# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1831105'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 O5, 2(C6 H9 N2), H2O'
_chemical_formula_sum            'C26 H28 N4 O6'
_chemical_formula_weight         492.52

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

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

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

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

_cell_length_a                   13.864(11)
_cell_length_b                   12.086(11)
_cell_length_c                   14.994(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.62(2)
_cell_angle_gamma                90
_cell_volume                     2336(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1200
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9037
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2021
_reflns_number_gt                1803
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0845P)²+0.6212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2021
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.085
_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 0.63806(7) 0.47914(8) 0.35006(7) 0.0275(3) Uani 1 1 d . . . . .
O3 O 1.000000 0.26803(11) 0.250000 0.0287(4) Uani 1 2 d S T P . .
O2 O 0.76324(8) 0.59776(8) 0.41803(7) 0.0298(3) Uani 1 1 d . . . . .
C13 C 0.27004(12) 0.06793(13) 0.11485(10) 0.0315(4) Uani 1 1 d . . . . .
H13A H 0.311980 0.124736 0.155649 0.047 Uiso 1 1 calc R U . . .
H13B H 0.290565 0.057481 0.060871 0.047 Uiso 1 1 calc R U . . .
H13C H 0.279217 0.000027 0.150233 0.047 Uiso 1 1 calc R U . . .
N1 N -0.00595(9) 0.09019(9) 0.08634(7) 0.0219(3) Uani 1 1 d . . . . .
H1 H -0.046949 0.059104 0.110056 0.026 Uiso 1 1 calc R U . . .
C9 C 0.02302(11) 0.21663(12) -0.01862(9) 0.0258(4) Uani 1 1 d . . . . .
H9 H -0.000841 0.271312 -0.065261 0.031 Uiso 1 1 calc R U . . .
C6 C 0.83520(11) 0.29384(11) 0.25473(9) 0.0228(4) Uani 1 1 d . . . . .
H6 H 0.812184 0.232544 0.215045 0.027 Uiso 1 1 calc R U . . .
C11 C 0.16039(11) 0.10093(11) 0.08085(9) 0.0239(4) Uani 1 1 d . . . . .
C12 C 0.09306(11) 0.05613(11) 0.11619(9) 0.0233(4) Uani 1 1 d . . . . .
H12 H 0.115530 0.000545 0.162139 0.028 Uiso 1 1 calc R U . . .
C8 C -0.04331(11) 0.16990(11) 0.02172(9) 0.0232(4) Uani 1 1 d . . . . .
N2 N -0.14006(10) 0.19919(11) -0.00268(9) 0.0320(4) Uani 1 1 d . . . . .
H2A H -0.178817 0.167054 0.022965 0.038 Uiso 1 1 calc R U . . .
H2B H -0.165178 0.250671 -0.044423 0.038 Uiso 1 1 calc R U . . .
C10 C 0.12102(11) 0.18210(12) 0.01039(9) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.164776 0.213107 -0.017227 0.031 Uiso 1 1 calc R U . . .
C1 C 0.72897(11) 0.51121(11) 0.37320(9) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.80148(11) 0.44228(11) 0.34444(9) 0.0214(4) Uani 1 1 d . . . . .
C3 C 0.90331(11) 0.47327(12) 0.37292(10) 0.0252(4) Uani 1 1 d . . . . .
H3 H 0.926912 0.533869 0.413355 0.030 Uiso 1 1 calc R U . . .
C4 C 0.97056(12) 0.41647(12) 0.34279(10) 0.0284(4) Uani 1 1 d . . . . .
H4 H 1.039908 0.437330 0.363194 0.034 Uiso 1 1 calc R U . . .
C5 C 0.93483(11) 0.32797(12) 0.28191(10) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.76886(11) 0.35070(11) 0.28643(9) 0.0220(4) Uani 1 1 d . . . . .
H7 H 0.700458 0.327149 0.268516 0.026 Uiso 1 1 calc R U . . .
O1W O 1.000000 0.81127(14) 0.250000 0.0423(5) Uani 1 2 d DS T P . .
H1W H 0.957750 0.855601 0.215081 0.063 Uiso 1 1 d DR U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2396(19) . ?
O3 C5 1.3742(17) 2_755 ?
O3 C5 1.3742(17) . ?
O2 C1 1.2396(18) . ?
C13 C11 1.469(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 C8 1.3288(19) . ?
N1 C12 1.342(2) . ?
N1 H1 0.8600 . ?
C9 C10 1.332(2) . ?
C9 C8 1.393(2) . ?
C9 H9 0.9300 . ?
C6 C5 1.353(2) . ?
C6 C7 1.366(2) . ?
C6 H6 0.9300 . ?
C11 C12 1.345(2) . ?
C11 C10 1.397(2) . ?
C12 H12 0.9300 . ?
C8 N2 1.303(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C10 H10 0.9300 . ?
C1 C2 1.487(2) . ?
C2 C3 1.368(2) . ?
C2 C7 1.377(2) . ?
C3 C4 1.362(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
O1W H1W 0.8236 . ?
O1W H1W 0.8237 2_755 ?

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
C5 O3 C5 116.37(16) 2_755 . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 N1 C12 122.80(12) . . ?
C8 N1 H1 118.6 . . ?
C12 N1 H1 118.6 . . ?
C10 C9 C8 119.24(14) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C5 C6 C7 119.04(14) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C12 C11 C10 116.49(14) . . ?
C12 C11 C13 122.24(14) . . ?
C10 C11 C13 121.27(13) . . ?
N1 C12 C11 121.20(13) . . ?
N1 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N2 C8 N1 119.10(12) . . ?
N2 C8 C9 122.96(13) . . ?
N1 C8 C9 117.92(13) . . ?
C8 N2 H2A 120.0 . . ?
C8 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C9 C10 C11 122.30(13) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
O1 C1 O2 124.24(13) . . ?
O1 C1 C2 118.04(13) . . ?
O2 C1 C2 117.72(13) . . ?
C3 C2 C7 118.57(13) . . ?
C3 C2 C1 119.11(13) . . ?
C7 C2 C1 122.26(13) . . ?
C4 C3 C2 120.81(14) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.30(14) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 O3 117.63(13) . . ?
C6 C5 C4 121.03(13) . . ?
O3 C5 C4 121.28(13) . . ?
C6 C7 C2 121.17(14) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
H1W O1W H1W 98.8 . 2_755 ?

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
C8 N1 C12 C11 -0.7(2) . . . . ?
C10 C11 C12 N1 -1.51(19) . . . . ?
C13 C11 C12 N1 177.74(12) . . . . ?
C12 N1 C8 N2 -179.18(12) . . . . ?
C12 N1 C8 C9 2.31(18) . . . . ?
C10 C9 C8 N2 179.93(13) . . . . ?
C10 C9 C8 N1 -1.6(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C12 C11 C10 C9 2.1(2) . . . . ?
C13 C11 C10 C9 -177.11(13) . . . . ?
O1 C1 C2 C3 -177.03(12) . . . . ?
O2 C1 C2 C3 3.68(18) . . . . ?
O1 C1 C2 C7 5.90(18) . . . . ?
O2 C1 C2 C7 -173.40(12) . . . . ?
C7 C2 C3 C4 1.5(2) . . . . ?
C1 C2 C3 C4 -175.64(12) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C7 C6 C5 O3 179.04(11) . . . . ?
C7 C6 C5 C4 1.9(2) . . . . ?
C5 O3 C5 C6 136.88(14) 2_755 . . . ?
C5 O3 C5 C4 -46.01(11) 2_755 . . . ?
C3 C4 C5 C6 -2.7(2) . . . . ?
C3 C4 C5 O3 -179.74(12) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C3 C2 C7 C6 -2.4(2) . . . . ?
C1 C2 C7 C6 174.72(12) . . . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.070

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1831106'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 O5, C6 H9 N2'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.075(3)
_cell_length_b                   19.857(2)
_cell_length_c                   12.811(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.991(2)
_cell_angle_gamma                90
_cell_volume                     1793.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1720
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20967
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3155
_reflns_number_gt                2657
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0506P)²+0.5361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3155
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O3 O 0.36117(15) 0.08159(5) 0.65123(8) 0.0365(3) Uani 1 1 d . . . . .
O1 O -0.34073(14) 0.17212(5) 0.90584(8) 0.0328(3) Uani 1 1 d . . . . .
O5 O 0.94015(15) -0.15893(6) 0.58562(9) 0.0410(3) Uani 1 1 d . . . . .
O4 O 0.68314(15) -0.21418(5) 0.63294(9) 0.0370(3) Uani 1 1 d . . . . .
H4A H 0.746223 -0.247478 0.620845 0.056 Uiso 1 1 d R U . . .
O2 O -0.28878(15) 0.06687(5) 0.96158(9) 0.0397(3) Uani 1 1 d . . . . .
C11 C 0.6629(2) -0.09673(7) 0.62159(11) 0.0268(3) Uani 1 1 d . . . . .
C2 C -0.0822(2) 0.10976(7) 0.84223(11) 0.0259(3) Uani 1 1 d . . . . .
C9 C 0.6464(2) 0.02447(7) 0.62669(11) 0.0305(3) Uani 1 1 d . . . . .
H9 H 0.704996 0.066248 0.623215 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4554(2) 0.02040(7) 0.64387(11) 0.0283(3) Uani 1 1 d . . . . .
C10 C 0.7489(2) -0.03391(7) 0.61480(12) 0.0307(3) Uani 1 1 d . . . . .
H10 H 0.876112 -0.031251 0.602182 0.037 Uiso 1 1 calc R U . . .
C7 C 0.0551(2) 0.06051(7) 0.86815(11) 0.0291(3) Uani 1 1 d . . . . .
H7 H 0.045018 0.034010 0.927250 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2062(2) 0.05024(7) 0.80777(12) 0.0317(3) Uani 1 1 d . . . . .
H6 H 0.299756 0.018765 0.827834 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3648(2) -0.04161(7) 0.64673(12) 0.0311(3) Uani 1 1 d . . . . .
H13 H 0.235778 -0.043980 0.655156 0.037 Uiso 1 1 calc R U . . .
C1 C -0.2480(2) 0.11676(7) 0.90783(11) 0.0283(3) Uani 1 1 d . . . . .
C3 C -0.0648(2) 0.14904(7) 0.75335(11) 0.0282(3) Uani 1 1 d . . . . .
H3 H -0.151289 0.183479 0.736705 0.034 Uiso 1 1 calc R U . . .
C14 C 0.7775(2) -0.15914(7) 0.61120(11) 0.0293(3) Uani 1 1 d . . . . .
C5 C 0.2153(2) 0.08779(7) 0.71686(11) 0.0288(3) Uani 1 1 d . . . . .
C4 C 0.0806(2) 0.13722(7) 0.68941(11) 0.0297(3) Uani 1 1 d . . . . .
H4 H 0.087872 0.162234 0.628516 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4697(2) -0.09985(7) 0.63683(11) 0.0295(3) Uani 1 1 d . . . . .
H12 H 0.410843 -0.141564 0.640366 0.035 Uiso 1 1 calc R U . . .
N1 N 0.64745(16) 0.81791(6) 0.97414(9) 0.0277(3) Uani 1 1 d . . . . .
H1A H 0.545779 0.821235 1.006010 0.033 Uiso 1 1 calc R U . . .
N2 N 0.60722(18) 0.92892(6) 0.92455(10) 0.0336(3) Uani 1 1 d . . . . .
H2A H 0.503959 0.929616 0.955344 0.040 Uiso 1 1 calc R U . . .
H2B H 0.643919 0.964458 0.893705 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7402(2) 0.75764(7) 0.97503(12) 0.0316(3) Uani 1 1 d . . . . .
H15 H 0.692028 0.721038 1.009456 0.038 Uiso 1 1 calc R U . . .
C16 C 0.9019(2) 0.75044(7) 0.92621(12) 0.0326(3) Uani 1 1 d . . . . .
H16 H 0.962799 0.708938 0.925950 0.039 Uiso 1 1 calc R U . . .
C17 C 0.9773(2) 0.80668(8) 0.87567(11) 0.0307(3) Uani 1 1 d . . . . .
C18 C 0.8810(2) 0.86669(7) 0.87554(11) 0.0304(3) Uani 1 1 d . . . . .
H18 H 0.928699 0.903994 0.842638 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7106(2) 0.87262(7) 0.92465(11) 0.0270(3) Uani 1 1 d . . . . .
C20 C 1.1594(2) 0.80012(9) 0.82330(14) 0.0444(4) Uani 1 1 d . . . . .
H20A H 1.139592 0.770678 0.763919 0.067 Uiso 1 1 calc R U . . .
H20B H 1.256589 0.781832 0.872166 0.067 Uiso 1 1 calc R U . . .
H20C H 1.197904 0.843683 0.800491 0.067 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
O3 C5 1.3922(18) . ?
O3 C8 1.3931(17) . ?
O1 C1 1.2794(17) . ?
O5 C14 1.2236(18) . ?
O4 C14 1.3229(18) . ?
O4 H4A 0.8200 . ?
O2 C1 1.2545(17) . ?
C11 C10 1.394(2) . ?
C11 C12 1.399(2) . ?
C11 C14 1.4933(19) . ?
C2 C3 1.395(2) . ?
C2 C7 1.398(2) . ?
C2 C1 1.507(2) . ?
C9 C10 1.383(2) . ?
C9 C8 1.391(2) . ?
C9 H9 0.9300 . ?
C8 C13 1.390(2) . ?
C10 H10 0.9300 . ?
C7 C6 1.388(2) . ?
C7 H7 0.9300 . ?
C6 C5 1.389(2) . ?
C6 H6 0.9300 . ?
C13 C12 1.386(2) . ?
C13 H13 0.9300 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9300 . ?
C5 C4 1.392(2) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
N1 C19 1.3531(18) . ?
N1 C15 1.3643(18) . ?
N1 H1A 0.8600 . ?
N2 C19 1.3359(19) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C15 C16 1.359(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.418(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(2) . ?
C17 C20 1.509(2) . ?
C18 C19 1.413(2) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C5 O3 C8 120.14(11) . . ?
C14 O4 H4A 109.5 . . ?
C10 C11 C12 119.03(13) . . ?
C10 C11 C14 119.61(13) . . ?
C12 C11 C14 121.35(13) . . ?
C3 C2 C7 118.43(13) . . ?
C3 C2 C1 122.14(12) . . ?
C7 C2 C1 119.37(13) . . ?
C10 C9 C8 119.64(13) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C13 C8 C9 120.81(13) . . ?
C13 C8 O3 123.15(13) . . ?
C9 C8 O3 115.93(12) . . ?
C9 C10 C11 120.53(13) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C6 C7 C2 121.58(13) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C7 C6 C5 118.83(13) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C12 C13 C8 119.04(13) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
O2 C1 O1 123.19(13) . . ?
O2 C1 C2 117.42(12) . . ?
O1 C1 C2 119.38(12) . . ?
C4 C3 C2 120.63(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O5 C14 O4 124.26(13) . . ?
O5 C14 C11 123.47(13) . . ?
O4 C14 C11 112.27(12) . . ?
C6 C5 C4 120.66(13) . . ?
C6 C5 O3 123.34(13) . . ?
C4 C5 O3 115.91(12) . . ?
C3 C4 C5 119.73(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C13 C12 C11 120.87(13) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C19 N1 C15 122.01(12) . . ?
C19 N1 H1A 119.0 . . ?
C15 N1 H1A 119.0 . . ?
C19 N2 H2A 120.0 . . ?
C19 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C16 C15 N1 120.80(13) . . ?
C16 C15 H15 119.6 . . ?
N1 C15 H15 119.6 . . ?
C15 C16 C17 119.52(13) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 118.54(14) . . ?
C18 C17 C20 121.15(14) . . ?
C16 C17 C20 120.31(14) . . ?
C17 C18 C19 120.98(13) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
N2 C19 N1 117.98(13) . . ?
N2 C19 C18 123.91(13) . . ?
N1 C19 C18 118.11(13) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 C9 C8 C13 -1.6(2) . . . . ?
C10 C9 C8 O3 -177.78(13) . . . . ?
C5 O3 C8 C13 36.8(2) . . . . ?
C5 O3 C8 C9 -147.06(14) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
C12 C11 C10 C9 2.3(2) . . . . ?
C14 C11 C10 C9 -178.46(13) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C1 C2 C7 C6 177.36(13) . . . . ?
C2 C7 C6 C5 -3.1(2) . . . . ?
C9 C8 C13 C12 2.8(2) . . . . ?
O3 C8 C13 C12 178.78(13) . . . . ?
C3 C2 C1 O2 155.87(14) . . . . ?
C7 C2 C1 O2 -21.4(2) . . . . ?
C3 C2 C1 O1 -23.6(2) . . . . ?
C7 C2 C1 O1 159.18(13) . . . . ?
C7 C2 C3 C4 3.1(2) . . . . ?
C1 C2 C3 C4 -174.22(13) . . . . ?
C10 C11 C14 O5 -8.2(2) . . . . ?
C12 C11 C14 O5 171.07(14) . . . . ?
C10 C11 C14 O4 171.72(13) . . . . ?
C12 C11 C14 O4 -9.05(19) . . . . ?
C7 C6 C5 C4 3.2(2) . . . . ?
C7 C6 C5 O3 179.65(13) . . . . ?
C8 O3 C5 C6 29.3(2) . . . . ?
C8 O3 C5 C4 -154.11(13) . . . . ?
C2 C3 C4 C5 -3.0(2) . . . . ?
C6 C5 C4 C3 -0.2(2) . . . . ?
O3 C5 C4 C3 -176.92(13) . . . . ?
C8 C13 C12 C11 -1.6(2) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C14 C11 C12 C13 179.78(13) . . . . ?
C19 N1 C15 C16 0.5(2) . . . . ?
N1 C15 C16 C17 1.3(2) . . . . ?
C15 C16 C17 C18 -1.6(2) . . . . ?
C15 C16 C17 C20 178.51(14) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C20 C17 C18 C19 179.99(14) . . . . ?
C15 N1 C19 N2 177.62(13) . . . . ?
C15 N1 C19 C18 -1.9(2) . . . . ?
C17 C18 C19 N2 -177.87(14) . . . . ?
C17 C18 C19 N1 1.7(2) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1831107'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 O5, 2(C6 H9 N2), H2O'
_chemical_formula_sum            'C26 H28 N4 O6'
_chemical_formula_weight         492.52

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                   6.855(4)
_cell_length_b                   7.642(3)
_cell_length_c                   24.281(4)
_cell_angle_alpha                90.019(3)
_cell_angle_beta                 92.555(2)
_cell_angle_gamma                107.022(4)
_cell_volume                     1214.9(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11530
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.679
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4260
_reflns_number_gt                3764
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0461P)²+0.3636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4260
_refine_ls_number_parameters     328
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.050
_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 0.17471(14) -0.11397(13) 0.43680(4) 0.0272(2) Uani 1 1 d . . . . .
O2 O -0.16095(14) -0.16123(13) 0.43973(4) 0.0279(2) Uani 1 1 d . . . . .
O3 O -0.00512(16) 0.12972(13) 0.19517(4) 0.0314(2) Uani 1 1 d . . . . .
O4 O 0.41251(17) 0.87283(13) 0.07976(4) 0.0354(3) Uani 1 1 d . . . . .
O5 O 0.46113(15) 0.98247(13) 0.16571(4) 0.0302(2) Uani 1 1 d . . . . .
C1 C 0.00306(19) -0.11340(16) 0.41539(5) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.00027(19) -0.04995(16) 0.35661(5) 0.0216(3) Uani 1 1 d . . . . .
C3 C -0.1713(2) -0.01220(18) 0.33307(6) 0.0254(3) Uani 1 1 d . . . . .
H3A H -0.286482 -0.028270 0.353597 0.031 Uiso 1 1 calc R U . . .
C4 C -0.1729(2) 0.04902(18) 0.27945(6) 0.0278(3) Uani 1 1 d . . . . .
H4 H -0.288042 0.074117 0.263848 0.033 Uiso 1 1 calc R U . . .
C5 C -0.0008(2) 0.07219(17) 0.24951(5) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.1701(2) 0.03088(19) 0.27115(6) 0.0281(3) Uani 1 1 d . . . . .
H6 H 0.283198 0.043542 0.250026 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1697(2) -0.02968(18) 0.32486(6) 0.0258(3) Uani 1 1 d . . . . .
H7 H 0.284074 -0.057245 0.339973 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1040(2) 0.30761(18) 0.18358(5) 0.0239(3) Uani 1 1 d . . . . .
C9 C 0.1206(2) 0.34706(19) 0.12786(5) 0.0269(3) Uani 1 1 d . . . . .
H9 H 0.067895 0.255364 0.101413 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2160(2) 0.52352(19) 0.11222(5) 0.0266(3) Uani 1 1 d . . . . .
H10 H 0.226020 0.549938 0.074881 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2977(2) 0.66315(18) 0.15078(5) 0.0236(3) Uani 1 1 d . . . . .
C12 C 0.2823(2) 0.62062(18) 0.20626(5) 0.0248(3) Uani 1 1 d . . . . .
H12 H 0.337250 0.711928 0.232691 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1856(2) 0.44327(18) 0.22298(5) 0.0256(3) Uani 1 1 d . . . . .
H13 H 0.175994 0.416243 0.260284 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3989(2) 0.85411(18) 0.13108(5) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.61857(17) 0.31644(15) 0.12230(4) 0.0254(3) Uani 1 1 d . . . . .
H1 H 0.564716 0.206450 0.133167 0.030 Uiso 1 1 calc R U . . .
N2 N 0.5532(2) 0.20995(16) 0.03314(5) 0.0422(4) Uani 1 1 d . . . . .
H2A H 0.499052 0.102107 0.045601 0.051 Uiso 1 1 calc R U . . .
H2B H 0.558005 0.227111 -0.001836 0.051 Uiso 1 1 calc R U . . .
C15 C 0.6907(2) 0.4526(2) 0.16020(6) 0.0301(3) Uani 1 1 d . . . . .
H15 H 0.680121 0.424843 0.197440 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7780(2) 0.6282(2) 0.14552(6) 0.0328(3) Uani 1 1 d . . . . .
H16 H 0.827057 0.719468 0.172274 0.039 Uiso 1 1 calc R U . . .
C17 C 0.7932(2) 0.67032(19) 0.08917(6) 0.0308(3) Uani 1 1 d . . . . .
C18 C 0.7186(2) 0.53133(19) 0.05135(6) 0.0312(3) Uani 1 1 d . . . . .
H18 H 0.727047 0.557200 0.013952 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6295(2) 0.34989(19) 0.06789(5) 0.0275(3) Uani 1 1 d . . . . .
C20 C 0.8916(3) 0.8627(2) 0.07143(7) 0.0430(4) Uani 1 1 d . . . . .
H20A H 1.036155 0.894622 0.079661 0.064 Uiso 1 1 calc R U . . .
H20B H 0.835322 0.944803 0.090789 0.064 Uiso 1 1 calc R U . . .
H20C H 0.866521 0.871838 0.032478 0.064 Uiso 1 1 calc R U . . .
N3 N 0.80404(16) 0.24500(14) 0.46261(4) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.822734 0.190968 0.492585 0.029 Uiso 1 1 calc R U . . .
N4 N 1.15273(17) 0.36807(16) 0.46057(5) 0.0291(3) Uani 1 1 d . . . . .
H4A H 1.165265 0.312285 0.490674 0.035 Uiso 1 1 calc R U . . .
H4B H 1.259541 0.434948 0.445315 0.035 Uiso 1 1 calc R U . . .
C21 C 0.6105(2) 0.22071(18) 0.44214(6) 0.0279(3) Uani 1 1 d . . . . .
H21 H 0.501544 0.146983 0.460806 0.033 Uiso 1 1 calc R U . . .
C22 C 0.5737(2) 0.30209(19) 0.39501(6) 0.0284(3) Uani 1 1 d . . . . .
H22 H 0.440471 0.285184 0.381333 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7403(2) 0.41322(18) 0.36677(5) 0.0260(3) Uani 1 1 d . . . . .
C24 C 0.9341(2) 0.43654(18) 0.38805(5) 0.0247(3) Uani 1 1 d . . . . .
H24 H 1.044685 0.509423 0.369750 0.030 Uiso 1 1 calc R U . . .
C25 C 0.9683(2) 0.35093(17) 0.43760(5) 0.0227(3) Uani 1 1 d . . . . .
C26 C 0.6986(3) 0.4999(2) 0.31392(6) 0.0359(4) Uani 1 1 d . . . . .
H26A H 0.634200 0.592595 0.321562 0.054 Uiso 1 1 calc R U . . .
H26B H 0.610085 0.408358 0.289758 0.054 Uiso 1 1 calc R U . . .
H26C H 0.824962 0.554324 0.296592 0.054 Uiso 1 1 calc R U . . .
O6 O 0.43093(15) 0.67824(14) 0.40881(4) 0.0352(3) Uani 1 1 d D . . . .
H6A H 0.367472 0.751534 0.416155 0.042 Uiso 1 1 d DR U . . .
H6B H 0.553352 0.730756 0.416057 0.042 Uiso 1 1 d DR U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2662(17) . ?
O2 C1 1.2513(17) . ?
O3 C8 1.3822(16) . ?
O3 C5 1.3927(16) . ?
O4 C14 1.2587(16) . ?
O5 C14 1.2546(17) . ?
C1 C2 1.5086(17) . ?
C2 C3 1.3902(19) . ?
C2 C7 1.393(2) . ?
C3 C4 1.3842(19) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C6 C7 1.3838(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.3838(19) . ?
C8 C9 1.3885(19) . ?
C9 C10 1.377(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.3898(19) . ?
C10 H10 0.9300 . ?
C11 C12 1.3874(18) . ?
C11 C14 1.5089(18) . ?
C12 C13 1.3925(19) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 C19 1.3468(17) . ?
N1 C15 1.3537(18) . ?
N1 H1 0.8600 . ?
N2 C19 1.3273(18) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C15 C16 1.354(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(2) . ?
C17 C20 1.499(2) . ?
C18 C19 1.408(2) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N3 C25 1.3487(18) . ?
N3 C21 1.3557(19) . ?
N3 H3 0.8600 . ?
N4 C25 1.3293(19) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C21 C22 1.352(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.413(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(2) . ?
C23 C26 1.4984(19) . ?
C24 C25 1.4127(18) . ?
C24 H24 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O6 H6A 0.8272 . ?
O6 H6B 0.8282 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 C5 118.09(10) . . ?
O2 C1 O1 124.37(12) . . ?
O2 C1 C2 118.93(11) . . ?
O1 C1 C2 116.70(11) . . ?
C3 C2 C7 118.91(12) . . ?
C3 C2 C1 120.73(12) . . ?
C7 C2 C1 120.36(12) . . ?
C4 C3 C2 120.81(13) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C5 C4 C3 118.90(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.71(13) . . ?
C4 C5 O3 118.59(12) . . ?
C6 C5 O3 119.62(12) . . ?
C5 C6 C7 118.71(13) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 120.91(13) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
O3 C8 C13 124.52(12) . . ?
O3 C8 C9 115.01(12) . . ?
C13 C8 C9 120.41(12) . . ?
C10 C9 C8 119.25(12) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.71(12) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 118.23(12) . . ?
C12 C11 C14 122.53(12) . . ?
C10 C11 C14 119.25(12) . . ?
C11 C12 C13 120.99(12) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 119.40(12) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
O5 C14 O4 124.38(12) . . ?
O5 C14 C11 119.31(11) . . ?
O4 C14 C11 116.31(12) . . ?
C19 N1 C15 121.26(12) . . ?
C19 N1 H1 119.4 . . ?
C15 N1 H1 119.4 . . ?
C19 N2 H2A 120.0 . . ?
C19 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C15 C16 121.97(13) . . ?
N1 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 119.00(13) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 118.35(13) . . ?
C18 C17 C20 121.20(14) . . ?
C16 C17 C20 120.44(13) . . ?
C17 C18 C19 121.34(13) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
N2 C19 N1 117.90(12) . . ?
N2 C19 C18 124.02(13) . . ?
N1 C19 C18 118.08(12) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 N3 C21 122.31(12) . . ?
C25 N3 H3 118.8 . . ?
C21 N3 H3 118.8 . . ?
C25 N4 H4A 120.0 . . ?
C25 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C22 C21 N3 120.96(13) . . ?
C22 C21 H21 119.5 . . ?
N3 C21 H21 119.5 . . ?
C21 C22 C23 119.15(13) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 119.10(13) . . ?
C24 C23 C26 122.01(13) . . ?
C22 C23 C26 118.89(13) . . ?
C23 C24 C25 120.59(12) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
N4 C25 N3 118.46(12) . . ?
N4 C25 C24 123.65(12) . . ?
N3 C25 C24 117.89(12) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H6A O6 H6B 106.9 . . ?

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
O2 C1 C2 C3 11.93(18) . . . . ?
O1 C1 C2 C3 -167.98(12) . . . . ?
O2 C1 C2 C7 -167.55(12) . . . . ?
O1 C1 C2 C7 12.54(18) . . . . ?
C7 C2 C3 C4 -1.6(2) . . . . ?
C1 C2 C3 C4 178.89(12) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C3 C4 C5 O3 178.52(11) . . . . ?
C8 O3 C5 C4 106.88(14) . . . . ?
C8 O3 C5 C6 -76.42(16) . . . . ?
C4 C5 C6 C7 -2.1(2) . . . . ?
O3 C5 C6 C7 -178.67(12) . . . . ?
C5 C6 C7 C2 0.4(2) . . . . ?
C3 C2 C7 C6 1.4(2) . . . . ?
C1 C2 C7 C6 -179.08(12) . . . . ?
C5 O3 C8 C13 -12.87(19) . . . . ?
C5 O3 C8 C9 169.98(12) . . . . ?
O3 C8 C9 C10 176.13(12) . . . . ?
C13 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C9 C10 C11 C14 -179.48(12) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C14 C11 C12 C13 179.20(12) . . . . ?
O3 C8 C13 C12 -176.13(12) . . . . ?
C9 C8 C13 C12 0.9(2) . . . . ?
C11 C12 C13 C8 0.0(2) . . . . ?
C12 C11 C14 O5 -4.3(2) . . . . ?
C10 C11 C14 O5 175.51(12) . . . . ?
C12 C11 C14 O4 176.41(12) . . . . ?
C10 C11 C14 O4 -3.74(19) . . . . ?
C19 N1 C15 C16 -0.3(2) . . . . ?
N1 C15 C16 C17 0.3(2) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C15 C16 C17 C20 -179.08(14) . . . . ?
C16 C17 C18 C19 -0.3(2) . . . . ?
C20 C17 C18 C19 178.80(14) . . . . ?
C15 N1 C19 N2 -179.16(13) . . . . ?
C15 N1 C19 C18 0.1(2) . . . . ?
C17 C18 C19 N2 179.43(15) . . . . ?
C17 C18 C19 N1 0.3(2) . . . . ?
C25 N3 C21 C22 0.3(2) . . . . ?
N3 C21 C22 C23 0.3(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C21 C22 C23 C26 178.75(13) . . . . ?
C22 C23 C24 C25 0.00(19) . . . . ?
C26 C23 C24 C25 -179.17(12) . . . . ?
C21 N3 C25 N4 179.70(12) . . . . ?
C21 N3 C25 C24 -0.78(18) . . . . ?
C23 C24 C25 N4 -179.91(12) . . . . ?
C23 C24 C25 N3 0.60(19) . . . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036

