# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 
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data_anm_18_23_echioidinin_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2072153'
loop_
_audit_author_name
_audit_author_address
'Narender Goel'
;National Institute of Pharmaceutical Education and Research, Kolkata, India
India
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-02-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Echioidinin
_chemical_formula_moiety         'C16 H12 O5'
_chemical_formula_sum            'C16 H12 O5'
_chemical_formula_weight         284.26
_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                   7.0308(2)
_cell_length_b                   14.1809(4)
_cell_length_c                   24.9877(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.5360(10)
_cell_angle_gamma                90
_cell_volume                     2488.91(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9777
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      3.54
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.535
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1426 before and 0.0839 after correction. The Ratio of minimum to maximum transmission is 0.6534. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            37622
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.623
_diffrn_reflns_theta_max         66.623
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4200
_reflns_number_total             4341
_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       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0082(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.113
_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)+(0.0669P)²+1.0840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1248
_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:
 C3(H3), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C2'(H2'),
 C3(H3A), C3'(H3'), C4'(H4'), C5'(H5'), C6(H6), C8(H8)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O3(H3), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_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
O1_1 O 0.51627(14) 0.64621(7) 0.28647(4) 0.0176(3) Uani 1 1 d . . . . .
O2_1 O 0.32948(17) 0.54328(8) 0.11068(4) 0.0272(3) Uani 1 1 d . . . . .
O3_1 O 0.44454(16) 0.38151(7) 0.34622(4) 0.0210(3) Uani 1 1 d . . . . .
O4_1 O 0.31278(17) 0.32777(8) 0.25168(4) 0.0242(3) Uani 1 1 d . . . . .
H4_1 H 0.341273 0.323178 0.284577 0.036 Uiso 1 1 calc GR . . . .
O5_1 O 0.72371(16) 0.62939(7) 0.44705(4) 0.0206(3) Uani 1 1 d . . . . .
H5_1 H 0.771068 0.639328 0.477990 0.031 Uiso 1 1 calc GR . . . .
C1_1 C 0.4505(2) 0.57602(11) 0.25291(6) 0.0167(3) Uani 1 1 d . . . . .
C2_1 C 0.5557(2) 0.62840(11) 0.33954(6) 0.0162(3) Uani 1 1 d . . . . .
C3_1 C 0.4209(2) 0.60095(11) 0.19941(6) 0.0188(3) Uani 1 1 d . . . . .
H3_1 H 0.442505 0.663434 0.187402 0.023 Uiso 1 1 calc R . . . .
C4_1 C 0.4199(2) 0.48509(11) 0.27206(6) 0.0172(3) Uani 1 1 d . . . . .
C5_1 C 0.6244(2) 0.71371(11) 0.36762(6) 0.0171(3) Uani 1 1 d . . . . .
C6_1 C 0.5323(2) 0.54074(11) 0.36025(6) 0.0170(3) Uani 1 1 d . . . . .
H6_1 H 0.561567 0.530137 0.397240 0.020 Uiso 1 1 calc R . . . .
C7_1 C 0.3583(2) 0.53058(11) 0.16431(6) 0.0202(3) Uani 1 1 d . . . . .
C8_1 C 0.4647(2) 0.46447(11) 0.32754(6) 0.0173(3) Uani 1 1 d . . . . .
C9_1 C 0.3494(2) 0.41651(11) 0.23498(6) 0.0188(3) Uani 1 1 d . . . . .
C10_1 C 0.7079(2) 0.71193(10) 0.42011(6) 0.0166(3) Uani 1 1 d . . . . .
C11_1 C 0.6115(2) 0.80152(11) 0.34143(6) 0.0207(3) Uani 1 1 d . . . . .
H11_1 H 0.553178 0.804491 0.306446 0.025 Uiso 1 1 calc R . . . .
C12_1 C 0.3184(2) 0.43904(11) 0.18192(6) 0.0211(4) Uani 1 1 d . . . . .
H12_1 H 0.270157 0.392972 0.157276 0.025 Uiso 1 1 calc R . . . .
C13_1 C 0.7778(2) 0.79501(11) 0.44328(6) 0.0202(3) Uani 1 1 d . . . . .
H13_1 H 0.834701 0.793328 0.478464 0.024 Uiso 1 1 calc R . . . .
C14_1 C 0.6807(2) 0.88329(11) 0.36483(7) 0.0237(4) Uani 1 1 d . . . . .
H14_1 H 0.670338 0.941511 0.346126 0.028 Uiso 1 1 calc R . . . .
C15_1 C 0.4067(3) 0.62674(12) 0.08770(7) 0.0299(4) Uani 1 1 d . . . . .
H15A_1 H 0.402670 0.620752 0.048599 0.045 Uiso 1 1 calc GR . . . .
H15B_1 H 0.538850 0.635009 0.100999 0.045 Uiso 1 1 calc GR . . . .
H15C_1 H 0.331300 0.681550 0.097798 0.045 Uiso 1 1 calc GR . . . .
C16_1 C 0.7659(2) 0.87978(11) 0.41615(7) 0.0233(4) Uani 1 1 d . . . . .
H16_1 H 0.815845 0.935570 0.432465 0.028 Uiso 1 1 calc R . . . .
O1_2 O 0.85647(14) 0.35126(7) 0.60012(4) 0.0166(3) Uani 1 1 d . . . . .
O2_2 O 0.87747(16) 0.62417(7) 0.54814(4) 0.0210(3) Uani 1 1 d . . . . .
O3_2 O 1.03948(16) 0.67070(8) 0.64036(4) 0.0227(3) Uani 1 1 d . . . . .
H3_2 H 1.000046 0.677454 0.608360 0.034 Uiso 1 1 calc GR . . . .
O4_2 O 1.12080(15) 0.43743(8) 0.77171(4) 0.0208(3) Uani 1 1 d . . . . .
O5_2 O 0.60435(17) 0.37950(7) 0.44425(4) 0.0231(3) Uani 1 1 d . . . . .
H5_2 H 0.556345 0.371485 0.413204 0.035 Uiso 1 1 calc GR . . . .
C1_2 C 1.1013(2) 0.34301(11) 0.79089(6) 0.0230(4) Uani 1 1 d . . . . .
H1A_2 H 1.168255 0.299640 0.767690 0.035 Uiso 1 1 calc GR . . . .
H1B_2 H 0.966044 0.326134 0.790566 0.035 Uiso 1 1 calc GR . . . .
H1C_2 H 1.156075 0.338595 0.827549 0.035 Uiso 1 1 calc GR . . . .
C1'_2 C 0.7221(2) 0.29027(11) 0.51982(6) 0.0168(3) Uani 1 1 d . . . . .
C2_2 C 0.7906(2) 0.37420(11) 0.54933(6) 0.0168(3) Uani 1 1 d . . . . .
C2'_2 C 0.7463(2) 0.20039(11) 0.54296(6) 0.0196(3) Uani 1 1 d . . . . .
H2'_2 H 0.806255 0.195517 0.577671 0.024 Uiso 1 1 calc R . . . .
C3_2 C 0.7949(2) 0.46473(11) 0.53160(6) 0.0186(3) Uani 1 1 d . . . . .
H3A_2 H 0.745189 0.478916 0.496551 0.022 Uiso 1 1 calc R . . . .
C3'_2 C 0.6859(2) 0.11898(11) 0.51707(7) 0.0216(4) Uani 1 1 d . . . . .
H3'_2 H 0.704879 0.059280 0.533707 0.026 Uiso 1 1 calc R . . . .
C4_2 C 0.8723(2) 0.53907(11) 0.56441(6) 0.0181(3) Uani 1 1 d . . . . .
C4'_2 C 0.5969(2) 0.12540(11) 0.46623(7) 0.0218(4) Uani 1 1 d . . . . .
H4'_2 H 0.554227 0.069931 0.448081 0.026 Uiso 1 1 calc R . . . .
C4A_2 C 0.9438(2) 0.51294(11) 0.61723(6) 0.0173(3) Uani 1 1 d . . . . .
C5_2 C 1.0227(2) 0.57902(11) 0.65477(6) 0.0180(3) Uani 1 1 d . . . . .
C5'_2 C 0.5709(2) 0.21252(11) 0.44225(6) 0.0207(4) Uani 1 1 d . . . . .
H5'_2 H 0.510346 0.216317 0.407579 0.025 Uiso 1 1 calc R . . . .
C6_2 C 1.0802(2) 0.55106(11) 0.70554(6) 0.0190(3) Uani 1 1 d . . . . .
H6_2 H 1.133415 0.595559 0.730366 0.023 Uiso 1 1 calc R . . . .
C6'_2 C 0.6322(2) 0.29508(11) 0.46814(6) 0.0181(3) Uani 1 1 d . . . . .
C7_2 C 1.0598(2) 0.45620(11) 0.72059(6) 0.0174(3) Uani 1 1 d . . . . .
C8_2 C 0.9837(2) 0.38893(11) 0.68517(6) 0.0176(3) Uani 1 1 d . . . . .
H8_2 H 0.969525 0.325000 0.695644 0.021 Uiso 1 1 calc R . . . .
C8A_2 C 0.9294(2) 0.41913(11) 0.63393(6) 0.0163(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1_1 C1_1 1.3686(18) . ?
O1_1 C2_1 1.3663(18) . ?
O2_1 C7_1 1.3584(19) . ?
O2_1 C15_1 1.433(2) . ?
O3_1 C8_1 1.2758(19) . ?
O4_1 H4_1 0.8400 . ?
O4_1 C9_1 1.3541(19) . ?
O5_1 H5_1 0.8400 . ?
O5_1 C10_1 1.3524(18) . ?
C1_1 C3_1 1.389(2) . ?
C1_1 C4_1 1.396(2) . ?
C2_1 C5_1 1.469(2) . ?
C2_1 C6_1 1.359(2) . ?
C3_1 H3_1 0.9500 . ?
C3_1 C7_1 1.387(2) . ?
C4_1 C8_1 1.438(2) . ?
C4_1 C9_1 1.418(2) . ?
C5_1 C10_1 1.413(2) . ?
C5_1 C11_1 1.408(2) . ?
C6_1 H6_1 0.9500 . ?
C6_1 C8_1 1.424(2) . ?
C7_1 C12_1 1.403(2) . ?
C9_1 C12_1 1.372(2) . ?
C10_1 C13_1 1.393(2) . ?
C11_1 H11_1 0.9500 . ?
C11_1 C14_1 1.378(2) . ?
C12_1 H12_1 0.9500 . ?
C13_1 H13_1 0.9500 . ?
C13_1 C16_1 1.381(2) . ?
C14_1 H14_1 0.9500 . ?
C14_1 C16_1 1.392(2) . ?
C15_1 H15A_1 0.9800 . ?
C15_1 H15B_1 0.9800 . ?
C15_1 H15C_1 0.9800 . ?
C16_1 H16_1 0.9500 . ?
O1_2 C2_2 1.3708(18) . ?
O1_2 C8A_2 1.3656(18) . ?
O2_2 C4_2 1.2745(19) . ?
O3_2 H3_2 0.8400 . ?
O3_2 C5_2 1.3557(19) . ?
O4_2 C1_2 1.4308(19) . ?
O4_2 C7_2 1.3555(18) . ?
O5_2 H5_2 0.8400 . ?
O5_2 C6'_2 1.3481(18) . ?
C1_2 H1A_2 0.9800 . ?
C1_2 H1B_2 0.9800 . ?
C1_2 H1C_2 0.9800 . ?
C1'_2 C2_2 1.470(2) . ?
C1'_2 C2'_2 1.407(2) . ?
C1'_2 C6'_2 1.414(2) . ?
C2_2 C3_2 1.359(2) . ?
C2'_2 H2'_2 0.9500 . ?
C2'_2 C3'_2 1.381(2) . ?
C3_2 H3A_2 0.9500 . ?
C3_2 C4_2 1.428(2) . ?
C3'_2 H3'_2 0.9500 . ?
C3'_2 C4'_2 1.394(2) . ?
C4_2 C4A_2 1.440(2) . ?
C4'_2 H4'_2 0.9500 . ?
C4'_2 C5'_2 1.382(2) . ?
C4A_2 C5_2 1.421(2) . ?
C4A_2 C8A_2 1.399(2) . ?
C5_2 C6_2 1.373(2) . ?
C5'_2 H5'_2 0.9500 . ?
C5'_2 C6'_2 1.397(2) . ?
C6_2 H6_2 0.9500 . ?
C6_2 C7_2 1.406(2) . ?
C7_2 C8_2 1.392(2) . ?
C8_2 H8_2 0.9500 . ?
C8_2 C8A_2 1.387(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
C2_1 O1_1 C1_1 120.58(12) . . ?
C7_1 O2_1 C15_1 117.53(12) . . ?
C9_1 O4_1 H4_1 109.5 . . ?
C10_1 O5_1 H5_1 109.5 . . ?
O1_1 C1_1 C3_1 115.89(13) . . ?
O1_1 C1_1 C4_1 120.99(13) . . ?
C3_1 C1_1 C4_1 123.10(14) . . ?
O1_1 C2_1 C5_1 111.08(13) . . ?
C6_1 C2_1 O1_1 121.05(14) . . ?
C6_1 C2_1 C5_1 127.87(14) . . ?
C1_1 C3_1 H3_1 121.5 . . ?
C7_1 C3_1 C1_1 117.08(14) . . ?
C7_1 C3_1 H3_1 121.5 . . ?
C1_1 C4_1 C8_1 119.21(14) . . ?
C1_1 C4_1 C9_1 117.68(14) . . ?
C9_1 C4_1 C8_1 123.10(14) . . ?
C10_1 C5_1 C2_1 122.87(13) . . ?
C11_1 C5_1 C2_1 119.56(14) . . ?
C11_1 C5_1 C10_1 117.56(14) . . ?
C2_1 C6_1 H6_1 119.4 . . ?
C2_1 C6_1 C8_1 121.26(14) . . ?
C8_1 C6_1 H6_1 119.4 . . ?
O2_1 C7_1 C3_1 123.89(14) . . ?
O2_1 C7_1 C12_1 114.14(14) . . ?
C3_1 C7_1 C12_1 121.97(14) . . ?
O3_1 C8_1 C4_1 121.13(14) . . ?
O3_1 C8_1 C6_1 122.00(14) . . ?
C6_1 C8_1 C4_1 116.87(14) . . ?
O4_1 C9_1 C4_1 120.12(14) . . ?
O4_1 C9_1 C12_1 119.34(14) . . ?
C12_1 C9_1 C4_1 120.54(14) . . ?
O5_1 C10_1 C5_1 119.93(13) . . ?
O5_1 C10_1 C13_1 120.37(13) . . ?
C13_1 C10_1 C5_1 119.68(14) . . ?
C5_1 C11_1 H11_1 118.9 . . ?
C14_1 C11_1 C5_1 122.21(15) . . ?
C14_1 C11_1 H11_1 118.9 . . ?
C7_1 C12_1 H12_1 120.2 . . ?
C9_1 C12_1 C7_1 119.55(15) . . ?
C9_1 C12_1 H12_1 120.2 . . ?
C10_1 C13_1 H13_1 119.3 . . ?
C16_1 C13_1 C10_1 121.33(15) . . ?
C16_1 C13_1 H13_1 119.3 . . ?
C11_1 C14_1 H14_1 120.3 . . ?
C11_1 C14_1 C16_1 119.37(15) . . ?
C16_1 C14_1 H14_1 120.3 . . ?
O2_1 C15_1 H15A_1 109.5 . . ?
O2_1 C15_1 H15B_1 109.5 . . ?
O2_1 C15_1 H15C_1 109.5 . . ?
H15A_1 C15_1 H15B_1 109.5 . . ?
H15A_1 C15_1 H15C_1 109.5 . . ?
H15B_1 C15_1 H15C_1 109.5 . . ?
C13_1 C16_1 C14_1 119.83(15) . . ?
C13_1 C16_1 H16_1 120.1 . . ?
C14_1 C16_1 H16_1 120.1 . . ?
C8A_2 O1_2 C2_2 120.52(12) . . ?
C5_2 O3_2 H3_2 109.5 . . ?
C7_2 O4_2 C1_2 117.93(12) . . ?
C6'_2 O5_2 H5_2 109.5 . . ?
O4_2 C1_2 H1A_2 109.5 . . ?
O4_2 C1_2 H1B_2 109.5 . . ?
O4_2 C1_2 H1C_2 109.5 . . ?
H1A_2 C1_2 H1B_2 109.5 . . ?
H1A_2 C1_2 H1C_2 109.5 . . ?
H1B_2 C1_2 H1C_2 109.5 . . ?
C2'_2 C1'_2 C2_2 119.76(13) . . ?
C2'_2 C1'_2 C6'_2 117.39(14) . . ?
C6'_2 C1'_2 C2_2 122.84(13) . . ?
O1_2 C2_2 C1'_2 111.23(12) . . ?
C3_2 C2_2 O1_2 120.97(14) . . ?
C3_2 C2_2 C1'_2 127.80(14) . . ?
C1'_2 C2'_2 H2'_2 118.8 . . ?
C3'_2 C2'_2 C1'_2 122.39(14) . . ?
C3'_2 C2'_2 H2'_2 118.8 . . ?
C2_2 C3_2 H3A_2 119.2 . . ?
C2_2 C3_2 C4_2 121.57(14) . . ?
C4_2 C3_2 H3A_2 119.2 . . ?
C2'_2 C3'_2 H3'_2 120.4 . . ?
C2'_2 C3'_2 C4'_2 119.25(14) . . ?
C4'_2 C3'_2 H3'_2 120.4 . . ?
O2_2 C4_2 C3_2 122.10(14) . . ?
O2_2 C4_2 C4A_2 121.48(14) . . ?
C3_2 C4_2 C4A_2 116.42(14) . . ?
C3'_2 C4'_2 H4'_2 120.0 . . ?
C5'_2 C4'_2 C3'_2 119.93(14) . . ?
C5'_2 C4'_2 H4'_2 120.0 . . ?
C5_2 C4A_2 C4_2 123.07(14) . . ?
C8A_2 C4A_2 C4_2 119.41(14) . . ?
C8A_2 C4A_2 C5_2 117.47(14) . . ?
O3_2 C5_2 C4A_2 119.53(13) . . ?
O3_2 C5_2 C6_2 119.81(14) . . ?
C6_2 C5_2 C4A_2 120.66(14) . . ?
C4'_2 C5'_2 H5'_2 119.4 . . ?
C4'_2 C5'_2 C6'_2 121.11(15) . . ?
C6'_2 C5'_2 H5'_2 119.4 . . ?
C5_2 C6_2 H6_2 120.2 . . ?
C5_2 C6_2 C7_2 119.62(14) . . ?
C7_2 C6_2 H6_2 120.2 . . ?
O5_2 C6'_2 C1'_2 119.84(13) . . ?
O5_2 C6'_2 C5'_2 120.24(14) . . ?
C5'_2 C6'_2 C1'_2 119.92(14) . . ?
O4_2 C7_2 C6_2 114.10(13) . . ?
O4_2 C7_2 C8_2 124.14(14) . . ?
C8_2 C7_2 C6_2 121.77(14) . . ?
C7_2 C8_2 H8_2 121.4 . . ?
C8A_2 C8_2 C7_2 117.22(14) . . ?
C8A_2 C8_2 H8_2 121.4 . . ?
O1_2 C8A_2 C4A_2 121.04(13) . . ?
O1_2 C8A_2 C8_2 115.71(13) . . ?
C8_2 C8A_2 C4A_2 123.24(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C1_1 C3_1 C7_1 178.59(13) . . . . ?
O1_1 C1_1 C4_1 C8_1 -2.2(2) . . . . ?
O1_1 C1_1 C4_1 C9_1 179.23(12) . . . . ?
O1_1 C2_1 C5_1 C10_1 -168.12(12) . . . . ?
O1_1 C2_1 C5_1 C11_1 10.46(19) . . . . ?
O1_1 C2_1 C6_1 C8_1 -0.4(2) . . . . ?
O2_1 C7_1 C12_1 C9_1 177.37(14) . . . . ?
O4_1 C9_1 C12_1 C7_1 -179.23(14) . . . . ?
O5_1 C10_1 C13_1 C16_1 178.94(14) . . . . ?
C1_1 O1_1 C2_1 C5_1 179.91(12) . . . . ?
C1_1 O1_1 C2_1 C6_1 0.5(2) . . . . ?
C1_1 C3_1 C7_1 O2_1 -177.61(14) . . . . ?
C1_1 C3_1 C7_1 C12_1 2.7(2) . . . . ?
C1_1 C4_1 C8_1 O3_1 -177.75(13) . . . . ?
C1_1 C4_1 C8_1 C6_1 2.2(2) . . . . ?
C1_1 C4_1 C9_1 O4_1 -178.39(13) . . . . ?
C1_1 C4_1 C9_1 C12_1 1.9(2) . . . . ?
C2_1 O1_1 C1_1 C3_1 -177.98(12) . . . . ?
C2_1 O1_1 C1_1 C4_1 0.8(2) . . . . ?
C2_1 C5_1 C10_1 O5_1 -1.4(2) . . . . ?
C2_1 C5_1 C10_1 C13_1 177.05(14) . . . . ?
C2_1 C5_1 C11_1 C14_1 -177.22(14) . . . . ?
C2_1 C6_1 C8_1 O3_1 179.01(14) . . . . ?
C2_1 C6_1 C8_1 C4_1 -1.0(2) . . . . ?
C3_1 C1_1 C4_1 C8_1 176.48(13) . . . . ?
C3_1 C1_1 C4_1 C9_1 -2.1(2) . . . . ?
C3_1 C7_1 C12_1 C9_1 -2.9(2) . . . . ?
C4_1 C1_1 C3_1 C7_1 -0.1(2) . . . . ?
C4_1 C9_1 C12_1 C7_1 0.5(2) . . . . ?
C5_1 C2_1 C6_1 C8_1 -179.67(14) . . . . ?
C5_1 C10_1 C13_1 C16_1 0.5(2) . . . . ?
C5_1 C11_1 C14_1 C16_1 -0.2(2) . . . . ?
C6_1 C2_1 C5_1 C10_1 11.2(2) . . . . ?
C6_1 C2_1 C5_1 C11_1 -170.24(15) . . . . ?
C8_1 C4_1 C9_1 O4_1 3.1(2) . . . . ?
C8_1 C4_1 C9_1 C12_1 -176.63(14) . . . . ?
C9_1 C4_1 C8_1 O3_1 0.7(2) . . . . ?
C9_1 C4_1 C8_1 C6_1 -179.28(13) . . . . ?
C10_1 C5_1 C11_1 C14_1 1.4(2) . . . . ?
C10_1 C13_1 C16_1 C14_1 0.8(2) . . . . ?
C11_1 C5_1 C10_1 O5_1 179.99(13) . . . . ?
C11_1 C5_1 C10_1 C13_1 -1.6(2) . . . . ?
C11_1 C14_1 C16_1 C13_1 -0.9(2) . . . . ?
C15_1 O2_1 C7_1 C3_1 14.1(2) . . . . ?
C15_1 O2_1 C7_1 C12_1 -166.13(15) . . . . ?
O1_2 C2_2 C3_2 C4_2 1.7(2) . . . . ?
O2_2 C4_2 C4A_2 C5_2 0.6(2) . . . . ?
O2_2 C4_2 C4A_2 C8A_2 177.91(13) . . . . ?
O3_2 C5_2 C6_2 C7_2 179.03(13) . . . . ?
O4_2 C7_2 C8_2 C8A_2 -179.38(13) . . . . ?
C1_2 O4_2 C7_2 C6_2 178.53(13) . . . . ?
C1_2 O4_2 C7_2 C8_2 -1.7(2) . . . . ?
C1'_2 C2_2 C3_2 C4_2 -177.73(14) . . . . ?
C1'_2 C2'_2 C3'_2 C4'_2 -0.3(2) . . . . ?
C2_2 O1_2 C8A_2 C4A_2 -1.8(2) . . . . ?
C2_2 O1_2 C8A_2 C8_2 177.11(12) . . . . ?
C2_2 C1'_2 C2'_2 C3'_2 -179.59(14) . . . . ?
C2_2 C1'_2 C6'_2 O5_2 -0.8(2) . . . . ?
C2_2 C1'_2 C6'_2 C5'_2 179.82(14) . . . . ?
C2_2 C3_2 C4_2 O2_2 179.82(14) . . . . ?
C2_2 C3_2 C4_2 C4A_2 -0.5(2) . . . . ?
C2'_2 C1'_2 C2_2 O1_2 -5.81(19) . . . . ?
C2'_2 C1'_2 C2_2 C3_2 173.64(15) . . . . ?
C2'_2 C1'_2 C6'_2 O5_2 179.56(13) . . . . ?
C2'_2 C1'_2 C6'_2 C5'_2 0.2(2) . . . . ?
C2'_2 C3'_2 C4'_2 C5'_2 0.3(2) . . . . ?
C3_2 C4_2 C4A_2 C5_2 -179.12(14) . . . . ?
C3_2 C4_2 C4A_2 C8A_2 -1.8(2) . . . . ?
C3'_2 C4'_2 C5'_2 C6'_2 -0.1(2) . . . . ?
C4_2 C4A_2 C5_2 O3_2 -2.6(2) . . . . ?
C4_2 C4A_2 C5_2 C6_2 176.75(14) . . . . ?
C4_2 C4A_2 C8A_2 O1_2 3.0(2) . . . . ?
C4_2 C4A_2 C8A_2 C8_2 -175.90(13) . . . . ?
C4'_2 C5'_2 C6'_2 O5_2 -179.52(14) . . . . ?
C4'_2 C5'_2 C6'_2 C1'_2 -0.2(2) . . . . ?
C4A_2 C5_2 C6_2 C7_2 -0.3(2) . . . . ?
C5_2 C4A_2 C8A_2 O1_2 -179.53(12) . . . . ?
C5_2 C4A_2 C8A_2 C8_2 1.6(2) . . . . ?
C5_2 C6_2 C7_2 O4_2 -179.72(13) . . . . ?
C5_2 C6_2 C7_2 C8_2 0.5(2) . . . . ?
C6_2 C7_2 C8_2 C8A_2 0.4(2) . . . . ?
C6'_2 C1'_2 C2_2 O1_2 174.61(13) . . . . ?
C6'_2 C1'_2 C2_2 C3_2 -5.9(2) . . . . ?
C6'_2 C1'_2 C2'_2 C3'_2 0.0(2) . . . . ?
C7_2 C8_2 C8A_2 O1_2 179.59(12) . . . . ?
C7_2 C8_2 C8A_2 C4A_2 -1.5(2) . . . . ?
C8A_2 O1_2 C2_2 C1'_2 178.98(12) . . . . ?
C8A_2 O1_2 C2_2 C3_2 -0.5(2) . . . . ?
C8A_2 C4A_2 C5_2 O3_2 179.99(13) . . . . ?
C8A_2 C4A_2 C5_2 C6_2 -0.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_anm_28_ml_25_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2072714'
loop_
_audit_author_name
_audit_author_address
'Narender Goel'
;National Institute of Pharmaceutical Education and Research, Kolkata, India
India
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'5,2?,6?-trihydroxy-7-methoxyflavone 2?-O-β-D-glucopyranoside'
_chemical_formula_moiety         'C H4 O, C22 H22 O11'
_chemical_formula_sum            'C23 H26 O12'
_chemical_formula_weight         494.44
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.5283(7)
_cell_length_b                   8.0352(5)
_cell_length_c                   24.3766(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.495(4)
_cell_angle_gamma                90
_cell_volume                     2195.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.4
_cell_measurement_theta_min      3.94
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  0.3593
_exptl_absorpt_correction_T_min  0.2656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1549 before and 0.1102 after correction. The Ratio of minimum to maximum transmission is 0.7451. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_preparation       'Slow Evaporation'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1096
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            75053
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.349
_diffrn_reflns_theta_max         67.349
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7303
_reflns_number_total             7767
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       0.0199(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         7767
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.090
_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)+(0.1310P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.1815
_refine_special_details          'Refined as a 4-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(3)
 0.20(4) 0.1(3) -0.11(4)
2. 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
3.a Ternary CH refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8A), C13(H13), C14(H14), C15(H15), C2(H2), C6(H6),
 C8(H8A), C13(H13), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C0AA(H0AB,H0AC,H0AD), C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C10(H10A,H10B,H10C)
3.e Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA), O1(H1), O3(H3), O5(H5), O8(H8), O9(H9), O10(H10), O11(H11),
 O3(H3), O5(H5), O8(H8), O9(H9), O10(H10), O11(H11)
;
_atom_sites_solution_hydrogens   geom
_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
O0AA O 0.2326(5) 0.1208(8) 0.1874(2) 0.0542(15) Uani 1 1 d . . . . .
H0AA H 0.233078 0.196372 0.211274 0.081 Uiso 1 1 calc GR . . . .
C0AA C 0.1275(7) 0.0241(11) 0.1815(3) 0.0474(18) Uani 1 1 d . . . . .
H0AB H 0.111943 -0.035912 0.145566 0.071 Uiso 1 1 calc GR . . . .
H0AC H 0.059929 0.097300 0.182366 0.071 Uiso 1 1 calc GR . . . .
H0AD H 0.138003 -0.055938 0.212651 0.071 Uiso 1 1 calc GR . . . .
O1 O -0.4465(4) 0.9756(6) 0.3626(2) 0.0395(11) Uani 1 1 d . . . . .
H1 H -0.463925 0.966990 0.394106 0.059 Uiso 1 1 calc GR . . . .
C1 C -0.5232(8) 0.8715(11) 0.3227(4) 0.055(2) Uani 1 1 d . . . . .
H1A H -0.524928 0.910554 0.284439 0.083 Uiso 1 1 calc GR . . . .
H1B H -0.603997 0.875373 0.329129 0.083 Uiso 1 1 calc GR . . . .
H1C H -0.493574 0.756788 0.327053 0.083 Uiso 1 1 calc GR . . . .
O1_1 O 0.4968(4) 0.2509(6) -0.01846(17) 0.0309(9) Uani 1 1 d . . . . .
O2_1 O 0.1632(4) 0.4507(5) -0.07086(19) 0.0339(10) Uani 1 1 d . . . . .
O3_1 O 0.1655(4) 0.3711(6) -0.17311(19) 0.0364(10) Uani 1 1 d . . . . .
H3_1 H 0.143384 0.425804 -0.148008 0.055 Uiso 1 1 calc GR . . . .
O4_1 O 0.5104(4) 0.1257(6) -0.20767(18) 0.0369(10) Uani 1 1 d . . . . .
O5_1 O 0.3255(4) 0.1544(6) 0.09801(18) 0.0362(10) Uani 1 1 d . . . . .
H5_1 H 0.298490 0.129439 0.126097 0.054 Uiso 1 1 calc GR . . . .
O6_1 O 0.6752(4) 0.3972(5) 0.06061(18) 0.0308(9) Uani 1 1 d . . . . .
O7_1 O 0.8583(4) 0.4777(6) 0.11318(18) 0.0316(9) Uani 1 1 d . . . . .
O8_1 O 1.1432(4) 0.5744(6) 0.0784(2) 0.0348(10) Uani 1 1 d . . . . .
H8_1 H 1.163601 0.669207 0.069617 0.052 Uiso 1 1 calc GR . . . .
O9_1 O 0.9729(4) 0.5670(6) -0.03189(18) 0.0343(10) Uani 1 1 d . . . . .
H9_1 H 1.036742 0.537455 -0.040037 0.051 Uiso 1 1 calc GR . . . .
O10_1 O 0.7706(4) 0.3601(5) -0.03542(19) 0.0328(10) Uani 1 1 d . . . . .
H10_1 H 0.729120 0.419849 -0.060877 0.049 Uiso 1 1 calc GR . . . .
O11_1 O 1.0155(4) 0.4517(7) 0.2226(2) 0.0421(11) Uani 1 1 d . . . . .
H11_1 H 0.950059 0.480870 0.229062 0.063 Uiso 1 1 calc GR . . . .
C1_1 C 0.4356(6) 0.3069(8) 0.0203(3) 0.0326(14) Uani 1 1 d . . . . .
C2_1 C 0.3276(6) 0.3777(8) 0.0046(3) 0.0309(13) Uani 1 1 d . . . . .
H2_1 H 0.290981 0.421176 0.032653 0.037 Uiso 1 1 calc R . . . .
C3_1 C 0.2659(5) 0.3893(7) -0.0540(3) 0.0282(12) Uani 1 1 d . . . . .
C4_1 C 0.3284(6) 0.3212(8) -0.0941(3) 0.0297(13) Uani 1 1 d . . . . .
C5_1 C 0.2756(6) 0.3116(8) -0.1524(3) 0.0313(13) Uani 1 1 d . . . . .
C6_1 C 0.3385(6) 0.2411(9) -0.1884(3) 0.0339(14) Uani 1 1 d . . . . .
H6_1 H 0.301998 0.229576 -0.227402 0.041 Uiso 1 1 calc R . . . .
C7_1 C 0.4558(6) 0.1867(8) -0.1675(3) 0.0331(14) Uani 1 1 d . . . . .
C8_1 C 0.5111(6) 0.1931(8) -0.1106(3) 0.0324(13) Uani 1 1 d . . . . .
H8A_1 H 0.590583 0.155244 -0.096799 0.039 Uiso 1 1 calc R . . . .
C9_1 C 0.4443(6) 0.2579(8) -0.0747(3) 0.0297(13) Uani 1 1 d . . . . .
C10_1 C 0.6332(6) 0.0837(11) -0.1891(3) 0.0448(17) Uani 1 1 d . . . . .
H10A_1 H 0.665174 0.053996 -0.221665 0.067 Uiso 1 1 calc GR . . . .
H10B_1 H 0.641849 -0.011080 -0.163126 0.067 Uiso 1 1 calc GR . . . .
H10C_1 H 0.677299 0.179261 -0.169592 0.067 Uiso 1 1 calc GR . . . .
C11_1 C 0.5030(6) 0.2692(7) 0.0783(3) 0.0293(13) Uani 1 1 d . . . . .
C12_1 C 0.6247(6) 0.3014(7) 0.0965(3) 0.0303(13) Uani 1 1 d . . . . .
C13_1 C 0.6895(6) 0.2495(8) 0.1492(3) 0.0342(14) Uani 1 1 d . . . . .
H13_1 H 0.772605 0.271313 0.161061 0.041 Uiso 1 1 calc R . . . .
C14_1 C 0.6297(6) 0.1645(8) 0.1843(3) 0.0346(14) Uani 1 1 d . . . . .
H14_1 H 0.673547 0.126189 0.220030 0.042 Uiso 1 1 calc R . . . .
C15_1 C 0.5097(6) 0.1350(8) 0.1687(3) 0.0334(14) Uani 1 1 d . . . . .
H15_1 H 0.470468 0.079404 0.193619 0.040 Uiso 1 1 calc R . . . .
C16_1 C 0.4450(6) 0.1876(8) 0.1153(3) 0.0335(14) Uani 1 1 d . . . . .
C17_1 C 0.7987(5) 0.3857(8) 0.0649(3) 0.0313(13) Uani 1 1 d . . . . .
H17_1 H 0.824698 0.266725 0.068581 0.038 Uiso 1 1 calc R . . . .
C18_1 C 0.8243(5) 0.4619(8) 0.0119(3) 0.0306(13) Uani 1 1 d . . . . .
H18_1 H 0.787630 0.575295 0.006329 0.037 Uiso 1 1 calc R . . . .
C19_1 C 0.9586(5) 0.4781(8) 0.0170(3) 0.0309(13) Uani 1 1 d . . . . .
H19_1 H 0.994671 0.364782 0.017388 0.037 Uiso 1 1 calc R . . . .
C20_1 C 1.0160(6) 0.5692(8) 0.0710(3) 0.0321(13) Uani 1 1 d . . . . .
H20_1 H 0.983601 0.684947 0.069870 0.038 Uiso 1 1 calc R . . . .
C21_1 C 0.9859(5) 0.4730(8) 0.1200(3) 0.0306(13) Uani 1 1 d . . . . .
H21_1 H 1.013302 0.355027 0.119565 0.037 Uiso 1 1 calc R . . . .
C22_1 C 1.0396(6) 0.5511(9) 0.1766(3) 0.0344(14) Uani 1 1 d . . . . .
H22A_1 H 1.126857 0.562159 0.181308 0.041 Uiso 1 1 calc R . . . .
H22B_1 H 1.005990 0.664047 0.177979 0.041 Uiso 1 1 calc R . . . .
O1_2 O 0.0245(4) 0.6953(6) 0.52120(17) 0.0315(10) Uani 1 1 d . . . . .
O2_2 O -0.2547(4) 0.4716(6) 0.56955(19) 0.0352(10) Uani 1 1 d . . . . .
O3_2 O -0.1486(4) 0.5285(6) 0.67454(19) 0.0381(11) Uani 1 1 d . . . . .
H3_2 H -0.198478 0.485211 0.647640 0.057 Uiso 1 1 calc GR . . . .
O4_2 O 0.2060(4) 0.8340(6) 0.71145(19) 0.0374(11) Uani 1 1 d . . . . .
O5_2 O -0.2446(4) 0.8355(7) 0.4144(2) 0.0421(12) Uani 1 1 d . . . . .
H5_2 H -0.297484 0.883905 0.390080 0.063 Uiso 1 1 calc GR . . . .
O6_2 O 0.1119(4) 0.5295(5) 0.43578(18) 0.0310(9) Uani 1 1 d . . . . .
O7_2 O 0.2410(4) 0.4184(6) 0.38647(18) 0.0331(10) Uani 1 1 d . . . . .
O8_2 O 0.5666(4) 0.3837(6) 0.42059(19) 0.0340(10) Uani 1 1 d . . . . .
H8_2 H 0.603646 0.295592 0.431982 0.051 Uiso 1 1 calc GR . . . .
O9_2 O 0.5084(4) 0.4312(6) 0.53190(18) 0.0320(10) Uani 1 1 d . . . . .
H9_2 H 0.581297 0.443380 0.533026 0.048 Uiso 1 1 calc GR . . . .
O10_2 O 0.2994(4) 0.6201(6) 0.52424(18) 0.0327(10) Uani 1 1 d . . . . .
H10_2 H 0.235472 0.603926 0.534324 0.049 Uiso 1 1 calc GR . . . .
O11_2 O 0.2659(4) 0.3485(6) 0.27850(18) 0.0364(10) Uani 1 1 d . . . . .
H11_2 H 0.200436 0.361962 0.287485 0.055 Uiso 1 1 calc GR . . . .
C1_2 C -0.0730(5) 0.6417(7) 0.4820(3) 0.0286(13) Uani 1 1 d . . . . .
C2_2 C -0.1673(5) 0.5679(8) 0.4971(3) 0.0294(13) Uani 1 1 d . . . . .
H2_2 H -0.233544 0.532373 0.468477 0.035 Uiso 1 1 calc R . . . .
C3_2 C -0.1689(5) 0.5425(7) 0.5550(3) 0.0299(13) Uani 1 1 d . . . . .
C4_2 C -0.0678(6) 0.6076(8) 0.5952(3) 0.0309(13) Uani 1 1 d . . . . .
C5_2 C -0.0621(6) 0.6054(8) 0.6545(3) 0.0329(14) Uani 1 1 d . . . . .
C6_2 C 0.0299(6) 0.6810(8) 0.6919(3) 0.0341(14) Uani 1 1 d . . . . .
H6_2 H 0.032378 0.680392 0.731079 0.041 Uiso 1 1 calc R . . . .
C7_2 C 0.1211(6) 0.7600(8) 0.6716(3) 0.0328(13) Uani 1 1 d . . . . .
C8_2 C 0.1232(6) 0.7578(8) 0.6141(3) 0.0296(13) Uani 1 1 d . . . . .
H8A_2 H 0.187500 0.803344 0.600680 0.036 Uiso 1 1 calc R . . . .
C9_2 C 0.0251(6) 0.6847(8) 0.5783(3) 0.0300(13) Uani 1 1 d . . . . .
C10_2 C 0.3094(6) 0.8989(10) 0.6950(3) 0.0400(16) Uani 1 1 d . . . . .
H10A_2 H 0.285141 0.988883 0.667623 0.060 Uiso 1 1 calc GR . . . .
H10B_2 H 0.347251 0.809864 0.677942 0.060 Uiso 1 1 calc GR . . . .
H10C_2 H 0.366171 0.942036 0.728363 0.060 Uiso 1 1 calc GR . . . .
C11_2 C -0.0667(5) 0.6804(8) 0.4238(3) 0.0282(12) Uani 1 1 d . . . . .
C12_2 C 0.0259(6) 0.6244(8) 0.4001(3) 0.0301(13) Uani 1 1 d . . . . .
C13_2 C 0.0268(6) 0.6581(9) 0.3446(3) 0.0345(14) Uani 1 1 d . . . . .
H13_2 H 0.089753 0.617910 0.329041 0.041 Uiso 1 1 calc R . . . .
C14_2 C -0.0651(6) 0.7513(9) 0.3118(3) 0.0347(14) Uani 1 1 d . . . . .
H14_2 H -0.064982 0.773762 0.273579 0.042 Uiso 1 1 calc R . . . .
C15_2 C -0.1576(6) 0.8125(8) 0.3341(3) 0.0328(14) Uani 1 1 d . . . . .
H15_2 H -0.219513 0.877499 0.311480 0.039 Uiso 1 1 calc R . . . .
C16_2 C -0.1578(6) 0.7772(8) 0.3896(3) 0.0316(13) Uani 1 1 d . . . . .
C17_2 C 0.2285(5) 0.5391(8) 0.4273(3) 0.0303(13) Uani 1 1 d . . . . .
H17_2 H 0.245104 0.653212 0.414663 0.036 Uiso 1 1 calc R . . . .
C18_2 C 0.3115(5) 0.4979(8) 0.4833(3) 0.0301(13) Uani 1 1 d . . . . .
H18_2 H 0.288545 0.386938 0.496083 0.036 Uiso 1 1 calc R . . . .
C19_2 C 0.4387(6) 0.4894(8) 0.4783(3) 0.0307(13) Uani 1 1 d . . . . .
H19_2 H 0.466082 0.603515 0.470883 0.037 Uiso 1 1 calc R . . . .
C20_2 C 0.4491(5) 0.3745(8) 0.4297(3) 0.0304(13) Uani 1 1 d . . . . .
H20_2 H 0.433065 0.257533 0.439791 0.037 Uiso 1 1 calc R . . . .
C21_2 C 0.3579(5) 0.4238(8) 0.3761(3) 0.0301(13) Uani 1 1 d . . . . .
H21_2 H 0.375311 0.538836 0.364598 0.036 Uiso 1 1 calc R . . . .
C22_2 C 0.3567(6) 0.3043(9) 0.3280(3) 0.0345(14) Uani 1 1 d . . . . .
H22A_2 H 0.435757 0.305279 0.318651 0.041 Uiso 1 1 calc R . . . .
H22B_2 H 0.341737 0.190068 0.339987 0.041 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O0AA H0AA 0.8400 . ?
O0AA C0AA 1.418(9) . ?
C0AA H0AB 0.9800 . ?
C0AA H0AC 0.9800 . ?
C0AA H0AD 0.9800 . ?
O1 H1 0.8400 . ?
O1 C1 1.424(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O1_1 C1_1 1.381(8) . ?
O1_1 C9_1 1.364(8) . ?
O2_1 C3_1 1.260(7) . ?
O3_1 H3_1 0.8400 . ?
O3_1 C5_1 1.340(8) . ?
O4_1 C7_1 1.373(8) . ?
O4_1 C10_1 1.423(8) . ?
O5_1 H5_1 0.8400 . ?
O5_1 C16_1 1.370(8) . ?
O6_1 C12_1 1.391(7) . ?
O6_1 C17_1 1.405(7) . ?
O7_1 C17_1 1.423(7) . ?
O7_1 C21_1 1.441(7) . ?
O8_1 H8_1 0.8400 . ?
O8_1 C20_1 1.435(7) . ?
O9_1 H9_1 0.8400 . ?
O9_1 C19_1 1.431(7) . ?
O10_1 H10_1 0.8400 . ?
O10_1 C18_1 1.431(7) . ?
O11_1 H11_1 0.8400 . ?
O11_1 C22_1 1.454(8) . ?
C1_1 C2_1 1.340(9) . ?
C1_1 C11_1 1.476(9) . ?
C2_1 H2_1 0.9500 . ?
C2_1 C3_1 1.442(9) . ?
C3_1 C4_1 1.451(9) . ?
C4_1 C5_1 1.411(9) . ?
C4_1 C9_1 1.404(9) . ?
C5_1 C6_1 1.385(9) . ?
C6_1 H6_1 0.9500 . ?
C6_1 C7_1 1.399(9) . ?
C7_1 C8_1 1.384(9) . ?
C8_1 H8A_1 0.9500 . ?
C8_1 C9_1 1.395(9) . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C11_1 C12_1 1.394(9) . ?
C11_1 C16_1 1.405(9) . ?
C12_1 C13_1 1.391(9) . ?
C13_1 H13_1 0.9500 . ?
C13_1 C14_1 1.396(9) . ?
C14_1 H14_1 0.9500 . ?
C14_1 C15_1 1.367(9) . ?
C15_1 H15_1 0.9500 . ?
C15_1 C16_1 1.405(9) . ?
C17_1 H17_1 1.0000 . ?
C17_1 C18_1 1.521(9) . ?
C18_1 H18_1 1.0000 . ?
C18_1 C19_1 1.529(8) . ?
C19_1 H19_1 1.0000 . ?
C19_1 C20_1 1.517(9) . ?
C20_1 H20_1 1.0000 . ?
C20_1 C21_1 1.530(9) . ?
C21_1 H21_1 1.0000 . ?
C21_1 C22_1 1.511(9) . ?
C22_1 H22A_1 0.9900 . ?
C22_1 H22B_1 0.9900 . ?
O1_2 C1_2 1.364(7) . ?
O1_2 C9_2 1.392(8) . ?
O2_2 C3_2 1.263(8) . ?
O3_2 H3_2 0.8400 . ?
O3_2 C5_2 1.358(8) . ?
O4_2 C7_2 1.346(8) . ?
O4_2 C10_2 1.440(8) . ?
O5_2 H5_2 0.8400 . ?
O5_2 C16_2 1.366(8) . ?
O6_2 C12_2 1.384(7) . ?
O6_2 C17_2 1.409(7) . ?
O7_2 C17_2 1.420(7) . ?
O7_2 C21_2 1.429(7) . ?
O8_2 H8_2 0.8400 . ?
O8_2 C20_2 1.425(7) . ?
O9_2 H9_2 0.8400 . ?
O9_2 C19_2 1.443(7) . ?
O10_2 H10_2 0.8400 . ?
O10_2 C18_2 1.429(7) . ?
O11_2 H11_2 0.8400 . ?
O11_2 C22_2 1.446(8) . ?
C1_2 C2_2 1.362(9) . ?
C1_2 C11_2 1.471(9) . ?
C2_2 H2_2 0.9500 . ?
C2_2 C3_2 1.429(9) . ?
C3_2 C4_2 1.436(9) . ?
C4_2 C5_2 1.430(9) . ?
C4_2 C9_2 1.381(9) . ?
C5_2 C6_2 1.369(9) . ?
C6_2 H6_2 0.9500 . ?
C6_2 C7_2 1.413(10) . ?
C7_2 C8_2 1.408(9) . ?
C8_2 H8A_2 0.9500 . ?
C8_2 C9_2 1.388(9) . ?
C10_2 H10A_2 0.9800 . ?
C10_2 H10B_2 0.9800 . ?
C10_2 H10C_2 0.9800 . ?
C11_2 C12_2 1.401(9) . ?
C11_2 C16_2 1.412(9) . ?
C12_2 C13_2 1.383(9) . ?
C13_2 H13_2 0.9500 . ?
C13_2 C14_2 1.388(9) . ?
C14_2 H14_2 0.9500 . ?
C14_2 C15_2 1.394(9) . ?
C15_2 H15_2 0.9500 . ?
C15_2 C16_2 1.384(9) . ?
C17_2 H17_2 1.0000 . ?
C17_2 C18_2 1.510(9) . ?
C18_2 H18_2 1.0000 . ?
C18_2 C19_2 1.501(8) . ?
C19_2 H19_2 1.0000 . ?
C19_2 C20_2 1.528(9) . ?
C20_2 H20_2 1.0000 . ?
C20_2 C21_2 1.526(8) . ?
C21_2 H21_2 1.0000 . ?
C21_2 C22_2 1.512(9) . ?
C22_2 H22A_2 0.9900 . ?
C22_2 H22B_2 0.9900 . ?

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
C0AA O0AA H0AA 109.5 . . ?
O0AA C0AA H0AB 109.5 . . ?
O0AA C0AA H0AC 109.5 . . ?
O0AA C0AA H0AD 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
H0AB C0AA H0AD 109.5 . . ?
H0AC C0AA H0AD 109.5 . . ?
C1 O1 H1 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9_1 O1_1 C1_1 119.8(5) . . ?
C5_1 O3_1 H3_1 109.5 . . ?
C7_1 O4_1 C10_1 116.4(5) . . ?
C16_1 O5_1 H5_1 109.5 . . ?
C12_1 O6_1 C17_1 118.8(5) . . ?
C17_1 O7_1 C21_1 111.4(5) . . ?
C20_1 O8_1 H8_1 109.5 . . ?
C19_1 O9_1 H9_1 109.5 . . ?
C18_1 O10_1 H10_1 109.5 . . ?
C22_1 O11_1 H11_1 109.5 . . ?
O1_1 C1_1 C11_1 110.5(5) . . ?
C2_1 C1_1 O1_1 122.1(6) . . ?
C2_1 C1_1 C11_1 127.4(6) . . ?
C1_1 C2_1 H2_1 119.3 . . ?
C1_1 C2_1 C3_1 121.4(6) . . ?
C3_1 C2_1 H2_1 119.3 . . ?
O2_1 C3_1 C2_1 123.9(6) . . ?
O2_1 C3_1 C4_1 120.3(6) . . ?
C2_1 C3_1 C4_1 115.8(5) . . ?
C5_1 C4_1 C3_1 122.2(6) . . ?
C9_1 C4_1 C3_1 119.5(6) . . ?
C9_1 C4_1 C5_1 118.2(6) . . ?
O3_1 C5_1 C4_1 120.6(6) . . ?
O3_1 C5_1 C6_1 119.8(6) . . ?
C6_1 C5_1 C4_1 119.6(6) . . ?
C5_1 C6_1 H6_1 120.0 . . ?
C5_1 C6_1 C7_1 120.1(6) . . ?
C7_1 C6_1 H6_1 120.0 . . ?
O4_1 C7_1 C6_1 114.6(6) . . ?
O4_1 C7_1 C8_1 123.2(6) . . ?
C8_1 C7_1 C6_1 122.2(6) . . ?
C7_1 C8_1 H8A_1 121.6 . . ?
C7_1 C8_1 C9_1 116.7(6) . . ?
C9_1 C8_1 H8A_1 121.6 . . ?
O1_1 C9_1 C4_1 121.2(6) . . ?
O1_1 C9_1 C8_1 115.8(5) . . ?
C8_1 C9_1 C4_1 123.0(6) . . ?
O4_1 C10_1 H10A_1 109.5 . . ?
O4_1 C10_1 H10B_1 109.5 . . ?
O4_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
C12_1 C11_1 C1_1 122.2(6) . . ?
C12_1 C11_1 C16_1 118.4(6) . . ?
C16_1 C11_1 C1_1 119.2(6) . . ?
O6_1 C12_1 C11_1 116.1(5) . . ?
O6_1 C12_1 C13_1 122.2(6) . . ?
C13_1 C12_1 C11_1 121.5(6) . . ?
C12_1 C13_1 H13_1 120.8 . . ?
C12_1 C13_1 C14_1 118.5(6) . . ?
C14_1 C13_1 H13_1 120.8 . . ?
C13_1 C14_1 H14_1 119.1 . . ?
C15_1 C14_1 C13_1 121.7(6) . . ?
C15_1 C14_1 H14_1 119.1 . . ?
C14_1 C15_1 H15_1 120.3 . . ?
C14_1 C15_1 C16_1 119.3(6) . . ?
C16_1 C15_1 H15_1 120.3 . . ?
O5_1 C16_1 C11_1 119.2(6) . . ?
O5_1 C16_1 C15_1 120.3(6) . . ?
C11_1 C16_1 C15_1 120.4(6) . . ?
O6_1 C17_1 O7_1 108.3(5) . . ?
O6_1 C17_1 H17_1 110.3 . . ?
O6_1 C17_1 C18_1 107.7(5) . . ?
O7_1 C17_1 H17_1 110.3 . . ?
O7_1 C17_1 C18_1 110.0(5) . . ?
C18_1 C17_1 H17_1 110.3 . . ?
O10_1 C18_1 C17_1 108.8(5) . . ?
O10_1 C18_1 H18_1 108.8 . . ?
O10_1 C18_1 C19_1 110.7(5) . . ?
C17_1 C18_1 H18_1 108.8 . . ?
C17_1 C18_1 C19_1 111.0(5) . . ?
C19_1 C18_1 H18_1 108.8 . . ?
O9_1 C19_1 C18_1 106.6(5) . . ?
O9_1 C19_1 H19_1 109.5 . . ?
O9_1 C19_1 C20_1 111.7(5) . . ?
C18_1 C19_1 H19_1 109.5 . . ?
C20_1 C19_1 C18_1 109.8(5) . . ?
C20_1 C19_1 H19_1 109.5 . . ?
O8_1 C20_1 C19_1 110.4(5) . . ?
O8_1 C20_1 H20_1 109.9 . . ?
O8_1 C20_1 C21_1 109.1(5) . . ?
C19_1 C20_1 H20_1 109.9 . . ?
C19_1 C20_1 C21_1 107.5(5) . . ?
C21_1 C20_1 H20_1 109.9 . . ?
O7_1 C21_1 C20_1 107.9(5) . . ?
O7_1 C21_1 H21_1 109.9 . . ?
O7_1 C21_1 C22_1 106.5(5) . . ?
C20_1 C21_1 H21_1 109.9 . . ?
C22_1 C21_1 C20_1 112.6(5) . . ?
C22_1 C21_1 H21_1 109.9 . . ?
O11_1 C22_1 C21_1 111.4(5) . . ?
O11_1 C22_1 H22A_1 109.4 . . ?
O11_1 C22_1 H22B_1 109.4 . . ?
C21_1 C22_1 H22A_1 109.4 . . ?
C21_1 C22_1 H22B_1 109.4 . . ?
H22A_1 C22_1 H22B_1 108.0 . . ?
C1_2 O1_2 C9_2 119.4(5) . . ?
C5_2 O3_2 H3_2 109.5 . . ?
C7_2 O4_2 C10_2 117.9(5) . . ?
C16_2 O5_2 H5_2 109.5 . . ?
C12_2 O6_2 C17_2 116.5(5) . . ?
C17_2 O7_2 C21_2 111.0(5) . . ?
C20_2 O8_2 H8_2 109.5 . . ?
C19_2 O9_2 H9_2 109.5 . . ?
C18_2 O10_2 H10_2 109.5 . . ?
C22_2 O11_2 H11_2 109.5 . . ?
O1_2 C1_2 C11_2 112.9(5) . . ?
C2_2 C1_2 O1_2 121.9(6) . . ?
C2_2 C1_2 C11_2 125.1(5) . . ?
C1_2 C2_2 H2_2 119.2 . . ?
C1_2 C2_2 C3_2 121.5(6) . . ?
C3_2 C2_2 H2_2 119.2 . . ?
O2_2 C3_2 C2_2 122.3(6) . . ?
O2_2 C3_2 C4_2 122.4(6) . . ?
C2_2 C3_2 C4_2 115.3(6) . . ?
C5_2 C4_2 C3_2 121.6(6) . . ?
C9_2 C4_2 C3_2 121.4(6) . . ?
C9_2 C4_2 C5_2 116.9(6) . . ?
O3_2 C5_2 C4_2 120.4(6) . . ?
O3_2 C5_2 C6_2 118.8(6) . . ?
C6_2 C5_2 C4_2 120.8(6) . . ?
C5_2 C6_2 H6_2 120.3 . . ?
C5_2 C6_2 C7_2 119.4(6) . . ?
C7_2 C6_2 H6_2 120.3 . . ?
O4_2 C7_2 C6_2 114.9(6) . . ?
O4_2 C7_2 C8_2 123.1(6) . . ?
C8_2 C7_2 C6_2 122.0(6) . . ?
C7_2 C8_2 H8A_2 122.2 . . ?
C9_2 C8_2 C7_2 115.5(6) . . ?
C9_2 C8_2 H8A_2 122.2 . . ?
C4_2 C9_2 O1_2 120.2(5) . . ?
C4_2 C9_2 C8_2 125.2(6) . . ?
C8_2 C9_2 O1_2 114.6(6) . . ?
O4_2 C10_2 H10A_2 109.5 . . ?
O4_2 C10_2 H10B_2 109.5 . . ?
O4_2 C10_2 H10C_2 109.5 . . ?
H10A_2 C10_2 H10B_2 109.5 . . ?
H10A_2 C10_2 H10C_2 109.5 . . ?
H10B_2 C10_2 H10C_2 109.5 . . ?
C12_2 C11_2 C1_2 123.0(5) . . ?
C12_2 C11_2 C16_2 117.8(6) . . ?
C16_2 C11_2 C1_2 119.2(5) . . ?
O6_2 C12_2 C11_2 114.9(5) . . ?
C13_2 C12_2 O6_2 123.7(6) . . ?
C13_2 C12_2 C11_2 121.4(6) . . ?
C12_2 C13_2 H13_2 120.3 . . ?
C12_2 C13_2 C14_2 119.3(6) . . ?
C14_2 C13_2 H13_2 120.3 . . ?
C13_2 C14_2 H14_2 119.4 . . ?
C13_2 C14_2 C15_2 121.1(6) . . ?
C15_2 C14_2 H14_2 119.4 . . ?
C14_2 C15_2 H15_2 120.5 . . ?
C16_2 C15_2 C14_2 119.0(6) . . ?
C16_2 C15_2 H15_2 120.5 . . ?
O5_2 C16_2 C11_2 116.7(6) . . ?
O5_2 C16_2 C15_2 122.0(6) . . ?
C15_2 C16_2 C11_2 121.3(6) . . ?
O6_2 C17_2 O7_2 108.8(5) . . ?
O6_2 C17_2 H17_2 110.7 . . ?
O6_2 C17_2 C18_2 106.3(5) . . ?
O7_2 C17_2 H17_2 110.7 . . ?
O7_2 C17_2 C18_2 109.7(5) . . ?
C18_2 C17_2 H17_2 110.7 . . ?
O10_2 C18_2 C17_2 109.7(5) . . ?
O10_2 C18_2 H18_2 108.6 . . ?
O10_2 C18_2 C19_2 110.1(5) . . ?
C17_2 C18_2 H18_2 108.6 . . ?
C19_2 C18_2 C17_2 111.2(5) . . ?
C19_2 C18_2 H18_2 108.6 . . ?
O9_2 C19_2 C18_2 106.8(5) . . ?
O9_2 C19_2 H19_2 109.2 . . ?
O9_2 C19_2 C20_2 112.3(5) . . ?
C18_2 C19_2 H19_2 109.2 . . ?
C18_2 C19_2 C20_2 110.2(5) . . ?
C20_2 C19_2 H19_2 109.2 . . ?
O8_2 C20_2 C19_2 109.8(5) . . ?
O8_2 C20_2 H20_2 108.9 . . ?
O8_2 C20_2 C21_2 110.1(5) . . ?
C19_2 C20_2 H20_2 108.9 . . ?
C21_2 C20_2 C19_2 110.1(5) . . ?
C21_2 C20_2 H20_2 108.9 . . ?
O7_2 C21_2 C20_2 109.3(5) . . ?
O7_2 C21_2 H21_2 109.7 . . ?
O7_2 C21_2 C22_2 106.2(5) . . ?
C20_2 C21_2 H21_2 109.7 . . ?
C22_2 C21_2 C20_2 112.3(5) . . ?
C22_2 C21_2 H21_2 109.7 . . ?
O11_2 C22_2 C21_2 111.4(5) . . ?
O11_2 C22_2 H22A_2 109.3 . . ?
O11_2 C22_2 H22B_2 109.3 . . ?
C21_2 C22_2 H22A_2 109.3 . . ?
C21_2 C22_2 H22B_2 109.3 . . ?
H22A_2 C22_2 H22B_2 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C1_1 C2_1 C3_1 4.2(10) . . . . ?
O1_1 C1_1 C11_1 C12_1 46.6(8) . . . . ?
O1_1 C1_1 C11_1 C16_1 -128.9(6) . . . . ?
O2_1 C3_1 C4_1 C5_1 -3.7(9) . . . . ?
O2_1 C3_1 C4_1 C9_1 178.0(5) . . . . ?
O3_1 C5_1 C6_1 C7_1 176.6(6) . . . . ?
O4_1 C7_1 C8_1 C9_1 -179.8(6) . . . . ?
O6_1 C12_1 C13_1 C14_1 175.2(6) . . . . ?
O6_1 C17_1 C18_1 O10_1 -66.4(6) . . . . ?
O6_1 C17_1 C18_1 C19_1 171.6(5) . . . . ?
O7_1 C17_1 C18_1 O10_1 175.8(5) . . . . ?
O7_1 C17_1 C18_1 C19_1 53.8(7) . . . . ?
O7_1 C21_1 C22_1 O11_1 65.3(7) . . . . ?
O8_1 C20_1 C21_1 O7_1 176.8(5) . . . . ?
O8_1 C20_1 C21_1 C22_1 59.6(7) . . . . ?
O9_1 C19_1 C20_1 O8_1 -66.2(6) . . . . ?
O9_1 C19_1 C20_1 C21_1 174.8(5) . . . . ?
O10_1 C18_1 C19_1 O9_1 65.3(6) . . . . ?
O10_1 C18_1 C19_1 C20_1 -173.4(5) . . . . ?
C1_1 O1_1 C9_1 C4_1 -0.1(9) . . . . ?
C1_1 O1_1 C9_1 C8_1 -177.8(5) . . . . ?
C1_1 C2_1 C3_1 O2_1 178.1(6) . . . . ?
C1_1 C2_1 C3_1 C4_1 -0.5(9) . . . . ?
C1_1 C11_1 C12_1 O6_1 10.9(9) . . . . ?
C1_1 C11_1 C12_1 C13_1 -173.2(6) . . . . ?
C1_1 C11_1 C16_1 O5_1 -4.1(9) . . . . ?
C1_1 C11_1 C16_1 C15_1 173.5(6) . . . . ?
C2_1 C1_1 C11_1 C12_1 -136.5(7) . . . . ?
C2_1 C1_1 C11_1 C16_1 48.1(10) . . . . ?
C2_1 C3_1 C4_1 C5_1 174.9(6) . . . . ?
C2_1 C3_1 C4_1 C9_1 -3.3(8) . . . . ?
C3_1 C4_1 C5_1 O3_1 2.2(10) . . . . ?
C3_1 C4_1 C5_1 C6_1 -178.2(6) . . . . ?
C3_1 C4_1 C9_1 O1_1 3.7(9) . . . . ?
C3_1 C4_1 C9_1 C8_1 -178.8(6) . . . . ?
C4_1 C5_1 C6_1 C7_1 -2.9(10) . . . . ?
C5_1 C4_1 C9_1 O1_1 -174.6(6) . . . . ?
C5_1 C4_1 C9_1 C8_1 2.9(9) . . . . ?
C5_1 C6_1 C7_1 O4_1 -177.3(6) . . . . ?
C5_1 C6_1 C7_1 C8_1 3.2(10) . . . . ?
C6_1 C7_1 C8_1 C9_1 -0.4(10) . . . . ?
C7_1 C8_1 C9_1 O1_1 175.0(6) . . . . ?
C7_1 C8_1 C9_1 C4_1 -2.7(10) . . . . ?
C9_1 O1_1 C1_1 C2_1 -3.9(9) . . . . ?
C9_1 O1_1 C1_1 C11_1 173.2(5) . . . . ?
C9_1 C4_1 C5_1 O3_1 -179.6(6) . . . . ?
C9_1 C4_1 C5_1 C6_1 0.0(9) . . . . ?
C10_1 O4_1 C7_1 C6_1 174.3(6) . . . . ?
C10_1 O4_1 C7_1 C8_1 -6.3(10) . . . . ?
C11_1 C1_1 C2_1 C3_1 -172.5(6) . . . . ?
C11_1 C12_1 C13_1 C14_1 -0.5(10) . . . . ?
C12_1 O6_1 C17_1 O7_1 -76.7(6) . . . . ?
C12_1 O6_1 C17_1 C18_1 164.4(5) . . . . ?
C12_1 C11_1 C16_1 O5_1 -179.7(6) . . . . ?
C12_1 C11_1 C16_1 C15_1 -2.2(9) . . . . ?
C12_1 C13_1 C14_1 C15_1 -1.5(10) . . . . ?
C13_1 C14_1 C15_1 C16_1 1.6(10) . . . . ?
C14_1 C15_1 C16_1 O5_1 177.8(6) . . . . ?
C14_1 C15_1 C16_1 C11_1 0.3(10) . . . . ?
C16_1 C11_1 C12_1 O6_1 -173.7(5) . . . . ?
C16_1 C11_1 C12_1 C13_1 2.3(9) . . . . ?
C17_1 O6_1 C12_1 C11_1 -157.4(5) . . . . ?
C17_1 O6_1 C12_1 C13_1 26.7(8) . . . . ?
C17_1 O7_1 C21_1 C20_1 67.3(6) . . . . ?
C17_1 O7_1 C21_1 C22_1 -171.5(5) . . . . ?
C17_1 C18_1 C19_1 O9_1 -173.8(5) . . . . ?
C17_1 C18_1 C19_1 C20_1 -52.5(7) . . . . ?
C18_1 C19_1 C20_1 O8_1 175.7(5) . . . . ?
C18_1 C19_1 C20_1 C21_1 56.7(6) . . . . ?
C19_1 C20_1 C21_1 O7_1 -63.4(6) . . . . ?
C19_1 C20_1 C21_1 C22_1 179.4(5) . . . . ?
C20_1 C21_1 C22_1 O11_1 -176.6(5) . . . . ?
C21_1 O7_1 C17_1 O6_1 -179.4(5) . . . . ?
C21_1 O7_1 C17_1 C18_1 -62.0(6) . . . . ?
O1_2 C1_2 C2_2 C3_2 -0.1(10) . . . . ?
O1_2 C1_2 C11_2 C12_2 58.4(8) . . . . ?
O1_2 C1_2 C11_2 C16_2 -122.1(6) . . . . ?
O2_2 C3_2 C4_2 C5_2 -4.1(9) . . . . ?
O2_2 C3_2 C4_2 C9_2 -180.0(6) . . . . ?
O3_2 C5_2 C6_2 C7_2 179.4(6) . . . . ?
O4_2 C7_2 C8_2 C9_2 -176.3(6) . . . . ?
O6_2 C12_2 C13_2 C14_2 178.4(6) . . . . ?
O6_2 C17_2 C18_2 O10_2 -63.0(6) . . . . ?
O6_2 C17_2 C18_2 C19_2 175.0(5) . . . . ?
O7_2 C17_2 C18_2 O10_2 179.6(5) . . . . ?
O7_2 C17_2 C18_2 C19_2 57.6(6) . . . . ?
O7_2 C21_2 C22_2 O11_2 57.8(6) . . . . ?
O8_2 C20_2 C21_2 O7_2 -178.4(5) . . . . ?
O8_2 C20_2 C21_2 C22_2 64.0(7) . . . . ?
O9_2 C19_2 C20_2 O8_2 -68.5(6) . . . . ?
O9_2 C19_2 C20_2 C21_2 170.1(5) . . . . ?
O10_2 C18_2 C19_2 O9_2 64.7(6) . . . . ?
O10_2 C18_2 C19_2 C20_2 -173.2(5) . . . . ?
C1_2 O1_2 C9_2 C4_2 5.5(8) . . . . ?
C1_2 O1_2 C9_2 C8_2 -173.8(5) . . . . ?
C1_2 C2_2 C3_2 O2_2 -178.8(6) . . . . ?
C1_2 C2_2 C3_2 C4_2 3.0(9) . . . . ?
C1_2 C11_2 C12_2 O6_2 -0.1(9) . . . . ?
C1_2 C11_2 C12_2 C13_2 177.7(6) . . . . ?
C1_2 C11_2 C16_2 O5_2 2.8(9) . . . . ?
C1_2 C11_2 C16_2 C15_2 -178.0(6) . . . . ?
C2_2 C1_2 C11_2 C12_2 -124.8(7) . . . . ?
C2_2 C1_2 C11_2 C16_2 54.8(9) . . . . ?
C2_2 C3_2 C4_2 C5_2 174.1(6) . . . . ?
C2_2 C3_2 C4_2 C9_2 -1.8(9) . . . . ?
C3_2 C4_2 C5_2 O3_2 5.4(9) . . . . ?
C3_2 C4_2 C5_2 C6_2 -174.2(6) . . . . ?
C3_2 C4_2 C9_2 O1_2 -2.4(9) . . . . ?
C3_2 C4_2 C9_2 C8_2 176.9(6) . . . . ?
C4_2 C5_2 C6_2 C7_2 -1.0(10) . . . . ?
C5_2 C4_2 C9_2 O1_2 -178.5(5) . . . . ?
C5_2 C4_2 C9_2 C8_2 0.8(10) . . . . ?
C5_2 C6_2 C7_2 O4_2 178.5(6) . . . . ?
C5_2 C6_2 C7_2 C8_2 -2.6(10) . . . . ?
C6_2 C7_2 C8_2 C9_2 4.9(9) . . . . ?
C7_2 C8_2 C9_2 O1_2 175.3(5) . . . . ?
C7_2 C8_2 C9_2 C4_2 -4.1(9) . . . . ?
C9_2 O1_2 C1_2 C2_2 -4.3(9) . . . . ?
C9_2 O1_2 C1_2 C11_2 172.7(5) . . . . ?
C9_2 C4_2 C5_2 O3_2 -178.5(6) . . . . ?
C9_2 C4_2 C5_2 C6_2 1.9(9) . . . . ?
C10_2 O4_2 C7_2 C6_2 172.4(6) . . . . ?
C10_2 O4_2 C7_2 C8_2 -6.4(9) . . . . ?
C11_2 C1_2 C2_2 C3_2 -176.7(6) . . . . ?
C11_2 C12_2 C13_2 C14_2 0.9(10) . . . . ?
C12_2 O6_2 C17_2 O7_2 -87.8(6) . . . . ?
C12_2 O6_2 C17_2 C18_2 154.1(5) . . . . ?
C12_2 C11_2 C16_2 O5_2 -177.6(6) . . . . ?
C12_2 C11_2 C16_2 C15_2 1.6(9) . . . . ?
C12_2 C13_2 C14_2 C15_2 0.6(10) . . . . ?
C13_2 C14_2 C15_2 C16_2 -0.9(10) . . . . ?
C14_2 C15_2 C16_2 O5_2 178.9(6) . . . . ?
C14_2 C15_2 C16_2 C11_2 -0.2(10) . . . . ?
C16_2 C11_2 C12_2 O6_2 -179.7(5) . . . . ?
C16_2 C11_2 C12_2 C13_2 -1.9(9) . . . . ?
C17_2 O6_2 C12_2 C11_2 -149.6(5) . . . . ?
C17_2 O6_2 C12_2 C13_2 32.7(8) . . . . ?
C17_2 O7_2 C21_2 C20_2 64.5(6) . . . . ?
C17_2 O7_2 C21_2 C22_2 -174.1(5) . . . . ?
C17_2 C18_2 C19_2 O9_2 -173.6(5) . . . . ?
C17_2 C18_2 C19_2 C20_2 -51.4(7) . . . . ?
C18_2 C19_2 C20_2 O8_2 172.6(5) . . . . ?
C18_2 C19_2 C20_2 C21_2 51.2(7) . . . . ?
C19_2 C20_2 C21_2 O7_2 -57.1(6) . . . . ?
C19_2 C20_2 C21_2 C22_2 -174.7(5) . . . . ?
C20_2 C21_2 C22_2 O11_2 177.2(5) . . . . ?
C21_2 O7_2 C17_2 O6_2 179.7(5) . . . . ?
C21_2 O7_2 C17_2 C18_2 -64.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(3)
2 0.20(4)
3 0.1(3)
4 -0.11(4)

####################################################################### 
# 
# 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_pj_kuc_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 2072155'
loop_
_audit_author_name
_audit_author_address
'Narender Goel'
;National Institute of Pharmaceutical Education and Research, Kolkata, India
India
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-02-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Skullcapflavone I'
_chemical_formula_moiety         'C17 H14 O6'
_chemical_formula_sum            'C17 H14 O6'
_chemical_formula_weight         314.28
_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                   4.9210(11)
_cell_length_b                   21.735(4)
_cell_length_c                   13.1847(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.263(11)
_cell_angle_gamma                90
_cell_volume                     1401.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.93
_cell_measurement_theta_min      3.95
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1236 before and 0.0769 after correction. The Ratio of minimum to maximum transmission is 0.8146. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_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             656
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29097
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.212
_diffrn_reflns_theta_max         66.212
_diffrn_reflns_theta_min         3.939
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2323
_reflns_number_total             2436
_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       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2014/5(Sheldrick 2014)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.066
_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)+(0.0578P)²+0.8470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1120
_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:
 C3(H3A), C6(H6A), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5')
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C), C00M(H00D,H00E,H00F)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.1833(2) 0.47644(5) 0.75977(8) 0.0199(3) Uani 1 1 d . . . . .
O2 O -0.0393(2) 0.38550(5) 0.49171(8) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.3702(2) 0.30931(5) 0.53715(9) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.241973 0.325222 0.501669 0.037 Uiso 1 1 calc GR . . . .
O4 O 0.8798(2) 0.33798(5) 0.86615(9) 0.0234(3) Uani 1 1 d . . . . .
O5 O 0.5903(2) 0.43963(5) 0.89893(9) 0.0235(3) Uani 1 1 d . . . . .
O6 O -0.5106(2) 0.56087(6) 0.60052(9) 0.0252(3) Uani 1 1 d . . . . .
H6 H -0.639912 0.583123 0.580434 0.038 Uiso 1 1 calc GR . . . .
C2 C -0.0274(3) 0.49813(8) 0.69265(12) 0.0184(4) Uani 1 1 d . . . . .
C3 C -0.1073(3) 0.46825(8) 0.60398(12) 0.0199(4) Uani 1 1 d . . . . .
H3A H -0.255521 0.483235 0.561302 0.024 Uiso 1 1 calc R . . . .
C4 C 0.0316(3) 0.41401(7) 0.57447(12) 0.0184(4) Uani 1 1 d . . . . .
C5 C 0.4235(3) 0.34175(8) 0.62524(12) 0.0197(4) Uani 1 1 d . . . . .
C6 C 0.6352(3) 0.32257(7) 0.69660(13) 0.0200(4) Uani 1 1 d . . . . .
H6A H 0.742266 0.288907 0.683066 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6861(3) 0.35446(8) 0.78931(13) 0.0198(4) Uani 1 1 d . . . . .
C8 C 0.5338(3) 0.40686(8) 0.80977(12) 0.0191(4) Uani 1 1 d . . . . .
C1' C -0.1322(3) 0.55633(8) 0.73075(12) 0.0193(4) Uani 1 1 d . . . . .
C2' C 0.0093(4) 0.58433(8) 0.81722(13) 0.0241(4) Uani 1 1 d . . . . .
H2' H 0.160582 0.564425 0.850779 0.029 Uiso 1 1 calc R . . . .
C3' C -0.0692(4) 0.64049(8) 0.85390(13) 0.0259(4) Uani 1 1 d . . . . .
H3' H 0.028514 0.658000 0.911045 0.031 Uiso 1 1 calc R . . . .
C4' C -0.2958(4) 0.67052(8) 0.80447(13) 0.0248(4) Uani 1 1 d . . . . .
H4' H -0.350054 0.708299 0.828557 0.030 Uiso 1 1 calc R . . . .
C5' C -0.4408(4) 0.64421(8) 0.71943(13) 0.0236(4) Uani 1 1 d . . . . .
H5' H -0.591373 0.664730 0.686646 0.028 Uiso 1 1 calc R . . . .
C6' C -0.3643(3) 0.58724(8) 0.68209(12) 0.0204(4) Uani 1 1 d . . . . .
C4A C 0.2618(3) 0.39350(7) 0.64400(12) 0.0187(4) Uani 1 1 d . . . . .
C8A C 0.3264(3) 0.42541(7) 0.73630(12) 0.0189(4) Uani 1 1 d . . . . .
C00I C 1.0404(4) 0.28431(8) 0.85185(14) 0.0255(4) Uani 1 1 d . . . . .
H00A H 1.135240 0.289617 0.792568 0.038 Uiso 1 1 calc GR . . . .
H00B H 0.922833 0.249039 0.842679 0.038 Uiso 1 1 calc GR . . . .
H00C H 1.170654 0.278306 0.910703 0.038 Uiso 1 1 calc GR . . . .
C00M C 0.4181(4) 0.42078(9) 0.97543(14) 0.0289(4) Uani 1 1 d . . . . .
H00D H 0.229823 0.423147 0.947647 0.043 Uiso 1 1 calc GR . . . .
H00E H 0.448773 0.447453 1.033591 0.043 Uiso 1 1 calc GR . . . .
H00F H 0.461505 0.379217 0.995871 0.043 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 C2 1.3710(19) . ?
O1 C8A 1.367(2) . ?
O2 C4 1.270(2) . ?
O3 H3 0.8200 . ?
O3 C5 1.360(2) . ?
O4 C7 1.361(2) . ?
O4 C00I 1.433(2) . ?
O5 C8 1.3765(19) . ?
O5 C00M 1.445(2) . ?
O6 H6 0.8200 . ?
O6 C6' 1.354(2) . ?
C2 C3 1.358(2) . ?
C2 C1' 1.475(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.438(2) . ?
C4 C4A 1.448(2) . ?
C5 C6 1.389(2) . ?
C5 C4A 1.415(2) . ?
C6 H6A 0.9300 . ?
C6 C7 1.404(2) . ?
C7 C8 1.405(2) . ?
C8 C8A 1.388(2) . ?
C1' C2' 1.408(2) . ?
C1' C6' 1.417(2) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.383(2) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.391(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.385(2) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.399(2) . ?
C4A C8A 1.407(2) . ?
C00I H00A 0.9600 . ?
C00I H00B 0.9600 . ?
C00I H00C 0.9600 . ?
C00M H00D 0.9600 . ?
C00M H00E 0.9600 . ?
C00M H00F 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
C8A O1 C2 120.31(13) . . ?
C5 O3 H3 109.5 . . ?
C7 O4 C00I 117.89(13) . . ?
C8 O5 C00M 111.73(13) . . ?
C6' O6 H6 109.5 . . ?
O1 C2 C1' 110.06(14) . . ?
C3 C2 O1 121.27(15) . . ?
C3 C2 C1' 128.63(15) . . ?
C2 C3 H3A 119.2 . . ?
C2 C3 C4 121.57(15) . . ?
C4 C3 H3A 119.2 . . ?
O2 C4 C3 122.58(15) . . ?
O2 C4 C4A 121.08(15) . . ?
C3 C4 C4A 116.33(14) . . ?
O3 C5 C6 118.90(15) . . ?
O3 C5 C4A 120.12(14) . . ?
C6 C5 C4A 120.97(15) . . ?
C5 C6 H6A 120.3 . . ?
C5 C6 C7 119.39(15) . . ?
C7 C6 H6A 120.3 . . ?
O4 C7 C6 124.19(15) . . ?
O4 C7 C8 114.53(14) . . ?
C6 C7 C8 121.28(15) . . ?
O5 C8 C7 121.40(14) . . ?
O5 C8 C8A 120.68(15) . . ?
C8A C8 C7 117.92(15) . . ?
C2' C1' C2 119.08(15) . . ?
C2' C1' C6' 117.71(15) . . ?
C6' C1' C2 123.16(15) . . ?
C1' C2' H2' 118.9 . . ?
C3' C2' C1' 122.14(16) . . ?
C3' C2' H2' 118.9 . . ?
C2' C3' H3' 120.3 . . ?
C2' C3' C4' 119.37(16) . . ?
C4' C3' H3' 120.3 . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' C3' 120.08(16) . . ?
C5' C4' H4' 120.0 . . ?
C4' C5' H5' 119.5 . . ?
C4' C5' C6' 121.04(16) . . ?
C6' C5' H5' 119.5 . . ?
O6 C6' C1' 119.42(15) . . ?
O6 C6' C5' 120.92(15) . . ?
C5' C6' C1' 119.65(15) . . ?
C5 C4A C4 123.38(15) . . ?
C8A C4A C4 118.89(15) . . ?
C8A C4A C5 117.71(15) . . ?
O1 C8A C8 115.81(14) . . ?
O1 C8A C4A 121.50(14) . . ?
C8 C8A C4A 122.68(15) . . ?
O4 C00I H00A 109.5 . . ?
O4 C00I H00B 109.5 . . ?
O4 C00I H00C 109.5 . . ?
H00A C00I H00B 109.5 . . ?
H00A C00I H00C 109.5 . . ?
H00B C00I H00C 109.5 . . ?
O5 C00M H00D 109.5 . . ?
O5 C00M H00E 109.5 . . ?
O5 C00M H00F 109.5 . . ?
H00D C00M H00E 109.5 . . ?
H00D C00M H00F 109.5 . . ?
H00E C00M H00F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -2.5(2) . . . . ?
O1 C2 C1' C2' 7.9(2) . . . . ?
O1 C2 C1' C6' -174.76(14) . . . . ?
O2 C4 C4A C5 0.6(2) . . . . ?
O2 C4 C4A C8A -177.86(14) . . . . ?
O3 C5 C6 C7 -177.84(14) . . . . ?
O3 C5 C4A C4 1.6(2) . . . . ?
O3 C5 C4A C8A -179.90(14) . . . . ?
O4 C7 C8 O5 3.1(2) . . . . ?
O4 C7 C8 C8A -177.99(14) . . . . ?
O5 C8 C8A O1 -1.3(2) . . . . ?
O5 C8 C8A C4A 179.83(14) . . . . ?
C2 O1 C8A C8 -179.39(14) . . . . ?
C2 O1 C8A C4A -0.5(2) . . . . ?
C2 C3 C4 O2 -179.75(15) . . . . ?
C2 C3 C4 C4A -0.5(2) . . . . ?
C2 C1' C2' C3' 176.58(16) . . . . ?
C2 C1' C6' O6 4.5(2) . . . . ?
C2 C1' C6' C5' -176.07(15) . . . . ?
C3 C2 C1' C2' -169.86(17) . . . . ?
C3 C2 C1' C6' 7.5(3) . . . . ?
C3 C4 C4A C5 -178.65(15) . . . . ?
C3 C4 C4A C8A 2.9(2) . . . . ?
C4 C4A C8A O1 -2.5(2) . . . . ?
C4 C4A C8A C8 176.34(15) . . . . ?
C5 C6 C7 O4 176.97(15) . . . . ?
C5 C6 C7 C8 -2.5(2) . . . . ?
C5 C4A C8A O1 178.98(14) . . . . ?
C5 C4A C8A C8 -2.2(2) . . . . ?
C6 C5 C4A C4 -177.28(15) . . . . ?
C6 C5 C4A C8A 1.2(2) . . . . ?
C6 C7 C8 O5 -177.43(15) . . . . ?
C6 C7 C8 C8A 1.5(2) . . . . ?
C7 C8 C8A O1 179.75(14) . . . . ?
C7 C8 C8A C4A 0.9(2) . . . . ?
C1' C2 C3 C4 175.00(16) . . . . ?
C1' C2' C3' C4' 0.3(3) . . . . ?
C2' C1' C6' O6 -178.04(15) . . . . ?
C2' C1' C6' C5' 1.3(2) . . . . ?
C2' C3' C4' C5' 0.1(3) . . . . ?
C3' C4' C5' C6' 0.4(3) . . . . ?
C4' C5' C6' O6 178.28(16) . . . . ?
C4' C5' C6' C1' -1.1(3) . . . . ?
C6' C1' C2' C3' -0.9(3) . . . . ?
C4A C5 C6 C7 1.1(2) . . . . ?
C8A O1 C2 C3 3.1(2) . . . . ?
C8A O1 C2 C1' -174.86(13) . . . . ?
C00I O4 C7 C6 -0.6(2) . . . . ?
C00I O4 C7 C8 178.87(14) . . . . ?
C00M O5 C8 C7 -95.55(18) . . . . ?
C00M O5 C8 C8A 85.55(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
