 
data_ms_a-cl 
 
_audit_creation_method            'CrystalClear-SM Expert 2.1 (Rigaku, 2013)' 
_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                    9.426(6) 
_cell_length_b                    11.630(4) 
_cell_length_c                    12.474(5) 
_cell_angle_alpha                 80.31(3) 
_cell_angle_beta                  83.65(6) 
_cell_angle_gamma                 81.13(5) 
_cell_volume                      1326.7(11) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used     3738 
_cell_measurement_theta_min       6.57 
_cell_measurement_theta_max       68.87 
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.03 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.401 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              584 
_exptl_absorpt_coefficient_mu     3.491 
_exptl_absorpt_correction_type    multi-scan  
_exptl_absorpt_correction_T_min   0.5419 
_exptl_absorpt_correction_T_max   0.9025 
_exptl_absorpt_process_details    'CrystalClear-SM Expert 2.1 (Rigaku, 2013)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       113(2) 
_diffrn_radiation_wavelength      1.54187 
_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             15639 
_diffrn_reflns_av_R_equivalents   0.0682 
_diffrn_reflns_av_sigmaI/netI     0.0600 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          6.57 
_diffrn_reflns_theta_max          68.87 
_reflns_number_total              4731 
_reflns_number_gt                 3738 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_cell_refinement        'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_data_reduction         'CrystalClear-SM Expert 2.1 (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)+(0.0729P)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_number_reflns          4731 
_refine_ls_number_parameters      331 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0553 
_refine_ls_R_factor_gt            0.0500 
_refine_ls_wR_factor_ref          0.1346 
_refine_ls_wR_factor_gt           0.1296 
_refine_ls_goodness_of_fit_ref    1.017 
_refine_ls_restrained_S_all       1.017 
_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 
N1 N 0.3501(2) 0.59309(15) 0.87083(15) 0.0232(4) Uani 1 1 d . . . 
C2 C 0.2677(2) 0.51278(18) 0.92909(18) 0.0224(5) Uani 1 1 d . . . 
C3 C 0.2014(2) 0.44248(18) 0.87386(17) 0.0221(5) Uani 1 1 d . . . 
C4 C 0.1147(2) 0.35798(18) 0.92945(17) 0.0213(5) Uani 1 1 d . . . 
N5 N 0.0555(2) 0.29138(15) 0.87127(15) 0.0228(4) Uani 1 1 d . . . 
C6 C -0.0262(2) 0.21607(18) 0.92731(18) 0.0232(5) Uani 1 1 d . . . 
C7 C -0.0574(2) 0.19840(19) 1.04168(18) 0.0250(5) Uani 1 1 d . . . 
H7 H -0.1184 0.1426 1.0762 0.030 Uiso 1 1 calc R . . 
C8 C 0.0024(2) 0.26367(19) 1.10130(18) 0.0237(5) Uani 1 1 d . . . 
C9 C 0.0931(2) 0.34765(18) 1.04608(17) 0.0223(5) Uani 1 1 d . . . 
C10 C 0.1574(2) 0.41635(18) 1.10209(17) 0.0225(5) Uani 1 1 d . . . 
H10 H 0.1418 0.4084 1.1794 0.027 Uiso 1 1 calc R . . 
C11 C 0.2445(2) 0.49666(18) 1.04576(18) 0.0226(5) Uani 1 1 d . . . 
C12 C 0.3144(2) 0.56650(19) 1.10161(18) 0.0243(5) Uani 1 1 d . . . 
C13 C 0.3984(2) 0.64504(18) 1.04271(18) 0.0247(5) Uani 1 1 d . . . 
H13 H 0.4468 0.6922 1.0778 0.030 Uiso 1 1 calc R . . 
C14 C 0.4107(2) 0.65358(18) 0.92787(18) 0.0237(5) Uani 1 1 d . . . 
C15 C -0.0887(2) 0.14325(19) 0.85926(19) 0.0255(5) Uani 1 1 d . . . 
O16 O -0.04872(19) 0.13325(16) 0.76683(14) 0.0373(4) Uani 1 1 d . . . 
O17 O -0.1960(2) 0.09195(15) 0.91728(14) 0.0365(4) Uani 1 1 d . . . 
C18 C -0.2670(3) 0.0205(2) 0.8606(2) 0.0424(7) Uani 1 1 d . . . 
H18A H -0.3102 0.0700 0.7976 0.064 Uiso 1 1 calc R . . 
H18B H -0.3424 -0.0141 0.9104 0.064 Uiso 1 1 calc R . . 
H18C H -0.1961 -0.0424 0.8355 0.064 Uiso 1 1 calc R . . 
O19 O -0.01507(17) 0.25774(13) 1.21045(12) 0.0273(4) Uani 1 1 d . . . 
C20 C -0.1182(3) 0.1855(2) 1.27072(19) 0.0285(5) Uani 1 1 d . . . 
H20A H -0.0864 0.1017 1.2638 0.034 Uiso 1 1 calc R . . 
H20B H -0.2137 0.2095 1.2417 0.034 Uiso 1 1 calc R . . 
C21 C -0.1279(3) 0.2021(2) 1.38893(19) 0.0309(5) Uani 1 1 d . . . 
H21 H -0.1563 0.2878 1.3929 0.037 Uiso 1 1 calc R . . 
C22 C 0.0167(3) 0.1630(2) 1.4367(2) 0.0385(6) Uani 1 1 d . . . 
H22A H 0.0041 0.1632 1.5157 0.058 Uiso 1 1 calc R . . 
H22B H 0.0846 0.2172 1.4030 0.058 Uiso 1 1 calc R . . 
H22C H 0.0546 0.0833 1.4221 0.058 Uiso 1 1 calc R . . 
C23 C -0.2452(3) 0.1356(2) 1.4530(2) 0.0408(6) Uani 1 1 d . . . 
H23A H -0.3383 0.1680 1.4244 0.061 Uiso 1 1 calc R . . 
H23B H -0.2499 0.1439 1.5302 0.061 Uiso 1 1 calc R . . 
H23C H -0.2230 0.0520 1.4455 0.061 Uiso 1 1 calc R . . 
O24 O 0.29006(18) 0.54565(14) 1.21074(12) 0.0277(4) Uani 1 1 d . . . 
C25 C 0.3544(3) 0.6120(2) 1.27573(19) 0.0300(5) Uani 1 1 d . . . 
H25A H 0.3227 0.6974 1.2556 0.036 Uiso 1 1 calc R . . 
H25B H 0.4608 0.5972 1.2639 0.036 Uiso 1 1 calc R . . 
C26 C 0.3053(3) 0.5713(2) 1.3933(2) 0.0353(6) Uani 1 1 d . . . 
H26 H 0.3442 0.6203 1.4388 0.042 Uiso 1 1 calc R . . 
C27 C 0.3685(4) 0.4432(2) 1.4288(2) 0.0502(8) Uani 1 1 d . . . 
H27A H 0.3227 0.3916 1.3927 0.075 Uiso 1 1 calc R . . 
H27B H 0.3506 0.4227 1.5081 0.075 Uiso 1 1 calc R . . 
H27C H 0.4725 0.4328 1.4083 0.075 Uiso 1 1 calc R . . 
C28 C 0.1427(3) 0.5906(3) 1.4136(2) 0.0487(7) Uani 1 1 d . . . 
H28A H 0.1062 0.6729 1.3873 0.073 Uiso 1 1 calc R . . 
H28B H 0.1150 0.5723 1.4920 0.073 Uiso 1 1 calc R . . 
H28C H 0.1014 0.5390 1.3745 0.073 Uiso 1 1 calc R . . 
C29 C 0.5039(2) 0.74236(19) 0.86775(19) 0.0256(5) Uani 1 1 d . . . 
O30 O 0.56711(19) 0.79898(14) 0.91323(14) 0.0349(4) Uani 1 1 d . . . 
O31 O 0.50944(18) 0.75038(14) 0.75906(13) 0.0302(4) Uani 1 1 d . . . 
C32 C 0.6032(3) 0.8315(2) 0.6994(2) 0.0354(6) Uani 1 1 d . . . 
H32A H 0.5659 0.9116 0.7131 0.053 Uiso 1 1 calc R . . 
H32B H 0.6067 0.8285 0.6211 0.053 Uiso 1 1 calc R . . 
H32C H 0.7004 0.8093 0.7237 0.053 Uiso 1 1 calc R . . 
Cl1 Cl 0.22339(6) 0.46146(5) 0.73289(4) 0.02747(17) Uani 1 1 d . . . 
C40 C 0.7279(3) 0.8606(2) 0.2892(2) 0.0372(6) Uani 1 1 d . . . 
H40A H 0.7887 0.8956 0.3313 0.045 Uiso 1 1 calc R . . 
H40B H 0.7819 0.7851 0.2716 0.045 Uiso 1 1 calc R . . 
Cl41 Cl 0.69226(7) 0.95719(6) 0.16668(5) 0.0430(2) Uani 1 1 d . . . 
Cl42 Cl 0.56578(8) 0.83386(6) 0.36931(6) 0.0504(2) 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 
N1 C14 1.307(3) . ? 
N1 C2 1.369(3) . ? 
C2 C3 1.405(3) . ? 
C2 C11 1.432(3) . ? 
C3 C4 1.417(3) . ? 
C3 Cl1 1.728(2) . ? 
C4 N5 1.360(3) . ? 
C4 C9 1.434(3) . ? 
N5 C6 1.316(3) . ? 
C6 C7 1.411(3) . ? 
C6 C15 1.513(3) . ? 
C7 C8 1.365(3) . ? 
C8 O19 1.345(3) . ? 
C8 C9 1.435(3) . ? 
C9 C10 1.387(3) . ? 
C10 C11 1.388(3) . ? 
C11 C12 1.427(3) . ? 
C12 O24 1.342(3) . ? 
C12 C13 1.367(3) . ? 
C13 C14 1.412(3) . ? 
C14 C29 1.508(3) . ? 
C15 O16 1.192(3) . ? 
C15 O17 1.335(3) . ? 
O17 C18 1.453(3) . ? 
O19 C20 1.447(3) . ? 
C20 C21 1.510(3) . ? 
C21 C22 1.522(4) . ? 
C21 C23 1.523(3) . ? 
O24 C25 1.443(3) . ? 
C25 C26 1.508(4) . ? 
C26 C28 1.514(4) . ? 
C26 C27 1.527(4) . ? 
C29 O30 1.197(3) . ? 
C29 O31 1.339(3) . ? 
O31 C32 1.449(3) . ? 
C40 Cl41 1.769(3) . ? 
C40 Cl42 1.771(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 
C14 N1 C2 116.23(19) . . ? 
N1 C2 C3 119.7(2) . . ? 
N1 C2 C11 122.8(2) . . ? 
C3 C2 C11 117.5(2) . . ? 
C2 C3 C4 122.39(19) . . ? 
C2 C3 Cl1 118.98(17) . . ? 
C4 C3 Cl1 118.63(17) . . ? 
N5 C4 C3 119.50(19) . . ? 
N5 C4 C9 123.0(2) . . ? 
C3 C4 C9 117.5(2) . . ? 
C6 N5 C4 116.66(19) . . ? 
N5 C6 C7 125.9(2) . . ? 
N5 C6 C15 114.8(2) . . ? 
C7 C6 C15 119.3(2) . . ? 
C8 C7 C6 118.1(2) . . ? 
O19 C8 C7 126.0(2) . . ? 
O19 C8 C9 114.7(2) . . ? 
C7 C8 C9 119.3(2) . . ? 
C10 C9 C4 121.0(2) . . ? 
C10 C9 C8 122.0(2) . . ? 
C4 C9 C8 117.0(2) . . ? 
C9 C10 C11 120.3(2) . . ? 
C10 C11 C12 121.4(2) . . ? 
C10 C11 C2 121.3(2) . . ? 
C12 C11 C2 117.3(2) . . ? 
O24 C12 C13 126.4(2) . . ? 
O24 C12 C11 114.2(2) . . ? 
C13 C12 C11 119.4(2) . . ? 
C12 C13 C14 117.6(2) . . ? 
N1 C14 C13 126.6(2) . . ? 
N1 C14 C29 118.4(2) . . ? 
C13 C14 C29 115.0(2) . . ? 
O16 C15 O17 124.5(2) . . ? 
O16 C15 C6 125.1(2) . . ? 
O17 C15 C6 110.4(2) . . ? 
C15 O17 C18 115.9(2) . . ? 
C8 O19 C20 117.97(18) . . ? 
O19 C20 C21 107.8(2) . . ? 
C20 C21 C22 111.3(2) . . ? 
C20 C21 C23 109.1(2) . . ? 
C22 C21 C23 111.7(2) . . ? 
C12 O24 C25 119.08(18) . . ? 
O24 C25 C26 106.7(2) . . ? 
C25 C26 C28 111.7(2) . . ? 
C25 C26 C27 110.7(2) . . ? 
C28 C26 C27 112.0(3) . . ? 
O30 C29 O31 123.7(2) . . ? 
O30 C29 C14 123.0(2) . . ? 
O31 C29 C14 113.2(2) . . ? 
C29 O31 C32 114.32(19) . . ? 
Cl41 C40 Cl42 110.99(15) . . ? 
 
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 -178.64(19) . . . . ? 
C14 N1 C2 C11 1.6(3) . . . . ? 
N1 C2 C3 C4 -179.91(19) . . . . ? 
C11 C2 C3 C4 -0.1(3) . . . . ? 
N1 C2 C3 Cl1 -1.2(3) . . . . ? 
C11 C2 C3 Cl1 178.57(16) . . . . ? 
C2 C3 C4 N5 -178.98(19) . . . . ? 
Cl1 C3 C4 N5 2.3(3) . . . . ? 
C2 C3 C4 C9 1.4(3) . . . . ? 
Cl1 C3 C4 C9 -177.30(15) . . . . ? 
C3 C4 N5 C6 -178.72(19) . . . . ? 
C9 C4 N5 C6 0.9(3) . . . . ? 
C4 N5 C6 C7 0.0(3) . . . . ? 
C4 N5 C6 C15 -179.48(18) . . . . ? 
N5 C6 C7 C8 -0.6(3) . . . . ? 
C15 C6 C7 C8 178.79(19) . . . . ? 
C6 C7 C8 O19 -179.6(2) . . . . ? 
C6 C7 C8 C9 0.5(3) . . . . ? 
N5 C4 C9 C10 179.09(19) . . . . ? 
C3 C4 C9 C10 -1.3(3) . . . . ? 
N5 C4 C9 C8 -1.0(3) . . . . ? 
C3 C4 C9 C8 178.62(19) . . . . ? 
O19 C8 C9 C10 0.3(3) . . . . ? 
C7 C8 C9 C10 -179.8(2) . . . . ? 
O19 C8 C9 C4 -179.67(18) . . . . ? 
C7 C8 C9 C4 0.3(3) . . . . ? 
C4 C9 C10 C11 -0.1(3) . . . . ? 
C8 C9 C10 C11 180.0(2) . . . . ? 
C9 C10 C11 C12 -178.6(2) . . . . ? 
C9 C10 C11 C2 1.4(3) . . . . ? 
N1 C2 C11 C10 178.44(19) . . . . ? 
C3 C2 C11 C10 -1.3(3) . . . . ? 
N1 C2 C11 C12 -1.5(3) . . . . ? 
C3 C2 C11 C12 178.73(19) . . . . ? 
C10 C11 C12 O24 1.1(3) . . . . ? 
C2 C11 C12 O24 -178.95(18) . . . . ? 
C10 C11 C12 C13 -179.6(2) . . . . ? 
C2 C11 C12 C13 0.4(3) . . . . ? 
O24 C12 C13 C14 179.76(19) . . . . ? 
C11 C12 C13 C14 0.5(3) . . . . ? 
C2 N1 C14 C13 -0.6(3) . . . . ? 
C2 N1 C14 C29 179.37(18) . . . . ? 
C12 C13 C14 N1 -0.4(3) . . . . ? 
C12 C13 C14 C29 179.57(19) . . . . ? 
N5 C6 C15 O16 15.0(3) . . . . ? 
C7 C6 C15 O16 -164.5(2) . . . . ? 
N5 C6 C15 O17 -164.66(19) . . . . ? 
C7 C6 C15 O17 15.9(3) . . . . ? 
O16 C15 O17 C18 -0.5(3) . . . . ? 
C6 C15 O17 C18 179.11(19) . . . . ? 
C7 C8 O19 C20 -7.1(3) . . . . ? 
C9 C8 O19 C20 172.86(19) . . . . ? 
C8 O19 C20 C21 -174.93(18) . . . . ? 
O19 C20 C21 C22 -61.2(3) . . . . ? 
O19 C20 C21 C23 175.07(19) . . . . ? 
C13 C12 O24 C25 1.2(3) . . . . ? 
C11 C12 O24 C25 -179.48(19) . . . . ? 
C12 O24 C25 C26 178.77(19) . . . . ? 
O24 C25 C26 C28 -59.0(3) . . . . ? 
O24 C25 C26 C27 66.6(3) . . . . ? 
N1 C14 C29 O30 -177.6(2) . . . . ? 
C13 C14 C29 O30 2.4(3) . . . . ? 
N1 C14 C29 O31 1.9(3) . . . . ? 
C13 C14 C29 O31 -178.14(18) . . . . ? 
O30 C29 O31 C32 1.9(3) . . . . ? 
C14 C29 O31 C32 -177.52(18) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.963 
_diffrn_reflns_theta_full              68.87 
_diffrn_measured_fraction_theta_full   0.963 
_refine_diff_density_max    0.553 
_refine_diff_density_min   -0.435 
_refine_diff_density_rms    0.075 
