# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_I_15
#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
4-(Benzyloxy)-8-(methyl)-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-
7,8-dihydrofuro[2,3-e]indol 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 N2 O6'
_chemical_formula_structural     ?
_chemical_formula_sum            'C30 H28 N2 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         512.54
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6.  CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   19.347(3)
_cell_length_b                   10.2965(8)
_cell_length_c                   12.7704(19)
_cell_angle_alpha                90
_cell_angle_beta                 105.329(15)
_cell_angle_gamma                90
_cell_volume                     2453.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200
_cell_measurement_reflns_used    577
_cell_measurement_theta_min      3.1914
_cell_measurement_theta_max      29.3570

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.097
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent, 2012),
;
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.993

#===============================================================================

# 7. EXPERIMENTAL DATA

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford-Diffraction GEMINI S Ultra'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0

# number of measured reflections (redundant set)
_diffrn_reflns_number            7634
_diffrn_reflns_av_R_equivalents  0.1494
_diffrn_reflns_av_sigmaI/netI    0.2832
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_reduction_process 
; ?
;

# number of unique reflections
_reflns_number_total             4292
# number of observed reflections (> n sig(I))
_reflns_number_gt                1312
_reflns_threshold_expression     I>2σ(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    
'TeXsan (Molecular Structure Corporation, 2001), SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  
'TeXSan (Molecular Structure Corporation, 2001), SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'

#===============================================================================

# 8. REFINEMENT DATA

_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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0534P)²]         where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none

_refine_ls_number_reflns         4292
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.2870
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.2699
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.066

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.9113(3) 0.5702(5) 0.5370(5) 1.000 0.056(2) . .
O2 O Uani 0.9613(3) 0.8124(5) 0.5555(5) 1.000 0.048(2) . .
O3 O Uani 0.9017(3) 1.0040(4) 0.6591(5) 1.000 0.048(2) . .
O4 O Uani 0.7184(3) 1.0281(4) 0.8809(5) 1.000 0.056(2) . .
O5 O Uani 0.5034(3) 0.7919(5) 1.1403(5) 1.000 0.055(2) . .
O6 O Uani 0.6044(3) 1.1983(4) 1.1503(5) 1.000 0.049(2) . .
N1 N Uani 0.7906(3) 0.9138(5) 0.7627(6) 1.000 0.044(3) . .
N2 N Uani 0.6665(3) 0.8471(5) 0.9264(6) 1.000 0.042(3) . .
C1 C Uani 0.7074(4) 0.9091(8) 0.8719(7) 1.000 0.043(3) . .
C2 C Uani 0.7441(4) 0.8389(7) 0.8006(6) 1.000 0.036(3) . .
C3 C Uani 0.7466(4) 0.7138(6) 0.7635(7) 1.000 0.044(3) . .
C4 C Uani 0.7963(4) 0.7134(7) 0.6984(7) 1.000 0.048(3) . .
C5 C Uani 0.8249(4) 0.6185(7) 0.6403(7) 1.000 0.042(3) . .
C6 C Uani 0.8768(4) 0.6524(7) 0.5921(7) 1.000 0.043(3) . .
C7 C Uani 0.9054(4) 0.7828(7) 0.5977(6) 1.000 0.039(3) . .
C8 C Uani 0.8771(4) 0.8774(7) 0.6521(7) 1.000 0.041(3) . .
C9 C Uani 0.8241(4) 0.8409(7) 0.6998(6) 1.000 0.038(3) . .
C10 C Uani 0.8906(4) 0.4359(7) 0.5306(8) 1.000 0.057(4) . .
C11 C Uani 0.9456(5) 0.8149(8) 0.4397(8) 1.000 0.063(4) . .
C12 C Uani 0.9642(5) 1.0229(7) 0.7489(7) 1.000 0.058(3) . .
C13 C Uani 0.6460(5) 0.7075(7) 0.9130(7) 1.000 0.052(4) . .
C14 C Uani 0.5914(6) 0.6877(7) 0.9785(9) 1.000 0.077(5) . .
C15 C Uani 0.5893(5) 0.8171(7) 1.0318(7) 1.000 0.045(3) . .
C16 C Uani 0.5511(5) 0.8592(7) 1.1017(7) 1.000 0.046(3) . .
C17 C Uani 0.4773(4) 0.8800(8) 1.2042(7) 1.000 0.054(4) . .
C18 C Uani 0.5077(4) 0.9974(7) 1.2067(7) 1.000 0.046(3) . .
C19 C Uani 0.5565(4) 0.9879(7) 1.1392(6) 1.000 0.038(3) . .
C20 C Uani 0.6021(4) 1.0754(6) 1.1084(7) 1.000 0.039(3) . .
C21 C Uani 0.6401(4) 1.0330(6) 1.0385(7) 1.000 0.039(3) . .
C22 C Uani 0.6332(4) 0.9057(7) 0.9987(7) 1.000 0.040(3) . .
C23 C Uani 0.5951(7) 0.5735(8) 1.0399(10) 1.000 0.107(6) . .
C24 C Uani 0.6704(4) 1.2697(6) 1.1629(7) 1.000 0.049(3) . .
C25 C Uani 0.7312(4) 1.2135(7) 1.2465(7) 1.000 0.039(3) . .
C26 C Uani 0.7214(5) 1.1526(7) 1.3389(8) 1.000 0.057(4) . .
C27 C Uani 0.7771(6) 1.1086(8) 1.4209(9) 1.000 0.069(4) . .
C28 C Uani 0.8451(7) 1.1296(9) 1.4119(9) 1.000 0.078(5) . .
C29 C Uani 0.8581(5) 1.1858(9) 1.3207(9) 1.000 0.065(4) . .
C30 C Uani 0.7998(5) 1.2307(7) 1.2376(7) 1.000 0.055(4) . .
H1 H Uiso 0.79790 0.99530 0.77580 1.000 0.0510 . .
H3 H Uiso 0.72000 0.64160 0.77750 1.000 0.0520 . .
H5 H Uiso 0.80720 0.53170 0.63490 1.000 0.0510 . .
H10A H Uiso 0.88550 0.40870 0.59940 1.000 0.0700 . .
H10B H Uiso 0.84630 0.42600 0.47750 1.000 0.0700 . .
H10C H Uiso 0.92640 0.38520 0.51160 1.000 0.0700 . .
H11A H Uiso 0.89520 0.81750 0.40990 1.000 0.0760 . .
H11B H Uiso 0.96440 0.73890 0.41540 1.000 0.0760 . .
H11C H Uiso 0.96680 0.88950 0.41770 1.000 0.0760 . .
H12A H Uiso 0.99830 0.95730 0.74680 1.000 0.0720 . .
H12B H Uiso 0.98390 1.10570 0.74280 1.000 0.0720 . .
H12C H Uiso 0.95060 1.01710 0.81470 1.000 0.0720 . .
H13A H Uiso 0.68640 0.65340 0.93920 1.000 0.0620 . .
H13B H Uiso 0.62470 0.68820 0.83820 1.000 0.0620 . .
H14A H Uiso 0.54690 0.68360 0.92510 1.000 0.0920 . .
H17 H Uiso 0.44200 0.85860 1.24130 1.000 0.0650 . .
H18 H Uiso 0.49830 1.07150 1.24490 1.000 0.0570 . .
H21 H Uiso 0.67270 1.09040 1.01660 1.000 0.0490 . .
H23A H Uiso 0.64000 0.54170 1.06340 1.000 0.1300 . .
H23B H Uiso 0.56260 0.51010 0.99610 1.000 0.1300 . .
H23C H Uiso 0.57500 0.59260 1.10110 1.000 0.1300 . .
H24A H Uiso 0.68200 1.26910 1.09480 1.000 0.0600 . .
H24B H Uiso 0.66300 1.35640 1.18230 1.000 0.0600 . .
H26 H Uiso 0.67380 1.14040 1.34360 1.000 0.0690 . .
H27 H Uiso 0.76840 1.06550 1.48190 1.000 0.0830 . .
H28 H Uiso 0.88460 1.10500 1.47060 1.000 0.0920 . .
H29 H Uiso 0.90550 1.19380 1.31340 1.000 0.0780 . .
H30 H Uiso 0.80800 1.27330 1.17590 1.000 0.0650 . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.380(10) . . yes
O1 C10 1.436(9) . . yes
O2 C7 1.364(10) . . yes
O2 C11 1.429(12) . . yes
O3 C8 1.383(9) . . yes
O3 C12 1.443(11) . . yes
O4 C1 1.244(9) . . yes
O5 C16 1.347(11) . . yes
O5 C17 1.401(10) . . yes
O6 C20 1.370(8) . . yes
O6 C24 1.445(9) . . yes
N1 C2 1.367(10) . . yes
N1 C9 1.380(10) . . yes
N2 C1 1.345(10) . . yes
N2 C13 1.489(9) . . yes
N2 C22 1.395(10) . . yes
N1 H1 0.8600 . . no
C1 C2 1.482(11) . . no
C2 C3 1.378(10) . . no
C3 C4 1.428(12) . . no
C4 C5 1.424(11) . . no
C4 C9 1.417(10) . . no
C5 C6 1.355(12) . . no
C6 C7 1.447(10) . . no
C7 C8 1.390(11) . . no
C8 C9 1.376(11) . . no
C13 C14 1.525(15) . . no
C14 C15 1.502(11) . . no
C14 C23 1.405(13) . . no
C15 C22 1.386(12) . . no
C15 C16 1.371(13) . . no
C16 C19 1.404(10) . . no
C17 C18 1.341(11) . . no
C18 C19 1.440(11) . . no
C19 C20 1.389(11) . . no
C20 C21 1.369(12) . . no
C21 C22 1.399(10) . . no
C24 C25 1.481(12) . . no
C25 C30 1.373(13) . . no
C25 C26 1.393(13) . . no
C26 C27 1.366(15) . . no
C27 C28 1.368(18) . . no
C28 C29 1.382(16) . . no
C29 C30 1.407(14) . . no
C3 H3 0.9500 . . no
C5 H5 0.9500 . . no
C10 H10A 0.9500 . . no
C10 H10B 0.9500 . . no
C10 H10C 0.9500 . . no
C11 H11A 0.9500 . . no
C11 H11B 0.9500 . . no
C11 H11C 0.9500 . . no
C12 H12A 0.9500 . . no
C12 H12B 0.9500 . . no
C12 H12C 0.9500 . . no
C13 H13A 0.9500 . . no
C13 H13B 0.9600 . . no
C14 H14A 0.9500 . . no
C17 H17 0.9500 . . no
C18 H18 0.9500 . . no
C21 H21 0.9600 . . no
C23 H23A 0.9000 . . no
C23 H23B 0.9700 . . no
C23 H23C 0.9800 . . no
C24 H24A 0.9500 . . no
C24 H24B 0.9500 . . no
C26 H26 0.9500 . . no
C27 H27 0.9500 . . no
C28 H28 0.9500 . . no
C29 H29 0.9500 . . no
C30 H30 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C10 117.0(6) . . . yes
C7 O2 C11 116.0(7) . . . yes
C8 O3 C12 112.4(6) . . . yes
C16 O5 C17 105.5(6) . . . yes
C20 O6 C24 116.7(6) . . . yes
C2 N1 C9 110.7(6) . . . yes
C1 N2 C13 125.0(7) . . . yes
C1 N2 C22 125.1(6) . . . yes
C13 N2 C22 109.8(6) . . . yes
C2 N1 H1 125.00 . . . no
C9 N1 H1 124.00 . . . no
O4 C1 N2 122.0(7) . . . yes
N2 C1 C2 122.0(7) . . . yes
O4 C1 C2 116.1(7) . . . yes
N1 C2 C3 108.6(7) . . . yes
N1 C2 C1 114.2(6) . . . yes
C1 C2 C3 137.2(7) . . . no
C2 C3 C4 107.1(6) . . . no
C3 C4 C5 136.0(7) . . . no
C5 C4 C9 116.3(7) . . . no
C3 C4 C9 107.6(6) . . . no
C4 C5 C6 119.8(7) . . . no
O1 C6 C7 111.4(7) . . . yes
O1 C6 C5 126.2(7) . . . yes
C5 C6 C7 122.4(7) . . . no
O2 C7 C8 119.9(7) . . . yes
O2 C7 C6 121.4(7) . . . yes
C6 C7 C8 118.6(7) . . . no
O3 C8 C9 120.9(7) . . . yes
C7 C8 C9 117.9(7) . . . no
O3 C8 C7 121.2(7) . . . yes
C4 C9 C8 124.9(7) . . . no
N1 C9 C4 106.0(7) . . . yes
N1 C9 C8 129.0(7) . . . yes
N2 C13 C14 105.6(6) . . . yes
C15 C14 C23 119.6(9) . . . no
C13 C14 C15 103.6(7) . . . no
C13 C14 C23 118.5(9) . . . no
C14 C15 C22 110.7(8) . . . no
C14 C15 C16 131.3(8) . . . no
C16 C15 C22 118.0(7) . . . no
O5 C16 C19 110.9(7) . . . yes
O5 C16 C15 127.9(7) . . . yes
C15 C16 C19 121.1(8) . . . no
O5 C17 C18 112.0(7) . . . yes
C17 C18 C19 106.1(7) . . . no
C16 C19 C18 105.5(7) . . . no
C16 C19 C20 120.8(7) . . . no
C18 C19 C20 133.8(7) . . . no
O6 C20 C19 116.5(7) . . . yes
C19 C20 C21 117.9(6) . . . no
O6 C20 C21 125.6(7) . . . yes
C20 C21 C22 121.3(7) . . . no
N2 C22 C21 129.0(7) . . . yes
N2 C22 C15 110.2(6) . . . yes
C15 C22 C21 120.9(8) . . . no
O6 C24 C25 113.1(6) . . . yes
C24 C25 C26 121.8(8) . . . no
C26 C25 C30 118.6(8) . . . no
C24 C25 C30 119.4(7) . . . no
C25 C26 C27 122.8(9) . . . no
C26 C27 C28 117.7(10) . . . no
C27 C28 C29 122.0(11) . . . no
C28 C29 C30 119.0(10) . . . no
C25 C30 C29 119.7(8) . . . no
C2 C3 H3 127.00 . . . no
C4 C3 H3 126.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
O1 C10 H10A 109.00 . . . no
O1 C10 H10B 109.00 . . . no
O1 C10 H10C 109.00 . . . no
H10A C10 H10B 110.00 . . . no
H10A C10 H10C 110.00 . . . no
H10B C10 H10C 110.00 . . . no
O2 C11 H11A 109.00 . . . no
O2 C11 H11B 109.00 . . . no
O2 C11 H11C 109.00 . . . no
H11A C11 H11B 110.00 . . . no
H11A C11 H11C 110.00 . . . no
H11B C11 H11C 110.00 . . . no
O3 C12 H12A 109.00 . . . no
O3 C12 H12B 109.00 . . . no
O3 C12 H12C 109.00 . . . no
H12A C12 H12B 110.00 . . . no
H12A C12 H12C 110.00 . . . no
H12B C12 H12C 110.00 . . . no
N2 C13 H13A 111.00 . . . no
N2 C13 H13B 110.00 . . . no
C14 C13 H13A 111.00 . . . no
C14 C13 H13B 110.00 . . . no
H13A C13 H13B 109.00 . . . no
C13 C14 H14A 104.00 . . . no
C15 C14 H14A 104.00 . . . no
C23 C14 H14A 105.00 . . . no
O5 C17 H17 124.00 . . . no
C18 C17 H17 124.00 . . . no
C17 C18 H18 126.00 . . . no
C19 C18 H18 127.00 . . . no
C20 C21 H21 120.00 . . . no
C22 C21 H21 119.00 . . . no
C14 C23 H23A 113.00 . . . no
C14 C23 H23B 108.00 . . . no
C14 C23 H23C 108.00 . . . no
H23A C23 H23B 111.00 . . . no
H23A C23 H23C 111.00 . . . no
H23B C23 H23C 105.00 . . . no
O6 C24 H24A 108.00 . . . no
O6 C24 H24B 109.00 . . . no
C25 C24 H24A 109.00 . . . no
C25 C24 H24B 109.00 . . . no
H24A C24 H24B 109.00 . . . no
C25 C26 H26 118.00 . . . no
C27 C26 H26 119.00 . . . no
C26 C27 H27 121.00 . . . no
C28 C27 H27 122.00 . . . no
C27 C28 H28 119.00 . . . no
C29 C28 H28 119.00 . . . no
C28 C29 H29 121.00 . . . no
C30 C29 H29 120.00 . . . no
C25 C30 H30 120.00 . . . no
C29 C30 H30 120.00 . . . no

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
C10 O1 C6 C5 -0.4(12) . . . . no
C10 O1 C6 C7 176.8(7) . . . . no
C11 O2 C7 C6 72.0(9) . . . . no
C11 O2 C7 C8 -111.2(8) . . . . no
C12 O3 C8 C7 -85.4(9) . . . . no
C12 O3 C8 C9 94.0(9) . . . . no
C17 O5 C16 C15 -177.4(9) . . . . no
C17 O5 C16 C19 0.1(9) . . . . no
C16 O5 C17 C18 -0.6(9) . . . . no
C24 O6 C20 C19 152.2(7) . . . . no
C24 O6 C20 C21 -28.6(11) . . . . no
C20 O6 C24 C25 -67.3(9) . . . . no
C9 N1 C2 C3 0.4(9) . . . . no
C2 N1 C9 C4 0.3(9) . . . . no
C9 N1 C2 C1 178.2(7) . . . . no
C2 N1 C9 C8 -176.0(8) . . . . no
C1 N2 C13 C14 -172.0(8) . . . . no
C22 N2 C13 C14 4.3(9) . . . . no
C22 N2 C1 C2 176.8(7) . . . . no
C13 N2 C1 O4 174.7(8) . . . . no
C13 N2 C1 C2 -7.5(12) . . . . no
C22 N2 C1 O4 -1.0(13) . . . . no
C1 N2 C22 C15 173.8(8) . . . . no
C1 N2 C22 C21 -7.2(14) . . . . no
C13 N2 C22 C15 -2.4(10) . . . . no
C13 N2 C22 C21 176.6(8) . . . . no
N2 C1 C2 N1 -172.0(7) . . . . no
N2 C1 C2 C3 5.0(15) . . . . no
O4 C1 C2 N1 5.9(11) . . . . no
O4 C1 C2 C3 -177.1(9) . . . . no
C1 C2 C3 C4 -178.0(9) . . . . no
N1 C2 C3 C4 -1.0(9) . . . . no
C2 C3 C4 C5 177.7(9) . . . . no
C2 C3 C4 C9 1.1(9) . . . . no
C3 C4 C5 C6 -175.1(9) . . . . no
C9 C4 C5 C6 1.2(12) . . . . no
C3 C4 C9 N1 -0.9(9) . . . . no
C3 C4 C9 C8 175.6(8) . . . . no
C5 C4 C9 N1 -178.2(7) . . . . no
C5 C4 C9 C8 -1.8(12) . . . . no
C4 C5 C6 C7 0.5(13) . . . . no
C4 C5 C6 O1 177.3(8) . . . . no
O1 C6 C7 O2 -2.2(11) . . . . no
O1 C6 C7 C8 -179.1(7) . . . . no
C5 C6 C7 O2 175.0(8) . . . . no
C5 C6 C7 C8 -1.8(12) . . . . no
C6 C7 C8 C9 1.3(11) . . . . no
C6 C7 C8 O3 -179.3(7) . . . . no
O2 C7 C8 O3 3.9(12) . . . . no
O2 C7 C8 C9 -175.6(7) . . . . no
C7 C8 C9 N1 176.1(8) . . . . no
C7 C8 C9 C4 0.5(12) . . . . no
O3 C8 C9 C4 -179.0(7) . . . . no
O3 C8 C9 N1 -3.4(13) . . . . no
N2 C13 C14 C15 -4.3(10) . . . . no
N2 C13 C14 C23 -139.5(9) . . . . no
C13 C14 C15 C16 -179.0(9) . . . . no
C13 C14 C15 C22 3.1(11) . . . . no
C23 C14 C15 C22 137.7(11) . . . . no
C23 C14 C15 C16 -44.4(17) . . . . no
C14 C15 C16 C19 -178.2(9) . . . . no
C14 C15 C16 O5 -0.8(17) . . . . no
C16 C15 C22 N2 -178.7(8) . . . . no
C16 C15 C22 C21 2.2(13) . . . . no
C22 C15 C16 C19 -0.4(13) . . . . no
C14 C15 C22 N2 -0.5(10) . . . . no
C22 C15 C16 O5 177.0(8) . . . . no
C14 C15 C22 C21 -179.6(8) . . . . no
O5 C16 C19 C18 0.3(9) . . . . no
O5 C16 C19 C20 -179.3(7) . . . . no
C15 C16 C19 C18 178.0(8) . . . . no
C15 C16 C19 C20 -1.5(13) . . . . no
O5 C17 C18 C19 0.8(10) . . . . no
C17 C18 C19 C20 178.8(9) . . . . no
C17 C18 C19 C16 -0.6(9) . . . . no
C16 C19 C20 O6 -179.2(7) . . . . no
C16 C19 C20 C21 1.6(12) . . . . no
C18 C19 C20 O6 1.4(14) . . . . no
C18 C19 C20 C21 -177.9(9) . . . . no
C19 C20 C21 C22 0.3(12) . . . . no
O6 C20 C21 C22 -179.0(8) . . . . no
C20 C21 C22 N2 178.9(8) . . . . no
C20 C21 C22 C15 -2.2(13) . . . . no
O6 C24 C25 C30 152.2(7) . . . . no
O6 C24 C25 C26 -33.2(10) . . . . no
C24 C25 C26 C27 -175.0(8) . . . . no
C24 C25 C30 C29 175.4(7) . . . . no
C26 C25 C30 C29 0.6(12) . . . . no
C30 C25 C26 C27 -0.3(12) . . . . no
C25 C26 C27 C28 2.0(13) . . . . no
C26 C27 C28 C29 -4.0(14) . . . . no
C27 C28 C29 C30 4.3(14) . . . . no
C28 C29 C30 C25 -2.5(13) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O2 2.663(7) . . no
O1 C11 2.961(10) . . no
O1 C12 3.167(11) . 2_746 no
O2 O1 2.663(7) . . no
O2 C12 3.275(10) . . no
O2 O3 2.789(8) . . no
O3 N1 2.956(9) . . no
O3 C28 3.318(12) . 1_554 no
O3 O2 2.789(8) . . no
O4 C21 2.821(10) . . no
O4 N1 2.594(9) . . no
O4 C10 3.395(11) . 4_565 no
O4 C26 3.334(8) . 4_574 no
O4 C24 3.403(10) . 4_574 no
O4 C25 3.211(9) . 4_574 no
O5 C23 3.324(13) . . no
O6 C17 3.317(10) . 2_657 no
O1 H12C 2.8900 . 2_746 no
O1 H11B 2.7100 . . no
O2 H29 2.6800 . 3_777 no
O2 H12A 2.7900 . . no
O3 H1 2.8000 . . no
O3 H28 2.5600 . 1_554 no
O4 H1 2.3200 . . no
O4 H24B 2.7500 . 4_574 no
O4 H21 2.2400 . . no
O4 H10B 2.5000 . 4_565 no
O5 H18 2.7100 . 2_647 no
O5 H23C 2.6000 . . no
O6 H26 2.5500 . . no
O6 H17 2.4700 . 2_657 no
N1 O3 2.956(9) . . no
N1 O4 2.594(9) . . no
C1 C5 3.589(12) . 4_565 no
C3 C13 3.066(13) . . no
C5 C1 3.589(12) . 4_564 no
C6 C12 3.473(12) . 2_746 no
C10 C28 3.509(12) . 1_544 no
C10 O4 3.395(11) . 4_564 no
C10 C12 3.527(13) . 2_746 no
C11 O1 2.961(10) . . no
C12 C6 3.473(12) . 2_756 no
C12 O1 3.167(11) . 2_756 no
C12 O2 3.275(10) . . no
C12 C10 3.527(13) . 2_756 no
C13 C3 3.066(13) . . no
C16 C20 3.498(12) . 3_677 no
C16 C19 3.590(11) . 3_677 no
C17 C21 3.442(12) . 3_677 no
C17 O6 3.317(10) . 2_647 no
C18 C22 3.395(12) . 3_677 no
C19 C16 3.590(11) . 3_677 no
C20 C16 3.498(12) . 3_677 no
C20 C26 3.321(13) . . no
C21 C17 3.442(12) . 3_677 no
C21 O4 2.821(10) . . no
C21 C25 3.338(11) . . no
C22 C18 3.395(12) . 3_677 no
C23 O5 3.324(13) . . no
C24 O4 3.403(10) . 4_575 no
C25 O4 3.211(9) . 4_575 no
C25 C21 3.338(11) . . no
C26 O4 3.334(8) . 4_575 no
C26 C20 3.321(13) . . no
C28 C10 3.509(12) . 1_566 no
C28 O3 3.318(12) . 1_556 no
C1 H21 2.8300 . . no
C2 H13A 3.0100 . . no
C2 H13B 2.9300 . . no
C3 H11A 3.0000 . 4_565 no
C3 H13B 2.7800 . . no
C3 H13A 2.8600 . . no
C4 H11A 2.8900 . 4_565 no
C5 H10B 2.9800 . . no
C5 H10A 2.5800 . . no
C6 H12B 2.9900 . 2_746 no
C6 H11A 2.9800 . . no
C7 H12A 2.8800 . . no
C9 H12C 3.0900 . . no
C10 H12A 3.0900 . 2_746 no
C10 H5 2.5500 . . no
C12 H11C 2.9400 . 3_776 no
C13 H3 2.6100 . . no
C16 H23C 2.7800 . . no
C16 H13B 3.0200 . 4_565 no
C17 H14A 2.8600 . 4_565 no
C17 H13B 3.0000 . 4_565 no
C18 H13B 3.1000 . 4_565 no
C20 H26 3.0300 . . no
C21 H24A 2.6000 . . no
C23 H24B 2.9600 . 1_545 no
C23 H23B 3.0900 . 3_667 no
C24 H21 2.6400 . . no
C24 H23A 3.0700 . 1_565 no
C24 H17 2.9100 . 2_657 no
C30 H1 2.8600 . 4_575 no
C30 H5 3.0200 . 4_565 no
C30 H10A 3.0800 . 4_565 no
H1 O3 2.8000 . . no
H1 O4 2.3200 . . no
H1 C30 2.8600 . 4_574 no
H3 C13 2.6100 . . no
H3 H13A 2.3300 . . no
H3 H13B 2.2300 . . no
H5 C10 2.5500 . . no
H5 H10A 2.1100 . . no
H5 H10B 2.5700 . . no
H5 C30 3.0200 . 4_564 no
H10A C5 2.5800 . . no
H10A H5 2.1100 . . no
H10A C30 3.0800 . 4_564 no
H10B C5 2.9800 . . no
H10B H5 2.5700 . . no
H10B O4 2.5000 . 4_564 no
H10C H11B 2.4300 . 3_766 no
H11A C6 2.9800 . . no
H11A C3 3.0000 . 4_564 no
H11A C4 2.8900 . 4_564 no
H11B O1 2.7100 . . no
H11B H10C 2.4300 . 3_766 no
H11C C12 2.9400 . 3_776 no
H11C H12B 2.4800 . 3_776 no
H12A O2 2.7900 . . no
H12A C7 2.8800 . . no
H12A C10 3.0900 . 2_756 no
H12B C6 2.9900 . 2_756 no
H12B H11C 2.4800 . 3_776 no
H12C C9 3.0900 . . no
H12C O1 2.8900 . 2_756 no
H13A C2 3.0100 . . no
H13A C3 2.8600 . . no
H13A H3 2.3300 . . no
H13A H23A 2.3200 . . no
H13B C2 2.9300 . . no
H13B C3 2.7800 . . no
H13B H3 2.2300 . . no
H13B C16 3.0200 . 4_564 no
H13B C17 3.0000 . 4_564 no
H13B C18 3.1000 . 4_564 no
H14A C17 2.8600 . 4_564 no
H17 O6 2.4700 . 2_647 no
H17 C24 2.9100 . 2_647 no
H17 H24B 2.4800 . 2_647 no
H18 O5 2.7100 . 2_657 no
H21 O4 2.2400 . . no
H21 C1 2.8300 . . no
H21 C24 2.6400 . . no
H21 H24A 2.0800 . . no
H23A C24 3.0700 . 1_545 no
H23A H13A 2.3200 . . no
H23A H24B 2.4100 . 1_545 no
H23B C23 3.0900 . 3_667 no
H23B H23B 2.4600 . 3_667 no
H23C O5 2.6000 . . no
H23C C16 2.7800 . . no
H24A C21 2.6000 . . no
H24A H21 2.0800 . . no
H24A H30 2.3800 . . no
H24B C23 2.9600 . 1_565 no
H24B H23A 2.4100 . 1_565 no
H24B H17 2.4800 . 2_657 no
H24B O4 2.7500 . 4_575 no
H26 O6 2.5500 . . no
H26 C20 3.0300 . . no
H28 O3 2.5600 . 1_556 no
H29 O2 2.6800 . 3_777 no
H30 H24A 2.3800 . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C10 H10B O4 0.9500 2.5000 3.395(11) 157.00 4_564 yes
C17 H17 O6 0.9500 2.4700 3.317(10) 148.00 2_647 yes
C21 H21 O4 0.9600 2.2400 2.821(10) 118.00 . yes
C23 H23C O5 0.9800 2.6000 3.324(13) 131.00 . yes
C26 H26 O6 0.9500 2.5500 2.875(12) 100.00 . yes
C28 H28 O3 0.9500 2.5600 3.318(12) 136.00 1_556 yes

#===END

_database_code_depnum_ccdc_archive 'CCDC 992249'
