data_2007src1354
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H25 Cl N2 O5'
_chemical_formula_weight          432.89
 
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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    9.7683(2)
_cell_length_b                    13.0654(2)
_cell_length_c                    16.8119(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2145.65(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     44602
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.35
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.340
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              912
_exptl_absorpt_coefficient_mu     0.214
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9288
_exptl_absorpt_correction_T_max   0.9584
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_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 Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             20476
_diffrn_reflns_av_R_equivalents   0.0487
_diffrn_reflns_av_sigmaI/netI     0.0419
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.12
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4898
_reflns_number_gt                 4406
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_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)+(0.0539P)²+0.6403P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.04(6)
_refine_ls_number_reflns          4898
_refine_ls_number_parameters      293
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0490
_refine_ls_R_factor_gt            0.0418
_refine_ls_wR_factor_ref          0.1051
_refine_ls_wR_factor_gt           0.1007
_refine_ls_goodness_of_fit_ref    1.038
_refine_ls_restrained_S_all       1.038
_refine_ls_shift/su_max           0.013
_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
O2 O 0.6173(3) 0.0423(3) 0.03264(16) 0.1014(10) Uani 1 1 d . A .
O3 O 0.4875(3) -0.06810(18) 0.11211(12) 0.0725(7) Uani 1 1 d . A .
O4 O 0.7061(4) -0.0371(3) 0.1332(4) 0.098(3) Uani 0.585(6) 1 d P A 1
O5 O 0.5659(8) 0.1010(3) 0.1519(4) 0.109(3) Uani 0.585(6) 1 d P A 1
O4' O 0.4387(6) 0.0837(3) 0.1152(3) 0.0543(18) Uani 0.415(6) 1 d P A 2
O5' O 0.6277(7) 0.0367(5) 0.1868(3) 0.073(3) Uani 0.415(6) 1 d P A 2
Cl1 Cl 0.57542(7) 0.01509(4) 0.10899(3) 0.04143(16) Uani 1 1 d . . .
C1 C 0.11480(18) 0.21191(14) 0.26738(11) 0.0200(4) Uani 1 1 d . . .
C2 C 0.0533(2) 0.19968(14) 0.34222(11) 0.0231(4) Uani 1 1 d . . .
H2 H 0.0855 0.2384 0.3862 0.028 Uiso 1 1 calc R . .
C3 C -0.0542(2) 0.13146(15) 0.35250(12) 0.0269(4) Uani 1 1 d . . .
H3 H -0.0945 0.1227 0.4035 0.032 Uiso 1 1 calc R . .
C4 C -0.1027(2) 0.07601(15) 0.28788(12) 0.0267(4) Uani 1 1 d . . .
H4 H -0.1764 0.0294 0.2947 0.032 Uiso 1 1 calc R . .
C5 C -0.0437(2) 0.08842(15) 0.21310(12) 0.0255(4) Uani 1 1 d . . .
H5 H -0.0777 0.0505 0.1691 0.031 Uiso 1 1 calc R . .
C6 C 0.06416(19) 0.15575(14) 0.20250(11) 0.0224(4) Uani 1 1 d . . .
H6 H 0.1040 0.1640 0.1513 0.027 Uiso 1 1 calc R . .
C7 C 0.23636(19) 0.27574(14) 0.26168(11) 0.0212(4) Uani 1 1 d . . .
H7 H 0.2645 0.3096 0.3089 0.025 Uiso 1 1 calc R . .
C8 C 0.31366(19) 0.29187(14) 0.19589(11) 0.0212(4) Uani 1 1 d . . .
H8 H 0.2830 0.2721 0.1445 0.025 Uiso 1 1 calc R . .
C9 C 0.44275(19) 0.33980(13) 0.20745(10) 0.0194(4) Uani 1 1 d . . .
H9 H 0.4610 0.3670 0.2588 0.023 Uiso 1 1 calc R . .
C10 C 0.68159(19) 0.38102(14) 0.17608(10) 0.0184(4) Uani 1 1 d . . .
C11 C 0.6897(2) 0.49468(14) 0.19458(11) 0.0227(4) Uani 1 1 d . . .
H11A H 0.7835 0.5123 0.2101 0.034 Uiso 1 1 calc R . .
H11B H 0.6270 0.5110 0.2383 0.034 Uiso 1 1 calc R . .
H11C H 0.6639 0.5340 0.1473 0.034 Uiso 1 1 calc R . .
C12 C 0.7318(2) 0.31634(15) 0.24584(11) 0.0266(4) Uani 1 1 d . . .
H12A H 0.7093 0.2443 0.2362 0.040 Uiso 1 1 calc R . .
H12B H 0.6870 0.3393 0.2949 0.040 Uiso 1 1 calc R . .
H12C H 0.8312 0.3239 0.2512 0.040 Uiso 1 1 calc R . .
C13 C 0.8986(2) 0.37401(17) 0.09247(13) 0.0298(4) Uani 1 1 d . . .
H13A H 0.9266 0.3547 0.0385 0.045 Uiso 1 1 calc R . .
H13B H 0.9509 0.3340 0.1313 0.045 Uiso 1 1 calc R . .
H13C H 0.9163 0.4471 0.1008 0.045 Uiso 1 1 calc R . .
C14 C 0.6742(2) 0.31622(13) 0.04404(10) 0.0206(4) Uani 1 1 d . . .
C15 C 0.52595(19) 0.31830(13) 0.06978(11) 0.0195(4) Uani 1 1 d . . .
H15 H 0.4857 0.2481 0.0662 0.023 Uiso 1 1 calc R . .
C16 C 0.44181(19) 0.39368(14) 0.01860(11) 0.0229(4) Uani 1 1 d . . .
H16A H 0.4419 0.3691 -0.0371 0.027 Uiso 1 1 calc R . .
H16B H 0.3458 0.3930 0.0375 0.027 Uiso 1 1 calc R . .
C17 C 0.49308(18) 0.50235(15) 0.01983(11) 0.0219(4) Uani 1 1 d . . .
C18 C 0.6130(2) 0.53096(14) -0.01999(11) 0.0241(4) Uani 1 1 d . . .
H18 H 0.6601 0.4820 -0.0516 0.029 Uiso 1 1 calc R . .
C19 C 0.6641(2) 0.63030(16) -0.01392(12) 0.0314(5) Uani 1 1 d . . .
H19 H 0.7465 0.6483 -0.0405 0.038 Uiso 1 1 calc R . .
C20 C 0.5946(3) 0.70292(15) 0.03100(12) 0.0349(5) Uani 1 1 d . . .
H20 H 0.6296 0.7705 0.0357 0.042 Uiso 1 1 calc R . .
C21 C 0.4745(3) 0.67614(17) 0.06875(13) 0.0365(5) Uani 1 1 d . . .
H21 H 0.4256 0.7259 0.0986 0.044 Uiso 1 1 calc R . .
C22 C 0.4244(2) 0.57691(16) 0.06338(12) 0.0313(4) Uani 1 1 d . . .
H22 H 0.3418 0.5596 0.0899 0.038 Uiso 1 1 calc R . .
N1 N 0.53782(16) 0.34978(11) 0.15427(9) 0.0179(3) Uani 1 1 d . . .
N2 N 0.75301(16) 0.35365(11) 0.10258(9) 0.0205(3) Uani 1 1 d . . .
O1 O 0.71343(15) 0.28891(10) -0.02224(8) 0.0268(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
O2 Cl1 1.393(2) . ?
O3 Cl1 1.386(2) . ?
O4 Cl1 1.503(4) . ?
O5 Cl1 1.337(4) . ?
O4' Cl1 1.612(4) . ?
O5' Cl1 1.433(5) . ?
C1 C2 1.403(2) . ?
C1 C6 1.405(3) . ?
C1 C7 1.454(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.384(3) . ?
C7 C8 1.356(3) . ?
C8 C9 1.421(3) . ?
C9 N1 1.296(2) . ?
C10 N2 1.463(2) . ?
C10 N1 1.508(2) . ?
C10 C11 1.519(3) . ?
C10 C12 1.526(3) . ?
C13 N2 1.457(2) . ?
C14 O1 1.231(2) . ?
C14 N2 1.342(2) . ?
C14 C15 1.512(3) . ?
C15 N1 1.483(2) . ?
C15 C16 1.545(3) . ?
C16 C17 1.506(3) . ?
C17 C22 1.391(3) . ?
C17 C18 1.400(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.390(3) . ?
C20 C21 1.380(4) . ?
C21 C22 1.388(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
O5 Cl1 O3 126.5(3) . . ?
O5 Cl1 O2 107.6(3) . . ?
O3 Cl1 O2 114.63(17) . . ?
O5 Cl1 O5' 50.7(4) . . ?
O3 Cl1 O5' 109.9(2) . . ?
O2 Cl1 O5' 133.4(3) . . ?
O5 Cl1 O4 107.1(4) . . ?
O3 Cl1 O4 99.22(18) . . ?
O2 Cl1 O4 96.6(3) . . ?
O5' Cl1 O4 62.6(3) . . ?
O5 Cl1 O4' 56.0(3) . . ?
O3 Cl1 O4' 85.4(2) . . ?
O2 Cl1 O4' 99.3(2) . . ?
O5' Cl1 O4' 97.3(4) . . ?
O4 Cl1 O4' 159.8(3) . . ?
C2 C1 C6 119.08(17) . . ?
C2 C1 C7 118.29(17) . . ?
C6 C1 C7 122.41(17) . . ?
C3 C2 C1 120.57(17) . . ?
C2 C3 C4 119.69(18) . . ?
C3 C4 C5 120.30(18) . . ?
C6 C5 C4 120.34(18) . . ?
C5 C6 C1 120.01(17) . . ?
C8 C7 C1 126.70(17) . . ?
C7 C8 C9 116.81(16) . . ?
N1 C9 C8 125.86(16) . . ?
N2 C10 N1 99.93(13) . . ?
N2 C10 C11 112.76(15) . . ?
N1 C10 C11 111.28(15) . . ?
N2 C10 C12 111.13(15) . . ?
N1 C10 C12 109.64(15) . . ?
C11 C10 C12 111.54(15) . . ?
O1 C14 N2 126.22(18) . . ?
O1 C14 C15 124.23(17) . . ?
N2 C14 C15 109.46(15) . . ?
N1 C15 C14 101.79(14) . . ?
N1 C15 C16 113.46(15) . . ?
C14 C15 C16 111.20(15) . . ?
C17 C16 C15 114.62(15) . . ?
C22 C17 C18 117.90(18) . . ?
C22 C17 C16 120.49(17) . . ?
C18 C17 C16 121.57(17) . . ?
C19 C18 C17 120.89(19) . . ?
C20 C19 C18 120.0(2) . . ?
C21 C20 C19 119.50(19) . . ?
C20 C21 C22 120.4(2) . . ?
C21 C22 C17 121.2(2) . . ?
C9 N1 C15 125.23(15) . . ?
C9 N1 C10 121.80(15) . . ?
C15 N1 C10 112.38(14) . . ?
C14 N2 C13 122.76(16) . . ?
C14 N2 C10 115.78(15) . . ?
C13 N2 C10 121.28(15) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.382
_refine_diff_density_min   -0.460
_refine_diff_density_rms    0.047
