# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_34-1
_database_code_depnum_ccdc_archive 'CCDC 1971064'
loop_
_audit_author_name
_audit_author_address
'Guo-Dong Chen'
;Jinan University
China
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'sporormielone A'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O6'
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.17188(13)
_cell_length_b                   12.40101(16)
_cell_length_c                   13.7935(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.4883(15)
_cell_angle_gamma                90
_cell_volume                     1397.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14077
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4630
_cell_measurement_theta_min      3.1340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63145
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17789
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.724
_diffrn_reflns_theta_min         4.796
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -40.98  38.00-180.00   99
  2  ω    -66.00  33.00   1.00    1.00    --  -40.98  38.00 150.00   99
  3  ω    -39.00  82.00   1.00    1.00    --   40.98 -19.00 -60.00  121
  4  ω     16.00 115.00   1.00    1.00    --   40.98  38.00 120.00   99
  5  ω      1.00  82.00   1.00    1.00    --   40.98 -99.00-180.00   81
  6  ω     23.00  97.00   1.00    1.00    --   40.98-125.00 -90.00   74
  7  ω     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
  8  ω     98.00 178.00   1.00    1.00    --  106.95  86.00 -85.00   80
  9  ω     79.00 178.00   1.00    1.00    --  106.95  30.00-120.00   99
 10  ω     81.00 178.00   1.00    1.00    --  106.95  45.00 -90.00   97
 11  ω     25.00 109.00   1.00    1.00    --  106.95 -95.00 120.00   84
 12  ω     78.00 178.00   1.00    1.00    --  106.95  61.00  30.00  100
 13  ω     34.00 121.00   1.00    1.00    --  106.95-125.00  60.00   87
 14  ω     81.00 178.00   1.00    1.00    --  106.95  45.00 -60.00   97
 15  ω     94.00 178.00   1.00    1.00    --  106.95 125.00  60.00   84
 16  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00 120.00   99
 17  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00-120.00   99
 18  ω     25.00 109.00   1.00    1.00    --  106.95 -95.00-120.00   84
 19  ω     13.00 113.00   1.00    1.00    --   40.98  57.00-120.00  100
 20  ω     13.00 113.00   1.00    1.00    --   40.98  57.00   0.00  100
 21  ω      8.00 117.00   1.00    1.00    --   40.98  77.00  30.00  109
 22  ω      8.00 117.00   1.00    1.00    --   40.98  77.00 -90.00  109
 23  ω      8.00 117.00   1.00    1.00    --   40.98  77.00 120.00  109
 24  ω     54.00 156.00   1.00    1.00    --  106.95  15.00 150.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1010055000
_diffrn_orient_matrix_UB_12      0.0514291000
_diffrn_orient_matrix_UB_13      -0.0807492000
_diffrn_orient_matrix_UB_21      -0.0108816000
_diffrn_orient_matrix_UB_22      -0.1058850000
_diffrn_orient_matrix_UB_23      -0.0582337000
_diffrn_orient_matrix_UB_31      -0.1587908000
_diffrn_orient_matrix_UB_32      0.0398635000
_diffrn_orient_matrix_UB_33      -0.0506955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2723
_reflns_number_total             2788
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.8790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6'(H6')
2.b Idealised Me refined as rotating group:
 C8(H8C,H8A,H8B), C1(H1C,H1B,H1A), C8'(H8'B,H8'C,H8'A), C1'(H1'A,H1'B,H1'C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3'(H3'), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.65554(11) 0.08094(8) 0.43257(7) 0.0165(2) Uani 1 1 d . . . . .
H1 H 0.6039 0.0853 0.3810 0.025 Uiso 1 1 calc GR . . . .
O3' O 0.44815(11) 0.33973(8) 0.86783(6) 0.0170(2) Uani 1 1 d . . . . .
H3' H 0.3654 0.3670 0.8896 0.025 Uiso 1 1 calc GR . . . .
O3 O 0.14206(11) 0.22964(8) 0.52415(7) 0.0174(2) Uani 1 1 d . . . . .
H3 H 0.1209 0.2042 0.4704 0.026 Uiso 1 1 calc GR . . . .
O2 O 0.34225(11) 0.13167(8) 0.39637(7) 0.0171(2) Uani 1 1 d . . . . .
O2' O 0.15535(11) 0.31302(8) 0.73674(7) 0.0188(2) Uani 1 1 d . . . . .
O1' O 0.34873(12) 0.53593(8) 0.76888(8) 0.0231(2) Uani 1 1 d . . . . .
C5 C 0.29455(15) 0.20206(10) 0.55200(9) 0.0128(3) Uani 1 1 d . . . . .
C3 C 0.56830(15) 0.12896(10) 0.50444(9) 0.0127(3) Uani 1 1 d . . . . .
C7 C 0.53449(15) 0.19629(10) 0.66992(9) 0.0121(3) Uani 1 1 d . . . . .
C4 C 0.39754(16) 0.15141(10) 0.47840(9) 0.0129(3) Uani 1 1 d . . . . .
C2 C 0.63705(15) 0.14930(10) 0.59215(9) 0.0126(3) Uani 1 1 d . . . . .
C6 C 0.36184(15) 0.22563(10) 0.63947(9) 0.0126(3) Uani 1 1 d . . . . .
C4' C 0.29610(15) 0.29558(10) 0.71538(9) 0.0131(3) Uani 1 1 d . . . . .
C6' C 0.59731(15) 0.30478(10) 0.71712(9) 0.0122(3) Uani 1 1 d . . . . .
H6' H 0.6847 0.2905 0.7654 0.015 Uiso 1 1 calc R . . . .
C3' C 0.43837(16) 0.46941(11) 0.73355(10) 0.0156(3) Uani 1 1 d . . . . .
C5' C 0.44585(15) 0.35113(10) 0.76599(9) 0.0130(3) Uani 1 1 d . . . . .
C7' C 0.64811(15) 0.39439(11) 0.64823(9) 0.0142(3) Uani 1 1 d . . . . .
C2' C 0.55663(16) 0.48432(11) 0.65688(10) 0.0158(3) Uani 1 1 d . . . . .
C8 C 0.52565(16) 0.11198(11) 0.75356(9) 0.0155(3) Uani 1 1 d . . . . .
H8C H 0.4737 0.0475 0.7297 0.023 Uiso 1 1 calc GR . . . .
H8A H 0.4634 0.1413 0.8054 0.023 Uiso 1 1 calc GR . . . .
H8B H 0.6344 0.0953 0.7770 0.023 Uiso 1 1 calc GR . . . .
C1 C 0.80947(16) 0.11547(11) 0.61724(10) 0.0163(3) Uani 1 1 d . . . . .
H1C H 0.8097 0.0423 0.6401 0.024 Uiso 1 1 calc GR . . . .
H1B H 0.8540 0.1618 0.6670 0.024 Uiso 1 1 calc GR . . . .
H1A H 0.8749 0.1206 0.5606 0.024 Uiso 1 1 calc GR . . . .
C8' C 0.79316(17) 0.38269(11) 0.58521(10) 0.0199(3) Uani 1 1 d . . . . .
H8'B H 0.8861 0.3597 0.6239 0.030 Uiso 1 1 calc GR . . . .
H8'C H 0.8168 0.4508 0.5556 0.030 Uiso 1 1 calc GR . . . .
H8'A H 0.7698 0.3301 0.5357 0.030 Uiso 1 1 calc GR . . . .
C1' C 0.56739(19) 0.59001(11) 0.60501(11) 0.0218(3) Uani 1 1 d . . . . .
H1'A H 0.4802 0.5951 0.5572 0.033 Uiso 1 1 calc GR . . . .
H1'B H 0.6707 0.5949 0.5737 0.033 Uiso 1 1 calc GR . . . .
H1'C H 0.5582 0.6479 0.6508 0.033 Uiso 1 1 calc GR . . . .


_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 H1 0.8200 . ?
O1 C3 1.3719(15) . ?
O3' H3' 0.8200 . ?
O3' C5' 1.4114(15) . ?
O3 H3 0.8200 . ?
O3 C5 1.3389(16) . ?
O2 C4 1.2319(16) . ?
O2' C4' 1.2141(16) . ?
O1' C3' 1.2137(17) . ?
C5 C4 1.4757(18) . ?
C5 C6 1.3450(18) . ?
C3 C4 1.4587(18) . ?
C3 C2 1.3445(18) . ?
C7 C2 1.4964(17) . ?
C7 C6 1.5062(17) . ?
C7 C6' 1.5749(17) . ?
C7 C8 1.5600(17) . ?
C2 C1 1.5019(17) . ?
C6 C4' 1.4720(18) . ?
C4' C5' 1.5540(17) . ?
C6' H6' 0.9800 . ?
C6' C5' 1.5362(17) . ?
C6' C7' 1.5267(17) . ?
C3' C5' 1.5343(18) . ?
C3' C2' 1.4628(19) . ?
C7' C2' 1.3496(19) . ?
C7' C8' 1.4950(18) . ?
C2' C1' 1.4969(18) . ?
C8 H8C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
C8' H8'A 0.9600 . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 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
C3 O1 H1 109.5 . . ?
C5' O3' H3' 109.5 . . ?
C5 O3 H3 109.5 . . ?
O3 C5 C4 117.04(11) . . ?
O3 C5 C6 123.89(12) . . ?
C6 C5 C4 118.84(11) . . ?
O1 C3 C4 114.62(11) . . ?
C2 C3 O1 121.26(11) . . ?
C2 C3 C4 124.09(12) . . ?
C2 C7 C6 115.61(10) . . ?
C2 C7 C6' 116.51(10) . . ?
C2 C7 C8 107.86(10) . . ?
C6 C7 C6' 101.64(10) . . ?
C6 C7 C8 107.88(10) . . ?
C8 C7 C6' 106.72(10) . . ?
O2 C4 C5 120.95(12) . . ?
O2 C4 C3 120.92(12) . . ?
C3 C4 C5 118.09(11) . . ?
C3 C2 C7 119.30(11) . . ?
C3 C2 C1 121.50(12) . . ?
C7 C2 C1 118.89(11) . . ?
C5 C6 C7 123.77(11) . . ?
C5 C6 C4' 128.16(12) . . ?
C4' C6 C7 107.49(10) . . ?
O2' C4' C6 130.03(12) . . ?
O2' C4' C5' 123.50(12) . . ?
C6 C4' C5' 106.44(10) . . ?
C7 C6' H6' 110.5 . . ?
C5' C6' C7 104.08(10) . . ?
C5' C6' H6' 110.5 . . ?
C7' C6' C7 117.10(10) . . ?
C7' C6' H6' 110.5 . . ?
C7' C6' C5' 103.65(10) . . ?
O1' C3' C5' 123.54(12) . . ?
O1' C3' C2' 128.42(13) . . ?
C2' C3' C5' 108.04(11) . . ?
O3' C5' C4' 113.12(10) . . ?
O3' C5' C6' 114.15(10) . . ?
O3' C5' C3' 112.67(10) . . ?
C6' C5' C4' 105.73(10) . . ?
C3' C5' C4' 105.53(10) . . ?
C3' C5' C6' 104.84(10) . . ?
C2' C7' C6' 112.72(11) . . ?
C2' C7' C8' 125.52(12) . . ?
C8' C7' C6' 121.58(12) . . ?
C3' C2' C1' 120.29(12) . . ?
C7' C2' C3' 109.72(12) . . ?
C7' C2' C1' 129.92(13) . . ?
C7 C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8C C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1A 109.5 . . ?
H1C C1 H1B 109.5 . . ?
H1C C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
C7' C8' H8'A 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
H8'B C8' H8'A 109.5 . . ?
H8'C C8' H8'A 109.5 . . ?
C2' C1' H1'A 109.5 . . ?
C2' C1' H1'B 109.5 . . ?
C2' C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.486
_oxdiff_exptl_absorpt_empirical_full_min 0.552
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_chemical_compound_source        Fungus
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_w15551
_database_code_depnum_ccdc_archive 'CCDC 1971068'
loop_
_audit_author_name
_audit_author_address
'Guo-Dong Chen'
;Jinan University
China
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'sporormielone E'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O6'
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.1094(2)
_cell_length_b                   10.3354(2)
_cell_length_c                   14.8756(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1400.53(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6718
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5470
_cell_measurement_theta_min      5.1560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78723
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.096
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9339
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.678
_diffrn_reflns_theta_min         5.211
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  62.00   1.00    1.00    --   40.98 -99.00 150.00   46
  2  ω     48.00  74.00   1.00    1.00    --  106.95 -61.00 150.00   26
  3  ω     37.00 134.00   1.00    1.00    --  106.95 -30.00  60.00   97
  4  ω     83.00 177.00   1.00    1.00    --  106.95  45.00  60.00   94
  5  ω    115.00 170.00   1.00    1.00    --  106.95 125.00  30.00   55
  6  ω    147.00 175.00   1.00    1.00    --  106.95  45.00-120.00   28
  7  ω     87.00 113.00   1.00    1.00    --  106.95-125.00   0.00   26
  8  ω     77.00 119.00   1.00    1.00    --  106.95-125.00  60.00   42
  9  ω     34.00 117.00   1.00    1.00    --  106.95-125.00 -90.00   83
 10  ω     31.00  95.00   1.00    1.00    --   40.98-125.00   0.00   64
 11  ω     36.00 124.00   1.00    1.00    --  106.95 -61.00 -90.00   88
 12  ω     32.00 128.00   1.00    1.00    --  106.95 -77.00  60.00   96
 13  ω     33.00 156.00   1.00    1.00    --  106.95 -15.00-120.00  123
 14  ω    -62.00  -5.00   1.00    1.00    --  -40.98 125.00-180.00   57
 15  ω    -88.00  30.00   1.00    1.00    --  -40.98   0.00  30.00  118
 16  ω   -100.00 -20.00   1.00    1.00    --  -40.98 -37.00   0.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0845544000
_diffrn_orient_matrix_UB_12      0.1290265000
_diffrn_orient_matrix_UB_13      0.0029520000
_diffrn_orient_matrix_UB_21      0.1459161000
_diffrn_orient_matrix_UB_22      0.0746485000
_diffrn_orient_matrix_UB_23      -0.0070556000
_diffrn_orient_matrix_UB_31      -0.0122449000
_diffrn_orient_matrix_UB_32      -0.0014717000
_diffrn_orient_matrix_UB_33      -0.1032871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2686
_reflns_number_total             2783
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1081 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+0.3171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6'(H6')
2.b Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C8'(H8'A,H8'B,H8'C), C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3'(H3'), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.2001(2) 0.70044(17) 0.14466(12) 0.0248(4) Uani 1 1 d . . . . .
H1 H 0.2634 0.6806 0.1814 0.037 Uiso 1 1 calc GR . . . .
O1' O 0.5535(2) 0.30238(19) -0.11971(12) 0.0255(4) Uani 1 1 d . . . . .
O2' O 0.1459(2) 0.29383(18) -0.18924(11) 0.0251(4) Uani 1 1 d . . . . .
O3 O 0.34268(18) 0.29521(16) 0.01689(11) 0.0204(4) Uani 1 1 d . . . . .
O3' O 0.1132(2) 0.07294(18) -0.05282(12) 0.0248(4) Uani 1 1 d . . . . .
H3' H 0.0844 0.1008 -0.0043 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.3717(2) 0.48461(18) 0.15806(11) 0.0240(4) Uani 1 1 d . . . . .
H2 H 0.4480 0.4495 0.1419 0.036 Uiso 1 1 calc GR . . . .
C3 C 0.1938(3) 0.6093(2) 0.07930(16) 0.0198(5) Uani 1 1 d . . . . .
C2 C 0.0990(3) 0.6328(2) 0.00549(16) 0.0209(5) Uani 1 1 d . . . . .
C4' C 0.1974(3) 0.3199(2) -0.11581(16) 0.0204(5) Uani 1 1 d . . . . .
C6 C 0.1755(3) 0.4295(2) -0.05637(16) 0.0196(5) Uani 1 1 d . . . . .
C1' C 0.5386(3) 0.0816(3) -0.25663(17) 0.0265(5) Uani 1 1 d . . . . .
H1'A H 0.5099 0.1338 -0.3071 0.040 Uiso 1 1 calc GR . . . .
H1'B H 0.5323 -0.0082 -0.2726 0.040 Uiso 1 1 calc GR . . . .
H1'C H 0.6377 0.1021 -0.2400 0.040 Uiso 1 1 calc GR . . . .
C4 C 0.2804(3) 0.4990(2) 0.08583(15) 0.0197(5) Uani 1 1 d . . . . .
C3' C 0.4529(3) 0.2248(2) -0.12375(16) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.2667(3) 0.4096(2) 0.01770(16) 0.0184(5) Uani 1 1 d . . . . .
C2' C 0.4383(3) 0.1085(2) -0.17880(16) 0.0214(5) Uani 1 1 d . . . . .
C8' C 0.2715(3) -0.0897(2) -0.18033(18) 0.0273(6) Uani 1 1 d . . . . .
H8'A H 0.1684 -0.0823 -0.1926 0.041 Uiso 1 1 calc GR . . . .
H8'B H 0.2873 -0.1558 -0.1361 0.041 Uiso 1 1 calc GR . . . .
H8'C H 0.3226 -0.1120 -0.2346 0.041 Uiso 1 1 calc GR . . . .
C8 C -0.0091(3) 0.5631(3) -0.14328(18) 0.0275(6) Uani 1 1 d . . . . .
H8A H -0.1067 0.5821 -0.1229 0.041 Uiso 1 1 calc GR . . . .
H8B H -0.0107 0.4862 -0.1795 0.041 Uiso 1 1 calc GR . . . .
H8C H 0.0272 0.6342 -0.1784 0.041 Uiso 1 1 calc GR . . . .
C7 C 0.0892(3) 0.5422(2) -0.06365(17) 0.0207(5) Uani 1 1 d . . . . .
C5' C 0.3132(3) 0.2341(2) -0.06743(16) 0.0195(5) Uani 1 1 d . . . . .
C7' C 0.3280(3) 0.0362(2) -0.14575(17) 0.0218(5) Uani 1 1 d . . . . .
C6' C 0.2658(3) 0.0928(2) -0.06020(17) 0.0210(5) Uani 1 1 d . . . . .
H6' H 0.3149 0.0530 -0.0085 0.025 Uiso 1 1 calc R . . . .
C1 C 0.0146(3) 0.7580(3) 0.0024(2) 0.0294(6) Uani 1 1 d . . . . .
H1A H -0.0837 0.7436 0.0234 0.044 Uiso 1 1 calc GR . . . .
H1B H 0.0117 0.7894 -0.0583 0.044 Uiso 1 1 calc GR . . . .
H1C H 0.0619 0.8207 0.0401 0.044 Uiso 1 1 calc GR . . . .


_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 C3 1.355(3) . ?
O1' C3' 1.220(3) . ?
O2' C4' 1.219(3) . ?
O3 C5 1.370(3) . ?
O3 C5' 1.430(3) . ?
O3' C6' 1.409(3) . ?
O2 C4 1.367(3) . ?
C3 C2 1.418(3) . ?
C3 C4 1.390(3) . ?
C2 C7 1.394(3) . ?
C2 C1 1.505(3) . ?
C4' C6 1.451(3) . ?
C4' C5' 1.554(3) . ?
C6 C5 1.395(3) . ?
C6 C7 1.409(3) . ?
C1' C2' 1.501(3) . ?
C4 C5 1.377(3) . ?
C3' C2' 1.460(4) . ?
C3' C5' 1.526(3) . ?
C2' C7' 1.345(4) . ?
C8' C7' 1.490(4) . ?
C8 C7 1.501(4) . ?
C5' C6' 1.527(3) . ?
C7' C6' 1.511(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
C5 O3 C5' 107.09(17) . . ?
O1 C3 C2 117.5(2) . . ?
O1 C3 C4 119.7(2) . . ?
C4 C3 C2 122.7(2) . . ?
C3 C2 C1 118.8(2) . . ?
C7 C2 C3 119.7(2) . . ?
C7 C2 C1 121.5(2) . . ?
O2' C4' C6 131.7(2) . . ?
O2' C4' C5' 123.4(2) . . ?
C6 C4' C5' 104.87(19) . . ?
C5 C6 C4' 106.5(2) . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 C4' 132.5(2) . . ?
O2 C4 C3 119.3(2) . . ?
O2 C4 C5 124.1(2) . . ?
C5 C4 C3 116.6(2) . . ?
O1' C3' C2' 129.6(2) . . ?
O1' C3' C5' 123.9(2) . . ?
C2' C3' C5' 106.5(2) . . ?
O3 C5 C6 114.9(2) . . ?
O3 C5 C4 122.7(2) . . ?
C4 C5 C6 122.4(2) . . ?
C3' C2' C1' 122.0(2) . . ?
C7' C2' C1' 129.3(2) . . ?
C7' C2' C3' 108.7(2) . . ?
C2 C7 C6 117.6(2) . . ?
C2 C7 C8 121.6(2) . . ?
C6 C7 C8 120.8(2) . . ?
O3 C5' C4' 106.37(18) . . ?
O3 C5' C3' 110.66(19) . . ?
O3 C5' C6' 114.4(2) . . ?
C3' C5' C4' 110.34(19) . . ?
C3' C5' C6' 102.34(19) . . ?
C6' C5' C4' 112.7(2) . . ?
C2' C7' C8' 128.0(2) . . ?
C2' C7' C6' 111.9(2) . . ?
C8' C7' C6' 120.0(2) . . ?
O3' C6' C5' 115.1(2) . . ?
O3' C6' C7' 112.3(2) . . ?
C7' C6' C5' 101.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.709
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_w1521
_database_code_depnum_ccdc_archive 'CCDC 1971067'
loop_
_audit_author_name
_audit_author_address
'Guo-Dong Chen'
;Jinan University
China
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'sporormielone D'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O6, H2 O'
_chemical_formula_sum            'C16 H18 O7'
_chemical_formula_weight         322.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.4502(10)
_cell_length_b                   7.6047(4)
_cell_length_c                   15.7124(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.641(9)
_cell_angle_gamma                90
_cell_volume                     1504.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.9730
_cell_measurement_theta_min      3.4740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71419
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9690
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.736
_diffrn_reflns_theta_min         3.511
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  34.00   1.00    1.00    --  -40.73  38.00 120.00   99
  2  ω     42.00  97.00   1.00    1.00    --   40.73-125.00 -30.00   55
  3  ω     48.00 127.00   1.00    3.00    --  107.58 -61.00-150.00   79
  4  ω     89.00 122.00   1.00    3.00    --  107.58-125.00 -30.00   33
  5  ω     38.00  96.00   1.00    1.00    --   40.73-125.00-180.00   58
  6  ω     29.00  60.00   1.00    3.00    --  107.58 -94.00-120.00   31
  7  ω     26.00 102.00   1.00    3.00    --  107.58 -94.00-180.00   76
  8  ω     28.00 127.00   1.00    3.00    --  107.58 -15.00-120.00   99
  9  ω     35.00 133.00   1.00    3.00    --  107.58 -45.00  30.00   98
 10  ω     34.00 122.00   1.00    3.00    --  107.58-125.00  90.00   88
 11  ω     29.00 151.00   1.00    3.00    --  107.58 -15.00 120.00  122
 12  ω    127.00 170.00   1.00    3.00    --  107.58 125.00 120.00   43
 13  ω    149.00 176.00   1.00    3.00    --  107.58 125.00-120.00   27
 14  ω    112.00 137.00   1.00    3.00    --  107.58 125.00-120.00   25
 15  ω    100.00 125.00   1.00    3.00    --  107.58 125.00-180.00   25
 16  ω     30.00  99.00   1.00    1.00    --   40.73  38.00-150.00   69
 17  ω    -49.00  -3.00   1.00    1.00    --  -40.73 125.00-180.00   46
 18  ω   -113.00 -16.00   1.00    1.00    --  -40.73 -38.00 -60.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0210252000
_diffrn_orient_matrix_UB_12      -0.0018945000
_diffrn_orient_matrix_UB_13      -0.0902358000
_diffrn_orient_matrix_UB_21      0.1204709000
_diffrn_orient_matrix_UB_22      -0.0094725000
_diffrn_orient_matrix_UB_23      0.0532639000
_diffrn_orient_matrix_UB_31      -0.0057930000
_diffrn_orient_matrix_UB_32      -0.2022911000
_diffrn_orient_matrix_UB_33      -0.0016484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2336
_reflns_number_total             2986
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         2.381
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.1378
_refine_ls_restrained_S_all      1.342
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3092
_refine_ls_wR_factor_ref         0.3308
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Ternary CH refined with riding coordinates:
 C6'(H6')
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C1'(H1'A,H1'B,H1'C), C8'(H8'A,H8'B,H8'C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3'(H3'), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O -0.8769(2) -0.5031(3) -0.00691(18) 0.0202(6) Uani 1 1 d . . . . .
H2 H -0.8214 -0.4576 0.0260 0.030 Uiso 1 1 calc GR . . . .
O2' O -0.6734(2) -0.4741(3) -0.28440(17) 0.0193(6) Uani 1 1 d . . . . .
O3 O -0.69113(19) -0.5363(3) -0.04372(16) 0.0186(6) Uani 1 1 d . . . . .
O3' O -0.50072(19) -0.5316(3) -0.13681(17) 0.0191(6) Uani 1 1 d . . . . .
H3' H -0.5028 -0.4953 -0.1866 0.029 Uiso 1 1 calc GR . . . .
O1 O -1.0660(2) -0.4913(4) -0.1475(2) 0.0323(8) Uani 1 1 d . . . . .
H1 H -1.0516 -0.4769 -0.0928 0.048 Uiso 1 1 calc GR . . . .
C4 C -0.8773(3) -0.5120(4) -0.0938(2) 0.0148(7) Uani 1 1 d . . . . .
C3 C -0.9752(3) -0.5071(4) -0.1653(3) 0.0172(8) Uani 1 1 d . . . . .
C2 C -0.9831(3) -0.5148(4) -0.2567(3) 0.0184(8) Uani 1 1 d . . . . .
C7 C -0.8917(3) -0.5290(5) -0.2777(2) 0.0188(8) Uani 1 1 d . . . . .
O4 O -0.7133(2) -0.3243(4) 0.0969(2) 0.0309(7) Uani 1 1 d . . . . .
H4A H -0.7145 -0.2492 0.1366 0.046 Uiso 1 1 d G . . . .
H4B H -0.6512 -0.3676 0.1115 0.046 Uiso 1 1 d G . . . .
C6 C -0.7919(3) -0.5407(5) -0.2060(2) 0.0184(8) Uani 1 1 d . . . . .
C5 C -0.7867(3) -0.5338(4) -0.1152(2) 0.0169(7) Uani 1 1 d . . . . .
O1' O -0.5560(2) -0.8507(3) -0.2399(2) 0.0289(7) Uani 1 1 d . . . . .
C7' C -0.6405(3) -0.8448(5) -0.0556(2) 0.0209(8) Uani 1 1 d . . . . .
C2' C -0.6240(3) -0.9345(5) -0.1227(2) 0.0213(8) Uani 1 1 d . . . . .
C4' C -0.6905(3) -0.5369(5) -0.2201(2) 0.0187(8) Uani 1 1 d . . . . .
C1 C -1.0919(3) -0.5057(5) -0.3292(3) 0.0246(9) Uani 1 1 d . . . . .
H1A H -1.1177 -0.6226 -0.3470 0.037 Uiso 1 1 calc GR . . . .
H1B H -1.0879 -0.4433 -0.3810 0.037 Uiso 1 1 calc GR . . . .
H1C H -1.1395 -0.4453 -0.3058 0.037 Uiso 1 1 calc GR . . . .
C8 C -0.8995(3) -0.5458(6) -0.3762(3) 0.0279(9) Uani 1 1 d . . . . .
H8A H -0.9625 -0.6103 -0.4098 0.042 Uiso 1 1 calc GR . . . .
H8B H -0.8382 -0.6070 -0.3789 0.042 Uiso 1 1 calc GR . . . .
H8C H -0.9026 -0.4308 -0.4022 0.042 Uiso 1 1 calc GR . . . .
C3' C -0.5888(3) -0.8164(5) -0.1789(2) 0.0203(8) Uani 1 1 d . . . . .
C5' C -0.5953(3) -0.6266(4) -0.1471(2) 0.0163(7) Uani 1 1 d . . . . .
C1' C -0.6348(3) -1.1276(5) -0.1424(3) 0.0305(9) Uani 1 1 d . . . . .
H1'A H -0.6371 -1.1895 -0.0898 0.046 Uiso 1 1 calc GR . . . .
H1'B H -0.5750 -1.1678 -0.1570 0.046 Uiso 1 1 calc GR . . . .
H1'C H -0.6991 -1.1494 -0.1929 0.046 Uiso 1 1 calc GR . . . .
C6' C -0.6126(3) -0.6530(4) -0.0569(2) 0.0166(7) Uani 1 1 d . . . . .
H6' H -0.5448 -0.6324 -0.0074 0.020 Uiso 1 1 calc R . . . .
C8' C -0.6776(3) -0.9082(5) 0.0176(3) 0.0294(9) Uani 1 1 d . . . . .
H8'A H -0.6857 -1.0337 0.0137 0.044 Uiso 1 1 calc GR . . . .
H8'B H -0.7447 -0.8548 0.0107 0.044 Uiso 1 1 calc GR . . . .
H8'C H -0.6265 -0.8770 0.0758 0.044 Uiso 1 1 calc GR . . . .


_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 C4 1.365(4) . ?
O2' C4' 1.210(4) . ?
O3 C5 1.377(4) . ?
O3 C6' 1.449(4) . ?
O3' C5' 1.422(4) . ?
O1 C3 1.350(4) . ?
C4 C3 1.399(5) . ?
C4 C5 1.383(5) . ?
C3 C2 1.403(5) . ?
C2 C7 1.385(5) . ?
C2 C1 1.506(5) . ?
C7 C6 1.418(5) . ?
C7 C8 1.520(5) . ?
C6 C5 1.406(5) . ?
C6 C4' 1.457(5) . ?
O1' C3' 1.216(5) . ?
C7' C2' 1.338(5) . ?
C7' C6' 1.507(5) . ?
C7' C8' 1.487(5) . ?
C2' C3' 1.450(5) . ?
C2' C1' 1.497(5) . ?
C4' C5' 1.544(5) . ?
C3' C5' 1.539(4) . ?
C5' C6' 1.529(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
C5 O3 C6' 114.2(3) . . ?
O2 C4 C3 118.2(3) . . ?
O2 C4 C5 123.8(3) . . ?
C5 C4 C3 118.0(3) . . ?
O1 C3 C4 120.0(3) . . ?
O1 C3 C2 117.9(3) . . ?
C4 C3 C2 122.1(3) . . ?
C3 C2 C1 118.4(3) . . ?
C7 C2 C3 119.5(3) . . ?
C7 C2 C1 122.1(3) . . ?
C2 C7 C6 119.2(3) . . ?
C2 C7 C8 120.1(3) . . ?
C6 C7 C8 120.6(3) . . ?
C7 C6 C4' 123.6(3) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 C4' 116.1(3) . . ?
O3 C5 C4 116.9(3) . . ?
O3 C5 C6 121.7(3) . . ?
C4 C5 C6 121.2(3) . . ?
C2' C7' C6' 111.8(3) . . ?
C2' C7' C8' 129.7(3) . . ?
C8' C7' C6' 118.5(3) . . ?
C7' C2' C3' 110.1(3) . . ?
C7' C2' C1' 129.2(4) . . ?
C3' C2' C1' 120.7(3) . . ?
O2' C4' C6 126.7(3) . . ?
O2' C4' C5' 116.3(3) . . ?
C6 C4' C5' 117.0(3) . . ?
O1' C3' C2' 129.3(3) . . ?
O1' C3' C5' 122.3(3) . . ?
C2' C3' C5' 108.4(3) . . ?
O3' C5' C4' 109.5(3) . . ?
O3' C5' C3' 111.3(3) . . ?
O3' C5' C6' 112.5(3) . . ?
C3' C5' C4' 107.5(3) . . ?
C6' C5' C4' 112.9(3) . . ?
C6' C5' C3' 102.8(3) . . ?
O3 C6' C7' 113.2(3) . . ?
O3 C6' C5' 114.1(3) . . ?
C7' C6' C5' 105.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.551
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_w1_5_5_4
_database_code_depnum_ccdc_archive 'CCDC 1971066'
loop_
_audit_author_name
_audit_author_address
'Guo-Dong Chen'
;Jinan University
China
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'sporormielone C'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O6'
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5190(7)
_cell_length_b                   16.0695(13)
_cell_length_c                   10.3653(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.495(8)
_cell_angle_gamma                90
_cell_volume                     1385.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2800
_cell_measurement_theta_min      5.1530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58819
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5373
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.416
_diffrn_reflns_theta_min         5.165
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  30.00   1.00    1.00    --  -40.98  57.00   0.00   27
  2  ω    -68.00  -9.00   1.00    1.00    --  -40.98  57.00   0.00   59
  3  ω     35.00  82.00   1.00    1.00    --   40.98-125.00-180.00   47
  4  ω     43.00 128.00   1.00    3.50    --  106.95 -30.00-120.00   85
  5  ω     64.00  96.00   1.00    1.00    --   40.98-125.00   0.00   32
  6  ω     34.00 132.00   1.00    3.50    --  106.95 -45.00  60.00   98
  7  ω     92.00 168.00   1.00    3.50    --  106.95  61.00  60.00   76
  8  ω    116.00 157.00   1.00    3.50    --  106.95 125.00 -30.00   41
  9  ω    149.00 176.00   1.00    3.50    --  106.95 125.00-120.00   27
 10  ω     98.00 125.00   1.00    3.50    --  106.95 125.00-120.00   27
 11  ω     40.00 116.00   1.00    3.50    --  106.95-125.00  60.00   76
 12  ω   -111.00 -22.00   1.00    1.00    --  -40.98 -57.00-150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1507327000
_diffrn_orient_matrix_UB_12      0.0055679000
_diffrn_orient_matrix_UB_13      0.0590359000
_diffrn_orient_matrix_UB_21      0.0388695000
_diffrn_orient_matrix_UB_22      -0.0860112000
_diffrn_orient_matrix_UB_23      0.0647014000
_diffrn_orient_matrix_UB_31      0.1002013000
_diffrn_orient_matrix_UB_32      0.0419777000
_diffrn_orient_matrix_UB_33      0.1246123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2205
_reflns_number_total             2717
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.357
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0769
_refine_ls_restrained_S_all      1.357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²+0.9468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2245
_refine_ls_wR_factor_ref         0.2333
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6'(H6')
2.b Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C1(H1A,H1B,H1C), C8'(H8'A,H8'B,H8'C), C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O1'(H1')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O3 O 0.5905(3) 0.32999(15) 0.6080(2) 0.0197(5) Uani 1 1 d . . . . .
O1 O 0.1586(3) 0.48341(16) 0.3552(2) 0.0235(6) Uani 1 1 d . . . . .
H1 H 0.1126 0.4622 0.4088 0.035 Uiso 1 1 calc GR . . . .
O2 O 0.2777(3) 0.38255(15) 0.5671(2) 0.0222(5) Uani 1 1 d . . . . .
H2 H 0.3329 0.3623 0.6345 0.033 Uiso 1 1 calc GR . . . .
O2' O 0.9034(3) 0.40395(17) 0.4105(3) 0.0272(6) Uani 1 1 d . . . . .
O1' O 0.9847(3) 0.28091(17) 0.5807(3) 0.0270(6) Uani 1 1 d . . . . .
H1' H 1.0380 0.3147 0.5493 0.041 Uiso 1 1 calc GR . . . .
O3' O 0.8735(3) 0.20675(17) 0.3196(3) 0.0307(6) Uani 1 1 d . . . . .
C5 C 0.5286(4) 0.3728(2) 0.4944(3) 0.0182(6) Uani 1 1 d . . . . .
C3 C 0.3093(4) 0.4524(2) 0.3730(3) 0.0187(7) Uani 1 1 d . . . . .
C2 C 0.3984(4) 0.4727(2) 0.2782(3) 0.0203(7) Uani 1 1 d . . . . .
C4 C 0.3730(4) 0.4014(2) 0.4808(3) 0.0189(6) Uani 1 1 d . . . . .
C6 C 0.6220(4) 0.3935(2) 0.4033(3) 0.0181(6) Uani 1 1 d . . . . .
C5' C 0.7931(4) 0.2152(2) 0.4022(3) 0.0226(7) Uani 1 1 d . . . . .
C7 C 0.5545(4) 0.4436(2) 0.2921(3) 0.0199(7) Uani 1 1 d . . . . .
C7' C 0.6075(4) 0.1900(2) 0.5303(3) 0.0211(7) Uani 1 1 d . . . . .
C4' C 0.7892(4) 0.3668(2) 0.4379(3) 0.0203(7) Uani 1 1 d . . . . .
C3' C 0.8243(4) 0.2845(2) 0.5117(3) 0.0208(7) Uani 1 1 d . . . . .
C2' C 0.7028(4) 0.2630(2) 0.5990(3) 0.0193(7) Uani 1 1 d . . . . .
C6' C 0.6593(4) 0.1648(2) 0.4229(3) 0.0237(7) Uani 1 1 d . . . . .
H6' H 0.6150 0.1208 0.3689 0.028 Uiso 1 1 calc R . . . .
C1' C 0.7828(4) 0.2455(2) 0.7414(3) 0.0226(7) Uani 1 1 d . . . . .
H1'A H 0.8415 0.2938 0.7792 0.034 Uiso 1 1 calc GR . . . .
H1'B H 0.8553 0.1994 0.7451 0.034 Uiso 1 1 calc GR . . . .
H1'C H 0.7023 0.2322 0.7902 0.034 Uiso 1 1 calc GR . . . .
C1 C 0.3192(4) 0.5249(2) 0.1608(3) 0.0250(7) Uani 1 1 d . . . . .
H1A H 0.3078 0.4925 0.0815 0.037 Uiso 1 1 calc GR . . . .
H1B H 0.3844 0.5728 0.1549 0.037 Uiso 1 1 calc GR . . . .
H1C H 0.2150 0.5424 0.1714 0.037 Uiso 1 1 calc GR . . . .
C8' C 0.4716(4) 0.1546(2) 0.5814(4) 0.0284(8) Uani 1 1 d . . . . .
H8'A H 0.5098 0.1366 0.6710 0.043 Uiso 1 1 calc GR . . . .
H8'B H 0.4270 0.1080 0.5278 0.043 Uiso 1 1 calc GR . . . .
H8'C H 0.3903 0.1964 0.5784 0.043 Uiso 1 1 calc GR . . . .
C8 C 0.6464(4) 0.4615(2) 0.1867(3) 0.0263(8) Uani 1 1 d . . . . .
H8A H 0.5903 0.4381 0.1044 0.039 Uiso 1 1 calc GR . . . .
H8B H 0.7517 0.4373 0.2112 0.039 Uiso 1 1 calc GR . . . .
H8C H 0.6559 0.5206 0.1772 0.039 Uiso 1 1 calc GR . . . .


_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
O3 C5 1.367(4) . ?
O3 C2' 1.457(4) . ?
O1 C3 1.353(4) . ?
O2 C4 1.366(4) . ?
O2' C4' 1.226(4) . ?
O1' C3' 1.399(4) . ?
O3' C5' 1.215(4) . ?
C5 C4 1.381(4) . ?
C5 C6 1.400(4) . ?
C3 C2 1.403(4) . ?
C3 C4 1.397(5) . ?
C2 C7 1.388(5) . ?
C2 C1 1.512(5) . ?
C6 C7 1.421(5) . ?
C6 C4' 1.457(4) . ?
C5' C3' 1.571(5) . ?
C5' C6' 1.451(5) . ?
C7 C8 1.503(4) . ?
C7' C2' 1.515(5) . ?
C7' C6' 1.344(5) . ?
C7' C8' 1.486(5) . ?
C4' C3' 1.524(5) . ?
C3' C2' 1.554(4) . ?
C2' C1' 1.512(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
C5 O3 C2' 116.9(2) . . ?
O3 C5 C4 116.0(3) . . ?
O3 C5 C6 122.1(3) . . ?
C4 C5 C6 121.6(3) . . ?
O1 C3 C2 117.4(3) . . ?
O1 C3 C4 121.2(3) . . ?
C4 C3 C2 121.4(3) . . ?
C3 C2 C1 118.6(3) . . ?
C7 C2 C3 120.0(3) . . ?
C7 C2 C1 121.4(3) . . ?
O2 C4 C5 123.5(3) . . ?
O2 C4 C3 118.1(3) . . ?
C5 C4 C3 118.4(3) . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 C4' 115.6(3) . . ?
C7 C6 C4' 124.7(3) . . ?
O3' C5' C3' 123.7(3) . . ?
O3' C5' C6' 128.5(3) . . ?
C6' C5' C3' 107.7(3) . . ?
C2 C7 C6 119.0(3) . . ?
C2 C7 C8 119.9(3) . . ?
C6 C7 C8 121.1(3) . . ?
C6' C7' C2' 112.6(3) . . ?
C6' C7' C8' 126.9(3) . . ?
C8' C7' C2' 120.5(3) . . ?
O2' C4' C6 125.6(3) . . ?
O2' C4' C3' 117.4(3) . . ?
C6 C4' C3' 117.1(3) . . ?
O1' C3' C5' 109.5(3) . . ?
O1' C3' C4' 110.8(3) . . ?
O1' C3' C2' 113.1(3) . . ?
C4' C3' C5' 105.6(3) . . ?
C4' C3' C2' 113.7(3) . . ?
C2' C3' C5' 103.5(3) . . ?
O3 C2' C7' 108.0(2) . . ?
O3 C2' C3' 113.7(3) . . ?
O3 C2' C1' 103.8(3) . . ?
C7' C2' C3' 104.8(3) . . ?
C1' C2' C7' 113.4(3) . . ?
C1' C2' C3' 113.2(3) . . ?
C7' C6' C5' 111.3(3) . . ?

_olex2_date_sample_data_collection 2018-07-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.485
_oxdiff_exptl_absorpt_empirical_full_min 0.434
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_w1-5-5
_database_code_depnum_ccdc_archive 'CCDC 1971065'
loop_
_audit_author_name
_audit_author_address
'Guo-Dong Chen'
;Jinan University
China
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'sporormielone B'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O6'
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.17259(16)
_cell_length_b                   11.66700(14)
_cell_length_c                   12.81692(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.1439(14)
_cell_angle_gamma                90
_cell_volume                     1357.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17109
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6370
_cell_measurement_theta_min      3.4360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61419
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27554
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.764
_diffrn_reflns_theta_min         5.150
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00  90.00  100
  2  ω    -69.00  32.00   1.00    1.00    --  -41.11  57.00-120.00  101
  3  ω     13.00 113.00   1.00    1.00    --   41.11  57.00-150.00  100
  4  ω     23.00  97.00   1.00    1.00    --   41.11-125.00 -30.00   74
  5  ω    -33.00  65.00   1.00    1.00    --   41.11 -37.00 -60.00   98
  6  ω    -39.00  82.00   1.00    1.00    --   41.11 -19.00  60.00  121
  7  ω     34.00 122.00   1.00    1.00    --  107.58-125.00  60.00   88
  8  ω     31.00 136.00   1.00    1.00    --  107.58 -30.00   0.00  105
  9  ω     31.00 140.00   1.00    1.00    --  107.58 -77.00  60.00  109
 10  ω     35.00 133.00   1.00    1.00    --  107.58 -45.00 -90.00   98
 11  ω     31.00 136.00   1.00    1.00    --  107.58 -30.00-150.00  105
 12  ω     31.00 136.00   1.00    1.00    --  107.58 -30.00  90.00  105
 13  ω     94.00 178.00   1.00    1.00    --  107.58 125.00 -90.00   84
 14  ω     94.00 178.00   1.00    1.00    --  107.58 125.00 -30.00   84
 15  ω     79.00 178.00   1.00    1.00    --  107.58  30.00  60.00   99
 16  ω     25.00 109.00   1.00    1.00    --  107.58 -94.00 -90.00   84
 17  ω   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 -90.00  100
 18  ω      9.00 117.00   1.00    1.00    --   41.11  77.00  60.00  108
 19  ω     23.00  97.00   1.00    1.00    --   41.11-125.00  90.00   74
 20  ω      9.00 117.00   1.00    1.00    --   41.11  77.00-120.00  108
 21  ω      9.00 117.00   1.00    1.00    --   41.11  77.00 -30.00  108
 22  ω     79.00 178.00   1.00    1.00    --  107.58  30.00 -30.00   99
 23  ω     75.00 178.00   1.00    1.00    --  107.58  77.00-150.00  103
 24  ω     55.00 178.00   1.00    1.00    --  107.58  15.00-120.00  123
 25  ω     75.00 178.00   1.00    1.00    --  107.58  77.00  60.00  103
 26  ω     82.00 178.00   1.00    1.00    --  107.58  45.00   0.00   96
 27  ω     78.00 178.00   1.00    1.00    --  107.58  61.00 -90.00  100
 28  ω     78.00 178.00   1.00    1.00    --  107.58  61.00 150.00  100
 29  ω     75.00 178.00   1.00    1.00    --  107.58  77.00-180.00  103
 30  ω     78.00 178.00   1.00    1.00    --  107.58  61.00 -30.00  100
 31  ω     78.00 178.00   1.00    1.00    --  107.58  61.00 120.00  100
 32  ω   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00  90.00  108
 33  ω   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00 120.00   99
 34  ω   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00-180.00   99
 35  ω   -121.00   0.00   1.00    1.00    --  -41.11 -19.00 150.00  121
 36  ω     13.00  76.00   1.00    1.00    --   41.11  57.00-180.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0371645000
_diffrn_orient_matrix_UB_12      0.1110581000
_diffrn_orient_matrix_UB_13      0.0632073000
_diffrn_orient_matrix_UB_21      -0.0269504000
_diffrn_orient_matrix_UB_22      0.0700926000
_diffrn_orient_matrix_UB_23      -0.1028169000
_diffrn_orient_matrix_UB_31      -0.1632759000
_diffrn_orient_matrix_UB_32      0.0136738000
_diffrn_orient_matrix_UB_33      0.0135913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2539
_reflns_number_total             2724
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.8309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8B,H8A)
2.b Aromatic/amide H refined with riding coordinates:
 C6'(H6')
2.c Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C1(H1C,H1B,H1A), C8'(H8'A,H8'B,H8'C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1'(H1'), O2(H2), O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.47298(11) 0.70314(8) 0.29826(8) 0.0165(2) Uani 1 1 d . . . . .
H1' H 0.3894 0.7100 0.2663 0.025 Uiso 1 1 calc GR . . . .
O2 O 0.38891(11) 0.11093(8) 0.44274(8) 0.0193(2) Uani 1 1 d . . . . .
H2 H 0.3025 0.1218 0.4183 0.029 Uiso 1 1 calc GR . . . .
O1 O 0.66972(11) 0.12482(8) 0.54446(8) 0.0189(2) Uani 1 1 d . . . . .
H1 H 0.6104 0.0718 0.5396 0.028 Uiso 1 1 calc GR . . . .
O3 O 0.26894(11) 0.29835(8) 0.32846(9) 0.0207(2) Uani 1 1 d . . . . .
H3 H 0.2420 0.3623 0.3072 0.031 Uiso 1 1 calc GR . . . .
O2' O 0.29821(11) 0.51042(8) 0.28446(9) 0.0208(2) Uani 1 1 d . . . . .
O3' O 0.41658(11) 0.60348(9) 0.09185(8) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.49824(15) 0.40200(11) 0.36860(10) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.61244(16) 0.21364(11) 0.48378(10) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.64403(15) 0.40549(11) 0.42199(10) 0.0143(3) Uani 1 1 d . . . . .
C7' C 0.75331(15) 0.51915(11) 0.22732(11) 0.0157(3) Uani 1 1 d . . . . .
C4 C 0.46880(15) 0.20859(11) 0.43165(11) 0.0152(3) Uani 1 1 d . . . . .
C2' C 0.69578(15) 0.58324(11) 0.31704(10) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.70228(15) 0.31089(12) 0.47965(10) 0.0152(3) Uani 1 1 d . . . . .
C4' C 0.43259(15) 0.50035(11) 0.31145(11) 0.0149(3) Uani 1 1 d . . . . .
C5 C 0.41089(15) 0.30319(11) 0.37482(11) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.72564(15) 0.51804(11) 0.42191(11) 0.0154(3) Uani 1 1 d . . . . .
H8B H 0.8305 0.5033 0.4380 0.018 Uiso 1 1 calc R . . . .
H8A H 0.6978 0.5663 0.4775 0.018 Uiso 1 1 calc R . . . .
C3' C 0.53007(15) 0.59561(11) 0.27572(10) 0.0138(3) Uani 1 1 d . . . . .
C5' C 0.52166(15) 0.57448(11) 0.15584(11) 0.0163(3) Uani 1 1 d . . . . .
C6' C 0.65612(16) 0.51755(12) 0.13860(11) 0.0185(3) Uani 1 1 d . . . . .
H6' H 0.6729 0.4846 0.0753 0.022 Uiso 1 1 calc R . . . .
C1' C 0.77032(16) 0.70160(11) 0.32903(12) 0.0186(3) Uani 1 1 d . . . . .
H1'A H 0.8749 0.6920 0.3465 0.028 Uiso 1 1 calc GR . . . .
H1'B H 0.7333 0.7436 0.3841 0.028 Uiso 1 1 calc GR . . . .
H1'C H 0.7492 0.7431 0.2639 0.028 Uiso 1 1 calc GR . . . .
C1 C 0.85417(16) 0.30876(13) 0.54199(12) 0.0208(3) Uani 1 1 d . . . . .
H1C H 0.9228 0.3429 0.5012 0.031 Uiso 1 1 calc GR . . . .
H1B H 0.8825 0.2309 0.5583 0.031 Uiso 1 1 calc GR . . . .
H1A H 0.8541 0.3511 0.6062 0.031 Uiso 1 1 calc GR . . . .
C8' C 0.90574(16) 0.47146(13) 0.23959(12) 0.0218(3) Uani 1 1 d . . . . .
H8'A H 0.9756 0.5325 0.2552 0.033 Uiso 1 1 calc GR . . . .
H8'B H 0.9219 0.4344 0.1753 0.033 Uiso 1 1 calc GR . . . .
H8'C H 0.9178 0.4168 0.2961 0.033 Uiso 1 1 calc GR . . . .


_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' C3' 1.4052(15) . ?
O2 C4 1.3730(16) . ?
O1 C3 1.3561(16) . ?
O3 C5 1.3536(17) . ?
O2' C4' 1.2377(17) . ?
O3' C5' 1.2216(17) . ?
C6 C7 1.4138(19) . ?
C6 C4' 1.4460(18) . ?
C6 C5 1.4126(19) . ?
C3 C4 1.3915(19) . ?
C3 C2 1.4077(19) . ?
C7 C2 1.3921(19) . ?
C7 C8 1.5116(18) . ?
C7' C2' 1.5270(18) . ?
C7' C6' 1.342(2) . ?
C7' C8' 1.492(2) . ?
C4 C5 1.3861(19) . ?
C2' C8 1.5349(18) . ?
C2' C3' 1.5439(18) . ?
C2' C1' 1.5390(18) . ?
C2 C1 1.5049(18) . ?
C4' C3' 1.5364(18) . ?
C3' C5' 1.5471(18) . ?
C5' C6' 1.445(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
C7 C6 C4' 121.32(12) . . ?
C5 C6 C7 120.09(12) . . ?
C5 C6 C4' 118.51(12) . . ?
O1 C3 C4 120.44(12) . . ?
O1 C3 C2 117.14(12) . . ?
C4 C3 C2 122.38(12) . . ?
C6 C7 C8 117.34(12) . . ?
C2 C7 C6 119.98(12) . . ?
C2 C7 C8 122.43(12) . . ?
C6' C7' C2' 112.71(12) . . ?
C6' C7' C8' 125.74(13) . . ?
C8' C7' C2' 121.45(12) . . ?
O2 C4 C3 117.93(12) . . ?
O2 C4 C5 123.01(12) . . ?
C5 C4 C3 119.01(12) . . ?
C7' C2' C8 112.27(11) . . ?
C7' C2' C3' 102.47(10) . . ?
C7' C2' C1' 108.57(11) . . ?
C8 C2' C3' 113.06(11) . . ?
C8 C2' C1' 109.61(11) . . ?
C1' C2' C3' 110.62(11) . . ?
C3 C2 C1 118.01(12) . . ?
C7 C2 C3 118.44(12) . . ?
C7 C2 C1 123.49(12) . . ?
O2' C4' C6 122.94(13) . . ?
O2' C4' C3' 116.53(12) . . ?
C6 C4' C3' 120.45(12) . . ?
O3 C5 C6 121.82(12) . . ?
O3 C5 C4 118.07(12) . . ?
C4 C5 C6 120.08(13) . . ?
C7 C8 C2' 113.84(11) . . ?
O1' C3' C2' 112.98(10) . . ?
O1' C3' C4' 109.57(11) . . ?
O1' C3' C5' 112.26(11) . . ?
C2' C3' C5' 103.53(11) . . ?
C4' C3' C2' 114.61(11) . . ?
C4' C3' C5' 103.39(10) . . ?
O3' C5' C3' 123.11(13) . . ?
O3' C5' C6' 129.34(13) . . ?
C6' C5' C3' 107.55(11) . . ?
C7' C6' C5' 110.06(12) . . ?

_olex2_date_sample_data_collection 2018-06-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.529
_oxdiff_exptl_absorpt_empirical_full_min 0.587
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
