 
data_exp_9781
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H13 O8 Zn' 
_chemical_formula_weight          326.57

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'
 'Zn'  'Zn'  -1.5491   0.6778
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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, -y, -z'
 
_cell_length_a                    7.6844(15)
_cell_length_b                    8.4799(12)
_cell_length_c                    9.8498(14)
_cell_angle_alpha                 67.682(14)
_cell_angle_beta                  82.043(14)
_cell_angle_gamma                 87.656(14)
_cell_volume                      588.00(18)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used   735
_cell_measurement_theta_min     4.8850
_cell_measurement_theta_max     67.0550
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.845          
_exptl_crystal_F_000              334
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     3.275
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_T_min                   0.94877
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_process_details    sadabs
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Xcalibur, Eos, Gemini'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             3581
_diffrn_reflns_av_unetI/netI      0.0993
_diffrn_reflns_av_R_equivalents   0.0523
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          4.897
_diffrn_reflns_theta_max          75.458
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.931
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.931
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.931
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              2274
_reflns_number_gt                 1492
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement     'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction      'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution     'SHELXL-2018/3 '
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0869P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     refU
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2274
_refine_ls_number_parameters      185
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1095
_refine_ls_R_factor_gt            0.0693
_refine_ls_wR_factor_ref          0.1912
_refine_ls_wR_factor_gt           0.1633
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.040
_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
Zn1 Zn 0.47048(15) 0.34592(12) 0.38535(10) 0.0424(3) Uani 1 1 d . . . . .
O1 O 0.8321(7) 1.2369(5) -0.0816(5) 0.0401(11) Uani 1 1 d . . . . .
O4 O 0.6384(7) 0.5343(6) 0.3414(5) 0.0441(12) Uani 1 1 d . . . . .
O3 O 0.5567(7) 0.6602(6) -0.1879(6) 0.0474(13) Uani 1 1 d . . . . .
O2 O 0.6216(8) 0.7611(6) 0.4031(5) 0.0515(15) Uani 1 1 d . . . . .
O5 O 0.6927(9) 0.8794(7) -0.3573(5) 0.0553(15) Uani 1 1 d . . . . .
O6 O 0.2481(8) 0.5270(7) 0.3567(6) 0.0554(15) Uani 1 1 d . . . . .
H9 H 0.222634 0.599983 0.275158 0.06(3) Uiso 1 1 d R . . . .
H8 H 0.239271 0.573712 0.419866 0.17(7) Uiso 1 1 d R . . . .
O7 O 0.6842(8) 0.1792(7) 0.4065(7) 0.0600(16) Uani 1 1 d . . . . .
H11 H 0.640474 0.095832 0.482636 0.07(3) Uiso 1 1 d R . . . .
H10 H 0.750131 0.236841 0.433550 0.14(6) Uiso 1 1 d R . . . .
C1 C 0.6403(10) 0.7962(9) -0.2257(8) 0.0399(16) Uani 1 1 d . . . . .
C8 C 0.7415(9) 1.0165(8) -0.1436(7) 0.0371(15) Uani 1 1 d . . . . .
H2 H 0.759027 1.085953 -0.243660 0.031(18) Uiso 1 1 d R . . . .
C3 C 0.6435(9) 0.7465(8) 0.0415(7) 0.0333(14) Uani 1 1 d . . . . .
H1 H 0.602752 0.636344 0.064466 0.030(17) Uiso 1 1 d R . . . .
C9 C 0.8835(10) 1.2962(8) 0.0258(7) 0.0367(15) Uani 1 1 d . . . . .
H5 H 0.783465 1.309858 0.091979 0.04(2) Uiso 1 1 d R . . . .
H4 H 0.967870 1.217998 0.080467 0.05(2) Uiso 1 1 d R . . . .
C2 C 0.6765(9) 0.8539(8) -0.1051(7) 0.0321(13) Uani 1 1 d . . . . .
C7 C 0.7728(9) 1.0732(8) -0.0329(7) 0.0313(13) Uani 1 1 d . . . . .
C4 C 0.6777(9) 0.8041(8) 0.1503(7) 0.0344(14) Uani 1 1 d . . . . .
C10 C 0.9673(9) 1.4681(8) -0.0539(8) 0.0377(15) Uani 1 1 d . . . . .
H6 H 1.065548 1.457907 -0.123239 0.05(2) Uiso 1 1 d R . . . .
H7 H 0.882009 1.548558 -0.104757 0.05(2) Uiso 1 1 d R . . . .
C5 C 0.6426(9) 0.6900(8) 0.3096(7) 0.0367(15) Uani 1 1 d . . . . .
C6 C 0.7384(9) 0.9678(8) 0.1147(7) 0.0341(14) Uani 1 1 d . . . . .
H3 H 0.747929 1.010404 0.187619 0.021(15) Uiso 1 1 d R . . . .
O8 O -0.0204(12) 0.2676(14) 0.4834(10) 0.097(3) Uani 1 1 d . . . . .
H12 H 0.051360 0.191813 0.475095 0.14(7) Uiso 1 1 d R . . . .
H13 H 0.033677 0.362994 0.449476 0.38(18) Uiso 1 1 d 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
Zn1 O2 1.968(5) 2_666 ?
Zn1 O4 1.973(4) . ?
Zn1 O3 2.005(5) 2_665 ?
Zn1 O7 2.102(6) . ?
Zn1 O6 2.224(6) . ?
Zn1 O5 2.448(6) 2_665 ?
Zn1 C1 2.558(7) 2_665 ?
O1 C7 1.360(7) . ?
O1 C9 1.437(8) . ?
O4 C5 1.236(8) . ?
O3 C1 1.245(8) . ?
O2 C5 1.269(8) . ?
O5 C1 1.235(9) . ?
C1 C2 1.507(9) . ?
C8 C2 1.379(9) . ?
C8 C7 1.400(9) . ?
C3 C2 1.378(9) . ?
C3 C4 1.394(9) . ?
C9 C10 1.491(8) . ?
C7 C6 1.382(9) . ?
C4 C6 1.381(8) . ?
C4 C5 1.490(8) . ?
C10 C10 1.508(13) 2_785 ?
 
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
O2 Zn1 O4 113.2(2) 2_666 . ?
O2 Zn1 O3 141.5(2) 2_666 2_665 ?
O4 Zn1 O3 105.1(2) . 2_665 ?
O2 Zn1 O7 92.8(2) 2_666 . ?
O4 Zn1 O7 88.6(2) . . ?
O3 Zn1 O7 91.0(2) 2_665 . ?
O2 Zn1 O6 88.8(2) 2_666 . ?
O4 Zn1 O6 90.4(2) . . ?
O3 Zn1 O6 88.0(2) 2_665 . ?
O7 Zn1 O6 178.4(2) . . ?
O2 Zn1 O5 85.29(19) 2_666 2_665 ?
O4 Zn1 O5 160.8(2) . 2_665 ?
O3 Zn1 O5 56.90(18) 2_665 2_665 ?
O7 Zn1 O5 85.3(2) . 2_665 ?
O6 Zn1 O5 95.3(2) . 2_665 ?
O2 Zn1 C1 113.6(2) 2_666 2_665 ?
O4 Zn1 C1 133.1(2) . 2_665 ?
O3 Zn1 C1 28.5(2) 2_665 2_665 ?
O7 Zn1 C1 86.7(2) . 2_665 ?
O6 Zn1 C1 93.0(2) . 2_665 ?
O5 Zn1 C1 28.4(2) 2_665 2_665 ?
C7 O1 C9 117.7(5) . . ?
C5 O4 Zn1 140.9(5) . . ?
C1 O3 Zn1 101.3(4) . 2_665 ?
C5 O2 Zn1 126.8(4) . 2_666 ?
C1 O5 Zn1 80.7(4) . 2_665 ?
O5 C1 O3 120.9(6) . . ?
O5 C1 C2 121.5(6) . . ?
O3 C1 C2 117.6(6) . . ?
O5 C1 Zn1 70.8(4) . 2_665 ?
O3 C1 Zn1 50.2(3) . 2_665 ?
C2 C1 Zn1 167.3(5) . 2_665 ?
C2 C8 C7 119.7(6) . . ?
C2 C3 C4 119.0(6) . . ?
O1 C9 C10 108.6(5) . . ?
C3 C2 C8 120.5(6) . . ?
C3 C2 C1 120.5(6) . . ?
C8 C2 C1 119.0(6) . . ?
O1 C7 C6 124.1(6) . . ?
O1 C7 C8 115.4(5) . . ?
C6 C7 C8 120.5(6) . . ?
C6 C4 C3 121.5(6) . . ?
C6 C4 C5 118.5(6) . . ?
C3 C4 C5 119.9(5) . . ?
C9 C10 C10 110.6(7) . 2_785 ?
O4 C5 O2 124.8(6) . . ?
O4 C5 C4 118.3(6) . . ?
O2 C5 C4 116.9(6) . . ?
C4 C6 C7 118.6(6) . . ?
 
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 
 _geom_hbond_publ_flag
O8 H13 O6  0.85 2.07 2.868(10) 155.9 . yes
O8 H12 O5  0.85 2.32 3.081(12) 149.2 2_665 yes
O7 H10 O8  0.85 1.95 2.708(10) 148.3 1_655 yes
O7 H11 O5  0.85 1.98 2.723(7) 145.0 1_546 yes
O6 H8 O8  0.85 2.43 3.106(12) 137.3 2_566 yes
O6 H8 O4  0.85 2.48 3.063(8) 126.4 2_666 yes
O6 H9 O1  0.85 1.97 2.823(7) 177.6 2_675 yes
O8 H13 O6  0.85 2.07 2.868(10) 155.9 . yes
O8 H12 O5  0.85 2.32 3.081(12) 149.2 2_665 yes
O7 H10 O8  0.85 1.95 2.708(10) 148.3 1_655 yes
O7 H11 O5  0.85 1.98 2.723(7) 145.0 1_546 yes
O6 H8 O8  0.85 2.43 3.106(12) 137.3 2_566 yes
O6 H8 O4  0.85 2.48 3.063(8) 126.4 2_666 yes
O6 H9 O1  0.85 1.97 2.823(7) 177.6 2_675 yes
 
_refine_diff_density_max    0.887
_refine_diff_density_min   -0.737
_refine_diff_density_rms    0.122



