# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20140210lt
_database_code_depnum_ccdc_archive 'CCDC 1031291'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N O4 S'
_chemical_formula_weight         365.39

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'
S S 0.1246 0.1234 '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)/c

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

_cell_length_a                   15.7471(4)
_cell_length_b                   7.1137(2)
_cell_length_c                   15.1029(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.4920(10)
_cell_angle_gamma                90.00
_cell_volume                     1686.63(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9391
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.88

_exptl_crystal_description       Block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44270
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         28.31
_reflns_number_total             4181
_reflns_number_gt                3319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0389P)²+0.7183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4181
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
S1 S 0.57999(2) 0.74822(5) -0.07597(2) 0.01538(9) Uani 1 1 d . . .
O1 O 0.41806(6) 0.66692(15) 0.23238(6) 0.0200(2) Uani 1 1 d . . .
O2 O 0.29579(6) 0.61354(14) 0.14758(6) 0.0166(2) Uani 1 1 d . . .
O3 O 0.24010(6) 0.95856(14) 0.08476(6) 0.0200(2) Uani 1 1 d . . .
O4 O 0.21909(6) 0.88325(15) -0.06003(6) 0.0194(2) Uani 1 1 d . . .
N1 N 0.40367(7) 0.75229(15) 0.08506(7) 0.0134(2) Uani 1 1 d . . .
C1 C 0.62657(8) 0.67864(19) 0.02821(9) 0.0145(3) Uani 1 1 d . . .
C2 C 0.71224(9) 0.6325(2) 0.04611(9) 0.0182(3) Uani 1 1 d . . .
H2A H 0.7504 0.6360 0.0004 0.022 Uiso 1 1 calc R . .
C3 C 0.74058(9) 0.5815(2) 0.13174(10) 0.0196(3) Uani 1 1 d . . .
H3A H 0.7990 0.5517 0.1452 0.023 Uiso 1 1 calc R . .
C4 C 0.68422(9) 0.57333(19) 0.19878(9) 0.0184(3) Uani 1 1 d . . .
H4A H 0.7048 0.5365 0.2570 0.022 Uiso 1 1 calc R . .
C5 C 0.59909(9) 0.61806(19) 0.18156(9) 0.0163(3) Uani 1 1 d . . .
H5A H 0.5614 0.6119 0.2276 0.020 Uiso 1 1 calc R . .
C6 C 0.56871(8) 0.67263(18) 0.09561(9) 0.0139(3) Uani 1 1 d . . .
C7 C 0.48585(8) 0.72983(18) 0.05756(9) 0.0137(3) Uani 1 1 d . . .
C8 C 0.35102(8) 0.81098(19) 0.01043(9) 0.0148(3) Uani 1 1 d . . .
C9 C 0.39867(8) 0.82541(18) -0.06160(9) 0.0147(3) Uani 1 1 d . . .
H9A H 0.3792 0.8632 -0.1200 0.018 Uiso 1 1 calc R . .
C10 C 0.48264(8) 0.77277(18) -0.03146(9) 0.0141(3) Uani 1 1 d . . .
C11 C 0.37552(8) 0.67531(19) 0.16322(9) 0.0148(3) Uani 1 1 d . . .
C12 C 0.25254(9) 0.5646(2) 0.22641(9) 0.0181(3) Uani 1 1 d . . .
H12A H 0.2549 0.6706 0.2690 0.022 Uiso 1 1 calc R . .
H12B H 0.2793 0.4531 0.2562 0.022 Uiso 1 1 calc R . .
C13 C 0.16195(9) 0.5230(2) 0.19309(9) 0.0187(3) Uani 1 1 d . . .
C14 C 0.14015(9) 0.3465(2) 0.15886(10) 0.0233(3) Uani 1 1 d . . .
H14A H 0.1820 0.2503 0.1593 0.028 Uiso 1 1 calc R . .
C15 C 0.05755(10) 0.3102(3) 0.12402(12) 0.0312(4) Uani 1 1 d . . .
H15A H 0.0432 0.1898 0.1001 0.037 Uiso 1 1 calc R . .
C16 C -0.00406(10) 0.4494(3) 0.12408(11) 0.0328(4) Uani 1 1 d . . .
H16A H -0.0605 0.4249 0.0998 0.039 Uiso 1 1 calc R . .
C17 C 0.01683(10) 0.6241(3) 0.15962(12) 0.0338(4) Uani 1 1 d . . .
H17A H -0.0256 0.7187 0.1610 0.041 Uiso 1 1 calc R . .
C18 C 0.09973(10) 0.6615(2) 0.19321(11) 0.0272(3) Uani 1 1 d . . .
H18A H 0.1140 0.7826 0.2164 0.033 Uiso 1 1 calc R . .
C19 C 0.26581(8) 0.88980(19) 0.01872(9) 0.0156(3) Uani 1 1 d . . .
C20 C 0.13667(9) 0.9713(2) -0.05958(10) 0.0234(3) Uani 1 1 d . . .
H20A H 0.1067 0.9613 -0.1188 0.035 Uiso 1 1 calc R . .
H20B H 0.1439 1.1042 -0.0436 0.035 Uiso 1 1 calc R . .
H20C H 0.1034 0.9083 -0.0161 0.035 Uiso 1 1 calc R . .


_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
S1 C10 1.7303(14) . ?
S1 C1 1.7544(13) . ?
O1 C11 1.1974(16) . ?
O2 C11 1.3337(16) . ?
O2 C12 1.4592(16) . ?
O3 C19 1.2088(16) . ?
O4 C19 1.3494(16) . ?
O4 C20 1.4417(17) . ?
N1 C7 1.3989(17) . ?
N1 C11 1.4042(17) . ?
N1 C8 1.4092(16) . ?
C1 C2 1.3942(18) . ?
C1 C6 1.4189(19) . ?
C2 C3 1.383(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.399(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3826(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4026(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4426(18) . ?
C7 C10 1.3757(18) . ?
C8 C9 1.3730(19) . ?
C8 C19 1.4686(19) . ?
C9 C10 1.4148(18) . ?
C9 H9A 0.9500 . ?
C12 C13 1.5046(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.390(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.389(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.389(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C10 S1 C1 90.05(6) . . ?
C11 O2 C12 115.29(10) . . ?
C19 O4 C20 114.19(11) . . ?
C7 N1 C11 124.43(11) . . ?
C7 N1 C8 107.24(11) . . ?
C11 N1 C8 125.67(11) . . ?
C2 C1 C6 121.32(12) . . ?
C2 C1 S1 124.79(11) . . ?
C6 C1 S1 113.89(10) . . ?
C3 C2 C1 118.65(13) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 120.74(13) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 121.00(13) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 119.56(13) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 C1 118.73(12) . . ?
C5 C6 C7 132.77(13) . . ?
C1 C6 C7 108.50(11) . . ?
C10 C7 N1 107.50(11) . . ?
C10 C7 C6 114.51(12) . . ?
N1 C7 C6 137.97(12) . . ?
C9 C8 N1 109.39(12) . . ?
C9 C8 C19 126.78(12) . . ?
N1 C8 C19 121.95(12) . . ?
C8 C9 C10 106.28(12) . . ?
C8 C9 H9A 126.9 . . ?
C10 C9 H9A 126.9 . . ?
C7 C10 C9 109.58(12) . . ?
C7 C10 S1 113.04(10) . . ?
C9 C10 S1 137.38(11) . . ?
O1 C11 O2 126.34(13) . . ?
O1 C11 N1 124.12(12) . . ?
O2 C11 N1 109.54(11) . . ?
O2 C12 C13 105.36(11) . . ?
O2 C12 H12A 110.7 . . ?
C13 C12 H12A 110.7 . . ?
O2 C12 H12B 110.7 . . ?
C13 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C18 C13 C14 119.16(14) . . ?
C18 C13 C12 120.67(14) . . ?
C14 C13 C12 120.13(13) . . ?
C15 C14 C13 120.36(14) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C16 C15 C14 120.11(16) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C17 C16 C15 119.79(15) . . ?
C17 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
C16 C17 C18 120.15(15) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C13 120.41(16) . . ?
C17 C18 H18A 119.8 . . ?
C13 C18 H18A 119.8 . . ?
O3 C19 O4 123.13(12) . . ?
O3 C19 C8 126.31(12) . . ?
O4 C19 C8 110.51(11) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 S1 C1 C2 -179.40(13) . . . . ?
C10 S1 C1 C6 0.52(11) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
S1 C1 C2 C3 179.41(11) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C4 C5 C6 C7 -178.76(14) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
S1 C1 C6 C5 179.77(10) . . . . ?
C2 C1 C6 C7 179.18(12) . . . . ?
S1 C1 C6 C7 -0.74(14) . . . . ?
C11 N1 C7 C10 162.01(12) . . . . ?
C8 N1 C7 C10 -0.36(14) . . . . ?
C11 N1 C7 C6 -16.4(2) . . . . ?
C8 N1 C7 C6 -178.80(15) . . . . ?
C5 C6 C7 C10 -179.96(14) . . . . ?
C1 C6 C7 C10 0.65(16) . . . . ?
C5 C6 C7 N1 -1.6(3) . . . . ?
C1 C6 C7 N1 179.02(15) . . . . ?
C7 N1 C8 C9 -0.15(15) . . . . ?
C11 N1 C8 C9 -162.25(12) . . . . ?
C7 N1 C8 C19 -165.54(12) . . . . ?
C11 N1 C8 C19 32.37(19) . . . . ?
N1 C8 C9 C10 0.59(15) . . . . ?
C19 C8 C9 C10 165.08(13) . . . . ?
N1 C7 C10 C9 0.73(15) . . . . ?
C6 C7 C10 C9 179.59(11) . . . . ?
N1 C7 C10 S1 -179.14(9) . . . . ?
C6 C7 C10 S1 -0.28(15) . . . . ?
C8 C9 C10 C7 -0.82(15) . . . . ?
C8 C9 C10 S1 179.00(12) . . . . ?
C1 S1 C10 C7 -0.13(11) . . . . ?
C1 S1 C10 C9 -179.95(15) . . . . ?
C12 O2 C11 O1 12.2(2) . . . . ?
C12 O2 C11 N1 -168.24(11) . . . . ?
C7 N1 C11 O1 38.9(2) . . . . ?
C8 N1 C11 O1 -161.92(13) . . . . ?
C7 N1 C11 O2 -140.60(12) . . . . ?
C8 N1 C11 O2 18.55(18) . . . . ?
C11 O2 C12 C13 173.18(11) . . . . ?
O2 C12 C13 C18 -94.92(15) . . . . ?
O2 C12 C13 C14 82.86(15) . . . . ?
C18 C13 C14 C15 1.0(2) . . . . ?
C12 C13 C14 C15 -176.83(14) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
C16 C17 C18 C13 -1.3(3) . . . . ?
C14 C13 C18 C17 0.0(2) . . . . ?
C12 C13 C18 C17 177.83(14) . . . . ?
C20 O4 C19 O3 2.04(19) . . . . ?
C20 O4 C19 C8 -175.40(12) . . . . ?
C9 C8 C19 O3 -141.93(15) . . . . ?
N1 C8 C19 O3 20.8(2) . . . . ?
C9 C8 C19 O4 35.40(19) . . . . ?
N1 C8 C19 O4 -161.89(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20140320lt
_database_code_depnum_ccdc_archive 'CCDC 1031292'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Cl N2 O4'
_chemical_formula_weight         344.74

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.7022(1)
_cell_length_b                   21.4243(3)
_cell_length_c                   8.4040(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.488(1)
_cell_angle_gamma                90.00
_cell_volume                     1523.61(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.20

_exptl_crystal_description       Block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9418
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41898
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         28.25
_reflns_number_total             3772
_reflns_number_gt                3300
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0345P)²+0.7924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3772
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.90162(4) 1.080655(14) 1.18199(4) 0.02078(8) Uani 1 1 d . . .
O1 O 0.27988(10) 1.01516(4) 0.55050(11) 0.01897(19) Uani 1 1 d . . .
O2 O 0.25019(10) 0.91240(4) 0.49014(10) 0.01517(17) Uani 1 1 d . . .
O3 O 0.50594(11) 0.83983(4) 0.42132(10) 0.01941(19) Uani 1 1 d . . .
O4 O 0.45735(11) 0.78302(4) 0.62949(10) 0.01785(18) Uani 1 1 d . . .
N1 N 0.64758(12) 1.07397(5) 0.94561(13) 0.0162(2) Uani 1 1 d . . .
N2 N 0.47095(11) 0.94480(4) 0.66652(12) 0.01350(19) Uani 1 1 d . . .
C1 C 0.76738(14) 1.04001(6) 1.02954(14) 0.0153(2) Uani 1 1 d . . .
C2 C 0.79453(14) 0.97750(6) 1.00584(14) 0.0164(2) Uani 1 1 d . . .
H2A H 0.8818 0.9558 1.0715 0.020 Uiso 1 1 calc R . .
C3 C 0.68566(13) 0.94836(5) 0.87933(14) 0.0143(2) Uani 1 1 d . . .
C4 C 0.67033(14) 0.88610(5) 0.81380(15) 0.0164(2) Uani 1 1 d . . .
H4A H 0.7376 0.8517 0.8527 0.020 Uiso 1 1 calc R . .
C5 C 0.54188(13) 0.88554(5) 0.68595(14) 0.0142(2) Uani 1 1 d . . .
C6 C 0.56016(13) 0.98394(5) 0.78699(14) 0.0131(2) Uani 1 1 d . . .
C7 C 0.54225(14) 1.04644(5) 0.82397(14) 0.0152(2) Uani 1 1 d . . .
H7A H 0.4552 1.0696 0.7629 0.018 Uiso 1 1 calc R . .
C8 C 0.32576(13) 0.96206(5) 0.56437(14) 0.0137(2) Uani 1 1 d . . .
C9 C 0.09963(14) 0.92705(5) 0.37697(15) 0.0176(2) Uani 1 1 d . . .
H9A H 0.1175 0.9542 0.2876 0.021 Uiso 1 1 calc R . .
H9B H 0.0295 0.9493 0.4353 0.021 Uiso 1 1 calc R . .
C10 C 0.02512(14) 0.86683(5) 0.30833(14) 0.0155(2) Uani 1 1 d . . .
C11 C 0.10026(15) 0.82799(6) 0.21689(16) 0.0220(3) Uani 1 1 d . . .
H11A H 0.2008 0.8393 0.2000 0.026 Uiso 1 1 calc R . .
C12 C 0.02896(17) 0.77304(6) 0.15053(18) 0.0255(3) Uani 1 1 d . . .
H12A H 0.0808 0.7466 0.0887 0.031 Uiso 1 1 calc R . .
C13 C -0.11873(16) 0.75654(6) 0.17456(16) 0.0218(3) Uani 1 1 d . . .
H13A H -0.1677 0.7189 0.1292 0.026 Uiso 1 1 calc R . .
C14 C -0.19443(15) 0.79514(6) 0.26469(15) 0.0201(3) Uani 1 1 d . . .
H14A H -0.2955 0.7840 0.2805 0.024 Uiso 1 1 calc R . .
C15 C -0.12275(14) 0.85017(6) 0.33196(15) 0.0173(2) Uani 1 1 d . . .
H15A H -0.1746 0.8764 0.3941 0.021 Uiso 1 1 calc R . .
C16 C 0.49684(13) 0.83472(5) 0.56138(14) 0.0139(2) Uani 1 1 d . . .
C17 C 0.42378(17) 0.72935(6) 0.52027(16) 0.0220(3) Uani 1 1 d . . .
H17A H 0.3960 0.6934 0.5801 0.033 Uiso 1 1 calc R . .
H17B H 0.5175 0.7193 0.4793 0.033 Uiso 1 1 calc R . .
H17C H 0.3353 0.7392 0.4280 0.033 Uiso 1 1 calc R . .


_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 1.7511(12) . ?
O1 C8 1.2024(14) . ?
O2 C8 1.3274(14) . ?
O2 C9 1.4623(14) . ?
O3 C16 1.2031(14) . ?
O4 C16 1.3283(14) . ?
O4 C17 1.4578(14) . ?
N1 C1 1.3307(16) . ?
N1 C7 1.3402(16) . ?
N2 C6 1.4015(14) . ?
N2 C8 1.4015(15) . ?
N2 C5 1.4043(14) . ?
C1 C2 1.3823(17) . ?
C2 C3 1.3956(16) . ?
C2 H2A 0.9500 . ?
C3 C6 1.4072(16) . ?
C3 C4 1.4375(16) . ?
C4 C5 1.3579(16) . ?
C4 H4A 0.9500 . ?
C5 C16 1.4979(16) . ?
C6 C7 1.3917(15) . ?
C7 H7A 0.9500 . ?
C9 C10 1.4977(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.3935(17) . ?
C10 C11 1.3946(17) . ?
C11 C12 1.3859(18) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3923(18) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3872(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3907(17) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O2 C9 113.84(9) . . ?
C16 O4 C17 114.86(9) . . ?
C1 N1 C7 118.40(10) . . ?
C6 N2 C8 123.57(9) . . ?
C6 N2 C5 107.60(9) . . ?
C8 N2 C5 128.22(10) . . ?
N1 C1 C2 126.33(11) . . ?
N1 C1 Cl1 114.98(9) . . ?
C2 C1 Cl1 118.68(9) . . ?
C1 C2 C3 115.76(11) . . ?
C1 C2 H2A 122.1 . . ?
C3 C2 H2A 122.1 . . ?
C2 C3 C6 118.65(10) . . ?
C2 C3 C4 133.85(11) . . ?
C6 C3 C4 107.50(10) . . ?
C5 C4 C3 107.27(10) . . ?
C5 C4 H4A 126.4 . . ?
C3 C4 H4A 126.4 . . ?
C4 C5 N2 110.03(10) . . ?
C4 C5 C16 126.32(10) . . ?
N2 C5 C16 122.65(10) . . ?
C7 C6 N2 131.68(11) . . ?
C7 C6 C3 120.72(11) . . ?
N2 C6 C3 107.59(10) . . ?
N1 C7 C6 120.10(11) . . ?
N1 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
O1 C8 O2 126.58(11) . . ?
O1 C8 N2 122.72(10) . . ?
O2 C8 N2 110.70(9) . . ?
O2 C9 C10 107.90(9) . . ?
O2 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
O2 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C15 C10 C11 119.53(11) . . ?
C15 C10 C9 119.80(11) . . ?
C11 C10 C9 120.64(11) . . ?
C12 C11 C10 120.34(12) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 119.94(12) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 119.99(12) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.15(11) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C14 C15 C10 120.05(11) . . ?
C14 C15 H15A 120.0 . . ?
C10 C15 H15A 120.0 . . ?
O3 C16 O4 125.46(11) . . ?
O3 C16 C5 123.47(10) . . ?
O4 C16 C5 110.90(10) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C7 N1 C1 C2 -1.02(18) . . . . ?
C7 N1 C1 Cl1 178.26(9) . . . . ?
N1 C1 C2 C3 1.07(18) . . . . ?
Cl1 C1 C2 C3 -178.19(8) . . . . ?
C1 C2 C3 C6 0.39(16) . . . . ?
C1 C2 C3 C4 179.39(12) . . . . ?
C2 C3 C4 C5 -178.13(13) . . . . ?
C6 C3 C4 C5 0.94(13) . . . . ?
C3 C4 C5 N2 -0.86(13) . . . . ?
C3 C4 C5 C16 167.87(11) . . . . ?
C6 N2 C5 C4 0.45(13) . . . . ?
C8 N2 C5 C4 -170.82(11) . . . . ?
C6 N2 C5 C16 -168.77(10) . . . . ?
C8 N2 C5 C16 19.96(17) . . . . ?
C8 N2 C6 C7 -7.61(19) . . . . ?
C5 N2 C6 C7 -179.38(12) . . . . ?
C8 N2 C6 C3 171.93(10) . . . . ?
C5 N2 C6 C3 0.16(12) . . . . ?
C2 C3 C6 C7 -1.83(17) . . . . ?
C4 C3 C6 C7 178.93(10) . . . . ?
C2 C3 C6 N2 178.57(10) . . . . ?
C4 C3 C6 N2 -0.67(13) . . . . ?
C1 N1 C7 C6 -0.52(17) . . . . ?
N2 C6 C7 N1 -178.59(11) . . . . ?
C3 C6 C7 N1 1.93(17) . . . . ?
C9 O2 C8 O1 2.51(17) . . . . ?
C9 O2 C8 N2 -178.06(9) . . . . ?
C6 N2 C8 O1 14.18(17) . . . . ?
C5 N2 C8 O1 -175.81(11) . . . . ?
C6 N2 C8 O2 -165.27(10) . . . . ?
C5 N2 C8 O2 4.74(16) . . . . ?
C8 O2 C9 C10 -177.63(10) . . . . ?
O2 C9 C10 C15 120.31(12) . . . . ?
O2 C9 C10 C11 -61.51(15) . . . . ?
C15 C10 C11 C12 -0.31(19) . . . . ?
C9 C10 C11 C12 -178.50(12) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C10 0.29(19) . . . . ?
C11 C10 C15 C14 0.04(18) . . . . ?
C9 C10 C15 C14 178.24(11) . . . . ?
C17 O4 C16 O3 0.14(17) . . . . ?
C17 O4 C16 C5 -175.33(10) . . . . ?
C4 C5 C16 O3 -108.82(15) . . . . ?
N2 C5 C16 O3 58.58(16) . . . . ?
C4 C5 C16 O4 66.76(15) . . . . ?
N2 C5 C16 O4 -125.84(11) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.047
