 
data_ms_a-ch2br 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C25 H29 Br N2 O6' 
_chemical_formula_weight          533.41 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'  -0.6763   1.2805 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            triclinic 
_symmetry_space_group_name_H-M    P-1 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    9.505(5) 
_cell_length_b                    10.865(5) 
_cell_length_c                    12.959(6) 
_cell_angle_alpha                 112.60(3) 
_cell_angle_beta                  99.94(4) 
_cell_angle_gamma                 95.09(4) 
_cell_volume                      1199.2(10) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used     1068 
_cell_measurement_theta_min       6.54 
_cell_measurement_theta_max       71.75 
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.14 
_exptl_crystal_size_mid           0.09 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.477 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              552 
_exptl_absorpt_coefficient_mu     2.708 
_exptl_absorpt_correction_type    multi-scan  
_exptl_absorpt_correction_T_min   0.7030 
_exptl_absorpt_correction_T_max   0.9478 
_exptl_absorpt_process_details    'CrystalClear (Rigaku/MSC Inc., 2005)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       113(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'micro-focus rotating anode' 
_diffrn_radiation_monochromator   'confocal' 
_diffrn_measurement_device_type   'Rigaku RAXIS Rapid' 
_diffrn_measurement_method        ω-scans 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3044 
_diffrn_reflns_av_R_equivalents   0.0981 
_diffrn_reflns_av_sigmaI/netI     0.1934 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          6.54 
_diffrn_reflns_theta_max          71.75 
_reflns_number_total              2321 
_reflns_number_gt                 1068 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrystalClear (Rigaku/MSC Inc., 2005)'  
_computing_cell_refinement        'CrystalClear (Rigaku/MSC Inc., 2005)'  
_computing_data_reduction         'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution     'SHELXS (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL (Sheldrick, 2008)' 
_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)+(0.0437P)²+1.5326P] 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_number_reflns          2321 
_refine_ls_number_parameters      301 
_refine_ls_number_restraints      26 
_refine_ls_R_factor_all           0.1552 
_refine_ls_R_factor_gt            0.1141 
_refine_ls_wR_factor_ref          0.2423 
_refine_ls_wR_factor_gt           0.2167 
_refine_ls_goodness_of_fit_ref    1.051 
_refine_ls_restrained_S_all       1.049 
_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 
N1 N 0.2483(14) 0.9652(12) 0.3612(10) 0.075(5) Uani 1 1 d . . . 
C2 C 0.3023(11) 0.9245(11) 0.4463(8) 0.076(6) Uani 1 1 d G . . 
C3 C 0.3914(11) 0.8279(11) 0.4155(6) 0.079(6) Uani 1 1 d GU . . 
C4 C 0.4479(10) 0.7744(9) 0.4923(9) 0.082(7) Uani 1 1 d G . . 
C9 C 0.4152(11) 0.8176(10) 0.5999(8) 0.054(5) Uani 1 1 d G . . 
C10 C 0.3261(11) 0.9142(11) 0.6306(6) 0.056(5) Uani 1 1 d G . . 
H10 H 0.3037 0.9437 0.7041 0.067 Uiso 1 1 calc R . . 
C11 C 0.2696(10) 0.9677(10) 0.5538(9) 0.090(7) Uani 1 1 d G . . 
N5 N 0.5513(12) 0.6914(11) 0.4649(8) 0.059(4) Uani 1 1 d . . . 
C15 C 0.723(2) 0.5574(16) 0.5055(15) 0.062(6) Uani 1 1 d DU . . 
C7 C 0.5650(19) 0.6684(16) 0.6410(12) 0.060(6) Uani 1 1 d . . . 
H7 H 0.6071 0.6277 0.6891 0.072 Uiso 1 1 calc R . . 
C8 C 0.4641(19) 0.7536(16) 0.6774(13) 0.056(6) Uani 1 1 d . . . 
C12 C 0.1864(16) 1.0779(15) 0.5825(12) 0.068(6) Uani 1 1 d . . . 
C13 C 0.1300(15) 1.1192(13) 0.5002(11) 0.080(5) Uani 1 1 d . . . 
H13 H 0.0693 1.1860 0.5142 0.096 Uiso 1 1 calc R . . 
C14 C 0.1670(18) 1.0563(15) 0.3897(12) 0.067(7) Uani 1 1 d D . . 
C33 C 0.4246(13) 0.7786(11) 0.3003(9) 0.048(4) Uani 1 1 d U . . 
H33A H 0.5229 0.7548 0.3057 0.057 Uiso 1 1 calc R . . 
H33B H 0.4238 0.8518 0.2727 0.057 Uiso 1 1 calc R . . 
Br34 Br 0.28201(18) 0.61757(16) 0.18817(12) 0.0905(10) Uani 1 1 d U . . 
C6 C 0.605(2) 0.6415(16) 0.5382(13) 0.078(7) Uani 1 1 d D . . 
O16 O 0.7757(11) 0.5418(10) 0.4230(9) 0.075(4) Uani 1 1 d U . . 
O17 O 0.7626(11) 0.5046(9) 0.5816(7) 0.077(4) Uani 1 1 d U . . 
C18 C 0.8802(18) 0.4309(15) 0.5705(12) 0.088(7) Uani 1 1 d . . . 
H18A H 0.8548 0.3512 0.4973 0.131 Uiso 1 1 calc R . . 
H18B H 0.8996 0.4019 0.6338 0.131 Uiso 1 1 calc R . . 
H18C H 0.9668 0.4888 0.5729 0.131 Uiso 1 1 calc R . . 
O19 O 0.4156(11) 0.7830(9) 0.7705(8) 0.079(4) Uani 1 1 d . . . 
C20 C 0.4502(17) 0.7053(14) 0.8363(11) 0.082(6) Uani 1 1 d . . . 
H20A H 0.5518 0.7367 0.8808 0.098 Uiso 1 1 calc R . . 
H20B H 0.4394 0.6086 0.7845 0.098 Uiso 1 1 calc R . . 
C21 C 0.3472(16) 0.7231(15) 0.9176(12) 0.056(5) Uani 1 1 d . . . 
H21 H 0.3741 0.6687 0.9628 0.068 Uiso 1 1 calc R . . 
C22 C 0.1885(15) 0.6640(14) 0.8495(11) 0.085(6) Uani 1 1 d . . . 
H22A H 0.1570 0.7166 0.8056 0.127 Uiso 1 1 calc R . . 
H22B H 0.1258 0.6685 0.9030 0.127 Uiso 1 1 calc R . . 
H22C H 0.1823 0.5695 0.7967 0.127 Uiso 1 1 calc R . . 
C23 C 0.363(2) 0.8695(16) 1.0036(12) 0.111(7) Uani 1 1 d . . . 
H23A H 0.4615 0.8998 1.0513 0.166 Uiso 1 1 calc R . . 
H23B H 0.2933 0.8753 1.0525 0.166 Uiso 1 1 calc R . . 
H23C H 0.3431 0.9273 0.9623 0.166 Uiso 1 1 calc R . . 
O24 O 0.1705(10) 1.1268(10) 0.6921(8) 0.062(3) Uani 1 1 d . . . 
C25 C 0.1167(16) 1.2518(15) 0.7321(11) 0.084(6) Uani 1 1 d . . . 
H25A H 0.0100 1.2348 0.7049 0.100 Uiso 1 1 calc R . . 
H25B H 0.1590 1.3133 0.7013 0.100 Uiso 1 1 calc R . . 
C26 C 0.1560(15) 1.3154(13) 0.8592(10) 0.068(5) Uani 1 1 d . . . 
H26 H 0.1183 1.4028 0.8846 0.081 Uiso 1 1 calc R . . 
C27 C 0.0882(15) 1.2290(13) 0.9130(10) 0.074(5) Uani 1 1 d . . . 
H27A H -0.0176 1.2150 0.8891 0.111 Uiso 1 1 calc R . . 
H27B H 0.1178 1.2753 0.9967 0.111 Uiso 1 1 calc R . . 
H27C H 0.1210 1.1413 0.8876 0.111 Uiso 1 1 calc R . . 
C28 C 0.3234(16) 1.3487(14) 0.9022(10) 0.098(6) Uani 1 1 d . . . 
H28A H 0.3610 1.2659 0.8969 0.146 Uiso 1 1 calc R . . 
H28B H 0.3488 1.4150 0.9822 0.146 Uiso 1 1 calc R . . 
H28C H 0.3661 1.3863 0.8547 0.146 Uiso 1 1 calc R . . 
C29 C 0.105(2) 1.1153(16) 0.3077(15) 0.062(7) Uani 1 1 d D . . 
O30 O 0.0232(13) 1.1954(11) 0.3248(9) 0.089(5) Uani 1 1 d . . . 
O31 O 0.1633(12) 1.0714(9) 0.2120(8) 0.076(4) Uani 1 1 d . . . 
C32 C 0.1212(15) 1.1304(14) 0.1318(10) 0.096(6) Uani 1 1 d . . . 
H32A H 0.0152 1.1150 0.1083 0.144 Uiso 1 1 calc R . . 
H32B H 0.1615 1.0886 0.0643 0.144 Uiso 1 1 calc R . . 
H32C H 0.1582 1.2279 0.1681 0.144 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 
N1 C14 1.291(18) . ? 
N1 C2 1.376(12) . ? 
C2 C3 1.3900 . ? 
C2 C11 1.3900 . ? 
C3 C4 1.3900 . ? 
C3 C33 1.481(13) . ? 
C4 N5 1.392(13) . ? 
C4 C9 1.3900 . ? 
C9 C10 1.3900 . ? 
C9 C8 1.463(15) . ? 
C10 C11 1.3900 . ? 
C11 C12 1.457(17) . ? 
N5 C6 1.318(15) . ? 
C15 O16 1.216(19) . ? 
C15 O17 1.337(15) . ? 
C15 C6 1.524(15) . ? 
C7 C6 1.379(19) . ? 
C7 C8 1.406(18) . ? 
C8 O19 1.301(17) . ? 
C12 O24 1.353(15) . ? 
C12 C13 1.357(14) . ? 
C13 C14 1.45(2) . ? 
C14 C29 1.505(14) . ? 
C33 Br34 1.988(11) . ? 
O17 C18 1.427(15) . ? 
O19 C20 1.433(12) . ? 
C20 C21 1.529(16) . ? 
C21 C23 1.528(17) . ? 
C21 C22 1.549(16) . ? 
O24 C25 1.431(15) . ? 
C25 C26 1.482(15) . ? 
C26 C27 1.528(14) . ? 
C26 C28 1.553(17) . ? 
C29 O30 1.200(19) . ? 
C29 O31 1.38(2) . ? 
O31 C32 1.436(11) . ? 
 
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 
C14 N1 C2 114.8(14) . . ? 
N1 C2 C3 114.5(11) . . ? 
N1 C2 C11 125.5(11) . . ? 
C3 C2 C11 120.0 . . ? 
C2 C3 C4 120.0 . . ? 
C2 C3 C33 120.7(9) . . ? 
C4 C3 C33 119.3(9) . . ? 
N5 C4 C9 121.0(9) . . ? 
N5 C4 C3 118.4(9) . . ? 
C9 C4 C3 120.0 . . ? 
C4 C9 C10 120.0 . . ? 
C4 C9 C8 120.2(12) . . ? 
C10 C9 C8 119.6(12) . . ? 
C11 C10 C9 120.0 . . ? 
C10 C11 C2 120.0 . . ? 
C10 C11 C12 123.6(9) . . ? 
C2 C11 C12 116.2(10) . . ? 
C6 N5 C4 118.3(14) . . ? 
O16 C15 O17 125(2) . . ? 
O16 C15 C6 125.0(16) . . ? 
O17 C15 C6 110.1(17) . . ? 
C6 C7 C8 122.7(17) . . ? 
O19 C8 C7 127.9(15) . . ? 
O19 C8 C9 118.7(17) . . ? 
C7 C8 C9 113.4(16) . . ? 
O24 C12 C13 126.3(16) . . ? 
O24 C12 C11 114.3(11) . . ? 
C13 C12 C11 119.3(14) . . ? 
C12 C13 C14 116.7(15) . . ? 
N1 C14 C13 127.0(13) . . ? 
N1 C14 C29 121.1(18) . . ? 
C13 C14 C29 111.9(16) . . ? 
C3 C33 Br34 111.8(7) . . ? 
N5 C6 C7 123(2) . . ? 
N5 C6 C15 115.4(16) . . ? 
C7 C6 C15 121.4(17) . . ? 
C15 O17 C18 118.4(14) . . ? 
C8 O19 C20 117.1(14) . . ? 
O19 C20 C21 108.6(13) . . ? 
C23 C21 C20 112.9(13) . . ? 
C23 C21 C22 111.8(14) . . ? 
C20 C21 C22 110.9(11) . . ? 
C12 O24 C25 116.7(11) . . ? 
O24 C25 C26 109.3(11) . . ? 
C25 C26 C27 112.8(11) . . ? 
C25 C26 C28 110.1(12) . . ? 
C27 C26 C28 110.9(10) . . ? 
O30 C29 O31 124.2(15) . . ? 
O30 C29 C14 126(2) . . ? 
O31 C29 C14 110.1(17) . . ? 
C29 O31 C32 115.1(12) . . ? 
 
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 
C14 N1 C2 C3 -179.1(10) . . . . ? 
C14 N1 C2 C11 3.7(15) . . . . ? 
N1 C2 C3 C4 -177.3(8) . . . . ? 
C11 C2 C3 C4 0.0 . . . . ? 
N1 C2 C3 C33 1.2(10) . . . . ? 
C11 C2 C3 C33 178.6(8) . . . . ? 
C2 C3 C4 N5 -171.8(8) . . . . ? 
C33 C3 C4 N5 9.6(9) . . . . ? 
C2 C3 C4 C9 0.0 . . . . ? 
C33 C3 C4 C9 -178.6(8) . . . . ? 
N5 C4 C9 C10 171.6(9) . . . . ? 
C3 C4 C9 C10 0.0 . . . . ? 
N5 C4 C9 C8 -13.6(10) . . . . ? 
C3 C4 C9 C8 174.8(9) . . . . ? 
C4 C9 C10 C11 0.0 . . . . ? 
C8 C9 C10 C11 -174.8(8) . . . . ? 
C9 C10 C11 C2 0.0 . . . . ? 
C9 C10 C11 C12 -174.2(9) . . . . ? 
N1 C2 C11 C10 177.0(9) . . . . ? 
C3 C2 C11 C10 0.0 . . . . ? 
N1 C2 C11 C12 -8.4(10) . . . . ? 
C3 C2 C11 C12 174.6(9) . . . . ? 
C9 C4 N5 C6 7.9(12) . . . . ? 
C3 C4 N5 C6 179.6(8) . . . . ? 
C6 C7 C8 O19 178.1(12) . . . . ? 
C6 C7 C8 C9 -4.2(19) . . . . ? 
C4 C9 C8 O19 -170.8(9) . . . . ? 
C10 C9 C8 O19 4.0(14) . . . . ? 
C4 C9 C8 C7 11.3(14) . . . . ? 
C10 C9 C8 C7 -173.9(9) . . . . ? 
C10 C11 C12 O24 1.3(13) . . . . ? 
C2 C11 C12 O24 -173.1(7) . . . . ? 
C10 C11 C12 C13 -177.0(8) . . . . ? 
C2 C11 C12 C13 8.6(13) . . . . ? 
O24 C12 C13 C14 177.2(12) . . . . ? 
C11 C12 C13 C14 -4.7(16) . . . . ? 
C2 N1 C14 C13 1(2) . . . . ? 
C2 N1 C14 C29 177.4(10) . . . . ? 
C12 C13 C14 N1 0(2) . . . . ? 
C12 C13 C14 C29 -177.0(11) . . . . ? 
C2 C3 C33 Br34 -90.4(8) . . . . ? 
C4 C3 C33 Br34 88.2(7) . . . . ? 
C4 N5 C6 C7 -0.5(17) . . . . ? 
C4 N5 C6 C15 -177.0(9) . . . . ? 
C8 C7 C6 N5 -1(2) . . . . ? 
C8 C7 C6 C15 175.3(12) . . . . ? 
O16 C15 C6 N5 5.1(19) . . . . ? 
O17 C15 C6 N5 -175.7(9) . . . . ? 
O16 C15 C6 C7 -171.5(13) . . . . ? 
O17 C15 C6 C7 7.7(16) . . . . ? 
O16 C15 O17 C18 3.9(19) . . . . ? 
C6 C15 O17 C18 -175.3(10) . . . . ? 
C7 C8 O19 C20 -11(2) . . . . ? 
C9 C8 O19 C20 171.9(9) . . . . ? 
C8 O19 C20 C21 -162.4(11) . . . . ? 
O19 C20 C21 C23 -62.1(14) . . . . ? 
O19 C20 C21 C22 64.2(14) . . . . ? 
C13 C12 O24 C25 -14.4(18) . . . . ? 
C11 C12 O24 C25 167.5(10) . . . . ? 
C12 O24 C25 C26 -159.3(11) . . . . ? 
O24 C25 C26 C27 -62.2(16) . . . . ? 
O24 C25 C26 C28 62.2(14) . . . . ? 
N1 C14 C29 O30 176.4(15) . . . . ? 
C13 C14 C29 O30 -7(2) . . . . ? 
N1 C14 C29 O31 -7.9(19) . . . . ? 
C13 C14 C29 O31 169.1(11) . . . . ? 
O30 C29 O31 C32 1(2) . . . . ? 
C14 C29 O31 C32 -174.9(10) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.494 
_diffrn_reflns_theta_full              71.75 
_diffrn_measured_fraction_theta_full   0.494 
_refine_diff_density_max    0.903 
_refine_diff_density_min   -1.006 
_refine_diff_density_rms    0.132 
