 
data_shelxl 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C25 H29 Cl3 N2 O6' 
_chemical_formula_weight          559.85 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.3639   0.7018 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            triclinic 
_symmetry_space_group_name_H-M    P-1
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    9.393(2) 
_cell_length_b                    11.183(3) 
_cell_length_c                    14.185(2) 
_cell_angle_alpha                 75.57(3) 
_cell_angle_beta                  71.46(4) 
_cell_angle_gamma                 80.53(4) 
_cell_volume                      1362.2(5) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.15 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.365 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              584 
_exptl_absorpt_coefficient_mu     3.400 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.4836 
_exptl_absorpt_correction_T_max   0.6295 
_exptl_absorpt_process_details    'CrystalClear-SM Expert 2.1 b25 (Rigaku, 2013)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54190 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'Rotating Anode'
_diffrn_radiation_monochromator   'Confocal'
_diffrn_detector                  'PILT'
_diffrn_measurement_device        'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type   'Rigaku PILATUS conversion'
_diffrn_measurement_method        'profile data from ω-scans' 
_diffrn_detector_area_resol_mean  5.8140  
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             17304 
_diffrn_reflns_av_R_equivalents   0.0576 
_diffrn_reflns_av_sigmaI/netI     0.0477 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          6.73 
_diffrn_reflns_theta_max          68.49 
_reflns_number_total              4806 
_reflns_number_gt                 3841 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrystalClear-SM Expert 2.1 b25 (Rigaku, 2013)'
_computing_cell_refinement        'CrystalClear-SM Expert 2.1 b25 (Rigaku, 2013)'
_computing_data_reduction         'CrystalClear-SM Expert 2.1 b25 (Rigaku, 2013)'
_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)+(0.0987P)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     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0026(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          4806 
_refine_ls_number_parameters      332 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0553 
_refine_ls_R_factor_gt            0.0497 
_refine_ls_wR_factor_ref          0.1485 
_refine_ls_wR_factor_gt           0.1416 
_refine_ls_goodness_of_fit_ref    1.054 
_refine_ls_restrained_S_all       1.054 
_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 
C1 C 0.5179(2) 0.79876(16) 1.53217(14) 0.0219(4) Uani 1 1 d . . . 
C2 C 0.5792(2) 0.81257(16) 1.42518(14) 0.0230(4) Uani 1 1 d . . . 
H2 H 0.6533 0.8687 1.3877 0.028 Uiso 1 1 calc R . . 
C3 C 0.5290(2) 0.74316(16) 1.37733(14) 0.0222(4) Uani 1 1 d . . . 
C4 C 0.4200(2) 0.65741(16) 1.43675(14) 0.0214(4) Uani 1 1 d . . . 
C5 C 0.3685(2) 0.65004(16) 1.54458(14) 0.0216(4) Uani 1 1 d . . . 
N6 N 0.41698(19) 0.72281(13) 1.59152(11) 0.0213(4) Uani 1 1 d . . . 
C7 C 0.5712(2) 0.87514(16) 1.58671(15) 0.0236(4) Uani 1 1 d . . . 
O8 O 0.51549(17) 0.88157(13) 1.67411(10) 0.0315(4) Uani 1 1 d . . . 
O9 O 0.68968(16) 0.93423(12) 1.52376(10) 0.0279(3) Uani 1 1 d . . . 
C10 C 0.7621(2) 1.00370(18) 1.56603(16) 0.0289(5) Uani 1 1 d . . . 
H10A H 0.6893 1.0291 1.6261 0.043 Uiso 1 1 calc R . . 
H10B H 0.7990 1.0775 1.5151 0.043 Uiso 1 1 calc R . . 
H10C H 0.8471 0.9516 1.5856 0.043 Uiso 1 1 calc R . . 
O11 O 0.57456(16) 0.74709(12) 1.27648(10) 0.0254(3) Uani 1 1 d . . . 
C12 C 0.6961(2) 0.82357(18) 1.21597(15) 0.0286(5) Uani 1 1 d . . . 
H12A H 0.7823 0.8009 1.2449 0.034 Uiso 1 1 calc R . . 
H12B H 0.6614 0.9121 1.2161 0.034 Uiso 1 1 calc R . . 
C13 C 0.7442(3) 0.80263(19) 1.10805(15) 0.0318(5) Uani 1 1 d . . . 
H13 H 0.8358 0.8480 1.0699 0.038 Uiso 1 1 calc R . . 
C14 C 0.6255(3) 0.8558(2) 1.05341(18) 0.0446(6) Uani 1 1 d . . . 
H14A H 0.5374 0.8080 1.0846 0.067 Uiso 1 1 calc R . . 
H14B H 0.6670 0.8511 0.9816 0.067 Uiso 1 1 calc R . . 
H14C H 0.5952 0.9426 1.0588 0.067 Uiso 1 1 calc R . . 
C15 C 0.7910(3) 0.6654(2) 1.10707(17) 0.0410(6) Uani 1 1 d . . . 
H15A H 0.7023 0.6186 1.1393 0.061 Uiso 1 1 calc R . . 
H15B H 0.8656 0.6344 1.1447 0.061 Uiso 1 1 calc R . . 
H15C H 0.8352 0.6552 1.0367 0.061 Uiso 1 1 calc R . . 
C16 C 0.3658(2) 0.58055(16) 1.39439(14) 0.0225(4) Uani 1 1 d . . . 
H16 H 0.3999 0.5859 1.3230 0.027 Uiso 1 1 calc R . . 
C17 C 0.2631(2) 0.49679(16) 1.45518(14) 0.0211(4) Uani 1 1 d . . . 
C18 C 0.2114(2) 0.48703(16) 1.56363(14) 0.0214(4) Uani 1 1 d . . . 
C19 C 0.2648(2) 0.56476(16) 1.60544(14) 0.0225(4) Uani 1 1 d . . . 
H19 H 0.2301 0.5597 1.6768 0.027 Uiso 1 1 calc R . . 
C20 C 0.2034(2) 0.41707(16) 1.41475(14) 0.0227(4) Uani 1 1 d . . . 
C21 C 0.1026(2) 0.33643(16) 1.48009(15) 0.0235(4) Uani 1 1 d . . . 
H21 H 0.0602 0.2834 1.4555 0.028 Uiso 1 1 calc R . . 
C22 C 0.0635(2) 0.33432(16) 1.58567(15) 0.0233(4) Uani 1 1 d . . . 
N23 N 0.11211(19) 0.40462(13) 1.62827(12) 0.0228(4) Uani 1 1 d . . . 
O24 O 0.25413(16) 0.42987(12) 1.31322(10) 0.0250(3) Uani 1 1 d . . . 
C25 C 0.1909(2) 0.35676(18) 1.26773(15) 0.0276(4) Uani 1 1 d . . . 
H25A H 0.0804 0.3776 1.2830 0.033 Uiso 1 1 calc R . . 
H25B H 0.2105 0.2673 1.2956 0.033 Uiso 1 1 calc R . . 
C26 C 0.2644(3) 0.38604(19) 1.15405(15) 0.0312(5) Uani 1 1 d . . . 
H26 H 0.2174 0.3371 1.1236 0.037 Uiso 1 1 calc R . . 
C27 C 0.4330(3) 0.3460(2) 1.12544(17) 0.0387(5) Uani 1 1 d . . . 
H27A H 0.4831 0.3917 1.1545 0.058 Uiso 1 1 calc R . . 
H27B H 0.4746 0.3638 1.0512 0.058 Uiso 1 1 calc R . . 
H27C H 0.4496 0.2569 1.1522 0.058 Uiso 1 1 calc R . . 
C28 C 0.2316(3) 0.5226(2) 1.10844(18) 0.0425(6) Uani 1 1 d . . . 
H28A H 0.1235 0.5472 1.1336 0.064 Uiso 1 1 calc R . . 
H28B H 0.2615 0.5354 1.0341 0.064 Uiso 1 1 calc R . . 
H28C H 0.2888 0.5730 1.1283 0.064 Uiso 1 1 calc R . . 
C29 C -0.0436(2) 0.24014(17) 1.65421(15) 0.0254(4) Uani 1 1 d . . . 
O30 O -0.08358(18) 0.16442(14) 1.62319(11) 0.0357(4) Uani 1 1 d . . . 
O31 O -0.08586(18) 0.24885(13) 1.75114(11) 0.0337(4) Uani 1 1 d . . . 
C32 C -0.1930(3) 0.1637(2) 1.81855(17) 0.0414(6) Uani 1 1 d . . . 
H32A H -0.2808 0.1733 1.7933 0.062 Uiso 1 1 calc R . . 
H32B H -0.2252 0.1815 1.8869 0.062 Uiso 1 1 calc R . . 
H32C H -0.1456 0.0785 1.8213 0.062 Uiso 1 1 calc R . . 
C50 C 0.1924(3) 0.80010(19) 0.80300(16) 0.0326(5) Uani 1 1 d . . . 
H50 H 0.2998 0.7885 0.7614 0.039 Uiso 1 1 calc R . . 
Cl1 Cl 0.12207(7) 0.65457(5) 0.85497(4) 0.0399(2) Uani 1 1 d . . . 
Cl2 Cl 0.18470(9) 0.86997(6) 0.90384(5) 0.0590(3) Uani 1 1 d . . . 
Cl3 Cl 0.08793(9) 0.89569(7) 0.72535(5) 0.0663(3) Uani 1 1 d . . . 
 
 
_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 
C1 N6 1.315(3) . ? 
C1 C2 1.420(3) . ? 
C1 C7 1.515(3) . ? 
C2 C3 1.368(3) . ? 
C3 O11 1.348(2) . ? 
C3 C4 1.432(3) . ? 
C4 C16 1.398(3) . ? 
C4 C5 1.435(3) . ? 
C5 N6 1.378(2) . ? 
C5 C19 1.401(3) . ? 
C7 O8 1.198(2) . ? 
C7 O9 1.337(3) . ? 
O9 C10 1.446(2) . ? 
O11 C12 1.450(2) . ? 
C12 C13 1.519(3) . ? 
C13 C14 1.517(3) . ? 
C13 C15 1.527(3) . ? 
C16 C17 1.384(3) . ? 
C17 C20 1.436(3) . ? 
C17 C18 1.440(3) . ? 
C18 N23 1.370(3) . ? 
C18 C19 1.396(3) . ? 
C20 O24 1.344(2) . ? 
C20 C21 1.369(3) . ? 
C21 C22 1.419(3) . ? 
C22 N23 1.313(3) . ? 
C22 C29 1.510(3) . ? 
O24 C25 1.451(2) . ? 
C25 C26 1.513(3) . ? 
C26 C27 1.523(3) . ? 
C26 C28 1.525(3) . ? 
C29 O30 1.203(2) . ? 
C29 O31 1.328(3) . ? 
O31 C32 1.443(3) . ? 
C50 Cl3 1.753(2) . ? 
C50 Cl1 1.753(2) . ? 
C50 Cl2 1.770(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 
N6 C1 C2 125.86(18) . . ? 
N6 C1 C7 114.79(17) . . ? 
C2 C1 C7 119.35(17) . . ? 
C3 C2 C1 118.42(18) . . ? 
O11 C3 C2 125.42(18) . . ? 
O11 C3 C4 115.45(17) . . ? 
C2 C3 C4 119.14(17) . . ? 
C16 C4 C3 122.87(18) . . ? 
C16 C4 C5 119.78(18) . . ? 
C3 C4 C5 117.34(17) . . ? 
N6 C5 C19 118.15(17) . . ? 
N6 C5 C4 122.94(18) . . ? 
C19 C5 C4 118.91(17) . . ? 
C1 N6 C5 116.27(16) . . ? 
O8 C7 O9 124.61(18) . . ? 
O8 C7 C1 124.88(18) . . ? 
O9 C7 C1 110.52(16) . . ? 
C7 O9 C10 117.60(15) . . ? 
C3 O11 C12 116.48(15) . . ? 
O11 C12 C13 108.38(17) . . ? 
C14 C13 C12 112.45(19) . . ? 
C14 C13 C15 112.2(2) . . ? 
C12 C13 C15 110.66(17) . . ? 
C17 C16 C4 120.86(18) . . ? 
C16 C17 C20 122.69(17) . . ? 
C16 C17 C18 120.19(17) . . ? 
C20 C17 C18 117.13(18) . . ? 
N23 C18 C19 118.12(17) . . ? 
N23 C18 C17 123.15(17) . . ? 
C19 C18 C17 118.72(18) . . ? 
C18 C19 C5 121.53(17) . . ? 
O24 C20 C21 125.85(18) . . ? 
O24 C20 C17 115.06(17) . . ? 
C21 C20 C17 119.09(17) . . ? 
C20 C21 C22 118.09(18) . . ? 
N23 C22 C21 126.41(18) . . ? 
N23 C22 C29 117.95(17) . . ? 
C21 C22 C29 115.64(18) . . ? 
C22 N23 C18 116.11(16) . . ? 
C20 O24 C25 117.36(16) . . ? 
O24 C25 C26 107.95(17) . . ? 
C25 C26 C27 112.50(18) . . ? 
C25 C26 C28 111.28(18) . . ? 
C27 C26 C28 111.6(2) . . ? 
O30 C29 O31 124.20(19) . . ? 
O30 C29 C22 122.70(19) . . ? 
O31 C29 C22 113.09(17) . . ? 
C29 O31 C32 114.80(17) . . ? 
Cl3 C50 Cl1 111.21(13) . . ? 
Cl3 C50 Cl2 110.02(12) . . ? 
Cl1 C50 Cl2 108.57(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 
N6 C1 C2 C3 1.1(3) . . . . ? 
C7 C1 C2 C3 -179.68(16) . . . . ? 
C1 C2 C3 O11 179.03(16) . . . . ? 
C1 C2 C3 C4 -1.5(3) . . . . ? 
O11 C3 C4 C16 1.3(3) . . . . ? 
C2 C3 C4 C16 -178.22(17) . . . . ? 
O11 C3 C4 C5 179.92(15) . . . . ? 
C2 C3 C4 C5 0.4(3) . . . . ? 
C16 C4 C5 N6 179.99(16) . . . . ? 
C3 C4 C5 N6 1.3(3) . . . . ? 
C16 C4 C5 C19 0.4(3) . . . . ? 
C3 C4 C5 C19 -178.30(16) . . . . ? 
C2 C1 N6 C5 0.6(3) . . . . ? 
C7 C1 N6 C5 -178.69(15) . . . . ? 
C19 C5 N6 C1 177.84(16) . . . . ? 
C4 C5 N6 C1 -1.8(3) . . . . ? 
N6 C1 C7 O8 -9.6(3) . . . . ? 
C2 C1 C7 O8 171.05(18) . . . . ? 
N6 C1 C7 O9 170.13(15) . . . . ? 
C2 C1 C7 O9 -9.2(2) . . . . ? 
O8 C7 O9 C10 4.6(3) . . . . ? 
C1 C7 O9 C10 -175.20(15) . . . . ? 
C2 C3 O11 C12 5.6(3) . . . . ? 
C4 C3 O11 C12 -173.84(16) . . . . ? 
C3 O11 C12 C13 172.72(16) . . . . ? 
O11 C12 C13 C14 69.4(2) . . . . ? 
O11 C12 C13 C15 -57.0(2) . . . . ? 
C3 C4 C16 C17 178.38(16) . . . . ? 
C5 C4 C16 C17 -0.2(3) . . . . ? 
C4 C16 C17 C20 179.33(16) . . . . ? 
C4 C16 C17 C18 -0.5(3) . . . . ? 
C16 C17 C18 N23 -178.78(17) . . . . ? 
C20 C17 C18 N23 1.4(3) . . . . ? 
C16 C17 C18 C19 1.0(3) . . . . ? 
C20 C17 C18 C19 -178.79(16) . . . . ? 
N23 C18 C19 C5 178.94(16) . . . . ? 
C17 C18 C19 C5 -0.9(3) . . . . ? 
N6 C5 C19 C18 -179.44(16) . . . . ? 
C4 C5 C19 C18 0.2(3) . . . . ? 
C16 C17 C20 O24 -0.2(3) . . . . ? 
C18 C17 C20 O24 179.63(15) . . . . ? 
C16 C17 C20 C21 179.77(17) . . . . ? 
C18 C17 C20 C21 -0.4(3) . . . . ? 
O24 C20 C21 C22 179.06(16) . . . . ? 
C17 C20 C21 C22 -0.9(3) . . . . ? 
C20 C21 C22 N23 1.5(3) . . . . ? 
C20 C21 C22 C29 -177.78(16) . . . . ? 
C21 C22 N23 C18 -0.6(3) . . . . ? 
C29 C22 N23 C18 178.70(15) . . . . ? 
C19 C18 N23 C22 179.28(16) . . . . ? 
C17 C18 N23 C22 -0.9(3) . . . . ? 
C21 C20 O24 C25 3.5(3) . . . . ? 
C17 C20 O24 C25 -176.51(15) . . . . ? 
C20 O24 C25 C26 -179.89(16) . . . . ? 
O24 C25 C26 C27 64.5(2) . . . . ? 
O24 C25 C26 C28 -61.6(2) . . . . ? 
N23 C22 C29 O30 -173.25(18) . . . . ? 
C21 C22 C29 O30 6.1(3) . . . . ? 
N23 C22 C29 O31 5.7(3) . . . . ? 
C21 C22 C29 O31 -174.91(16) . . . . ? 
O30 C29 O31 C32 -3.4(3) . . . . ? 
C22 C29 O31 C32 177.61(17) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.958 
_diffrn_reflns_theta_full              68.49 
_diffrn_measured_fraction_theta_full   0.958 
_refine_diff_density_max    0.367 
_refine_diff_density_min   -0.564 
_refine_diff_density_rms    0.071 
