# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_monomer1
_database_code_depnum_ccdc_archive 'CCDC 2038869'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N3 O5'
_chemical_formula_sum            'C9 H13 N3 O5'
_chemical_formula_weight         243.22

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                   6.6496(5)
_cell_length_b                   18.782(2)
_cell_length_c                   9.0830(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.116(5)
_cell_angle_gamma                90
_cell_volume                     1095.14(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2816
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.93

_exptl_crystal_description       long-plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.475
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            8110
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1920
_reflns_number_gt                1523
_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, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0410P)²+0.3202P] 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         1920
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.054
_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
C1 C 0.2973(2) 0.71040(9) 0.48241(17) 0.0293(4) Uani 1 1 d . . . . .
H1 H 0.2191 0.7202 0.3771 0.035 Uiso 1 1 calc R U . . .
C2 C 0.4777(2) 0.66122(9) 0.47747(17) 0.0288(4) Uani 1 1 d . . . . .
H2 H 0.4234 0.6158 0.4305 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6132(2) 0.69568(9) 0.38631(17) 0.0285(4) Uani 1 1 d . . . . .
H3 H 0.5223 0.7076 0.2859 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7044(2) 0.76485(9) 0.46061(17) 0.0271(4) Uani 1 1 d . . . . .
H4 H 0.7974 0.7544 0.5611 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5330(2) 0.81518(9) 0.48036(17) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.4577 0.8341 0.3806 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3791(2) 0.78067(9) 0.55627(17) 0.0284(4) Uani 1 1 d . . . . .
H6 H 0.4499 0.7719 0.6636 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5898(3) 0.57950(10) 0.6891(2) 0.0414(4) Uani 1 1 d . . . . .
H7A H 0.4565 0.5583 0.6393 0.050 Uiso 1 1 calc R U . . .
H7B H 0.5995 0.5823 0.7974 0.050 Uiso 1 1 calc R U . . .
C8 C 0.7559(3) 0.53411(10) 0.6658(2) 0.0461(5) Uani 1 1 d . . . . .
C9 C 0.8925(4) 0.49763(13) 0.6533(3) 0.0711(7) Uani 1 1 d . . . . .
H9 H 1.0014 0.4685 0.6433 0.085 Uiso 1 1 calc R U . . .
N1 N 0.6295(2) 0.87492(9) 0.58136(18) 0.0439(4) Uani 1 1 d . U . . .
N2 N 0.6913(2) 0.92497(10) 0.52008(19) 0.0494(4) Uani 1 1 d . U . . .
N3 N 0.7539(4) 0.97472(12) 0.4795(3) 0.0877(7) Uani 1 1 d . . . . .
O1 O 0.15910(15) 0.67757(7) 0.55773(13) 0.0383(3) Uani 1 1 d . . . . .
H1A H 0.2086 0.6799 0.6503 0.057 Uiso 1 1 calc R U . . .
O2 O 0.59874(16) 0.64939(6) 0.63112(12) 0.0336(3) Uani 1 1 d . . . . .
O3 O 0.76813(16) 0.64807(6) 0.36220(13) 0.0359(3) Uani 1 1 d . . . . .
H3A H 0.8744 0.6523 0.4318 0.054 Uiso 1 1 calc R U . . .
O4 O 0.82004(16) 0.79973(7) 0.37036(12) 0.0365(3) Uani 1 1 d . . . . .
H4A H 0.9357 0.8102 0.4240 0.055 Uiso 1 1 calc R U . . .
O6 O 0.20926(16) 0.82814(7) 0.54951(13) 0.0362(3) Uani 1 1 d . . . . .
H6A H 0.2260 0.8484 0.6317 0.054 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
C1 O1 1.4214(18) . ?
C1 C6 1.516(2) . ?
C1 C2 1.524(2) . ?
C1 H1 0.9800 . ?
C2 O2 1.4350(18) . ?
C2 C3 1.518(2) . ?
C2 H2 0.9800 . ?
C3 O3 1.4237(18) . ?
C3 C4 1.516(2) . ?
C3 H3 0.9800 . ?
C4 O4 1.4219(18) . ?
C4 C5 1.527(2) . ?
C4 H4 0.9800 . ?
C5 N1 1.485(2) . ?
C5 C6 1.520(2) . ?
C5 H5 0.9800 . ?
C6 O6 1.4276(18) . ?
C6 H6 0.9800 . ?
C7 O2 1.421(2) . ?
C7 C8 1.454(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.167(3) . ?
C9 H9 0.9300 . ?
N1 N2 1.217(2) . ?
N2 N3 1.123(2) . ?
O1 H1A 0.8200 . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?
O6 H6A 0.8200 . ?

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
O1 C1 C6 111.54(12) . . ?
O1 C1 C2 111.34(14) . . ?
C6 C1 C2 110.27(12) . . ?
O1 C1 H1 107.8 . . ?
C6 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
O2 C2 C3 109.53(12) . . ?
O2 C2 C1 108.15(12) . . ?
C3 C2 C1 109.95(13) . . ?
O2 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
O3 C3 C4 112.65(12) . . ?
O3 C3 C2 111.86(13) . . ?
C4 C3 C2 110.36(12) . . ?
O3 C3 H3 107.2 . . ?
C4 C3 H3 107.2 . . ?
C2 C3 H3 107.2 . . ?
O4 C4 C3 110.61(12) . . ?
O4 C4 C5 108.36(13) . . ?
C3 C4 C5 111.02(12) . . ?
O4 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
N1 C5 C6 106.00(12) . . ?
N1 C5 C4 108.94(12) . . ?
C6 C5 C4 113.62(14) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
O6 C6 C1 109.64(12) . . ?
O6 C6 C5 109.44(13) . . ?
C1 C6 C5 112.14(12) . . ?
O6 C6 H6 108.5 . . ?
C1 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
O2 C7 C8 112.39(14) . . ?
O2 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
O2 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 177.3(2) . . ?
C8 C9 H9 180.0 . . ?
N2 N1 C5 116.37(15) . . ?
N3 N2 N1 172.1(2) . . ?
C1 O1 H1A 109.5 . . ?
C7 O2 C2 115.88(13) . . ?
C3 O3 H3A 109.5 . . ?
C4 O4 H4A 109.5 . . ?
C6 O6 H6A 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
O1 C1 C2 O2 -64.61(16) . . . . ?
C6 C1 C2 O2 59.75(16) . . . . ?
O1 C1 C2 C3 175.84(12) . . . . ?
C6 C1 C2 C3 -59.80(16) . . . . ?
O2 C2 C3 O3 68.75(16) . . . . ?
C1 C2 C3 O3 -172.55(11) . . . . ?
O2 C2 C3 C4 -57.52(16) . . . . ?
C1 C2 C3 C4 61.19(16) . . . . ?
O3 C3 C4 O4 58.06(16) . . . . ?
C2 C3 C4 O4 -176.11(12) . . . . ?
O3 C3 C4 C5 178.40(12) . . . . ?
C2 C3 C4 C5 -55.78(16) . . . . ?
O4 C4 C5 N1 -70.07(15) . . . . ?
C3 C4 C5 N1 168.27(13) . . . . ?
O4 C4 C5 C6 172.02(11) . . . . ?
C3 C4 C5 C6 50.36(16) . . . . ?
O1 C1 C6 O6 -60.21(16) . . . . ?
C2 C1 C6 O6 175.55(12) . . . . ?
O1 C1 C6 C5 178.02(12) . . . . ?
C2 C1 C6 C5 53.77(16) . . . . ?
N1 C5 C6 O6 68.84(15) . . . . ?
C4 C5 C6 O6 -171.56(12) . . . . ?
N1 C5 C6 C1 -169.27(13) . . . . ?
C4 C5 C6 C1 -49.67(17) . . . . ?
C6 C5 N1 N2 -152.20(15) . . . . ?
C4 C5 N1 N2 85.18(19) . . . . ?
C8 C7 O2 C2 92.59(17) . . . . ?
C3 C2 O2 C7 -129.38(14) . . . . ?
C1 C2 O2 C7 110.81(15) . . . . ?

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
C6 H6 O4 0.98 2.63 3.3403(19) 129.3 4_576
O1 H1A O4 0.82 1.98 2.7938(16) 171.7 4_576
O3 H3A O1 0.82 2.00 2.7950(15) 164.3 1_655
O4 H4A O6 0.82 1.91 2.7267(15) 176.2 1_655
O6 H6A O3 0.82 2.04 2.7999(16) 154.1 4_576

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_POLYMER2
_database_code_depnum_ccdc_archive 'CCDC 2038870'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N3 O5'
_chemical_formula_sum            'C9 H13 N3 O5'
_chemical_formula_weight         243.22

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/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                   6.792(2)
_cell_length_b                   17.062(5)
_cell_length_c                   9.698(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.159(8)
_cell_angle_gamma                90
_cell_volume                     1061.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1701
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      20.62

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.521
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            14418
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1868
_reflns_number_gt                1238
_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, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT 2013/5 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0636P)²+0.4424P] 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         1868
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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
C4 C 0.7644(4) 0.73138(16) 0.1667(3) 0.0249(7) Uani 1 1 d . . . . .
H4 H 0.7750 0.7343 0.2698 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7977(4) 0.64583(16) 0.1286(3) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.7927 0.6431 0.0266 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6266(4) 0.59268(16) 0.1495(3) 0.0240(7) Uani 1 1 d . . . . .
H2 H 0.6512 0.5384 0.1263 0.029 Uiso 1 1 calc R U . . .
C1 C 0.4099(4) 0.61967(16) 0.0483(3) 0.0250(7) Uani 1 1 d . . . . .
H1 H 0.4106 0.6173 -0.0525 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3657(4) 0.70514(16) 0.0802(3) 0.0251(7) Uani 1 1 d . . . . .
H6 H 0.3547 0.7083 0.1783 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5449(4) 0.75981(15) 0.0715(3) 0.0246(7) Uani 1 1 d . . . . .
H5 H 0.5415 0.7610 -0.0303 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3547(5) 0.89301(17) 0.0400(3) 0.0313(7) Uani 1 1 d . . . . .
H9 H 0.2512 0.8850 -0.0495 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7376(5) 0.53558(17) 0.3949(3) 0.0325(8) Uani 1 1 d . . . . .
H7B H 0.7715 0.5529 0.4953 0.039 Uiso 1 1 calc R U . . .
H7A H 0.8673 0.5261 0.3762 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6133(4) 0.45915(17) 0.3744(3) 0.0287(7) Uani 1 1 d . . . . .
N1 N 0.5064(4) 0.84169(13) 0.1137(2) 0.0250(6) Uani 1 1 d . . . . .
N2 N 0.6311(4) 0.87322(15) 0.2407(3) 0.0346(7) Uani 1 1 d . . . . .
N3 N 0.4420(4) 0.44552(15) 0.2523(3) 0.0341(7) Uani 1 1 d . . . . .
O4 O 0.9241(3) 0.78099(13) 0.1425(2) 0.0387(6) Uani 1 1 d . . . . .
H4A H 1.0039 0.7961 0.2212 0.058 Uiso 1 1 calc R U . . .
O3 O 1.0005(3) 0.62021(13) 0.2218(2) 0.0348(6) Uani 1 1 d . . . . .
H3A H 1.0731 0.6092 0.1716 0.052 Uiso 1 1 calc R U . . .
O2 O 0.6228(3) 0.59680(11) 0.2984(2) 0.0287(5) Uani 1 1 d . . . . .
O1 O 0.2436(3) 0.56958(12) 0.0587(2) 0.0324(5) Uani 1 1 d . . . . .
H1A H 0.2926 0.5345 0.1177 0.049 Uiso 1 1 calc R U . . .
O6 O 0.1706(3) 0.72921(12) -0.0257(2) 0.0339(6) Uani 1 1 d . . . . .
H6A H 0.0938 0.7468 0.0168 0.051 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
C4 O4 1.454(3) . ?
C4 C3 1.540(4) . ?
C4 C5 1.551(4) . ?
C4 H4 0.9800 . ?
C3 O3 1.445(3) . ?
C3 C2 1.539(4) . ?
C3 H3 0.9800 . ?
C2 O2 1.454(3) . ?
C2 C1 1.548(4) . ?
C2 H2 0.9800 . ?
C1 O1 1.446(3) . ?
C1 C6 1.541(4) . ?
C1 H1 0.9800 . ?
C6 O6 1.444(3) . ?
C6 C5 1.558(4) . ?
C6 H6 0.9800 . ?
C5 N1 1.503(3) . ?
C5 H5 0.9800 . ?
C9 N1 1.363(4) . ?
C9 C8 1.376(4) 2_655 ?
C9 H9 0.9300 . ?
C7 O2 1.448(3) . ?
C7 C8 1.530(4) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C8 C9 1.375(4) 2_645 ?
C8 N3 1.381(4) . ?
N1 N2 1.355(3) . ?
N2 N3 1.340(3) 2_655 ?
N3 N2 1.340(3) 2_645 ?
O4 H4A 0.8200 . ?
O3 H3A 0.8200 . ?
O1 H1A 0.8200 . ?
O6 H6A 0.8200 . ?

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
O4 C4 C3 109.7(2) . . ?
O4 C4 C5 110.1(2) . . ?
C3 C4 C5 110.0(2) . . ?
O4 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
O3 C3 C2 110.2(2) . . ?
O3 C3 C4 108.8(2) . . ?
C2 C3 C4 110.5(2) . . ?
O3 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
O2 C2 C3 111.3(2) . . ?
O2 C2 C1 107.0(2) . . ?
C3 C2 C1 110.1(2) . . ?
O2 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
O1 C1 C6 109.7(2) . . ?
O1 C1 C2 112.4(2) . . ?
C6 C1 C2 111.2(2) . . ?
O1 C1 H1 107.8 . . ?
C6 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
O6 C6 C1 108.6(2) . . ?
O6 C6 C5 110.0(2) . . ?
C1 C6 C5 110.4(2) . . ?
O6 C6 H6 109.3 . . ?
C1 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
N1 C5 C4 110.3(2) . . ?
N1 C5 C6 109.4(2) . . ?
C4 C5 C6 113.3(2) . . ?
N1 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
N1 C9 C8 105.5(2) . 2_655 ?
N1 C9 H9 127.2 . . ?
C8 C9 H9 127.2 2_655 . ?
O2 C7 C8 112.0(2) . . ?
O2 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O2 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
H7B C7 H7A 107.9 . . ?
C9 C8 N3 107.5(2) 2_645 . ?
C9 C8 C7 130.5(3) 2_645 . ?
N3 C8 C7 121.9(2) . . ?
N2 N1 C9 111.2(2) . . ?
N2 N1 C5 120.3(2) . . ?
C9 N1 C5 128.6(2) . . ?
N3 N2 N1 106.3(2) 2_655 . ?
N2 N3 C8 109.5(2) 2_645 . ?
C4 O4 H4A 109.5 . . ?
C3 O3 H3A 109.5 . . ?
C7 O2 C2 115.2(2) . . ?
C1 O1 H1A 109.5 . . ?
C6 O6 H6A 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
O4 C4 C3 O3 60.5(3) . . . . ?
C5 C4 C3 O3 -178.3(2) . . . . ?
O4 C4 C3 C2 -178.5(2) . . . . ?
C5 C4 C3 C2 -57.2(3) . . . . ?
O3 C3 C2 O2 62.2(3) . . . . ?
C4 C3 C2 O2 -58.0(3) . . . . ?
O3 C3 C2 C1 -179.3(2) . . . . ?
C4 C3 C2 C1 60.4(3) . . . . ?
O2 C2 C1 O1 -61.5(3) . . . . ?
C3 C2 C1 O1 177.5(2) . . . . ?
O2 C2 C1 C6 61.9(3) . . . . ?
C3 C2 C1 C6 -59.1(3) . . . . ?
O1 C1 C6 O6 -60.1(3) . . . . ?
C2 C1 C6 O6 174.9(2) . . . . ?
O1 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C6 C5 54.2(3) . . . . ?
O4 C4 C5 N1 -62.2(3) . . . . ?
C3 C4 C5 N1 176.8(2) . . . . ?
O4 C4 C5 C6 174.7(2) . . . . ?
C3 C4 C5 C6 53.7(3) . . . . ?
O6 C6 C5 N1 64.2(3) . . . . ?
C1 C6 C5 N1 -175.9(2) . . . . ?
O6 C6 C5 C4 -172.2(2) . . . . ?
C1 C6 C5 C4 -52.3(3) . . . . ?
O2 C7 C8 C9 -166.0(3) . . . 2_645 ?
O2 C7 C8 N3 16.7(4) . . . . ?
C8 C9 N1 N2 -0.2(3) 2_655 . . . ?
C8 C9 N1 C5 179.4(2) 2_655 . . . ?
C4 C5 N1 N2 -14.7(3) . . . . ?
C6 C5 N1 N2 110.6(3) . . . . ?
C4 C5 N1 C9 165.6(3) . . . . ?
C6 C5 N1 C9 -69.0(3) . . . . ?
C9 N1 N2 N3 -0.1(3) . . . 2_655 ?
C5 N1 N2 N3 -179.8(2) . . . 2_655 ?
C9 C8 N3 N2 -0.5(3) 2_645 . . 2_645 ?
C7 C8 N3 N2 177.3(3) . . . 2_645 ?
C8 C7 O2 C2 -80.4(3) . . . . ?
C3 C2 O2 C7 -95.9(3) . . . . ?
C1 C2 O2 C7 143.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 N2 0.98 2.64 3.570(4) 158.4 4_575
C1 H1 N3 0.98 2.68 3.560(4) 149.7 3_665
C9 H9 O3 0.93 2.31 3.238(4) 173.4 4_475
C7 H7A O3 0.97 2.56 3.172(4) 121.5 .
O4 H4A O6 0.82 2.38 3.107(3) 148.0 4_676
O3 H3A O1 0.82 1.96 2.772(3) 173.0 1_655
O1 H1A N3 0.82 2.04 2.857(3) 172.9 .
O6 H6A O4 0.82 2.02 2.834(3) 172.7 1_455

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.082



