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


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#  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. 
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data_sd-88_0m
_database_code_depnum_ccdc_archive 'CCDC 878092'
#TrackingRef 'CIF-4b.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H35 Cl2 N9 O5'
_chemical_formula_weight         756.64
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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
_cell_length_a                   16.0317(17)
_cell_length_b                   22.181(2)
_cell_length_c                   10.2433(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3642.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(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            31686
_diffrn_reflns_av_R_equivalents  0.1051
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3292
_reflns_number_gt                1970
_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^)+(0.1000P)^2^+0.5270P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3292
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2467
_refine_ls_wR_factor_gt          0.2139
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.003
_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 0.52701(9) 0.16574(8) 0.50020(16) 0.1082(7) Uani 1 1 d . . .
O1 O -0.0386(2) 0.11830(15) 0.3652(3) 0.0771(10) Uani 1 1 d . . .
O2 O -0.1850(2) 0.00688(15) 0.6584(4) 0.0836(11) Uani 1 1 d . . .
C20 C 0.1094(3) 0.11807(19) 0.5179(5) 0.0546(11) Uani 1 1 d . . .
N1 N -0.1142(2) 0.06515(17) 0.5147(4) 0.0667(11) Uani 1 1 d . . .
N2 N -0.0507(2) 0.02826(15) 0.7054(4) 0.0621(10) Uani 1 1 d . . .
N3 N 0.0875(3) 0.04684(18) 0.7565(4) 0.0719(11) Uani 1 1 d . . .
C14 C 0.1096(3) 0.21887(19) 0.4027(4) 0.0631(12) Uani 1 1 d . . .
H14 H 0.1136 0.1982 0.3240 0.076 Uiso 1 1 calc R . .
C12 C 0.1037(3) 0.18705(19) 0.5179(4) 0.0519(10) Uani 1 1 d . . .
C13 C 0.0959(3) 0.21868(18) 0.6336(4) 0.0560(11) Uani 1 1 d . . .
H13 H 0.0905 0.1979 0.7120 0.067 Uiso 1 1 calc R . .
C1 C 0.4232(3) 0.1475(2) 0.5310(6) 0.0686(13) Uani 1 1 d . . .
C2 C 0.3871(3) 0.1647(2) 0.6460(5) 0.0770(15) Uani 1 1 d . . .
H2 H 0.4176 0.1861 0.7075 0.092 Uiso 1 1 calc R . .
C3 C 0.3046(3) 0.1497(2) 0.6699(5) 0.0703(13) Uani 1 1 d . . .
H3 H 0.2791 0.1622 0.7469 0.084 Uiso 1 1 calc R . .
C4 C 0.2606(3) 0.11684(18) 0.5812(5) 0.0583(11) Uani 1 1 d . . .
C5 C 0.2976(3) 0.1000(2) 0.4663(5) 0.0692(13) Uani 1 1 d . . .
H5 H 0.2674 0.0779 0.4054 0.083 Uiso 1 1 calc R . .
C6 C 0.3792(3) 0.1156(2) 0.4402(5) 0.0745(14) Uani 1 1 d . . .
H6 H 0.4040 0.1044 0.3617 0.089 Uiso 1 1 calc R . .
N5 N 0.1759(2) 0.09832(15) 0.6080(4) 0.0587(10) Uani 1 1 d . . .
C7 C 0.1591(3) 0.0680(2) 0.7174(5) 0.0710(13) Uani 1 1 d . . .
H7 H 0.2041 0.0611 0.7727 0.085 Uiso 1 1 calc R . .
C9 C 0.0289(3) 0.08737(17) 0.5571(5) 0.0550(11) Uani 1 1 d . . .
C8 C 0.0233(3) 0.05603(18) 0.6703(5) 0.0588(11) Uani 1 1 d . . .
C16 C -0.0591(3) -0.0074(2) 0.8258(5) 0.0817(15) Uani 1 1 d . . .
H16A H -0.1098 0.0036 0.8696 0.122 Uiso 1 1 calc R . .
H16B H -0.0125 0.0005 0.8820 0.122 Uiso 1 1 calc R . .
H16C H -0.0606 -0.0495 0.8043 0.122 Uiso 1 1 calc R . .
C11 C -0.1199(3) 0.03198(19) 0.6282(5) 0.0658(13) Uani 1 1 d . . .
C10 C -0.0403(3) 0.0922(2) 0.4711(5) 0.0627(12) Uani 1 1 d . . .
C15 C -0.1891(3) 0.0723(3) 0.4344(6) 0.0927(17) Uani 1 1 d . . .
H15A H -0.2287 0.0414 0.4564 0.139 Uiso 1 1 calc R . .
H15B H -0.1745 0.0690 0.3439 0.139 Uiso 1 1 calc R . .
H15C H -0.2133 0.1112 0.4505 0.139 Uiso 1 1 calc R . .
O21 O 0.3546(6) 0.2500 -0.1000(8) 0.179(4) Uani 1 2 d S . .
N6 N 0.3185(5) 0.2500 0.1035(7) 0.0881(19) Uani 1 2 d S . .
C19 C 0.3739(6) 0.2500 0.0101(9) 0.095(2) Uani 1 2 d S . .
H19 H 0.4303 0.2500 0.0316 0.114 Uiso 1 2 calc SR . .
C17 C 0.2311(6) 0.2500 0.0663(15) 0.168(5) Uani 1 2 d S . .
H17A H 0.2101 0.2905 0.0683 0.252 Uiso 0.50 1 calc PR . .
H17B H 0.2000 0.2255 0.1264 0.252 Uiso 0.50 1 calc PR . .
H17C H 0.2255 0.2340 -0.0203 0.252 Uiso 0.50 1 calc PR . .
C18 C 0.3460(9) 0.2500 0.2339(10) 0.166(5) Uani 1 2 d S . .
H18A H 0.4037 0.2386 0.2370 0.250 Uiso 0.50 1 calc PR . .
H18B H 0.3135 0.2217 0.2835 0.250 Uiso 0.50 1 calc PR . .
H18C H 0.3394 0.2896 0.2702 0.250 Uiso 0.50 1 calc PR . .
H20 H 0.123(3) 0.1081(16) 0.433(4) 0.052(11) Uiso 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 0.0660(10) 0.1280(14) 0.1305(15) -0.0011(10) 0.0028(9) -0.0304(8)
O1 0.073(2) 0.079(2) 0.079(2) 0.0048(18) -0.0144(19) -0.0088(17)
O2 0.061(2) 0.071(2) 0.119(3) -0.0167(19) 0.015(2) -0.0088(17)
C20 0.046(3) 0.056(3) 0.062(3) -0.005(2) 0.000(2) 0.0012(19)
N1 0.050(2) 0.060(2) 0.090(3) -0.010(2) -0.007(2) -0.0005(18)
N2 0.054(2) 0.052(2) 0.081(3) -0.0019(18) 0.004(2) 0.0034(17)
N3 0.056(3) 0.078(3) 0.082(3) 0.016(2) -0.006(2) 0.002(2)
C14 0.075(3) 0.058(2) 0.056(3) -0.003(2) 0.003(2) -0.003(2)
C12 0.044(2) 0.049(2) 0.063(3) -0.0018(19) -0.002(2) 0.0007(18)
C13 0.059(3) 0.053(2) 0.056(2) 0.0074(19) 0.002(2) 0.0004(19)
C1 0.052(3) 0.064(3) 0.090(4) 0.008(3) -0.005(3) -0.008(2)
C2 0.062(3) 0.071(3) 0.099(4) -0.010(3) -0.015(3) -0.007(2)
C3 0.060(3) 0.070(3) 0.081(3) -0.008(2) -0.001(3) 0.005(2)
C4 0.049(3) 0.051(2) 0.075(3) 0.002(2) -0.004(2) 0.004(2)
C5 0.056(3) 0.068(3) 0.083(3) -0.003(3) -0.005(3) -0.006(2)
C6 0.066(3) 0.080(3) 0.078(3) -0.002(3) 0.005(3) 0.000(3)
N5 0.049(2) 0.053(2) 0.074(2) 0.0016(18) -0.0035(19) 0.0054(16)
C7 0.060(3) 0.071(3) 0.082(3) 0.012(3) -0.004(3) 0.005(2)
C9 0.049(3) 0.044(2) 0.072(3) -0.007(2) -0.004(2) 0.0020(19)
C8 0.052(3) 0.050(2) 0.075(3) -0.002(2) 0.005(2) 0.004(2)
C16 0.073(3) 0.080(3) 0.092(4) 0.004(3) 0.011(3) 0.000(3)
C11 0.053(3) 0.046(2) 0.098(4) -0.016(2) 0.017(3) 0.002(2)
C10 0.059(3) 0.051(2) 0.079(3) -0.014(2) 0.002(3) 0.001(2)
C15 0.063(3) 0.095(4) 0.121(5) -0.004(3) -0.020(3) -0.009(3)
O21 0.183(9) 0.251(11) 0.102(5) 0.000 0.018(6) 0.000
N6 0.095(5) 0.088(4) 0.081(5) 0.000 0.020(4) 0.000
C19 0.088(6) 0.112(7) 0.084(6) 0.000 -0.006(6) 0.000
C17 0.072(8) 0.191(12) 0.241(14) 0.000 0.035(8) 0.000
C18 0.263(17) 0.139(10) 0.097(8) 0.000 -0.006(9) 0.000
_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 C1 1.742(5) . ?
O1 C10 1.229(5) . ?
O2 C11 1.223(5) . ?
C20 N5 1.477(5) . ?
C20 C9 1.513(6) . ?
C20 C12 1.533(6) . ?
C20 H20 0.93(4) . ?
N1 C11 1.379(6) . ?
N1 C10 1.402(6) . ?
N1 C15 1.464(6) . ?
N2 C11 1.364(6) . ?
N2 C8 1.384(5) . ?
N2 C16 1.471(6) . ?
N3 C7 1.303(6) . ?
N3 C8 1.371(6) . ?
C14 C12 1.378(6) . ?
C14 C14 1.381(8) 8_565 ?
C14 H14 0.9300 . ?
C12 C13 1.383(5) . ?
C13 C13 1.389(8) 8_565 ?
C13 H13 0.9300 . ?
C1 C6 1.365(7) . ?
C1 C2 1.366(7) . ?
C2 C3 1.385(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(6) . ?
C4 N5 1.445(6) . ?
C5 C6 1.380(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N5 C7 1.335(6) . ?
C7 H7 0.9300 . ?
C9 C8 1.355(6) . ?
C9 C10 1.420(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O21 C19 1.169(10) . ?
N6 C19 1.306(10) . ?
N6 C18 1.406(12) . ?
N6 C17 1.452(12) . ?
C19 H19 0.9300 . ?
C17 H17A 0.9693 . ?
C17 H17B 0.9693 . ?
C17 H17C 0.9692 . ?
C18 H18A 0.9615 . ?
C18 H18B 0.9615 . ?
C18 H18C 0.9615 . ?
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
N5 C20 C9 108.4(4) . . ?
N5 C20 C12 109.8(3) . . ?
C9 C20 C12 113.5(4) . . ?
N5 C20 H20 110(3) . . ?
C9 C20 H20 110(2) . . ?
C12 C20 H20 105(2) . . ?
C11 N1 C10 123.6(4) . . ?
C11 N1 C15 118.5(4) . . ?
C10 N1 C15 117.9(4) . . ?
C11 N2 C8 121.3(4) . . ?
C11 N2 C16 116.3(4) . . ?
C8 N2 C16 122.4(4) . . ?
C7 N3 C8 114.2(4) . . ?
C12 C14 C14 120.8(2) . 8_565 ?
C12 C14 H14 119.6 . . ?
C14 C14 H14 119.6 8_565 . ?
C14 C12 C13 118.7(4) . . ?
C14 C12 C20 120.5(4) . . ?
C13 C12 C20 120.8(4) . . ?
C12 C13 C13 120.5(2) . 8_565 ?
C12 C13 H13 119.8 . . ?
C13 C13 H13 119.8 8_565 . ?
C6 C1 C2 120.9(5) . . ?
C6 C1 Cl1 119.3(4) . . ?
C2 C1 Cl1 119.8(4) . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 N5 120.8(4) . . ?
C5 C4 N5 119.5(4) . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.2(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C7 N5 C4 119.5(4) . . ?
C7 N5 C20 121.9(4) . . ?
C4 N5 C20 118.4(3) . . ?
N3 C7 N5 128.1(5) . . ?
N3 C7 H7 115.9 . . ?
N5 C7 H7 115.9 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 C20 121.0(4) . . ?
C10 C9 C20 117.8(4) . . ?
C9 C8 N3 125.3(4) . . ?
C9 C8 N2 120.5(4) . . ?
N3 C8 N2 114.2(4) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C11 N2 121.3(5) . . ?
O2 C11 N1 120.8(5) . . ?
N2 C11 N1 117.9(4) . . ?
O1 C10 N1 120.1(5) . . ?
O1 C10 C9 124.5(5) . . ?
N1 C10 C9 115.5(5) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 N6 C18 118.9(9) . . ?
C19 N6 C17 117.7(9) . . ?
C18 N6 C17 123.4(10) . . ?
O21 C19 N6 121.7(10) . . ?
O21 C19 H19 119.1 . . ?
N6 C19 H19 119.1 . . ?
N6 C17 H17A 110.5 . . ?
N6 C17 H17B 110.5 . . ?
H17A C17 H17B 108.5 . . ?
N6 C17 H17C 110.4 . . ?
H17A C17 H17C 108.5 . . ?
H17B C17 H17C 108.5 . . ?
N6 C18 H18A 109.6 . . ?
N6 C18 H18B 109.6 . . ?
H18A C18 H18B 109.3 . . ?
N6 C18 H18C 109.6 . . ?
H18A C18 H18C 109.3 . . ?
H18B C18 H18C 109.3 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.062