# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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data_cd212483
#TrackingRef 'web_deposit_cif_file_0_Ran-NingGuo_1356867993.cd212483.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Br F N O'
_chemical_formula_weight         376.26

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                   5.8517(5)
_cell_length_b                   16.9278(15)
_cell_length_c                   17.4654(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1730.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2290
_cell_measurement_theta_min      4.813
_cell_measurement_theta_max      40.047

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.389
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.49503
_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            10163
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3388
_reflns_number_gt                2512
_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^)+(0.0455P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3388
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_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 0.23912(8) 0.27057(2) 0.322745(19) 0.08304(18) Uani 1 1 d . . .
F1 F 0.8044(5) -0.08990(17) 0.77018(13) 0.1122(10) Uani 1 1 d . . .
N1 N 0.5547(5) 0.00809(16) 0.60619(15) 0.0561(7) Uani 1 1 d . . .
O1 O 0.8668(5) 0.01011(18) 0.53132(15) 0.0793(8) Uani 1 1 d . . .
C1 C 0.6358(6) -0.0595(2) 0.6495(2) 0.0649(9) Uani 1 1 d . . .
H1 H 0.7589 -0.0841 0.6198 0.078 Uiso 1 1 calc R . .
C2 C 0.7415(8) -0.0271(2) 0.72308(18) 0.0712(9) Uani 1 1 d . . .
H2 H 0.8792 0.0028 0.7097 0.085 Uiso 1 1 calc R . .
C3 C 0.5811(6) 0.0265(2) 0.76410(18) 0.0577(8) Uani 1 1 d . . .
C4 C 0.6107(8) 0.0410(2) 0.8423(2) 0.0739(11) Uani 1 1 d . . .
H4 H 0.7304 0.0170 0.8684 0.089 Uiso 1 1 calc R . .
C5 C 0.4661(10) 0.0900(3) 0.8806(2) 0.0875(13) Uani 1 1 d . . .
H5 H 0.4864 0.0984 0.9328 0.105 Uiso 1 1 calc R . .
C6 C 0.2922(9) 0.1266(3) 0.8433(2) 0.0875(13) Uani 1 1 d . . .
H6 H 0.1952 0.1606 0.8697 0.105 Uiso 1 1 calc R . .
C7 C 0.2598(8) 0.1134(2) 0.76615(18) 0.0723(9) Uani 1 1 d . . .
H7 H 0.1395 0.1379 0.7407 0.087 Uiso 1 1 calc R . .
C8 C 0.4065(6) 0.0635(2) 0.72612(18) 0.0557(8) Uani 1 1 d . . .
C9 C 0.3663(6) 0.0509(2) 0.64094(16) 0.0570(8) Uani 1 1 d . . .
H9A H 0.2257 0.0214 0.6336 0.068 Uiso 1 1 calc R . .
H9B H 0.3492 0.1017 0.6159 0.068 Uiso 1 1 calc R . .
C10 C 0.6757(5) 0.0347(2) 0.54626(19) 0.0543(9) Uani 1 1 d . . .
C11 C 0.5653(6) 0.09298(19) 0.49407(15) 0.0506(8) Uani 1 1 d . . .
C12 C 0.6852(6) 0.16034(19) 0.47142(18) 0.0587(9) Uani 1 1 d . . .
H12 H 0.8305 0.1700 0.4909 0.070 Uiso 1 1 calc R . .
C13 C 0.5884(6) 0.2126(2) 0.42023(19) 0.0617(9) Uani 1 1 d . . .
H13 H 0.6666 0.2582 0.4062 0.074 Uiso 1 1 calc R . .
C14 C 0.3786(6) 0.1974(2) 0.39027(17) 0.0582(8) Uani 1 1 d . . .
C15 C 0.2588(7) 0.13075(19) 0.40916(16) 0.0584(7) Uani 1 1 d . . .
H15 H 0.1176 0.1202 0.3870 0.070 Uiso 1 1 calc R . .
C16 C 0.3535(6) 0.0793(2) 0.46236(18) 0.0588(9) Uani 1 1 d . . .
H16 H 0.2720 0.0346 0.4769 0.071 Uiso 1 1 calc R . .
C17 C 0.4525(7) -0.1215(2) 0.6617(2) 0.0739(10) Uani 1 1 d . . .
H17A H 0.5187 -0.1661 0.6886 0.089 Uiso 1 1 calc R . .
H17B H 0.3332 -0.0996 0.6939 0.089 Uiso 1 1 calc R . .
C18 C 0.3478(10) -0.1502(3) 0.5879(3) 0.1114(18) Uani 1 1 d . . .
H18A H 0.2781 -0.1057 0.5619 0.134 Uiso 1 1 calc R . .
H18B H 0.4682 -0.1705 0.5552 0.134 Uiso 1 1 calc R . .
C19 C 0.1710(10) -0.2134(3) 0.5984(3) 0.125(2) Uani 1 1 d . . .
H19A H 0.2425 -0.2604 0.6178 0.188 Uiso 1 1 calc R . .
H19B H 0.1000 -0.2248 0.5501 0.188 Uiso 1 1 calc R . .
H19C H 0.0573 -0.1956 0.6341 0.188 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 0.1004(3) 0.0799(3) 0.0688(2) 0.01545(18) -0.0016(3) 0.0058(3)
F1 0.124(2) 0.1135(19) 0.0992(15) 0.0131(14) -0.0368(16) 0.0516(18)
N1 0.0496(16) 0.0579(16) 0.0608(16) 0.0089(13) 0.0098(14) 0.0110(14)
O1 0.0495(15) 0.115(2) 0.0731(16) 0.0086(16) 0.0124(13) 0.0156(15)
C1 0.056(2) 0.066(2) 0.072(2) 0.0051(18) 0.0052(17) 0.0133(19)
C2 0.057(2) 0.077(2) 0.079(2) 0.0162(18) -0.004(2) 0.010(3)
C3 0.053(2) 0.061(2) 0.0596(19) 0.0090(16) 0.0052(17) -0.0077(18)
C4 0.079(3) 0.074(3) 0.069(2) 0.012(2) -0.010(2) -0.011(2)
C5 0.121(4) 0.085(3) 0.057(2) 0.003(2) 0.001(3) -0.015(3)
C6 0.112(4) 0.081(3) 0.069(2) -0.0008(19) 0.030(3) 0.014(3)
C7 0.072(2) 0.080(2) 0.0658(18) 0.0083(17) 0.014(2) 0.013(3)
C8 0.0472(19) 0.0605(19) 0.0593(18) 0.0116(16) 0.0109(16) -0.0053(17)
C9 0.0465(18) 0.067(2) 0.0574(18) 0.0109(17) 0.0096(14) 0.0094(17)
C10 0.0416(19) 0.068(2) 0.0532(18) -0.0036(17) 0.0036(14) -0.0026(16)
C11 0.0416(18) 0.0631(19) 0.0470(16) -0.0052(15) 0.0059(14) -0.0021(17)
C12 0.045(2) 0.070(2) 0.0608(18) -0.0081(17) 0.0061(15) -0.0117(16)
C13 0.063(2) 0.059(2) 0.0633(19) -0.0008(17) 0.0114(18) -0.0175(18)
C14 0.065(2) 0.0588(19) 0.0505(17) -0.0023(15) 0.0097(16) 0.0022(19)
C15 0.0493(17) 0.071(2) 0.0551(15) -0.0024(15) -0.002(2) -0.006(2)
C16 0.051(2) 0.063(2) 0.0620(18) 0.0093(18) 0.0074(16) -0.0129(17)
C17 0.076(3) 0.061(2) 0.085(2) 0.0093(19) -0.005(2) 0.005(2)
C18 0.151(5) 0.082(3) 0.101(3) 0.001(3) -0.016(3) -0.022(3)
C19 0.142(5) 0.083(3) 0.151(5) -0.011(3) -0.036(4) -0.012(3)

_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 C14 1.895(3) . ?
F1 C2 1.393(4) . ?
N1 C10 1.342(4) . ?
N1 C1 1.451(4) . ?
N1 C9 1.452(4) . ?
O1 C10 1.222(4) . ?
C1 C17 1.517(5) . ?
C1 C2 1.528(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.489(5) . ?
C2 H2 0.9800 . ?
C3 C8 1.370(5) . ?
C3 C4 1.399(5) . ?
C4 C5 1.360(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.521(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.490(5) . ?
C11 C16 1.377(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(5) . ?
C15 C16 1.389(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.508(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.500(7) . ?
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
C10 N1 C1 119.9(3) . . ?
C10 N1 C9 124.0(3) . . ?
C1 N1 C9 115.1(3) . . ?
N1 C1 C17 112.8(3) . . ?
N1 C1 C2 106.8(3) . . ?
C17 C1 C2 114.5(3) . . ?
N1 C1 H1 107.5 . . ?
C17 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
F1 C2 C3 110.3(3) . . ?
F1 C2 C1 109.3(3) . . ?
C3 C2 C1 111.6(3) . . ?
F1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C8 C3 C4 119.0(3) . . ?
C8 C3 C2 121.0(3) . . ?
C4 C3 C2 120.0(4) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 120.3(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 119.6(3) . . ?
C3 C8 C9 121.7(3) . . ?
C7 C8 C9 118.7(3) . . ?
N1 C9 C8 111.2(3) . . ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O1 C10 N1 122.3(4) . . ?
O1 C10 C11 119.5(3) . . ?
N1 C10 C11 118.1(3) . . ?
C16 C11 C12 118.4(3) . . ?
C16 C11 C10 121.6(3) . . ?
C12 C11 C10 119.7(3) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 Br1 120.3(3) . . ?
C15 C14 Br1 117.9(3) . . ?
C14 C15 C16 118.3(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 121.5(3) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C1 112.9(4) . . ?
C18 C17 H17A 109.0 . . ?
C1 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C1 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 113.9(4) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
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 . . ?

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
C10 N1 C1 C17 -130.9(3) . . . . ?
C9 N1 C1 C17 60.2(4) . . . . ?
C10 N1 C1 C2 102.4(3) . . . . ?
C9 N1 C1 C2 -66.5(4) . . . . ?
N1 C1 C2 F1 174.8(3) . . . . ?
C17 C1 C2 F1 49.1(4) . . . . ?
N1 C1 C2 C3 52.5(4) . . . . ?
C17 C1 C2 C3 -73.2(4) . . . . ?
F1 C2 C3 C8 -144.3(3) . . . . ?
C1 C2 C3 C8 -22.6(5) . . . . ?
F1 C2 C3 C4 37.0(5) . . . . ?
C1 C2 C3 C4 158.8(3) . . . . ?
C8 C3 C4 C5 1.2(5) . . . . ?
C2 C3 C4 C5 179.8(4) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C5 C6 C7 C8 -0.9(7) . . . . ?
C4 C3 C8 C7 -1.2(5) . . . . ?
C2 C3 C8 C7 -179.9(3) . . . . ?
C4 C3 C8 C9 179.4(3) . . . . ?
C2 C3 C8 C9 0.8(5) . . . . ?
C6 C7 C8 C3 1.1(6) . . . . ?
C6 C7 C8 C9 -179.5(4) . . . . ?
C10 N1 C9 C8 -124.0(3) . . . . ?
C1 N1 C9 C8 44.5(4) . . . . ?
C3 C8 C9 N1 -10.0(4) . . . . ?
C7 C8 C9 N1 170.6(3) . . . . ?
C1 N1 C10 O1 -8.6(5) . . . . ?
C9 N1 C10 O1 159.3(3) . . . . ?
C1 N1 C10 C11 167.8(3) . . . . ?
C9 N1 C10 C11 -24.3(5) . . . . ?
O1 C10 C11 C16 124.7(4) . . . . ?
N1 C10 C11 C16 -51.7(4) . . . . ?
O1 C10 C11 C12 -50.0(4) . . . . ?
N1 C10 C11 C12 133.5(3) . . . . ?
C16 C11 C12 C13 1.9(4) . . . . ?
C10 C11 C12 C13 176.9(3) . . . . ?
C11 C12 C13 C14 -1.7(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C12 C13 C14 Br1 177.7(2) . . . . ?
C13 C14 C15 C16 2.2(5) . . . . ?
Br1 C14 C15 C16 -176.0(2) . . . . ?
C12 C11 C16 C15 -0.1(5) . . . . ?
C10 C11 C16 C15 -174.9(3) . . . . ?
C14 C15 C16 C11 -1.9(5) . . . . ?
N1 C1 C17 C18 55.9(5) . . . . ?
C2 C1 C17 C18 178.3(4) . . . . ?
C1 C17 C18 C19 178.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.046


_database_code_depnum_ccdc_archive 'CCDC 917645'