# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_C:\Users\JRWang\Desktop\1.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'COCRYSTAL 1'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Cl N6 O5 S2'
_chemical_formula_weight         420.87

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'
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   P212121

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

_cell_length_a                   7.673(6)
_cell_length_b                   13.318(11)
_cell_length_c                   16.250(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1661(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   sadabs

_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  'Bruker APEX-II CCD'
_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            7041
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_sigmaI/netI    0.1293
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         24.41
_reflns_number_total             2711
_reflns_number_gt                1744
_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)+(0.0271P)²+0.0000P] where P=(Fo²+2Fc²)/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       0.0039(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_number_reflns         2711
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Cl1 Cl 0.4235(2) 0.41285(13) 0.38868(10) 0.0442(5) Uani 1 1 d . . .
S1 S 0.0141(2) 0.40662(14) 0.45232(10) 0.0359(5) Uani 1 1 d . . .
S2 S -0.1778(2) 0.36336(13) 0.12993(10) 0.0343(4) Uani 1 1 d . . .
O1 O -0.3227(5) 0.4260(3) 0.1519(3) 0.0468(13) Uani 1 1 d . . .
O2 O -0.2076(6) 0.2586(3) 0.1154(3) 0.0453(12) Uani 1 1 d . . .
O3 O 0.0742(6) 0.5027(3) 0.4818(3) 0.0480(13) Uani 1 1 d . . .
O4 O -0.1712(5) 0.3848(4) 0.4547(3) 0.0483(13) Uani 1 1 d . . .
O5 O 0.4686(5) 0.3644(3) 0.5853(3) 0.0450(13) Uani 1 1 d . . .
C1 C 0.0817(9) 0.3626(5) 0.0298(4) 0.0410(18) Uani 1 1 d . . .
H1A H 0.0660 0.2907 0.0239 0.049 Uiso 1 1 calc R . .
H1B H 0.1262 0.3883 -0.0220 0.049 Uiso 1 1 calc R . .
C6 C 0.2500(8) 0.4031(5) 0.3193(4) 0.0310(16) Uani 1 1 d . . .
N5 N 0.9418(7) 0.3468(4) 0.7172(4) 0.0449(15) Uani 1 1 d . . .
N3 N 0.1106(7) 0.3218(4) 0.5052(3) 0.0450(16) Uani 1 1 d . . .
H4 H 0.1832 0.3386 0.5431 0.054 Uiso 1 1 calc R . .
H3 H 0.0898 0.2594 0.4958 0.054 Uiso 1 1 calc R . .
C5 C 0.0765(8) 0.3963(5) 0.3477(3) 0.0282(15) Uani 1 1 d . . .
C4 C -0.0520(7) 0.3842(4) 0.2873(4) 0.0261(15) Uani 1 1 d . . .
H8 H -0.1681 0.3803 0.3036 0.031 Uiso 1 1 calc R . .
C3 C -0.0122(7) 0.3776(4) 0.2039(4) 0.0270(15) Uani 1 1 d . . .
C2 C 0.1631(8) 0.3864(4) 0.1760(4) 0.0290(16) Uani 1 1 d . . .
N2 N 0.2090(8) 0.3821(5) 0.0946(4) 0.0439(17) Uani 1 1 d . . .
C7 C 0.2928(8) 0.3993(5) 0.2376(4) 0.0353(16) Uani 1 1 d . . .
H9 H 0.4090 0.4053 0.2221 0.042 Uiso 1 1 calc R . .
N1 N -0.0867(6) 0.4092(4) 0.0470(3) 0.0367(13) Uani 1 1 d . . .
H1 H -0.1327 0.4554 0.0171 0.044 Uiso 1 1 calc R . .
N4 N 0.6164(6) 0.3673(4) 0.7938(3) 0.0383(14) Uani 1 1 d . . .
C8 C 0.6328(7) 0.3594(5) 0.7117(4) 0.0314(16) Uani 1 1 d . . .
C10 C 0.9247(9) 0.3550(5) 0.7985(5) 0.048(2) Uani 1 1 d . . .
H10 H 1.0246 0.3522 0.8308 0.057 Uiso 1 1 calc R . .
C9 C 0.7935(8) 0.3508(5) 0.6737(4) 0.0340(17) Uani 1 1 d . . .
H9A H 0.7988 0.3477 0.6166 0.041 Uiso 1 1 calc R . .
C11 C 0.7640(9) 0.3675(5) 0.8376(4) 0.0452(19) Uani 1 1 d . . .
H11 H 0.7596 0.3761 0.8943 0.054 Uiso 1 1 calc R . .
C12 C 0.4659(8) 0.3595(5) 0.6619(5) 0.0338(16) Uani 1 1 d . . .
N6 N 0.3219(6) 0.3538(4) 0.7084(3) 0.0437(15) Uani 1 1 d . . .
H6A H 0.2208 0.3534 0.6854 0.052 Uiso 1 1 calc R . .
H6B H 0.3305 0.3506 0.7611 0.052 Uiso 1 1 calc R . .
H2 H 0.301(8) 0.395(4) 0.076(3) 0.023(19) Uiso 1 1 d . . .


_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 C6 1.749(6) . ?
S1 O3 1.441(4) . ?
S1 O4 1.451(4) . ?
S1 N3 1.601(5) . ?
S1 C5 1.772(6) . ?
S2 O2 1.434(4) . ?
S2 O1 1.436(4) . ?
S2 N1 1.636(5) . ?
S2 C3 1.760(6) . ?
O5 C12 1.246(8) . ?
C1 N2 1.460(8) . ?
C1 N1 1.461(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C6 C7 1.369(8) . ?
C6 C5 1.412(8) . ?
N5 C10 1.332(9) . ?
N5 C9 1.340(8) . ?
N3 H4 0.8600 . ?
N3 H3 0.8600 . ?
C5 C4 1.400(8) . ?
C4 C3 1.392(8) . ?
C4 H8 0.9300 . ?
C3 C2 1.424(8) . ?
C2 N2 1.370(8) . ?
C2 C7 1.422(8) . ?
N2 H2 0.79(6) . ?
C7 H9 0.9300 . ?
N1 H1 0.8600 . ?
N4 C11 1.337(8) . ?
N4 C8 1.344(8) . ?
C8 C9 1.384(8) . ?
C8 C12 1.515(9) . ?
C10 C11 1.397(9) . ?
C10 H10 0.9300 . ?
C9 H9A 0.9300 . ?
C11 H11 0.9300 . ?
C12 N6 1.341(8) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?

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
O3 S1 O4 118.8(3) . . ?
O3 S1 N3 107.4(3) . . ?
O4 S1 N3 107.3(3) . . ?
O3 S1 C5 107.5(3) . . ?
O4 S1 C5 106.0(3) . . ?
N3 S1 C5 109.6(3) . . ?
O2 S2 O1 118.9(3) . . ?
O2 S2 N1 107.2(3) . . ?
O1 S2 N1 108.6(3) . . ?
O2 S2 C3 109.5(3) . . ?
O1 S2 C3 109.1(3) . . ?
N1 S2 C3 102.4(3) . . ?
N2 C1 N1 112.2(5) . . ?
N2 C1 H1A 109.2 . . ?
N1 C1 H1A 109.2 . . ?
N2 C1 H1B 109.2 . . ?
N1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C7 C6 C5 122.7(5) . . ?
C7 C6 Cl1 116.4(5) . . ?
C5 C6 Cl1 120.8(5) . . ?
C10 N5 C9 115.8(6) . . ?
S1 N3 H4 120.0 . . ?
S1 N3 H3 120.0 . . ?
H4 N3 H3 120.0 . . ?
C4 C5 C6 116.3(5) . . ?
C4 C5 S1 119.4(4) . . ?
C6 C5 S1 124.3(4) . . ?
C3 C4 C5 122.3(5) . . ?
C3 C4 H8 118.8 . . ?
C5 C4 H8 118.8 . . ?
C4 C3 C2 120.8(6) . . ?
C4 C3 S2 120.9(5) . . ?
C2 C3 S2 118.2(5) . . ?
N2 C2 C7 120.3(6) . . ?
N2 C2 C3 123.2(6) . . ?
C7 C2 C3 116.5(6) . . ?
C2 N2 C1 122.2(6) . . ?
C2 N2 H2 127(4) . . ?
C1 N2 H2 111(4) . . ?
C6 C7 C2 121.3(6) . . ?
C6 C7 H9 119.4 . . ?
C2 C7 H9 119.4 . . ?
C1 N1 S2 112.2(4) . . ?
C1 N1 H1 123.9 . . ?
S2 N1 H1 123.9 . . ?
C11 N4 C8 116.7(6) . . ?
N4 C8 C9 122.2(6) . . ?
N4 C8 C12 116.8(6) . . ?
C9 C8 C12 121.0(6) . . ?
N5 C10 C11 123.2(7) . . ?
N5 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
N5 C9 C8 121.7(6) . . ?
N5 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
N4 C11 C10 120.3(7) . . ?
N4 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O5 C12 N6 125.4(6) . . ?
O5 C12 C8 121.3(6) . . ?
N6 C12 C8 113.3(6) . . ?
C12 N6 H6A 120.0 . . ?
C12 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?

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 C6 C5 C4 0.7(10) . . . . ?
Cl1 C6 C5 C4 -177.2(5) . . . . ?
C7 C6 C5 S1 -176.9(5) . . . . ?
Cl1 C6 C5 S1 5.2(8) . . . . ?
O3 S1 C5 C4 -119.8(5) . . . . ?
O4 S1 C5 C4 8.3(6) . . . . ?
N3 S1 C5 C4 123.7(5) . . . . ?
O3 S1 C5 C6 57.8(6) . . . . ?
O4 S1 C5 C6 -174.2(5) . . . . ?
N3 S1 C5 C6 -58.7(6) . . . . ?
C6 C5 C4 C3 0.9(9) . . . . ?
S1 C5 C4 C3 178.7(5) . . . . ?
C5 C4 C3 C2 -2.1(9) . . . . ?
C5 C4 C3 S2 -179.5(5) . . . . ?
O2 S2 C3 C4 -91.1(5) . . . . ?
O1 S2 C3 C4 40.5(6) . . . . ?
N1 S2 C3 C4 155.4(5) . . . . ?
O2 S2 C3 C2 91.4(5) . . . . ?
O1 S2 C3 C2 -137.0(5) . . . . ?
N1 S2 C3 C2 -22.1(5) . . . . ?
C4 C3 C2 N2 -179.0(6) . . . . ?
S2 C3 C2 N2 -1.5(8) . . . . ?
C4 C3 C2 C7 1.6(8) . . . . ?
S2 C3 C2 C7 179.1(4) . . . . ?
C7 C2 N2 C1 176.1(6) . . . . ?
C3 C2 N2 C1 -3.3(10) . . . . ?
N1 C1 N2 C2 36.3(9) . . . . ?
C5 C6 C7 C2 -1.1(10) . . . . ?
Cl1 C6 C7 C2 176.9(5) . . . . ?
N2 C2 C7 C6 -179.5(6) . . . . ?
C3 C2 C7 C6 -0.1(9) . . . . ?
N2 C1 N1 S2 -63.3(6) . . . . ?
O2 S2 N1 C1 -62.0(5) . . . . ?
O1 S2 N1 C1 168.4(4) . . . . ?
C3 S2 N1 C1 53.2(5) . . . . ?
C11 N4 C8 C9 0.7(10) . . . . ?
C11 N4 C8 C12 -179.8(5) . . . . ?
C9 N5 C10 C11 -0.3(11) . . . . ?
C10 N5 C9 C8 -2.1(10) . . . . ?
N4 C8 C9 N5 2.0(11) . . . . ?
C12 C8 C9 N5 -177.4(6) . . . . ?
C8 N4 C11 C10 -3.1(10) . . . . ?
N5 C10 C11 N4 3.1(12) . . . . ?
N4 C8 C12 O5 171.5(6) . . . . ?
C9 C8 C12 O5 -9.1(10) . . . . ?
N4 C8 C12 N6 -8.5(8) . . . . ?
C9 C8 C12 N6 170.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.41
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 989055'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_C:\Users\JRWang\Desktop\5.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'COCRYSTAL 5'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Cl N6 O5 S2'
_chemical_formula_weight         550.05

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'
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   P21/n

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

_cell_length_a                   7.5201(11)
_cell_length_b                   18.295(3)
_cell_length_c                   17.782(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.534(9)
_cell_angle_gamma                90.00
_cell_volume                     2441.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   sadabs

_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  'Bruker APEX-II CCD'
_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            34209
_diffrn_reflns_av_R_equivalents  0.1591
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4291
_reflns_number_gt                2541
_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)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(17)
_refine_ls_number_reflns         4291
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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
Cl1 Cl 0.54551(11) 0.23266(5) -0.11323(5) 0.0693(3) Uani 1 1 d . . .
S2 S 0.11879(11) 0.22760(4) -0.15842(5) 0.0474(3) Uani 1 1 d . . .
S1 S 0.01646(10) 0.35774(4) 0.11026(4) 0.0436(3) Uani 1 1 d . . .
O1S O 0.0432(3) 0.19390(13) 0.21309(15) 0.0568(6) Uani 1 1 d D . .
O1 O -0.1439(3) 0.31573(11) 0.10655(11) 0.0545(6) Uani 1 1 d . . .
O2 O 0.0033(3) 0.43479(11) 0.10088(11) 0.0584(6) Uani 1 1 d . . .
O3 O 0.1836(3) 0.15500(11) -0.16311(13) 0.0718(7) Uani 1 1 d . . .
O4 O -0.0688(3) 0.23913(13) -0.15733(12) 0.0651(7) Uani 1 1 d . . .
N4 N 0.4125(5) 0.58677(15) 0.17292(16) 0.0673(9) Uani 1 1 d . . .
N2 N 0.4110(3) 0.34013(13) 0.13776(15) 0.0520(7) Uani 1 1 d . . .
H2 H 0.5227 0.3339 0.1492 0.062 Uiso 1 1 calc R . .
N3 N 0.1835(4) 0.27115(16) -0.22832(16) 0.0515(8) Uani 1 1 d . . .
H4 H 0.282(5) 0.2710(19) -0.241(2) 0.077 Uiso 1 1 d . . .
H3 H 0.144(5) 0.3135(18) -0.231(2) 0.077 Uiso 1 1 d . . .
N1 N 0.1242(3) 0.34219(16) 0.19026(14) 0.0487(7) Uani 1 1 d . . .
N5 N 0.1052(4) -0.09923(17) -0.09869(17) 0.0607(8) Uani 1 1 d . . .
N6 N 0.4981(4) 0.09778(16) 0.21307(16) 0.0582(7) Uani 1 1 d . . .
C8 C 0.5712(6) 0.5613(2) 0.1581(2) 0.0794(12) Uani 1 1 d . . .
H27 H 0.6627 0.5672 0.1952 0.095 Uiso 1 1 calc R . .
C9 C 0.6129(5) 0.52742(19) 0.0933(2) 0.0705(11) Uani 1 1 d . . .
H25 H 0.7282 0.5109 0.0875 0.085 Uiso 1 1 calc R . .
C10 C 0.4813(4) 0.51791(14) 0.03611(16) 0.0437(8) Uani 1 1 d . . .
C11 C 0.3160(4) 0.54371(18) 0.05126(19) 0.0563(9) Uani 1 1 d . . .
H23 H 0.2216 0.5383 0.0154 0.068 Uiso 1 1 calc R . .
C12 C 0.2875(5) 0.57734(19) 0.1182(2) 0.0655(10) Uani 1 1 d . . .
H21 H 0.1735 0.5945 0.1257 0.079 Uiso 1 1 calc R . .
C1 C 0.3039(4) 0.37262(17) 0.19324(19) 0.0556(9) Uani 1 1 d . . .
H5 H 0.2969 0.4250 0.1848 0.067 Uiso 1 1 calc R . .
H26 H 0.3607 0.3646 0.2430 0.067 Uiso 1 1 calc R . .
C2 C 0.3454(4) 0.31867(15) 0.06825(17) 0.0407(8) Uani 1 1 d . . .
C7 C 0.4590(4) 0.28980(16) 0.0158(2) 0.0476(8) Uani 1 1 d . . .
H8 H 0.5810 0.2878 0.0280 0.057 Uiso 1 1 calc R . .
C6 C 0.3939(4) 0.26461(16) -0.05265(18) 0.0445(8) Uani 1 1 d . . .
C5 C 0.2113(4) 0.26655(14) -0.07376(17) 0.0397(8) Uani 1 1 d . . .
C3 C 0.1614(3) 0.32313(14) 0.04660(16) 0.0363(7) Uani 1 1 d . . .
C4 C 0.0986(4) 0.29661(14) -0.02278(16) 0.0384(7) Uani 1 1 d . . .
H10 H -0.0229 0.2989 -0.0358 0.046 Uiso 1 1 calc R . .
C21 C 0.1556(4) -0.0303(2) -0.10396(18) 0.0580(9) Uani 1 1 d . . .
H24 H 0.1394 -0.0078 -0.1508 0.070 Uiso 1 1 calc R . .
C20 C 0.2303(4) 0.01070(17) -0.04514(18) 0.0506(9) Uani 1 1 d . . .
H18 H 0.2664 0.0585 -0.0532 0.061 Uiso 1 1 calc R . .
C19 C 0.2510(4) -0.01988(15) 0.02559(17) 0.0407(8) Uani 1 1 d . . .
C15 C 0.3330(4) 0.02100(15) 0.09114(17) 0.0412(8) Uani 1 1 d . . .
C16 C 0.3581(4) 0.09536(17) 0.0894(2) 0.0627(10) Uani 1 1 d . . .
H17 H 0.3203 0.1220 0.0469 0.075 Uiso 1 1 calc R . .
C22 C 0.4392(5) 0.13017(18) 0.1509(2) 0.0669(11) Uani 1 1 d . . .
H22 H 0.4534 0.1806 0.1480 0.080 Uiso 1 1 calc R . .
C17 C 0.1247(5) -0.12788(19) -0.0306(2) 0.0683(11) Uani 1 1 d . . .
H29 H 0.0898 -0.1762 -0.0247 0.082 Uiso 1 1 calc R . .
C18 C 0.1934(4) -0.09092(17) 0.03246(19) 0.0567(9) Uani 1 1 d . . .
H19 H 0.2007 -0.1139 0.0792 0.068 Uiso 1 1 calc R . .
C13 C 0.4724(5) 0.0266(2) 0.2152(2) 0.0669(10) Uani 1 1 d . . .
H16 H 0.5103 0.0018 0.2589 0.080 Uiso 1 1 calc R . .
C14 C 0.3931(5) -0.01318(18) 0.15693(19) 0.0601(10) Uani 1 1 d . . .
H28 H 0.3800 -0.0635 0.1619 0.072 Uiso 1 1 calc R . .
H1S H 0.076(5) 0.163(2) 0.246(2) 0.089(15) Uiso 1 1 d . . .
H1 H 0.114(4) 0.2965(16) 0.2032(16) 0.051(10) Uiso 1 1 d . . .
H2S H -0.003(5) 0.1651(17) 0.1823(17) 0.101(17) Uiso 1 1 d D . .


_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 C6 1.718(3) . ?
S2 O3 1.419(2) . ?
S2 O4 1.428(2) . ?
S2 N3 1.578(3) . ?
S2 C5 1.769(3) . ?
S1 O2 1.422(2) . ?
S1 O1 1.428(2) . ?
S1 N1 1.618(2) . ?
S1 C3 1.739(3) . ?
O1S H1S 0.84(4) . ?
O1S H2S 0.8201(10) . ?
N4 C12 1.322(4) . ?
N4 C8 1.323(5) . ?
N2 C2 1.360(4) . ?
N2 C1 1.440(4) . ?
N2 H2 0.8600 . ?
N3 H4 0.79(4) . ?
N3 H3 0.83(3) . ?
N1 C1 1.460(4) . ?
N1 H1 0.87(3) . ?
N5 C17 1.319(4) . ?
N5 C21 1.323(4) . ?
N6 C22 1.308(4) . ?
N6 C13 1.317(4) . ?
C8 C9 1.362(5) . ?
C8 H27 0.9300 . ?
C9 C10 1.386(4) . ?
C9 H25 0.9300 . ?
C10 C11 1.372(4) . ?
C10 C10 1.484(6) 3_665 ?
C11 C12 1.369(4) . ?
C11 H23 0.9300 . ?
C12 H21 0.9300 . ?
C1 H5 0.9700 . ?
C1 H26 0.9700 . ?
C2 C7 1.406(4) . ?
C2 C3 1.416(4) . ?
C7 C6 1.363(4) . ?
C7 H8 0.9300 . ?
C6 C5 1.402(4) . ?
C5 C4 1.392(4) . ?
C3 C4 1.381(4) . ?
C4 H10 0.9300 . ?
C21 C20 1.378(4) . ?
C21 H24 0.9300 . ?
C20 C19 1.377(4) . ?
C20 H18 0.9300 . ?
C19 C18 1.378(4) . ?
C19 C15 1.486(4) . ?
C15 C16 1.374(4) . ?
C15 C14 1.378(4) . ?
C16 C22 1.375(4) . ?
C16 H17 0.9300 . ?
C22 H22 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H29 0.9300 . ?
C18 H19 0.9300 . ?
C13 C14 1.372(4) . ?
C13 H16 0.9300 . ?
C14 H28 0.9300 . ?

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
O3 S2 O4 118.83(15) . . ?
O3 S2 N3 107.62(15) . . ?
O4 S2 N3 106.78(14) . . ?
O3 S2 C5 107.98(14) . . ?
O4 S2 C5 105.43(13) . . ?
N3 S2 C5 110.04(15) . . ?
O2 S1 O1 118.38(13) . . ?
O2 S1 N1 107.75(14) . . ?
O1 S1 N1 108.76(14) . . ?
O2 S1 C3 109.06(13) . . ?
O1 S1 C3 109.60(13) . . ?
N1 S1 C3 102.03(13) . . ?
H1S O1S H2S 98(4) . . ?
C12 N4 C8 114.6(3) . . ?
C2 N2 C1 123.7(2) . . ?
C2 N2 H2 118.1 . . ?
C1 N2 H2 118.1 . . ?
S2 N3 H4 124(3) . . ?
S2 N3 H3 113(3) . . ?
H4 N3 H3 109(4) . . ?
C1 N1 S1 112.2(2) . . ?
C1 N1 H1 117(2) . . ?
S1 N1 H1 110.7(19) . . ?
C17 N5 C21 115.3(3) . . ?
C22 N6 C13 115.4(3) . . ?
N4 C8 C9 125.9(3) . . ?
N4 C8 H27 117.0 . . ?
C9 C8 H27 117.0 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H25 120.4 . . ?
C10 C9 H25 120.4 . . ?
C11 C10 C9 115.3(3) . . ?
C11 C10 C10 123.0(3) . 3_665 ?
C9 C10 C10 121.7(4) . 3_665 ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H23 119.4 . . ?
C10 C11 H23 119.4 . . ?
N4 C12 C11 123.8(3) . . ?
N4 C12 H21 118.1 . . ?
C11 C12 H21 118.1 . . ?
N2 C1 N1 111.9(2) . . ?
N2 C1 H5 109.2 . . ?
N1 C1 H5 109.2 . . ?
N2 C1 H26 109.2 . . ?
N1 C1 H26 109.2 . . ?
H5 C1 H26 107.9 . . ?
N2 C2 C7 120.7(3) . . ?
N2 C2 C3 121.6(3) . . ?
C7 C2 C3 117.7(3) . . ?
C6 C7 C2 121.3(3) . . ?
C6 C7 H8 119.3 . . ?
C2 C7 H8 119.3 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 Cl1 117.3(2) . . ?
C5 C6 Cl1 121.2(3) . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 S2 119.3(2) . . ?
C6 C5 S2 123.0(2) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 S1 121.0(2) . . ?
C2 C3 S1 119.0(2) . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 H10 118.9 . . ?
C5 C4 H10 118.9 . . ?
N5 C21 C20 124.8(3) . . ?
N5 C21 H24 117.6 . . ?
C20 C21 H24 117.6 . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H18 120.3 . . ?
C21 C20 H18 120.3 . . ?
C20 C19 C18 116.5(3) . . ?
C20 C19 C15 122.0(3) . . ?
C18 C19 C15 121.5(3) . . ?
C16 C15 C14 115.4(3) . . ?
C16 C15 C19 122.1(3) . . ?
C14 C15 C19 122.4(3) . . ?
C15 C16 C22 119.7(3) . . ?
C15 C16 H17 120.1 . . ?
C22 C16 H17 120.1 . . ?
N6 C22 C16 125.0(3) . . ?
N6 C22 H22 117.5 . . ?
C16 C22 H22 117.5 . . ?
N5 C17 C18 124.4(3) . . ?
N5 C17 H29 117.8 . . ?
C18 C17 H29 117.8 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H19 120.2 . . ?
C17 C18 H19 120.2 . . ?
N6 C13 C14 124.1(3) . . ?
N6 C13 H16 118.0 . . ?
C14 C13 H16 118.0 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H28 119.8 . . ?
C15 C14 H28 119.8 . . ?

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
O2 S1 N1 C1 -60.7(2) . . . . ?
O1 S1 N1 C1 169.8(2) . . . . ?
C3 S1 N1 C1 54.0(2) . . . . ?
C12 N4 C8 C9 -0.2(6) . . . . ?
N4 C8 C9 C10 0.4(6) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C8 C9 C10 C10 179.3(4) . . . 3_665 ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C10 C11 C12 -179.1(3) 3_665 . . . ?
C8 N4 C12 C11 0.4(5) . . . . ?
C10 C11 C12 N4 -0.9(5) . . . . ?
C2 N2 C1 N1 34.8(4) . . . . ?
S1 N1 C1 N2 -62.3(3) . . . . ?
C1 N2 C2 C7 177.6(3) . . . . ?
C1 N2 C2 C3 -3.6(4) . . . . ?
N2 C2 C7 C6 176.6(3) . . . . ?
C3 C2 C7 C6 -2.2(4) . . . . ?
C2 C7 C6 C5 0.2(4) . . . . ?
C2 C7 C6 Cl1 178.4(2) . . . . ?
C7 C6 C5 C4 1.3(4) . . . . ?
Cl1 C6 C5 C4 -176.9(2) . . . . ?
C7 C6 C5 S2 -174.5(2) . . . . ?
Cl1 C6 C5 S2 7.3(3) . . . . ?
O3 S2 C5 C4 -125.5(2) . . . . ?
O4 S2 C5 C4 2.5(3) . . . . ?
N3 S2 C5 C4 117.3(2) . . . . ?
O3 S2 C5 C6 50.2(3) . . . . ?
O4 S2 C5 C6 178.2(2) . . . . ?
N3 S2 C5 C6 -67.0(3) . . . . ?
N2 C2 C3 C4 -176.0(2) . . . . ?
C7 C2 C3 C4 2.8(4) . . . . ?
N2 C2 C3 S1 0.6(4) . . . . ?
C7 C2 C3 S1 179.4(2) . . . . ?
O2 S1 C3 C4 -94.1(2) . . . . ?
O1 S1 C3 C4 37.0(3) . . . . ?
N1 S1 C3 C4 152.1(2) . . . . ?
O2 S1 C3 C2 89.3(2) . . . . ?
O1 S1 C3 C2 -139.6(2) . . . . ?
N1 S1 C3 C2 -24.4(2) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
S1 C3 C4 C5 -178.0(2) . . . . ?
C6 C5 C4 C3 -0.7(4) . . . . ?
S2 C5 C4 C3 175.3(2) . . . . ?
C17 N5 C21 C20 2.4(5) . . . . ?
N5 C21 C20 C19 -2.1(5) . . . . ?
C21 C20 C19 C18 -0.2(4) . . . . ?
C21 C20 C19 C15 179.1(3) . . . . ?
C20 C19 C15 C16 14.1(5) . . . . ?
C18 C19 C15 C16 -166.6(3) . . . . ?
C20 C19 C15 C14 -164.1(3) . . . . ?
C18 C19 C15 C14 15.1(4) . . . . ?
C14 C15 C16 C22 0.3(5) . . . . ?
C19 C15 C16 C22 -178.1(3) . . . . ?
C13 N6 C22 C16 -1.2(5) . . . . ?
C15 C16 C22 N6 0.5(6) . . . . ?
C21 N5 C17 C18 -0.5(5) . . . . ?
C20 C19 C18 C17 2.0(5) . . . . ?
C15 C19 C18 C17 -177.4(3) . . . . ?
N5 C17 C18 C19 -1.7(5) . . . . ?
C22 N6 C13 C14 1.3(5) . . . . ?
N6 C13 C14 C15 -0.6(6) . . . . ?
C16 C15 C14 C13 -0.2(5) . . . . ?
C19 C15 C14 C13 178.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 989056'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_C:\Users\JRWang\Desktop\6.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'COCRYSTAL 6'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 Cl N5 O4 S2'
_chemical_formula_weight         481.99

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'
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'
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   P21/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                   10.676(2)
_cell_length_b                   23.734(5)
_cell_length_c                   8.5560(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.786(8)
_cell_angle_gamma                90.00
_cell_volume                     2156.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9893
_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  'Bruker APEX-II CCD'
_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            11378
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_sigmaI/netI    0.1734
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3720
_reflns_number_gt                1689
_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)+(0.0313P)²+0.0000P] where P=(Fo²+2Fc²)/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       0.0039(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(17)
_refine_ls_number_reflns         3720
_refine_ls_number_parameters     288
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1882
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Cl1 Cl 0.40786(11) 0.31001(6) 0.20119(13) 0.0495(4) Uani 1 1 d . . .
S1 S -0.00374(12) 0.13784(6) 0.35336(16) 0.0424(4) Uani 1 1 d . . .
S2 S 0.48883(11) 0.18162(6) 0.30468(14) 0.0412(4) Uani 1 1 d U . .
O1 O 0.0229(3) 0.08395(14) 0.2906(4) 0.0528(10) Uani 1 1 d . . .
O2 O -0.0198(3) 0.14172(14) 0.5174(4) 0.0517(10) Uani 1 1 d . . .
O3 O 0.5708(3) 0.22172(15) 0.3895(3) 0.0495(9) Uani 1 1 d U . .
O4 O 0.4863(3) 0.12508(14) 0.3614(4) 0.0520(9) Uani 1 1 d U . .
N1 N -0.1273(3) 0.16255(17) 0.2542(4) 0.0421(11) Uani 1 1 d . . .
H1 H -0.1426 0.1492 0.1422 0.051 Uiso 1 1 d R . .
N2 N -0.0452(4) 0.25611(17) 0.2334(5) 0.0508(12) Uani 1 1 d . . .
H2 H -0.0625 0.2901 0.2063 0.061 Uiso 1 1 d R . .
N3 N 0.5266(5) 0.1788(3) 0.1281(6) 0.0484(14) Uani 1 1 d . . .
C1 C -0.1483(4) 0.2223(2) 0.2793(6) 0.0521(16) Uani 1 1 d . . .
H1A H -0.2258 0.2338 0.2187 0.063 Uiso 1 1 calc R . .
H1B H -0.1577 0.2289 0.3894 0.063 Uiso 1 1 calc R . .
C2 C 0.0773(4) 0.2401(2) 0.2587(5) 0.0344(13) Uani 1 1 d . . .
C3 C 0.1127(4) 0.1858(2) 0.3128(5) 0.0327(12) Uani 1 1 d . . .
C4 C 0.2377(4) 0.1694(2) 0.3264(5) 0.0351(13) Uani 1 1 d . . .
H8 H 0.2588 0.1328 0.3574 0.042 Uiso 1 1 calc R . .
C5 C 0.3320(4) 0.2066(2) 0.2944(5) 0.0332(13) Uani 1 1 d . . .
C6 C 0.2961(4) 0.2604(2) 0.2456(5) 0.0337(13) Uani 1 1 d . . .
C7 C 0.1729(4) 0.2771(2) 0.2268(5) 0.0376(13) Uani 1 1 d . . .
H6 H 0.1528 0.3134 0.1923 0.045 Uiso 1 1 calc R . .
N4 N 0.6435(6) -0.0908(2) 0.0282(5) 0.0716(16) Uani 1 1 d . . .
N5 N 0.8170(4) 0.1175(2) 0.9481(5) 0.0567(13) Uani 1 1 d . . .
C8 C 0.7635(7) -0.0896(3) 0.0877(7) 0.0731(19) Uani 1 1 d . . .
H13 H 0.8210 -0.1121 0.0417 0.088 Uiso 1 1 calc R . .
C9 C 0.8066(6) -0.0565(3) 0.2151(7) 0.0674(19) Uani 1 1 d . . .
H12 H 0.8907 -0.0584 0.2555 0.081 Uiso 1 1 calc R . .
C10 C 0.7273(6) -0.0212(3) 0.2814(6) 0.0583(17) Uani 1 1 d . . .
C11 C 0.6033(6) -0.0217(3) 0.2178(6) 0.0707(19) Uani 1 1 d . . .
H15 H 0.5448 0.0018 0.2582 0.085 Uiso 1 1 calc R . .
C12 C 0.5666(6) -0.0574(3) 0.0936(8) 0.074(2) Uani 1 1 d . . .
H14 H 0.4822 -0.0576 0.0543 0.089 Uiso 1 1 calc R . .
C13 C 0.7375(5) 0.1368(2) 0.8310(7) 0.0517(15) Uani 1 1 d . . .
H9 H 0.7071 0.1734 0.8382 0.062 Uiso 1 1 calc R . .
C14 C 0.6975(5) 0.1058(3) 0.6995(6) 0.0592(17) Uani 1 1 d . . .
H10 H 0.6430 0.1216 0.6197 0.071 Uiso 1 1 calc R . .
C15 C 0.7390(5) 0.0510(3) 0.6872(6) 0.0525(16) Uani 1 1 d . . .
C16 C 0.8194(5) 0.0301(2) 0.8069(7) 0.0697(19) Uani 1 1 d . . .
H17 H 0.8488 -0.0067 0.8051 0.084 Uiso 1 1 calc R . .
C17 C 0.8557(5) 0.0655(3) 0.9305(7) 0.072(2) Uani 1 1 d . . .
H18 H 0.9133 0.0513 1.0095 0.086 Uiso 1 1 calc R . .
C18 C 0.6932(5) 0.0133(3) 0.5487(6) 0.079(2) Uani 1 1 d . . .
H12A H 0.6927 -0.0255 0.5845 0.095 Uiso 1 1 calc R . .
H12B H 0.6072 0.0235 0.5121 0.095 Uiso 1 1 calc R . .
C19 C 0.7689(5) 0.0170(3) 0.4189(6) 0.086(2) Uani 1 1 d . . .
H11A H 0.8553 0.0078 0.4565 0.104 Uiso 1 1 calc R . .
H11B H 0.7676 0.0556 0.3818 0.104 Uiso 1 1 calc R . .
H3 H 0.537(4) 0.2108(19) 0.081(5) 0.044(19) Uiso 1 1 d . . .
H4 H 0.479(4) 0.156(2) 0.072(5) 0.06(2) Uiso 1 1 d . . .


_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 C6 1.746(5) . ?
S1 O1 1.427(3) . ?
S1 O2 1.434(3) . ?
S1 N1 1.606(4) . ?
S1 C3 1.746(5) . ?
S2 O4 1.428(3) . ?
S2 O3 1.439(3) . ?
S2 N3 1.604(5) . ?
S2 C5 1.770(4) . ?
N1 C1 1.456(6) . ?
N1 H1 1.0071 . ?
N2 C2 1.358(5) . ?
N2 C1 1.448(5) . ?
N2 H2 0.8540 . ?
N3 H3 0.88(4) . ?
N3 H4 0.85(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.393(6) . ?
C2 C3 1.409(6) . ?
C3 C4 1.383(5) . ?
C4 C5 1.387(5) . ?
C4 H8 0.9300 . ?
C5 C6 1.385(6) . ?
C6 C7 1.367(5) . ?
C7 H6 0.9300 . ?
N4 C12 1.307(7) . ?
N4 C8 1.330(7) . ?
N5 C17 1.315(6) . ?
N5 C13 1.328(5) . ?
C8 C9 1.385(7) . ?
C8 H13 0.9300 . ?
C9 C10 1.355(7) . ?
C9 H12 0.9300 . ?
C10 C11 1.379(7) . ?
C10 C19 1.515(7) . ?
C11 C12 1.385(7) . ?
C11 H15 0.9300 . ?
C12 H14 0.9300 . ?
C13 C14 1.375(6) . ?
C13 H9 0.9300 . ?
C14 C15 1.383(7) . ?
C14 H10 0.9300 . ?
C15 C16 1.361(6) . ?
C15 C18 1.526(6) . ?
C16 C17 1.376(7) . ?
C16 H17 0.9300 . ?
C17 H18 0.9300 . ?
C18 C19 1.441(7) . ?
C18 H12A 0.9700 . ?
C18 H12B 0.9700 . ?
C19 H11A 0.9700 . ?
C19 H11B 0.9700 . ?

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
O1 S1 O2 118.3(2) . . ?
O1 S1 N1 108.3(2) . . ?
O2 S1 N1 108.7(2) . . ?
O1 S1 C3 109.7(2) . . ?
O2 S1 C3 108.1(2) . . ?
N1 S1 C3 102.7(2) . . ?
O4 S2 O3 118.8(2) . . ?
O4 S2 N3 107.2(3) . . ?
O3 S2 N3 107.8(3) . . ?
O4 S2 C5 106.3(2) . . ?
O3 S2 C5 109.1(2) . . ?
N3 S2 C5 107.1(2) . . ?
C1 N1 S1 114.1(3) . . ?
C1 N1 H1 115.6 . . ?
S1 N1 H1 115.7 . . ?
C2 N2 C1 123.3(4) . . ?
C2 N2 H2 119.0 . . ?
C1 N2 H2 116.5 . . ?
S2 N3 H3 117(3) . . ?
S2 N3 H4 112(3) . . ?
H3 N3 H4 112(5) . . ?
N2 C1 N1 111.5(4) . . ?
N2 C1 H1A 109.3 . . ?
N1 C1 H1A 109.3 . . ?
N2 C1 H1B 109.3 . . ?
N1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N2 C2 C7 120.4(5) . . ?
N2 C2 C3 122.0(4) . . ?
C7 C2 C3 117.5(4) . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 S1 120.0(4) . . ?
C2 C3 S1 119.3(3) . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H8 119.4 . . ?
C5 C4 H8 119.4 . . ?
C6 C5 C4 117.5(4) . . ?
C6 C5 S2 123.7(4) . . ?
C4 C5 S2 118.6(4) . . ?
C7 C6 C5 122.4(5) . . ?
C7 C6 Cl1 116.7(4) . . ?
C5 C6 Cl1 120.9(4) . . ?
C6 C7 C2 120.7(5) . . ?
C6 C7 H6 119.7 . . ?
C2 C7 H6 119.7 . . ?
C12 N4 C8 116.5(6) . . ?
C17 N5 C13 114.9(5) . . ?
N4 C8 C9 123.0(6) . . ?
N4 C8 H13 118.5 . . ?
C9 C8 H13 118.5 . . ?
C10 C9 C8 120.6(6) . . ?
C10 C9 H12 119.7 . . ?
C8 C9 H12 119.7 . . ?
C9 C10 C11 116.4(6) . . ?
C9 C10 C19 123.2(6) . . ?
C11 C10 C19 120.4(6) . . ?
C10 C11 C12 119.6(6) . . ?
C10 C11 H15 120.2 . . ?
C12 C11 H15 120.2 . . ?
N4 C12 C11 123.9(6) . . ?
N4 C12 H14 118.0 . . ?
C11 C12 H14 118.0 . . ?
N5 C13 C14 123.7(5) . . ?
N5 C13 H9 118.1 . . ?
C14 C13 H9 118.1 . . ?
C13 C14 C15 119.3(5) . . ?
C13 C14 H10 120.3 . . ?
C15 C14 H10 120.3 . . ?
C16 C15 C14 117.9(5) . . ?
C16 C15 C18 120.0(6) . . ?
C14 C15 C18 122.1(6) . . ?
C15 C16 C17 117.6(6) . . ?
C15 C16 H17 121.2 . . ?
C17 C16 H17 121.2 . . ?
N5 C17 C16 126.5(5) . . ?
N5 C17 H18 116.8 . . ?
C16 C17 H18 116.8 . . ?
C19 C18 C15 113.7(5) . . ?
C19 C18 H12A 108.8 . . ?
C15 C18 H12A 108.8 . . ?
C19 C18 H12B 108.8 . . ?
C15 C18 H12B 108.8 . . ?
H12A C18 H12B 107.7 . . ?
C18 C19 C10 114.7(5) . . ?
C18 C19 H11A 108.6 . . ?
C10 C19 H11A 108.6 . . ?
C18 C19 H11B 108.6 . . ?
C10 C19 H11B 108.6 . . ?
H11A C19 H11B 107.6 . . ?

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
O1 S1 N1 C1 -165.9(3) . . . . ?
O2 S1 N1 C1 64.4(4) . . . . ?
C3 S1 N1 C1 -49.9(4) . . . . ?
C2 N2 C1 N1 -38.3(6) . . . . ?
S1 N1 C1 N2 61.0(5) . . . . ?
C1 N2 C2 C7 -173.2(4) . . . . ?
C1 N2 C2 C3 8.7(7) . . . . ?
N2 C2 C3 C4 175.2(4) . . . . ?
C7 C2 C3 C4 -2.9(7) . . . . ?
N2 C2 C3 S1 -1.5(6) . . . . ?
C7 C2 C3 S1 -179.6(3) . . . . ?
O1 S1 C3 C4 -40.9(4) . . . . ?
O2 S1 C3 C4 89.3(4) . . . . ?
N1 S1 C3 C4 -155.9(3) . . . . ?
O1 S1 C3 C2 135.8(4) . . . . ?
O2 S1 C3 C2 -93.9(4) . . . . ?
N1 S1 C3 C2 20.9(4) . . . . ?
C2 C3 C4 C5 3.1(7) . . . . ?
S1 C3 C4 C5 179.8(3) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
C3 C4 C5 S2 -176.9(3) . . . . ?
O4 S2 C5 C6 179.4(4) . . . . ?
O3 S2 C5 C6 50.1(4) . . . . ?
N3 S2 C5 C6 -66.2(5) . . . . ?
O4 S2 C5 C4 -5.3(4) . . . . ?
O3 S2 C5 C4 -134.5(3) . . . . ?
N3 S2 C5 C4 109.1(4) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
S2 C5 C6 C7 174.6(3) . . . . ?
C4 C5 C6 Cl1 -179.5(3) . . . . ?
S2 C5 C6 Cl1 -4.1(6) . . . . ?
C5 C6 C7 C2 0.9(7) . . . . ?
Cl1 C6 C7 C2 179.7(3) . . . . ?
N2 C2 C7 C6 -177.2(4) . . . . ?
C3 C2 C7 C6 0.9(6) . . . . ?
C12 N4 C8 C9 1.9(9) . . . . ?
N4 C8 C9 C10 -3.0(10) . . . . ?
C8 C9 C10 C11 1.6(9) . . . . ?
C8 C9 C10 C19 -178.8(5) . . . . ?
C9 C10 C11 C12 0.4(9) . . . . ?
C19 C10 C11 C12 -179.2(6) . . . . ?
C8 N4 C12 C11 0.3(10) . . . . ?
C10 C11 C12 N4 -1.5(10) . . . . ?
C17 N5 C13 C14 -0.3(8) . . . . ?
N5 C13 C14 C15 1.4(8) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C13 C14 C15 C18 176.8(5) . . . . ?
C14 C15 C16 C17 -1.2(8) . . . . ?
C18 C15 C16 C17 -178.6(5) . . . . ?
C13 N5 C17 C16 -1.7(9) . . . . ?
C15 C16 C17 N5 2.5(10) . . . . ?
C16 C15 C18 C19 -93.0(7) . . . . ?
C14 C15 C18 C19 89.8(7) . . . . ?
C15 C18 C19 C10 178.5(5) . . . . ?
C9 C10 C19 C18 -129.1(7) . . . . ?
C11 C10 C19 C18 50.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 989057'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_C:\Users\JRWang\Desktop\3161\2013316.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            HCTEN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H64 Cl2 N14 O8 S4'
_chemical_formula_weight         1324.40

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'
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   P21/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                   11.2718(14)
_cell_length_b                   26.189(3)
_cell_length_c                   21.160(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.349(9)
_cell_angle_gamma                90.00
_cell_volume                     6235.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2672
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7990
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_process_details   sadabs

_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  'Bruker APEX-II CCD'
_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            43859
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_sigmaI/netI    0.1371
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             10978
_reflns_number_gt                4943
_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)+(0.0871P)²+22.9049P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.00031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10978
_refine_ls_number_parameters     840
_refine_ls_number_restraints     286
_refine_ls_R_factor_all          0.2088
_refine_ls_R_factor_gt           0.0912
_refine_ls_wR_factor_ref         0.2664
_refine_ls_wR_factor_gt          0.2063
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.010

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 0.13907(8) 0.08042(3) 0.96473(5) 0.0728(2) Uani 1 1 d U . .
Cl2 Cl 0.64033(8) 0.40626(3) 0.01019(6) 0.0831(3) Uani 1 1 d U . .
S1 S 0.20682(7) 0.09721(3) 0.81611(4) 0.05222(16) Uani 1 1 d U . .
S2 S 0.47220(6) 0.25978(3) 0.89487(4) 0.04434(15) Uani 1 1 d U . .
S3 S 0.77270(7) 0.40249(3) 0.15257(4) 0.05706(16) Uani 1 1 d U . .
S4 S 1.00351(7) 0.23298(3) 0.07999(4) 0.04481(15) Uani 1 1 d U . .
O1 O 0.23110(19) 0.04488(8) 0.83142(12) 0.0691(4) Uani 1 1 d U . .
O2 O 0.59315(16) 0.24278(8) 0.90568(10) 0.0607(4) Uani 1 1 d U . .
O3 O 0.4361(2) 0.28061(8) 0.83482(10) 0.0704(4) Uani 1 1 d U . .
O4 O 0.2608(2) 0.11796(8) 0.76223(10) 0.0717(3) Uani 1 1 d U . .
O5 O 0.8495(2) 0.38633(8) 0.20513(11) 0.0794(3) Uani 1 1 d U . .
O6 O 0.78593(19) 0.45340(7) 0.12920(12) 0.0709(4) Uani 1 1 d U . .
O7 O 1.12240(17) 0.24982(8) 0.07122(10) 0.0570(4) Uani 1 1 d U . .
O8 O 0.9772(2) 0.21254(8) 0.13998(10) 0.0650(4) Uani 1 1 d U . .
N5 N 0.2569(2) 0.85092(10) 0.93981(14) 0.0738(3) Uani 1 1 d U . .
N3' N 0.3741(2) 0.23983(9) 1.02214(11) 0.0513(3) Uani 1 1 d U . .
H14 H 0.3458 0.2367 1.0588 0.062 Uiso 1 1 calc R . .
N2' N 0.4462(2) 0.30158(8) 0.94883(11) 0.0468(3) Uani 1 1 d U . .
N6 N 0.5122(2) 0.51199(9) 0.83346(13) 0.0597(4) Uani 1 1 d U . .
N12 N 0.9896(2) 0.21904(10) 0.78921(13) 0.0632(6) Uani 1 1 d U . .
N10 N 0.5436(2) 0.20952(10) 0.67835(13) 0.0605(6) Uani 1 1 d U . .
N8 N 1.2156(2) 0.34483(9) 0.91241(12) 0.0566(3) Uani 1 1 d U . .
C5' C 0.9055(2) 0.28296(10) 0.05943(13) 0.03667(19) Uani 1 1 d U . .
N3 N 0.8706(2) 0.24893(10) -0.04595(12) 0.0576(3) Uani 1 1 d U . .
N2 N 0.9682(2) 0.19024(8) 0.02644(11) 0.0476(3) Uani 1 1 d U . .
C8 C 0.2432(4) 0.88826(15) 0.8979(2) 0.1041(3) Uani 1 1 d U . .
H1 H 0.1731 0.8889 0.8725 0.125 Uiso 1 1 calc R . .
C9 C 0.3255(3) 0.92628(14) 0.8893(2) 0.0926(3) Uani 1 1 d U . .
H3 H 0.3113 0.9512 0.8584 0.111 Uiso 1 1 calc R . .
C10 C 0.4290(3) 0.92659(12) 0.92706(16) 0.0622(3) Uani 1 1 d U . .
C18 C 0.5223(3) 0.96694(13) 0.92273(19) 0.0854(5) Uani 1 1 d U . .
H4 H 0.5935 0.9603 0.9457 0.102 Uiso 1 1 calc R . .
C19 C 0.5192(3) 1.00658(13) 0.89405(19) 0.0851(5) Uani 1 1 d U . .
H8 H 0.4491 1.0130 0.8700 0.102 Uiso 1 1 calc R . .
C15 C 0.6119(3) 1.04662(12) 0.89185(17) 0.0674(4) Uani 1 1 d U . .
C14 C 0.7217(3) 1.04480(14) 0.92568(19) 0.0788(4) Uani 1 1 d U . .
H5 H 0.7431 1.0173 0.9517 0.095 Uiso 1 1 calc R . .
C13 C 0.7984(3) 1.08624(14) 0.91878(19) 0.0823(4) Uani 1 1 d U . .
H2 H 0.8722 1.0850 0.9408 0.099 Uiso 1 1 calc R . .
C12 C 0.3584(3) 0.85201(12) 0.97386(16) 0.0625(3) Uani 1 1 d U . .
H10 H 0.3721 0.8263 1.0037 0.075 Uiso 1 1 calc R . .
C11 C 0.4442(3) 0.88746(12) 0.96886(17) 0.0627(3) Uani 1 1 d U . .
H9 H 0.5142 0.8851 0.9942 0.075 Uiso 1 1 calc R . .
C16 C 0.5875(3) 1.08820(13) 0.85467(19) 0.0758(4) Uani 1 1 d U . .
H7 H 0.5155 1.0906 0.8310 0.091 Uiso 1 1 calc R . .
C17 C 0.6695(3) 1.12604(14) 0.85251(19) 0.0803(4) Uani 1 1 d U . .
H6 H 0.6498 1.1539 0.8267 0.096 Uiso 1 1 calc R . .
N4 N 0.7745(2) 1.12700(11) 0.88356(15) 0.0789(4) Uani 1 1 d U . .
C3 C 0.2586(2) 0.13667(10) 0.87942(14) 0.0401(2) Uani 1 1 d U . .
C4 C 0.3342(2) 0.17643(10) 0.86691(14) 0.0410(3) Uani 1 1 d U . .
H12 H 0.3574 0.1809 0.8258 0.049 Uiso 1 1 calc R . .
C5 C 0.3768(2) 0.21004(10) 0.91407(13) 0.03609(19) Uani 1 1 d U . .
C6 C 0.3394(2) 0.20571(10) 0.97573(13) 0.0405(2) Uani 1 1 d U . .
C7 C 0.4568(3) 0.28102(11) 1.01205(14) 0.0484(3) Uani 1 1 d U . .
H13 H 0.4434 0.3082 1.0420 0.058 Uiso 1 1 calc R . .
H11 H 0.5372 0.2686 1.0206 0.058 Uiso 1 1 calc R . .
N1' N 0.0670(2) 0.10426(10) 0.81271(15) 0.0669(5) Uani 1 1 d U . .
C2 C 0.2253(2) 0.13052(10) 0.94319(14) 0.0451(3) Uani 1 1 d U . .
C1 C 0.2636(2) 0.16489(10) 0.98856(14) 0.0462(3) Uani 1 1 d U . .
H15 H 0.2386 0.1611 1.0294 0.055 Uiso 1 1 calc R . .
C25 C 0.8712(3) 0.22058(12) 0.78713(15) 0.0635(7) Uani 1 1 d U . .
H16 H 0.8299 0.1899 0.7828 0.076 Uiso 1 1 calc R . .
C26 C 0.8063(3) 0.26506(12) 0.79107(15) 0.0568(7) Uani 1 1 d U . .
H19 H 0.7237 0.2637 0.7903 0.068 Uiso 1 1 calc R . .
C27 C 0.8635(3) 0.31153(11) 0.79615(14) 0.0499(6) Uani 1 1 d U . .
C31 C 0.8020(3) 0.36186(13) 0.80106(16) 0.0632(7) Uani 1 1 d U . .
H20 H 0.8489 0.3908 0.7975 0.076 Uiso 1 1 calc R . .
C30 C 0.6937(3) 0.36932(13) 0.80947(16) 0.0655(6) Uani 1 1 d U . .
H21 H 0.6458 0.3405 0.8114 0.079 Uiso 1 1 calc R . .
C22 C 0.6346(3) 0.41988(12) 0.81666(14) 0.0523(4) Uani 1 1 d U . .
C21 C 0.5304(3) 0.42184(12) 0.84642(17) 0.0682(4) Uani 1 1 d U . .
H24 H 0.4975 0.3920 0.8615 0.082 Uiso 1 1 calc R . .
C20 C 0.4739(3) 0.46764(12) 0.85428(18) 0.0684(5) Uani 1 1 d U . .
H25 H 0.4041 0.4675 0.8756 0.082 Uiso 1 1 calc R . .
C29 C 1.0427(3) 0.26361(12) 0.79485(17) 0.0678(8) Uani 1 1 d U . .
H18 H 1.1253 0.2640 0.7969 0.081 Uiso 1 1 calc R . .
C28 C 0.9848(3) 0.30990(12) 0.79798(16) 0.0613(8) Uani 1 1 d U . .
H17 H 1.0285 0.3400 0.8014 0.074 Uiso 1 1 calc R . .
C23 C 0.6757(3) 0.46597(12) 0.79399(16) 0.0621(4) Uani 1 1 d U . .
H23 H 0.7459 0.4669 0.7730 0.074 Uiso 1 1 calc R . .
C24 C 0.6134(3) 0.51008(13) 0.80238(17) 0.0664(4) Uani 1 1 d U . .
H22 H 0.6423 0.5402 0.7859 0.080 Uiso 1 1 calc R . .
C49 C 0.4284(3) 0.20960(14) 0.68915(15) 0.0665(6) Uani 1 1 d U . .
H26 H 0.3918 0.1784 0.6959 0.080 Uiso 1 1 calc R . .
C50 C 0.3590(3) 0.25376(13) 0.69090(15) 0.0667(7) Uani 1 1 d U . .
H34 H 0.2783 0.2513 0.6973 0.080 Uiso 1 1 calc R . .
C51 C 0.41070(9) 0.301402(19) 0.68298(14) 0.0727(6) Uani 1 1 d DU . .
C55 C 0.35821(4) 0.35350(2) 0.68629(16) 0.0866(2) Uani 1 1 d DU . .
H33 H 0.4102 0.3811 0.6896 0.104 Uiso 1 1 calc R . .
C54 C 0.25366(4) 0.362393(18) 0.68502(15) 0.0867(2) Uani 1 1 d DU . .
H32 H 0.2022 0.3347 0.6813 0.104 Uiso 1 1 calc R . .
C46 C 0.19935(10) 0.41410(2) 0.68883(16) 0.0823(7) Uani 1 1 d DU . .
N9 N 0.0709(3) 0.50636(12) 0.69608(16) 0.0859(8) Uani 1 1 d U . .
C45 C 0.2505(3) 0.45920(14) 0.70950(15) 0.0687(6) Uani 1 1 d U . .
H31 H 0.3310 0.4600 0.7217 0.082 Uiso 1 1 calc R . .
C44 C 0.1841(3) 0.50310(14) 0.71237(16) 0.0701(7) Uani 1 1 d U . .
H30 H 0.2227 0.5326 0.7270 0.084 Uiso 1 1 calc R . .
C53 C 0.5905(3) 0.25507(12) 0.66982(16) 0.0672(7) Uani 1 1 d U . .
H36 H 0.6711 0.2567 0.6626 0.081 Uiso 1 1 calc R . .
C52 C 0.5284(3) 0.30044(13) 0.67086(16) 0.0696(7) Uani 1 1 d U . .
H35 H 0.5674 0.3309 0.6632 0.084 Uiso 1 1 calc R . .
C37 C 1.1293(3) 0.34556(13) 0.95232(17) 0.0698(3) Uani 1 1 d U . .
H46 H 1.1257 0.3191 0.9814 0.084 Uiso 1 1 calc R . .
C38 C 1.0445(3) 0.38344(13) 0.95303(16) 0.0665(3) Uani 1 1 d U . .
H45 H 0.9850 0.3820 0.9816 0.080 Uiso 1 1 calc R . .
C39 C 1.04876(7) 0.42355(2) 0.91100(13) 0.0725(3) Uani 1 1 d DU . .
C34 C 0.84376(9) 0.53832(2) 0.91904(12) 0.0954(3) Uani 1 1 d DU . .
C33 C 0.8609(3) 0.58098(15) 0.88476(18) 0.0840(3) Uani 1 1 d U . .
H43 H 0.9231 0.5826 0.8578 0.101 Uiso 1 1 calc R . .
C32 C 0.7864(3) 0.62175(16) 0.88983(19) 0.0904(3) Uani 1 1 d U . .
H42 H 0.8018 0.6507 0.8661 0.109 Uiso 1 1 calc R . .
N7 N 0.6937(3) 0.62349(11) 0.92589(16) 0.0802(3) Uani 1 1 d U . .
C41 C 1.2182(3) 0.38275(12) 0.87032(17) 0.0663(3) Uani 1 1 d U . .
H39 H 1.2766 0.3822 0.8411 0.080 Uiso 1 1 calc R . .
C36 C 0.6777(4) 0.58255(15) 0.9602(2) 0.0973(3) Uani 1 1 d U . .
H41 H 0.6150 0.5825 0.9870 0.117 Uiso 1 1 calc R . .
C35 C 0.7489(3) 0.53958(14) 0.9589(2) 0.0883(3) Uani 1 1 d U . .
H40 H 0.7338 0.5116 0.9843 0.106 Uiso 1 1 calc R . .
C40 C 1.1387(3) 0.42244(12) 0.86817(16) 0.0629(3) Uani 1 1 d U . .
H44 H 1.1446 0.4484 0.8385 0.075 Uiso 1 1 calc R . .
C3' C 0.7993(2) 0.35843(10) 0.09230(15) 0.0447(2) Uani 1 1 d U . .
C4' C 0.8800(2) 0.31908(10) 0.10443(14) 0.0393(3) Uani 1 1 d U . .
H48 H 0.9186 0.3169 0.1444 0.047 Uiso 1 1 calc R . .
C6' C 0.8470(2) 0.28387(10) -0.00131(13) 0.0418(2) Uani 1 1 d U . .
C7' C 0.9633(3) 0.21104(11) -0.03781(14) 0.0541(3) Uani 1 1 d U . .
H49 H 1.0392 0.2264 -0.0460 0.065 Uiso 1 1 calc R . .
H47 H 0.9484 0.1836 -0.0681 0.065 Uiso 1 1 calc R . .
N1 N 0.6367(2) 0.39578(9) 0.16802(16) 0.0813(4) Uani 1 1 d U . .
C2' C 0.7418(2) 0.35885(10) 0.03130(15) 0.0465(3) Uani 1 1 d U . .
C1' C 0.7644(3) 0.32317(11) -0.01374(15) 0.0510(3) Uani 1 1 d U . .
H50 H 0.7243 0.3250 -0.0533 0.061 Uiso 1 1 calc R . .
C43 C 0.90122(5) 0.48785(2) 0.93200(4) 0.1085(2) Uani 1 1 d DU . .
H100 H 0.8759 0.4680 0.9650 0.130 Uiso 1 1 calc R . .
C47 C 0.0809(3) 0.41624(15) 0.67379(19) 0.0870(2) Uani 1 1 d U . .
H102 H 0.0399 0.3868 0.6610 0.104 Uiso 1 1 calc R . .
C48 C 0.0204(4) 0.46260(15) 0.67752(19) 0.0877(2) Uani 1 1 d U . .
H103 H -0.0606 0.4629 0.6663 0.105 Uiso 1 1 calc R . .
C42 C 0.98047(5) 0.47185(2) 0.90055(4) 0.1058(2) Uani 1 1 d DU . .
H104 H 1.0004 0.4919 0.8665 0.127 Uiso 1 1 calc R . .
H201 H 0.907(2) 0.1749(10) 0.0357(12) 0.059(8) Uiso 1 1 d . . .
H200 H 0.840(2) 0.2460(9) -0.0739(11) 0.042(7) Uiso 1 1 d . . .
H203 H 0.588(2) 0.4194(10) 0.1582(12) 0.055(8) Uiso 1 1 d . . .
H202 H 0.621(3) 0.3655(11) 0.1848(14) 0.075(10) Uiso 1 1 d . . .
H204 H 0.379(2) 0.3169(10) 0.9359(12) 0.060(8) Uiso 1 1 d . . .
H205 H 0.020(2) 0.0819(8) 0.8073(11) 0.037(7) Uiso 1 1 d . . .
H206 H 0.044(2) 0.1306(10) 0.7975(13) 0.067(9) Uiso 1 1 d . . .


_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 C2 1.710(3) . ?
Cl2 C2' 1.729(3) . ?
S1 O4 1.431(2) . ?
S1 O1 1.431(2) . ?
S1 N1' 1.584(3) . ?
S1 C3 1.764(3) . ?
S2 O3 1.420(2) . ?
S2 O2 1.440(2) . ?
S2 N2' 1.621(2) . ?
S2 C5 1.752(3) . ?
S3 O5 1.433(3) . ?
S3 O6 1.433(2) . ?
S3 N1 1.596(3) . ?
S3 C3' 1.759(3) . ?
S4 O8 1.425(2) . ?
S4 O7 1.433(2) . ?
S4 N2 1.626(2) . ?
S4 C5' 1.752(3) . ?
N5 C12 1.316(4) . ?
N5 C8 1.323(5) . ?
N3' C6 1.368(4) . ?
N3' C7 1.449(4) . ?
N3' H14 0.8600 . ?
N2' C7 1.441(4) . ?
N2' H204 0.88(3) . ?
N6 C20 1.323(4) . ?
N6 C24 1.351(4) . ?
N12 C29 1.314(4) . ?
N12 C25 1.333(4) . ?
N10 C53 1.322(4) . ?
N10 C49 1.333(4) . ?
N8 C37 1.325(4) . ?
N8 C41 1.335(4) . ?
C5' C4' 1.384(4) . ?
C5' C6' 1.410(4) . ?
N3 C6' 1.353(4) . ?
N3 C7' 1.444(4) . ?
N3 H200 0.67(2) . ?
N2 C7' 1.463(4) . ?
N2 H201 0.83(3) . ?
C8 C9 1.381(5) . ?
C8 H1 0.9300 . ?
C9 C10 1.375(5) . ?
C9 H3 0.9300 . ?
C10 C11 1.358(5) . ?
C10 C18 1.497(5) . ?
C18 C19 1.202(5) . ?
C18 H4 0.9300 . ?
C19 C15 1.483(5) . ?
C19 H8 0.9300 . ?
C15 C16 1.362(5) . ?
C15 C14 1.394(5) . ?
C14 C13 1.400(5) . ?
C14 H5 0.9300 . ?
C13 N4 1.321(5) . ?
C13 H2 0.9300 . ?
C12 C11 1.349(4) . ?
C12 H10 0.9300 . ?
C11 H9 0.9300 . ?
C16 C17 1.357(5) . ?
C16 H7 0.9300 . ?
C17 N4 1.320(4) . ?
C17 H6 0.9300 . ?
C3 C4 1.381(4) . ?
C3 C2 1.431(4) . ?
C4 C5 1.395(4) . ?
C4 H12 0.9300 . ?
C5 C6 1.399(4) . ?
C6 C1 1.405(4) . ?
C7 H13 0.9700 . ?
C7 H11 0.9700 . ?
N1' H205 0.79(2) . ?
N1' H206 0.80(3) . ?
C2 C1 1.368(4) . ?
C1 H15 0.9300 . ?
C25 C26 1.381(4) . ?
C25 H16 0.9300 . ?
C26 C27 1.379(4) . ?
C26 H19 0.9300 . ?
C27 C28 1.366(4) . ?
C27 C31 1.496(4) . ?
C31 C30 1.259(5) . ?
C31 H20 0.9300 . ?
C30 C22 1.494(5) . ?
C30 H21 0.9300 . ?
C22 C21 1.366(5) . ?
C22 C23 1.389(4) . ?
C21 C20 1.373(4) . ?
C21 H24 0.9300 . ?
C20 H25 0.9300 . ?
C29 C28 1.380(5) . ?
C29 H18 0.9300 . ?
C28 H17 0.9300 . ?
C23 C24 1.368(5) . ?
C23 H23 0.9300 . ?
C24 H22 0.9300 . ?
C49 C50 1.398(5) . ?
C49 H26 0.9300 . ?
C50 C51 1.391(4) . ?
C50 H34 0.9300 . ?
C51 C52 1.366(4) . ?
C51 C55 1.4905(7) . ?
C55 C54 1.2000(6) . ?
C55 H33 0.9300 . ?
C54 C46 1.4902(7) . ?
C54 H32 0.9300 . ?
C46 C47 1.356(4) . ?
C46 C45 1.374(4) . ?
N9 C44 1.306(4) . ?
N9 C48 1.328(5) . ?
C45 C44 1.375(5) . ?
C45 H31 0.9300 . ?
C44 H30 0.9300 . ?
C53 C52 1.380(5) . ?
C53 H36 0.9300 . ?
C52 H35 0.9300 . ?
C37 C38 1.377(5) . ?
C37 H46 0.9300 . ?
C38 C39 1.379(4) . ?
C38 H45 0.9300 . ?
C39 C40 1.399(4) . ?
C39 C42 1.4904(7) . ?
C34 C33 1.352(4) . ?
C34 C35 1.400(5) . ?
C34 C43 1.4904(7) . ?
C33 C32 1.366(5) . ?
C33 H43 0.9300 . ?
C32 N7 1.330(5) . ?
C32 H42 0.9300 . ?
N7 C36 1.314(5) . ?
C41 C40 1.371(5) . ?
C41 H39 0.9300 . ?
C36 C35 1.384(5) . ?
C36 H41 0.9300 . ?
C35 H40 0.9300 . ?
C40 H44 0.9300 . ?
C3' C4' 1.389(4) . ?
C3' C2' 1.410(4) . ?
C4' H48 0.9300 . ?
C6' C1' 1.402(4) . ?
C7' H49 0.9700 . ?
C7' H47 0.9700 . ?
N1 H203 0.85(2) . ?
N1 H202 0.89(3) . ?
C2' C1' 1.369(4) . ?
C1' H50 0.9300 . ?
C43 C42 1.2190(7) . ?
C43 H100 0.9300 . ?
C47 C48 1.397(5) . ?
C47 H102 0.9300 . ?
C48 H103 0.9300 . ?
C42 H104 0.9300 . ?

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
O4 S1 O1 117.36(14) . . ?
O4 S1 N1' 112.83(15) . . ?
O1 S1 N1' 107.37(14) . . ?
O4 S1 C3 104.20(13) . . ?
O1 S1 C3 109.79(14) . . ?
N1' S1 C3 104.50(14) . . ?
O3 S2 O2 118.70(14) . . ?
O3 S2 N2' 108.47(13) . . ?
O2 S2 N2' 107.78(13) . . ?
O3 S2 C5 110.22(13) . . ?
O2 S2 C5 108.74(12) . . ?
N2' S2 C5 101.54(13) . . ?
O5 S3 O6 118.20(14) . . ?
O5 S3 N1 110.62(16) . . ?
O6 S3 N1 107.09(13) . . ?
O5 S3 C3' 104.37(14) . . ?
O6 S3 C3' 109.55(15) . . ?
N1 S3 C3' 106.44(14) . . ?
O8 S4 O7 118.42(13) . . ?
O8 S4 N2 107.89(13) . . ?
O7 S4 N2 108.33(13) . . ?
O8 S4 C5' 109.93(13) . . ?
O7 S4 C5' 108.61(12) . . ?
N2 S4 C5' 102.48(12) . . ?
C12 N5 C8 114.5(3) . . ?
C6 N3' C7 122.7(2) . . ?
C6 N3' H14 118.7 . . ?
C7 N3' H14 118.7 . . ?
C7 N2' S2 113.16(18) . . ?
C7 N2' H204 118.7(17) . . ?
S2 N2' H204 105.9(17) . . ?
C20 N6 C24 115.5(3) . . ?
C29 N12 C25 115.2(3) . . ?
C53 N10 C49 115.1(3) . . ?
C37 N8 C41 117.4(3) . . ?
C4' C5' C6' 120.7(2) . . ?
C4' C5' S4 119.5(2) . . ?
C6' C5' S4 119.6(2) . . ?
C6' N3 C7' 123.5(2) . . ?
C6' N3 H200 125(2) . . ?
C7' N3 H200 111(2) . . ?
C7' N2 S4 112.70(18) . . ?
C7' N2 H201 114.3(18) . . ?
S4 N2 H201 109.9(18) . . ?
N5 C8 C9 124.7(4) . . ?
N5 C8 H1 117.7 . . ?
C9 C8 H1 117.7 . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 H3 120.6 . . ?
C8 C9 H3 120.6 . . ?
C11 C10 C9 116.4(3) . . ?
C11 C10 C18 120.7(3) . . ?
C9 C10 C18 122.9(3) . . ?
C19 C18 C10 129.8(4) . . ?
C19 C18 H4 115.1 . . ?
C10 C18 H4 115.1 . . ?
C18 C19 C15 128.8(4) . . ?
C18 C19 H8 115.6 . . ?
C15 C19 H8 115.6 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 C19 117.7(3) . . ?
C14 C15 C19 124.5(3) . . ?
C15 C14 C13 117.1(3) . . ?
C15 C14 H5 121.5 . . ?
C13 C14 H5 121.5 . . ?
N4 C13 C14 125.3(3) . . ?
N4 C13 H2 117.3 . . ?
C14 C13 H2 117.3 . . ?
N5 C12 C11 125.2(3) . . ?
N5 C12 H10 117.4 . . ?
C11 C12 H10 117.4 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H9 119.8 . . ?
C10 C11 H9 119.8 . . ?
C17 C16 C15 119.2(3) . . ?
C17 C16 H7 120.4 . . ?
C15 C16 H7 120.4 . . ?
N4 C17 C16 126.1(4) . . ?
N4 C17 H6 116.9 . . ?
C16 C17 H6 116.9 . . ?
C13 N4 C17 114.4(3) . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 S1 118.5(2) . . ?
C2 C3 S1 123.8(2) . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H12 119.0 . . ?
C5 C4 H12 119.0 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 S2 119.6(2) . . ?
C6 C5 S2 119.9(2) . . ?
N3' C6 C5 121.8(2) . . ?
N3' C6 C1 120.7(3) . . ?
C5 C6 C1 117.5(2) . . ?
N2' C7 N3' 113.3(2) . . ?
N2' C7 H13 108.9 . . ?
N3' C7 H13 108.9 . . ?
N2' C7 H11 108.9 . . ?
N3' C7 H11 108.9 . . ?
H13 C7 H11 107.7 . . ?
S1 N1' H205 125.1(16) . . ?
S1 N1' H206 115(2) . . ?
H205 N1' H206 113(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 Cl1 118.6(2) . . ?
C3 C2 Cl1 121.5(2) . . ?
C2 C1 C6 122.4(3) . . ?
C2 C1 H15 118.8 . . ?
C6 C1 H15 118.8 . . ?
N12 C25 C26 123.8(3) . . ?
N12 C25 H16 118.1 . . ?
C26 C25 H16 118.1 . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 H19 119.9 . . ?
C25 C26 H19 119.9 . . ?
C28 C27 C26 116.0(3) . . ?
C28 C27 C31 119.5(3) . . ?
C26 C27 C31 124.5(3) . . ?
C30 C31 C27 127.2(3) . . ?
C30 C31 H20 116.4 . . ?
C27 C31 H20 116.4 . . ?
C31 C30 C22 126.4(3) . . ?
C31 C30 H21 116.8 . . ?
C22 C30 H21 116.8 . . ?
C21 C22 C23 116.1(3) . . ?
C21 C22 C30 118.8(3) . . ?
C23 C22 C30 125.1(3) . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H24 119.8 . . ?
C20 C21 H24 119.8 . . ?
N6 C20 C21 124.3(3) . . ?
N6 C20 H25 117.8 . . ?
C21 C20 H25 117.8 . . ?
N12 C29 C28 124.8(3) . . ?
N12 C29 H18 117.6 . . ?
C28 C29 H18 117.6 . . ?
C27 C28 C29 120.1(3) . . ?
C27 C28 H17 120.0 . . ?
C29 C28 H17 120.0 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
N6 C24 C23 123.2(3) . . ?
N6 C24 H22 118.4 . . ?
C23 C24 H22 118.4 . . ?
N10 C49 C50 124.0(3) . . ?
N10 C49 H26 118.0 . . ?
C50 C49 H26 118.0 . . ?
C51 C50 C49 120.0(3) . . ?
C51 C50 H34 120.0 . . ?
C49 C50 H34 120.0 . . ?
C52 C51 C50 115.1(2) . . ?
C52 C51 C55 114.73(16) . . ?
C50 C51 C55 130.16(17) . . ?
C54 C55 C51 124.65(6) . . ?
C54 C55 H33 117.7 . . ?
C51 C55 H33 117.7 . . ?
C55 C54 C46 125.52(7) . . ?
C55 C54 H32 117.2 . . ?
C46 C54 H32 117.2 . . ?
C47 C46 C45 115.3(2) . . ?
C47 C46 C54 115.27(19) . . ?
C45 C46 C54 129.22(18) . . ?
C44 N9 C48 114.6(3) . . ?
C46 C45 C44 120.9(3) . . ?
C46 C45 H31 119.5 . . ?
C44 C45 H31 119.5 . . ?
N9 C44 C45 124.7(3) . . ?
N9 C44 H30 117.7 . . ?
C45 C44 H30 117.7 . . ?
N10 C53 C52 124.6(3) . . ?
N10 C53 H36 117.7 . . ?
C52 C53 H36 117.7 . . ?
C51 C52 C53 121.2(3) . . ?
C51 C52 H35 119.4 . . ?
C53 C52 H35 119.4 . . ?
N8 C37 C38 123.5(3) . . ?
N8 C37 H46 118.2 . . ?
C38 C37 H46 118.2 . . ?
C39 C38 C37 119.4(3) . . ?
C39 C38 H45 120.3 . . ?
C37 C38 H45 120.3 . . ?
C38 C39 C40 117.09(19) . . ?
C38 C39 C42 134.8(2) . . ?
C40 C39 C42 108.00(18) . . ?
C33 C34 C35 116.2(2) . . ?
C33 C34 C43 139.2(2) . . ?
C35 C34 C43 104.42(19) . . ?
C34 C33 C32 119.7(3) . . ?
C34 C33 H43 120.1 . . ?
C32 C33 H43 120.1 . . ?
N7 C32 C33 125.4(4) . . ?
N7 C32 H42 117.3 . . ?
C33 C32 H42 117.3 . . ?
C36 N7 C32 115.3(3) . . ?
N8 C41 C40 123.1(3) . . ?
N8 C41 H39 118.4 . . ?
C40 C41 H39 118.4 . . ?
N7 C36 C35 123.6(4) . . ?
N7 C36 H41 118.2 . . ?
C35 C36 H41 118.2 . . ?
C36 C35 C34 119.8(3) . . ?
C36 C35 H40 120.1 . . ?
C34 C35 H40 120.1 . . ?
C41 C40 C39 119.4(3) . . ?
C41 C40 H44 120.3 . . ?
C39 C40 H44 120.3 . . ?
C4' C3' C2' 115.9(3) . . ?
C4' C3' S3 119.4(2) . . ?
C2' C3' S3 124.7(2) . . ?
C5' C4' C3' 122.7(3) . . ?
C5' C4' H48 118.7 . . ?
C3' C4' H48 118.7 . . ?
N3 C6' C1' 121.4(3) . . ?
N3 C6' C5' 121.6(2) . . ?
C1' C6' C5' 117.0(3) . . ?
N3 C7' N2 110.8(2) . . ?
N3 C7' H49 109.5 . . ?
N2 C7' H49 109.5 . . ?
N3 C7' H47 109.5 . . ?
N2 C7' H47 109.5 . . ?
H49 C7' H47 108.1 . . ?
S3 N1 H203 119.4(18) . . ?
S3 N1 H202 113.1(19) . . ?
H203 N1 H202 127(3) . . ?
C1' C2' C3' 122.5(3) . . ?
C1' C2' Cl2 117.2(2) . . ?
C3' C2' Cl2 120.3(2) . . ?
C2' C1' C6' 121.3(3) . . ?
C2' C1' H50 119.4 . . ?
C6' C1' H50 119.4 . . ?
C42 C43 C34 121.93(10) . . ?
C42 C43 H100 119.0 . . ?
C34 C43 H100 119.0 . . ?
C46 C47 C48 120.0(3) . . ?
C46 C47 H102 120.0 . . ?
C48 C47 H102 120.0 . . ?
N9 C48 C47 124.4(4) . . ?
N9 C48 H103 117.8 . . ?
C47 C48 H103 117.8 . . ?
C43 C42 C39 126.82(11) . . ?
C43 C42 H104 116.6 . . ?
C39 C42 H104 116.6 . . ?

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
O3 S2 N2' C7 168.2(2) . . . . ?
O2 S2 N2' C7 -62.1(2) . . . . ?
C5 S2 N2' C7 52.1(2) . . . . ?
O8 S4 C5' C4' 44.2(2) . . . . ?
O7 S4 C5' C4' -86.8(2) . . . . ?
N2 S4 C5' C4' 158.7(2) . . . . ?
O8 S4 C5' C6' -131.3(2) . . . . ?
O7 S4 C5' C6' 97.7(2) . . . . ?
N2 S4 C5' C6' -16.8(2) . . . . ?
O8 S4 N2 C7' 165.8(2) . . . . ?
O7 S4 N2 C7' -64.9(2) . . . . ?
C5' S4 N2 C7' 49.8(2) . . . . ?
C12 N5 C8 C9 -0.5(6) . . . . ?
N5 C8 C9 C10 -1.1(7) . . . . ?
C8 C9 C10 C11 2.7(5) . . . . ?
C8 C9 C10 C18 -178.2(4) . . . . ?
C11 C10 C18 C19 -171.2(4) . . . . ?
C9 C10 C18 C19 9.8(7) . . . . ?
C10 C18 C19 C15 178.2(4) . . . . ?
C18 C19 C15 C16 179.0(4) . . . . ?
C18 C19 C15 C14 -1.6(7) . . . . ?
C16 C15 C14 C13 0.2(5) . . . . ?
C19 C15 C14 C13 -179.2(3) . . . . ?
C15 C14 C13 N4 0.9(6) . . . . ?
C8 N5 C12 C11 0.4(5) . . . . ?
N5 C12 C11 C10 1.3(6) . . . . ?
C9 C10 C11 C12 -2.8(5) . . . . ?
C18 C10 C11 C12 178.1(3) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C19 C15 C16 C17 178.7(3) . . . . ?
C15 C16 C17 N4 0.2(6) . . . . ?
C14 C13 N4 C17 -1.3(6) . . . . ?
C16 C17 N4 C13 0.8(6) . . . . ?
O4 S1 C3 C4 0.0(2) . . . . ?
O1 S1 C3 C4 126.5(2) . . . . ?
N1' S1 C3 C4 -118.6(2) . . . . ?
O4 S1 C3 C2 178.9(2) . . . . ?
O1 S1 C3 C2 -54.6(3) . . . . ?
N1' S1 C3 C2 60.3(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
S1 C3 C4 C5 178.5(2) . . . . ?
C3 C4 C5 C6 -2.9(4) . . . . ?
C3 C4 C5 S2 -179.8(2) . . . . ?
O3 S2 C5 C4 38.7(3) . . . . ?
O2 S2 C5 C4 -93.0(2) . . . . ?
N2' S2 C5 C4 153.5(2) . . . . ?
O3 S2 C5 C6 -138.2(2) . . . . ?
O2 S2 C5 C6 90.0(2) . . . . ?
N2' S2 C5 C6 -23.4(2) . . . . ?
C7 N3' C6 C5 -3.5(4) . . . . ?
C7 N3' C6 C1 176.9(2) . . . . ?
C4 C5 C6 N3' -176.2(2) . . . . ?
S2 C5 C6 N3' 0.7(4) . . . . ?
C4 C5 C6 C1 3.5(4) . . . . ?
S2 C5 C6 C1 -179.6(2) . . . . ?
S2 N2' C7 N3' -60.9(3) . . . . ?
C6 N3' C7 N2' 34.0(4) . . . . ?
C4 C3 C2 C1 3.1(4) . . . . ?
S1 C3 C2 C1 -175.8(2) . . . . ?
C4 C3 C2 Cl1 -176.2(2) . . . . ?
S1 C3 C2 Cl1 4.9(3) . . . . ?
C3 C2 C1 C6 -2.5(4) . . . . ?
Cl1 C2 C1 C6 176.8(2) . . . . ?
N3' C6 C1 C2 178.8(3) . . . . ?
C5 C6 C1 C2 -0.8(4) . . . . ?
C29 N12 C25 C26 -0.6(5) . . . . ?
N12 C25 C26 C27 1.4(5) . . . . ?
C25 C26 C27 C28 -1.0(5) . . . . ?
C25 C26 C27 C31 -179.6(3) . . . . ?
C28 C27 C31 C30 -168.7(4) . . . . ?
C26 C27 C31 C30 9.9(5) . . . . ?
C27 C31 C30 C22 177.6(3) . . . . ?
C31 C30 C22 C21 -157.6(4) . . . . ?
C31 C30 C22 C23 23.9(5) . . . . ?
C23 C22 C21 C20 -1.9(5) . . . . ?
C30 C22 C21 C20 179.6(3) . . . . ?
C24 N6 C20 C21 0.4(5) . . . . ?
C22 C21 C20 N6 1.5(6) . . . . ?
C25 N12 C29 C28 -0.6(5) . . . . ?
C26 C27 C28 C29 -0.1(5) . . . . ?
C31 C27 C28 C29 178.6(3) . . . . ?
N12 C29 C28 C27 0.9(5) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C30 C22 C23 C24 179.0(3) . . . . ?
C20 N6 C24 C23 -1.8(5) . . . . ?
C22 C23 C24 N6 1.4(5) . . . . ?
C53 N10 C49 C50 0.8(5) . . . . ?
N10 C49 C50 C51 -2.0(5) . . . . ?
C49 C50 C51 C52 3.0(4) . . . . ?
C49 C50 C51 C55 -176.3(3) . . . . ?
C52 C51 C55 C54 165.9(4) . . . . ?
C50 C51 C55 C54 -14.8(6) . . . . ?
C51 C55 C54 C46 179.4(3) . . . . ?
C55 C54 C46 C47 167.2(4) . . . . ?
C55 C54 C46 C45 -17.7(6) . . . . ?
C47 C46 C45 C44 -1.8(5) . . . . ?
C54 C46 C45 C44 -176.9(3) . . . . ?
C48 N9 C44 C45 2.0(5) . . . . ?
C46 C45 C44 N9 -0.4(5) . . . . ?
C49 N10 C53 C52 -0.7(5) . . . . ?
C50 C51 C52 C53 -2.9(5) . . . . ?
C55 C51 C52 C53 176.5(3) . . . . ?
N10 C53 C52 C51 1.9(5) . . . . ?
C41 N8 C37 C38 -1.0(5) . . . . ?
N8 C37 C38 C39 -0.9(5) . . . . ?
C37 C38 C39 C40 1.8(4) . . . . ?
C37 C38 C39 C42 -175.1(2) . . . . ?
C35 C34 C33 C32 -0.8(5) . . . . ?
C43 C34 C33 C32 -175.8(3) . . . . ?
C34 C33 C32 N7 -1.1(6) . . . . ?
C33 C32 N7 C36 2.3(6) . . . . ?
C37 N8 C41 C40 2.1(5) . . . . ?
C32 N7 C36 C35 -1.6(6) . . . . ?
N7 C36 C35 C34 -0.2(6) . . . . ?
C33 C34 C35 C36 1.4(5) . . . . ?
C43 C34 C35 C36 178.0(3) . . . . ?
N8 C41 C40 C39 -1.1(5) . . . . ?
C38 C39 C40 C41 -0.9(4) . . . . ?
C42 C39 C40 C41 176.8(3) . . . . ?
O5 S3 C3' C4' 0.9(3) . . . . ?
O6 S3 C3' C4' 128.4(2) . . . . ?
N1 S3 C3' C4' -116.2(2) . . . . ?
O5 S3 C3' C2' 179.1(2) . . . . ?
O6 S3 C3' C2' -53.4(3) . . . . ?
N1 S3 C3' C2' 62.1(3) . . . . ?
C6' C5' C4' C3' -1.7(4) . . . . ?
S4 C5' C4' C3' -177.1(2) . . . . ?
C2' C3' C4' C5' 1.5(4) . . . . ?
S3 C3' C4' C5' 179.9(2) . . . . ?
C7' N3 C6' C1' 173.4(3) . . . . ?
C7' N3 C6' C5' -5.6(4) . . . . ?
C4' C5' C6' N3 180.0(3) . . . . ?
S4 C5' C6' N3 -4.6(4) . . . . ?
C4' C5' C6' C1' 1.0(4) . . . . ?
S4 C5' C6' C1' 176.4(2) . . . . ?
C6' N3 C7' N2 40.3(4) . . . . ?
S4 N2 C7' N3 -63.8(3) . . . . ?
C4' C3' C2' C1' -0.7(4) . . . . ?
S3 C3' C2' C1' -179.0(2) . . . . ?
C4' C3' C2' Cl2 -179.4(2) . . . . ?
S3 C3' C2' Cl2 2.3(4) . . . . ?
C3' C2' C1' C6' 0.1(4) . . . . ?
Cl2 C2' C1' C6' 178.8(2) . . . . ?
N3 C6' C1' C2' -179.2(3) . . . . ?
C5' C6' C1' C2' -0.2(4) . . . . ?
C33 C34 C43 C42 -12.2(4) . . . . ?
C35 C34 C43 C42 172.46(19) . . . . ?
C45 C46 C47 C48 2.4(5) . . . . ?
C54 C46 C47 C48 178.2(3) . . . . ?
C44 N9 C48 C47 -1.3(6) . . . . ?
C46 C47 C48 N9 -1.0(6) . . . . ?
C34 C43 C42 C39 176.52(12) . . . . ?
C38 C39 C42 C43 2.9(3) . . . . ?
C40 C39 C42 C43 -174.22(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.360
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.079
_database_code_depnum_ccdc_archive 'CCDC 989058'
