# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         177

_publ_contact_author_name        'Yongming Wu'

_publ_contact_author_email       ymwu@sioc.ac.cn

_publ_contact_author_address     
;
Shanghai Institute of Organic
Chemistry
;
loop_
_publ_author_name
'Zixian Chen'
'Jiangtao Zhu'
'Haibo Xie'
'Shan Li'
'Yongming Wu'
'Yuefa Gong'

# Attachment '3645_web_deposit_cif_file_0_YongmingWu_1294129804.cif'

data_cd27589
_database_code_depnum_ccdc_archive 'CCDC 806367'
#TrackingRef '3645_web_deposit_cif_file_0_YongmingWu_1294129804.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 F2 N O2'
_chemical_formula_weight         239.22

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   5.8677(8)
_cell_length_b                   12.9406(18)
_cell_length_c                   14.433(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.076(2)
_cell_angle_gamma                90.00
_cell_volume                     1093.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1932
_cell_measurement_theta_min      6.477
_cell_measurement_theta_max      50.817

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.451
_exptl_crystal_size_min          0.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7644
_exptl_absorpt_correction_T_max  1.0000
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6380
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2393
_reflns_number_gt                1730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0770P)^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       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2393
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1407
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
F1 F 0.73155(19) 0.33132(10) 0.35256(7) 0.0617(4) Uani 1 1 d . . .
F2 F 0.4879(2) 0.20772(8) 0.34523(7) 0.0624(4) Uani 1 1 d . . .
O1 O 0.1630(3) 0.43084(11) 0.57912(9) 0.0638(4) Uani 1 1 d . . .
O2 O 0.3008(2) 0.40271(10) 0.01238(8) 0.0540(4) Uani 1 1 d . . .
N1 N 0.2108(3) 0.41468(12) 0.38807(10) 0.0427(4) Uani 1 1 d . . .
C1 C 0.2085(3) 0.41630(12) 0.29103(11) 0.0383(4) Uani 1 1 d . . .
C2 C 0.0617(3) 0.46784(14) 0.22801(13) 0.0478(5) Uani 1 1 d . . .
H2 H -0.0600 0.5065 0.2473 0.057 Uiso 1 1 calc R . .
C3 C 0.1019(3) 0.45994(14) 0.13573(13) 0.0484(5) Uani 1 1 d . . .
H3 H 0.0055 0.4943 0.0920 0.058 Uiso 1 1 calc R . .
C4 C 0.2810(3) 0.40261(13) 0.10588(12) 0.0407(4) Uani 1 1 d . . .
C5 C 0.4255(3) 0.35084(13) 0.16911(12) 0.0414(4) Uani 1 1 d . . .
H5 H 0.5469 0.3118 0.1502 0.050 Uiso 1 1 calc R . .
C6 C 0.3839(3) 0.35892(11) 0.26147(11) 0.0361(4) Uani 1 1 d . . .
C7 C 0.5048(3) 0.31263(13) 0.34469(11) 0.0402(4) Uani 1 1 d . . .
C8 C 0.3856(3) 0.35752(12) 0.42521(12) 0.0383(4) Uani 1 1 d . . .
C9 C 0.4521(3) 0.33961(13) 0.51475(12) 0.0445(5) Uani 1 1 d . . .
H9 H 0.5810 0.2989 0.5279 0.053 Uiso 1 1 calc R . .
C10 C 0.3366(3) 0.37930(14) 0.59098(12) 0.0441(5) Uani 1 1 d . . .
C11 C 0.4364(4) 0.35404(16) 0.68639(13) 0.0583(6) Uani 1 1 d . . .
H11A H 0.3334 0.3760 0.7313 0.087 Uiso 1 1 calc R . .
H11B H 0.5799 0.3891 0.6976 0.087 Uiso 1 1 calc R . .
H11C H 0.4599 0.2808 0.6916 0.087 Uiso 1 1 calc R . .
C12 C 0.4934(4) 0.35196(16) -0.02054(13) 0.0567(5) Uani 1 1 d . . .
H12A H 0.6306 0.3812 0.0087 0.085 Uiso 1 1 calc R . .
H12B H 0.4930 0.3606 -0.0866 0.085 Uiso 1 1 calc R . .
H12C H 0.4869 0.2797 -0.0060 0.085 Uiso 1 1 calc R . .
H1 H 0.123(4) 0.4511(16) 0.4205(15) 0.063(7) Uiso 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
F1 0.0431(7) 0.0975(9) 0.0448(7) 0.0052(6) 0.0048(5) 0.0101(6)
F2 0.0993(10) 0.0398(6) 0.0484(7) 0.0037(5) 0.0083(6) 0.0168(6)
O1 0.0732(10) 0.0750(10) 0.0440(8) 0.0007(7) 0.0096(7) 0.0266(8)
O2 0.0674(9) 0.0642(9) 0.0301(7) -0.0003(6) 0.0022(6) 0.0118(7)
N1 0.0462(9) 0.0492(9) 0.0332(8) 0.0013(7) 0.0072(7) 0.0096(7)
C1 0.0434(10) 0.0387(9) 0.0330(9) 0.0006(7) 0.0052(7) 0.0002(7)
C2 0.0498(11) 0.0537(11) 0.0402(10) 0.0026(8) 0.0051(8) 0.0151(9)
C3 0.0538(12) 0.0510(11) 0.0394(10) 0.0053(8) -0.0038(8) 0.0090(9)
C4 0.0494(11) 0.0416(9) 0.0311(9) -0.0002(7) 0.0019(7) -0.0014(8)
C5 0.0455(11) 0.0430(10) 0.0363(10) -0.0016(7) 0.0064(7) 0.0067(8)
C6 0.0400(10) 0.0344(8) 0.0341(9) 0.0004(7) 0.0039(7) 0.0009(7)
C7 0.0421(10) 0.0418(9) 0.0370(10) 0.0020(7) 0.0050(7) 0.0039(7)
C8 0.0418(10) 0.0371(9) 0.0363(9) 0.0018(7) 0.0056(7) -0.0005(7)
C9 0.0492(11) 0.0490(10) 0.0352(10) 0.0034(7) 0.0021(8) 0.0088(8)
C10 0.0538(12) 0.0421(10) 0.0366(10) 0.0016(7) 0.0050(8) 0.0009(8)
C11 0.0734(15) 0.0679(13) 0.0336(11) 0.0010(9) 0.0043(9) 0.0051(10)
C12 0.0671(14) 0.0684(13) 0.0357(11) -0.0056(9) 0.0108(9) 0.0000(10)

_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
F1 C7 1.349(2) . ?
F2 C7 1.361(2) . ?
O1 C10 1.219(2) . ?
O2 C4 1.363(2) . ?
O2 C12 1.418(2) . ?
N1 C8 1.345(2) . ?
N1 C1 1.400(2) . ?
N1 H1 0.86(2) . ?
C1 C6 1.362(2) . ?
C1 C2 1.379(2) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C5 C6 1.376(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.478(2) . ?
C7 C8 1.514(2) . ?
C8 C9 1.343(2) . ?
C9 C10 1.428(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.494(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C4 O2 C12 117.25(14) . . ?
C8 N1 C1 111.10(15) . . ?
C8 N1 H1 123.6(14) . . ?
C1 N1 H1 124.9(14) . . ?
C6 C1 C2 120.49(16) . . ?
C6 C1 N1 110.57(14) . . ?
C2 C1 N1 128.92(16) . . ?
C3 C2 C1 117.47(17) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 122.02(16) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
O2 C4 C5 124.44(16) . . ?
O2 C4 C3 115.43(15) . . ?
C5 C4 C3 120.13(17) . . ?
C4 C5 C6 117.55(16) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 122.33(15) . . ?
C1 C6 C7 107.23(14) . . ?
C5 C6 C7 130.44(16) . . ?
F1 C7 F2 104.50(14) . . ?
F1 C7 C6 114.17(14) . . ?
F2 C7 C6 112.19(13) . . ?
F1 C7 C8 111.92(14) . . ?
F2 C7 C8 109.89(14) . . ?
C6 C7 C8 104.30(14) . . ?
C9 C8 N1 129.76(17) . . ?
C9 C8 C7 123.62(16) . . ?
N1 C8 C7 106.62(15) . . ?
C8 C9 C10 123.91(17) . . ?
C8 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
O1 C10 C9 121.73(17) . . ?
O1 C10 C11 121.19(18) . . ?
C9 C10 C11 117.07(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 0.3(2) . . . . ?
C8 N1 C1 C2 -178.17(17) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
N1 C1 C2 C3 177.43(17) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C12 O2 C4 C5 -4.7(3) . . . . ?
C12 O2 C4 C3 174.87(16) . . . . ?
C2 C3 C4 O2 -179.42(16) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
O2 C4 C5 C6 179.52(15) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
N1 C1 C6 C5 -177.54(15) . . . . ?
C2 C1 C6 C7 -178.92(16) . . . . ?
N1 C1 C6 C7 2.47(19) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 179.42(17) . . . . ?
C1 C6 C7 F1 -126.42(16) . . . . ?
C5 C6 C7 F1 53.6(2) . . . . ?
C1 C6 C7 F2 114.93(16) . . . . ?
C5 C6 C7 F2 -65.1(2) . . . . ?
C1 C6 C7 C8 -3.96(18) . . . . ?
C5 C6 C7 C8 176.04(17) . . . . ?
C1 N1 C8 C9 177.37(18) . . . . ?
C1 N1 C8 C7 -2.84(19) . . . . ?
F1 C7 C8 C9 -52.2(2) . . . . ?
F2 C7 C8 C9 63.5(2) . . . . ?
C6 C7 C8 C9 -176.07(16) . . . . ?
F1 C7 C8 N1 128.05(15) . . . . ?
F2 C7 C8 N1 -116.32(15) . . . . ?
C6 C7 C8 N1 4.13(18) . . . . ?
N1 C8 C9 C10 1.6(3) . . . . ?
C7 C8 C9 C10 -178.15(16) . . . . ?
C8 C9 C10 O1 2.0(3) . . . . ?
C8 C9 C10 C11 -178.61(17) . . . . ?

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
N1 H1 O1 0.86(2) 2.27(2) 3.030(2) 147.3(19) 3_566
N1 H1 O1 0.86(2) 2.30(2) 2.799(2) 117.1(17) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049