# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a16316t5
_database_code_depnum_ccdc_archive 'CCDC 1814198'
_audit_update_record             
;
2018-01-01 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Ce H4 N5 O17, 2(H2 O), 2(N H4)'
_chemical_formula_sum            'Ce H16 N7 O19'
_chemical_formula_weight         558.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.0806(4)
_cell_length_b                   8.8522(4)
_cell_length_c                   17.7829(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.8202(18)
_cell_angle_gamma                90
_cell_volume                     1700.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5054
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      36.17

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.180
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    2.790
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.344314
_exptl_absorpt_correction_T_max  0.438258
_exptl_absorpt_process_details   'TWINABS Version 2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4419
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         36.304
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4419
_reflns_number_gt                4001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+20.6965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4419
_refine_ls_number_parameters     164
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.163
_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
Ce1 Ce 0.5000 0.56147(3) 0.7500 0.00926(7) Uani 1 2 d DS T P . .
O1 O 0.5801(3) 0.7526(4) 0.86178(19) 0.0218(6) Uani 1 1 d . . . . .
O2 O 0.3918(3) 0.7975(4) 0.80063(18) 0.0211(6) Uani 1 1 d . . . . .
O3 O 0.4816(10) 0.9525(9) 0.8902(6) 0.0238(12) Uani 0.401(11) 1 d D . P A 1
O3' O 0.4656(7) 0.9091(8) 0.9128(4) 0.0238(12) Uani 0.599(11) 1 d D . P A 2
O4 O 0.4126(3) 0.4155(4) 0.61796(17) 0.0200(6) Uani 1 1 d . . . . .
O5 O 0.5963(3) 0.5082(4) 0.62908(17) 0.0228(6) Uani 1 1 d . . . . .
O6 O 0.5131(10) 0.3871(10) 0.5249(4) 0.0192(17) Uani 0.401(11) 1 d D . P A 1
O6' O 0.5288(7) 0.3272(10) 0.5427(4) 0.0325(17) Uani 0.599(11) 1 d D . P A 2
O9 O 0.7357(2) 0.5588(3) 0.79236(16) 0.0141(4) Uani 1 1 d . . . . .
H9A H 0.7662 0.6476 0.7830 0.021 Uiso 1 1 d R U . . .
H9B H 0.7669 0.4883 0.7669 0.021 Uiso 1 1 d R U . . .
N1 N 0.4819(3) 0.8273(5) 0.8573(2) 0.0286(9) Uani 1 1 d D . . . .
N2 N 0.5108(4) 0.4242(6) 0.5921(2) 0.0282(9) Uani 1 1 d D . . . .
N3 N 0.5000 0.2094(4) 0.7500 0.0168(8) Uani 1 2 d DS T P . .
O7 O 0.4061(12) 0.2810(7) 0.7584(18) 0.0178(9) Uani 0.5 1 d D . P B -1
O8 O 0.4770(6) 0.0762(6) 0.7248(4) 0.0223(12) Uani 0.5 1 d D . P B -1
O7' O 0.5929(12) 0.2812(7) 0.7395(18) 0.0178(9) Uani 0.5 1 d D . P B -1
O1S O 0.6898(8) 0.1370(10) 0.5422(5) 0.0264(16) Uani 0.568(18) 1 d . . P C 1
N4 N 0.2620(7) 0.1748(9) 0.5552(4) 0.0205(17) Uani 0.568(18) 1 d . . P C 1
O1S' O 0.7091(8) 0.1005(11) 0.5188(6) 0.0175(18) Uani 0.432(18) 1 d . . P C 2
N4' N 0.2922(8) 0.0967(12) 0.5610(5) 0.017(2) Uani 0.432(18) 1 d . . P C 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
Ce1 O9 2.553(3) . ?
Ce1 O9 2.553(3) 2_656 ?
Ce1 O1 2.611(3) . ?
Ce1 O1 2.611(3) 2_656 ?
Ce1 O5 2.646(3) 2_656 ?
Ce1 O5 2.646(3) . ?
Ce1 O2 2.663(3) 2_656 ?
Ce1 O2 2.663(3) . ?
Ce1 O4 2.667(3) 2_656 ?
Ce1 O4 2.667(3) . ?
Ce1 O7' 2.708(6) . ?
Ce1 O7 2.709(6) . ?
O1 N1 1.261(4) . ?
O2 N1 1.278(4) . ?
O3 N1 1.254(7) . ?
O3' N1 1.269(6) . ?
O4 N2 1.275(5) . ?
O5 N2 1.268(5) . ?
O6 N2 1.244(6) . ?
O6' N2 1.274(6) . ?
O9 H9A 0.8857 . ?
O9 H9B 0.8860 . ?
N3 O7 1.255(6) . ?
N3 O7' 1.259(6) . ?
N3 O8 1.267(5) . ?

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
O9 Ce1 O9 178.94(13) . 2_656 ?
O9 Ce1 O1 68.20(9) . . ?
O9 Ce1 O1 112.54(9) 2_656 . ?
O9 Ce1 O1 112.54(9) . 2_656 ?
O9 Ce1 O1 68.20(9) 2_656 2_656 ?
O1 Ce1 O1 99.24(15) . 2_656 ?
O9 Ce1 O5 109.22(9) . 2_656 ?
O9 Ce1 O5 70.58(9) 2_656 2_656 ?
O1 Ce1 O5 68.10(11) . 2_656 ?
O1 Ce1 O5 127.13(10) 2_656 2_656 ?
O9 Ce1 O5 70.58(9) . . ?
O9 Ce1 O5 109.22(9) 2_656 . ?
O1 Ce1 O5 127.14(11) . . ?
O1 Ce1 O5 68.10(11) 2_656 . ?
O5 Ce1 O5 159.48(17) 2_656 . ?
O9 Ce1 O2 66.38(9) . 2_656 ?
O9 Ce1 O2 114.53(9) 2_656 2_656 ?
O1 Ce1 O2 69.30(11) . 2_656 ?
O1 Ce1 O2 48.45(9) 2_656 2_656 ?
O5 Ce1 O2 135.01(11) 2_656 2_656 ?
O5 Ce1 O2 64.67(11) . 2_656 ?
O9 Ce1 O2 114.53(9) . . ?
O9 Ce1 O2 66.38(9) 2_656 . ?
O1 Ce1 O2 48.45(8) . . ?
O1 Ce1 O2 69.30(11) 2_656 . ?
O5 Ce1 O2 64.67(11) 2_656 . ?
O5 Ce1 O2 135.01(11) . . ?
O2 Ce1 O2 76.62(15) 2_656 . ?
O9 Ce1 O4 65.67(9) . 2_656 ?
O9 Ce1 O4 113.77(9) 2_656 2_656 ?
O1 Ce1 O4 69.39(11) . 2_656 ?
O1 Ce1 O4 168.50(10) 2_656 2_656 ?
O5 Ce1 O4 48.04(9) 2_656 2_656 ?
O5 Ce1 O4 119.74(10) . 2_656 ?
O2 Ce1 O4 125.12(9) 2_656 2_656 ?
O2 Ce1 O4 100.68(10) . 2_656 ?
O9 Ce1 O4 113.77(9) . . ?
O9 Ce1 O4 65.67(9) 2_656 . ?
O1 Ce1 O4 168.50(10) . . ?
O1 Ce1 O4 69.39(11) 2_656 . ?
O5 Ce1 O4 119.74(10) 2_656 . ?
O5 Ce1 O4 48.03(9) . . ?
O2 Ce1 O4 100.68(10) 2_656 . ?
O2 Ce1 O4 125.12(9) . . ?
O4 Ce1 O4 122.02(15) 2_656 . ?
O9 Ce1 O7' 68.4(3) . . ?
O9 Ce1 O7' 110.5(3) 2_656 . ?
O1 Ce1 O7' 125.2(6) . . ?
O1 Ce1 O7' 127.7(7) 2_656 . ?
O5 Ce1 O7' 96.9(5) 2_656 . ?
O5 Ce1 O7' 63.4(5) . . ?
O2 Ce1 O7' 119.3(3) 2_656 . ?
O2 Ce1 O7' 161.5(5) . . ?
O4 Ce1 O7' 63.1(7) 2_656 . ?
O4 Ce1 O7' 64.2(7) . . ?
O9 Ce1 O7 110.8(3) . . ?
O9 Ce1 O7 68.1(3) 2_656 . ?
O1 Ce1 O7 128.4(7) . . ?
O1 Ce1 O7 124.5(6) 2_656 . ?
O5 Ce1 O7 64.1(5) 2_656 . ?
O5 Ce1 O7 96.4(5) . . ?
O2 Ce1 O7 160.9(5) 2_656 . ?
O2 Ce1 O7 119.6(2) . . ?
O4 Ce1 O7 64.9(7) 2_656 . ?
O4 Ce1 O7 62.3(7) . . ?
O7' Ce1 O7 47.22(12) . . ?
N1 O1 Ce1 98.6(2) . . ?
N1 O2 Ce1 95.6(2) . . ?
N2 O4 Ce1 96.7(2) . . ?
N2 O5 Ce1 97.9(2) . . ?
Ce1 O9 H9A 110.1 . . ?
Ce1 O9 H9B 110.2 . . ?
H9A O9 H9B 108.7 . . ?
O3 N1 O1 121.7(6) . . ?
O1 N1 O3' 121.3(4) . . ?
O3 N1 O2 117.9(6) . . ?
O1 N1 O2 117.0(3) . . ?
O3' N1 O2 120.7(4) . . ?
O6 N2 O5 118.8(6) . . ?
O5 N2 O6' 122.7(5) . . ?
O6 N2 O4 122.1(6) . . ?
O5 N2 O4 116.6(3) . . ?
O6' N2 O4 119.0(5) . . ?
O7 N3 O7' 119.3(4) . . ?
O7 N3 O8 113.9(7) . . ?
O7' N3 O8 121.6(7) . . ?
N3 O7 Ce1 96.7(4) . . ?
N3 O7' Ce1 96.7(4) . . ?

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
Ce1 O1 N1 O3 -165.5(8) . . . . ?
Ce1 O1 N1 O3' 161.6(6) . . . . ?
Ce1 O1 N1 O2 -6.8(5) . . . . ?
Ce1 O2 N1 O3 166.1(8) . . . . ?
Ce1 O2 N1 O1 6.6(5) . . . . ?
Ce1 O2 N1 O3' -161.9(6) . . . . ?
Ce1 O5 N2 O6 171.5(6) . . . . ?
Ce1 O5 N2 O6' -155.4(7) . . . . ?
Ce1 O5 N2 O4 9.2(5) . . . . ?
Ce1 O4 N2 O6 -170.8(7) . . . . ?
Ce1 O4 N2 O5 -9.1(5) . . . . ?
Ce1 O4 N2 O6' 156.1(6) . . . . ?
O7' N3 O7 Ce1 -2(3) . . . . ?
O8 N3 O7 Ce1 -156.9(4) . . . . ?
O7 N3 O7' Ce1 2(3) . . . . ?
O8 N3 O7' Ce1 154.9(4) . . . . ?

_refine_diff_density_max         1.057
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.284


# start Validation Reply Form
_vrf_PLAT043_a16316t5            
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      12.10 Check 
RESPONSE: 
All H positions could not be calculated or located.
;
_vrf_PLAT430_a16316t5            
;
PROBLEM: Short Inter D...A Contact O4       ..N4        .       2.78 Ang.  
RESPONSE:

N4 and N4' are disordered ammonium ion N atoms.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_d12917
_database_code_depnum_ccdc_archive 'CCDC 1814199'
_audit_update_record             
;
2018-01-01 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N O12'
_chemical_formula_sum            'C14 H19 N O12'
_chemical_formula_weight         393.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5311(7)
_cell_length_b                   13.8941(17)
_cell_length_c                   23.168(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1780.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4353
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.99

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.627
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8656
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            22069
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.709
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4099
_reflns_number_gt                3092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.1985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.4(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4099
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.7567(3) 0.46581(13) 0.42688(8) 0.0167(4) Uani 1 1 d . . . . .
O2 O 0.7638(3) 0.62796(13) 0.43634(9) 0.0200(5) Uani 1 1 d . . . . .
O3 O 0.6410(5) 0.59925(15) 0.52813(9) 0.0293(5) Uani 1 1 d . . . . .
O4 O 0.9349(4) 0.69887(16) 0.50978(10) 0.0371(6) Uani 1 1 d . . . . .
O5 O 0.3772(3) 0.64208(12) 0.35399(8) 0.0164(5) Uani 1 1 d . . . . .
O6 O 0.6617(4) 0.73935(14) 0.31573(9) 0.0218(5) Uani 1 1 d . . . . .
O7 O 0.3930(3) 0.48080(14) 0.27524(8) 0.0142(4) Uani 1 1 d . . . . .
O8 O -0.0147(3) 0.47329(16) 0.27878(9) 0.0230(5) Uani 1 1 d . . . . .
O9 O 0.3729(3) 0.30678(13) 0.34071(8) 0.0138(4) Uani 1 1 d . . . . .
O10 O 0.6630(3) 0.21420(13) 0.30084(9) 0.0192(5) Uani 1 1 d . . . . .
O11 O 0.6460(3) 0.21233(13) 0.43437(8) 0.0178(5) Uani 1 1 d . . . . .
O12 O 0.9908(4) 0.12988(15) 0.44690(9) 0.0239(5) Uani 1 1 d . . . . .
N1 N 0.7789(5) 0.64233(17) 0.49770(12) 0.0249(6) Uani 1 1 d . . . . .
C1 C 0.6144(5) 0.54915(18) 0.42070(12) 0.0169(7) Uani 1 1 d . . . . .
H1 H 0.4674 0.5460 0.4457 0.020 Uiso 1 1 calc R U . . .
C2 C 0.5459(5) 0.56404(18) 0.35778(12) 0.0133(6) Uani 1 1 d . . . . .
H2 H 0.6922 0.5767 0.3336 0.016 Uiso 1 1 calc R U . . .
C3 C 0.4123(5) 0.4749(2) 0.33706(11) 0.0131(6) Uani 1 1 d . . . . .
H3 H 0.2470 0.4732 0.3545 0.016 Uiso 1 1 calc R U . . .
C4 C 0.5454(5) 0.38244(19) 0.35144(13) 0.0137(6) Uani 1 1 d . . . . .
H4 H 0.6902 0.3747 0.3260 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6196(5) 0.38030(19) 0.41486(12) 0.0151(6) Uani 1 1 d . . . . .
H5 H 0.4724 0.3783 0.4399 0.018 Uiso 1 1 calc R U . . .
C6 C 0.7895(5) 0.29932(19) 0.43109(14) 0.0196(7) Uani 1 1 d . . . . .
H6A H 0.9179 0.2923 0.4016 0.023 Uiso 1 1 calc R U . . .
H6B H 0.8667 0.3127 0.4688 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7733(5) 0.1306(2) 0.44352(12) 0.0164(6) Uani 1 1 d . . . . .
C8 C 0.6105(5) 0.04629(19) 0.45058(13) 0.0206(7) Uani 1 1 d . . . . .
H8A H 0.4693 0.0538 0.4254 0.031 Uiso 1 1 calc R U . . .
H8B H 0.5573 0.0421 0.4909 0.031 Uiso 1 1 calc R U . . .
H8C H 0.6975 -0.0126 0.4401 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4566(5) 0.7268(2) 0.33147(13) 0.0157(7) Uani 1 1 d . . . . .
C10 C 0.2573(5) 0.7982(2) 0.33012(14) 0.0211(7) Uani 1 1 d . . . . .
H10A H 0.2428 0.8289 0.3680 0.032 Uiso 1 1 calc R U . . .
H10B H 0.1053 0.7656 0.3206 0.032 Uiso 1 1 calc R U . . .
H10C H 0.2921 0.8472 0.3009 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1682(5) 0.4771(2) 0.25117(12) 0.0153(6) Uani 1 1 d . . . . .
C12 C 0.1884(5) 0.4777(2) 0.18721(12) 0.0172(6) Uani 1 1 d . . . . .
H12A H 0.2699 0.4189 0.1743 0.026 Uiso 1 1 calc R U . . .
H12B H 0.2822 0.5340 0.1750 0.026 Uiso 1 1 calc R U . . .
H12C H 0.0264 0.4808 0.1702 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4556(5) 0.22529(19) 0.31484(13) 0.0148(6) Uani 1 1 d . . . . .
C14 C 0.2550(5) 0.15454(19) 0.30951(14) 0.0183(7) Uani 1 1 d . . . . .
H14A H 0.1195 0.1842 0.2888 0.027 Uiso 1 1 calc R U . . .
H14B H 0.2018 0.1348 0.3481 0.027 Uiso 1 1 calc R U . . .
H14C H 0.3115 0.0980 0.2881 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.407(3) . ?
O1 C5 1.437(3) . ?
O2 C1 1.419(3) . ?
O2 N1 1.438(3) . ?
O3 N1 1.199(3) . ?
O4 N1 1.200(3) . ?
O5 C9 1.360(3) . ?
O5 C2 1.433(3) . ?
O6 C9 1.204(3) . ?
O7 C11 1.363(3) . ?
O7 C3 1.439(3) . ?
O8 C11 1.198(3) . ?
O9 C13 1.360(3) . ?
O9 C4 1.441(3) . ?
O10 C13 1.202(3) . ?
O11 C7 1.353(3) . ?
O11 C6 1.448(3) . ?
O12 C7 1.206(3) . ?
C1 C2 1.520(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.521(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.517(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.526(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.514(4) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.486(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.484(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.486(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.487(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 111.42(19) . . ?
C1 O2 N1 113.2(2) . . ?
C9 O5 C2 117.9(2) . . ?
C11 O7 C3 118.2(2) . . ?
C13 O9 C4 117.4(2) . . ?
C7 O11 C6 115.1(2) . . ?
O3 N1 O4 130.3(3) . . ?
O3 N1 O2 118.4(2) . . ?
O4 N1 O2 111.3(3) . . ?
O1 C1 O2 106.5(2) . . ?
O1 C1 C2 110.4(2) . . ?
O2 C1 C2 106.6(2) . . ?
O1 C1 H1 111.1 . . ?
O2 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
O5 C2 C1 108.9(2) . . ?
O5 C2 C3 106.3(2) . . ?
C1 C2 C3 108.2(2) . . ?
O5 C2 H2 111.1 . . ?
C1 C2 H2 111.1 . . ?
C3 C2 H2 111.1 . . ?
O7 C3 C4 107.7(2) . . ?
O7 C3 C2 107.7(2) . . ?
C4 C3 C2 112.6(2) . . ?
O7 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
O9 C4 C3 104.9(2) . . ?
O9 C4 C5 109.3(2) . . ?
C3 C4 C5 111.0(2) . . ?
O9 C4 H4 110.5 . . ?
C3 C4 H4 110.5 . . ?
C5 C4 H4 110.5 . . ?
O1 C5 C6 103.8(2) . . ?
O1 C5 C4 108.2(2) . . ?
C6 C5 C4 114.9(2) . . ?
O1 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
O11 C6 C5 107.0(2) . . ?
O11 C6 H6A 110.3 . . ?
C5 C6 H6A 110.3 . . ?
O11 C6 H6B 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
O12 C7 O11 122.4(3) . . ?
O12 C7 C8 126.2(3) . . ?
O11 C7 C8 111.3(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C9 O5 123.1(3) . . ?
O6 C9 C10 126.6(3) . . ?
O5 C9 C10 110.3(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O8 C11 O7 123.6(3) . . ?
O8 C11 C12 126.6(3) . . ?
O7 C11 C12 109.8(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O10 C13 O9 123.1(2) . . ?
O10 C13 C14 127.2(3) . . ?
O9 C13 C14 109.6(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C1 O2 N1 O3 -11.5(3) . . . . ?
C1 O2 N1 O4 168.9(2) . . . . ?
C5 O1 C1 O2 177.1(2) . . . . ?
C5 O1 C1 C2 -67.6(3) . . . . ?
N1 O2 C1 O1 -81.5(3) . . . . ?
N1 O2 C1 C2 160.6(2) . . . . ?
C9 O5 C2 C1 107.6(3) . . . . ?
C9 O5 C2 C3 -135.9(2) . . . . ?
O1 C1 C2 O5 172.9(2) . . . . ?
O2 C1 C2 O5 -71.9(3) . . . . ?
O1 C1 C2 C3 57.7(3) . . . . ?
O2 C1 C2 C3 172.9(2) . . . . ?
C11 O7 C3 C4 115.2(3) . . . . ?
C11 O7 C3 C2 -123.2(3) . . . . ?
O5 C2 C3 O7 74.9(3) . . . . ?
C1 C2 C3 O7 -168.2(2) . . . . ?
O5 C2 C3 C4 -166.6(2) . . . . ?
C1 C2 C3 C4 -49.7(3) . . . . ?
C13 O9 C4 C3 139.5(2) . . . . ?
C13 O9 C4 C5 -101.4(3) . . . . ?
O7 C3 C4 O9 -73.8(3) . . . . ?
C2 C3 C4 O9 167.7(2) . . . . ?
O7 C3 C4 C5 168.3(2) . . . . ?
C2 C3 C4 C5 49.8(3) . . . . ?
C1 O1 C5 C6 -172.9(2) . . . . ?
C1 O1 C5 C4 64.7(3) . . . . ?
O9 C4 C5 O1 -169.9(2) . . . . ?
C3 C4 C5 O1 -54.7(3) . . . . ?
O9 C4 C5 C6 74.6(3) . . . . ?
C3 C4 C5 C6 -170.1(2) . . . . ?
C7 O11 C6 C5 174.4(2) . . . . ?
O1 C5 C6 O11 165.6(2) . . . . ?
C4 C5 C6 O11 -76.4(3) . . . . ?
C6 O11 C7 O12 -2.2(4) . . . . ?
C6 O11 C7 C8 175.8(2) . . . . ?
C2 O5 C9 O6 -1.4(4) . . . . ?
C2 O5 C9 C10 179.1(2) . . . . ?
C3 O7 C11 O8 3.3(4) . . . . ?
C3 O7 C11 C12 -176.3(2) . . . . ?
C4 O9 C13 O10 0.0(4) . . . . ?
C4 O9 C13 C14 177.8(2) . . . . ?

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
#C5 H5 O12  1.00 2.63 3.284(4) 123.3 4_456 
C2 H2 O8 1.00 2.51 3.293(3) 134.9 1_655
C4 H4 O8 1.00 2.40 3.217(3) 138.9 1_655
C8 H8B O1 0.98 2.53 3.452(4) 156.4 4_456
C10 H10B O6 0.98 2.48 3.410(3) 157.8 1_455
C12 H12A O6 0.98 2.53 3.415(4) 149.5 3_645
C12 H12B O10 0.98 2.58 3.398(4) 140.5 3_655
C14 H14A O10 0.98 2.57 3.383(3) 140.0 1_455
C14 H14B O12 0.98 2.57 3.519(4) 162.9 1_455

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_d14017_sq
_database_code_depnum_ccdc_archive 'CCDC 1814200'
_audit_update_record             
;
2018-01-01 deposited with the CCDC.
2018-04-11 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         'C34 H27 N O12 [+ solvent]'
_chemical_formula_sum            'C34 H27 N O12'
_chemical_formula_weight         641.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   14.9257(16)
_cell_length_b                   5.4551(6)
_cell_length_c                   21.093(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.990(7)
_cell_angle_gamma                90
_cell_volume                     1708.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1879
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      19.10

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8124
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            17263
_diffrn_reflns_av_unetI/netI     0.1392
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.596
_diffrn_reflns_theta_max         25.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             6067
_reflns_number_gt                3117
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.893
_reflns_Friedel_fraction_full    0.909

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 900 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6067
_refine_ls_number_parameters     497
_refine_ls_number_restraints     471
_refine_ls_R_factor_all          0.1668
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.2084
_refine_ls_wR_factor_gt          0.1695
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.004
_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 0.3140(3) 0.3962(10) 0.2193(3) 0.0467(14) Uani 1 1 d . . . . .
O2 O 0.2177(4) 0.3326(12) 0.1322(3) 0.0609(18) Uani 1 1 d . . . . .
O3 O 0.3341(5) 0.4394(16) 0.0775(3) 0.089(2) Uani 1 1 d . . . . .
O4 O 0.2610(5) 0.1009(17) 0.0567(4) 0.101(3) Uani 1 1 d . . . . .
O5 O 0.1097(3) 0.7264(11) 0.1669(2) 0.0456(14) Uani 1 1 d . . . . .
O6 O -0.0133(4) 0.5212(12) 0.1926(3) 0.0587(18) Uani 1 1 d . . . . .
O7 O 0.1165(3) 0.7500(9) 0.3031(2) 0.0329(12) Uani 1 1 d . . . . .
O8 O 0.1400(4) 1.1503(10) 0.3229(3) 0.0530(16) Uani 1 1 d . . . . .
O9 O 0.3047(3) 0.7720(10) 0.3604(2) 0.0385(13) Uani 1 1 d . . . . .
O10 O 0.2264(5) 0.5816(16) 0.4297(3) 0.093(3) Uani 1 1 d . . . . .
O11 O 0.4988(3) 0.3920(11) 0.2772(3) 0.0592(17) Uani 1 1 d . . . . .
O12 O 0.5196(7) 0.0061(17) 0.3105(5) 0.079(3) Uani 0.736(11) 1 d D . P A 1
O12' O 0.5575(18) 0.161(6) 0.3493(9) 0.079(3) Uani 0.264(11) 1 d D . P A 2
N1 N 0.2774(6) 0.289(2) 0.0846(4) 0.081(3) Uani 1 1 d . . . . .
C1 C 0.2486(5) 0.5113(17) 0.1774(4) 0.048(2) Uani 1 1 d . . . . .
H1 H 0.273578 0.657436 0.156674 0.058 Uiso 1 1 calc R U . . .
C2 C 0.1666(5) 0.5784(15) 0.2109(3) 0.0368(18) Uani 1 1 d . . . . .
H2 H 0.133992 0.427372 0.222473 0.044 Uiso 1 1 calc R U . . .
C3 C 0.1946(4) 0.7288(16) 0.2691(3) 0.0344(17) Uani 1 1 d . . . . .
H3 H 0.214133 0.895180 0.256180 0.041 Uiso 1 1 calc R U . . .
C4 C 0.2705(5) 0.6062(15) 0.3110(3) 0.0351(17) Uani 1 1 d . . . . .
H4 H 0.248346 0.452564 0.330033 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3480(5) 0.5482(15) 0.2717(4) 0.041(2) Uani 1 1 d . . . . .
H5 H 0.374626 0.702323 0.256158 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4179(5) 0.4017(17) 0.3110(4) 0.051(2) Uani 1 1 d . . . . .
H6A H 0.432175 0.479210 0.353308 0.061 Uiso 1 1 calc R U . . .
H6B H 0.395344 0.233793 0.317475 0.061 Uiso 1 1 calc R U . . .
C7 C 0.5510(6) 0.202(2) 0.2892(5) 0.067(3) Uani 1 1 d D . . . .
C8 C 0.637(2) 0.240(8) 0.261(3) 0.054(4) Uani 0.529(13) 1 d D . P A 1
C9 C 0.6387(12) 0.343(4) 0.2022(10) 0.062(6) Uani 0.529(13) 1 d . . P A 1
H9 H 0.584644 0.407883 0.180949 0.074 Uiso 0.529(13) 1 calc R U P A 1
C10 C 0.7211(12) 0.355(4) 0.1709(10) 0.088(8) Uani 0.529(13) 1 d . . P A 1
H10 H 0.722223 0.427202 0.130011 0.105 Uiso 0.529(13) 1 calc R U P A 1
C11 C 0.7982(14) 0.256(5) 0.2042(12) 0.056(5) Uani 0.529(13) 1 d . . P A 1
H11 H 0.854180 0.275787 0.187120 0.067 Uiso 0.529(13) 1 calc R U P A 1
C12 C 0.797(2) 0.132(7) 0.2595(17) 0.089(11) Uani 0.529(13) 1 d . . P A 1
H12 H 0.849343 0.049685 0.278167 0.107 Uiso 0.529(13) 1 calc R U P A 1
C13 C 0.7185(14) 0.126(5) 0.2883(13) 0.084(8) Uani 0.529(13) 1 d . . P A 1
H13 H 0.718334 0.043737 0.327898 0.101 Uiso 0.529(13) 1 calc R U P A 1
C8' C 0.641(2) 0.185(9) 0.266(3) 0.054(4) Uani 0.471(13) 1 d D . P A 2
C9' C 0.6746(12) 0.415(4) 0.2575(11) 0.056(6) Uani 0.471(13) 1 d . . P A 2
H9' H 0.638538 0.556629 0.261136 0.067 Uiso 0.471(13) 1 calc R U P A 2
C10' C 0.7679(12) 0.435(4) 0.2424(10) 0.062(6) Uani 0.471(13) 1 d . . P A 2
H10' H 0.795740 0.588145 0.235310 0.074 Uiso 0.471(13) 1 calc R U P A 2
C11' C 0.8122(18) 0.213(6) 0.2392(17) 0.056(5) Uani 0.471(13) 1 d . . P A 2
H11' H 0.873701 0.211041 0.231403 0.067 Uiso 0.471(13) 1 calc R U P A 2
C12' C 0.7652(16) -0.018(5) 0.2479(12) 0.058(6) Uani 0.471(13) 1 d . . P A 2
H12' H 0.793658 -0.171126 0.242657 0.070 Uiso 0.471(13) 1 calc R U P A 2
C13' C 0.6862(15) -0.006(5) 0.2624(11) 0.056(6) Uani 0.471(13) 1 d . . P A 2
H13' H 0.657899 -0.156704 0.271213 0.068 Uiso 0.471(13) 1 calc R U P A 2
C14 C 0.0184(5) 0.6803(17) 0.1627(4) 0.044(2) Uani 1 1 d . . . . .
C15 C -0.0308(6) 0.8512(17) 0.1176(4) 0.050(2) Uani 1 1 d . . . . .
C16 C -0.1236(6) 0.808(2) 0.1026(4) 0.076(3) Uani 1 1 d . . . . .
H16 H -0.152039 0.673300 0.120763 0.092 Uiso 1 1 calc R U . . .
C17 C -0.1730(8) 0.968(3) 0.0607(5) 0.088(4) Uani 1 1 d . . . . .
H17 H -0.235465 0.939931 0.049679 0.106 Uiso 1 1 calc R U . . .
C18 C -0.1320(9) 1.165(3) 0.0353(5) 0.089(3) Uani 1 1 d . . . . .
H18 H -0.166269 1.275219 0.007679 0.106 Uiso 1 1 calc R U . . .
C19 C -0.0400(8) 1.201(2) 0.0502(5) 0.081(3) Uani 1 1 d . . . . .
H19 H -0.011417 1.333465 0.031005 0.097 Uiso 1 1 calc R U . . .
C20 C 0.0100(7) 1.0505(19) 0.0919(4) 0.064(3) Uani 1 1 d . . . . .
H20 H 0.072198 1.082374 0.103072 0.077 Uiso 1 1 calc R U . . .
C21 C 0.0977(5) 0.9678(14) 0.3300(4) 0.0320(17) Uani 1 1 d . . . . .
C22 C 0.0214(5) 0.9460(14) 0.3673(3) 0.0337(17) Uani 1 1 d . . . . .
C23 C -0.0373(4) 0.7433(15) 0.3607(3) 0.0342(17) Uani 1 1 d . . . . .
H23 H -0.028780 0.619580 0.330190 0.041 Uiso 1 1 calc R U . . .
C24 C -0.1072(5) 0.7241(16) 0.3983(4) 0.0396(19) Uani 1 1 d . . . . .
H24 H -0.146809 0.587561 0.393376 0.048 Uiso 1 1 calc R U . . .
C25 C -0.1198(5) 0.9010(15) 0.4429(4) 0.0391(19) Uani 1 1 d . . . . .
H25 H -0.167832 0.886421 0.468917 0.047 Uiso 1 1 calc R U . . .
C26 C -0.0618(5) 1.1024(15) 0.4498(4) 0.042(2) Uani 1 1 d . . . . .
H26 H -0.070801 1.225056 0.480518 0.050 Uiso 1 1 calc R U . . .
C27 C 0.0090(5) 1.1253(14) 0.4124(4) 0.0391(19) Uani 1 1 d . . . . .
H27 H 0.048575 1.262026 0.417536 0.047 Uiso 1 1 calc R U . . .
C28 C 0.2789(5) 0.735(2) 0.4197(4) 0.053(2) Uani 1 1 d . . . . .
C29 C 0.3080(17) 0.875(5) 0.4745(12) 0.046(3) Uani 0.32(2) 1 d G . P B 1
C30 C 0.3060(18) 0.812(5) 0.5381(13) 0.060(10) Uani 0.32(2) 1 d G . P B 1
H30 H 0.282435 0.657379 0.549012 0.072 Uiso 0.32(2) 1 calc R U P B 1
C31 C 0.338(2) 0.974(6) 0.5859(11) 0.067(10) Uani 0.32(2) 1 d G . P B 1
H31 H 0.336928 0.931003 0.629382 0.080 Uiso 0.32(2) 1 calc R U P B 1
C32 C 0.373(3) 1.200(5) 0.5700(13) 0.11(2) Uani 0.32(2) 1 d G . P B 1
H32 H 0.394889 1.311386 0.602590 0.126 Uiso 0.32(2) 1 calc R U P B 1
C33 C 0.375(3) 1.264(4) 0.5063(14) 0.094(15) Uani 0.32(2) 1 d G . P B 1
H33 H 0.398356 1.418149 0.495427 0.113 Uiso 0.32(2) 1 calc R U P B 1
C34 C 0.342(2) 1.101(5) 0.4586(11) 0.063(9) Uani 0.32(2) 1 d G . P B 1
H34 H 0.343863 1.144528 0.415056 0.076 Uiso 0.32(2) 1 calc R U P B 1
C29' C 0.3278(8) 0.920(2) 0.4635(5) 0.046(3) Uani 0.68(2) 1 d G . P B 2
C30' C 0.3015(8) 0.938(3) 0.5246(6) 0.068(5) Uani 0.68(2) 1 d G . P B 2
H30' H 0.253697 0.839069 0.536637 0.082 Uiso 0.68(2) 1 calc R U P B 2
C31' C 0.3451(8) 1.101(4) 0.5681(5) 0.074(6) Uani 0.68(2) 1 d G . P B 2
H31' H 0.327074 1.113651 0.609861 0.088 Uiso 0.68(2) 1 calc R U P B 2
C32' C 0.4150(8) 1.246(3) 0.5505(5) 0.090(6) Uani 0.68(2) 1 d G . P B 2
H32' H 0.444784 1.357396 0.580200 0.108 Uiso 0.68(2) 1 calc R U P B 2
C33' C 0.4413(10) 1.228(2) 0.4894(5) 0.084(6) Uani 0.68(2) 1 d G . P B 2
H33' H 0.489118 1.326562 0.477313 0.101 Uiso 0.68(2) 1 calc R U P B 2
C34' C 0.3977(10) 1.064(2) 0.4459(4) 0.063(5) Uani 0.68(2) 1 d G . P B 2
H34' H 0.415741 1.051981 0.404087 0.076 Uiso 0.68(2) 1 calc R U P B 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 C1 1.396(10) . ?
O1 C5 1.433(9) . ?
O2 C1 1.407(9) . ?
O2 N1 1.430(9) . ?
O3 N1 1.197(11) . ?
O4 N1 1.197(11) . ?
O5 C14 1.380(9) . ?
O5 C2 1.438(9) . ?
O6 C14 1.200(9) . ?
O7 C21 1.359(8) . ?
O7 C3 1.435(7) . ?
O8 C21 1.197(8) . ?
O9 C28 1.361(10) . ?
O9 C4 1.433(9) . ?
O10 C28 1.182(11) . ?
O11 C7 1.306(11) . ?
O11 C6 1.466(8) . ?
O12 C7 1.268(12) . ?
O12' C7 1.281(15) . ?
C1 C2 1.520(10) . ?
C1 H1 1.0000 . ?
C2 C3 1.500(10) . ?
C2 H2 1.0000 . ?
C3 C4 1.517(10) . ?
C3 H3 1.0000 . ?
C4 C5 1.525(10) . ?
C4 H4 1.0000 . ?
C5 C6 1.494(11) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8' 1.475(15) . ?
C7 C8 1.479(14) . ?
C8 C9 1.36(5) . ?
C8 C13 1.44(5) . ?
C9 C10 1.46(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.39(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.35(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.38(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C8' C13' 1.25(4) . ?
C8' C9' 1.37(5) . ?
C9' C10' 1.47(2) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.38(4) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.46(4) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.25(3) . ?
C12' H12' 0.9500 . ?
C13' H13' 0.9500 . ?
C14 C15 1.473(12) . ?
C15 C20 1.384(12) . ?
C15 C16 1.408(12) . ?
C16 C17 1.395(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.367(14) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.454(10) . ?
C22 C27 1.390(10) . ?
C22 C23 1.409(10) . ?
C23 C24 1.379(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(11) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(10) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.42(2) . ?
C28 C29' 1.503(13) . ?
C29 C30 1.3900 . ?
C29 C34 1.3900 . ?
C30 C31 1.3900 . ?
C30 H30 0.9500 . ?
C31 C32 1.3900 . ?
C31 H31 0.9500 . ?
C32 C33 1.3900 . ?
C32 H32 0.9500 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C29' C30' 1.3900 . ?
C29' C34' 1.3900 . ?
C30' C31' 1.3900 . ?
C30' H30' 0.9500 . ?
C31' C32' 1.3900 . ?
C31' H31' 0.9500 . ?
C32' C33' 1.3900 . ?
C32' H32' 0.9500 . ?
C33' C34' 1.3900 . ?
C33' H33' 0.9500 . ?
C34' H34' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 113.4(6) . . ?
C1 O2 N1 114.0(6) . . ?
C14 O5 C2 116.8(6) . . ?
C21 O7 C3 119.6(6) . . ?
C28 O9 C4 117.5(6) . . ?
C7 O11 C6 116.1(7) . . ?
O3 N1 O4 129.5(9) . . ?
O3 N1 O2 118.4(9) . . ?
O4 N1 O2 112.1(8) . . ?
O1 C1 O2 105.9(7) . . ?
O1 C1 C2 111.0(6) . . ?
O2 C1 C2 105.0(6) . . ?
O1 C1 H1 111.5 . . ?
O2 C1 H1 111.5 . . ?
C2 C1 H1 111.5 . . ?
O5 C2 C3 108.5(6) . . ?
O5 C2 C1 106.5(6) . . ?
C3 C2 C1 110.0(6) . . ?
O5 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
C1 C2 H2 110.6 . . ?
O7 C3 C2 106.3(5) . . ?
O7 C3 C4 109.9(5) . . ?
C2 C3 C4 111.3(6) . . ?
O7 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
O9 C4 C3 109.5(6) . . ?
O9 C4 C5 107.0(6) . . ?
C3 C4 C5 109.7(6) . . ?
O9 C4 H4 110.2 . . ?
C3 C4 H4 110.2 . . ?
C5 C4 H4 110.2 . . ?
O1 C5 C6 106.8(7) . . ?
O1 C5 C4 108.1(6) . . ?
C6 C5 C4 109.6(6) . . ?
O1 C5 H5 110.7 . . ?
C6 C5 H5 110.7 . . ?
C4 C5 H5 110.7 . . ?
O11 C6 C5 108.2(6) . . ?
O11 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O11 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O12 C7 O11 120.1(8) . . ?
O12' C7 O11 108.1(13) . . ?
O12' C7 C8' 110(3) . . ?
O11 C7 C8' 122.0(17) . . ?
O12 C7 C8 129.0(16) . . ?
O11 C7 C8 109.4(15) . . ?
C9 C8 C13 116.3(16) . . ?
C9 C8 C7 122(3) . . ?
C13 C8 C7 121(3) . . ?
C8 C9 C10 122.1(18) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C9 116.5(19) . . ?
C11 C10 H10 121.8 . . ?
C9 C10 H10 121.8 . . ?
C12 C11 C10 123(2) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 119(2) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 123(2) . . ?
C12 C13 H13 118.6 . . ?
C8 C13 H13 118.6 . . ?
C13' C8' C9' 123.1(19) . . ?
C13' C8' C7 126(3) . . ?
C9' C8' C7 110(3) . . ?
C8' C9' C10' 118.0(19) . . ?
C8' C9' H9' 121.0 . . ?
C10' C9' H9' 121.0 . . ?
C11' C10' C9' 114(2) . . ?
C11' C10' H10' 122.8 . . ?
C9' C10' H10' 122.8 . . ?
C10' C11' C12' 121(2) . . ?
C10' C11' H11' 119.7 . . ?
C12' C11' H11' 119.7 . . ?
C13' C12' C11' 118(2) . . ?
C13' C12' H12' 121.2 . . ?
C11' C12' H12' 121.2 . . ?
C12' C13' C8' 126(3) . . ?
C12' C13' H13' 117.0 . . ?
C8' C13' H13' 117.0 . . ?
O6 C14 O5 122.7(8) . . ?
O6 C14 C15 126.9(7) . . ?
O5 C14 C15 110.4(7) . . ?
C20 C15 C16 120.4(9) . . ?
C20 C15 C14 122.7(8) . . ?
C16 C15 C14 116.9(8) . . ?
C17 C16 C15 118.7(11) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C18 C17 C16 120.6(11) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.6(11) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 121.3(12) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C15 119.4(10) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
O8 C21 O7 122.7(6) . . ?
O8 C21 C22 126.1(7) . . ?
O7 C21 C22 111.2(6) . . ?
C27 C22 C23 119.6(7) . . ?
C27 C22 C21 118.7(7) . . ?
C23 C22 C21 121.7(7) . . ?
C24 C23 C22 120.2(7) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.4(8) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.7(7) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.7(7) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 119.3(7) . . ?
C26 C27 H27 120.4 . . ?
C22 C27 H27 120.4 . . ?
O10 C28 O9 121.7(9) . . ?
O10 C28 C29 112.9(14) . . ?
O9 C28 C29 125.4(14) . . ?
O10 C28 C29' 130.8(9) . . ?
O9 C28 C29' 107.5(8) . . ?
C30 C29 C34 120.0 . . ?
C30 C29 C28 128.2(18) . . ?
C34 C29 C28 111.8(18) . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C29 120.0 . . ?
C33 C34 H34 120.0 . . ?
C29 C34 H34 120.0 . . ?
C30' C29' C34' 120.0 . . ?
C30' C29' C28 116.9(7) . . ?
C34' C29' C28 123.1(7) . . ?
C29' C30' C31' 120.0 . . ?
C29' C30' H30' 120.0 . . ?
C31' C30' H30' 120.0 . . ?
C32' C31' C30' 120.0 . . ?
C32' C31' H31' 120.0 . . ?
C30' C31' H31' 120.0 . . ?
C33' C32' C31' 120.0 . . ?
C33' C32' H32' 120.0 . . ?
C31' C32' H32' 120.0 . . ?
C32' C33' C34' 120.0 . . ?
C32' C33' H33' 120.0 . . ?
C34' C33' H33' 120.0 . . ?
C33' C34' C29' 120.0 . . ?
C33' C34' H34' 120.0 . . ?
C29' C34' H34' 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 N1 O3 -17.4(13) . . . . ?
C1 O2 N1 O4 163.3(9) . . . . ?
C5 O1 C1 O2 -175.5(6) . . . . ?
C5 O1 C1 C2 -62.0(8) . . . . ?
N1 O2 C1 O1 -77.7(8) . . . . ?
N1 O2 C1 C2 164.7(7) . . . . ?
C14 O5 C2 C3 -103.5(7) . . . . ?
C14 O5 C2 C1 138.0(7) . . . . ?
O1 C1 C2 O5 171.7(6) . . . . ?
O2 C1 C2 O5 -74.3(8) . . . . ?
O1 C1 C2 C3 54.3(9) . . . . ?
O2 C1 C2 C3 168.3(7) . . . . ?
C21 O7 C3 C2 -138.9(7) . . . . ?
C21 O7 C3 C4 100.5(8) . . . . ?
O5 C2 C3 O7 72.9(7) . . . . ?
C1 C2 C3 O7 -170.9(7) . . . . ?
O5 C2 C3 C4 -167.4(5) . . . . ?
C1 C2 C3 C4 -51.2(8) . . . . ?
C28 O9 C4 C3 102.4(7) . . . . ?
C28 O9 C4 C5 -138.7(7) . . . . ?
O7 C3 C4 O9 -71.5(7) . . . . ?
C2 C3 C4 O9 170.9(6) . . . . ?
O7 C3 C4 C5 171.3(6) . . . . ?
C2 C3 C4 C5 53.8(8) . . . . ?
C1 O1 C5 C6 -178.9(6) . . . . ?
C1 O1 C5 C4 63.2(8) . . . . ?
O9 C4 C5 O1 -176.0(6) . . . . ?
C3 C4 C5 O1 -57.3(8) . . . . ?
O9 C4 C5 C6 67.9(8) . . . . ?
C3 C4 C5 C6 -173.4(7) . . . . ?
C7 O11 C6 C5 -153.3(8) . . . . ?
O1 C5 C6 O11 74.5(8) . . . . ?
C4 C5 C6 O11 -168.6(7) . . . . ?
C6 O11 C7 O12 22.5(15) . . . . ?
C6 O11 C7 O12' -42.4(18) . . . . ?
C6 O11 C7 C8' -171(4) . . . . ?
C6 O11 C7 C8 -170(3) . . . . ?
O12 C7 C8 C9 125(3) . . . . ?
O11 C7 C8 C9 -41(6) . . . . ?
O12 C7 C8 C13 -42(7) . . . . ?
O11 C7 C8 C13 152(4) . . . . ?
C13 C8 C9 C10 -5(6) . . . . ?
C7 C8 C9 C10 -173(3) . . . . ?
C8 C9 C10 C11 0(5) . . . . ?
C9 C10 C11 C12 6(4) . . . . ?
C10 C11 C12 C13 -8(5) . . . . ?
C11 C12 C13 C8 2(6) . . . . ?
C9 C8 C13 C12 4(7) . . . . ?
C7 C8 C13 C12 172(4) . . . . ?
O12' C7 C8' C13' 70(8) . . . . ?
O11 C7 C8' C13' -162(5) . . . . ?
O12' C7 C8' C9' -102(4) . . . . ?
O11 C7 C8' C9' 26(7) . . . . ?
C13' C8' C9' C10' 0(9) . . . . ?
C7 C8' C9' C10' 173(3) . . . . ?
C8' C9' C10' C11' -1(5) . . . . ?
C9' C10' C11' C12' 3(4) . . . . ?
C10' C11' C12' C13' -5(4) . . . . ?
C11' C12' C13' C8' 5(6) . . . . ?
C9' C8' C13' C12' -3(10) . . . . ?
C7 C8' C13' C12' -174(4) . . . . ?
C2 O5 C14 O6 -1.9(11) . . . . ?
C2 O5 C14 C15 178.1(6) . . . . ?
O6 C14 C15 C20 170.8(9) . . . . ?
O5 C14 C15 C20 -9.2(11) . . . . ?
O6 C14 C15 C16 -7.3(13) . . . . ?
O5 C14 C15 C16 172.8(8) . . . . ?
C20 C15 C16 C17 1.1(14) . . . . ?
C14 C15 C16 C17 179.2(9) . . . . ?
C15 C16 C17 C18 -0.9(16) . . . . ?
C16 C17 C18 C19 1.7(18) . . . . ?
C17 C18 C19 C20 -2.8(17) . . . . ?
C18 C19 C20 C15 2.9(15) . . . . ?
C16 C15 C20 C19 -2.1(14) . . . . ?
C14 C15 C20 C19 179.9(9) . . . . ?
C3 O7 C21 O8 5.5(10) . . . . ?
C3 O7 C21 C22 -174.4(6) . . . . ?
O8 C21 C22 C27 -18.5(11) . . . . ?
O7 C21 C22 C27 161.5(6) . . . . ?
O8 C21 C22 C23 164.4(8) . . . . ?
O7 C21 C22 C23 -15.7(10) . . . . ?
C27 C22 C23 C24 0.6(11) . . . . ?
C21 C22 C23 C24 177.8(7) . . . . ?
C22 C23 C24 C25 -0.5(11) . . . . ?
C23 C24 C25 C26 0.4(11) . . . . ?
C24 C25 C26 C27 -0.4(11) . . . . ?
C25 C26 C27 C22 0.5(11) . . . . ?
C23 C22 C27 C26 -0.6(11) . . . . ?
C21 C22 C27 C26 -177.8(7) . . . . ?
C4 O9 C28 O10 -4.0(13) . . . . ?
C4 O9 C28 C29 177.9(15) . . . . ?
C4 O9 C28 C29' 176.3(7) . . . . ?
O10 C28 C29 C30 22(2) . . . . ?
O9 C28 C29 C30 -160.2(15) . . . . ?
O10 C28 C29 C34 -158.8(15) . . . . ?
O9 C28 C29 C34 20(2) . . . . ?
C34 C29 C30 C31 0.0 . . . . ?
C28 C29 C30 C31 180(2) . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C29 0.0 . . . . ?
C30 C29 C34 C33 0.0 . . . . ?
C28 C29 C34 C33 -180(2) . . . . ?
O10 C28 C29' C30' -8.7(17) . . . . ?
O9 C28 C29' C30' 171.0(8) . . . . ?
O10 C28 C29' C34' 170.0(12) . . . . ?
O9 C28 C29' C34' -10.4(13) . . . . ?
C34' C29' C30' C31' 0.0 . . . . ?
C28 C29' C30' C31' 178.7(11) . . . . ?
C29' C30' C31' C32' 0.0 . . . . ?
C30' C31' C32' C33' 0.0 . . . . ?
C31' C32' C33' C34' 0.0 . . . . ?
C32' C33' C34' C29' 0.0 . . . . ?
C30' C29' C34' C33' 0.0 . . . . ?
C28 C29' C34' C33' -178.6(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
C2 H2 O8 1.00 2.60 3.375(10) 134.7 1_545
C4 H4 O8 1.00 2.30 3.185(10) 146.4 1_545

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.064



# start Validation Reply Form
_vrf_PLAT340_d14017_sq           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01258 Ang.  
RESPONSE:
The data set is of poor quality and weak resulting in low bond precision
;
# end Validation Reply Form
