# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1435076'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C62 H50 N4 O2 Sn'
_chemical_formula_sum            'C62 H50 N4 O2 Sn'
_chemical_formula_weight         1001.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   36.657(3)
_cell_length_b                   36.657(3)
_cell_length_c                   10.4610(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     12173(2)
_cell_formula_units_Z            9
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3228
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      24.29

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4644
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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 KAPPA APEX II CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25040
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_sigmaI/netI    0.0852
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4782
_reflns_number_gt                3349
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4782
_refine_ls_number_parameters     281
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2084
_refine_ls_wR_factor_gt          0.1869
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.009 554 88 ' '
2 0.333 0.667 0.447 556 89 ' '
3 0.667 0.333 0.113 555 89 ' '
_platon_squeeze_details          
;
;
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 0.0000 0.5000 0.0000 0.0359(3) Uani 1 2 d S . .
O1 O 0.04204(12) 0.52917(12) 0.1445(4) 0.0478(10) Uani 1 1 d . . .
N2 N 0.04598(13) 0.49696(13) -0.1095(4) 0.0378(11) Uani 1 1 d . . .
N3 N -0.01852(13) 0.44040(12) 0.0757(4) 0.0343(10) Uani 1 1 d . . .
C13 C 0.05237(16) 0.39907(15) -0.0423(5) 0.0344(12) Uani 1 1 d . . .
C20 C 0.00001(16) 0.41642(16) 0.0492(5) 0.0386(13) Uani 1 1 d . . .
C10 C 0.09134(17) 0.47681(17) -0.1871(5) 0.0431(14) Uani 1 1 d . . .
H6 H 0.1045 0.4606 -0.2036 0.052 Uiso 1 1 calc R . .
C23 C -0.05046(16) 0.41914(16) 0.1639(5) 0.0364(12) Uani 1 1 d . . .
C12 C 0.03467(16) 0.42815(16) -0.0326(5) 0.0369(13) Uani 1 1 d . . .
C8 C 0.07488(16) 0.52877(16) -0.1888(5) 0.0378(13) Uani 1 1 d . . .
C11 C 0.05571(17) 0.46454(17) -0.1041(5) 0.0393(13) Uani 1 1 d . . .
C9 C 0.10308(18) 0.51521(17) -0.2381(5) 0.0455(14) Uani 1 1 d . . .
H11 H 0.1257 0.5304 -0.2959 0.055 Uiso 1 1 calc R . .
C16 C 0.09238(17) 0.35100(17) -0.0683(5) 0.0412(14) Uani 1 1 d . . .
C15 C 0.09844(19) 0.37498(19) 0.0389(5) 0.0465(15) Uani 1 1 d . . .
H13 H 0.1168 0.3758 0.1044 0.056 Uiso 1 1 calc R . .
C21 C -0.02240(17) 0.37783(16) 0.1199(5) 0.0429(14) Uani 1 1 d . . .
H14 H -0.0167 0.3553 0.1193 0.052 Uiso 1 1 calc R . .
C18 C 0.04560(17) 0.37497(16) -0.1523(5) 0.0408(13) Uani 1 1 d . . .
H15 H 0.0278 0.3749 -0.2185 0.049 Uiso 1 1 calc R . .
C22 C -0.05312(17) 0.37927(17) 0.1876(5) 0.0411(13) Uani 1 1 d . . .
H16 H -0.0730 0.3576 0.2416 0.049 Uiso 1 1 calc R . .
C24 C -0.07629(16) 0.43322(16) 0.2156(5) 0.0357(12) Uani 1 1 d . . .
C25 C -0.11026(18) 0.40486(17) 0.3084(5) 0.0411(14) Uani 1 1 d . . .
C14 C 0.07798(18) 0.39806(18) 0.0527(5) 0.0451(14) Uani 1 1 d . . .
H19 H 0.0817 0.4135 0.1292 0.054 Uiso 1 1 calc R . .
C17 C 0.06559(17) 0.35070(17) -0.1637(6) 0.0430(14) Uani 1 1 d . . .
H20 H 0.0607 0.3339 -0.2378 0.052 Uiso 1 1 calc R . .
C27 C -0.1805(2) 0.3500(2) 0.3543(8) 0.070(2) Uani 1 1 d . . .
H21 H -0.2073 0.3292 0.3235 0.084 Uiso 1 1 calc R . .
C19 C 0.1155(2) 0.3269(2) -0.0873(6) 0.0623(18) Uani 1 1 d . . .
H19A H 0.1367 0.3345 -0.0198 0.093 Uiso 1 1 calc R . .
H19B H 0.1294 0.3339 -0.1709 0.093 Uiso 1 1 calc R . .
H19C H 0.0954 0.2966 -0.0834 0.093 Uiso 1 1 calc R . .
C28 C -0.1750(3) 0.3558(2) 0.4810(8) 0.073(2) Uani 1 1 d . . .
C30 C -0.1049(2) 0.4115(2) 0.4356(6) 0.0609(18) Uani 1 1 d . . .
H24 H -0.0787 0.4332 0.4675 0.073 Uiso 1 1 calc R . .
C26 C -0.1481(2) 0.37329(19) 0.2637(7) 0.0612(18) Uani 1 1 d . . .
H25 H -0.1526 0.3672 0.1750 0.073 Uiso 1 1 calc R . .
C29 C -0.1373(3) 0.3867(3) 0.5213(7) 0.079(2) Uani 1 1 d . . .
H27 H -0.1326 0.3919 0.6105 0.095 Uiso 1 1 calc R . .
C31 C -0.2099(3) 0.3287(3) 0.5748(10) 0.126(4) Uani 1 1 d . . .
H31A H -0.2353 0.3089 0.5275 0.189 Uiso 1 1 calc R . .
H31B H -0.2162 0.3468 0.6286 0.189 Uiso 1 1 calc R . .
H31C H -0.2007 0.3130 0.6289 0.189 Uiso 1 1 calc R . .
C1 C 0.0710(2) 0.5219(2) 0.1920(7) 0.079(2) Uiso 1 1 d D . .
C7 C 0.1262(3) 0.5863(3) 0.0985(8) 0.095(3) Uiso 1 1 d . . .
H7A H 0.1196 0.5789 0.0081 0.143 Uiso 1 1 calc R . .
H7B H 0.1565 0.6053 0.1085 0.143 Uiso 1 1 calc R . .
H7C H 0.1110 0.6004 0.1289 0.143 Uiso 1 1 calc R . .
C2 C 0.0593(3) 0.4861(3) 0.2701(7) 0.101(3) Uiso 1 1 d D . .
H2 H 0.0303 0.4674 0.2863 0.121 Uiso 1 1 calc R . .
C3 C 0.0885(3) 0.4778(3) 0.3229(9) 0.129(4) Uiso 1 1 d D . .
H3 H 0.0794 0.4535 0.3747 0.155 Uiso 1 1 calc R . .
C5 C 0.1432(3) 0.5407(3) 0.2287(9) 0.113(3) Uiso 1 1 d D . .
H5 H 0.1723 0.5603 0.2172 0.136 Uiso 1 1 calc R . .
C6 C 0.1136(3) 0.5492(3) 0.1711(9) 0.113(3) Uiso 1 1 d D . .
C4 C 0.1319(4) 0.5049(4) 0.3016(11) 0.157(5) Uiso 1 1 d D . .
H4 H 0.1524 0.4989 0.3354 0.189 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 O1 2.039(4) 10_565 ?
Sn1 O1 2.039(4) . ?
Sn1 N2 2.086(4) 10_565 ?
Sn1 N2 2.086(4) . ?
Sn1 N3 2.092(4) 10_565 ?
Sn1 N3 2.092(4) . ?
O1 C1 1.316(8) . ?
N2 C8 1.391(7) . ?
N2 C11 1.402(6) . ?
N3 C20 1.382(6) . ?
N3 C23 1.384(6) . ?
C13 C14 1.380(7) . ?
C13 C18 1.395(7) . ?
C13 C12 1.503(7) . ?
C20 C12 1.409(7) . ?
C20 C21 1.435(7) . ?
C10 C9 1.359(7) . ?
C10 C11 1.440(7) . ?
C10 H6 0.9500 . ?
C23 C24 1.395(7) . ?
C23 C22 1.437(7) . ?
C12 C11 1.380(7) . ?
C8 C24 1.396(7) 10_565 ?
C8 C9 1.448(7) . ?
C9 H11 0.9500 . ?
C16 C15 1.373(8) . ?
C16 C17 1.397(8) . ?
C16 C19 1.513(7) . ?
C15 C14 1.391(8) . ?
C15 H13 0.9500 . ?
C21 C22 1.354(7) . ?
C21 H14 0.9500 . ?
C18 C17 1.412(7) . ?
C18 H15 0.9500 . ?
C22 H16 0.9500 . ?
C24 C8 1.396(7) 10_565 ?
C24 C25 1.509(7) . ?
C25 C30 1.350(8) . ?
C25 C26 1.369(8) . ?
C14 H19 0.9500 . ?
C17 H20 0.9500 . ?
C27 C28 1.342(10) . ?
C27 C26 1.422(9) . ?
C27 H21 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C28 C29 1.343(11) . ?
C28 C31 1.522(10) . ?
C30 C29 1.401(9) . ?
C30 H24 0.9500 . ?
C26 H25 0.9500 . ?
C29 H27 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C1 C6 1.387(10) . ?
C1 C2 1.416(9) . ?
C7 C6 1.420(11) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C2 C3 1.368(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(12) . ?
C3 H3 0.9500 . ?
C5 C4 1.389(11) . ?
C5 C6 1.406(10) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sn1 O1 180.000(1) 10_565 . ?
O1 Sn1 N2 90.92(16) 10_565 10_565 ?
O1 Sn1 N2 89.08(16) . 10_565 ?
O1 Sn1 N2 89.08(16) 10_565 . ?
O1 Sn1 N2 90.92(16) . . ?
N2 Sn1 N2 180.0(2) 10_565 . ?
O1 Sn1 N3 91.85(15) 10_565 10_565 ?
O1 Sn1 N3 88.15(15) . 10_565 ?
N2 Sn1 N3 90.06(16) 10_565 10_565 ?
N2 Sn1 N3 89.94(16) . 10_565 ?
O1 Sn1 N3 88.15(15) 10_565 . ?
O1 Sn1 N3 91.85(15) . . ?
N2 Sn1 N3 89.94(16) 10_565 . ?
N2 Sn1 N3 90.06(16) . . ?
N3 Sn1 N3 180.0 10_565 . ?
C1 O1 Sn1 130.4(4) . . ?
C8 N2 C11 109.0(4) . . ?
C8 N2 Sn1 125.4(3) . . ?
C11 N2 Sn1 125.3(3) . . ?
C20 N3 C23 108.8(4) . . ?
C20 N3 Sn1 125.6(3) . . ?
C23 N3 Sn1 125.6(3) . . ?
C14 C13 C18 119.0(5) . . ?
C14 C13 C12 120.7(5) . . ?
C18 C13 C12 120.1(5) . . ?
N3 C20 C12 125.7(5) . . ?
N3 C20 C21 107.6(4) . . ?
C12 C20 C21 126.7(5) . . ?
C9 C10 C11 109.2(5) . . ?
C9 C10 H6 125.4 . . ?
C11 C10 H6 125.4 . . ?
N3 C23 C24 126.1(5) . . ?
N3 C23 C22 107.2(4) . . ?
C24 C23 C22 126.6(5) . . ?
C11 C12 C20 127.4(5) . . ?
C11 C12 C13 114.7(4) . . ?
C20 C12 C13 117.9(5) . . ?
C24 C8 N2 126.1(5) 10_565 . ?
C24 C8 C9 126.4(5) 10_565 . ?
N2 C8 C9 107.5(4) . . ?
C12 C11 N2 125.8(5) . . ?
C12 C11 C10 127.6(5) . . ?
N2 C11 C10 106.6(5) . . ?
C10 C9 C8 107.8(5) . . ?
C10 C9 H11 126.1 . . ?
C8 C9 H11 126.1 . . ?
C15 C16 C17 118.5(5) . . ?
C15 C16 C19 121.5(5) . . ?
C17 C16 C19 119.9(5) . . ?
C16 C15 C14 120.7(5) . . ?
C16 C15 H13 119.7 . . ?
C14 C15 H13 119.7 . . ?
C22 C21 C20 108.0(5) . . ?
C22 C21 H14 126.0 . . ?
C20 C21 H14 126.0 . . ?
C13 C18 C17 119.0(5) . . ?
C13 C18 H15 120.5 . . ?
C17 C18 H15 120.5 . . ?
C21 C22 C23 108.4(5) . . ?
C21 C22 H16 125.8 . . ?
C23 C22 H16 125.8 . . ?
C8 C24 C23 126.7(5) 10_565 . ?
C8 C24 C25 115.0(5) 10_565 . ?
C23 C24 C25 118.2(4) . . ?
C30 C25 C26 118.9(6) . . ?
C30 C25 C24 121.0(5) . . ?
C26 C25 C24 120.1(5) . . ?
C13 C14 C15 121.5(5) . . ?
C13 C14 H19 119.2 . . ?
C15 C14 H19 119.2 . . ?
C16 C17 C18 121.2(5) . . ?
C16 C17 H20 119.4 . . ?
C18 C17 H20 119.4 . . ?
C28 C27 C26 123.3(7) . . ?
C28 C27 H21 118.3 . . ?
C26 C27 H21 118.3 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C27 C28 C29 117.0(7) . . ?
C27 C28 C31 121.6(9) . . ?
C29 C28 C31 121.4(9) . . ?
C25 C30 C29 121.0(7) . . ?
C25 C30 H24 119.5 . . ?
C29 C30 H24 119.5 . . ?
C25 C26 C27 118.0(6) . . ?
C25 C26 H25 121.0 . . ?
C27 C26 H25 121.0 . . ?
C28 C29 C30 121.8(7) . . ?
C28 C29 H27 119.1 . . ?
C30 C29 H27 119.1 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O1 C1 C6 121.7(7) . . ?
O1 C1 C2 120.2(7) . . ?
C6 C1 C2 118.0(7) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C2 C1 122.0(8) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 120.8(9) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C5 C6 123.1(9) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C1 C6 C5 119.1(8) . . ?
C1 C6 C7 119.0(9) . . ?
C5 C6 C7 121.7(9) . . ?
C5 C4 C3 116.7(9) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 H4 121.6 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.330
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.101
