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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6
#TrackingRef 'web_deposit_cif_file_0_Chun-JiangWang_1366768679.6.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C16 H16 Cl N O4'

_chemical_formula_weight         321.75



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   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                   6.4177(9)

_cell_length_b                   12.2541(18)

_cell_length_c                   19.540(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1536.7(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    3544

_cell_measurement_theta_min      2.67

_cell_measurement_theta_max      27.65



_exptl_crystal_description       block

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.32

_exptl_crystal_size_mid          0.29

_exptl_crystal_size_min          0.25

_exptl_crystal_density_meas      0

_exptl_crystal_density_diffrn    ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.266

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9197

_exptl_absorpt_correction_T_max  0.9365

_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            8555

_diffrn_reflns_av_R_equivalents  0.0162

_diffrn_reflns_av_sigmaI/netI    0.0181

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -24

_diffrn_reflns_limit_l_max       23

_diffrn_reflns_theta_min         2.08

_diffrn_reflns_theta_max         25.98

_reflns_number_total             3006

_reflns_number_gt                2619

_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^)+(0.1668P)^2^+1.0765P] 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     SHELXL

_refine_ls_extinction_coef       0.008(5)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.2(2)

_refine_ls_number_reflns         3006

_refine_ls_number_parameters     200

_refine_ls_number_restraints     13

_refine_ls_R_factor_all          0.0884

_refine_ls_R_factor_gt           0.0805

_refine_ls_wR_factor_ref         0.2547

_refine_ls_wR_factor_gt          0.2433

_refine_ls_goodness_of_fit_ref   1.048

_refine_ls_restrained_S_all      1.127

_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






































C1 C 0.3664(13) 0.3762(5) 0.0500(3) 0.0770(19) Uani 1 1 d . . .
C2 C 0.5404(14) 0.3137(6) 0.0623(3) 0.087(2) Uani 1 1 d . . .
H2 H 0.6462 0.3081 0.0300 0.104 Uiso 1 1 calc R . .
C3 C 0.5533(10) 0.2602(5) 0.1233(3) 0.0681(14) Uani 1 1 d . . .
H3 H 0.6731 0.2206 0.1333 0.082 Uiso 1 1 calc R . .
C4 C 0.3939(7) 0.2630(3) 0.1706(2) 0.0484(11) Uani 1 1 d . . .
C5 C 0.2216(10) 0.3243(4) 0.1555(3) 0.0615(13) Uani 1 1 d . . .
H5 H 0.1131 0.3270 0.1870 0.074 Uiso 1 1 calc R . .
C6 C 0.2032(12) 0.3816(5) 0.0958(3) 0.0739(17) Uani 1 1 d . . .
H6 H 0.0849 0.4228 0.0864 0.089 Uiso 1 1 calc R . .
C7 C 0.4112(7) 0.1969(3) 0.2364(2) 0.0432(9) Uani 1 1 d . . .
H7 H 0.5572 0.1954 0.2510 0.052 Uiso 1 1 calc R . .
C8 C 0.3198(8) 0.0510(3) 0.3093(3) 0.0512(11) Uani 1 1 d . . .
H8A H 0.4535 0.0242 0.3251 0.061 Uiso 1 1 calc R . .
H8B H 0.2144 -0.0039 0.3183 0.061 Uiso 1 1 calc R . .
C9 C 0.3281(6) 0.0791(3) 0.2330(2) 0.0416(9) Uani 1 1 d . . .
C10 C 0.1201(6) 0.0620(3) 0.1967(3) 0.0494(10) Uani 1 1 d . . .
H10A H 0.0040 0.0746 0.2275 0.059 Uiso 1 1 calc R . .
H10B H 0.1069 0.1097 0.1574 0.059 Uiso 1 1 calc R . .
C11 C 0.1307(7) -0.0550(4) 0.1754(3) 0.0573(12) Uani 1 1 d . . .
H11A H 0.0803 -0.1025 0.2115 0.069 Uiso 1 1 calc R . .
H11B H 0.0486 -0.0675 0.1345 0.069 Uiso 1 1 calc R . .
C12 C 0.4682(7) 0.0009(3) 0.1948(3) 0.0472(11) Uani 1 1 d . . .
C13 C 0.2635(7) 0.1601(4) 0.3449(2) 0.0455(10) Uani 1 1 d . . .
C14 C 0.0402(7) 0.1619(4) 0.3714(3) 0.0525(11) Uani 1 1 d . . .
C15 C 0.2395(17) 0.1340(11) 0.4636(6) 0.146(4) Uani 1 1 d DU . .
H15A H 0.2460 0.0550 0.4643 0.175 Uiso 1 1 calc R . .
H15B H 0.2667 0.1623 0.5091 0.175 Uiso 1 1 calc R . .
C16 C 0.3834(8) 0.1821(6) 0.4112(3) 0.0729(16) Uani 1 1 d . . .
H16A H 0.5177 0.1458 0.4112 0.087 Uiso 1 1 calc R . .
H16B H 0.4037 0.2597 0.4185 0.087 Uiso 1 1 calc R . .
Cl1 Cl 0.3378(5) 0.44647(15) -0.02760(8) 0.1153(10) Uani 1 1 d . . .
N1 N 0.2847(6) 0.2419(3) 0.29119(19) 0.0493(9) Uani 1 1 d . . .
H1 H 0.2311 0.3062 0.2919 0.059 Uiso 1 1 calc R . .
O1 O 0.6533(6) -0.0024(3) 0.1918(2) 0.0686(11) Uani 1 1 d . . .
O2 O 0.3519(5) -0.0741(3) 0.1622(2) 0.0588(9) Uani 1 1 d . . .
O3 O 0.0402(9) 0.1740(9) 0.4359(3) 0.162(3) Uani 1 1 d DU . .
O4 O -0.1189(6) 0.1565(6) 0.3424(3) 0.1038(19) 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






















C1 0.128(6) 0.051(3) 0.051(3) -0.004(2) 0.016(3) -0.015(3)
C2 0.115(6) 0.073(4) 0.071(4) -0.004(3) 0.033(4) -0.020(4)
C3 0.068(3) 0.064(3) 0.072(3) 0.003(3) 0.023(3) -0.006(3)
C4 0.057(3) 0.033(2) 0.055(2) -0.0021(17) 0.010(2) -0.0047(17)
C5 0.079(3) 0.046(2) 0.060(3) 0.005(2) 0.016(2) 0.011(2)
C6 0.103(5) 0.054(3) 0.065(3) 0.004(2) -0.003(3) 0.009(3)
C7 0.0370(19) 0.0342(19) 0.058(2) -0.0021(17) 0.0008(17) -0.0051(16)
C8 0.049(2) 0.041(2) 0.064(3) 0.0123(19) 0.005(2) 0.0078(19)
C9 0.0329(18) 0.0321(19) 0.060(2) 0.0017(16) 0.0007(17) 0.0007(15)
C10 0.037(2) 0.039(2) 0.072(3) -0.001(2) -0.005(2) -0.0011(17)
C11 0.044(2) 0.050(2) 0.078(3) -0.005(2) -0.007(2) -0.0036(19)
C12 0.035(2) 0.038(2) 0.068(3) 0.0024(19) 0.0013(19) 0.0046(16)
C13 0.040(2) 0.049(2) 0.048(2) 0.0065(18) -0.0010(17) -0.0031(17)
C14 0.049(3) 0.048(2) 0.060(3) -0.006(2) 0.007(2) -0.005(2)
C15 0.163(8) 0.152(7) 0.122(6) 0.014(6) 0.005(6) 0.002(7)
C16 0.049(3) 0.109(5) 0.061(3) -0.005(3) -0.011(2) -0.005(3)
Cl1 0.211(3) 0.0797(11) 0.0552(8) 0.0126(7) 0.0021(12) -0.0330(14)
N1 0.060(2) 0.0362(17) 0.052(2) 0.0021(15) 0.0099(17) -0.0029(16)
O1 0.0406(18) 0.062(2) 0.103(3) -0.002(2) 0.0110(19) 0.0083(15)
O2 0.0529(18) 0.0443(17) 0.079(2) -0.0124(16) 0.0070(17) 0.0013(14)
O3 0.064(3) 0.319(8) 0.103(4) -0.066(5) 0.010(3) 0.013(5)
O4 0.041(2) 0.177(6) 0.094(3) -0.004(4) 0.000(2) -0.011(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

























C1 C2 1.375(11) . ?
C1 C6 1.379(10) . ?
C1 Cl1 1.754(6) . ?
C2 C3 1.362(9) . ?
C3 C4 1.379(7) . ?
C4 C5 1.369(7) . ?
C4 C7 1.523(6) . ?
C5 C6 1.367(8) . ?
C7 N1 1.452(6) . ?
C7 C9 1.541(5) . ?
C8 C9 1.531(6) . ?
C8 C13 1.549(6) . ?
C9 C12 1.512(6) . ?
C9 C10 1.526(6) . ?
C10 C11 1.494(6) . ?
C11 O2 1.462(6) . ?
C12 O1 1.190(6) . ?
C12 O2 1.345(6) . ?
C13 N1 1.457(6) . ?
C13 C14 1.524(6) . ?
C13 C16 1.530(7) . ?
C14 O4 1.169(7) . ?
C14 O3 1.270(8) . ?
C15 O3 1.472(9) . ?
C15 C16 1.500(13) . ?



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







































C2 C1 C6 122.0(6) . . ?
C2 C1 Cl1 120.6(5) . . ?
C6 C1 Cl1 117.2(6) . . ?
C3 C2 C1 118.0(6) . . ?
C2 C3 C4 122.0(6) . . ?
C5 C4 C3 117.9(5) . . ?
C5 C4 C7 122.2(4) . . ?
C3 C4 C7 119.9(5) . . ?
C6 C5 C4 122.4(5) . . ?
C5 C6 C1 117.6(6) . . ?
N1 C7 C4 112.3(3) . . ?
N1 C7 C9 101.1(3) . . ?
C4 C7 C9 115.9(4) . . ?
C9 C8 C13 104.6(3) . . ?
C12 C9 C10 101.8(4) . . ?
C12 C9 C8 111.1(4) . . ?
C10 C9 C8 113.0(4) . . ?
C12 C9 C7 114.1(3) . . ?
C10 C9 C7 116.8(3) . . ?
C8 C9 C7 100.4(3) . . ?
C11 C10 C9 102.8(3) . . ?
O2 C11 C10 104.3(4) . . ?
O1 C12 O2 120.5(4) . . ?
O1 C12 C9 129.8(5) . . ?
O2 C12 C9 109.7(4) . . ?
N1 C13 C14 108.8(4) . . ?
N1 C13 C16 116.2(4) . . ?
C14 C13 C16 100.5(4) . . ?
N1 C13 C8 104.4(3) . . ?
C14 C13 C8 112.6(4) . . ?
C16 C13 C8 114.5(4) . . ?
O4 C14 O3 119.2(5) . . ?
O4 C14 C13 131.0(5) . . ?
O3 C14 C13 109.8(5) . . ?
O3 C15 C16 98.8(7) . . ?
C15 C16 C13 101.5(6) . . ?
C7 N1 C13 108.8(3) . . ?
C12 O2 C11 110.2(4) . . ?
C14 O3 C15 109.1(7) . . ?



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 -3.1(10) . . . . ?
Cl1 C1 C2 C3 -179.5(5) . . . . ?
C1 C2 C3 C4 3.2(10) . . . . ?
C2 C3 C4 C5 -1.8(8) . . . . ?
C2 C3 C4 C7 176.7(5) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C7 C4 C5 C6 -178.4(5) . . . . ?
C4 C5 C6 C1 0.0(9) . . . . ?
C2 C1 C6 C5 1.6(10) . . . . ?
Cl1 C1 C6 C5 178.0(5) . . . . ?
C5 C4 C7 N1 -26.2(6) . . . . ?
C3 C4 C7 N1 155.4(4) . . . . ?
C5 C4 C7 C9 89.4(5) . . . . ?
C3 C4 C7 C9 -89.0(5) . . . . ?
C13 C8 C9 C12 154.7(3) . . . . ?
C13 C8 C9 C10 -91.6(4) . . . . ?
C13 C8 C9 C7 33.6(4) . . . . ?
N1 C7 C9 C12 -163.5(4) . . . . ?
C4 C7 C9 C12 74.8(5) . . . . ?
N1 C7 C9 C10 78.1(5) . . . . ?
C4 C7 C9 C10 -43.7(5) . . . . ?
N1 C7 C9 C8 -44.6(4) . . . . ?
C4 C7 C9 C8 -166.3(4) . . . . ?
C12 C9 C10 C11 31.0(5) . . . . ?
C8 C9 C10 C11 -88.2(5) . . . . ?
C7 C9 C10 C11 156.0(4) . . . . ?
C9 C10 C11 O2 -32.1(5) . . . . ?
C10 C9 C12 O1 161.8(6) . . . . ?
C8 C9 C12 O1 -77.6(7) . . . . ?
C7 C9 C12 O1 35.1(8) . . . . ?
C10 C9 C12 O2 -19.6(5) . . . . ?
C8 C9 C12 O2 101.0(5) . . . . ?
C7 C9 C12 O2 -146.3(4) . . . . ?
C9 C8 C13 N1 -10.7(4) . . . . ?
C9 C8 C13 C14 107.2(4) . . . . ?
C9 C8 C13 C16 -138.8(4) . . . . ?
N1 C13 C14 O4 52.0(8) . . . . ?
C16 C13 C14 O4 174.5(7) . . . . ?
C8 C13 C14 O4 -63.2(8) . . . . ?
N1 C13 C14 O3 -126.2(7) . . . . ?
C16 C13 C14 O3 -3.7(8) . . . . ?
C8 C13 C14 O3 118.6(7) . . . . ?
O3 C15 C16 C13 -42.0(9) . . . . ?
N1 C13 C16 C15 146.3(6) . . . . ?
C14 C13 C16 C15 29.1(7) . . . . ?
C8 C13 C16 C15 -91.8(7) . . . . ?
C4 C7 N1 C13 164.5(3) . . . . ?
C9 C7 N1 C13 40.3(4) . . . . ?
C14 C13 N1 C7 -139.1(4) . . . . ?
C16 C13 N1 C7 108.4(5) . . . . ?
C8 C13 N1 C7 -18.7(5) . . . . ?
O1 C12 O2 C11 178.2(5) . . . . ?
C9 C12 O2 C11 -0.5(6) . . . . ?
C10 C11 O2 C12 21.1(6) . . . . ?
O4 C14 O3 C15 156.8(8) . . . . ?
C13 C14 O3 C15 -24.8(11) . . . . ?
C16 C15 O3 C14 43.0(12) . . . . ?



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.98

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         1.217

_refine_diff_density_min         -0.698

_refine_diff_density_rms         0.077



_database_code_depnum_ccdc_archive 'CCDC 935824'