 
data_01esp002
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C26 H33 Cl N4 O12' 
_chemical_formula_weight          629.01 
 
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 '-x+1/2, -y, z+1/2' 
 
_cell_length_a                    8.4889(2) 
_cell_length_b                    11.5350(2) 
_cell_length_c                    31.9275(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3126.32(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     11194
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.05 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.336 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1320 
_exptl_absorpt_coefficient_mu     0.188 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9815 
_exptl_absorpt_correction_T_max   0.9907 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             9693 
_diffrn_reflns_av_R_equivalents   0.0763 
_diffrn_reflns_av_sigmaI/netI     0.0996 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -35 
_diffrn_reflns_limit_l_max        38 
_diffrn_reflns_theta_min          2.98 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              5286 
_reflns_number_gt                 3997 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection         'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_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)+(0.0567P)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      SHELXL 
_refine_ls_extinction_coef        0.0067(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.11(9) 
_refine_ls_number_reflns          5286 
_refine_ls_number_parameters      389 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0784 
_refine_ls_R_factor_gt            0.0498 
_refine_ls_wR_factor_ref          0.1224 
_refine_ls_wR_factor_gt           0.1105 
_refine_ls_goodness_of_fit_ref    0.988 
_refine_ls_restrained_S_all       0.988 
_refine_ls_shift/su_max           0.006 
_refine_ls_shift/su_mean          0.001 
 
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 -0.0563(3) -0.2409(2) 0.36565(8) 0.0227(7) Uani 1 1 d . . . 
N2 N 0.0054(3) -0.3511(2) 0.37233(9) 0.0230(7) Uani 1 1 d . . . 
N3 N 0.2436(3) -0.5426(2) 0.31730(9) 0.0238(7) Uani 1 1 d . . . 
N4 N 0.3250(3) -0.6444(2) 0.31950(9) 0.0260(7) Uani 1 1 d . . . 
H4A H 0.3185 -0.6888 0.3418 0.031 Uiso 1 1 calc R . . 
O1 O -0.2240(3) -0.10228(18) 0.38530(7) 0.0293(6) Uani 1 1 d . . . 
O2 O -0.2234(3) -0.27121(19) 0.42141(7) 0.0280(6) Uani 1 1 d . . . 
O3 O 0.4315(3) -0.6218(2) 0.25386(8) 0.0344(6) Uani 1 1 d . . . 
O4 O 0.4914(3) -0.7746(2) 0.29623(8) 0.0337(6) Uani 1 1 d . . . 
O5 O 0.1594(3) -0.68640(18) 0.39000(7) 0.0242(6) Uani 1 1 d . . . 
O6 O -0.1013(3) -0.7058(2) 0.39493(13) 0.0706(11) Uani 1 1 d . . . 
O7 O 0.4244(3) -0.54061(18) 0.40599(7) 0.0236(6) Uani 1 1 d . . . 
O8 O 0.4428(3) -0.3582(2) 0.38055(8) 0.0365(7) Uani 1 1 d . . . 
O9 O 0.1077(3) -0.53969(18) 0.48132(7) 0.0242(6) Uani 1 1 d . . . 
O10 O 0.0408(3) -0.7247(2) 0.49259(12) 0.0607(10) Uani 1 1 d . . . 
O11 O 0.3974(3) -0.40895(17) 0.49250(7) 0.0248(6) Uani 1 1 d . . . 
O12 O 0.5826(3) -0.4109(2) 0.54290(8) 0.0353(6) Uani 1 1 d . . . 
Cl1 Cl 0.19600(12) 0.08715(8) 0.23960(3) 0.0428(3) Uani 1 1 d . . . 
C1 C 0.1611(4) -0.1297(3) 0.33660(11) 0.0245(8) Uani 1 1 d . . . 
H1 H 0.2265 -0.1583 0.3584 0.029 Uiso 1 1 calc R . . 
C2 C 0.2215(4) -0.0540(3) 0.30705(11) 0.0278(9) Uani 1 1 d . . . 
H2 H 0.3290 -0.0311 0.3081 0.033 Uiso 1 1 calc R . . 
C3 C 0.1228(5) -0.0120(3) 0.27591(11) 0.0281(9) Uani 1 1 d . . . 
C4 C -0.0317(4) -0.0466(3) 0.27335(11) 0.0278(9) Uani 1 1 d . . . 
H4 H -0.0976 -0.0175 0.2517 0.033 Uiso 1 1 calc R . . 
C5 C -0.0911(4) -0.1243(3) 0.30252(10) 0.0249(8) Uani 1 1 d . . . 
H5 H -0.1971 -0.1501 0.3006 0.030 Uiso 1 1 calc R . . 
C6 C 0.0039(4) -0.1638(3) 0.33417(11) 0.0224(8) Uani 1 1 d . . . 
C7 C -0.1745(4) -0.2095(3) 0.39369(11) 0.0235(8) Uani 1 1 d . . . 
C8 C -0.3666(4) -0.0674(3) 0.40778(11) 0.0316(9) Uani 1 1 d . . . 
H8A H -0.3452 -0.0612 0.4382 0.038 Uiso 1 1 calc R . . 
H8B H -0.4515 -0.1250 0.4034 0.038 Uiso 1 1 calc R . . 
C9 C -0.4144(5) 0.0485(3) 0.39036(13) 0.0477(11) Uani 1 1 d . . . 
H9A H -0.5092 0.0758 0.4048 0.072 Uiso 1 1 calc R . . 
H9B H -0.4363 0.0408 0.3604 0.072 Uiso 1 1 calc R . . 
H9C H -0.3288 0.1043 0.3946 0.072 Uiso 1 1 calc R . . 
C10 C 0.0923(4) -0.3938(3) 0.34333(10) 0.0208(8) Uani 1 1 d . . . 
H10 H 0.1101 -0.3517 0.3182 0.025 Uiso 1 1 calc R . . 
C11 C 0.1636(4) -0.5076(3) 0.34936(10) 0.0198(8) Uani 1 1 d . . . 
C12 C 0.4172(4) -0.6760(3) 0.28620(12) 0.0276(9) Uani 1 1 d . . . 
C13 C 0.6148(5) -0.8138(3) 0.26712(13) 0.0427(11) Uani 1 1 d . . . 
H13A H 0.5928 -0.7841 0.2386 0.051 Uiso 1 1 calc R . . 
H13B H 0.6164 -0.8995 0.2660 0.051 Uiso 1 1 calc R . . 
C14 C 0.7701(5) -0.7698(3) 0.28186(13) 0.0417(11) Uani 1 1 d . . . 
H14A H 0.8530 -0.7960 0.2627 0.063 Uiso 1 1 calc R . . 
H14B H 0.7913 -0.7997 0.3100 0.063 Uiso 1 1 calc R . . 
H14C H 0.7682 -0.6849 0.2826 0.063 Uiso 1 1 calc R . . 
C15 C 0.1461(4) -0.5619(3) 0.39217(11) 0.0219(8) Uani 1 1 d . . . 
H15 H 0.0395 -0.5418 0.4034 0.026 Uiso 1 1 calc R . . 
C16 C 0.0242(5) -0.7491(3) 0.39095(12) 0.0305(9) Uani 1 1 d . . . 
C17 C 0.0590(4) -0.8751(3) 0.38732(12) 0.0353(10) Uani 1 1 d . . . 
H17A H 0.1729 -0.8865 0.3845 0.053 Uiso 1 1 calc R . . 
H17B H 0.0056 -0.9066 0.3626 0.053 Uiso 1 1 calc R . . 
H17C H 0.0214 -0.9153 0.4125 0.053 Uiso 1 1 calc R . . 
C18 C 0.2701(4) -0.5163(3) 0.42238(10) 0.0203(8) Uani 1 1 d . . . 
H18 H 0.2572 -0.4305 0.4254 0.024 Uiso 1 1 calc R . . 
C19 C 0.4995(4) -0.4531(3) 0.38485(11) 0.0278(8) Uani 1 1 d . . . 
C20 C 0.6519(4) -0.4942(3) 0.36751(12) 0.0408(11) Uani 1 1 d . . . 
H20A H 0.6692 -0.5751 0.3758 0.061 Uiso 1 1 calc R . . 
H20B H 0.7377 -0.4460 0.3784 0.061 Uiso 1 1 calc R . . 
H20C H 0.6495 -0.4888 0.3369 0.061 Uiso 1 1 calc R . . 
C21 C 0.2612(4) -0.5721(3) 0.46540(10) 0.0211(8) Uani 1 1 d . . . 
H21 H 0.2661 -0.6583 0.4623 0.025 Uiso 1 1 calc R . . 
C22 C 0.0055(4) -0.6238(3) 0.49207(12) 0.0286(9) Uani 1 1 d . . . 
C23 C -0.1526(4) -0.5740(3) 0.50132(14) 0.0399(10) Uani 1 1 d . . . 
H23A H -0.1480 -0.4893 0.4991 0.060 Uiso 1 1 calc R . . 
H23B H -0.1844 -0.5957 0.5298 0.060 Uiso 1 1 calc R . . 
H23C H -0.2296 -0.6042 0.4812 0.060 Uiso 1 1 calc R . . 
C24 C 0.3884(4) -0.5332(3) 0.49521(11) 0.0228(8) Uani 1 1 d . . . 
H24A H 0.3623 -0.5572 0.5242 0.027 Uiso 1 1 calc R . . 
H24B H 0.4906 -0.5684 0.4874 0.027 Uiso 1 1 calc R . . 
C25 C 0.5080(4) -0.3584(3) 0.51717(12) 0.0248(8) Uani 1 1 d . . . 
C26 C 0.5263(4) -0.2324(3) 0.50723(12) 0.0313(9) Uani 1 1 d . . . 
H26A H 0.4520 -0.2108 0.4851 0.047 Uiso 1 1 calc R . . 
H26B H 0.6342 -0.2175 0.4977 0.047 Uiso 1 1 calc R . . 
H26C H 0.5048 -0.1864 0.5324 0.047 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 N2 1.392(4) . ? 
N1 C7 1.393(4) . ? 
N1 C6 1.436(4) . ? 
N2 C10 1.282(4) . ? 
N3 C11 1.293(4) . ? 
N3 N4 1.365(4) . ? 
N4 C12 1.369(4) . ? 
O1 C7 1.333(4) . ? 
O1 C8 1.464(4) . ? 
O2 C7 1.209(4) . ? 
O3 C12 1.213(4) . ? 
O4 C12 1.338(4) . ? 
O4 C13 1.472(4) . ? 
O5 C16 1.357(4) . ? 
O5 C15 1.443(4) . ? 
O6 C16 1.184(4) . ? 
O7 C19 1.372(4) . ? 
O7 C18 1.438(4) . ? 
O8 C19 1.204(4) . ? 
O9 C22 1.346(4) . ? 
O9 C21 1.447(4) . ? 
O10 C22 1.201(4) . ? 
O11 C25 1.357(4) . ? 
O11 C24 1.438(3) . ? 
O12 C25 1.201(4) . ? 
Cl1 C3 1.743(4) . ? 
C1 C2 1.384(5) . ? 
C1 C6 1.394(5) . ? 
C2 C3 1.388(5) . ? 
C3 C4 1.373(5) . ? 
C4 C5 1.387(5) . ? 
C5 C6 1.371(5) . ? 
C8 C9 1.503(5) . ? 
C10 C11 1.458(4) . ? 
C11 C15 1.511(5) . ? 
C13 C14 1.489(5) . ? 
C15 C18 1.522(4) . ? 
C16 C17 1.488(5) . ? 
C18 C21 1.519(5) . ? 
C19 C20 1.485(5) . ? 
C21 C24 1.508(4) . ? 
C22 C23 1.490(5) . ? 
C25 C26 1.496(5) . ? 
 
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 
N2 N1 C7 114.2(3) . . ? 
N2 N1 C6 122.6(3) . . ? 
C7 N1 C6 123.1(3) . . ? 
C10 N2 N1 117.2(3) . . ? 
C11 N3 N4 119.6(3) . . ? 
N3 N4 C12 118.6(3) . . ? 
C7 O1 C8 114.6(3) . . ? 
C12 O4 C13 116.4(3) . . ? 
C16 O5 C15 117.6(3) . . ? 
C19 O7 C18 117.3(3) . . ? 
C22 O9 C21 118.9(3) . . ? 
C25 O11 C24 115.5(3) . . ? 
C2 C1 C6 119.7(3) . . ? 
C1 C2 C3 119.0(3) . . ? 
C4 C3 C2 121.2(3) . . ? 
C4 C3 Cl1 119.5(3) . . ? 
C2 C3 Cl1 119.3(3) . . ? 
C3 C4 C5 119.7(3) . . ? 
C6 C5 C4 119.7(3) . . ? 
C5 C6 C1 120.7(3) . . ? 
C5 C6 N1 120.9(3) . . ? 
C1 C6 N1 118.4(3) . . ? 
O2 C7 O1 125.8(3) . . ? 
O2 C7 N1 124.4(3) . . ? 
O1 C7 N1 109.8(3) . . ? 
O1 C8 C9 106.6(3) . . ? 
N2 C10 C11 119.3(3) . . ? 
N3 C11 C10 113.2(3) . . ? 
N3 C11 C15 129.7(3) . . ? 
C10 C11 C15 116.9(3) . . ? 
O3 C12 O4 126.5(3) . . ? 
O3 C12 N4 125.5(3) . . ? 
O4 C12 N4 108.0(3) . . ? 
O4 C13 C14 109.0(3) . . ? 
O5 C15 C11 111.2(3) . . ? 
O5 C15 C18 108.7(3) . . ? 
C11 C15 C18 111.2(3) . . ? 
O6 C16 O5 122.6(3) . . ? 
O6 C16 C17 126.8(3) . . ? 
O5 C16 C17 110.6(3) . . ? 
O7 C18 C21 107.0(2) . . ? 
O7 C18 C15 109.4(3) . . ? 
C21 C18 C15 113.1(3) . . ? 
O8 C19 O7 122.6(3) . . ? 
O8 C19 C20 126.6(3) . . ? 
O7 C19 C20 110.7(3) . . ? 
O9 C21 C24 110.2(3) . . ? 
O9 C21 C18 104.6(2) . . ? 
C24 C21 C18 114.2(3) . . ? 
O10 C22 O9 122.7(3) . . ? 
O10 C22 C23 126.5(3) . . ? 
O9 C22 C23 110.7(3) . . ? 
O11 C24 C21 107.2(3) . . ? 
O12 C25 O11 123.0(3) . . ? 
O12 C25 C26 125.5(3) . . ? 
O11 C25 C26 111.5(3) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N4 H4A O5  0.88 2.05 2.698(4) 130.0 . 
 
_diffrn_measured_fraction_theta_max    0.991 
_diffrn_reflns_theta_full              25.03 
_diffrn_measured_fraction_theta_full   0.991 
_refine_diff_density_max    0.435 
_refine_diff_density_min   -0.259 
_refine_diff_density_rms    0.056 
