  
data_bo2359 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C25 H27 Br N2 O7' 
_chemical_formula_weight          547.40 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 '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                    8.604(2) 
_cell_length_b                    29.351(8) 
_cell_length_c                    9.698(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.108(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      2449.1(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     153(2) 
_cell_measurement_reflns_used     8996 
_cell_measurement_theta_min       2.467 
_cell_measurement_theta_max       29.127 
  
_exptl_crystal_description        Chip 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.36 
_exptl_crystal_size_mid           0.31 
_exptl_crystal_size_min           0.25 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.485 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1128 
_exptl_absorpt_coefficient_mu     1.727 
_exptl_absorpt_correction_type    Multi-scans 
_exptl_absorpt_correction_T_min   0.5753 
_exptl_absorpt_correction_T_max   0.6721 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       153(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Rotating Anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   AFC10/Saturn724+ 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  28.5714 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             25254 
_diffrn_reflns_av_R_equivalents   0.0367 
_diffrn_reflns_av_sigmaI/netI     0.0882 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -39 
_diffrn_reflns_limit_k_max        39 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.78 
_diffrn_reflns_theta_max          28.40 
_reflns_number_total              12014 
_reflns_number_gt                 8703 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'CrystalClear (Rigaku Inc., 2008)' 
_computing_cell_refinement        'CrystalClear (Rigaku Inc., 2008)' 
_computing_data_reduction         'CrystalClear (Rigaku Inc., 2008)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0390P] 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      SHELXL 
_refine_ls_extinction_coef        0.0006(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_chemical_absolute_configuration  ad
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.043(7) 
_refine_ls_number_reflns          12014 
_refine_ls_number_parameters      638 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0657 
_refine_ls_R_factor_gt            0.0499 
_refine_ls_wR_factor_ref          0.1047 
_refine_ls_wR_factor_gt           0.0988 
_refine_ls_goodness_of_fit_ref    1.004 
_refine_ls_restrained_S_all       1.004 
_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 0.67013(7) 0.847058(15) 0.55151(5) 0.04978(15) Uani 1 1 d . . . 
O1 O 0.5315(3) 0.66190(9) 0.3152(2) 0.0223(6) Uani 1 1 d . . . 
O2 O 0.3366(3) 0.55924(10) 0.0950(2) 0.0251(6) Uani 1 1 d . . . 
O3 O 0.2690(3) 0.63170(9) 0.1370(2) 0.0259(6) Uani 1 1 d . . . 
O4 O 0.4541(4) 0.56110(10) 0.6523(3) 0.0351(7) Uani 1 1 d . . . 
O5 O 0.2492(3) 0.60301(10) 0.6289(3) 0.0317(7) Uani 1 1 d . . . 
N1 N 0.5493(4) 0.66757(12) 0.9811(3) 0.0255(8) Uani 1 1 d . . . 
H1 H 0.5216 0.6647 1.0680 0.031 Uiso 1 1 calc R . . 
N2 N 0.3871(4) 0.59538(11) 0.6131(3) 0.0214(7) Uani 1 1 d . . . 
C1 C 0.6995(5) 0.66909(12) 0.9337(4) 0.0214(8) Uani 1 1 d . . . 
C2 C 0.8385(5) 0.66596(14) 1.0076(4) 0.0300(9) Uani 1 1 d . . . 
H2 H 0.8397 0.6623 1.1050 0.036 Uiso 1 1 calc R . . 
C3 C 0.9757(5) 0.66843(16) 0.9313(4) 0.0369(11) Uani 1 1 d . . . 
H3 H 1.0724 0.6652 0.9776 0.044 Uiso 1 1 calc R . . 
C4 C 0.9750(5) 0.67549(17) 0.7885(4) 0.0347(10) Uani 1 1 d . . . 
H4 H 1.0705 0.6782 0.7401 0.042 Uiso 1 1 calc R . . 
C5 C 0.8357(4) 0.67849(15) 0.7175(4) 0.0270(9) Uani 1 1 d . . . 
H5 H 0.8351 0.6830 0.6205 0.032 Uiso 1 1 calc R . . 
C6 C 0.6945(4) 0.67475(14) 0.7904(4) 0.0217(8) Uani 1 1 d . . . 
C7 C 0.5330(4) 0.67520(13) 0.7517(4) 0.0202(8) Uani 1 1 d . . . 
C8 C 0.4498(5) 0.67128(14) 0.8718(4) 0.0242(8) Uani 1 1 d . . . 
H8 H 0.3396 0.6712 0.8779 0.029 Uiso 1 1 calc R . . 
C9 C 0.5656(4) 0.70276(14) 0.3770(4) 0.0220(8) Uani 1 1 d . . . 
C10 C 0.6378(5) 0.73507(15) 0.2937(4) 0.0313(10) Uani 1 1 d . . . 
H10 H 0.6624 0.7280 0.2007 0.038 Uiso 1 1 calc R . . 
C11 C 0.6736(5) 0.77781(16) 0.3471(4) 0.0334(10) Uani 1 1 d . . . 
H11 H 0.7239 0.8000 0.2917 0.040 Uiso 1 1 calc R . . 
C12 C 0.6351(5) 0.78727(17) 0.4812(4) 0.0331(9) Uani 1 1 d . . . 
C13 C 0.5689(5) 0.75501(14) 0.5641(4) 0.0249(9) Uani 1 1 d . . . 
H13 H 0.5461 0.7625 0.6572 0.030 Uiso 1 1 calc R . . 
C14 C 0.5344(4) 0.71202(14) 0.5165(4) 0.0218(8) Uani 1 1 d . . . 
C15 C 0.4654(4) 0.67631(13) 0.6082(3) 0.0202(8) Uani 1 1 d . . . 
H15 H 0.3520 0.6831 0.6172 0.024 Uiso 1 1 calc R . . 
C16 C 0.4802(4) 0.63000(13) 0.5369(3) 0.0215(8) Uani 1 1 d . . . 
H16 H 0.5918 0.6205 0.5359 0.026 Uiso 1 1 calc R . . 
C17 C 0.4210(4) 0.63447(13) 0.3884(3) 0.0201(8) Uani 1 1 d . . . 
H17 H 0.3182 0.6504 0.3889 0.024 Uiso 1 1 calc R . . 
C18 C 0.4048(5) 0.58958(14) 0.3121(3) 0.0240(8) Uani 1 1 d . . . 
H18A H 0.5087 0.5757 0.3001 0.029 Uiso 1 1 calc R . . 
H18B H 0.3406 0.5684 0.3672 0.029 Uiso 1 1 calc R . . 
C19 C 0.3301(4) 0.59655(13) 0.1723(3) 0.0193(8) Uani 1 1 d . . . 
C20 C 0.2618(5) 0.56283(14) -0.0403(4) 0.0267(9) Uani 1 1 d . . . 
H20A H 0.3249 0.5823 -0.1021 0.032 Uiso 1 1 calc R . . 
H20B H 0.1575 0.5767 -0.0309 0.032 Uiso 1 1 calc R . . 
C21 C 0.2481(5) 0.51573(14) -0.0991(4) 0.0318(10) Uani 1 1 d . . . 
H21A H 0.3514 0.5018 -0.1043 0.038 Uiso 1 1 calc R . . 
H21B H 0.2026 0.5174 -0.1917 0.038 Uiso 1 1 calc R . . 
H21C H 0.1812 0.4972 -0.0396 0.038 Uiso 1 1 calc R . . 
Br1' Br 0.57932(8) 0.285314(17) 1.04798(5) 0.05616(17) Uani 1 1 d . . . 
O1' O 0.6788(3) 0.47261(10) 0.8096(2) 0.0265(6) Uani 1 1 d . . . 
O2' O 0.8608(3) 0.57682(9) 0.5872(2) 0.0254(6) Uani 1 1 d . . . 
O3' O 0.9373(3) 0.50538(10) 0.6348(2) 0.0275(6) Uani 1 1 d . . . 
O4' O 0.9442(3) 0.53641(11) 1.1244(3) 0.0337(7) Uani 1 1 d . . . 
O5' O 0.7318(3) 0.57502(10) 1.1515(3) 0.0368(7) Uani 1 1 d . . . 
N1' N 0.6459(4) 0.46996(12) 1.4766(3) 0.0288(8) Uani 1 1 d . . . 
H1' H 0.6739 0.4736 1.5632 0.035 Uiso 1 1 calc R . . 
N2' N 0.8028(4) 0.54211(12) 1.1086(3) 0.0251(7) Uani 1 1 d . . . 
C1' C 0.4971(5) 0.46619(14) 1.4320(4) 0.0253(9) Uani 1 1 d . . . 
C2' C 0.3552(5) 0.46803(14) 1.5041(4) 0.0315(10) Uani 1 1 d . . . 
H2' H 0.3533 0.4729 1.6010 0.038 Uiso 1 1 calc R . . 
C3' C 0.2221(5) 0.46273(16) 1.4322(4) 0.0366(11) Uani 1 1 d . . . 
H3' H 0.1256 0.4634 1.4795 0.044 Uiso 1 1 calc R . . 
C4' C 0.2234(5) 0.45608(16) 1.2859(4) 0.0329(10) Uani 1 1 d . . . 
H4' H 0.1277 0.4527 1.2379 0.040 Uiso 1 1 calc R . . 
C5' C 0.3612(4) 0.45445(14) 1.2134(4) 0.0259(9) Uani 1 1 d . . . 
H5' H 0.3609 0.4495 1.1166 0.031 Uiso 1 1 calc R . . 
C6' C 0.5015(5) 0.46021(14) 1.2849(4) 0.0225(8) Uani 1 1 d . . . 
C7' C 0.6627(4) 0.46146(14) 1.2482(3) 0.0216(8) Uani 1 1 d . . . 
C8' C 0.7488(5) 0.46714(14) 1.3650(4) 0.0268(9) Uani 1 1 d . . . 
H8' H 0.8590 0.4689 1.3700 0.032 Uiso 1 1 calc R . . 
C9' C 0.6537(4) 0.43025(14) 0.8687(4) 0.0232(8) Uani 1 1 d . . . 
C10' C 0.6060(6) 0.39568(17) 0.7845(4) 0.0379(11) Uani 1 1 d . . . 
H10' H 0.5882 0.4014 0.6893 0.045 Uiso 1 1 calc R . . 
C11' C 0.5836(6) 0.35282(18) 0.8363(4) 0.0444(12) Uani 1 1 d . . . 
H11' H 0.5542 0.3285 0.7770 0.053 Uiso 1 1 calc R . . 
C12' C 0.6042(5) 0.34523(18) 0.9749(4) 0.0388(11) Uani 1 1 d . . . 
C13' C 0.6467(5) 0.37977(15) 1.0632(4) 0.0286(9) Uani 1 1 d . . . 
H13' H 0.6562 0.3741 1.1593 0.034 Uiso 1 1 calc R . . 
C14' C 0.6758(4) 0.42323(14) 1.0110(4) 0.0228(8) Uani 1 1 d . . . 
C15' C 0.7324(4) 0.46105(13) 1.1043(3) 0.0211(8) Uani 1 1 d . . . 
H15' H 0.8466 0.4561 1.1167 0.025 Uiso 1 1 calc R . . 
C16' C 0.7151(4) 0.50645(13) 1.0305(3) 0.0210(8) Uani 1 1 d . . . 
H16' H 0.6027 0.5150 1.0251 0.025 Uiso 1 1 calc R . . 
C17' C 0.7824(4) 0.50228(13) 0.8849(3) 0.0201(7) Uani 1 1 d . . . 
H17' H 0.8879 0.4880 0.8901 0.024 Uiso 1 1 calc R . . 
C18' C 0.7923(4) 0.54664(13) 0.8045(3) 0.0220(8) Uani 1 1 d . . . 
H18C H 0.6863 0.5587 0.7891 0.026 Uiso 1 1 calc R . . 
H18D H 0.8509 0.5694 0.8593 0.026 Uiso 1 1 calc R . . 
C19' C 0.8719(4) 0.53991(13) 0.6666(3) 0.0205(8) Uani 1 1 d . . . 
C20' C 0.9400(5) 0.57391(14) 0.4554(4) 0.0272(9) Uani 1 1 d . . . 
H20C H 0.8813 0.5538 0.3920 0.033 Uiso 1 1 calc R . . 
H20D H 1.0453 0.5610 0.4682 0.033 Uiso 1 1 calc R . . 
C21' C 0.9509(5) 0.62124(15) 0.3953(4) 0.0285(9) Uani 1 1 d . . . 
H21D H 0.8462 0.6337 0.3829 0.034 Uiso 1 1 calc R . . 
H21E H 1.0037 0.6199 0.3060 0.034 Uiso 1 1 calc R . . 
H21F H 1.0100 0.6409 0.4582 0.034 Uiso 1 1 calc R . . 
O11 O 0.8768(5) 0.84748(15) 1.0705(3) 0.0730(13) Uani 1 1 d . . . 
O12 O 0.9448(4) 0.91764(12) 1.0171(3) 0.0489(9) Uani 1 1 d . . . 
C43 C 0.9383(8) 0.8970(2) 1.2539(5) 0.074(2) Uani 1 1 d . . . 
H43A H 0.9976 0.9250 1.2694 0.089 Uiso 1 1 calc R . . 
H43B H 0.9930 0.8713 1.2964 0.089 Uiso 1 1 calc R . . 
H43C H 0.8350 0.9000 1.2952 0.089 Uiso 1 1 calc R . . 
C44 C 0.9220(6) 0.88872(18) 1.1011(5) 0.0442(12) Uani 1 1 d . . . 
C45 C 0.8532(10) 0.8360(2) 0.9293(5) 0.095(3) Uani 1 1 d . . . 
H45A H 0.9284 0.8527 0.8708 0.113 Uiso 1 1 calc R . . 
H45B H 0.7468 0.8447 0.9003 0.113 Uiso 1 1 calc R . . 
C46 C 0.8745(8) 0.7881(2) 0.9135(6) 0.080(2) Uani 1 1 d . . . 
H46A H 0.9825 0.7802 0.9348 0.096 Uiso 1 1 calc R . . 
H46B H 0.8505 0.7793 0.8184 0.096 Uiso 1 1 calc R . . 
H46C H 0.8049 0.7719 0.9767 0.096 Uiso 1 1 calc R . . 
O13 O 0.1352(5) 0.79360(15) 0.4288(4) 0.0670(12) Uani 1 1 d . . . 
O14 O 0.1427(5) 0.72007(15) 0.4783(4) 0.0670(12) Uani 1 1 d . . . 
C47 C 0.1336(9) 0.7429(2) 0.2441(6) 0.079(2) Uani 1 1 d . . . 
H47A H 0.2267 0.7566 0.2036 0.095 Uiso 1 1 calc R . . 
H47B H 0.0407 0.7573 0.2050 0.095 Uiso 1 1 calc R . . 
H47C H 0.1319 0.7102 0.2236 0.095 Uiso 1 1 calc R . . 
C48 C 0.1356(6) 0.7496(2) 0.3930(6) 0.0524(14) Uani 1 1 d . . . 
C49 C 0.1314(9) 0.8034(3) 0.5762(6) 0.079(2) Uani 1 1 d . . . 
H49A H 0.2174 0.7875 0.6242 0.094 Uiso 1 1 calc R . . 
H49B H 0.0316 0.7932 0.6166 0.094 Uiso 1 1 calc R . . 
C50 C 0.1484(11) 0.8527(3) 0.5892(7) 0.115(3) Uani 1 1 d . . . 
H50A H 0.2421 0.8626 0.5403 0.138 Uiso 1 1 calc R . . 
H50B H 0.1570 0.8609 0.6868 0.138 Uiso 1 1 calc R . . 
H50C H 0.0573 0.8678 0.5490 0.138 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 C12 1.906(5) . ? 
O1 C9 1.372(5) . ? 
O1 C17 1.435(4) . ? 
O2 C19 1.328(4) . ? 
O2 C20 1.464(4) . ? 
O3 C19 1.207(4) . ? 
O4 N2 1.220(4) . ? 
O5 N2 1.217(4) . ? 
N1 C8 1.366(5) . ? 
N1 C1 1.373(5) . ? 
N1 H1 0.8800 . ? 
N2 C16 1.491(5) . ? 
C1 C2 1.396(5) . ? 
C1 C6 1.400(5) . ? 
C2 C3 1.396(6) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.401(6) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.384(5) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.411(5) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.439(5) . ? 
C7 C8 1.373(5) . ? 
C7 C15 1.507(5) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.393(5) . ? 
C9 C14 1.406(5) . ? 
C10 C11 1.392(6) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.371(5) . ? 
C11 H11 0.9500 . ? 
C12 C13 1.367(6) . ? 
C13 C14 1.376(6) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.498(5) . ? 
C15 C16 1.531(5) . ? 
C15 H15 1.0000 . ? 
C16 C17 1.533(5) . ? 
C16 H16 1.0000 . ? 
C17 C18 1.518(5) . ? 
C17 H17 1.0000 . ? 
C18 C19 1.513(5) . ? 
C18 H18A 0.9900 . ? 
C18 H18B 0.9900 . ? 
C20 C21 1.500(5) . ? 
C20 H20A 0.9900 . ? 
C20 H20B 0.9900 . ? 
C21 H21A 0.9800 . ? 
C21 H21B 0.9800 . ? 
C21 H21C 0.9800 . ? 
Br1' C12' 1.908(5) . ? 
O1' C9' 1.386(5) . ? 
O1' C17' 1.444(4) . ? 
O2' C19' 1.333(4) . ? 
O2' C20' 1.452(4) . ? 
O3' C19' 1.199(4) . ? 
O4' N2' 1.237(4) . ? 
O5' N2' 1.216(4) . ? 
N1' C1' 1.355(5) . ? 
N1' C8' 1.402(5) . ? 
N1' H1' 0.8800 . ? 
N2' C16' 1.496(5) . ? 
C1' C2' 1.410(6) . ? 
C1' C6' 1.438(5) . ? 
C2' C3' 1.348(6) . ? 
C2' H2' 0.9500 . ? 
C3' C4' 1.432(6) . ? 
C3' H3' 0.9500 . ? 
C4' C5' 1.380(5) . ? 
C4' H4' 0.9500 . ? 
C5' C6' 1.401(5) . ? 
C5' H5' 0.9500 . ? 
C6' C7' 1.433(5) . ? 
C7' C8' 1.363(5) . ? 
C7' C15' 1.520(5) . ? 
C8' H8' 0.9500 . ? 
C9' C10' 1.365(6) . ? 
C9' C14' 1.408(5) . ? 
C10' C11' 1.369(7) . ? 
C10' H10' 0.9500 . ? 
C11' C12' 1.374(6) . ? 
C11' H11' 0.9500 . ? 
C12' C13' 1.376(6) . ? 
C13' C14' 1.395(6) . ? 
C13' H13' 0.9500 . ? 
C14' C15' 1.512(5) . ? 
C15' C16' 1.520(5) . ? 
C15' H15' 1.0000 . ? 
C16' C17' 1.532(5) . ? 
C16' H16' 1.0000 . ? 
C17' C18' 1.520(5) . ? 
C17' H17' 1.0000 . ? 
C18' C19' 1.517(5) . ? 
C18' H18C 0.9900 . ? 
C18' H18D 0.9900 . ? 
C20' C21' 1.509(5) . ? 
C20' H20C 0.9900 . ? 
C20' H20D 0.9900 . ? 
C21' H21D 0.9800 . ? 
C21' H21E 0.9800 . ? 
C21' H21F 0.9800 . ? 
O11 C44 1.306(6) . ? 
O11 C45 1.425(6) . ? 
O12 C44 1.193(6) . ? 
C43 C44 1.507(7) . ? 
C43 H43A 0.9800 . ? 
C43 H43B 0.9800 . ? 
C43 H43C 0.9800 . ? 
C45 C46 1.426(9) . ? 
C45 H45A 0.9900 . ? 
C45 H45B 0.9900 . ? 
C46 H46A 0.9800 . ? 
C46 H46B 0.9800 . ? 
C46 H46C 0.9800 . ? 
O13 C48 1.338(7) . ? 
O13 C49 1.458(6) . ? 
O14 C48 1.200(7) . ? 
C47 C48 1.457(8) . ? 
C47 H47A 0.9800 . ? 
C47 H47B 0.9800 . ? 
C47 H47C 0.9800 . ? 
C49 C50 1.461(10) . ? 
C49 H49A 0.9900 . ? 
C49 H49B 0.9900 . ? 
C50 H50A 0.9800 . ? 
C50 H50B 0.9800 . ? 
C50 H50C 0.9800 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C9 O1 C17 114.5(3) . . ? 
C19 O2 C20 115.3(3) . . ? 
C8 N1 C1 109.0(3) . . ? 
C8 N1 H1 125.5 . . ? 
C1 N1 H1 125.5 . . ? 
O5 N2 O4 125.0(3) . . ? 
O5 N2 C16 117.5(3) . . ? 
O4 N2 C16 117.5(3) . . ? 
N1 C1 C2 129.2(3) . . ? 
N1 C1 C6 108.0(3) . . ? 
C2 C1 C6 122.9(4) . . ? 
C1 C2 C3 116.6(4) . . ? 
C1 C2 H2 121.7 . . ? 
C3 C2 H2 121.7 . . ? 
C2 C3 C4 122.0(4) . . ? 
C2 C3 H3 119.0 . . ? 
C4 C3 H3 119.0 . . ? 
C5 C4 C3 120.2(4) . . ? 
C5 C4 H4 119.9 . . ? 
C3 C4 H4 119.9 . . ? 
C4 C5 C6 119.4(4) . . ? 
C4 C5 H5 120.3 . . ? 
C6 C5 H5 120.3 . . ? 
C1 C6 C5 118.8(4) . . ? 
C1 C6 C7 106.8(3) . . ? 
C5 C6 C7 134.5(3) . . ? 
C8 C7 C6 106.4(3) . . ? 
C8 C7 C15 125.8(4) . . ? 
C6 C7 C15 127.7(3) . . ? 
N1 C8 C7 109.8(3) . . ? 
N1 C8 H8 125.1 . . ? 
C7 C8 H8 125.1 . . ? 
O1 C9 C10 115.9(3) . . ? 
O1 C9 C14 123.2(3) . . ? 
C10 C9 C14 120.8(4) . . ? 
C11 C10 C9 119.8(4) . . ? 
C11 C10 H10 120.1 . . ? 
C9 C10 H10 120.1 . . ? 
C12 C11 C10 118.8(4) . . ? 
C12 C11 H11 120.6 . . ? 
C10 C11 H11 120.6 . . ? 
C13 C12 C11 121.3(4) . . ? 
C13 C12 Br1 119.6(3) . . ? 
C11 C12 Br1 119.2(3) . . ? 
C12 C13 C14 121.9(4) . . ? 
C12 C13 H13 119.1 . . ? 
C14 C13 H13 119.1 . . ? 
C13 C14 C9 117.3(3) . . ? 
C13 C14 C15 121.8(3) . . ? 
C9 C14 C15 120.9(4) . . ? 
C14 C15 C7 114.3(3) . . ? 
C14 C15 C16 108.6(3) . . ? 
C7 C15 C16 111.5(3) . . ? 
C14 C15 H15 107.4 . . ? 
C7 C15 H15 107.4 . . ? 
C16 C15 H15 107.4 . . ? 
N2 C16 C15 109.6(3) . . ? 
N2 C16 C17 110.3(3) . . ? 
C15 C16 C17 108.7(3) . . ? 
N2 C16 H16 109.4 . . ? 
C15 C16 H16 109.4 . . ? 
C17 C16 H16 109.4 . . ? 
O1 C17 C18 107.8(3) . . ? 
O1 C17 C16 107.1(3) . . ? 
C18 C17 C16 114.5(3) . . ? 
O1 C17 H17 109.1 . . ? 
C18 C17 H17 109.1 . . ? 
C16 C17 H17 109.1 . . ? 
C19 C18 C17 111.0(3) . . ? 
C19 C18 H18A 109.4 . . ? 
C17 C18 H18A 109.4 . . ? 
C19 C18 H18B 109.4 . . ? 
C17 C18 H18B 109.4 . . ? 
H18A C18 H18B 108.0 . . ? 
O3 C19 O2 124.3(3) . . ? 
O3 C19 C18 123.6(3) . . ? 
O2 C19 C18 112.0(3) . . ? 
O2 C20 C21 108.0(3) . . ? 
O2 C20 H20A 110.1 . . ? 
C21 C20 H20A 110.1 . . ? 
O2 C20 H20B 110.1 . . ? 
C21 C20 H20B 110.1 . . ? 
H20A C20 H20B 108.4 . . ? 
C20 C21 H21A 109.5 . . ? 
C20 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
C20 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
C9' O1' C17' 115.4(3) . . ? 
C19' O2' C20' 115.3(3) . . ? 
C1' N1' C8' 110.3(3) . . ? 
C1' N1' H1' 124.8 . . ? 
C8' N1' H1' 124.8 . . ? 
O5' N2' O4' 124.0(4) . . ? 
O5' N2' C16' 118.4(3) . . ? 
O4' N2' C16' 117.6(3) . . ? 
N1' C1' C2' 131.1(4) . . ? 
N1' C1' C6' 107.4(3) . . ? 
C2' C1' C6' 121.5(4) . . ? 
C3' C2' C1' 118.3(4) . . ? 
C3' C2' H2' 120.9 . . ? 
C1' C2' H2' 120.9 . . ? 
C2' C3' C4' 121.3(4) . . ? 
C2' C3' H3' 119.3 . . ? 
C4' C3' H3' 119.3 . . ? 
C5' C4' C3' 121.2(4) . . ? 
C5' C4' H4' 119.4 . . ? 
C3' C4' H4' 119.4 . . ? 
C4' C5' C6' 118.9(4) . . ? 
C4' C5' H5' 120.5 . . ? 
C6' C5' H5' 120.5 . . ? 
C5' C6' C7' 135.5(3) . . ? 
C5' C6' C1' 118.7(3) . . ? 
C7' C6' C1' 105.7(3) . . ? 
C8' C7' C6' 108.7(3) . . ? 
C8' C7' C15' 123.3(3) . . ? 
C6' C7' C15' 127.7(3) . . ? 
C7' C8' N1' 107.8(3) . . ? 
C7' C8' H8' 126.1 . . ? 
N1' C8' H8' 126.1 . . ? 
C10' C9' O1' 117.8(3) . . ? 
C10' C9' C14' 121.2(4) . . ? 
O1' C9' C14' 121.0(3) . . ? 
C9' C10' C11' 120.4(4) . . ? 
C9' C10' H10' 119.8 . . ? 
C11' C10' H10' 119.8 . . ? 
C10' C11' C12' 119.4(4) . . ? 
C10' C11' H11' 120.3 . . ? 
C12' C11' H11' 120.3 . . ? 
C11' C12' C13' 121.5(5) . . ? 
C11' C12' Br1' 119.9(4) . . ? 
C13' C12' Br1' 118.6(3) . . ? 
C12' C13' C14' 119.7(4) . . ? 
C12' C13' H13' 120.1 . . ? 
C14' C13' H13' 120.1 . . ? 
C13' C14' C9' 117.7(4) . . ? 
C13' C14' C15' 120.8(3) . . ? 
C9' C14' C15' 121.5(3) . . ? 
C14' C15' C7' 115.3(3) . . ? 
C14' C15' C16' 109.3(3) . . ? 
C7' C15' C16' 112.7(3) . . ? 
C14' C15' H15' 106.3 . . ? 
C7' C15' H15' 106.3 . . ? 
C16' C15' H15' 106.3 . . ? 
N2' C16' C15' 109.0(3) . . ? 
N2' C16' C17' 109.3(3) . . ? 
C15' C16' C17' 109.1(3) . . ? 
N2' C16' H16' 109.8 . . ? 
C15' C16' H16' 109.8 . . ? 
C17' C16' H16' 109.8 . . ? 
O1' C17' C18' 107.0(3) . . ? 
O1' C17' C16' 106.3(3) . . ? 
C18' C17' C16' 115.2(3) . . ? 
O1' C17' H17' 109.4 . . ? 
C18' C17' H17' 109.4 . . ? 
C16' C17' H17' 109.4 . . ? 
C19' C18' C17' 111.5(3) . . ? 
C19' C18' H18C 109.3 . . ? 
C17' C18' H18C 109.3 . . ? 
C19' C18' H18D 109.3 . . ? 
C17' C18' H18D 109.3 . . ? 
H18C C18' H18D 108.0 . . ? 
O3' C19' O2' 124.9(3) . . ? 
O3' C19' C18' 123.3(3) . . ? 
O2' C19' C18' 111.8(3) . . ? 
O2' C20' C21' 108.4(3) . . ? 
O2' C20' H20C 110.0 . . ? 
C21' C20' H20C 110.0 . . ? 
O2' C20' H20D 110.0 . . ? 
C21' C20' H20D 110.0 . . ? 
H20C C20' H20D 108.4 . . ? 
C20' C21' H21D 109.5 . . ? 
C20' C21' H21E 109.5 . . ? 
H21D C21' H21E 109.5 . . ? 
C20' C21' H21F 109.5 . . ? 
H21D C21' H21F 109.5 . . ? 
H21E C21' H21F 109.5 . . ? 
C44 O11 C45 118.7(5) . . ? 
C44 C43 H43A 109.5 . . ? 
C44 C43 H43B 109.5 . . ? 
H43A C43 H43B 109.5 . . ? 
C44 C43 H43C 109.5 . . ? 
H43A C43 H43C 109.5 . . ? 
H43B C43 H43C 109.5 . . ? 
O12 C44 O11 123.6(5) . . ? 
O12 C44 C43 122.8(5) . . ? 
O11 C44 C43 113.6(5) . . ? 
O11 C45 C46 108.5(5) . . ? 
O11 C45 H45A 110.0 . . ? 
C46 C45 H45A 110.0 . . ? 
O11 C45 H45B 110.0 . . ? 
C46 C45 H45B 110.0 . . ? 
H45A C45 H45B 108.4 . . ? 
C45 C46 H46A 109.5 . . ? 
C45 C46 H46B 109.5 . . ? 
H46A C46 H46B 109.5 . . ? 
C45 C46 H46C 109.5 . . ? 
H46A C46 H46C 109.5 . . ? 
H46B C46 H46C 109.5 . . ? 
C48 O13 C49 116.4(5) . . ? 
C48 C47 H47A 109.5 . . ? 
C48 C47 H47B 109.5 . . ? 
H47A C47 H47B 109.5 . . ? 
C48 C47 H47C 109.5 . . ? 
H47A C47 H47C 109.5 . . ? 
H47B C47 H47C 109.5 . . ? 
O14 C48 O13 121.2(6) . . ? 
O14 C48 C47 125.9(6) . . ? 
O13 C48 C47 112.8(5) . . ? 
O13 C49 C50 106.1(6) . . ? 
O13 C49 H49A 110.5 . . ? 
C50 C49 H49A 110.5 . . ? 
O13 C49 H49B 110.5 . . ? 
C50 C49 H49B 110.5 . . ? 
H49A C49 H49B 108.7 . . ? 
C49 C50 H50A 109.5 . . ? 
C49 C50 H50B 109.5 . . ? 
H50A C50 H50B 109.5 . . ? 
C49 C50 H50C 109.5 . . ? 
H50A C50 H50C 109.5 . . ? 
H50B C50 H50C 109.5 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C8 N1 C1 C2 -179.1(4) . . . . ? 
C8 N1 C1 C6 1.1(4) . . . . ? 
N1 C1 C2 C3 179.8(4) . . . . ? 
C6 C1 C2 C3 -0.5(6) . . . . ? 
C1 C2 C3 C4 2.5(7) . . . . ? 
C2 C3 C4 C5 -2.5(7) . . . . ? 
C3 C4 C5 C6 0.5(7) . . . . ? 
N1 C1 C6 C5 178.4(4) . . . . ? 
C2 C1 C6 C5 -1.5(6) . . . . ? 
N1 C1 C6 C7 -1.8(4) . . . . ? 
C2 C1 C6 C7 178.4(4) . . . . ? 
C4 C5 C6 C1 1.4(6) . . . . ? 
C4 C5 C6 C7 -178.4(4) . . . . ? 
C1 C6 C7 C8 1.8(4) . . . . ? 
C5 C6 C7 C8 -178.4(4) . . . . ? 
C1 C6 C7 C15 -174.2(4) . . . . ? 
C5 C6 C7 C15 5.6(7) . . . . ? 
C1 N1 C8 C7 0.1(5) . . . . ? 
C6 C7 C8 N1 -1.2(4) . . . . ? 
C15 C7 C8 N1 174.9(4) . . . . ? 
C17 O1 C9 C10 -163.4(3) . . . . ? 
C17 O1 C9 C14 18.1(5) . . . . ? 
O1 C9 C10 C11 178.7(4) . . . . ? 
C14 C9 C10 C11 -2.8(6) . . . . ? 
C9 C10 C11 C12 -0.7(7) . . . . ? 
C10 C11 C12 C13 2.9(7) . . . . ? 
C10 C11 C12 Br1 -175.6(3) . . . . ? 
C11 C12 C13 C14 -1.5(7) . . . . ? 
Br1 C12 C13 C14 176.9(3) . . . . ? 
C12 C13 C14 C9 -1.9(6) . . . . ? 
C12 C13 C14 C15 178.5(4) . . . . ? 
O1 C9 C14 C13 -177.5(4) . . . . ? 
C10 C9 C14 C13 4.1(6) . . . . ? 
O1 C9 C14 C15 2.1(6) . . . . ? 
C10 C9 C14 C15 -176.3(4) . . . . ? 
C13 C14 C15 C7 -40.4(5) . . . . ? 
C9 C14 C15 C7 140.0(4) . . . . ? 
C13 C14 C15 C16 -165.6(4) . . . . ? 
C9 C14 C15 C16 14.8(5) . . . . ? 
C8 C7 C15 C14 135.8(4) . . . . ? 
C6 C7 C15 C14 -49.0(5) . . . . ? 
C8 C7 C15 C16 -100.6(4) . . . . ? 
C6 C7 C15 C16 74.6(5) . . . . ? 
O5 N2 C16 C15 56.8(4) . . . . ? 
O4 N2 C16 C15 -124.8(3) . . . . ? 
O5 N2 C16 C17 -62.8(4) . . . . ? 
O4 N2 C16 C17 115.6(4) . . . . ? 
C14 C15 C16 N2 -169.5(3) . . . . ? 
C7 C15 C16 N2 63.7(4) . . . . ? 
C14 C15 C16 C17 -48.9(4) . . . . ? 
C7 C15 C16 C17 -175.7(3) . . . . ? 
C9 O1 C17 C18 -176.2(3) . . . . ? 
C9 O1 C17 C16 -52.6(4) . . . . ? 
N2 C16 C17 O1 -170.0(3) . . . . ? 
C15 C16 C17 O1 69.7(4) . . . . ? 
N2 C16 C17 C18 -50.6(4) . . . . ? 
C15 C16 C17 C18 -170.8(3) . . . . ? 
O1 C17 C18 C19 -67.0(4) . . . . ? 
C16 C17 C18 C19 174.0(3) . . . . ? 
C20 O2 C19 O3 -0.5(5) . . . . ? 
C20 O2 C19 C18 178.0(3) . . . . ? 
C17 C18 C19 O3 -11.3(5) . . . . ? 
C17 C18 C19 O2 170.2(3) . . . . ? 
C19 O2 C20 C21 -167.3(3) . . . . ? 
C8' N1' C1' C2' -178.3(4) . . . . ? 
C8' N1' C1' C6' 0.5(5) . . . . ? 
N1' C1' C2' C3' -179.4(4) . . . . ? 
C6' C1' C2' C3' 1.9(6) . . . . ? 
C1' C2' C3' C4' -1.0(7) . . . . ? 
C2' C3' C4' C5' 0.6(7) . . . . ? 
C3' C4' C5' C6' -1.1(6) . . . . ? 
C4' C5' C6' C7' -178.8(4) . . . . ? 
C4' C5' C6' C1' 1.9(6) . . . . ? 
N1' C1' C6' C5' 178.7(4) . . . . ? 
C2' C1' C6' C5' -2.4(6) . . . . ? 
N1' C1' C6' C7' -0.8(4) . . . . ? 
C2' C1' C6' C7' 178.2(4) . . . . ? 
C5' C6' C7' C8' -178.5(5) . . . . ? 
C1' C6' C7' C8' 0.8(5) . . . . ? 
C5' C6' C7' C15' 6.7(8) . . . . ? 
C1' C6' C7' C15' -174.0(4) . . . . ? 
C6' C7' C8' N1' -0.5(5) . . . . ? 
C15' C7' C8' N1' 174.6(4) . . . . ? 
C1' N1' C8' C7' 0.0(5) . . . . ? 
C17' O1' C9' C10' -157.0(4) . . . . ? 
C17' O1' C9' C14' 23.3(5) . . . . ? 
O1' C9' C10' C11' 178.1(4) . . . . ? 
C14' C9' C10' C11' -2.2(7) . . . . ? 
C9' C10' C11' C12' 2.3(8) . . . . ? 
C10' C11' C12' C13' 0.1(8) . . . . ? 
C10' C11' C12' Br1' -178.2(4) . . . . ? 
C11' C12' C13' C14' -2.6(7) . . . . ? 
Br1' C12' C13' C14' 175.7(3) . . . . ? 
C12' C13' C14' C9' 2.6(6) . . . . ? 
C12' C13' C14' C15' -176.1(4) . . . . ? 
C10' C9' C14' C13' -0.3(6) . . . . ? 
O1' C9' C14' C13' 179.4(3) . . . . ? 
C10' C9' C14' C15' 178.5(4) . . . . ? 
O1' C9' C14' C15' -1.9(6) . . . . ? 
C13' C14' C15' C7' -37.5(5) . . . . ? 
C9' C14' C15' C7' 143.8(4) . . . . ? 
C13' C14' C15' C16' -165.7(3) . . . . ? 
C9' C14' C15' C16' 15.6(5) . . . . ? 
C8' C7' C15' C14' 134.2(4) . . . . ? 
C6' C7' C15' C14' -51.7(5) . . . . ? 
C8' C7' C15' C16' -99.3(5) . . . . ? 
C6' C7' C15' C16' 74.8(5) . . . . ? 
O5' N2' C16' C15' -121.1(3) . . . . ? 
O4' N2' C16' C15' 59.6(4) . . . . ? 
O5' N2' C16' C17' 119.7(3) . . . . ? 
O4' N2' C16' C17' -59.5(4) . . . . ? 
C14' C15' C16' N2' -167.4(3) . . . . ? 
C7' C15' C16' N2' 62.9(4) . . . . ? 
C14' C15' C16' C17' -48.0(4) . . . . ? 
C7' C15' C16' C17' -177.7(3) . . . . ? 
C9' O1' C17' C18' -179.3(3) . . . . ? 
C9' O1' C17' C16' -55.7(4) . . . . ? 
N2' C16' C17' O1' -171.7(3) . . . . ? 
C15' C16' C17' O1' 69.2(4) . . . . ? 
N2' C16' C17' C18' -53.4(4) . . . . ? 
C15' C16' C17' C18' -172.5(3) . . . . ? 
O1' C17' C18' C19' -66.6(4) . . . . ? 
C16' C17' C18' C19' 175.5(3) . . . . ? 
C20' O2' C19' O3' -2.1(5) . . . . ? 
C20' O2' C19' C18' 177.4(3) . . . . ? 
C17' C18' C19' O3' -9.7(5) . . . . ? 
C17' C18' C19' O2' 170.8(3) . . . . ? 
C19' O2' C20' C21' -165.9(3) . . . . ? 
C45 O11 C44 O12 0.1(9) . . . . ? 
C45 O11 C44 C43 178.3(6) . . . . ? 
C44 O11 C45 C46 154.0(6) . . . . ? 
C49 O13 C48 O14 -4.7(8) . . . . ? 
C49 O13 C48 C47 177.8(5) . . . . ? 
C48 O13 C49 C50 174.1(6) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              28.40 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.433 
_refine_diff_density_min   -0.487 
_refine_diff_density_rms    0.070 

