# 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_gadadm
_database_code_depnum_ccdc_archive 'CCDC 1034759'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H49 Ga N2 O'
_chemical_formula_weight         547.45

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'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.4025(4)
_cell_length_b                   9.5037(4)
_cell_length_c                   34.1500(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9760(10)
_cell_angle_gamma                90.00
_cell_volume                     3035.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9126
_exptl_absorpt_correction_T_max  0.9549
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'

_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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25545
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5958
_reflns_number_gt                5449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0387P)²+2.0321P] 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         5958
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Ga1 Ga 0.466181(18) -0.235663(18) 0.102642(5) 0.01817(7) Uani 1 1 d . . .
O1 O 0.34776(12) -0.09453(12) 0.12803(3) 0.0214(2) Uani 1 1 d . . .
N1 N 0.61397(14) -0.16381(14) 0.14860(4) 0.0174(3) Uani 1 1 d . . .
C1 C 0.41824(16) -0.01244(16) 0.15385(4) 0.0177(3) Uani 1 1 d . . .
N2 N 0.69316(14) -0.34669(13) 0.09770(4) 0.0174(3) Uani 1 1 d . . .
C2 C 0.56233(16) -0.04632(16) 0.16760(4) 0.0171(3) Uani 1 1 d . . .
C3 C 0.64564(16) 0.04257(17) 0.19353(4) 0.0179(3) Uani 1 1 d . . .
H3A H 0.7427 0.0193 0.2014 0.021 Uiso 1 1 calc R . .
C4 C 0.58827(17) 0.16312(16) 0.20769(4) 0.0183(3) Uani 1 1 d . . .
C5 C 0.44352(17) 0.19293(17) 0.19539(5) 0.0190(3) Uani 1 1 d . . .
H5A H 0.4026 0.2742 0.2059 0.023 Uiso 1 1 calc R . .
C6 C 0.35726(16) 0.11146(16) 0.16902(4) 0.0173(3) Uani 1 1 d . . .
C7 C 0.67634(18) 0.26018(17) 0.23693(5) 0.0213(3) Uani 1 1 d . . .
C8 C 0.6286(2) 0.4138(2) 0.23197(7) 0.0426(5) Uani 1 1 d . . .
H8A H 0.6304 0.4421 0.2044 0.064 Uiso 1 1 calc R . .
H8B H 0.6936 0.4740 0.2489 0.064 Uiso 1 1 calc R . .
H8C H 0.5313 0.4237 0.2394 0.064 Uiso 1 1 calc R . .
C9 C 0.6555(3) 0.2140(2) 0.27866(6) 0.0464(6) Uani 1 1 d . . .
H9A H 0.6887 0.1168 0.2827 0.070 Uiso 1 1 calc R . .
H9B H 0.5538 0.2197 0.2825 0.070 Uiso 1 1 calc R . .
H9C H 0.7106 0.2758 0.2976 0.070 Uiso 1 1 calc R . .
C10 C 0.8342(2) 0.2542(3) 0.23114(9) 0.0650(9) Uani 1 1 d . . .
H10A H 0.8719 0.1605 0.2384 0.097 Uiso 1 1 calc R . .
H10B H 0.8862 0.3252 0.2478 0.097 Uiso 1 1 calc R . .
H10C H 0.8465 0.2730 0.2035 0.097 Uiso 1 1 calc R . .
C11 C 0.20179(16) 0.15180(16) 0.15548(5) 0.0185(3) Uani 1 1 d . . .
C12 C 0.10023(17) 0.03211(18) 0.16513(5) 0.0226(3) Uani 1 1 d . . .
H12A H 0.1068 0.0186 0.1937 0.034 Uiso 1 1 calc R . .
H12B H 0.1276 -0.0551 0.1526 0.034 Uiso 1 1 calc R . .
H12C H 0.0018 0.0568 0.1553 0.034 Uiso 1 1 calc R . .
C13 C 0.18448(17) 0.18027(18) 0.11087(5) 0.0224(3) Uani 1 1 d . . .
H13A H 0.2492 0.2563 0.1048 0.034 Uiso 1 1 calc R . .
H13B H 0.0855 0.2079 0.1026 0.034 Uiso 1 1 calc R . .
H13C H 0.2077 0.0948 0.0968 0.034 Uiso 1 1 calc R . .
C14 C 0.15588(18) 0.28546(18) 0.17598(5) 0.0241(3) Uani 1 1 d . . .
H14A H 0.1659 0.2707 0.2045 0.036 Uiso 1 1 calc R . .
H14B H 0.0559 0.3068 0.1669 0.036 Uiso 1 1 calc R . .
H14C H 0.2166 0.3643 0.1696 0.036 Uiso 1 1 calc R . .
C15 C 0.72514(17) -0.23979(16) 0.16029(5) 0.0179(3) Uani 1 1 d . . .
C16 C 0.80694(18) -0.23493(17) 0.20040(5) 0.0227(3) Uani 1 1 d . . .
H16A H 0.7449 -0.1988 0.2195 0.034 Uiso 1 1 calc R . .
H16B H 0.8900 -0.1729 0.1998 0.034 Uiso 1 1 calc R . .
H16C H 0.8393 -0.3299 0.2081 0.034 Uiso 1 1 calc R . .
C17 C 0.77420(17) -0.33738(16) 0.13004(5) 0.0185(3) Uani 1 1 d . . .
C18 C 0.91647(18) -0.40916(19) 0.13898(5) 0.0273(4) Uani 1 1 d . . .
H18A H 0.9443 -0.4533 0.1150 0.041 Uiso 1 1 calc R . .
H18B H 0.9091 -0.4814 0.1592 0.041 Uiso 1 1 calc R . .
H18C H 0.9887 -0.3396 0.1486 0.041 Uiso 1 1 calc R . .
C19 C 0.73757(16) -0.41499(16) 0.06349(4) 0.0177(3) Uani 1 1 d . . .
C20 C 0.71112(16) -0.55844(17) 0.05629(5) 0.0197(3) Uani 1 1 d . . .
C21 C 0.74709(17) -0.61393(18) 0.02074(5) 0.0227(3) Uani 1 1 d . . .
H21A H 0.7307 -0.7109 0.0153 0.027 Uiso 1 1 calc R . .
C22 C 0.80573(18) -0.53137(19) -0.00659(5) 0.0249(4) Uani 1 1 d . . .
H22A H 0.8280 -0.5711 -0.0307 0.030 Uiso 1 1 calc R . .
C23 C 0.83215(18) -0.39028(18) 0.00127(5) 0.0238(3) Uani 1 1 d . . .
H23A H 0.8736 -0.3342 -0.0176 0.029 Uiso 1 1 calc R . .
C24 C 0.79936(17) -0.32902(17) 0.03615(5) 0.0199(3) Uani 1 1 d . . .
C25 C 0.64678(17) -0.65421(17) 0.08544(5) 0.0220(3) Uani 1 1 d . . .
H25A H 0.6152 -0.5944 0.1070 0.026 Uiso 1 1 calc R . .
C26 C 0.7575(2) -0.76008(19) 0.10390(6) 0.0297(4) Uani 1 1 d . . .
H26A H 0.8406 -0.7092 0.1166 0.045 Uiso 1 1 calc R . .
H26B H 0.7879 -0.8217 0.0833 0.045 Uiso 1 1 calc R . .
H26C H 0.7148 -0.8168 0.1236 0.045 Uiso 1 1 calc R . .
C27 C 0.51628(19) -0.73332(19) 0.06617(6) 0.0291(4) Uani 1 1 d . . .
H27A H 0.4467 -0.6658 0.0538 0.044 Uiso 1 1 calc R . .
H27B H 0.4725 -0.7872 0.0862 0.044 Uiso 1 1 calc R . .
H27C H 0.5460 -0.7977 0.0461 0.044 Uiso 1 1 calc R . .
C28 C 0.83497(19) -0.17491(17) 0.04493(5) 0.0241(4) Uani 1 1 d . . .
H28A H 0.7750 -0.1424 0.0657 0.029 Uiso 1 1 calc R . .
C29 C 0.9924(2) -0.1592(2) 0.06117(6) 0.0343(4) Uani 1 1 d . . .
H29A H 1.0119 -0.2176 0.0848 0.051 Uiso 1 1 calc R . .
H29B H 1.0124 -0.0604 0.0679 0.051 Uiso 1 1 calc R . .
H29C H 1.0535 -0.1894 0.0412 0.051 Uiso 1 1 calc R . .
C30 C 0.8026(2) -0.08013(19) 0.00906(6) 0.0322(4) Uani 1 1 d . . .
H30A H 0.7034 -0.0945 -0.0021 0.048 Uiso 1 1 calc R . .
H30B H 0.8672 -0.1035 -0.0107 0.048 Uiso 1 1 calc R . .
H30C H 0.8163 0.0185 0.0170 0.048 Uiso 1 1 calc R . .
C31 C 0.46038(19) -0.15133(18) 0.05029(5) 0.0255(4) Uani 1 1 d . . .
H31A H 0.3613 -0.1285 0.0406 0.038 Uiso 1 1 calc R . .
H31B H 0.4990 -0.2180 0.0322 0.038 Uiso 1 1 calc R . .
H31C H 0.5180 -0.0652 0.0518 0.038 Uiso 1 1 calc R . .
C32 C 0.37750(18) -0.41114(18) 0.11894(5) 0.0247(3) Uani 1 1 d . . .
H32A H 0.2796 -0.3918 0.1248 0.037 Uiso 1 1 calc R . .
H32B H 0.4333 -0.4486 0.1425 0.037 Uiso 1 1 calc R . .
H32C H 0.3755 -0.4803 0.0976 0.037 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
Ga1 C31 1.9548(17) . ?
Ga1 C32 1.9705(17) . ?
Ga1 O1 1.9978(11) . ?
Ga1 N1 2.0991(13) . ?
Ga1 N2 2.4023(13) . ?
O1 C1 1.3052(19) . ?
N1 C15 1.299(2) . ?
N1 C2 1.403(2) . ?
C1 C2 1.424(2) . ?
C1 C6 1.430(2) . ?
N2 C17 1.278(2) . ?
N2 C19 1.4362(19) . ?
C2 C3 1.403(2) . ?
C3 C4 1.375(2) . ?
C4 C5 1.411(2) . ?
C4 C7 1.537(2) . ?
C5 C6 1.384(2) . ?
C6 C11 1.535(2) . ?
C7 C10 1.519(3) . ?
C7 C9 1.523(3) . ?
C7 C8 1.532(3) . ?
C11 C14 1.534(2) . ?
C11 C13 1.539(2) . ?
C11 C12 1.543(2) . ?
C15 C17 1.496(2) . ?
C15 C16 1.500(2) . ?
C17 C18 1.504(2) . ?
C19 C20 1.403(2) . ?
C19 C24 1.410(2) . ?
C20 C21 1.397(2) . ?
C20 C25 1.520(2) . ?
C21 C22 1.378(2) . ?
C22 C23 1.385(2) . ?
C23 C24 1.389(2) . ?
C24 C28 1.525(2) . ?
C25 C27 1.528(2) . ?
C25 C26 1.535(2) . ?
C28 C30 1.526(2) . ?
C28 C29 1.533(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
C31 Ga1 C32 129.27(7) . . ?
C31 Ga1 O1 99.08(6) . . ?
C32 Ga1 O1 100.04(6) . . ?
C31 Ga1 N1 120.24(6) . . ?
C32 Ga1 N1 109.32(6) . . ?
O1 Ga1 N1 79.20(5) . . ?
C31 Ga1 N2 93.23(6) . . ?
C32 Ga1 N2 93.05(6) . . ?
O1 Ga1 N2 149.84(4) . . ?
N1 Ga1 N2 70.83(5) . . ?
C1 O1 Ga1 115.33(10) . . ?
C15 N1 C2 127.34(13) . . ?
C15 N1 Ga1 119.86(11) . . ?
C2 N1 Ga1 111.75(10) . . ?
O1 C1 C2 119.10(14) . . ?
O1 C1 C6 122.85(14) . . ?
C2 C1 C6 118.06(14) . . ?
C17 N2 C19 122.46(13) . . ?
C17 N2 Ga1 111.29(10) . . ?
C19 N2 Ga1 126.25(10) . . ?
C3 C2 N1 125.02(14) . . ?
C3 C2 C1 121.45(14) . . ?
N1 C2 C1 113.00(13) . . ?
C4 C3 C2 120.66(14) . . ?
C3 C4 C5 117.65(14) . . ?
C3 C4 C7 121.60(14) . . ?
C5 C4 C7 120.72(14) . . ?
C6 C5 C4 124.28(15) . . ?
C5 C6 C1 117.80(14) . . ?
C5 C6 C11 122.09(14) . . ?
C1 C6 C11 120.10(14) . . ?
C10 C7 C9 109.5(2) . . ?
C10 C7 C8 107.49(18) . . ?
C9 C7 C8 108.27(16) . . ?
C10 C7 C4 111.13(14) . . ?
C9 C7 C4 108.77(14) . . ?
C8 C7 C4 111.62(14) . . ?
C14 C11 C6 111.94(13) . . ?
C14 C11 C13 107.48(13) . . ?
C6 C11 C13 109.96(12) . . ?
C14 C11 C12 107.65(13) . . ?
C6 C11 C12 110.04(13) . . ?
C13 C11 C12 109.70(13) . . ?
N1 C15 C17 115.38(14) . . ?
N1 C15 C16 125.68(14) . . ?
C17 C15 C16 118.93(14) . . ?
N2 C17 C15 116.14(14) . . ?
N2 C17 C18 125.57(14) . . ?
C15 C17 C18 118.19(14) . . ?
C20 C19 C24 121.64(14) . . ?
C20 C19 N2 121.37(14) . . ?
C24 C19 N2 116.83(14) . . ?
C21 C20 C19 117.69(15) . . ?
C21 C20 C25 119.46(14) . . ?
C19 C20 C25 122.85(14) . . ?
C22 C21 C20 121.59(15) . . ?
C21 C22 C23 119.78(16) . . ?
C22 C23 C24 121.37(16) . . ?
C23 C24 C19 117.92(15) . . ?
C23 C24 C28 120.48(14) . . ?
C19 C24 C28 121.56(14) . . ?
C20 C25 C27 111.66(14) . . ?
C20 C25 C26 111.23(14) . . ?
C27 C25 C26 109.52(14) . . ?
C24 C28 C30 112.82(14) . . ?
C24 C28 C29 110.41(14) . . ?
C30 C28 C29 109.71(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_indado
_database_code_depnum_ccdc_archive 'CCDC 1034760'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H49 In N2 O'
_chemical_formula_weight         592.55

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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.3801(7)
_cell_length_b                   9.5414(7)
_cell_length_c                   34.908(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.4420(10)
_cell_angle_gamma                90.00
_cell_volume                     3097.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30

_exptl_crystal_description       plate
_exptl_crystal_colour            dark_red
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'

_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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25613
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6058
_reflns_number_gt                5468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0446P)²+5.2746P] 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         6058
_refine_ls_number_parameters     352
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.164
_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
In1 In 0.549988(19) -0.232738(18) -0.098724(5) 0.01931(5) Uani 1 1 d . . .
O1 O 0.6652(2) -0.07321(19) -0.12806(6) 0.0232(4) Uani 1 1 d . . .
N1 N 0.3898(2) -0.1439(2) -0.14911(6) 0.0195(5) Uani 1 1 d . . .
N2 N 0.3077(2) -0.3341(2) -0.10063(6) 0.0190(5) Uani 1 1 d . . .
C1 C 0.4444(3) -0.0295(3) -0.16751(8) 0.0188(6) Uani 1 1 d . . .
C2 C 0.5898(3) 0.0051(3) -0.15391(8) 0.0193(6) Uani 1 1 d . . .
C3 C 0.6509(3) 0.1264(3) -0.16971(8) 0.0191(6) Uani 1 1 d . . .
C4 C 0.5636(3) 0.2063(3) -0.19629(8) 0.0213(6) Uani 1 1 d . . .
H4A H 0.6045 0.2861 -0.2069 0.026 Uiso 1 1 calc R . .
C5 C 0.4174(3) 0.1763(3) -0.20850(8) 0.0211(6) Uani 1 1 d . A .
C6 C 0.3598(3) 0.0581(3) -0.19403(7) 0.0200(6) Uani 1 1 d . . .
H6A H 0.2619 0.0350 -0.2020 0.024 Uiso 1 1 calc R . .
C7 C 0.8088(3) 0.1656(3) -0.15692(8) 0.0203(6) Uani 1 1 d . . .
C8 C 0.8320(3) 0.1973(3) -0.11329(8) 0.0234(6) Uani 1 1 d . . .
H8A H 0.8003 0.1170 -0.0991 0.035 Uiso 1 1 calc R . .
H8B H 0.7763 0.2804 -0.1080 0.035 Uiso 1 1 calc R . .
H8C H 0.9343 0.2148 -0.1050 0.035 Uiso 1 1 calc R . .
C9 C 0.9080(3) 0.0438(3) -0.16568(9) 0.0245(6) Uani 1 1 d . . .
H9A H 0.8810 -0.0413 -0.1527 0.037 Uiso 1 1 calc R . .
H9B H 1.0080 0.0679 -0.1563 0.037 Uiso 1 1 calc R . .
H9C H 0.8980 0.0276 -0.1936 0.037 Uiso 1 1 calc R . .
C10 C 0.8550(3) 0.2964(3) -0.17773(9) 0.0268(7) Uani 1 1 d . . .
H10A H 0.7956 0.3763 -0.1720 0.040 Uiso 1 1 calc R . .
H10B H 0.8427 0.2795 -0.2057 0.040 Uiso 1 1 calc R . .
H10C H 0.9562 0.3169 -0.1688 0.040 Uiso 1 1 calc R . .
C11 C 0.3274(3) 0.2721(3) -0.23773(9) 0.0264(6) Uani 1 1 d . . .
C12 C 0.3481(7) 0.2232(5) -0.27919(14) 0.0410(14) Uani 0.679(5) 1 d P A 1
H12A H 0.3231 0.1237 -0.2822 0.061 Uiso 0.679(5) 1 calc PR A 1
H12B H 0.4486 0.2368 -0.2833 0.061 Uiso 0.679(5) 1 calc PR A 1
H12C H 0.2855 0.2783 -0.2982 0.061 Uiso 0.679(5) 1 calc PR A 1
C13 C 0.1705(6) 0.2722(6) -0.23177(17) 0.0438(12) Uani 0.679(5) 1 d PU A 1
H13A H 0.1295 0.1790 -0.2376 0.066 Uiso 0.679(5) 1 calc PR A 1
H13B H 0.1183 0.3415 -0.2490 0.066 Uiso 0.679(5) 1 calc PR A 1
H13C H 0.1620 0.2963 -0.2049 0.066 Uiso 0.679(5) 1 calc PR A 1
C14 C 0.3789(6) 0.4279(5) -0.23380(14) 0.0355(13) Uani 0.679(5) 1 d P A 1
H14A H 0.4776 0.4347 -0.2400 0.053 Uiso 0.679(5) 1 calc PR A 1
H14B H 0.3758 0.4600 -0.2072 0.053 Uiso 0.679(5) 1 calc PR A 1
H14C H 0.3155 0.4867 -0.2517 0.053 Uiso 0.679(5) 1 calc PR A 1
C12' C 0.3816(17) 0.2681(12) -0.2742(3) 0.0410(14) Uani 0.321(5) 1 d P A 2
H12D H 0.3939 0.1704 -0.2818 0.061 Uiso 0.321(5) 1 calc PR A 2
H12E H 0.4745 0.3164 -0.2720 0.061 Uiso 0.321(5) 1 calc PR A 2
H12F H 0.3135 0.3148 -0.2938 0.061 Uiso 0.321(5) 1 calc PR A 2
C13' C 0.1693(12) 0.2141(14) -0.2479(4) 0.0438(12) Uani 0.321(5) 1 d PU A 2
H13D H 0.1729 0.1175 -0.2573 0.066 Uiso 0.321(5) 1 calc PR A 2
H13E H 0.1166 0.2727 -0.2680 0.066 Uiso 0.321(5) 1 calc PR A 2
H13F H 0.1205 0.2161 -0.2247 0.066 Uiso 0.321(5) 1 calc PR A 2
C14' C 0.3243(14) 0.4169(11) -0.2213(3) 0.0355(13) Uani 0.321(5) 1 d P A 2
H14D H 0.2638 0.4176 -0.2004 0.053 Uiso 0.321(5) 1 calc PR A 2
H14E H 0.2849 0.4823 -0.2416 0.053 Uiso 0.321(5) 1 calc PR A 2
H14F H 0.4222 0.4456 -0.2111 0.053 Uiso 0.321(5) 1 calc PR A 2
C15 C 0.2792(3) -0.2205(3) -0.16162(8) 0.0206(6) Uani 1 1 d . . .
C16 C 0.2260(3) -0.3158(3) -0.13243(8) 0.0209(6) Uani 1 1 d . . .
C17 C 0.1989(3) -0.2187(3) -0.20176(8) 0.0260(6) Uani 1 1 d . . .
H17A H 0.2622 -0.1837 -0.2199 0.039 Uiso 1 1 calc R . .
H17B H 0.1149 -0.1572 -0.2024 0.039 Uiso 1 1 calc R . .
H17C H 0.1673 -0.3139 -0.2092 0.039 Uiso 1 1 calc R . .
C18 C 0.0777(3) -0.3771(4) -0.14176(9) 0.0335(8) Uani 1 1 d . . .
H18A H 0.0504 -0.4242 -0.1188 0.050 Uiso 1 1 calc R . .
H18B H 0.0773 -0.4451 -0.1628 0.050 Uiso 1 1 calc R . .
H18C H 0.0089 -0.3020 -0.1497 0.050 Uiso 1 1 calc R . .
C19 C 0.2606(3) -0.4020(3) -0.06770(8) 0.0201(6) Uani 1 1 d . . .
C20 C 0.1863(3) -0.3219(3) -0.04293(8) 0.0248(6) Uani 1 1 d . . .
C21 C 0.1566(3) -0.3829(3) -0.00887(9) 0.0296(7) Uani 1 1 d . . .
H21A H 0.1078 -0.3298 0.0084 0.036 Uiso 1 1 calc R . .
C22 C 0.1966(3) -0.5200(3) 0.00051(9) 0.0323(7) Uani 1 1 d . . .
H22A H 0.1761 -0.5600 0.0241 0.039 Uiso 1 1 calc R . .
C23 C 0.2666(3) -0.5980(3) -0.02487(9) 0.0311(7) Uani 1 1 d . . .
H23A H 0.2920 -0.6924 -0.0187 0.037 Uiso 1 1 calc R . .
C24 C 0.3006(3) -0.5411(3) -0.05915(8) 0.0232(6) Uani 1 1 d . . .
C25 C 0.1338(4) -0.1724(3) -0.05253(10) 0.0358(8) Uani 1 1 d . . .
H25A H 0.1760 -0.1408 -0.0760 0.043 Uiso 1 1 calc R . .
C26 C -0.0298(4) -0.1700(4) -0.06201(11) 0.0459(10) Uani 1 1 d . . .
H26A H -0.0597 -0.2373 -0.0827 0.069 Uiso 1 1 calc R . .
H26B H -0.0611 -0.0757 -0.0705 0.069 Uiso 1 1 calc R . .
H26C H -0.0735 -0.1953 -0.0389 0.069 Uiso 1 1 calc R . .
C27 C 0.1801(4) -0.0694(4) -0.01998(13) 0.0518(11) Uani 1 1 d . . .
H27A H 0.2852 -0.0693 -0.0143 0.078 Uiso 1 1 calc R . .
H27B H 0.1383 -0.0974 0.0032 0.078 Uiso 1 1 calc R . .
H27C H 0.1466 0.0248 -0.0278 0.078 Uiso 1 1 calc R . .
C28 C 0.3743(3) -0.6312(3) -0.08667(9) 0.0286(7) Uani 1 1 d . . .
H28A H 0.4125 -0.5677 -0.1057 0.034 Uiso 1 1 calc R . .
C29 C 0.2661(4) -0.7311(4) -0.10908(11) 0.0479(10) Uani 1 1 d . . .
H29A H 0.3131 -0.7827 -0.1282 0.072 Uiso 1 1 calc R . .
H29B H 0.1853 -0.6771 -0.1222 0.072 Uiso 1 1 calc R . .
H29C H 0.2305 -0.7975 -0.0911 0.072 Uiso 1 1 calc R . .
C30 C 0.4996(4) -0.7155(3) -0.06633(11) 0.0381(8) Uani 1 1 d . . .
H30A H 0.5703 -0.6516 -0.0526 0.057 Uiso 1 1 calc R . .
H30B H 0.5448 -0.7690 -0.0855 0.057 Uiso 1 1 calc R . .
H30C H 0.4643 -0.7801 -0.0479 0.057 Uiso 1 1 calc R . .
C31 C 0.5507(3) -0.1358(3) -0.04368(9) 0.0296(7) Uani 1 1 d . . .
H31A H 0.6502 -0.1202 -0.0320 0.044 Uiso 1 1 calc R . .
H31B H 0.5020 -0.1968 -0.0269 0.044 Uiso 1 1 calc R . .
H31C H 0.5003 -0.0457 -0.0469 0.044 Uiso 1 1 calc R . .
C32 C 0.6511(3) -0.4121(3) -0.12135(9) 0.0293(7) Uani 1 1 d . . .
H32A H 0.7403 -0.3828 -0.1309 0.044 Uiso 1 1 calc R . .
H32B H 0.5859 -0.4531 -0.1426 0.044 Uiso 1 1 calc R . .
H32C H 0.6731 -0.4819 -0.1008 0.044 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
In1 C31 2.132(3) . ?
In1 C32 2.156(3) . ?
In1 O1 2.1956(19) . ?
In1 N1 2.320(2) . ?
In1 N2 2.463(2) . ?
O1 C2 1.307(3) . ?
N1 C15 1.298(3) . ?
N1 C1 1.397(3) . ?
N2 C16 1.277(3) . ?
N2 C19 1.438(4) . ?
C1 C6 1.412(4) . ?
C1 C2 1.423(4) . ?
C2 C3 1.434(4) . ?
C3 C4 1.384(4) . ?
C3 C7 1.536(4) . ?
C4 C5 1.412(4) . ?
C5 C6 1.375(4) . ?
C5 C11 1.538(4) . ?
C7 C10 1.534(4) . ?
C7 C8 1.540(4) . ?
C7 C9 1.544(4) . ?
C11 C12' 1.431(14) . ?
C11 C14' 1.498(11) . ?
C11 C13 1.513(6) . ?
C11 C12 1.556(6) . ?
C11 C14 1.564(6) . ?
C11 C13' 1.580(12) . ?
C15 C16 1.499(4) . ?
C15 C17 1.502(4) . ?
C16 C18 1.505(4) . ?
C19 C24 1.401(4) . ?
C19 C20 1.405(4) . ?
C20 C21 1.384(4) . ?
C20 C25 1.531(4) . ?
C21 C22 1.388(5) . ?
C22 C23 1.386(5) . ?
C23 C24 1.388(4) . ?
C24 C28 1.520(4) . ?
C25 C27 1.522(5) . ?
C25 C26 1.527(5) . ?
C28 C30 1.522(4) . ?
C28 C29 1.531(5) . ?

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
C31 In1 C32 136.44(12) . . ?
C31 In1 O1 100.08(10) . . ?
C32 In1 O1 96.49(10) . . ?
C31 In1 N1 116.80(10) . . ?
C32 In1 N1 106.54(10) . . ?
O1 In1 N1 72.71(7) . . ?
C31 In1 N2 95.17(10) . . ?
C32 In1 N2 97.27(10) . . ?
O1 In1 N2 140.18(7) . . ?
N1 In1 N2 67.57(8) . . ?
C2 O1 In1 117.58(17) . . ?
C15 N1 C1 127.6(2) . . ?
C15 N1 In1 117.41(18) . . ?
C1 N1 In1 113.21(16) . . ?
C16 N2 C19 123.0(2) . . ?
C16 N2 In1 114.69(18) . . ?
C19 N2 In1 122.24(16) . . ?
N1 C1 C6 123.7(2) . . ?
N1 C1 C2 114.8(2) . . ?
C6 C1 C2 120.9(2) . . ?
O1 C2 C1 120.5(2) . . ?
O1 C2 C3 121.3(2) . . ?
C1 C2 C3 118.2(2) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 C7 121.7(2) . . ?
C2 C3 C7 120.2(2) . . ?
C3 C4 C5 123.9(2) . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 C11 121.6(2) . . ?
C4 C5 C11 120.5(2) . . ?
C5 C6 C1 120.8(2) . . ?
C10 C7 C3 112.4(2) . . ?
C10 C7 C8 107.2(2) . . ?
C3 C7 C8 110.1(2) . . ?
C10 C7 C9 107.7(2) . . ?
C3 C7 C9 110.0(2) . . ?
C8 C7 C9 109.4(2) . . ?
C12' C11 C14' 113.1(7) . . ?
C12' C11 C13 125.9(6) . . ?
C14' C11 C13 83.0(6) . . ?
C12' C11 C5 110.3(6) . . ?
C14' C11 C5 109.3(5) . . ?
C13 C11 C5 111.7(3) . . ?
C12' C11 C12 20.5(5) . . ?
C14' C11 C12 130.1(5) . . ?
C13 C11 C12 111.6(4) . . ?
C5 C11 C12 108.4(3) . . ?
C12' C11 C14 87.8(5) . . ?
C14' C11 C14 27.2(5) . . ?
C13 C11 C14 106.4(4) . . ?
C5 C11 C14 111.7(3) . . ?
C12 C11 C14 107.0(3) . . ?
C12' C11 C13' 102.8(7) . . ?
C14' C11 C13' 110.2(7) . . ?
C13 C11 C13' 29.5(5) . . ?
C5 C11 C13' 111.1(5) . . ?
C12 C11 C13' 85.0(6) . . ?
C14 C11 C13' 128.5(5) . . ?
N1 C15 C16 115.8(2) . . ?
N1 C15 C17 126.1(3) . . ?
C16 C15 C17 118.1(2) . . ?
N2 C16 C15 117.3(2) . . ?
N2 C16 C18 124.7(3) . . ?
C15 C16 C18 117.9(2) . . ?
C24 C19 C20 121.7(3) . . ?
C24 C19 N2 119.7(2) . . ?
C20 C19 N2 118.4(2) . . ?
C21 C20 C19 118.1(3) . . ?
C21 C20 C25 119.0(3) . . ?
C19 C20 C25 122.9(3) . . ?
C20 C21 C22 121.4(3) . . ?
C23 C22 C21 119.4(3) . . ?
C22 C23 C24 121.5(3) . . ?
C23 C24 C19 118.0(3) . . ?
C23 C24 C28 119.9(3) . . ?
C19 C24 C28 122.2(3) . . ?
C27 C25 C26 109.5(3) . . ?
C27 C25 C20 112.7(3) . . ?
C26 C25 C20 110.3(3) . . ?
C24 C28 C30 113.0(3) . . ?
C24 C28 C29 110.4(3) . . ?
C30 C28 C29 109.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         2.066
_refine_diff_density_min         -1.054
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_tlapme
_database_code_depnum_ccdc_archive 'CCDC 1034761'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H49 N2 O Tl'
_chemical_formula_weight         682.10

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'
Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/m

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

_cell_length_a                   9.4850(6)
_cell_length_b                   9.6118(6)
_cell_length_c                   17.0918(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.3000(10)
_cell_angle_gamma                90.00
_cell_volume                     1541.90(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    5.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3204
_exptl_absorpt_correction_T_max  0.7788
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'

_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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14206
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3567
_reflns_number_gt                3365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0223P)²+0.6656P] 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         3567
_refine_ls_number_parameters     336
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0399
_refine_ls_wR_factor_gt          0.0393
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.090
_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
Tl1 Tl 0.071170(7) 0.2500 0.316280(4) 0.02028(2) Uani 1 2 d S . .
O1 O 0.1807(2) 0.4125(2) 0.24385(12) 0.0215(5) Uani 0.50 1 d P A -1
N1 N -0.1015(2) 0.3461(2) 0.20441(13) 0.0188(5) Uani 0.50 1 d P A -1
N2 N -0.1930(2) 0.1584(2) 0.30203(13) 0.0198(5) Uani 0.50 1 d P A -1
C1 C 0.0998(3) 0.4932(3) 0.19338(15) 0.0197(6) Uani 0.50 1 d P A -1
C2 C 0.1554(3) 0.6162(3) 0.16172(15) 0.0181(6) Uani 0.50 1 d P A -1
C3 C 0.0650(3) 0.6968(3) 0.10904(15) 0.0199(6) Uani 0.50 1 d P A -1
H3A H 0.1038 0.7769 0.0875 0.024 Uiso 0.50 1 calc PR A -1
C4 C -0.0802(3) 0.6677(3) 0.08539(15) 0.0198(6) Uani 0.50 1 d P A -1
C5 C -0.1341(3) 0.5492(3) 0.11530(15) 0.0202(6) Uani 0.50 1 d P A -1
H5A H -0.2320 0.5272 0.1008 0.024 Uiso 0.50 1 calc PR A -1
C6 C -0.0472(3) 0.4597(3) 0.16691(15) 0.0177(6) Uani 0.50 1 d P A -1
C7 C -0.2110(2) 0.2711(3) 0.17706(13) 0.0186(7) Uani 0.50 1 d P A -1
C8 C -0.2867(3) 0.2712(4) 0.09228(13) 0.0280(9) Uani 0.50 1 d P A -1
H8A H -0.2170 0.2554 0.0561 0.042 Uiso 0.50 1 calc PR A -1
H8B H -0.3335 0.3612 0.0805 0.042 Uiso 0.50 1 calc PR A -1
H8C H -0.3583 0.1970 0.0857 0.042 Uiso 0.50 1 calc PR A -1
C9 C -0.2678(3) 0.1762(3) 0.23483(16) 0.0210(6) Uani 0.50 1 d P A -1
C10 C -0.4130(3) 0.1141(4) 0.21069(19) 0.0364(8) Uani 0.50 1 d P A -1
H10A H -0.4436 0.0663 0.2560 0.055 Uiso 0.50 1 calc PR A -1
H10B H -0.4091 0.0473 0.1677 0.055 Uiso 0.50 1 calc PR A -1
H10C H -0.4810 0.1881 0.1926 0.055 Uiso 0.50 1 calc PR A -1
C11 C -0.2416(3) 0.0899(3) 0.36721(16) 0.0201(6) Uani 0.50 1 d P A -1
C12 C -0.2029(3) -0.0492(3) 0.38471(16) 0.0237(6) Uani 0.50 1 d P A -1
C13 C -0.2378(3) -0.1062(3) 0.45444(18) 0.0327(7) Uani 0.50 1 d P A -1
H13A H -0.2133 -0.2002 0.4671 0.039 Uiso 0.50 1 calc PR A -1
C14 C -0.3064(3) -0.0298(4) 0.50517(18) 0.0330(8) Uani 0.50 1 d P A -1
H14A H -0.3265 -0.0706 0.5530 0.040 Uiso 0.50 1 calc PR A -1
C15 C -0.3474(3) 0.1084(3) 0.48710(18) 0.0252(7) Uani 0.50 1 d P A -1
H15A H -0.3965 0.1605 0.5220 0.030 Uiso 0.50 1 calc PR A -1
C16 C -0.3158(3) 0.1675(3) 0.41845(18) 0.0249(7) Uani 0.50 1 d P A -1
C17 C 0.3123(3) 0.6565(3) 0.18775(15) 0.0185(6) Uani 0.50 1 d P A -1
C18 C 0.3373(3) 0.6846(3) 0.27763(15) 0.0225(6) Uani 0.50 1 d P A -1
H18A H 0.4393 0.6981 0.2953 0.034 Uiso 0.50 1 calc PR A -1
H18B H 0.3033 0.6051 0.3055 0.034 Uiso 0.50 1 calc PR A -1
H18C H 0.2852 0.7685 0.2891 0.034 Uiso 0.50 1 calc PR A -1
C19 C 0.4115(3) 0.5397(3) 0.16732(17) 0.0239(7) Uani 0.50 1 d P A -1
H19A H 0.4005 0.5278 0.1098 0.036 Uiso 0.50 1 calc PR A -1
H19B H 0.3868 0.4527 0.1919 0.036 Uiso 0.50 1 calc PR A -1
H19C H 0.5105 0.5643 0.1872 0.036 Uiso 0.50 1 calc PR A -1
C20 C 0.3528(3) 0.7898(2) 0.14688(17) 0.0238(7) Uani 0.50 1 d P A -1
H20A H 0.3360 0.7767 0.0894 0.036 Uiso 0.50 1 calc PR A -1
H20B H 0.4538 0.8106 0.1638 0.036 Uiso 0.50 1 calc PR A -1
H20C H 0.2945 0.8674 0.1613 0.036 Uiso 0.50 1 calc PR A -1
C21 C -0.1722(2) 0.7663(3) 0.02684(13) 0.0203(6) Uani 0.50 1 d P A -1
C22 C -0.1277(4) 0.9156(3) 0.0374(2) 0.0473(10) Uani 0.50 1 d P A -1
H22A H -0.1971 0.9748 0.0048 0.071 Uiso 0.50 1 calc PR A -1
H22B H -0.0336 0.9278 0.0211 0.071 Uiso 0.50 1 calc PR A -1
H22C H -0.1234 0.9417 0.0931 0.071 Uiso 0.50 1 calc PR A -1
C23 C -0.1526(4) 0.7185(3) -0.05690(18) 0.0462(12) Uani 0.50 1 d P A -1
H23A H -0.2090 0.7782 -0.0961 0.069 Uiso 0.50 1 calc PR A -1
H23B H -0.1847 0.6219 -0.0648 0.069 Uiso 0.50 1 calc PR A -1
H23C H -0.0517 0.7249 -0.0631 0.069 Uiso 0.50 1 calc PR A -1
C24 C -0.3291(3) 0.7348(7) 0.0347(2) 0.0521(10) Uani 0.50 1 d PU A -1
H24A H -0.3873 0.8177 0.0202 0.078 Uiso 0.50 1 calc PR A -1
H24B H -0.3363 0.7090 0.0894 0.078 Uiso 0.50 1 calc PR A -1
H24C H -0.3635 0.6579 -0.0006 0.078 Uiso 0.50 1 calc PR A -1
C25 C -0.1291(3) -0.1374(3) 0.32907(18) 0.0284(7) Uani 0.50 1 d P A -1
H25A H -0.1006 -0.0754 0.2871 0.034 Uiso 0.50 1 calc PR A -1
C26 C -0.2309(3) -0.2580(9) 0.28680(17) 0.0457(8) Uani 0.50 1 d P A -1
H26A H -0.1836 -0.3038 0.2464 0.069 Uiso 0.50 1 calc PR A -1
H26B H -0.3209 -0.2170 0.2619 0.069 Uiso 0.50 1 calc PR A -1
H26C H -0.2501 -0.3266 0.3264 0.069 Uiso 0.50 1 calc PR A -1
C27 C 0.0041(3) -0.2087(3) 0.3709(2) 0.0396(9) Uani 0.50 1 d P A -1
H27A H 0.0691 -0.1387 0.3977 0.059 Uiso 0.50 1 calc PR A -1
H27B H 0.0515 -0.2587 0.3321 0.059 Uiso 0.50 1 calc PR A -1
H27C H -0.0226 -0.2747 0.4100 0.059 Uiso 0.50 1 calc PR A -1
C28 C -0.3633(4) 0.3156(4) 0.3981(2) 0.0370(9) Uani 0.50 1 d P A -1
H28A H -0.3153 0.3480 0.3530 0.044 Uiso 0.50 1 calc PR A -1
C29 C -0.3246(4) 0.4175(5) 0.4683(3) 0.0528(13) Uani 0.50 1 d P A -1
H29A H -0.2232 0.4082 0.4891 0.079 Uiso 0.50 1 calc PR A -1
H29B H -0.3818 0.3955 0.5100 0.079 Uiso 0.50 1 calc PR A -1
H29C H -0.3443 0.5131 0.4500 0.079 Uiso 0.50 1 calc PR A -1
C30 C -0.5260(4) 0.3204(4) 0.3720(2) 0.0511(11) Uani 0.50 1 d P A -1
H30A H -0.5523 0.2542 0.3287 0.077 Uiso 0.50 1 calc PR A -1
H30B H -0.5540 0.4145 0.3539 0.077 Uiso 0.50 1 calc PR A -1
H30C H -0.5749 0.2956 0.4167 0.077 Uiso 0.50 1 calc PR A -1
C31 C 0.1475(3) 0.0771(4) 0.2545(2) 0.0271(8) Uani 0.50 1 d P A -1
H31A H 0.2306 0.1062 0.2304 0.041 Uiso 0.50 1 calc PR A -1
H31B H 0.0721 0.0453 0.2130 0.041 Uiso 0.50 1 calc PR A -1
H31C H 0.1747 0.0010 0.2917 0.041 Uiso 0.50 1 calc PR A -1
C32 C 0.0377(4) 0.3861(4) 0.40947(19) 0.0362(8) Uani 0.50 1 d P A -1
H32A H 0.1287 0.4277 0.4324 0.054 Uiso 0.50 1 calc PR A -1
H32B H -0.0022 0.3337 0.4503 0.054 Uiso 0.50 1 calc PR A -1
H32C H -0.0289 0.4597 0.3888 0.054 Uiso 0.50 1 calc PR A -1


_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
Tl1 C32 2.120(3) . ?
Tl1 C32 2.120(3) 4_565 ?
Tl1 C31 2.150(4) 4_565 ?
Tl1 C31 2.150(4) . ?
Tl1 O1 2.328(2) . ?
Tl1 O1 2.328(2) 4_565 ?
Tl1 N1 2.507(2) . ?
Tl1 N1 2.507(2) 4_565 ?
Tl1 N2 2.634(2) . ?
Tl1 N2 2.634(2) 4_565 ?
O1 C1 1.321(3) . ?
N1 C7 1.295(3) . ?
N1 C6 1.401(3) . ?
N2 C9 1.271(3) . ?
N2 C11 1.427(3) . ?
C1 C2 1.432(4) . ?
C1 C6 1.439(4) . ?
C2 C3 1.386(4) . ?
C2 C17 1.540(3) . ?
C3 C4 1.407(4) . ?
C4 C5 1.377(4) . ?
C4 C21 1.552(4) . ?
C5 C6 1.410(4) . ?
C7 C9 1.500(4) . ?
C7 C8 1.521(3) . ?
C9 C10 1.503(4) . ?
C11 C12 1.407(4) . ?
C11 C16 1.413(4) . ?
C12 C13 1.394(4) . ?
C12 C25 1.518(4) . ?
C13 C14 1.370(5) . ?
C14 C15 1.406(5) . ?
C15 C16 1.375(4) . ?
C16 C28 1.518(4) . ?
C17 C20 1.535(4) . ?
C17 C19 1.537(4) . ?
C17 C18 1.544(4) . ?
C21 C22 1.500(5) . ?
C21 C23 1.540(4) . ?
C21 C24 1.543(4) . ?
C25 C27 1.522(4) . ?
C25 C26 1.612(7) . ?
C28 C30 1.543(6) . ?
C28 C29 1.551(6) . ?

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
C32 Tl1 C32 76.18(19) . 4_565 ?
C32 Tl1 C31 89.42(14) . 4_565 ?
C32 Tl1 C31 160.66(13) 4_565 4_565 ?
C32 Tl1 C31 160.66(13) . . ?
C32 Tl1 C31 89.42(14) 4_565 . ?
C31 Tl1 C31 101.23(19) 4_565 . ?
C32 Tl1 O1 96.46(11) . . ?
C32 Tl1 O1 160.04(10) 4_565 . ?
C31 Tl1 O1 9.13(11) 4_565 . ?
C31 Tl1 O1 92.83(11) . . ?
C32 Tl1 O1 160.04(10) . 4_565 ?
C32 Tl1 O1 96.46(11) 4_565 4_565 ?
C31 Tl1 O1 92.83(11) 4_565 4_565 ?
C31 Tl1 O1 9.13(11) . 4_565 ?
O1 Tl1 O1 84.23(10) . 4_565 ?
C32 Tl1 N1 101.16(10) . . ?
C32 Tl1 N1 130.39(11) 4_565 . ?
C31 Tl1 N1 64.52(10) 4_565 . ?
C31 Tl1 N1 98.00(11) . . ?
O1 Tl1 N1 68.90(7) . . ?
O1 Tl1 N1 97.70(7) 4_565 . ?
C32 Tl1 N1 130.39(11) . 4_565 ?
C32 Tl1 N1 101.16(10) 4_565 4_565 ?
C31 Tl1 N1 98.00(11) 4_565 4_565 ?
C31 Tl1 N1 64.52(10) . 4_565 ?
O1 Tl1 N1 97.70(7) . 4_565 ?
O1 Tl1 N1 68.90(7) 4_565 4_565 ?
N1 Tl1 N1 43.23(10) . 4_565 ?
C32 Tl1 N2 91.83(11) . . ?
C32 Tl1 N2 67.64(10) 4_565 . ?
C31 Tl1 N2 126.60(10) 4_565 . ?
C31 Tl1 N2 94.56(10) . . ?
O1 Tl1 N2 131.80(7) . . ?
O1 Tl1 N2 102.60(7) 4_565 . ?
N1 Tl1 N2 62.91(7) . . ?
N1 Tl1 N2 45.44(7) 4_565 . ?
C32 Tl1 N2 67.64(10) . 4_565 ?
C32 Tl1 N2 91.83(11) 4_565 4_565 ?
C31 Tl1 N2 94.56(10) 4_565 4_565 ?
C31 Tl1 N2 126.60(10) . 4_565 ?
O1 Tl1 N2 102.60(7) . 4_565 ?
O1 Tl1 N2 131.80(7) 4_565 4_565 ?
N1 Tl1 N2 45.44(7) . 4_565 ?
N1 Tl1 N2 62.91(7) 4_565 4_565 ?
N2 Tl1 N2 39.05(10) . 4_565 ?
C1 O1 Tl1 118.67(16) . . ?
C7 N1 C6 126.7(2) . . ?
C7 N1 Tl1 118.16(17) . . ?
C6 N1 Tl1 113.14(15) . . ?
C9 N2 C11 124.5(2) . . ?
C9 N2 Tl1 115.98(18) . . ?
C11 N2 Tl1 119.50(15) . . ?
O1 C1 C2 121.4(2) . . ?
O1 C1 C6 121.2(2) . . ?
C2 C1 C6 117.3(2) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 C17 121.9(2) . . ?
C1 C2 C17 119.4(2) . . ?
C2 C3 C4 124.3(2) . . ?
C5 C4 C3 117.3(2) . . ?
C5 C4 C21 122.7(2) . . ?
C3 C4 C21 120.0(2) . . ?
C4 C5 C6 121.5(2) . . ?
N1 C6 C5 122.8(2) . . ?
N1 C6 C1 115.7(2) . . ?
C5 C6 C1 120.8(2) . . ?
N1 C7 C9 116.5(2) . . ?
N1 C7 C8 125.9(2) . . ?
C9 C7 C8 117.5(2) . . ?
N2 C9 C7 118.0(2) . . ?
N2 C9 C10 124.4(3) . . ?
C7 C9 C10 117.6(2) . . ?
C12 C11 C16 120.5(3) . . ?
C12 C11 N2 120.0(2) . . ?
C16 C11 N2 119.1(2) . . ?
C13 C12 C11 117.9(3) . . ?
C13 C12 C25 120.3(3) . . ?
C11 C12 C25 121.8(3) . . ?
C14 C13 C12 121.6(3) . . ?
C13 C14 C15 120.6(3) . . ?
C16 C15 C14 119.3(3) . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 C28 119.2(3) . . ?
C11 C16 C28 120.7(3) . . ?
C20 C17 C19 107.7(2) . . ?
C20 C17 C2 111.9(2) . . ?
C19 C17 C2 110.4(2) . . ?
C20 C17 C18 107.1(2) . . ?
C19 C17 C18 110.0(2) . . ?
C2 C17 C18 109.6(2) . . ?
C22 C21 C23 109.1(3) . . ?
C22 C21 C24 115.8(3) . . ?
C23 C21 C24 105.7(3) . . ?
C22 C21 C4 112.6(2) . . ?
C23 C21 C4 106.6(2) . . ?
C24 C21 C4 106.5(3) . . ?
C12 C25 C27 112.5(3) . . ?
C12 C25 C26 112.5(3) . . ?
C27 C25 C26 106.8(3) . . ?
C16 C28 C30 110.3(3) . . ?
C16 C28 C29 112.6(3) . . ?
C30 C28 C29 108.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.501
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.074
