# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_r20220504d
_database_code_depnum_ccdc_archive 'CCDC 2224173'
loop_
_audit_author_name
_audit_author_address
'Mukaidaisi Taiwaikuli'
;Tianjin University
China
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ARB
_chemical_name_systematic        arbutin
_chemical_formula_moiety         'C12 H16 O7'
_chemical_formula_sum            'C12 H16 O7'
_chemical_formula_weight         272.25
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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        P21
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   21.5133(14)
_cell_length_b                   4.9621(4)
_cell_length_c                   24.1452(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.496(6)
_cell_angle_gamma                90
_cell_volume                     2565.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5377
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      31.7690
_cell_measurement_theta_min      3.0020
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0920
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22331
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.862
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50   12.00    --  -30.00  45.00   0.00  360
  2  ω   -120.00  45.00   0.50   12.00    --  -30.00  45.00  90.00  330
  3  ω   -120.00  45.00   0.50   12.00    --  -30.00  45.00 180.00  330
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0061259000
_diffrn_orient_matrix_UB_12      0.0203119000
_diffrn_orient_matrix_UB_13      0.0280505000
_diffrn_orient_matrix_UB_21      -0.0324505000
_diffrn_orient_matrix_UB_22      0.0070580000
_diffrn_orient_matrix_UB_23      -0.0084531000
_diffrn_orient_matrix_UB_31      -0.0025103000
_diffrn_orient_matrix_UB_32      -0.1412949000
_diffrn_orient_matrix_UB_33      0.0036182000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                4692
_reflns_number_total             10224
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       0.0061(6)
_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   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         10224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1558
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7A), C8(H8), C9(H9), C10(H10), C11(H11), C7A(H7AB), C8A(H8A), C9A(H9A),
 C10A(H10A), C11A(H11A), C7B(H7BA), C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B),
 C7D(H7DA), C8D(H8D), C9D(H9D), C10D(H10D), C11D(H11D)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D), C12B(H12E,H12F), C12D(H12G,H12H)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5A), C6(H6A), C2A(H2A), C3A(H3A), C5A(H5AB), C6A(H6AB),
 C2B(H2B), C3B(H3B), C5B(H5BA), C6B(H6BA), C2D(H2D), C3D(H3D), C5D(H5DA),
 C6D(H6DA)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O5(H5), O6(H6), O7(H7), O1A(H1A), O4A(H4A), O5A(H5AA),
 O6A(H6AA), O7A(H7AA), O1B(H1B), O4B(H4B), O5B(H5B), O6B(H6B), O7B(H7B),
 O1D(H1D), O4D(H4D), O5D(H5D), O6D(H6D), O7D(H7D)
;
_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 -0.21583(17) -0.2601(9) 0.3508(2) 0.0619(13) Uani 1 1 d . . . . .
H1 H -0.231496 -0.117416 0.339420 0.093 Uiso 1 1 calc R U . . .
O2 O 0.04006(16) -0.2497(8) 0.33676(14) 0.0358(10) Uani 1 1 d . . . . .
O3 O 0.09131(17) -0.4187(8) 0.41537(13) 0.0362(10) Uani 1 1 d . . . . .
O4 O 0.17526(19) -0.3370(9) 0.51371(15) 0.0490(12) Uani 1 1 d . . . . .
H4 H 0.169633 -0.228982 0.488015 0.073 Uiso 1 1 calc R U . . .
O5 O 0.21066(18) -0.9374(9) 0.43940(17) 0.0495(12) Uani 1 1 d . . . . .
H5 H 0.247627 -0.912927 0.449858 0.074 Uiso 1 1 calc R U . . .
O6 O 0.23138(18) -0.7301(8) 0.32980(18) 0.0473(11) Uani 1 1 d . . . . .
H6 H 0.243869 -0.576134 0.325437 0.071 Uiso 1 1 calc R U . . .
O7 O 0.1190(2) -0.5362(8) 0.27059(14) 0.0491(12) Uani 1 1 d . . . . .
H7 H 0.121359 -0.698220 0.264402 0.074 Uiso 1 1 calc R U . . .
C1 C -0.1522(3) -0.2519(13) 0.3475(2) 0.0417(15) Uani 1 1 d . . . . .
C2 C -0.1154(3) -0.4374(12) 0.3777(2) 0.0388(15) Uani 1 1 d . . . . .
H2 H -0.133983 -0.564063 0.399265 0.047 Uiso 1 1 calc R U . . .
C3 C -0.0511(3) -0.4382(12) 0.3766(2) 0.0366(14) Uani 1 1 d . . . . .
H3 H -0.026603 -0.559598 0.398332 0.044 Uiso 1 1 calc R U . . .
C4 C -0.0238(2) -0.2572(12) 0.34282(19) 0.0296(13) Uani 1 1 d . . . . .
C5 C -0.0594(2) -0.0690(12) 0.3124(2) 0.0340(14) Uani 1 1 d . . . . .
H5A H -0.040799 0.055447 0.290362 0.041 Uiso 1 1 calc R U . . .
C6 C -0.1241(3) -0.0674(12) 0.3150(2) 0.0414(15) Uani 1 1 d . . . . .
H6A H -0.148465 0.059435 0.294567 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0755(2) -0.4694(12) 0.3580(2) 0.0302(13) Uani 1 1 d . . . . .
H7A H 0.051255 -0.636275 0.352947 0.036 Uiso 1 1 calc R U . . .
C8 C 0.1237(3) -0.6396(12) 0.4426(2) 0.0367(15) Uani 1 1 d . . . . .
H8 H 0.097307 -0.800775 0.438820 0.044 Uiso 1 1 calc R U . . .
C9 C 0.1841(3) -0.6924(12) 0.4165(2) 0.0343(14) Uani 1 1 d . . . . .
H9 H 0.213172 -0.543405 0.425579 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1725(2) -0.7210(13) 0.3533(2) 0.0351(14) Uani 1 1 d . . . . .
H10 H 0.149864 -0.889308 0.344521 0.042 Uiso 1 1 calc R U . . .
C11 C 0.1342(2) -0.4874(12) 0.32830(19) 0.0319(14) Uani 1 1 d . . . . .
H11 H 0.158092 -0.319737 0.333539 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1342(3) -0.5603(14) 0.5035(2) 0.0463(17) Uani 1 1 d . . . . .
H12A H 0.094238 -0.516341 0.516691 0.056 Uiso 1 1 calc R U . . .
H12B H 0.151208 -0.713721 0.524729 0.056 Uiso 1 1 calc R U . . .
O1A O 0.28154(16) -0.2363(9) 0.31484(18) 0.0538(12) Uani 1 1 d . . . . .
H1A H 0.267531 -0.111203 0.332022 0.081 Uiso 1 1 calc R U . . .
O2A O 0.54068(16) -0.2392(8) 0.33841(14) 0.0371(10) Uani 1 1 d . . . . .
O3A O 0.58549(17) -0.4028(8) 0.42019(14) 0.0385(10) Uani 1 1 d . . . . .
O4A O 0.66749(19) -0.3323(10) 0.52337(15) 0.0504(12) Uani 1 1 d . . . . .
H4A H 0.662951 -0.215636 0.499260 0.076 Uiso 1 1 calc R U . . .
O5A O 0.70242(19) -0.9263(9) 0.45374(17) 0.0527(12) Uani 1 1 d . . . . .
H5AA H 0.737690 -0.895084 0.468325 0.079 Uiso 1 1 calc R U . . .
O6A O 0.72758(17) -0.7717(8) 0.34157(18) 0.0465(11) Uani 1 1 d . . . . .
H6AA H 0.745056 -0.626001 0.339006 0.070 Uiso 1 1 calc R U . . .
O7A O 0.6194(2) -0.5575(8) 0.27806(14) 0.0473(12) Uani 1 1 d . . . . .
H7AA H 0.619621 -0.721299 0.273518 0.071 Uiso 1 1 calc R U . . .
C1A C 0.3467(2) -0.2372(12) 0.3241(2) 0.0353(13) Uani 1 1 d . . . . .
C2A C 0.3777(3) -0.4157(12) 0.3605(2) 0.0362(14) Uani 1 1 d . . . . .
H2A H 0.355126 -0.535754 0.380411 0.043 Uiso 1 1 calc R U . . .
C3A C 0.4427(3) -0.4169(13) 0.3677(2) 0.0387(15) Uani 1 1 d . . . . .
H3A H 0.463521 -0.533162 0.393429 0.046 Uiso 1 1 calc R U . . .
C4A C 0.4761(2) -0.2457(12) 0.3368(2) 0.0303(13) Uani 1 1 d . . . . .
C5A C 0.4452(2) -0.0620(12) 0.3011(2) 0.0358(14) Uani 1 1 d . . . . .
H5AB H 0.467674 0.058333 0.281211 0.043 Uiso 1 1 calc R U . . .
C6A C 0.3804(3) -0.0582(12) 0.2950(2) 0.0425(15) Uani 1 1 d . . . . .
H6AB H 0.359508 0.066164 0.271194 0.051 Uiso 1 1 calc R U . . .
C7A C 0.5723(2) -0.4624(13) 0.3627(2) 0.0327(14) Uani 1 1 d . . . . .
H7AB H 0.546339 -0.624506 0.357642 0.039 Uiso 1 1 calc R U . . .
C8A C 0.6158(3) -0.6201(13) 0.4501(2) 0.0384(16) Uani 1 1 d . . . . .
H8A H 0.588619 -0.778738 0.445766 0.046 Uiso 1 1 calc R U . . .
C9A C 0.6771(3) -0.6869(12) 0.4270(2) 0.0360(15) Uani 1 1 d . . . . .
H9A H 0.706357 -0.537780 0.435267 0.043 Uiso 1 1 calc R U . . .
C10A C 0.6688(2) -0.7317(13) 0.3639(2) 0.0367(14) Uani 1 1 d . . . . .
H10A H 0.643849 -0.895589 0.356732 0.044 Uiso 1 1 calc R U . . .
C11A C 0.6327(3) -0.4982(11) 0.3354(2) 0.0321(14) Uani 1 1 d . . . . .
H11A H 0.657700 -0.333050 0.339791 0.039 Uiso 1 1 calc R U . . .
C12A C 0.6230(3) -0.5422(14) 0.5109(2) 0.0499(18) Uani 1 1 d . . . . .
H12C H 0.582846 -0.484323 0.521622 0.060 Uiso 1 1 calc R U . . .
H12D H 0.635796 -0.699722 0.532894 0.060 Uiso 1 1 calc R U . . .
O1B O 0.46620(17) 0.2435(9) 0.1548(2) 0.0612(13) Uani 1 1 d . . . . .
H1B H 0.481108 0.390282 0.164386 0.092 Uiso 1 1 calc R U . . .
O2B O 0.20881(16) 0.2521(8) 0.15791(14) 0.0366(10) Uani 1 1 d . . . . .
O3B O 0.16168(17) 0.0748(8) 0.07868(14) 0.0364(10) Uani 1 1 d . . . . .
O4B O 0.0809(2) 0.1493(10) -0.02208(15) 0.0531(12) Uani 1 1 d . . . . .
H4B H 0.082296 0.248826 0.005127 0.080 Uiso 1 1 calc R U . . .
O5B O 0.04328(19) -0.4444(9) 0.05147(19) 0.0568(13) Uani 1 1 d . . . . .
H5B H 0.005549 -0.426858 0.043741 0.085 Uiso 1 1 calc R U . . .
O6B O 0.01752(19) -0.2250(9) 0.15961(19) 0.0540(12) Uani 1 1 d . . . . .
H6B H 0.010405 -0.375379 0.171566 0.081 Uiso 1 1 calc R U . . .
O7B O 0.1269(2) -0.0345(8) 0.22201(15) 0.0488(12) Uani 1 1 d . . . . .
H7B H 0.142520 -0.183882 0.227580 0.073 Uiso 1 1 calc R U . . .
C1B C 0.4013(2) 0.2538(13) 0.1544(2) 0.0376(14) Uani 1 1 d . . . . .
C2B C 0.3673(3) 0.0675(13) 0.1227(2) 0.0416(15) Uani 1 1 d . . . . .
H2B H 0.387300 -0.056969 0.101650 0.050 Uiso 1 1 calc R U . . .
C3B C 0.3024(3) 0.0660(13) 0.1221(2) 0.0396(15) Uani 1 1 d . . . . .
H3B H 0.278829 -0.056089 0.099700 0.048 Uiso 1 1 calc R U . . .
C4B C 0.2735(2) 0.2443(12) 0.1545(2) 0.0305(13) Uani 1 1 d . . . . .
C5B C 0.3078(3) 0.4319(12) 0.1857(2) 0.0373(15) Uani 1 1 d . . . . .
H5BA H 0.287855 0.555534 0.206894 0.045 Uiso 1 1 calc R U . . .
C6B C 0.3727(3) 0.4385(13) 0.1859(2) 0.0416(16) Uani 1 1 d . . . . .
H6BA H 0.396196 0.566011 0.206952 0.050 Uiso 1 1 calc R U . . .
C7B C 0.1746(2) 0.0294(12) 0.13678(19) 0.0303(14) Uani 1 1 d . . . . .
H7BA H 0.199276 -0.135568 0.143351 0.036 Uiso 1 1 calc R U . . .
C8B C 0.1304(3) -0.1475(13) 0.0505(2) 0.0366(15) Uani 1 1 d . . . . .
H8B H 0.156878 -0.308020 0.055478 0.044 Uiso 1 1 calc R U . . .
C9B C 0.0685(2) -0.2011(13) 0.0752(2) 0.0339(14) Uani 1 1 d . . . . .
H9B H 0.039581 -0.053029 0.064917 0.041 Uiso 1 1 calc R U . . .
C10B C 0.0771(2) -0.2247(12) 0.1380(2) 0.0294(13) Uani 1 1 d . . . . .
H10B H 0.098833 -0.393688 0.148276 0.035 Uiso 1 1 calc R U . . .
C11B C 0.1143(2) 0.0080(12) 0.16407(19) 0.0319(14) Uani 1 1 d . . . . .
H11B H 0.090312 0.174844 0.157614 0.038 Uiso 1 1 calc R U . . .
C12B C 0.1224(3) -0.0742(14) -0.0104(2) 0.0500(18) Uani 1 1 d . . . . .
H12E H 0.162896 -0.029710 -0.022518 0.060 Uiso 1 1 calc R U . . .
H12F H 0.106362 -0.229247 -0.031701 0.060 Uiso 1 1 calc R U . . .
O1D O 0.03170(17) -0.2353(9) -0.1814(2) 0.0573(12) Uani 1 1 d . . . . .
H1D H 0.017964 -0.374424 -0.168890 0.086 Uiso 1 1 calc R U . . .
O2D O 0.29028(16) -0.2407(8) -0.16727(14) 0.0366(10) Uani 1 1 d . . . . .
O3D O 0.33871(16) -0.4002(8) -0.08641(13) 0.0347(10) Uani 1 1 d . . . . .
O4D O 0.42327(19) -0.3225(9) 0.01480(15) 0.0490(11) Uani 1 1 d . . . . .
H4D H 0.416690 -0.205054 -0.008927 0.073 Uiso 1 1 calc R U . . .
O5D O 0.45658(19) -0.9205(9) -0.05557(18) 0.0539(13) Uani 1 1 d . . . . .
H5D H 0.491819 -0.889210 -0.040944 0.081 Uiso 1 1 calc R U . . .
O6D O 0.47696(18) -0.7666(9) -0.16869(18) 0.0499(12) Uani 1 1 d . . . . .
H6D H 0.497625 -0.627506 -0.166675 0.075 Uiso 1 1 calc R U . . .
O7D O 0.3678(2) -0.5577(8) -0.22966(14) 0.0462(11) Uani 1 1 d . . . . .
H7D H 0.343772 -0.686362 -0.232625 0.069 Uiso 1 1 calc R U . . .
C1D C 0.0969(2) -0.2413(13) -0.1748(2) 0.0393(14) Uani 1 1 d . . . . .
C2D C 0.1288(3) -0.4210(13) -0.1395(2) 0.0425(16) Uani 1 1 d . . . . .
H2D H 0.107222 -0.541389 -0.118836 0.051 Uiso 1 1 calc R U . . .
C3D C 0.1940(3) -0.4212(13) -0.1349(2) 0.0405(15) Uani 1 1 d . . . . .
H3D H 0.216195 -0.538276 -0.110300 0.049 Uiso 1 1 calc R U . . .
C4D C 0.2253(2) -0.2478(12) -0.1669(2) 0.0314(13) Uani 1 1 d . . . . .
C5D C 0.1925(3) -0.0661(12) -0.2015(2) 0.0379(15) Uani 1 1 d . . . . .
H5DA H 0.213770 0.054675 -0.222341 0.046 Uiso 1 1 calc R U . . .
C6D C 0.1279(3) -0.0630(13) -0.2053(2) 0.0434(16) Uani 1 1 d . . . . .
H6DA H 0.105704 0.060125 -0.228560 0.052 Uiso 1 1 calc R U . . .
C7D C 0.3235(2) -0.4597(12) -0.1438(2) 0.0312(14) Uani 1 1 d . . . . .
H7DA H 0.297827 -0.623021 -0.147786 0.037 Uiso 1 1 calc R U . . .
C8D C 0.3699(3) -0.6201(12) -0.0569(2) 0.0374(15) Uani 1 1 d . . . . .
H8D H 0.343044 -0.779764 -0.060773 0.045 Uiso 1 1 calc R U . . .
C9D C 0.4310(2) -0.6817(12) -0.0814(2) 0.0321(14) Uani 1 1 d . . . . .
H9D H 0.460181 -0.531835 -0.073534 0.039 Uiso 1 1 calc R U . . .
C10D C 0.4201(2) -0.7245(12) -0.1439(2) 0.0311(13) Uani 1 1 d . . . . .
H10D H 0.395166 -0.888931 -0.149955 0.037 Uiso 1 1 calc R U . . .
C11D C 0.3829(2) -0.4972(12) -0.1724(2) 0.0319(14) Uani 1 1 d . . . . .
H11D H 0.407632 -0.330962 -0.168982 0.038 Uiso 1 1 calc R U . . .
C12D C 0.3789(3) -0.5398(14) 0.0037(2) 0.0463(17) Uani 1 1 d . . . . .
H12G H 0.338961 -0.485018 0.015540 0.056 Uiso 1 1 calc R U . . .
H12H H 0.393151 -0.695472 0.025686 0.056 Uiso 1 1 calc R U . . .


_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 C1 1.381(6) . ?
O2 C4 1.396(5) . ?
O2 C7 1.399(6) . ?
O3 C7 1.416(5) . ?
O3 C8 1.425(6) . ?
O4 H4 0.8200 . ?
O4 C12 1.424(7) . ?
O5 H5 0.8200 . ?
O5 C9 1.431(6) . ?
O6 H6 0.8200 . ?
O6 C10 1.438(5) . ?
O7 H7 0.8200 . ?
O7 C11 1.421(6) . ?
C1 C2 1.377(7) . ?
C1 C6 1.382(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(7) . ?
C4 C5 1.376(7) . ?
C5 H5A 0.9300 . ?
C5 C6 1.397(7) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9800 . ?
C7 C11 1.514(7) . ?
C8 H8 0.9800 . ?
C8 C9 1.518(7) . ?
C8 C12 1.518(7) . ?
C9 H9 0.9800 . ?
C9 C10 1.529(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.514(7) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O1A H1A 0.8200 . ?
O1A C1A 1.399(6) . ?
O2A C4A 1.386(6) . ?
O2A C7A 1.398(6) . ?
O3A C7A 1.422(5) . ?
O3A C8A 1.421(6) . ?
O4A H4A 0.8200 . ?
O4A C12A 1.427(7) . ?
O5A H5AA 0.8200 . ?
O5A C9A 1.435(7) . ?
O6A H6AA 0.8200 . ?
O6A C10A 1.436(6) . ?
O7A H7AA 0.8200 . ?
O7A C11A 1.417(6) . ?
C1A C2A 1.375(7) . ?
C1A C6A 1.379(8) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.393(7) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.379(7) . ?
C4A C5A 1.380(7) . ?
C5A H5AB 0.9300 . ?
C5A C6A 1.388(7) . ?
C6A H6AB 0.9300 . ?
C7A H7AB 0.9800 . ?
C7A C11A 1.524(7) . ?
C8A H8A 0.9800 . ?
C8A C9A 1.517(7) . ?
C8A C12A 1.510(7) . ?
C9A H9A 0.9800 . ?
C9A C10A 1.533(7) . ?
C10A H10A 0.9800 . ?
C10A C11A 1.522(7) . ?
C11A H11A 0.9800 . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
O1B H1B 0.8200 . ?
O1B C1B 1.395(6) . ?
O2B C4B 1.402(6) . ?
O2B C7B 1.396(6) . ?
O3B C7B 1.422(5) . ?
O3B C8B 1.430(7) . ?
O4B H4B 0.8200 . ?
O4B C12B 1.435(7) . ?
O5B H5B 0.8200 . ?
O5B C9B 1.422(7) . ?
O6B H6B 0.8200 . ?
O6B C10B 1.430(6) . ?
O7B H7B 0.8200 . ?
O7B C11B 1.415(6) . ?
C1B C2B 1.368(7) . ?
C1B C6B 1.373(7) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.395(7) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.370(7) . ?
C4B C5B 1.369(7) . ?
C5B H5BA 0.9300 . ?
C5B C6B 1.396(7) . ?
C6B H6BA 0.9300 . ?
C7B H7BA 0.9800 . ?
C7B C11B 1.515(7) . ?
C8B H8B 0.9800 . ?
C8B C9B 1.533(7) . ?
C8B C12B 1.509(7) . ?
C9B H9B 0.9800 . ?
C9B C10B 1.514(6) . ?
C10B H10B 0.9800 . ?
C10B C11B 1.507(7) . ?
C11B H11B 0.9800 . ?
C12B H12E 0.9700 . ?
C12B H12F 0.9700 . ?
O1D H1D 0.8200 . ?
O1D C1D 1.397(6) . ?
O2D C4D 1.399(6) . ?
O2D C7D 1.391(6) . ?
O3D C7D 1.423(5) . ?
O3D C8D 1.434(6) . ?
O4D H4D 0.8200 . ?
O4D C12D 1.448(7) . ?
O5D H5D 0.8200 . ?
O5D C9D 1.425(7) . ?
O6D H6D 0.8200 . ?
O6D C10D 1.427(6) . ?
O7D H7D 0.8200 . ?
O7D C11D 1.422(6) . ?
C1D C2D 1.371(8) . ?
C1D C6D 1.366(8) . ?
C2D H2D 0.9300 . ?
C2D C3D 1.397(7) . ?
C3D H3D 0.9300 . ?
C3D C4D 1.375(7) . ?
C4D C5D 1.377(7) . ?
C5D H5DA 0.9300 . ?
C5D C6D 1.384(7) . ?
C6D H6DA 0.9300 . ?
C7D H7DA 0.9800 . ?
C7D C11D 1.523(7) . ?
C8D H8D 0.9800 . ?
C8D C9D 1.522(7) . ?
C8D C12D 1.512(7) . ?
C9D H9D 0.9800 . ?
C9D C10D 1.520(6) . ?
C10D H10D 0.9800 . ?
C10D C11D 1.510(7) . ?
C11D H11D 0.9800 . ?
C12D H12G 0.9700 . ?
C12D H12H 0.9700 . ?

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
C1 O1 H1 109.5 . . ?
C4 O2 C7 116.6(4) . . ?
C7 O3 C8 112.0(4) . . ?
C12 O4 H4 109.5 . . ?
C9 O5 H5 109.5 . . ?
C10 O6 H6 109.5 . . ?
C11 O7 H7 109.5 . . ?
O1 C1 C6 122.9(6) . . ?
C2 C1 O1 118.2(6) . . ?
C2 C1 C6 118.9(6) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(6) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 O2 123.9(5) . . ?
C5 C4 O2 115.4(5) . . ?
C5 C4 C3 120.7(5) . . ?
C4 C5 H5A 120.5 . . ?
C4 C5 C6 119.0(5) . . ?
C6 C5 H5A 120.5 . . ?
C1 C6 C5 120.9(6) . . ?
C1 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
O2 C7 O3 107.0(4) . . ?
O2 C7 H7A 110.4 . . ?
O2 C7 C11 108.8(4) . . ?
O3 C7 H7A 110.4 . . ?
O3 C7 C11 109.9(4) . . ?
C11 C7 H7A 110.4 . . ?
O3 C8 H8 109.4 . . ?
O3 C8 C9 110.0(4) . . ?
O3 C8 C12 105.5(5) . . ?
C9 C8 H8 109.4 . . ?
C9 C8 C12 113.1(5) . . ?
C12 C8 H8 109.4 . . ?
O5 C9 C8 108.3(5) . . ?
O5 C9 H9 109.4 . . ?
O5 C9 C10 109.1(5) . . ?
C8 C9 H9 109.4 . . ?
C8 C9 C10 111.4(4) . . ?
C10 C9 H9 109.4 . . ?
O6 C10 C9 109.4(4) . . ?
O6 C10 H10 109.0 . . ?
O6 C10 C11 109.4(4) . . ?
C9 C10 H10 109.0 . . ?
C11 C10 C9 111.0(4) . . ?
C11 C10 H10 109.0 . . ?
O7 C11 C7 110.6(4) . . ?
O7 C11 C10 109.0(4) . . ?
O7 C11 H11 109.9 . . ?
C7 C11 H11 109.9 . . ?
C10 C11 C7 107.6(4) . . ?
C10 C11 H11 109.9 . . ?
O4 C12 C8 113.7(5) . . ?
O4 C12 H12A 108.8 . . ?
O4 C12 H12B 108.8 . . ?
C8 C12 H12A 108.8 . . ?
C8 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C1A O1A H1A 109.5 . . ?
C4A O2A C7A 116.0(4) . . ?
C8A O3A C7A 112.2(4) . . ?
C12A O4A H4A 109.5 . . ?
C9A O5A H5AA 109.5 . . ?
C10A O6A H6AA 109.5 . . ?
C11A O7A H7AA 109.5 . . ?
C2A C1A O1A 121.3(5) . . ?
C2A C1A C6A 119.6(5) . . ?
C6A C1A O1A 119.0(5) . . ?
C1A C2A H2A 119.9 . . ?
C1A C2A C3A 120.1(6) . . ?
C3A C2A H2A 119.9 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 119.9(5) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A O2A 124.9(5) . . ?
C3A C4A C5A 120.0(5) . . ?
C5A C4A O2A 115.1(5) . . ?
C4A C5A H5AB 120.2 . . ?
C4A C5A C6A 119.6(5) . . ?
C6A C5A H5AB 120.2 . . ?
C1A C6A C5A 120.6(6) . . ?
C1A C6A H6AB 119.7 . . ?
C5A C6A H6AB 119.7 . . ?
O2A C7A O3A 106.7(5) . . ?
O2A C7A H7AB 110.5 . . ?
O2A C7A C11A 108.2(4) . . ?
O3A C7A H7AB 110.5 . . ?
O3A C7A C11A 110.3(4) . . ?
C11A C7A H7AB 110.5 . . ?
O3A C8A H8A 108.4 . . ?
O3A C8A C9A 110.5(4) . . ?
O3A C8A C12A 107.4(5) . . ?
C9A C8A H8A 108.4 . . ?
C12A C8A H8A 108.4 . . ?
C12A C8A C9A 113.6(5) . . ?
O5A C9A C8A 108.7(5) . . ?
O5A C9A H9A 108.9 . . ?
O5A C9A C10A 109.3(5) . . ?
C8A C9A H9A 108.9 . . ?
C8A C9A C10A 112.0(4) . . ?
C10A C9A H9A 108.9 . . ?
O6A C10A C9A 111.7(4) . . ?
O6A C10A H10A 107.8 . . ?
O6A C10A C11A 111.4(5) . . ?
C9A C10A H10A 107.8 . . ?
C11A C10A C9A 110.2(5) . . ?
C11A C10A H10A 107.8 . . ?
O7A C11A C7A 110.2(4) . . ?
O7A C11A C10A 109.3(4) . . ?
O7A C11A H11A 109.7 . . ?
C7A C11A H11A 109.7 . . ?
C10A C11A C7A 108.2(4) . . ?
C10A C11A H11A 109.7 . . ?
O4A C12A C8A 113.4(5) . . ?
O4A C12A H12C 108.9 . . ?
O4A C12A H12D 108.9 . . ?
C8A C12A H12C 108.9 . . ?
C8A C12A H12D 108.9 . . ?
H12C C12A H12D 107.7 . . ?
C1B O1B H1B 109.5 . . ?
C7B O2B C4B 116.6(4) . . ?
C7B O3B C8B 112.7(4) . . ?
C12B O4B H4B 109.5 . . ?
C9B O5B H5B 109.5 . . ?
C10B O6B H6B 109.5 . . ?
C11B O7B H7B 109.5 . . ?
C2B C1B O1B 117.4(5) . . ?
C2B C1B C6B 121.1(5) . . ?
C6B C1B O1B 121.5(6) . . ?
C1B C2B H2B 120.3 . . ?
C1B C2B C3B 119.4(6) . . ?
C3B C2B H2B 120.3 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B C2B 120.0(5) . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B O2B 124.0(5) . . ?
C5B C4B O2B 115.8(5) . . ?
C5B C4B C3B 120.2(5) . . ?
C4B C5B H5BA 119.8 . . ?
C4B C5B C6B 120.3(5) . . ?
C6B C5B H5BA 119.8 . . ?
C1B C6B C5B 118.9(6) . . ?
C1B C6B H6BA 120.5 . . ?
C5B C6B H6BA 120.5 . . ?
O2B C7B O3B 106.4(4) . . ?
O2B C7B H7BA 110.1 . . ?
O2B C7B C11B 109.9(4) . . ?
O3B C7B H7BA 110.1 . . ?
O3B C7B C11B 110.2(4) . . ?
C11B C7B H7BA 110.1 . . ?
O3B C8B H8B 109.1 . . ?
O3B C8B C9B 109.6(4) . . ?
O3B C8B C12B 106.4(5) . . ?
C9B C8B H8B 109.1 . . ?
C12B C8B H8B 109.1 . . ?
C12B C8B C9B 113.5(5) . . ?
O5B C9B C8B 107.6(5) . . ?
O5B C9B H9B 109.0 . . ?
O5B C9B C10B 110.1(5) . . ?
C8B C9B H9B 109.0 . . ?
C10B C9B C8B 112.1(4) . . ?
C10B C9B H9B 109.0 . . ?
O6B C10B C9B 109.7(4) . . ?
O6B C10B H10B 109.2 . . ?
O6B C10B C11B 107.8(4) . . ?
C9B C10B H10B 109.2 . . ?
C11B C10B C9B 111.6(4) . . ?
C11B C10B H10B 109.2 . . ?
O7B C11B C7B 110.5(4) . . ?
O7B C11B C10B 110.0(4) . . ?
O7B C11B H11B 109.3 . . ?
C7B C11B H11B 109.3 . . ?
C10B C11B C7B 108.3(4) . . ?
C10B C11B H11B 109.3 . . ?
O4B C12B C8B 112.8(5) . . ?
O4B C12B H12E 109.0 . . ?
O4B C12B H12F 109.0 . . ?
C8B C12B H12E 109.0 . . ?
C8B C12B H12F 109.0 . . ?
H12E C12B H12F 107.8 . . ?
C1D O1D H1D 109.5 . . ?
C7D O2D C4D 116.9(4) . . ?
C7D O3D C8D 112.2(4) . . ?
C12D O4D H4D 109.5 . . ?
C9D O5D H5D 109.5 . . ?
C10D O6D H6D 109.5 . . ?
C11D O7D H7D 109.5 . . ?
C2D C1D O1D 121.4(6) . . ?
C6D C1D O1D 117.5(6) . . ?
C6D C1D C2D 121.1(6) . . ?
C1D C2D H2D 120.4 . . ?
C1D C2D C3D 119.2(6) . . ?
C3D C2D H2D 120.4 . . ?
C2D C3D H3D 120.1 . . ?
C4D C3D C2D 119.9(6) . . ?
C4D C3D H3D 120.1 . . ?
C3D C4D O2D 124.3(5) . . ?
C3D C4D C5D 120.0(5) . . ?
C5D C4D O2D 115.7(5) . . ?
C4D C5D H5DA 120.0 . . ?
C4D C5D C6D 120.0(5) . . ?
C6D C5D H5DA 120.0 . . ?
C1D C6D C5D 119.8(6) . . ?
C1D C6D H6DA 120.1 . . ?
C5D C6D H6DA 120.1 . . ?
O2D C7D O3D 107.2(4) . . ?
O2D C7D H7DA 110.1 . . ?
O2D C7D C11D 109.3(4) . . ?
O3D C7D H7DA 110.1 . . ?
O3D C7D C11D 110.0(4) . . ?
C11D C7D H7DA 110.1 . . ?
O3D C8D H8D 108.9 . . ?
O3D C8D C9D 109.9(4) . . ?
O3D C8D C12D 106.9(5) . . ?
C9D C8D H8D 108.9 . . ?
C12D C8D H8D 108.9 . . ?
C12D C8D C9D 113.2(5) . . ?
O5D C9D C8D 108.0(4) . . ?
O5D C9D H9D 109.5 . . ?
O5D C9D C10D 109.5(5) . . ?
C8D C9D H9D 109.5 . . ?
C10D C9D C8D 110.9(4) . . ?
C10D C9D H9D 109.5 . . ?
O6D C10D C9D 112.4(4) . . ?
O6D C10D H10D 107.1 . . ?
O6D C10D C11D 110.8(4) . . ?
C9D C10D H10D 107.1 . . ?
C11D C10D C9D 111.9(4) . . ?
C11D C10D H10D 107.1 . . ?
O7D C11D C7D 110.0(4) . . ?
O7D C11D C10D 110.3(4) . . ?
O7D C11D H11D 109.3 . . ?
C7D C11D H11D 109.3 . . ?
C10D C11D C7D 108.4(4) . . ?
C10D C11D H11D 109.3 . . ?
O4D C12D C8D 113.3(5) . . ?
O4D C12D H12G 108.9 . . ?
O4D C12D H12H 108.9 . . ?
C8D C12D H12G 108.9 . . ?
C8D C12D H12H 108.9 . . ?
H12G C12D H12H 107.7 . . ?

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 C1 C2 C3 -179.4(5) . . . . ?
O1 C1 C6 C5 -179.2(5) . . . . ?
O2 C4 C5 C6 178.4(5) . . . . ?
O2 C7 C11 O7 -62.7(6) . . . . ?
O2 C7 C11 C10 178.3(4) . . . . ?
O3 C7 C11 O7 -179.6(5) . . . . ?
O3 C7 C11 C10 61.4(6) . . . . ?
O3 C8 C9 O5 -171.9(4) . . . . ?
O3 C8 C9 C10 -52.0(6) . . . . ?
O3 C8 C12 O4 -66.0(6) . . . . ?
O5 C9 C10 O6 -69.1(6) . . . . ?
O5 C9 C10 C11 170.0(4) . . . . ?
O6 C10 C11 O7 65.3(6) . . . . ?
O6 C10 C11 C7 -174.8(4) . . . . ?
C1 C2 C3 C4 -2.6(8) . . . . ?
C2 C1 C6 C5 0.4(8) . . . . ?
C2 C3 C4 O2 -177.0(5) . . . . ?
C2 C3 C4 C5 2.9(8) . . . . ?
C3 C4 C5 C6 -1.5(8) . . . . ?
C4 O2 C7 O3 -84.5(5) . . . . ?
C4 O2 C7 C11 156.8(4) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
C6 C1 C2 C3 1.0(8) . . . . ?
C7 O2 C4 C3 12.2(7) . . . . ?
C7 O2 C4 C5 -167.7(4) . . . . ?
C7 O3 C8 C9 60.6(6) . . . . ?
C7 O3 C8 C12 -177.2(4) . . . . ?
C8 O3 C7 O2 175.6(4) . . . . ?
C8 O3 C7 C11 -66.5(6) . . . . ?
C8 C9 C10 O6 171.4(5) . . . . ?
C8 C9 C10 C11 50.6(6) . . . . ?
C9 C8 C12 O4 54.2(7) . . . . ?
C9 C10 C11 O7 -173.9(5) . . . . ?
C9 C10 C11 C7 -53.9(6) . . . . ?
C12 C8 C9 O5 70.4(6) . . . . ?
C12 C8 C9 C10 -169.7(5) . . . . ?
O1A C1A C2A C3A 178.2(5) . . . . ?
O1A C1A C6A C5A -176.9(5) . . . . ?
O2A C4A C5A C6A 177.9(5) . . . . ?
O2A C7A C11A O7A -63.6(6) . . . . ?
O2A C7A C11A C10A 177.0(4) . . . . ?
O3A C7A C11A O7A 180.0(5) . . . . ?
O3A C7A C11A C10A 60.6(6) . . . . ?
O3A C8A C9A O5A -173.2(4) . . . . ?
O3A C8A C9A C10A -52.3(6) . . . . ?
O3A C8A C12A O4A -70.0(6) . . . . ?
O5A C9A C10A O6A -64.4(6) . . . . ?
O5A C9A C10A C11A 171.2(5) . . . . ?
O6A C10A C11A O7A 62.0(6) . . . . ?
O6A C10A C11A C7A -178.0(4) . . . . ?
C1A C2A C3A C4A -2.4(8) . . . . ?
C2A C1A C6A C5A 1.9(9) . . . . ?
C2A C3A C4A O2A -176.5(5) . . . . ?
C2A C3A C4A C5A 3.8(8) . . . . ?
C3A C4A C5A C6A -2.5(8) . . . . ?
C4A O2A C7A O3A -90.8(5) . . . . ?
C4A O2A C7A C11A 150.4(4) . . . . ?
C4A C5A C6A C1A -0.4(8) . . . . ?
C6A C1A C2A C3A -0.5(8) . . . . ?
C7A O2A C4A C3A 15.9(7) . . . . ?
C7A O2A C4A C5A -164.5(4) . . . . ?
C7A O3A C8A C9A 59.6(6) . . . . ?
C7A O3A C8A C12A -175.9(4) . . . . ?
C8A O3A C7A O2A 177.8(4) . . . . ?
C8A O3A C7A C11A -64.9(6) . . . . ?
C8A C9A C10A O6A 175.0(5) . . . . ?
C8A C9A C10A C11A 50.6(6) . . . . ?
C9A C8A C12A O4A 52.6(7) . . . . ?
C9A C10A C11A O7A -173.5(5) . . . . ?
C9A C10A C11A C7A -53.4(6) . . . . ?
C12A C8A C9A O5A 65.9(6) . . . . ?
C12A C8A C9A C10A -173.2(5) . . . . ?
O1B C1B C2B C3B 178.4(5) . . . . ?
O1B C1B C6B C5B -177.3(5) . . . . ?
O2B C4B C5B C6B 179.0(5) . . . . ?
O2B C7B C11B O7B -62.5(6) . . . . ?
O2B C7B C11B C10B 176.9(4) . . . . ?
O3B C7B C11B O7B -179.4(4) . . . . ?
O3B C7B C11B C10B 60.0(6) . . . . ?
O3B C8B C9B O5B -172.2(4) . . . . ?
O3B C8B C9B C10B -51.0(6) . . . . ?
O3B C8B C12B O4B -66.2(6) . . . . ?
O5B C9B C10B O6B -70.8(6) . . . . ?
O5B C9B C10B C11B 169.7(4) . . . . ?
O6B C10B C11B O7B 65.4(6) . . . . ?
O6B C10B C11B C7B -173.8(4) . . . . ?
C1B C2B C3B C4B -2.1(9) . . . . ?
C2B C1B C6B C5B 0.9(8) . . . . ?
C2B C3B C4B O2B -178.0(5) . . . . ?
C2B C3B C4B C5B 2.8(8) . . . . ?
C3B C4B C5B C6B -1.7(8) . . . . ?
C4B O2B C7B O3B -84.8(5) . . . . ?
C4B O2B C7B C11B 156.0(4) . . . . ?
C4B C5B C6B C1B -0.2(8) . . . . ?
C6B C1B C2B C3B 0.2(9) . . . . ?
C7B O2B C4B C3B 14.5(7) . . . . ?
C7B O2B C4B C5B -166.3(4) . . . . ?
C7B O3B C8B C9B 59.1(6) . . . . ?
C7B O3B C8B C12B -177.7(4) . . . . ?
C8B O3B C7B O2B 175.8(4) . . . . ?
C8B O3B C7B C11B -65.1(6) . . . . ?
C8B C9B C10B O6B 169.5(5) . . . . ?
C8B C9B C10B C11B 50.0(6) . . . . ?
C9B C8B C12B O4B 54.4(7) . . . . ?
C9B C10B C11B O7B -174.0(4) . . . . ?
C9B C10B C11B C7B -53.2(6) . . . . ?
C12B C8B C9B O5B 69.0(6) . . . . ?
C12B C8B C9B C10B -169.8(5) . . . . ?
O1D C1D C2D C3D 179.2(5) . . . . ?
O1D C1D C6D C5D -178.1(5) . . . . ?
O2D C4D C5D C6D 178.1(5) . . . . ?
O2D C7D C11D O7D -62.7(6) . . . . ?
O2D C7D C11D C10D 176.5(4) . . . . ?
O3D C7D C11D O7D 179.8(4) . . . . ?
O3D C7D C11D C10D 59.0(6) . . . . ?
O3D C8D C9D O5D -173.1(4) . . . . ?
O3D C8D C9D C10D -53.0(6) . . . . ?
O3D C8D C12D O4D -68.6(6) . . . . ?
O5D C9D C10D O6D -64.5(6) . . . . ?
O5D C9D C10D C11D 170.1(4) . . . . ?
O6D C10D C11D O7D 60.1(6) . . . . ?
O6D C10D C11D C7D -179.3(4) . . . . ?
C1D C2D C3D C4D -1.9(9) . . . . ?
C2D C1D C6D C5D 1.3(9) . . . . ?
C2D C3D C4D O2D -177.0(5) . . . . ?
C2D C3D C4D C5D 2.9(9) . . . . ?
C3D C4D C5D C6D -1.9(9) . . . . ?
C4D O2D C7D O3D -90.2(5) . . . . ?
C4D O2D C7D C11D 150.6(4) . . . . ?
C4D C5D C6D C1D -0.2(9) . . . . ?
C6D C1D C2D C3D -0.2(9) . . . . ?
C7D O2D C4D C3D 15.0(8) . . . . ?
C7D O2D C4D C5D -165.0(5) . . . . ?
C7D O3D C8D C9D 61.1(6) . . . . ?
C7D O3D C8D C12D -175.7(4) . . . . ?
C8D O3D C7D O2D 176.4(4) . . . . ?
C8D O3D C7D C11D -64.8(6) . . . . ?
C8D C9D C10D O6D 176.4(5) . . . . ?
C8D C9D C10D C11D 51.0(6) . . . . ?
C9D C8D C12D O4D 52.6(7) . . . . ?
C9D C10D C11D O7D -173.6(4) . . . . ?
C9D C10D C11D C7D -53.0(6) . . . . ?
C12D C8D C9D O5D 67.5(6) . . . . ?
C12D C8D C9D C10D -172.4(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 2.737
_oxdiff_exptl_absorpt_empirical_full_min 0.566
####################################################################### 
# 
# 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_r20220306b
_database_code_depnum_ccdc_archive 'CCDC 2224588'
loop_
_audit_author_name
_audit_author_address
'Mukaidaisi Taiwaikuli'
;Tianjin University
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Arbutin DMA solvent compound; solvate S4'
_chemical_name_systematic        'Arbutin DMA solvate'
_chemical_formula_moiety         '2(C12 H16 O7), C4 H9 N O'
_chemical_formula_sum            'C28 H41 N O15'
_chemical_formula_weight         631.62
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3532(4)
_cell_length_b                   21.0244(12)
_cell_length_c                   22.6649(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3027.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6723
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      30.5780
_cell_measurement_theta_min      2.6650
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26780
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.937
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    4.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    4.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    4.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054347000
_diffrn_orient_matrix_UB_12      -0.0125150000
_diffrn_orient_matrix_UB_13      -0.0290174000
_diffrn_orient_matrix_UB_21      -0.0013987000
_diffrn_orient_matrix_UB_22      0.0313250000
_diffrn_orient_matrix_UB_23      -0.0116131000
_diffrn_orient_matrix_UB_31      0.1115159000
_diffrn_orient_matrix_UB_32      -0.0002320000
_diffrn_orient_matrix_UB_33      -0.0015846000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4212
_reflns_number_total             6186
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(10)
_refine_ls_extinction_coef       0.0034(8)
_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   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.032
_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)+(0.0374P)²+1.2677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1346
_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. Restrained distances
 O4-H4 = O5-H5 = O7-H7
 0.85 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C7(H7A), C8(H8), C9(H9), C10(H10), C11(H11), C7A(H7AB), C8A(H8A), C9A(H9A),
 C10A(H10A), C11A(H11A)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5A), C6(H6A), C2A(H2A), C3A(H3A), C5A(H5AB), C6A(H6AB)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O6(H6), O1A(H1A), O4A(H4A), O5A(H5AA), O6A(H6AA), O7A(H7AA)
;
_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
O1 O 0.6445(6) 0.75399(18) 0.68187(16) 0.0321(9) Uani 1 1 d . . . . .
H1 H 0.761677 0.751584 0.698889 0.048 Uiso 1 1 calc R U . . .
O2 O 0.6775(5) 0.63430(15) 0.46372(15) 0.0251(8) Uani 1 1 d . . . . .
O3 O 0.3633(5) 0.58287(15) 0.45517(15) 0.0239(8) Uani 1 1 d . . . . .
O4 O 0.1276(6) 0.46427(17) 0.45781(18) 0.0289(9) Uani 1 1 d D . . . .
H4 H 0.088(14) 0.444(4) 0.427(2) 0.12(4) Uiso 1 1 d D . . . .
O5 O 0.0239(6) 0.55585(16) 0.32608(17) 0.0243(9) Uani 1 1 d D . . . .
H5 H -0.030(7) 0.5202(13) 0.317(2) 0.026(15) Uiso 1 1 d D . . . .
O6 O 0.4499(5) 0.56558(16) 0.27570(16) 0.0237(8) Uani 1 1 d . . . . .
H6 H 0.346670 0.557610 0.253751 0.036 Uiso 1 1 calc R U . . .
O7 O 0.7137(6) 0.64646(17) 0.34184(16) 0.0235(8) Uani 1 1 d D . . . .
H7 H 0.837(5) 0.631(3) 0.338(3) 0.07(3) Uiso 1 1 d D . . . .
C1 C 0.6581(9) 0.7259(2) 0.6267(2) 0.0263(13) Uani 1 1 d . . . . .
C2 C 0.4845(9) 0.7293(2) 0.5908(2) 0.0270(13) Uani 1 1 d . . . . .
H2 H 0.364290 0.752251 0.603672 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4808(9) 0.6997(2) 0.5357(2) 0.0251(12) Uani 1 1 d . . . . .
H3 H 0.359018 0.701796 0.511470 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6590(9) 0.6670(2) 0.5170(2) 0.0220(12) Uani 1 1 d . . . . .
C5 C 0.8368(9) 0.6659(2) 0.5518(2) 0.0265(12) Uani 1 1 d . . . . .
H5A H 0.960430 0.645345 0.537977 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8363(9) 0.6948(2) 0.6069(2) 0.0266(13) Uani 1 1 d . . . . .
H6A H 0.958522 0.693231 0.631028 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4981(8) 0.6282(2) 0.4284(2) 0.0207(12) Uani 1 1 d . . . . .
H7A H 0.424960 0.670074 0.424201 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1688(8) 0.5745(2) 0.4228(2) 0.0201(11) Uani 1 1 d . . . . .
H8 H 0.091546 0.615954 0.421605 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2131(8) 0.5529(2) 0.3599(2) 0.0215(12) Uani 1 1 d . . . . .
H9 H 0.264124 0.507872 0.360772 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3770(8) 0.5941(2) 0.3293(2) 0.0209(12) Uani 1 1 d . . . . .
H10 H 0.313843 0.636502 0.320138 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5677(8) 0.6033(2) 0.3683(2) 0.0200(12) Uani 1 1 d . . . . .
H11 H 0.638717 0.561306 0.373878 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0404(8) 0.5267(2) 0.4581(2) 0.0260(12) Uani 1 1 d . . . . .
H12A H 0.029908 0.541666 0.499407 0.031 Uiso 1 1 calc R U . . .
H12B H -0.103879 0.524920 0.441706 0.031 Uiso 1 1 calc R U . . .
O1A O 1.0282(6) 0.08348(19) 0.52751(19) 0.0407(11) Uani 1 1 d . . . . .
H1A H 0.911669 0.065353 0.532306 0.061 Uiso 1 1 calc R U . . .
O2A O 0.9847(6) 0.28131(16) 0.36613(16) 0.0281(9) Uani 1 1 d . . . . .
O3A O 0.6649(6) 0.27914(15) 0.31815(16) 0.0243(8) Uani 1 1 d . . . . .
O4A O 0.4419(6) 0.24849(18) 0.21855(16) 0.0307(9) Uani 1 1 d . . . . .
H4A H 0.388283 0.215671 0.203671 0.046 Uiso 1 1 calc R U . . .
O5A O 0.3112(6) 0.40547(16) 0.26909(18) 0.0290(9) Uani 1 1 d . . . . .
H5AA H 0.320268 0.434620 0.243871 0.043 Uiso 1 1 calc R U . . .
O6A O 0.7340(6) 0.46810(16) 0.27327(18) 0.0294(9) Uani 1 1 d . . . . .
H6AA H 0.635882 0.494862 0.272038 0.044 Uiso 1 1 calc R U . . .
O7A O 1.0130(6) 0.41284(16) 0.35163(17) 0.0285(9) Uani 1 1 d . . . . .
H7AA H 1.130700 0.410386 0.334898 0.043 Uiso 1 1 calc R U . . .
C1A C 1.0050(9) 0.1335(2) 0.4881(2) 0.0297(13) Uani 1 1 d . . . . .
C2A C 0.8171(9) 0.1445(2) 0.4585(3) 0.0316(13) Uani 1 1 d . . . . .
H2A H 0.698360 0.118033 0.465489 0.038 Uiso 1 1 calc R U . . .
C3A C 0.8045(9) 0.1949(2) 0.4183(2) 0.0293(13) Uani 1 1 d . . . . .
H3A H 0.676424 0.202863 0.397975 0.035 Uiso 1 1 calc R U . . .
C4A C 0.9764(9) 0.2327(2) 0.4081(2) 0.0239(12) Uani 1 1 d . . . . .
C5A C 1.1648(9) 0.2213(2) 0.4379(2) 0.0284(13) Uani 1 1 d . . . . .
H5AB H 1.283597 0.247803 0.431224 0.034 Uiso 1 1 calc R U . . .
C6A C 1.1774(9) 0.1714(2) 0.4771(2) 0.0299(13) Uani 1 1 d . . . . .
H6AB H 1.306444 0.163018 0.496811 0.036 Uiso 1 1 calc R U . . .
C7A C 0.8008(8) 0.3160(2) 0.3548(2) 0.0239(12) Uani 1 1 d . . . . .
H7AB H 0.728736 0.327971 0.392429 0.029 Uiso 1 1 calc R U . . .
C8A C 0.4676(8) 0.3106(2) 0.3060(2) 0.0232(12) Uani 1 1 d . . . . .
H8A H 0.396052 0.320132 0.344286 0.028 Uiso 1 1 calc R U . . .
C9A C 0.5105(8) 0.3732(2) 0.2738(2) 0.0218(12) Uani 1 1 d . . . . .
H9A H 0.565466 0.363940 0.233345 0.026 Uiso 1 1 calc R U . . .
C10A C 0.6683(8) 0.4141(2) 0.3067(2) 0.0208(11) Uani 1 1 d . . . . .
H10A H 0.604241 0.428786 0.344667 0.025 Uiso 1 1 calc R U . . .
C11A C 0.8623(8) 0.3750(2) 0.3199(2) 0.0231(12) Uani 1 1 d . . . . .
H11A H 0.926766 0.361220 0.281765 0.028 Uiso 1 1 calc R U . . .
C12A C 0.3360(8) 0.2635(2) 0.2722(2) 0.0271(12) Uani 1 1 d . . . . .
H12C H 0.315566 0.224444 0.295947 0.032 Uiso 1 1 calc R U . . .
H12D H 0.196029 0.281971 0.263582 0.032 Uiso 1 1 calc R U . . .
O8 O 0.2752(6) 0.4946(2) 0.69558(17) 0.0396(11) Uani 1 1 d . . . . .
N1 N 0.5720(9) 0.4707(3) 0.6477(3) 0.0554(17) Uani 1 1 d . . . . .
C13 C 0.4062(13) 0.5689(3) 0.6215(3) 0.068(2) Uani 1 1 d . . . . .
H13A H 0.268282 0.588932 0.627028 0.102 Uiso 1 1 calc R U . . .
H13B H 0.426259 0.558795 0.579667 0.102 Uiso 1 1 calc R U . . .
H13C H 0.516880 0.598229 0.634460 0.102 Uiso 1 1 calc R U . . .
C14 C 0.4174(12) 0.5080(3) 0.6578(3) 0.0538(19) Uani 1 1 d . . . . .
C15 C 0.7509(11) 0.4856(3) 0.6086(3) 0.061(2) Uani 1 1 d . . . . .
H15A H 0.706837 0.516838 0.578947 0.091 Uiso 1 1 calc R U . . .
H15B H 0.797976 0.446672 0.588769 0.091 Uiso 1 1 calc R U . . .
H15C H 0.866867 0.503159 0.631978 0.091 Uiso 1 1 calc R U . . .
C16 C 0.5869(11) 0.4093(3) 0.6824(3) 0.0508(19) Uani 1 1 d . . . . .
H16A H 0.697605 0.413154 0.712272 0.076 Uiso 1 1 calc R U . . .
H16B H 0.620821 0.374230 0.655539 0.076 Uiso 1 1 calc R U . . .
H16C H 0.451895 0.400813 0.701749 0.076 Uiso 1 1 calc R U . . .


_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 0.8400 . ?
O1 C1 1.386(6) . ?
O2 C4 1.395(6) . ?
O2 C7 1.399(6) . ?
O3 C7 1.418(6) . ?
O3 C8 1.448(6) . ?
O4 H4 0.848(14) . ?
O4 C12 1.424(6) . ?
O5 H5 0.847(14) . ?
O5 C9 1.427(6) . ?
O6 H6 0.8400 . ?
O6 C10 1.431(6) . ?
O7 H7 0.851(14) . ?
O7 C11 1.429(6) . ?
C1 C2 1.373(7) . ?
C1 C6 1.381(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(7) . ?
C4 C5 1.378(7) . ?
C5 H5A 0.9500 . ?
C5 C6 1.390(7) . ?
C6 H6A 0.9500 . ?
C7 H7A 1.0000 . ?
C7 C11 1.524(7) . ?
C8 H8 1.0000 . ?
C8 C9 1.522(7) . ?
C8 C12 1.522(7) . ?
C9 H9 1.0000 . ?
C9 C10 1.523(7) . ?
C10 H10 1.0000 . ?
C10 C11 1.513(7) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1A H1A 0.8400 . ?
O1A C1A 1.389(6) . ?
O2A C4A 1.398(6) . ?
O2A C7A 1.401(6) . ?
O3A C7A 1.427(6) . ?
O3A C8A 1.444(6) . ?
O4A H4A 0.8400 . ?
O4A C12A 1.425(6) . ?
O5A H5AA 0.8400 . ?
O5A C9A 1.440(6) . ?
O6A H6AA 0.8400 . ?
O6A C10A 1.428(6) . ?
O7A H7AA 0.8400 . ?
O7A C11A 1.438(6) . ?
C1A C2A 1.388(8) . ?
C1A C6A 1.377(8) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.400(7) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.370(7) . ?
C4A C5A 1.395(7) . ?
C5A H5AB 0.9500 . ?
C5A C6A 1.377(7) . ?
C6A H6AB 0.9500 . ?
C7A H7AB 1.0000 . ?
C7A C11A 1.520(7) . ?
C8A H8A 1.0000 . ?
C8A C9A 1.531(7) . ?
C8A C12A 1.505(7) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.517(7) . ?
C10A H10A 1.0000 . ?
C10A C11A 1.512(7) . ?
C11A H11A 1.0000 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
O8 C14 1.276(8) . ?
N1 C14 1.277(9) . ?
N1 C15 1.475(8) . ?
N1 C16 1.515(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C14 1.525(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C1 O1 H1 109.5 . . ?
C4 O2 C7 118.2(4) . . ?
C7 O3 C8 112.3(4) . . ?
C12 O4 H4 110(6) . . ?
C9 O5 H5 115(4) . . ?
C10 O6 H6 109.5 . . ?
C11 O7 H7 114(5) . . ?
C2 C1 O1 117.6(5) . . ?
C2 C1 C6 119.4(5) . . ?
C6 C1 O1 123.1(5) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(5) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 O2 125.2(5) . . ?
C5 C4 O2 114.7(5) . . ?
C5 C4 C3 120.1(5) . . ?
C4 C5 H5A 119.8 . . ?
C4 C5 C6 120.4(5) . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 120.0(5) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
O2 C7 O3 108.0(4) . . ?
O2 C7 H7A 110.6 . . ?
O2 C7 C11 107.8(4) . . ?
O3 C7 H7A 110.6 . . ?
O3 C7 C11 109.1(4) . . ?
C11 C7 H7A 110.6 . . ?
O3 C8 H8 109.1 . . ?
O3 C8 C9 110.7(4) . . ?
O3 C8 C12 105.7(4) . . ?
C9 C8 H8 109.1 . . ?
C9 C8 C12 113.2(4) . . ?
C12 C8 H8 109.1 . . ?
O5 C9 C8 109.5(4) . . ?
O5 C9 H9 109.0 . . ?
O5 C9 C10 107.8(4) . . ?
C8 C9 H9 109.0 . . ?
C8 C9 C10 112.5(4) . . ?
C10 C9 H9 109.0 . . ?
O6 C10 C9 111.7(4) . . ?
O6 C10 H10 109.1 . . ?
O6 C10 C11 106.9(4) . . ?
C9 C10 H10 109.1 . . ?
C11 C10 C9 110.8(4) . . ?
C11 C10 H10 109.1 . . ?
O7 C11 C7 110.2(4) . . ?
O7 C11 C10 110.9(4) . . ?
O7 C11 H11 108.7 . . ?
C7 C11 H11 108.7 . . ?
C10 C11 C7 109.5(4) . . ?
C10 C11 H11 108.7 . . ?
O4 C12 C8 113.5(4) . . ?
O4 C12 H12A 108.9 . . ?
O4 C12 H12B 108.9 . . ?
C8 C12 H12A 108.9 . . ?
C8 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C1A O1A H1A 109.5 . . ?
C4A O2A C7A 118.3(4) . . ?
C7A O3A C8A 112.8(4) . . ?
C12A O4A H4A 109.5 . . ?
C9A O5A H5AA 109.5 . . ?
C10A O6A H6AA 109.5 . . ?
C11A O7A H7AA 109.5 . . ?
C2A C1A O1A 121.8(5) . . ?
C6A C1A O1A 118.0(5) . . ?
C6A C1A C2A 120.1(5) . . ?
C1A C2A H2A 120.4 . . ?
C1A C2A C3A 119.2(5) . . ?
C3A C2A H2A 120.4 . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A C2A 120.2(5) . . ?
C4A C3A H3A 119.9 . . ?
C3A C4A O2A 124.7(5) . . ?
C3A C4A C5A 120.2(5) . . ?
C5A C4A O2A 115.0(5) . . ?
C4A C5A H5AB 120.2 . . ?
C6A C5A C4A 119.5(5) . . ?
C6A C5A H5AB 120.2 . . ?
C1A C6A C5A 120.7(5) . . ?
C1A C6A H6AB 119.7 . . ?
C5A C6A H6AB 119.7 . . ?
O2A C7A O3A 109.1(4) . . ?
O2A C7A H7AB 110.9 . . ?
O2A C7A C11A 107.8(4) . . ?
O3A C7A H7AB 110.9 . . ?
O3A C7A C11A 107.2(4) . . ?
C11A C7A H7AB 110.9 . . ?
O3A C8A H8A 108.7 . . ?
O3A C8A C9A 109.3(4) . . ?
O3A C8A C12A 106.2(4) . . ?
C9A C8A H8A 108.7 . . ?
C12A C8A H8A 108.7 . . ?
C12A C8A C9A 115.0(4) . . ?
O5A C9A C8A 106.5(4) . . ?
O5A C9A H9A 109.3 . . ?
O5A C9A C10A 110.5(4) . . ?
C8A C9A H9A 109.3 . . ?
C10A C9A C8A 111.7(4) . . ?
C10A C9A H9A 109.3 . . ?
O6A C10A C9A 112.4(4) . . ?
O6A C10A H10A 109.2 . . ?
O6A C10A C11A 107.4(4) . . ?
C9A C10A H10A 109.2 . . ?
C11A C10A C9A 109.2(4) . . ?
C11A C10A H10A 109.2 . . ?
O7A C11A C7A 111.3(4) . . ?
O7A C11A C10A 109.9(4) . . ?
O7A C11A H11A 108.6 . . ?
C7A C11A H11A 108.6 . . ?
C10A C11A C7A 109.7(4) . . ?
C10A C11A H11A 108.6 . . ?
O4A C12A C8A 108.5(4) . . ?
O4A C12A H12C 110.0 . . ?
O4A C12A H12D 110.0 . . ?
C8A C12A H12C 110.0 . . ?
C8A C12A H12D 110.0 . . ?
H12C C12A H12D 108.4 . . ?
C14 N1 C15 124.8(7) . . ?
C14 N1 C16 118.5(6) . . ?
C15 N1 C16 116.4(6) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
O8 C14 N1 122.0(7) . . ?
O8 C14 C13 120.9(7) . . ?
N1 C14 C13 117.0(7) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C1 C2 C3 -176.9(4) . . . . ?
O1 C1 C6 C5 178.0(5) . . . . ?
O2 C4 C5 C6 -177.7(4) . . . . ?
O2 C7 C11 O7 -59.6(5) . . . . ?
O2 C7 C11 C10 178.2(4) . . . . ?
O3 C7 C11 O7 -176.6(4) . . . . ?
O3 C7 C11 C10 61.2(5) . . . . ?
O3 C8 C9 O5 -169.8(4) . . . . ?
O3 C8 C9 C10 -49.9(5) . . . . ?
O3 C8 C12 O4 -68.4(5) . . . . ?
O5 C9 C10 O6 -71.6(5) . . . . ?
O5 C9 C10 C11 169.3(4) . . . . ?
O6 C10 C11 O7 63.1(5) . . . . ?
O6 C10 C11 C7 -175.0(4) . . . . ?
C1 C2 C3 C4 -1.0(8) . . . . ?
C2 C1 C6 C5 -1.7(8) . . . . ?
C2 C3 C4 O2 178.8(4) . . . . ?
C2 C3 C4 C5 -2.0(7) . . . . ?
C3 C4 C5 C6 3.1(8) . . . . ?
C4 O2 C7 O3 -73.7(5) . . . . ?
C4 O2 C7 C11 168.6(4) . . . . ?
C4 C5 C6 C1 -1.2(8) . . . . ?
C6 C1 C2 C3 2.8(8) . . . . ?
C7 O2 C4 C3 -6.6(7) . . . . ?
C7 O2 C4 C5 174.2(4) . . . . ?
C7 O3 C8 C9 59.0(5) . . . . ?
C7 O3 C8 C12 -178.1(4) . . . . ?
C8 O3 C7 O2 178.2(4) . . . . ?
C8 O3 C7 C11 -64.9(5) . . . . ?
C8 C9 C10 O6 167.5(4) . . . . ?
C8 C9 C10 C11 48.4(5) . . . . ?
C9 C8 C12 O4 52.9(6) . . . . ?
C9 C10 C11 O7 -174.9(4) . . . . ?
C9 C10 C11 C7 -53.1(5) . . . . ?
C12 C8 C9 O5 71.8(5) . . . . ?
C12 C8 C9 C10 -168.3(4) . . . . ?
O1A C1A C2A C3A -178.6(5) . . . . ?
O1A C1A C6A C5A 179.3(5) . . . . ?
O2A C4A C5A C6A -175.3(5) . . . . ?
O2A C7A C11A O7A -58.1(5) . . . . ?
O2A C7A C11A C10A -179.9(4) . . . . ?
O3A C7A C11A O7A -175.5(4) . . . . ?
O3A C7A C11A C10A 62.7(5) . . . . ?
O3A C8A C9A O5A -173.5(4) . . . . ?
O3A C8A C9A C10A -52.7(5) . . . . ?
O3A C8A C12A O4A -61.3(5) . . . . ?
O5A C9A C10A O6A -70.4(5) . . . . ?
O5A C9A C10A C11A 170.5(4) . . . . ?
O6A C10A C11A O7A 58.3(5) . . . . ?
O6A C10A C11A C7A -179.1(4) . . . . ?
C1A C2A C3A C4A 0.3(8) . . . . ?
C2A C1A C6A C5A 1.5(9) . . . . ?
C2A C3A C4A O2A 175.4(5) . . . . ?
C2A C3A C4A C5A -0.1(8) . . . . ?
C3A C4A C5A C6A 0.7(8) . . . . ?
C4A O2A C7A O3A -77.6(5) . . . . ?
C4A O2A C7A C11A 166.3(4) . . . . ?
C4A C5A C6A C1A -1.3(8) . . . . ?
C6A C1A C2A C3A -1.0(9) . . . . ?
C7A O2A C4A C3A 33.9(7) . . . . ?
C7A O2A C4A C5A -150.3(5) . . . . ?
C7A O3A C8A C9A 60.7(5) . . . . ?
C7A O3A C8A C12A -174.7(4) . . . . ?
C8A O3A C7A O2A 177.9(4) . . . . ?
C8A O3A C7A C11A -65.6(5) . . . . ?
C8A C9A C10A O6A 171.2(4) . . . . ?
C8A C9A C10A C11A 52.1(6) . . . . ?
C9A C8A C12A O4A 59.6(6) . . . . ?
C9A C10A C11A O7A -179.5(4) . . . . ?
C9A C10A C11A C7A -56.9(6) . . . . ?
C12A C8A C9A O5A 67.2(5) . . . . ?
C12A C8A C9A C10A -172.0(4) . . . . ?
C15 N1 C14 O8 -174.5(6) . . . . ?
C15 N1 C14 C13 7.0(10) . . . . ?
C16 N1 C14 O8 -0.7(10) . . . . ?
C16 N1 C14 C13 -179.3(6) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.333
_oxdiff_exptl_absorpt_empirical_full_min 0.663
####################################################################### 
# 
# 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_r20220327a
_database_code_depnum_ccdc_archive 'CCDC 2224584'
loop_
_audit_author_name
_audit_author_address
'Mukaidaisi Taiwaikuli'
;Tianjin University
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Arbutin DMF solvent compound; solvate S1'
_chemical_name_systematic        'Arbutin DMF solvate'
_chemical_formula_moiety         'C12 H16 O7, 2(C3 H7 N O)'
_chemical_formula_sum            'C18 H30 N2 O9'
_chemical_formula_weight         418.44
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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        P21
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5631(3)
_cell_length_b                   8.5283(3)
_cell_length_c                   15.1997(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.747(3)
_cell_angle_gamma                90
_cell_volume                     1073.45(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10120
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8240
_cell_measurement_theta_min      2.4270
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13440
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.912
_diffrn_reflns_theta_min         2.459
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0603257000
_diffrn_orient_matrix_UB_12      -0.0376850000
_diffrn_orient_matrix_UB_13      0.0168726000
_diffrn_orient_matrix_UB_21      -0.0413430000
_diffrn_orient_matrix_UB_22      -0.0215750000
_diffrn_orient_matrix_UB_23      -0.0449515000
_diffrn_orient_matrix_UB_31      0.0446291000
_diffrn_orient_matrix_UB_32      -0.0709243000
_diffrn_orient_matrix_UB_33      0.0047321000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.831
_reflns_Friedel_fraction_max     0.710
_reflns_number_gt                6034
_reflns_number_total             6617
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 2160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_coef       0.041(4)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6617
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.038
_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)+(0.0465P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0959
_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 Ternary CH refined with riding coordinates:
 C7(H7A), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5A), C6(H6A), C13(H13), C16(H16)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O5(H5), O6(H6), O7(H7)
;
_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 -0.74217(17) -0.72839(19) -0.91935(9) 0.0340(3) Uani 1 1 d . . . . .
H1 H -0.815119 -0.746705 -0.892811 0.051 Uiso 1 1 calc R U . . .
O2 O -0.31218(14) -0.27212(15) -0.74724(7) 0.0195(2) Uani 1 1 d . . . . .
O3 O -0.37577(12) -0.17920(15) -0.62010(7) 0.0173(2) Uani 1 1 d . . . . .
O4 O -0.62609(12) -0.17973(18) -0.53430(8) 0.0247(3) Uani 1 1 d . . . . .
H4 H -0.655741 -0.163857 -0.590648 0.037 Uiso 1 1 calc R U . . .
O5 O -0.14257(13) -0.08280(15) -0.39073(7) 0.0192(2) Uani 1 1 d . . . . .
H5 H -0.090413 -0.000787 -0.371888 0.029 Uiso 1 1 calc R U . . .
O6 O 0.09284(13) -0.07116(15) -0.49475(9) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.170675 -0.116496 -0.508256 0.033 Uiso 1 1 calc R U . . .
O7 O 0.01692(13) -0.29123(15) -0.65023(8) 0.0208(2) Uani 1 1 d . . . . .
H7 H 0.074533 -0.237126 -0.675842 0.031 Uiso 1 1 calc R U . . .
C1 C -0.64310(19) -0.6134(2) -0.87391(11) 0.0227(3) Uani 1 1 d . . . . .
C2 C -0.65081(19) -0.5555(2) -0.78964(11) 0.0217(3) Uani 1 1 d . . . . .
H2 H -0.730018 -0.594780 -0.761508 0.026 Uiso 1 1 calc R U . . .
C3 C -0.54346(19) -0.4407(2) -0.74626(10) 0.0192(3) Uani 1 1 d . . . . .
H3 H -0.550674 -0.400360 -0.689164 0.023 Uiso 1 1 calc R U . . .
C4 C -0.42567(18) -0.3848(2) -0.78630(10) 0.0176(3) Uani 1 1 d . . . . .
C5 C -0.4180(2) -0.4410(2) -0.87117(10) 0.0216(3) Uani 1 1 d . . . . .
H5A H -0.338753 -0.401553 -0.899224 0.026 Uiso 1 1 calc R U . . .
C6 C -0.5263(2) -0.5545(2) -0.91459(11) 0.0237(3) Uani 1 1 d . . . . .
H6A H -0.521033 -0.592606 -0.972496 0.028 Uiso 1 1 calc R U . . .
C7 C -0.26208(17) -0.2706(2) -0.65157(10) 0.0155(3) Uani 1 1 d . . . . .
H7A H -0.256825 -0.379618 -0.626832 0.019 Uiso 1 1 calc R U . . .
C8 C -0.33805(16) -0.1766(2) -0.52252(10) 0.0161(3) Uani 1 1 d . . . . .
H8 H -0.325470 -0.286291 -0.498452 0.019 Uiso 1 1 calc R U . . .
C9 C -0.18044(16) -0.08670(19) -0.48736(10) 0.0149(3) Uani 1 1 d . . . . .
H9 H -0.194342 0.022971 -0.511374 0.018 Uiso 1 1 calc R U . . .
C10 C -0.04711(16) -0.16712(19) -0.52054(10) 0.0158(3) Uani 1 1 d . . . . .
H10 H -0.023323 -0.271170 -0.489705 0.019 Uiso 1 1 calc R U . . .
C11 C -0.09723(17) -0.19253(19) -0.62363(10) 0.0156(3) Uani 1 1 d . . . . .
H11 H -0.101833 -0.089053 -0.655138 0.019 Uiso 1 1 calc R U . . .
C12 C -0.47874(18) -0.0983(2) -0.49709(12) 0.0232(3) Uani 1 1 d . . . . .
H12A H -0.458060 -0.094875 -0.430004 0.028 Uiso 1 1 calc R U . . .
H12B H -0.488760 0.011019 -0.519806 0.028 Uiso 1 1 calc R U . . .
O8 O -0.77981(15) -0.1177(2) -0.71451(8) 0.0317(3) Uani 1 1 d . . . . .
N1 N -0.82141(19) -0.1541(2) -0.86663(10) 0.0286(3) Uani 1 1 d . . . . .
C13 C -0.7426(2) -0.0984(3) -0.78734(12) 0.0277(4) Uani 1 1 d . . . . .
H13 H -0.648732 -0.037990 -0.785611 0.033 Uiso 1 1 calc R U . . .
C14 C -0.7675(4) -0.1239(4) -0.94837(16) 0.0524(7) Uani 1 1 d . . . . .
H14A H -0.672969 -0.054787 -0.933551 0.079 Uiso 1 1 calc R U . . .
H14B H -0.854550 -0.073454 -0.994072 0.079 Uiso 1 1 calc R U . . .
H14C H -0.738493 -0.223246 -0.972563 0.079 Uiso 1 1 calc R U . . .
C15 C -0.9661(3) -0.2478(4) -0.87652(15) 0.0471(6) Uani 1 1 d . . . . .
H15A H -0.937604 -0.359268 -0.873723 0.071 Uiso 1 1 calc R U . . .
H15B H -1.041713 -0.224750 -0.935254 0.071 Uiso 1 1 calc R U . . .
H15C H -1.016818 -0.222580 -0.827281 0.071 Uiso 1 1 calc R U . . .
O9 O 0.00785(18) 0.1828(2) -0.86001(10) 0.0369(4) Uani 1 1 d . . . . .
N2 N -0.19376(19) 0.1660(2) -0.78807(10) 0.0267(3) Uani 1 1 d . . . . .
C16 C -0.0482(2) 0.2113(3) -0.79447(13) 0.0303(4) Uani 1 1 d . . . . .
H16 H 0.016840 0.269461 -0.745322 0.036 Uiso 1 1 calc R U . . .
C17 C -0.2992(2) 0.0756(3) -0.86022(13) 0.0299(4) Uani 1 1 d . . . . .
H17A H -0.397264 0.136143 -0.886645 0.045 Uiso 1 1 calc R U . . .
H17B H -0.328468 -0.022816 -0.835237 0.045 Uiso 1 1 calc R U . . .
H17C H -0.243183 0.052623 -0.907474 0.045 Uiso 1 1 calc R U . . .
C18 C -0.2573(3) 0.2138(3) -0.71178(13) 0.0337(4) Uani 1 1 d . . . . .
H18A H -0.172101 0.266194 -0.665836 0.051 Uiso 1 1 calc R U . . .
H18B H -0.294566 0.121057 -0.684898 0.051 Uiso 1 1 calc R U . . .
H18C H -0.347869 0.286110 -0.733356 0.051 Uiso 1 1 calc R U . . .


_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 0.8400 . ?
O1 C1 1.364(2) . ?
O2 C4 1.388(2) . ?
O2 C7 1.4076(17) . ?
O3 C7 1.4215(18) . ?
O3 C8 1.4355(17) . ?
O4 H4 0.8400 . ?
O4 C12 1.4253(19) . ?
O5 H5 0.8400 . ?
O5 C9 1.4217(17) . ?
O6 H6 0.8400 . ?
O6 C10 1.4214(18) . ?
O7 H7 0.8400 . ?
O7 C11 1.4243(18) . ?
C1 C2 1.390(2) . ?
C1 C6 1.396(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(2) . ?
C4 C5 1.393(2) . ?
C5 H5A 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 1.0000 . ?
C7 C11 1.520(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.526(2) . ?
C8 C12 1.511(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.524(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.531(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O8 C13 1.238(2) . ?
N1 C13 1.311(3) . ?
N1 C14 1.455(2) . ?
N1 C15 1.449(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O9 C16 1.235(2) . ?
N2 C16 1.332(2) . ?
N2 C17 1.452(2) . ?
N2 C18 1.459(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C1 O1 H1 109.5 . . ?
C4 O2 C7 116.39(12) . . ?
C7 O3 C8 111.27(11) . . ?
C12 O4 H4 109.5 . . ?
C9 O5 H5 109.5 . . ?
C10 O6 H6 109.5 . . ?
C11 O7 H7 109.5 . . ?
O1 C1 C2 123.55(15) . . ?
O1 C1 C6 117.25(15) . . ?
C2 C1 C6 119.19(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.45(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.05(14) . . ?
C4 C3 H3 120.0 . . ?
O2 C4 C3 123.92(13) . . ?
O2 C4 C5 116.18(14) . . ?
C3 C4 C5 119.90(15) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 C4 119.83(15) . . ?
C6 C5 H5A 120.1 . . ?
C1 C6 H6A 119.7 . . ?
C5 C6 C1 120.56(15) . . ?
C5 C6 H6A 119.7 . . ?
O2 C7 O3 107.35(12) . . ?
O2 C7 H7A 110.6 . . ?
O2 C7 C11 108.05(11) . . ?
O3 C7 H7A 110.6 . . ?
O3 C7 C11 109.45(12) . . ?
C11 C7 H7A 110.6 . . ?
O3 C8 H8 109.8 . . ?
O3 C8 C9 108.41(11) . . ?
O3 C8 C12 106.65(12) . . ?
C9 C8 H8 109.8 . . ?
C12 C8 H8 109.8 . . ?
C12 C8 C9 112.32(13) . . ?
O5 C9 C8 108.81(11) . . ?
O5 C9 H9 109.3 . . ?
O5 C9 C10 111.06(12) . . ?
C8 C9 H9 109.3 . . ?
C10 C9 C8 109.17(12) . . ?
C10 C9 H9 109.3 . . ?
O6 C10 C9 107.44(13) . . ?
O6 C10 H10 108.9 . . ?
O6 C10 C11 111.15(12) . . ?
C9 C10 H10 108.9 . . ?
C9 C10 C11 111.35(12) . . ?
C11 C10 H10 108.9 . . ?
O7 C11 C7 108.52(13) . . ?
O7 C11 C10 109.90(12) . . ?
O7 C11 H11 109.4 . . ?
C7 C11 C10 110.26(11) . . ?
C7 C11 H11 109.4 . . ?
C10 C11 H11 109.4 . . ?
O4 C12 C8 111.45(14) . . ?
O4 C12 H12A 109.3 . . ?
O4 C12 H12B 109.3 . . ?
C8 C12 H12A 109.3 . . ?
C8 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C13 N1 C14 121.34(19) . . ?
C13 N1 C15 121.41(16) . . ?
C15 N1 C14 117.25(19) . . ?
O8 C13 N1 125.78(18) . . ?
O8 C13 H13 117.1 . . ?
N1 C13 H13 117.1 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 N2 C17 120.84(16) . . ?
C16 N2 C18 121.50(17) . . ?
C17 N2 C18 117.54(16) . . ?
O9 C16 N2 124.39(18) . . ?
O9 C16 H16 117.8 . . ?
N2 C16 H16 117.8 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C1 C2 C3 178.53(17) . . . . ?
O1 C1 C6 C5 -178.01(17) . . . . ?
O2 C4 C5 C6 179.53(15) . . . . ?
O2 C7 C11 O7 -67.39(15) . . . . ?
O2 C7 C11 C10 172.20(13) . . . . ?
O3 C7 C11 O7 176.02(12) . . . . ?
O3 C7 C11 C10 55.60(16) . . . . ?
O3 C8 C9 O5 179.68(12) . . . . ?
O3 C8 C9 C10 -58.96(16) . . . . ?
O3 C8 C12 O4 58.50(18) . . . . ?
O5 C9 C10 O6 -66.10(16) . . . . ?
O5 C9 C10 C11 171.98(12) . . . . ?
O6 C10 C11 O7 70.31(16) . . . . ?
O6 C10 C11 C7 -170.11(12) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C3 C4 O2 -178.99(15) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 O2 C7 O3 -85.02(16) . . . . ?
C4 O2 C7 C11 157.03(13) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C7 O2 C4 C3 31.6(2) . . . . ?
C7 O2 C4 C5 -149.12(14) . . . . ?
C7 O3 C8 C9 67.26(16) . . . . ?
C7 O3 C8 C12 -171.59(13) . . . . ?
C8 O3 C7 O2 177.49(12) . . . . ?
C8 O3 C7 C11 -65.47(16) . . . . ?
C8 C9 C10 O6 173.93(12) . . . . ?
C8 C9 C10 C11 52.00(17) . . . . ?
C9 C8 C12 O4 177.13(13) . . . . ?
C9 C10 C11 O7 -169.94(12) . . . . ?
C9 C10 C11 C7 -50.36(17) . . . . ?
C12 C8 C9 O5 62.09(17) . . . . ?
C12 C8 C9 C10 -176.55(14) . . . . ?
C14 N1 C13 O8 179.8(2) . . . . ?
C15 N1 C13 O8 0.0(3) . . . . ?
C17 N2 C16 O9 0.5(3) . . . . ?
C18 N2 C16 O9 -175.3(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 1.195
_oxdiff_exptl_absorpt_empirical_full_min 0.870
####################################################################### 
# 
# 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_r20220306a
_database_code_depnum_ccdc_archive 'CCDC 2224586'
loop_
_audit_author_name
_audit_author_address
'Mukaidaisi Taiwaikuli'
;Tianjin University
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Arbutin NMP solvent compound;solvate S5'
_chemical_name_systematic        'Arbutin NMP solvate'
_chemical_formula_moiety         '2(C12 H16 O7), C5 H9 N O'
_chemical_formula_sum            'C29 H41 N O15'
_chemical_formula_weight         643.63
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3606(3)
_cell_length_b                   20.5593(9)
_cell_length_c                   23.4018(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3060.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11208
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.7100
_cell_measurement_theta_min      2.6230
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            37615
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.555
_diffrn_reflns_theta_min         1.981
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    3.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    3.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    3.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0378577000
_diffrn_orient_matrix_UB_12      0.0054834000
_diffrn_orient_matrix_UB_13      -0.0280900000
_diffrn_orient_matrix_UB_21      -0.0094832000
_diffrn_orient_matrix_UB_22      -0.0336786000
_diffrn_orient_matrix_UB_23      -0.0060187000
_diffrn_orient_matrix_UB_31      -0.1044762000
_diffrn_orient_matrix_UB_32      0.0050627000
_diffrn_orient_matrix_UB_33      -0.0096650000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                7609
_reflns_number_total             11199
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 2160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(6)
_refine_ls_extinction_coef       0.0081(8)
_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   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         11199
_refine_ls_number_restraints     324
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.2219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1239
_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. Restrained distances
 O7A-H7AA
 0.85 with sigma of 0.01
 O5A-H5AA
 0.85 with sigma of 0.01
 O8-C16 \\sim O8A-C16A
 with sigma of 0.02
 N1-C16 \\sim N1A-C16A
 with sigma of 0.02
 N1-C13 \\sim N1A-C13A
 with sigma of 0.02
 N1-C17 \\sim N1A-C17A
 with sigma of 0.02
 C16-C15 \\sim C16A-C15A
 with sigma of 0.02
 C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 C14-C13 \\sim C14A-C13A
 with sigma of 0.02
 O8-N1 \\sim O8A-N1A
 with sigma of 0.04
 O8-C15 \\sim O8A-C15A
 with sigma of 0.04
 N1-C15 \\sim N1A-C15A
 with sigma of 0.04
 N1-C14 \\sim N1A-C14A
 with sigma of 0.04
 C16-C14 \\sim C16A-C14A
 with sigma of 0.04
 C16-C13 \\sim C16A-C13A
 with sigma of 0.04
 C16-C17 \\sim C16A-C17A
 with sigma of 0.04
 C15-C13 \\sim C15A-C13A
 with sigma of 0.04
 C13-C17 \\sim C13A-C17A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O8 \\sim N1 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim O8A \\sim
N1A \\sim C13A \\sim C14A \\sim C15A \\sim C16A \\sim C17A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O8) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(O8A) \\sim Ueq, Uanis(N1A) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14A)
\\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O8A)=Sof(N1A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(C17A)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=1-FVAR(1)
 Sof(O8)=Sof(N1)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7A), C8(H8), C9(H9), C10(H10), C11(H11), C7A(H7AB), C8A(H8A), C9A(H9A),
 C10A(H10A), C11A(H11A)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C13A(H13C,H13D), C14A(H14C,H14D), C15A(H15C,H15D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5A), C6(H6A), C2A(H2A), C3A(H3A), C5A(H5AB), C6A(H6AB)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O5(H5), O6(H6), O7(H7), O1A(H1A), O4A(H4A), O6A(H6AA)
;
_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
O1 O 1.0320(4) 0.08820(11) 0.53222(9) 0.0413(5) Uani 1 1 d . . . . .
H1 H 0.921068 0.066070 0.533450 0.062 Uiso 1 1 calc R U . . .
O2 O 0.9973(3) 0.27836(9) 0.36447(8) 0.0285(4) Uani 1 1 d . . . . .
O3 O 0.6805(3) 0.27544(8) 0.31758(8) 0.0246(4) Uani 1 1 d . . . . .
O4 O 0.4570(3) 0.24605(10) 0.21923(8) 0.0322(5) Uani 1 1 d . . . . .
H4 H 0.394532 0.215696 0.202225 0.048 Uiso 1 1 calc R U . . .
O5 O 0.3219(3) 0.40351(10) 0.27172(9) 0.0309(4) Uani 1 1 d . . . . .
H5 H 0.323577 0.430736 0.244965 0.046 Uiso 1 1 calc R U . . .
O6 O 0.7401(3) 0.46976(9) 0.27656(9) 0.0291(4) Uani 1 1 d . . . . .
H6 H 0.648070 0.498818 0.279944 0.044 Uiso 1 1 calc R U . . .
O7 O 1.0226(3) 0.41273(9) 0.35079(8) 0.0286(4) Uani 1 1 d . . . . .
H7 H 1.137565 0.412964 0.333130 0.043 Uiso 1 1 calc R U . . .
C1 C 1.0133(5) 0.13535(14) 0.49085(11) 0.0297(6) Uani 1 1 d . . . . .
C2 C 0.8302(5) 0.14405(14) 0.45960(13) 0.0322(6) Uani 1 1 d . . . . .
H2 H 0.711423 0.117289 0.466903 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8197(5) 0.19178(14) 0.41766(13) 0.0322(7) Uani 1 1 d . . . . .
H3 H 0.695015 0.196964 0.395794 0.039 Uiso 1 1 calc R U . . .
C4 C 0.9905(5) 0.23169(13) 0.40771(11) 0.0257(6) Uani 1 1 d . . . . .
C5 C 1.1730(5) 0.22381(14) 0.43959(12) 0.0298(6) Uani 1 1 d . . . . .
H5A H 1.290164 0.251501 0.433062 0.036 Uiso 1 1 calc R U . . .
C6 C 1.1845(5) 0.17556(14) 0.48095(12) 0.0318(6) Uani 1 1 d . . . . .
H6A H 1.309816 0.170072 0.502505 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8135(4) 0.31344(12) 0.35337(11) 0.0237(5) Uani 1 1 d . . . . .
H7A H 0.740232 0.325094 0.389763 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4843(4) 0.30691(12) 0.30568(11) 0.0231(5) Uani 1 1 d . . . . .
H8 H 0.411695 0.315806 0.342766 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5216(4) 0.37193(12) 0.27515(11) 0.0227(5) Uani 1 1 d . . . . .
H9 H 0.576379 0.363663 0.235761 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6780(4) 0.41369(12) 0.30814(11) 0.0228(5) Uani 1 1 d . . . . .
H10 H 0.613205 0.427652 0.345091 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8744(4) 0.37420(12) 0.32032(11) 0.0220(5) Uani 1 1 d . . . . .
H11 H 0.938529 0.360772 0.283132 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3542(4) 0.25898(14) 0.27225(12) 0.0276(6) Uani 1 1 d . . . . .
H12A H 0.338213 0.218147 0.294253 0.033 Uiso 1 1 calc R U . . .
H12B H 0.212447 0.277161 0.265123 0.033 Uiso 1 1 calc R U . . .
O1A O 0.6316(3) 0.74854(11) 0.68272(8) 0.0332(5) Uani 1 1 d . . . . .
H1A H 0.750563 0.749414 0.698283 0.050 Uiso 1 1 calc R U . . .
O2A O 0.6792(3) 0.63478(9) 0.46788(8) 0.0259(4) Uani 1 1 d . . . . .
O3A O 0.3674(3) 0.58166(8) 0.45800(7) 0.0225(4) Uani 1 1 d . . . . .
O4A O 0.1308(3) 0.46043(9) 0.45684(8) 0.0286(4) Uani 1 1 d . . . . .
H4A H 0.085328 0.441374 0.427594 0.043 Uiso 1 1 calc R U . . .
O5A O 0.0286(3) 0.55719(9) 0.33305(8) 0.0228(4) Uani 1 1 d D . . . .
H5AA H -0.024(5) 0.5201(10) 0.3259(17) 0.059(12) Uiso 1 1 d D . . . .
O6A O 0.4566(3) 0.56856(9) 0.28488(7) 0.0237(4) Uani 1 1 d . . . . .
H6AA H 0.354037 0.560598 0.263368 0.036 Uiso 1 1 calc R U . . .
O7A O 0.7155(3) 0.65050(9) 0.34970(8) 0.0231(4) Uani 1 1 d D . . . .
H7AA H 0.829(3) 0.6302(15) 0.3434(15) 0.049(11) Uiso 1 1 d D . . . .
C1A C 0.6487(5) 0.72189(13) 0.62914(11) 0.0261(6) Uani 1 1 d . . . . .
C2A C 0.4720(5) 0.72352(14) 0.59439(13) 0.0320(7) Uani 1 1 d . . . . .
H2A H 0.347559 0.744219 0.607530 0.038 Uiso 1 1 calc R U . . .
C3A C 0.4757(5) 0.69492(14) 0.54016(12) 0.0312(6) Uani 1 1 d . . . . .
H3A H 0.353446 0.695721 0.516852 0.037 Uiso 1 1 calc R U . . .
C4A C 0.6566(4) 0.66560(12) 0.52056(11) 0.0232(5) Uani 1 1 d . . . . .
C5A C 0.8359(4) 0.66594(13) 0.55454(11) 0.0257(6) Uani 1 1 d . . . . .
H5AB H 0.962260 0.647117 0.540571 0.031 Uiso 1 1 calc R U . . .
C6A C 0.8322(5) 0.69353(13) 0.60872(11) 0.0264(6) Uani 1 1 d . . . . .
H6AB H 0.955028 0.693015 0.631801 0.032 Uiso 1 1 calc R U . . .
C7A C 0.5015(4) 0.62927(12) 0.43311(10) 0.0208(5) Uani 1 1 d . . . . .
H7AB H 0.427622 0.672028 0.429725 0.025 Uiso 1 1 calc R U . . .
C8A C 0.1739(4) 0.57434(12) 0.42716(10) 0.0203(5) Uani 1 1 d . . . . .
H8A H 0.097597 0.616862 0.426841 0.024 Uiso 1 1 calc R U . . .
C9A C 0.2191(4) 0.55360(12) 0.36573(10) 0.0183(5) Uani 1 1 d . . . . .
H9A H 0.270347 0.507618 0.365773 0.022 Uiso 1 1 calc R U . . .
C10A C 0.3824(4) 0.59634(12) 0.33692(10) 0.0183(5) Uani 1 1 d . . . . .
H10A H 0.318966 0.639843 0.328671 0.022 Uiso 1 1 calc R U . . .
C11A C 0.5725(4) 0.60531(12) 0.37508(10) 0.0190(5) Uani 1 1 d . . . . .
H11A H 0.644900 0.562463 0.379782 0.023 Uiso 1 1 calc R U . . .
C12A C 0.0437(4) 0.52445(12) 0.45965(11) 0.0240(5) Uani 1 1 d . . . . .
H12C H 0.033462 0.537883 0.500180 0.029 Uiso 1 1 calc R U . . .
H12D H -0.100416 0.523653 0.443665 0.029 Uiso 1 1 calc R U . . .
O8 O 0.242(2) 0.5034(5) 0.2050(8) 0.0311(18) Uani 0.618(5) 1 d D U P A 1
N1 N -0.0393(8) 0.5630(2) 0.1750(2) 0.0346(11) Uani 0.618(5) 1 d D U P A 1
C13 C -0.2385(12) 0.5559(3) 0.1432(3) 0.0462(16) Uani 0.618(5) 1 d D U P A 1
H13A H -0.258654 0.592180 0.115888 0.055 Uiso 0.618(5) 1 calc R U P A 1
H13B H -0.360231 0.554092 0.169455 0.055 Uiso 0.618(5) 1 calc R U P A 1
C14 C -0.2097(14) 0.4925(4) 0.1124(4) 0.064(2) Uani 0.618(5) 1 d D U P A 1
H14A H -0.176101 0.500234 0.071654 0.077 Uiso 0.618(5) 1 calc R U P A 1
H14B H -0.339515 0.466087 0.114669 0.077 Uiso 0.618(5) 1 calc R U P A 1
C15 C -0.0283(11) 0.4577(3) 0.1419(3) 0.0464(14) Uani 0.618(5) 1 d D U P A 1
H15A H -0.080861 0.421793 0.166290 0.056 Uiso 0.618(5) 1 calc R U P A 1
H15B H 0.071299 0.439653 0.113543 0.056 Uiso 0.618(5) 1 calc R U P A 1
C16 C 0.0750(12) 0.5093(3) 0.1775(3) 0.0294(14) Uani 0.618(5) 1 d D U P A 1
C17 C 0.0085(12) 0.6221(3) 0.2064(2) 0.0488(17) Uani 0.618(5) 1 d D U P A 1
H17A H -0.072975 0.622952 0.241907 0.073 Uiso 0.618(5) 1 calc R U P A 1
H17B H -0.028028 0.660027 0.183032 0.073 Uiso 0.618(5) 1 calc R U P A 1
H17C H 0.158960 0.623222 0.215404 0.073 Uiso 0.618(5) 1 calc R U P A 1
O8A O 0.225(4) 0.5193(9) 0.2041(14) 0.035(3) Uani 0.382(5) 1 d D U P A 2
N1A N -0.0192(12) 0.4970(4) 0.1358(3) 0.0366(16) Uani 0.382(5) 1 d D U P A 2
C13A C -0.2290(19) 0.5219(6) 0.1188(6) 0.048(2) Uani 0.382(5) 1 d D U P A 2
H13C H -0.230308 0.532508 0.077517 0.057 Uiso 0.382(5) 1 calc R U P A 2
H13D H -0.338061 0.488637 0.126202 0.057 Uiso 0.382(5) 1 calc R U P A 2
C14A C -0.272(2) 0.5810(5) 0.1529(5) 0.043(2) Uani 0.382(5) 1 d D U P A 2
H14C H -0.403919 0.576026 0.174732 0.051 Uiso 0.382(5) 1 calc R U P A 2
H14D H -0.284421 0.619469 0.127700 0.051 Uiso 0.382(5) 1 calc R U P A 2
C15A C -0.0889(16) 0.5888(5) 0.1928(4) 0.0361(19) Uani 0.382(5) 1 d D U P A 2
H15C H -0.135672 0.587070 0.233091 0.043 Uiso 0.382(5) 1 calc R U P A 2
H15D H -0.016176 0.630705 0.186030 0.043 Uiso 0.382(5) 1 calc R U P A 2
C16A C 0.054(2) 0.5320(5) 0.1789(6) 0.032(2) Uani 0.382(5) 1 d D U P A 2
C17A C 0.0892(18) 0.4425(5) 0.1122(4) 0.060(3) Uani 0.382(5) 1 d D U P A 2
H17D H 0.238832 0.445360 0.121835 0.090 Uiso 0.382(5) 1 calc R U P A 2
H17E H 0.072487 0.442373 0.070596 0.090 Uiso 0.382(5) 1 calc R U P A 2
H17F H 0.030581 0.402262 0.128086 0.090 Uiso 0.382(5) 1 calc R U P A 2


_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 0.8400 . ?
O1 C1 1.375(3) . ?
O2 C4 1.395(3) . ?
O2 C7 1.398(3) . ?
O3 C7 1.424(3) . ?
O3 C8 1.433(3) . ?
O4 H4 0.8400 . ?
O4 C12 1.428(3) . ?
O5 H5 0.8400 . ?
O5 C9 1.429(3) . ?
O6 H6 0.8400 . ?
O6 C10 1.425(3) . ?
O7 H7 0.8400 . ?
O7 C11 1.423(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.387(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 C5 1.389(4) . ?
C5 H5A 0.9500 . ?
C5 C6 1.388(4) . ?
C6 H6A 0.9500 . ?
C7 H7A 1.0000 . ?
C7 C11 1.519(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.534(4) . ?
C8 C12 1.506(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.524(4) . ?
C10 H10 1.0000 . ?
C10 C11 1.517(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1A H1A 0.8400 . ?
O1A C1A 1.373(3) . ?
O2A C4A 1.394(3) . ?
O2A C7A 1.397(3) . ?
O3A C7A 1.423(3) . ?
O3A C8A 1.435(3) . ?
O4A H4A 0.8400 . ?
O4A C12A 1.430(3) . ?
O5A H5AA 0.851(13) . ?
O5A C9A 1.435(3) . ?
O6A H6AA 0.8400 . ?
O6A C10A 1.425(3) . ?
O7A H7AA 0.845(13) . ?
O7A C11A 1.429(3) . ?
C1A C2A 1.387(4) . ?
C1A C6A 1.389(4) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.399(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.378(4) . ?
C4A C5A 1.390(4) . ?
C5A H5AB 0.9500 . ?
C5A C6A 1.389(4) . ?
C6A H6AB 0.9500 . ?
C7A H7AB 1.0000 . ?
C7A C11A 1.514(3) . ?
C8A H8A 1.0000 . ?
C8A C9A 1.527(3) . ?
C8A C12A 1.522(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.519(3) . ?
C10A H10A 1.0000 . ?
C10A C11A 1.514(3) . ?
C11A H11A 1.0000 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
O8 C16 1.248(10) . ?
N1 C13 1.477(8) . ?
N1 C16 1.323(7) . ?
N1 C17 1.452(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.500(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.524(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.500(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O8A C16A 1.263(15) . ?
N1A C13A 1.483(13) . ?
N1A C16A 1.325(12) . ?
N1A C17A 1.427(11) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A C14A 1.479(13) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C14A C15A 1.499(14) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.515(13) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?

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
C1 O1 H1 109.5 . . ?
C4 O2 C7 117.6(2) . . ?
C7 O3 C8 112.58(19) . . ?
C12 O4 H4 109.5 . . ?
C9 O5 H5 109.5 . . ?
C10 O6 H6 109.5 . . ?
C11 O7 H7 109.5 . . ?
O1 C1 C2 122.3(3) . . ?
O1 C1 C6 118.0(3) . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 O2 123.7(3) . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 O2 116.3(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
O2 C7 O3 108.9(2) . . ?
O2 C7 H7A 110.8 . . ?
O2 C7 C11 107.8(2) . . ?
O3 C7 H7A 110.8 . . ?
O3 C7 C11 107.6(2) . . ?
C11 C7 H7A 110.8 . . ?
O3 C8 H8 108.4 . . ?
O3 C8 C9 110.5(2) . . ?
O3 C8 C12 106.5(2) . . ?
C9 C8 H8 108.4 . . ?
C12 C8 H8 108.4 . . ?
C12 C8 C9 114.4(2) . . ?
O5 C9 C8 106.5(2) . . ?
O5 C9 H9 109.6 . . ?
O5 C9 C10 110.7(2) . . ?
C8 C9 H9 109.6 . . ?
C10 C9 C8 110.8(2) . . ?
C10 C9 H9 109.6 . . ?
O6 C10 C9 111.9(2) . . ?
O6 C10 H10 109.3 . . ?
O6 C10 C11 107.6(2) . . ?
C9 C10 H10 109.3 . . ?
C11 C10 C9 109.3(2) . . ?
C11 C10 H10 109.3 . . ?
O7 C11 C7 111.8(2) . . ?
O7 C11 C10 109.98(19) . . ?
O7 C11 H11 108.7 . . ?
C7 C11 H11 108.7 . . ?
C10 C11 C7 109.0(2) . . ?
C10 C11 H11 108.7 . . ?
O4 C12 C8 108.7(2) . . ?
O4 C12 H12A 109.9 . . ?
O4 C12 H12B 109.9 . . ?
C8 C12 H12A 109.9 . . ?
C8 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C1A O1A H1A 109.5 . . ?
C4A O2A C7A 117.9(2) . . ?
C7A O3A C8A 112.37(18) . . ?
C12A O4A H4A 109.5 . . ?
C9A O5A H5AA 113(3) . . ?
C10A O6A H6AA 109.5 . . ?
C11A O7A H7AA 107(2) . . ?
O1A C1A C2A 117.5(3) . . ?
O1A C1A C6A 123.2(2) . . ?
C2A C1A C6A 119.3(2) . . ?
C1A C2A H2A 119.7 . . ?
C1A C2A C3A 120.5(3) . . ?
C3A C2A H2A 119.7 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 120.0(3) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A O2A 125.4(2) . . ?
C3A C4A C5A 119.5(2) . . ?
C5A C4A O2A 115.1(2) . . ?
C4A C5A H5AB 119.7 . . ?
C6A C5A C4A 120.7(3) . . ?
C6A C5A H5AB 119.7 . . ?
C1A C6A H6AB 120.0 . . ?
C5A C6A C1A 120.0(3) . . ?
C5A C6A H6AB 120.0 . . ?
O2A C7A O3A 107.60(19) . . ?
O2A C7A H7AB 110.8 . . ?
O2A C7A C11A 107.9(2) . . ?
O3A C7A H7AB 110.8 . . ?
O3A C7A C11A 108.79(19) . . ?
C11A C7A H7AB 110.8 . . ?
O3A C8A H8A 109.2 . . ?
O3A C8A C9A 110.0(2) . . ?
O3A C8A C12A 106.6(2) . . ?
C9A C8A H8A 109.2 . . ?
C12A C8A H8A 109.2 . . ?
C12A C8A C9A 112.6(2) . . ?
O5A C9A C8A 109.2(2) . . ?
O5A C9A H9A 108.9 . . ?
O5A C9A C10A 108.13(19) . . ?
C8A C9A H9A 108.9 . . ?
C10A C9A C8A 112.7(2) . . ?
C10A C9A H9A 108.9 . . ?
O6A C10A C9A 112.0(2) . . ?
O6A C10A H10A 109.1 . . ?
O6A C10A C11A 106.8(2) . . ?
C9A C10A H10A 109.1 . . ?
C11A C10A C9A 110.78(19) . . ?
C11A C10A H10A 109.1 . . ?
O7A C11A C7A 110.5(2) . . ?
O7A C11A C10A 110.0(2) . . ?
O7A C11A H11A 109.0 . . ?
C7A C11A C10A 109.3(2) . . ?
C7A C11A H11A 109.0 . . ?
C10A C11A H11A 109.0 . . ?
O4A C12A C8A 112.7(2) . . ?
O4A C12A H12C 109.0 . . ?
O4A C12A H12D 109.0 . . ?
C8A C12A H12C 109.0 . . ?
C8A C12A H12D 109.0 . . ?
H12C C12A H12D 107.8 . . ?
C16 N1 C13 114.2(6) . . ?
C16 N1 C17 124.1(5) . . ?
C17 N1 C13 121.2(6) . . ?
N1 C13 H13A 111.2 . . ?
N1 C13 H13B 111.2 . . ?
N1 C13 C14 102.9(6) . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 H13A 111.2 . . ?
C14 C13 H13B 111.2 . . ?
C13 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
C13 C14 C15 106.5(6) . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.4 . . ?
C15 C14 H14B 110.4 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 C14 104.5(6) . . ?
C16 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
O8 C16 N1 124.8(8) . . ?
O8 C16 C15 126.2(8) . . ?
N1 C16 C15 109.0(6) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16A N1A C13A 109.5(9) . . ?
C16A N1A C17A 123.4(8) . . ?
C17A N1A C13A 127.0(8) . . ?
N1A C13A H13C 110.2 . . ?
N1A C13A H13D 110.2 . . ?
H13C C13A H13D 108.5 . . ?
C14A C13A N1A 107.7(10) . . ?
C14A C13A H13C 110.2 . . ?
C14A C13A H13D 110.2 . . ?
C13A C14A H14C 110.5 . . ?
C13A C14A H14D 110.5 . . ?
C13A C14A C15A 106.4(10) . . ?
H14C C14A H14D 108.6 . . ?
C15A C14A H14C 110.5 . . ?
C15A C14A H14D 110.5 . . ?
C14A C15A H15C 110.9 . . ?
C14A C15A H15D 110.9 . . ?
C14A C15A C16A 104.4(9) . . ?
H15C C15A H15D 108.9 . . ?
C16A C15A H15C 110.9 . . ?
C16A C15A H15D 110.9 . . ?
O8A C16A N1A 123.0(15) . . ?
O8A C16A C15A 125.2(14) . . ?
N1A C16A C15A 111.7(9) . . ?
N1A C17A H17D 109.5 . . ?
N1A C17A H17E 109.5 . . ?
N1A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 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 C1 C2 C3 -179.1(3) . . . . ?
O1 C1 C6 C5 180.0(3) . . . . ?
O2 C4 C5 C6 -175.8(2) . . . . ?
O2 C7 C11 O7 -57.6(3) . . . . ?
O2 C7 C11 C10 -179.4(2) . . . . ?
O3 C7 C11 O7 -174.9(2) . . . . ?
O3 C7 C11 C10 63.3(3) . . . . ?
O3 C8 C9 O5 -172.65(19) . . . . ?
O3 C8 C9 C10 -52.2(3) . . . . ?
O3 C8 C12 O4 -63.5(3) . . . . ?
O5 C9 C10 O6 -71.0(3) . . . . ?
O5 C9 C10 C11 169.8(2) . . . . ?
O6 C10 C11 O7 57.8(3) . . . . ?
O6 C10 C11 C7 -179.3(2) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C3 C4 O2 176.4(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 O2 C7 O3 -81.8(3) . . . . ?
C4 O2 C7 C11 161.7(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C7 O2 C4 C3 38.4(4) . . . . ?
C7 O2 C4 C5 -145.3(2) . . . . ?
C7 O3 C8 C9 60.2(3) . . . . ?
C7 O3 C8 C12 -175.0(2) . . . . ?
C8 O3 C7 O2 177.90(19) . . . . ?
C8 O3 C7 C11 -65.5(3) . . . . ?
C8 C9 C10 O6 171.0(2) . . . . ?
C8 C9 C10 C11 51.9(3) . . . . ?
C9 C8 C12 O4 58.9(3) . . . . ?
C9 C10 C11 O7 179.6(2) . . . . ?
C9 C10 C11 C7 -57.5(3) . . . . ?
C12 C8 C9 O5 67.2(3) . . . . ?
C12 C8 C9 C10 -172.3(2) . . . . ?
O1A C1A C2A C3A -177.4(3) . . . . ?
O1A C1A C6A C5A 178.2(3) . . . . ?
O2A C4A C5A C6A -178.2(2) . . . . ?
O2A C7A C11A O7A -60.9(3) . . . . ?
O2A C7A C11A C10A 177.88(19) . . . . ?
O3A C7A C11A O7A -177.36(19) . . . . ?
O3A C7A C11A C10A 61.4(3) . . . . ?
O3A C8A C9A O5A -170.31(19) . . . . ?
O3A C8A C9A C10A -50.2(3) . . . . ?
O3A C8A C12A O4A -68.5(3) . . . . ?
O5A C9A C10A O6A -72.0(3) . . . . ?
O5A C9A C10A C11A 168.91(19) . . . . ?
O6A C10A C11A O7A 63.3(2) . . . . ?
O6A C10A C11A C7A -175.10(19) . . . . ?
C1A C2A C3A C4A -0.9(5) . . . . ?
C2A C1A C6A C5A -1.4(4) . . . . ?
C2A C3A C4A O2A 179.1(3) . . . . ?
C2A C3A C4A C5A -1.4(4) . . . . ?
C3A C4A C5A C6A 2.2(4) . . . . ?
C4A O2A C7A O3A -72.5(3) . . . . ?
C4A O2A C7A C11A 170.2(2) . . . . ?
C4A C5A C6A C1A -0.8(4) . . . . ?
C6A C1A C2A C3A 2.3(4) . . . . ?
C7A O2A C4A C3A -4.2(4) . . . . ?
C7A O2A C4A C5A 176.2(2) . . . . ?
C7A O3A C8A C9A 59.9(2) . . . . ?
C7A O3A C8A C12A -177.72(19) . . . . ?
C8A O3A C7A O2A 177.06(18) . . . . ?
C8A O3A C7A C11A -66.3(2) . . . . ?
C8A C9A C10A O6A 167.2(2) . . . . ?
C8A C9A C10A C11A 48.1(3) . . . . ?
C9A C8A C12A O4A 52.2(3) . . . . ?
C9A C10A C11A O7A -174.53(19) . . . . ?
C9A C10A C11A C7A -53.0(3) . . . . ?
C12A C8A C9A O5A 70.9(3) . . . . ?
C12A C8A C9A C10A -168.9(2) . . . . ?
N1 C13 C14 C15 16.8(8) . . . . ?
C13 N1 C16 O8 -175.4(13) . . . . ?
C13 N1 C16 C15 4.7(9) . . . . ?
C13 C14 C15 C16 -14.7(9) . . . . ?
C14 C15 C16 O8 -173.4(14) . . . . ?
C14 C15 C16 N1 6.4(9) . . . . ?
C16 N1 C13 C14 -13.9(8) . . . . ?
C17 N1 C13 C14 173.5(6) . . . . ?
C17 N1 C16 O8 -3.1(16) . . . . ?
C17 N1 C16 C15 177.1(6) . . . . ?
N1A C13A C14A C15A -3.0(13) . . . . ?
C13A N1A C16A O8A 176(2) . . . . ?
C13A N1A C16A C15A -5.3(13) . . . . ?
C13A C14A C15A C16A 0.1(12) . . . . ?
C14A C15A C16A O8A -178(2) . . . . ?
C14A C15A C16A N1A 3.3(13) . . . . ?
C16A N1A C13A C14A 5.2(13) . . . . ?
C17A N1A C13A C14A -177.2(10) . . . . ?
C17A N1A C16A O8A -2(2) . . . . ?
C17A N1A C16A C15A 177.1(9) . . . . ?

_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 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.713
