# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_mcg1662
_database_code_depnum_ccdc_archive 'CCDC 1876028'
loop_
_audit_author_name
_audit_author_address
'Dale Swenson'
;UIOWA
United States of America
;
_audit_update_record             
;
2018-10-29 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_audit_creation_date             2018-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration unk
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 O5, C12 H10 N2'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2700(8)
_cell_length_b                   9.1848(9)
_cell_length_c                   12.4194(12)
_cell_angle_alpha                71.619(5)
_cell_angle_beta                 82.065(5)
_cell_angle_gamma                79.191(5)
_cell_volume                     876.19(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5206
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.315
_diffrn_reflns_theta_min         1.734
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2399
_reflns_number_total             3148
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0805P)²+0.3884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1734
_refine_special_details          
'All nonhydrogen atoms were identified from the difference Fourier map within several refinement steps. Hydrogen atoms associated with carbon atoms were refined in geometrically constrained positions with isotropic thermal parameter. some reflections were omitted due to beamstop shadowing.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H003-O003
 0.85 with sigma of 0.02
 O002-H002
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00N(H00N)
3.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O -0.3637(2) 0.77172(19) 0.77588(13) 0.0604(5) Uani 1 1 d . . . . .
O002 O -0.1242(3) 0.3158(2) 0.92726(17) 0.0834(7) Uani 1 1 d D . . . .
O003 O 0.1358(2) 0.5395(3) 0.80488(16) 0.0867(7) Uani 1 1 d D . . . .
N004 N 0.3052(3) 0.3973(2) 0.66020(17) 0.0630(6) Uani 1 1 d . . . . .
N005 N 1.0069(3) -0.1338(2) 0.20205(19) 0.0656(6) Uani 1 1 d . . . . .
C006 C -0.2509(3) 0.5672(2) 0.92118(17) 0.0494(5) Uani 1 1 d . . . . .
H006 H -0.2445 0.5361 1.0037 0.059 Uiso 1 1 calc R . . . .
O007 O -0.3254(3) 0.4151(3) 0.8161(2) 0.1046(8) Uani 1 1 d . . . . .
O008 O -0.0345(3) 0.6434(4) 0.67450(17) 0.1125(9) Uani 1 1 d . . . . .
C009 C -0.1170(3) 0.6739(2) 0.85929(17) 0.0476(5) Uani 1 1 d . . . . .
H009 H -0.0528 0.6873 0.9153 0.057 Uiso 1 1 calc R . . . .
C00A C -0.4113(3) 0.6828(3) 0.8890(2) 0.0590(6) Uani 1 1 d . . . . .
H00A H -0.5104 0.6350 0.8968 0.071 Uiso 1 1 calc R . . . .
C00B C 0.4990(3) 0.2525(3) 0.51094(19) 0.0511(5) Uani 1 1 d . . . . .
C00C C 0.8189(3) 0.0023(3) 0.36060(19) 0.0517(5) Uani 1 1 d . . . . .
C00D C -0.2380(3) 0.4258(3) 0.88257(19) 0.0558(6) Uani 1 1 d . . . . .
C00E C 1.0316(3) -0.1906(3) 0.3099(2) 0.0662(7) Uani 1 1 d . . . . .
H00E H 1.1132 -0.2762 0.3323 0.079 Uiso 1 1 calc R . . . .
C00F C -0.0024(3) 0.6179(3) 0.7694(2) 0.0552(6) Uani 1 1 d . . . . .
C00G C 0.8013(3) 0.0582(3) 0.2449(2) 0.0653(7) Uani 1 1 d . . . . .
H00G H 0.7237 0.1453 0.2173 0.078 Uiso 1 1 calc R . . . .
C00H C 0.8947(4) -0.0111(3) 0.1710(2) 0.0706(7) Uani 1 1 d . . . . .
H00H H 0.8783 0.0307 0.0940 0.085 Uiso 1 1 calc R . . . .
C00I C 0.5226(3) 0.2095(3) 0.6242(2) 0.0684(7) Uani 1 1 d . . . . .
H00I H 0.6060 0.1287 0.6533 0.082 Uiso 1 1 calc R . . . .
C00J C 0.4265(4) 0.2826(3) 0.6943(2) 0.0722(7) Uani 1 1 d . . . . .
H00J H 0.4470 0.2504 0.7707 0.087 Uiso 1 1 calc R . . . .
C00K C 0.2760(3) 0.4394(3) 0.5508(2) 0.0686(7) Uani 1 1 d . . . . .
H00K H 0.1890 0.5182 0.5253 0.082 Uiso 1 1 calc R . . . .
C00L C -0.4252(3) 0.8000(3) 0.9533(2) 0.0698(7) Uani 1 1 d . . . . .
H00L H -0.4975 0.8073 1.0164 0.084 Uiso 1 1 calc R . . . .
C00M C 0.9406(3) -0.1282(3) 0.3939(2) 0.0665(7) Uani 1 1 d . . . . .
H00M H 0.9607 -0.1727 0.4701 0.080 Uiso 1 1 calc R . . . .
C00N C -0.2311(3) 0.8277(3) 0.8058(2) 0.0569(6) Uani 1 1 d . . . . .
H00N H -0.1778 0.9028 0.7429 0.068 Uiso 1 1 calc R . . . .
C00O C 0.3712(3) 0.3700(3) 0.4730(2) 0.0607(6) Uani 1 1 d . . . . .
H00O H 0.3485 0.4026 0.3971 0.073 Uiso 1 1 calc R . . . .
C00P C -0.3140(3) 0.8891(3) 0.9018(2) 0.0694(7) Uani 1 1 d . . . . .
H00P H -0.2911 0.9731 0.9205 0.083 Uiso 1 1 calc R . . . .
C00Q C 0.6030(3) 0.1846(3) 0.4258(2) 0.0620(6) Uani 1 1 d . . . . .
H00Q H 0.5815 0.2316 0.3501 0.074 Uiso 1 1 calc R . . . .
C00R C 0.7202(3) 0.0671(3) 0.4459(2) 0.0642(7) Uani 1 1 d . . . . .
H00R H 0.7434 0.0200 0.5213 0.077 Uiso 1 1 calc R . . . .
H002 H -0.110(5) 0.250(4) 0.889(3) 0.123(13) Uiso 1 1 d D . . . .
H003 H 0.192(5) 0.494(4) 0.755(3) 0.134(14) Uiso 1 1 d 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
O001 C00A 1.428(3) . ?
O001 C00N 1.432(3) . ?
O002 C00D 1.284(3) . ?
O002 H002 0.859(19) . ?
O003 C00F 1.284(3) . ?
O003 H003 0.886(19) . ?
N004 C00J 1.318(3) . ?
N004 C00K 1.333(3) . ?
N005 C00E 1.305(3) . ?
N005 C00H 1.308(3) . ?
C006 H006 0.9800 . ?
C006 C009 1.573(3) . ?
C006 C00A 1.548(3) . ?
C006 C00D 1.501(3) . ?
O007 C00D 1.206(3) . ?
O008 C00F 1.185(3) . ?
C009 H009 0.9800 . ?
C009 C00F 1.515(3) . ?
C009 C00N 1.552(3) . ?
C00A H00A 0.9800 . ?
C00A C00L 1.510(4) . ?
C00B C00I 1.367(3) . ?
C00B C00O 1.376(3) . ?
C00B C00Q 1.486(3) . ?
C00C C00G 1.384(3) . ?
C00C C00M 1.404(3) . ?
C00C C00R 1.456(3) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.408(4) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.354(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00J 1.349(4) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00O 1.396(4) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.309(4) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9800 . ?
C00N C00P 1.504(4) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.292(4) . ?
C00R H00R 0.9300 . ?

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
C00A O001 C00N 95.91(17) . . ?
C00D O002 H002 107(3) . . ?
C00F O003 H003 112(3) . . ?
C00J N004 C00K 117.2(2) . . ?
C00E N005 C00H 118.1(2) . . ?
C009 C006 H006 109.8 . . ?
C00A C006 H006 109.8 . . ?
C00A C006 C009 100.53(17) . . ?
C00D C006 H006 109.8 . . ?
C00D C006 C009 113.83(18) . . ?
C00D C006 C00A 112.8(2) . . ?
C006 C009 H009 110.2 . . ?
C00F C009 C006 114.25(18) . . ?
C00F C009 H009 110.2 . . ?
C00F C009 C00N 111.69(18) . . ?
C00N C009 C006 99.91(17) . . ?
C00N C009 H009 110.2 . . ?
O001 C00A C006 101.60(17) . . ?
O001 C00A H00A 115.1 . . ?
O001 C00A C00L 101.6(2) . . ?
C006 C00A H00A 115.1 . . ?
C00L C00A C006 106.8(2) . . ?
C00L C00A H00A 115.1 . . ?
C00I C00B C00O 117.1(2) . . ?
C00I C00B C00Q 125.0(2) . . ?
C00O C00B C00Q 117.9(2) . . ?
C00G C00C C00M 115.1(2) . . ?
C00G C00C C00R 124.8(2) . . ?
C00M C00C C00R 120.1(2) . . ?
O002 C00D C006 113.5(2) . . ?
O007 C00D O002 122.7(2) . . ?
O007 C00D C006 123.8(2) . . ?
N005 C00E H00E 118.5 . . ?
N005 C00E C00M 123.0(2) . . ?
C00M C00E H00E 118.5 . . ?
O003 C00F C009 113.9(2) . . ?
O008 C00F O003 122.0(2) . . ?
O008 C00F C009 124.1(2) . . ?
C00C C00G H00G 119.3 . . ?
C00H C00G C00C 121.4(2) . . ?
C00H C00G H00G 119.3 . . ?
N005 C00H C00G 123.5(2) . . ?
N005 C00H H00H 118.2 . . ?
C00G C00H H00H 118.2 . . ?
C00B C00I H00I 119.5 . . ?
C00J C00I C00B 120.9(2) . . ?
C00J C00I H00I 119.5 . . ?
N004 C00J C00I 123.4(2) . . ?
N004 C00J H00J 118.3 . . ?
C00I C00J H00J 118.3 . . ?
N004 C00K H00K 118.7 . . ?
N004 C00K C00O 122.6(2) . . ?
C00O C00K H00K 118.7 . . ?
C00A C00L H00L 127.2 . . ?
C00P C00L C00A 105.6(2) . . ?
C00P C00L H00L 127.2 . . ?
C00C C00M C00E 118.8(2) . . ?
C00C C00M H00M 120.6 . . ?
C00E C00M H00M 120.6 . . ?
O001 C00N C009 101.61(17) . . ?
O001 C00N H00N 114.9 . . ?
O001 C00N C00P 101.7(2) . . ?
C009 C00N H00N 114.9 . . ?
C00P C00N C009 107.25(19) . . ?
C00P C00N H00N 114.9 . . ?
C00B C00O C00K 118.7(2) . . ?
C00B C00O H00O 120.6 . . ?
C00K C00O H00O 120.6 . . ?
C00L C00P C00N 105.7(2) . . ?
C00L C00P H00P 127.1 . . ?
C00N C00P H00P 127.1 . . ?
C00B C00Q H00Q 116.5 . . ?
C00R C00Q C00B 126.9(2) . . ?
C00R C00Q H00Q 116.5 . . ?
C00C C00R H00R 117.2 . . ?
C00Q C00R C00C 125.6(2) . . ?
C00Q C00R H00R 117.2 . . ?

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
C006 H006 O003 0.98 2.50 3.447(3) 162.2 2_567
C009 H009 O002 0.98 2.59 3.564(3) 172.6 2_567
C00M H00M O008 0.93 2.57 3.466(3) 162.4 1_645
O002 H002 N005 0.859(19) 1.82(2) 2.640(3) 159(4) 2_656
O003 H003 N004 0.886(19) 1.759(19) 2.644(3) 178(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
O001 C00A C00L C00P -32.3(3) . . . . ?
O001 C00N C00P C00L 32.4(3) . . . . ?
N004 C00K C00O C00B 0.6(4) . . . . ?
N005 C00E C00M C00C -0.9(4) . . . . ?
C006 C009 C00F O003 -96.9(2) . . . . ?
C006 C009 C00F O008 83.4(3) . . . . ?
C006 C009 C00N O001 -36.38(19) . . . . ?
C006 C009 C00N C00P 69.9(2) . . . . ?
C006 C00A C00L C00P 73.8(3) . . . . ?
C009 C006 C00A O001 35.9(2) . . . . ?
C009 C006 C00A C00L -70.1(2) . . . . ?
C009 C006 C00D O002 79.3(2) . . . . ?
C009 C006 C00D O007 -100.8(3) . . . . ?
C009 C00N C00P C00L -73.9(3) . . . . ?
C00A O001 C00N C009 60.28(19) . . . . ?
C00A O001 C00N C00P -50.3(2) . . . . ?
C00A C006 C009 C00F -119.04(19) . . . . ?
C00A C006 C009 C00N 0.31(19) . . . . ?
C00A C006 C00D O002 -167.0(2) . . . . ?
C00A C006 C00D O007 12.9(3) . . . . ?
C00A C00L C00P C00N -0.1(3) . . . . ?
C00B C00I C00J N004 0.4(5) . . . . ?
C00B C00Q C00R C00C 179.4(2) . . . . ?
C00C C00G C00H N005 -0.1(5) . . . . ?
C00D C006 C009 C00F 1.8(3) . . . . ?
C00D C006 C009 C00N 121.13(19) . . . . ?
C00D C006 C00A O001 -85.6(2) . . . . ?
C00D C006 C00A C00L 168.3(2) . . . . ?
C00E N005 C00H C00G -1.2(4) . . . . ?
C00F C009 C00N O001 84.8(2) . . . . ?
C00F C009 C00N C00P -168.9(2) . . . . ?
C00G C00C C00M C00E -0.3(4) . . . . ?
C00G C00C C00R C00Q 0.2(4) . . . . ?
C00H N005 C00E C00M 1.6(4) . . . . ?
C00I C00B C00O C00K 1.1(4) . . . . ?
C00I C00B C00Q C00R 6.8(4) . . . . ?
C00J N004 C00K C00O -1.8(4) . . . . ?
C00K N004 C00J C00I 1.3(4) . . . . ?
C00M C00C C00G C00H 0.8(4) . . . . ?
C00M C00C C00R C00Q -178.6(3) . . . . ?
C00N O001 C00A C006 -60.0(2) . . . . ?
C00N O001 C00A C00L 50.1(2) . . . . ?
C00N C009 C00F O003 150.6(2) . . . . ?
C00N C009 C00F O008 -29.0(4) . . . . ?
C00O C00B C00I C00J -1.6(4) . . . . ?
C00O C00B C00Q C00R -174.7(3) . . . . ?
C00Q C00B C00I C00J 176.9(3) . . . . ?
C00Q C00B C00O C00K -177.5(2) . . . . ?
C00R C00C C00G C00H -178.0(3) . . . . ?
C00R C00C C00M C00E 178.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Photo-sensitive
####################################################################### 
# 
# 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_mcg18136d
_database_code_depnum_ccdc_archive 'CCDC 1895859'
loop_
_audit_author_name
_audit_author_address
'Dale C. Swenson'
;University of Iowa
United States of America
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H8 O5), C24 H20 N4, C4 H8 O'
_chemical_formula_sum            'C44 H44 N4 O11'
_chemical_formula_weight         804.83
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.9162(11)
_cell_length_b                   11.3807(11)
_cell_length_c                   31.809(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3951.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8057
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      46.14
_cell_measurement_theta_min      4.401
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0567 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.9375.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            40673
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.280
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius APEX II Kappa'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5696
_reflns_number_total             6949
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 2140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         6949
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²+2.7214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O4-H4
 0.85 with sigma of 0.02
 H4-O4
 0.85 with sigma of 0.02
 C41-C42 = C42-C43 = C43-C44
 1.54 with sigma of 0.02
 C41-O9 = O9-C44
 1.46 with sigma of 0.02
 O9-C41 \\sim O9'-C41 \\sim O9-C44 \\sim O9'-C44
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O9, C41, C42, C43, C44, O9', C41', C42', C43', C44'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{O9, C41, C42, C43, C44} sigma for 1-2: 0.002, 1-3: 0.002
as
{O9', C41', C42', C43', C44'}
5. Others
 Sof(O9')=Sof(C41')=Sof(H41C)=Sof(H41D)=Sof(C42')=Sof(H42C)=Sof(H42D)=
 Sof(C43')=Sof(H43C)=Sof(H43D)=Sof(C44')=Sof(H44C)=Sof(H44D)=1-FVAR(1)
 Sof(O9)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C29(H29), C35(H35), C23(H23), C22(H22), C4(H4A), C8(H8), C1(H1), C11(H11),
 C5(H5), C14(H14), C10(H10), C15(H15)
6.b Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C41'(H41C,
 H41D), C42'(H42C,H42D), C43'(H43C,H43D), C44'(H44C,H44D)
6.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C20(H20), C40(H40), C21(H21), C3(H3), C38(H38), C18(H18), C31(H31),
 C34(H34), C2(H2A), C39(H39), C28(H28), C12(H12), C17(H17), C33(H33), C26(H26),
 C32(H32), C25(H25), C27(H27), C13(H13)
6.d Tetrahedral OH refined with riding coordinates:
 O6(H6)
6.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.2616(3) 0.5259(3) 1.39665(10) 0.0251(8) Uani 1 1 d . . . . .
O002 O 0.6671(3) 0.9549(3) 0.84931(11) 0.0298(8) Uani 1 1 d . . . . .
O2 O 0.1759(4) 0.2134(3) 1.33222(11) 0.0378(10) Uani 1 1 d . . . . .
H2 H 0.1358 0.2146 1.3097 0.057 Uiso 1 1 calc GR . . . .
O4 O 0.4807(4) 0.3348(4) 1.31247(12) 0.0494(12) Uani 1 1 d D . . . .
H4 H 0.506(8) 0.369(7) 1.2902(16) 0.09(3) Uiso 1 1 d D . . . .
O1 O 0.0561(4) 0.3655(3) 1.34963(12) 0.0397(10) Uani 1 1 d . . . . .
O8 O 0.9843(4) 1.0749(4) 0.90479(12) 0.0458(11) Uani 1 1 d . . . . .
H8A H 0.9743 1.1314 0.9215 0.069 Uiso 1 1 calc GR . . . .
O3 O 0.3124(4) 0.4424(4) 1.30713(12) 0.0482(11) Uani 1 1 d . . . . .
O6 O 0.8861(4) 0.7647(4) 0.93524(12) 0.0549(13) Uani 1 1 d . . . . .
H6 H 0.8742 0.7165 0.9548 0.082 Uiso 1 1 calc R . . . .
N1 N 1.0666(4) 0.2066(4) 1.25993(12) 0.0288(10) Uani 1 1 d . . . . .
O7 O 0.8016(4) 1.0149(4) 0.92949(13) 0.0512(12) Uani 1 1 d . . . . .
N3 N 0.9985(4) 0.1987(4) 0.97660(13) 0.0317(10) Uani 1 1 d . . . . .
N4 N 0.5604(4) 0.3721(5) 1.23403(14) 0.0392(12) Uani 1 1 d . . . . .
N2 N 0.8479(6) 0.6598(4) 1.00995(14) 0.0441(13) Uani 1 1 d . . . . .
O5 O 0.6867(5) 0.7487(4) 0.92770(14) 0.0592(13) Uani 1 1 d . . . . .
C24 C 0.7188(4) 0.3488(4) 1.16545(14) 0.0220(10) Uani 1 1 d . . . . .
C19 C 0.9672(4) 0.2348(4) 1.17926(14) 0.0192(10) Uani 1 1 d . . . . .
C36 C 0.9913(4) 0.2800(4) 1.05987(14) 0.0212(10) Uani 1 1 d . . . . .
C37 C 0.9088(5) 0.1972(4) 1.04502(14) 0.0230(10) Uani 1 1 d . . . . .
H37 H 0.8474 0.1666 1.0632 0.028 Uiso 1 1 calc R . . . .
C29 C 0.8947(4) 0.4241(4) 1.11354(13) 0.0187(10) Uani 1 1 d . . . . .
H29 H 0.9235 0.4705 1.1384 0.022 Uiso 1 1 calc R . . . .
C35 C 0.9903(4) 0.3241(4) 1.10469(13) 0.0195(10) Uani 1 1 d . . . . .
H35 H 1.0740 0.3434 1.1154 0.023 Uiso 1 1 calc R . . . .
C23 C 0.8043(4) 0.3294(4) 1.12911(14) 0.0200(10) Uani 1 1 d . . . . .
H23 H 0.7554 0.3010 1.1046 0.024 Uiso 1 1 calc R . . . .
C7 C 0.3820(5) 0.3840(5) 1.32760(15) 0.0280(12) Uani 1 1 d . . . . .
C22 C 0.9161(4) 0.2447(4) 1.13551(14) 0.0196(10) Uani 1 1 d . . . . .
H22 H 0.8999 0.1655 1.1231 0.023 Uiso 1 1 calc R . . . .
C30 C 0.8693(5) 0.5079(4) 1.07810(14) 0.0229(10) Uani 1 1 d . . . . .
C20 C 1.0312(5) 0.3246(4) 1.19930(15) 0.0255(11) Uani 1 1 d . . . . .
H20 H 1.0426 0.3979 1.1856 0.031 Uiso 1 1 calc R . . . .
C6 C 0.1472(5) 0.3061(4) 1.35499(16) 0.0283(12) Uani 1 1 d . . . . .
C40 C 1.0769(5) 0.3223(5) 1.03108(16) 0.0294(12) Uani 1 1 d . . . . .
H40 H 1.1347 0.3803 1.0393 0.035 Uiso 1 1 calc R . . . .
C4 C 0.2055(5) 0.4295(4) 1.41877(15) 0.0261(11) Uani 1 1 d . . . . .
H4A H 0.1162 0.4392 1.4248 0.031 Uiso 1 1 calc R . . . .
C21 C 1.0780(5) 0.3072(4) 1.23886(15) 0.0276(11) Uani 1 1 d . . . . .
H21 H 1.1207 0.3701 1.2519 0.033 Uiso 1 1 calc R . . . .
C8 C 0.3687(5) 0.3615(4) 1.37444(14) 0.0239(11) Uani 1 1 d . . . . .
H8 H 0.4313 0.3033 1.3842 0.029 Uiso 1 1 calc R . . . .
C3 C 0.2870(6) 0.4192(4) 1.45726(15) 0.0321(13) Uani 1 1 d . . . . .
H3 H 0.2637 0.3948 1.4847 0.039 Uiso 1 1 calc R . . . .
C38 C 0.9158(5) 0.1593(5) 1.00400(14) 0.0273(11) Uani 1 1 d . . . . .
H38 H 0.8586 0.1019 0.9947 0.033 Uiso 1 1 calc R . . . .
C1 C 0.3846(4) 0.4813(5) 1.39814(15) 0.0261(11) Uani 1 1 d . . . . .
H1 H 0.4486 0.5348 1.3863 0.031 Uiso 1 1 calc R . . . .
C18 C 0.9551(5) 0.1307(4) 1.20104(15) 0.0304(12) Uani 1 1 d . . . . .
H18 H 0.9124 0.0665 1.1888 0.036 Uiso 1 1 calc R . . . .
C31 C 0.7654(6) 0.5089(5) 1.05438(17) 0.0374(13) Uani 1 1 d . . . . .
H31 H 0.6990 0.4583 1.0611 0.045 Uiso 1 1 calc R . . . .
C11 C 0.7789(5) 1.0005(5) 0.83247(16) 0.0323(12) Uani 1 1 d . . . . .
H11 H 0.7837 1.0881 0.8306 0.039 Uiso 1 1 calc R . . . .
C34 C 0.9608(6) 0.5878(4) 1.06781(16) 0.0335(13) Uani 1 1 d . . . . .
H34 H 1.0335 0.5915 1.0842 0.040 Uiso 1 1 calc R . . . .
C2 C 0.3991(5) 0.4521(5) 1.44428(16) 0.0307(12) Uani 1 1 d . . . . .
H2A H 0.4719 0.4562 1.4606 0.037 Uiso 1 1 calc R . . . .
C39 C 1.0766(5) 0.2793(5) 0.99072(16) 0.0347(13) Uani 1 1 d . . . . .
H39 H 1.1360 0.3090 0.9717 0.042 Uiso 1 1 calc R . . . .
C9 C 0.8804(5) 1.0124(5) 0.90230(18) 0.0374(14) Uani 1 1 d . . . . .
C28 C 0.7025(6) 0.4539(5) 1.18524(18) 0.0381(14) Uani 1 1 d . . . . .
H28 H 0.7452 0.5217 1.1758 0.046 Uiso 1 1 calc R . . . .
C5 C 0.2381(4) 0.3252(4) 1.38988(14) 0.0232(11) Uani 1 1 d . . . . .
H5 H 0.2444 0.2520 1.4071 0.028 Uiso 1 1 calc R . . . .
C12 C 0.7874(5) 0.9355(5) 0.79080(16) 0.0355(13) Uani 1 1 d . . . . .
H12 H 0.8211 0.9635 0.7652 0.043 Uiso 1 1 calc R . . . .
C17 C 1.0057(6) 0.1201(5) 1.24092(17) 0.0386(14) Uani 1 1 d . . . . .
H17 H 0.9966 0.0475 1.2554 0.046 Uiso 1 1 calc R . . . .
C14 C 0.6971(6) 0.8332(5) 0.84324(16) 0.0346(13) Uani 1 1 d . . . . .
H14 H 0.6300 0.7766 0.8502 0.042 Uiso 1 1 calc R . . . .
C33 C 0.9463(6) 0.6611(5) 1.03404(17) 0.0414(15) Uani 1 1 d . . . . .
H33 H 1.0099 0.7153 1.0277 0.050 Uiso 1 1 calc R . . . .
C10 C 0.8736(5) 0.9418(6) 0.86294(16) 0.0388(15) Uani 1 1 d . . . . .
H10 H 0.9560 0.9346 0.8494 0.047 Uiso 1 1 calc R . . . .
C26 C 0.5742(6) 0.2699(6) 1.21426(18) 0.0451(16) Uani 1 1 d . . . . .
H26 H 0.5277 0.2044 1.2237 0.054 Uiso 1 1 calc R . . . .
C32 C 0.7577(6) 0.5857(6) 1.01989(19) 0.0463(16) Uani 1 1 d . . . . .
H32 H 0.6858 0.5849 1.0031 0.056 Uiso 1 1 calc R . . . .
C25 C 0.6529(6) 0.2545(5) 1.18064(17) 0.0391(14) Uani 1 1 d . . . . .
H25 H 0.6616 0.1792 1.1681 0.047 Uiso 1 1 calc R . . . .
C27 C 0.6231(6) 0.4614(6) 1.2193(2) 0.0499(17) Uani 1 1 d . . . . .
H27 H 0.6137 0.5355 1.2326 0.060 Uiso 1 1 calc R . . . .
C16 C 0.7875(7) 0.7781(6) 0.9145(2) 0.0498(17) Uani 1 1 d . . . . .
C15 C 0.8143(6) 0.8196(6) 0.86957(16) 0.0410(15) Uani 1 1 d . . . . .
H15 H 0.8674 0.7595 0.8557 0.049 Uiso 1 1 calc R . . . .
C13 C 0.7381(5) 0.8324(5) 0.79794(17) 0.0385(14) Uani 1 1 d . . . . .
H13 H 0.7299 0.7696 0.7785 0.046 Uiso 1 1 calc R . . . .
O9 O 0.8633(19) 0.3438(17) 0.8618(5) 0.156(8) Uani 0.59(2) 1 d D U P A 1
C41 C 0.795(2) 0.3557(16) 0.8995(5) 0.109(7) Uani 0.59(2) 1 d D U P A 1
H41A H 0.8503 0.3730 0.9233 0.131 Uiso 0.59(2) 1 calc R . P A 1
H41B H 0.7501 0.2821 0.9056 0.131 Uiso 0.59(2) 1 calc R . P A 1
C42 C 0.7053(17) 0.4566(12) 0.8929(5) 0.083(5) Uani 0.59(2) 1 d D U P A 1
H42A H 0.6192 0.4294 0.8933 0.100 Uiso 0.59(2) 1 calc R . P A 1
H42B H 0.7165 0.5195 0.9141 0.100 Uiso 0.59(2) 1 calc R . P A 1
C43 C 0.7450(14) 0.4956(12) 0.8494(5) 0.076(4) Uani 0.59(2) 1 d D U P A 1
H43A H 0.6723 0.5179 0.8325 0.091 Uiso 0.59(2) 1 calc R . P A 1
H43B H 0.7992 0.5651 0.8516 0.091 Uiso 0.59(2) 1 calc R . P A 1
C44 C 0.807(2) 0.4044(15) 0.8299(5) 0.106(7) Uani 0.59(2) 1 d D U P A 1
H44A H 0.7486 0.3528 0.8147 0.127 Uiso 0.59(2) 1 calc R . P A 1
H44B H 0.8677 0.4351 0.8097 0.127 Uiso 0.59(2) 1 calc R . P A 1
O9' O 0.792(4) 0.311(2) 0.8567(5) 0.31(3) Uani 0.41(2) 1 d D U P A 2
C41' C 0.824(4) 0.321(3) 0.8997(7) 0.169(18) Uani 0.41(2) 1 d D U P A 2
H41C H 0.9142 0.3184 0.9031 0.202 Uiso 0.41(2) 1 calc R . P A 2
H41D H 0.7880 0.2556 0.9161 0.202 Uiso 0.41(2) 1 calc R . P A 2
C42' C 0.774(2) 0.438(2) 0.9151(6) 0.104(9) Uani 0.41(2) 1 d D U P A 2
H42C H 0.7162 0.4284 0.9388 0.125 Uiso 0.41(2) 1 calc R . P A 2
H42D H 0.8405 0.4928 0.9234 0.125 Uiso 0.41(2) 1 calc R . P A 2
C43' C 0.710(4) 0.478(3) 0.8753(11) 0.31(4) Uani 0.41(2) 1 d D U P A 2
H43C H 0.6207 0.4625 0.8776 0.370 Uiso 0.41(2) 1 calc R . P A 2
H43D H 0.7212 0.5640 0.8715 0.370 Uiso 0.41(2) 1 calc R . P A 2
C44' C 0.758(6) 0.418(3) 0.8413(8) 0.41(5) Uani 0.41(2) 1 d D U P A 2
H44C H 0.6959 0.4098 0.8188 0.491 Uiso 0.41(2) 1 calc R . P A 2
H44D H 0.8297 0.4606 0.8297 0.491 Uiso 0.41(2) 1 calc R . 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
O001 C4 1.440(6) . ?
O001 C1 1.437(6) . ?
O002 C11 1.430(7) . ?
O002 C14 1.436(6) . ?
O2 H2 0.8400 . ?
O2 C6 1.318(6) . ?
O4 H4 0.85(2) . ?
O4 C7 1.306(6) . ?
O1 C6 1.214(6) . ?
O8 H8A 0.8400 . ?
O8 C9 1.341(7) . ?
O3 C7 1.201(6) . ?
O6 H6 0.8400 . ?
O6 C16 1.272(8) . ?
N1 C21 1.332(7) . ?
N1 C17 1.333(7) . ?
O7 C9 1.220(7) . ?
N3 C38 1.333(7) . ?
N3 C39 1.331(7) . ?
N4 C26 1.331(8) . ?
N4 C27 1.313(8) . ?
N2 C33 1.319(8) . ?
N2 C32 1.335(8) . ?
O5 C16 1.225(8) . ?
C24 C23 1.502(6) . ?
C24 C28 1.363(8) . ?
C24 C25 1.380(7) . ?
C19 C22 1.503(6) . ?
C19 C20 1.392(7) . ?
C19 C18 1.379(7) . ?
C36 C37 1.387(7) . ?
C36 C35 1.511(6) . ?
C36 C40 1.394(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.376(7) . ?
C29 H29 1.0000 . ?
C29 C35 1.569(7) . ?
C29 C23 1.543(6) . ?
C29 C30 1.502(6) . ?
C35 H35 1.0000 . ?
C35 C22 1.560(6) . ?
C23 H23 1.0000 . ?
C23 C22 1.569(7) . ?
C7 C8 1.519(6) . ?
C22 H22 1.0000 . ?
C30 C31 1.362(8) . ?
C30 C34 1.390(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.372(7) . ?
C6 C5 1.504(7) . ?
C40 H40 0.9500 . ?
C40 C39 1.374(7) . ?
C4 H4A 1.0000 . ?
C4 C3 1.518(8) . ?
C4 C5 1.542(6) . ?
C21 H21 0.9500 . ?
C8 H8 1.0000 . ?
C8 C1 1.568(7) . ?
C8 C5 1.564(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.345(8) . ?
C38 H38 0.9500 . ?
C1 H1 1.0000 . ?
C1 C2 1.513(7) . ?
C18 H18 0.9500 . ?
C18 C17 1.389(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.405(8) . ?
C11 H11 1.0000 . ?
C11 C12 1.521(8) . ?
C11 C10 1.567(8) . ?
C34 H34 0.9500 . ?
C34 C33 1.369(8) . ?
C2 H2A 0.9500 . ?
C39 H39 0.9500 . ?
C9 C10 1.490(8) . ?
C28 H28 0.9500 . ?
C28 C27 1.389(8) . ?
C5 H5 1.0000 . ?
C12 H12 0.9500 . ?
C12 C13 1.310(9) . ?
C17 H17 0.9500 . ?
C14 H14 1.0000 . ?
C14 C15 1.537(8) . ?
C14 C13 1.509(7) . ?
C33 H33 0.9500 . ?
C10 H10 1.0000 . ?
C10 C15 1.549(9) . ?
C26 H26 0.9500 . ?
C26 C25 1.383(8) . ?
C32 H32 0.9500 . ?
C25 H25 0.9500 . ?
C27 H27 0.9500 . ?
C16 C15 1.532(8) . ?
C15 H15 1.0000 . ?
C13 H13 0.9500 . ?
O9 C41 1.418(14) . ?
O9 C44 1.372(15) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C42 1.523(18) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 C43 1.518(18) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.383(17) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
O9' C41' 1.418(15) . ?
O9' C44' 1.373(15) . ?
C41' H41C 0.9900 . ?
C41' H41D 0.9900 . ?
C41' C42' 1.523(18) . ?
C42' H42C 0.9900 . ?
C42' H42D 0.9900 . ?
C42' C43' 1.517(18) . ?
C43' H43C 0.9900 . ?
C43' H43D 0.9900 . ?
C43' C44' 1.384(17) . ?
C44' H44C 0.9900 . ?
C44' H44D 0.9900 . ?

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 O001 C4 96.5(4) . . ?
C11 O002 C14 96.0(4) . . ?
C6 O2 H2 109.5 . . ?
C7 O4 H4 112(6) . . ?
C9 O8 H8A 109.5 . . ?
C16 O6 H6 109.5 . . ?
C21 N1 C17 116.9(4) . . ?
C39 N3 C38 116.5(4) . . ?
C27 N4 C26 116.7(5) . . ?
C33 N2 C32 118.1(5) . . ?
C28 C24 C23 124.4(5) . . ?
C28 C24 C25 116.9(5) . . ?
C25 C24 C23 118.6(5) . . ?
C20 C19 C22 123.7(4) . . ?
C18 C19 C22 119.6(4) . . ?
C18 C19 C20 116.6(4) . . ?
C37 C36 C35 122.8(4) . . ?
C37 C36 C40 116.5(4) . . ?
C40 C36 C35 120.7(4) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.0(4) . . ?
C38 C37 H37 120.0 . . ?
C35 C29 H29 108.4 . . ?
C23 C29 H29 108.4 . . ?
C23 C29 C35 88.6(3) . . ?
C30 C29 H29 108.4 . . ?
C30 C29 C35 116.6(4) . . ?
C30 C29 C23 124.4(4) . . ?
C36 C35 C29 114.6(4) . . ?
C36 C35 H35 112.8 . . ?
C36 C35 C22 113.8(4) . . ?
C29 C35 H35 112.8 . . ?
C22 C35 C29 87.8(3) . . ?
C22 C35 H35 112.8 . . ?
C24 C23 C29 122.8(4) . . ?
C24 C23 H23 108.5 . . ?
C24 C23 C22 118.3(4) . . ?
C29 C23 H23 108.5 . . ?
C29 C23 C22 88.5(3) . . ?
C22 C23 H23 108.5 . . ?
O4 C7 C8 111.6(4) . . ?
O3 C7 O4 124.0(5) . . ?
O3 C7 C8 124.4(5) . . ?
C19 C22 C35 115.6(4) . . ?
C19 C22 C23 117.0(4) . . ?
C19 C22 H22 111.4 . . ?
C35 C22 C23 88.0(3) . . ?
C35 C22 H22 111.4 . . ?
C23 C22 H22 111.4 . . ?
C31 C30 C29 125.1(5) . . ?
C31 C30 C34 117.5(5) . . ?
C34 C30 C29 117.3(5) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20 120.0 . . ?
O2 C6 C5 111.4(4) . . ?
O1 C6 O2 124.3(5) . . ?
O1 C6 C5 124.3(5) . . ?
C36 C40 H40 120.3 . . ?
C39 C40 C36 119.3(5) . . ?
C39 C40 H40 120.3 . . ?
O001 C4 H4A 115.1 . . ?
O001 C4 C3 101.7(4) . . ?
O001 C4 C5 101.4(3) . . ?
C3 C4 H4A 115.1 . . ?
C3 C4 C5 106.6(4) . . ?
C5 C4 H4A 115.1 . . ?
N1 C21 C20 123.4(5) . . ?
N1 C21 H21 118.3 . . ?
C20 C21 H21 118.3 . . ?
C7 C8 H8 110.5 . . ?
C7 C8 C1 108.3(4) . . ?
C7 C8 C5 116.1(4) . . ?
C1 C8 H8 110.5 . . ?
C5 C8 H8 110.5 . . ?
C5 C8 C1 100.3(4) . . ?
C4 C3 H3 127.3 . . ?
C2 C3 C4 105.3(4) . . ?
C2 C3 H3 127.3 . . ?
N3 C38 C37 123.5(5) . . ?
N3 C38 H38 118.2 . . ?
C37 C38 H38 118.2 . . ?
O001 C1 C8 100.8(4) . . ?
O001 C1 H1 115.2 . . ?
O001 C1 C2 101.9(4) . . ?
C8 C1 H1 115.2 . . ?
C2 C1 C8 106.7(4) . . ?
C2 C1 H1 115.2 . . ?
C19 C18 H18 120.1 . . ?
C19 C18 C17 119.7(5) . . ?
C17 C18 H18 120.1 . . ?
C30 C31 H31 120.4 . . ?
C30 C31 C32 119.2(6) . . ?
C32 C31 H31 120.4 . . ?
O002 C11 H11 115.4 . . ?
O002 C11 C12 101.6(4) . . ?
O002 C11 C10 100.2(4) . . ?
C12 C11 H11 115.4 . . ?
C12 C11 C10 106.9(4) . . ?
C10 C11 H11 115.4 . . ?
C30 C34 H34 120.0 . . ?
C33 C34 C30 120.0(6) . . ?
C33 C34 H34 120.0 . . ?
C3 C2 C1 105.3(5) . . ?
C3 C2 H2A 127.3 . . ?
C1 C2 H2A 127.3 . . ?
N3 C39 C40 124.2(5) . . ?
N3 C39 H39 117.9 . . ?
C40 C39 H39 117.9 . . ?
O8 C9 C10 112.2(5) . . ?
O7 C9 O8 122.8(5) . . ?
O7 C9 C10 125.0(6) . . ?
C24 C28 H28 120.2 . . ?
C24 C28 C27 119.7(5) . . ?
C27 C28 H28 120.2 . . ?
C6 C5 C4 113.5(4) . . ?
C6 C5 C8 114.1(4) . . ?
C6 C5 H5 109.2 . . ?
C4 C5 C8 101.2(4) . . ?
C4 C5 H5 109.2 . . ?
C8 C5 H5 109.2 . . ?
C11 C12 H12 127.5 . . ?
C13 C12 C11 105.0(5) . . ?
C13 C12 H12 127.5 . . ?
N1 C17 C18 123.2(5) . . ?
N1 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
O002 C14 H14 115.1 . . ?
O002 C14 C15 102.3(5) . . ?
O002 C14 C13 101.6(4) . . ?
C15 C14 H14 115.1 . . ?
C13 C14 H14 115.1 . . ?
C13 C14 C15 105.8(5) . . ?
N2 C33 C34 122.9(6) . . ?
N2 C33 H33 118.6 . . ?
C34 C33 H33 118.6 . . ?
C11 C10 H10 111.2 . . ?
C9 C10 C11 108.8(5) . . ?
C9 C10 H10 111.2 . . ?
C9 C10 C15 113.0(5) . . ?
C15 C10 C11 101.0(4) . . ?
C15 C10 H10 111.2 . . ?
N4 C26 H26 118.5 . . ?
N4 C26 C25 123.1(6) . . ?
C25 C26 H26 118.5 . . ?
N2 C32 C31 122.3(6) . . ?
N2 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C24 C25 C26 119.8(5) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
N4 C27 C28 123.8(6) . . ?
N4 C27 H27 118.1 . . ?
C28 C27 H27 118.1 . . ?
O6 C16 C15 111.1(6) . . ?
O5 C16 O6 123.3(6) . . ?
O5 C16 C15 125.1(6) . . ?
C14 C15 C10 100.6(4) . . ?
C14 C15 H15 108.1 . . ?
C10 C15 H15 108.1 . . ?
C16 C15 C14 112.4(5) . . ?
C16 C15 C10 118.9(5) . . ?
C16 C15 H15 108.1 . . ?
C12 C13 C14 106.4(5) . . ?
C12 C13 H13 126.8 . . ?
C14 C13 H13 126.8 . . ?
C44 O9 C41 109.8(15) . . ?
O9 C41 H41A 110.3 . . ?
O9 C41 H41B 110.3 . . ?
O9 C41 C42 107.1(12) . . ?
H41A C41 H41B 108.5 . . ?
C42 C41 H41A 110.3 . . ?
C42 C41 H41B 110.3 . . ?
C41 C42 H42A 111.9 . . ?
C41 C42 H42B 111.9 . . ?
H42A C42 H42B 109.6 . . ?
C43 C42 C41 99.3(11) . . ?
C43 C42 H42A 111.9 . . ?
C43 C42 H42B 111.9 . . ?
C42 C43 H43A 109.9 . . ?
C42 C43 H43B 109.9 . . ?
H43A C43 H43B 108.3 . . ?
C44 C43 C42 109.1(13) . . ?
C44 C43 H43A 109.9 . . ?
C44 C43 H43B 109.9 . . ?
O9 C44 C43 105.5(14) . . ?
O9 C44 H44A 110.6 . . ?
O9 C44 H44B 110.6 . . ?
C43 C44 H44A 110.6 . . ?
C43 C44 H44B 110.6 . . ?
H44A C44 H44B 108.8 . . ?
C44' O9' C41' 109.7(15) . . ?
O9' C41' H41C 110.3 . . ?
O9' C41' H41D 110.3 . . ?
O9' C41' C42' 107.1(13) . . ?
H41C C41' H41D 108.6 . . ?
C42' C41' H41C 110.3 . . ?
C42' C41' H41D 110.3 . . ?
C41' C42' H42C 111.9 . . ?
C41' C42' H42D 111.9 . . ?
H42C C42' H42D 109.6 . . ?
C43' C42' C41' 99.4(11) . . ?
C43' C42' H42C 111.9 . . ?
C43' C42' H42D 111.9 . . ?
C42' C43' H43C 109.9 . . ?
C42' C43' H43D 109.9 . . ?
H43C C43' H43D 108.3 . . ?
C44' C43' C42' 109.1(13) . . ?
C44' C43' H43C 109.9 . . ?
C44' C43' H43D 109.9 . . ?
O9' C44' C43' 105.3(14) . . ?
O9' C44' H44C 110.7 . . ?
O9' C44' H44D 110.7 . . ?
C43' C44' H44C 110.7 . . ?
C43' C44' H44D 110.7 . . ?
H44C C44' H44D 108.8 . . ?

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
O001 C4 C3 C2 -31.8(5) . . . . ?
O001 C4 C5 C6 -86.9(5) . . . . ?
O001 C4 C5 C8 35.8(4) . . . . ?
O001 C1 C2 C3 32.3(5) . . . . ?
O002 C11 C12 C13 -33.1(6) . . . . ?
O002 C11 C10 C9 -81.8(6) . . . . ?
O002 C11 C10 C15 37.4(5) . . . . ?
O002 C14 C15 C10 -34.5(5) . . . . ?
O002 C14 C15 C16 93.0(6) . . . . ?
O002 C14 C13 C12 31.2(6) . . . . ?
O2 C6 C5 C4 -177.3(4) . . . . ?
O2 C6 C5 C8 67.4(5) . . . . ?
O4 C7 C8 C1 112.9(5) . . . . ?
O4 C7 C8 C5 -135.3(5) . . . . ?
O1 C6 C5 C4 -0.4(7) . . . . ?
O1 C6 C5 C8 -115.6(6) . . . . ?
O8 C9 C10 C11 -106.3(6) . . . . ?
O8 C9 C10 C15 142.3(5) . . . . ?
O3 C7 C8 C1 -65.3(7) . . . . ?
O3 C7 C8 C5 46.6(7) . . . . ?
O6 C16 C15 C14 178.3(5) . . . . ?
O6 C16 C15 C10 -64.7(7) . . . . ?
O7 C9 C10 C11 73.4(8) . . . . ?
O7 C9 C10 C15 -37.9(8) . . . . ?
N4 C26 C25 C24 -2.0(10) . . . . ?
O5 C16 C15 C14 6.1(9) . . . . ?
O5 C16 C15 C10 123.1(7) . . . . ?
C24 C23 C22 C19 -29.0(6) . . . . ?
C24 C23 C22 C35 -146.9(4) . . . . ?
C24 C28 C27 N4 -0.4(10) . . . . ?
C19 C20 C21 N1 0.5(8) . . . . ?
C19 C18 C17 N1 0.1(10) . . . . ?
C36 C37 C38 N3 -0.6(8) . . . . ?
C36 C35 C22 C19 144.4(4) . . . . ?
C36 C35 C22 C23 -96.4(4) . . . . ?
C36 C40 C39 N3 0.4(9) . . . . ?
C37 C36 C35 C29 -82.2(5) . . . . ?
C37 C36 C35 C22 16.8(6) . . . . ?
C37 C36 C40 C39 -1.3(8) . . . . ?
C29 C35 C22 C19 -99.6(4) . . . . ?
C29 C35 C22 C23 19.6(3) . . . . ?
C29 C23 C22 C19 98.0(4) . . . . ?
C29 C23 C22 C35 -19.9(3) . . . . ?
C29 C30 C31 C32 -174.7(5) . . . . ?
C29 C30 C34 C33 175.7(5) . . . . ?
C35 C36 C37 C38 -179.0(5) . . . . ?
C35 C36 C40 C39 179.1(5) . . . . ?
C35 C29 C23 C24 142.9(4) . . . . ?
C35 C29 C23 C22 19.8(3) . . . . ?
C35 C29 C30 C31 106.1(6) . . . . ?
C35 C29 C30 C34 -71.6(6) . . . . ?
C23 C24 C28 C27 -178.4(5) . . . . ?
C23 C24 C25 C26 179.6(5) . . . . ?
C23 C29 C35 C36 95.4(4) . . . . ?
C23 C29 C35 C22 -19.9(3) . . . . ?
C23 C29 C30 C31 -2.1(7) . . . . ?
C23 C29 C30 C34 -179.7(4) . . . . ?
C7 C8 C1 O001 86.2(5) . . . . ?
C7 C8 C1 C2 -167.7(4) . . . . ?
C7 C8 C5 C6 5.9(6) . . . . ?
C7 C8 C5 C4 -116.3(4) . . . . ?
C22 C19 C20 C21 -178.1(5) . . . . ?
C22 C19 C18 C17 177.9(5) . . . . ?
C30 C29 C35 C36 -33.0(6) . . . . ?
C30 C29 C35 C22 -148.3(4) . . . . ?
C30 C29 C23 C24 -95.2(5) . . . . ?
C30 C29 C23 C22 141.6(4) . . . . ?
C30 C31 C32 N2 -1.4(9) . . . . ?
C30 C34 C33 N2 -0.3(8) . . . . ?
C20 C19 C22 C35 31.7(7) . . . . ?
C20 C19 C22 C23 -70.0(6) . . . . ?
C20 C19 C18 C17 0.1(8) . . . . ?
C40 C36 C37 C38 1.4(7) . . . . ?
C40 C36 C35 C29 97.4(5) . . . . ?
C40 C36 C35 C22 -163.6(4) . . . . ?
C4 O001 C1 C8 59.4(4) . . . . ?
C4 O001 C1 C2 -50.4(4) . . . . ?
C4 C3 C2 C1 -0.3(5) . . . . ?
C21 N1 C17 C18 0.0(9) . . . . ?
C8 C1 C2 C3 -72.9(5) . . . . ?
C3 C4 C5 C6 167.0(4) . . . . ?
C3 C4 C5 C8 -70.3(5) . . . . ?
C38 N3 C39 C40 0.4(8) . . . . ?
C1 O001 C4 C3 50.1(4) . . . . ?
C1 O001 C4 C5 -59.8(4) . . . . ?
C1 C8 C5 C6 122.3(4) . . . . ?
C1 C8 C5 C4 0.1(4) . . . . ?
C18 C19 C22 C35 -145.9(5) . . . . ?
C18 C19 C22 C23 112.4(5) . . . . ?
C18 C19 C20 C21 -0.4(7) . . . . ?
C31 C30 C34 C33 -2.1(8) . . . . ?
C11 O002 C14 C15 59.6(4) . . . . ?
C11 O002 C14 C13 -49.7(5) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C11 C10 C15 C14 -1.7(5) . . . . ?
C11 C10 C15 C16 -124.8(5) . . . . ?
C34 C30 C31 C32 2.9(8) . . . . ?
C39 N3 C38 C37 -0.3(8) . . . . ?
C9 C10 C15 C14 114.4(5) . . . . ?
C9 C10 C15 C16 -8.7(7) . . . . ?
C28 C24 C23 C29 7.4(8) . . . . ?
C28 C24 C23 C22 115.5(6) . . . . ?
C28 C24 C25 C26 0.5(8) . . . . ?
C5 C4 C3 C2 74.0(5) . . . . ?
C5 C8 C1 O001 -35.9(4) . . . . ?
C5 C8 C1 C2 70.2(5) . . . . ?
C12 C11 C10 C9 172.6(5) . . . . ?
C12 C11 C10 C15 -68.2(5) . . . . ?
C17 N1 C21 C20 -0.3(8) . . . . ?
C14 O002 C11 C12 50.4(4) . . . . ?
C14 O002 C11 C10 -59.5(4) . . . . ?
C33 N2 C32 C31 -1.1(9) . . . . ?
C10 C11 C12 C13 71.4(6) . . . . ?
C26 N4 C27 C28 -1.0(10) . . . . ?
C32 N2 C33 C34 1.9(9) . . . . ?
C25 C24 C23 C29 -171.6(5) . . . . ?
C25 C24 C23 C22 -63.5(6) . . . . ?
C25 C24 C28 C27 0.6(9) . . . . ?
C27 N4 C26 C25 2.1(9) . . . . ?
C15 C14 C13 C12 -75.3(6) . . . . ?
C13 C14 C15 C10 71.6(5) . . . . ?
C13 C14 C15 C16 -161.0(5) . . . . ?
O9 C41 C42 C43 -4(2) . . . . ?
C41 O9 C44 C43 29(2) . . . . ?
C41 C42 C43 C44 21.0(19) . . . . ?
C42 C43 C44 O9 -31(2) . . . . ?
C44 O9 C41 C42 -15(3) . . . . ?
O9' C41' C42' C43' 3(2) . . . . ?
C41' O9' C44' C43' -29(3) . . . . ?
C41' C42' C43' C44' -21(2) . . . . ?
C42' C43' C44' O9' 31(2) . . . . ?
C44' O9' C41' C42' 16(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT260_mcg18136d           
;
PROBLEM: Large Average Ueq of Residue Including       O9'      0.261 Check 
RESPONSE: Large Average Ueq of Residue Is Due To The Disordered Solvent Molecule
;
_vrf_PLAT097_mcg18136d           
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.86 eA-3  
RESPONSE:90% Of The Most Disagreeable Reflections Have Fo^2>Fc^2 Indicates 
         Undetected Non-Merohedral Twin
;
# 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_dalecorrectedmcg1797a_a
_database_code_depnum_ccdc_archive 'CCDC 1876029'
loop_
_audit_author_name
_audit_author_address
'Dale C. Swenson' 'University of Iowa'
_audit_update_record             
;
2019-03-04 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_audit_creation_date             2018-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'exo,exo-7-oxa-5-norbornene-2,3-dicarboxylic acid'
_chemical_formula_moiety         'C8 H8 O5'
_chemical_formula_sum            'C8 H8 O5'
_chemical_formula_weight         184.14
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2321(19)
_cell_length_b                   18.768(4)
_cell_length_c                   18.876(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.72(3)
_cell_angle_gamma                90
_cell_volume                     3263.8(11)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    6898
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      48.97
_cell_measurement_theta_min      6.128
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7253
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0696 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'slow evaporation from ethyl acetate'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            50626
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_temperature      190.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius APEX II Kappa'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                7838
_reflns_number_total             12483
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 2575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1156
_refine_ls_number_reflns         12483
_refine_ls_number_restraints     1296
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0672P)²+1.6901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1632
_refine_special_details          
'All nonhydrogen atoms were identified from the difference Fourier map within several refinement steps. Hydrogen atoms associated with carbon atoms were refined in geometrically constrained positions with isotropic thermal parameter. some reflections were omitted due to beamstop shadowing.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1 times of:
  All O(O,O) groups
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 C6-C8 \\sim C6'-C8 \\sim C7-C9 \\sim C7'-C9
 with sigma of 0.01
 C16-C18 \\sim C16'-C18 \\sim C17-C19 \\sim C17'-C19
 with sigma of 0.01
 C26-C28 \\sim C26'-C28 \\sim C27-C29 \\sim C27'-C29
 with sigma of 0.02
 C36-C38 \\sim C36'-C38 \\sim C37-C39 \\sim C37'-C39
 with sigma of 0.01
 C69-O69A \\sim C69-O69C
 with sigma of 0.01
 C69-O69B \\sim C69-O69D
 with sigma of 0.01
 O69A-O69B \\sim O69C-O69D
 with sigma of 0.01
 C78-O78A \\sim C78-O78C
 with sigma of 0.01
 C78-O78B \\sim C78-O78B
 with sigma of 0.01
 O78A-O78B \\sim O78C-O78D
 with sigma of 0.01
3. Restrained planarity
 C67, C69, O69C, O69D
 with sigma of 0.1
 C76, C78, O78C, O78D
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6')
Uanis(C7) = Uanis(C7')
Uanis(C16) = Uanis(C16')
Uanis(C17) = Uanis(C17')
Uanis(C27) = Uanis(C26')
Uanis(C27) = Uanis(C27')
Uanis(C36) = Uanis(C36')
Uanis(C37) = Uanis(C37')
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{O1, C2, C3, C4, C5, C6, C7} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1', C2', C3', C4', C5', C6', C7'}
{O11, C12, C13, C14, C15, C16, C17} sigma for 1-2: 0.02, 1-3: 0.04
as
{O11', C12', C13', C14', C15', C16', C17'}
{O21, C22, C23, C24, C25, C26, C27} sigma for 1-2: 0.02, 1-3: 0.04
as
{O21', C22', C23', C24', C25', C26', C27'}
{O31, C32, C33, C34, C35, C36, C37} sigma for 1-2: 0.02, 1-3: 0.04
as
{O31', C32', C33', C34', C35', C36', C37'}
7. Others
 Sof(O1')=Sof(C2')=Sof(H2')=Sof(C3')=Sof(H3')=Sof(C4')=Sof(H4')=Sof(C5')=
 Sof(H5')=Sof(C6')=Sof(H6')=Sof(C7')=Sof(H7')=Sof(O21')=Sof(C22')=Sof(H22')=
 Sof(C23')=Sof(H23')=Sof(C24')=Sof(H24')=Sof(C25')=Sof(H25')=Sof(C26')=
 Sof(H26')=Sof(C27')=Sof(H27')=1-FVAR(1)
 Sof(O1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(O21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=FVAR(1)
 Sof(O11')=Sof(C12')=Sof(H12')=Sof(C13')=Sof(H13')=Sof(C14')=Sof(H14')=
 Sof(C15')=Sof(H15')=Sof(C16')=Sof(H16')=Sof(C17')=Sof(H17')=Sof(O31')=
 Sof(C32')=Sof(H32')=Sof(C33')=Sof(H33')=Sof(C34')=Sof(H34')=Sof(C35')=
 Sof(H35')=Sof(C36')=Sof(H36')=Sof(C37')=Sof(H37')=1-FVAR(2)
 Sof(O11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(O31)=Sof(C32)=Sof(H32)=
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=
 Sof(C37)=Sof(H37)=FVAR(2)
 Sof(O69C)=Sof(H69C)=Sof(O69D)=Sof(O78C)=Sof(H78C)=Sof(O78D)=1-FVAR(3)
 Sof(O69B)=Sof(O69A)=Sof(H69A)=Sof(O78B)=Sof(O78A)=Sof(H78A)=FVAR(3)
8.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C2'(H2'), C5'(H5'), C6'(H6'), C7'(H7'),
 C12(H12), C15(H15), C16(H16), C17(H17), C12'(H12'), C15'(H15'), C16'(H16'),
 C17'(H17'), C22(H22), C25(H25), C26(H26), C27(H27), C22'(H22'), C25'(H25'),
 C26'(H26'), C27'(H27'), C32(H32), C35(H35), C36(H36), C37(H37), C32'(H32'),
 C35'(H35'), C36'(H36'), C37'(H37'), C42(H42), C45(H45), C46(H46), C47(H47),
 C52(H52), C55(H55), C56(H56), C57(H57), C62(H62), C65(H65), C66(H66), C67(H67),
  C72(H72), C75(H75), C76(H76), C77(H77)
8.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C3'(H3'), C4'(H4'), C13(H13), C14(H14), C13'(H13'),
 C14'(H14'), C23(H23), C24(H24), C23'(H23'), C24'(H24'), C33(H33), C34(H34),
 C33'(H33'), C34'(H34'), C43(H43), C44(H44), C53(H53), C54(H54), C63(H63),
 C64(H64), C73(H73), C74(H74)
8.c Tetrahedral OH refined with riding coordinates:
 O8A(H8A), O9A(H9A), O18A(H18A), O19A(H19A), O28A(H28A), O29A(H29A),
 O38A(H38A), O39A(H39A), O48A(H48A), O49A(H49A), O58A(H58A), O59A(H59A),
 O68A(H68A), O69A(H69A), O69C(H69C), O78A(H78A), O78C(H78C), O79A(H79A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0249(5) 0.6837(3) 0.4009(3) 0.0237(12) Uani 0.825(3) 1 d D U P A 1
C2 C 0.1259(8) 0.7120(4) 0.4528(4) 0.0195(15) Uani 0.825(3) 1 d D U P A 1
H2 H 0.0938 0.7113 0.5024 0.023 Uiso 0.825(3) 1 calc R . P A 1
C3 C 0.1558(8) 0.7856(4) 0.4240(4) 0.0175(15) Uani 0.825(3) 1 d D U P A 1
H3 H 0.1789 0.8276 0.4505 0.021 Uiso 0.825(3) 1 calc R . P A 1
C4 C 0.1430(8) 0.7789(4) 0.3542(4) 0.0224(17) Uani 0.825(3) 1 d D U P A 1
H4 H 0.1554 0.8149 0.3198 0.027 Uiso 0.825(3) 1 calc R . P A 1
C5 C 0.1044(8) 0.7014(4) 0.3410(4) 0.0238(16) Uani 0.825(3) 1 d D U P A 1
H5 H 0.0536 0.6910 0.2937 0.029 Uiso 0.825(3) 1 calc R . P A 1
C6 C 0.2550(12) 0.6600(4) 0.3572(5) 0.0231(17) Uani 0.825(3) 1 d D U P A 1
H6 H 0.3369 0.6887 0.3399 0.028 Uiso 0.825(3) 1 calc R . P A 1
C7 C 0.2557(12) 0.6648(4) 0.4404(5) 0.0198(18) Uani 0.825(3) 1 d D U P A 1
H7 H 0.3455 0.6908 0.4580 0.024 Uiso 0.825(3) 1 calc R . P A 1
O1' O 0.472(2) 0.6925(13) 0.3821(14) 0.042(6) Uani 0.175(3) 1 d D U P A 2
C2' C 0.396(3) 0.7177(15) 0.4376(15) 0.038(6) Uani 0.175(3) 1 d D U P A 2
H2' H 0.4538 0.7206 0.4840 0.045 Uiso 0.175(3) 1 calc R . P A 2
C3' C 0.336(5) 0.7890(16) 0.4101(19) 0.057(9) Uani 0.175(3) 1 d D U P A 2
H3' H 0.3163 0.8299 0.4376 0.068 Uiso 0.175(3) 1 calc R . P A 2
C4' C 0.316(5) 0.7825(16) 0.3396(19) 0.051(8) Uani 0.175(3) 1 d D U P A 2
H4' H 0.2797 0.8168 0.3060 0.061 Uiso 0.175(3) 1 calc R . P A 2
C5' C 0.367(3) 0.7074(16) 0.3263(15) 0.040(6) Uani 0.175(3) 1 d D U P A 2
H5' H 0.3962 0.6973 0.2773 0.048 Uiso 0.175(3) 1 calc R . P A 2
C6' C 0.234(5) 0.6608(11) 0.352(2) 0.0231(17) Uani 0.175(3) 1 d D U P A 2
H6' H 0.1362 0.6816 0.3390 0.028 Uiso 0.175(3) 1 calc R . P A 2
C7' C 0.277(6) 0.6605(16) 0.435(2) 0.0198(18) Uani 0.175(3) 1 d D U P A 2
H7' H 0.1954 0.6902 0.4506 0.024 Uiso 0.175(3) 1 calc R . P A 2
C8 C 0.2542(7) 0.5873(4) 0.3248(4) 0.0281(16) Uani 1 1 d D U . . .
O8A O 0.1508(5) 0.5440(3) 0.3381(3) 0.0323(12) Uani 1 1 d . U . . .
H8A H 0.1617 0.5055 0.3163 0.048 Uiso 1 1 calc R . . . .
O8B O 0.3529(5) 0.5705(3) 0.2864(3) 0.0407(14) Uani 1 1 d . U . . .
C9 C 0.2529(7) 0.5955(3) 0.4777(4) 0.0235(14) Uani 1 1 d D U . . .
O9A O 0.3608(5) 0.5525(3) 0.4640(3) 0.0327(13) Uani 1 1 d . U . . .
H9A H 0.3529 0.5142 0.4864 0.049 Uiso 1 1 calc R . . . .
O9B O 0.1616(5) 0.5803(3) 0.5200(3) 0.0348(13) Uani 1 1 d . U . . .
O11 O 0.0449(5) 0.3171(3) 0.1408(3) 0.0392(15) Uani 0.854(3) 1 d D U P B 1
C12 C 0.1415(8) 0.2901(4) 0.1979(4) 0.0284(17) Uani 0.854(3) 1 d D U P B 1
H12 H 0.1005 0.2909 0.2456 0.034 Uiso 0.854(3) 1 calc R . P B 1
C13 C 0.1786(8) 0.2163(4) 0.1716(4) 0.0248(17) Uani 0.854(3) 1 d D U P B 1
H13 H 0.1981 0.1746 0.1991 0.030 Uiso 0.854(3) 1 calc R . P B 1
C14 C 0.1776(9) 0.2227(4) 0.1028(4) 0.032(2) Uani 0.854(3) 1 d D U P B 1
H14 H 0.1973 0.1865 0.0696 0.039 Uiso 0.854(3) 1 calc R . P B 1
C15 C 0.1387(9) 0.2996(4) 0.0864(4) 0.0323(18) Uani 0.854(3) 1 d D U P B 1
H15 H 0.0979 0.3087 0.0369 0.039 Uiso 0.854(3) 1 calc R . P B 1
C16 C 0.2781(8) 0.3432(3) 0.1095(4) 0.0190(15) Uani 0.854(3) 1 d D U P B 1
H16 H 0.3660 0.3185 0.0933 0.023 Uiso 0.854(3) 1 calc R . P B 1
C17 C 0.2732(8) 0.3362(4) 0.1918(4) 0.0208(16) Uani 0.854(3) 1 d D U P B 1
H17 H 0.3616 0.3105 0.2117 0.025 Uiso 0.854(3) 1 calc R . P B 1
O11' O 0.448(3) 0.3267(17) 0.1347(17) 0.047(7) Uani 0.146(3) 1 d D U P B 2
C12' C 0.358(4) 0.2960(18) 0.1863(16) 0.040(6) Uani 0.146(3) 1 d D U P B 2
H12' H 0.4038 0.2929 0.2357 0.048 Uiso 0.146(3) 1 calc R . P B 2
C13' C 0.308(5) 0.2254(17) 0.154(2) 0.049(9) Uani 0.146(3) 1 d D U P B 2
H13' H 0.2645 0.1873 0.1779 0.058 Uiso 0.146(3) 1 calc R . P B 2
C14' C 0.335(6) 0.2266(18) 0.088(2) 0.054(9) Uani 0.146(3) 1 d D U P B 2
H14' H 0.3381 0.1879 0.0556 0.065 Uiso 0.146(3) 1 calc R . P B 2
C15' C 0.360(4) 0.3052(19) 0.0740(17) 0.044(6) Uani 0.146(3) 1 d D U P B 2
H15' H 0.3953 0.3179 0.0267 0.052 Uiso 0.146(3) 1 calc R . P B 2
C16' C 0.215(3) 0.3416(9) 0.0939(17) 0.0190(15) Uani 0.146(3) 1 d D U P B 2
H16' H 0.1213 0.3234 0.0712 0.023 Uiso 0.146(3) 1 calc R . P B 2
C17' C 0.232(4) 0.3461(15) 0.1770(16) 0.0208(16) Uani 0.146(3) 1 d D U P B 2
H17' H 0.1472 0.3198 0.1944 0.025 Uiso 0.146(3) 1 calc R . P B 2
C18 C 0.2634(8) 0.4166(4) 0.0754(4) 0.0290(16) Uani 1 1 d D U . . .
O18B O 0.1654(6) 0.4599(3) 0.0881(3) 0.0442(15) Uani 1 1 d . U . . .
O18A O 0.3541(7) 0.4291(4) 0.0304(4) 0.080(3) Uani 1 1 d . U . . .
H18A H 0.3365 0.4690 0.0116 0.120 Uiso 1 1 calc R . . . .
C19 C 0.2608(8) 0.4079(4) 0.2288(4) 0.0266(15) Uani 1 1 d D U . . .
O19B O 0.1618(5) 0.4198(3) 0.2687(3) 0.0321(12) Uani 1 1 d . U . . .
O19A O 0.3664(5) 0.4503(3) 0.2195(3) 0.0389(13) Uani 1 1 d . U . . .
H19A H 0.3488 0.4903 0.2370 0.058 Uiso 1 1 calc R . . . .
O21 O 0.5302(6) 0.8082(3) 0.3653(3) 0.0323(14) Uani 0.825(3) 1 d D U P A 1
C22 C 0.6233(9) 0.7815(4) 0.3127(4) 0.0305(18) Uani 0.825(3) 1 d D U P A 1
H22 H 0.5793 0.7822 0.2629 0.037 Uiso 0.825(3) 1 calc R . P A 1
C23 C 0.6625(9) 0.7075(4) 0.3413(4) 0.0305(19) Uani 0.825(3) 1 d D U P A 1
H23 H 0.6808 0.6657 0.3149 0.037 Uiso 0.825(3) 1 calc R . P A 1
C24 C 0.6651(9) 0.7146(4) 0.4101(4) 0.0294(18) Uani 0.825(3) 1 d D U P A 1
H24 H 0.6866 0.6783 0.4443 0.035 Uiso 0.825(3) 1 calc R . P A 1
C25 C 0.6278(9) 0.7908(4) 0.4252(4) 0.0267(17) Uani 0.825(3) 1 d D U P A 1
H25 H 0.5896 0.7998 0.4728 0.032 Uiso 0.825(3) 1 calc R . P A 1
C26 C 0.7630(12) 0.8354(4) 0.4084(5) 0.025(2) Uani 0.825(3) 1 d D U P A 1
H26 H 0.8523 0.8131 0.4316 0.030 Uiso 0.825(3) 1 calc R . P A 1
C27 C 0.7661(9) 0.8285(4) 0.3256(4) 0.0226(17) Uani 0.825(3) 1 d D U P A 1
H27 H 0.8528 0.8001 0.3135 0.027 Uiso 0.825(3) 1 calc R . P A 1
O21' O 0.974(3) 0.8238(16) 0.3530(17) 0.057(7) Uani 0.175(3) 1 d D U P A 2
C22' C 0.877(3) 0.7911(18) 0.2972(16) 0.047(6) Uani 0.175(3) 1 d D U P A 2
H22' H 0.9075 0.7951 0.2475 0.057 Uiso 0.175(3) 1 calc R . P A 2
C23' C 0.856(5) 0.7153(16) 0.326(2) 0.054(9) Uani 0.175(3) 1 d D U P A 2
H23' H 0.8404 0.6723 0.2997 0.065 Uiso 0.175(3) 1 calc R . P A 2
C24' C 0.866(5) 0.7248(17) 0.393(2) 0.061(9) Uani 0.175(3) 1 d D U P A 2
H24' H 0.8597 0.6884 0.4280 0.074 Uiso 0.175(3) 1 calc R . P A 2
C25' C 0.890(4) 0.8033(18) 0.4092(17) 0.049(6) Uani 0.175(3) 1 d D U P A 2
H25' H 0.9368 0.8134 0.4575 0.058 Uiso 0.175(3) 1 calc R . P A 2
C26' C 0.747(5) 0.8432(17) 0.392(2) 0.0226(17) Uani 0.175(3) 1 d D U P A 2
H26' H 0.6728 0.8133 0.4143 0.027 Uiso 0.175(3) 1 calc R . P A 2
C27' C 0.728(4) 0.8252(13) 0.3120(18) 0.0226(17) Uani 0.175(3) 1 d D U P A 2
H27' H 0.6380 0.7996 0.2945 0.027 Uiso 0.175(3) 1 calc R . P A 2
C28 C 0.7498(7) 0.9111(4) 0.4339(4) 0.0250(15) Uani 1 1 d D U . . .
O28B O 0.6534(6) 0.9292(3) 0.4721(3) 0.0473(16) Uani 1 1 d . U . . .
O28A O 0.8564(5) 0.9530(3) 0.4186(3) 0.0332(13) Uani 1 1 d . U . . .
H28A H 0.8479 0.9924 0.4390 0.050 Uiso 1 1 calc R . . . .
C29 C 0.7566(7) 0.8959(4) 0.2816(4) 0.0294(16) Uani 1 1 d D U . . .
O29B O 0.8506(5) 0.9089(3) 0.2400(3) 0.0352(13) Uani 1 1 d . U . . .
O29A O 0.6483(5) 0.9375(3) 0.2902(3) 0.0355(13) Uani 1 1 d . U . . .
H29A H 0.6628 0.9770 0.2710 0.053 Uiso 1 1 calc R . . . .
O31 O 0.4477(6) 0.6846(3) 0.8888(3) 0.0396(14) Uani 0.854(3) 1 d D U P B 1
C32 C 0.3537(9) 0.7101(4) 0.9396(4) 0.0354(19) Uani 0.854(3) 1 d D U P B 1
H32 H 0.3949 0.7102 0.9899 0.042 Uiso 0.854(3) 1 calc R . P B 1
C33 C 0.3073(10) 0.7818(4) 0.9099(4) 0.035(2) Uani 0.854(3) 1 d D U P B 1
H33 H 0.2828 0.8229 0.9359 0.042 Uiso 0.854(3) 1 calc R . P B 1
C34 C 0.3079(9) 0.7752(4) 0.8399(4) 0.0296(18) Uani 0.854(3) 1 d D U P B 1
H34 H 0.2845 0.8107 0.8051 0.036 Uiso 0.854(3) 1 calc R . P B 1
C35 C 0.3543(9) 0.6985(4) 0.8273(4) 0.0326(18) Uani 0.854(3) 1 d D U P B 1
H35 H 0.3988 0.6901 0.7811 0.039 Uiso 0.854(3) 1 calc R . P B 1
C36 C 0.2240(14) 0.6505(4) 0.8406(5) 0.0312(18) Uani 0.854(3) 1 d D U P B 1
H36 H 0.1348 0.6719 0.8163 0.037 Uiso 0.854(3) 1 calc R . P B 1
C37 C 0.2149(8) 0.6587(4) 0.9231(4) 0.0293(18) Uani 0.854(3) 1 d D U P B 1
H37 H 0.1233 0.6835 0.9342 0.035 Uiso 0.854(3) 1 calc R . P B 1
O31' O 0.034(3) 0.6880(17) 0.8958(18) 0.050(7) Uani 0.146(3) 1 d D U P B 2
C32' C 0.138(4) 0.7136(19) 0.9482(17) 0.041(6) Uani 0.146(3) 1 d D U P B 2
H32' H 0.1073 0.7123 0.9980 0.049 Uiso 0.146(3) 1 calc R . P B 2
C33' C 0.167(5) 0.7861(17) 0.9198(19) 0.040(9) Uani 0.146(3) 1 d D U P B 2
H33' H 0.1773 0.8298 0.9451 0.047 Uiso 0.146(3) 1 calc R . P B 2
C34' C 0.176(6) 0.7747(19) 0.8498(19) 0.050(10) Uani 0.146(3) 1 d D U P B 2
H34' H 0.2150 0.8059 0.8162 0.060 Uiso 0.146(3) 1 calc R . P B 2
C35' C 0.110(4) 0.701(2) 0.8357(17) 0.047(7) Uani 0.146(3) 1 d D U P B 2
H35' H 0.0533 0.6955 0.7892 0.056 Uiso 0.146(3) 1 calc R . P B 2
C36' C 0.237(7) 0.6474(15) 0.850(3) 0.0312(18) Uani 0.146(3) 1 d D U P B 2
H36' H 0.3193 0.6727 0.8289 0.037 Uiso 0.146(3) 1 calc R . P B 2
C37' C 0.268(4) 0.6617(13) 0.932(2) 0.0293(18) Uani 0.146(3) 1 d D U P B 2
H37' H 0.3667 0.6816 0.9447 0.035 Uiso 0.146(3) 1 calc R . P B 2
C38 C 0.2403(8) 0.5762(4) 0.8144(4) 0.0358(18) Uani 1 1 d D U . . .
O38B O 0.3422(6) 0.5585(3) 0.7793(3) 0.0472(15) Uani 1 1 d . U . . .
O38A O 0.1370(5) 0.5332(3) 0.8285(3) 0.0471(15) Uani 1 1 d . U . . .
H38A H 0.1544 0.4925 0.8125 0.071 Uiso 1 1 calc R . . . .
C39 C 0.2368(7) 0.5930(4) 0.9676(4) 0.0304(16) Uani 1 1 d D U . . .
O39B O 0.3371(6) 0.5487(3) 0.9566(3) 0.0557(18) Uani 1 1 d . U . . .
O39A O 0.1497(5) 0.5825(3) 1.0160(3) 0.0459(15) Uani 1 1 d . U . . .
H39A H 0.1664 0.5425 1.0348 0.069 Uiso 1 1 calc R . . . .
O41 O 0.2185(5) 0.9350(3) 0.5223(3) 0.0331(12) Uani 1 1 d . U . . .
C42 C 0.1167(8) 0.9603(4) 0.5697(4) 0.0259(16) Uani 1 1 d . U . . .
H42 H 0.0129 0.9588 0.5510 0.031 Uiso 1 1 calc R . . . .
C43 C 0.1761(7) 1.0348(4) 0.5876(4) 0.0243(16) Uani 1 1 d . U . . .
H43 H 0.1219 1.0757 0.5992 0.029 Uiso 1 1 calc R . . . .
C44 C 0.3161(8) 1.0304(4) 0.5836(4) 0.0296(17) Uani 1 1 d . U . . .
H44 H 0.3855 1.0676 0.5908 0.035 Uiso 1 1 calc R . . . .
C45 C 0.3446(8) 0.9530(4) 0.5649(4) 0.0297(17) Uani 1 1 d . U . . .
H45 H 0.4381 0.9442 0.5424 0.036 Uiso 1 1 calc R . . . .
C46 C 0.3236(7) 0.9089(4) 0.6344(4) 0.0227(15) Uani 1 1 d . U . . .
H46 H 0.3688 0.9349 0.6765 0.027 Uiso 1 1 calc R . . . .
C47 C 0.1547(7) 0.9125(4) 0.6351(4) 0.0200(14) Uani 1 1 d . U . . .
H47 H 0.1275 0.9376 0.6790 0.024 Uiso 1 1 calc R . . . .
C48 C 0.3902(7) 0.8360(4) 0.6299(4) 0.0229(15) Uani 1 1 d . U . . .
O48A O 0.3507(5) 0.7958(3) 0.5790(3) 0.0405(14) Uani 1 1 d . U . . .
H48A H 0.4021 0.7588 0.5805 0.061 Uiso 1 1 calc R . . . .
O48B O 0.4864(6) 0.8186(3) 0.6763(3) 0.0519(15) Uani 1 1 d . U . . .
C49 C 0.0790(7) 0.8422(4) 0.6297(4) 0.0251(16) Uani 1 1 d . U . . .
O49A O 0.1212(5) 0.7966(3) 0.6793(3) 0.0356(13) Uani 1 1 d . U . . .
H49A H 0.0812 0.7570 0.6707 0.053 Uiso 1 1 calc R . . . .
O49B O -0.0178(5) 0.8292(3) 0.5841(3) 0.0348(13) Uani 1 1 d . U . . .
O51 O 0.7753(5) 0.5600(3) 0.7274(2) 0.0293(11) Uani 1 1 d . U . . .
C52 C 0.8767(7) 0.5373(4) 0.6772(4) 0.0238(15) Uani 1 1 d . U . . .
H52 H 0.9812 0.5407 0.6944 0.029 Uiso 1 1 calc R . . . .
C53 C 0.8251(7) 0.4638(4) 0.6584(4) 0.0267(16) Uani 1 1 d . U . . .
H53 H 0.8828 0.4245 0.6459 0.032 Uiso 1 1 calc R . . . .
C54 C 0.6835(7) 0.4648(4) 0.6629(4) 0.0300(17) Uani 1 1 d . U . . .
H54 H 0.6177 0.4263 0.6541 0.036 Uiso 1 1 calc R . . . .
C55 C 0.6477(7) 0.5391(4) 0.6847(4) 0.0298(16) Uani 1 1 d . U . . .
H55 H 0.5541 0.5444 0.7080 0.036 Uiso 1 1 calc R . . . .
C56 C 0.6620(7) 0.5862(4) 0.6159(4) 0.0195(14) Uani 1 1 d . U . . .
H56 H 0.6188 0.5599 0.5736 0.023 Uiso 1 1 calc R . . . .
C57 C 0.8312(7) 0.5861(3) 0.6142(3) 0.0174(14) Uani 1 1 d . U . . .
H57 H 0.8586 0.5629 0.5693 0.021 Uiso 1 1 calc R . . . .
C58 C 0.5864(7) 0.6560(4) 0.6218(4) 0.0225(15) Uani 1 1 d . U . . .
O58A O 0.6242(5) 0.6950(3) 0.6748(3) 0.0389(14) Uani 1 1 d . U . . .
H58A H 0.5757 0.7329 0.6728 0.058 Uiso 1 1 calc R . . . .
O58B O 0.4868(6) 0.6719(3) 0.5783(3) 0.0548(17) Uani 1 1 d . U . . .
C59 C 0.9008(7) 0.6584(4) 0.6202(4) 0.0188(14) Uani 1 1 d . U . . .
O59A O 0.8525(6) 0.7044(3) 0.5724(3) 0.0369(13) Uani 1 1 d . U . . .
H59A H 0.8982 0.7429 0.5781 0.055 Uiso 1 1 calc R . . . .
O59B O 0.9970(5) 0.6721(3) 0.6673(3) 0.0346(13) Uani 1 1 d . U . . .
O61 O 0.7672(6) 0.4378(3) 0.9787(3) 0.0407(13) Uani 1 1 d . U . . .
C62 C 0.6458(8) 0.4597(4) 0.9359(4) 0.0348(18) Uani 1 1 d . U . . .
H62 H 0.5511 0.4547 0.9583 0.042 Uiso 1 1 calc R . . . .
C63 C 0.6841(8) 0.5362(4) 0.9155(4) 0.0320(17) Uani 1 1 d . U . . .
H63 H 0.6204 0.5754 0.9069 0.038 Uiso 1 1 calc R . . . .
C64 C 0.8260(7) 0.5346(4) 0.9126(4) 0.0281(16) Uani 1 1 d . U . . .
H64 H 0.8872 0.5731 0.9013 0.034 Uiso 1 1 calc R . . . .
C65 C 0.8723(8) 0.4588(4) 0.9308(4) 0.0293(16) Uani 1 1 d . U . . .
H65 H 0.9755 0.4535 0.9495 0.035 Uiso 1 1 calc R . . . .
C66 C 0.8277(7) 0.4114(4) 0.8651(4) 0.0254(15) Uani 1 1 d . U . . .
H66 H 0.8573 0.4356 0.8210 0.031 Uiso 1 1 calc R . . . .
C67 C 0.6591(7) 0.4139(4) 0.8668(4) 0.0284(16) Uani 1 1 d . U . . .
H67 H 0.6152 0.4397 0.8243 0.034 Uiso 1 1 calc R . . . .
C68 C 0.8974(8) 0.3392(4) 0.8708(4) 0.0321(17) Uani 1 1 d . U . . .
O68B O 0.9752(6) 0.3203(3) 0.9213(3) 0.0413(14) Uani 1 1 d . U . . .
O68A O 0.8723(6) 0.3004(3) 0.8145(3) 0.0505(16) Uani 1 1 d . U . . .
H68A H 0.9127 0.2606 0.8205 0.076 Uiso 1 1 calc R . . . .
C69 C 0.5861(8) 0.3432(4) 0.8753(4) 0.0320(17) Uani 1 1 d D U . . .
O69B O 0.6432(7) 0.2882(3) 0.9015(4) 0.047(2) Uani 0.840(9) 1 d D U P C 1
O69A O 0.4455(6) 0.3459(3) 0.8545(4) 0.044(2) Uani 0.840(9) 1 d D U P C 1
H69A H 0.4111 0.3044 0.8530 0.066 Uiso 0.840(9) 1 calc R . P C 1
O69C O 0.496(3) 0.322(2) 0.8211(12) 0.044 Uiso 0.160(9) 1 d DR U P C 2
H69C H 0.4898 0.2771 0.8215 0.066 Uiso 0.160(9) 1 calc R . P C 2
O69D O 0.613(4) 0.3041(18) 0.9278(12) 0.044 Uiso 0.160(9) 1 d DR U P C 2
O71 O 0.2102(5) 0.0638(3) 0.7698(2) 0.0320(12) Uani 1 1 d . U . . .
C72 C 0.1084(8) 0.0374(4) 0.8185(4) 0.0269(16) Uani 1 1 d . U . . .
H72 H 0.0040 0.0399 0.8008 0.032 Uiso 1 1 calc R . . . .
C73 C 0.1640(7) -0.0364(4) 0.8352(4) 0.0295(17) Uani 1 1 d . U . . .
H73 H 0.1087 -0.0771 0.8461 0.035 Uiso 1 1 calc R . . . .
C74 C 0.3081(8) -0.0325(4) 0.8313(5) 0.0354(19) Uani 1 1 d . U . . .
H74 H 0.3770 -0.0698 0.8390 0.042 Uiso 1 1 calc R . . . .
C75 C 0.3367(8) 0.0433(4) 0.8123(4) 0.0363(18) Uani 1 1 d . U . . .
H75 H 0.4304 0.0515 0.7898 0.044 Uiso 1 1 calc R . . . .
C76 C 0.3178(7) 0.0880(4) 0.8820(4) 0.0234(15) Uani 1 1 d . U . . .
H76 H 0.3642 0.0622 0.9239 0.028 Uiso 1 1 calc R . . . .
C77 C 0.1505(7) 0.0850(4) 0.8843(3) 0.0212(14) Uani 1 1 d . U . . .
H77 H 0.1250 0.0596 0.9284 0.025 Uiso 1 1 calc R . . . .
C78 C 0.3870(8) 0.1592(4) 0.8753(4) 0.0319(17) Uani 1 1 d D U . . .
O78B O 0.3275(7) 0.2121(4) 0.8486(4) 0.045(2) Uani 0.840(9) 1 d D U P C 1
O78A O 0.5267(6) 0.1570(3) 0.8948(4) 0.044(2) Uani 0.840(9) 1 d D U P C 1
H78A H 0.5639 0.1971 0.8885 0.066 Uiso 0.840(9) 1 calc R . P C 1
O78C O 0.470(3) 0.1794(18) 0.9314(12) 0.044 Uiso 0.160(9) 1 d DR U P C 2
H78C H 0.4965 0.2219 0.9262 0.066 Uiso 0.160(9) 1 calc R . P C 2
O78D O 0.366(4) 0.198(3) 0.8237(13) 0.044 Uiso 0.160(9) 1 d DR U P C 2
C79 C 0.0734(7) 0.1561(4) 0.8800(3) 0.0216(15) Uani 1 1 d . U . . .
O79B O -0.0113(6) 0.1731(3) 0.8305(3) 0.0409(13) Uani 1 1 d . U . . .
O79A O 0.0989(5) 0.1942(3) 0.9369(2) 0.0376(13) Uani 1 1 d . U . . .
H79A H 0.0597 0.2344 0.9311 0.056 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.412(8) . ?
O1 C5 1.427(9) . ?
C2 H2 1.0000 . ?
C2 C3 1.516(9) . ?
C2 C7 1.521(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.321(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.515(9) . ?
C5 H5 1.0000 . ?
C5 C6 1.605(12) . ?
C6 H6 1.0000 . ?
C6 C7 1.571(10) . ?
C6 C8 1.495(9) . ?
C7 H7 1.0000 . ?
C7 C9 1.480(9) . ?
O1' C2' 1.38(2) . ?
O1' C5' 1.41(2) . ?
C2' H2' 1.0000 . ?
C2' C3' 1.52(3) . ?
C2' C7' 1.53(3) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.34(3) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.51(3) . ?
C5' H5' 1.0000 . ?
C5' C6' 1.60(3) . ?
C6' H6' 1.0000 . ?
C6' C7' 1.58(3) . ?
C6' C8 1.487(13) . ?
C7' H7' 1.0000 . ?
C7' C9 1.490(13) . ?
C8 O8A 1.291(8) . ?
C8 O8B 1.242(8) . ?
O8A H8A 0.8400 . ?
C9 O9A 1.321(8) . ?
C9 O9B 1.232(8) . ?
O9A H9A 0.8400 . ?
O11 C12 1.444(9) . ?
O11 C15 1.424(9) . ?
C12 H12 1.0000 . ?
C12 C13 1.518(9) . ?
C12 C17 1.503(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.303(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.514(10) . ?
C15 H15 1.0000 . ?
C15 C16 1.562(10) . ?
C16 H16 1.0000 . ?
C16 C17 1.562(9) . ?
C16 C18 1.523(8) . ?
C17 H17 1.0000 . ?
C17 C19 1.525(8) . ?
O11' C12' 1.44(3) . ?
O11' C15' 1.42(3) . ?
C12' H12' 1.0000 . ?
C12' C13' 1.52(3) . ?
C12' C17' 1.50(3) . ?
C13' H13' 0.9500 . ?
C13' C14' 1.29(3) . ?
C14' H14' 0.9500 . ?
C14' C15' 1.52(3) . ?
C15' H15' 1.0000 . ?
C15' C16' 1.57(3) . ?
C16' H16' 1.0000 . ?
C16' C17' 1.57(3) . ?
C16' C18 1.524(14) . ?
C17' H17' 1.0000 . ?
C17' C19 1.530(13) . ?
C18 O18B 1.250(8) . ?
C18 O18A 1.253(8) . ?
O18A H18A 0.8400 . ?
C19 O19B 1.242(8) . ?
C19 O19A 1.278(8) . ?
O19A H19A 0.8400 . ?
O21 C22 1.445(9) . ?
O21 C25 1.437(9) . ?
C22 H22 1.0000 . ?
C22 C23 1.525(10) . ?
C22 C27 1.591(11) . ?
C23 H23 0.9500 . ?
C23 C24 1.305(10) . ?
C24 H24 0.9500 . ?
C24 C25 1.504(10) . ?
C25 H25 1.0000 . ?
C25 C26 1.553(13) . ?
C26 H26 1.0000 . ?
C26 C27 1.570(11) . ?
C26 C28 1.508(10) . ?
C27 H27 1.0000 . ?
C27 C29 1.512(10) . ?
O21' C22' 1.47(3) . ?
O21' C25' 1.40(3) . ?
C22' H22' 1.0000 . ?
C22' C23' 1.54(3) . ?
C22' C27' 1.56(3) . ?
C23' H23' 0.9500 . ?
C23' C24' 1.29(3) . ?
C24' H24' 0.9500 . ?
C24' C25' 1.52(3) . ?
C25' H25' 1.0000 . ?
C25' C26' 1.53(3) . ?
C26' H26' 1.0000 . ?
C26' C27' 1.55(3) . ?
C26' C28 1.50(2) . ?
C27' H27' 1.0000 . ?
C27' C29 1.48(2) . ?
C28 O28B 1.230(8) . ?
C28 O28A 1.306(8) . ?
O28A H28A 0.8400 . ?
C29 O29B 1.232(8) . ?
C29 O29A 1.289(8) . ?
O29A H29A 0.8400 . ?
O31 C32 1.418(9) . ?
O31 C35 1.424(9) . ?
C32 H32 1.0000 . ?
C32 C33 1.509(10) . ?
C32 C37 1.617(11) . ?
C33 H33 0.9500 . ?
C33 C34 1.328(10) . ?
C34 H34 0.9500 . ?
C34 C35 1.525(10) . ?
C35 H35 1.0000 . ?
C35 C36 1.536(14) . ?
C36 H36 1.0000 . ?
C36 C37 1.574(10) . ?
C36 C38 1.490(9) . ?
C37 H37 1.0000 . ?
C37 C39 1.498(9) . ?
O31' C32' 1.42(3) . ?
O31' C35' 1.40(3) . ?
C32' H32' 1.0000 . ?
C32' C33' 1.49(3) . ?
C32' C37' 1.59(3) . ?
C33' H33' 0.9500 . ?
C33' C34' 1.35(3) . ?
C34' H34' 0.9500 . ?
C34' C35' 1.53(3) . ?
C35' H35' 1.0000 . ?
C35' C36' 1.55(3) . ?
C36' H36' 1.0000 . ?
C36' C37' 1.58(3) . ?
C36' C38 1.495(14) . ?
C37' H37' 1.0000 . ?
C37' C39 1.493(14) . ?
C38 O38B 1.232(8) . ?
C38 O38A 1.291(8) . ?
O38A H38A 0.8400 . ?
C39 O39B 1.271(8) . ?
C39 O39A 1.271(8) . ?
O39A H39A 0.8400 . ?
O41 C42 1.421(8) . ?
O41 C45 1.412(9) . ?
C42 H42 1.0000 . ?
C42 C43 1.530(10) . ?
C42 C47 1.548(9) . ?
C43 H43 0.9500 . ?
C43 C44 1.303(9) . ?
C44 H44 0.9500 . ?
C44 C45 1.523(11) . ?
C45 H45 1.0000 . ?
C45 C46 1.575(10) . ?
C46 H46 1.0000 . ?
C46 C47 1.562(10) . ?
C46 C48 1.504(10) . ?
C47 H47 1.0000 . ?
C47 C49 1.493(10) . ?
C48 O48A 1.256(8) . ?
C48 O48B 1.249(8) . ?
O48A H48A 0.8400 . ?
C49 O49A 1.310(8) . ?
C49 O49B 1.224(8) . ?
O49A H49A 0.8400 . ?
O51 C52 1.439(8) . ?
O51 C55 1.438(8) . ?
C52 H52 1.0000 . ?
C52 C53 1.493(10) . ?
C52 C57 1.537(9) . ?
C53 H53 0.9500 . ?
C53 C54 1.316(10) . ?
C54 H54 0.9500 . ?
C54 C55 1.498(11) . ?
C55 H55 1.0000 . ?
C55 C56 1.583(10) . ?
C56 H56 1.0000 . ?
C56 C57 1.565(9) . ?
C56 C58 1.492(9) . ?
C57 H57 1.0000 . ?
C57 C59 1.503(9) . ?
C58 O58A 1.270(8) . ?
C58 O58B 1.229(8) . ?
O58A H58A 0.8400 . ?
C59 O59A 1.306(8) . ?
C59 O59B 1.242(8) . ?
O59A H59A 0.8400 . ?
O61 C62 1.400(9) . ?
O61 C65 1.425(9) . ?
C62 H62 1.0000 . ?
C62 C63 1.533(11) . ?
C62 C67 1.573(10) . ?
C63 H63 0.9500 . ?
C63 C64 1.315(10) . ?
C64 H64 0.9500 . ?
C64 C65 1.519(10) . ?
C65 H65 1.0000 . ?
C65 C66 1.559(10) . ?
C66 H66 1.0000 . ?
C66 C67 1.560(10) . ?
C66 C68 1.500(10) . ?
C67 H67 1.0000 . ?
C67 C69 1.503(11) . ?
C68 O68B 1.208(9) . ?
C68 O68A 1.298(9) . ?
O68A H68A 0.8400 . ?
C69 O69B 1.247(9) . ?
C69 O69A 1.332(8) . ?
C69 O69C 1.337(15) . ?
C69 O69D 1.245(16) . ?
O69A H69A 0.8400 . ?
O69C H69C 0.8400 . ?
O71 C72 1.446(8) . ?
O71 C75 1.426(9) . ?
C72 H72 1.0000 . ?
C72 C73 1.502(10) . ?
C72 C77 1.559(9) . ?
C73 H73 0.9500 . ?
C73 C74 1.339(10) . ?
C74 H74 0.9500 . ?
C74 C75 1.496(11) . ?
C75 H75 1.0000 . ?
C75 C76 1.580(10) . ?
C76 H76 1.0000 . ?
C76 C77 1.548(10) . ?
C76 C78 1.491(10) . ?
C77 H77 1.0000 . ?
C77 C79 1.512(10) . ?
C78 O78B 1.226(10) . ?
C78 O78A 1.318(8) . ?
C78 O78C 1.324(15) . ?
C78 O78D 1.22(3) . ?
O78A H78A 0.8400 . ?
O78C H78C 0.8400 . ?
C79 O79B 1.220(8) . ?
C79 O79A 1.300(8) . ?
O79A H79A 0.8400 . ?

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
C2 O1 C5 96.4(5) . . ?
O1 C2 H2 114.9 . . ?
O1 C2 C3 102.8(5) . . ?
O1 C2 C7 99.5(6) . . ?
C3 C2 H2 114.9 . . ?
C3 C2 C7 108.1(6) . . ?
C7 C2 H2 114.9 . . ?
C2 C3 H3 127.3 . . ?
C4 C3 C2 105.3(6) . . ?
C4 C3 H3 127.3 . . ?
C3 C4 H4 127.4 . . ?
C3 C4 C5 105.1(6) . . ?
C5 C4 H4 127.4 . . ?
O1 C5 C4 102.8(6) . . ?
O1 C5 H5 115.2 . . ?
O1 C5 C6 102.7(6) . . ?
C4 C5 H5 115.2 . . ?
C4 C5 C6 103.9(6) . . ?
C6 C5 H5 115.2 . . ?
C5 C6 H6 110.0 . . ?
C7 C6 C5 96.3(7) . . ?
C7 C6 H6 110.0 . . ?
C8 C6 C5 112.4(7) . . ?
C8 C6 H6 110.0 . . ?
C8 C6 C7 117.4(8) . . ?
C2 C7 C6 103.6(7) . . ?
C2 C7 H7 108.0 . . ?
C6 C7 H7 108.0 . . ?
C9 C7 C2 113.6(7) . . ?
C9 C7 C6 115.2(8) . . ?
C9 C7 H7 108.0 . . ?
C2' O1' C5' 97.9(19) . . ?
O1' C2' H2' 114.3 . . ?
O1' C2' C3' 104(2) . . ?
O1' C2' C7' 97(2) . . ?
C3' C2' H2' 114.3 . . ?
C3' C2' C7' 111(3) . . ?
C7' C2' H2' 114.3 . . ?
C2' C3' H3' 126.9 . . ?
C4' C3' C2' 106(2) . . ?
C4' C3' H3' 126.9 . . ?
C3' C4' H4' 128.4 . . ?
C3' C4' C5' 103(2) . . ?
C5' C4' H4' 128.4 . . ?
O1' C5' C4' 105(2) . . ?
O1' C5' H5' 115.9 . . ?
O1' C5' C6' 100(2) . . ?
C4' C5' H5' 115.9 . . ?
C4' C5' C6' 102(2) . . ?
C6' C5' H5' 115.9 . . ?
C5' C6' H6' 114.1 . . ?
C7' C6' C5' 99(2) . . ?
C7' C6' H6' 114.1 . . ?
C8 C6' C5' 107(2) . . ?
C8 C6' H6' 114.1 . . ?
C8 C6' C7' 108(3) . . ?
C2' C7' C6' 99.6(18) . . ?
C2' C7' H7' 98.6 . . ?
C6' C7' H7' 98.6 . . ?
C9 C7' C2' 133(3) . . ?
C9 C7' C6' 120(3) . . ?
C9 C7' H7' 98.6 . . ?
O8A C8 C6 118.7(7) . . ?
O8A C8 C6' 114.1(17) . . ?
O8B C8 C6 119.1(7) . . ?
O8B C8 C6' 123.4(17) . . ?
O8B C8 O8A 122.2(7) . . ?
C8 O8A H8A 109.5 . . ?
O9A C9 C7 114.1(6) . . ?
O9A C9 C7' 105(2) . . ?
O9B C9 C7 123.1(7) . . ?
O9B C9 C7' 133(2) . . ?
O9B C9 O9A 122.8(6) . . ?
C9 O9A H9A 109.5 . . ?
C15 O11 C12 94.7(5) . . ?
O11 C12 H12 114.5 . . ?
O11 C12 C13 102.6(6) . . ?
O11 C12 C17 101.8(6) . . ?
C13 C12 H12 114.5 . . ?
C17 C12 H12 114.5 . . ?
C17 C12 C13 107.4(6) . . ?
C12 C13 H13 127.7 . . ?
C14 C13 C12 104.7(6) . . ?
C14 C13 H13 127.7 . . ?
C13 C14 H14 126.9 . . ?
C13 C14 C15 106.2(7) . . ?
C15 C14 H14 126.9 . . ?
O11 C15 C14 102.7(6) . . ?
O11 C15 H15 115.1 . . ?
O11 C15 C16 101.9(6) . . ?
C14 C15 H15 115.1 . . ?
C14 C15 C16 105.2(6) . . ?
C16 C15 H15 115.1 . . ?
C15 C16 H16 110.0 . . ?
C17 C16 C15 99.1(5) . . ?
C17 C16 H16 110.0 . . ?
C18 C16 C15 107.9(6) . . ?
C18 C16 H16 110.0 . . ?
C18 C16 C17 119.2(6) . . ?
C12 C17 C16 101.5(5) . . ?
C12 C17 H17 109.7 . . ?
C12 C17 C19 112.9(6) . . ?
C16 C17 H17 109.7 . . ?
C19 C17 C16 113.0(6) . . ?
C19 C17 H17 109.7 . . ?
C15' O11' C12' 96(2) . . ?
O11' C12' H12' 115.1 . . ?
O11' C12' C13' 105(2) . . ?
O11' C12' C17' 99(2) . . ?
C13' C12' H12' 115.1 . . ?
C17' C12' H12' 115.1 . . ?
C17' C12' C13' 107(3) . . ?
C12' C13' H13' 126.2 . . ?
C14' C13' C12' 108(2) . . ?
C14' C13' H13' 126.2 . . ?
C13' C14' H14' 128.5 . . ?
C13' C14' C15' 103(2) . . ?
C15' C14' H14' 128.5 . . ?
O11' C15' C14' 103(2) . . ?
O11' C15' H15' 116.5 . . ?
O11' C15' C16' 98(2) . . ?
C14' C15' H15' 116.5 . . ?
C14' C15' C16' 104(3) . . ?
C16' C15' H15' 116.5 . . ?
C15' C16' H16' 118.4 . . ?
C15' C16' C17' 103(2) . . ?
C17' C16' H16' 118.4 . . ?
C18 C16' C15' 94.6(19) . . ?
C18 C16' H16' 118.4 . . ?
C18 C16' C17' 100(2) . . ?
C12' C17' C16' 96.4(18) . . ?
C12' C17' H17' 105.7 . . ?
C12' C17' C19 108(2) . . ?
C16' C17' H17' 105.7 . . ?
C19 C17' C16' 133(3) . . ?
C19 C17' H17' 105.7 . . ?
O18B C18 C16 123.6(6) . . ?
O18B C18 C16' 109.3(13) . . ?
O18B C18 O18A 122.1(7) . . ?
O18A C18 C16 114.2(6) . . ?
O18A C18 C16' 123.1(14) . . ?
C18 O18A H18A 109.5 . . ?
O19B C19 C17 121.1(6) . . ?
O19B C19 C17' 114.9(16) . . ?
O19B C19 O19A 124.7(6) . . ?
O19A C19 C17 113.9(6) . . ?
O19A C19 C17' 119.0(16) . . ?
C19 O19A H19A 109.5 . . ?
C25 O21 C22 95.2(5) . . ?
O21 C22 H22 114.7 . . ?
O21 C22 C23 102.2(6) . . ?
O21 C22 C27 103.1(6) . . ?
C23 C22 H22 114.7 . . ?
C23 C22 C27 106.0(6) . . ?
C27 C22 H22 114.7 . . ?
C22 C23 H23 127.8 . . ?
C24 C23 C22 104.4(7) . . ?
C24 C23 H23 127.8 . . ?
C23 C24 H24 126.4 . . ?
C23 C24 C25 107.2(7) . . ?
C25 C24 H24 126.4 . . ?
O21 C25 C24 101.9(6) . . ?
O21 C25 H25 115.4 . . ?
O21 C25 C26 100.8(6) . . ?
C24 C25 H25 115.4 . . ?
C24 C25 C26 106.1(6) . . ?
C26 C25 H25 115.4 . . ?
C25 C26 H26 109.6 . . ?
C25 C26 C27 103.1(7) . . ?
C27 C26 H26 109.6 . . ?
C28 C26 C25 111.1(7) . . ?
C28 C26 H26 109.6 . . ?
C28 C26 C27 113.8(7) . . ?
C22 C27 H27 109.7 . . ?
C26 C27 C22 97.5(7) . . ?
C26 C27 H27 109.7 . . ?
C29 C27 C22 111.2(6) . . ?
C29 C27 C26 118.2(7) . . ?
C29 C27 H27 109.7 . . ?
C25' O21' C22' 95.0(19) . . ?
O21' C22' H22' 116.4 . . ?
O21' C22' C23' 103(2) . . ?
O21' C22' C27' 102(2) . . ?
C23' C22' H22' 116.4 . . ?
C23' C22' C27' 101(2) . . ?
C27' C22' H22' 116.4 . . ?
C22' C23' H23' 128.8 . . ?
C24' C23' C22' 102(2) . . ?
C24' C23' H23' 128.8 . . ?
C23' C24' H24' 125.3 . . ?
C23' C24' C25' 109(2) . . ?
C25' C24' H24' 125.4 . . ?
O21' C25' C24' 101(2) . . ?
O21' C25' H25' 114.3 . . ?
O21' C25' C26' 103(2) . . ?
C24' C25' H25' 114.3 . . ?
C24' C25' C26' 109(3) . . ?
C26' C25' H25' 114.3 . . ?
C25' C26' H26' 104.3 . . ?
C25' C26' C27' 98(2) . . ?
C27' C26' H26' 104.3 . . ?
C28 C26' C25' 109(3) . . ?
C28 C26' H26' 104.3 . . ?
C28 C26' C27' 134(3) . . ?
C22' C27' H27' 117.9 . . ?
C26' C27' C22' 103(2) . . ?
C26' C27' H27' 117.9 . . ?
C29 C27' C22' 97(2) . . ?
C29 C27' C26' 100(3) . . ?
C29 C27' H27' 117.9 . . ?
O28B C28 C26 121.6(7) . . ?
O28B C28 C26' 123.8(19) . . ?
O28B C28 O28A 123.3(7) . . ?
O28A C28 C26 114.7(7) . . ?
O28A C28 C26' 112.4(19) . . ?
C28 O28A H28A 109.5 . . ?
O29B C29 C27 119.9(7) . . ?
O29B C29 C27' 125.3(15) . . ?
O29B C29 O29A 123.0(7) . . ?
O29A C29 C27 117.1(7) . . ?
O29A C29 C27' 109.7(14) . . ?
C29 O29A H29A 109.5 . . ?
C32 O31 C35 97.1(5) . . ?
O31 C32 H32 115.5 . . ?
O31 C32 C33 102.8(6) . . ?
O31 C32 C37 100.5(6) . . ?
C33 C32 H32 115.5 . . ?
C33 C32 C37 105.0(6) . . ?
C37 C32 H32 115.5 . . ?
C32 C33 H33 127.3 . . ?
C34 C33 C32 105.5(7) . . ?
C34 C33 H33 127.3 . . ?
C33 C34 H34 127.4 . . ?
C33 C34 C35 105.2(6) . . ?
C35 C34 H34 127.4 . . ?
O31 C35 C34 101.9(6) . . ?
O31 C35 H35 114.8 . . ?
O31 C35 C36 101.5(6) . . ?
C34 C35 H35 114.8 . . ?
C34 C35 C36 107.3(6) . . ?
C36 C35 H35 114.8 . . ?
C35 C36 H36 108.7 . . ?
C35 C36 C37 101.4(7) . . ?
C37 C36 H36 108.7 . . ?
C38 C36 C35 113.4(8) . . ?
C38 C36 H36 108.7 . . ?
C38 C36 C37 115.6(8) . . ?
C32 C37 H37 110.6 . . ?
C36 C37 C32 98.9(7) . . ?
C36 C37 H37 110.6 . . ?
C39 C37 C32 107.9(6) . . ?
C39 C37 C36 117.5(7) . . ?
C39 C37 H37 110.6 . . ?
C35' O31' C32' 99(2) . . ?
O31' C32' H32' 115.4 . . ?
O31' C32' C33' 101(2) . . ?
O31' C32' C37' 98(2) . . ?
C33' C32' H32' 115.4 . . ?
C33' C32' C37' 109(2) . . ?
C37' C32' H32' 115.4 . . ?
C32' C33' H33' 128.3 . . ?
C34' C33' C32' 103(2) . . ?
C34' C33' H33' 128.3 . . ?
C33' C34' H34' 127.3 . . ?
C33' C34' C35' 105(2) . . ?
C35' C34' H34' 127.3 . . ?
O31' C35' C34' 104(2) . . ?
O31' C35' H35' 115.4 . . ?
O31' C35' C36' 99(3) . . ?
C34' C35' H35' 115.4 . . ?
C34' C35' C36' 106(3) . . ?
C36' C35' H35' 115.4 . . ?
C35' C36' H36' 102.1 . . ?
C35' C36' C37' 98(2) . . ?
C37' C36' H36' 102.1 . . ?
C38 C36' C35' 123(4) . . ?
C38 C36' H36' 102.1 . . ?
C38 C36' C37' 125(4) . . ?
C32' C37' H37' 114.2 . . ?
C36' C37' C32' 102(2) . . ?
C36' C37' H37' 114.2 . . ?
C39 C37' C32' 106(2) . . ?
C39 C37' C36' 106(3) . . ?
C39 C37' H37' 114.2 . . ?
O38B C38 C36 121.9(8) . . ?
O38B C38 C36' 121(3) . . ?
O38B C38 O38A 122.8(7) . . ?
O38A C38 C36 115.2(8) . . ?
O38A C38 C36' 115(3) . . ?
C38 O38A H38A 109.5 . . ?
O39B C39 C37 121.3(6) . . ?
O39B C39 C37' 109.0(15) . . ?
O39B C39 O39A 121.2(7) . . ?
O39A C39 C37 117.5(6) . . ?
O39A C39 C37' 127.6(16) . . ?
C39 O39A H39A 109.5 . . ?
C45 O41 C42 96.6(5) . . ?
O41 C42 H42 115.2 . . ?
O41 C42 C43 101.7(5) . . ?
O41 C42 C47 100.6(5) . . ?
C43 C42 H42 115.2 . . ?
C43 C42 C47 107.1(5) . . ?
C47 C42 H42 115.2 . . ?
C42 C43 H43 127.1 . . ?
C44 C43 C42 105.8(6) . . ?
C44 C43 H43 127.1 . . ?
C43 C44 H44 127.5 . . ?
C43 C44 C45 105.0(6) . . ?
C45 C44 H44 127.5 . . ?
O41 C45 C44 102.3(6) . . ?
O41 C45 H45 115.0 . . ?
O41 C45 C46 102.0(5) . . ?
C44 C45 H45 115.0 . . ?
C44 C45 C46 106.0(6) . . ?
C46 C45 H45 115.0 . . ?
C45 C46 H46 109.7 . . ?
C47 C46 C45 99.2(5) . . ?
C47 C46 H46 109.7 . . ?
C48 C46 C45 111.0(6) . . ?
C48 C46 H46 109.7 . . ?
C48 C46 C47 116.9(5) . . ?
C42 C47 C46 101.2(5) . . ?
C42 C47 H47 109.4 . . ?
C46 C47 H47 109.4 . . ?
C49 C47 C42 112.1(6) . . ?
C49 C47 C46 115.1(5) . . ?
C49 C47 H47 109.4 . . ?
O48A C48 C46 119.3(6) . . ?
O48B C48 C46 118.2(6) . . ?
O48B C48 O48A 122.5(7) . . ?
C48 O48A H48A 109.5 . . ?
O49A C49 C47 114.4(6) . . ?
O49B C49 C47 122.8(7) . . ?
O49B C49 O49A 122.8(7) . . ?
C49 O49A H49A 109.5 . . ?
C55 O51 C52 95.4(5) . . ?
O51 C52 H52 115.0 . . ?
O51 C52 C53 102.6(6) . . ?
O51 C52 C57 100.1(5) . . ?
C53 C52 H52 115.0 . . ?
C53 C52 C57 107.5(6) . . ?
C57 C52 H52 115.0 . . ?
C52 C53 H53 127.0 . . ?
C54 C53 C52 106.0(6) . . ?
C54 C53 H53 127.0 . . ?
C53 C54 H54 127.2 . . ?
C53 C54 C55 105.5(6) . . ?
C55 C54 H54 127.2 . . ?
O51 C55 C54 102.7(5) . . ?
O51 C55 H55 115.2 . . ?
O51 C55 C56 101.4(5) . . ?
C54 C55 H55 115.2 . . ?
C54 C55 C56 105.3(6) . . ?
C56 C55 H55 115.2 . . ?
C55 C56 H56 109.2 . . ?
C57 C56 C55 98.8(5) . . ?
C57 C56 H56 109.2 . . ?
C58 C56 C55 111.4(5) . . ?
C58 C56 H56 109.2 . . ?
C58 C56 C57 118.4(5) . . ?
C52 C57 C56 102.0(5) . . ?
C52 C57 H57 109.0 . . ?
C56 C57 H57 109.0 . . ?
C59 C57 C52 112.7(6) . . ?
C59 C57 C56 114.8(5) . . ?
C59 C57 H57 109.0 . . ?
O58A C58 C56 117.2(6) . . ?
O58B C58 C56 119.8(6) . . ?
O58B C58 O58A 122.8(7) . . ?
C58 O58A H58A 109.5 . . ?
O59A C59 C57 114.8(6) . . ?
O59B C59 C57 121.5(6) . . ?
O59B C59 O59A 123.6(7) . . ?
C59 O59A H59A 109.5 . . ?
C62 O61 C65 96.0(6) . . ?
O61 C62 H62 114.6 . . ?
O61 C62 C63 103.4(6) . . ?
O61 C62 C67 102.4(6) . . ?
C63 C62 H62 114.6 . . ?
C63 C62 C67 105.7(6) . . ?
C67 C62 H62 114.6 . . ?
C62 C63 H63 128.2 . . ?
C64 C63 C62 103.7(6) . . ?
C64 C63 H63 128.2 . . ?
C63 C64 H64 126.9 . . ?
C63 C64 C65 106.1(6) . . ?
C65 C64 H64 126.9 . . ?
O61 C65 C64 102.1(6) . . ?
O61 C65 H65 114.9 . . ?
O61 C65 C66 101.1(6) . . ?
C64 C65 H65 114.9 . . ?
C64 C65 C66 107.4(6) . . ?
C66 C65 H65 114.9 . . ?
C65 C66 H66 109.3 . . ?
C65 C66 C67 100.3(5) . . ?
C67 C66 H66 109.3 . . ?
C68 C66 C65 111.5(6) . . ?
C68 C66 H66 109.3 . . ?
C68 C66 C67 116.7(6) . . ?
C62 C67 H67 110.6 . . ?
C66 C67 C62 99.5(6) . . ?
C66 C67 H67 110.6 . . ?
C69 C67 C62 109.6(6) . . ?
C69 C67 C66 115.5(6) . . ?
C69 C67 H67 110.6 . . ?
O68B C68 C66 123.5(7) . . ?
O68B C68 O68A 123.2(7) . . ?
O68A C68 C66 113.2(7) . . ?
C68 O68A H68A 109.5 . . ?
O69B C69 C67 126.3(7) . . ?
O69B C69 O69A 121.9(7) . . ?
O69A C69 C67 111.7(7) . . ?
O69C C69 C67 116.4(16) . . ?
O69D C69 C67 122.5(18) . . ?
O69D C69 O69C 121.0(17) . . ?
C69 O69A H69A 109.5 . . ?
C69 O69C H69C 109.5 . . ?
C75 O71 C72 95.2(5) . . ?
O71 C72 H72 115.0 . . ?
O71 C72 C73 102.8(6) . . ?
O71 C72 C77 99.8(5) . . ?
C73 C72 H72 115.0 . . ?
C73 C72 C77 107.3(6) . . ?
C77 C72 H72 115.0 . . ?
C72 C73 H73 127.3 . . ?
C74 C73 C72 105.4(6) . . ?
C74 C73 H73 127.3 . . ?
C73 C74 H74 127.6 . . ?
C73 C74 C75 104.8(7) . . ?
C75 C74 H74 127.6 . . ?
O71 C75 C74 103.9(6) . . ?
O71 C75 H75 114.8 . . ?
O71 C75 C76 101.3(6) . . ?
C74 C75 H75 114.8 . . ?
C74 C75 C76 105.9(6) . . ?
C76 C75 H75 114.8 . . ?
C75 C76 H76 109.7 . . ?
C77 C76 C75 99.7(5) . . ?
C77 C76 H76 109.7 . . ?
C78 C76 C75 109.4(6) . . ?
C78 C76 H76 109.7 . . ?
C78 C76 C77 117.9(6) . . ?
C72 C77 H77 109.2 . . ?
C76 C77 C72 101.3(5) . . ?
C76 C77 H77 109.2 . . ?
C79 C77 C72 111.8(5) . . ?
C79 C77 C76 115.7(5) . . ?
C79 C77 H77 109.2 . . ?
O78B C78 C76 125.3(7) . . ?
O78B C78 O78A 123.0(7) . . ?
O78A C78 C76 111.4(7) . . ?
O78C C78 C76 114.7(16) . . ?
O78D C78 C76 123(2) . . ?
O78D C78 O78C 122(2) . . ?
C78 O78A H78A 109.5 . . ?
C78 O78C H78C 109.5 . . ?
O79B C79 C77 123.3(6) . . ?
O79B C79 O79A 124.1(7) . . ?
O79A C79 C77 112.4(6) . . ?
C79 O79A H79A 109.5 . . ?

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
O8A H8A O19B 0.84 1.84 2.678(7) 173.1 .
O9A H9A O28B 0.84 1.78 2.616(8) 174.5 2_646
O18A H18A O39B 0.84 1.82 2.642(8) 164.9 1_554
O19A H19A O8B 0.84 1.77 2.593(7) 165.7 .
O28A H28A O9B 0.84 1.83 2.665(7) 176.4 2_656
O29A H29A O38B 0.84 1.80 2.626(8) 168.3 2_656
O38A H38A O29B 0.84 1.86 2.673(8) 164.1 2_646
O39A H39A O18B 0.84 1.85 2.673(8) 166.3 1_556
O48A H48A O58B 0.84 1.81 2.643(8) 170.7 .
O49A H49A O59B 0.84 1.77 2.605(7) 171.0 1_455
O58A H58A O48B 0.84 1.81 2.647(7) 173.3 .
O59A H59A O49B 0.84 1.80 2.634(7) 174.1 1_655
O68A H68A O79B 0.84 1.79 2.630(8) 176.2 1_655
O69A H69A O78B 0.84 1.90 2.737(9) 178.2 .
O69C H69C O78D 0.84 1.88 2.63(6) 146.4 .
O78A H78A O69B 0.84 1.87 2.687(9) 164.2 .
O78C H78C O69D 0.84 1.88 2.69(5) 160.8 .
O79A H79A O68B 0.84 1.80 2.636(8) 178.5 1_455

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -31.9(7) . . . . ?
O1 C2 C7 C6 42.0(7) . . . . ?
O1 C2 C7 C9 -83.8(8) . . . . ?
O1 C5 C6 C7 -30.7(7) . . . . ?
O1 C5 C6 C8 92.5(8) . . . . ?
C2 O1 C5 C4 -48.8(6) . . . . ?
C2 O1 C5 C6 59.0(6) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C2 C7 C9 O9A 176.4(7) . . . . ?
C2 C7 C9 O9B -6.4(12) . . . . ?
C3 C2 C7 C6 -65.0(8) . . . . ?
C3 C2 C7 C9 169.3(7) . . . . ?
C3 C4 C5 O1 30.8(8) . . . . ?
C3 C4 C5 C6 -76.0(8) . . . . ?
C4 C5 C6 C7 76.1(7) . . . . ?
C4 C5 C6 C8 -160.7(8) . . . . ?
C5 O1 C2 C3 49.0(6) . . . . ?
C5 O1 C2 C7 -62.3(6) . . . . ?
C5 C6 C7 C2 -6.4(8) . . . . ?
C5 C6 C7 C9 118.4(8) . . . . ?
C5 C6 C8 O8A -53.4(10) . . . . ?
C5 C6 C8 O8B 126.9(8) . . . . ?
C6 C7 C9 O9A 57.0(11) . . . . ?
C6 C7 C9 O9B -125.8(9) . . . . ?
C7 C2 C3 C4 72.7(8) . . . . ?
C7 C6 C8 O8A 57.0(11) . . . . ?
C7 C6 C8 O8B -122.7(10) . . . . ?
O1' C2' C3' C4' 30(4) . . . . ?
O1' C2' C7' C6' -48(3) . . . . ?
O1' C2' C7' C9 102(5) . . . . ?
O1' C5' C6' C7' 26(3) . . . . ?
O1' C5' C6' C8 -86(3) . . . . ?
C2' O1' C5' C4' 46(3) . . . . ?
C2' O1' C5' C6' -59(2) . . . . ?
C2' C3' C4' C5' -1(4) . . . . ?
C2' C7' C9 O9A -66(5) . . . . ?
C2' C7' C9 O9B 111(5) . . . . ?
C3' C2' C7' C6' 60(3) . . . . ?
C3' C2' C7' C9 -151(4) . . . . ?
C3' C4' C5' O1' -28(4) . . . . ?
C3' C4' C5' C6' 75(3) . . . . ?
C4' C5' C6' C7' -82(3) . . . . ?
C4' C5' C6' C8 166(3) . . . . ?
C5' O1' C2' C3' -45(3) . . . . ?
C5' O1' C2' C7' 68(2) . . . . ?
C5' C6' C7' C2' 12(3) . . . . ?
C5' C6' C7' C9 -143(4) . . . . ?
C5' C6' C8 O8A -176.5(17) . . . . ?
C5' C6' C8 O8B -4(3) . . . . ?
C6' C7' C9 O9A 78(4) . . . . ?
C6' C7' C9 O9B -105(4) . . . . ?
C7' C2' C3' C4' -74(4) . . . . ?
C7' C6' C8 O8A 78(3) . . . . ?
C7' C6' C8 O8B -109(3) . . . . ?
C8 C6 C7 C2 -125.7(8) . . . . ?
C8 C6 C7 C9 -1.0(13) . . . . ?
C8 C6' C7' C2' 123(3) . . . . ?
C8 C6' C7' C9 -32(5) . . . . ?
O11 C12 C13 C14 32.7(8) . . . . ?
O11 C12 C17 C16 -38.1(6) . . . . ?
O11 C12 C17 C19 83.1(7) . . . . ?
O11 C15 C16 C17 35.3(6) . . . . ?
O11 C15 C16 C18 -89.5(6) . . . . ?
C12 O11 C15 C14 49.5(6) . . . . ?
C12 O11 C15 C16 -59.3(6) . . . . ?
C12 C13 C14 C15 -0.6(8) . . . . ?
C12 C17 C19 O19B 10.9(9) . . . . ?
C12 C17 C19 O19A -174.7(6) . . . . ?
C13 C12 C17 C16 69.3(7) . . . . ?
C13 C12 C17 C19 -169.5(6) . . . . ?
C13 C14 C15 O11 -32.2(8) . . . . ?
C13 C14 C15 C16 74.1(8) . . . . ?
C14 C15 C16 C17 -71.5(7) . . . . ?
C14 C15 C16 C18 163.7(6) . . . . ?
C15 O11 C12 C13 -50.1(6) . . . . ?
C15 O11 C12 C17 61.1(6) . . . . ?
C15 C16 C17 C12 1.9(6) . . . . ?
C15 C16 C17 C19 -119.2(6) . . . . ?
C15 C16 C18 O18B 62.3(9) . . . . ?
C15 C16 C18 O18A -114.3(8) . . . . ?
C16 C17 C19 O19B 125.3(7) . . . . ?
C16 C17 C19 O19A -60.2(8) . . . . ?
C17 C12 C13 C14 -74.1(8) . . . . ?
C17 C16 C18 O18B -49.4(10) . . . . ?
C17 C16 C18 O18A 134.0(8) . . . . ?
O11' C12' C13' C14' -15(4) . . . . ?
O11' C12' C17' C16' 49(2) . . . . ?
O11' C12' C17' C19 -90(3) . . . . ?
O11' C15' C16' C17' -26(3) . . . . ?
O11' C15' C16' C18 75(2) . . . . ?
C12' O11' C15' C14' -50(3) . . . . ?
C12' O11' C15' C16' 57(2) . . . . ?
C12' C13' C14' C15' -16(5) . . . . ?
C12' C17' C19 O19B -126(2) . . . . ?
C12' C17' C19 O19A 67(3) . . . . ?
C13' C12' C17' C16' -59(3) . . . . ?
C13' C12' C17' C19 162(3) . . . . ?
C13' C14' C15' O11' 44(4) . . . . ?
C13' C14' C15' C16' -58(4) . . . . ?
C14' C15' C16' C17' 80(3) . . . . ?
C14' C15' C16' C18 -179(2) . . . . ?
C15' O11' C12' C13' 40(3) . . . . ?
C15' O11' C12' C17' -70(2) . . . . ?
C15' C16' C17' C12' -14(3) . . . . ?
C15' C16' C17' C19 107(3) . . . . ?
C15' C16' C18 O18B -178.6(15) . . . . ?
C15' C16' C18 O18A 27(2) . . . . ?
C16' C17' C19 O19B 117(3) . . . . ?
C16' C17' C19 O19A -51(4) . . . . ?
C17' C12' C13' C14' 89(4) . . . . ?
C17' C16' C18 O18B -74.2(19) . . . . ?
C17' C16' C18 O18A 131.5(17) . . . . ?
C18 C16 C17 C12 118.3(7) . . . . ?
C18 C16 C17 C19 -2.8(9) . . . . ?
C18 C16' C17' C12' -111(2) . . . . ?
C18 C16' C17' C19 10(4) . . . . ?
O21 C22 C23 C24 -32.5(8) . . . . ?
O21 C22 C27 C26 34.9(7) . . . . ?
O21 C22 C27 C29 -89.3(7) . . . . ?
O21 C25 C26 C27 -37.8(7) . . . . ?
O21 C25 C26 C28 84.4(7) . . . . ?
C22 O21 C25 C24 -49.5(7) . . . . ?
C22 O21 C25 C26 59.7(6) . . . . ?
C22 C23 C24 C25 0.3(9) . . . . ?
C22 C27 C29 O29B -123.3(8) . . . . ?
C22 C27 C29 O29A 57.1(9) . . . . ?
C23 C22 C27 C26 -72.1(7) . . . . ?
C23 C22 C27 C29 163.7(7) . . . . ?
C23 C24 C25 O21 32.1(8) . . . . ?
C23 C24 C25 C26 -73.0(8) . . . . ?
C24 C25 C26 C27 68.1(8) . . . . ?
C24 C25 C26 C28 -169.7(7) . . . . ?
C25 O21 C22 C23 49.9(6) . . . . ?
C25 O21 C22 C27 -59.9(6) . . . . ?
C25 C26 C27 C22 1.7(7) . . . . ?
C25 C26 C27 C29 120.7(7) . . . . ?
C25 C26 C28 O28B 10.0(11) . . . . ?
C25 C26 C28 O28A -176.8(6) . . . . ?
C26 C27 C29 O29B 125.2(8) . . . . ?
C26 C27 C29 O29A -54.4(10) . . . . ?
C27 C22 C23 C24 75.2(8) . . . . ?
C27 C26 C28 O28B 125.8(8) . . . . ?
C27 C26 C28 O28A -61.1(10) . . . . ?
O21' C22' C23' C24' 31(4) . . . . ?
O21' C22' C27' C26' -26(3) . . . . ?
O21' C22' C27' C29 76(2) . . . . ?
O21' C25' C26' C27' 46(3) . . . . ?
O21' C25' C26' C28 -96(3) . . . . ?
C22' O21' C25' C24' 49(3) . . . . ?
C22' O21' C25' C26' -63(2) . . . . ?
C22' C23' C24' C25' 1(4) . . . . ?
C22' C27' C29 O29B 19(2) . . . . ?
C22' C27' C29 O29A -177.0(14) . . . . ?
C23' C22' C27' C26' 80(3) . . . . ?
C23' C22' C27' C29 -178(2) . . . . ?
C23' C24' C25' O21' -34(4) . . . . ?
C23' C24' C25' C26' 74(4) . . . . ?
C24' C25' C26' C27' -61(3) . . . . ?
C24' C25' C26' C28 157(3) . . . . ?
C25' O21' C22' C23' -50(3) . . . . ?
C25' O21' C22' C27' 54(2) . . . . ?
C25' C26' C27' C22' -10(3) . . . . ?
C25' C26' C27' C29 -109(3) . . . . ?
C25' C26' C28 O28B -128(2) . . . . ?
C25' C26' C28 O28A 60(3) . . . . ?
C26' C27' C29 O29B 123(2) . . . . ?
C26' C27' C29 O29A -73(2) . . . . ?
C27' C22' C23' C24' -74(3) . . . . ?
C27' C26' C28 O28B 110(4) . . . . ?
C27' C26' C28 O28A -62(4) . . . . ?
C28 C26 C27 C22 -118.7(8) . . . . ?
C28 C26 C27 C29 0.3(12) . . . . ?
C28 C26' C27' C22' 116(4) . . . . ?
C28 C26' C27' C29 17(5) . . . . ?
O31 C32 C33 C34 30.9(8) . . . . ?
O31 C32 C37 C36 -34.0(7) . . . . ?
O31 C32 C37 C39 88.8(7) . . . . ?
O31 C35 C36 C37 37.7(7) . . . . ?
O31 C35 C36 C38 -86.8(9) . . . . ?
C32 O31 C35 C34 48.8(7) . . . . ?
C32 O31 C35 C36 -61.9(6) . . . . ?
C32 C33 C34 C35 0.4(9) . . . . ?
C32 C37 C39 O39B -67.3(9) . . . . ?
C32 C37 C39 O39A 114.0(8) . . . . ?
C33 C32 C37 C36 72.4(7) . . . . ?
C33 C32 C37 C39 -164.8(6) . . . . ?
C33 C34 C35 O31 -31.3(8) . . . . ?
C33 C34 C35 C36 74.9(9) . . . . ?
C34 C35 C36 C37 -68.8(8) . . . . ?
C34 C35 C36 C38 166.6(8) . . . . ?
C35 O31 C32 C33 -49.0(7) . . . . ?
C35 O31 C32 C37 59.2(6) . . . . ?
C35 C36 C37 C32 -2.1(7) . . . . ?
C35 C36 C37 C39 -117.7(7) . . . . ?
C35 C36 C38 O38B -7.1(13) . . . . ?
C35 C36 C38 O38A 176.0(7) . . . . ?
C36 C37 C39 O39B 43.3(12) . . . . ?
C36 C37 C39 O39A -135.4(8) . . . . ?
C37 C32 C33 C34 -73.8(8) . . . . ?
C37 C36 C38 O38B -123.6(10) . . . . ?
C37 C36 C38 O38A 59.5(12) . . . . ?
O31' C32' C33' C34' -43(4) . . . . ?
O31' C32' C37' C36' 30(3) . . . . ?
O31' C32' C37' C39 -81(3) . . . . ?
O31' C35' C36' C37' -42(3) . . . . ?
O31' C35' C36' C38 100(4) . . . . ?
C32' O31' C35' C34' -42(3) . . . . ?
C32' O31' C35' C36' 66(3) . . . . ?
C32' C33' C34' C35' 15(4) . . . . ?
C32' C37' C39 O39B 180.0(19) . . . . ?
C32' C37' C39 O39A -17(3) . . . . ?
C33' C32' C37' C36' -75(3) . . . . ?
C33' C32' C37' C39 175(3) . . . . ?
C33' C34' C35' O31' 17(4) . . . . ?
C33' C34' C35' C36' -87(4) . . . . ?
C34' C35' C36' C37' 65(3) . . . . ?
C34' C35' C36' C38 -153(4) . . . . ?
C35' O31' C32' C33' 52(3) . . . . ?
C35' O31' C32' C37' -59(2) . . . . ?
C35' C36' C37' C32' 7(3) . . . . ?
C35' C36' C37' C39 117(3) . . . . ?
C35' C36' C38 O38B 123(4) . . . . ?
C35' C36' C38 O38A -63(5) . . . . ?
C36' C37' C39 O39B 73(3) . . . . ?
C36' C37' C39 O39A -124(3) . . . . ?
C37' C32' C33' C34' 60(4) . . . . ?
C37' C36' C38 O38B -104(5) . . . . ?
C37' C36' C38 O38A 70(5) . . . . ?
C38 C36 C37 C32 121.0(9) . . . . ?
C38 C36 C37 C39 5.4(13) . . . . ?
C38 C36' C37' C32' -134(5) . . . . ?
C38 C36' C37' C39 -24(5) . . . . ?
O41 C42 C43 C44 -30.4(7) . . . . ?
O41 C42 C47 C46 38.3(6) . . . . ?
O41 C42 C47 C49 -84.9(7) . . . . ?
O41 C45 C46 C47 -33.5(6) . . . . ?
O41 C45 C46 C48 90.0(6) . . . . ?
C42 O41 C45 C44 -50.2(6) . . . . ?
C42 O41 C45 C46 59.4(6) . . . . ?
C42 C43 C44 C45 -1.2(8) . . . . ?
C42 C47 C49 O49A 171.9(6) . . . . ?
C42 C47 C49 O49B -10.3(9) . . . . ?
C43 C42 C47 C46 -67.5(6) . . . . ?
C43 C42 C47 C49 169.3(6) . . . . ?
C43 C44 C45 O41 32.9(7) . . . . ?
C43 C44 C45 C46 -73.5(7) . . . . ?
C44 C45 C46 C47 73.1(6) . . . . ?
C44 C45 C46 C48 -163.3(6) . . . . ?
C45 O41 C42 C43 49.0(6) . . . . ?
C45 O41 C42 C47 -61.1(6) . . . . ?
C45 C46 C47 C42 -2.9(6) . . . . ?
C45 C46 C47 C49 118.2(7) . . . . ?
C45 C46 C48 O48A -56.4(8) . . . . ?
C45 C46 C48 O48B 121.7(7) . . . . ?
C46 C47 C49 O49A 57.0(8) . . . . ?
C46 C47 C49 O49B -125.2(7) . . . . ?
C47 C42 C43 C44 74.6(7) . . . . ?
C47 C46 C48 O48A 56.4(9) . . . . ?
C47 C46 C48 O48B -125.5(7) . . . . ?
C48 C46 C47 C42 -122.2(7) . . . . ?
C48 C46 C47 C49 -1.1(9) . . . . ?
O51 C52 C53 C54 31.7(7) . . . . ?
O51 C52 C57 C56 -39.4(6) . . . . ?
O51 C52 C57 C59 84.2(6) . . . . ?
O51 C55 C56 C57 34.2(6) . . . . ?
O51 C55 C56 C58 -91.1(6) . . . . ?
C52 O51 C55 C54 48.6(6) . . . . ?
C52 O51 C55 C56 -60.2(6) . . . . ?
C52 C53 C54 C55 -0.2(8) . . . . ?
C52 C57 C59 O59A -172.3(5) . . . . ?
C52 C57 C59 O59B 7.9(9) . . . . ?
C53 C52 C57 C56 67.4(6) . . . . ?
C53 C52 C57 C59 -169.0(5) . . . . ?
C53 C54 C55 O51 -31.5(8) . . . . ?
C53 C54 C55 C56 74.3(7) . . . . ?
C54 C55 C56 C57 -72.5(6) . . . . ?
C54 C55 C56 C58 162.2(6) . . . . ?
C55 O51 C52 C53 -48.6(6) . . . . ?
C55 O51 C52 C57 62.0(6) . . . . ?
C55 C56 C57 C52 3.1(6) . . . . ?
C55 C56 C57 C59 -119.2(6) . . . . ?
C55 C56 C58 O58A 56.3(8) . . . . ?
C55 C56 C58 O58B -119.9(7) . . . . ?
C56 C57 C59 O59A -56.1(8) . . . . ?
C56 C57 C59 O59B 124.1(7) . . . . ?
C57 C52 C53 C54 -73.3(7) . . . . ?
C57 C56 C58 O58A -57.2(9) . . . . ?
C57 C56 C58 O58B 126.6(7) . . . . ?
C58 C56 C57 C52 123.3(6) . . . . ?
C58 C56 C57 C59 1.1(9) . . . . ?
O61 C62 C63 C64 32.3(8) . . . . ?
O61 C62 C67 C66 -34.4(7) . . . . ?
O61 C62 C67 C69 87.2(7) . . . . ?
O61 C65 C66 C67 38.0(6) . . . . ?
O61 C65 C66 C68 -86.3(7) . . . . ?
C62 O61 C65 C64 49.6(6) . . . . ?
C62 O61 C65 C66 -61.1(6) . . . . ?
C62 C63 C64 C65 0.1(8) . . . . ?
C62 C67 C69 O69B -88.4(10) . . . . ?
C62 C67 C69 O69A 88.2(8) . . . . ?
C62 C67 C69 O69C 133(2) . . . . ?
C62 C67 C69 O69D -51(2) . . . . ?
C63 C62 C67 C66 73.6(7) . . . . ?
C63 C62 C67 C69 -164.9(6) . . . . ?
C63 C64 C65 O61 -31.6(7) . . . . ?
C63 C64 C65 C66 74.2(8) . . . . ?
C64 C65 C66 C67 -68.5(6) . . . . ?
C64 C65 C66 C68 167.2(6) . . . . ?
C65 O61 C62 C63 -50.1(6) . . . . ?
C65 O61 C62 C67 59.6(6) . . . . ?
C65 C66 C67 C62 -2.5(6) . . . . ?
C65 C66 C67 C69 -119.7(7) . . . . ?
C65 C66 C68 O68B 1.8(10) . . . . ?
C65 C66 C68 O68A -174.7(6) . . . . ?
C66 C67 C69 O69B 23.0(12) . . . . ?
C66 C67 C69 O69A -160.4(7) . . . . ?
C66 C67 C69 O69C -116(2) . . . . ?
C66 C67 C69 O69D 60(2) . . . . ?
C67 C62 C63 C64 -75.0(7) . . . . ?
C67 C66 C68 O68B -112.6(8) . . . . ?
C67 C66 C68 O68A 70.9(9) . . . . ?
C68 C66 C67 C62 118.1(7) . . . . ?
C68 C66 C67 C69 0.9(10) . . . . ?
O71 C72 C73 C74 31.4(7) . . . . ?
O71 C72 C77 C76 -38.7(6) . . . . ?
O71 C72 C77 C79 85.1(6) . . . . ?
O71 C75 C76 C77 35.3(6) . . . . ?
O71 C75 C76 C78 -89.1(7) . . . . ?
C72 O71 C75 C74 49.0(6) . . . . ?
C72 O71 C75 C76 -60.7(6) . . . . ?
C72 C73 C74 C75 -0.1(8) . . . . ?
C72 C77 C79 O79B 0.1(9) . . . . ?
C72 C77 C79 O79A 175.1(6) . . . . ?
C73 C72 C77 C76 68.2(6) . . . . ?
C73 C72 C77 C79 -168.0(6) . . . . ?
C73 C74 C75 O71 -31.9(8) . . . . ?
C73 C74 C75 C76 74.4(8) . . . . ?
C74 C75 C76 C77 -72.9(7) . . . . ?
C74 C75 C76 C78 162.8(6) . . . . ?
C75 O71 C72 C73 -48.5(6) . . . . ?
C75 O71 C72 C77 61.9(6) . . . . ?
C75 C76 C77 C72 2.3(6) . . . . ?
C75 C76 C77 C79 -118.7(6) . . . . ?
C75 C76 C78 O78B 87.4(10) . . . . ?
C75 C76 C78 O78A -85.8(8) . . . . ?
C75 C76 C78 O78C -133.5(18) . . . . ?
C75 C76 C78 O78D 49(2) . . . . ?
C76 C77 C79 O79B 115.4(7) . . . . ?
C76 C77 C79 O79A -69.6(8) . . . . ?
C77 C72 C73 C74 -73.3(8) . . . . ?
C77 C76 C78 O78B -25.5(11) . . . . ?
C77 C76 C78 O78A 161.3(6) . . . . ?
C77 C76 C78 O78C 113.6(18) . . . . ?
C77 C76 C78 O78D -64(2) . . . . ?
C78 C76 C77 C72 120.6(7) . . . . ?
C78 C76 C77 C79 -0.5(9) . . . . ?

_olex2_submission_original_sample_id mcg1797
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT340_dalecorrectedmcg1797a_a 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01019 Ang.  
RESPONSE: Low Bond Precision is Due to The Large Amount of Disorder
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# end Validation Reply Form
