data_global
_journal_name_full               'Chemical Science'
_journal_coden_cambridge         1475
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
M.Movassaghi
D.Siegel
S.Han
_publ_contact_author_name        'Movassaghi, Mohammad'
_publ_contact_author_email       movassag@mit.edu

data_10026
_database_code_depnum_ccdc_archive 'CCDC 775302'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Br N4 O4.50'
_chemical_formula_weight         368.20
_chemical_absolute_configuration rmad

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   13.5873(14)
_cell_length_b                   6.9161(7)
_cell_length_c                   15.7114(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.786(2)
_cell_angle_gamma                90.00
_cell_volume                     1459.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      30.44

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    2.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3422
_exptl_absorpt_correction_T_max  0.8947
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
'Bruker three-circle diffractometer, Bruker APEX CCD'
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39133
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         30.03
_reflns_number_total             8508
_reflns_number_gt                7443
_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 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^)+(0.0420P)^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   0.015(5)
_refine_ls_number_reflns         8508
_refine_ls_number_parameters     426
_refine_ls_number_restraints     402
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      0.998
_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
Br1A Br 1.002362(17) 0.98001(4) 0.418058(17) 0.01990(6) Uani 1 1 d U . .
O1A O 0.76553(13) 0.2032(3) 0.31662(13) 0.0190(4) Uani 1 1 d U . .
O2A O 0.53804(13) 1.2339(3) 0.41928(12) 0.0148(4) Uani 1 1 d U . .
O3A O 0.65748(13) 0.7489(3) 0.58338(12) 0.0159(4) Uani 1 1 d DU . .
H3A H 0.5979(14) 0.740(5) 0.591(2) 0.024 Uiso 1 1 d D . .
N1A N 0.65435(15) 1.0312(3) 0.49604(13) 0.0132(4) Uani 1 1 d U . .
N3A N 0.54762(15) 0.9051(3) 0.39096(15) 0.0156(4) Uani 1 1 d DU . .
H3C H 0.5030(18) 0.897(5) 0.3485(14) 0.019 Uiso 1 1 d D . .
N9A N 0.69248(14) 0.4729(4) 0.36014(14) 0.0157(4) Uani 1 1 d DU . .
H9A H 0.6394(16) 0.414(4) 0.366(2) 0.019 Uiso 1 1 d D . .
N12A N 0.86661(14) 0.6765(3) 0.36934(14) 0.0127(4) Uani 1 1 d U . .
C2A C 0.57608(17) 1.0700(4) 0.43376(16) 0.0131(5) Uani 1 1 d U . .
C4A C 0.60996(17) 0.7438(4) 0.42143(16) 0.0131(5) Uani 1 1 d U . .
H4A H 0.5695 0.6311 0.4359 0.016 Uiso 1 1 calc R . .
C5A C 0.67706(17) 0.8256(4) 0.50386(16) 0.0131(5) Uani 1 1 d U . .
C6A C 0.78400(17) 0.7741(4) 0.49466(16) 0.0135(5) Uani 1 1 d U . .
H6A1 H 0.8314 0.8702 0.5242 0.016 Uiso 1 1 calc R . .
H6A2 H 0.8020 0.6441 0.5184 0.016 Uiso 1 1 calc R . .
C7A C 0.78296(16) 0.7787(4) 0.39760(16) 0.0125(4) Uani 1 1 d U . .
H7A H 0.7831 0.9163 0.3780 0.015 Uiso 1 1 calc R . .
C8A C 0.68341(17) 0.6839(3) 0.35922(16) 0.0128(5) Uani 1 1 d U . .
H8A H 0.6601 0.7324 0.2996 0.015 Uiso 1 1 calc R . .
C10A C 0.76996(18) 0.3773(4) 0.33537(16) 0.0151(5) Uani 1 1 d U . .
C11A C 0.86037(17) 0.4898(4) 0.33613(15) 0.0141(4) Uani 1 1 d U . .
C13A C 0.96183(17) 0.7390(4) 0.37132(17) 0.0153(5) Uani 1 1 d U . .
C14A C 1.01698(17) 0.5986(4) 0.33823(16) 0.0165(5) Uani 1 1 d U . .
H14A H 1.0852 0.6068 0.3316 0.020 Uiso 1 1 calc R . .
C15A C 0.95315(17) 0.4414(3) 0.31628(17) 0.0159(5) Uani 1 1 d U . .
H15A H 0.9704 0.3226 0.2921 0.019 Uiso 1 1 calc R . .
C16A C 0.7030(2) 1.1771(4) 0.55508(18) 0.0204(5) Uani 1 1 d U . .
H16A H 0.6673 1.3002 0.5450 0.031 Uiso 1 1 calc R . .
H16B H 0.7720 1.1939 0.5453 0.031 Uiso 1 1 calc R . .
H16C H 0.7023 1.1354 0.6146 0.031 Uiso 1 1 calc R . .
Br1B Br 0.06769(2) 0.10591(4) -0.08607(2) 0.02954(8) Uani 1 1 d U . .
O1B O 0.31604(16) 0.8724(3) 0.01753(14) 0.0285(5) Uani 1 1 d U . .
O2B O 0.38431(13) -0.1576(3) 0.25152(12) 0.0173(4) Uani 1 1 d U . .
O3B O 0.18977(13) 0.3202(3) 0.28245(12) 0.0218(4) Uani 1 1 d DU . .
H3B H 0.234(2) 0.297(5) 0.3263(17) 0.033 Uiso 1 1 d D . .
N1B N 0.24746(15) 0.0446(3) 0.21399(14) 0.0148(4) Uani 1 1 d U . .
N3B N 0.39836(15) 0.1698(3) 0.22745(15) 0.0163(4) Uani 1 1 d DU . .
H3D H 0.4624(13) 0.169(4) 0.2343(19) 0.020 Uiso 1 1 d D . .
N9B N 0.32928(17) 0.6008(4) 0.09879(15) 0.0207(5) Uani 1 1 d DU . .
H9B H 0.354(2) 0.662(4) 0.1443(15) 0.025 Uiso 1 1 d D . .
N12B N 0.19653(16) 0.4066(3) -0.01994(15) 0.0180(5) Uani 1 1 d U . .
C2B C 0.34727(17) 0.0041(4) 0.23252(16) 0.0140(5) Uani 1 1 d U . .
C4B C 0.33447(17) 0.3314(4) 0.20088(17) 0.0142(5) Uani 1 1 d U . .
H4B H 0.3520 0.4449 0.2396 0.017 Uiso 1 1 calc R . .
C5B C 0.22857(17) 0.2529(4) 0.20961(17) 0.0149(5) Uani 1 1 d U . .
C6B C 0.16148(18) 0.3162(4) 0.12793(17) 0.0182(5) Uani 1 1 d U . .
H6B1 H 0.1369 0.4497 0.1334 0.022 Uiso 1 1 calc R . .
H6B2 H 0.1039 0.2280 0.1140 0.022 Uiso 1 1 calc R . .
C7B C 0.23066(18) 0.3044(4) 0.05983(16) 0.0156(5) Uani 1 1 d U . .
H7B H 0.2412 0.1653 0.0463 0.019 Uiso 1 1 calc R . .
C8B C 0.32997(19) 0.3896(4) 0.10569(17) 0.0151(5) Uani 1 1 d U . .
H8B H 0.3876 0.3338 0.0813 0.018 Uiso 1 1 calc R . .
C10B C 0.2944(2) 0.6983(4) 0.02544(19) 0.0218(6) Uani 1 1 d U . .
C11B C 0.22748(19) 0.5912(4) -0.03821(17) 0.0198(5) Uani 1 1 d U . .
C13B C 0.13030(19) 0.3459(4) -0.08855(18) 0.0203(5) Uani 1 1 d U . .
C14B C 0.1190(2) 0.4839(5) -0.15157(18) 0.0253(5) Uani 1 1 d U . .
H14B H 0.0776 0.4761 -0.2060 0.030 Uiso 1 1 calc R . .
C15B C 0.1809(2) 0.6408(4) -0.11985(18) 0.0248(6) Uani 1 1 d U . .
H15B H 0.1889 0.7585 -0.1492 0.030 Uiso 1 1 calc R . .
C16B C 0.1704(2) -0.0950(4) 0.2232(2) 0.0259(6) Uani 1 1 d U . .
H16D H 0.2007 -0.2223 0.2361 0.039 Uiso 1 1 calc R . .
H16E H 0.1234 -0.1018 0.1694 0.039 Uiso 1 1 calc R . .
H16F H 0.1351 -0.0553 0.2702 0.039 Uiso 1 1 calc R . .
O1W O 0.59373(14) 0.1920(3) 0.19356(15) 0.0266(4) Uani 1 1 d D . .
H1WB H 0.598(3) 0.310(3) 0.178(2) 0.040 Uiso 1 1 d D . .
H1WA H 0.640(2) 0.166(5) 0.2325(18) 0.040 Uiso 1 1 d D . .
O2W O 0.3590(2) 0.0477(4) 0.86685(17) 0.0468(7) Uani 1 1 d D . .
H2WA H 0.398(3) 0.165(5) 0.879(3) 0.070 Uiso 1 1 d D . .
H2WB H 0.362(3) 0.009(6) 0.9199(16) 0.070 Uiso 1 1 d D . .
O3W O 0.4605(2) 0.3913(5) 0.9290(2) 0.0590(8) Uani 1 1 d D . .
H3WA H 0.429(3) 0.463(7) 0.884(3) 0.089 Uiso 1 1 d D . .
H3WB H 0.5240(15) 0.407(8) 0.923(3) 0.089 Uiso 1 1 d 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
Br1A 0.01345(10) 0.01690(11) 0.02957(14) -0.00457(11) 0.00393(9) -0.00490(10)
O1A 0.0196(9) 0.0116(8) 0.0253(10) -0.0016(8) 0.0018(8) -0.0003(7)
O2A 0.0104(7) 0.0132(8) 0.0207(10) 0.0021(7) 0.0015(7) 0.0012(7)
O3A 0.0119(8) 0.0220(9) 0.0140(9) 0.0038(7) 0.0025(7) 0.0003(7)
N1A 0.0117(9) 0.0130(10) 0.0145(10) -0.0019(8) 0.0006(7) 0.0004(7)
N3A 0.0106(9) 0.0128(9) 0.0215(12) -0.0013(9) -0.0038(8) 0.0025(8)
N9A 0.0125(8) 0.0103(9) 0.0249(11) -0.0014(10) 0.0044(8) -0.0041(9)
N12A 0.0097(8) 0.0125(9) 0.0157(10) 0.0001(8) 0.0020(7) -0.0005(7)
C2A 0.0085(10) 0.0168(13) 0.0144(12) -0.0007(9) 0.0038(9) 0.0004(9)
C4A 0.0079(9) 0.0144(11) 0.0170(12) 0.0021(9) 0.0011(8) 0.0012(9)
C5A 0.0091(9) 0.0134(11) 0.0169(12) 0.0004(9) 0.0023(8) 0.0012(9)
C6A 0.0091(9) 0.0164(12) 0.0151(12) -0.0010(10) 0.0016(8) 0.0012(9)
C7A 0.0091(9) 0.0105(10) 0.0179(12) -0.0005(9) 0.0019(8) 0.0001(8)
C8A 0.0111(10) 0.0110(11) 0.0159(12) -0.0001(9) 0.0006(9) -0.0004(9)
C10A 0.0139(11) 0.0146(12) 0.0162(12) 0.0022(10) -0.0001(9) 0.0006(9)
C11A 0.0148(10) 0.0122(10) 0.0156(11) 0.0003(11) 0.0028(8) 0.0015(10)
C13A 0.0123(10) 0.0136(11) 0.0199(13) -0.0004(10) 0.0023(9) -0.0040(9)
C14A 0.0129(10) 0.0174(11) 0.0198(12) 0.0034(11) 0.0047(9) 0.0029(10)
C15A 0.0163(11) 0.0130(12) 0.0190(12) 0.0006(9) 0.0050(9) 0.0021(9)
C16A 0.0192(12) 0.0159(12) 0.0244(14) -0.0053(11) -0.0028(10) -0.0017(10)
Br1B 0.02934(14) 0.02620(15) 0.02874(16) -0.00067(12) -0.00941(11) -0.00851(12)
O1B 0.0385(12) 0.0167(10) 0.0290(12) 0.0029(9) 0.0013(9) -0.0027(9)
O2B 0.0170(8) 0.0135(9) 0.0198(10) -0.0002(7) -0.0025(7) 0.0017(7)
O3B 0.0161(8) 0.0315(11) 0.0177(10) -0.0034(8) 0.0020(7) 0.0084(8)
N1B 0.0101(9) 0.0160(9) 0.0179(11) 0.0016(8) 0.0009(8) 0.0006(7)
N3B 0.0095(9) 0.0168(10) 0.0218(12) -0.0003(9) -0.0001(8) 0.0010(8)
N9B 0.0279(11) 0.0144(10) 0.0180(11) 0.0003(10) -0.0025(9) -0.0037(10)
N12B 0.0188(10) 0.0170(10) 0.0167(11) 0.0019(9) -0.0015(8) 0.0003(9)
C2B 0.0129(10) 0.0175(13) 0.0114(11) -0.0007(10) 0.0015(8) -0.0014(10)
C4B 0.0130(10) 0.0119(11) 0.0168(12) 0.0004(9) -0.0005(9) 0.0000(9)
C5B 0.0112(10) 0.0163(12) 0.0172(12) -0.0031(10) 0.0024(9) 0.0018(9)
C6B 0.0125(10) 0.0211(13) 0.0199(13) 0.0016(11) -0.0007(9) 0.0026(9)
C7B 0.0159(11) 0.0145(11) 0.0150(12) -0.0001(9) -0.0022(9) 0.0009(9)
C8B 0.0154(11) 0.0125(11) 0.0168(13) -0.0001(9) 0.0004(9) -0.0004(9)
C10B 0.0253(13) 0.0181(13) 0.0222(14) 0.0025(11) 0.0039(11) 0.0016(11)
C11B 0.0228(12) 0.0165(12) 0.0198(13) 0.0024(11) 0.0021(10) 0.0019(11)
C13B 0.0198(12) 0.0209(13) 0.0187(13) -0.0026(11) -0.0022(10) -0.0013(11)
C14B 0.0257(12) 0.0302(14) 0.0185(13) -0.0001(13) -0.0017(10) 0.0004(14)
C15B 0.0286(14) 0.0231(15) 0.0225(14) 0.0045(11) 0.0036(11) 0.0015(11)
C16B 0.0171(12) 0.0232(13) 0.0375(17) 0.0047(13) 0.0039(12) -0.0046(11)
O1W 0.0156(9) 0.0289(11) 0.0356(13) -0.0028(10) 0.0043(8) -0.0035(8)
O2W 0.0675(19) 0.0373(14) 0.0386(15) 0.0010(12) 0.0174(14) -0.0038(13)
O3W 0.0576(17) 0.0517(19) 0.070(2) 0.0138(16) 0.0167(16) 0.0041(16)

_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
Br1A C13A 1.870(3) . ?
O1A C10A 1.239(3) . ?
O2A C2A 1.252(3) . ?
O3A C5A 1.419(3) . ?
N1A C2A 1.357(3) . ?
N1A C5A 1.456(3) . ?
N1A C16A 1.459(3) . ?
N3A C2A 1.350(3) . ?
N3A C4A 1.438(3) . ?
N9A C10A 1.350(3) . ?
N9A C8A 1.465(3) . ?
N12A C13A 1.360(3) . ?
N12A C11A 1.391(3) . ?
N12A C7A 1.464(3) . ?
C4A C8A 1.556(3) . ?
C4A C5A 1.571(3) . ?
C5A C6A 1.524(3) . ?
C6A C7A 1.523(3) . ?
C7A C8A 1.541(3) . ?
C10A C11A 1.453(3) . ?
C11A C15A 1.385(3) . ?
C13A C14A 1.376(4) . ?
C14A C15A 1.401(4) . ?
Br1B C13B 1.868(3) . ?
O1B C10B 1.251(3) . ?
O2B C2B 1.244(3) . ?
O3B C5B 1.410(3) . ?
N1B C2B 1.372(3) . ?
N1B C16B 1.447(3) . ?
N1B C5B 1.463(3) . ?
N3B C2B 1.349(3) . ?
N3B C4B 1.437(3) . ?
N9B C10B 1.357(4) . ?
N9B C8B 1.465(3) . ?
N12B C13B 1.361(3) . ?
N12B C11B 1.388(4) . ?
N12B C7B 1.452(3) . ?
C4B C8B 1.541(4) . ?
C4B C5B 1.563(3) . ?
C5B C6B 1.521(4) . ?
C6B C7B 1.530(3) . ?
C7B C8B 1.546(3) . ?
C10B C11B 1.448(4) . ?
C11B C15B 1.384(4) . ?
C13B C14B 1.367(4) . ?
C14B C15B 1.416(4) . ?

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
C2A N1A C5A 112.7(2) . . ?
C2A N1A C16A 123.4(2) . . ?
C5A N1A C16A 123.5(2) . . ?
C2A N3A C4A 112.4(2) . . ?
C10A N9A C8A 123.6(2) . . ?
C13A N12A C11A 107.9(2) . . ?
C13A N12A C7A 128.3(2) . . ?
C11A N12A C7A 123.82(19) . . ?
O2A C2A N3A 126.5(2) . . ?
O2A C2A N1A 124.5(2) . . ?
N3A C2A N1A 109.0(2) . . ?
N3A C4A C8A 113.5(2) . . ?
N3A C4A C5A 103.5(2) . . ?
C8A C4A C5A 105.46(18) . . ?
O3A C5A N1A 111.9(2) . . ?
O3A C5A C6A 107.80(19) . . ?
N1A C5A C6A 114.4(2) . . ?
O3A C5A C4A 115.33(19) . . ?
N1A C5A C4A 101.15(19) . . ?
C6A C5A C4A 106.22(19) . . ?
C7A C6A C5A 103.11(19) . . ?
N12A C7A C6A 113.87(19) . . ?
N12A C7A C8A 110.6(2) . . ?
C6A C7A C8A 104.85(19) . . ?
N9A C8A C7A 110.6(2) . . ?
N9A C8A C4A 108.67(19) . . ?
C7A C8A C4A 104.47(19) . . ?
O1A C10A N9A 122.2(2) . . ?
O1A C10A C11A 122.2(2) . . ?
N9A C10A C11A 115.5(2) . . ?
C15A C11A N12A 107.7(2) . . ?
C15A C11A C10A 131.8(3) . . ?
N12A C11A C10A 120.2(2) . . ?
N12A C13A C14A 109.8(2) . . ?
N12A C13A Br1A 120.95(18) . . ?
C14A C13A Br1A 129.24(18) . . ?
C13A C14A C15A 106.8(2) . . ?
C11A C15A C14A 107.9(2) . . ?
C2B N1B C16B 123.3(2) . . ?
C2B N1B C5B 111.8(2) . . ?
C16B N1B C5B 122.5(2) . . ?
C2B N3B C4B 112.60(19) . . ?
C10B N9B C8B 123.8(2) . . ?
C13B N12B C11B 107.7(2) . . ?
C13B N12B C7B 128.2(2) . . ?
C11B N12B C7B 124.0(2) . . ?
O2B C2B N3B 125.8(2) . . ?
O2B C2B N1B 125.8(2) . . ?
N3B C2B N1B 108.4(2) . . ?
N3B C4B C8B 114.7(2) . . ?
N3B C4B C5B 103.2(2) . . ?
C8B C4B C5B 106.0(2) . . ?
O3B C5B N1B 111.8(2) . . ?
O3B C5B C6B 109.9(2) . . ?
N1B C5B C6B 113.7(2) . . ?
O3B C5B C4B 114.8(2) . . ?
N1B C5B C4B 100.89(19) . . ?
C6B C5B C4B 105.5(2) . . ?
C5B C6B C7B 102.81(19) . . ?
N12B C7B C6B 115.4(2) . . ?
N12B C7B C8B 111.0(2) . . ?
C6B C7B C8B 103.9(2) . . ?
N9B C8B C4B 109.3(2) . . ?
N9B C8B C7B 110.5(2) . . ?
C4B C8B C7B 104.8(2) . . ?
O1B C10B N9B 120.4(3) . . ?
O1B C10B C11B 123.8(3) . . ?
N9B C10B C11B 115.7(3) . . ?
C15B C11B N12B 108.0(2) . . ?
C15B C11B C10B 131.6(3) . . ?
N12B C11B C10B 120.4(2) . . ?
N12B C13B C14B 110.2(3) . . ?
N12B C13B Br1B 120.4(2) . . ?
C14B C13B Br1B 129.4(2) . . ?
C13B C14B C15B 106.6(2) . . ?
C11B C15B C14B 107.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.087


# Attachment 'AgelastatinB.cif'

data_agb
_database_code_depnum_ccdc_archive 'CCDC 775303'
#TrackingRef 'AgelastatinB.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Br2 N4 O3'
_chemical_formula_weight         420.08
_chemical_absolute_configuration rmad

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.7838(7)
_cell_length_b                   8.1180(9)
_cell_length_c                   12.9579(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.117(2)
_cell_angle_gamma                90.00
_cell_volume                     702.51(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      30.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    5.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2366
_exptl_absorpt_correction_T_max  0.5954
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
'Bruker three-circle diffractometer, Bruker APEX CCD'
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12240
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         29.13
_reflns_number_total             3735
_reflns_number_gt                3555
_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 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^)+(0.0108P)^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   0.012(6)
_refine_ls_number_reflns         3735
_refine_ls_number_parameters     200
_refine_ls_number_restraints     200
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0491
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      0.982
_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
Br1 Br 0.02190(3) 1.00311(3) -0.143243(18) 0.01825(6) Uani 1 1 d U . .
N12 N 0.3774(3) 0.9351(2) 0.13772(15) 0.0120(4) Uani 1 1 d U . .
O1 O 0.0936(2) 1.1219(2) 0.31624(13) 0.0170(4) Uani 1 1 d U . .
C13 C 0.3279(3) 0.9108(3) 0.03238(18) 0.0134(4) Uani 1 1 d U . .
Br2 Br 0.49988(3) 0.80716(3) -0.043886(18) 0.02044(6) Uani 1 1 d U . .
O2 O 0.4807(2) 0.6491(2) 0.44655(13) 0.0148(4) Uani 1 1 d DU . .
H2O2 H 0.357(3) 0.650(3) 0.419(2) 0.018 Uiso 1 1 d D . .
N9 N 0.4149(3) 1.0321(2) 0.34376(15) 0.0145(4) Uani 1 1 d DU . .
H1N9 H 0.430(4) 1.068(3) 0.4091(15) 0.017 Uiso 1 1 d D . .
C14 C 0.1454(3) 0.9862(3) -0.00276(17) 0.0146(4) Uani 1 1 d U . .
O3 O 1.1057(2) 0.5858(2) 0.38018(14) 0.0184(4) Uani 1 1 d U . .
N3 N 0.9069(3) 0.8190(3) 0.37770(15) 0.0147(4) Uani 1 1 d DU . .
H1N3 H 1.005(3) 0.888(3) 0.390(2) 0.018 Uiso 1 1 d D . .
C15 C 0.0788(3) 1.0545(3) 0.08489(19) 0.0153(5) Uani 1 1 d U . .
H3A H -0.0430 1.1122 0.0848 0.018 Uiso 1 1 calc R . .
N1 N 0.7672(3) 0.5736(2) 0.38146(16) 0.0122(4) Uani 1 1 d U . .
C11 C 0.2239(3) 1.0217(3) 0.17065(17) 0.0126(4) Uani 1 1 d U . .
C10 C 0.2364(3) 1.0642(3) 0.28142(18) 0.0130(4) Uani 1 1 d U . .
C8 C 0.5955(3) 0.9731(3) 0.30772(18) 0.0119(4) Uani 1 1 d U . .
H6 H 0.6830 1.0660 0.2927 0.014 Uiso 1 1 calc R . .
C7 C 0.5382(3) 0.8591(3) 0.21251(17) 0.0100(4) Uani 1 1 d U . .
H7 H 0.6574 0.8405 0.1783 0.012 Uiso 1 1 calc R . .
C6 C 0.4762(3) 0.6961(3) 0.25797(17) 0.0118(4) Uani 1 1 d U . .
H8A H 0.5086 0.6017 0.2156 0.014 Uiso 1 1 calc R . .
H8B H 0.3306 0.6953 0.2591 0.014 Uiso 1 1 calc R . .
C5 C 0.5979(3) 0.6866(3) 0.37116(17) 0.0096(4) Uani 1 1 d U . .
C4 C 0.7047(3) 0.8570(3) 0.39163(18) 0.0113(4) Uani 1 1 d U . .
H10 H 0.7008 0.8984 0.4639 0.014 Uiso 1 1 calc R . .
C2 C 0.9426(3) 0.6543(3) 0.38102(18) 0.0137(5) Uani 1 1 d U . .
C16 C 0.7436(3) 0.3975(3) 0.37007(19) 0.0149(5) Uani 1 1 d U . .
H12A H 0.6600 0.3725 0.3022 0.022 Uiso 1 1 calc R . .
H12B H 0.6795 0.3544 0.4266 0.022 Uiso 1 1 calc R . .
H12C H 0.8753 0.3461 0.3736 0.022 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
Br1 0.01927(10) 0.02332(12) 0.01064(11) 0.00287(10) -0.00154(8) 0.00363(10)
N12 0.0146(8) 0.0125(9) 0.0083(9) 0.0012(7) 0.0006(7) 0.0018(7)
O1 0.0184(7) 0.0175(9) 0.0166(9) -0.0002(7) 0.0073(7) 0.0012(7)
C13 0.0185(10) 0.0120(11) 0.0093(10) 0.0000(8) 0.0014(9) 0.0015(9)
Br2 0.02616(12) 0.02399(13) 0.01150(11) -0.00045(10) 0.00423(9) 0.01146(11)
O2 0.0089(7) 0.0257(10) 0.0096(8) 0.0027(7) 0.0012(6) -0.0011(6)
N9 0.0184(8) 0.0160(11) 0.0087(9) -0.0030(8) 0.0009(8) 0.0021(8)
C14 0.0178(9) 0.0152(12) 0.0100(10) 0.0019(9) 0.0005(8) 0.0005(9)
O3 0.0090(7) 0.0258(10) 0.0203(9) -0.0023(8) 0.0022(7) -0.0005(7)
N3 0.0098(8) 0.0160(10) 0.0174(10) 0.0010(9) 0.0003(7) -0.0041(8)
C15 0.0153(10) 0.0153(12) 0.0154(12) 0.0018(9) 0.0025(9) 0.0006(8)
N1 0.0095(8) 0.0127(10) 0.0144(10) 0.0012(8) 0.0024(8) 0.0002(7)
C11 0.0143(9) 0.0103(11) 0.0130(10) 0.0003(9) 0.0018(8) 0.0007(9)
C10 0.0171(10) 0.0096(10) 0.0129(11) 0.0009(8) 0.0040(9) -0.0015(8)
C8 0.0144(9) 0.0090(11) 0.0127(11) -0.0009(8) 0.0034(8) -0.0002(8)
C7 0.0111(9) 0.0097(10) 0.0087(10) 0.0004(8) 0.0005(8) 0.0006(7)
C6 0.0144(9) 0.0110(10) 0.0091(10) 0.0005(9) -0.0003(8) 0.0005(9)
C5 0.0093(8) 0.0114(10) 0.0081(10) 0.0004(8) 0.0015(8) -0.0004(8)
C4 0.0121(9) 0.0132(11) 0.0083(10) -0.0022(8) 0.0009(8) -0.0009(8)
C2 0.0114(9) 0.0215(13) 0.0077(10) -0.0003(9) 0.0006(9) -0.0010(8)
C16 0.0160(10) 0.0108(11) 0.0173(12) 0.0031(9) 0.0016(10) 0.0017(9)

_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 C14 1.870(2) . ?
N12 C13 1.362(3) . ?
N12 C11 1.384(3) . ?
N12 C7 1.462(3) . ?
O1 C10 1.231(3) . ?
C13 C14 1.384(3) . ?
C13 Br2 1.857(2) . ?
O2 C5 1.397(3) . ?
N9 C10 1.358(3) . ?
N9 C8 1.466(3) . ?
C14 C15 1.408(3) . ?
O3 C2 1.240(3) . ?
N3 C2 1.358(3) . ?
N3 C4 1.448(3) . ?
C15 C11 1.375(3) . ?
N1 C2 1.359(3) . ?
N1 C16 1.443(3) . ?
N1 C5 1.458(3) . ?
C11 C10 1.464(3) . ?
C8 C4 1.528(3) . ?
C8 C7 1.536(3) . ?
C7 C6 1.537(3) . ?
C6 C5 1.553(3) . ?
C5 C4 1.562(3) . ?

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 N12 C11 108.44(18) . . ?
C13 N12 C7 128.84(19) . . ?
C11 N12 C7 121.58(19) . . ?
N12 C13 C14 108.33(19) . . ?
N12 C13 Br2 122.12(16) . . ?
C14 C13 Br2 129.36(18) . . ?
C10 N9 C8 125.5(2) . . ?
C13 C14 C15 107.7(2) . . ?
C13 C14 Br1 125.06(17) . . ?
C15 C14 Br1 127.15(17) . . ?
C2 N3 C4 111.91(19) . . ?
C11 C15 C14 106.9(2) . . ?
C2 N1 C16 124.0(2) . . ?
C2 N1 C5 111.90(18) . . ?
C16 N1 C5 122.83(19) . . ?
C15 C11 N12 108.6(2) . . ?
C15 C11 C10 131.0(2) . . ?
N12 C11 C10 120.32(19) . . ?
O1 C10 N9 122.1(2) . . ?
O1 C10 C11 122.4(2) . . ?
N9 C10 C11 115.46(19) . . ?
N9 C8 C4 107.60(18) . . ?
N9 C8 C7 110.16(17) . . ?
C4 C8 C7 102.86(17) . . ?
N12 C7 C8 109.41(17) . . ?
N12 C7 C6 113.27(17) . . ?
C8 C7 C6 104.97(18) . . ?
C7 C6 C5 105.61(17) . . ?
O2 C5 N1 109.58(18) . . ?
O2 C5 C6 113.45(16) . . ?
N1 C5 C6 113.41(18) . . ?
O2 C5 C4 112.21(18) . . ?
N1 C5 C4 101.94(16) . . ?
C6 C5 C4 105.65(18) . . ?
N3 C4 C8 113.20(18) . . ?
N3 C4 C5 102.22(17) . . ?
C8 C4 C5 105.84(17) . . ?
O3 C2 N3 126.5(2) . . ?
O3 C2 N1 124.6(2) . . ?
N3 C2 N1 108.85(19) . . ?

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
O2 H2O2 O3 0.850(16) 1.770(18) 2.589(2) 161(3) 1_455
N3 H1N3 O1 0.863(17) 2.25(2) 2.940(3) 137(2) 1_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.076

# Attachment 'AgelastatinD.cif'

data_10087
_database_code_depnum_ccdc_archive 'CCDC 775304'
#TrackingRef 'AgelastatinD.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 Br N4 O3'
_chemical_formula_weight         327.15
_chemical_absolute_configuration rmad

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                   6.1269(7)
_cell_length_b                   6.8919(9)
_cell_length_c                   29.087(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1228.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      30.44

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    3.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2846
_exptl_absorpt_correction_T_max  0.8501
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
'Bruker three-circle diffractometer, Bruker APEX CCD'
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33337
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         30.48
_reflns_number_total             3716
_reflns_number_gt                3417
_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 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^)+(0.0466P)^2^+2.0961P] 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   0.046(11)
_refine_ls_number_reflns         3716
_refine_ls_number_parameters     184
_refine_ls_number_restraints     188
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.133
_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
Br1 Br 0.42973(7) 0.13213(6) 0.022018(13) 0.02404(11) Uani 1 1 d U . .
O1 O 1.1956(4) -0.1060(4) 0.15802(10) 0.0177(5) Uani 1 1 d U . .
O2 O 0.7309(4) 0.6416(4) 0.18623(8) 0.0120(4) Uani 1 1 d DU . .
H1O2 H 0.860(4) 0.599(6) 0.1906(15) 0.014 Uiso 1 1 d D . .
O3 O 0.0922(4) 0.4877(4) 0.21936(9) 0.0135(5) Uani 1 1 d U . .
N1 N 0.3860(4) 0.5223(4) 0.16962(10) 0.0112(5) Uani 1 1 d DU . .
H1N1 H 0.341(7) 0.639(4) 0.1609(14) 0.013 Uiso 1 1 d D . .
C2 C 0.2793(5) 0.4438(5) 0.20639(12) 0.0114(6) Uani 1 1 d U . .
N3 N 0.4067(5) 0.3057(4) 0.22560(10) 0.0123(5) Uani 1 1 d DU . .
H1N3 H 0.377(7) 0.263(7) 0.2528(9) 0.015 Uiso 1 1 d D . .
C4 C 0.6225(5) 0.2994(5) 0.20557(12) 0.0103(6) Uani 1 1 d U . .
H4 H 0.7377 0.3178 0.2295 0.012 Uiso 1 1 calc R . .
C5 C 0.6171(5) 0.4758(4) 0.17102(12) 0.0098(6) Uani 1 1 d U . .
C6 C 0.7005(5) 0.3941(5) 0.12487(12) 0.0130(6) Uani 1 1 d U . .
H6A H 0.6362 0.4645 0.0985 0.016 Uiso 1 1 calc R . .
H6B H 0.8617 0.4009 0.1229 0.016 Uiso 1 1 calc R . .
C7 C 0.6208(5) 0.1825(4) 0.12661(11) 0.0103(6) Uani 1 1 d U . .
H7 H 0.4595 0.1804 0.1214 0.012 Uiso 1 1 calc R . .
C8 C 0.6677(5) 0.1162(5) 0.17633(11) 0.0109(6) Uani 1 1 d U . .
H8 H 0.5710 0.0060 0.1856 0.013 Uiso 1 1 calc R . .
N9 N 0.8996(5) 0.0658(4) 0.18142(11) 0.0127(5) Uani 1 1 d DU . .
H1N9 H 0.945(8) 0.055(7) 0.2091(8) 0.015 Uiso 1 1 d D . .
C10 C 1.0128(5) -0.0366(5) 0.14936(13) 0.0129(6) Uani 1 1 d U . .
C11 C 0.9127(6) -0.0516(5) 0.10451(12) 0.0155(6) Uani 1 1 d U . .
N12 N 0.7237(5) 0.0518(4) 0.09427(11) 0.0144(6) Uani 1 1 d U . .
C13 C 0.6672(6) 0.0098(5) 0.04970(14) 0.0173(7) Uani 1 1 d U . .
C14 C 0.8155(7) -0.1229(6) 0.03157(14) 0.0257(8) Uani 1 1 d U . .
H14 H 0.8143 -0.1764 0.0015 0.031 Uiso 1 1 calc R . .
C15 C 0.9677(6) -0.1621(5) 0.06665(14) 0.0200(7) Uani 1 1 d U . .
H15 H 1.0873 -0.2493 0.0646 0.024 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
Br1 0.02629(18) 0.02516(19) 0.02066(17) -0.00264(16) -0.00735(15) 0.00134(16)
O1 0.0126(11) 0.0098(12) 0.0306(14) -0.0011(10) 0.0006(10) 0.0051(9)
O2 0.0099(10) 0.0058(10) 0.0203(12) -0.0019(10) 0.0007(8) -0.0017(9)
O3 0.0047(10) 0.0150(11) 0.0208(12) -0.0022(9) -0.0005(9) 0.0008(9)
N1 0.0075(12) 0.0086(13) 0.0176(14) 0.0011(10) -0.0002(9) 0.0035(9)
C2 0.0087(13) 0.0104(14) 0.0151(16) -0.0029(12) -0.0020(11) -0.0010(11)
N3 0.0122(13) 0.0093(12) 0.0153(13) 0.0026(10) 0.0031(11) 0.0028(10)
C4 0.0069(13) 0.0073(13) 0.0168(15) 0.0004(11) 0.0006(10) 0.0002(10)
C5 0.0081(13) 0.0043(13) 0.0169(15) 0.0011(11) -0.0015(10) 0.0022(10)
C6 0.0124(13) 0.0081(15) 0.0183(15) -0.0020(12) 0.0000(11) -0.0010(11)
C7 0.0078(13) 0.0088(14) 0.0144(14) -0.0010(11) -0.0001(10) 0.0008(9)
C8 0.0078(12) 0.0108(14) 0.0141(14) -0.0001(12) 0.0009(10) 0.0022(11)
N9 0.0096(12) 0.0091(12) 0.0195(14) -0.0020(10) -0.0019(10) 0.0024(9)
C10 0.0112(13) 0.0049(13) 0.0225(17) 0.0006(12) 0.0041(11) -0.0008(10)
C11 0.0166(15) 0.0084(13) 0.0216(16) -0.0011(12) 0.0030(13) 0.0044(13)
N12 0.0163(13) 0.0079(12) 0.0191(15) -0.0029(11) 0.0001(11) 0.0024(11)
C13 0.0165(16) 0.0145(17) 0.0208(17) -0.0022(13) -0.0016(13) -0.0010(12)
C14 0.034(2) 0.0167(17) 0.026(2) -0.0070(16) -0.0047(15) -0.0011(16)
C15 0.0224(18) 0.0124(17) 0.0252(18) -0.0054(14) 0.0042(14) 0.0024(13)

_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 C13 1.864(4) . ?
O1 C10 1.244(4) . ?
O2 C5 1.409(4) . ?
O3 C2 1.244(4) . ?
N1 C2 1.365(4) . ?
N1 C5 1.452(4) . ?
C2 N3 1.352(4) . ?
N3 C4 1.446(4) . ?
C4 C8 1.547(5) . ?
C4 C5 1.578(5) . ?
C5 C6 1.543(5) . ?
C6 C7 1.538(5) . ?
C7 N12 1.447(4) . ?
C7 C8 1.544(5) . ?
C8 N9 1.470(4) . ?
N9 C10 1.360(5) . ?
C10 C11 1.445(5) . ?
C11 C15 1.381(5) . ?
C11 N12 1.391(4) . ?
N12 C13 1.373(5) . ?
C13 C14 1.393(5) . ?
C14 C15 1.408(6) . ?

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
C2 N1 C5 111.0(3) . . ?
O3 C2 N3 125.3(3) . . ?
O3 C2 N1 125.6(3) . . ?
N3 C2 N1 109.0(3) . . ?
C2 N3 C4 112.5(3) . . ?
N3 C4 C8 114.2(3) . . ?
N3 C4 C5 102.4(2) . . ?
C8 C4 C5 106.4(3) . . ?
O2 C5 N1 108.2(3) . . ?
O2 C5 C6 113.9(3) . . ?
N1 C5 C6 112.3(3) . . ?
O2 C5 C4 114.5(3) . . ?
N1 C5 C4 102.0(2) . . ?
C6 C5 C4 105.4(2) . . ?
C7 C6 C5 102.3(3) . . ?
N12 C7 C6 115.5(3) . . ?
N12 C7 C8 110.1(3) . . ?
C6 C7 C8 104.6(3) . . ?
N9 C8 C7 110.1(3) . . ?
N9 C8 C4 108.1(3) . . ?
C7 C8 C4 103.9(3) . . ?
C10 N9 C8 123.1(3) . . ?
O1 C10 N9 121.3(4) . . ?
O1 C10 C11 122.5(3) . . ?
N9 C10 C11 116.1(3) . . ?
C15 C11 N12 108.3(3) . . ?
C15 C11 C10 131.0(3) . . ?
N12 C11 C10 120.7(3) . . ?
C13 N12 C11 107.7(3) . . ?
C13 N12 C7 129.4(3) . . ?
C11 N12 C7 122.8(3) . . ?
N12 C13 C14 109.3(3) . . ?
N12 C13 Br1 120.6(3) . . ?
C14 C13 Br1 130.0(3) . . ?
C13 C14 C15 106.5(3) . . ?
C11 C15 C14 108.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.323
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.124

# Attachment 'MethylEster.cif'

data_10011
_database_code_depnum_ccdc_archive 'CCDC 775305'
#TrackingRef 'MethylEster.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 Br N2 O4'
_chemical_formula_weight         317.14
_chemical_absolute_configuration rmad

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                   8.4061(9)
_cell_length_b                   9.2037(10)
_cell_length_c                   17.3522(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1342.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    3.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4129
_exptl_absorpt_correction_T_max  0.6559
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
'Bruker three-circle diffractometer, Bruker APEX CCD'
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35594
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         29.56
_reflns_number_total             3764
_reflns_number_gt                3605
_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 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^)+(0.0287P)^2^+0.3533P] 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   0.009(6)
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     168
_refine_ls_number_restraints     155
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.009
_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 0.45303(2) 1.23443(2) 0.761152(11) 0.02535(6) Uani 1 1 d U . .
O3 O -0.05881(15) 1.10047(13) 0.75964(7) 0.0224(2) Uani 1 1 d U . .
O1 O 0.37837(13) 0.75117(15) 0.50300(7) 0.0211(3) Uani 1 1 d U . .
C11 C 0.43144(19) 0.94398(17) 0.58949(9) 0.0129(3) Uani 1 1 d U . .
C8 C 0.1060(2) 1.00163(17) 0.59190(9) 0.0133(3) Uani 1 1 d U . .
H8 H -0.0075 0.9846 0.6065 0.016 Uiso 1 1 calc R . .
C13 C 0.49127(19) 1.10630(17) 0.67985(9) 0.0149(3) Uani 1 1 d U . .
O2 O 0.11365(15) 1.12359(13) 0.54253(7) 0.0180(3) Uani 1 1 d U . .
C6 C 0.16386(19) 0.94340(17) 0.73314(10) 0.0148(3) Uani 1 1 d U . .
H6A H 0.1454 0.8430 0.7148 0.018 Uiso 1 1 calc R . .
H6B H 0.2569 0.9420 0.7681 0.018 Uiso 1 1 calc R . .
N9 N 0.16809(17) 0.87074(16) 0.55612(8) 0.0147(3) Uani 1 1 d DU . .
H9 H 0.107(2) 0.820(2) 0.5292(12) 0.018 Uiso 1 1 d D . .
C7 C 0.19942(18) 1.04208(17) 0.66415(9) 0.0121(3) Uani 1 1 d U . .
H7 H 0.1718 1.1442 0.6786 0.014 Uiso 1 1 calc R . .
C10 C 0.32703(19) 0.84818(18) 0.54510(9) 0.0144(3) Uani 1 1 d U . .
N12 N 0.36849(16) 1.03679(15) 0.64430(8) 0.0129(3) Uani 1 1 d U . .
C5 C 0.01938(19) 0.99545(16) 0.77685(9) 0.0146(3) Uani 1 1 d U . .
O4 O -0.00977(17) 0.91247(14) 0.83815(8) 0.0256(3) Uani 1 1 d U . .
C14 C 0.6335(2) 1.06253(19) 0.64770(10) 0.0163(3) Uani 1 1 d U . .
H14 H 0.7367 1.0959 0.6613 0.020 Uiso 1 1 calc R . .
C16 C -0.1439(3) 0.9579(2) 0.88503(13) 0.0295(5) Uani 1 1 d U . .
H16A H -0.1233 1.0550 0.9060 0.044 Uiso 1 1 calc R . .
H16B H -0.1588 0.8890 0.9275 0.044 Uiso 1 1 calc R . .
H16C H -0.2402 0.9605 0.8532 0.044 Uiso 1 1 calc R . .
C15 C 0.5961(2) 0.95844(18) 0.59068(10) 0.0152(3) Uani 1 1 d U . .
H15 H 0.6697 0.9077 0.5590 0.018 Uiso 1 1 calc R . .
C17 C 0.0016(3) 1.1172(3) 0.48062(13) 0.0346(5) Uani 1 1 d U . .
H17A H 0.0261 1.0338 0.4475 0.052 Uiso 1 1 calc R . .
H17B H 0.0079 1.2068 0.4503 0.052 Uiso 1 1 calc R . .
H17C H -0.1060 1.1065 0.5016 0.052 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
Br1 0.02073(8) 0.02815(9) 0.02718(9) -0.01637(7) 0.00330(6) -0.00725(7)
O3 0.0211(6) 0.0248(6) 0.0213(6) 0.0038(5) 0.0040(5) 0.0081(5)
O1 0.0159(6) 0.0221(6) 0.0252(6) -0.0110(5) 0.0009(4) 0.0009(5)
C11 0.0134(8) 0.0137(7) 0.0116(6) -0.0008(5) 0.0006(5) 0.0007(6)
C8 0.0118(7) 0.0131(7) 0.0150(7) -0.0006(6) 0.0004(6) -0.0004(6)
C13 0.0152(8) 0.0146(7) 0.0148(7) -0.0026(6) -0.0002(6) -0.0024(6)
O2 0.0200(6) 0.0167(6) 0.0173(6) 0.0040(5) -0.0052(5) -0.0005(5)
C6 0.0150(7) 0.0139(6) 0.0156(7) -0.0004(6) 0.0033(6) 0.0016(5)
N9 0.0109(6) 0.0147(6) 0.0186(7) -0.0047(5) -0.0013(5) -0.0013(5)
C7 0.0102(7) 0.0118(7) 0.0143(7) -0.0007(6) 0.0006(5) -0.0010(5)
C10 0.0143(8) 0.0149(7) 0.0140(7) -0.0012(6) -0.0001(6) 0.0003(6)
N12 0.0114(6) 0.0137(6) 0.0135(6) -0.0019(5) 0.0007(5) -0.0002(5)
C5 0.0159(7) 0.0142(7) 0.0138(7) -0.0018(5) 0.0002(5) -0.0015(6)
O4 0.0331(8) 0.0196(6) 0.0240(6) 0.0058(5) 0.0159(5) 0.0077(5)
C14 0.0130(8) 0.0184(8) 0.0174(7) -0.0009(6) -0.0017(6) -0.0020(6)
C16 0.0361(11) 0.0233(9) 0.0291(10) 0.0015(8) 0.0202(9) 0.0034(8)
C15 0.0131(7) 0.0171(7) 0.0155(7) -0.0013(6) 0.0007(6) 0.0013(6)
C17 0.0381(12) 0.0373(11) 0.0284(10) 0.0121(9) -0.0178(9) -0.0071(9)

_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 C13 1.8667(16) . ?
O3 C5 1.2064(19) . ?
O1 C10 1.232(2) . ?
C11 N12 1.384(2) . ?
C11 C15 1.390(2) . ?
C11 C10 1.463(2) . ?
C8 O2 1.4135(19) . ?
C8 N9 1.452(2) . ?
C8 C7 1.525(2) . ?
C13 N12 1.362(2) . ?
C13 C14 1.379(2) . ?
O2 C17 1.430(2) . ?
C6 C5 1.510(2) . ?
C6 C7 1.532(2) . ?
N9 C10 1.366(2) . ?
C7 N12 1.463(2) . ?
C5 O4 1.3321(19) . ?
O4 C16 1.452(2) . ?
C14 C15 1.413(2) . ?

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
N12 C11 C15 108.14(14) . . ?
N12 C11 C10 120.30(14) . . ?
C15 C11 C10 131.49(15) . . ?
O2 C8 N9 112.54(14) . . ?
O2 C8 C7 106.33(13) . . ?
N9 C8 C7 111.66(13) . . ?
N12 C13 C14 109.66(14) . . ?
N12 C13 Br1 120.57(12) . . ?
C14 C13 Br1 129.74(12) . . ?
C8 O2 C17 113.14(14) . . ?
C5 C6 C7 111.19(13) . . ?
C10 N9 C8 122.51(14) . . ?
N12 C7 C8 107.35(13) . . ?
N12 C7 C6 110.72(13) . . ?
C8 C7 C6 113.40(13) . . ?
O1 C10 N9 122.42(15) . . ?
O1 C10 C11 122.61(15) . . ?
N9 C10 C11 114.93(14) . . ?
C13 N12 C11 108.15(13) . . ?
C13 N12 C7 127.87(14) . . ?
C11 N12 C7 123.63(13) . . ?
O3 C5 O4 123.83(16) . . ?
O3 C5 C6 124.62(15) . . ?
O4 C5 C6 111.54(14) . . ?
C5 O4 C16 115.14(14) . . ?
C13 C14 C15 106.74(15) . . ?
C11 C15 C14 107.28(14) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.56
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.061

# Attachment 'PreagelastatinA.cif'

data_10012
_database_code_depnum_ccdc_archive 'CCDC 775306'
#TrackingRef 'PreagelastatinA.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 Br N4 O4'
_chemical_formula_weight         387.24

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                   10.3843(11)
_cell_length_b                   10.7461(11)
_cell_length_c                   14.0947(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1572.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.76

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    2.640
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.3578
_exptl_absorpt_correction_T_max  0.6479
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
'Bruker three-circle diffractometer, Bruker APEX CCD'
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31959
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0403
_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       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         29.56
_reflns_number_total             4413
_reflns_number_gt                4052
_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 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^)+(0.0343P)^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   -0.007(6)
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     214
_refine_ls_number_restraints     197
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      0.993
_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
Br1 Br -0.98411(2) -0.427290(19) -0.130645(14) 0.01899(6) Uani 1 1 d U . .
C7 C -0.97016(19) -0.14214(18) -0.04987(12) 0.0119(4) Uani 1 1 d U . .
H7 H -1.0318 -0.2048 -0.0236 0.014 Uiso 1 1 calc R . .
O1 O -0.62639(14) 0.04576(14) -0.07162(10) 0.0173(3) Uani 1 1 d U . .
N9 N -0.82300(17) 0.02526(16) -0.00394(11) 0.0138(3) Uani 1 1 d U . .
H9 H -0.8253 0.1049 0.0105 0.017 Uiso 1 1 calc R . .
C13 C -0.84437(19) -0.31791(18) -0.12841(15) 0.0144(4) Uani 1 1 d U . .
C4 C -1.27787(19) -0.0642(2) -0.11210(13) 0.0155(4) Uani 1 1 d U . .
H4 H -1.2975 -0.1503 -0.1162 0.019 Uiso 1 1 calc R . .
N1 N -1.17642(16) 0.11683(16) -0.10696(12) 0.0130(3) Uani 1 1 d U . .
O2 O -1.35528(15) 0.24820(13) -0.08853(11) 0.0185(3) Uani 1 1 d U . .
O3 O -0.88676(14) -0.13182(13) 0.10515(9) 0.0158(3) Uani 1 1 d U . .
C17 C -0.8600(2) -0.0638(2) 0.19089(13) 0.0205(4) Uani 1 1 d U . .
H17A H -0.7886 -0.0060 0.1798 0.031 Uiso 1 1 calc R . .
H17B H -0.8365 -0.1222 0.2414 0.031 Uiso 1 1 calc R . .
H17C H -0.9368 -0.0169 0.2099 0.031 Uiso 1 1 calc R . .
N3 N -1.36623(18) 0.03162(16) -0.10023(13) 0.0159(4) Uani 1 1 d U . .
H3 H -1.4501 0.0214 -0.0954 0.019 Uiso 1 1 calc R . .
C15 C -0.6564(2) -0.21915(19) -0.14613(13) 0.0145(4) Uani 1 1 d U . .
H15 H -0.5706 -0.1996 -0.1643 0.017 Uiso 1 1 calc R . .
C8 C -0.92603(19) -0.05450(19) 0.02946(12) 0.0123(4) Uani 1 1 d U . .
H8 H -1.0003 -0.0020 0.0504 0.015 Uiso 1 1 calc R . .
N12 N -0.85485(16) -0.20505(16) -0.08406(11) 0.0121(3) Uani 1 1 d U . .
C6 C -1.03253(17) -0.07442(19) -0.13492(13) 0.0146(3) Uani 1 1 d U . .
H6A H -0.9716 -0.0102 -0.1577 0.018 Uiso 1 1 calc R . .
H6B H -1.0440 -0.1354 -0.1869 0.018 Uiso 1 1 calc R . .
C10 C -0.72298(19) -0.01814(19) -0.05670(13) 0.0125(4) Uani 1 1 d U . .
C2 C -1.3051(2) 0.1429(2) -0.09712(14) 0.0149(4) Uani 1 1 d U . .
C16 C -1.0794(2) 0.21495(19) -0.11117(15) 0.0183(4) Uani 1 1 d U . .
H16A H -1.1190 0.2948 -0.0947 0.027 Uiso 1 1 calc R . .
H16B H -1.0439 0.2195 -0.1755 0.027 Uiso 1 1 calc R . .
H16C H -1.0101 0.1964 -0.0661 0.027 Uiso 1 1 calc R . .
C11 C -0.73891(19) -0.14368(19) -0.09534(14) 0.0129(4) Uani 1 1 d U . .
C5 C -1.1592(2) -0.01329(19) -0.11679(13) 0.0137(4) Uani 1 1 d U . .
C14 C -0.7229(2) -0.3308(2) -0.16609(14) 0.0164(4) Uani 1 1 d U . .
H14 H -0.6902 -0.4011 -0.1991 0.020 Uiso 1 1 calc R . .
O1S O -1.08249(16) 0.16557(17) 0.18437(12) 0.0269(4) Uani 1 1 d DU . .
H1O1 H -1.026(2) 0.199(2) 0.1520(16) 0.032 Uiso 1 1 d D . .
C1S C -1.2049(2) 0.1693(2) 0.14036(17) 0.0237(5) Uani 1 1 d U . .
H1S1 H -1.2716 0.1499 0.1872 0.036 Uiso 1 1 calc R . .
H1S2 H -1.2079 0.1081 0.0889 0.036 Uiso 1 1 calc R . .
H1S3 H -1.2200 0.2527 0.1145 0.036 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
Br1 0.02168(10) 0.01490(9) 0.02039(9) -0.00394(8) 0.00140(8) -0.00412(9)
C7 0.0095(9) 0.0123(9) 0.0141(8) -0.0018(7) 0.0010(7) 0.0001(8)
O1 0.0113(7) 0.0176(8) 0.0228(7) 0.0020(6) 0.0016(5) 0.0001(6)
N9 0.0137(9) 0.0100(8) 0.0176(8) -0.0010(6) 0.0028(6) -0.0013(7)
C13 0.0174(10) 0.0118(9) 0.0140(8) -0.0018(8) -0.0025(8) -0.0002(7)
C4 0.0155(9) 0.0139(9) 0.0172(9) -0.0024(8) -0.0001(7) 0.0012(9)
N1 0.0111(8) 0.0112(8) 0.0167(8) -0.0021(6) -0.0007(6) 0.0000(6)
O2 0.0169(8) 0.0143(7) 0.0243(8) -0.0042(6) -0.0013(6) 0.0041(6)
O3 0.0200(8) 0.0154(7) 0.0119(6) -0.0004(5) -0.0019(5) -0.0009(6)
C17 0.0265(11) 0.0213(11) 0.0136(8) -0.0022(9) -0.0027(7) 0.0012(11)
N3 0.0114(8) 0.0153(8) 0.0210(8) 0.0008(7) 0.0014(6) 0.0003(7)
C15 0.0131(10) 0.0154(9) 0.0151(9) 0.0001(8) 0.0014(7) 0.0028(8)
C8 0.0122(9) 0.0112(10) 0.0135(8) -0.0008(7) 0.0014(7) 0.0010(8)
N12 0.0112(8) 0.0116(8) 0.0135(7) -0.0011(6) 0.0006(6) 0.0009(7)
C6 0.0138(9) 0.0164(8) 0.0136(7) -0.0011(8) -0.0010(7) 0.0017(8)
C10 0.0108(9) 0.0116(9) 0.0150(9) 0.0035(7) -0.0025(7) 0.0003(8)
C2 0.0124(10) 0.0191(10) 0.0132(8) -0.0018(8) -0.0006(7) 0.0010(8)
C16 0.0142(10) 0.0159(10) 0.0248(11) -0.0033(8) -0.0010(8) -0.0034(8)
C11 0.0107(9) 0.0147(10) 0.0134(8) 0.0019(8) -0.0003(7) 0.0011(8)
C5 0.0146(10) 0.0135(9) 0.0130(9) -0.0024(7) -0.0008(7) 0.0011(8)
C14 0.0173(11) 0.0158(10) 0.0160(9) -0.0012(8) -0.0001(8) 0.0040(9)
O1S 0.0192(9) 0.0288(9) 0.0325(9) 0.0060(7) 0.0045(7) -0.0018(7)
C1S 0.0273(12) 0.0191(11) 0.0247(11) 0.0037(9) -0.0019(10) -0.0025(9)

_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 C13 1.8677(19) . ?
C7 N12 1.457(2) . ?
C7 C8 1.532(3) . ?
C7 C6 1.545(3) . ?
O1 C10 1.234(2) . ?
N9 C10 1.360(3) . ?
N9 C8 1.449(3) . ?
C13 N12 1.369(2) . ?
C13 C14 1.375(3) . ?
C4 C5 1.350(3) . ?
C4 N3 1.389(3) . ?
N1 C2 1.372(3) . ?
N1 C5 1.416(3) . ?
N1 C16 1.460(3) . ?
O2 C2 1.251(3) . ?
O3 C8 1.412(2) . ?
O3 C17 1.439(2) . ?
N3 C2 1.355(3) . ?
C15 C11 1.380(3) . ?
C15 C14 1.413(3) . ?
N12 C11 1.382(3) . ?
C6 C5 1.493(3) . ?
C10 C11 1.464(3) . ?
O1S C1S 1.415(3) . ?

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
N12 C7 C8 106.30(16) . . ?
N12 C7 C6 107.85(14) . . ?
C8 C7 C6 113.71(16) . . ?
C10 N9 C8 122.59(17) . . ?
N12 C13 C14 109.78(18) . . ?
N12 C13 Br1 120.24(15) . . ?
C14 C13 Br1 129.99(16) . . ?
C5 C4 N3 107.99(19) . . ?
C2 N1 C5 109.53(17) . . ?
C2 N1 C16 121.91(17) . . ?
C5 N1 C16 128.47(17) . . ?
C8 O3 C17 113.03(15) . . ?
C2 N3 C4 110.40(17) . . ?
C11 C15 C14 107.37(18) . . ?
O3 C8 N9 112.34(16) . . ?
O3 C8 C7 106.02(15) . . ?
N9 C8 C7 110.32(15) . . ?
C13 N12 C11 107.52(17) . . ?
C13 N12 C7 128.86(17) . . ?
C11 N12 C7 122.18(16) . . ?
C5 C6 C7 116.36(16) . . ?
O1 C10 N9 121.55(19) . . ?
O1 C10 C11 122.77(19) . . ?
N9 C10 C11 115.66(18) . . ?
O2 C2 N3 127.32(19) . . ?
O2 C2 N1 126.9(2) . . ?
N3 C2 N1 105.81(17) . . ?
C15 C11 N12 108.68(18) . . ?
C15 C11 C10 131.62(19) . . ?
N12 C11 C10 119.69(18) . . ?
C4 C5 N1 106.26(18) . . ?
C4 C5 C6 129.41(19) . . ?
N1 C5 C6 124.22(18) . . ?
C13 C14 C15 106.63(18) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.56
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.073

# Attachment 'Thioester.cif'

data_10013
_database_code_depnum_ccdc_archive 'CCDC 775307'
#TrackingRef 'Thioester.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Br N2 O3 S'
_chemical_formula_weight         409.30
_chemical_absolute_configuration rmad

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'
Br Br -0.2901 2.4595 '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)

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

_cell_length_a                   9.2556(9)
_cell_length_b                   8.0917(8)
_cell_length_c                   11.7613(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.799(2)
_cell_angle_gamma                90.00
_cell_volume                     880.41(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      30.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4785
_exptl_absorpt_correction_T_max  0.7082
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
'Bruker three-circle diffractometer, Bruker APEX CCD'
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19103
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         29.13
_reflns_number_total             4583
_reflns_number_gt                4269
_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 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^)+(0.0222P)^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   0.014(5)
_refine_ls_number_reflns         4583
_refine_ls_number_parameters     222
_refine_ls_number_restraints     203
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0560
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      0.986
_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
Br1 Br 0.013457(18) 0.94927(3) 0.376844(14) 0.02018(5) Uani 1 1 d U . .
S1 S 0.39981(5) 0.47120(9) 0.53703(4) 0.02648(14) Uani 1 1 d U . .
O3 O 0.16183(13) 0.42930(19) 0.40732(10) 0.0170(3) Uani 1 1 d U . .
C5 C 0.2720(2) 0.5054(2) 0.42213(15) 0.0154(4) Uani 1 1 d U . .
C7 C 0.2125(2) 0.6816(2) 0.24696(16) 0.0138(4) Uani 1 1 d U . .
H7 H 0.1129 0.6547 0.2719 0.017 Uiso 1 1 calc R . .
C19 C 0.2830(2) 0.1758(3) 0.79264(18) 0.0216(4) Uani 1 1 d U . .
H19 H 0.2827 0.1836 0.8732 0.026 Uiso 1 1 calc R . .
C17 C 0.3282(2) 0.3004(3) 0.61160(17) 0.0176(4) Uani 1 1 d U . .
C22 C 0.2870(2) 0.1547(3) 0.55763(17) 0.0212(4) Uani 1 1 d U . .
H22 H 0.2896 0.1463 0.4772 0.025 Uiso 1 1 calc R . .
C18 C 0.3263(2) 0.3118(3) 0.73005(17) 0.0206(4) Uani 1 1 d U . .
H18 H 0.3544 0.4114 0.7674 0.025 Uiso 1 1 calc R . .
C6 C 0.3212(2) 0.6452(3) 0.34606(17) 0.0180(4) Uani 1 1 d U . .
H6A H 0.4158 0.6159 0.3146 0.022 Uiso 1 1 calc R . .
H6B H 0.3347 0.7464 0.3925 0.022 Uiso 1 1 calc R . .
C20 C 0.2403(2) 0.0297(3) 0.74103(19) 0.0223(4) Uani 1 1 d U . .
C23 C 0.1951(3) -0.1187(3) 0.8091(2) 0.0327(6) Uani 1 1 d U . .
H23A H 0.2805 -0.1851 0.8298 0.049 Uiso 1 1 calc R . .
H23B H 0.1270 -0.1858 0.7633 0.049 Uiso 1 1 calc R . .
H23C H 0.1485 -0.0817 0.8783 0.049 Uiso 1 1 calc R . .
C21 C 0.2420(2) 0.0214(3) 0.62164(18) 0.0246(5) Uani 1 1 d U . .
H21 H 0.2118 -0.0773 0.5842 0.030 Uiso 1 1 calc R . .
O1 O 0.49805(16) 0.85755(17) 0.01168(12) 0.0180(3) Uani 1 1 d U . .
O2 O 0.11478(15) 0.59432(19) 0.07063(11) 0.0186(3) Uani 1 1 d U . .
C11 C 0.31370(19) 0.9187(2) 0.13943(15) 0.0141(4) Uani 1 1 d U . .
N12 N 0.21766(17) 0.8549(2) 0.21654(14) 0.0137(3) Uani 1 1 d U . .
C13 C 0.15092(19) 0.9849(2) 0.26705(15) 0.0155(4) Uani 1 1 d U . .
C16 C 0.1114(2) 0.4835(3) -0.02387(17) 0.0255(5) Uani 1 1 d U . .
H16A H 0.1943 0.5053 -0.0715 0.038 Uiso 1 1 calc R . .
H16B H 0.0216 0.4999 -0.0688 0.038 Uiso 1 1 calc R . .
H16C H 0.1159 0.3694 0.0038 0.038 Uiso 1 1 calc R . .
N9 N 0.36973(18) 0.6443(2) 0.08326(15) 0.0162(3) Uani 1 1 d DU . .
H9 H 0.412(2) 0.575(3) 0.0416(17) 0.019 Uiso 1 1 d D . .
C10 C 0.4007(2) 0.8076(2) 0.07234(16) 0.0147(4) Uani 1 1 d U . .
C8 C 0.2425(2) 0.5821(2) 0.13929(16) 0.0153(4) Uani 1 1 d U . .
H8 H 0.2588 0.4638 0.1605 0.018 Uiso 1 1 calc R . .
C15 C 0.3040(2) 1.0894(3) 0.14187(17) 0.0169(4) Uani 1 1 d U . .
H15 H 0.3573 1.1647 0.0975 0.020 Uiso 1 1 calc R . .
C14 C 0.2000(2) 1.1308(3) 0.22286(17) 0.0178(4) Uani 1 1 d U . .
H14 H 0.1699 1.2389 0.2428 0.021 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
Br1 0.01811(8) 0.02404(10) 0.01883(9) -0.00308(10) 0.00773(6) -0.00386(10)
S1 0.0199(2) 0.0354(4) 0.0237(2) 0.0133(3) -0.00677(18) -0.0085(3)
O3 0.0191(6) 0.0165(8) 0.0154(6) 0.0023(6) 0.0015(5) -0.0003(6)
C5 0.0168(9) 0.0176(10) 0.0118(8) 0.0010(7) 0.0006(7) 0.0018(7)
C7 0.0156(9) 0.0125(10) 0.0133(9) 0.0008(7) 0.0011(7) -0.0033(7)
C19 0.0214(10) 0.0304(12) 0.0131(9) 0.0026(8) 0.0020(8) 0.0023(9)
C17 0.0125(9) 0.0228(11) 0.0174(10) 0.0075(8) -0.0006(8) 0.0012(8)
C22 0.0223(10) 0.0267(12) 0.0143(9) 0.0019(8) -0.0011(8) 0.0060(9)
C18 0.0199(10) 0.0231(11) 0.0184(10) 0.0000(8) -0.0036(8) 0.0018(8)
C6 0.0188(10) 0.0184(11) 0.0167(10) 0.0023(8) -0.0008(8) -0.0059(8)
C20 0.0191(10) 0.0284(12) 0.0194(10) 0.0055(9) -0.0011(8) 0.0028(9)
C23 0.0385(13) 0.0321(13) 0.0273(12) 0.0097(10) -0.0019(11) -0.0075(11)
C21 0.0314(11) 0.0211(11) 0.0210(10) 0.0013(9) -0.0040(9) 0.0019(9)
O1 0.0203(7) 0.0151(7) 0.0189(7) 0.0010(6) 0.0070(6) -0.0009(6)
O2 0.0209(7) 0.0189(8) 0.0157(7) -0.0045(6) -0.0027(6) -0.0005(6)
C11 0.0159(8) 0.0145(12) 0.0120(8) 0.0019(7) 0.0034(6) -0.0009(7)
N12 0.0149(8) 0.0115(9) 0.0148(8) 0.0011(6) 0.0021(6) -0.0018(6)
C13 0.0141(8) 0.0195(13) 0.0129(8) -0.0033(7) 0.0030(7) -0.0022(7)
C16 0.0328(11) 0.0258(15) 0.0175(9) -0.0071(8) -0.0021(8) -0.0029(9)
N9 0.0191(8) 0.0121(9) 0.0177(8) -0.0012(6) 0.0050(7) 0.0005(6)
C10 0.0171(9) 0.0140(10) 0.0128(9) 0.0003(7) -0.0009(7) 0.0016(7)
C8 0.0194(9) 0.0118(9) 0.0148(9) 0.0018(7) 0.0007(7) -0.0019(8)
C15 0.0219(10) 0.0114(10) 0.0178(10) 0.0004(8) 0.0041(8) -0.0003(8)
C14 0.0204(10) 0.0137(11) 0.0196(10) -0.0027(8) 0.0048(8) 0.0008(8)

_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 C13 1.8635(17) . ?
S1 C17 1.776(2) . ?
S1 C5 1.789(2) . ?
O3 C5 1.199(2) . ?
C5 C6 1.521(3) . ?
C7 N12 1.448(3) . ?
C7 C8 1.533(3) . ?
C7 C6 1.544(3) . ?
C19 C20 1.381(3) . ?
C19 C18 1.390(3) . ?
C17 C22 1.387(3) . ?
C17 C18 1.397(3) . ?
C22 C21 1.387(3) . ?
C20 C21 1.406(3) . ?
C20 C23 1.510(3) . ?
O1 C10 1.235(2) . ?
O2 C8 1.414(2) . ?
O2 C16 1.427(2) . ?
C11 C15 1.385(3) . ?
C11 N12 1.389(2) . ?
C11 C10 1.456(2) . ?
N12 C13 1.365(2) . ?
C13 C14 1.373(3) . ?
N9 C10 1.358(3) . ?
N9 C8 1.457(2) . ?
C15 C14 1.416(3) . ?

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
C17 S1 C5 104.18(9) . . ?
O3 C5 C6 124.42(18) . . ?
O3 C5 S1 124.72(15) . . ?
C6 C5 S1 110.86(14) . . ?
N12 C7 C8 107.21(15) . . ?
N12 C7 C6 110.21(16) . . ?
C8 C7 C6 113.14(17) . . ?
C20 C19 C18 121.9(2) . . ?
C22 C17 C18 120.05(19) . . ?
C22 C17 S1 122.48(16) . . ?
C18 C17 S1 117.23(17) . . ?
C17 C22 C21 119.72(19) . . ?
C19 C18 C17 119.3(2) . . ?
C5 C6 C7 112.71(16) . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 C23 121.89(19) . . ?
C21 C20 C23 120.2(2) . . ?
C22 C21 C20 121.2(2) . . ?
C8 O2 C16 113.47(15) . . ?
C15 C11 N12 108.31(16) . . ?
C15 C11 C10 131.64(17) . . ?
N12 C11 C10 120.04(17) . . ?
C13 N12 C11 107.77(15) . . ?
C13 N12 C7 128.29(16) . . ?
C11 N12 C7 123.21(16) . . ?
N12 C13 C14 109.77(16) . . ?
N12 C13 Br1 120.69(14) . . ?
C14 C13 Br1 129.53(15) . . ?
C10 N9 C8 123.69(17) . . ?
O1 C10 N9 122.22(18) . . ?
O1 C10 C11 122.47(18) . . ?
N9 C10 C11 115.29(17) . . ?
O2 C8 N9 112.99(15) . . ?
O2 C8 C7 105.37(15) . . ?
N9 C8 C7 111.24(16) . . ?
C11 C15 C14 107.20(18) . . ?
C13 C14 C15 106.95(19) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.063