 
data_61-62-2
 
_audit_creation_method            'SHELXL-2016/4'
_shelx_SHELXL_version_number      '2016/4'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H32 O4' 
_chemical_formula_weight          360.47

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'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_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                    6.08570(10)
_cell_length_b                    16.6326(3)
_cell_length_c                    19.5442(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1978.28(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used   5838
_cell_measurement_theta_min     3.4580
_cell_measurement_theta_max     73.3460
 
_exptl_crystal_description                block
_exptl_crystal_colour                     colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.210          
_exptl_crystal_F_000              784
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max                             0.110
_exptl_crystal_size_mid                             0.100
_exptl_crystal_size_min                             0.080
_exptl_absorpt_coefficient_mu     0.650
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_correction_T_min                   0.82437
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean 5.2684
_diffrn_reflns_number             8039
_diffrn_reflns_av_unetI/netI      0.0308
_diffrn_reflns_av_R_equivalents   0.0241
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          3.489
_diffrn_reflns_theta_max          73.724
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.966
_diffrn_measured_fraction_theta_full  0.992
_diffrn_reflns_Laue_measured_fraction_max    0.966
_diffrn_reflns_Laue_measured_fraction_full   0.992
_diffrn_reflns_point_group_measured_fraction_max   0.948
_diffrn_reflns_point_group_measured_fraction_full  0.985
_reflns_number_total              3806
_reflns_number_gt                 3699
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.695
_reflns_Friedel_fraction_max      0.924
_reflns_Friedel_fraction_full     0.976
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection     'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement     'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction      'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0849P)²+0.6009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_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 x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.05(9)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          3806
_refine_ls_number_parameters      241
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0475
_refine_ls_R_factor_gt            0.0462
_refine_ls_wR_factor_ref          0.1318
_refine_ls_wR_factor_gt           0.1296
_refine_ls_goodness_of_fit_ref    1.067
_refine_ls_restrained_S_all       1.067
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.6942(4) 0.50635(15) 0.38288(12) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.8191(4) 0.58442(15) 0.39528(13) 0.0188(5) Uani 1 1 d . . . . .
H2 H 0.923727 0.598942 0.359213 0.023 Uiso 1 1 calc R U . . .
C3 C 0.9175(4) 0.58183(16) 0.46859(13) 0.0220(5) Uani 1 1 d . . . . .
H3A H 0.948532 0.528087 0.485274 0.026 Uiso 1 1 calc R U . . .
H3B H 1.041902 0.617424 0.475404 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6962(4) 0.61655(16) 0.49312(13) 0.0215(5) Uani 1 1 d . . . . .
H4 H 0.705296 0.654717 0.531209 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5401(4) 0.54593(16) 0.50390(13) 0.0217(5) Uani 1 1 d . . . . .
H5A H 0.394302 0.566544 0.513674 0.026 Uiso 1 1 calc R U . . .
H5B H 0.588294 0.515405 0.543434 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5269(4) 0.48879(16) 0.44111(12) 0.0208(5) Uani 1 1 d . . . . .
H6A H 0.379746 0.491866 0.422214 0.025 Uiso 1 1 calc R U . . .
H6B H 0.549323 0.434088 0.456846 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5913(4) 0.50071(15) 0.31132(12) 0.0192(5) Uani 1 1 d . . . . .
H7A H 0.704765 0.509069 0.277183 0.023 Uiso 1 1 calc R U . . .
H7B H 0.483214 0.543125 0.306126 0.023 Uiso 1 1 calc R U . . .
C8 C 0.6694(4) 0.65507(16) 0.42055(13) 0.0202(5) Uani 1 1 d . . . . .
C9 C 0.7929(5) 0.73519(15) 0.41482(15) 0.0262(6) Uani 1 1 d . . . . .
H9A H 0.801947 0.750822 0.367620 0.039 Uiso 1 1 calc R U . . .
H9B H 0.938429 0.729107 0.433090 0.039 Uiso 1 1 calc R U . . .
H9C H 0.715781 0.775776 0.440167 0.039 Uiso 1 1 calc R U . . .
C10 C 0.4386(4) 0.66845(16) 0.39211(14) 0.0232(5) Uani 1 1 d . . . . .
H10A H 0.367877 0.710777 0.417210 0.035 Uiso 1 1 calc R U . . .
H10B H 0.354765 0.619835 0.396535 0.035 Uiso 1 1 calc R U . . .
H10C H 0.448074 0.683146 0.344702 0.035 Uiso 1 1 calc R U . . .
C1' C 0.6378(4) 0.35584(16) 0.32290(13) 0.0202(5) Uani 1 1 d . . . . .
C2' C 0.6263(5) 0.26925(16) 0.31537(13) 0.0225(6) Uani 1 1 d . . . . .
C3' C 0.8068(5) 0.23254(15) 0.36252(14) 0.0232(6) Uani 1 1 d . . . . .
C4' C 0.9648(5) 0.30305(15) 0.37620(14) 0.0228(6) Uani 1 1 d . . . . .
H4'1 H 1.014787 0.303630 0.423322 0.027 Uiso 1 1 calc R U . . .
H4'2 H 1.090916 0.301528 0.345877 0.027 Uiso 1 1 calc R U . . .
C5' C 0.8190(4) 0.37303(15) 0.36092(13) 0.0191(5) Uani 1 1 d . . . . .
C6' C 0.4803(4) 0.41898(15) 0.29853(13) 0.0199(5) Uani 1 1 d . . . . .
H6' H 0.349737 0.416313 0.327811 0.024 Uiso 1 1 calc R U . . .
C7' C 0.4039(5) 0.40540(16) 0.22374(13) 0.0236(6) Uani 1 1 d . . . . .
H7' H 0.339615 0.351442 0.221654 0.028 Uiso 1 1 calc R U . . .
C8' C 0.5906(5) 0.40759(19) 0.17192(14) 0.0305(6) Uani 1 1 d . . . . .
H8'1 H 0.536525 0.391291 0.127914 0.046 Uiso 1 1 calc R U . . .
H8'2 H 0.705124 0.371609 0.186200 0.046 Uiso 1 1 calc R U . . .
H8'3 H 0.647937 0.461252 0.168969 0.046 Uiso 1 1 calc R U . . .
C9' C 0.2229(5) 0.4646(2) 0.20462(15) 0.0317(6) Uani 1 1 d . . . . .
H9'1 H 0.282094 0.518039 0.203373 0.048 Uiso 1 1 calc R U . . .
H9'2 H 0.107479 0.461967 0.238021 0.048 Uiso 1 1 calc R U . . .
H9'3 H 0.165113 0.450936 0.160409 0.048 Uiso 1 1 calc R U . . .
C10' C 0.6809(5) 0.21140(17) 0.42877(14) 0.0274(6) Uani 1 1 d . . . . .
C11' C 0.5808(8) 0.12899(19) 0.4329(2) 0.0487(10) Uani 1 1 d . . . . .
H11A H 0.478698 0.127118 0.470331 0.073 Uiso 1 1 calc R U . . .
H11B H 0.694611 0.089922 0.440134 0.073 Uiso 1 1 calc R U . . .
H11C H 0.505244 0.117271 0.390988 0.073 Uiso 1 1 calc R U . . .
C12' C 0.9902(7) 0.1651(2) 0.27241(19) 0.0437(8) Uani 1 1 d . . . . .
H12A H 0.875587 0.173804 0.239486 0.066 Uiso 1 1 calc R U . . .
H12B H 1.064204 0.115487 0.262321 0.066 Uiso 1 1 calc R U . . .
H12C H 1.093398 0.208653 0.270381 0.066 Uiso 1 1 calc R U . . .
O1 O 0.6556(4) 0.26186(12) 0.47262(10) 0.0306(5) Uani 1 1 d . . . . .
O2 O 0.9000(4) 0.16110(12) 0.33728(12) 0.0350(5) Uani 1 1 d . . . . .
O3 O 0.8727(3) 0.44464(10) 0.38637(9) 0.0196(4) Uani 1 1 d . . . . .
O4 O 0.4967(4) 0.22842(12) 0.28243(11) 0.0298(5) 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
C1 O3 1.496(3) . ?
C1 C2 1.524(3) . ?
C1 C7 1.535(3) . ?
C1 C6 1.555(3) . ?
C2 C3 1.554(3) . ?
C2 C8 1.567(3) . ?
C3 C4 1.542(4) . ?
C4 C5 1.525(4) . ?
C4 C8 1.565(3) . ?
C5 C6 1.554(3) . ?
C7 C6' 1.539(3) . ?
C8 C10 1.527(4) . ?
C8 C9 1.534(4) . ?
C1' C5' 1.360(4) . ?
C1' C2' 1.450(4) . ?
C1' C6' 1.500(4) . ?
C2' O4 1.224(3) . ?
C2' C3' 1.559(4) . ?
C3' O2 1.406(3) . ?
C3' C4' 1.540(3) . ?
C3' C10' 1.545(4) . ?
C4' C5' 1.494(3) . ?
C5' O3 1.331(3) . ?
C6' C7' 1.550(3) . ?
C7' C8' 1.522(4) . ?
C7' C9' 1.524(4) . ?
C10' O1 1.209(4) . ?
C10' C11' 1.502(4) . ?
C12' O2 1.383(4) . ?
 
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
O3 C1 C2 102.44(18) . . ?
O3 C1 C7 107.20(19) . . ?
C2 C1 C7 113.6(2) . . ?
O3 C1 C6 108.26(19) . . ?
C2 C1 C6 111.7(2) . . ?
C7 C1 C6 112.8(2) . . ?
C1 C2 C3 108.4(2) . . ?
C1 C2 C8 113.5(2) . . ?
C3 C2 C8 87.38(18) . . ?
C4 C3 C2 86.53(19) . . ?
C5 C4 C3 107.4(2) . . ?
C5 C4 C8 112.1(2) . . ?
C3 C4 C8 87.86(19) . . ?
C4 C5 C6 113.2(2) . . ?
C5 C6 C1 115.4(2) . . ?
C1 C7 C6' 112.4(2) . . ?
C10 C8 C9 107.3(2) . . ?
C10 C8 C4 119.0(2) . . ?
C9 C8 C4 111.8(2) . . ?
C10 C8 C2 122.0(2) . . ?
C9 C8 C2 110.1(2) . . ?
C4 C8 C2 85.30(18) . . ?
C5' C1' C2' 107.7(2) . . ?
C5' C1' C6' 123.0(2) . . ?
C2' C1' C6' 129.2(2) . . ?
O4 C2' C1' 129.5(3) . . ?
O4 C2' C3' 123.2(2) . . ?
C1' C2' C3' 107.2(2) . . ?
O2 C3' C4' 116.9(2) . . ?
O2 C3' C10' 107.6(2) . . ?
C4' C3' C10' 109.7(2) . . ?
O2 C3' C2' 114.1(2) . . ?
C4' C3' C2' 104.2(2) . . ?
C10' C3' C2' 103.6(2) . . ?
C5' C4' C3' 100.8(2) . . ?
O3 C5' C1' 126.2(2) . . ?
O3 C5' C4' 118.5(2) . . ?
C1' C5' C4' 115.3(2) . . ?
C1' C6' C7 106.6(2) . . ?
C1' C6' C7' 112.9(2) . . ?
C7 C6' C7' 114.4(2) . . ?
C8' C7' C9' 111.2(2) . . ?
C8' C7' C6' 113.6(2) . . ?
C9' C7' C6' 110.7(2) . . ?
O1 C10' C11' 122.9(3) . . ?
O1 C10' C3' 119.9(2) . . ?
C11' C10' C3' 117.0(2) . . ?
C12' O2 C3' 116.2(2) . . ?
C5' O3 C1 114.74(19) . . ?
 
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
O3 C1 C2 C3 -63.8(2) . . . . ?
C7 C1 C2 C3 -179.1(2) . . . . ?
C6 C1 C2 C3 51.9(3) . . . . ?
O3 C1 C2 C8 -159.10(19) . . . . ?
C7 C1 C2 C8 85.6(3) . . . . ?
C6 C1 C2 C8 -43.4(3) . . . . ?
C1 C2 C3 C4 -87.1(2) . . . . ?
C8 C2 C3 C4 26.85(19) . . . . ?
C2 C3 C4 C5 85.6(2) . . . . ?
C2 C3 C4 C8 -26.88(18) . . . . ?
C3 C4 C5 C6 -51.4(3) . . . . ?
C8 C4 C5 C6 43.4(3) . . . . ?
C4 C5 C6 C1 7.6(3) . . . . ?
O3 C1 C6 C5 104.3(2) . . . . ?
C2 C1 C6 C5 -7.8(3) . . . . ?
C7 C1 C6 C5 -137.2(2) . . . . ?
O3 C1 C7 C6' 63.6(2) . . . . ?
C2 C1 C7 C6' 176.0(2) . . . . ?
C6 C1 C7 C6' -55.5(3) . . . . ?
C5 C4 C8 C10 43.0(3) . . . . ?
C3 C4 C8 C10 150.9(2) . . . . ?
C5 C4 C8 C9 169.0(2) . . . . ?
C3 C4 C8 C9 -83.1(2) . . . . ?
C5 C4 C8 C2 -81.2(2) . . . . ?
C3 C4 C8 C2 26.68(18) . . . . ?
C1 C2 C8 C10 -39.1(3) . . . . ?
C3 C2 C8 C10 -148.0(2) . . . . ?
C1 C2 C8 C9 -166.1(2) . . . . ?
C3 C2 C8 C9 85.0(2) . . . . ?
C1 C2 C8 C4 82.4(2) . . . . ?
C3 C2 C8 C4 -26.47(19) . . . . ?
C5' C1' C2' O4 -176.0(3) . . . . ?
C6' C1' C2' O4 7.3(5) . . . . ?
C5' C1' C2' C3' 7.8(3) . . . . ?
C6' C1' C2' C3' -168.9(2) . . . . ?
O4 C2' C3' O2 36.1(4) . . . . ?
C1' C2' C3' O2 -147.4(2) . . . . ?
O4 C2' C3' C4' 164.7(2) . . . . ?
C1' C2' C3' C4' -18.9(3) . . . . ?
O4 C2' C3' C10' -80.5(3) . . . . ?
C1' C2' C3' C10' 95.9(2) . . . . ?
O2 C3' C4' C5' 148.0(2) . . . . ?
C10' C3' C4' C5' -89.2(2) . . . . ?
C2' C3' C4' C5' 21.2(2) . . . . ?
C2' C1' C5' O3 -171.1(2) . . . . ?
C6' C1' C5' O3 5.9(4) . . . . ?
C2' C1' C5' C4' 7.2(3) . . . . ?
C6' C1' C5' C4' -175.8(2) . . . . ?
C3' C4' C5' O3 159.7(2) . . . . ?
C3' C4' C5' C1' -18.7(3) . . . . ?
C5' C1' C6' C7 11.8(3) . . . . ?
C2' C1' C6' C7 -171.9(2) . . . . ?
C5' C1' C6' C7' 138.3(2) . . . . ?
C2' C1' C6' C7' -45.4(4) . . . . ?
C1 C7 C6' C1' -45.9(3) . . . . ?
C1 C7 C6' C7' -171.5(2) . . . . ?
C1' C6' C7' C8' -61.3(3) . . . . ?
C7 C6' C7' C8' 60.9(3) . . . . ?
C1' C6' C7' C9' 172.8(2) . . . . ?
C7 C6' C7' C9' -65.0(3) . . . . ?
O2 C3' C10' O1 153.0(3) . . . . ?
C4' C3' C10' O1 24.8(4) . . . . ?
C2' C3' C10' O1 -85.9(3) . . . . ?
O2 C3' C10' C11' -31.3(4) . . . . ?
C4' C3' C10' C11' -159.5(3) . . . . ?
C2' C3' C10' C11' 89.8(3) . . . . ?
C4' C3' O2 C12' -66.1(4) . . . . ?
C10' C3' O2 C12' 170.0(3) . . . . ?
C2' C3' O2 C12' 55.7(3) . . . . ?
C1' C5' O3 C1 11.9(3) . . . . ?
C4' C5' O3 C1 -166.3(2) . . . . ?
C2 C1 O3 C5' -164.3(2) . . . . ?
C7 C1 O3 C5' -44.5(3) . . . . ?
C6 C1 O3 C5' 77.5(2) . . . . ?
 
_refine_diff_density_max    1.135
_refine_diff_density_min   -0.435
_refine_diff_density_rms    0.058



