# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Jian Wang'
_publ_contact_author_email       chmwangj@nus.edu.sg
loop_
_publ_author_name
'Yaojun Gao'
'Qiao Ren'

data_a812
_database_code_depnum_ccdc_archive 'CCDC 813006'
#TrackingRef '- Crystal CCDC 813006.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 Br Cl N O6'
_chemical_formula_weight         544.77

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'
Cl Cl 0.1484 0.1585 '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                   6.0482(2)
_cell_length_b                   15.3621(6)
_cell_length_c                   24.9148(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2314.91(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4422
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      24.61

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3899
_exptl_absorpt_correction_T_max  0.6984
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(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            16388
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5282
_reflns_number_gt                4394
_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^)+(0.0140P)^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   0.002(6)
_refine_ls_number_reflns         5282
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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 0.15129(5) 0.859072(18) 0.863957(12) 0.05207(10) Uani 1 1 d . . .
Cl1 Cl 1.41882(14) 0.17707(6) 0.71239(3) 0.0597(2) Uani 1 1 d . . .
O1 O 0.7386(3) 0.50598(10) 0.93845(6) 0.0296(4) Uani 1 1 d . . .
O2 O 0.8659(3) 0.42510(10) 1.00710(6) 0.0332(4) Uani 1 1 d . . .
O3 O 0.6427(3) 0.36721(10) 0.87898(5) 0.0273(3) Uani 1 1 d . . .
O4 O 0.3330(3) 0.39314(12) 0.92628(6) 0.0385(4) Uani 1 1 d . . .
O5 O 0.8207(4) -0.02632(11) 0.95635(8) 0.0501(5) Uani 1 1 d . . .
O6 O 0.6715(4) 0.02801(11) 0.88569(7) 0.0476(5) Uani 1 1 d . . .
N1 N 0.7734(3) 0.03475(13) 0.92751(8) 0.0304(5) Uani 1 1 d . . .
C1 C 0.3320(5) 0.77445(15) 0.89865(9) 0.0340(6) Uani 1 1 d . . .
C2 C 0.5328(5) 0.79930(16) 0.91915(11) 0.0391(6) Uani 1 1 d . . .
H2 H 0.5788 0.8577 0.9172 0.047 Uiso 1 1 calc R . .
C3 C 0.6665(5) 0.73705(15) 0.94280(9) 0.0359(6) Uani 1 1 d . . .
H3 H 0.8046 0.7534 0.9569 0.043 Uiso 1 1 calc R . .
C4 C 0.5997(4) 0.65101(15) 0.94599(9) 0.0306(5) Uani 1 1 d . . .
C5 C 0.3927(4) 0.62816(15) 0.92594(10) 0.0352(6) Uani 1 1 d . . .
H5 H 0.3433 0.5703 0.9289 0.042 Uiso 1 1 calc R . .
C6 C 0.2599(4) 0.68939(15) 0.90188(10) 0.0357(6) Uani 1 1 d . . .
H6A H 0.1215 0.6735 0.8878 0.043 Uiso 1 1 calc R . .
C7 C 0.7450(4) 0.58399(15) 0.97220(10) 0.0336(6) Uani 1 1 d . . .
H7A H 0.8969 0.6057 0.9751 0.040 Uiso 1 1 calc R . .
H7B H 0.6907 0.5706 1.0083 0.040 Uiso 1 1 calc R . .
C8 C 0.7953(4) 0.43150(14) 0.96196(9) 0.0262(5) Uani 1 1 d . . .
C9 C 0.7595(4) 0.35458(15) 0.92651(8) 0.0252(5) Uani 1 1 d . . .
C10 C 0.4261(4) 0.39382(15) 0.88352(10) 0.0280(5) Uani 1 1 d . . .
C11 C 0.3323(4) 0.42202(14) 0.83207(9) 0.0279(5) Uani 1 1 d . . .
C12 C 0.4433(4) 0.41209(16) 0.78339(9) 0.0344(6) Uani 1 1 d . . .
H12 H 0.5831 0.3855 0.7825 0.041 Uiso 1 1 calc R . .
C13 C 0.3474(5) 0.44144(17) 0.73638(10) 0.0429(6) Uani 1 1 d . . .
H13 H 0.4209 0.4338 0.7035 0.051 Uiso 1 1 calc R . .
C14 C 0.1436(5) 0.48206(17) 0.73778(10) 0.0438(7) Uani 1 1 d . . .
H14 H 0.0801 0.5028 0.7058 0.053 Uiso 1 1 calc R . .
C15 C 0.0334(5) 0.49225(17) 0.78547(11) 0.0432(7) Uani 1 1 d . . .
H15 H -0.1053 0.5198 0.7861 0.052 Uiso 1 1 calc R . .
C16 C 0.1263(4) 0.46197(16) 0.83257(10) 0.0361(6) Uani 1 1 d . . .
H16 H 0.0497 0.4685 0.8651 0.043 Uiso 1 1 calc R . .
C17 C 0.8513(4) 0.27878(14) 0.93713(8) 0.0260(5) Uani 1 1 d . . .
H17 H 0.9465 0.2765 0.9669 0.031 Uiso 1 1 calc R . .
C18 C 0.8190(4) 0.19531(13) 0.90637(8) 0.0255(5) Uani 1 1 d . . .
H18 H 0.6654 0.1945 0.8926 0.031 Uiso 1 1 calc R . .
C19 C 0.8416(4) 0.12234(13) 0.94741(9) 0.0285(5) Uani 1 1 d . . .
H19A H 0.9962 0.1193 0.9591 0.034 Uiso 1 1 calc R . .
H19B H 0.7519 0.1369 0.9789 0.034 Uiso 1 1 calc R . .
C20 C 0.9756(4) 0.18820(14) 0.85820(9) 0.0250(5) Uani 1 1 d . . .
C21 C 1.1814(4) 0.14885(15) 0.86082(9) 0.0336(5) Uani 1 1 d . . .
H21 H 1.2296 0.1246 0.8934 0.040 Uiso 1 1 calc R . .
C22 C 1.3181(4) 0.14465(18) 0.81593(10) 0.0392(6) Uani 1 1 d . . .
H22 H 1.4563 0.1168 0.8179 0.047 Uiso 1 1 calc R . .
C23 C 1.2475(4) 0.18194(17) 0.76850(10) 0.0360(6) Uani 1 1 d . . .
C24 C 1.0445(5) 0.22141(17) 0.76503(10) 0.0398(7) Uani 1 1 d . . .
H24 H 0.9975 0.2465 0.7326 0.048 Uiso 1 1 calc R . .
C25 C 0.9108(4) 0.22384(16) 0.80954(9) 0.0358(6) Uani 1 1 d . . .
H25 H 0.7713 0.2504 0.8070 0.043 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 0.05982(19) 0.04057(15) 0.05583(18) 0.00374(14) -0.00222(16) 0.01071(15)
Cl1 0.0615(5) 0.0845(6) 0.0331(4) 0.0019(4) 0.0191(4) -0.0084(4)
O1 0.0398(9) 0.0242(8) 0.0250(8) -0.0037(7) 0.0025(7) -0.0005(7)
O2 0.0365(9) 0.0374(9) 0.0255(9) -0.0038(7) -0.0047(8) 0.0008(8)
O3 0.0290(8) 0.0328(8) 0.0200(8) -0.0009(6) -0.0028(7) 0.0047(8)
O4 0.0331(9) 0.0581(11) 0.0241(9) 0.0033(8) 0.0032(8) -0.0045(9)
O5 0.0655(13) 0.0299(10) 0.0549(12) 0.0077(9) -0.0136(12) 0.0047(10)
O6 0.0720(14) 0.0400(10) 0.0308(9) -0.0022(8) -0.0128(11) -0.0143(10)
N1 0.0345(12) 0.0272(11) 0.0295(11) 0.0004(9) 0.0037(10) 0.0003(9)
C1 0.0394(14) 0.0304(13) 0.0321(13) -0.0029(10) 0.0063(13) 0.0064(12)
C2 0.0469(16) 0.0251(13) 0.0453(17) -0.0059(11) 0.0048(13) -0.0039(12)
C3 0.0371(14) 0.0337(13) 0.0370(14) -0.0085(11) 0.0012(13) -0.0089(12)
C4 0.0359(14) 0.0278(12) 0.0281(12) -0.0054(10) 0.0080(10) -0.0022(10)
C5 0.0344(14) 0.0254(13) 0.0457(15) -0.0027(10) 0.0072(11) -0.0056(11)
C6 0.0330(13) 0.0354(14) 0.0388(14) -0.0066(12) 0.0035(12) -0.0041(11)
C7 0.0371(13) 0.0306(14) 0.0330(14) -0.0078(10) 0.0020(12) -0.0048(11)
C8 0.0222(12) 0.0293(12) 0.0270(13) -0.0016(10) 0.0034(10) -0.0023(9)
C9 0.0248(11) 0.0306(12) 0.0203(11) -0.0003(10) 0.0018(9) -0.0030(10)
C10 0.0293(12) 0.0279(12) 0.0267(13) 0.0007(10) -0.0003(10) -0.0042(10)
C11 0.0300(12) 0.0265(11) 0.0273(12) 0.0014(9) -0.0020(11) -0.0056(11)
C12 0.0372(14) 0.0375(14) 0.0286(14) 0.0018(11) 0.0001(12) 0.0023(12)
C13 0.0583(17) 0.0469(16) 0.0235(13) 0.0049(11) 0.0003(14) 0.0045(16)
C14 0.0519(17) 0.0470(16) 0.0324(14) 0.0114(12) -0.0164(15) -0.0045(15)
C15 0.0321(14) 0.0453(16) 0.0523(18) 0.0135(14) -0.0066(14) 0.0008(13)
C16 0.0332(15) 0.0412(14) 0.0338(14) 0.0039(11) 0.0031(12) -0.0042(12)
C17 0.0260(11) 0.0327(12) 0.0193(11) 0.0003(9) -0.0033(11) -0.0033(11)
C18 0.0261(12) 0.0285(12) 0.0218(11) 0.0013(9) -0.0047(10) -0.0021(10)
C19 0.0317(12) 0.0307(12) 0.0232(11) -0.0021(9) -0.0010(11) -0.0042(11)
C20 0.0303(12) 0.0223(11) 0.0224(12) -0.0001(10) -0.0011(10) -0.0035(9)
C21 0.0339(13) 0.0439(14) 0.0230(12) 0.0044(11) -0.0023(12) -0.0006(12)
C22 0.0315(13) 0.0550(15) 0.0311(13) 0.0001(12) -0.0013(11) 0.0024(14)
C23 0.0434(16) 0.0380(15) 0.0268(13) -0.0017(11) 0.0098(12) -0.0103(13)
C24 0.0578(18) 0.0399(15) 0.0217(13) 0.0069(11) -0.0025(13) 0.0019(14)
C25 0.0415(16) 0.0377(14) 0.0282(14) 0.0023(11) -0.0031(12) 0.0077(12)

_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 C1 1.906(3) . ?
Cl1 C23 1.742(3) . ?
O1 C8 1.330(3) . ?
O1 C7 1.465(3) . ?
O2 C8 1.207(3) . ?
O3 C10 1.377(3) . ?
O3 C9 1.392(3) . ?
O4 C10 1.205(3) . ?
O5 N1 1.216(2) . ?
O6 N1 1.215(3) . ?
N1 C19 1.492(3) . ?
C1 C2 1.371(4) . ?
C1 C6 1.380(3) . ?
C2 C3 1.384(4) . ?
C3 C4 1.384(3) . ?
C4 C5 1.393(3) . ?
C4 C7 1.503(3) . ?
C5 C6 1.374(3) . ?
C8 C9 1.491(3) . ?
C9 C17 1.317(3) . ?
C10 C11 1.467(3) . ?
C11 C16 1.389(4) . ?
C11 C12 1.395(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.382(4) . ?
C14 C15 1.371(4) . ?
C15 C16 1.382(4) . ?
C17 C18 1.506(3) . ?
C18 C19 1.523(3) . ?
C18 C20 1.533(3) . ?
C20 C21 1.386(3) . ?
C20 C25 1.387(3) . ?
C21 C22 1.392(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.372(4) . ?
C24 C25 1.373(4) . ?

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
C8 O1 C7 116.35(17) . . ?
C10 O3 C9 117.00(16) . . ?
O6 N1 O5 124.1(2) . . ?
O6 N1 C19 120.13(19) . . ?
O5 N1 C19 115.8(2) . . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 Br1 119.14(18) . . ?
C6 C1 Br1 119.4(2) . . ?
C1 C2 C3 118.9(2) . . ?
C2 C3 C4 120.9(3) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C7 120.5(2) . . ?
C5 C4 C7 120.6(2) . . ?
C6 C5 C4 120.6(2) . . ?
C5 C6 C1 119.3(2) . . ?
O1 C7 C4 107.18(19) . . ?
O2 C8 O1 124.9(2) . . ?
O2 C8 C9 122.6(2) . . ?
O1 C8 C9 112.53(19) . . ?
C17 C9 O3 120.5(2) . . ?
C17 C9 C8 121.4(2) . . ?
O3 C9 C8 117.8(2) . . ?
O4 C10 O3 121.0(2) . . ?
O4 C10 C11 126.5(2) . . ?
O3 C10 C11 112.6(2) . . ?
C16 C11 C12 119.2(2) . . ?
C16 C11 C10 118.0(2) . . ?
C12 C11 C10 122.8(2) . . ?
C13 C12 C11 120.0(2) . . ?
C14 C13 C12 120.0(3) . . ?
C15 C14 C13 120.5(2) . . ?
C14 C15 C16 120.0(3) . . ?
C15 C16 C11 120.4(2) . . ?
C9 C17 C18 126.6(2) . . ?
C17 C18 C19 105.86(17) . . ?
C17 C18 C20 112.26(18) . . ?
C19 C18 C20 114.69(19) . . ?
N1 C19 C18 114.56(18) . . ?
C21 C20 C25 117.8(2) . . ?
C21 C20 C18 123.3(2) . . ?
C25 C20 C18 118.8(2) . . ?
C20 C21 C22 121.0(2) . . ?
C23 C22 C21 119.0(2) . . ?
C24 C23 C22 120.9(2) . . ?
C24 C23 Cl1 120.1(2) . . ?
C22 C23 Cl1 119.0(2) . . ?
C23 C24 C25 119.2(2) . . ?
C24 C25 C20 122.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051