# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_lamb
_database_code_depnum_ccdc_archive 'CCDC 794601'
#TrackingRef 'bTbKphaseToluene.cif'


_audit_creation_date             2010-04-21T11:35:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C13.83 H22.67 N1 O3'
_chemical_formula_sum            'C13.83 H22.67 N O3'
_chemical_formula_weight         251
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3 c'
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_Int_Tables_number      167
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'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-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'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+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-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+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-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+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   25.1040(4)
_cell_length_b                   25.1040(4)
_cell_length_c                   30.000(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     16373.3(17)
_cell_formula_units_Z            36
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    28637
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.96
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    0.916
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4920
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
#_diffrn_standards_number none
#0.0000
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_number            28637
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_reflns_number_total             3318
_reflns_number_gt                2403
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1504P)^2^+21.9740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3318
_refine_ls_number_parameters     192
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.081
_refine_ls_wR_factor_ref         0.2575
_refine_ls_wR_factor_gt          0.2304
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.27311(11) 0.22184(9) 0.01353(7) 0.0700(7) Uani 1 1 d . . .
O2 O 0.27844(8) 0.04642(8) 0.11776(5) 0.0499(5) Uani 1 1 d . . .
O3 O 0.35344(7) 0.10314(7) 0.06474(5) 0.0459(5) Uani 1 1 d . . .
N1 N 0.27548(11) 0.18007(10) 0.03700(7) 0.0528(6) Uani 1 1 d . . .
C1 C 0.29650(12) 0.09123(11) 0.08316(8) 0.0448(6) Uani 1 1 d . . .
C2 C 0.24503(12) 0.07106(11) 0.04893(8) 0.0466(6) Uani 1 1 d . . .
H2A H 0.2068 0.0584 0.0647 0.056 Uiso 1 1 calc R . .
H2B H 0.2408 0.0354 0.0332 0.056 Uiso 1 1 calc R . .
C3 C 0.25408(13) 0.11989(12) 0.01462(9) 0.0510(7) Uani 1 1 d . . .
C4 C 0.31691(15) 0.20261(12) 0.07658(9) 0.0582(8) Uani 1 1 d . . .
C5 C 0.30624(14) 0.14888(13) 0.10615(9) 0.0557(7) Uani 1 1 d . . .
H5A H 0.3413 0.1629 0.1259 0.067 Uiso 1 1 calc R . .
H5B H 0.2705 0.1381 0.1246 0.067 Uiso 1 1 calc R . .
C6 C 0.29979(17) 0.12793(15) -0.02179(9) 0.0682(9) Uani 1 1 d . . .
H6A H 0.3042 0.1595 -0.0421 0.102 Uiso 1 1 calc R . .
H6B H 0.285 0.0899 -0.0377 0.102 Uiso 1 1 calc R . .
H6C H 0.3389 0.1395 -0.0086 0.102 Uiso 1 1 calc R . .
C7 C 0.19162(16) 0.10095(15) -0.00638(12) 0.0729(10) Uani 1 1 d . . .
H7A H 0.164 0.1 0.0162 0.109 Uiso 1 1 calc R . .
H7B H 0.1751 0.0608 -0.0195 0.109 Uiso 1 1 calc R . .
H7C H 0.1966 0.1301 -0.029 0.109 Uiso 1 1 calc R . .
C8 C 0.38337(16) 0.23975(14) 0.06028(12) 0.0759(10) Uani 1 1 d . . .
H8A H 0.395 0.2127 0.0463 0.114 Uiso 1 1 calc R . .
H8B H 0.41 0.2598 0.0852 0.114 Uiso 1 1 calc R . .
H8C H 0.3868 0.2701 0.0392 0.114 Uiso 1 1 calc R . .
C9 C 0.3001(2) 0.24439(16) 0.10315(13) 0.0860(11) Uani 1 1 d . . .
H9A H 0.3041 0.2771 0.0844 0.129 Uiso 1 1 calc R . .
H9B H 0.3272 0.2614 0.1282 0.129 Uiso 1 1 calc R . .
H9C H 0.2584 0.2208 0.1135 0.129 Uiso 1 1 calc R . .
C10 C 0.35279(12) 0.04953(12) 0.04760(8) 0.0456(6) Uani 1 1 d . . .
H10A H 0.3935 0.0607 0.0368 0.055 Uiso 1 1 calc R . .
H10B H 0.3245 0.0333 0.0227 0.055 Uiso 1 1 calc R . .
C11 C 0.33336(14) 0.00002(14) 0.0833 0.0432(8) Uani 1 2 d S . .
C12 C 0.27378(12) -0.01014(11) 0.10371(9) 0.0479(7) Uani 1 1 d . . .
H12A H 0.241 -0.0298 0.082 0.058 Uiso 1 1 calc R . .
H12B H 0.2634 -0.0375 0.1291 0.058 Uiso 1 1 calc R . .
C13 C 0.5980(5) 0.1935(5) 0.0018(5) 0.168(10) Uani 0.33 1 d PG . .
C14 C 0.5449(6) 0.1732(4) 0.0269(4) 0.124(6) Uani 0.33 1 d PGD . .
H14 H 0.5402 0.1522 0.0535 0.149 Uiso 0.33 1 calc PR . .
C15 C 0.4987(5) 0.1842(5) 0.0124(5) 0.136(6) Uani 0.33 1 d PGU . .
H15 H 0.4631 0.1706 0.0292 0.163 Uiso 0.33 1 calc PR . .
C16 C 0.5057(6) 0.2155(7) -0.0274(5) 0.188(8) Uani 0.33 1 d PGU . .
H16 H 0.4748 0.2229 -0.0371 0.225 Uiso 0.33 1 calc PR . .
C17 C 0.5589(8) 0.2358(7) -0.0525(3) 0.217(13) Uani 0.33 1 d PGU . .
H17 H 0.5636 0.2568 -0.0791 0.26 Uiso 0.33 1 calc PR . .
C18 C 0.6051(6) 0.2248(6) -0.0379(4) 0.159(8) Uani 0.33 1 d PGDU . .
H18 H 0.6406 0.2384 -0.0548 0.19 Uiso 0.33 1 calc PR . .
C19 C 0.6513(9) 0.1826(10) 0.0154(7) 0.215(14) Uani 0.33 1 d PD . .
H19A H 0.6706 0.2056 0.0419 0.322 Uiso 0.33 1 calc PR . .
H19B H 0.6809 0.1958 -0.0083 0.322 Uiso 0.33 1 calc PR . .
H19C H 0.6353 0.1396 0.021 0.322 Uiso 0.33 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0876(15) 0.0512(12) 0.0753(14) 0.0119(10) -0.0143(11) 0.0378(11)
O2 0.0636(11) 0.0523(10) 0.0407(9) 0.0113(8) 0.0065(8) 0.0343(9)
O3 0.0483(10) 0.0438(9) 0.0434(9) 0.0062(7) 0.0004(7) 0.0214(8)
N1 0.0669(15) 0.0417(12) 0.0525(13) 0.0038(9) -0.0078(11) 0.0292(11)
C1 0.0534(14) 0.0452(13) 0.0376(12) 0.0069(10) 0.0024(11) 0.0260(12)
C2 0.0499(14) 0.0415(13) 0.0489(14) 0.0014(10) -0.0028(11) 0.0232(12)
C3 0.0626(16) 0.0441(14) 0.0482(14) -0.0010(11) -0.0118(12) 0.0280(13)
C4 0.077(2) 0.0444(14) 0.0516(15) -0.0056(12) -0.0148(14) 0.0294(14)
C5 0.0740(19) 0.0549(16) 0.0425(14) -0.0050(12) -0.0074(12) 0.0354(15)
C6 0.098(2) 0.0692(19) 0.0446(15) 0.0065(14) 0.0021(15) 0.0472(18)
C7 0.079(2) 0.0569(18) 0.082(2) -0.0022(16) -0.0325(17) 0.0331(16)
C8 0.073(2) 0.0519(17) 0.081(2) 0.0053(16) -0.0200(17) 0.0156(16)
C9 0.133(3) 0.062(2) 0.075(2) -0.0158(17) -0.017(2) 0.058(2)
C10 0.0476(14) 0.0510(14) 0.0408(13) 0.0038(11) -0.0001(10) 0.0264(12)
C11 0.0447(14) 0.0447(14) 0.0421(17) 0.0034(7) -0.0034(7) 0.0237(16)
C12 0.0488(14) 0.0448(14) 0.0519(14) 0.0106(11) 0.0025(11) 0.0246(12)
C13 0.144(17) 0.074(10) 0.26(3) -0.090(15) -0.031(19) 0.037(11)
C14 0.104(11) 0.065(7) 0.177(16) -0.011(8) 0.046(11) 0.021(7)
C15 0.080(9) 0.066(8) 0.228(18) -0.006(9) 0.039(11) 0.012(7)
C16 0.185(17) 0.123(16) 0.21(2) -0.003(13) 0.047(16) 0.045(15)
C17 0.21(2) 0.34(3) 0.075(10) -0.037(14) -0.001(11) 0.12(2)
C18 0.170(15) 0.107(13) 0.143(16) -0.014(11) 0.065(13) 0.027(12)
C19 0.26(3) 0.138(17) 0.138(16) -0.012(14) 0.01(2) 0.02(2)


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
O1 N1 1.289(3) . ?
O2 C1 1.428(3) . ?
O2 C12 1.429(3) . ?
O3 C1 1.418(3) . ?
O3 C10 1.433(3) . ?
N1 C3 1.487(3) . ?
N1 C4 1.491(3) . ?
C1 C5 1.509(4) . ?
C1 C2 1.525(3) . ?
C2 C3 1.528(3) . ?
C3 C6 1.523(4) . ?
C3 C7 1.528(4) . ?
C4 C5 1.522(4) . ?
C4 C8 1.528(5) . ?
C4 C9 1.535(4) . ?
C10 C11 1.525(3) . ?
C11 C12 1.515(3) . ?
C11 C12 1.515(3) 18_544 ?
C11 C10 1.525(3) 18_544 ?
C13 C14 1.39 . ?
C13 C18 1.39 . ?
C13 C19 1.546(15) . ?
C14 C15 1.39 . ?
C15 C16 1.39 . ?
C16 C17 1.39 . ?
C17 C18 1.39 . ?

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
C1 O2 C12 113.86(18) . . ?
C1 O3 C10 113.87(18) . . ?
O1 N1 C3 116.1(2) . . ?
O1 N1 C4 115.7(2) . . ?
C3 N1 C4 125.1(2) . . ?
O3 C1 O2 109.82(19) . . ?
O3 C1 C5 108.2(2) . . ?
O2 C1 C5 105.00(19) . . ?
O3 C1 C2 113.89(19) . . ?
O2 C1 C2 110.2(2) . . ?
C5 C1 C2 109.3(2) . . ?
C1 C2 C3 115.2(2) . . ?
N1 C3 C6 108.9(2) . . ?
N1 C3 C2 110.1(2) . . ?
C6 C3 C2 112.9(2) . . ?
N1 C3 C7 107.2(2) . . ?
C6 C3 C7 109.5(3) . . ?
C2 C3 C7 108.1(2) . . ?
N1 C4 C5 110.3(2) . . ?
N1 C4 C8 108.6(2) . . ?
C5 C4 C8 112.4(3) . . ?
N1 C4 C9 107.1(2) . . ?
C5 C4 C9 108.4(3) . . ?
C8 C4 C9 109.8(3) . . ?
C1 C5 C4 117.1(2) . . ?
O3 C10 C11 111.23(17) . . ?
C12 C11 C12 109.4(3) . 18_544 ?
C12 C11 C10 110.40(14) . 18_544 ?
C12 C11 C10 107.91(13) 18_544 18_544 ?
C12 C11 C10 107.91(13) . . ?
C12 C11 C10 110.39(14) 18_544 . ?
C10 C11 C10 110.9(3) 18_544 . ?
O2 C12 C11 111.6(2) . . ?
C14 C13 C18 120 . . ?
C14 C13 C19 123.2(9) . . ?
C18 C13 C19 116.8(9) . . ?
C15 C14 C13 120 . . ?
C14 C15 C16 120 . . ?
C15 C16 C17 120 . . ?
C18 C17 C16 120 . . ?
C17 C18 C13 120 . . ?

# END of CIF