# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_procjanidyna_A2
_database_code_depnum_ccdc_archive 'CCDC 1519315'
_audit_update_record             
;
2016-11-25 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_cell_length_a                   7.17009(12)
_cell_length_b                   13.9391(2)
_cell_length_c                   25.7472(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     2573.30(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12264
_cell_measurement_theta_min      3.3840
_cell_measurement_theta_max      75.2820
_cell_measurement_temperature    100.0(1)
_cell_oxdiff_length_a            7.1713(2)
_cell_oxdiff_length_b            13.9394(3)
_cell_oxdiff_length_c            25.7424(5)
_cell_oxdiff_angle_alpha         89.9832(17)
_cell_oxdiff_angle_beta          89.9910(19)
_cell_oxdiff_angle_gamma         89.989(2)
_cell_oxdiff_volume              2573.30(10)
_cell_oxdiff_measurement_reflns_used 12264
_exptl_crystal_description       nidle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04

_exptl_absorpt_correction_T_min  0.77593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, TitanS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            TitanS2
_diffrn_detector_area_resol_mean 4.1685
_diffrn_reflns_number            19455
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.1704
_diffrn_reflns_theta_max         75.5736
_diffrn_measured_fraction_theta_max 0.9836
_diffrn_reflns_theta_full        66.9682
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_orient_matrix_UB_11      -0.1763067000
_diffrn_orient_matrix_UB_12      0.0623671000
_diffrn_orient_matrix_UB_13      -0.0054096000
_diffrn_orient_matrix_UB_21      0.1025659000
_diffrn_orient_matrix_UB_22      0.0652307000
_diffrn_orient_matrix_UB_23      -0.0389642000
_diffrn_orient_matrix_UB_31      -0.0674200000
_diffrn_orient_matrix_UB_32      -0.0637937000
_diffrn_orient_matrix_UB_33      -0.0450998000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   11.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7274   37.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7274 -125.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega   30.00   95.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7274 -125.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega   28.00  108.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -94.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega   94.00  119.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090 -125.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   42.00  136.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  105.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -94.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   88.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -30.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   89.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -30.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   92.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -45.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   67.00  178.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090   15.0000   90.0000 111

#__ type_ start__ end____ width___ exp.time_
 12 omega  107.00  155.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  125.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 13 omega   83.00  175.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090   45.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   97.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -45.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
 15 omega   32.00  102.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -94.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega -123.00   21.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7274    0.0000 -180.0000 144

;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 21 21 21'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1
_chemical_name_common            'Procyanidyn A2'
_chemical_name_systematic        
(2R,3R,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-2,3,4,14-tetrahydro-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
_chemical_formula_moiety         'C30 H24 O12, 2(H2 O)'
_chemical_formula_sum            'C30 H28 O14'
_chemical_formula_weight         612.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_exptl_absorpt_coefficient_mu    1.084
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_diffrn_ambient_temperature      100.0(1)
_reflns_number_gt                5038
_reflns_number_total             5244
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_coef       0.00144(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.4992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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, All O(H,H) groups
2.a Free rotating group:
 O12(H12A,H12B), O10(H10A,H10B)
2.b Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4A), C2'(H2'A), C3'(H3'A)
2.c Secondary CH2 refined with riding coordinates:
 C4'(H4'A,H4'B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6A), C8(H8), C12(H12), C15(H15), C16(H16), C6'(H6'A), C12'(H12'),
 C15'(H15'), C16'(H16')
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4), O5(H5), O6(H6), O2'(H2'), O3'(H3'), O5'(H5'), O6'(H6')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.22264(17) 0.88390(9) 0.44342(4) 0.0342(3) Uani 1 d . . .
O2 O 0.57010(19) 0.94156(8) 0.40354(5) 0.0344(3) Uani 1 d . . .
H2 H 0.6173 0.9756 0.4260 0.052 Uiso 1 calc . . GR
O3 O 0.3262(2) 0.74363(11) 0.27315(5) 0.0444(3) Uani 1 d . . .
H3 H 0.3993 0.7083 0.2885 0.067 Uiso 1 calc . . GR
O4 O -0.22014(19) 0.92165(11) 0.30986(5) 0.0432(3) Uani 1 d . . .
H4 H -0.2868 0.9311 0.3352 0.065 Uiso 1 calc . . GR
O5 O 0.4280(3) 1.15454(10) 0.55548(6) 0.0516(4) Uani 1 d . . .
H5 H 0.4807 1.1780 0.5807 0.077 Uiso 1 calc . . GR
O6 O 0.5565(2) 1.07341(10) 0.64199(5) 0.0455(3) Uani 1 d . . .
H6 H 0.6395 1.0495 0.6597 0.068 Uiso 1 calc . . GR
C2 C 0.3893(2) 0.84541(11) 0.46485(6) 0.0290(3) Uani 1 d . . .
C3 C 0.5440(2) 0.84752(11) 0.42348(6) 0.0295(3) Uani 1 d . . .
H3A H 0.6610 0.8239 0.4384 0.035 Uiso 1 calc . . R
C4 C 0.4830(2) 0.78200(11) 0.37902(6) 0.0284(3) Uani 1 d . . .
H4A H 0.5755 0.7841 0.3510 0.034 Uiso 1 calc . . R
C5 C 0.2271(3) 0.79753(12) 0.30892(6) 0.0333(4) Uani 1 d . . .
C6 C 0.0568(3) 0.83307(13) 0.29208(6) 0.0370(4) Uani 1 d . . .
H6A H 0.0156 0.8211 0.2585 0.044 Uiso 1 calc . . R
C7 C -0.0504(3) 0.88646(13) 0.32590(7) 0.0345(4) Uani 1 d . . .
C8 C 0.0094(3) 0.90393(12) 0.37626(7) 0.0331(4) Uani 1 d . . .
H8 H -0.0627 0.9402 0.3990 0.040 Uiso 1 calc . . R
C9 C 0.1791(2) 0.86606(12) 0.39198(6) 0.0295(3) Uani 1 d . . .
C10 C 0.2952(2) 0.81487(11) 0.35884(6) 0.0290(3) Uani 1 d . . .
C11 C 0.4258(2) 0.90384(12) 0.51389(6) 0.0295(3) Uani 1 d . . .
C12 C 0.4060(3) 1.00358(12) 0.51258(7) 0.0335(4) Uani 1 d . . .
H12 H 0.3631 1.0337 0.4826 0.040 Uiso 1 calc . . R
C13 C 0.4504(3) 1.05734(12) 0.55601(7) 0.0355(4) Uani 1 d . . .
C14 C 0.5151(3) 1.01334(14) 0.60103(7) 0.0363(4) Uani 1 d . . .
C15 C 0.5265(3) 0.91488(14) 0.60316(7) 0.0374(4) Uani 1 d . . .
H15 H 0.5632 0.8848 0.6337 0.045 Uiso 1 calc . . R
C16 C 0.4830(3) 0.86018(13) 0.55942(7) 0.0347(4) Uani 1 d . . .
H16 H 0.4925 0.7937 0.5609 0.042 Uiso 1 calc . . R
O1' O 0.57530(19) 0.61705(8) 0.32319(4) 0.0336(3) Uani 1 d . . .
O2' O 0.3444(2) 0.47170(11) 0.28892(5) 0.0458(3) Uani 1 d . . .
H2' H 0.3177 0.4442 0.2618 0.069 Uiso 1 calc . . GR
O3' O 0.4373(2) 0.41222(8) 0.46710(5) 0.0443(3) Uani 1 d . . .
H3' H 0.3925 0.4157 0.4963 0.066 Uiso 1 calc . . GR
O4' O 0.35870(19) 0.74906(8) 0.48200(4) 0.0337(3) Uani 1 d . . .
O5' O 1.1226(2) 0.67663(17) 0.17729(7) 0.0671(5) Uani 1 d . . .
H5' H 1.1846 0.6768 0.2040 0.101 Uiso 1 calc . . GR
O6' O 0.8714(3) 0.69283(14) 0.10265(6) 0.0594(4) Uani 1 d . . .
H6' H 0.7820 0.6975 0.0830 0.089 Uiso 1 calc . . GR
C2' C 0.6617(3) 0.53617(12) 0.29690(6) 0.0320(3) Uani 1 d . . .
H2'A H 0.7782 0.5218 0.3152 0.038 Uiso 1 calc . . R
C3' C 0.5337(3) 0.44879(13) 0.30322(7) 0.0365(4) Uani 1 d . . .
H3'A H 0.5796 0.3956 0.2819 0.044 Uiso 1 calc . . R
C4' C 0.5364(3) 0.42055(12) 0.36034(7) 0.0361(4) Uani 1 d . . .
H4'A H 0.4399 0.3733 0.3670 0.043 Uiso 1 calc . . R
H4'B H 0.6559 0.3921 0.3689 0.043 Uiso 1 calc . . R
C5' C 0.4492(3) 0.50220(11) 0.44608(7) 0.0318(3) Uani 1 d . . .
C6' C 0.4060(3) 0.58203(12) 0.47537(6) 0.0310(3) Uani 1 d . . .
H6'A H 0.3714 0.5757 0.5100 0.037 Uiso 1 calc . . R
C7' C 0.4152(2) 0.67202(12) 0.45226(6) 0.0294(3) Uani 1 d . . .
C8' C 0.4742(2) 0.68263(11) 0.40157(6) 0.0287(3) Uani 1 d . . .
C9' C 0.5190(2) 0.60029(12) 0.37367(6) 0.0292(3) Uani 1 d . . .
C10' C 0.5037(2) 0.50846(12) 0.39386(6) 0.0301(3) Uani 1 d . . .
C11' C 0.7129(3) 0.57274(12) 0.24386(6) 0.0339(4) Uani 1 d . . .
C12' C 0.8948(3) 0.60354(15) 0.23491(7) 0.0416(4) Uani 1 d . . .
H12' H 0.9837 0.5967 0.2610 0.050 Uiso 1 calc . . R
C13' C 0.9460(3) 0.64426(16) 0.18793(8) 0.0446(4) Uani 1 d . . .
C14' C 0.8139(3) 0.65377(15) 0.14893(7) 0.0449(5) Uani 1 d . . .
C15' C 0.6337(4) 0.62345(17) 0.15752(8) 0.0521(5) Uani 1 d . . .
H15' H 0.5455 0.6295 0.1312 0.062 Uiso 1 calc . . R
C16' C 0.5818(3) 0.58392(16) 0.20490(7) 0.0461(5) Uani 1 d . . .
H16' H 0.4590 0.5650 0.2104 0.055 Uiso 1 calc . . R
O12 O 0.2668(2) 0.39201(11) 0.56063(6) 0.0497(3) Uani 1 d . . .
H12A H 0.3503 0.3726 0.5816 0.075 Uiso 1 d . . G
H12B H 0.1800 0.3507 0.5589 0.075 Uiso 1 d . . G
O10 O 0.4479(3) 0.22133(11) 0.45614(6) 0.0612(5) Uani 1 d . . .
H10A H 0.4473 0.2052 0.4880 0.092 Uiso 1 d . . G
H10B H 0.4672 0.2813 0.4537 0.092 Uiso 1 d . . G


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.421(2) . ?
O1 C9 1.3830(19) . ?
O2 C3 1.4203(19) . ?
O3 C5 1.385(2) . ?
O4 C7 1.376(2) . ?
O5 C13 1.365(2) . ?
O6 C14 1.379(2) . ?
C2 C3 1.538(2) . ?
C2 C11 1.525(2) . ?
C2 O4' 1.4306(19) . ?
C3 C4 1.528(2) . ?
C4 C10 1.514(2) . ?
C4 C8' 1.503(2) . ?
C5 C6 1.387(3) . ?
C5 C10 1.396(2) . ?
C6 C7 1.380(3) . ?
C7 C8 1.387(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.389(2) . ?
C11 C12 1.398(2) . ?
C11 C16 1.383(2) . ?
C12 C13 1.383(2) . ?
C13 C14 1.391(3) . ?
C14 C15 1.376(3) . ?
C15 C16 1.395(2) . ?
O1' C2' 1.454(2) . ?
O1' C9' 1.3809(19) . ?
O2' C3' 1.442(2) . ?
O3' C5' 1.369(2) . ?
O4' C7' 1.3796(19) . ?
O5' C13' 1.372(3) . ?
O6' C14' 1.373(2) . ?
C2' C3' 1.534(3) . ?
C2' C11' 1.503(2) . ?
C3' C4' 1.523(2) . ?
C4' C10' 1.517(2) . ?
C5' C6' 1.379(2) . ?
C5' C10' 1.403(2) . ?
C6' C7' 1.390(2) . ?
C7' C8' 1.380(2) . ?
C8' C9' 1.391(2) . ?
C9' C10' 1.386(2) . ?
C11' C12' 1.393(3) . ?
C11' C16' 1.384(3) . ?
C12' C13' 1.385(3) . ?
C13' C14' 1.387(3) . ?
C14' C15' 1.378(3) . ?
C15' C16' 1.389(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C2 119.57(13) . . ?
O1 C2 C3 109.27(13) . . ?
O1 C2 C11 105.32(13) . . ?
O1 C2 O4' 110.20(13) . . ?
C11 C2 C3 116.06(14) . . ?
O4' C2 C3 110.01(13) . . ?
O4' C2 C11 105.79(12) . . ?
O2 C3 C2 111.29(13) . . ?
O2 C3 C4 108.58(13) . . ?
C4 C3 C2 107.53(13) . . ?
C10 C4 C3 109.29(13) . . ?
C8' C4 C3 105.86(13) . . ?
C8' C4 C10 111.97(14) . . ?
O3 C5 C6 115.96(15) . . ?
O3 C5 C10 121.77(17) . . ?
C6 C5 C10 122.27(16) . . ?
C7 C6 C5 119.08(16) . . ?
O4 C7 C6 119.73(16) . . ?
O4 C7 C8 119.44(16) . . ?
C6 C7 C8 120.81(17) . . ?
C9 C8 C7 118.51(16) . . ?
O1 C9 C8 114.14(15) . . ?
O1 C9 C10 123.05(15) . . ?
C8 C9 C10 122.81(15) . . ?
C5 C10 C4 125.07(15) . . ?
C9 C10 C4 118.52(14) . . ?
C9 C10 C5 116.41(16) . . ?
C12 C11 C2 119.58(15) . . ?
C16 C11 C2 121.17(14) . . ?
C16 C11 C12 119.23(15) . . ?
C13 C12 C11 119.72(16) . . ?
O5 C13 C12 120.18(17) . . ?
O5 C13 C14 119.05(16) . . ?
C12 C13 C14 120.77(16) . . ?
O6 C14 C13 116.19(16) . . ?
C15 C14 O6 124.22(18) . . ?
C15 C14 C13 119.53(16) . . ?
C14 C15 C16 119.97(17) . . ?
C11 C16 C15 120.66(16) . . ?
C9' O1' C2' 115.57(13) . . ?
C7' O4' C2 120.97(12) . . ?
O1' C2' C3' 108.16(14) . . ?
O1' C2' C11' 105.32(13) . . ?
C11' C2' C3' 120.79(15) . . ?
O2' C3' C2' 111.12(15) . . ?
O2' C3' C4' 108.40(15) . . ?
C4' C3' C2' 107.47(15) . . ?
C10' C4' C3' 109.79(14) . . ?
O3' C5' C6' 120.60(15) . . ?
O3' C5' C10' 116.96(15) . . ?
C6' C5' C10' 122.43(15) . . ?
C5' C6' C7' 118.91(15) . . ?
O4' C7' C6' 116.81(14) . . ?
O4' C7' C8' 122.10(15) . . ?
C8' C7' C6' 121.07(15) . . ?
C7' C8' C4 118.49(14) . . ?
C7' C8' C9' 118.07(15) . . ?
C9' C8' C4 123.43(14) . . ?
O1' C9' C8' 114.44(14) . . ?
O1' C9' C10' 122.16(14) . . ?
C10' C9' C8' 123.36(15) . . ?
C5' C10' C4' 122.54(15) . . ?
C9' C10' C4' 121.37(15) . . ?
C9' C10' C5' 116.04(14) . . ?
C12' C11' C2' 118.94(16) . . ?
C16' C11' C2' 122.05(18) . . ?
C16' C11' C12' 118.81(17) . . ?
C13' C12' C11' 121.25(19) . . ?
O5' C13' C12' 123.6(2) . . ?
O5' C13' C14' 117.02(18) . . ?
C12' C13' C14' 119.38(19) . . ?
O6' C14' C13' 117.5(2) . . ?
O6' C14' C15' 122.8(2) . . ?
C15' C14' C13' 119.67(18) . . ?
C14' C15' C16' 120.9(2) . . ?
C11' C16' C15' 119.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_colour            colorless
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/water'
_chemical_compound_source        yes
