# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Xiaojun Peng'
_publ_contact_author_email       PENGXJ@DLUT.EDU.CN

_publ_section_title              
;
A Fluorescent Chemodosimeter Specific for Cysteine:
Effective Discrimination of Cysteine from Homocysteine
;
loop_
_publ_author_name
'Xiaojun Peng'
'Jianjun Du'
'Jiangli Fan'
'Honglin Li'
'Shiguo Sun'
;
Pingping Sun
;
'Maozhong Tian'
'Jingyun Wang'

# Attachment 'D1.cif'

data_d1
_database_code_depnum_ccdc_archive 'CCDC 727935'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 N4 O3'
_chemical_formula_weight         468.54

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pnma '

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

_cell_length_a                   19.352(4)
_cell_length_b                   15.755(3)
_cell_length_c                   8.3951(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2559.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2496
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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       'phi and omega scans'
_diffrn_reflns_number            7957
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2289
_reflns_number_gt                1526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0820P)^2^+0.9738P] 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    'riding model'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2289
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
O1 O 0.38138(13) 0.2500 -0.2182(3) 0.0523(7) Uani 1 2 d S . .
O2 O 0.0746(2) 0.2500 -0.3498(5) 0.141(2) Uani 1 2 d S . .
O3 O 0.12633(12) 0.2500 0.2738(3) 0.0414(6) Uani 1 2 d S . .
N1 N 0.27958(14) 0.2500 -0.0752(3) 0.0347(7) Uani 1 2 d S . .
N2 N 0.23984(16) 0.2500 -0.2062(3) 0.0436(8) Uani 1 2 d S . .
N3 N 0.10001(15) -0.04912(16) 0.2276(4) 0.0776(9) Uani 1 1 d . . .
H3A H 0.1170 -0.0964 0.1946 0.093 Uiso 1 1 calc R . .
C1 C 0.32448(16) 0.2500 0.1780(4) 0.0314(7) Uani 1 2 d S . .
C2 C 0.33722(18) 0.2500 0.3401(4) 0.0359(8) Uani 1 2 d S . .
H2B H 0.3009 0.2500 0.4127 0.043 Uiso 1 2 calc SR . .
C3 C 0.40479(18) 0.2500 0.3918(4) 0.0424(9) Uani 1 2 d S . .
H3B H 0.4140 0.2500 0.5005 0.051 Uiso 1 2 calc SR . .
C4 C 0.4592(2) 0.2500 0.2844(4) 0.0493(10) Uani 1 2 d S . .
H4A H 0.5044 0.2500 0.3221 0.059 Uiso 1 2 calc SR . .
C5 C 0.44715(19) 0.2500 0.1217(4) 0.0440(9) Uani 1 2 d S . .
H5A H 0.4834 0.2500 0.0491 0.053 Uiso 1 2 calc SR . .
C6 C 0.37912(17) 0.2500 0.0715(4) 0.0347(8) Uani 1 2 d S . .
C7 C 0.35097(18) 0.2500 -0.0909(4) 0.0369(8) Uani 1 2 d S . .
C8 C 0.1742(2) 0.2500 -0.1950(4) 0.0521(10) Uani 1 2 d S . .
H8A H 0.1519 0.2500 -0.0968 0.062 Uiso 1 2 calc SR . .
C9 C 0.1363(3) 0.2500 -0.3424(6) 0.0875(18) Uani 1 2 d S . .
H9A H 0.1612 0.2500 -0.4372 0.105 Uiso 1 2 calc SR . .
C10 C 0.25536(16) 0.2500 0.0953(3) 0.0305(7) Uani 1 2 d S . .
C11 C 0.21393(12) 0.17151(14) 0.1311(3) 0.0320(6) Uani 1 1 d . . .
C12 C 0.23492(13) 0.09103(15) 0.0798(3) 0.0425(6) Uani 1 1 d . . .
H12A H 0.2759 0.0869 0.0227 0.051 Uiso 1 1 calc R . .
C13 C 0.19874(15) 0.01836(16) 0.1087(3) 0.0468(7) Uani 1 1 d . . .
C14 C 0.13699(14) 0.02378(16) 0.1973(3) 0.0470(7) Uani 1 1 d . . .
C15 C 0.11531(13) 0.10273(16) 0.2514(3) 0.0426(6) Uani 1 1 d . . .
H15A H 0.0750 0.1073 0.3110 0.051 Uiso 1 1 calc R . .
C16 C 0.15366(12) 0.17446(14) 0.2169(2) 0.0326(5) Uani 1 1 d . . .
C17 C 0.22295(19) -0.06520(19) 0.0435(5) 0.0849(12) Uani 1 1 d . . .
H17A H 0.2657 -0.0572 -0.0127 0.127 Uiso 1 1 calc R . .
H17B H 0.1888 -0.0875 -0.0280 0.127 Uiso 1 1 calc R . .
H17C H 0.2299 -0.1044 0.1296 0.127 Uiso 1 1 calc R . .
C18 C 0.03506(19) -0.0519(2) 0.3102(5) 0.0818(11) Uani 1 1 d . . .
H18A H 0.0370 -0.0124 0.3989 0.098 Uiso 1 1 calc R . .
H18B H 0.0289 -0.1084 0.3541 0.098 Uiso 1 1 calc R . .
C19 C -0.0247(3) -0.0316(4) 0.2138(7) 0.148(2) Uani 1 1 d . . .
H19A H -0.0656 -0.0345 0.2782 0.222 Uiso 1 1 calc R . .
H19B H -0.0282 -0.0715 0.1278 0.222 Uiso 1 1 calc R . .
H19C H -0.0198 0.0247 0.1714 0.222 Uiso 1 1 calc 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
O1 0.0551(17) 0.0697(19) 0.0321(13) 0.000 0.0133(12) 0.000
O2 0.062(3) 0.283(7) 0.078(2) 0.000 -0.031(2) 0.000
O3 0.0409(14) 0.0348(13) 0.0487(14) 0.000 0.0139(11) 0.000
N1 0.0381(18) 0.0403(17) 0.0256(13) 0.000 -0.0006(12) 0.000
N2 0.048(2) 0.0494(19) 0.0329(15) 0.000 -0.0090(14) 0.000
N3 0.088(2) 0.0404(14) 0.105(2) -0.0057(14) 0.0414(17) -0.0191(14)
C1 0.0343(19) 0.0259(17) 0.0340(16) 0.000 0.0022(14) 0.000
C2 0.040(2) 0.0389(19) 0.0286(16) 0.000 0.0072(15) 0.000
C3 0.045(2) 0.052(2) 0.0306(17) 0.000 -0.0018(16) 0.000
C4 0.036(2) 0.065(3) 0.046(2) 0.000 -0.0070(17) 0.000
C5 0.034(2) 0.053(2) 0.045(2) 0.000 0.0093(16) 0.000
C6 0.035(2) 0.038(2) 0.0315(16) 0.000 0.0051(14) 0.000
C7 0.043(2) 0.0333(19) 0.0341(18) 0.000 0.0063(16) 0.000
C8 0.048(3) 0.069(3) 0.039(2) 0.000 -0.0092(18) 0.000
C9 0.057(3) 0.151(6) 0.054(3) 0.000 -0.018(2) 0.000
C10 0.0329(19) 0.0322(18) 0.0263(15) 0.000 0.0038(13) 0.000
C11 0.0330(14) 0.0312(13) 0.0318(11) -0.0011(9) -0.0009(10) -0.0007(10)
C12 0.0447(16) 0.0386(15) 0.0441(13) -0.0007(11) 0.0101(12) -0.0006(12)
C13 0.0605(18) 0.0309(14) 0.0491(14) -0.0035(11) 0.0105(13) -0.0023(13)
C14 0.0595(18) 0.0363(15) 0.0452(14) 0.0001(11) 0.0063(13) -0.0078(13)
C15 0.0429(16) 0.0415(15) 0.0434(13) 0.0004(11) 0.0109(11) -0.0027(12)
C16 0.0347(14) 0.0310(13) 0.0322(11) -0.0009(9) 0.0000(10) 0.0013(10)
C17 0.111(3) 0.0403(18) 0.104(3) -0.0079(17) 0.048(2) -0.0021(18)
C18 0.090(3) 0.056(2) 0.099(3) 0.0033(19) 0.029(2) -0.0261(19)
C19 0.108(4) 0.178(6) 0.159(5) 0.045(4) -0.009(4) -0.023(4)

_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 C7 1.220(4) . ?
O2 C9 1.196(5) . ?
O3 C16 1.387(2) . ?
O3 C16 1.387(2) 7_565 ?
N1 N2 1.342(4) . ?
N1 C7 1.388(4) . ?
N1 C10 1.506(4) . ?
N2 C8 1.274(5) . ?
N3 C14 1.377(3) . ?
N3 C18 1.436(4) . ?
N3 H3A 0.8600 . ?
C1 C2 1.383(4) . ?
C1 C6 1.384(4) . ?
C1 C10 1.507(4) . ?
C2 C3 1.378(5) . ?
C2 H2B 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3B 0.9300 . ?
C4 C5 1.386(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.468(4) . ?
C8 C9 1.438(6) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.504(3) . ?
C10 C11 1.504(3) 7_565 ?
C11 C16 1.372(3) . ?
C11 C12 1.399(3) . ?
C12 C13 1.364(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.410(4) . ?
C13 C17 1.501(4) . ?
C14 C15 1.389(4) . ?
C15 C16 1.382(3) . ?
C15 H15A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.447(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C16 O3 C16 118.2(2) . 7_565 ?
N2 N1 C7 119.5(3) . . ?
N2 N1 C10 126.9(3) . . ?
C7 N1 C10 113.6(2) . . ?
C8 N2 N1 120.8(3) . . ?
C14 N3 C18 124.7(3) . . ?
C14 N3 H3A 117.6 . . ?
C18 N3 H3A 117.6 . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 C10 127.7(3) . . ?
C6 C1 C10 112.4(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2B 120.7 . . ?
C1 C2 H2B 120.7 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3B 119.5 . . ?
C4 C3 H3B 119.5 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 H5A 121.3 . . ?
C4 C5 H5A 121.3 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 C7 129.5(3) . . ?
C1 C6 C7 108.4(3) . . ?
O1 C7 N1 124.3(3) . . ?
O1 C7 C6 129.4(3) . . ?
N1 C7 C6 106.3(3) . . ?
N2 C8 C9 116.4(4) . . ?
N2 C8 H8A 121.8 . . ?
C9 C8 H8A 121.8 . . ?
O2 C9 C8 123.7(5) . . ?
O2 C9 H9A 118.2 . . ?
C8 C9 H9A 118.2 . . ?
C11 C10 C11 110.6(3) . 7_565 ?
C11 C10 N1 110.87(16) . . ?
C11 C10 N1 110.87(16) 7_565 . ?
C11 C10 C1 112.38(16) . . ?
C11 C10 C1 112.38(16) 7_565 . ?
N1 C10 C1 99.3(2) . . ?
C16 C11 C12 116.0(2) . . ?
C16 C11 C10 122.0(2) . . ?
C12 C11 C10 121.9(2) . . ?
C13 C12 C11 123.8(2) . . ?
C13 C12 H12A 118.1 . . ?
C11 C12 H12A 118.1 . . ?
C12 C13 C14 118.6(2) . . ?
C12 C13 C17 120.7(2) . . ?
C14 C13 C17 120.7(2) . . ?
N3 C14 C15 122.0(2) . . ?
N3 C14 C13 119.2(2) . . ?
C15 C14 C13 118.9(2) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C11 C16 C15 122.6(2) . . ?
C11 C16 O3 122.3(2) . . ?
C15 C16 O3 115.1(2) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 115.0(4) . . ?
N3 C18 H18A 108.5 . . ?
C19 C18 H18A 108.5 . . ?
N3 C18 H18B 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.046