 
data_sh3991a 
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C19 H14 O5, H2 O'  
_chemical_formula_sum 
 'C19 H16 O6' 
_chemical_formula_weight          340.32 
  
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                    5.5027(4) 
_cell_length_b                    7.9285(5) 
_cell_length_c                    36.706(2) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      1601.42(18) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     152(2) 
_cell_measurement_reflns_used     9833 
_cell_measurement_theta_min       5.58 
_cell_measurement_theta_max       80.32 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.412 
_exptl_crystal_F_000              712 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.630 
_exptl_crystal_size_mid           0.120 
_exptl_crystal_size_min           0.057 
_exptl_absorpt_coefficient_mu     0.885 
_shelx_estimated_absorpt_T_min    0.606 
_shelx_estimated_absorpt_T_max    0.951 
_exptl_absorpt_correction_type   multi-scan 
_exptl_absorpt_correction_T_min  0.6382 
_exptl_absorpt_correction_T_max  0.7543 
_exptl_absorpt_process_details 
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       152(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             24154 
_diffrn_reflns_av_unetI/netI      0.0137 
_diffrn_reflns_av_R_equivalents   0.0189 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -46 
_diffrn_reflns_limit_l_max        46 
_diffrn_reflns_theta_min          6.080 
_diffrn_reflns_theta_max          80.377 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.982 
_diffrn_measured_fraction_theta_full  0.988 
_diffrn_reflns_Laue_measured_fraction_max    0.982 
_diffrn_reflns_Laue_measured_fraction_full   0.988 
_diffrn_reflns_point_group_measured_fraction_max   0.971 
_diffrn_reflns_point_group_measured_fraction_full  0.982 
_reflns_number_total              3406 
_reflns_number_gt                 3406 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.666 
_reflns_Friedel_fraction_max      0.954 
_reflns_Friedel_fraction_full     0.973 
  
_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        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_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)+(0.0339P)²+0.3211P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    0.03(2) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          3406 
_refine_ls_number_parameters      290 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0244 
_refine_ls_R_factor_gt            0.0244 
_refine_ls_wR_factor_ref          0.0640 
_refine_ls_wR_factor_gt           0.0640 
_refine_ls_goodness_of_fit_ref    1.063 
_refine_ls_restrained_S_all       1.063 
_refine_ls_shift/su_max           0.002 
_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 
O1 O 0.73419(19) 0.34704(12) 0.10154(2) 0.0194(2) Uani 1 1 d . . . . . 
O2 O 0.48733(18) 0.11555(12) 0.11645(3) 0.0195(2) Uani 1 1 d . . . . . 
O3 O 0.41320(19) 0.28297(13) 0.21868(3) 0.0220(2) Uani 1 1 d . . . . . 
O4 O -0.37595(19) 0.79989(13) 0.17074(3) 0.0221(2) Uani 1 1 d . . . . . 
O5 O -0.08749(19) 0.80176(14) 0.21356(3) 0.0240(2) Uani 1 1 d . . . . . 
C1 C 0.6396(3) 0.24634(16) 0.13087(3) 0.0176(3) Uani 1 1 d . . . . . 
C2 C 0.8366(3) 0.17819(17) 0.15557(4) 0.0192(3) Uani 1 1 d . . . . . 
C3 C 0.8084(3) 0.23168(18) 0.18953(4) 0.0206(3) Uani 1 1 d . . . . . 
C4 C 0.5931(3) 0.34769(17) 0.19396(4) 0.0189(3) Uani 1 1 d . . . . . 
C5 C 0.4929(3) 0.35932(17) 0.15563(3) 0.0173(3) Uani 1 1 d . . . . . 
C6 C 0.3095(3) 0.45620(18) 0.14426(4) 0.0191(3) Uani 1 1 d . . . . . 
C7 C 0.1734(3) 0.56734(17) 0.16803(4) 0.0196(3) Uani 1 1 d . . . . . 
C8 C -0.0186(3) 0.65786(18) 0.15707(4) 0.0204(3) Uani 1 1 d . . . . . 
C9 C -0.1589(3) 0.76046(16) 0.18318(4) 0.0185(3) Uani 1 1 d . . . . . 
C10 C 0.8643(3) 0.25336(17) 0.07642(3) 0.0188(3) Uani 1 1 d . . . . . 
C11 C 1.0438(3) 0.3267(2) 0.05612(4) 0.0225(3) Uani 1 1 d . . . . . 
C12 C 1.1764(3) 0.2257(2) 0.03144(4) 0.0264(3) Uani 1 1 d . . . . . 
C13 C 1.1243(3) 0.0575(2) 0.02689(4) 0.0267(3) Uani 1 1 d . . . . . 
C14 C 0.9322(3) -0.0187(2) 0.04648(4) 0.0234(3) Uani 1 1 d . . . . . 
C15 C 0.8558(3) -0.1885(2) 0.04189(4) 0.0287(3) Uani 1 1 d . . . . . 
C16 C 0.6624(3) -0.25076(19) 0.06117(4) 0.0292(3) Uani 1 1 d . . . . . 
C17 C 0.5344(3) -0.15053(19) 0.08666(4) 0.0246(3) Uani 1 1 d . . . . . 
C18 C 0.6070(3) 0.01249(18) 0.09195(4) 0.0196(3) Uani 1 1 d . . . . . 
C19 C 0.8023(3) 0.08177(18) 0.07197(4) 0.0196(3) Uani 1 1 d . . . . . 
H1 H 0.967(4) 0.104(2) 0.1468(5) 0.028(5) Uiso 1 1 d . . . . . 
H2 H 0.915(4) 0.203(2) 0.2107(5) 0.026(5) Uiso 1 1 d . . . . . 
H3 H 0.644(3) 0.456(2) 0.2028(5) 0.021(4) Uiso 1 1 d . . . . . 
H4 H 0.262(3) 0.451(2) 0.1183(5) 0.017(4) Uiso 1 1 d . . . . . 
H5 H 0.226(3) 0.572(2) 0.1944(5) 0.021(4) Uiso 1 1 d . . . . . 
H6 H -0.084(4) 0.654(2) 0.1321(5) 0.024(5) Uiso 1 1 d . . . . . 
H7 H 1.082(4) 0.446(3) 0.0592(5) 0.026(5) Uiso 1 1 d . . . . . 
H8 H 1.308(4) 0.277(3) 0.0184(5) 0.032(5) Uiso 1 1 d . . . . . 
H9 H 1.216(4) -0.009(3) 0.0093(5) 0.032(5) Uiso 1 1 d . . . . . 
H10 H 0.947(4) -0.259(3) 0.0242(5) 0.034(5) Uiso 1 1 d . . . . . 
H11 H 0.614(4) -0.363(3) 0.0584(5) 0.025(5) Uiso 1 1 d . . . . . 
H12 H 0.403(4) -0.194(3) 0.1003(5) 0.032(5) Uiso 1 1 d . . . . . 
H13 H 0.436(5) 0.330(3) 0.2398(7) 0.050(7) Uiso 1 1 d . . . . . 
H14 H -0.461(5) 0.860(4) 0.1888(7) 0.066(8) Uiso 1 1 d . . . . . 
O6 O 0.6359(2) 0.44457(14) 0.27867(3) 0.0220(2) Uani 1 1 d . . . . . 
H15 H 0.785(5) 0.405(3) 0.2808(6) 0.041(6) Uiso 1 1 d . . . . . 
H16 H 0.636(4) 0.553(3) 0.2791(6) 0.037(6) Uiso 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 
O1 C10 1.3839(16) . ? 
O1 C1 1.4376(15) . ? 
O2 C18 1.3819(16) . ? 
O2 C1 1.4343(16) . ? 
O3 C4 1.4376(17) . ? 
O3 H13 0.87(2) . ? 
O4 C9 1.3165(17) . ? 
O4 H14 0.94(3) . ? 
O5 C9 1.2266(17) . ? 
C1 C5 1.5099(18) . ? 
C1 C2 1.5133(19) . ? 
C2 C3 1.326(2) . ? 
C2 H1 0.98(2) . ? 
C3 C4 1.509(2) . ? 
C3 H2 1.000(19) . ? 
C4 C5 1.5136(18) . ? 
C4 H3 0.960(19) . ? 
C5 C6 1.335(2) . ? 
C6 C7 1.4486(19) . ? 
C6 H4 0.990(17) . ? 
C7 C8 1.339(2) . ? 
C7 H5 1.011(17) . ? 
C8 C9 1.4750(19) . ? 
C8 H6 0.985(19) . ? 
C10 C11 1.367(2) . ? 
C10 C19 1.4120(19) . ? 
C11 C12 1.412(2) . ? 
C11 H7 0.97(2) . ? 
C12 C13 1.374(2) . ? 
C12 H8 0.96(2) . ? 
C13 C14 1.414(2) . ? 
C13 H9 0.97(2) . ? 
C14 C15 1.420(2) . ? 
C14 C19 1.422(2) . ? 
C15 C16 1.371(3) . ? 
C15 H10 0.99(2) . ? 
C16 C17 1.415(2) . ? 
C16 H11 0.94(2) . ? 
C17 C18 1.367(2) . ? 
C17 H12 0.94(2) . ? 
C18 C19 1.412(2) . ? 
O6 H15 0.88(3) . ? 
O6 H16 0.86(2) . ? 
  
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 
C10 O1 C1 112.85(10) . . ? 
C18 O2 C1 112.90(11) . . ? 
C4 O3 H13 107.9(17) . . ? 
C9 O4 H14 109.2(17) . . ? 
O2 C1 O1 109.68(10) . . ? 
O2 C1 C5 109.81(11) . . ? 
O1 C1 C5 108.35(10) . . ? 
O2 C1 C2 112.42(11) . . ? 
O1 C1 C2 112.80(11) . . ? 
C5 C1 C2 103.53(10) . . ? 
C3 C2 C1 111.42(12) . . ? 
C3 C2 H1 126.0(11) . . ? 
C1 C2 H1 122.6(11) . . ? 
C2 C3 C4 112.85(12) . . ? 
C2 C3 H2 126.0(11) . . ? 
C4 C3 H2 121.2(11) . . ? 
O3 C4 C3 113.02(11) . . ? 
O3 C4 C5 110.96(11) . . ? 
C3 C4 C5 102.89(11) . . ? 
O3 C4 H3 107.9(11) . . ? 
C3 C4 H3 110.5(11) . . ? 
C5 C4 H3 111.6(10) . . ? 
C6 C5 C1 123.84(12) . . ? 
C6 C5 C4 126.93(12) . . ? 
C1 C5 C4 109.20(11) . . ? 
C5 C6 C7 123.53(13) . . ? 
C5 C6 H4 118.6(10) . . ? 
C7 C6 H4 117.9(10) . . ? 
C8 C7 C6 123.57(13) . . ? 
C8 C7 H5 119.5(10) . . ? 
C6 C7 H5 116.9(11) . . ? 
C7 C8 C9 120.88(13) . . ? 
C7 C8 H6 123.3(11) . . ? 
C9 C8 H6 115.6(11) . . ? 
O5 C9 O4 122.85(13) . . ? 
O5 C9 C8 124.76(13) . . ? 
O4 C9 C8 112.36(12) . . ? 
C11 C10 O1 120.59(13) . . ? 
C11 C10 C19 121.43(13) . . ? 
O1 C10 C19 117.97(12) . . ? 
C10 C11 C12 118.79(14) . . ? 
C10 C11 H7 120.4(11) . . ? 
C12 C11 H7 120.8(11) . . ? 
C13 C12 C11 121.38(15) . . ? 
C13 C12 H8 120.6(12) . . ? 
C11 C12 H8 118.0(12) . . ? 
C12 C13 C14 120.58(14) . . ? 
C12 C13 H9 119.9(12) . . ? 
C14 C13 H9 119.4(12) . . ? 
C13 C14 C15 124.47(14) . . ? 
C13 C14 C19 118.11(14) . . ? 
C15 C14 C19 117.41(14) . . ? 
C16 C15 C14 120.68(14) . . ? 
C16 C15 H10 122.0(13) . . ? 
C14 C15 H10 117.3(13) . . ? 
C15 C16 C17 121.71(15) . . ? 
C15 C16 H11 120.5(12) . . ? 
C17 C16 H11 117.8(12) . . ? 
C18 C17 C16 118.64(15) . . ? 
C18 C17 H12 119.5(13) . . ? 
C16 C17 H12 121.8(13) . . ? 
C17 C18 O2 120.80(13) . . ? 
C17 C18 C19 121.11(13) . . ? 
O2 C18 C19 118.07(12) . . ? 
C10 C19 C18 119.91(13) . . ? 
C10 C19 C14 119.63(14) . . ? 
C18 C19 C14 120.43(13) . . ? 
H15 O6 H16 110(2) . . ? 
  
_refine_diff_density_max    0.204 
_refine_diff_density_min   -0.140 
_refine_diff_density_rms    0.030 
  
  
  
