 
data_92src122
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C13 H19 Cl O8'
_chemical_formula_sum
 'C13 H19 Cl O8'
_chemical_formula_weight          338.73
_chemical_absolute_configuration  unk
 
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'
 '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    P212121
_symmetry_space_group_name_hall   'P 2ac 2ab'
 
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                    7.9919(4)
_cell_length_b                    22.982(6)
_cell_length_c                    8.845(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1624.6(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unk
_exptl_crystal_colour             unk
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.385
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              712
_exptl_absorpt_coefficient_mu     0.271
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             5750
_diffrn_reflns_av_R_equivalents   0.0400
_diffrn_reflns_av_sigmaI/netI     0.1869
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.44
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2778
_reflns_number_gt                 2122
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0000P)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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.04(8)
_refine_ls_number_reflns          2778
_refine_ls_number_parameters      199
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0409
_refine_ls_R_factor_gt            0.0316
_refine_ls_wR_factor_ref          0.0900
_refine_ls_wR_factor_gt           0.0763
_refine_ls_goodness_of_fit_ref    0.406
_refine_ls_restrained_S_all       0.406
_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
Cl Cl 0.65323(8) 0.22574(3) 0.03880(8) 0.04580(19) Uani 1 1 d . . .
C1 C 0.7615(3) 0.25953(10) 0.1929(3) 0.0329(5) Uani 1 1 d . . .
H1A H 0.6992 0.2533 0.2857 0.039 Uiso 1 1 calc R . .
H1B H 0.8707 0.2417 0.2046 0.039 Uiso 1 1 calc R . .
C2 C 0.7821(3) 0.32364(10) 0.1663(3) 0.0268(5) Uani 1 1 d . . .
H2 H 0.8314 0.3299 0.0662 0.032 Uiso 1 1 calc R . .
C3 C 0.8948(3) 0.35102(10) 0.2864(2) 0.0250(5) Uani 1 1 d . . .
H3 H 1.0058 0.3330 0.2819 0.030 Uiso 1 1 calc R . .
C4 C 0.9121(3) 0.41654(10) 0.2681(3) 0.0272(5) Uani 1 1 d . . .
H4 H 0.8009 0.4343 0.2733 0.033 Uiso 1 1 calc R . .
C5 C 1.0239(3) 0.44444(10) 0.3863(3) 0.0313(5) Uani 1 1 d . . .
H5A H 1.0540 0.4835 0.3552 0.038 Uiso 1 1 calc R . .
H5B H 0.9655 0.4468 0.4822 0.038 Uiso 1 1 calc R . .
O1 O 0.61977(18) 0.35095(7) 0.17219(17) 0.0287(4) Uani 1 1 d . . .
O11 O 0.6370(2) 0.37711(10) -0.0723(2) 0.0548(5) Uani 1 1 d . . .
C11 C 0.5607(3) 0.37587(10) 0.0431(3) 0.0313(5) Uani 1 1 d . . .
C12 C 0.3929(3) 0.40225(11) 0.0684(3) 0.0391(6) Uani 1 1 d . . .
H12A H 0.4059 0.4400 0.1132 0.059 Uiso 1 1 calc R . .
H12B H 0.3290 0.3778 0.1349 0.059 Uiso 1 1 calc R . .
H12C H 0.3357 0.4059 -0.0265 0.059 Uiso 1 1 calc R . .
O2 O 0.82369(18) 0.34185(6) 0.43428(16) 0.0283(3) Uani 1 1 d . . .
O21 O 1.0219(2) 0.27620(9) 0.4902(2) 0.0538(5) Uani 1 1 d . . .
C21 C 0.9015(3) 0.30371(10) 0.5271(3) 0.0337(5) Uani 1 1 d . . .
C22 C 0.8146(3) 0.30043(13) 0.6760(3) 0.0447(7) Uani 1 1 d . . .
H22A H 0.8761 0.2753 0.7425 0.067 Uiso 1 1 calc R . .
H22B H 0.7037 0.2852 0.6619 0.067 Uiso 1 1 calc R . .
H22C H 0.8079 0.3386 0.7194 0.067 Uiso 1 1 calc R . .
O3 O 0.97910(19) 0.42450(7) 0.11779(18) 0.0294(4) Uani 1 1 d . . .
O31 O 0.8055(2) 0.49987(8) 0.0784(2) 0.0539(5) Uani 1 1 d . . .
C31 C 0.9090(3) 0.46675(11) 0.0315(3) 0.0360(6) Uani 1 1 d . . .
C32 C 0.9777(4) 0.46510(13) -0.1247(3) 0.0460(7) Uani 1 1 d . . .
H32A H 0.9155 0.4913 -0.1879 0.069 Uiso 1 1 calc R . .
H32B H 0.9688 0.4263 -0.1641 0.069 Uiso 1 1 calc R . .
H32C H 1.0931 0.4766 -0.1231 0.069 Uiso 1 1 calc R . .
O4 O 1.1728(2) 0.40918(7) 0.40195(19) 0.0354(4) Uani 1 1 d . . .
O41 O 1.2415(2) 0.45862(9) 0.6089(2) 0.0517(5) Uani 1 1 d . . .
C41 C 1.2687(3) 0.41935(10) 0.5230(3) 0.0315(5) Uani 1 1 d . . .
C42 C 1.4115(3) 0.37797(11) 0.5335(4) 0.0457(7) Uani 1 1 d . . .
H42A H 1.4708 0.3844 0.6264 0.069 Uiso 1 1 calc R . .
H42B H 1.4858 0.3840 0.4497 0.069 Uiso 1 1 calc R . .
H42C H 1.3701 0.3388 0.5313 0.069 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl C1 1.792(2) . ?
C1 C2 1.501(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O1 1.442(3) . ?
C2 C3 1.528(3) . ?
C2 H2 0.9800 . ?
C3 O2 1.442(3) . ?
C3 C4 1.521(3) . ?
C3 H3 0.9800 . ?
C4 O3 1.445(3) . ?
C4 C5 1.517(3) . ?
C4 H4 0.9800 . ?
C5 O4 1.446(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O1 C11 1.362(3) . ?
O11 C11 1.189(3) . ?
C11 C12 1.489(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O2 C21 1.353(3) . ?
O21 C21 1.197(3) . ?
C21 C22 1.491(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O3 C31 1.356(3) . ?
O31 C31 1.198(3) . ?
C31 C32 1.487(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
O4 C41 1.337(3) . ?
O41 C41 1.200(3) . ?
C41 C42 1.489(3) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
 
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 C1 Cl 111.05(17) . . ?
C2 C1 H1A 109.4 . . ?
Cl C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
Cl C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O1 C2 C1 108.84(18) . . ?
O1 C2 C3 109.04(17) . . ?
C1 C2 C3 111.09(19) . . ?
O1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
O2 C3 C4 106.06(17) . . ?
O2 C3 C2 109.75(17) . . ?
C4 C3 C2 112.82(18) . . ?
O2 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
O3 C4 C5 111.23(18) . . ?
O3 C4 C3 104.87(17) . . ?
C5 C4 C3 113.53(19) . . ?
O3 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
O4 C5 C4 108.30(17) . . ?
O4 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
O4 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C11 O1 C2 117.69(17) . . ?
O11 C11 O1 123.5(2) . . ?
O11 C11 C12 125.5(2) . . ?
O1 C11 C12 110.9(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C21 O2 C3 117.67(17) . . ?
O21 C21 O2 123.1(2) . . ?
O21 C21 C22 126.1(2) . . ?
O2 C21 C22 110.8(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C31 O3 C4 117.11(18) . . ?
O31 C31 O3 123.0(2) . . ?
O31 C31 C32 126.4(2) . . ?
O3 C31 C32 110.6(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C41 O4 C5 116.76(17) . . ?
O41 C41 O4 122.3(2) . . ?
O41 C41 C42 125.4(2) . . ?
O4 C41 C42 112.2(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.967
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.967
_refine_diff_density_max    0.167
_refine_diff_density_min   -0.161
_refine_diff_density_rms    0.034
