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


data_global
_journal_name_full               'The Analyst'
_journal_coden_cambridge         0091
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'An-Tai Wu'
_publ_contact_author_name        'An-Tai Wu'
_publ_contact_author_email       anantaitai@yahoo.com.tw

data_qwe
_database_code_depnum_ccdc_archive 'CCDC 894614'
#TrackingRef 'qwe.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24

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   C2/c

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

_cell_length_a                   15.982(16)
_cell_length_b                   4.957(5)
_cell_length_c                   27.97(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.77(5)
_cell_angle_gamma                90.00
_cell_volume                     2142(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12599
_diffrn_reflns_av_R_equivalents  0.2121
_diffrn_reflns_av_sigmaI/netI    0.2110
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         28.29
_reflns_number_total             2583
_reflns_number_gt                705
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0891P)^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    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0082(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2583
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2329
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2033
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   0.728
_refine_ls_restrained_S_all      0.728
_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 0.87144(15) 0.6942(5) 1.04965(11) 0.0622(8) Uani 1 1 d . . .
H1 H 0.9141 0.6069 1.0639 0.093 Uiso 1 1 calc R . .
O2 O 0.97400(17) 0.5428(5) 0.91402(10) 0.0686(8) Uani 1 1 d . . .
N1 N 0.8639(2) 0.8106(6) 0.94662(11) 0.0583(9) Uani 1 1 d . . .
H1A H 0.9168 0.7842 0.9461 0.070 Uiso 1 1 calc R . .
C1 C 0.8981(3) 0.9415(7) 1.03325(15) 0.0622(11) Uani 1 1 d . . .
H1B H 0.9591 0.9313 1.0340 0.075 Uiso 1 1 calc R . .
H1C H 0.8908 1.0850 1.0554 0.075 Uiso 1 1 calc R . .
C2 C 0.8470(3) 1.0055(7) 0.98202(14) 0.0588(10) Uani 1 1 d . . .
H2A H 0.7858 1.0042 0.9808 0.071 Uiso 1 1 calc R . .
H2B H 0.8619 1.1848 0.9731 0.071 Uiso 1 1 calc R . .
C3 C 0.8047(2) 0.6747(7) 0.91602(14) 0.0524(10) Uani 1 1 d . . .
H3 H 0.7471 0.7098 0.9150 0.063 Uiso 1 1 calc R . .
C4 C 0.8230(2) 0.4749(7) 0.88393(13) 0.0495(9) Uani 1 1 d . . .
C5 C 0.7531(2) 0.3257(7) 0.85183(13) 0.0495(9) Uani 1 1 d . . .
C6 C 0.6651(2) 0.3662(8) 0.84861(16) 0.0649(11) Uani 1 1 d . . .
H6 H 0.6493 0.5010 0.8677 0.078 Uiso 1 1 calc R . .
C7 C 0.6021(3) 0.2162(9) 0.81867(18) 0.0789(13) Uani 1 1 d . . .
H7 H 0.5445 0.2477 0.8180 0.095 Uiso 1 1 calc R . .
C8 C 0.6231(3) 0.0159(9) 0.78911(18) 0.0776(13) Uani 1 1 d . . .
H8 H 0.5799 -0.0846 0.7680 0.093 Uiso 1 1 calc R . .
C9 C 0.7072(3) -0.0309(8) 0.79143(15) 0.0686(12) Uani 1 1 d . . .
H9 H 0.7212 -0.1680 0.7721 0.082 Uiso 1 1 calc R . .
C10 C 0.7743(2) 0.1192(7) 0.82180(14) 0.0544(10) Uani 1 1 d . . .
C11 C 0.8616(3) 0.0725(8) 0.82324(15) 0.0623(11) Uani 1 1 d . . .
H11 H 0.8750 -0.0606 0.8030 0.075 Uiso 1 1 calc R . .
C12 C 0.9264(3) 0.2133(8) 0.85288(15) 0.0628(11) Uani 1 1 d . . .
H12 H 0.9832 0.1754 0.8525 0.075 Uiso 1 1 calc R . .
C13 C 0.9098(2) 0.4204(7) 0.88503(14) 0.0533(10) Uani 1 1 d . . .

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 0.0489(14) 0.0545(15) 0.084(2) 0.0125(14) 0.0185(14) -0.0012(13)
O2 0.0498(16) 0.0668(17) 0.085(2) -0.0091(15) 0.0089(14) 0.0073(14)
N1 0.0507(17) 0.0569(19) 0.067(2) -0.0023(17) 0.0144(16) 0.0041(16)
C1 0.065(3) 0.055(2) 0.066(3) -0.007(2) 0.017(2) -0.010(2)
C2 0.065(2) 0.047(2) 0.065(3) -0.010(2) 0.018(2) -0.0023(19)
C3 0.047(2) 0.052(2) 0.056(2) 0.0048(19) 0.0090(18) 0.0053(19)
C4 0.048(2) 0.047(2) 0.055(2) 0.0041(19) 0.0154(18) 0.0073(18)
C5 0.048(2) 0.048(2) 0.052(2) 0.0092(18) 0.0126(18) 0.0032(18)
C6 0.048(2) 0.064(3) 0.083(3) -0.010(2) 0.019(2) 0.005(2)
C7 0.049(2) 0.085(3) 0.100(4) -0.015(3) 0.014(2) -0.004(2)
C8 0.067(3) 0.068(3) 0.092(4) -0.011(2) 0.009(3) -0.003(2)
C9 0.077(3) 0.056(2) 0.070(3) -0.010(2) 0.014(2) 0.005(2)
C10 0.058(2) 0.048(2) 0.057(2) 0.003(2) 0.0143(19) 0.007(2)
C11 0.067(3) 0.055(2) 0.067(3) -0.001(2) 0.022(2) 0.012(2)
C12 0.052(2) 0.068(3) 0.072(3) 0.001(2) 0.023(2) 0.020(2)
C13 0.048(2) 0.051(2) 0.060(3) 0.003(2) 0.0127(19) 0.0099(19)

_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 C1 1.413(4) . ?
O1 H1 0.8200 . ?
O2 C13 1.286(4) . ?
N1 C3 1.292(4) . ?
N1 C2 1.457(4) . ?
N1 H1A 0.8600 . ?
C1 C2 1.492(5) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.417(5) . ?
C3 H3 0.9300 . ?
C4 C13 1.406(5) . ?
C4 C5 1.446(5) . ?
C5 C6 1.401(5) . ?
C5 C10 1.418(5) . ?
C6 C7 1.355(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.350(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.399(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(6) . ?
C11 C12 1.345(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.433(5) . ?
C12 H12 0.9300 . ?

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 O1 H1 109.5 . . ?
C3 N1 C2 124.4(3) . . ?
C3 N1 H1A 117.8 . . ?
C2 N1 H1A 117.8 . . ?
O1 C1 C2 111.1(3) . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
O1 C1 H1C 109.4 . . ?
C2 C1 H1C 109.4 . . ?
H1B C1 H1C 108.0 . . ?
N1 C2 C1 111.2(3) . . ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C4 123.3(4) . . ?
N1 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C13 C4 C3 118.9(4) . . ?
C13 C4 C5 121.2(3) . . ?
C3 C4 C5 119.9(3) . . ?
C6 C5 C10 116.9(4) . . ?
C6 C5 C4 124.8(4) . . ?
C10 C5 C4 118.3(3) . . ?
C7 C6 C5 122.4(4) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 122.5(4) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 C5 118.8(4) . . ?
C11 C10 C5 119.1(4) . . ?
C12 C11 C10 122.4(4) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
O2 C13 C4 123.2(3) . . ?
O2 C13 C12 119.3(3) . . ?
C4 C13 C12 117.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.072