 
data_mo_zm12_0m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C17 H19 Br N2 O6' 
_chemical_formula_sum 
 'C17 H19 Br N2 O6' 
_chemical_formula_weight          427.25 
_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'   0.0033   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           'Triclinic'
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 
_cell_length_a                    9.380(4) 
_cell_length_b                    9.756(4) 
_cell_length_c                    10.518(5) 
_cell_angle_alpha                 94.969(6) 
_cell_angle_beta                  90.378(6) 
_cell_angle_gamma                 103.743(6) 
_cell_volume                      931.1(7) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     3286
_cell_measurement_theta_min       2.71
_cell_measurement_theta_max       23.93

_exptl_crystal_description       'sheet'
_exptl_crystal_colour            'colourless'
_exptl_crystal_size_max           0.74 
_exptl_crystal_size_mid           0.26 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.524 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              436 
_exptl_absorpt_coefficient_mu     2.243 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.2876 
_exptl_absorpt_correction_T_max   0.8961 
_exptl_absorpt_process_details    'sadabs' 
 
_exptl_special_details 
; 
 ? 
; 
 
_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       'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             11667 
_diffrn_reflns_av_R_equivalents   0.0527 
_diffrn_reflns_av_sigmaI/netI     0.1262 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          1.94 
_diffrn_reflns_theta_max          28.35 
_reflns_number_total              8465 
_reflns_number_gt                 6111 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection      'Bruker APEX2'
_computing_cell_refinement      'Bruker SAINT'
_computing_data_reduction       'Bruker SAINT' 
_computing_structure_solution   'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics   'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.1165P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     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    0.054(13) 
_refine_ls_number_reflns          8465 
_refine_ls_number_parameters      476 
_refine_ls_number_restraints      27 
_refine_ls_R_factor_all           0.1035 
_refine_ls_R_factor_gt            0.0742 
_refine_ls_wR_factor_ref          0.2053 
_refine_ls_wR_factor_gt           0.1870 
_refine_ls_goodness_of_fit_ref    1.004 
_refine_ls_restrained_S_all       1.008 
_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 0.92095(8) 1.30047(8) 0.72640(7) 0.0346(2) Uani 1 1 d . . . 
Br2 Br 0.24316(8) 0.58773(8) -0.09772(7) 0.0354(2) Uani 1 1 d . . . 
O1 O 0.3625(6) 1.0633(6) 0.5671(5) 0.0228(12) Uani 1 1 d . . . 
O2 O 0.5186(5) 0.5658(5) 0.3121(5) 0.0209(10) Uani 1 1 d . . . 
O3 O 0.1872(6) 0.9439(6) 0.4234(5) 0.0251(11) Uani 1 1 d . . . 
O4 O 0.3826(5) 0.7919(5) 0.2304(4) 0.0179(10) Uani 1 1 d . . . 
H4 H 0.4703 0.8327 0.2185 0.027 Uiso 1 1 calc R . . 
O5 O 0.2870(6) 0.5588(6) 0.5379(5) 0.0290(12) Uani 1 1 d . . . 
O6 O 0.0542(6) 0.5209(6) 0.4886(5) 0.0270(12) Uani 1 1 d . . . 
O7 O -0.2040(6) 0.8086(6) 0.0695(5) 0.0206(12) Uani 1 1 d . . . 
C15 C -0.3004(11) 0.6075(10) -0.0710(9) 0.039(2) Uani 1 1 d U . . 
H15A H -0.2543 0.6658 -0.1377 0.058 Uiso 1 1 calc R . . 
H15B H -0.3901 0.5407 -0.1059 0.058 Uiso 1 1 calc R . . 
H15C H -0.2322 0.5547 -0.0404 0.058 Uiso 1 1 calc R . . 
O9 O 0.1994(5) 1.3105(5) 0.3260(5) 0.0199(10) Uani 1 1 d . . . 
O10 O -0.3203(5) 0.9320(6) 0.2087(5) 0.0229(11) Uani 1 1 d . . . 
O11 O -0.0400(7) 1.3246(7) 0.1107(6) 0.0349(15) Uani 1 1 d . . . 
O12 O -0.0425(5) 1.0767(5) 0.4070(4) 0.0199(10) Uani 1 1 d . . . 
H12 H 0.0192 1.0273 0.4114 0.030 Uiso 1 1 calc R . . 
N1 N 0.5784(6) 0.7376(6) 0.4811(5) 0.0183(12) Uani 1 1 d . . . 
N2 N 0.1735(6) 1.1357(6) 0.1591(5) 0.0159(11) Uani 1 1 d U . . 
N3 N -0.1334(7) 1.3226(7) 0.1892(7) 0.0265(14) Uani 1 1 d . . . 
O8 O -0.2271(8) 1.3889(9) 0.1879(9) 0.059(2) Uani 1 1 d . . . 
C1 C 0.6981(8) 1.1243(8) 0.8615(7) 0.0238(15) Uani 1 1 d . . . 
H1 H 0.7354 1.1875 0.9343 0.029 Uiso 1 1 calc R . . 
C2 C 0.7596(8) 1.1449(9) 0.7434(8) 0.0260(16) Uani 1 1 d . . . 
C3 C 0.7044(7) 1.0529(7) 0.6338(7) 0.0179(13) Uani 1 1 d . . . 
H3 H 0.7487 1.0678 0.5536 0.021 Uiso 1 1 calc R . . 
C4 C 0.5843(7) 0.9404(7) 0.6452(6) 0.0173(13) Uani 1 1 d . . . 
C5 C 0.5182(7) 0.8491(7) 0.5288(6) 0.0160(13) Uani 1 1 d . . . 
C6 C 0.3950(7) 0.8546(7) 0.4615(6) 0.0167(13) Uani 1 1 d . . . 
C7 C 0.3053(8) 0.9549(7) 0.4829(7) 0.0168(13) Uani 1 1 d . . . 
C8 C 0.2829(9) 1.1749(8) 0.5937(7) 0.0254(16) Uani 1 1 d . . . 
H8A H 0.2878 1.2317 0.5195 0.031 Uiso 1 1 calc R . . 
H8B H 0.1784 1.1318 0.6086 0.031 Uiso 1 1 calc R . . 
C9 C 0.3491(8) 1.2656(8) 0.7061(7) 0.0257(16) Uani 1 1 d U . . 
H9A H 0.3299 1.2126 0.7817 0.039 Uiso 1 1 calc R . . 
H9B H 0.3068 1.3484 0.7167 0.039 Uiso 1 1 calc R . . 
H9C H 0.4553 1.2969 0.6957 0.039 Uiso 1 1 calc R . . 
C10 C 0.5797(9) 1.0081(9) 0.8709(7) 0.0257(17) Uani 1 1 d . . . 
H10 H 0.5364 0.9923 0.9513 0.031 Uiso 1 1 calc R . . 
C11 C 0.5239(8) 0.9148(8) 0.7644(7) 0.0216(15) Uani 1 1 d . . . 
H11 H 0.4454 0.8345 0.7729 0.026 Uiso 1 1 calc R . . 
C12 C 0.4949(7) 0.6655(7) 0.3751(6) 0.0176(13) Uani 1 1 d . . . 
C13 C 0.3711(7) 0.7407(7) 0.3541(6) 0.0134(12) Uani 1 1 d . . . 
C14 C 0.2228(8) 0.6347(8) 0.3459(7) 0.0207(15) Uani 1 1 d . . . 
H14A H 0.1461 0.6837 0.3240 0.025 Uiso 1 1 calc R . . 
H14B H 0.2237 0.5600 0.2762 0.025 Uiso 1 1 calc R . . 
N4 N 0.1841(7) 0.5672(7) 0.4666(6) 0.0197(13) Uani 1 1 d . . . 
C16 C 0.7100(8) 0.6990(8) 0.5309(8) 0.0239(15) Uani 1 1 d . . . 
H16 H 0.7469 0.7646 0.6088 0.029 Uiso 1 1 calc R . . 
C17 C 0.8294(8) 0.7208(10) 0.4344(9) 0.035(2) Uani 1 1 d . . . 
H17A H 0.8029 0.6473 0.3629 0.053 Uiso 1 1 calc R . . 
H17B H 0.9220 0.7149 0.4746 0.053 Uiso 1 1 calc R . . 
H17C H 0.8408 0.8143 0.4028 0.053 Uiso 1 1 calc R . . 
C18 C 0.6688(9) 0.5481(9) 0.5713(8) 0.0314(18) Uani 1 1 d . . . 
H18A H 0.5904 0.5402 0.6333 0.047 Uiso 1 1 calc R . . 
H18B H 0.7549 0.5260 0.6102 0.047 Uiso 1 1 calc R . . 
H18C H 0.6346 0.4812 0.4962 0.047 Uiso 1 1 calc R . . 
C19 C 0.1028(8) 0.7648(9) -0.2271(7) 0.0286(17) Uani 1 1 d . . . 
H19 H 0.1081 0.7020 -0.3003 0.034 Uiso 1 1 calc R . . 
C20 C 0.0416(9) 0.8817(9) -0.2383(7) 0.0269(16) Uani 1 1 d . . . 
H20 H 0.0087 0.9014 -0.3189 0.032 Uiso 1 1 calc R . . 
C21 C 0.0304(8) 0.9684(8) -0.1273(7) 0.0236(15) Uani 1 1 d . . . 
H21 H -0.0114 1.0474 -0.1330 0.028 Uiso 1 1 calc R . . 
C22 C 0.0780(7) 0.9419(7) -0.0115(6) 0.0174(13) Uani 1 1 d U . . 
C23 C 0.0552(7) 1.0271(7) 0.1062(6) 0.0144(12) Uani 1 1 d . . . 
C24 C -0.0673(7) 1.0213(7) 0.1758(7) 0.0183(13) Uani 1 1 d . . . 
C25 C -0.2091(8) 0.9197(7) 0.1538(7) 0.0165(13) Uani 1 1 d . . . 
C26 C -0.3385(8) 0.7013(8) 0.0382(7) 0.0250(16) Uani 1 1 d . . . 
H26A H -0.4180 0.7450 0.0124 0.030 Uiso 1 1 calc R . . 
H26B H -0.3706 0.6465 0.1122 0.030 Uiso 1 1 calc R . . 
C27 C 0.1547(8) 0.7414(8) -0.1113(7) 0.0219(14) Uani 1 1 d . . . 
C28 C 0.1440(8) 0.8273(7) -0.0018(7) 0.0207(14) Uani 1 1 d . . . 
H28 H 0.1804 0.8096 0.0781 0.025 Uiso 1 1 calc R . . 
C29 C 0.3215(7) 1.1757(8) 0.1069(7) 0.0217(15) Uani 1 1 d . . . 
H29 H 0.3267 1.1069 0.0318 0.026 Uiso 1 1 calc R . . 
C30 C 0.3493(9) 1.3205(9) 0.0615(8) 0.0284(17) Uani 1 1 d . . . 
H30A H 0.2650 1.3280 0.0094 0.043 Uiso 1 1 calc R . . 
H30B H 0.4376 1.3370 0.0103 0.043 Uiso 1 1 calc R . . 
H30C H 0.3635 1.3914 0.1353 0.043 Uiso 1 1 calc R . . 
C31 C 0.4365(8) 1.1640(9) 0.2080(8) 0.0291(17) Uani 1 1 d . . . 
H31A H 0.4436 1.2399 0.2769 0.044 Uiso 1 1 calc R . . 
H31B H 0.5322 1.1727 0.1685 0.044 Uiso 1 1 calc R . . 
H31C H 0.4068 1.0719 0.2430 0.044 Uiso 1 1 calc R . . 
C32 C 0.1260(7) 1.2101(7) 0.2626(6) 0.0134(12) Uani 1 1 d . . . 
C33 C -0.0350(7) 1.1327(7) 0.2859(6) 0.0156(13) Uani 1 1 d . . . 
C34 C -0.1325(8) 1.2361(8) 0.2998(7) 0.0193(14) Uani 1 1 d . . . 
H34A H -0.2343 1.1823 0.3126 0.023 Uiso 1 1 calc R . . 
H34B H -0.1004 1.3012 0.3776 0.023 Uiso 1 1 calc R . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Br1 C2 1.894(8) . ? 
Br2 C27 1.893(7) . ? 
O1 C7 1.324(9) . ? 
O1 C8 1.469(9) . ? 
O2 C12 1.195(8) . ? 
O3 C7 1.247(8) . ? 
O4 C13 1.430(8) . ? 
O4 H4 0.8400 . ? 
O5 N4 1.240(8) . ? 
O6 N4 1.226(8) . ? 
O7 C25 1.349(9) . ? 
O7 C26 1.450(9) . ? 
C15 C26 1.504(11) . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 0.9800 . ? 
O9 C32 1.199(8) . ? 
O10 C25 1.221(9) . ? 
O11 N3 1.205(9) . ? 
O12 C33 1.425(8) . ? 
O12 H12 0.8400 . ? 
N1 C12 1.393(8) . ? 
N1 C5 1.399(8) . ? 
N1 C16 1.478(9) . ? 
N2 C32 1.391(8) . ? 
N2 C23 1.412(8) . ? 
N2 C29 1.474(9) . ? 
N3 O8 1.209(9) . ? 
N3 C34 1.497(10) . ? 
C1 C2 1.383(11) . ? 
C1 C10 1.396(11) . ? 
C1 H1 0.9500 . ? 
C2 C3 1.413(10) . ? 
C3 C4 1.387(9) . ? 
C3 H3 0.9500 . ? 
C4 C11 1.397(10) . ? 
C4 C5 1.489(9) . ? 
C5 C6 1.365(9) . ? 
C6 C7 1.440(9) . ? 
C6 C13 1.490(9) . ? 
C8 C9 1.454(10) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
C10 C11 1.395(10) . ? 
C10 H10 0.9500 . ? 
C11 H11 0.9500 . ? 
C12 C13 1.538(9) . ? 
C13 C14 1.520(9) . ? 
C14 N4 1.489(10) . ? 
C14 H14A 0.9900 . ? 
C14 H14B 0.9900 . ? 
C16 C17 1.507(12) . ? 
C16 C18 1.529(11) . ? 
C16 H16 1.0000 . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C18 H18C 0.9800 . ? 
C19 C27 1.366(11) . ? 
C19 C20 1.407(12) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.400(10) . ? 
C20 H20 0.9500 . ? 
C21 C22 1.362(10) . ? 
C21 H21 0.9500 . ? 
C22 C28 1.411(10) . ? 
C22 C23 1.475(9) . ? 
C23 C24 1.359(10) . ? 
C24 C25 1.462(9) . ? 
C24 C33 1.494(9) . ? 
C26 H26A 0.9900 . ? 
C26 H26B 0.9900 . ? 
C27 C28 1.383(10) . ? 
C28 H28 0.9500 . ? 
C29 C30 1.495(11) . ? 
C29 C31 1.540(11) . ? 
C29 H29 1.0000 . ? 
C30 H30A 0.9800 . ? 
C30 H30B 0.9800 . ? 
C30 H30C 0.9800 . ? 
C31 H31A 0.9800 . ? 
C31 H31B 0.9800 . ? 
C31 H31C 0.9800 . ? 
C32 C33 1.551(9) . ? 
C33 C34 1.513(9) . ? 
C34 H34A 0.9900 . ? 
C34 H34B 0.9900 . ? 
 
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 O1 C8 118.9(6) . . ? 
C13 O4 H4 109.5 . . ? 
C25 O7 C26 118.6(6) . . ? 
C26 C15 H15A 109.5 . . ? 
C26 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C26 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C33 O12 H12 109.5 . . ? 
C12 N1 C5 109.2(5) . . ? 
C12 N1 C16 123.7(6) . . ? 
C5 N1 C16 127.1(6) . . ? 
C32 N2 C23 109.7(5) . . ? 
C32 N2 C29 123.9(5) . . ? 
C23 N2 C29 126.1(5) . . ? 
O11 N3 O8 125.0(8) . . ? 
O11 N3 C34 118.5(6) . . ? 
O8 N3 C34 116.4(7) . . ? 
C2 C1 C10 118.3(7) . . ? 
C2 C1 H1 120.8 . . ? 
C10 C1 H1 120.8 . . ? 
C1 C2 C3 121.6(7) . . ? 
C1 C2 Br1 119.8(6) . . ? 
C3 C2 Br1 118.6(6) . . ? 
C4 C3 C2 118.9(7) . . ? 
C4 C3 H3 120.6 . . ? 
C2 C3 H3 120.6 . . ? 
C3 C4 C11 120.4(6) . . ? 
C3 C4 C5 119.4(6) . . ? 
C11 C4 C5 120.2(6) . . ? 
C6 C5 N1 112.4(6) . . ? 
C6 C5 C4 127.5(6) . . ? 
N1 C5 C4 120.0(6) . . ? 
C5 C6 C7 127.7(6) . . ? 
C5 C6 C13 107.8(6) . . ? 
C7 C6 C13 124.4(6) . . ? 
O3 C7 O1 122.9(6) . . ? 
O3 C7 C6 122.9(6) . . ? 
O1 C7 C6 114.1(6) . . ? 
C9 C8 O1 109.1(6) . . ? 
C9 C8 H8A 109.9 . . ? 
O1 C8 H8A 109.9 . . ? 
C9 C8 H8B 109.9 . . ? 
O1 C8 H8B 109.9 . . ? 
H8A C8 H8B 108.3 . . ? 
C8 C9 H9A 109.5 . . ? 
C8 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C8 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C11 C10 C1 121.3(7) . . ? 
C11 C10 H10 119.4 . . ? 
C1 C10 H10 119.4 . . ? 
C10 C11 C4 119.5(7) . . ? 
C10 C11 H11 120.3 . . ? 
C4 C11 H11 120.3 . . ? 
O2 C12 N1 125.6(6) . . ? 
O2 C12 C13 127.3(6) . . ? 
N1 C12 C13 107.1(5) . . ? 
O4 C13 C6 114.0(5) . . ? 
O4 C13 C14 102.9(5) . . ? 
C6 C13 C14 116.7(6) . . ? 
O4 C13 C12 109.4(5) . . ? 
C6 C13 C12 103.4(5) . . ? 
C14 C13 C12 110.5(6) . . ? 
N4 C14 C13 113.1(6) . . ? 
N4 C14 H14A 109.0 . . ? 
C13 C14 H14A 109.0 . . ? 
N4 C14 H14B 109.0 . . ? 
C13 C14 H14B 109.0 . . ? 
H14A C14 H14B 107.8 . . ? 
O6 N4 O5 124.0(6) . . ? 
O6 N4 C14 118.7(6) . . ? 
O5 N4 C14 117.2(6) . . ? 
N1 C16 C17 110.2(6) . . ? 
N1 C16 C18 110.0(6) . . ? 
C17 C16 C18 113.2(6) . . ? 
N1 C16 H16 107.7 . . ? 
C17 C16 H16 107.7 . . ? 
C18 C16 H16 107.7 . . ? 
C16 C17 H17A 109.5 . . ? 
C16 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
C16 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
C16 C18 H18A 109.5 . . ? 
C16 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
C16 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C27 C19 C20 120.1(7) . . ? 
C27 C19 H19 119.9 . . ? 
C20 C19 H19 119.9 . . ? 
C21 C20 C19 118.1(7) . . ? 
C21 C20 H20 120.9 . . ? 
C19 C20 H20 120.9 . . ? 
C22 C21 C20 121.5(7) . . ? 
C22 C21 H21 119.3 . . ? 
C20 C21 H21 119.3 . . ? 
C21 C22 C28 120.0(6) . . ? 
C21 C22 C23 121.0(6) . . ? 
C28 C22 C23 118.9(6) . . ? 
C24 C23 N2 111.0(5) . . ? 
C24 C23 C22 130.2(6) . . ? 
N2 C23 C22 118.8(6) . . ? 
C23 C24 C25 126.8(6) . . ? 
C23 C24 C33 109.7(6) . . ? 
C25 C24 C33 123.4(6) . . ? 
O10 C25 O7 123.3(6) . . ? 
O10 C25 C24 123.3(6) . . ? 
O7 C25 C24 113.3(6) . . ? 
O7 C26 C15 104.9(6) . . ? 
O7 C26 H26A 110.8 . . ? 
C15 C26 H26A 110.8 . . ? 
O7 C26 H26B 110.8 . . ? 
C15 C26 H26B 110.8 . . ? 
H26A C26 H26B 108.8 . . ? 
C19 C27 C28 121.6(7) . . ? 
C19 C27 Br2 120.0(6) . . ? 
C28 C27 Br2 118.4(6) . . ? 
C27 C28 C22 118.6(6) . . ? 
C27 C28 H28 120.7 . . ? 
C22 C28 H28 120.7 . . ? 
N2 C29 C30 110.6(6) . . ? 
N2 C29 C31 109.5(6) . . ? 
C30 C29 C31 112.4(6) . . ? 
N2 C29 H29 108.1 . . ? 
C30 C29 H29 108.1 . . ? 
C31 C29 H29 108.1 . . ? 
C29 C30 H30A 109.5 . . ? 
C29 C30 H30B 109.5 . . ? 
H30A C30 H30B 109.5 . . ? 
C29 C30 H30C 109.5 . . ? 
H30A C30 H30C 109.5 . . ? 
H30B C30 H30C 109.5 . . ? 
C29 C31 H31A 109.5 . . ? 
C29 C31 H31B 109.5 . . ? 
H31A C31 H31B 109.5 . . ? 
C29 C31 H31C 109.5 . . ? 
H31A C31 H31C 109.5 . . ? 
H31B C31 H31C 109.5 . . ? 
O9 C32 N2 125.9(6) . . ? 
O9 C32 C33 126.7(6) . . ? 
N2 C32 C33 107.2(5) . . ? 
O12 C33 C24 113.5(6) . . ? 
O12 C33 C34 103.4(5) . . ? 
C24 C33 C34 117.5(6) . . ? 
O12 C33 C32 109.3(5) . . ? 
C24 C33 C32 102.1(5) . . ? 
C34 C33 C32 111.1(6) . . ? 
N3 C34 C33 115.0(6) . . ? 
N3 C34 H34A 108.5 . . ? 
C33 C34 H34A 108.5 . . ? 
N3 C34 H34B 108.5 . . ? 
C33 C34 H34B 108.5 . . ? 
H34A C34 H34B 107.5 . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C10 C1 C2 C3 0.8(11) . . . . ? 
C10 C1 C2 Br1 -179.7(6) . . . . ? 
C1 C2 C3 C4 0.8(11) . . . . ? 
Br1 C2 C3 C4 -178.7(5) . . . . ? 
C2 C3 C4 C11 -3.1(10) . . . . ? 
C2 C3 C4 C5 175.5(6) . . . . ? 
C12 N1 C5 C6 1.2(8) . . . . ? 
C16 N1 C5 C6 -179.3(7) . . . . ? 
C12 N1 C5 C4 178.0(6) . . . . ? 
C16 N1 C5 C4 -2.5(10) . . . . ? 
C3 C4 C5 C6 -100.1(9) . . . . ? 
C11 C4 C5 C6 78.4(10) . . . . ? 
C3 C4 C5 N1 83.6(9) . . . . ? 
C11 C4 C5 N1 -97.8(8) . . . . ? 
N1 C5 C6 C7 -179.7(7) . . . . ? 
C4 C5 C6 C7 3.8(12) . . . . ? 
N1 C5 C6 C13 -2.5(8) . . . . ? 
C4 C5 C6 C13 -179.0(7) . . . . ? 
C8 O1 C7 O3 1.0(11) . . . . ? 
C8 O1 C7 C6 178.0(7) . . . . ? 
C5 C6 C7 O3 -173.4(7) . . . . ? 
C13 C6 C7 O3 9.9(11) . . . . ? 
C5 C6 C7 O1 9.6(11) . . . . ? 
C13 C6 C7 O1 -167.1(7) . . . . ? 
C7 O1 C8 C9 168.3(7) . . . . ? 
C2 C1 C10 C11 -0.1(13) . . . . ? 
C1 C10 C11 C4 -2.1(13) . . . . ? 
C3 C4 C11 C10 3.7(11) . . . . ? 
C5 C4 C11 C10 -174.8(8) . . . . ? 
C5 N1 C12 O2 179.3(7) . . . . ? 
C16 N1 C12 O2 -0.3(11) . . . . ? 
C5 N1 C12 C13 0.6(7) . . . . ? 
C16 N1 C12 C13 -178.9(6) . . . . ? 
C5 C6 C13 O4 -116.0(6) . . . . ? 
C7 C6 C13 O4 61.3(9) . . . . ? 
C5 C6 C13 C14 124.1(7) . . . . ? 
C7 C6 C13 C14 -58.5(9) . . . . ? 
C5 C6 C13 C12 2.7(7) . . . . ? 
C7 C6 C13 C12 180.0(7) . . . . ? 
O2 C12 C13 O4 -58.8(9) . . . . ? 
N1 C12 C13 O4 119.8(6) . . . . ? 
O2 C12 C13 C6 179.4(7) . . . . ? 
N1 C12 C13 C6 -2.0(7) . . . . ? 
O2 C12 C13 C14 53.8(9) . . . . ? 
N1 C12 C13 C14 -127.5(6) . . . . ? 
O4 C13 C14 N4 -179.1(6) . . . . ? 
C6 C13 C14 N4 -53.5(9) . . . . ? 
C12 C13 C14 N4 64.2(8) . . . . ? 
C13 C14 N4 O6 154.9(6) . . . . ? 
C13 C14 N4 O5 -26.6(9) . . . . ? 
C12 N1 C16 C17 64.9(9) . . . . ? 
C5 N1 C16 C17 -114.6(8) . . . . ? 
C12 N1 C16 C18 -60.7(9) . . . . ? 
C5 N1 C16 C18 119.9(7) . . . . ? 
C27 C19 C20 C21 -2.5(12) . . . . ? 
C19 C20 C21 C22 0.4(12) . . . . ? 
C20 C21 C22 C28 1.8(11) . . . . ? 
C20 C21 C22 C23 -175.1(7) . . . . ? 
C32 N2 C23 C24 -3.7(8) . . . . ? 
C29 N2 C23 C24 -177.9(7) . . . . ? 
C32 N2 C23 C22 175.1(6) . . . . ? 
C29 N2 C23 C22 0.9(10) . . . . ? 
C21 C22 C23 C24 77.8(10) . . . . ? 
C28 C22 C23 C24 -99.1(9) . . . . ? 
C21 C22 C23 N2 -100.7(8) . . . . ? 
C28 C22 C23 N2 82.3(8) . . . . ? 
N2 C23 C24 C25 -177.4(7) . . . . ? 
C22 C23 C24 C25 4.0(12) . . . . ? 
N2 C23 C24 C33 -0.1(8) . . . . ? 
C22 C23 C24 C33 -178.7(7) . . . . ? 
C26 O7 C25 O10 2.7(11) . . . . ? 
C26 O7 C25 C24 -179.1(6) . . . . ? 
C23 C24 C25 O10 -169.5(7) . . . . ? 
C33 C24 C25 O10 13.5(11) . . . . ? 
C23 C24 C25 O7 12.4(11) . . . . ? 
C33 C24 C25 O7 -164.6(6) . . . . ? 
C25 O7 C26 C15 171.4(7) . . . . ? 
C20 C19 C27 C28 2.4(11) . . . . ? 
C20 C19 C27 Br2 -177.8(6) . . . . ? 
C19 C27 C28 C22 -0.2(11) . . . . ? 
Br2 C27 C28 C22 -179.9(5) . . . . ? 
C21 C22 C28 C27 -1.9(10) . . . . ? 
C23 C22 C28 C27 175.1(6) . . . . ? 
C32 N2 C29 C30 -60.4(8) . . . . ? 
C23 N2 C29 C30 113.0(7) . . . . ? 
C32 N2 C29 C31 63.9(9) . . . . ? 
C23 N2 C29 C31 -122.6(7) . . . . ? 
C23 N2 C32 O9 -178.2(7) . . . . ? 
C29 N2 C32 O9 -3.9(11) . . . . ? 
C23 N2 C32 C33 5.7(7) . . . . ? 
C29 N2 C32 C33 -179.9(6) . . . . ? 
C23 C24 C33 O12 -114.2(6) . . . . ? 
C25 C24 C33 O12 63.2(8) . . . . ? 
C23 C24 C33 C34 125.1(7) . . . . ? 
C25 C24 C33 C34 -57.5(10) . . . . ? 
C23 C24 C33 C32 3.3(7) . . . . ? 
C25 C24 C33 C32 -179.3(6) . . . . ? 
O9 C32 C33 O12 -60.9(9) . . . . ? 
N2 C32 C33 O12 115.1(6) . . . . ? 
O9 C32 C33 C24 178.6(7) . . . . ? 
N2 C32 C33 C24 -5.4(7) . . . . ? 
O9 C32 C33 C34 52.5(9) . . . . ? 
N2 C32 C33 C34 -131.5(6) . . . . ? 
O11 N3 C34 C33 -13.6(10) . . . . ? 
O8 N3 C34 C33 168.5(7) . . . . ? 
O12 C33 C34 N3 174.1(6) . . . . ? 
C24 C33 C34 N3 -60.0(9) . . . . ? 
C32 C33 C34 N3 57.1(7) . . . . ? 
 
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 
O4 H4 O10  0.84 1.98 2.818(7) 174.4 1_655 
O12 H12 O3  0.84 1.95 2.777(7) 170.0 . 
 
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              28.35 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    2.249 
_refine_diff_density_min   -1.301 
_refine_diff_density_rms    0.163 
