# 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
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Weiguo Cao'
_publ_contact_author_email       wgcao@staff.shu.edu.cnwgcao@staff.shu.edu.cn
loop_
_publ_author_name
'Jiechao Xu'
'Jiamei Wei'
'Jiaping Zhang'
'Wenwen Zhao'
'Jie Chen'
'Hongmei Deng'
'Min Shao'
'Xiaoyu Wu'
'Hui Zhang'
'Weiguo Cao'

# Attachment 'f91211a.cif'

data_f91211a
_database_code_depnum_ccdc_archive 'CCDC 762456'
#TrackingRef 'f91211a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 F3 N3 O4'
_chemical_formula_weight         392.31

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           TRICLINILIC
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.825(6)
_cell_length_b                   9.598(7)
_cell_length_c                   12.295(9)
_cell_angle_alpha                88.156(10)
_cell_angle_beta                 70.934(9)
_cell_angle_gamma                63.004(8)
_cell_volume                     868.7(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1957
_cell_measurement_theta_min      2.405
_cell_measurement_theta_max      26.48

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3680
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.20
_reflns_number_total             3062
_reflns_number_gt                2264
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.1581P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3062
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2275
_refine_ls_wR_factor_gt          0.2149
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.086
_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
N2 N 0.9191(3) 0.9066(3) 0.18441(19) 0.0464(6) Uani 1 1 d . . .
N1 N 0.4995(3) 1.0558(3) 0.2877(2) 0.0511(6) Uani 1 1 d D . .
C13 C 0.7909(4) 1.0659(3) 0.2044(2) 0.0450(7) Uani 1 1 d . . .
F2 F 1.0738(3) 0.5357(2) 0.0790(2) 0.0929(8) Uani 1 1 d . . .
C14 C 0.8947(3) 0.7863(3) 0.1865(2) 0.0435(7) Uani 1 1 d . . .
C8 C 0.5997(4) 1.1357(3) 0.2532(2) 0.0448(7) Uani 1 1 d . . .
C5 C 0.2724(4) 0.9059(3) 0.3284(2) 0.0493(7) Uani 1 1 d . . .
H5 H 0.2666 0.9695 0.2696 0.059 Uiso 1 1 calc R . .
C4 C 0.4174(3) 0.8550(3) 0.3679(2) 0.0433(7) Uani 1 1 d . . .
C9 C 0.5007(4) 1.3008(3) 0.2655(3) 0.0507(7) Uani 1 1 d . . .
H9 H 0.3749 1.3487 0.2991 0.061 Uiso 1 1 calc R . .
F3 F 1.2138(3) 0.6357(3) 0.1310(3) 0.1118(10) Uani 1 1 d . . .
C3 C 0.4243(4) 0.7591(4) 0.4546(2) 0.0551(8) Uani 1 1 d . . .
H3 H 0.5216 0.7227 0.4808 0.066 Uiso 1 1 calc R . .
F1 F 1.0562(3) 0.5546(3) 0.2529(2) 0.1044(9) Uani 1 1 d . . .
C1 C 0.1485(4) 0.7691(4) 0.4610(3) 0.0582(8) Uani 1 1 d . . .
C6 C 0.1374(4) 0.8634(4) 0.3753(3) 0.0542(8) Uani 1 1 d . . .
H6 H 0.0402 0.8984 0.3490 0.065 Uiso 1 1 calc R . .
C12 C 0.8698(5) 1.1654(4) 0.1699(3) 0.0588(8) Uani 1 1 d . . .
H12 H 0.9957 1.1206 0.1388 0.071 Uiso 1 1 calc R . .
C10 C 0.5831(5) 1.3934(4) 0.2297(3) 0.0616(8) Uani 1 1 d . . .
H10 H 0.5134 1.5025 0.2387 0.074 Uiso 1 1 calc R . .
C15 C 1.0615(4) 0.6292(3) 0.1622(3) 0.0557(8) Uani 1 1 d . . .
O1 O -0.1288(4) 0.7844(4) 0.4807(3) 0.0936(10) Uani 1 1 d . . .
C11 C 0.7696(5) 1.3251(4) 0.1802(3) 0.0651(9) Uani 1 1 d . . .
H11 H 0.8264 1.3873 0.1542 0.078 Uiso 1 1 calc R . .
C2 C 0.2897(5) 0.7168(4) 0.5026(3) 0.0666(9) Uani 1 1 d . . .
H2 H 0.2938 0.6541 0.5620 0.080 Uiso 1 1 calc R . .
N3 N -0.0001(5) 0.7306(4) 0.5128(3) 0.0831(10) Uani 1 1 d . . .
C7 C 0.5698(3) 0.8966(3) 0.3182(2) 0.0441(7) Uani 1 1 d . . .
O2 O 0.0087(7) 0.6507(7) 0.5893(4) 0.178(2) Uani 1 1 d . . .
C16 C 0.7222(3) 0.7764(3) 0.2100(2) 0.0414(6) Uani 1 1 d D . .
C17 C 0.6714(4) 0.8004(3) 0.1012(2) 0.0444(7) Uani 1 1 d . . .
C18 C 0.5048(5) 0.7551(4) 0.0034(3) 0.0675(9) Uani 1 1 d . . .
H18A H 0.3987 0.8556 0.0175 0.101 Uiso 1 1 calc R . .
H18B H 0.4757 0.6724 -0.0062 0.101 Uiso 1 1 calc R . .
H18C H 0.5990 0.7500 -0.0658 0.101 Uiso 1 1 calc R . .
O3 O 0.5672(3) 0.7358(2) 0.10195(18) 0.0568(6) Uani 1 1 d . . .
O4 O 0.7209(3) 0.8662(3) 0.0260(2) 0.0680(7) Uani 1 1 d . . .
H1A H 0.385(3) 1.116(3) 0.328(2) 0.055(9) Uiso 1 1 d D . .
H16 H 0.738(4) 0.675(2) 0.234(2) 0.051(8) Uiso 1 1 d 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
N2 0.0401(13) 0.0457(13) 0.0546(13) 0.0072(10) -0.0189(10) -0.0196(11)
N1 0.0368(13) 0.0367(12) 0.0677(15) 0.0008(11) -0.0100(11) -0.0127(10)
C13 0.0450(15) 0.0432(14) 0.0489(15) 0.0059(11) -0.0198(12) -0.0202(12)
F2 0.0764(15) 0.0597(12) 0.1125(18) -0.0278(12) -0.0342(13) -0.0042(11)
C14 0.0338(14) 0.0420(14) 0.0499(15) 0.0039(11) -0.0152(11) -0.0133(12)
C8 0.0498(16) 0.0411(14) 0.0434(14) 0.0022(11) -0.0190(12) -0.0192(12)
C5 0.0469(16) 0.0485(15) 0.0524(16) 0.0068(12) -0.0201(13) -0.0204(13)
C4 0.0396(14) 0.0429(14) 0.0412(13) -0.0014(11) -0.0123(11) -0.0151(12)
C9 0.0518(17) 0.0424(15) 0.0548(16) 0.0044(12) -0.0241(13) -0.0157(13)
F3 0.0363(11) 0.0669(14) 0.211(3) -0.0030(15) -0.0300(13) -0.0143(10)
C3 0.0547(18) 0.0640(18) 0.0494(16) 0.0140(14) -0.0219(13) -0.0280(15)
F1 0.0874(17) 0.0723(14) 0.0985(17) 0.0288(13) -0.0316(13) 0.0055(12)
C1 0.0518(18) 0.0660(19) 0.0537(17) -0.0052(15) -0.0070(14) -0.0320(16)
C6 0.0437(16) 0.0545(16) 0.0610(18) -0.0036(14) -0.0162(13) -0.0210(14)
C12 0.0593(19) 0.0594(19) 0.0658(19) 0.0107(15) -0.0218(15) -0.0346(16)
C10 0.083(2) 0.0407(15) 0.0650(19) 0.0109(13) -0.0336(17) -0.0268(16)
C15 0.0417(16) 0.0449(15) 0.072(2) 0.0034(14) -0.0181(14) -0.0144(13)
O1 0.0580(16) 0.104(2) 0.113(2) -0.0144(17) -0.0102(15) -0.0446(16)
C11 0.081(2) 0.0552(19) 0.073(2) 0.0168(16) -0.0276(18) -0.0432(18)
C2 0.073(2) 0.077(2) 0.0512(17) 0.0191(15) -0.0164(16) -0.0409(19)
N3 0.086(2) 0.098(3) 0.077(2) 0.0096(18) -0.0157(18) -0.061(2)
C7 0.0350(14) 0.0402(14) 0.0501(15) 0.0026(11) -0.0110(11) -0.0145(11)
O2 0.193(4) 0.302(7) 0.166(4) 0.140(4) -0.094(3) -0.205(5)
C16 0.0375(14) 0.0310(13) 0.0526(15) 0.0067(11) -0.0167(11) -0.0129(11)
C17 0.0430(15) 0.0338(13) 0.0519(16) 0.0036(11) -0.0148(12) -0.0155(12)
C18 0.074(2) 0.074(2) 0.071(2) 0.0080(16) -0.0409(18) -0.0374(19)
O3 0.0669(14) 0.0613(13) 0.0588(12) 0.0097(9) -0.0281(10) -0.0395(11)
O4 0.0814(16) 0.0820(16) 0.0683(14) 0.0308(12) -0.0373(12) -0.0546(15)

_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
N2 C14 1.265(3) . ?
N2 C13 1.397(4) . ?
N1 C8 1.377(3) . ?
N1 C7 1.455(4) . ?
C13 C12 1.400(4) . ?
C13 C8 1.412(4) . ?
F2 C15 1.327(4) . ?
C14 C16 1.500(4) . ?
C14 C15 1.502(4) . ?
C8 C9 1.403(4) . ?
C5 C6 1.377(4) . ?
C5 C4 1.391(4) . ?
C4 C3 1.384(4) . ?
C4 C7 1.509(4) . ?
C9 C10 1.365(4) . ?
F3 C15 1.302(4) . ?
C3 C2 1.374(4) . ?
F1 C15 1.305(4) . ?
C1 C6 1.366(5) . ?
C1 C2 1.378(5) . ?
C1 N3 1.463(5) . ?
C12 C11 1.362(5) . ?
C10 C11 1.379(5) . ?
O1 N3 1.207(5) . ?
N3 O2 1.194(5) . ?
C7 C16 1.559(4) . ?
C16 C17 1.524(4) . ?
C17 O4 1.180(3) . ?
C17 O3 1.320(3) . ?
C18 O3 1.461(4) . ?

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
C14 N2 C13 128.8(2) . . ?
C8 N1 C7 124.2(2) . . ?
N2 C13 C12 112.9(3) . . ?
N2 C13 C8 129.1(2) . . ?
C12 C13 C8 118.1(3) . . ?
N2 C14 C16 129.5(2) . . ?
N2 C14 C15 116.1(2) . . ?
C16 C14 C15 114.4(2) . . ?
N1 C8 C9 116.3(2) . . ?
N1 C8 C13 125.8(2) . . ?
C9 C8 C13 117.8(2) . . ?
C6 C5 C4 120.8(3) . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 C7 118.7(2) . . ?
C5 C4 C7 122.7(2) . . ?
C10 C9 C8 122.2(3) . . ?
C2 C3 C4 121.1(3) . . ?
C6 C1 C2 121.9(3) . . ?
C6 C1 N3 118.0(3) . . ?
C2 C1 N3 120.0(3) . . ?
C1 C6 C5 118.9(3) . . ?
C11 C12 C13 122.6(3) . . ?
C9 C10 C11 119.9(3) . . ?
F3 C15 F1 106.0(3) . . ?
F3 C15 F2 107.4(3) . . ?
F1 C15 F2 105.9(3) . . ?
F3 C15 C14 114.9(2) . . ?
F1 C15 C14 111.7(3) . . ?
F2 C15 C14 110.6(3) . . ?
C12 C11 C10 119.3(3) . . ?
C3 C2 C1 118.6(3) . . ?
O2 N3 O1 122.5(4) . . ?
O2 N3 C1 117.6(4) . . ?
O1 N3 C1 119.8(4) . . ?
N1 C7 C4 110.0(2) . . ?
N1 C7 C16 110.3(2) . . ?
C4 C7 C16 111.3(2) . . ?
C14 C16 C17 109.5(2) . . ?
C14 C16 C7 110.0(2) . . ?
C17 C16 C7 113.1(2) . . ?
O4 C17 O3 124.8(3) . . ?
O4 C17 C16 124.3(3) . . ?
O3 C17 C16 110.8(2) . . ?
C17 O3 C18 116.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.070