# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_18a
_database_code_depnum_ccdc_archive 'CCDC 1404687'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Ethyl 2,2-dioxo-6-phenyl-1H,3H-pyrazolo[1,5-c][1,3]thiazole-7-carboxylate'
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H14 N2 O4 S'
_chemical_formula_sum            'C14 H14 N2 O4 S'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         306.33

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7862(3)
_cell_length_b                   20.9598(7)
_cell_length_c                   8.5716(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.059(2)
_cell_angle_gamma                90
_cell_volume                     1405.73(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6245
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      30.58
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18485
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.943
_diffrn_reflns_theta_max         31.969
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4845
_reflns_number_gt                3803
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.2227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4845
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.25385(4) 0.15170(2) 0.59266(4) 0.02871(9) Uani 1 1 d . . . . .
O1 O 0.09649(13) 0.17786(5) 0.57532(13) 0.0364(2) Uani 1 1 d . . . . .
O2 O 0.33919(15) 0.18230(5) 0.50586(14) 0.0443(3) Uani 1 1 d . . . . .
O3 O 0.45065(13) 0.02254(5) 1.29589(12) 0.0407(2) Uani 1 1 d . . . . .
O4 O 0.49694(12) 0.11496(4) 1.19252(12) 0.0338(2) Uani 1 1 d . . . . .
N4 N 0.23855(13) 0.04328(5) 0.70508(13) 0.0267(2) Uani 1 1 d . . . . .
N5 N 0.17104(13) -0.01121(5) 0.73100(13) 0.0268(2) Uani 1 1 d . . . . .
C1 C 0.39378(17) 0.13859(6) 0.82267(17) 0.0325(3) Uani 1 1 d . . . . .
H1A H 0.5148 0.1357 0.8462 0.039 Uiso 1 1 calc R U . . .
H1B H 0.3816 0.1727 0.8960 0.039 Uiso 1 1 calc R U . . .
C3 C 0.22052(17) 0.06756(6) 0.53998(16) 0.0297(2) Uani 1 1 d . . . . .
H3A H 0.1054 0.0590 0.4432 0.036 Uiso 1 1 calc R U . . .
H3B H 0.3084 0.0499 0.5099 0.036 Uiso 1 1 calc R U . . .
C6 C 0.22488(14) -0.01314(5) 0.90481(14) 0.0241(2) Uani 1 1 d . . . . .
C7 C 0.32700(14) 0.04133(5) 0.98828(15) 0.0246(2) Uani 1 1 d . . . . .
C7A C 0.32965(15) 0.07632(6) 0.85247(15) 0.0258(2) Uani 1 1 d . . . . .
C8 C 0.16419(14) -0.06684(5) 0.97293(15) 0.0245(2) Uani 1 1 d . . . . .
C9 C 0.11452(17) -0.12346(6) 0.87669(17) 0.0310(2) Uani 1 1 d . . . . .
H9 H 0.1299 -0.1281 0.7745 0.037 Uiso 1 1 calc R U . . .
C10 C 0.0434(2) -0.17277(6) 0.9284(2) 0.0382(3) Uani 1 1 d . . . . .
H10 H 0.0081 -0.2107 0.8603 0.046 Uiso 1 1 calc R U . . .
C11 C 0.02331(19) -0.16722(7) 1.0789(2) 0.0389(3) Uani 1 1 d . . . . .
H11 H -0.0251 -0.2012 1.1149 0.047 Uiso 1 1 calc R U . . .
C12 C 0.07443(17) -0.11169(7) 1.17644(18) 0.0353(3) Uani 1 1 d . . . . .
H12 H 0.0622 -0.1079 1.2806 0.042 Uiso 1 1 calc R U . . .
C13 C 0.14342(16) -0.06149(6) 1.12375(16) 0.0296(2) Uani 1 1 d . . . . .
H13 H 0.1765 -0.0234 1.1910 0.036 Uiso 1 1 calc R U . . .
C14 C 0.42717(15) 0.05705(6) 1.17395(16) 0.0275(2) Uani 1 1 d . . . . .
C15 C 0.61109(18) 0.13499(7) 1.36960(18) 0.0384(3) Uani 1 1 d . . . . .
H15A H 0.7219 0.1125 1.4125 0.046 Uiso 1 1 calc R U . . .
H15B H 0.5605 0.1251 1.4490 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6365(3) 0.20495(9) 1.3648(3) 0.0585(5) Uani 1 1 d . . . . .
H16A H 0.6897 0.2140 1.2885 0.088 Uiso 1 1 calc R U . . .
H16B H 0.7109 0.2203 1.4834 0.088 Uiso 1 1 calc R U . . .
H16C H 0.5257 0.2266 1.3194 0.088 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O2 1.4265(10) . ?
S2 O1 1.4309(10) . ?
S2 C1 1.8080(13) . ?
S2 C3 1.8108(13) . ?
O3 C14 1.2092(15) . ?
O4 C14 1.3361(15) . ?
O4 C15 1.4495(16) . ?
N4 C7A 1.3403(15) . ?
N4 N5 1.3511(14) . ?
N4 C3 1.4432(14) . ?
N5 C6 1.3431(14) . ?
C1 C7A 1.4890(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C7 1.4269(17) . ?
C6 C8 1.4749(15) . ?
C7 C7A 1.3849(15) . ?
C7 C14 1.4635(16) . ?
C8 C13 1.3899(16) . ?
C8 C9 1.3970(17) . ?
C9 C10 1.3809(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3883(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.487(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S2 O1 119.06(6) . . ?
O2 S2 C1 112.28(6) . . ?
O1 S2 C1 108.49(6) . . ?
O2 S2 C3 111.82(6) . . ?
O1 S2 C3 107.96(6) . . ?
C1 S2 C3 94.39(6) . . ?
C14 O4 C15 116.69(10) . . ?
C7A N4 N5 113.60(9) . . ?
C7A N4 C3 119.62(10) . . ?
N5 N4 C3 126.78(10) . . ?
C6 N5 N4 104.38(9) . . ?
C7A C1 S2 101.40(8) . . ?
C7A C1 H1A 111.5 . . ?
S2 C1 H1A 111.5 . . ?
C7A C1 H1B 111.5 . . ?
S2 C1 H1B 111.5 . . ?
H1A C1 H1B 109.3 . . ?
N4 C3 S2 99.54(8) . . ?
N4 C3 H3A 111.9 . . ?
S2 C3 H3A 111.9 . . ?
N4 C3 H3B 111.9 . . ?
S2 C3 H3B 111.9 . . ?
H3A C3 H3B 109.6 . . ?
N5 C6 C7 110.86(10) . . ?
N5 C6 C8 116.98(10) . . ?
C7 C6 C8 132.08(10) . . ?
C7A C7 C6 104.44(10) . . ?
C7A C7 C14 124.27(11) . . ?
C6 C7 C14 130.95(10) . . ?
N4 C7A C7 106.71(10) . . ?
N4 C7A C1 113.67(10) . . ?
C7 C7A C1 139.52(11) . . ?
C13 C8 C9 118.67(11) . . ?
C13 C8 C6 122.05(11) . . ?
C9 C8 C6 119.12(10) . . ?
C10 C9 C8 120.79(12) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.28(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.33(13) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.72(12) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 120.20(12) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
O3 C14 O4 123.50(12) . . ?
O3 C14 C7 125.94(12) . . ?
O4 C14 C7 110.51(10) . . ?
O4 C15 C16 107.33(13) . . ?
O4 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O4 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7A N4 N5 C6 -1.01(13) . . . . ?
C3 N4 N5 C6 179.33(11) . . . . ?
O2 S2 C1 C7A -144.49(9) . . . . ?
O1 S2 C1 C7A 81.83(9) . . . . ?
C3 S2 C1 C7A -28.76(9) . . . . ?
C7A N4 C3 S2 -24.58(13) . . . . ?
N5 N4 C3 S2 155.06(10) . . . . ?
O2 S2 C3 N4 146.01(8) . . . . ?
O1 S2 C3 N4 -81.16(9) . . . . ?
C1 S2 C3 N4 29.89(9) . . . . ?
N4 N5 C6 C7 0.30(12) . . . . ?
N4 N5 C6 C8 177.38(9) . . . . ?
N5 C6 C7 C7A 0.45(13) . . . . ?
C8 C6 C7 C7A -176.04(11) . . . . ?
N5 C6 C7 C14 -172.86(11) . . . . ?
C8 C6 C7 C14 10.6(2) . . . . ?
N5 N4 C7A C7 1.32(14) . . . . ?
C3 N4 C7A C7 -178.99(10) . . . . ?
N5 N4 C7A C1 -175.89(10) . . . . ?
C3 N4 C7A C1 3.79(16) . . . . ?
C6 C7 C7A N4 -1.02(13) . . . . ?
C14 C7 C7A N4 172.87(10) . . . . ?
C6 C7 C7A C1 175.05(14) . . . . ?
C14 C7 C7A C1 -11.1(2) . . . . ?
S2 C1 C7A N4 19.37(12) . . . . ?
S2 C1 C7A C7 -156.52(14) . . . . ?
N5 C6 C8 C13 -150.84(11) . . . . ?
C7 C6 C8 C13 25.48(19) . . . . ?
N5 C6 C8 C9 24.56(16) . . . . ?
C7 C6 C8 C9 -159.12(12) . . . . ?
C13 C8 C9 C10 1.13(19) . . . . ?
C6 C8 C9 C10 -174.43(11) . . . . ?
C8 C9 C10 C11 -1.3(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C8 -0.9(2) . . . . ?
C9 C8 C13 C12 -0.05(18) . . . . ?
C6 C8 C13 C12 175.37(11) . . . . ?
C15 O4 C14 O3 2.32(18) . . . . ?
C15 O4 C14 C7 -175.28(10) . . . . ?
C7A C7 C14 O3 -166.77(13) . . . . ?
C6 C7 C14 O3 5.4(2) . . . . ?
C7A C7 C14 O4 10.76(16) . . . . ?
C6 C7 C14 O4 -177.09(11) . . . . ?
C14 O4 C15 C16 -165.42(13) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.051

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_41
_database_code_depnum_ccdc_archive 'CCDC 1404688'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"'(4aR,7aR,8aR)-Dimethyl 8-benzyl-5,7-dioxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-1H,3H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyridine-2,3-dicarboxylate'"
_chemical_name_common            ?
_chemical_formula_moiety         'C26 H23 N3 O6'
_chemical_formula_sum            'C26 H23 N3 O6'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         473.47

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.8055(17)
_cell_length_b                   14.5445(19)
_cell_length_c                   14.594(2)
_cell_angle_alpha                98.060(6)
_cell_angle_beta                 99.289(7)
_cell_angle_gamma                115.517(6)
_cell_volume                     2352.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1801
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      20.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25820
_diffrn_reflns_av_unetI/netI     0.1663
_diffrn_reflns_av_R_equivalents  0.1036
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.596
_diffrn_reflns_theta_max         25.909
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9063
_reflns_number_gt                4179
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9063
_refine_ls_number_parameters     635
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1744
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_restrained_S_all      0.872
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0963(2) 0.2028(2) 0.44974(17) 0.0429(7) Uani 1 1 d . . . . .
O2 O 0.0567(2) 0.29517(19) 0.57804(17) 0.0366(7) Uani 1 1 d . . . . .
O3 O 0.0512(2) 0.12118(19) 0.66493(16) 0.0330(6) Uani 1 1 d . . . . .
O4 O 0.1968(2) 0.07592(19) 0.65825(16) 0.0334(6) Uani 1 1 d . . . . .
O5 O 0.4895(2) 0.16954(19) 0.57363(17) 0.0391(7) Uani 1 1 d . . . . .
O6 O 0.4054(2) 0.28007(19) 0.30815(17) 0.0360(7) Uani 1 1 d . . . . .
N1 N 0.0852(2) 0.1603(2) 0.38275(19) 0.0247(7) Uani 1 1 d . . . . .
N6 N 0.4644(2) 0.2484(2) 0.45202(19) 0.0246(7) Uani 1 1 d . . . . .
N9 N 0.1496(2) 0.1068(2) 0.38148(18) 0.0223(7) Uani 1 1 d . . . . .
C2 C 0.0704(3) 0.1694(2) 0.4711(2) 0.0227(8) Uani 1 1 d . . . . .
C3 C 0.1246(3) 0.1221(3) 0.5259(2) 0.0225(8) Uani 1 1 d . . . . .
C3A C 0.1734(3) 0.0806(2) 0.4641(2) 0.0213(8) Uani 1 1 d . . . . .
C4 C 0.2374(3) 0.0162(3) 0.4657(2) 0.0221(8) Uani 1 1 d . . . . .
H4A H 0.1831 -0.0562 0.4277 0.026 Uiso 1 1 calc R U . . .
H4B H 0.2646 0.0132 0.5321 0.026 Uiso 1 1 calc R U . . .
C4A C 0.3450(3) 0.0660(3) 0.4233(2) 0.0229(8) Uani 1 1 d . . . . .
H40A H 0.3768 0.0150 0.4092 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4413(3) 0.1639(3) 0.4932(3) 0.0267(9) Uani 1 1 d . . . . .
C7 C 0.3970(3) 0.2190(3) 0.3572(2) 0.0251(8) Uani 1 1 d . . . . .
C7A C 0.3177(3) 0.1025(2) 0.3316(2) 0.0213(8) Uani 1 1 d . . . . .
H7A H 0.3414 0.0695 0.2795 0.026 Uiso 1 1 calc R U . . .
C8 C 0.1845(3) 0.0731(3) 0.2980(2) 0.0247(8) Uani 1 1 d . . . . .
H8 H 0.1392 -0.0052 0.2790 0.030 Uiso 1 1 calc R U . . .
C10 C 0.1490(3) 0.1134(3) 0.2134(2) 0.0283(9) Uani 1 1 d . . . . .
H10A H 0.0627 0.0931 0.2014 0.034 Uiso 1 1 calc R U . . .
H10B H 0.1937 0.1909 0.2293 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0003(3) 0.2232(3) 0.4963(2) 0.0265(8) Uani 1 1 d . . . . .
C12 C -0.0108(4) 0.3437(3) 0.6144(3) 0.0552(13) Uani 1 1 d . . . . .
H12A H -0.0307 0.3803 0.5685 0.083 Uiso 1 1 calc R U . . .
H12B H 0.0372 0.3940 0.6755 0.083 Uiso 1 1 calc R U . . .
H12C H -0.0844 0.2897 0.6238 0.083 Uiso 1 1 calc R U . . .
C13 C 0.1180(3) 0.1079(3) 0.6226(2) 0.0251(8) Uani 1 1 d . . . . .
C14 C 0.1896(3) 0.0472(3) 0.7485(2) 0.0381(10) Uani 1 1 d . . . . .
H14A H 0.1990 0.1065 0.7964 0.057 Uiso 1 1 calc R U . . .
H14B H 0.2532 0.0286 0.7692 0.057 Uiso 1 1 calc R U . . .
H14C H 0.1118 -0.0131 0.7413 0.057 Uiso 1 1 calc R U . . .
C15 C 0.5462(3) 0.3537(3) 0.5026(2) 0.0282(9) Uani 1 1 d . . . . .
C16 C 0.6500(4) 0.4053(3) 0.4769(3) 0.0494(11) Uani 1 1 d . . . . .
H16 H 0.6685 0.3716 0.4261 0.059 Uiso 1 1 calc R U . . .
C17 C 0.7289(4) 0.5086(3) 0.5260(3) 0.0653(14) Uani 1 1 d . . . . .
H17 H 0.8012 0.5462 0.5084 0.078 Uiso 1 1 calc R U . . .
C18 C 0.7009(4) 0.5554(3) 0.6003(3) 0.0519(12) Uani 1 1 d . . . . .
H18 H 0.7550 0.6252 0.6349 0.062 Uiso 1 1 calc R U . . .
C19 C 0.5968(4) 0.5026(3) 0.6245(3) 0.0392(10) Uani 1 1 d . . . . .
H19 H 0.5781 0.5356 0.6757 0.047 Uiso 1 1 calc R U . . .
C20 C 0.5184(3) 0.4016(3) 0.5754(2) 0.0331(9) Uani 1 1 d . . . . .
H20 H 0.4450 0.3651 0.5918 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1741(3) 0.0702(3) 0.1242(2) 0.0285(9) Uani 1 1 d . . . . .
C22 C 0.2556(3) 0.1342(3) 0.0822(2) 0.0363(10) Uani 1 1 d . . . . .
H22 H 0.2977 0.2074 0.1097 0.044 Uiso 1 1 calc R U . . .
C23 C 0.2779(4) 0.0942(4) 0.0006(3) 0.0510(12) Uani 1 1 d . . . . .
H23 H 0.3338 0.1403 -0.0283 0.061 Uiso 1 1 calc R U . . .
C24 C 0.2200(5) -0.0116(4) -0.0392(3) 0.0631(15) Uani 1 1 d . . . . .
H24 H 0.2371 -0.0393 -0.0944 0.076 Uiso 1 1 calc R U . . .
C25 C 0.1386(6) -0.0757(4) 0.0010(3) 0.084(2) Uani 1 1 d . . . . .
H25 H 0.0970 -0.1489 -0.0268 0.101 Uiso 1 1 calc R U . . .
C26 C 0.1149(5) -0.0354(3) 0.0828(3) 0.0658(15) Uani 1 1 d . . . . .
H26 H 0.0571 -0.0815 0.1103 0.079 Uiso 1 1 calc R U . . .
O1' O 0.8852(3) 0.4226(2) 1.23232(17) 0.0452(8) Uani 1 1 d . . . . .
O2' O 0.9123(2) 0.2898(2) 1.16672(16) 0.0384(7) Uani 1 1 d . . . . .
O3' O 1.0953(2) 0.37581(19) 1.06290(17) 0.0364(7) Uani 1 1 d . . . . .
O4' O 1.0180(2) 0.30619(19) 0.90550(17) 0.0371(7) Uani 1 1 d . . . . .
O5' O 0.7308(2) 0.1474(2) 0.70190(19) 0.0437(7) Uani 1 1 d . . . . .
O6' O 0.4620(2) 0.18676(18) 0.84820(19) 0.0383(7) Uani 1 1 d . . . . .
N1' N 0.7662(2) 0.3958(2) 1.03659(18) 0.0247(7) Uani 1 1 d . . . . .
N6' N 0.5841(2) 0.1441(2) 0.77469(19) 0.0244(7) Uani 1 1 d . . . . .
N9' N 0.7590(2) 0.3934(2) 0.94315(18) 0.0230(7) Uani 1 1 d . . . . .
C2' C 0.8580(3) 0.3775(3) 1.0639(2) 0.0243(8) Uani 1 1 d . . . . .
C3' C 0.9090(3) 0.3630(3) 0.9886(2) 0.0240(8) Uani 1 1 d . . . . .
C3A' C 0.8414(3) 0.3748(3) 0.9108(2) 0.0233(8) Uani 1 1 d . . . . .
C4' C 0.8403(3) 0.3741(3) 0.8086(2) 0.0261(8) Uani 1 1 d . . . . .
H4'1 H 0.8930 0.3456 0.7888 0.031 Uiso 1 1 calc R U . . .
H4'2 H 0.8706 0.4465 0.7996 0.031 Uiso 1 1 calc R U . . .
C4A' C 0.7114(3) 0.3057(3) 0.7468(2) 0.0240(8) Uani 1 1 d . . . . .
H4A' H 0.7053 0.3218 0.6824 0.029 Uiso 1 1 calc R U . . .
C5' C 0.6802(3) 0.1908(3) 0.7359(2) 0.0298(9) Uani 1 1 d . . . . .
C7' C 0.5440(3) 0.2134(3) 0.8108(2) 0.0265(8) Uani 1 1 d . . . . .
C7A' C 0.6158(3) 0.3184(3) 0.7911(2) 0.0236(8) Uani 1 1 d . . . . .
H7A' H 0.5627 0.3314 0.7421 0.028 Uiso 1 1 calc R U . . .
C8' C 0.6678(3) 0.4088(3) 0.8799(2) 0.0237(8) Uani 1 1 d . . . . .
H8' H 0.7106 0.4752 0.8594 0.028 Uiso 1 1 calc R U . . .
C10' C 0.5813(3) 0.4223(3) 0.9325(2) 0.0269(9) Uani 1 1 d . . . . .
H10C H 0.6262 0.4781 0.9918 0.032 Uiso 1 1 calc R U . . .
H10D H 0.5339 0.3563 0.9506 0.032 Uiso 1 1 calc R U . . .
C11' C 0.8867(3) 0.3680(3) 1.1636(2) 0.0270(9) Uani 1 1 d . . . . .
C12' C 0.9497(4) 0.2764(3) 1.2600(3) 0.0521(12) Uani 1 1 d . . . . .
H12D H 1.0114 0.3440 1.3008 0.078 Uiso 1 1 calc R U . . .
H12E H 0.9823 0.2265 1.2547 0.078 Uiso 1 1 calc R U . . .
H12F H 0.8811 0.2495 1.2882 0.078 Uiso 1 1 calc R U . . .
C13' C 1.0170(3) 0.3505(3) 0.9918(3) 0.0286(9) Uani 1 1 d . . . . .
C14' C 1.1248(4) 0.2973(4) 0.9004(3) 0.0578(13) Uani 1 1 d . . . . .
H14D H 1.1924 0.3675 0.9129 0.087 Uiso 1 1 calc R U . . .
H14E H 1.1141 0.2577 0.8365 0.087 Uiso 1 1 calc R U . . .
H14F H 1.1404 0.2607 0.9481 0.087 Uiso 1 1 calc R U . . .
C15' C 0.4977(3) 0.4508(3) 0.8709(2) 0.0249(8) Uani 1 1 d . . . . .
C16' C 0.5289(3) 0.5547(3) 0.8753(2) 0.0310(9) Uani 1 1 d . . . . .
H16' H 0.6029 0.6074 0.9160 0.037 Uiso 1 1 calc R U . . .
C17' C 0.4541(4) 0.5837(3) 0.8213(3) 0.0384(10) Uani 1 1 d . . . . .
H17' H 0.4764 0.6559 0.8261 0.046 Uiso 1 1 calc R U . . .
C18' C 0.3482(4) 0.5090(3) 0.7609(3) 0.0413(11) Uani 1 1 d . . . . .
H18' H 0.2969 0.5288 0.7236 0.050 Uiso 1 1 calc R U . . .
C19' C 0.3172(4) 0.4049(3) 0.7550(3) 0.0426(11) Uani 1 1 d . . . . .
H19' H 0.2443 0.3523 0.7129 0.051 Uiso 1 1 calc R U . . .
C20' C 0.3919(3) 0.3764(3) 0.8104(3) 0.0352(10) Uani 1 1 d . . . . .
H20' H 0.3694 0.3042 0.8061 0.042 Uiso 1 1 calc R U . . .
C21' C 0.5208(3) 0.0339(3) 0.7703(3) 0.0285(9) Uani 1 1 d . . . . .
C22' C 0.5362(4) -0.0036(3) 0.8496(3) 0.0415(10) Uani 1 1 d . . . . .
H22' H 0.5915 0.0420 0.9077 0.050 Uiso 1 1 calc R U . . .
C23' C 0.4684(4) -0.1106(3) 0.8431(3) 0.0476(11) Uani 1 1 d . . . . .
H23' H 0.4779 -0.1383 0.8972 0.057 Uiso 1 1 calc R U . . .
C24' C 0.3887(4) -0.1757(3) 0.7596(3) 0.0486(12) Uani 1 1 d . . . . .
H24' H 0.3423 -0.2481 0.7563 0.058 Uiso 1 1 calc R U . . .
C25' C 0.3754(3) -0.1371(3) 0.6804(3) 0.0428(11) Uani 1 1 d . . . . .
H25' H 0.3212 -0.1829 0.6221 0.051 Uiso 1 1 calc R U . . .
C26' C 0.4407(3) -0.0316(3) 0.6857(3) 0.0321(9) Uani 1 1 d . . . . .
H26' H 0.4306 -0.0042 0.6315 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.198(4) . ?
O2 C11 1.327(4) . ?
O2 C12 1.448(4) . ?
O3 C13 1.196(4) . ?
O4 C13 1.344(4) . ?
O4 C14 1.442(4) . ?
O5 C5 1.209(4) . ?
O6 C7 1.197(4) . ?
N1 C2 1.329(4) . ?
N1 N9 1.356(4) . ?
N6 C5 1.383(4) . ?
N6 C7 1.405(4) . ?
N6 C15 1.428(4) . ?
N9 C3A 1.343(4) . ?
N9 C8 1.457(4) . ?
C2 C3 1.407(4) . ?
C2 C11 1.478(5) . ?
C3 C3A 1.387(5) . ?
C3 C13 1.465(5) . ?
C3A C4 1.487(4) . ?
C4 C4A 1.532(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4A C5 1.504(4) . ?
C4A C7A 1.550(4) . ?
C4A H40A 1.0000 . ?
C7 C7A 1.504(5) . ?
C7A C8 1.541(4) . ?
C7A H7A 1.0000 . ?
C8 C10 1.525(4) . ?
C8 H8 1.0000 . ?
C10 C21 1.508(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.361(5) . ?
C15 C20 1.367(5) . ?
C16 C17 1.395(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.356(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.364(5) . ?
C21 C26 1.374(5) . ?
C22 C23 1.377(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.346(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
O1' C11' 1.197(4) . ?
O2' C11' 1.318(4) . ?
O2' C12' 1.437(4) . ?
O3' C13' 1.207(4) . ?
O4' C13' 1.336(4) . ?
O4' C14' 1.440(4) . ?
O5' C5' 1.197(4) . ?
O6' C7' 1.202(4) . ?
N1' C2' 1.326(4) . ?
N1' N9' 1.346(4) . ?
N6' C5' 1.381(5) . ?
N6' C7' 1.394(4) . ?
N6' C21' 1.437(4) . ?
N9' C3A' 1.335(4) . ?
N9' C8' 1.484(4) . ?
C2' C3' 1.401(5) . ?
C2' C11' 1.483(5) . ?
C3' C3A' 1.391(4) . ?
C3' C13' 1.465(5) . ?
C3A' C4' 1.487(5) . ?
C4' C4A' 1.543(4) . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?
C4A' C5' 1.518(5) . ?
C4A' C7A' 1.539(5) . ?
C4A' H4A' 1.0000 . ?
C7' C7A' 1.503(5) . ?
C7A' C8' 1.530(4) . ?
C7A' H7A' 1.0000 . ?
C8' C10' 1.508(5) . ?
C8' H8' 1.0000 . ?
C10' C15' 1.517(4) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' C20' 1.368(5) . ?
C15' C16' 1.375(5) . ?
C16' C17' 1.383(5) . ?
C16' H16' 0.9500 . ?
C17' C18' 1.369(5) . ?
C17' H17' 0.9500 . ?
C18' C19' 1.376(5) . ?
C18' H18' 0.9500 . ?
C19' C20' 1.388(5) . ?
C19' H19' 0.9500 . ?
C20' H20' 0.9500 . ?
C21' C22' 1.368(5) . ?
C21' C26' 1.379(5) . ?
C22' C23' 1.397(5) . ?
C22' H22' 0.9500 . ?
C23' C24' 1.366(6) . ?
C23' H23' 0.9500 . ?
C24' C25' 1.371(6) . ?
C24' H24' 0.9500 . ?
C25' C26' 1.378(5) . ?
C25' H25' 0.9500 . ?
C26' H26' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C12 115.5(3) . . ?
C13 O4 C14 116.4(3) . . ?
C2 N1 N9 103.6(2) . . ?
C5 N6 C7 112.6(3) . . ?
C5 N6 C15 122.8(3) . . ?
C7 N6 C15 124.6(3) . . ?
C3A N9 N1 113.8(3) . . ?
C3A N9 C8 121.3(3) . . ?
N1 N9 C8 124.8(3) . . ?
N1 C2 C3 112.1(3) . . ?
N1 C2 C11 117.7(3) . . ?
C3 C2 C11 130.2(3) . . ?
C3A C3 C2 104.7(3) . . ?
C3A C3 C13 127.1(3) . . ?
C2 C3 C13 127.8(3) . . ?
N9 C3A C3 105.8(3) . . ?
N9 C3A C4 116.5(3) . . ?
C3 C3A C4 137.6(3) . . ?
C3A C4 C4A 108.7(3) . . ?
C3A C4 H4A 110.0 . . ?
C4A C4 H4A 110.0 . . ?
C3A C4 H4B 110.0 . . ?
C4A C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4A C4 109.9(3) . . ?
C5 C4A C7A 104.7(3) . . ?
C4 C4A C7A 114.1(3) . . ?
C5 C4A H40A 109.3 . . ?
C4 C4A H40A 109.3 . . ?
C7A C4A H40A 109.3 . . ?
O5 C5 N6 124.7(3) . . ?
O5 C5 C4A 126.1(3) . . ?
N6 C5 C4A 109.2(3) . . ?
O6 C7 N6 123.2(3) . . ?
O6 C7 C7A 128.3(3) . . ?
N6 C7 C7A 108.5(3) . . ?
C7 C7A C8 112.5(3) . . ?
C7 C7A C4A 104.9(3) . . ?
C8 C7A C4A 112.4(3) . . ?
C7 C7A H7A 109.0 . . ?
C8 C7A H7A 109.0 . . ?
C4A C7A H7A 109.0 . . ?
N9 C8 C10 111.6(3) . . ?
N9 C8 C7A 106.6(2) . . ?
C10 C8 C7A 117.0(3) . . ?
N9 C8 H8 107.1 . . ?
C10 C8 H8 107.1 . . ?
C7A C8 H8 107.1 . . ?
C21 C10 C8 111.8(3) . . ?
C21 C10 H10A 109.3 . . ?
C8 C10 H10A 109.3 . . ?
C21 C10 H10B 109.3 . . ?
C8 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O1 C11 O2 124.4(3) . . ?
O1 C11 C2 124.2(3) . . ?
O2 C11 C2 111.4(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 123.6(3) . . ?
O3 C13 C3 125.5(3) . . ?
O4 C13 C3 110.9(3) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 121.0(3) . . ?
C16 C15 N6 119.5(3) . . ?
C20 C15 N6 119.5(3) . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 119.8(4) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C26 118.1(4) . . ?
C22 C21 C10 121.3(3) . . ?
C26 C21 C10 120.6(4) . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.2(4) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.5(5) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.7(5) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C11' O2' C12' 116.5(3) . . ?
C13' O4' C14' 115.4(3) . . ?
C2' N1' N9' 103.6(3) . . ?
C5' N6' C7' 112.9(3) . . ?
C5' N6' C21' 125.3(3) . . ?
C7' N6' C21' 121.4(3) . . ?
C3A' N9' N1' 114.0(3) . . ?
C3A' N9' C8' 121.9(3) . . ?
N1' N9' C8' 124.1(3) . . ?
N1' C2' C3' 112.3(3) . . ?
N1' C2' C11' 117.9(3) . . ?
C3' C2' C11' 129.6(3) . . ?
C3A' C3' C2' 104.2(3) . . ?
C3A' C3' C13' 126.8(3) . . ?
C2' C3' C13' 128.6(3) . . ?
N9' C3A' C3' 105.8(3) . . ?
N9' C3A' C4' 116.7(3) . . ?
C3' C3A' C4' 137.5(3) . . ?
C3A' C4' C4A' 109.2(3) . . ?
C3A' C4' H4'1 109.8 . . ?
C4A' C4' H4'1 109.8 . . ?
C3A' C4' H4'2 109.8 . . ?
C4A' C4' H4'2 109.8 . . ?
H4'1 C4' H4'2 108.3 . . ?
C5' C4A' C7A' 105.1(3) . . ?
C5' C4A' C4' 109.3(3) . . ?
C7A' C4A' C4' 114.1(3) . . ?
C5' C4A' H4A' 109.4 . . ?
C7A' C4A' H4A' 109.4 . . ?
C4' C4A' H4A' 109.4 . . ?
O5' C5' N6' 125.0(3) . . ?
O5' C5' C4A' 126.7(4) . . ?
N6' C5' C4A' 108.3(3) . . ?
O6' C7' N6' 122.2(3) . . ?
O6' C7' C7A' 128.7(3) . . ?
N6' C7' C7A' 109.0(3) . . ?
C7' C7A' C8' 113.1(3) . . ?
C7' C7A' C4A' 104.5(3) . . ?
C8' C7A' C4A' 113.5(3) . . ?
C7' C7A' H7A' 108.5 . . ?
C8' C7A' H7A' 108.5 . . ?
C4A' C7A' H7A' 108.5 . . ?
N9' C8' C10' 111.4(3) . . ?
N9' C8' C7A' 105.6(2) . . ?
C10' C8' C7A' 117.3(3) . . ?
N9' C8' H8' 107.4 . . ?
C10' C8' H8' 107.4 . . ?
C7A' C8' H8' 107.4 . . ?
C8' C10' C15' 110.9(3) . . ?
C8' C10' H10C 109.5 . . ?
C15' C10' H10C 109.5 . . ?
C8' C10' H10D 109.5 . . ?
C15' C10' H10D 109.5 . . ?
H10C C10' H10D 108.0 . . ?
O1' C11' O2' 124.1(3) . . ?
O1' C11' C2' 125.0(3) . . ?
O2' C11' C2' 110.9(3) . . ?
O2' C12' H12D 109.5 . . ?
O2' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
O2' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
O3' C13' O4' 123.7(3) . . ?
O3' C13' C3' 124.9(3) . . ?
O4' C13' C3' 111.4(3) . . ?
O4' C14' H14D 109.5 . . ?
O4' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
O4' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C20' C15' C16' 118.5(3) . . ?
C20' C15' C10' 122.1(3) . . ?
C16' C15' C10' 119.4(3) . . ?
C15' C16' C17' 121.0(3) . . ?
C15' C16' H16' 119.5 . . ?
C17' C16' H16' 119.5 . . ?
C18' C17' C16' 120.3(4) . . ?
C18' C17' H17' 119.8 . . ?
C16' C17' H17' 119.8 . . ?
C17' C18' C19' 119.0(3) . . ?
C17' C18' H18' 120.5 . . ?
C19' C18' H18' 120.5 . . ?
C18' C19' C20' 120.3(4) . . ?
C18' C19' H19' 119.8 . . ?
C20' C19' H19' 119.8 . . ?
C15' C20' C19' 120.8(4) . . ?
C15' C20' H20' 119.6 . . ?
C19' C20' H20' 119.6 . . ?
C22' C21' C26' 121.3(4) . . ?
C22' C21' N6' 120.4(3) . . ?
C26' C21' N6' 118.3(3) . . ?
C21' C22' C23' 118.3(4) . . ?
C21' C22' H22' 120.9 . . ?
C23' C22' H22' 120.9 . . ?
C24' C23' C22' 120.7(4) . . ?
C24' C23' H23' 119.7 . . ?
C22' C23' H23' 119.7 . . ?
C23' C24' C25' 120.4(4) . . ?
C23' C24' H24' 119.8 . . ?
C25' C24' H24' 119.8 . . ?
C24' C25' C26' 119.8(4) . . ?
C24' C25' H25' 120.1 . . ?
C26' C25' H25' 120.1 . . ?
C25' C26' C21' 119.6(4) . . ?
C25' C26' H26' 120.2 . . ?
C21' C26' H26' 120.2 . . ?

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
C2 N1 N9 C3A 1.2(4) . . . . ?
C2 N1 N9 C8 177.2(3) . . . . ?
N9 N1 C2 C3 -0.1(4) . . . . ?
N9 N1 C2 C11 -178.8(3) . . . . ?
N1 C2 C3 C3A -0.9(4) . . . . ?
C11 C2 C3 C3A 177.5(3) . . . . ?
N1 C2 C3 C13 -173.9(3) . . . . ?
C11 C2 C3 C13 4.6(6) . . . . ?
N1 N9 C3A C3 -1.8(4) . . . . ?
C8 N9 C3A C3 -178.0(3) . . . . ?
N1 N9 C3A C4 176.4(3) . . . . ?
C8 N9 C3A C4 0.2(4) . . . . ?
C2 C3 C3A N9 1.6(4) . . . . ?
C13 C3 C3A N9 174.6(3) . . . . ?
C2 C3 C3A C4 -176.0(4) . . . . ?
C13 C3 C3A C4 -3.0(6) . . . . ?
N9 C3A C4 C4A 48.4(4) . . . . ?
C3 C3A C4 C4A -134.2(4) . . . . ?
C3A C4 C4A C5 73.7(3) . . . . ?
C3A C4 C4A C7A -43.6(4) . . . . ?
C7 N6 C5 O5 179.1(4) . . . . ?
C15 N6 C5 O5 -2.4(6) . . . . ?
C7 N6 C5 C4A -2.6(4) . . . . ?
C15 N6 C5 C4A 175.9(3) . . . . ?
C4 C4A C5 O5 58.2(5) . . . . ?
C7A C4A C5 O5 -178.9(4) . . . . ?
C4 C4A C5 N6 -120.1(3) . . . . ?
C7A C4A C5 N6 2.8(4) . . . . ?
C5 N6 C7 O6 -178.4(3) . . . . ?
C15 N6 C7 O6 3.1(5) . . . . ?
C5 N6 C7 C7A 1.2(4) . . . . ?
C15 N6 C7 C7A -177.3(3) . . . . ?
O6 C7 C7A C8 -57.2(5) . . . . ?
N6 C7 C7A C8 123.2(3) . . . . ?
O6 C7 C7A C4A -179.7(4) . . . . ?
N6 C7 C7A C4A 0.6(4) . . . . ?
C5 C4A C7A C7 -2.1(3) . . . . ?
C4 C4A C7A C7 118.1(3) . . . . ?
C5 C4A C7A C8 -124.6(3) . . . . ?
C4 C4A C7A C8 -4.4(4) . . . . ?
C3A N9 C8 C10 -179.4(3) . . . . ?
N1 N9 C8 C10 4.9(4) . . . . ?
C3A N9 C8 C7A -50.5(4) . . . . ?
N1 N9 C8 C7A 133.8(3) . . . . ?
C7 C7A C8 N9 -69.0(3) . . . . ?
C4A C7A C8 N9 49.2(3) . . . . ?
C7 C7A C8 C10 56.7(4) . . . . ?
C4A C7A C8 C10 174.8(3) . . . . ?
N9 C8 C10 C21 -174.5(3) . . . . ?
C7A C8 C10 C21 62.4(4) . . . . ?
C12 O2 C11 O1 5.5(5) . . . . ?
C12 O2 C11 C2 -173.2(3) . . . . ?
N1 C2 C11 O1 50.1(5) . . . . ?
C3 C2 C11 O1 -128.3(4) . . . . ?
N1 C2 C11 O2 -131.3(3) . . . . ?
C3 C2 C11 O2 50.3(5) . . . . ?
C14 O4 C13 O3 6.2(5) . . . . ?
C14 O4 C13 C3 -173.0(3) . . . . ?
C3A C3 C13 O3 -160.1(3) . . . . ?
C2 C3 C13 O3 11.3(6) . . . . ?
C3A C3 C13 O4 19.1(5) . . . . ?
C2 C3 C13 O4 -169.5(3) . . . . ?
C5 N6 C15 C16 112.1(4) . . . . ?
C7 N6 C15 C16 -69.6(5) . . . . ?
C5 N6 C15 C20 -68.8(4) . . . . ?
C7 N6 C15 C20 109.6(4) . . . . ?
C20 C15 C16 C17 0.2(6) . . . . ?
N6 C15 C16 C17 179.4(4) . . . . ?
C15 C16 C17 C18 1.0(7) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C16 C15 C20 C19 -1.2(5) . . . . ?
N6 C15 C20 C19 179.7(3) . . . . ?
C18 C19 C20 C15 0.9(6) . . . . ?
C8 C10 C21 C22 -115.8(4) . . . . ?
C8 C10 C21 C26 64.3(5) . . . . ?
C26 C21 C22 C23 0.0(6) . . . . ?
C10 C21 C22 C23 -179.8(3) . . . . ?
C21 C22 C23 C24 -1.3(6) . . . . ?
C22 C23 C24 C25 1.8(7) . . . . ?
C23 C24 C25 C26 -1.1(8) . . . . ?
C22 C21 C26 C25 0.7(7) . . . . ?
C10 C21 C26 C25 -179.5(4) . . . . ?
C24 C25 C26 C21 -0.2(8) . . . . ?
C2' N1' N9' C3A' -0.1(4) . . . . ?
C2' N1' N9' C8' 179.3(3) . . . . ?
N9' N1' C2' C3' -0.3(4) . . . . ?
N9' N1' C2' C11' -176.2(3) . . . . ?
N1' C2' C3' C3A' 0.5(4) . . . . ?
C11' C2' C3' C3A' 175.8(3) . . . . ?
N1' C2' C3' C13' 174.1(3) . . . . ?
C11' C2' C3' C13' -10.6(6) . . . . ?
N1' N9' C3A' C3' 0.4(4) . . . . ?
C8' N9' C3A' C3' -179.0(3) . . . . ?
N1' N9' C3A' C4' -178.4(3) . . . . ?
C8' N9' C3A' C4' 2.2(4) . . . . ?
C2' C3' C3A' N9' -0.5(4) . . . . ?
C13' C3' C3A' N9' -174.3(3) . . . . ?
C2' C3' C3A' C4' 177.8(4) . . . . ?
C13' C3' C3A' C4' 4.1(6) . . . . ?
N9' C3A' C4' C4A' -48.0(4) . . . . ?
C3' C3A' C4' C4A' 133.8(4) . . . . ?
C3A' C4' C4A' C5' -77.3(3) . . . . ?
C3A' C4' C4A' C7A' 39.9(4) . . . . ?
C7' N6' C5' O5' 178.9(3) . . . . ?
C21' N6' C5' O5' -7.9(5) . . . . ?
C7' N6' C5' C4A' 0.5(4) . . . . ?
C21' N6' C5' C4A' 173.8(3) . . . . ?
C7A' C4A' C5' O5' 178.0(3) . . . . ?
C4' C4A' C5' O5' -59.2(5) . . . . ?
C7A' C4A' C5' N6' -3.6(3) . . . . ?
C4' C4A' C5' N6' 119.2(3) . . . . ?
C5' N6' C7' O6' -179.2(3) . . . . ?
C21' N6' C7' O6' 7.3(5) . . . . ?
C5' N6' C7' C7A' 2.9(4) . . . . ?
C21' N6' C7' C7A' -170.6(3) . . . . ?
O6' C7' C7A' C8' 53.3(5) . . . . ?
N6' C7' C7A' C8' -129.0(3) . . . . ?
O6' C7' C7A' C4A' 177.3(3) . . . . ?
N6' C7' C7A' C4A' -5.0(3) . . . . ?
C5' C4A' C7A' C7' 5.1(3) . . . . ?
C4' C4A' C7A' C7' -114.5(3) . . . . ?
C5' C4A' C7A' C8' 128.8(3) . . . . ?
C4' C4A' C7A' C8' 9.2(4) . . . . ?
C3A' N9' C8' C10' 176.7(3) . . . . ?
N1' N9' C8' C10' -2.6(4) . . . . ?
C3A' N9' C8' C7A' 48.3(4) . . . . ?
N1' N9' C8' C7A' -131.0(3) . . . . ?
C7' C7A' C8' N9' 68.0(3) . . . . ?
C4A' C7A' C8' N9' -50.8(4) . . . . ?
C7' C7A' C8' C10' -56.7(4) . . . . ?
C4A' C7A' C8' C10' -175.5(3) . . . . ?
N9' C8' C10' C15' 173.2(3) . . . . ?
C7A' C8' C10' C15' -65.0(4) . . . . ?
C12' O2' C11' O1' -5.2(5) . . . . ?
C12' O2' C11' C2' 175.9(3) . . . . ?
N1' C2' C11' O1' -41.4(5) . . . . ?
C3' C2' C11' O1' 143.5(4) . . . . ?
N1' C2' C11' O2' 137.5(3) . . . . ?
C3' C2' C11' O2' -37.6(5) . . . . ?
C14' O4' C13' O3' -4.7(5) . . . . ?
C14' O4' C13' C3' 175.9(3) . . . . ?
C3A' C3' C13' O3' 153.1(4) . . . . ?
C2' C3' C13' O3' -19.2(6) . . . . ?
C3A' C3' C13' O4' -27.5(5) . . . . ?
C2' C3' C13' O4' 160.3(3) . . . . ?
C8' C10' C15' C20' 88.8(4) . . . . ?
C8' C10' C15' C16' -90.8(4) . . . . ?
C20' C15' C16' C17' 1.3(5) . . . . ?
C10' C15' C16' C17' -179.0(3) . . . . ?
C15' C16' C17' C18' -1.2(6) . . . . ?
C16' C17' C18' C19' 0.2(6) . . . . ?
C17' C18' C19' C20' 0.6(6) . . . . ?
C16' C15' C20' C19' -0.5(6) . . . . ?
C10' C15' C20' C19' 179.9(3) . . . . ?
C18' C19' C20' C15' -0.5(6) . . . . ?
C5' N6' C21' C22' 105.9(4) . . . . ?
C7' N6' C21' C22' -81.3(4) . . . . ?
C5' N6' C21' C26' -76.9(4) . . . . ?
C7' N6' C21' C26' 95.8(4) . . . . ?
C26' C21' C22' C23' 0.0(6) . . . . ?
N6' C21' C22' C23' 177.0(3) . . . . ?
C21' C22' C23' C24' -0.2(6) . . . . ?
C22' C23' C24' C25' 1.0(7) . . . . ?
C23' C24' C25' C26' -1.5(6) . . . . ?
C24' C25' C26' C21' 1.3(6) . . . . ?
C22' C21' C26' C25' -0.5(6) . . . . ?
N6' C21' C26' C25' -177.6(3) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.063

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
