# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Compex1
_database_code_depnum_ccdc_archive 'CCDC 958823'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O2 Sn'
_chemical_formula_sum            'C23 H21 N3 O2 Sn'
_chemical_formula_weight         490.12

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   P21/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                   9.0499(5)
_cell_length_b                   22.576(4)
_cell_length_c                   10.339(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.574(3)
_cell_angle_gamma                90.00
_cell_volume                     2102.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7389
_exptl_absorpt_correction_T_max  0.8264
_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 SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11284
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3900
_reflns_number_gt                3255
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  ?

_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)+(0.0430P)²+7.9765P] 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         3900
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_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
C1 C 0.3368(5) 0.9790(2) 0.3545(5) 0.0218(10) Uani 1 1 d . . .
C2 C 0.2398(5) 1.0319(2) 0.3399(5) 0.0224(11) Uani 1 1 d . . .
C3 C 0.1527(6) 1.0494(2) 0.4367(5) 0.0306(12) Uani 1 1 d . . .
H3 H 0.1577 1.0295 0.5158 0.037 Uiso 1 1 calc R . .
C4 C 0.0581(7) 1.0974(3) 0.4123(5) 0.0373(14) Uani 1 1 d . . .
H4 H -0.0003 1.1085 0.4774 0.045 Uiso 1 1 calc R . .
C5 C 0.1321(6) 1.1122(2) 0.2110(5) 0.0305(12) Uani 1 1 d . . .
H5 H 0.1274 1.1340 0.1343 0.037 Uiso 1 1 calc R . .
C6 C 0.2285(6) 1.0649(2) 0.2243(5) 0.0262(11) Uani 1 1 d . . .
H6 H 0.2854 1.0549 0.1574 0.031 Uiso 1 1 calc R . .
C7 C 0.4599(5) 0.8727(2) 0.5777(4) 0.0210(10) Uani 1 1 d . . .
C8 C 0.5483(5) 0.8205(2) 0.5922(5) 0.0238(11) Uani 1 1 d D . .
C9 C 0.6086(6) 0.7892(2) 0.4979(5) 0.0254(11) Uani 1 1 d . . .
C10 C 0.6968(6) 0.7342(2) 0.5327(6) 0.0346(13) Uani 1 1 d . . .
H10A H 0.7315 0.7176 0.4557 0.052 Uiso 1 1 calc R . .
H10B H 0.6351 0.7059 0.5712 0.052 Uiso 1 1 calc R . .
H10C H 0.7802 0.7440 0.5936 0.052 Uiso 1 1 calc R . .
C11 C 0.3923(6) 0.8968(2) 0.6934(5) 0.0265(11) Uani 1 1 d . . .
H11A H 0.3361 0.9318 0.6688 0.040 Uiso 1 1 calc R . .
H11B H 0.4696 0.9065 0.7603 0.040 Uiso 1 1 calc R . .
H11C H 0.3280 0.8675 0.7253 0.040 Uiso 1 1 calc R . .
C12 C 0.7175(5) 0.9078(2) 0.2291(4) 0.0215(10) Uani 1 1 d . . .
C13 C 0.8432(5) 0.8722(2) 0.2554(5) 0.0240(11) Uani 1 1 d . . .
H13 H 0.8350 0.8362 0.2981 0.029 Uiso 1 1 calc R . .
C14 C 0.9800(5) 0.8897(2) 0.2186(5) 0.0299(12) Uani 1 1 d . . .
H14 H 1.0624 0.8652 0.2339 0.036 Uiso 1 1 calc R . .
C15 C 0.9926(6) 0.9443(2) 0.1587(5) 0.0312(12) Uani 1 1 d . . .
H15 H 1.0844 0.9567 0.1355 0.037 Uiso 1 1 calc R . .
C16 C 0.8690(6) 0.9806(2) 0.1332(6) 0.0339(13) Uani 1 1 d . . .
H16 H 0.8777 1.0170 0.0928 0.041 Uiso 1 1 calc R . .
C17 C 0.7333(6) 0.9619(2) 0.1684(5) 0.0259(11) Uani 1 1 d . . .
H17 H 0.6506 0.9861 0.1511 0.031 Uiso 1 1 calc R . .
C18 C 0.3508(5) 0.8327(2) 0.1571(5) 0.0221(10) Uani 1 1 d . . .
C19 C 0.2904(5) 0.7793(2) 0.1961(5) 0.0238(11) Uani 1 1 d . . .
H19 H 0.3234 0.7634 0.2767 0.029 Uiso 1 1 calc R . .
C20 C 0.1825(6) 0.7499(2) 0.1167(5) 0.0303(12) Uani 1 1 d . . .
H20 H 0.1413 0.7149 0.1445 0.036 Uiso 1 1 calc R . .
C21 C 0.1362(6) 0.7733(3) -0.0057(6) 0.0326(13) Uani 1 1 d . . .
H21 H 0.0652 0.7534 -0.0604 0.039 Uiso 1 1 calc R . .
C22 C 0.1953(6) 0.8260(2) -0.0460(5) 0.0286(12) Uani 1 1 d . . .
H22 H 0.1641 0.8412 -0.1277 0.034 Uiso 1 1 calc R . .
C23 C 0.2998(5) 0.8559(2) 0.0344(5) 0.0242(11) Uani 1 1 d . . .
H23 H 0.3370 0.8918 0.0075 0.029 Uiso 1 1 calc R . .
N1 N 0.4347(4) 0.90100(18) 0.4653(4) 0.0215(9) Uani 1 1 d . . .
N2 N 0.3431(4) 0.95089(17) 0.4653(4) 0.0205(9) Uani 1 1 d . . .
N3 N 0.0449(6) 1.1288(2) 0.3017(5) 0.0370(12) Uani 1 1 d . . .
O1 O 0.4055(4) 0.96348(14) 0.2538(3) 0.0230(7) Uani 1 1 d . . .
O2 O 0.5940(4) 0.80180(14) 0.3744(3) 0.0250(8) Uani 1 1 d . . .
Sn1 Sn 0.50944(3) 0.879210(14) 0.28210(3) 0.01913(13) Uani 1 1 d . . .
H8 H 0.569(6) 0.806(2) 0.673(3) 0.042(17) Uiso 1 1 d 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
C1 N2 1.306(6) . ?
C1 O1 1.311(6) . ?
C1 C2 1.480(7) . ?
C2 C3 1.391(7) . ?
C2 C6 1.404(7) . ?
C3 C4 1.388(7) . ?
C4 N3 1.341(7) . ?
C5 N3 1.336(7) . ?
C5 C6 1.378(7) . ?
C7 N1 1.326(6) . ?
C7 C8 1.424(7) . ?
C7 C11 1.498(7) . ?
C8 C9 1.360(7) . ?
C9 O2 1.302(6) . ?
C9 C10 1.500(7) . ?
C12 C17 1.385(7) . ?
C12 C13 1.399(7) . ?
C12 Sn1 2.112(5) . ?
C13 C14 1.387(7) . ?
C14 C15 1.389(8) . ?
C15 C16 1.391(8) . ?
C16 C17 1.381(7) . ?
C18 C19 1.399(7) . ?
C18 C23 1.408(7) . ?
C18 Sn1 2.115(5) . ?
C19 C20 1.383(7) . ?
C20 C21 1.398(8) . ?
C21 C22 1.384(8) . ?
C22 C23 1.374(7) . ?
N1 N2 1.398(5) . ?
N1 Sn1 2.129(4) . ?
O1 Sn1 2.130(3) . ?
O2 Sn1 2.100(3) . ?

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
N2 C1 O1 125.6(4) . . ?
N2 C1 C2 117.2(4) . . ?
O1 C1 C2 117.2(4) . . ?
C3 C2 C6 117.5(5) . . ?
C3 C2 C1 121.9(5) . . ?
C6 C2 C1 120.6(4) . . ?
C4 C3 C2 118.3(5) . . ?
N3 C4 C3 124.7(5) . . ?
N3 C5 C6 123.9(5) . . ?
C5 C6 C2 119.3(5) . . ?
N1 C7 C8 122.5(4) . . ?
N1 C7 C11 118.5(4) . . ?
C8 C7 C11 119.0(4) . . ?
C9 C8 C7 127.9(5) . . ?
O2 C9 C8 125.4(5) . . ?
O2 C9 C10 114.7(5) . . ?
C8 C9 C10 119.9(5) . . ?
C17 C12 C13 118.5(5) . . ?
C17 C12 Sn1 121.4(4) . . ?
C13 C12 Sn1 120.2(4) . . ?
C14 C13 C12 120.9(5) . . ?
C13 C14 C15 119.3(5) . . ?
C14 C15 C16 120.5(5) . . ?
C17 C16 C15 119.3(5) . . ?
C16 C17 C12 121.5(5) . . ?
C19 C18 C23 118.5(5) . . ?
C19 C18 Sn1 120.8(4) . . ?
C23 C18 Sn1 120.6(4) . . ?
C20 C19 C18 121.1(5) . . ?
C19 C20 C21 119.1(5) . . ?
C22 C21 C20 120.5(5) . . ?
C23 C22 C21 120.2(5) . . ?
C22 C23 C18 120.5(5) . . ?
C7 N1 N2 116.0(4) . . ?
C7 N1 Sn1 128.7(3) . . ?
N2 N1 Sn1 115.2(3) . . ?
C1 N2 N1 111.5(4) . . ?
C5 N3 C4 116.2(5) . . ?
C1 O1 Sn1 111.6(3) . . ?
C9 O2 Sn1 128.7(3) . . ?
O2 Sn1 C12 94.47(17) . . ?
O2 Sn1 C18 93.46(16) . . ?
C12 Sn1 C18 124.22(18) . . ?
O2 Sn1 N1 85.49(14) . . ?
C12 Sn1 N1 121.87(16) . . ?
C18 Sn1 N1 113.76(17) . . ?
O2 Sn1 O1 160.46(13) . . ?
C12 Sn1 O1 94.83(16) . . ?
C18 Sn1 O1 95.45(16) . . ?
N1 Sn1 O1 75.01(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.525
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.146
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
