# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       hongbing.fu@iccas.ac.cn
_publ_contact_author_name        'Hongbing Fu'
loop_
_publ_author_name
'Jiannian Yao'
'Xinqiang Cao'
'Shuming Bao'
'Yi-Shi Wu'
'Qing Liao'
'Qiang Shi'
'Hongbing Fu'

data_a
_database_code_depnum_ccdc_archive 'CCDC 858806'
#TrackingRef '8662_web_deposit_cif_file_0_ChrisCao_1323871893.a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 Cl4 N2 O4'
_chemical_formula_sum            'C24 H6 Cl4 N2 O4'
_chemical_formula_weight         528.11

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   14.324(3)
_cell_length_b                   7.1135(14)
_cell_length_c                   19.269(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1963.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4193
_cell_measurement_theta_min      1.7715
_cell_measurement_theta_max      27.4650

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7509
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5341
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2234
_reflns_number_gt                2039
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_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^)+(0.0410P)^2^+2.7905P] 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         2234
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.166
_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
Cl1 Cl 0.59363(6) 1.06989(13) 0.92906(4) 0.0364(2) Uani 0.906(2) 1 d P A 1
Cl2 Cl 0.49503(5) 0.68000(13) 0.55519(4) 0.0313(2) Uani 0.906(2) 1 d P A 1
Cl3 Cl 0.7854(4) 1.0336(9) 0.9150(3) 0.0182(18) Uiso 0.094(2) 1 d P A 2
Cl4 Cl 0.7035(7) 0.6414(17) 0.5315(5) 0.055(3) Uani 0.094(2) 1 d P A 2
O1 O 0.91769(15) 0.9252(4) 0.80772(12) 0.0414(6) Uani 1 1 d . A .
O2 O 0.86016(17) 0.7659(4) 0.58450(13) 0.0533(7) Uani 1 1 d . . .
N1 N 0.88573(18) 0.8485(4) 0.69637(14) 0.0366(6) Uani 1 1 d . A .
H1A H 0.9461 0.8459 0.6880 0.044 Uiso 1 1 calc R . .
C1 C 0.8278(2) 0.8048(5) 0.64077(16) 0.0356(7) Uani 1 1 d . . .
C2 C 0.7262(2) 0.8093(4) 0.65575(15) 0.0312(7) Uani 1 1 d . A .
C3 C 0.6629(2) 0.7580(5) 0.60570(15) 0.0325(7) Uani 1 1 d . . .
H4 H 0.6847 0.7117 0.5618 0.039 Uiso 0.906(2) 1 d PR A .
C4 C 0.5671(2) 0.7721(4) 0.61808(14) 0.0296(6) Uani 1 1 d . A .
H2 H 0.5240 0.7320 0.5829 0.036 Uiso 0.094(2) 1 d PR . .
C5 C 0.5323(2) 0.8439(4) 0.68048(14) 0.0266(6) Uani 1 1 d . . .
C6 C 0.59740(19) 0.8663(4) 0.73589(14) 0.0254(6) Uani 1 1 d . A .
C7 C 0.56531(19) 0.8932(4) 0.80546(14) 0.0267(6) Uani 1 1 d . . .
C8 C 0.6291(2) 0.9633(5) 0.85339(15) 0.0313(7) Uani 1 1 d . A .
H1 H 0.6069 1.0101 0.8971 0.038 Uiso 0.094(2) 1 d PR . .
C9 C 0.7254(2) 0.9652(5) 0.83942(16) 0.0330(7) Uani 1 1 d . . .
H3 H 0.7685 1.0086 0.8741 0.040 Uiso 0.906(2) 1 d PR A .
C10 C 0.7579(2) 0.9066(4) 0.77599(15) 0.0296(6) Uani 1 1 d . A .
C11 C 0.69444(19) 0.8611(4) 0.72253(15) 0.0278(6) Uani 1 1 d . . .
C12 C 0.8597(2) 0.8951(5) 0.76276(16) 0.0324(7) Uani 1 1 d . . .

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
Cl1 0.0366(5) 0.0473(5) 0.0253(4) -0.0129(4) -0.0009(3) 0.0005(4)
Cl2 0.0264(4) 0.0472(5) 0.0204(3) -0.0067(3) -0.0009(3) -0.0064(3)
Cl4 0.046(5) 0.077(8) 0.041(5) 0.003(5) 0.009(4) 0.006(5)
O1 0.0222(10) 0.0574(16) 0.0447(13) -0.0025(12) -0.0046(10) -0.0007(10)
O2 0.0335(12) 0.079(2) 0.0478(14) -0.0142(14) 0.0124(11) 0.0002(13)
N1 0.0212(12) 0.0446(17) 0.0441(15) 0.0000(13) 0.0041(11) 0.0010(12)
C1 0.0259(15) 0.0427(19) 0.0383(16) 0.0006(14) 0.0049(13) 0.0009(13)
C2 0.0236(14) 0.0351(17) 0.0348(14) 0.0012(13) 0.0031(12) 0.0004(12)
C3 0.0308(15) 0.0408(18) 0.0260(13) -0.0017(13) 0.0050(12) 0.0002(14)
C4 0.0243(14) 0.0381(17) 0.0264(13) -0.0005(13) -0.0012(11) -0.0047(12)
C5 0.0242(13) 0.0299(15) 0.0255(13) 0.0020(11) 0.0013(11) -0.0032(12)
C6 0.0224(13) 0.0269(15) 0.0267(13) 0.0010(11) 0.0017(11) -0.0009(11)
C7 0.0226(14) 0.0292(15) 0.0284(13) 0.0004(12) 0.0008(11) 0.0023(12)
C8 0.0291(15) 0.0376(18) 0.0272(14) -0.0025(13) 0.0003(12) 0.0004(13)
C9 0.0276(15) 0.0358(17) 0.0357(15) -0.0008(13) -0.0083(12) -0.0013(13)
C10 0.0215(13) 0.0318(16) 0.0354(14) 0.0013(13) -0.0003(12) -0.0004(12)
C11 0.0234(13) 0.0282(15) 0.0318(14) 0.0016(12) 0.0017(12) -0.0012(12)
C12 0.0216(13) 0.0337(17) 0.0418(16) 0.0039(14) -0.0016(13) -0.0015(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
Cl1 C8 1.720(3) . ?
Cl1 H1 0.7718 . ?
Cl2 C4 1.721(3) . ?
Cl2 H2 0.7708 . ?
Cl3 C9 1.760(7) . ?
Cl3 H3 0.8447 . ?
Cl4 C3 1.753(10) . ?
Cl4 H4 0.8151 . ?
O1 C12 1.219(4) . ?
O2 C1 1.211(4) . ?
N1 C12 1.373(4) . ?
N1 C1 1.390(4) . ?
N1 H1A 0.8800 . ?
C1 C2 1.484(4) . ?
C2 C3 1.373(4) . ?
C2 C11 1.414(4) . ?
C3 C4 1.397(4) . ?
C3 H4 0.9596 . ?
C4 C5 1.398(4) . ?
C4 H2 0.9601 . ?
C5 C6 1.427(4) . ?
C5 C7 1.466(4) 3_656 ?
C6 C11 1.414(4) . ?
C6 C7 1.430(4) . ?
C7 C8 1.392(4) . ?
C7 C5 1.466(4) 3_656 ?
C8 C9 1.406(4) . ?
C8 H1 0.9601 . ?
C9 C10 1.373(4) . ?
C9 H3 0.9601 . ?
C10 C11 1.411(4) . ?
C10 C12 1.483(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 Cl1 H1 7.5 . . ?
C4 Cl2 H2 6.7 . . ?
C9 Cl3 H3 13.6 . . ?
C3 Cl4 H4 9.8 . . ?
C12 N1 C1 127.6(3) . . ?
C12 N1 H1A 116.2 . . ?
C1 N1 H1A 116.2 . . ?
O2 C1 N1 120.8(3) . . ?
O2 C1 C2 123.7(3) . . ?
N1 C1 C2 115.5(3) . . ?
C3 C2 C11 119.8(3) . . ?
C3 C2 C1 120.3(3) . . ?
C11 C2 C1 119.9(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 Cl4 118.7(4) . . ?
C4 C3 Cl4 119.9(4) . . ?
C2 C3 H4 119.7 . . ?
C4 C3 H4 119.6 . . ?
Cl4 C3 H4 8.3 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 Cl2 116.2(2) . . ?
C5 C4 Cl2 122.1(2) . . ?
C3 C4 H2 119.3 . . ?
C5 C4 H2 119.1 . . ?
Cl2 C4 H2 5.4 . . ?
C4 C5 C6 116.8(3) . . ?
C4 C5 C7 125.9(3) . 3_656 ?
C6 C5 C7 117.3(2) . 3_656 ?
C11 C6 C5 120.2(3) . . ?
C11 C6 C7 119.4(3) . . ?
C5 C6 C7 120.4(3) . . ?
C8 C7 C6 117.3(3) . . ?
C8 C7 C5 126.1(3) . 3_656 ?
C6 C7 C5 116.6(2) . 3_656 ?
C7 C8 C9 121.4(3) . . ?
C7 C8 Cl1 121.8(2) . . ?
C9 C8 Cl1 116.6(2) . . ?
C7 C8 H1 119.3 . . ?
C9 C8 H1 119.3 . . ?
Cl1 C8 H1 6.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 Cl3 131.0(3) . . ?
C8 C9 Cl3 108.9(3) . . ?
C10 C9 H3 119.9 . . ?
C8 C9 H3 120.0 . . ?
Cl3 C9 H3 12.0 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 C12 120.2(3) . . ?
C11 C10 C12 119.7(3) . . ?
C10 C11 C2 121.1(3) . . ?
C10 C11 C6 119.6(3) . . ?
C2 C11 C6 119.3(3) . . ?
O1 C12 N1 121.3(3) . . ?
O1 C12 C10 122.6(3) . . ?
N1 C12 C10 116.1(3) . . ?

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
C12 N1 C1 O2 180.0(3) . . . . ?
C12 N1 C1 C2 -0.2(5) . . . . ?
O2 C1 C2 C3 3.6(5) . . . . ?
N1 C1 C2 C3 -176.2(3) . . . . ?
O2 C1 C2 C11 -178.4(3) . . . . ?
N1 C1 C2 C11 1.8(5) . . . . ?
C11 C2 C3 C4 5.6(5) . . . . ?
C1 C2 C3 C4 -176.3(3) . . . . ?
C11 C2 C3 Cl4 -164.7(5) . . . . ?
C1 C2 C3 Cl4 13.3(6) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
Cl4 C3 C4 C5 172.3(5) . . . . ?
C2 C3 C4 Cl2 -173.2(3) . . . . ?
Cl4 C3 C4 Cl2 -3.0(6) . . . . ?
C3 C4 C5 C6 -12.3(5) . . . . ?
Cl2 C4 C5 C6 162.6(2) . . . . ?
C3 C4 C5 C7 169.5(3) . . . 3_656 ?
Cl2 C4 C5 C7 -15.6(4) . . . 3_656 ?
C4 C5 C6 C11 15.3(4) . . . . ?
C7 C5 C6 C11 -166.3(3) 3_656 . . . ?
C4 C5 C6 C7 -164.4(3) . . . . ?
C7 C5 C6 C7 14.0(4) 3_656 . . . ?
C11 C6 C7 C8 17.1(4) . . . . ?
C5 C6 C7 C8 -163.2(3) . . . . ?
C11 C6 C7 C5 -162.9(3) . . . 3_656 ?
C5 C6 C7 C5 16.7(4) . . . 3_656 ?
C6 C7 C8 C9 -15.0(5) . . . . ?
C5 C7 C8 C9 165.1(3) 3_656 . . . ?
C6 C7 C8 Cl1 159.4(2) . . . . ?
C5 C7 C8 Cl1 -20.6(5) 3_656 . . . ?
C7 C8 C9 C10 3.6(5) . . . . ?
Cl1 C8 C9 C10 -171.0(2) . . . . ?
C7 C8 C9 Cl3 -172.3(3) . . . . ?
Cl1 C8 C9 Cl3 13.1(4) . . . . ?
C8 C9 C10 C11 6.0(5) . . . . ?
Cl3 C9 C10 C11 -179.2(4) . . . . ?
C8 C9 C10 C12 -175.5(3) . . . . ?
Cl3 C9 C10 C12 -0.7(6) . . . . ?
C9 C10 C11 C2 176.8(3) . . . . ?
C12 C10 C11 C2 -1.7(5) . . . . ?
C9 C10 C11 C6 -3.5(5) . . . . ?
C12 C10 C11 C6 178.0(3) . . . . ?
C3 C2 C11 C10 177.2(3) . . . . ?
C1 C2 C11 C10 -0.9(5) . . . . ?
C3 C2 C11 C6 -2.5(5) . . . . ?
C1 C2 C11 C6 179.5(3) . . . . ?
C5 C6 C11 C10 172.1(3) . . . . ?
C7 C6 C11 C10 -8.2(4) . . . . ?
C5 C6 C11 C2 -8.2(4) . . . . ?
C7 C6 C11 C2 171.5(3) . . . . ?
C1 N1 C12 O1 177.8(3) . . . . ?
C1 N1 C12 C10 -2.3(5) . . . . ?
C9 C10 C12 O1 4.6(5) . . . . ?
C11 C10 C12 O1 -176.9(3) . . . . ?
C9 C10 C12 N1 -175.4(3) . . . . ?
C11 C10 C12 N1 3.1(4) . . . . ?

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
N1 H1A O1 0.88 2.03 2.869(3) 158.5 3_756

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.073