# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Tao, Xutang'
_publ_contact_author_email       txt@sdu.edu.cn

_publ_section_title              
;
Aggregation-Induced Emission Enhancement of Polycyclic
Aromatic Alkaloids Derivatives and the Crucial Role of
Excited-State Proton- Transfer
;
loop_
_publ_author_name
'Tao He'
'Xutang Tao'
'Jia Yang'
'Dan Guo'
'Haibing Xia'
'Jiong Jia'
;
Minhua Jiang
;

# Attachment '- x1.cif'

data_x1
_database_code_depnum_ccdc_archive 'CCDC 799380'
#TrackingRef '- x1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C88 H64 N8 O12'
_chemical_formula_sum            'C88 H64 N8 O12'
_chemical_formula_weight         1425.47

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'

_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                   10.898(3)
_cell_length_b                   22.742(7)
_cell_length_c                   7.482(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.178(4)
_cell_angle_gamma                90.00
_cell_volume                     1780.8(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    949
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      17.89

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19956
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         26.73
_reflns_number_total             3798
_reflns_number_gt                1508
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker,2005)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker,2005)'
_computing_data_reduction        'APEX2 Software Suite (Bruker,2005)'
_computing_structure_solution    'SIR97 (Altomare,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'WINGX (Farrugia,1999)'

_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^)+(0.1270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3798
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1929
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2666
_refine_ls_wR_factor_gt          0.2020
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.1996(6) 0.5489(2) 0.2428(8) 0.0825(17) Uani 1 1 d . . .
H1A H 0.2899 0.5554 0.2690 0.124 Uiso 1 1 calc R . .
H1B H 0.1624 0.5795 0.2992 0.124 Uiso 1 1 calc R . .
H1C H 0.1616 0.5493 0.1106 0.124 Uiso 1 1 calc R . .
C5 C -0.1810(6) 0.4954(2) 0.2204(7) 0.0742(15) Uani 1 1 d . . .
H5A H -0.2456 0.5230 0.1787 0.089 Uiso 1 1 calc R . .
C17 C 0.6746(5) 0.2578(2) 0.8924(6) 0.0621(13) Uani 1 1 d . . .
H17A H 0.7539 0.2445 0.9631 0.075 Uiso 1 1 calc R . .
C4 C -0.0554(5) 0.5104(2) 0.2359(6) 0.0607(13) Uani 1 1 d . . .
H4A H -0.0365 0.5482 0.2043 0.073 Uiso 1 1 calc R . .
C6 C -0.2103(5) 0.4399(2) 0.2666(6) 0.0635(13) Uani 1 1 d . . .
H6A H -0.2946 0.4296 0.2564 0.076 Uiso 1 1 calc R . .
C18 C 0.6528(4) 0.3174(2) 0.8679(6) 0.0634(13) Uani 1 1 d . . .
H18A H 0.7180 0.3437 0.9208 0.076 Uiso 1 1 calc R . .
C7 C -0.1131(4) 0.3989(2) 0.3287(6) 0.0569(12) Uani 1 1 d . . .
H7A H -0.1329 0.3616 0.3630 0.068 Uiso 1 1 calc R . .
C2 C 0.1758(5) 0.4902(2) 0.3206(7) 0.0610(13) Uani 1 1 d . . .
C16 C 0.5814(4) 0.2185(2) 0.8145(6) 0.0551(12) Uani 1 1 d . . .
H16A H 0.5987 0.1785 0.8315 0.066 Uiso 1 1 calc R . .
C20 C 0.4365(4) 0.29793(19) 0.6854(5) 0.0460(11) Uani 1 1 d . . .
C8 C 0.0132(4) 0.41267(18) 0.3407(5) 0.0466(11) Uani 1 1 d . . .
C22 C 0.3807(5) 0.13257(19) 0.6366(7) 0.0664(14) Uani 1 1 d . . .
H22C H 0.3135 0.1127 0.5463 0.100 Uiso 1 1 calc R . .
H22B H 0.3821 0.1195 0.7592 0.100 Uiso 1 1 calc R . .
H22A H 0.4612 0.1238 0.6139 0.100 Uiso 1 1 calc R . .
C3 C 0.0427(4) 0.47010(18) 0.2975(6) 0.0498(11) Uani 1 1 d . . .
C19 C 0.5359(4) 0.3381(2) 0.7663(6) 0.0582(13) Uani 1 1 d . . .
H19A H 0.5220 0.3784 0.7506 0.070 Uiso 1 1 calc R . .
C14 C 0.3579(4) 0.19714(18) 0.6219(5) 0.0460(10) Uani 1 1 d . . .
C13 C 0.2430(4) 0.22183(17) 0.5232(5) 0.0429(10) Uani 1 1 d . . .
C15 C 0.4584(4) 0.23664(18) 0.7080(5) 0.0434(10) Uani 1 1 d . . .
C11 C 0.0133(4) 0.21628(19) 0.2991(6) 0.0486(11) Uani 1 1 d . . .
C12 C 0.1282(4) 0.18625(19) 0.4344(6) 0.0493(11) Uani 1 1 d . . .
C10 C 0.0102(4) 0.27825(18) 0.2937(6) 0.0497(11) Uani 1 1 d . . .
H10A H -0.0608 0.2969 0.2161 0.060 Uiso 1 1 calc R . .
C21 C 0.2298(4) 0.28379(18) 0.5090(5) 0.0411(10) Uani 1 1 d . . .
C9 C 0.1085(4) 0.31216(18) 0.3990(5) 0.0425(10) Uani 1 1 d . . .
N1 N 0.1108(3) 0.37142(14) 0.4085(5) 0.0481(9) Uani 1 1 d . . .
H1D H 0.1839 0.3863 0.4651 0.058 Uiso 1 1 calc R . .
N2 N 0.3215(3) 0.32114(14) 0.5863(5) 0.0457(9) Uani 1 1 d . . .
O1 O 0.2682(3) 0.46034(14) 0.4047(5) 0.0723(10) Uani 1 1 d . . .
O2 O 0.1165(3) 0.13423(14) 0.4685(5) 0.0810(11) Uani 1 1 d . . .
O3 O -0.0711(3) 0.18480(14) 0.2031(4) 0.0690(10) Uani 1 1 d . . .
O4 O 0.5114(11) 0.4943(7) 0.300(2) 0.548(17) Uani 1 1 d . . .
H24 H 0.5006 0.4580 0.2731 0.822 Uiso 1 1 d R . .
H23 H 0.5849 0.4982 0.3770 0.822 Uiso 1 1 d R . .

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
C1 0.106(5) 0.054(3) 0.097(4) 0.009(3) 0.044(4) -0.014(3)
C5 0.077(4) 0.069(4) 0.069(4) 0.006(3) 0.008(3) 0.023(3)
C17 0.047(3) 0.079(4) 0.054(3) 0.004(3) 0.003(2) 0.003(3)
C4 0.080(4) 0.048(3) 0.056(3) 0.008(2) 0.023(3) 0.008(3)
C6 0.060(3) 0.066(3) 0.062(3) 0.002(3) 0.012(3) 0.016(3)
C18 0.053(3) 0.068(3) 0.063(3) 0.002(3) 0.006(2) -0.005(3)
C7 0.056(3) 0.051(3) 0.063(3) 0.005(2) 0.015(2) 0.002(2)
C2 0.081(4) 0.045(3) 0.065(3) -0.011(2) 0.033(3) 0.000(3)
C16 0.052(3) 0.059(3) 0.051(3) 0.008(2) 0.010(2) 0.011(2)
C20 0.044(3) 0.050(3) 0.044(2) -0.002(2) 0.012(2) 0.002(2)
C8 0.050(3) 0.048(3) 0.041(2) -0.0008(19) 0.011(2) 0.003(2)
C22 0.072(3) 0.045(3) 0.080(4) 0.003(2) 0.017(3) 0.008(2)
C3 0.057(3) 0.044(3) 0.048(3) 0.001(2) 0.014(2) 0.002(2)
C19 0.055(3) 0.051(3) 0.063(3) -0.002(2) 0.007(2) -0.010(2)
C14 0.053(3) 0.043(2) 0.044(2) 0.002(2) 0.016(2) 0.003(2)
C13 0.049(3) 0.035(2) 0.046(2) -0.0048(18) 0.016(2) -0.0040(19)
C15 0.046(3) 0.048(3) 0.038(2) -0.0001(19) 0.0145(19) 0.001(2)
C11 0.046(3) 0.050(3) 0.049(3) -0.006(2) 0.013(2) -0.009(2)
C12 0.058(3) 0.039(3) 0.053(3) -0.007(2) 0.018(2) -0.003(2)
C10 0.049(3) 0.048(3) 0.050(3) 0.000(2) 0.009(2) 0.003(2)
C21 0.044(2) 0.045(2) 0.036(2) -0.0001(19) 0.0144(19) -0.002(2)
C9 0.043(2) 0.042(2) 0.042(2) -0.0007(19) 0.0135(19) -0.003(2)
N1 0.047(2) 0.038(2) 0.056(2) 0.0023(17) 0.0101(17) 0.0015(16)
N2 0.042(2) 0.043(2) 0.048(2) 0.0028(17) 0.0066(16) -0.0022(17)
O1 0.061(2) 0.051(2) 0.106(3) -0.0038(19) 0.025(2) -0.0039(17)
O2 0.084(3) 0.044(2) 0.101(3) -0.0017(19) 0.002(2) -0.0133(18)
O3 0.060(2) 0.058(2) 0.079(2) -0.0090(17) 0.0021(18) -0.0171(17)
O4 0.255(13) 0.47(2) 0.94(5) -0.34(3) 0.20(2) -0.099(13)

_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 C2 1.509(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C5 C6 1.370(7) . ?
C5 C4 1.384(7) . ?
C5 H5A 0.9300 . ?
C17 C16 1.358(6) . ?
C17 C18 1.378(6) . ?
C17 H17A 0.9300 . ?
C4 C3 1.386(6) . ?
C4 H4A 0.9300 . ?
C6 C7 1.389(6) . ?
C6 H6A 0.9300 . ?
C18 C19 1.373(6) . ?
C18 H18A 0.9300 . ?
C7 C8 1.389(6) . ?
C7 H7A 0.9300 . ?
C2 O1 1.232(5) . ?
C2 C3 1.485(6) . ?
C16 C15 1.416(5) . ?
C16 H16A 0.9300 . ?
C20 N2 1.372(5) . ?
C20 C15 1.416(6) . ?
C20 C19 1.418(6) . ?
C8 N1 1.403(5) . ?
C8 C3 1.404(6) . ?
C22 C14 1.488(6) . ?
C22 H22C 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22A 0.9600 . ?
C19 H19A 0.9300 . ?
C14 C13 1.383(5) . ?
C14 C15 1.425(5) . ?
C13 C21 1.417(5) . ?
C13 C12 1.483(5) . ?
C11 O3 1.227(5) . ?
C11 C10 1.410(6) . ?
C11 C12 1.534(6) . ?
C12 O2 1.224(5) . ?
C10 C9 1.375(5) . ?
C10 H10A 0.9300 . ?
C21 N2 1.316(5) . ?
C21 C9 1.495(5) . ?
C9 N1 1.349(5) . ?
N1 H1D 0.8600 . ?
O4 H24 0.8503 . ?
O4 H23 0.8500 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C16 C17 C18 120.7(5) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
C8 C7 C6 121.3(5) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
O1 C2 C3 121.6(4) . . ?
O1 C2 C1 118.8(5) . . ?
C3 C2 C1 119.7(5) . . ?
C17 C16 C15 121.8(4) . . ?
C17 C16 H16A 119.1 . . ?
C15 C16 H16A 119.1 . . ?
N2 C20 C15 122.8(4) . . ?
N2 C20 C19 117.2(4) . . ?
C15 C20 C19 120.0(4) . . ?
C7 C8 N1 120.7(4) . . ?
C7 C8 C3 118.7(4) . . ?
N1 C8 C3 120.4(4) . . ?
C14 C22 H22C 109.5 . . ?
C14 C22 H22B 109.5 . . ?
H22C C22 H22B 109.5 . . ?
C14 C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
C4 C3 C8 119.2(4) . . ?
C4 C3 C2 118.3(4) . . ?
C8 C3 C2 122.6(4) . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C13 C14 C15 116.9(4) . . ?
C13 C14 C22 123.2(4) . . ?
C15 C14 C22 119.8(4) . . ?
C14 C13 C21 120.1(4) . . ?
C14 C13 C12 122.9(4) . . ?
C21 C13 C12 117.0(4) . . ?
C16 C15 C20 117.1(4) . . ?
C16 C15 C14 124.0(4) . . ?
C20 C15 C14 118.9(4) . . ?
O3 C11 C10 123.9(4) . . ?
O3 C11 C12 117.9(4) . . ?
C10 C11 C12 118.2(4) . . ?
O2 C12 C13 123.9(4) . . ?
O2 C12 C11 117.1(4) . . ?
C13 C12 C11 119.0(4) . . ?
C9 C10 C11 122.4(4) . . ?
C9 C10 H10A 118.8 . . ?
C11 C10 H10A 118.8 . . ?
N2 C21 C13 124.0(4) . . ?
N2 C21 C9 114.2(4) . . ?
C13 C21 C9 121.7(3) . . ?
N1 C9 C10 126.2(4) . . ?
N1 C9 C21 113.6(3) . . ?
C10 C9 C21 120.1(4) . . ?
C9 N1 C8 130.3(4) . . ?
C9 N1 H1D 114.8 . . ?
C8 N1 H1D 114.8 . . ?
C21 N2 C20 117.2(4) . . ?
H24 O4 H23 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H23 O1 0.85 2.16 2.958(14) 156.4 3_666
N1 H1D O1 0.86 2.03 2.657(4) 129.1 .
N1 H1D N2 0.86 2.12 2.578(5) 112.5 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.069