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


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       slyou@sioc.ac.cn
_publ_contact_author_name        'Shuli You'
_publ_author_name                'Shuli You'

data_cd211246
_database_code_depnum_ccdc_archive 'CCDC 859342'
#TrackingRef 'cd211246.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Br F3 N O'
_chemical_formula_weight         396.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.2256(14)
_cell_length_b                   11.0205(18)
_cell_length_c                   18.212(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1650.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3899
_cell_measurement_theta_min      4.473
_cell_measurement_theta_max      51.188

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    2.525
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.57501
_exptl_absorpt_correction_T_max  1.00000
_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            8973
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3202
_reflns_number_gt                2721
_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^)+(0.0314P)^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       0.0035(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     218
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Br1 Br 0.13184(4) -0.38707(2) 0.068711(18) 0.06625(14) Uani 1 1 d . . .
F1 F 0.2121(3) 0.1599(2) -0.05560(11) 0.0912(7) Uani 1 1 d . . .
F2 F 0.0060(3) 0.2679(2) -0.07884(11) 0.0890(7) Uani 1 1 d . . .
F3 F -0.0247(3) 0.08588(18) -0.04396(9) 0.0727(5) Uani 1 1 d . . .
N1 N 0.0480(3) 0.15615(18) 0.10015(11) 0.0454(5) Uani 1 1 d . . .
O1 O 0.0759(3) 0.34247(18) 0.05025(13) 0.0764(7) Uani 1 1 d . . .
C1 C 0.0642(4) 0.2339(2) 0.04433(14) 0.0487(7) Uani 1 1 d . . .
C2 C 0.0644(4) 0.1841(3) -0.03382(15) 0.0540(7) Uani 1 1 d . . .
C3 C 0.0712(4) 0.0272(2) 0.09391(13) 0.0421(6) Uani 1 1 d . . .
C4 C 0.2214(4) -0.0192(2) 0.07973(16) 0.0504(7) Uani 1 1 d . . .
H4 H 0.3102 0.0327 0.0755 0.060 Uiso 1 1 calc R . .
C5 C 0.2427(4) -0.1431(3) 0.07162(17) 0.0546(7) Uani 1 1 d . . .
H5 H 0.3443 -0.1755 0.0608 0.066 Uiso 1 1 calc R . .
C6 C 0.1092(4) -0.2168(2) 0.08008(13) 0.0478(6) Uani 1 1 d . . .
C7 C -0.0414(4) -0.1712(2) 0.09625(14) 0.0471(7) Uani 1 1 d . . .
H7 H -0.1289 -0.2236 0.1027 0.056 Uiso 1 1 calc R . .
C8 C -0.0637(4) -0.0469(2) 0.10304(14) 0.0433(6) Uani 1 1 d . . .
C9 C -0.2285(4) 0.0057(3) 0.11688(16) 0.0537(7) Uani 1 1 d . . .
H9A H -0.2603 0.0536 0.0746 0.064 Uiso 1 1 calc R . .
H9B H -0.3060 -0.0602 0.1218 0.064 Uiso 1 1 calc R . .
C10 C -0.2377(4) 0.0838(3) 0.18389(17) 0.0638(8) Uani 1 1 d . . .
H10 H -0.3304 0.0735 0.2125 0.077 Uiso 1 1 calc R . .
C11 C -0.1346(4) 0.1641(3) 0.20797(16) 0.0634(8) Uani 1 1 d . . .
H11 H -0.1628 0.2004 0.2523 0.076 Uiso 1 1 calc R . .
C12 C 0.0220(4) 0.2070(2) 0.17552(15) 0.0543(7) Uani 1 1 d . . .
H12 H 0.0114 0.2950 0.1695 0.065 Uiso 1 1 calc R . .
C13 C 0.1673(4) 0.1872(3) 0.22396(15) 0.0576(8) Uani 1 1 d . . .
C14 C 0.1817(5) 0.0857(3) 0.26638(18) 0.0783(10) Uani 1 1 d U . .
H14 H 0.1010 0.0267 0.2647 0.094 Uiso 1 1 calc R . .
C15 C 0.3136(6) 0.0696(5) 0.3116(2) 0.1023(14) Uani 1 1 d U . .
H15 H 0.3222 -0.0001 0.3401 0.123 Uiso 1 1 calc R . .
C16 C 0.4322(6) 0.1563(6) 0.3146(3) 0.1085(17) Uani 1 1 d U . .
H16 H 0.5217 0.1460 0.3452 0.130 Uiso 1 1 calc R . .
C17 C 0.4184(5) 0.2569(5) 0.2729(3) 0.0983(14) Uani 1 1 d U . .
H17 H 0.4989 0.3160 0.2752 0.118 Uiso 1 1 calc R . .
C18 C 0.2887(5) 0.2736(4) 0.22743(18) 0.0751(10) Uani 1 1 d . . .
H18 H 0.2819 0.3433 0.1987 0.090 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
Br1 0.0946(2) 0.03096(15) 0.0731(2) -0.00784(13) 0.00283(18) 0.01307(14)
F1 0.0743(13) 0.1249(19) 0.0743(13) -0.0190(13) 0.0203(10) -0.0075(13)
F2 0.1292(18) 0.0775(14) 0.0603(11) 0.0260(10) -0.0187(12) -0.0117(13)
F3 0.1016(14) 0.0676(12) 0.0489(9) -0.0015(8) -0.0034(9) -0.0351(11)
N1 0.0708(15) 0.0258(10) 0.0395(10) -0.0015(8) 0.0024(10) 0.0053(10)
O1 0.122(2) 0.0316(11) 0.0754(15) 0.0049(10) 0.0001(13) -0.0120(12)
C1 0.0576(17) 0.0344(15) 0.0541(15) 0.0026(11) -0.0007(12) -0.0064(12)
C2 0.0625(18) 0.0505(17) 0.0490(15) 0.0078(13) 0.0029(14) -0.0106(14)
C3 0.0634(18) 0.0266(12) 0.0362(12) -0.0014(9) 0.0048(11) 0.0057(12)
C4 0.0577(18) 0.0382(14) 0.0552(17) -0.0040(12) 0.0048(14) -0.0032(12)
C5 0.0575(17) 0.0438(15) 0.0626(17) -0.0017(14) 0.0106(15) 0.0105(12)
C6 0.0716(19) 0.0273(12) 0.0446(13) 0.0003(10) 0.0030(14) 0.0089(12)
C7 0.0633(19) 0.0319(14) 0.0460(14) 0.0027(10) 0.0070(12) -0.0013(12)
C8 0.0562(17) 0.0362(14) 0.0375(12) 0.0029(10) 0.0055(11) 0.0055(11)
C9 0.0578(18) 0.0452(15) 0.0581(17) 0.0015(13) 0.0065(14) 0.0090(13)
C10 0.0631(19) 0.076(2) 0.0520(16) 0.0001(16) 0.0154(14) 0.0195(17)
C11 0.077(2) 0.0670(18) 0.0466(15) -0.0124(14) 0.0042(16) 0.0237(19)
C12 0.081(2) 0.0372(15) 0.0443(14) -0.0065(12) -0.0021(14) 0.0179(14)
C13 0.079(2) 0.0513(17) 0.0423(14) -0.0135(12) 0.0002(14) 0.0116(15)
C14 0.099(3) 0.074(2) 0.062(2) 0.0079(17) -0.0132(17) 0.013(2)
C15 0.118(4) 0.114(4) 0.075(3) 0.009(2) -0.023(2) 0.041(3)
C16 0.081(3) 0.165(5) 0.079(3) -0.038(3) -0.014(2) 0.045(3)
C17 0.067(3) 0.135(4) 0.093(3) -0.052(3) 0.014(2) -0.002(3)
C18 0.084(3) 0.084(2) 0.0580(19) -0.0251(17) 0.0059(18) -0.003(2)

_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
Br1 C6 1.897(2) . ?
F1 C2 1.306(4) . ?
F2 C2 1.325(4) . ?
F3 C2 1.321(3) . ?
N1 C1 1.337(3) . ?
N1 C3 1.439(3) . ?
N1 C12 1.498(3) . ?
O1 C1 1.205(3) . ?
C1 C2 1.525(4) . ?
C3 C4 1.361(4) . ?
C3 C8 1.388(4) . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(4) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.496(4) . ?
C9 C10 1.495(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.302(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.494(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.502(5) . ?
C12 H12 0.9800 . ?
C13 C14 1.364(5) . ?
C13 C18 1.381(5) . ?
C14 C15 1.373(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.349(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(6) . ?
C17 H17 0.9300 . ?
C18 H18 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 N1 C3 124.1(2) . . ?
C1 N1 C12 118.1(2) . . ?
C3 N1 C12 117.5(2) . . ?
O1 C1 N1 125.2(3) . . ?
O1 C1 C2 116.1(3) . . ?
N1 C1 C2 118.6(2) . . ?
F1 C2 F3 107.8(3) . . ?
F1 C2 F2 107.0(3) . . ?
F3 C2 F2 106.4(2) . . ?
F1 C2 C1 111.0(3) . . ?
F3 C2 C1 115.1(2) . . ?
F2 C2 C1 109.0(3) . . ?
C4 C3 C8 121.8(2) . . ?
C4 C3 N1 120.4(3) . . ?
C8 C3 N1 117.8(2) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C7 C6 C5 122.0(2) . . ?
C7 C6 Br1 118.4(2) . . ?
C5 C6 Br1 119.6(2) . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 117.7(3) . . ?
C7 C8 C9 121.2(3) . . ?
C3 C8 C9 121.1(2) . . ?
C10 C9 C8 114.0(3) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 129.3(3) . . ?
C11 C10 H10 115.4 . . ?
C9 C10 H10 115.4 . . ?
C10 C11 C12 130.1(3) . . ?
C10 C11 H11 115.0 . . ?
C12 C11 H11 115.0 . . ?
C11 C12 N1 111.5(2) . . ?
C11 C12 C13 114.1(2) . . ?
N1 C12 C13 111.7(2) . . ?
C11 C12 H12 106.3 . . ?
N1 C12 H12 106.3 . . ?
C13 C12 H12 106.3 . . ?
C14 C13 C18 118.5(3) . . ?
C14 C13 C12 121.4(3) . . ?
C18 C13 C12 120.1(3) . . ?
C13 C14 C15 120.9(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.3(5) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?

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
C3 N1 C1 O1 -165.2(3) . . . . ?
C12 N1 C1 O1 7.8(5) . . . . ?
C3 N1 C1 C2 16.3(4) . . . . ?
C12 N1 C1 C2 -170.7(3) . . . . ?
O1 C1 C2 F1 89.9(4) . . . . ?
N1 C1 C2 F1 -91.5(3) . . . . ?
O1 C1 C2 F3 -147.3(3) . . . . ?
N1 C1 C2 F3 31.4(4) . . . . ?
O1 C1 C2 F2 -27.7(4) . . . . ?
N1 C1 C2 F2 150.9(3) . . . . ?
C1 N1 C3 C4 67.1(4) . . . . ?
C12 N1 C3 C4 -105.9(3) . . . . ?
C1 N1 C3 C8 -113.1(3) . . . . ?
C12 N1 C3 C8 73.9(3) . . . . ?
C8 C3 C4 C5 2.1(4) . . . . ?
N1 C3 C4 C5 -178.1(3) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C4 C5 C6 Br1 179.5(2) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
Br1 C6 C7 C8 -178.3(2) . . . . ?
C6 C7 C8 C3 -0.9(4) . . . . ?
C6 C7 C8 C9 176.9(2) . . . . ?
C4 C3 C8 C7 -0.8(4) . . . . ?
N1 C3 C8 C7 179.4(2) . . . . ?
C4 C3 C8 C9 -178.6(3) . . . . ?
N1 C3 C8 C9 1.6(3) . . . . ?
C7 C8 C9 C10 124.0(3) . . . . ?
C3 C8 C9 C10 -58.3(4) . . . . ?
C8 C9 C10 C11 41.7(5) . . . . ?
C9 C10 C11 C12 2.4(6) . . . . ?
C10 C11 C12 N1 7.2(4) . . . . ?
C10 C11 C12 C13 -120.6(4) . . . . ?
C1 N1 C12 C11 120.5(3) . . . . ?
C3 N1 C12 C11 -66.0(3) . . . . ?
C1 N1 C12 C13 -110.4(3) . . . . ?
C3 N1 C12 C13 63.0(4) . . . . ?
C11 C12 C13 C14 37.2(4) . . . . ?
N1 C12 C13 C14 -90.5(4) . . . . ?
C11 C12 C13 C18 -141.6(3) . . . . ?
N1 C12 C13 C18 90.8(3) . . . . ?
C18 C13 C14 C15 0.0(5) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C16 C17 C18 C13 0.6(6) . . . . ?
C14 C13 C18 C17 -0.5(5) . . . . ?
C12 C13 C18 C17 178.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051