# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1528254'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O6'
_chemical_formula_sum            'C22 H20 O6'
_chemical_formula_weight         380.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7557(4)
_cell_length_b                   10.3822(4)
_cell_length_c                   11.1677(5)
_cell_angle_alpha                63.052(4)
_cell_angle_beta                 82.840(4)
_cell_angle_gamma                86.270(4)
_cell_volume                     897.85(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    5102
_cell_measurement_theta_min      4.9420
_cell_measurement_theta_max      76.4780

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 -5 0.1206
0 4 -3 0.1039
-4 5 2 0.1434
-4 4 4 0.1377
1 -4 3 0.0823
4 -1 -5 0.1269
-4 0 -6 0.0802
4 1 5 0.0535
-2 -5 2 0.0779
-4 -5 -2 0.0718
-5 -3 -4 0.0705
-2 -1 -7 0.0754
2 6 4 0.1188
3 5 6 0.0904
-2 5 -2 0.1137
2 5 6 0.0951
-5 -1 -3 0.0903
-5 -3 -1 0.0902
5 3 1 0.1255
4 -1 4 0.0626
-1 6 3 0.1181
0 -1 -7 0.0927
1 6 6 0.1039
1 -6 -1 0.1249

_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus 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, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1333
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  30.00   1.00    2.50    --  -42.26  57.00  30.00   96
  2  ω     42.00  69.00   1.00    2.50    --   42.26-125.00-150.00   27
  3  ω     45.00  97.00   1.00    2.50    --   42.26-125.00-180.00   52
  4  ω     85.00 110.00   1.00   10.00    --  112.00-111.00 -90.00   25
  5  ω     76.00 115.00   1.00   10.00    --  112.00-111.00 -30.00   39
  6  ω     83.00 138.00   1.00   10.00    --  112.00 -45.00   0.00   55
  7  ω     88.00 116.00   1.00   10.00    --  112.00-111.00  60.00   28
  8  ω     79.00 116.00   1.00   10.00    --  112.00-111.00 120.00   37
  9  ω     64.00 108.00   1.00   10.00    --  112.00 -61.00  60.00   44
 10  ω     53.00  80.00   1.00   10.00    --  112.00 -45.00   0.00   27
 11  ω     59.00 145.00   1.00   10.00    --  112.00 -77.00 -60.00   86
 12  ω     81.00 139.00   1.00   10.00    --  112.00 -30.00 -90.00   58
 13  ω    128.00 171.00   1.00   10.00    --  112.00  45.00 -90.00   43
 14  ω    116.00 178.00   1.00   10.00    --  112.00 111.00  30.00   62
 15  ω    121.00 151.00   1.00   10.00    --  112.00 178.00 -30.00   30
 16  ω     84.00 150.00   1.00   10.00    --  112.00 178.00 -90.00   66
 17  ω     80.00 132.00   1.00   10.00    --  112.00 178.00 -60.00   52
 18  ω     60.00 118.00   1.00   10.00    --  112.00 178.00 -30.00   58
 19  ω     96.00 145.00   1.00   10.00    --  112.00  61.00 150.00   49
 20  ω     93.00 172.00   1.00   10.00    --  112.00  45.00  90.00   79
 21  ω     89.00 178.00   1.00   10.00    --  112.00  45.00   0.00   89
 22  ω     47.00  74.00   1.00   10.00    --  112.00-111.00  30.00   27
 23  ω     40.00  72.00   1.00   10.00    --  112.00-111.00 -30.00   32
 24  ω     38.00  72.00   1.00   10.00    --  112.00 -30.00 -90.00   34
 25  ω   -109.00 -19.00   1.00    2.50    --  -42.26 -57.00-120.00   90
 26  ω   -110.00 -14.00   1.00    2.50    --  -42.26 -57.00 120.00   96
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7574
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.467
_diffrn_reflns_theta_max         76.788
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3705
_reflns_number_gt                3511
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.3559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3705
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.57636(9) 0.37447(8) 0.28257(8) 0.02003(18) Uani 1 1 d . . . . .
O2 O 0.75822(10) 0.37764(9) 0.11958(9) 0.0249(2) Uani 1 1 d . . . . .
O3 O 0.41857(9) 0.98753(8) -0.16186(8) 0.01994(18) Uani 1 1 d . . . . .
O4 O 0.22003(9) 1.10909(8) -0.08361(8) 0.02033(18) Uani 1 1 d . . . . .
O5 O -0.16367(10) 0.94329(9) 0.49269(9) 0.02433(19) Uani 1 1 d . . . . .
O6 O -0.03449(10) 0.73960(9) 0.51695(8) 0.0250(2) Uani 1 1 d . . . . .
C1 C 0.50291(18) 0.29658(15) 0.56011(13) 0.0328(3) Uani 1 1 d . . . . .
H1A H 0.445(2) 0.378(2) 0.5007(19) 0.040(5) Uiso 1 1 d . . . . .
H1B H 0.441(2) 0.259(2) 0.648(2) 0.049(5) Uiso 1 1 d . . . . .
H1C H 0.606(3) 0.334(2) 0.568(2) 0.056(6) Uiso 1 1 d . . . . .
C2 C 0.53059(15) 0.18433(13) 0.50721(12) 0.0250(3) Uani 1 1 d . . . . .
H2A H 0.4313(19) 0.1551(17) 0.4937(16) 0.027(4) Uiso 1 1 d . . . . .
H2B H 0.5800(19) 0.0977(18) 0.5747(17) 0.032(4) Uiso 1 1 d . . . . .
C3 C 0.63587(14) 0.23585(12) 0.37695(12) 0.0212(2) Uani 1 1 d . . . . .
H3A H 0.6405(18) 0.1678(17) 0.3373(15) 0.026(4) Uiso 1 1 d . . . . .
H3B H 0.7408(18) 0.2525(16) 0.3890(15) 0.021(3) Uiso 1 1 d . . . . .
C4 C 0.65243(13) 0.43538(12) 0.15811(11) 0.0186(2) Uani 1 1 d . . . . .
C5 C 0.59181(12) 0.58310(12) 0.07450(11) 0.0176(2) Uani 1 1 d . . . . .
C6 C 0.65488(13) 0.65605(12) -0.06052(11) 0.0196(2) Uani 1 1 d . . . . .
H6 H 0.7376(19) 0.6098(17) -0.0956(16) 0.028(4) Uiso 1 1 d . . . . .
C7 C 0.60334(13) 0.79327(12) -0.14627(11) 0.0200(2) Uani 1 1 d . . . . .
H7 H 0.6487(18) 0.8449(17) -0.2397(16) 0.028(4) Uiso 1 1 d . . . . .
C8 C 0.48713(13) 0.85171(12) -0.09055(11) 0.0184(2) Uani 1 1 d . . . . .
C9 C 0.42280(12) 0.78292(12) 0.04602(11) 0.0172(2) Uani 1 1 d . . . . .
C10 C 0.47667(12) 0.64601(12) 0.12944(11) 0.0174(2) Uani 1 1 d . . . . .
H10 H 0.4355(18) 0.5951(17) 0.2244(16) 0.025(4) Uiso 1 1 d . . . . .
C11 C 0.30967(13) 0.88439(12) 0.05903(11) 0.0179(2) Uani 1 1 d . . . . .
C12 C 0.31635(13) 0.99692(12) -0.06532(11) 0.0185(2) Uani 1 1 d . . . . .
C13 C 0.13990(13) 1.06346(12) 0.04586(11) 0.0184(2) Uani 1 1 d . . . . .
C14 C 0.02681(13) 1.14308(12) 0.08025(12) 0.0206(2) Uani 1 1 d . . . . .
H14 H -0.0058(18) 1.2350(17) 0.0168(15) 0.024(4) Uiso 1 1 d . . . . .
C15 C -0.03948(13) 1.08007(12) 0.21389(12) 0.0202(2) Uani 1 1 d . . . . .
H15 H -0.1177(18) 1.1327(17) 0.2414(16) 0.027(4) Uiso 1 1 d . . . . .
C16 C 0.00712(13) 0.94289(12) 0.30736(11) 0.0190(2) Uani 1 1 d . . . . .
C17 C 0.12308(13) 0.86505(12) 0.27026(11) 0.0182(2) Uani 1 1 d . . . . .
H17 H 0.1556(18) 0.7698(17) 0.3358(16) 0.025(4) Uiso 1 1 d . . . . .
C18 C 0.19132(12) 0.92560(11) 0.13756(11) 0.0176(2) Uani 1 1 d . . . . .
C19 C -0.07309(13) 0.87980(12) 0.44731(12) 0.0196(2) Uani 1 1 d . . . . .
C20 C -0.10932(15) 0.66276(13) 0.65344(12) 0.0256(3) Uani 1 1 d . . . . .
H20A H -0.0580(18) 0.6918(16) 0.7095(16) 0.026(4) Uiso 1 1 d . . . . .
H20B H -0.218(2) 0.6920(17) 0.6527(16) 0.030(4) Uiso 1 1 d . . . . .
C21 C -0.08902(14) 0.50308(13) 0.69349(12) 0.0246(3) Uani 1 1 d . . . . .
H21A H -0.139(2) 0.4807(18) 0.6318(17) 0.032(4) Uiso 1 1 d . . . . .
H21B H -0.148(2) 0.4500(18) 0.7851(17) 0.035(4) Uiso 1 1 d . . . . .
C22 C 0.07752(15) 0.45169(14) 0.69750(14) 0.0293(3) Uani 1 1 d . . . . .
H22A H 0.142(2) 0.506(2) 0.609(2) 0.045(5) Uiso 1 1 d . . . . .
H22B H 0.123(2) 0.459(2) 0.771(2) 0.053(5) Uiso 1 1 d . . . . .
H22C H 0.088(2) 0.348(2) 0.7177(18) 0.040(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.3427(13) . ?
O1 C3 1.4554(13) . ?
O2 C4 1.2102(14) . ?
O3 C12 1.3477(14) . ?
O3 C8 1.4050(13) . ?
O4 C12 1.3449(14) . ?
O4 C13 1.4060(13) . ?
O5 C19 1.2062(14) . ?
O6 C19 1.3466(14) . ?
O6 C20 1.4512(13) . ?
C1 C2 1.5224(18) . ?
C1 H1A 0.964(19) . ?
C1 H1B 0.98(2) . ?
C1 H1C 1.04(2) . ?
C2 C3 1.5088(16) . ?
C2 H2A 0.990(16) . ?
C2 H2B 0.990(17) . ?
C3 H3A 0.986(16) . ?
C3 H3B 0.982(15) . ?
C4 C5 1.4918(15) . ?
C5 C10 1.3938(15) . ?
C5 C6 1.4014(15) . ?
C6 C7 1.3921(16) . ?
C6 H6 0.981(17) . ?
C7 C8 1.3766(16) . ?
C7 H7 0.975(16) . ?
C8 C9 1.4158(15) . ?
C9 C10 1.3903(15) . ?
C9 C11 1.4419(15) . ?
C10 H10 0.977(15) . ?
C11 C12 1.3473(15) . ?
C11 C18 1.4429(15) . ?
C13 C14 1.3775(16) . ?
C13 C18 1.4152(15) . ?
C14 C15 1.3931(16) . ?
C14 H14 0.947(16) . ?
C15 C16 1.4028(16) . ?
C15 H15 0.956(16) . ?
C16 C17 1.3955(15) . ?
C16 C19 1.4911(15) . ?
C17 C18 1.3900(15) . ?
C17 H17 0.977(16) . ?
C20 C21 1.5131(17) . ?
C20 H20A 0.971(16) . ?
C20 H20B 0.981(17) . ?
C21 C22 1.5187(18) . ?
C21 H21A 0.977(17) . ?
C21 H21B 1.004(17) . ?
C22 H22A 1.00(2) . ?
C22 H22B 0.99(2) . ?
C22 H22C 1.000(19) . ?

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
C4 O1 C3 116.22(8) . . ?
C12 O3 C8 101.95(8) . . ?
C12 O4 C13 101.92(8) . . ?
C19 O6 C20 116.89(9) . . ?
C2 C1 H1A 110.7(11) . . ?
C2 C1 H1B 112.1(12) . . ?
H1A C1 H1B 105.4(16) . . ?
C2 C1 H1C 110.9(12) . . ?
H1A C1 H1C 108.8(16) . . ?
H1B C1 H1C 108.8(16) . . ?
C3 C2 C1 113.38(10) . . ?
C3 C2 H2A 109.1(9) . . ?
C1 C2 H2A 109.9(9) . . ?
C3 C2 H2B 106.9(10) . . ?
C1 C2 H2B 109.1(9) . . ?
H2A C2 H2B 108.3(13) . . ?
O1 C3 C2 107.49(9) . . ?
O1 C3 H3A 109.2(9) . . ?
C2 C3 H3A 112.2(9) . . ?
O1 C3 H3B 106.9(9) . . ?
C2 C3 H3B 111.9(8) . . ?
H3A C3 H3B 109.0(12) . . ?
O2 C4 O1 123.89(10) . . ?
O2 C4 C5 124.43(10) . . ?
O1 C4 C5 111.67(9) . . ?
C10 C5 C6 121.39(10) . . ?
C10 C5 C4 120.89(10) . . ?
C6 C5 C4 117.72(10) . . ?
C7 C6 C5 121.51(10) . . ?
C7 C6 H6 119.1(9) . . ?
C5 C6 H6 119.4(9) . . ?
C8 C7 C6 116.01(10) . . ?
C8 C7 H7 122.4(9) . . ?
C6 C7 H7 121.5(9) . . ?
C7 C8 O3 124.19(10) . . ?
C7 C8 C9 124.18(10) . . ?
O3 C8 C9 111.63(9) . . ?
C10 C9 C8 118.56(10) . . ?
C10 C9 C11 136.77(10) . . ?
C8 C9 C11 104.67(9) . . ?
C9 C10 C5 118.33(10) . . ?
C9 C10 H10 121.0(9) . . ?
C5 C10 H10 120.6(9) . . ?
C12 C11 C9 104.49(10) . . ?
C12 C11 C18 104.15(10) . . ?
C9 C11 C18 151.35(10) . . ?
O4 C12 C11 117.57(10) . . ?
O4 C12 O3 125.19(10) . . ?
C11 C12 O3 117.24(10) . . ?
C14 C13 O4 124.55(10) . . ?
C14 C13 C18 123.98(10) . . ?
O4 C13 C18 111.47(9) . . ?
C13 C14 C15 116.34(10) . . ?
C13 C14 H14 122.3(9) . . ?
C15 C14 H14 121.3(9) . . ?
C14 C15 C16 121.35(10) . . ?
C14 C15 H15 118.5(9) . . ?
C16 C15 H15 120.1(9) . . ?
C17 C16 C15 121.18(10) . . ?
C17 C16 C19 120.40(10) . . ?
C15 C16 C19 118.41(10) . . ?
C18 C17 C16 118.62(10) . . ?
C18 C17 H17 120.5(9) . . ?
C16 C17 H17 120.9(9) . . ?
C17 C18 C13 118.53(10) . . ?
C17 C18 C11 136.57(10) . . ?
C13 C18 C11 104.90(9) . . ?
O5 C19 O6 123.70(10) . . ?
O5 C19 C16 125.27(10) . . ?
O6 C19 C16 111.00(9) . . ?
O6 C20 C21 106.94(9) . . ?
O6 C20 H20A 106.5(9) . . ?
C21 C20 H20A 112.2(9) . . ?
O6 C20 H20B 107.9(9) . . ?
C21 C20 H20B 112.0(10) . . ?
H20A C20 H20B 111.0(13) . . ?
C20 C21 C22 114.17(11) . . ?
C20 C21 H21A 108.7(10) . . ?
C22 C21 H21A 110.5(10) . . ?
C20 C21 H21B 106.9(10) . . ?
C22 C21 H21B 109.9(10) . . ?
H21A C21 H21B 106.3(14) . . ?
C21 C22 H22A 112.7(11) . . ?
C21 C22 H22B 110.2(12) . . ?
H22A C22 H22B 110.0(16) . . ?
C21 C22 H22C 112.4(10) . . ?
H22A C22 H22C 105.7(14) . . ?
H22B C22 H22C 105.6(15) . . ?

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
C4 O1 C3 C2 -177.62(9) . . . . ?
C1 C2 C3 O1 -51.60(14) . . . . ?
C3 O1 C4 O2 5.01(16) . . . . ?
C3 O1 C4 C5 -174.22(9) . . . . ?
O2 C4 C5 C10 -175.41(11) . . . . ?
O1 C4 C5 C10 3.82(15) . . . . ?
O2 C4 C5 C6 4.41(17) . . . . ?
O1 C4 C5 C6 -176.36(9) . . . . ?
C10 C5 C6 C7 -1.23(17) . . . . ?
C4 C5 C6 C7 178.95(10) . . . . ?
C5 C6 C7 C8 -0.29(17) . . . . ?
C6 C7 C8 O3 -178.80(10) . . . . ?
C6 C7 C8 C9 1.76(17) . . . . ?
C12 O3 C8 C7 -178.76(11) . . . . ?
C12 O3 C8 C9 0.74(12) . . . . ?
C7 C8 C9 C10 -1.70(17) . . . . ?
O3 C8 C9 C10 178.80(9) . . . . ?
C7 C8 C9 C11 178.56(11) . . . . ?
O3 C8 C9 C11 -0.93(12) . . . . ?
C8 C9 C10 C5 0.10(16) . . . . ?
C11 C9 C10 C5 179.72(12) . . . . ?
C6 C5 C10 C9 1.29(16) . . . . ?
C4 C5 C10 C9 -178.89(10) . . . . ?
C10 C9 C11 C12 -178.93(13) . . . . ?
C8 C9 C11 C12 0.73(12) . . . . ?
C10 C9 C11 C18 -0.4(3) . . . . ?
C8 C9 C11 C18 179.25(19) . . . . ?
C13 O4 C12 C11 -0.11(13) . . . . ?
C13 O4 C12 O3 179.41(10) . . . . ?
C9 C11 C12 O4 179.24(9) . . . . ?
C18 C11 C12 O4 -0.03(14) . . . . ?
C9 C11 C12 O3 -0.31(14) . . . . ?
C18 C11 C12 O3 -179.59(9) . . . . ?
C8 O3 C12 O4 -179.76(11) . . . . ?
C8 O3 C12 C11 -0.25(13) . . . . ?
C12 O4 C13 C14 179.47(11) . . . . ?
C12 O4 C13 C18 0.21(12) . . . . ?
O4 C13 C14 C15 -179.85(10) . . . . ?
C18 C13 C14 C15 -0.68(17) . . . . ?
C13 C14 C15 C16 -0.11(17) . . . . ?
C14 C15 C16 C17 0.76(17) . . . . ?
C14 C15 C16 C19 -177.69(10) . . . . ?
C15 C16 C17 C18 -0.62(17) . . . . ?
C19 C16 C17 C18 177.79(10) . . . . ?
C16 C17 C18 C13 -0.13(16) . . . . ?
C16 C17 C18 C11 -179.70(12) . . . . ?
C14 C13 C18 C17 0.81(17) . . . . ?
O4 C13 C18 C17 -179.93(9) . . . . ?
C14 C13 C18 C11 -179.50(11) . . . . ?
O4 C13 C18 C11 -0.23(12) . . . . ?
C12 C11 C18 C17 179.76(13) . . . . ?
C9 C11 C18 C17 1.2(3) . . . . ?
C12 C11 C18 C13 0.15(12) . . . . ?
C9 C11 C18 C13 -178.37(19) . . . . ?
C20 O6 C19 O5 0.80(17) . . . . ?
C20 O6 C19 C16 -177.53(10) . . . . ?
C17 C16 C19 O5 172.47(11) . . . . ?
C15 C16 C19 O5 -9.07(18) . . . . ?
C17 C16 C19 O6 -9.22(15) . . . . ?
C15 C16 C19 O6 169.23(10) . . . . ?
C19 O6 C20 C21 162.29(10) . . . . ?
O6 C20 C21 C22 62.48(14) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1528255'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H24 N2 O5), 3(C2 H6 O)'
_chemical_formula_sum            'C50 H66 N4 O13'
_chemical_formula_weight         931.06

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'
N N 0.0311 0.0180 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1910(3)
_cell_length_b                   13.7072(3)
_cell_length_c                   19.0724(5)
_cell_angle_alpha                90.789(2)
_cell_angle_beta                 103.313(3)
_cell_angle_gamma                109.953(2)
_cell_volume                     2424.57(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    140.00(10)
_cell_measurement_reflns_used    10960
_cell_measurement_theta_min      3.9640
_cell_measurement_theta_max      75.5850

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.545
_exptl_crystal_size_mid          0.445
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 9 1 0.4607
-6 0 2 0.2676
-1 9 1 0.4573
-1 1 -12 0.1545
1 -9 -1 0.4492
1 0 12 0.1757
6 -1 -8 0.2659
4 5 -6 0.3019
-6 0 8 0.2641
-3 0 12 0.2197
1 6 -8 0.2987
-3 0 -10 0.1784
2 0 10 0.1749
6 1 0 0.2139
_diffrn_ambient_temperature      140.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus 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, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1333
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  31.00   1.00    1.00    --  -42.26  57.00 -90.00   88
  2  ω     30.00  83.00   1.00    1.00    --   42.26-125.00-180.00   53
  3  ω     37.00 122.00   1.00    1.00    --  110.51-125.00-180.00   85
  4  ω     76.00 122.00   1.00    1.00    --  110.51-125.00 -30.00   46
  5  ω     54.00  80.00   1.00    1.00    --  110.51 -94.00   0.00   26
  6  ω     45.00  78.00   1.00    1.00    --  110.51 -61.00  60.00   33
  7  ω     42.00 108.00   1.00    1.00    --  110.51 -94.00  30.00   66
  8  ω     35.00 136.00   1.00    1.00    --  110.51 -30.00 -30.00  101
  9  ω    117.00 178.00   1.00    1.00    --  110.51  45.00 -30.00   61
 10  ω    122.00 178.00   1.00    1.00    --  110.51 125.00 -30.00   56
 11  ω    117.00 159.00   1.00    1.00    --  110.51 117.00 -65.00   42
 12  ω     38.00 136.00   1.00    1.00    --  110.51 -45.00-120.00   98
 13  ω     32.00  83.00   1.00    1.00    --   42.26-125.00  30.00   51
 14  ω     23.00  50.00   1.00    1.00    --   42.26-125.00 120.00   27
 15  ω     34.00 159.00   1.00    1.00    --  110.51 -15.00 150.00  125
 16  ω     29.00  78.00   1.00    1.00    --  110.51 -94.00 -90.00   49
 17  ω   -130.00  42.00   1.00    1.00    --  -42.26   0.00 -90.00  172
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            17613
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.448
_diffrn_reflns_theta_max         76.154
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9787
_reflns_number_gt                8567
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)²+0.4636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9787
_refine_ls_number_parameters     664
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.65319(11) -0.09374(7) -0.02190(5) 0.0287(2) Uani 1 1 d . . . . .
O2 O 0.85389(10) 0.35834(7) -0.12301(5) 0.0264(2) Uani 1 1 d . . . . .
O3 O 0.69899(10) 0.45103(7) -0.13864(5) 0.0262(2) Uani 1 1 d . . . . .
O4 O 0.82727(9) 0.42871(7) 0.04495(4) 0.02141(18) Uani 1 1 d . . . . .
H4 H 0.835(2) 0.4947(15) 0.0445(10) 0.038(5) Uiso 1 1 d . . . . .
O5 O 0.14801(9) 0.37960(7) -0.01757(5) 0.0260(2) Uani 1 1 d . . . . .
O6 O 0.65285(11) -0.09774(7) 0.46815(5) 0.0277(2) Uani 1 1 d . . . . .
O7 O 0.84758(10) 0.35689(7) 0.36901(5) 0.0255(2) Uani 1 1 d . . . . .
O8 O 0.70873(10) 0.46092(7) 0.36214(5) 0.02517(19) Uani 1 1 d . . . . .
O9 O 0.83082(9) 0.41870(7) 0.54244(4) 0.02126(18) Uani 1 1 d . . . . .
H9 H 0.839(2) 0.4864(17) 0.5452(11) 0.049(5) Uiso 1 1 d . . . . .
O10 O 0.15126(10) 0.38560(7) 0.47862(5) 0.0276(2) Uani 1 1 d . . . . .
O11 O 0.74307(12) 0.17677(8) 0.18317(5) 0.0369(2) Uani 1 1 d . . . . .
H11A H 0.815(3) 0.2389(19) 0.1776(13) 0.074(7) Uiso 1 1 d . . . . .
O12 O 0.95204(12) 0.35421(8) 0.16880(6) 0.0394(2) Uani 1 1 d . . . . .
H12 H 0.914(3) 0.3861(19) 0.1330(13) 0.076(7) Uiso 1 1 d . . . . .
O13 O 0.40875(13) 0.86334(9) 0.35093(6) 0.0430(3) Uani 1 1 d D . . . .
H13A H 0.492037 0.874906 0.377103 0.064 Uiso 0.736(5) 1 calc R U P A 1
H13B H 0.484688 0.869297 0.382286 0.064 Uiso 0.264(5) 1 calc R U P A 2
N1 N 0.66218(12) -0.00189(8) 0.08007(6) 0.0241(2) Uani 1 1 d . . . . .
H1 H 0.6871(17) 0.0580(13) 0.1030(9) 0.026(4) Uiso 1 1 d . . . . .
N2 N 0.21330(11) 0.24583(8) 0.02564(6) 0.0235(2) Uani 1 1 d . . . . .
H2 H 0.2659(18) 0.2078(12) 0.0206(8) 0.025(4) Uiso 1 1 d . . . . .
N3 N 0.66731(12) -0.00509(8) 0.57053(6) 0.0232(2) Uani 1 1 d . . . . .
H3 H 0.6802(17) 0.0532(13) 0.5902(9) 0.025(4) Uiso 1 1 d . . . . .
N4 N 0.22049(12) 0.25608(8) 0.52638(6) 0.0250(2) Uani 1 1 d . . . . .
H4A H 0.2705(18) 0.2168(13) 0.5230(8) 0.025(4) Uiso 1 1 d . . . . .
C1 C 0.88501(17) -0.08535(13) 0.16079(9) 0.0412(4) Uani 1 1 d . . . . .
H1A H 0.963035 -0.080524 0.203331 0.062 Uiso 1 1 calc R U . . .
H1B H 0.916561 -0.025810 0.133055 0.062 Uiso 1 1 calc R U . . .
H1C H 0.860227 -0.150345 0.130290 0.062 Uiso 1 1 calc R U . . .
C2 C 0.75382(16) -0.08437(12) 0.18508(8) 0.0342(3) Uani 1 1 d . . . . .
H2A H 0.780368 -0.019377 0.216895 0.041 Uiso 1 1 calc R U . . .
H2B H 0.723796 -0.143885 0.213879 0.041 Uiso 1 1 calc R U . . .
C3 C 0.62681(14) -0.09132(10) 0.12195(7) 0.0271(3) Uani 1 1 d . . . . .
H3A H 0.599680 -0.156264 0.089988 0.033 Uiso 1 1 calc R U . . .
H3B H 0.542926 -0.094386 0.140846 0.033 Uiso 1 1 calc R U . . .
C4 C 0.67622(13) -0.00955(9) 0.01244(7) 0.0220(2) Uani 1 1 d . . . . .
C5 C 0.72320(13) 0.09037(9) -0.02183(6) 0.0204(2) Uani 1 1 d . . . . .
C6 C 0.78631(14) 0.08947(10) -0.07952(7) 0.0252(3) Uani 1 1 d . . . . .
H6 H 0.796881 0.026854 -0.094686 0.030 Uiso 1 1 calc R U . . .
C7 C 0.83397(14) 0.17723(11) -0.11527(7) 0.0267(3) Uani 1 1 d . . . . .
H7 H 0.877674 0.176181 -0.154088 0.032 Uiso 1 1 calc R U . . .
C8 C 0.81504(13) 0.26627(10) -0.09192(6) 0.0222(2) Uani 1 1 d . . . . .
C9 C 0.75406(12) 0.27011(9) -0.03453(6) 0.0184(2) Uani 1 1 d . . . . .
C10 C 0.70680(12) 0.18235(9) 0.00090(6) 0.0188(2) Uani 1 1 d . . . . .
H10 H 0.663991 0.184326 0.039940 0.023 Uiso 1 1 calc R U . . .
C11 C 0.81117(13) 0.43025(9) -0.08782(6) 0.0216(2) Uani 1 1 d . . . . .
H11 H 0.894982 0.496197 -0.068738 0.026 Uiso 1 1 calc R U . . .
C12 C 0.74715(12) 0.37756(9) -0.02472(6) 0.0182(2) Uani 1 1 d . . . . .
C13 C 0.59623(12) 0.37998(8) -0.04653(6) 0.0183(2) Uani 1 1 d . . . . .
C14 C 0.57829(13) 0.42163(9) -0.11223(6) 0.0218(2) Uani 1 1 d . . . . .
C15 C 0.45012(15) 0.43389(11) -0.14652(7) 0.0276(3) Uani 1 1 d . . . . .
H15 H 0.438966 0.462395 -0.191693 0.033 Uiso 1 1 calc R U . . .
C16 C 0.33883(14) 0.40267(10) -0.11193(7) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.249886 0.410687 -0.133762 0.030 Uiso 1 1 calc R U . . .
C17 C 0.35418(13) 0.35973(9) -0.04578(6) 0.0199(2) Uani 1 1 d . . . . .
C18 C 0.48494(13) 0.34843(9) -0.01258(6) 0.0188(2) Uani 1 1 d . . . . .
H18 H 0.496899 0.319604 0.032445 0.023 Uiso 1 1 calc R U . . .
C19 C 0.23023(13) 0.32920(9) -0.01133(6) 0.0203(2) Uani 1 1 d . . . . .
C20 C 0.10472(14) 0.21078(11) 0.06701(7) 0.0299(3) Uani 1 1 d . . . . .
H20A H 0.032437 0.142404 0.044226 0.036 Uiso 1 1 calc R U . . .
H20B H 0.054341 0.261222 0.065991 0.036 Uiso 1 1 calc R U . . .
C21 C 0.17208(17) 0.20064(11) 0.14521(7) 0.0333(3) Uani 1 1 d . . . . .
H21A H 0.095591 0.178815 0.171746 0.040 Uiso 1 1 calc R U . . .
H21B H 0.214239 0.145281 0.146096 0.040 Uiso 1 1 calc R U . . .
C22 C 0.2884(2) 0.30105(12) 0.18386(9) 0.0447(4) Uani 1 1 d . . . . .
H22A H 0.324114 0.290926 0.234486 0.067 Uiso 1 1 calc R U . . .
H22B H 0.248190 0.356787 0.181988 0.067 Uiso 1 1 calc R U . . .
H22C H 0.368024 0.320335 0.160091 0.067 Uiso 1 1 calc R U . . .
C23 C 0.89208(17) -0.08940(13) 0.65338(9) 0.0394(3) Uani 1 1 d . . . . .
H23A H 0.970774 -0.082003 0.696170 0.059 Uiso 1 1 calc R U . . .
H23B H 0.923759 -0.033449 0.622884 0.059 Uiso 1 1 calc R U . . .
H23C H 0.865137 -0.157139 0.625793 0.059 Uiso 1 1 calc R U . . .
C24 C 0.76298(15) -0.08259(11) 0.67703(7) 0.0294(3) Uani 1 1 d . . . . .
H24A H 0.792127 -0.014894 0.706182 0.035 Uiso 1 1 calc R U . . .
H24B H 0.732958 -0.138567 0.708518 0.035 Uiso 1 1 calc R U . . .
C25 C 0.63443(14) -0.09251(10) 0.61413(7) 0.0245(3) Uani 1 1 d . . . . .
H25A H 0.607626 -0.158443 0.583301 0.029 Uiso 1 1 calc R U . . .
H25B H 0.550978 -0.095190 0.633276 0.029 Uiso 1 1 calc R U . . .
C26 C 0.67619(13) -0.01278(9) 0.50211(7) 0.0212(2) Uani 1 1 d . . . . .
C27 C 0.71782(13) 0.08628(9) 0.46705(6) 0.0199(2) Uani 1 1 d . . . . .
C28 C 0.77085(14) 0.08486(10) 0.40572(7) 0.0244(3) Uani 1 1 d . . . . .
H28 H 0.775687 0.021479 0.387829 0.029 Uiso 1 1 calc R U . . .
C29 C 0.81663(14) 0.17336(10) 0.37023(7) 0.0260(3) Uani 1 1 d . . . . .
H29 H 0.853622 0.172101 0.328970 0.031 Uiso 1 1 calc R U . . .
C30 C 0.80585(13) 0.26343(9) 0.39778(6) 0.0213(2) Uani 1 1 d . . . . .
C31 C 0.75152(12) 0.26691(9) 0.45767(6) 0.0182(2) Uani 1 1 d . . . . .
C32 C 0.70742(12) 0.17897(9) 0.49316(6) 0.0185(2) Uani 1 1 d . . . . .
H32 H 0.670742 0.181117 0.534431 0.022 Uiso 1 1 calc R U . . .
C33 C 0.81632(13) 0.43083(9) 0.40951(6) 0.0212(2) Uani 1 1 d . . . . .
H33 H 0.905260 0.492922 0.430023 0.025 Uiso 1 1 calc R U . . .
C34 C 0.75060(12) 0.37513(9) 0.47157(6) 0.0182(2) Uani 1 1 d . . . . .
C35 C 0.60212(12) 0.38253(8) 0.45135(6) 0.0180(2) Uani 1 1 d . . . . .
C36 C 0.58856(13) 0.43227(9) 0.38867(6) 0.0206(2) Uani 1 1 d . . . . .
C37 C 0.46525(14) 0.45332(10) 0.35784(7) 0.0249(3) Uani 1 1 d . . . . .
H37 H 0.457780 0.488188 0.315206 0.030 Uiso 1 1 calc R U . . .
C38 C 0.35309(13) 0.42132(10) 0.39186(7) 0.0238(2) Uani 1 1 d . . . . .
H38 H 0.267270 0.434851 0.372058 0.029 Uiso 1 1 calc R U . . .
C39 C 0.36312(13) 0.36959(9) 0.45462(6) 0.0199(2) Uani 1 1 d . . . . .
C40 C 0.49016(12) 0.35069(8) 0.48489(6) 0.0188(2) Uani 1 1 d . . . . .
H40 H 0.499052 0.316533 0.527802 0.023 Uiso 1 1 calc R U . . .
C41 C 0.23685(13) 0.33801(9) 0.48760(7) 0.0214(2) Uani 1 1 d . . . . .
C42 C 0.10183(14) 0.21891(10) 0.56135(8) 0.0282(3) Uani 1 1 d . . . . .
H42A H 0.068578 0.141831 0.558827 0.034 Uiso 1 1 calc R U . . .
H42B H 0.020410 0.238232 0.534408 0.034 Uiso 1 1 calc R U . . .
C43 C 0.14272(17) 0.26298(12) 0.63987(8) 0.0377(3) Uani 1 1 d . . . . .
H43A H 0.184917 0.340025 0.643132 0.045 Uiso 1 1 calc R U . . .
H43B H 0.216961 0.237609 0.668090 0.045 Uiso 1 1 calc R U . . .
C44 C 0.0135(2) 0.23157(14) 0.67255(9) 0.0477(4) Uani 1 1 d . . . . .
H44A H 0.044596 0.259238 0.723674 0.072 Uiso 1 1 calc R U . . .
H44B H -0.029633 0.155320 0.668629 0.072 Uiso 1 1 calc R U . . .
H44C H -0.057990 0.259906 0.646430 0.072 Uiso 1 1 calc R U . . .
C45 C 0.6294(2) 0.20572(14) 0.19735(9) 0.0439(4) Uani 1 1 d . . . . .
H45A H 0.588893 0.237800 0.155582 0.053 Uiso 1 1 calc R U . . .
H45B H 0.666471 0.257270 0.240580 0.053 Uiso 1 1 calc R U . . .
C46 C 0.51451(19) 0.10941(16) 0.21008(10) 0.0525(4) Uani 1 1 d . . . . .
H46A H 0.438290 0.128617 0.223071 0.079 Uiso 1 1 calc R U . . .
H46B H 0.556758 0.075868 0.249612 0.079 Uiso 1 1 calc R U . . .
H46C H 0.473546 0.060912 0.165863 0.079 Uiso 1 1 calc R U . . .
C47 C 1.02621(16) 0.42584(12) 0.23265(8) 0.0365(3) Uani 1 1 d . . . . .
H47A H 1.126578 0.463683 0.230022 0.044 Uiso 1 1 calc R U . . .
H47B H 1.030121 0.385857 0.275436 0.044 Uiso 1 1 calc R U . . .
C48 C 0.9570(2) 0.50382(13) 0.24294(9) 0.0451(4) Uani 1 1 d . . . . .
H48A H 1.006928 0.545751 0.289646 0.068 Uiso 1 1 calc R U . . .
H48B H 0.855473 0.467090 0.242042 0.068 Uiso 1 1 calc R U . . .
H48C H 0.963396 0.549547 0.203847 0.068 Uiso 1 1 calc R U . . .
C49A C 0.3836(4) 0.7942(2) 0.28974(12) 0.0464(7) Uani 0.736(5) 1 d D U P A 1
H49A H 0.454476 0.826540 0.261314 0.056 Uiso 0.736(5) 1 calc R U P A 1
H49B H 0.286035 0.781631 0.258572 0.056 Uiso 0.736(5) 1 calc R U P A 1
C50A C 0.3957(4) 0.6921(2) 0.31111(14) 0.0556(8) Uani 0.736(5) 1 d D U P A 1
H50A H 0.495808 0.703075 0.336156 0.083 Uiso 0.736(5) 1 calc R U P A 1
H50B H 0.366209 0.643087 0.267678 0.083 Uiso 0.736(5) 1 calc R U P A 1
H50C H 0.332997 0.663485 0.343470 0.083 Uiso 0.736(5) 1 calc R U P A 1
C49B C 0.3459(7) 0.7577(4) 0.3140(4) 0.0489(16) Uani 0.264(5) 1 d D U P A 2
H49C H 0.260978 0.752487 0.274319 0.059 Uiso 0.264(5) 1 calc R U P A 2
H49D H 0.312805 0.707442 0.348549 0.059 Uiso 0.264(5) 1 calc R U P A 2
C50B C 0.4527(8) 0.7305(7) 0.2836(4) 0.0546(18) Uani 0.264(5) 1 d D U P A 2
H50D H 0.481089 0.777695 0.247224 0.082 Uiso 0.264(5) 1 calc R U P A 2
H50E H 0.409332 0.658434 0.261026 0.082 Uiso 0.264(5) 1 calc R U P A 2
H50F H 0.537916 0.737621 0.322636 0.082 Uiso 0.264(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 C4 1.2407(15) . ?
O2 C8 1.3743(15) . ?
O2 C11 1.4214(14) . ?
O3 C14 1.3718(14) . ?
O3 C11 1.4308(14) . ?
O4 C12 1.4171(14) . ?
O4 H4 0.882(19) . ?
O5 C19 1.2429(15) . ?
O6 C26 1.2455(15) . ?
O7 C30 1.3704(14) . ?
O7 C33 1.4275(14) . ?
O8 C36 1.3685(14) . ?
O8 C33 1.4322(14) . ?
O9 C34 1.4099(14) . ?
O9 H9 0.90(2) . ?
O10 C41 1.2404(15) . ?
O11 C45 1.4243(19) . ?
O11 H11A 0.94(3) . ?
O12 C47 1.4336(18) . ?
O12 H12 0.90(3) . ?
O13 C49A 1.411(2) . ?
O13 C49B 1.461(4) . ?
O13 H13A 0.8400 . ?
O13 H13B 0.8400 . ?
N1 C4 1.3367(17) . ?
N1 C3 1.4590(15) . ?
N1 H1 0.852(17) . ?
N2 C19 1.3329(15) . ?
N2 C20 1.4586(16) . ?
N2 H2 0.884(17) . ?
N3 C26 1.3339(16) . ?
N3 C25 1.4565(15) . ?
N3 H3 0.833(17) . ?
N4 C41 1.3371(16) . ?
N4 C42 1.4583(16) . ?
N4 H4A 0.869(17) . ?
C1 C2 1.516(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5262(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5012(16) . ?
C5 C6 1.3983(17) . ?
C5 C10 1.4028(16) . ?
C6 C7 1.3872(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3821(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3861(16) . ?
C9 C10 1.3829(16) . ?
C9 C12 1.5095(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.5684(15) . ?
C11 H11 1.0000 . ?
C12 C13 1.5100(15) . ?
C13 C18 1.3799(16) . ?
C13 C14 1.3837(16) . ?
C14 C15 1.3861(17) . ?
C15 C16 1.3878(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3982(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3984(16) . ?
C17 C19 1.4938(16) . ?
C18 H18 0.9500 . ?
C20 C21 1.5212(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.516(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.516(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.5245(17) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.4944(16) . ?
C27 C28 1.3994(17) . ?
C27 C32 1.4045(16) . ?
C28 C29 1.3890(18) . ?
C28 H28 0.9500 . ?
C29 C30 1.3834(17) . ?
C29 H29 0.9500 . ?
C30 C31 1.3861(16) . ?
C31 C32 1.3805(16) . ?
C31 C34 1.5069(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.5726(15) . ?
C33 H33 1.0000 . ?
C34 C35 1.5119(15) . ?
C35 C40 1.3806(16) . ?
C35 C36 1.3869(16) . ?
C36 C37 1.3856(17) . ?
C37 C38 1.3882(18) . ?
C37 H37 0.9500 . ?
C38 C39 1.4009(17) . ?
C38 H38 0.9500 . ?
C39 C40 1.4019(16) . ?
C39 C41 1.4965(16) . ?
C40 H40 0.9500 . ?
C42 C43 1.516(2) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.519(2) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.502(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C48 1.500(2) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49A C50A 1.500(3) . ?
C49A H49A 0.9900 . ?
C49A H49B 0.9900 . ?
C50A H50A 0.9800 . ?
C50A H50B 0.9800 . ?
C50A H50C 0.9800 . ?
C49B C50B 1.490(5) . ?
C49B H49C 0.9900 . ?
C49B H49D 0.9900 . ?
C50B H50D 0.9800 . ?
C50B H50E 0.9800 . ?
C50B H50F 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
C8 O2 C11 108.01(9) . . ?
C14 O3 C11 108.31(9) . . ?
C12 O4 H4 107.6(12) . . ?
C30 O7 C33 108.15(9) . . ?
C36 O8 C33 108.26(9) . . ?
C34 O9 H9 106.6(13) . . ?
C45 O11 H11A 106.7(15) . . ?
C47 O12 H12 110.4(16) . . ?
C49A O13 H13A 109.5 . . ?
C49B O13 H13B 109.5 . . ?
C4 N1 C3 122.93(11) . . ?
C4 N1 H1 119.9(11) . . ?
C3 N1 H1 116.5(11) . . ?
C19 N2 C20 123.20(11) . . ?
C19 N2 H2 116.6(10) . . ?
C20 N2 H2 119.9(10) . . ?
C26 N3 C25 124.57(11) . . ?
C26 N3 H3 118.9(11) . . ?
C25 N3 H3 116.6(11) . . ?
C41 N4 C42 121.60(11) . . ?
C41 N4 H4A 118.4(11) . . ?
C42 N4 H4A 118.7(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 112.94(12) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C2 111.41(11) . . ?
N1 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 N1 123.31(11) . . ?
O1 C4 C5 119.87(11) . . ?
N1 C4 C5 116.81(10) . . ?
C6 C5 C10 119.47(11) . . ?
C6 C5 C4 116.92(11) . . ?
C10 C5 C4 123.61(11) . . ?
C7 C6 C5 122.00(11) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C8 C7 C6 117.04(11) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
O2 C8 C7 123.68(11) . . ?
O2 C8 C9 113.88(10) . . ?
C7 C8 C9 122.44(11) . . ?
C10 C9 C8 120.22(11) . . ?
C10 C9 C12 131.28(10) . . ?
C8 C9 C12 108.45(10) . . ?
C9 C10 C5 118.82(11) . . ?
C9 C10 H10 120.6 . . ?
C5 C10 H10 120.6 . . ?
O2 C11 O3 108.49(10) . . ?
O2 C11 C12 108.40(9) . . ?
O3 C11 C12 107.84(9) . . ?
O2 C11 H11 110.7 . . ?
O3 C11 H11 110.7 . . ?
C12 C11 H11 110.7 . . ?
O4 C12 C9 111.61(9) . . ?
O4 C12 C13 114.12(9) . . ?
C9 C12 C13 113.84(9) . . ?
O4 C12 C11 113.68(9) . . ?
C9 C12 C11 101.13(9) . . ?
C13 C12 C11 101.35(9) . . ?
C18 C13 C14 120.51(11) . . ?
C18 C13 C12 130.91(10) . . ?
C14 C13 C12 108.58(10) . . ?
O3 C14 C13 113.81(10) . . ?
O3 C14 C15 123.95(11) . . ?
C13 C14 C15 122.23(11) . . ?
C14 C15 C16 117.05(11) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
C15 C16 C17 121.72(11) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 119.82(11) . . ?
C16 C17 C19 118.67(10) . . ?
C18 C17 C19 121.50(10) . . ?
C13 C18 C17 118.67(10) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
O5 C19 N2 122.59(11) . . ?
O5 C19 C17 120.93(11) . . ?
N2 C19 C17 116.48(10) . . ?
N2 C20 C21 111.43(11) . . ?
N2 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N2 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 113.11(12) . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C23 C24 C25 113.60(11) . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
N3 C25 C24 111.31(11) . . ?
N3 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
N3 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
O6 C26 N3 122.56(11) . . ?
O6 C26 C27 120.41(11) . . ?
N3 C26 C27 117.03(10) . . ?
C28 C27 C32 119.55(11) . . ?
C28 C27 C26 117.22(10) . . ?
C32 C27 C26 123.22(11) . . ?
C29 C28 C27 121.96(11) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C30 C29 C28 116.89(11) . . ?
C30 C29 H29 121.6 . . ?
C28 C29 H29 121.6 . . ?
O7 C30 C29 123.64(11) . . ?
O7 C30 C31 113.84(10) . . ?
C29 C30 C31 122.53(11) . . ?
C32 C31 C30 120.36(11) . . ?
C32 C31 C34 130.88(10) . . ?
C30 C31 C34 108.76(10) . . ?
C31 C32 C27 118.70(10) . . ?
C31 C32 H32 120.6 . . ?
C27 C32 H32 120.6 . . ?
O7 C33 O8 107.96(9) . . ?
O7 C33 C34 108.17(9) . . ?
O8 C33 C34 108.06(9) . . ?
O7 C33 H33 110.8 . . ?
O8 C33 H33 110.8 . . ?
C34 C33 H33 110.8 . . ?
O9 C34 C31 110.61(9) . . ?
O9 C34 C35 114.18(9) . . ?
C31 C34 C35 114.03(9) . . ?
O9 C34 C33 114.97(9) . . ?
C31 C34 C33 101.04(9) . . ?
C35 C34 C33 101.04(9) . . ?
C40 C35 C36 120.32(11) . . ?
C40 C35 C34 130.95(10) . . ?
C36 C35 C34 108.72(10) . . ?
O8 C36 C37 123.83(11) . . ?
O8 C36 C35 113.90(10) . . ?
C37 C36 C35 122.23(11) . . ?
C36 C37 C38 117.21(11) . . ?
C36 C37 H37 121.4 . . ?
C38 C37 H37 121.4 . . ?
C37 C38 C39 121.73(11) . . ?
C37 C38 H38 119.1 . . ?
C39 C38 H38 119.1 . . ?
C38 C39 C40 119.57(11) . . ?
C38 C39 C41 118.03(10) . . ?
C40 C39 C41 122.39(11) . . ?
C35 C40 C39 118.92(11) . . ?
C35 C40 H40 120.5 . . ?
C39 C40 H40 120.5 . . ?
O10 C41 N4 121.98(11) . . ?
O10 C41 C39 121.11(11) . . ?
N4 C41 C39 116.91(10) . . ?
N4 C42 C43 113.09(11) . . ?
N4 C42 H42A 109.0 . . ?
C43 C42 H42A 109.0 . . ?
N4 C42 H42B 109.0 . . ?
C43 C42 H42B 109.0 . . ?
H42A C42 H42B 107.8 . . ?
C42 C43 C44 111.81(13) . . ?
C42 C43 H43A 109.3 . . ?
C44 C43 H43A 109.3 . . ?
C42 C43 H43B 109.3 . . ?
C44 C43 H43B 109.3 . . ?
H43A C43 H43B 107.9 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O11 C45 C46 108.41(14) . . ?
O11 C45 H45A 110.0 . . ?
C46 C45 H45A 110.0 . . ?
O11 C45 H45B 110.0 . . ?
C46 C45 H45B 110.0 . . ?
H45A C45 H45B 108.4 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O12 C47 C48 113.54(13) . . ?
O12 C47 H47A 108.9 . . ?
C48 C47 H47A 108.9 . . ?
O12 C47 H47B 108.9 . . ?
C48 C47 H47B 108.9 . . ?
H47A C47 H47B 107.7 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O13 C49A C50A 111.5(2) . . ?
O13 C49A H49A 109.3 . . ?
C50A C49A H49A 109.3 . . ?
O13 C49A H49B 109.3 . . ?
C50A C49A H49B 109.3 . . ?
H49A C49A H49B 108.0 . . ?
C49A C50A H50A 109.5 . . ?
C49A C50A H50B 109.5 . . ?
H50A C50A H50B 109.5 . . ?
C49A C50A H50C 109.5 . . ?
H50A C50A H50C 109.5 . . ?
H50B C50A H50C 109.5 . . ?
O13 C49B C50B 111.1(5) . . ?
O13 C49B H49C 109.4 . . ?
C50B C49B H49C 109.4 . . ?
O13 C49B H49D 109.4 . . ?
C50B C49B H49D 109.4 . . ?
H49C C49B H49D 108.0 . . ?
C49B C50B H50D 109.5 . . ?
C49B C50B H50E 109.5 . . ?
H50D C50B H50E 109.5 . . ?
C49B C50B H50F 109.5 . . ?
H50D C50B H50F 109.5 . . ?
H50E C50B H50F 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
C4 N1 C3 C2 111.45(14) . . . . ?
C1 C2 C3 N1 -62.19(16) . . . . ?
C3 N1 C4 O1 3.87(19) . . . . ?
C3 N1 C4 C5 -175.77(10) . . . . ?
O1 C4 C5 C6 -21.58(17) . . . . ?
N1 C4 C5 C6 158.08(11) . . . . ?
O1 C4 C5 C10 158.36(12) . . . . ?
N1 C4 C5 C10 -21.98(17) . . . . ?
C10 C5 C6 C7 0.13(19) . . . . ?
C4 C5 C6 C7 -179.93(11) . . . . ?
C5 C6 C7 C8 -0.68(19) . . . . ?
C11 O2 C8 C7 176.75(12) . . . . ?
C11 O2 C8 C9 -3.07(14) . . . . ?
C6 C7 C8 O2 -178.55(11) . . . . ?
C6 C7 C8 C9 1.26(19) . . . . ?
O2 C8 C9 C10 178.54(10) . . . . ?
C7 C8 C9 C10 -1.28(19) . . . . ?
O2 C8 C9 C12 0.93(14) . . . . ?
C7 C8 C9 C12 -178.89(11) . . . . ?
C8 C9 C10 C5 0.67(17) . . . . ?
C12 C9 C10 C5 177.65(11) . . . . ?
C6 C5 C10 C9 -0.12(17) . . . . ?
C4 C5 C10 C9 179.95(10) . . . . ?
C8 O2 C11 O3 -113.04(10) . . . . ?
C8 O2 C11 C12 3.82(13) . . . . ?
C14 O3 C11 O2 119.83(10) . . . . ?
C14 O3 C11 C12 2.62(12) . . . . ?
C10 C9 C12 O4 62.91(16) . . . . ?
C8 C9 C12 O4 -119.84(10) . . . . ?
C10 C9 C12 C13 -68.05(16) . . . . ?
C8 C9 C12 C13 109.20(11) . . . . ?
C10 C9 C12 C11 -175.89(12) . . . . ?
C8 C9 C12 C11 1.36(12) . . . . ?
O2 C11 C12 O4 116.61(10) . . . . ?
O3 C11 C12 O4 -126.12(10) . . . . ?
O2 C11 C12 C9 -3.13(12) . . . . ?
O3 C11 C12 C9 114.14(10) . . . . ?
O2 C11 C12 C13 -120.49(10) . . . . ?
O3 C11 C12 C13 -3.22(12) . . . . ?
O4 C12 C13 C18 -55.02(16) . . . . ?
C9 C12 C13 C18 74.69(15) . . . . ?
C11 C12 C13 C18 -177.62(12) . . . . ?
O4 C12 C13 C14 125.33(10) . . . . ?
C9 C12 C13 C14 -104.96(11) . . . . ?
C11 C12 C13 C14 2.73(12) . . . . ?
C11 O3 C14 C13 -0.85(14) . . . . ?
C11 O3 C14 C15 177.83(12) . . . . ?
C18 C13 C14 O3 178.93(10) . . . . ?
C12 C13 C14 O3 -1.37(14) . . . . ?
C18 C13 C14 C15 0.22(18) . . . . ?
C12 C13 C14 C15 179.92(11) . . . . ?
O3 C14 C15 C16 -178.38(11) . . . . ?
C13 C14 C15 C16 0.19(19) . . . . ?
C14 C15 C16 C17 -0.63(19) . . . . ?
C15 C16 C17 C18 0.67(19) . . . . ?
C15 C16 C17 C19 179.23(11) . . . . ?
C14 C13 C18 C17 -0.20(17) . . . . ?
C12 C13 C18 C17 -179.82(11) . . . . ?
C16 C17 C18 C13 -0.23(17) . . . . ?
C19 C17 C18 C13 -178.75(10) . . . . ?
C20 N2 C19 O5 -5.12(19) . . . . ?
C20 N2 C19 C17 175.09(11) . . . . ?
C16 C17 C19 O5 -33.80(17) . . . . ?
C18 C17 C19 O5 144.74(12) . . . . ?
C16 C17 C19 N2 145.99(11) . . . . ?
C18 C17 C19 N2 -35.47(16) . . . . ?
C19 N2 C20 C21 -125.56(13) . . . . ?
N2 C20 C21 C22 56.99(16) . . . . ?
C26 N3 C25 C24 113.66(13) . . . . ?
C23 C24 C25 N3 -65.19(15) . . . . ?
C25 N3 C26 O6 2.00(19) . . . . ?
C25 N3 C26 C27 -177.23(11) . . . . ?
O6 C26 C27 C28 -18.72(17) . . . . ?
N3 C26 C27 C28 160.53(11) . . . . ?
O6 C26 C27 C32 161.96(11) . . . . ?
N3 C26 C27 C32 -18.79(17) . . . . ?
C32 C27 C28 C29 1.28(19) . . . . ?
C26 C27 C28 C29 -178.07(11) . . . . ?
C27 C28 C29 C30 -0.78(19) . . . . ?
C33 O7 C30 C29 178.02(12) . . . . ?
C33 O7 C30 C31 -2.11(14) . . . . ?
C28 C29 C30 O7 179.51(11) . . . . ?
C28 C29 C30 C31 -0.35(19) . . . . ?
O7 C30 C31 C32 -178.90(10) . . . . ?
C29 C30 C31 C32 0.96(18) . . . . ?
O7 C30 C31 C34 1.91(14) . . . . ?
C29 C30 C31 C34 -178.23(11) . . . . ?
C30 C31 C32 C27 -0.44(17) . . . . ?
C34 C31 C32 C27 178.55(11) . . . . ?
C28 C27 C32 C31 -0.64(17) . . . . ?
C26 C27 C32 C31 178.67(10) . . . . ?
C30 O7 C33 O8 -115.28(10) . . . . ?
C30 O7 C33 C34 1.42(12) . . . . ?
C36 O8 C33 O7 117.96(10) . . . . ?
C36 O8 C33 C34 1.19(12) . . . . ?
C32 C31 C34 O9 57.85(16) . . . . ?
C30 C31 C34 O9 -123.08(10) . . . . ?
C32 C31 C34 C35 -72.45(15) . . . . ?
C30 C31 C34 C35 106.63(11) . . . . ?
C32 C31 C34 C33 -179.95(12) . . . . ?
C30 C31 C34 C33 -0.87(12) . . . . ?
O7 C33 C34 O9 118.79(10) . . . . ?
O8 C33 C34 O9 -124.58(10) . . . . ?
O7 C33 C34 C31 -0.32(12) . . . . ?
O8 C33 C34 C31 116.31(10) . . . . ?
O7 C33 C34 C35 -117.76(10) . . . . ?
O8 C33 C34 C35 -1.13(11) . . . . ?
O9 C34 C35 C40 -54.13(16) . . . . ?
C31 C34 C35 C40 74.37(15) . . . . ?
C33 C34 C35 C40 -178.13(11) . . . . ?
O9 C34 C35 C36 124.69(10) . . . . ?
C31 C34 C35 C36 -106.81(11) . . . . ?
C33 C34 C35 C36 0.69(12) . . . . ?
C33 O8 C36 C37 177.26(11) . . . . ?
C33 O8 C36 C35 -0.77(13) . . . . ?
C40 C35 C36 O8 178.96(10) . . . . ?
C34 C35 C36 O8 -0.01(14) . . . . ?
C40 C35 C36 C37 0.89(18) . . . . ?
C34 C35 C36 C37 -178.07(11) . . . . ?
O8 C36 C37 C38 -178.62(11) . . . . ?
C35 C36 C37 C38 -0.75(18) . . . . ?
C36 C37 C38 C39 -0.19(18) . . . . ?
C37 C38 C39 C40 0.99(18) . . . . ?
C37 C38 C39 C41 179.98(11) . . . . ?
C36 C35 C40 C39 -0.07(17) . . . . ?
C34 C35 C40 C39 178.64(11) . . . . ?
C38 C39 C40 C35 -0.84(17) . . . . ?
C41 C39 C40 C35 -179.79(10) . . . . ?
C42 N4 C41 O10 -0.95(19) . . . . ?
C42 N4 C41 C39 179.60(11) . . . . ?
C38 C39 C41 O10 -25.98(17) . . . . ?
C40 C39 C41 O10 152.99(12) . . . . ?
C38 C39 C41 N4 153.48(11) . . . . ?
C40 C39 C41 N4 -27.56(16) . . . . ?
C41 N4 C42 C43 -95.09(15) . . . . ?
N4 C42 C43 C44 174.29(12) . . . . ?

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
O4 H4 O5 0.882(19) 1.767(19) 2.6243(12) 163.5(17) 2_665
O9 H9 O10 0.90(2) 1.79(2) 2.6682(12) 162.3(19) 2_666
O11 H11A O12 0.94(3) 1.75(3) 2.6978(16) 179(2) .
O12 H12 O4 0.90(3) 1.91(3) 2.7943(14) 168(2) .
O13 H13B O6 0.84 2.00 2.8234(15) 168.4 1_565
N1 H1 O11 0.852(17) 2.052(17) 2.8787(15) 163.3(15) .
N2 H2 O1 0.884(17) 1.999(17) 2.8599(14) 164.3(15) 2_655
N3 H3 O13 0.833(17) 2.129(17) 2.8464(15) 144.2(15) 2_666
N4 H4A O6 0.869(17) 2.029(17) 2.8712(14) 162.9(15) 2_656
C11 H11 O4 1.00 2.59 3.4191(15) 140.8 2_765
C11 H11 O5 1.00 2.56 3.1206(15) 115.1 2_665
C33 H33 O9 1.00 2.47 3.3754(15) 150.8 2_766
C43 H43A O8 0.99 2.58 3.5689(18) 174.3 2_666
C50A H50B O3 0.98 2.60 3.559(3) 167.8 2_665
C50B H50E O3 0.98 2.55 3.383(7) 142.8 2_665

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045

