

data_global


data_a
#TrackingRef '902002.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H52 Br2 N10 O8 S2'
_chemical_formula_weight         1217.02

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'
Br Br -0.2901 2.4595 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.497(2)
_cell_length_b                   11.542(2)
_cell_length_c                   12.417(3)
_cell_angle_alpha                113.90(3)
_cell_angle_beta                 106.80(3)
_cell_angle_gamma                99.11(3)
_cell_volume                     1368.9(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    1.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5491
_exptl_absorpt_correction_T_max  0.7930
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11331
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5068
_reflns_number_gt                3535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
DFIX 1.38 0.001 C10 C11 C12 C13
DFIX 1.65 0.001 C10 S C13 S
DFIX 1.45 0.001 C11 C12
DFIX 1.38 0.001 C10 C11' C12' C13'
DFIX 1.65 0.001 C10 S' C13' S'
DFIX 1.45 0.001 C11'F C12'
DFIX 0.84 0.03 O4 H4AO O4 H4BO O3 H3O
DFIX 0.86 0.03 N4 H4N N5 H5N
DFIX 0.82 0.03 O1 H1O
ISOR 0.01 C12' C13' S'
;

_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)+(0.0631P)²+1.1632P] 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       0.0086(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5068
_refine_ls_number_parameters     415
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001

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
Br Br 0.94470(4) 0.73539(5) 1.03097(4) 0.0679(2) Uani 1 1 d . . .
O1 O 0.2853(2) 0.2975(2) 0.6128(3) 0.0410(6) Uani 1 1 d D . .
O2 O 0.5638(2) 0.7152(3) 0.5111(2) 0.0413(6) Uani 1 1 d . . .
O3 O 0.7930(3) 0.7666(3) 0.7021(3) 0.0600(8) Uani 1 1 d D . .
O4 O 0.8530(2) 0.5313(3) 0.6295(3) 0.0587(8) Uani 1 1 d D . .
N1 N 0.1279(2) 0.3957(3) 0.6355(3) 0.0347(6) Uani 1 1 d . . .
N2 N 0.1110(2) 0.5188(3) 0.6846(3) 0.0367(7) Uani 1 1 d . . .
N3 N 0.4972(2) 0.6318(3) 0.6621(3) 0.0336(6) Uani 1 1 d . . .
N4 N 0.4088(3) 0.6104(3) 0.5495(3) 0.0406(7) Uani 1 1 d D . .
N5 N 0.3545(3) 0.6445(3) 0.3757(3) 0.0409(7) Uani 1 1 d D . .
C1 C -0.0490(3) 0.2641(4) 0.6480(4) 0.0474(9) Uani 1 1 d . . .
H1A H -0.0317 0.3328 0.7287 0.057 Uiso 1 1 calc R . .
C2 C -0.1479(4) 0.1464(5) 0.5929(5) 0.0637(13) Uani 1 1 d . . .
H2B H -0.1982 0.1358 0.6371 0.076 Uiso 1 1 calc R . .
C3 C -0.1729(4) 0.0442(5) 0.4730(6) 0.0690(14) Uani 1 1 d . . .
H3B H -0.2395 -0.0345 0.4369 0.083 Uiso 1 1 calc R . .
C4 C -0.0993(4) 0.0595(4) 0.4080(5) 0.0659(13) Uani 1 1 d . . .
H4B H -0.1156 -0.0097 0.3277 0.079 Uiso 1 1 calc R . .
C5 C -0.0009(4) 0.1763(4) 0.4600(4) 0.0510(10) Uani 1 1 d . . .
H5B H 0.0482 0.1869 0.4148 0.061 Uiso 1 1 calc R . .
C6 C 0.0233(3) 0.2765(3) 0.5791(3) 0.0365(8) Uani 1 1 d . . .
C7 C 0.2251(3) 0.6060(3) 0.7254(3) 0.0315(7) Uani 1 1 d . A .
C8 C 0.3163(3) 0.5405(3) 0.7020(3) 0.0312(7) Uani 1 1 d . . .
C9 C 0.2504(3) 0.4074(3) 0.6461(3) 0.0316(7) Uani 1 1 d . . .
C10 C 0.2436(3) 0.7498(3) 0.7901(3) 0.0373(8) Uani 1 1 d D . .
S S 0.1371(4) 0.8065(3) 0.8429(5) 0.0468(8) Uani 0.582(6) 1 d PD A 1
C11 C 0.3451(17) 0.8519(11) 0.815(2) 0.074(6) Uani 0.582(6) 1 d PD A 1
H11A H 0.4098 0.8421 0.7846 0.088 Uiso 0.582(6) 1 calc PR A 1
C12 C 0.3335(14) 0.9773(14) 0.8979(18) 0.058(4) Uani 0.582(6) 1 d PD A 1
H12A H 0.4010 1.0569 0.9484 0.069 Uiso 0.582(6) 1 calc PR A 1
C13 C 0.2103(11) 0.9646(6) 0.8926(15) 0.061(5) Uani 0.582(6) 1 d PD A 1
H13A H 0.1747 1.0335 0.9136 0.073 Uiso 0.582(6) 1 calc PR A 1
S' S 0.3719(7) 0.8644(5) 0.8205(8) 0.0549(15) Uani 0.418(6) 1 d PDU A 2
C11' C 0.1655(16) 0.8107(12) 0.843(3) 0.092(13) Uani 0.418(6) 1 d PD A 2
H11B H 0.0853 0.7667 0.8342 0.110 Uiso 0.418(6) 1 calc PR A 2
C12' C 0.2275(14) 0.9540(12) 0.9155(18) 0.031(3) Uani 0.418(6) 1 d PDU A 2
H12B H 0.2041 1.0117 0.9772 0.037 Uiso 0.418(6) 1 calc PR A 2
C13' C 0.325(2) 0.9954(14) 0.883(3) 0.052(6) Uani 0.418(6) 1 d PDU A 2
H13B H 0.3580 1.0801 0.8936 0.062 Uiso 0.418(6) 1 calc PR A 2
C14 C 0.4546(3) 0.6001(3) 0.7353(3) 0.0294(7) Uani 1 1 d . . .
C15 C 0.5506(3) 0.6306(3) 0.8605(3) 0.0318(7) Uani 1 1 d . . .
C16 C 0.6815(3) 0.6623(3) 0.8827(3) 0.0375(8) Uani 1 1 d . . .
H16A H 0.7087 0.6614 0.8188 0.045 Uiso 1 1 calc R . .
C17 C 0.7687(3) 0.6949(4) 1.0020(3) 0.0400(8) Uani 1 1 d . . .
C18 C 0.7318(3) 0.6993(4) 1.0996(3) 0.0456(9) Uani 1 1 d . . .
H18A H 0.7924 0.7221 1.1792 0.055 Uiso 1 1 calc R . .
C19 C 0.6039(4) 0.6694(4) 1.0769(3) 0.0447(9) Uani 1 1 d . . .
H19A H 0.5774 0.6728 1.1419 0.054 Uiso 1 1 calc R . .
C20 C 0.5134(3) 0.6339(4) 0.9569(3) 0.0388(8) Uani 1 1 d . . .
H20A H 0.4268 0.6121 0.9421 0.047 Uiso 1 1 calc R . .
C21 C 0.4496(3) 0.6601(3) 0.4800(3) 0.0339(8) Uani 1 1 d . . .
C22 C 0.3643(3) 0.7083(4) 0.3016(3) 0.0371(8) Uani 1 1 d . . .
C23 C 0.2727(4) 0.6501(4) 0.1781(4) 0.0459(9) Uani 1 1 d . . .
H23A H 0.2112 0.5684 0.1450 0.055 Uiso 1 1 calc R . .
C24 C 0.2720(4) 0.7124(5) 0.1041(4) 0.0555(11) Uani 1 1 d . . .
H24A H 0.2101 0.6725 0.0213 0.067 Uiso 1 1 calc R . .
C25 C 0.3616(4) 0.8323(5) 0.1512(5) 0.0616(12) Uani 1 1 d . . .
H25A H 0.3606 0.8741 0.1010 0.074 Uiso 1 1 calc R . .
C26 C 0.4537(4) 0.8910(5) 0.2737(5) 0.0603(12) Uani 1 1 d . . .
H26A H 0.5151 0.9725 0.3058 0.072 Uiso 1 1 calc R . .
C27 C 0.4553(4) 0.8292(4) 0.3499(4) 0.0489(10) Uani 1 1 d . . .
H27A H 0.5174 0.8692 0.4327 0.059 Uiso 1 1 calc R . .
C28 C 0.8327(5) 0.9035(6) 0.7760(5) 0.0893(17) Uani 1 1 d . . .
H28A H 0.9139 0.9319 0.8446 0.134 Uiso 1 1 calc R . .
H28B H 0.7707 0.9291 0.8108 0.134 Uiso 1 1 calc R . .
H28C H 0.8411 0.9448 0.7242 0.134 Uiso 1 1 calc R . .
H4N H 0.333(2) 0.580(3) 0.536(3) 0.031(9) Uiso 1 1 d D . .
H5N H 0.284(3) 0.595(3) 0.361(3) 0.037(10) Uiso 1 1 d D . .
H1O H 0.342(3) 0.306(4) 0.590(4) 0.050(12) Uiso 1 1 d D . .
H4AO H 0.851(5) 0.610(3) 0.662(5) 0.087(19) Uiso 1 1 d D . .
H3O H 0.715(3) 0.745(6) 0.661(5) 0.11(2) Uiso 1 1 d D . .
H4BO H 0.926(3) 0.529(5) 0.634(5) 0.085(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
Br C17 1.894(3) . ?
O1 C9 1.331(4) . ?
O1 H1O 0.80(3) . ?
O2 C21 1.233(4) . ?
O3 C28 1.379(6) . ?
O3 H3O 0.83(3) . ?
O4 H4AO 0.84(3) . ?
O4 H4BO 0.84(3) . ?
N1 C9 1.356(4) . ?
N1 N2 1.372(4) . ?
N1 C6 1.428(4) . ?
N2 C7 1.333(4) . ?
N3 C14 1.293(4) . ?
N3 N4 1.368(4) . ?
N4 C21 1.357(4) . ?
N4 H4N 0.83(2) . ?
N5 C21 1.356(4) . ?
N5 C22 1.407(5) . ?
N5 H5N 0.84(2) . ?
C1 C6 1.383(5) . ?
C1 C2 1.384(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.383(7) . ?
C2 H2B 0.9300 . ?
C3 C4 1.365(7) . ?
C3 H3B 0.9300 . ?
C4 C5 1.380(6) . ?
C4 H4B 0.9300 . ?
C5 C6 1.370(5) . ?
C5 H5B 0.9300 . ?
C7 C8 1.416(4) . ?
C7 C10 1.467(4) . ?
C8 C9 1.370(5) . ?
C8 C14 1.489(4) . ?
C10 C11 1.3802(12) . ?
C10 C11' 1.3802(11) . ?
C10 S' 1.6506(13) . ?
C10 S 1.6519(11) . ?
S C13 1.6500(13) . ?
C11 C12 1.4500(12) . ?
C11 H11A 0.9300 . ?
C12 C13 1.3800(11) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
S' C13' 1.6500(12) . ?
C11' C12' 1.4501(13) . ?
C11' H11B 0.9300 . ?
C12' C13' 1.3801(11) . ?
C12' H12B 0.9300 . ?
C13' H13B 0.9300 . ?
C14 C15 1.483(4) . ?
C15 C20 1.373(5) . ?
C15 C16 1.407(4) . ?
C16 C17 1.383(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.381(5) . ?
C18 C19 1.371(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.395(5) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C22 C27 1.378(5) . ?
C22 C23 1.386(5) . ?
C23 C24 1.377(6) . ?
C23 H23A 0.9300 . ?
C24 C25 1.364(6) . ?
C24 H24A 0.9300 . ?
C25 C26 1.378(6) . ?
C25 H25A 0.9300 . ?
C26 C27 1.395(6) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
C9 O1 H1O 110(3) . . ?
C28 O3 H3O 106(4) . . ?
H4AO O4 H4BO 112(5) . . ?
C9 N1 N2 111.0(3) . . ?
C9 N1 C6 128.2(3) . . ?
N2 N1 C6 120.9(2) . . ?
C7 N2 N1 105.1(2) . . ?
C14 N3 N4 117.2(3) . . ?
C21 N4 N3 118.1(3) . . ?
C21 N4 H4N 125(2) . . ?
N3 N4 H4N 116(2) . . ?
C21 N5 C22 126.6(3) . . ?
C21 N5 H5N 112(3) . . ?
C22 N5 H5N 122(3) . . ?
C6 C1 C2 118.0(4) . . ?
C6 C1 H1A 121.0 . . ?
C2 C1 H1A 121.0 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2B 119.6 . . ?
C1 C2 H2B 119.6 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3B 120.1 . . ?
C2 C3 H3B 120.1 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4B 119.7 . . ?
C5 C4 H4B 119.7 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5B 120.5 . . ?
C4 C5 H5B 120.5 . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 N1 119.3(3) . . ?
C1 C6 N1 118.9(3) . . ?
N2 C7 C8 111.4(3) . . ?
N2 C7 C10 119.8(3) . . ?
C8 C7 C10 128.7(3) . . ?
C9 C8 C7 104.6(3) . . ?
C9 C8 C14 126.6(3) . . ?
C7 C8 C14 128.7(3) . . ?
O1 C9 N1 118.3(3) . . ?
O1 C9 C8 133.4(3) . . ?
N1 C9 C8 108.0(3) . . ?
C11 C10 C11' 105.9(8) . . ?
C11 C10 C7 127.2(7) . . ?
C11' C10 C7 126.8(7) . . ?
C11 C10 S' 4.4(13) . . ?
C11' C10 S' 109.7(6) . . ?
C7 C10 S' 123.3(3) . . ?
C11 C10 S 111.9(7) . . ?
C11' C10 S 6.5(7) . . ?
C7 C10 S 120.8(2) . . ?
S' C10 S 115.8(3) . . ?
C13 S C10 95.2(6) . . ?
C10 C11 C12 108.1(10) . . ?
C10 C11 H11A 126.0 . . ?
C12 C11 H11A 126.0 . . ?
C13 C12 C11 112.0(14) . . ?
C13 C12 H12A 124.0 . . ?
C11 C12 H12A 124.0 . . ?
C12 C13 S 108.4(10) . . ?
C12 C13 H13A 125.8 . . ?
S C13 H13A 125.8 . . ?
C13' S' C10 97.2(8) . . ?
C10 C11' C12' 109.5(12) . . ?
C10 C11' H11B 125.2 . . ?
C12' C11' H11B 125.2 . . ?
C13' C12' C11' 112.6(17) . . ?
C13' C12' H12B 123.7 . . ?
C11' C12' H12B 123.7 . . ?
C12' C13' S' 106.3(12) . . ?
C12' C13' H13B 126.8 . . ?
S' C13' H13B 126.8 . . ?
N3 C14 C15 116.8(3) . . ?
N3 C14 C8 123.5(3) . . ?
C15 C14 C8 119.7(3) . . ?
C20 C15 C16 119.6(3) . . ?
C20 C15 C14 120.5(3) . . ?
C16 C15 C14 119.8(3) . . ?
C17 C16 C15 118.2(3) . . ?
C17 C16 H16A 120.9 . . ?
C15 C16 H16A 120.9 . . ?
C18 C17 C16 122.4(3) . . ?
C18 C17 Br 119.4(3) . . ?
C16 C17 Br 118.2(3) . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18A 120.7 . . ?
C17 C18 H18A 120.7 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
O2 C21 N5 123.7(3) . . ?
O2 C21 N4 122.1(3) . . ?
N5 C21 N4 114.2(3) . . ?
C27 C22 C23 119.5(3) . . ?
C27 C22 N5 122.6(3) . . ?
C23 C22 N5 117.8(3) . . ?
C24 C23 C22 120.5(4) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24A 119.8 . . ?
C23 C24 H24A 119.8 . . ?
C24 C25 C26 119.7(4) . . ?
C24 C25 H25A 120.2 . . ?
C26 C25 H25A 120.2 . . ?
C25 C26 C27 120.5(4) . . ?
C25 C26 H26A 119.8 . . ?
C27 C26 H26A 119.8 . . ?
C22 C27 C26 119.4(4) . . ?
C22 C27 H27A 120.3 . . ?
C26 C27 H27A 120.3 . . ?
O3 C28 H28A 109.5 . . ?
O3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C9 N1 N2 C7 0.0(4) . . . . ?
C6 N1 N2 C7 -178.3(3) . . . . ?
C14 N3 N4 C21 170.8(3) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 C1 -0.7(6) . . . . ?
C4 C5 C6 N1 177.8(4) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C2 C1 C6 N1 -178.4(3) . . . . ?
C9 N1 C6 C5 -48.9(5) . . . . ?
N2 N1 C6 C5 129.2(4) . . . . ?
C9 N1 C6 C1 129.6(4) . . . . ?
N2 N1 C6 C1 -52.3(4) . . . . ?
N1 N2 C7 C8 0.6(4) . . . . ?
N1 N2 C7 C10 -177.1(3) . . . . ?
N2 C7 C8 C9 -0.9(4) . . . . ?
C10 C7 C8 C9 176.4(3) . . . . ?
N2 C7 C8 C14 -178.3(3) . . . . ?
C10 C7 C8 C14 -0.9(6) . . . . ?
N2 N1 C9 O1 174.3(3) . . . . ?
C6 N1 C9 O1 -7.5(5) . . . . ?
N2 N1 C9 C8 -0.6(4) . . . . ?
C6 N1 C9 C8 177.6(3) . . . . ?
C7 C8 C9 O1 -173.0(4) . . . . ?
C14 C8 C9 O1 4.4(6) . . . . ?
C7 C8 C9 N1 0.9(4) . . . . ?
C14 C8 C9 N1 178.3(3) . . . . ?
N2 C7 C10 C11 -166.1(16) . . . . ?
C8 C7 C10 C11 16.7(17) . . . . ?
N2 C7 C10 C11' 17.0(19) . . . . ?
C8 C7 C10 C11' -160.1(19) . . . . ?
N2 C7 C10 S' -168.6(5) . . . . ?
C8 C7 C10 S' 14.3(7) . . . . ?
N2 C7 C10 S 14.2(5) . . . . ?
C8 C7 C10 S -163.0(4) . . . . ?
C11 C10 S C13 3.5(15) . . . . ?
C11' C10 S C13 24(14) . . . . ?
C7 C10 S C13 -176.7(6) . . . . ?
S' C10 S C13 5.8(8) . . . . ?
C11' C10 C11 C12 6(3) . . . . ?
C7 C10 C11 C12 -171.1(11) . . . . ?
S' C10 C11 C12 -143(19) . . . . ?
S C10 C11 C12 9(2) . . . . ?
C10 C11 C12 C13 -20(3) . . . . ?
C11 C12 C13 S 23(2) . . . . ?
C10 S C13 C12 -15.1(12) . . . . ?
C11 C10 S' C13' 23(17) . . . . ?
C11' C10 S' C13' -8.1(19) . . . . ?
C7 C10 S' C13' 176.7(10) . . . . ?
S C10 S' C13' -5.9(11) . . . . ?
C11 C10 C11' C12' -7(3) . . . . ?
C7 C10 C11' C12' 170.8(12) . . . . ?
S' C10 C11' C12' -4(3) . . . . ?
S C10 C11' C12' -167(16) . . . . ?
C10 C11' C12' C13' 18(3) . . . . ?
C11' C12' C13' S' -23(2) . . . . ?
C10 S' C13' C12' 18.0(17) . . . . ?
N4 N3 C14 C15 -176.7(3) . . . . ?
N4 N3 C14 C8 1.0(5) . . . . ?
C9 C8 C14 N3 95.7(4) . . . . ?
C7 C8 C14 N3 -87.5(5) . . . . ?
C9 C8 C14 C15 -86.7(4) . . . . ?
C7 C8 C14 C15 90.1(4) . . . . ?
N3 C14 C15 C20 162.7(3) . . . . ?
C8 C14 C15 C20 -15.0(5) . . . . ?
N3 C14 C15 C16 -14.5(5) . . . . ?
C8 C14 C15 C16 167.8(3) . . . . ?
C20 C15 C16 C17 0.6(5) . . . . ?
C14 C15 C16 C17 177.8(3) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
C15 C16 C17 Br 179.2(3) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
Br C17 C18 C19 -179.9(3) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C16 C15 C20 C19 0.6(5) . . . . ?
C14 C15 C20 C19 -176.6(3) . . . . ?
C18 C19 C20 C15 -1.2(6) . . . . ?
C22 N5 C21 O2 -13.2(6) . . . . ?
C22 N5 C21 N4 166.3(3) . . . . ?
N3 N4 C21 O2 4.9(5) . . . . ?
N3 N4 C21 N5 -174.6(3) . . . . ?
C21 N5 C22 C27 -25.1(6) . . . . ?
C21 N5 C22 C23 159.3(4) . . . . ?
C27 C22 C23 C24 -0.2(5) . . . . ?
N5 C22 C23 C24 175.6(3) . . . . ?
C22 C23 C24 C25 0.0(6) . . . . ?
C23 C24 C25 C26 0.3(7) . . . . ?
C24 C25 C26 C27 -0.4(7) . . . . ?
C23 C22 C27 C26 0.1(6) . . . . ?
N5 C22 C27 C26 -175.5(3) . . . . ?
C25 C26 C27 C22 0.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4N O4 0.83(2) 2.21(3) 2.881(4) 138(3) 2_666
N5 H5N O4 0.84(2) 2.03(3) 2.844(4) 163(3) 2_666
O1 H1O O2 0.80(3) 1.84(3) 2.615(3) 162(4) 2_666
O4 H4AO O3 0.84(3) 1.95(3) 2.763(5) 163(5) .
O3 H3O O2 0.83(3) 2.01(4) 2.769(4) 152(6) .
O3 H3O N3 0.83(3) 2.64(5) 3.310(4) 139(5) .
O4 H4BO N2 0.84(3) 2.07(3) 2.886(4) 166(5) 1_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.080




data_global

# Attachment '902003.cif'


data_a2
#TrackingRef '902003.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 Cl N5 O3 S'
_chemical_formula_weight         532.01

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   P2(1)/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                   12.380(3)
_cell_length_b                   11.605(2)
_cell_length_c                   19.026(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.66(3)
_cell_angle_gamma                90.00
_cell_volume                     2644.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21068
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4900
_reflns_number_gt                3056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0919P)²+0.7438P] 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       0.0057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4900
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
S S 0.86397(11) 0.43720(12) 0.02464(8) 0.1077(5) Uani 1 1 d . . .
Cl Cl 0.89914(12) -0.25275(10) 0.07089(8) 0.1132(5) Uani 1 1 d . . .
O1 O 0.43279(19) 0.1779(2) -0.12724(13) 0.0575(6) Uani 1 1 d . . .
N1 N 0.5209(2) 0.3546(2) -0.10342(13) 0.0466(6) Uani 1 1 d . . .
C1 C 0.4894(4) 0.5075(4) -0.1924(2) 0.0845(12) Uani 1 1 d . . .
H1B H 0.5662 0.5186 -0.1825 0.101 Uiso 1 1 calc R . .
O2 O 0.49490(17) 0.01781(17) 0.16112(11) 0.0516(5) Uani 1 1 d . . .
N2 N 0.6134(2) 0.4055(2) -0.05827(14) 0.0512(7) Uani 1 1 d . . .
C2 C 0.4180(5) 0.5756(5) -0.2426(3) 0.1135(18) Uani 1 1 d . . .
H2B H 0.4466 0.6336 -0.2664 0.136 Uiso 1 1 calc R . .
N3 N 0.5946(2) 0.0670(2) 0.05389(13) 0.0453(6) Uani 1 1 d . . .
C3 C 0.3063(5) 0.5587(5) -0.2576(3) 0.1130(18) Uani 1 1 d . . .
H3B H 0.2586 0.6050 -0.2917 0.136 Uiso 1 1 calc R . .
O3 O 0.3757(3) 0.3546(3) 0.02601(18) 0.0754(8) Uani 1 1 d . . .
N4 N 0.5176(2) 0.1385(2) 0.07098(13) 0.0495(6) Uani 1 1 d . . .
H4A H 0.4971 0.2006 0.0466 0.059 Uiso 1 1 calc R . .
C4 C 0.2632(4) 0.4736(4) -0.2227(3) 0.1034(15) Uani 1 1 d . . .
H4B H 0.1864 0.4621 -0.2335 0.124 Uiso 1 1 calc R . .
N5 N 0.4051(2) 0.1915(2) 0.14226(14) 0.0562(7) Uani 1 1 d . . .
H5A H 0.3961 0.2515 0.1149 0.067 Uiso 1 1 calc R . .
C5 C 0.3327(3) 0.4051(3) -0.1718(2) 0.0714(10) Uani 1 1 d . . .
H5B H 0.3036 0.3478 -0.1478 0.086 Uiso 1 1 calc R . .
C6 C 0.4460(3) 0.4229(3) -0.15705(17) 0.0539(8) Uani 1 1 d . . .
C7 C 0.6660(2) 0.3191(2) -0.01756(15) 0.0468(7) Uani 1 1 d . . .
C8 C 0.6093(2) 0.2134(2) -0.03455(15) 0.0431(7) Uani 1 1 d . . .
C9 C 0.5175(2) 0.2404(2) -0.08931(15) 0.0428(7) Uani 1 1 d . . .
C10 C 0.7698(3) 0.3396(3) 0.03803(18) 0.0591(9) Uani 1 1 d . . .
C11 C 0.8057(3) 0.2805(3) 0.1080(2) 0.0795(12) Uani 1 1 d . . .
H11 H 0.7669 0.2241 0.1263 0.095 Uiso 1 1 calc R . .
C12 C 0.9127(4) 0.3276(5) 0.1425(3) 0.1166(18) Uani 1 1 d . . .
H12A H 0.9531 0.3033 0.1881 0.140 Uiso 1 1 calc R . .
C13 C 0.9506(4) 0.4078(5) 0.1055(3) 0.1119(17) Uani 1 1 d . . .
H13 H 1.0191 0.4443 0.1228 0.134 Uiso 1 1 calc R . .
C14 C 0.6398(2) 0.1021(2) 0.00359(15) 0.0431(7) Uani 1 1 d . . .
C15 C 0.7294(2) 0.0284(2) -0.01203(16) 0.0462(7) Uani 1 1 d . . .
C16 C 0.7670(3) -0.0683(3) 0.03055(19) 0.0579(9) Uani 1 1 d . . .
H16A H 0.7355 -0.0883 0.0683 0.069 Uiso 1 1 calc R . .
C17 C 0.8514(3) -0.1337(3) 0.0159(2) 0.0654(10) Uani 1 1 d . . .
C18 C 0.8989(3) -0.1089(3) -0.0394(2) 0.0745(11) Uani 1 1 d . . .
H18A H 0.9555 -0.1549 -0.0483 0.089 Uiso 1 1 calc R . .
C19 C 0.8609(3) -0.0136(4) -0.0819(2) 0.0769(11) Uani 1 1 d . . .
H19A H 0.8921 0.0047 -0.1201 0.092 Uiso 1 1 calc R . .
C20 C 0.7772(3) 0.0551(3) -0.06824(19) 0.0628(9) Uani 1 1 d . . .
H20A H 0.7529 0.1194 -0.0970 0.075 Uiso 1 1 calc R . .
C21 C 0.4737(3) 0.1091(2) 0.12778(16) 0.0464(7) Uani 1 1 d . . .
C22 C 0.3467(3) 0.1907(3) 0.19691(17) 0.0511(8) Uani 1 1 d . . .
C23 C 0.2704(3) 0.2773(3) 0.1945(2) 0.0723(10) Uani 1 1 d . . .
H23A H 0.2587 0.3318 0.1575 0.087 Uiso 1 1 calc R . .
C24 C 0.2110(3) 0.2839(4) 0.2464(2) 0.0826(12) Uani 1 1 d . . .
H24A H 0.1608 0.3440 0.2451 0.099 Uiso 1 1 calc R . .
C25 C 0.2250(4) 0.2036(4) 0.2996(2) 0.0814(12) Uani 1 1 d . . .
H25A H 0.1824 0.2060 0.3334 0.098 Uiso 1 1 calc R . .
C26 C 0.3013(4) 0.1205(4) 0.3027(2) 0.1002(16) Uani 1 1 d . . .
H26A H 0.3125 0.0664 0.3399 0.120 Uiso 1 1 calc R . .
C27 C 0.3637(4) 0.1133(3) 0.2522(2) 0.0834(13) Uani 1 1 d . . .
H27A H 0.4171 0.0557 0.2560 0.100 Uiso 1 1 calc R . .
H1A H 0.450(3) 0.114(3) -0.1339(18) 0.061(11) Uiso 1 1 d . . .
H2 H 0.319(4) 0.344(4) -0.002(2) 0.074(16) Uiso 1 1 d . . .
H3 H 0.383(4) 0.423(4) 0.036(2) 0.092(16) 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
S C13 1.673(5) . ?
S C10 1.690(4) . ?
Cl C17 1.744(4) . ?
O1 C9 1.328(4) . ?
O1 H1A 0.79(4) . ?
N1 C9 1.354(4) . ?
N1 N2 1.378(3) . ?
N1 C6 1.433(4) . ?
C1 C2 1.374(6) . ?
C1 C6 1.375(5) . ?
C1 H1B 0.9300 . ?
O2 C21 1.229(3) . ?
N2 C7 1.332(4) . ?
C2 C3 1.354(7) . ?
C2 H2B 0.9300 . ?
N3 C14 1.291(4) . ?
N3 N4 1.363(3) . ?
C3 C4 1.372(7) . ?
C3 H3B 0.9300 . ?
O3 H2 0.78(4) . ?
O3 H3 0.81(5) . ?
N4 C21 1.370(4) . ?
N4 H4A 0.8600 . ?
C4 C5 1.373(6) . ?
C4 H4B 0.9300 . ?
N5 C21 1.352(4) . ?
N5 C22 1.409(4) . ?
N5 H5A 0.8600 . ?
C5 C6 1.374(5) . ?
C5 H5B 0.9300 . ?
C7 C8 1.410(4) . ?
C7 C10 1.463(4) . ?
C8 C9 1.370(4) . ?
C8 C14 1.483(4) . ?
C10 C11 1.464(5) . ?
C11 C12 1.429(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.323(7) . ?
C12 H12A 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.489(4) . ?
C15 C20 1.382(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.377(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.359(5) . ?
C18 C19 1.381(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.383(5) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C22 C27 1.359(5) . ?
C22 C23 1.372(4) . ?
C23 C24 1.375(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.354(6) . ?
C24 H24A 0.9300 . ?
C25 C26 1.341(6) . ?
C25 H25A 0.9300 . ?
C26 C27 1.378(5) . ?
C26 H26A 0.9300 . ?
C27 H27A 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
C13 S C10 91.8(2) . . ?
C9 O1 H1A 113(3) . . ?
C9 N1 N2 111.0(2) . . ?
C9 N1 C6 129.4(3) . . ?
N2 N1 C6 119.5(2) . . ?
C2 C1 C6 119.2(4) . . ?
C2 C1 H1B 120.4 . . ?
C6 C1 H1B 120.4 . . ?
C7 N2 N1 104.3(2) . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2B 119.8 . . ?
C1 C2 H2B 119.8 . . ?
C14 N3 N4 116.4(2) . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3B 119.9 . . ?
C4 C3 H3B 119.9 . . ?
H2 O3 H3 110(4) . . ?
N3 N4 C21 118.6(2) . . ?
N3 N4 H4A 120.7 . . ?
C21 N4 H4A 120.7 . . ?
C3 C4 C5 120.5(5) . . ?
C3 C4 H4B 119.8 . . ?
C5 C4 H4B 119.8 . . ?
C21 N5 C22 127.7(3) . . ?
C21 N5 H5A 116.1 . . ?
C22 N5 H5A 116.1 . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5B 120.6 . . ?
C6 C5 H5B 120.6 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 N1 120.4(3) . . ?
C1 C6 N1 118.7(3) . . ?
N2 C7 C8 112.4(3) . . ?
N2 C7 C10 120.6(3) . . ?
C8 C7 C10 127.0(3) . . ?
C9 C8 C7 104.1(2) . . ?
C9 C8 C14 129.1(3) . . ?
C7 C8 C14 126.6(3) . . ?
O1 C9 N1 119.1(3) . . ?
O1 C9 C8 132.6(3) . . ?
N1 C9 C8 108.2(3) . . ?
C7 C10 C11 126.2(3) . . ?
C7 C10 S 120.9(3) . . ?
C11 C10 S 112.9(3) . . ?
C12 C11 C10 105.7(4) . . ?
C12 C11 H11 127.1 . . ?
C10 C11 H11 127.1 . . ?
C13 C12 C11 116.0(4) . . ?
C13 C12 H12A 122.0 . . ?
C11 C12 H12A 122.0 . . ?
C12 C13 S 113.7(4) . . ?
C12 C13 H13 123.2 . . ?
S C13 H13 123.2 . . ?
N3 C14 C8 122.2(3) . . ?
N3 C14 C15 116.9(3) . . ?
C8 C14 C15 120.8(3) . . ?
C20 C15 C16 119.0(3) . . ?
C20 C15 C14 120.8(3) . . ?
C16 C15 C14 120.1(3) . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
C18 C17 C16 122.7(3) . . ?
C18 C17 Cl 119.0(3) . . ?
C16 C17 Cl 118.3(3) . . ?
C17 C18 C19 118.2(3) . . ?
C17 C18 H18A 120.9 . . ?
C19 C18 H18A 120.9 . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19A 119.6 . . ?
C20 C19 H19A 119.6 . . ?
C15 C20 C19 120.3(3) . . ?
C15 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
O2 C21 N5 124.6(3) . . ?
O2 C21 N4 123.1(3) . . ?
N5 C21 N4 112.4(3) . . ?
C27 C22 C23 118.7(3) . . ?
C27 C22 N5 124.6(3) . . ?
C23 C22 N5 116.7(3) . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C26 C25 C24 118.9(3) . . ?
C26 C25 H25A 120.6 . . ?
C24 C25 H25A 120.6 . . ?
C25 C26 C27 121.8(4) . . ?
C25 C26 H26A 119.1 . . ?
C27 C26 H26A 119.1 . . ?
C22 C27 C26 119.6(4) . . ?
C22 C27 H27A 120.2 . . ?
C26 C27 H27A 120.2 . . ?

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
C9 N1 N2 C7 0.9(3) . . . . ?
C6 N1 N2 C7 -178.0(3) . . . . ?
C6 C1 C2 C3 -0.7(8) . . . . ?
C1 C2 C3 C4 0.2(9) . . . . ?
C14 N3 N4 C21 -175.1(3) . . . . ?
C2 C3 C4 C5 0.5(9) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C4 C5 C6 N1 178.9(4) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C1 C6 N1 -178.3(4) . . . . ?
C9 N1 C6 C5 40.1(5) . . . . ?
N2 N1 C6 C5 -141.3(3) . . . . ?
C9 N1 C6 C1 -141.0(4) . . . . ?
N2 N1 C6 C1 37.7(4) . . . . ?
N1 N2 C7 C8 -0.7(3) . . . . ?
N1 N2 C7 C10 -180.0(3) . . . . ?
N2 C7 C8 C9 0.3(3) . . . . ?
C10 C7 C8 C9 179.5(3) . . . . ?
N2 C7 C8 C14 -175.2(3) . . . . ?
C10 C7 C8 C14 4.0(5) . . . . ?
N2 N1 C9 O1 179.1(2) . . . . ?
C6 N1 C9 O1 -2.2(5) . . . . ?
N2 N1 C9 C8 -0.7(3) . . . . ?
C6 N1 C9 C8 178.0(3) . . . . ?
C7 C8 C9 O1 -179.5(3) . . . . ?
C14 C8 C9 O1 -4.2(5) . . . . ?
C7 C8 C9 N1 0.3(3) . . . . ?
C14 C8 C9 N1 175.6(3) . . . . ?
N2 C7 C10 C11 145.5(4) . . . . ?
C8 C7 C10 C11 -33.7(5) . . . . ?
N2 C7 C10 S -35.8(4) . . . . ?
C8 C7 C10 S 145.1(3) . . . . ?
C13 S C10 C7 -178.9(3) . . . . ?
C13 S C10 C11 0.0(3) . . . . ?
C7 C10 C11 C12 178.8(4) . . . . ?
S C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C11 C12 C13 S -0.2(7) . . . . ?
C10 S C13 C12 0.1(5) . . . . ?
N4 N3 C14 C8 -0.7(4) . . . . ?
N4 N3 C14 C15 176.0(2) . . . . ?
C9 C8 C14 N3 -78.3(4) . . . . ?
C7 C8 C14 N3 96.0(4) . . . . ?
C9 C8 C14 C15 105.1(4) . . . . ?
C7 C8 C14 C15 -80.6(4) . . . . ?
N3 C14 C15 C20 175.6(3) . . . . ?
C8 C14 C15 C20 -7.7(4) . . . . ?
N3 C14 C15 C16 -5.0(4) . . . . ?
C8 C14 C15 C16 171.8(3) . . . . ?
C20 C15 C16 C17 0.7(5) . . . . ?
C14 C15 C16 C17 -178.8(3) . . . . ?
C15 C16 C17 C18 -1.0(5) . . . . ?
C15 C16 C17 Cl 178.8(2) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
Cl C17 C18 C19 -179.3(3) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C16 C15 C20 C19 0.1(5) . . . . ?
C14 C15 C20 C19 179.5(3) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?
C22 N5 C21 O2 0.7(5) . . . . ?
C22 N5 C21 N4 -179.4(3) . . . . ?
N3 N4 C21 O2 -4.8(4) . . . . ?
N3 N4 C21 N5 175.3(3) . . . . ?
C21 N5 C22 C27 10.9(6) . . . . ?
C21 N5 C22 C23 -171.3(3) . . . . ?
C27 C22 C23 C24 -1.1(6) . . . . ?
N5 C22 C23 C24 -179.0(4) . . . . ?
C22 C23 C24 C25 -1.6(6) . . . . ?
C23 C24 C25 C26 3.0(7) . . . . ?
C24 C25 C26 C27 -1.6(8) . . . . ?
C23 C22 C27 C26 2.5(6) . . . . ?
N5 C22 C27 C26 -179.8(4) . . . . ?
C25 C26 C27 C22 -1.1(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O3 0.86 2.30 3.058(4) 146.4 .
N5 H5A O3 0.86 2.03 2.864(4) 161.8 .
O1 H1A O2 0.79(4) 1.80(4) 2.582(3) 168(4) 3_655
O3 H2 Cl 0.78(4) 2.89(4) 3.633(5) 162(4) 3_655
O3 H3 N2 0.81(5) 2.04(5) 2.846(4) 175(4) 3_665

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.050



