 
data_mscl 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H31 Cl N2 O6' 
_chemical_formula_weight          478.96 
 
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            monoclinic 
_symmetry_space_group_name_H-M    P21/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    12.5630(8) 
_cell_length_b                    21.5829(13) 
_cell_length_c                    9.2102(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  106.995(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      2388.3(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used     3729 
_cell_measurement_theta_min       6.70 
_cell_measurement_theta_max       71.99 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.16 
_exptl_crystal_size_mid           0.13 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.332 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1016 
_exptl_absorpt_coefficient_mu     1.773 
_exptl_absorpt_correction_type    multi-scan  
_exptl_absorpt_correction_T_min   0.7645 
_exptl_absorpt_correction_T_max   0.8426 
_exptl_absorpt_process_details    'CrystalClear (Rigaku/MSC Inc., 2005)'  
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       113(2) 
_diffrn_radiation_wavelength      1.54180 
_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             35972 
_diffrn_reflns_av_R_equivalents   0.0681 
_diffrn_reflns_av_sigmaI/netI     0.0454 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -26 
_diffrn_reflns_limit_k_max        24 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          6.70 
_diffrn_reflns_theta_max          71.99 
_reflns_number_total              4610 
_reflns_number_gt                 3729 
_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)+(0.0856P)²+0.8622P] 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          4610 
_refine_ls_number_parameters      304 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0634 
_refine_ls_R_factor_gt            0.0587 
_refine_ls_wR_factor_ref          0.1421 
_refine_ls_wR_factor_gt           0.1400 
_refine_ls_goodness_of_fit_ref    1.008 
_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 
N1 N 0.19244(14) 0.24089(8) 0.0016(2) 0.0270(4) Uani 1 1 d . . . 
H1 H 0.1843 0.2035 -0.0385 0.032 Uiso 1 1 calc R . . 
C2 C 0.27262(16) 0.24950(10) 0.1367(2) 0.0226(4) Uani 1 1 d . . . 
C3 C 0.33382(17) 0.20036(9) 0.2168(2) 0.0221(4) Uani 1 1 d . . . 
C4 C 0.41830(16) 0.20823(9) 0.3562(2) 0.0224(4) Uani 1 1 d . . . 
N5 N 0.46795(14) 0.15783(8) 0.4365(2) 0.0240(4) Uani 1 1 d . . . 
C6 C 0.54722(17) 0.16905(10) 0.5651(2) 0.0246(5) Uani 1 1 d . . . 
C7 C 0.58593(17) 0.22800(10) 0.6221(2) 0.0261(5) Uani 1 1 d . . . 
H7 H 0.6459 0.2324 0.7125 0.031 Uiso 1 1 calc R . . 
C8 C 0.53408(17) 0.27900(10) 0.5427(2) 0.0243(5) Uani 1 1 d . . . 
C9 C 0.44592(16) 0.27017(10) 0.4075(2) 0.0231(4) Uani 1 1 d . . . 
C10 C 0.38314(17) 0.31985(10) 0.3259(2) 0.0241(4) Uani 1 1 d . . . 
H10 H 0.4016 0.3610 0.3609 0.029 Uiso 1 1 calc R . . 
C11 C 0.29665(16) 0.31048(10) 0.1982(2) 0.0239(5) Uani 1 1 d . . . 
C12 C 0.22324(17) 0.36319(10) 0.1237(2) 0.0249(5) Uani 1 1 d . . . 
H12 H 0.2678 0.4023 0.1413 0.030 Uiso 1 1 calc R . . 
C13 C 0.17574(18) 0.35281(10) -0.0455(3) 0.0282(5) Uani 1 1 d . . . 
H13A H 0.2362 0.3558 -0.0941 0.034 Uiso 1 1 calc R . . 
H13B H 0.1205 0.3856 -0.0892 0.034 Uiso 1 1 calc R . . 
C14 C 0.12018(18) 0.28955(10) -0.0793(3) 0.0273(5) Uani 1 1 d . . . 
H14 H 0.1083 0.2816 -0.1899 0.033 Uiso 1 1 calc R . . 
C15 C 0.60120(18) 0.11519(10) 0.6620(3) 0.0282(5) Uani 1 1 d . . . 
O16 O 0.67451(14) 0.12133(7) 0.7796(2) 0.0409(4) Uani 1 1 d . . . 
O17 O 0.56028(12) 0.06055(7) 0.60525(18) 0.0320(4) Uani 1 1 d . . . 
C18 C 0.6137(2) 0.00703(11) 0.6909(3) 0.0356(5) Uani 1 1 d . . . 
H18A H 0.6941 0.0092 0.7061 0.053 Uiso 1 1 calc R . . 
H18B H 0.5840 -0.0308 0.6349 0.053 Uiso 1 1 calc R . . 
H18C H 0.5991 0.0065 0.7898 0.053 Uiso 1 1 calc R . . 
O19 O 0.55721(12) 0.33824(7) 0.58439(17) 0.0285(4) Uani 1 1 d . . . 
C20 C 0.64930(17) 0.35103(10) 0.7174(2) 0.0276(5) Uani 1 1 d . . . 
H20A H 0.7206 0.3411 0.6973 0.033 Uiso 1 1 calc R . . 
H20B H 0.6432 0.3255 0.8039 0.033 Uiso 1 1 calc R . . 
C21 C 0.64510(18) 0.41899(10) 0.7543(3) 0.0298(5) Uani 1 1 d . . . 
H21 H 0.5731 0.4272 0.7766 0.036 Uiso 1 1 calc R . . 
C22 C 0.73958(19) 0.43349(11) 0.8962(3) 0.0347(5) Uani 1 1 d . . . 
H22A H 0.7375 0.4044 0.9769 0.052 Uiso 1 1 calc R . . 
H22B H 0.7313 0.4759 0.9294 0.052 Uiso 1 1 calc R . . 
H22C H 0.8109 0.4296 0.8738 0.052 Uiso 1 1 calc R . . 
C23 C 0.6500(3) 0.45990(12) 0.6222(3) 0.0500(7) Uani 1 1 d . . . 
H23A H 0.7207 0.4530 0.5997 0.075 Uiso 1 1 calc R . . 
H23B H 0.6446 0.5035 0.6491 0.075 Uiso 1 1 calc R . . 
H23C H 0.5880 0.4496 0.5327 0.075 Uiso 1 1 calc R . . 
O24 O 0.13788(12) 0.36752(7) 0.19997(17) 0.0266(3) Uani 1 1 d . . . 
C25 C 0.07635(19) 0.42452(10) 0.1699(3) 0.0301(5) Uani 1 1 d . . . 
H25A H 0.0135 0.4203 0.0761 0.036 Uiso 1 1 calc R . . 
H25B H 0.1252 0.4583 0.1543 0.036 Uiso 1 1 calc R . . 
C26 C 0.0327(2) 0.44027(11) 0.3012(3) 0.0347(5) Uani 1 1 d . . . 
H26 H 0.0975 0.4442 0.3946 0.042 Uiso 1 1 calc R . . 
C27 C -0.0264(2) 0.50315(12) 0.2702(3) 0.0435(6) Uani 1 1 d . . . 
H27A H 0.0259 0.5347 0.2564 0.065 Uiso 1 1 calc R . . 
H27B H -0.0533 0.5145 0.3564 0.065 Uiso 1 1 calc R . . 
H27C H -0.0896 0.5004 0.1781 0.065 Uiso 1 1 calc R . . 
C28 C -0.0434(2) 0.39080(14) 0.3285(4) 0.0548(8) Uani 1 1 d . . . 
H28A H -0.1070 0.3859 0.2376 0.082 Uiso 1 1 calc R . . 
H28B H -0.0700 0.4027 0.4146 0.082 Uiso 1 1 calc R . . 
H28C H -0.0027 0.3515 0.3511 0.082 Uiso 1 1 calc R . . 
C29 C 0.00435(18) 0.29083(10) -0.0552(3) 0.0290(5) Uani 1 1 d . . . 
O30 O -0.06500(13) 0.32832(8) -0.11623(19) 0.0391(4) Uani 1 1 d . . . 
O31 O -0.01292(12) 0.24448(8) 0.03100(18) 0.0341(4) Uani 1 1 d . . . 
C32 C -0.1261(2) 0.23913(14) 0.0393(3) 0.0478(7) Uani 1 1 d . . . 
H32A H -0.1465 0.2771 0.0830 0.072 Uiso 1 1 calc R . . 
H32B H -0.1313 0.2037 0.1034 0.072 Uiso 1 1 calc R . . 
H32C H -0.1769 0.2329 -0.0629 0.072 Uiso 1 1 calc R . . 
Cl33 Cl 0.30183(4) 0.12623(2) 0.14317(6) 0.02654(16) 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 C2 1.366(3) . ? 
N1 C14 1.445(3) . ? 
C2 C3 1.389(3) . ? 
C2 C11 1.430(3) . ? 
C3 C4 1.416(3) . ? 
C3 Cl33 1.739(2) . ? 
C4 N5 1.360(3) . ? 
C4 C9 1.427(3) . ? 
N5 C6 1.328(3) . ? 
C6 C7 1.408(3) . ? 
C6 C15 1.501(3) . ? 
C7 C8 1.376(3) . ? 
C8 O19 1.342(2) . ? 
C8 C9 1.417(3) . ? 
C9 C10 1.411(3) . ? 
C10 C11 1.363(3) . ? 
C11 C12 1.499(3) . ? 
C12 O24 1.447(2) . ? 
C12 C13 1.513(3) . ? 
C13 C14 1.524(3) . ? 
C14 C29 1.535(3) . ? 
C15 O16 1.207(3) . ? 
C15 O17 1.331(3) . ? 
O17 C18 1.448(3) . ? 
O19 C20 1.445(2) . ? 
C20 C21 1.510(3) . ? 
C21 C23 1.519(3) . ? 
C21 C22 1.519(3) . ? 
O24 C25 1.436(2) . ? 
C25 C26 1.506(3) . ? 
C26 C28 1.502(4) . ? 
C26 C27 1.533(3) . ? 
C29 O30 1.201(3) . ? 
C29 O31 1.334(3) . ? 
O31 C32 1.451(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 
C2 N1 C14 123.78(18) . . ? 
N1 C2 C3 121.78(19) . . ? 
N1 C2 C11 120.01(18) . . ? 
C3 C2 C11 118.21(19) . . ? 
C2 C3 C4 122.81(19) . . ? 
C2 C3 Cl33 117.81(16) . . ? 
C4 C3 Cl33 119.37(16) . . ? 
N5 C4 C3 120.02(19) . . ? 
N5 C4 C9 122.71(19) . . ? 
C3 C4 C9 117.26(18) . . ? 
C6 N5 C4 116.39(18) . . ? 
N5 C6 C7 125.80(19) . . ? 
N5 C6 C15 118.65(19) . . ? 
C7 C6 C15 115.55(19) . . ? 
C8 C7 C6 117.8(2) . . ? 
O19 C8 C7 125.5(2) . . ? 
O19 C8 C9 115.32(18) . . ? 
C7 C8 C9 119.13(19) . . ? 
C10 C9 C8 122.54(19) . . ? 
C10 C9 C4 119.4(2) . . ? 
C8 C9 C4 118.00(19) . . ? 
C11 C10 C9 121.8(2) . . ? 
C10 C11 C2 120.06(19) . . ? 
C10 C11 C12 120.74(19) . . ? 
C2 C11 C12 119.16(18) . . ? 
O24 C12 C11 105.72(16) . . ? 
O24 C12 C13 112.61(17) . . ? 
C11 C12 C13 111.33(17) . . ? 
C12 C13 C14 111.25(18) . . ? 
N1 C14 C13 111.40(18) . . ? 
N1 C14 C29 114.70(18) . . ? 
C13 C14 C29 110.56(17) . . ? 
O16 C15 O17 123.8(2) . . ? 
O16 C15 C6 122.8(2) . . ? 
O17 C15 C6 113.41(19) . . ? 
C15 O17 C18 115.37(17) . . ? 
C8 O19 C20 118.51(16) . . ? 
O19 C20 C21 107.72(17) . . ? 
C20 C21 C23 111.9(2) . . ? 
C20 C21 C22 108.90(18) . . ? 
C23 C21 C22 111.4(2) . . ? 
C25 O24 C12 113.27(15) . . ? 
O24 C25 C26 109.89(18) . . ? 
C28 C26 C25 111.9(2) . . ? 
C28 C26 C27 111.3(2) . . ? 
C25 C26 C27 108.71(19) . . ? 
O30 C29 O31 124.2(2) . . ? 
O30 C29 C14 122.2(2) . . ? 
O31 C29 C14 113.49(18) . . ? 
C29 O31 C32 115.06(18) . . ? 
 
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 174.45(18) . . . . ? 
C14 N1 C2 C11 -6.5(3) . . . . ? 
N1 C2 C3 C4 179.20(17) . . . . ? 
C11 C2 C3 C4 0.1(3) . . . . ? 
N1 C2 C3 Cl33 -2.3(3) . . . . ? 
C11 C2 C3 Cl33 178.62(14) . . . . ? 
C2 C3 C4 N5 173.68(18) . . . . ? 
Cl33 C3 C4 N5 -4.8(2) . . . . ? 
C2 C3 C4 C9 -5.1(3) . . . . ? 
Cl33 C3 C4 C9 176.49(14) . . . . ? 
C3 C4 N5 C6 179.26(17) . . . . ? 
C9 C4 N5 C6 -2.1(3) . . . . ? 
C4 N5 C6 C7 -2.0(3) . . . . ? 
C4 N5 C6 C15 177.23(17) . . . . ? 
N5 C6 C7 C8 3.4(3) . . . . ? 
C15 C6 C7 C8 -175.79(18) . . . . ? 
C6 C7 C8 O19 177.00(18) . . . . ? 
C6 C7 C8 C9 -0.8(3) . . . . ? 
O19 C8 C9 C10 -2.9(3) . . . . ? 
C7 C8 C9 C10 175.12(18) . . . . ? 
O19 C8 C9 C4 179.18(16) . . . . ? 
C7 C8 C9 C4 -2.8(3) . . . . ? 
N5 C4 C9 C10 -173.57(17) . . . . ? 
C3 C4 C9 C10 5.1(3) . . . . ? 
N5 C4 C9 C8 4.4(3) . . . . ? 
C3 C4 C9 C8 -176.86(17) . . . . ? 
C8 C9 C10 C11 -178.25(18) . . . . ? 
C4 C9 C10 C11 -0.3(3) . . . . ? 
C9 C10 C11 C2 -4.8(3) . . . . ? 
C9 C10 C11 C12 172.99(18) . . . . ? 
N1 C2 C11 C10 -174.20(17) . . . . ? 
C3 C2 C11 C10 4.9(3) . . . . ? 
N1 C2 C11 C12 8.0(3) . . . . ? 
C3 C2 C11 C12 -172.95(17) . . . . ? 
C10 C11 C12 O24 -86.5(2) . . . . ? 
C2 C11 C12 O24 91.3(2) . . . . ? 
C10 C11 C12 C13 150.90(19) . . . . ? 
C2 C11 C12 C13 -31.3(2) . . . . ? 
O24 C12 C13 C14 -66.5(2) . . . . ? 
C11 C12 C13 C14 52.0(2) . . . . ? 
C2 N1 C14 C13 28.1(3) . . . . ? 
C2 N1 C14 C29 -98.5(2) . . . . ? 
C12 C13 C14 N1 -50.3(2) . . . . ? 
C12 C13 C14 C29 78.5(2) . . . . ? 
N5 C6 C15 O16 179.3(2) . . . . ? 
C7 C6 C15 O16 -1.4(3) . . . . ? 
N5 C6 C15 O17 -0.7(3) . . . . ? 
C7 C6 C15 O17 178.58(17) . . . . ? 
O16 C15 O17 C18 -3.0(3) . . . . ? 
C6 C15 O17 C18 176.99(17) . . . . ? 
C7 C8 O19 C20 4.9(3) . . . . ? 
C9 C8 O19 C20 -177.30(16) . . . . ? 
C8 O19 C20 C21 -170.49(17) . . . . ? 
O19 C20 C21 C23 -57.8(2) . . . . ? 
O19 C20 C21 C22 178.68(17) . . . . ? 
C11 C12 O24 C25 165.51(17) . . . . ? 
C13 C12 O24 C25 -72.7(2) . . . . ? 
C12 O24 C25 C26 -152.48(18) . . . . ? 
O24 C25 C26 C28 -60.1(3) . . . . ? 
O24 C25 C26 C27 176.60(19) . . . . ? 
N1 C14 C29 O30 -179.3(2) . . . . ? 
C13 C14 C29 O30 53.7(3) . . . . ? 
N1 C14 C29 O31 -3.3(3) . . . . ? 
C13 C14 C29 O31 -130.26(19) . . . . ? 
O30 C29 O31 C32 4.0(3) . . . . ? 
C14 C29 O31 C32 -171.90(19) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.981 
_diffrn_reflns_theta_full              71.99 
_diffrn_measured_fraction_theta_full   0.981 
_refine_diff_density_max    0.656 
_refine_diff_density_min   -0.336 
_refine_diff_density_rms    0.118 
