2 N1 C6 125.5(4) . . ?
C2 N1 H1 113(4) . . ?
C6 N1 H1 122(4) . . ?
C2 N3 C4 111.2(4) . . ?
C4 C5 N7 109.8(4) . . ?
C4 C5 C6 119.3(4) . . ?
N7 C5 C6 130.9(5) . . ?
C8 N7 C5 104.5(4) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O6 C6 N1 120.3(5) . . ?
O6 C6 C5 128.7(5) . . ?
N1 C6 C5 111.1(5) . . ?
N3 C4 C5 128.4(4) . . ?
N3 C4 N9 125.0(4) . . ?
C5 C4 N9 106.6(4) . . ?
O2 C11 O1 123.6(5) . . ?
O2 C11 C10 119.8(4) . . ?
O1 C11 C10 116.5(4) . . ?
C11 C10 C9 113.2(4) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
N9 C9 C10 111.6(4) . . ?
N9 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N9 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N3 C2 N2 118.4(5) . . ?
N3 C2 N1 124.5(4) . . ?
N2 C2 N1 117.1(4) . . ?
N7 C8 N9 113.5(4) . . ?
N7 C8 H8 123.3 . . ?
N9 C8 H8 123.3 . . ?
C21 C20 Sn1 113.6(4) . . ?
C21 C20 H20A 108.8 . . ?
Sn1 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
Sn1 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C13 C12 Sn1 120.5(6) . . ?
C13 C12 H12A 107.2 . . ?
Sn1 C12 H12A 107.2 . . ?
C13 C12 H12B 107.2 . . ?
Sn1 C12 H12B 107.2 . . ?
H12A C12 H12B 106.8 . . ?
C17 C16 Sn1 117.6(6) . . ?
C17 C16 H16A 107.9 . . ?
Sn1 C16 H16A 107.9 . . ?
C17 C16 H16B 107.9 . . ?
Sn1 C16 H16B 107.9 . . ?
H16A C16 H16B 107.2 . . ?
C21 C22 C23 104.8(9) . . ?
C21 C22 H22A 110.8 . . ?
C23 C22 H22A 110.8 . . ?
C21 C22 H22B 110.8 . . ?
C23 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
C15 C14 C13 117.8(11) . . ?
C15 C14 H14A 107.9 . . ?
C13 C14 H14A 107.9 . . ?
C15 C14 H14B 107.9 . . ?
C13 C14 H14B 107.9 . . ?
H14A C14 H14B 107.2 . . ?
C12 C13 C14 119.0(8) . . ?
C12 C13 H13A 107.6 . . ?
C14 C13 H13A 107.6 . . ?
C12 C13 H13B 107.6 . . ?
C14 C13 H13B 107.6 . . ?
H13A C13 H13B 107.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C21 C20 116.4(7) . . ?
C22 C21 H21A 108.2 . . ?
C20 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
C20 C21 H21B 108.2 . . ?
H21A C21 H21B 107.3 . . ?
C16 C17 C18 114.8(9) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 112.3(12) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.378
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.099
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex3
_database_code_depnum_ccdc_archive 'CCDC 1444874'
_audit_update_record             
;
2015-12-31 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H17 N5 O3 Sn'
_chemical_formula_sum            'C11 H17 N5 O3 Sn'
_chemical_formula_weight         385.99

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.117(5)
_cell_length_b                   9.762(5)
_cell_length_c                   12.936(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.504(5)
_cell_angle_gamma                90.00
_cell_volume                     1487.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2815
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.44

_exptl_crystal_description       bloc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    1.732
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.785
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            7788
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2763
_reflns_number_gt                2278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+3.4965P] where P=(Fo²+2Fc²)/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_number_reflns         2763
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 1.04915(3) 0.83010(3) 0.81039(3) 0.04084(14) Uani 1 1 d . . .
O2 O 1.1014(3) 0.6576(3) 0.9250(3) 0.0394(8) Uani 1 1 d . . .
O1 O 0.9965(3) 1.0128(3) 0.6909(3) 0.0471(8) Uani 1 1 d . . .
N1 N 0.5513(4) 0.8748(4) 0.7233(4) 0.0460(11) Uani 1 1 d . . .
O6 O 0.6457(3) 0.7512(3) 0.6212(3) 0.0513(9) Uani 1 1 d . . .
C11 C 0.9235(4) 1.0368(5) 0.6084(4) 0.0369(11) Uani 1 1 d . . .
N7 N 0.6728(3) 1.0337(4) 0.5171(3) 0.0442(10) Uani 1 1 d . . .
C6 C 0.6109(4) 0.8623(5) 0.6438(4) 0.0414(12) Uani 1 1 d . . .
N3 N 0.5178(4) 1.1135(4) 0.7089(4) 0.0479(11) Uani 1 1 d . . .
C10 C 0.8591(4) 0.9181(5) 0.5464(4) 0.0437(12) Uani 1 1 d . . .
H10A H 0.8409 0.8528 0.5964 0.052 Uiso 1 1 calc R . .
H10B H 0.9086 0.8724 0.5082 0.052 Uiso 1 1 calc R . .
N9 N 0.5948(4) 1.2197(4) 0.5729(4) 0.0467(10) Uani 1 1 d . . .
C5 C 0.6245(4) 0.9919(5) 0.5988(4) 0.0427(11) Uani 1 1 d . . .
C2 C 0.5068(4) 0.9945(5) 0.7537(5) 0.0467(12) Uani 1 1 d . . .
C9 C 0.7499(4) 0.9573(5) 0.4673(4) 0.0447(12) Uani 1 1 d . . .
H9A H 0.7682 1.0125 0.4112 0.054 Uiso 1 1 calc R . .
H9B H 0.7122 0.8749 0.4351 0.054 Uiso 1 1 calc R . .
C8 C 0.6527(4) 1.1699(5) 0.5067(4) 0.0466(12) Uani 1 1 d . . .
H8 H 0.6776 1.2238 0.4574 0.056 Uiso 1 1 calc R . .
C4 C 0.5769(4) 1.1081(5) 0.6312(4) 0.0430(12) Uani 1 1 d . . .
N2 N 0.4489(5) 0.9861(5) 0.8290(4) 0.0732(16) Uani 1 1 d . . .
H2A H 0.4185 1.0583 0.8485 0.088 Uiso 1 1 calc R . .
H2B H 0.4418 0.9084 0.8581 0.088 Uiso 1 1 calc R . .
C13 C 1.1272(5) 0.7379(6) 0.6980(5) 0.0599(16) Uani 1 1 d . . .
H13A H 1.1510 0.8077 0.6556 0.090 Uiso 1 1 calc R . .
H13B H 1.0740 0.6781 0.6528 0.090 Uiso 1 1 calc R . .
H13C H 1.1920 0.6861 0.7343 0.090 Uiso 1 1 calc R . .
C14 C 1.1486(6) 0.9706(6) 0.9179(5) 0.0622(16) Uani 1 1 d . . .
H14A H 1.1753 0.9273 0.9857 0.093 Uiso 1 1 calc R . .
H14B H 1.1033 1.0489 0.9257 0.093 Uiso 1 1 calc R . .
H14C H 1.2123 0.9993 0.8909 0.093 Uiso 1 1 calc R . .
C12 C 0.8773(5) 0.8164(6) 0.8191(5) 0.0536(14) Uani 1 1 d . . .
H12A H 0.8729 0.8175 0.8922 0.080 Uiso 1 1 calc R . .
H12B H 0.8452 0.7327 0.7864 0.080 Uiso 1 1 calc R . .
H12C H 0.8358 0.8928 0.7825 0.080 Uiso 1 1 calc R . .
H1 H 0.534(4) 0.801(6) 0.746(4) 0.047(16) Uiso 1 1 d . . .


_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 C13 2.112(5) . ?
Sn1 C12 2.116(6) . ?
Sn1 C14 2.118(5) . ?
Sn1 O2 2.235(3) . ?
Sn1 O1 2.348(3) . ?
O2 C11 1.268(5) 2_746 ?
O1 C11 1.239(6) . ?
N1 C2 1.381(7) . ?
N1 C6 1.393(7) . ?
N1 H1 0.82(6) . ?
O6 C6 1.224(6) . ?
C11 O2 1.268(5) 2_756 ?
C11 C10 1.518(7) . ?
N7 C8 1.353(6) . ?
N7 C5 1.384(6) . ?
N7 C9 1.457(6) . ?
C6 C5 1.418(7) . ?
N3 C2 1.319(7) . ?
N3 C4 1.364(6) . ?
C10 C9 1.520(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N9 C8 1.319(7) . ?
N9 C4 1.371(7) . ?
C5 C4 1.381(7) . ?
C2 N2 1.330(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8 0.9300 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 Sn1 C12 127.9(3) . . ?
C13 Sn1 C14 116.8(3) . . ?
C12 Sn1 C14 115.0(2) . . ?
C13 Sn1 O2 91.87(18) . . ?
C12 Sn1 O2 92.69(17) . . ?
C14 Sn1 O2 91.33(19) . . ?
C13 Sn1 O1 88.10(19) . . ?
C12 Sn1 O1 87.91(18) . . ?
C14 Sn1 O1 88.03(19) . . ?
O2 Sn1 O1 179.27(13) . . ?
C11 O2 Sn1 117.8(3) 2_746 . ?
C11 O1 Sn1 137.7(3) . . ?
C2 N1 C6 126.0(5) . . ?
C2 N1 H1 119(4) . . ?
C6 N1 H1 114(4) . . ?
O1 C11 O2 122.3(4) . 2_756 ?
O1 C11 C10 119.1(4) . . ?
O2 C11 C10 118.5(4) 2_756 . ?
C8 N7 C5 105.5(4) . . ?
C8 N7 C9 125.3(4) . . ?
C5 N7 C9 128.0(4) . . ?
O6 C6 N1 121.4(5) . . ?
O6 C6 C5 127.8(5) . . ?
N1 C6 C5 110.8(4) . . ?
C2 N3 C4 114.4(4) . . ?
C11 C10 C9 115.0(4) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C8 N9 C4 104.0(4) . . ?
C4 C5 N7 105.7(4) . . ?
C4 C5 C6 120.8(5) . . ?
N7 C5 C6 133.4(5) . . ?
N3 C2 N2 120.0(5) . . ?
N3 C2 N1 122.3(5) . . ?
N2 C2 N1 117.7(5) . . ?
N7 C9 C10 112.2(4) . . ?
N7 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N7 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N9 C8 N7 114.1(5) . . ?
N9 C8 H8 122.9 . . ?
N7 C8 H8 122.9 . . ?
N3 C4 N9 123.5(4) . . ?
N3 C4 C5 125.7(5) . . ?
N9 C4 C5 110.7(5) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
Sn1 C13 H13A 109.5 . . ?
Sn1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Sn1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Sn1 C14 H14A 109.5 . . ?
Sn1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Sn1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Sn1 C12 H12A 109.5 . . ?
Sn1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Sn1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.112
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex4
_database_code_depnum_ccdc_archive 'CCDC 1444875'
_audit_update_record             
;
2015-12-31 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H62 N4 O9 Sn2'
_chemical_formula_sum            'C34 H62 N4 O9 Sn2'
_chemical_formula_weight         908.26

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   16.6335(8)
_cell_length_b                   18.0945(9)
_cell_length_c                   15.1131(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.7970(10)
_cell_angle_gamma                90.00
_cell_volume                     4223.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9112
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1864
_exptl_absorpt_coefficient_mu    1.233
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29097
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.50
_reflns_number_total             7861
_reflns_number_gt                6844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+11.8291P] where P=(Fo²+2Fc²)/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_number_reflns         7861
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.900766(14) 0.869843(12) 0.278107(17) 0.02029(7) Uani 1 1 d . . .
Sn2 Sn 0.509511(14) 0.625065(12) 0.123331(18) 0.02181(8) Uani 1 1 d . . .
O5 O 0.83403(15) 0.79041(14) 0.16361(19) 0.0301(6) Uani 1 1 d . . .
O6 O 0.95666(15) 0.73493(14) 0.1708(2) 0.0320(6) Uani 1 1 d . . .
O2 O 0.62371(15) 0.57867(14) 0.05866(19) 0.0283(6) Uani 1 1 d . . .
O4 O 0.86517(17) 0.49948(15) 0.0173(3) 0.0499(9) Uani 1 1 d . . .
O5A O 0.40990(15) 0.65967(13) 0.17479(18) 0.0259(5) Uani 1 1 d . . .
O6A O 0.31731(15) 0.58709(13) 0.06364(19) 0.0270(6) Uani 1 1 d . . .
O2A O 0.04496(16) 0.60667(18) 0.0966(2) 0.0411(6) Uani 1 1 d . . .
O4A O 0.21070(18) 0.76042(17) 0.3327(2) 0.0450(8) Uani 1 1 d . . .
N1 N 0.74235(18) 0.66183(16) 0.0992(2) 0.0252(4) Uani 1 1 d . . .
H1 H 0.7163 0.6978 0.1144 0.030 Uiso 1 1 calc R . .
N3 N 0.74443(18) 0.54232(16) 0.0361(2) 0.0252(4) Uani 1 1 d . . .
H3 H 0.7183 0.5021 0.0112 0.030 Uiso 1 1 calc R . .
O7 O 0.96057(17) 0.94989(16) 0.4040(2) 0.0404(7) Uani 1 1 d . . .
H7A H 0.9625 0.9930 0.3825 0.061 Uiso 1 1 d R . .
H7B H 0.9295 0.9505 0.4377 0.061 Uiso 1 1 d R . .
N1A N 0.18681(17) 0.62024(16) 0.1190(2) 0.0235(6) Uani 1 1 d . . .
H1A H 0.1824 0.5883 0.0753 0.028 Uiso 1 1 calc R . .
C16 C 0.7744(2) 0.9101(2) 0.2621(3) 0.0309(8) Uani 1 1 d . . .
H16A H 0.7420 0.8699 0.2756 0.037 Uiso 1 1 calc R . .
H16B H 0.7810 0.9484 0.3092 0.037 Uiso 1 1 calc R . .
C17 C 0.7211(2) 0.9415(2) 0.1629(3) 0.0382(10) Uani 1 1 d . . .
H17A H 0.7197 0.9052 0.1152 0.046 Uiso 1 1 calc R . .
H17B H 0.6620 0.9492 0.1586 0.046 Uiso 1 1 calc R . .
C18 C 0.7552(3) 1.0128(3) 0.1404(4) 0.0477(11) Uani 1 1 d . . .
H18A H 0.8136 1.0048 0.1429 0.057 Uiso 1 1 calc R . .
H18B H 0.7581 1.0487 0.1892 0.057 Uiso 1 1 calc R . .
C19 C 0.7009(4) 1.0448(3) 0.0434(4) 0.0651(15) Uani 1 1 d . . .
H19A H 0.6966 1.0093 -0.0054 0.098 Uiso 1 1 calc R . .
H19B H 0.7279 1.0890 0.0326 0.098 Uiso 1 1 calc R . .
H19C H 0.6440 1.0563 0.0417 0.098 Uiso 1 1 calc R . .
C12 C 0.9736(2) 0.9282(2) 0.2106(3) 0.0331(9) Uani 1 1 d . . .
H12A H 0.9464 0.9202 0.1425 0.040 Uiso 1 1 calc R . .
H12B H 0.9694 0.9806 0.2218 0.040 Uiso 1 1 calc R . .
C13 C 1.0682(3) 0.9088(2) 0.2409(3) 0.0393(10) Uani 1 1 d . . .
H13A H 1.0732 0.8589 0.2200 0.047 Uiso 1 1 calc R . .
H13B H 1.0944 0.9096 0.3099 0.047 Uiso 1 1 calc R . .
C14 C 1.1181(3) 0.9611(3) 0.2009(4) 0.0458(11) Uani 1 1 d . . .
H14A H 1.1181 1.0102 0.2267 0.055 Uiso 1 1 calc R . .
H14B H 1.0889 0.9640 0.1322 0.055 Uiso 1 1 calc R . .
C15 C 1.2127(3) 0.9360(3) 0.2248(5) 0.0671(16) Uani 1 1 d . . .
H15A H 1.2413 0.9315 0.2926 0.101 Uiso 1 1 calc R . .
H15B H 1.2424 0.9718 0.2012 0.101 Uiso 1 1 calc R . .
H15C H 1.2130 0.8890 0.1954 0.101 Uiso 1 1 calc R . .
C7 C 0.8782(2) 0.7373(2) 0.1504(3) 0.0247(7) Uani 1 1 d . . .
C6 C 0.8256(2) 0.66918(19) 0.1076(3) 0.0252(4) Uani 1 1 d . . .
C2 C 0.6973(2) 0.59344(19) 0.0645(3) 0.0242(7) Uani 1 1 d . . .
C4 C 0.8288(2) 0.5492(2) 0.0436(3) 0.0301(8) Uani 1 1 d . . .
C5 C 0.8681(2) 0.61342(19) 0.0815(3) 0.0252(4) Uani 1 1 d . . .
H5 H 0.9260 0.6200 0.0901 0.030 Uiso 1 1 calc R . .
C8 C 0.9520(2) 0.7831(2) 0.3790(3) 0.0311(8) Uani 1 1 d . . .
H8A H 0.9357 0.7923 0.4334 0.037 Uiso 1 1 calc R . .
H8B H 0.9251 0.7370 0.3502 0.037 Uiso 1 1 calc R . .
C9 C 1.0499(3) 0.7737(2) 0.4147(3) 0.0365(9) Uani 1 1 d . . .
H9A H 1.0770 0.8188 0.4468 0.044 Uiso 1 1 calc R . .
H9B H 1.0667 0.7669 0.3603 0.044 Uiso 1 1 calc R . .
C10 C 1.0844(3) 0.7084(3) 0.4833(4) 0.0533(12) Uani 1 1 d . . .
H10A H 1.1465 0.7140 0.5157 0.064 Uiso 1 1 calc R . .
H10B H 1.0586 0.7101 0.5312 0.064 Uiso 1 1 calc R . .
C11 C 1.0663(4) 0.6345(3) 0.4357(4) 0.0636(15) Uani 1 1 d . . .
H11A H 1.0049 0.6266 0.4082 0.095 Uiso 1 1 calc R . .
H11B H 1.0926 0.5966 0.4819 0.095 Uiso 1 1 calc R . .
H11C H 1.0899 0.6329 0.3866 0.095 Uiso 1 1 calc R . .
C28 C 0.5122(2) 0.50989(19) 0.1562(3) 0.0247(7) Uani 1 1 d . . .
H28A H 0.4783 0.4839 0.0982 0.030 Uiso 1 1 calc R . .
H28B H 0.5715 0.4929 0.1748 0.030 Uiso 1 1 calc R . .
C29 C 0.4793(3) 0.4867(2) 0.2339(3) 0.0361(9) Uani 1 1 d . . .
H29A H 0.5145 0.5103 0.2932 0.043 Uiso 1 1 calc R . .
H29B H 0.4203 0.5042 0.2170 0.043 Uiso 1 1 calc R . .
C30 C 0.4810(3) 0.4032(2) 0.2496(3) 0.0378(10) Uani 1 1 d . . .
H30A H 0.4516 0.3923 0.2928 0.045 Uiso 1 1 calc R . .
H30B H 0.4487 0.3795 0.1892 0.045 Uiso 1 1 calc R . .
C31 C 0.5711(3) 0.3699(2) 0.2897(3) 0.0372(9) Uani 1 1 d . . .
H31A H 0.5981 0.3748 0.2438 0.056 Uiso 1 1 calc R . .
H31B H 0.5672 0.3186 0.3035 0.056 Uiso 1 1 calc R . .
H31C H 0.6051 0.3954 0.3471 0.056 Uiso 1 1 calc R . .
C20 C 0.4509(2) 0.6643(2) -0.0196(3) 0.0279(8) Uani 1 1 d . . .
H20A H 0.4467 0.6231 -0.0622 0.033 Uiso 1 1 calc R . .
H20B H 0.3923 0.6798 -0.0297 0.033 Uiso 1 1 calc R . .
C21 C 0.4960(2) 0.7280(2) -0.0491(3) 0.0309(8) Uani 1 1 d . . .
H21A H 0.5571 0.7165 -0.0300 0.037 Uiso 1 1 calc R . .
H21B H 0.4721 0.7324 -0.1180 0.037 Uiso 1 1 calc R . .
C22 C 0.4867(3) 0.8012(2) -0.0060(3) 0.0381(9) Uani 1 1 d . . .
H22A H 0.5159 0.7986 0.0627 0.046 Uiso 1 1 calc R . .
H22B H 0.4258 0.8106 -0.0197 0.046 Uiso 1 1 calc R . .
C23 C 0.5246(3) 0.8653(2) -0.0444(4) 0.0472(11) Uani 1 1 d . . .
H23A H 0.5850 0.8565 -0.0303 0.071 Uiso 1 1 calc R . .
H23B H 0.5177 0.9106 -0.0150 0.071 Uiso 1 1 calc R . .
H23C H 0.4947 0.8689 -0.1122 0.071 Uiso 1 1 calc R . .
C7A C 0.3355(2) 0.63081(18) 0.1303(3) 0.0224(7) Uani 1 1 d . . .
C6A C 0.2659(2) 0.65361(18) 0.1659(3) 0.0224(7) Uani 1 1 d . . .
C2A C 0.1155(2) 0.6362(3) 0.1395(3) 0.0411(6) Uani 1 1 d . . .
N3A N 0.12807(18) 0.68610(17) 0.2105(2) 0.0277(7) Uani 1 1 d . . .
H3A H 0.0830 0.6984 0.2221 0.033 Uiso 1 1 calc R . .
C4A C 0.2069(2) 0.7200(2) 0.2673(3) 0.0315(9) Uani 1 1 d . . .
C5A C 0.2780(2) 0.7009(2) 0.2377(3) 0.0284(8) Uani 1 1 d . . .
H5A H 0.3324 0.7217 0.2689 0.034 Uiso 1 1 calc R . .
C24 C 0.6048(2) 0.6884(2) 0.2327(3) 0.0280(8) Uani 1 1 d . . .
H24A H 0.6297 0.7247 0.2030 0.034 Uiso 1 1 calc R . .
H24B H 0.5766 0.7150 0.2689 0.034 Uiso 1 1 calc R . .
C25 C 0.6778(2) 0.6411(2) 0.3012(3) 0.0317(9) Uani 1 1 d . . .
H25A H 0.6528 0.6053 0.3314 0.038 Uiso 1 1 calc R . .
H25B H 0.7051 0.6139 0.2647 0.038 Uiso 1 1 calc R . .
C26 C 0.7469(3) 0.6849(3) 0.3784(3) 0.0409(10) Uani 1 1 d . . .
H26A H 0.7204 0.7103 0.4173 0.049 Uiso 1 1 calc R . .
H26B H 0.7706 0.7221 0.3487 0.049 Uiso 1 1 calc R . .
C27 C 0.8202(3) 0.6358(3) 0.4422(3) 0.0472(11) Uani 1 1 d . . .
H27A H 0.7974 0.6001 0.4737 0.071 Uiso 1 1 calc R . .
H27B H 0.8628 0.6657 0.4890 0.071 Uiso 1 1 calc R . .
H27C H 0.8467 0.6106 0.4040 0.071 Uiso 1 1 calc R . .


_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 C12 2.131(4) . ?
Sn1 C8 2.133(4) . ?
Sn1 C16 2.152(3) . ?
Sn1 O5 2.206(2) . ?
Sn1 O7 2.302(3) . ?
Sn2 C20 2.135(4) . ?
Sn2 C28 2.139(3) . ?
Sn2 C24 2.148(3) . ?
Sn2 O5A 2.168(2) . ?
O5 C7 1.270(4) . ?
O6 C7 1.226(4) . ?
O2 C2 1.223(4) . ?
O4 C4 1.229(4) . ?
O5A C7A 1.280(4) . ?
O6A C7A 1.228(4) . ?
O2A C2A 1.233(5) . ?
O4A C4A 1.212(5) . ?
N1 C6 1.350(4) . ?
N1 C2 1.441(4) . ?
N1 H1 0.8600 . ?
N3 C4 1.371(4) . ?
N3 C2 1.380(4) . ?
N3 H3 0.8600 . ?
O7 H7A 0.8505 . ?
O7 H7B 0.8504 . ?
N1A C2A 1.363(4) . ?
N1A C6A 1.380(4) . ?
N1A H1A 0.8600 . ?
C16 C17 1.538(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.498(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.523(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C12 C13 1.509(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.525(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.546(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C7 C6 1.510(5) . ?
C6 C5 1.371(5) . ?
C4 C5 1.351(5) . ?
C5 H5 0.9300 . ?
C8 C9 1.522(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.535(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.495(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C28 C29 1.527(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.527(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.518(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C20 C21 1.529(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.509(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.535(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C7A C6A 1.504(4) . ?
C6A C5A 1.336(5) . ?
C2A N3A 1.357(5) . ?
N3A C4A 1.413(5) . ?
N3A H3A 0.8600 . ?
C4A C5A 1.454(5) . ?
C5A H5A 0.9300 . ?
C24 C25 1.531(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.521(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.529(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Sn1 C8 124.05(14) . . ?
C12 Sn1 C16 118.92(15) . . ?
C8 Sn1 C16 116.33(15) . . ?
C12 Sn1 O5 99.06(13) . . ?
C8 Sn1 O5 91.86(13) . . ?
C16 Sn1 O5 86.90(12) . . ?
C12 Sn1 O7 86.30(14) . . ?
C8 Sn1 O7 86.38(14) . . ?
C16 Sn1 O7 89.13(12) . . ?
O5 Sn1 O7 174.41(10) . . ?
C20 Sn2 C28 121.43(14) . . ?
C20 Sn2 C24 122.03(15) . . ?
C28 Sn2 C24 113.29(15) . . ?
C20 Sn2 O5A 98.31(12) . . ?
C28 Sn2 O5A 98.68(11) . . ?
C24 Sn2 O5A 90.80(11) . . ?
C7 O5 Sn1 117.7(2) . . ?
C7A O5A Sn2 114.4(2) . . ?
C6 N1 C2 119.8(3) . . ?
C6 N1 H1 120.1 . . ?
C2 N1 H1 120.1 . . ?
C4 N3 C2 126.6(3) . . ?
C4 N3 H3 116.7 . . ?
C2 N3 H3 116.7 . . ?
Sn1 O7 H7A 109.2 . . ?
Sn1 O7 H7B 109.4 . . ?
H7A O7 H7B 109.5 . . ?
C2A N1A C6A 122.2(3) . . ?
C2A N1A H1A 118.9 . . ?
C6A N1A H1A 118.9 . . ?
C17 C16 Sn1 114.8(2) . . ?
C17 C16 H16A 108.6 . . ?
Sn1 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
Sn1 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 114.2(3) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 114.1(4) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
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 . . ?
C13 C12 Sn1 117.0(3) . . ?
C13 C12 H12A 108.1 . . ?
Sn1 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
Sn1 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C12 C13 C14 113.3(4) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 112.4(4) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C7 O5 127.7(3) . . ?
O6 C7 C6 118.2(3) . . ?
O5 C7 C6 114.1(3) . . ?
N1 C6 C5 121.4(3) . . ?
N1 C6 C7 122.1(3) . . ?
C5 C6 C7 116.5(3) . . ?
O2 C2 N3 120.0(3) . . ?
O2 C2 N1 125.9(3) . . ?
N3 C2 N1 114.2(3) . . ?
O4 C4 C5 123.2(3) . . ?
O4 C4 N3 121.2(3) . . ?
C5 C4 N3 115.6(3) . . ?
C4 C5 C6 122.4(3) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C9 C8 Sn1 115.2(3) . . ?
C9 C8 H8A 108.5 . . ?
Sn1 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
Sn1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 114.0(4) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 114.0(4) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C29 C28 Sn2 117.7(2) . . ?
C29 C28 H28A 107.9 . . ?
Sn2 C28 H28A 107.9 . . ?
C29 C28 H28B 107.9 . . ?
Sn2 C28 H28B 107.9 . . ?
H28A C28 H28B 107.2 . . ?
C30 C29 C28 113.6(3) . . ?
C30 C29 H29A 108.9 . . ?
C28 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C28 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C31 C30 C29 114.4(3) . . ?
C31 C30 H30A 108.7 . . ?
C29 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
C29 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C20 Sn2 117.1(3) . . ?
C21 C20 H20A 108.0 . . ?
Sn2 C20 H20A 108.0 . . ?
C21 C20 H20B 108.0 . . ?
Sn2 C20 H20B 108.0 . . ?
H20A C20 H20B 107.3 . . ?
C22 C21 C20 113.3(3) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 112.1(3) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6A C7A O5A 126.1(3) . . ?
O6A C7A C6A 118.9(3) . . ?
O5A C7A C6A 115.0(3) . . ?
C5A C6A N1A 121.7(3) . . ?
C5A C6A C7A 124.1(3) . . ?
N1A C6A C7A 114.1(3) . . ?
O2A C2A N3A 122.7(3) . . ?
O2A C2A N1A 121.8(3) . . ?
N3A C2A N1A 115.4(3) . . ?
C2A N3A C4A 127.2(3) . . ?
C2A N3A H3A 116.4 . . ?
C4A N3A H3A 116.4 . . ?
O4A C4A N3A 120.9(3) . . ?
O4A C4A C5A 126.3(3) . . ?
N3A C4A C5A 112.8(3) . . ?
C6A C5A C4A 120.4(3) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
C25 C24 Sn2 113.2(2) . . ?
C25 C24 H24A 108.9 . . ?
Sn2 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
Sn2 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C26 C25 C24 114.2(3) . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25B 108.7 . . ?
C24 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C25 C26 C27 112.3(4) . . ?
C25 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C12 Sn1 O5 C7 74.2(3) . . . . ?
C8 Sn1 O5 C7 -50.7(3) . . . . ?
C16 Sn1 O5 C7 -167.0(3) . . . . ?
O7 Sn1 O5 C7 -122.2(10) . . . . ?
C20 Sn2 O5A C7A 60.5(3) . . . . ?
C28 Sn2 O5A C7A -63.3(3) . . . . ?
C24 Sn2 O5A C7A -177.0(3) . . . . ?
C12 Sn1 C16 C17 37.7(3) . . . . ?
C8 Sn1 C16 C17 -151.5(3) . . . . ?
O5 Sn1 C16 C17 -60.9(3) . . . . ?
O7 Sn1 C16 C17 123.0(3) . . . . ?
Sn1 C16 C17 C18 -69.4(4) . . . . ?
C16 C17 C18 C19 -178.4(4) . . . . ?
C8 Sn1 C12 C13 -3.3(4) . . . . ?
C16 Sn1 C12 C13 166.8(3) . . . . ?
O5 Sn1 C12 C13 -101.7(3) . . . . ?
O7 Sn1 C12 C13 79.8(3) . . . . ?
Sn1 C12 C13 C14 -171.0(3) . . . . ?
C12 C13 C14 C15 -174.5(4) . . . . ?
Sn1 O5 C7 O6 -24.7(5) . . . . ?
Sn1 O5 C7 C6 153.1(2) . . . . ?
C2 N1 C6 C5 1.7(6) . . . . ?
C2 N1 C6 C7 -175.3(3) . . . . ?
O6 C7 C6 N1 167.7(4) . . . . ?
O5 C7 C6 N1 -10.3(5) . . . . ?
O6 C7 C6 C5 -9.5(5) . . . . ?
O5 C7 C6 C5 172.6(3) . . . . ?
C4 N3 C2 O2 -175.9(4) . . . . ?
C4 N3 C2 N1 4.3(6) . . . . ?
C6 N1 C2 O2 175.8(4) . . . . ?
C6 N1 C2 N3 -4.5(5) . . . . ?
C2 N3 C4 O4 178.8(4) . . . . ?
C2 N3 C4 C5 -1.0(6) . . . . ?
O4 C4 C5 C6 177.9(4) . . . . ?
N3 C4 C5 C6 -2.3(6) . . . . ?
N1 C6 C5 C4 1.9(6) . . . . ?
C7 C6 C5 C4 179.1(4) . . . . ?
C12 Sn1 C8 C9 10.7(4) . . . . ?
C16 Sn1 C8 C9 -159.6(3) . . . . ?
O5 Sn1 C8 C9 112.9(3) . . . . ?
O7 Sn1 C8 C9 -72.4(3) . . . . ?
Sn1 C8 C9 C10 -177.0(3) . . . . ?
C8 C9 C10 C11 73.8(5) . . . . ?
C20 Sn2 C28 C29 -128.3(3) . . . . ?
C24 Sn2 C28 C29 71.7(3) . . . . ?
O5A Sn2 C28 C29 -22.9(3) . . . . ?
Sn2 C28 C29 C30 178.0(3) . . . . ?
C28 C29 C30 C31 66.6(5) . . . . ?
C28 Sn2 C20 C21 -141.5(2) . . . . ?
C24 Sn2 C20 C21 16.8(3) . . . . ?
O5A Sn2 C20 C21 113.0(3) . . . . ?
Sn2 C20 C21 C22 -72.6(4) . . . . ?
C20 C21 C22 C23 -174.3(4) . . . . ?
Sn2 O5A C7A O6A -0.2(5) . . . . ?
Sn2 O5A C7A C6A 179.3(2) . . . . ?
C2A N1A C6A C5A 3.4(6) . . . . ?
C2A N1A C6A C7A -177.7(4) . . . . ?
O6A C7A C6A C5A -179.8(4) . . . . ?
O5A C7A C6A C5A 0.7(5) . . . . ?
O6A C7A C6A N1A 1.3(5) . . . . ?
O5A C7A C6A N1A -178.2(3) . . . . ?
C6A N1A C2A O2A 179.3(4) . . . . ?
C6A N1A C2A N3A -1.2(6) . . . . ?
O2A C2A N3A C4A 176.3(4) . . . . ?
N1A C2A N3A C4A -3.2(7) . . . . ?
C2A N3A C4A O4A -175.4(4) . . . . ?
C2A N3A C4A C5A 4.9(6) . . . . ?
N1A C6A C5A C4A -1.4(6) . . . . ?
C7A C6A C5A C4A 179.9(3) . . . . ?
O4A C4A C5A C6A 177.9(4) . . . . ?
N3A C4A C5A C6A -2.4(6) . . . . ?
C20 Sn2 C24 C25 -141.6(2) . . . . ?
C28 Sn2 C24 C25 18.3(3) . . . . ?
O5A Sn2 C24 C25 118.1(3) . . . . ?
Sn2 C24 C25 C26 179.1(3) . . . . ?
C24 C25 C26 C27 -177.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.010
_refine_diff_density_min         -1.778
_refine_diff_density_rms         0.091
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex5
_database_code_depnum_ccdc_archive 'CCDC 1444876'
_audit_update_record             
;
2015-12-31 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H19 N5 O3 Sn'
_chemical_formula_sum            'C11 H19 N5 O3 Sn'
_chemical_formula_weight         388.00

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   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7847(6)
_cell_length_b                   7.4633(4)
_cell_length_c                   19.1432(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.6840(10)
_cell_angle_gamma                90.00
_cell_volume                     1514.11(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9811
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  0.660
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11962
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2803
_reflns_number_gt                2597
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0290P)²+2.1847P] where P=(Fo²+2Fc²)/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_number_reflns         2803
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0599
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 1.070176(15) -0.08029(2) 0.164437(9) 0.01500(8) Uani 1 1 d . . .
O3 O 1.2445(2) -0.2452(3) 0.14360(12) 0.0310(5) Uani 1 1 d . . .
O1 O 0.91053(17) 0.0744(2) 0.18750(10) 0.0184(4) Uani 1 1 d . . .
O2 O 1.02931(17) 0.2818(3) 0.25392(10) 0.0221(4) Uani 1 1 d . . .
N9 N 0.69298(19) 0.3278(3) 0.10426(11) 0.0135(4) Uani 1 1 d . . .
N3 N 0.6051(2) 0.6240(3) 0.11087(11) 0.0138(4) Uani 1 1 d . . .
N1 N 0.5893(2) 0.7873(3) 0.00022(11) 0.0159(5) Uani 1 1 d . . .
C12 C 1.1139(3) 0.1199(4) 0.09431(16) 0.0299(7) Uani 1 1 d . . .
H12A H 1.1318 0.2306 0.1197 0.045 Uiso 1 1 calc R . .
H12B H 1.0433 0.1361 0.0561 0.045 Uiso 1 1 calc R . .
H12C H 1.1864 0.0836 0.0753 0.045 Uiso 1 1 calc R . .
C14 C 1.1516(3) -0.1274(4) 0.27248(14) 0.0245(6) Uani 1 1 d . . .
H14A H 1.1048 -0.0635 0.3025 0.037 Uiso 1 1 calc R . .
H14B H 1.2376 -0.0866 0.2814 0.037 Uiso 1 1 calc R . .
H14C H 1.1494 -0.2533 0.2824 0.037 Uiso 1 1 calc R . .
C13 C 0.9495(3) -0.2863(4) 0.11503(16) 0.0263(6) Uani 1 1 d . . .
H13A H 0.9672 -0.3954 0.1416 0.039 Uiso 1 1 calc R . .
H13B H 0.9634 -0.3042 0.0674 0.039 Uiso 1 1 calc R . .
H13C H 0.8632 -0.2525 0.1137 0.039 Uiso 1 1 calc R . .
C11 C 0.9262(3) 0.2211(4) 0.22361(13) 0.0165(5) Uani 1 1 d . . .
C10 C 0.8064(2) 0.3210(4) 0.22913(13) 0.0161(5) Uani 1 1 d . . .
H10A H 0.8210 0.4479 0.2232 0.019 Uiso 1 1 calc R . .
H10B H 0.7895 0.3042 0.2767 0.019 Uiso 1 1 calc R . .
C9 C 0.6896(2) 0.2674(4) 0.17645(13) 0.0151(5) Uani 1 1 d . . .
H9A H 0.6815 0.1380 0.1765 0.018 Uiso 1 1 calc R . .
H9B H 0.6158 0.3177 0.1915 0.018 Uiso 1 1 calc R . .
C8 C 0.7322(2) 0.2371(4) 0.05010(13) 0.0176(5) Uani 1 1 d . . .
H8 H 0.7624 0.1202 0.0546 0.021 Uiso 1 1 calc R . .
N7 N 0.7231(2) 0.3301(3) -0.00865(11) 0.0177(5) Uani 1 1 d . . .
C5 C 0.6733(2) 0.4943(4) 0.00749(13) 0.0151(5) Uani 1 1 d . . .
C4 C 0.6536(2) 0.4929(3) 0.07747(13) 0.0126(5) Uani 1 1 d . . .
C2 C 0.5734(2) 0.7684(3) 0.06896(13) 0.0145(5) Uani 1 1 d . . .
C6 C 0.6377(2) 0.6502(4) -0.03019(13) 0.0170(5) Uani 1 1 d . . .
H6 H 0.6477 0.6592 -0.0773 0.020 Uiso 1 1 calc R . .
N2 N 0.5256(2) 0.9105(3) 0.09821(13) 0.0180(5) Uani 1 1 d . . .
H2B H 0.497(3) 0.895(4) 0.1368(18) 0.018(8) Uiso 1 1 d . . .
H2A H 0.492(3) 0.988(5) 0.0720(19) 0.028(9) Uiso 1 1 d . . .
H3A H 1.315(4) -0.248(6) 0.173(2) 0.050(12) Uiso 1 1 d . . .
H3B H 1.262(4) -0.261(6) 0.101(2) 0.051(12) Uiso 1 1 d . . .


_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 C12 2.119(3) . ?
Sn1 C13 2.120(3) . ?
Sn1 C14 2.121(3) . ?
Sn1 O1 2.1848(18) . ?
Sn1 O3 2.343(2) . ?
O3 H3A 0.86(4) . ?
O3 H3B 0.87(4) . ?
O1 C11 1.289(3) . ?
O2 C11 1.240(3) . ?
N9 C8 1.369(3) . ?
N9 C4 1.372(3) . ?
N9 C9 1.460(3) . ?
N3 C4 1.328(3) . ?
N3 C2 1.349(3) . ?
N1 C6 1.330(4) . ?
N1 C2 1.365(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 C10 1.513(4) . ?
C10 C9 1.514(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 N7 1.310(4) . ?
C8 H8 0.9300 . ?
N7 C5 1.396(4) . ?
C5 C6 1.385(4) . ?
C5 C4 1.395(3) . ?
C2 N2 1.346(4) . ?
C6 H6 0.9300 . ?
N2 H2B 0.86(3) . ?
N2 H2A 0.80(4) . ?

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
C12 Sn1 C13 114.76(12) . . ?
C12 Sn1 C14 129.34(12) . . ?
C13 Sn1 C14 115.08(12) . . ?
C12 Sn1 O1 91.82(11) . . ?
C13 Sn1 O1 91.80(10) . . ?
C14 Sn1 O1 95.16(9) . . ?
C12 Sn1 O3 89.01(11) . . ?
C13 Sn1 O3 89.36(10) . . ?
C14 Sn1 O3 83.03(10) . . ?
O1 Sn1 O3 178.13(7) . . ?
Sn1 O3 H3A 123(3) . . ?
Sn1 O3 H3B 123(3) . . ?
H3A O3 H3B 106(4) . . ?
C11 O1 Sn1 121.79(17) . . ?
C8 N9 C4 106.2(2) . . ?
C8 N9 C9 129.0(2) . . ?
C4 N9 C9 124.8(2) . . ?
C4 N3 C2 112.4(2) . . ?
C6 N1 C2 118.2(2) . . ?
Sn1 C12 H12A 109.5 . . ?
Sn1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Sn1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Sn1 C14 H14A 109.5 . . ?
Sn1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Sn1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Sn1 C13 H13A 109.5 . . ?
Sn1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Sn1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C11 O1 125.4(3) . . ?
O2 C11 C10 119.4(2) . . ?
O1 C11 C10 115.3(2) . . ?
C11 C10 C9 116.1(2) . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
N9 C9 C10 112.6(2) . . ?
N9 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N9 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N7 C8 N9 113.8(2) . . ?
N7 C8 H8 123.1 . . ?
N9 C8 H8 123.1 . . ?
C8 N7 C5 104.2(2) . . ?
C6 C5 C4 115.4(2) . . ?
C6 C5 N7 134.7(2) . . ?
C4 C5 N7 109.9(2) . . ?
N3 C4 N9 127.2(2) . . ?
N3 C4 C5 126.9(2) . . ?
N9 C4 C5 105.9(2) . . ?
N2 C2 N3 117.1(2) . . ?
N2 C2 N1 116.5(2) . . ?
N3 C2 N1 126.3(2) . . ?
N1 C6 C5 120.7(2) . . ?
N1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C2 N2 H2B 118(2) . . ?
C2 N2 H2A 118(2) . . ?
H2B N2 H2A 117(3) . . ?

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
C12 Sn1 O1 C11 -69.4(2) . . . . ?
C13 Sn1 O1 C11 175.7(2) . . . . ?
C14 Sn1 O1 C11 60.3(2) . . . . ?
O3 Sn1 O1 C11 47(2) . . . . ?
Sn1 O1 C11 O2 -6.6(4) . . . . ?
Sn1 O1 C11 C10 174.54(16) . . . . ?
O2 C11 C10 C9 164.8(2) . . . . ?
O1 C11 C10 C9 -16.3(3) . . . . ?
C8 N9 C9 C10 94.6(3) . . . . ?
C4 N9 C9 C10 -86.5(3) . . . . ?
C11 C10 C9 N9 -72.1(3) . . . . ?
C4 N9 C8 N7 0.9(3) . . . . ?
C9 N9 C8 N7 180.0(2) . . . . ?
N9 C8 N7 C5 -0.5(3) . . . . ?
C8 N7 C5 C6 -178.2(3) . . . . ?
C8 N7 C5 C4 -0.2(3) . . . . ?
C2 N3 C4 N9 -178.7(2) . . . . ?
C2 N3 C4 C5 0.4(4) . . . . ?
C8 N9 C4 N3 178.3(2) . . . . ?
C9 N9 C4 N3 -0.8(4) . . . . ?
C8 N9 C4 C5 -0.9(3) . . . . ?
C9 N9 C4 C5 179.9(2) . . . . ?
C6 C5 C4 N3 -0.1(4) . . . . ?
N7 C5 C4 N3 -178.5(2) . . . . ?
C6 C5 C4 N9 179.1(2) . . . . ?
N7 C5 C4 N9 0.7(3) . . . . ?
C4 N3 C2 N2 -178.7(2) . . . . ?
C4 N3 C2 N1 -1.2(4) . . . . ?
C6 N1 C2 N2 179.2(2) . . . . ?
C6 N1 C2 N3 1.7(4) . . . . ?
C2 N1 C6 C5 -1.3(4) . . . . ?
C4 C5 C6 N1 0.6(4) . . . . ?
N7 C5 C6 N1 178.5(3) . . . . ?


_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.097
