# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
#TrackingRef '- 10116_0M.CIF.txt'

_journal_coden_Cambridge         182
loop_
_publ_author_name
'Christian Wolf'
'Hanhui Xu.'
_publ_contact_author_address     
;
Department of Chemistry
Georgetown University
37th and O Streets NW
Washington DC 20057
USA
;
_publ_contact_author_email       cw27@georgetown.edu
_publ_contact_author_fax         '(202) 687 6209'
_publ_contact_author_phone       '(202) 687 3468'

_publ_contact_author_name        'Christian Wolf'

_publ_contact_letter             
;

Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

_publ_requested_journal          'Chemical Communications'

data_c:\docume~1\daniwa~1\desktop\10116\work\10116_0m
_database_code_depnum_ccdc_archive 'CCDC 783420'

#==============================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 F3 N O3'
_chemical_formula_weight         249.19

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   p21/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                   12.8876(15)
_cell_length_b                   5.7106(7)
_cell_length_c                   14.2015(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.7800(10)
_cell_angle_gamma                90.00
_cell_volume                     1045.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1788
_cell_measurement_theta_min      5.706
_cell_measurement_theta_max      52.808

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.97
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS.G.Sheldrick(1999)

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Siemens SMART,Bruker APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7268
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0093
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1842
_reflns_number_gt                1788
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-SEED,L.Barbour(1999):http://x-seed.net/
_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^)+(0.0396P)^2^+0.6116P] 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_number_reflns         1842
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C8 C 0.61997(10) 0.0523(2) 0.59098(9) 0.0182(3) Uani 1 1 d . . .
H8 H 0.6078 -0.0691 0.5464 0.022 Uiso 1 1 calc R . .
C10 C 0.58693(10) 0.2246(3) 0.74249(9) 0.0214(3) Uani 1 1 d . . .
H10 H 0.5528 0.2211 0.8013 0.026 Uiso 1 1 calc R . .
C11 C 0.57026(10) 0.0479(3) 0.67732(9) 0.0212(3) Uani 1 1 d . . .
H11 H 0.5246 -0.0773 0.6916 0.025 Uiso 1 1 calc R . .
C12 C 0.74557(10) 0.2329(2) 0.47603(9) 0.0158(3) Uani 1 1 d . . .
C14 C 0.65366(11) 0.4066(3) 0.72138(9) 0.0223(3) Uani 1 1 d . . .
H14 H 0.6650 0.5285 0.7658 0.027 Uiso 1 1 calc R . .
C15 C 0.70403(10) 0.4120(2) 0.63558(9) 0.0197(3) Uani 1 1 d . . .
H15 H 0.7499 0.5372 0.6217 0.024 Uiso 1 1 calc R . .
C16 C 0.68763(9) 0.2345(2) 0.56986(8) 0.0153(3) Uani 1 1 d . . .
F1 F 0.91314(6) 0.14184(15) 0.41675(6) 0.0269(2) Uani 1 1 d . . .
F3 F 0.90928(6) 0.34229(16) 0.54505(6) 0.0298(2) Uani 1 1 d . . .
F7 F 0.86906(6) -0.02487(15) 0.54591(6) 0.0279(2) Uani 1 1 d . . .
C1 C 0.86079(10) 0.1744(3) 0.49660(9) 0.0210(3) Uani 1 1 d . . .
C2 C 0.73269(10) 0.4761(2) 0.42877(9) 0.0156(3) Uani 1 1 d . . .
H2 H 0.7528 0.6001 0.4752 0.019 Uiso 1 1 calc R . .
O1 O 0.78004(8) 0.37282(17) 0.27484(6) 0.0245(2) Uani 1 1 d . . .
O2 O 0.87477(7) 0.63147(17) 0.34701(7) 0.0233(2) Uani 1 1 d . . .
O3 O 0.70540(7) 0.05012(16) 0.42019(6) 0.0182(2) Uani 1 1 d . . .
H3 H 0.7251 0.0668 0.3645 0.022 Uiso 1 1 calc R . .
N4 N 0.80216(9) 0.49549(19) 0.34363(7) 0.0173(3) Uani 1 1 d . . .
C3 C 0.62115(10) 0.5179(2) 0.39650(10) 0.0207(3) Uani 1 1 d . . .
H3A H 0.6151 0.6749 0.3691 0.031 Uiso 1 1 calc R . .
H3B H 0.5750 0.5052 0.4505 0.031 Uiso 1 1 calc R . .
H3C H 0.6015 0.4007 0.3491 0.031 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
C8 0.0190(6) 0.0175(7) 0.0179(6) -0.0012(5) -0.0005(5) 0.0008(5)
C10 0.0193(6) 0.0296(8) 0.0155(6) 0.0024(6) 0.0034(5) 0.0058(6)
C11 0.0171(6) 0.0238(7) 0.0228(7) 0.0046(6) 0.0025(5) -0.0014(5)
C12 0.0181(6) 0.0152(6) 0.0142(6) -0.0004(5) 0.0004(5) -0.0004(5)
C14 0.0270(7) 0.0237(7) 0.0161(6) -0.0037(6) -0.0010(5) 0.0030(6)
C15 0.0217(7) 0.0200(7) 0.0173(6) 0.0001(5) -0.0005(5) -0.0021(5)
C16 0.0149(6) 0.0174(6) 0.0136(6) 0.0020(5) -0.0004(5) 0.0034(5)
F1 0.0227(4) 0.0333(5) 0.0251(4) 0.0067(4) 0.0095(3) 0.0092(4)
F3 0.0187(4) 0.0389(5) 0.0316(5) -0.0017(4) -0.0048(3) -0.0017(4)
F7 0.0260(4) 0.0317(5) 0.0260(4) 0.0118(4) 0.0031(3) 0.0109(4)
C1 0.0208(7) 0.0250(7) 0.0173(6) 0.0041(6) 0.0033(5) 0.0037(6)
C2 0.0170(6) 0.0163(6) 0.0134(6) -0.0003(5) 0.0022(5) 0.0001(5)
O1 0.0384(6) 0.0200(5) 0.0151(5) -0.0025(4) 0.0026(4) -0.0013(4)
O2 0.0212(5) 0.0240(5) 0.0249(5) 0.0023(4) 0.0039(4) -0.0056(4)
O3 0.0270(5) 0.0149(5) 0.0127(4) -0.0019(4) 0.0033(4) -0.0018(4)
N4 0.0216(6) 0.0151(6) 0.0152(5) 0.0014(4) 0.0013(4) 0.0013(5)
C3 0.0178(7) 0.0214(7) 0.0229(7) 0.0034(5) -0.0007(5) 0.0014(5)

_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
C8 C11 1.3913(18) . ?
C8 C16 1.3930(19) . ?
C10 C14 1.384(2) . ?
C10 C11 1.384(2) . ?
C12 O3 1.4055(15) . ?
C12 C16 1.5363(16) . ?
C12 C1 1.5460(18) . ?
C12 C2 1.5503(18) . ?
C14 C15 1.3888(19) . ?
C15 C16 1.3920(19) . ?
F1 C1 1.3403(15) . ?
F3 C1 1.3309(17) . ?
F7 C1 1.3399(16) . ?
C2 N4 1.5183(16) . ?
C2 C3 1.5217(18) . ?
O1 N4 1.2324(14) . ?
O2 N4 1.2165(15) . ?

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
C11 C8 C16 120.02(12) . . ?
C14 C10 C11 119.59(12) . . ?
C10 C11 C8 120.47(13) . . ?
O3 C12 C16 108.30(10) . . ?
O3 C12 C1 106.95(10) . . ?
C16 C12 C1 108.32(10) . . ?
O3 C12 C2 112.62(10) . . ?
C16 C12 C2 108.65(10) . . ?
C1 C12 C2 111.85(11) . . ?
C10 C14 C15 120.38(13) . . ?
C14 C15 C16 120.24(13) . . ?
C15 C16 C8 119.30(12) . . ?
C15 C16 C12 120.97(11) . . ?
C8 C16 C12 119.70(11) . . ?
F3 C1 F7 107.94(11) . . ?
F3 C1 F1 107.41(11) . . ?
F7 C1 F1 106.67(11) . . ?
F3 C1 C12 112.65(11) . . ?
F7 C1 C12 110.59(11) . . ?
F1 C1 C12 111.31(11) . . ?
N4 C2 C3 108.27(10) . . ?
N4 C2 C12 110.44(10) . . ?
C3 C2 C12 111.48(11) . . ?
O2 N4 O1 124.30(11) . . ?
O2 N4 C2 118.48(10) . . ?
O1 N4 C2 117.22(10) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040

#===END