# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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data_362
_database_code_depnum_ccdc_archive 'CCDC 865440'
#TrackingRef 'cd103602.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 Cl2 N4 O7'
_chemical_formula_sum            'C26 H22 Cl2 N4 O7'
_chemical_formula_weight         573.38
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   8.5141(17)
_cell_length_b                   11.318(2)
_cell_length_c                   26.647(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2567.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4420
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      66.94

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    2.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7070
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            11972
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         66.94
_reflns_number_total             4396
_reflns_number_gt                3953
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.1772P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(15)
_refine_ls_number_reflns         4396
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.59749(13) 0.29806(9) 0.99107(3) 0.0929(3) Uani 1 1 d . . .
Cl2 Cl 0.14920(8) 0.38949(9) 0.86469(4) 0.0879(3) Uani 1 1 d . . .
O1 O 0.90851(19) 0.30156(14) 0.76972(6) 0.0503(4) Uani 1 1 d . . .
O2 O 0.8544(2) 0.22590(16) 0.66872(6) 0.0534(4) Uani 1 1 d . . .
O3 O 0.9150(2) 0.2972(2) 0.59324(7) 0.0691(5) Uani 1 1 d . . .
O4 O 0.2375(3) 0.1016(2) 0.54579(8) 0.0773(6) Uani 1 1 d . . .
O5 O 1.10417(19) 0.07723(15) 0.79387(6) 0.0518(4) Uani 1 1 d . . .
O6 O 1.3079(2) 0.04728(17) 0.74194(7) 0.0572(4) Uani 1 1 d . . .
O7 O 1.6059(3) -0.0080(2) 0.96040(8) 0.0743(6) Uani 1 1 d . . .
N1 N 0.6647(2) 0.26129(18) 0.80507(7) 0.0472(5) Uani 1 1 d . . .
N2 N 0.4203(2) 0.32055(18) 0.78420(8) 0.0539(5) Uani 1 1 d . . .
N3 N 0.6459(3) 0.27759(19) 0.89571(8) 0.0541(5) Uani 1 1 d . . .
N4 N 0.3901(3) 0.3420(2) 0.92229(9) 0.0641(6) Uani 1 1 d . . .
C1 C 1.0244(3) 0.2403(2) 0.73963(9) 0.0462(5) Uani 1 1 d . . .
H1A H 1.1292 0.2656 0.7504 0.055 Uiso 1 1 calc R . .
C2 C 1.0052(3) 0.1099(2) 0.75197(9) 0.0469(5) Uani 1 1 d . . .
H2A H 1.0226 0.0593 0.7226 0.056 Uiso 1 1 calc R . .
C3 C 0.8388(3) 0.1016(2) 0.77139(9) 0.0491(5) Uani 1 1 d . . .
H3A H 0.8254 0.0347 0.7937 0.059 Uiso 1 1 calc R . .
H3B H 0.7634 0.0962 0.7442 0.059 Uiso 1 1 calc R . .
C4 C 0.8246(3) 0.2181(2) 0.79931(9) 0.0482(5) Uani 1 1 d . . .
H4A H 0.8742 0.2111 0.8324 0.058 Uiso 1 1 calc R . .
C5 C 0.5571(3) 0.2841(2) 0.76800(9) 0.0507(6) Uani 1 1 d . . .
H5A H 0.5795 0.2744 0.7341 0.061 Uiso 1 1 calc R . .
C6 C 0.4392(3) 0.3223(2) 0.83539(9) 0.0476(5) Uani 1 1 d . . .
C7 C 0.5903(3) 0.2867(2) 0.84929(9) 0.0458(5) Uani 1 1 d . . .
C8 C 0.5369(4) 0.3073(3) 0.92930(10) 0.0618(7) Uani 1 1 d . . .
C9 C 0.3421(3) 0.3486(2) 0.87571(11) 0.0566(6) Uani 1 1 d . . .
C10 C 1.0038(3) 0.2720(2) 0.68576(9) 0.0492(5) Uani 1 1 d . . .
H10A H 1.0061 0.3572 0.6818 0.059 Uiso 1 1 calc R . .
H10B H 1.0884 0.2385 0.6660 0.059 Uiso 1 1 calc R . .
C11 C 0.8224(3) 0.2471(2) 0.61961(9) 0.0495(5) Uani 1 1 d . . .
C12 C 0.6669(3) 0.2050(2) 0.60391(9) 0.0489(5) Uani 1 1 d . . .
C13 C 0.6204(3) 0.2303(3) 0.55507(9) 0.0595(7) Uani 1 1 d . . .
H13A H 0.6874 0.2727 0.5342 0.071 Uiso 1 1 calc R . .
C14 C 0.4783(3) 0.1938(3) 0.53719(10) 0.0640(7) Uani 1 1 d . . .
H14A H 0.4503 0.2102 0.5042 0.077 Uiso 1 1 calc R . .
C15 C 0.3759(3) 0.1330(2) 0.56781(10) 0.0568(6) Uani 1 1 d . . .
C16 C 0.4180(3) 0.1078(2) 0.61697(9) 0.0556(6) Uani 1 1 d . . .
H16A H 0.3494 0.0669 0.6378 0.067 Uiso 1 1 calc R . .
C17 C 0.5629(3) 0.1443(2) 0.63468(9) 0.0532(6) Uani 1 1 d . . .
H17A H 0.5910 0.1279 0.6677 0.064 Uiso 1 1 calc R . .
C18 C 0.1255(4) 0.0360(3) 0.57373(12) 0.0692(7) Uani 1 1 d . . .
H18A H 0.0356 0.0201 0.5531 0.104 Uiso 1 1 calc R . .
H18B H 0.0936 0.0809 0.6026 0.104 Uiso 1 1 calc R . .
H18C H 0.1715 -0.0372 0.5845 0.104 Uiso 1 1 calc R . .
C19 C 1.2562(3) 0.0505(2) 0.78371(10) 0.0458(5) Uani 1 1 d . . .
C20 C 1.3440(3) 0.0268(2) 0.83050(9) 0.0461(5) Uani 1 1 d . . .
C21 C 1.4983(3) -0.0109(2) 0.82744(10) 0.0480(5) Uani 1 1 d . . .
H21A H 1.5414 -0.0264 0.7961 0.058 Uiso 1 1 calc R . .
C22 C 1.5898(3) -0.0261(2) 0.86954(10) 0.0534(6) Uani 1 1 d . . .
H22A H 1.6930 -0.0519 0.8666 0.064 Uiso 1 1 calc R . .
C23 C 1.5263(3) -0.0024(2) 0.91648(10) 0.0564(6) Uani 1 1 d . . .
C24 C 1.3694(4) 0.0315(3) 0.92015(11) 0.0633(7) Uani 1 1 d . . .
H24A H 1.3251 0.0449 0.9515 0.076 Uiso 1 1 calc R . .
C25 C 1.2797(3) 0.0453(2) 0.87771(10) 0.0553(6) Uani 1 1 d . . .
H25A H 1.1748 0.0672 0.8806 0.066 Uiso 1 1 calc R . .
C26 C 1.7721(4) -0.0199(4) 0.95794(15) 0.0947(12) Uani 1 1 d . . .
H26A H 1.8143 -0.0229 0.9913 0.142 Uiso 1 1 calc R . .
H26B H 1.8158 0.0464 0.9404 0.142 Uiso 1 1 calc R . .
H26C H 1.7982 -0.0915 0.9405 0.142 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.1084(6) 0.1224(7) 0.0479(4) -0.0113(4) -0.0023(4) -0.0053(6)
Cl2 0.0464(3) 0.1092(6) 0.1080(6) -0.0252(5) 0.0093(4) 0.0128(4)
O1 0.0459(8) 0.0492(8) 0.0557(10) -0.0023(7) 0.0073(7) -0.0013(7)
O2 0.0525(8) 0.0605(10) 0.0471(9) 0.0067(7) -0.0049(7) -0.0074(8)
O3 0.0568(10) 0.0994(15) 0.0513(10) 0.0131(10) 0.0045(9) -0.0030(11)
O4 0.0632(12) 0.1077(17) 0.0611(12) 0.0169(12) -0.0106(10) -0.0109(12)
O5 0.0405(8) 0.0635(10) 0.0513(9) 0.0059(8) 0.0010(7) 0.0091(8)
O6 0.0471(9) 0.0733(12) 0.0513(10) 0.0020(8) 0.0048(8) 0.0044(8)
O7 0.0768(14) 0.0882(15) 0.0580(12) 0.0072(10) -0.0158(11) 0.0016(12)
N1 0.0409(9) 0.0537(11) 0.0470(11) 0.0006(8) -0.0010(8) 0.0014(9)
N2 0.0422(9) 0.0586(12) 0.0608(13) -0.0015(10) -0.0034(9) 0.0024(9)
N3 0.0568(11) 0.0578(12) 0.0475(11) -0.0038(9) -0.0004(10) -0.0039(11)
N4 0.0638(14) 0.0691(14) 0.0592(14) -0.0126(11) 0.0148(12) -0.0080(12)
C1 0.0354(9) 0.0513(13) 0.0519(13) -0.0028(10) -0.0008(9) -0.0004(10)
C2 0.0422(11) 0.0516(13) 0.0469(13) 0.0017(10) -0.0034(10) 0.0053(10)
C3 0.0419(11) 0.0468(12) 0.0587(15) 0.0054(11) -0.0026(10) 0.0006(10)
C4 0.0393(11) 0.0567(14) 0.0488(13) 0.0042(10) 0.0000(10) -0.0003(10)
C5 0.0477(12) 0.0577(14) 0.0468(13) 0.0025(11) -0.0041(10) 0.0018(11)
C6 0.0386(11) 0.0483(13) 0.0558(14) -0.0049(10) 0.0038(10) -0.0016(9)
C7 0.0458(11) 0.0454(12) 0.0463(12) -0.0041(9) 0.0015(10) -0.0038(10)
C8 0.0691(16) 0.0653(16) 0.0510(15) -0.0088(12) 0.0049(13) -0.0102(14)
C9 0.0436(12) 0.0568(14) 0.0695(18) -0.0104(12) 0.0056(12) -0.0011(11)
C10 0.0440(11) 0.0532(14) 0.0504(13) 0.0016(10) 0.0012(10) -0.0067(11)
C11 0.0523(13) 0.0537(13) 0.0426(13) 0.0028(10) 0.0013(10) 0.0089(11)
C12 0.0528(13) 0.0509(13) 0.0428(12) -0.0001(10) 0.0010(10) 0.0102(11)
C13 0.0568(14) 0.0781(18) 0.0436(13) 0.0072(12) 0.0044(11) 0.0043(13)
C14 0.0597(15) 0.089(2) 0.0429(14) 0.0111(14) -0.0048(12) 0.0030(15)
C15 0.0539(14) 0.0634(15) 0.0529(15) 0.0015(11) -0.0065(12) 0.0090(12)
C16 0.0581(13) 0.0545(14) 0.0541(14) 0.0043(11) 0.0037(12) -0.0011(13)
C17 0.0619(14) 0.0538(14) 0.0440(13) 0.0029(10) -0.0074(12) 0.0026(11)
C18 0.0597(16) 0.0766(18) 0.0714(19) 0.0018(14) 0.0027(14) -0.0004(14)
C19 0.0416(11) 0.0421(12) 0.0537(15) 0.0019(10) -0.0006(11) -0.0013(9)
C20 0.0457(11) 0.0405(11) 0.0522(14) 0.0041(9) 0.0017(10) -0.0016(10)
C21 0.0423(12) 0.0485(13) 0.0531(14) -0.0003(10) 0.0002(10) -0.0042(10)
C22 0.0413(10) 0.0553(13) 0.0637(16) 0.0058(11) -0.0029(12) 0.0007(11)
C23 0.0607(15) 0.0552(15) 0.0532(15) 0.0077(11) -0.0067(12) -0.0031(12)
C24 0.0668(16) 0.0716(17) 0.0515(15) 0.0025(13) 0.0050(13) 0.0060(14)
C25 0.0468(12) 0.0646(15) 0.0546(15) 0.0050(12) 0.0031(11) 0.0056(11)
C26 0.074(2) 0.125(3) 0.086(2) 0.010(2) -0.032(2) 0.000(2)

_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 C8 1.728(3) . ?
Cl2 C9 1.731(3) . ?
O1 C4 1.422(3) . ?
O1 C1 1.448(3) . ?
O2 C11 1.358(3) . ?
O2 C10 1.448(3) . ?
O3 C11 1.199(3) . ?
O4 C15 1.363(3) . ?
O4 C18 1.420(4) . ?
O5 C19 1.357(3) . ?
O5 C2 1.446(3) . ?
O6 C19 1.197(3) . ?
O7 C23 1.354(3) . ?
O7 C26 1.423(4) . ?
N1 C7 1.369(3) . ?
N1 C5 1.372(3) . ?
N1 C4 1.455(3) . ?
N2 C5 1.309(3) . ?
N2 C6 1.374(3) . ?
N3 C7 1.329(3) . ?
N3 C8 1.332(3) . ?
N4 C9 1.309(4) . ?
N4 C8 1.323(4) . ?
C1 C10 1.490(3) . ?
C1 C2 1.521(3) . ?
C1 H1A 0.9800 . ?
C2 C3 1.512(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.519(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9800 . ?
C5 H5A 0.9300 . ?
C6 C9 1.388(3) . ?
C6 C7 1.397(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.468(4) . ?
C12 C17 1.389(4) . ?
C12 C13 1.390(3) . ?
C13 C14 1.364(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.388(3) . ?
C16 C17 1.384(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.478(3) . ?
C20 C21 1.383(3) . ?
C20 C25 1.388(3) . ?
C21 C22 1.377(3) . ?
C21 H21A 0.9300 . ?
C22 C23 1.389(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.394(4) . ?
C24 C25 1.373(4) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C4 O1 C1 109.34(17) . . ?
C11 O2 C10 114.49(19) . . ?
C15 O4 C18 119.4(2) . . ?
C19 O5 C2 117.30(18) . . ?
C23 O7 C26 117.5(3) . . ?
C7 N1 C5 105.7(2) . . ?
C7 N1 C4 126.5(2) . . ?
C5 N1 C4 127.7(2) . . ?
C5 N2 C6 103.2(2) . . ?
C7 N3 C8 110.9(2) . . ?
C9 N4 C8 116.5(2) . . ?
O1 C1 C10 109.74(19) . . ?
O1 C1 C2 105.76(18) . . ?
C10 C1 C2 115.4(2) . . ?
O1 C1 H1A 108.6 . . ?
C10 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
O5 C2 C3 105.43(18) . . ?
O5 C2 C1 110.61(19) . . ?
C3 C2 C1 103.59(19) . . ?
O5 C2 H2A 112.2 . . ?
C3 C2 H2A 112.2 . . ?
C1 C2 H2A 112.2 . . ?
C2 C3 C4 100.84(19) . . ?
C2 C3 H3A 111.6 . . ?
C4 C3 H3A 111.6 . . ?
C2 C3 H3B 111.6 . . ?
C4 C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
O1 C4 N1 107.79(19) . . ?
O1 C4 C3 105.38(18) . . ?
N1 C4 C3 114.7(2) . . ?
O1 C4 H4A 109.6 . . ?
N1 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N2 C5 N1 114.6(2) . . ?
N2 C5 H5A 122.7 . . ?
N1 C5 H5A 122.7 . . ?
N2 C6 C9 134.6(2) . . ?
N2 C6 C7 111.5(2) . . ?
C9 C6 C7 113.9(2) . . ?
N3 C7 N1 128.3(2) . . ?
N3 C7 C6 126.7(2) . . ?
N1 C7 C6 105.0(2) . . ?
N4 C8 N3 129.6(3) . . ?
N4 C8 Cl1 115.7(2) . . ?
N3 C8 Cl1 114.6(2) . . ?
N4 C9 C6 122.4(2) . . ?
N4 C9 Cl2 118.2(2) . . ?
C6 C9 Cl2 119.4(2) . . ?
O2 C10 C1 108.60(18) . . ?
O2 C10 H10A 110.0 . . ?
C1 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
C1 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O3 C11 O2 121.1(2) . . ?
O3 C11 C12 125.4(2) . . ?
O2 C11 C12 113.4(2) . . ?
C17 C12 C13 118.2(2) . . ?
C17 C12 C11 124.6(2) . . ?
C13 C12 C11 117.2(2) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
O4 C15 C14 115.0(2) . . ?
O4 C15 C16 125.2(3) . . ?
C14 C15 C16 119.9(2) . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C12 121.0(2) . . ?
C16 C17 H17A 119.5 . . ?
C12 C17 H17A 119.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O5 122.9(2) . . ?
O6 C19 C20 126.4(2) . . ?
O5 C19 C20 110.8(2) . . ?
C21 C20 C25 118.3(2) . . ?
C21 C20 C19 119.1(2) . . ?
C25 C20 C19 122.5(2) . . ?
C22 C21 C20 121.9(2) . . ?
C22 C21 H21A 119.1 . . ?
C20 C21 H21A 119.1 . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
O7 C23 C22 125.1(3) . . ?
O7 C23 C24 115.6(3) . . ?
C22 C23 C24 119.3(3) . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24A 119.8 . . ?
C23 C24 H24A 119.8 . . ?
C24 C25 C20 120.6(2) . . ?
C24 C25 H25A 119.7 . . ?
C20 C25 H25A 119.7 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C4 O1 C1 C10 126.1(2) . . . . ?
C4 O1 C1 C2 0.9(2) . . . . ?
C19 O5 C2 C3 164.9(2) . . . . ?
C19 O5 C2 C1 -83.7(2) . . . . ?
O1 C1 C2 O5 -89.8(2) . . . . ?
C10 C1 C2 O5 148.73(19) . . . . ?
O1 C1 C2 C3 22.8(2) . . . . ?
C10 C1 C2 C3 -98.7(2) . . . . ?
O5 C2 C3 C4 80.3(2) . . . . ?
C1 C2 C3 C4 -36.0(2) . . . . ?
C1 O1 C4 N1 -147.27(19) . . . . ?
C1 O1 C4 C3 -24.4(2) . . . . ?
C7 N1 C4 O1 -120.5(2) . . . . ?
C5 N1 C4 O1 60.1(3) . . . . ?
C7 N1 C4 C3 122.5(2) . . . . ?
C5 N1 C4 C3 -56.9(3) . . . . ?
C2 C3 C4 O1 37.5(2) . . . . ?
C2 C3 C4 N1 155.8(2) . . . . ?
C6 N2 C5 N1 0.2(3) . . . . ?
C7 N1 C5 N2 -0.7(3) . . . . ?
C4 N1 C5 N2 178.9(2) . . . . ?
C5 N2 C6 C9 -178.0(3) . . . . ?
C5 N2 C6 C7 0.3(3) . . . . ?
C8 N3 C7 N1 -178.2(2) . . . . ?
C8 N3 C7 C6 0.1(4) . . . . ?
C5 N1 C7 N3 179.3(2) . . . . ?
C4 N1 C7 N3 -0.2(4) . . . . ?
C5 N1 C7 C6 0.8(3) . . . . ?
C4 N1 C7 C6 -178.8(2) . . . . ?
N2 C6 C7 N3 -179.3(2) . . . . ?
C9 C6 C7 N3 -0.6(4) . . . . ?
N2 C6 C7 N1 -0.7(3) . . . . ?
C9 C6 C7 N1 178.0(2) . . . . ?
C9 N4 C8 N3 0.2(5) . . . . ?
C9 N4 C8 Cl1 -179.5(2) . . . . ?
C7 N3 C8 N4 0.2(4) . . . . ?
C7 N3 C8 Cl1 179.88(19) . . . . ?
C8 N4 C9 C6 -0.8(4) . . . . ?
C8 N4 C9 Cl2 178.1(2) . . . . ?
N2 C6 C9 N4 179.2(3) . . . . ?
C7 C6 C9 N4 1.0(4) . . . . ?
N2 C6 C9 Cl2 0.3(4) . . . . ?
C7 C6 C9 Cl2 -177.91(19) . . . . ?
C11 O2 C10 C1 -178.8(2) . . . . ?
O1 C1 C10 O2 -66.2(2) . . . . ?
C2 C1 C10 O2 53.2(3) . . . . ?
C10 O2 C11 O3 2.0(3) . . . . ?
C10 O2 C11 C12 -177.0(2) . . . . ?
O3 C11 C12 C17 178.3(3) . . . . ?
O2 C11 C12 C17 -2.9(3) . . . . ?
O3 C11 C12 C13 -3.2(4) . . . . ?
O2 C11 C12 C13 175.7(2) . . . . ?
C17 C12 C13 C14 -1.8(4) . . . . ?
C11 C12 C13 C14 179.6(3) . . . . ?
C12 C13 C14 C15 1.4(5) . . . . ?
C18 O4 C15 C14 178.4(3) . . . . ?
C18 O4 C15 C16 -1.2(4) . . . . ?
C13 C14 C15 O4 179.8(3) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
O4 C15 C16 C17 179.6(3) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C12 -0.4(4) . . . . ?
C13 C12 C17 C16 1.2(4) . . . . ?
C11 C12 C17 C16 179.8(2) . . . . ?
C2 O5 C19 O6 -3.8(3) . . . . ?
C2 O5 C19 C20 176.26(19) . . . . ?
O6 C19 C20 C21 -4.8(4) . . . . ?
O5 C19 C20 C21 175.1(2) . . . . ?
O6 C19 C20 C25 172.6(3) . . . . ?
O5 C19 C20 C25 -7.5(3) . . . . ?
C25 C20 C21 C22 -2.4(4) . . . . ?
C19 C20 C21 C22 175.2(2) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C26 O7 C23 C22 10.8(5) . . . . ?
C26 O7 C23 C24 -168.3(3) . . . . ?
C21 C22 C23 O7 -176.4(2) . . . . ?
C21 C22 C23 C24 2.7(4) . . . . ?
O7 C23 C24 C25 177.0(3) . . . . ?
C22 C23 C24 C25 -2.2(4) . . . . ?
C23 C24 C25 C20 -0.6(4) . . . . ?
C21 C20 C25 C24 2.9(4) . . . . ?
C19 C20 C25 C24 -174.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        66.94
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.041


data_cd211183
_database_code_depnum_ccdc_archive 'CCDC 865441'
#TrackingRef 'cd211183.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H32 Br N5 O9'
_chemical_formula_weight         698.53

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.4310(5)
_cell_length_b                   19.4670(17)
_cell_length_c                   30.338(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3207.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3745
_cell_measurement_theta_min      4.395
_cell_measurement_theta_max      47.884

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    1.343
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17333
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6234
_reflns_number_gt                4536
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6234
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.51296(9) 1.175777(19) 0.185745(11) 0.06118(15) Uani 1 1 d . . .
N1 N 0.0719(6) 1.00518(13) 0.28220(8) 0.0426(8) Uani 1 1 d . . .
N2 N 0.1074(6) 1.05289(16) 0.21477(9) 0.0532(9) Uani 1 1 d . . .
N3 N 0.6022(6) 1.14738(14) 0.27278(9) 0.0445(8) Uani 1 1 d . . .
N4 N 0.3929(5) 1.06735(13) 0.32037(8) 0.0402(7) Uani 1 1 d . . .
N5 N 0.7263(7) 1.13536(16) 0.34411(9) 0.0526(9) Uani 1 1 d . . .
O1 O 0.1588(5) 0.89337(12) 0.30109(8) 0.0510(7) Uani 1 1 d . . .
O2 O 0.7086(6) 1.04640(13) 0.39284(8) 0.0562(7) Uani 1 1 d . . .
O3 O 0.9214(5) 1.14346(13) 0.40688(7) 0.0592(8) Uani 1 1 d . . .
O4 O -0.1679(5) 0.81897(12) 0.23999(7) 0.0517(6) Uani 1 1 d . . .
O5 O -0.0811(6) 0.73541(15) 0.19262(8) 0.0739(9) Uani 1 1 d . . .
O6 O -0.8689(7) 0.89618(19) 0.08106(10) 0.0970(12) Uani 1 1 d . . .
O7 O -0.2006(5) 0.85339(12) 0.37773(7) 0.0479(6) Uani 1 1 d . . .
O8 O -0.5426(7) 0.79073(17) 0.38434(8) 0.0811(10) Uani 1 1 d . . .
O9 O -0.3403(7) 0.88199(15) 0.58163(8) 0.0727(9) Uani 1 1 d . . .
C1 C 0.0244(7) 0.83142(15) 0.31074(10) 0.0429(8) Uani 1 1 d . . .
H1 H 0.1148 0.8056 0.3333 0.052 Uiso 1 1 calc R . .
C2 C -0.2203(7) 0.85423(17) 0.33017(10) 0.0404(8) Uani 1 1 d . . .
H2 H -0.3573 0.8258 0.3197 0.048 Uiso 1 1 calc R . .
C3 C -0.2454(7) 0.92761(16) 0.31575(11) 0.0412(8) Uani 1 1 d . . .
H3A H -0.3393 0.9542 0.3369 0.049 Uiso 1 1 calc R . .
H3B H -0.3239 0.9308 0.2871 0.049 Uiso 1 1 calc R . .
C4 C 0.0189(7) 0.95134(15) 0.31379(10) 0.0403(7) Uani 1 1 d . . .
H4 H 0.0711 0.9663 0.3432 0.048 Uiso 1 1 calc R . .
C5 C -0.0055(9) 1.00806(18) 0.23893(10) 0.0553(10) Uani 1 1 d . . .
H5 H -0.1295 0.9799 0.2279 0.066 Uiso 1 1 calc R . .
C6 C 0.2741(7) 1.08179(17) 0.24372(10) 0.0410(9) Uani 1 1 d . . .
C7 C 0.2553(7) 1.05252(16) 0.28531(10) 0.0364(8) Uani 1 1 d . . .
C8 C 0.5639(7) 1.11429(16) 0.31144(10) 0.0432(9) Uani 1 1 d . . .
C9 C 0.4586(7) 1.13048(16) 0.23979(10) 0.0428(9) Uani 1 1 d . . .
C10 C 0.7788(8) 1.1018(2) 0.38285(11) 0.0457(9) Uani 1 1 d . . .
C11 C 1.0221(9) 1.12013(19) 0.44929(10) 0.0550(10) Uani 1 1 d . . .
C12 C 1.1675(10) 1.0542(2) 0.44314(16) 0.0817(14) Uani 1 1 d . . .
H12A H 1.0564 1.0171 0.4370 0.123 Uiso 1 1 calc R . .
H12B H 1.2581 1.0443 0.4696 0.123 Uiso 1 1 calc R . .
H12C H 1.2800 1.0596 0.4190 0.123 Uiso 1 1 calc R . .
C13 C 0.8212(10) 1.1100(3) 0.48241(13) 0.0937(18) Uani 1 1 d . . .
H13A H 0.7258 1.1514 0.4848 0.141 Uiso 1 1 calc R . .
H13B H 0.8921 1.0993 0.5106 0.141 Uiso 1 1 calc R . .
H13C H 0.7167 1.0729 0.4732 0.141 Uiso 1 1 calc R . .
C14 C 1.1881(10) 1.1793(2) 0.46213(13) 0.0841(16) Uani 1 1 d . . .
H14A H 1.3152 1.1846 0.4404 0.126 Uiso 1 1 calc R . .
H14B H 1.2614 1.1701 0.4903 0.126 Uiso 1 1 calc R . .
H14C H 1.0930 1.2208 0.4638 0.126 Uiso 1 1 calc R . .
C15 C 0.0071(9) 0.78790(17) 0.26982(10) 0.0498(9) Uani 1 1 d . . .
H15A H 0.1672 0.7848 0.2558 0.060 Uiso 1 1 calc R . .
H15B H -0.0460 0.7419 0.2775 0.060 Uiso 1 1 calc R . .
C16 C -0.1941(8) 0.7857(2) 0.20170(11) 0.0509(10) Uani 1 1 d . . .
C17 C -0.3781(7) 0.81744(18) 0.17246(10) 0.0476(9) Uani 1 1 d . . .
C18 C -0.4093(10) 0.7899(2) 0.13078(12) 0.0713(15) Uani 1 1 d . . .
H18 H -0.3153 0.7522 0.1225 0.086 Uiso 1 1 calc R . .
C19 C -0.5733(11) 0.8165(2) 0.10172(13) 0.0816(17) Uani 1 1 d . . .
H19 H -0.5904 0.7968 0.0740 0.098 Uiso 1 1 calc R . .
C20 C -0.7136(9) 0.8721(2) 0.11299(13) 0.0670(13) Uani 1 1 d . . .
C21 C -0.6911(9) 0.9011(2) 0.15395(13) 0.0674(12) Uani 1 1 d . . .
H21 H -0.7865 0.9388 0.1619 0.081 Uiso 1 1 calc R . .
C22 C -0.5225(8) 0.87294(18) 0.18338(11) 0.0586(10) Uani 1 1 d . . .
H22 H -0.5070 0.8922 0.2113 0.070 Uiso 1 1 calc R . .
C23 C -1.0074(15) 0.9550(3) 0.09040(18) 0.125(2) Uani 1 1 d . . .
H23A H -1.1123 0.9463 0.1153 0.188 Uiso 1 1 calc R . .
H23B H -1.1064 0.9667 0.0653 0.188 Uiso 1 1 calc R . .
H23C H -0.8986 0.9925 0.0971 0.188 Uiso 1 1 calc R . .
C24 C -0.3826(7) 0.82563(19) 0.40055(11) 0.0466(9) Uani 1 1 d . . .
C25 C -0.3647(7) 0.83943(17) 0.44849(11) 0.0421(9) Uani 1 1 d . . .
C26 C -0.1809(8) 0.87907(19) 0.46672(11) 0.0557(11) Uani 1 1 d . . .
H26 H -0.0577 0.8968 0.4487 0.067 Uiso 1 1 calc R . .
C27 C -0.1774(9) 0.8926(2) 0.51088(12) 0.0655(12) Uani 1 1 d . . .
H27 H -0.0545 0.9203 0.5227 0.079 Uiso 1 1 calc R . .
C28 C -0.3572(8) 0.8651(2) 0.53808(11) 0.0509(10) Uani 1 1 d . . .
C29 C -0.5401(8) 0.82516(19) 0.52050(11) 0.0556(10) Uani 1 1 d . . .
H29 H -0.6633 0.8073 0.5384 0.067 Uiso 1 1 calc R . .
C30 C -0.5391(8) 0.81188(18) 0.47589(11) 0.0545(10) Uani 1 1 d . . .
H30 H -0.6600 0.7835 0.4641 0.065 Uiso 1 1 calc R . .
C31 C -0.5226(11) 0.8560(3) 0.61057(12) 0.0837(14) Uani 1 1 d . . .
H31A H -0.6823 0.8707 0.6008 0.125 Uiso 1 1 calc R . .
H31B H -0.4931 0.8729 0.6398 0.125 Uiso 1 1 calc R . .
H31C H -0.5160 0.8067 0.6107 0.125 Uiso 1 1 calc R . .
H5A H 0.818(8) 1.1737(19) 0.3382(11) 0.059(12) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0746(3) 0.0696(3) 0.03933(19) 0.01709(16) -0.0088(2) -0.0131(2)
N1 0.050(2) 0.0475(17) 0.0305(14) -0.0011(12) -0.0061(13) -0.0083(14)
N2 0.061(2) 0.062(2) 0.0364(16) 0.0001(14) -0.0114(15) -0.0109(17)
N3 0.058(2) 0.0400(16) 0.0361(16) 0.0054(12) -0.0075(14) -0.0068(14)
N4 0.0544(18) 0.0390(15) 0.0271(14) -0.0024(12) -0.0071(13) -0.0031(13)
N5 0.069(2) 0.053(2) 0.0356(16) 0.0055(14) -0.0145(16) -0.0242(19)
O1 0.0451(15) 0.0426(14) 0.0652(17) -0.0001(12) 0.0085(13) -0.0002(12)
O2 0.070(2) 0.0542(17) 0.0445(15) 0.0094(12) -0.0124(14) -0.0133(15)
O3 0.083(2) 0.0556(15) 0.0394(13) 0.0034(11) -0.0228(14) -0.0194(15)
O4 0.0618(17) 0.0568(15) 0.0364(13) -0.0133(11) -0.0079(12) 0.0170(14)
O5 0.093(2) 0.0737(18) 0.0547(16) -0.0248(14) -0.0119(16) 0.0399(17)
O6 0.123(3) 0.100(3) 0.067(2) -0.0097(18) -0.044(2) 0.038(2)
O7 0.0502(17) 0.0624(16) 0.0312(12) -0.0026(11) 0.0013(12) -0.0151(13)
O8 0.089(3) 0.108(2) 0.0458(15) -0.0114(15) 0.0040(17) -0.050(2)
O9 0.091(2) 0.090(2) 0.0371(15) -0.0099(14) 0.0065(16) -0.0058(18)
C1 0.049(2) 0.0387(17) 0.0415(17) 0.0022(14) 0.004(2) 0.0004(18)
C2 0.044(2) 0.046(2) 0.0310(17) -0.0058(14) -0.0035(16) -0.0040(17)
C3 0.046(2) 0.046(2) 0.0314(17) -0.0074(16) -0.0026(18) -0.0005(16)
C4 0.051(2) 0.0400(17) 0.0303(15) -0.0022(13) -0.002(2) -0.0031(18)
C5 0.070(3) 0.060(2) 0.0362(18) -0.0002(15) -0.015(2) -0.021(2)
C6 0.052(2) 0.040(2) 0.0313(18) -0.0038(15) -0.0047(17) -0.0020(17)
C7 0.043(2) 0.0368(18) 0.0292(17) -0.0006(13) -0.0038(16) 0.0012(16)
C8 0.060(3) 0.0367(18) 0.0328(17) -0.0001(14) -0.0033(18) -0.0005(17)
C9 0.056(3) 0.0401(18) 0.0323(16) 0.0026(13) -0.0035(18) 0.0043(19)
C10 0.053(3) 0.055(2) 0.0293(19) -0.0030(17) -0.0011(17) 0.000(2)
C11 0.055(3) 0.076(3) 0.0337(17) 0.0041(16) -0.007(2) -0.010(3)
C12 0.063(3) 0.090(4) 0.092(3) 0.012(3) -0.019(3) 0.003(3)
C13 0.061(3) 0.173(6) 0.047(3) -0.007(3) -0.001(2) -0.019(4)
C14 0.108(4) 0.091(3) 0.054(3) -0.004(2) -0.033(3) -0.035(3)
C15 0.059(2) 0.051(2) 0.0391(17) -0.0063(14) -0.010(2) 0.006(2)
C16 0.060(3) 0.052(2) 0.040(2) -0.0106(17) 0.0074(19) 0.004(2)
C17 0.065(3) 0.044(2) 0.0342(18) -0.0066(15) -0.0017(17) 0.0089(19)
C18 0.103(4) 0.067(3) 0.043(2) -0.0155(19) -0.010(2) 0.029(3)
C19 0.129(5) 0.073(3) 0.043(2) -0.018(2) -0.026(3) 0.030(3)
C20 0.081(4) 0.066(3) 0.054(2) 0.002(2) -0.018(2) 0.009(3)
C21 0.077(3) 0.073(3) 0.053(2) -0.019(2) -0.017(2) 0.021(3)
C22 0.067(3) 0.066(2) 0.0425(19) -0.0172(17) -0.002(3) 0.003(2)
C23 0.147(6) 0.112(5) 0.116(4) -0.019(3) -0.066(5) 0.053(5)
C24 0.055(2) 0.046(2) 0.0384(19) -0.0049(17) 0.0035(18) -0.008(2)
C25 0.048(2) 0.040(2) 0.0389(19) -0.0003(15) 0.0018(18) -0.0018(17)
C26 0.061(3) 0.065(3) 0.041(2) -0.0060(18) 0.011(2) -0.013(2)
C27 0.070(3) 0.080(3) 0.047(2) -0.009(2) 0.002(2) -0.024(2)
C28 0.062(3) 0.055(2) 0.036(2) 0.0012(18) 0.0023(19) 0.005(2)
C29 0.057(3) 0.067(2) 0.043(2) 0.0066(18) 0.010(2) -0.009(3)
C30 0.058(3) 0.057(2) 0.048(2) -0.0007(16) 0.000(2) -0.015(2)
C31 0.099(4) 0.115(4) 0.037(2) 0.005(2) 0.017(3) 0.002(4)

_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
Br1 C9 1.885(3) . ?
N1 C7 1.360(4) . ?
N1 C5 1.380(4) . ?
N1 C4 1.449(4) . ?
N2 C5 1.294(5) . ?
N2 C6 1.381(4) . ?
N3 C9 1.311(4) . ?
N3 C8 1.354(4) . ?
N4 C8 1.331(4) . ?
N4 C7 1.332(4) . ?
N5 C10 1.375(4) . ?
N5 C8 1.389(4) . ?
N5 H5A 0.91(4) . ?
O1 C4 1.414(4) . ?
O1 C1 1.440(4) . ?
O2 C10 1.183(4) . ?
O3 C10 1.338(4) . ?
O3 C11 1.470(4) . ?
O4 C16 1.337(4) . ?
O4 C15 1.445(4) . ?
O5 C16 1.188(4) . ?
O6 C20 1.367(5) . ?
O6 C23 1.400(6) . ?
O7 C24 1.322(4) . ?
O7 C2 1.447(4) . ?
O8 C24 1.208(5) . ?
O9 C28 1.365(4) . ?
O9 C31 1.417(5) . ?
C1 C15 1.506(4) . ?
C1 C2 1.520(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.500(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.509(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4 0.9800 . ?
C5 H5 0.9300 . ?
C6 C9 1.384(5) . ?
C6 C7 1.388(4) . ?
C11 C13 1.496(6) . ?
C11 C14 1.514(6) . ?
C11 C12 1.518(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.472(5) . ?
C17 C22 1.376(5) . ?
C17 C18 1.384(5) . ?
C18 C19 1.356(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(5) . ?
C21 C22 1.391(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.482(5) . ?
C25 C30 1.370(5) . ?
C25 C26 1.378(5) . ?
C26 C27 1.365(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.386(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.369(6) . ?
C29 C30 1.378(5) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C7 N1 C5 105.2(3) . . ?
C7 N1 C4 126.1(3) . . ?
C5 N1 C4 126.7(3) . . ?
C5 N2 C6 103.0(3) . . ?
C9 N3 C8 116.8(3) . . ?
C8 N4 C7 112.2(3) . . ?
C10 N5 C8 126.9(3) . . ?
C10 N5 H5A 116(2) . . ?
C8 N5 H5A 117(2) . . ?
C4 O1 C1 109.9(3) . . ?
C10 O3 C11 120.3(3) . . ?
C16 O4 C15 114.3(3) . . ?
C20 O6 C23 117.9(4) . . ?
C24 O7 C2 118.1(3) . . ?
C28 O9 C31 117.8(4) . . ?
O1 C1 C15 109.6(3) . . ?
O1 C1 C2 106.1(2) . . ?
C15 C1 C2 115.4(3) . . ?
O1 C1 H1 108.5 . . ?
C15 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
O7 C2 C3 108.0(3) . . ?
O7 C2 C1 108.6(3) . . ?
C3 C2 C1 104.2(3) . . ?
O7 C2 H2 111.9 . . ?
C3 C2 H2 111.9 . . ?
C1 C2 H2 111.9 . . ?
C2 C3 C4 102.5(3) . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C4 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
O1 C4 N1 106.9(3) . . ?
O1 C4 C3 106.1(2) . . ?
N1 C4 C3 115.9(3) . . ?
O1 C4 H4 109.3 . . ?
N1 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
N2 C5 N1 115.0(3) . . ?
N2 C5 H5 122.5 . . ?
N1 C5 H5 122.5 . . ?
N2 C6 C9 134.3(3) . . ?
N2 C6 C7 111.3(3) . . ?
C9 C6 C7 114.4(3) . . ?
N4 C7 N1 127.8(3) . . ?
N4 C7 C6 126.6(3) . . ?
N1 C7 C6 105.6(3) . . ?
N4 C8 N3 127.6(3) . . ?
N4 C8 N5 120.1(3) . . ?
N3 C8 N5 112.3(3) . . ?
N3 C9 C6 122.5(3) . . ?
N3 C9 Br1 117.0(3) . . ?
C6 C9 Br1 120.6(2) . . ?
O2 C10 O3 126.8(3) . . ?
O2 C10 N5 125.9(4) . . ?
O3 C10 N5 107.3(3) . . ?
O3 C11 C13 110.9(4) . . ?
O3 C11 C14 102.2(3) . . ?
C13 C11 C14 111.2(4) . . ?
O3 C11 C12 110.3(3) . . ?
C13 C11 C12 110.5(4) . . ?
C14 C11 C12 111.4(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C1 108.8(3) . . ?
O4 C15 H15A 109.9 . . ?
C1 C15 H15A 109.9 . . ?
O4 C15 H15B 109.9 . . ?
C1 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O5 C16 O4 123.1(4) . . ?
O5 C16 C17 123.8(3) . . ?
O4 C16 C17 113.1(3) . . ?
C22 C17 C18 117.0(4) . . ?
C22 C17 C16 124.9(3) . . ?
C18 C17 C16 118.1(3) . . ?
C19 C18 C17 121.8(4) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
O6 C20 C19 116.0(4) . . ?
O6 C20 C21 123.8(4) . . ?
C19 C20 C21 120.2(4) . . ?
C20 C21 C22 118.6(4) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C17 C22 C21 122.0(3) . . ?
C17 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 C24 O7 123.7(3) . . ?
O8 C24 C25 123.3(3) . . ?
O7 C24 C25 113.0(3) . . ?
C30 C25 C26 118.5(3) . . ?
C30 C25 C24 118.6(3) . . ?
C26 C25 C24 122.9(3) . . ?
C27 C26 C25 120.8(4) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 120.0(4) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
O9 C28 C29 124.2(4) . . ?
O9 C28 C27 115.8(4) . . ?
C29 C28 C27 119.9(3) . . ?
C28 C29 C30 119.1(4) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C25 C30 C29 121.7(4) . . ?
C25 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
O9 C31 H31A 109.5 . . ?
O9 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O9 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C4 O1 C1 C15 126.4(3) . . . . ?
C4 O1 C1 C2 1.2(3) . . . . ?
C24 O7 C2 C3 113.0(3) . . . . ?
C24 O7 C2 C1 -134.6(3) . . . . ?
O1 C1 C2 O7 -95.4(3) . . . . ?
C15 C1 C2 O7 143.0(3) . . . . ?
O1 C1 C2 C3 19.4(3) . . . . ?
C15 C1 C2 C3 -102.2(3) . . . . ?
O7 C2 C3 C4 84.2(3) . . . . ?
C1 C2 C3 C4 -31.1(3) . . . . ?
C1 O1 C4 N1 -145.6(3) . . . . ?
C1 O1 C4 C3 -21.4(3) . . . . ?
C7 N1 C4 O1 -89.6(4) . . . . ?
C5 N1 C4 O1 72.0(5) . . . . ?
C7 N1 C4 C3 152.4(3) . . . . ?
C5 N1 C4 C3 -46.0(5) . . . . ?
C2 C3 C4 O1 32.7(3) . . . . ?
C2 C3 C4 N1 151.1(3) . . . . ?
C6 N2 C5 N1 0.5(5) . . . . ?
C7 N1 C5 N2 -1.0(5) . . . . ?
C4 N1 C5 N2 -165.7(3) . . . . ?
C5 N2 C6 C9 176.9(4) . . . . ?
C5 N2 C6 C7 0.1(4) . . . . ?
C8 N4 C7 N1 177.1(3) . . . . ?
C8 N4 C7 C6 -1.5(5) . . . . ?
C5 N1 C7 N4 -177.9(4) . . . . ?
C4 N1 C7 N4 -13.0(5) . . . . ?
C5 N1 C7 C6 0.9(4) . . . . ?
C4 N1 C7 C6 165.8(3) . . . . ?
N2 C6 C7 N4 178.2(3) . . . . ?
C9 C6 C7 N4 0.7(5) . . . . ?
N2 C6 C7 N1 -0.7(4) . . . . ?
C9 C6 C7 N1 -178.1(3) . . . . ?
C7 N4 C8 N3 2.0(5) . . . . ?
C7 N4 C8 N5 -179.2(3) . . . . ?
C9 N3 C8 N4 -1.7(5) . . . . ?
C9 N3 C8 N5 179.5(3) . . . . ?
C10 N5 C8 N4 18.2(6) . . . . ?
C10 N5 C8 N3 -162.9(4) . . . . ?
C8 N3 C9 C6 0.6(5) . . . . ?
C8 N3 C9 Br1 -179.4(2) . . . . ?
N2 C6 C9 N3 -176.9(4) . . . . ?
C7 C6 C9 N3 -0.2(5) . . . . ?
N2 C6 C9 Br1 3.2(6) . . . . ?
C7 C6 C9 Br1 179.9(3) . . . . ?
C11 O3 C10 O2 4.3(6) . . . . ?
C11 O3 C10 N5 -176.1(3) . . . . ?
C8 N5 C10 O2 6.8(7) . . . . ?
C8 N5 C10 O3 -172.8(4) . . . . ?
C10 O3 C11 C13 -66.9(5) . . . . ?
C10 O3 C11 C14 174.5(4) . . . . ?
C10 O3 C11 C12 55.9(5) . . . . ?
C16 O4 C15 C1 178.2(3) . . . . ?
O1 C1 C15 O4 -73.6(4) . . . . ?
C2 C1 C15 O4 46.1(4) . . . . ?
C15 O4 C16 O5 -0.9(6) . . . . ?
C15 O4 C16 C17 178.5(3) . . . . ?
O5 C16 C17 C22 175.5(4) . . . . ?
O4 C16 C17 C22 -3.9(6) . . . . ?
O5 C16 C17 C18 -4.6(6) . . . . ?
O4 C16 C17 C18 176.0(4) . . . . ?
C22 C17 C18 C19 0.5(7) . . . . ?
C16 C17 C18 C19 -179.4(4) . . . . ?
C17 C18 C19 C20 0.2(8) . . . . ?
C23 O6 C20 C19 -177.0(6) . . . . ?
C23 O6 C20 C21 2.0(8) . . . . ?
C18 C19 C20 O6 178.4(5) . . . . ?
C18 C19 C20 C21 -0.6(8) . . . . ?
O6 C20 C21 C22 -178.6(5) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C18 C17 C22 C21 -0.7(6) . . . . ?
C16 C17 C22 C21 179.1(4) . . . . ?
C20 C21 C22 C17 0.3(7) . . . . ?
C2 O7 C24 O8 13.2(6) . . . . ?
C2 O7 C24 C25 -169.1(3) . . . . ?
O8 C24 C25 C30 -0.6(6) . . . . ?
O7 C24 C25 C30 -178.3(3) . . . . ?
O8 C24 C25 C26 179.7(4) . . . . ?
O7 C24 C25 C26 2.0(5) . . . . ?
C30 C25 C26 C27 -2.3(6) . . . . ?
C24 C25 C26 C27 177.4(4) . . . . ?
C25 C26 C27 C28 1.5(7) . . . . ?
C31 O9 C28 C29 0.7(6) . . . . ?
C31 O9 C28 C27 178.9(4) . . . . ?
C26 C27 C28 O9 -179.3(4) . . . . ?
C26 C27 C28 C29 -1.0(7) . . . . ?
O9 C28 C29 C30 179.5(4) . . . . ?
C27 C28 C29 C30 1.3(6) . . . . ?
C26 C25 C30 C29 2.7(6) . . . . ?
C24 C25 C30 C29 -177.0(4) . . . . ?
C28 C29 C30 C25 -2.2(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
N5 H5A O5 0.91(4) 2.09(4) 2.958(4) 158(3) 3_655

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.052