# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Wei Wang'
'Hao Li'
'Xixi Song'
'Chenguang Yu'
'Shilei Zhang'
_publ_contact_author_name        'Wei Wang'
_publ_contact_author_email       WWANG@UNM.EDU

data_3n
_database_code_depnum_ccdc_archive 'CCDC 716267'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_absolute_configuration ad

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C13 H13 Cl F N O6'

_chemical_formula_sum            'C13 H13 Cl F N O6'

_chemical_formula_weight         333.69

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'
Cl Cl 0.1484 0.1585 '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)

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   9.2128(6)

_cell_length_b                   7.5548(5)

_cell_length_c                   11.3782(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 112.449(4)

_cell_angle_gamma                90.00

_cell_volume                     731.92(9)

_cell_formula_units_Z            2

_cell_measurement_temperature    225(2)

_cell_measurement_reflns_used    7017

_cell_measurement_theta_min      2.39

_cell_measurement_theta_max      32.11

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.50

_exptl_crystal_size_mid          0.46

_exptl_crystal_size_min          0.46

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.514

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             344

_exptl_absorpt_coefficient_mu    0.301

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.8641

_exptl_absorpt_correction_T_max  0.8739

_exptl_absorpt_process_details   Bruker,SADABS

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      225(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            21749

_diffrn_reflns_av_R_equivalents  0.0235

_diffrn_reflns_av_sigmaI/netI    0.0228

_diffrn_reflns_limit_h_min       -13

_diffrn_reflns_limit_h_max       13

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         3.61

_diffrn_reflns_theta_max         32.19

_reflns_number_total             5088

_reflns_number_gt                4524

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_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^)+(0.0469P)^2^+0.0651P] 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    noref

_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   0.07(5)

_refine_ls_number_reflns         5088

_refine_ls_number_parameters     201

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0405

_refine_ls_R_factor_gt           0.0341

_refine_ls_wR_factor_ref         0.0875

_refine_ls_wR_factor_gt          0.0834

_refine_ls_goodness_of_fit_ref   1.025

_refine_ls_restrained_S_all      1.025

_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

Cl Cl 0.24482(5) 0.21424(7) 0.63722(4) 0.05402(12) Uani 1 1 d . . .
F F -0.08709(9) 0.44076(10) 0.89638(6) 0.03025(15) Uani 1 1 d . . .
N N -0.19407(14) 0.02364(15) 0.72338(12) 0.0345(2) Uani 1 1 d . . .
O1 O -0.17997(15) -0.05058(16) 0.63370(11) 0.0509(3) Uani 1 1 d . . .
O2 O -0.31923(15) 0.0432(2) 0.73444(14) 0.0680(4) Uani 1 1 d . . .
O3 O 0.08552(11) 0.69369(13) 0.85710(9) 0.0386(2) Uani 1 1 d . . .
O4 O 0.04743(11) 0.58288(14) 0.66385(9) 0.0353(2) Uani 1 1 d . . .
O5 O -0.26577(12) 0.35383(15) 0.57890(10) 0.0437(3) Uani 1 1 d . . .
O6 O -0.31047(11) 0.56818(14) 0.69675(10) 0.0380(2) Uani 1 1 d . . .
C1 C 0.30372(15) 0.25481(18) 0.79917(12) 0.0335(2) Uani 1 1 d . . .
C2 C 0.46367(16) 0.2761(3) 0.86961(17) 0.0468(4) Uani 1 1 d . . .
H2 H 0.5354 0.2710 0.8291 0.056 Uiso 1 1 calc R . .
C3 C 0.51644(17) 0.3046(3) 0.99834(17) 0.0520(4) Uani 1 1 d . . .
H3 H 0.6243 0.3205 1.0460 0.062 Uiso 1 1 calc R . .
C4 C 0.41084(17) 0.3099(3) 1.05784(15) 0.0478(4) Uani 1 1 d . . .
H4 H 0.4473 0.3270 1.1462 0.057 Uiso 1 1 calc R . .
C5 C 0.25118(15) 0.2899(2) 0.98764(12) 0.0363(3) Uani 1 1 d . . .
H5 H 0.1806 0.2931 1.0293 0.044 Uiso 1 1 calc R . .
C6 C 0.19372(13) 0.26516(15) 0.85595(11) 0.0264(2) Uani 1 1 d . . .
C7 C 0.01857(13) 0.25156(14) 0.77921(10) 0.02297(19) Uani 1 1 d . . .
H7 H 0.0034 0.2284 0.6896 0.028 Uiso 1 1 calc R . .
C8 C -0.04992(15) 0.09425(17) 0.82604(12) 0.0310(2) Uani 1 1 d . . .
H8A H 0.0290 0.0002 0.8555 0.037 Uiso 1 1 calc R . .
H8B H -0.0757 0.1317 0.8982 0.037 Uiso 1 1 calc R . .
C9 C -0.06610(12) 0.42667(15) 0.78292(9) 0.02195(18) Uani 1 1 d . . .
C10 C 0.03237(13) 0.58664(16) 0.77476(11) 0.0260(2) Uani 1 1 d . . .
C11 C 0.1441(2) 0.7192(3) 0.64086(18) 0.0519(4) Uani 1 1 d . . .
H11A H 0.0956 0.8339 0.6381 0.078 Uiso 1 1 calc R . .
H11B H 0.1540 0.6969 0.5603 0.078 Uiso 1 1 calc R . .
H11C H 0.2474 0.7181 0.7088 0.078 Uiso 1 1 calc R . .
C12 C -0.22770(12) 0.44113(16) 0.67297(11) 0.0248(2) Uani 1 1 d . . .
C13 C -0.46180(16) 0.6052(3) 0.59592(16) 0.0469(4) Uani 1 1 d . . .
H13A H -0.4482 0.6201 0.5161 0.070 Uiso 1 1 calc R . .
H13B H -0.5052 0.7128 0.6158 0.070 Uiso 1 1 calc R . .
H13C H -0.5329 0.5074 0.5887 0.070 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

Cl 0.04735(19) 0.0842(3) 0.03916(17) -0.00684(19) 0.02619(15) 0.0022(2)
F 0.0358(4) 0.0357(4) 0.0205(3) -0.0007(3) 0.0121(3) 0.0060(3)
N 0.0352(5) 0.0309(5) 0.0357(6) 0.0040(4) 0.0115(5) -0.0047(4)
O1 0.0546(7) 0.0464(6) 0.0433(6) -0.0173(5) 0.0095(5) -0.0007(5)
O2 0.0383(6) 0.1091(13) 0.0620(8) 0.0069(8) 0.0251(6) -0.0040(7)
O3 0.0382(5) 0.0283(4) 0.0401(5) -0.0058(4) 0.0046(4) -0.0036(4)
O4 0.0371(5) 0.0359(5) 0.0355(5) 0.0048(4) 0.0166(4) -0.0045(4)
O5 0.0365(5) 0.0483(6) 0.0318(5) -0.0119(4) -0.0032(4) 0.0098(4)
O6 0.0264(4) 0.0450(6) 0.0350(5) -0.0050(4) 0.0033(4) 0.0125(4)
C1 0.0312(6) 0.0358(6) 0.0348(6) 0.0019(5) 0.0140(5) 0.0050(5)
C2 0.0268(6) 0.0567(9) 0.0573(9) 0.0057(7) 0.0166(6) 0.0074(6)
C3 0.0267(6) 0.0618(10) 0.0548(9) 0.0021(8) 0.0013(6) 0.0073(7)
C4 0.0341(6) 0.0606(10) 0.0346(7) -0.0026(7) -0.0026(5) 0.0108(7)
C5 0.0306(6) 0.0449(7) 0.0280(6) -0.0017(5) 0.0053(5) 0.0097(5)
C6 0.0247(5) 0.0255(5) 0.0264(5) 0.0008(4) 0.0067(4) 0.0060(4)
C7 0.0246(4) 0.0230(5) 0.0199(4) -0.0001(4) 0.0069(3) 0.0030(4)
C8 0.0370(6) 0.0252(5) 0.0268(5) 0.0022(4) 0.0077(4) -0.0006(5)
C9 0.0230(4) 0.0238(4) 0.0175(4) -0.0005(4) 0.0059(3) 0.0019(4)
C10 0.0215(4) 0.0229(5) 0.0289(5) 0.0025(4) 0.0043(4) 0.0031(4)
C11 0.0454(8) 0.0526(9) 0.0641(10) 0.0151(8) 0.0281(7) -0.0085(7)
C12 0.0217(4) 0.0267(5) 0.0240(5) 0.0021(4) 0.0064(4) 0.0001(4)
C13 0.0256(6) 0.0590(9) 0.0455(8) 0.0013(7) 0.0017(5) 0.0128(6)

_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

Cl C1 1.7379(14) . ?
F C9 1.3806(12) . ?
N O1 1.2140(17) . ?
N O2 1.2158(17) . ?
N C8 1.4926(17) . ?
O3 C10 1.1921(15) . ?
O4 C10 1.3215(15) . ?
O4 C11 1.4492(17) . ?
O5 C12 1.1904(15) . ?
O6 C12 1.3166(15) . ?
O6 C13 1.4549(15) . ?
C1 C2 1.3921(19) . ?
C1 C6 1.3967(17) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.3881(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3980(17) . ?
C5 H5 0.9400 . ?
C6 C7 1.5168(15) . ?
C7 C8 1.5334(17) . ?
C7 C9 1.5445(15) . ?
C7 H7 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.5351(16) . ?
C9 C12 1.5398(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?

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

O1 N O2 123.60(14) . . ?
O1 N C8 118.30(12) . . ?
O2 N C8 118.10(13) . . ?
C10 O4 C11 116.93(12) . . ?
C12 O6 C13 115.72(11) . . ?
C2 C1 C6 121.51(13) . . ?
C2 C1 Cl 117.66(11) . . ?
C6 C1 Cl 120.83(10) . . ?
C3 C2 C1 119.88(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.91(13) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.30(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 121.04(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.30(11) . . ?
C1 C6 C7 122.02(10) . . ?
C5 C6 C7 120.68(11) . . ?
C6 C7 C8 109.94(9) . . ?
C6 C7 C9 111.32(9) . . ?
C8 C7 C9 112.04(9) . . ?
C6 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
C9 C7 H7 107.8 . . ?
N C8 C7 111.48(10) . . ?
N C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
F C9 C10 107.03(9) . . ?
F C9 C12 108.48(8) . . ?
C10 C9 C12 107.78(9) . . ?
F C9 C7 110.13(9) . . ?
C10 C9 C7 110.88(8) . . ?
C12 C9 C7 112.35(9) . . ?
O3 C10 O4 127.13(12) . . ?
O3 C10 C9 124.16(12) . . ?
O4 C10 C9 108.71(10) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 O6 126.43(11) . . ?
O5 C12 C9 123.55(10) . . ?
O6 C12 C9 109.93(9) . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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

C6 C1 C2 C3 1.3(3) . . . . ?
Cl C1 C2 C3 -178.59(15) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C2 C1 C6 C5 -2.8(2) . . . . ?
Cl C1 C6 C5 177.08(11) . . . . ?
C2 C1 C6 C7 176.80(13) . . . . ?
Cl C1 C6 C7 -3.31(16) . . . . ?
C4 C5 C6 C1 2.3(2) . . . . ?
C4 C5 C6 C7 -177.29(14) . . . . ?
C1 C6 C7 C8 120.47(12) . . . . ?
C5 C6 C7 C8 -59.93(14) . . . . ?
C1 C6 C7 C9 -114.78(12) . . . . ?
C5 C6 C7 C9 64.82(14) . . . . ?
O1 N C8 C7 68.67(15) . . . . ?
O2 N C8 C7 -111.55(15) . . . . ?
C6 C7 C8 N -153.50(10) . . . . ?
C9 C7 C8 N 82.16(12) . . . . ?
C6 C7 C9 F -78.76(11) . . . . ?
C8 C7 C9 F 44.81(11) . . . . ?
C6 C7 C9 C10 39.51(12) . . . . ?
C8 C7 C9 C10 163.08(9) . . . . ?
C6 C7 C9 C12 160.20(9) . . . . ?
C8 C7 C9 C12 -76.24(12) . . . . ?
C11 O4 C10 O3 2.66(18) . . . . ?
C11 O4 C10 C9 -176.93(11) . . . . ?
F C9 C10 O3 3.87(14) . . . . ?
C12 C9 C10 O3 120.38(12) . . . . ?
C7 C9 C10 O3 -116.27(12) . . . . ?
F C9 C10 O4 -176.53(9) . . . . ?
C12 C9 C10 O4 -60.02(11) . . . . ?
C7 C9 C10 O4 63.34(11) . . . . ?
C13 O6 C12 O5 -1.1(2) . . . . ?
C13 O6 C12 C9 175.58(12) . . . . ?
F C9 C12 O5 -140.50(13) . . . . ?
C10 C9 C12 O5 103.94(14) . . . . ?
C7 C9 C12 O5 -18.51(17) . . . . ?
F C9 C12 O6 42.69(13) . . . . ?
C10 C9 C12 O6 -72.87(12) . . . . ?
C7 C9 C12 O6 164.68(10) . . . . ?

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

C7 H7 Cl 0.99 2.52 3.0995(12) 117.5 .
C7 H7 O5 0.99 2.50 2.8450(14) 100.1 .
C8 H8A O3 0.98 2.37 3.2409(16) 147.4 1_545
C8 H8B F 0.98 2.34 2.7964(15) 107.8 .
C11 H11B O5 0.97 2.49 3.2687(19) 136.8 2_556

_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        32.19

_diffrn_measured_fraction_theta_full 0.991

_refine_diff_density_max         0.239

_refine_diff_density_min         -0.327

_refine_diff_density_rms         0.054