# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_b642
_database_code_depnum_ccdc_archive 'CCDC 2075478'
loop_
_audit_author_name
_audit_author_address
'Jagadese VITTAL'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 N4 O8'
_chemical_formula_weight         476.48

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                   7.2366(5)
_cell_length_b                   11.3931(8)
_cell_length_c                   14.1809(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.390(2)
_cell_angle_gamma                90
_cell_volume                     1161.91(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.43

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.50
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7902
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_full        25.242
_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             2663
_reflns_number_gt                2295
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 In P2(1)/c, Z = 2, asymmetric unit has one 4apy, half nda and two
 water molecules. No disorder. Coordinates and U(eq) of all the 
 O-H H atoms were fined.The H bond table is given in the 
 res file below.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+0.2446P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2663
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.50380(15) 0.48709(10) 0.32966(8) 0.0461(3) Uani 1 1 d . . . . .
O2 O 0.52254(16) 0.67628(10) 0.36479(8) 0.0459(3) Uani 1 1 d . . . . .
C1 C 0.45138(19) 0.57672(12) 0.37080(9) 0.0331(3) Uani 1 1 d . . . . .
C2 C 0.28833(18) 0.56407(12) 0.42793(9) 0.0307(3) Uani 1 1 d . . . . .
C3 C 0.19305(18) 0.46059(12) 0.42897(9) 0.0325(3) Uani 1 1 d . . . . .
H3 H 0.2356 0.3949 0.3976 0.039 Uiso 1 1 calc R U . . .
C4 C 0.03153(18) 0.45022(11) 0.47640(9) 0.0302(3) Uani 1 1 d . . . . .
C5 C -0.0703(2) 0.34421(12) 0.47781(10) 0.0367(3) Uani 1 1 d . . . . .
H5 H -0.0302 0.2777 0.4466 0.044 Uiso 1 1 calc R U . . .
C6 C -0.2251(2) 0.33734(12) 0.52366(10) 0.0352(3) Uani 1 1 d . . . . .
H6 H -0.2912 0.2663 0.5233 0.042 Uiso 1 1 calc R U . . .
N1 N 0.80006(18) 0.51670(12) 0.23763(9) 0.0437(3) Uani 1 1 d . . . . .
H1 H 0.7010 0.5099 0.2668 0.052 Uiso 1 1 calc R U . . .
C7 C 0.9130(2) 0.60888(15) 0.25549(11) 0.0423(4) Uani 1 1 d . . . . .
H7 H 0.8837 0.6656 0.2996 0.051 Uiso 1 1 calc R U . . .
C8 C 1.0691(2) 0.62248(14) 0.21139(10) 0.0389(3) Uani 1 1 d . . . . .
H8 H 1.1453 0.6886 0.2245 0.047 Uiso 1 1 calc R U . . .
C9 C 1.1165(2) 0.53731(13) 0.14599(10) 0.0364(3) Uani 1 1 d . . . . .
C10 C 0.9941(2) 0.44138(14) 0.12919(11) 0.0437(4) Uani 1 1 d . . . . .
H10 H 1.0198 0.3821 0.0864 0.052 Uiso 1 1 calc R U . . .
C11 C 0.8391(2) 0.43454(15) 0.17483(12) 0.0468(4) Uani 1 1 d . . . . .
H11 H 0.7574 0.3709 0.1622 0.056 Uiso 1 1 calc R U . . .
N2 N 1.26847(18) 0.54835(13) 0.10189(10) 0.0470(3) Uani 1 1 d . . . . .
H2A H 1.2949 0.4954 0.0613 0.056 Uiso 1 1 calc R U . . .
H2B H 1.3414 0.6085 0.1137 0.056 Uiso 1 1 calc R U . . .
O3 O 0.48062(18) 0.24435(11) 0.32436(9) 0.0488(3) Uani 1 1 d . . . . .
H3A H 0.485(3) 0.319(2) 0.3248(15) 0.068(7) Uiso 1 1 d . . . . .
H3B H 0.472(3) 0.228(2) 0.2650(17) 0.074(7) Uiso 1 1 d . . . . .
O4 O 0.3440(2) 0.15956(12) 0.49624(11) 0.0606(4) Uani 1 1 d . . . . .
H4A H 0.385(3) 0.213(2) 0.5408(17) 0.084(8) Uiso 1 1 d . . . . .
H4B H 0.366(3) 0.182(2) 0.4451(18) 0.079(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2555(17) . ?
O2 C1 1.2526(17) . ?
C1 C2 1.5107(17) . ?
C2 C3 1.3666(19) . ?
C2 C6 1.4185(19) 3_566 ?
C3 C4 1.4168(18) . ?
C4 C5 1.4161(19) . ?
C4 C4 1.418(3) 3_566 ?
C5 C6 1.359(2) . ?
C6 C2 1.4185(19) 3_566 ?
N1 C7 1.337(2) . ?
N1 C11 1.344(2) . ?
C7 C8 1.360(2) . ?
C8 C9 1.411(2) . ?
C9 N2 1.3305(19) . ?
C9 C10 1.410(2) . ?
C10 C11 1.358(2) . ?

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 C1 O1 123.87(12) . . ?
O2 C1 C2 118.32(12) . . ?
O1 C1 C2 117.77(12) . . ?
C3 C2 C6 119.18(12) . 3_566 ?
C3 C2 C1 120.88(12) . . ?
C6 C2 C1 119.82(12) 3_566 . ?
C2 C3 C4 121.39(12) . . ?
C5 C4 C3 122.40(12) . . ?
C5 C4 C4 118.70(15) . 3_566 ?
C3 C4 C4 118.90(15) . 3_566 ?
C6 C5 C4 120.92(12) . . ?
C5 C6 C2 120.90(12) . 3_566 ?
C7 N1 C11 120.23(13) . . ?
N1 C7 C8 121.58(14) . . ?
C7 C8 C9 119.95(14) . . ?
N2 C9 C10 122.02(14) . . ?
N2 C9 C8 121.22(14) . . ?
C10 C9 C8 116.76(13) . . ?
C11 C10 C9 120.02(15) . . ?
N1 C11 C10 121.44(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
N1 H1 O1 0.87 1.78 2.6527(16) 176.2 .
N2 H2B O3 0.87 2.14 2.9925(19) 166.9 2_755
N2 H2A O4 0.87 2.04 2.887(2) 163.9 4_665
O3 H3A O1 0.85(3) 1.92(3) 2.7711(17) 178(2) .
O3 H3B O2 0.86(2) 1.94(3) 2.7899(17) 173(2) 2_645
O4 H4A O2 0.90(3) 1.91(3) 2.8090(19) 178(2) 3_666
O4 H4B O3 0.80(3) 2.11(3) 2.8963(18) 168(2) .

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_b722
_database_code_depnum_ccdc_archive 'CCDC 2075480'
loop_
_audit_author_name
_audit_author_address
'Jagadese VITTAL'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N6 O5'
_chemical_formula_weight         500.51

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                   17.7868(13)
_cell_length_b                   9.9141(7)
_cell_length_c                   12.5079(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.210(2)
_cell_angle_gamma                90
_cell_volume                     2170.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4345
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.54

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   MUlti-scan
_exptl_absorpt_correction_T_min  0.6908
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7421
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2489
_reflns_number_gt                2362
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 In C2/c, Z = 4, the asymmetric unit contals one 2abi, half nda and
 one water molecule. No disorder. The H-atoms were constrained
 using DFIX for N-H and O-H hydrogen atoms. The hydrogen atom
 parameters are given below in res file.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+5.3646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2489
_refine_ls_number_parameters     184
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.074
_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
O1 O 0.31211(7) 0.36444(13) 0.47157(10) 0.0141(3) Uani 1 1 d . . . . .
O2 O 0.35952(7) 0.31826(13) 0.64534(10) 0.0138(3) Uani 1 1 d . . . . .
N1 N 0.26241(8) 0.06454(15) 0.93170(11) 0.0115(3) Uani 1 1 d D . . . .
H1 H 0.2373(14) 0.002(2) 0.959(2) 0.037(8) Uiso 1 1 d D . . . .
N2 N 0.30382(8) 0.19250(15) 0.81070(12) 0.0126(3) Uani 1 1 d D . . . .
H2 H 0.3119(13) 0.222(2) 0.7480(9) 0.015 Uiso 1 1 d D U . . .
N3 N 0.20869(9) 0.02946(16) 0.74660(12) 0.0148(3) Uani 1 1 d D . . . .
H3A H 0.1989(13) 0.066(2) 0.6826(9) 0.018 Uiso 1 1 d D U . . .
H3B H 0.1776(11) -0.0280(18) 0.7679(18) 0.018 Uiso 1 1 d D U . . .
C1 C 0.25543(10) 0.09244(17) 0.82540(13) 0.0118(3) Uani 1 1 d . . . . .
C2 C 0.31787(9) 0.14940(17) 0.98892(14) 0.0113(3) Uani 1 1 d . . . . .
C3 C 0.34684(10) 0.16160(18) 1.09916(14) 0.0131(4) Uani 1 1 d . . . . .
H3 H 0.3291 0.1062 1.1515 0.016 Uiso 1 1 calc R U . . .
C4 C 0.40316(10) 0.25910(19) 1.12947(15) 0.0151(4) Uani 1 1 d . . . . .
H4 H 0.4244 0.2702 1.2042 0.018 Uiso 1 1 calc R U . . .
C5 C 0.42898(10) 0.34052(18) 1.05264(15) 0.0154(4) Uani 1 1 d . . . . .
H5 H 0.4673 0.4060 1.0762 0.019 Uiso 1 1 calc R U . . .
C6 C 0.39999(10) 0.32825(18) 0.94223(15) 0.0144(4) Uani 1 1 d . . . . .
H6 H 0.4176 0.3839 0.8900 0.017 Uiso 1 1 calc R U . . .
C7 C 0.34428(10) 0.23129(17) 0.91207(14) 0.0121(3) Uani 1 1 d . . . . .
C8 C 0.35393(9) 0.29692(17) 0.54404(13) 0.0106(3) Uani 1 1 d . . . . .
C9 C 0.43881(10) 0.04651(17) 0.36775(13) 0.0118(3) Uani 1 1 d . . . . .
H9 H 0.4322 0.0215 0.2934 0.014 Uiso 1 1 calc R U . . .
C10 C 0.39343(10) 0.14522(17) 0.39921(13) 0.0115(3) Uani 1 1 d . . . . .
H10 H 0.3559 0.1878 0.3466 0.014 Uiso 1 1 calc R U . . .
C11 C 0.40207(9) 0.18424(17) 0.50971(13) 0.0104(3) Uani 1 1 d . . . . .
C12 C 0.45631(10) 0.12161(17) 0.58565(13) 0.0112(3) Uani 1 1 d . . . . .
H12 H 0.4617 0.1474 0.6598 0.013 Uiso 1 1 calc R U . . .
C13 C 0.50448(9) 0.01906(16) 0.55555(13) 0.0104(3) Uani 1 1 d . . . . .
O3 O 0.5000 0.4488(3) 0.7500 0.0419(6) Uani 1 2 d DS T P . .
H3W H 0.4660(15) 0.400(3) 0.709(2) 0.050 Uiso 1 1 d D 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 C8 1.259(2) . ?
O2 C8 1.271(2) . ?
N1 C1 1.342(2) . ?
N1 C2 1.394(2) . ?
N2 C1 1.347(2) . ?
N2 C7 1.396(2) . ?
N3 C1 1.328(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.401(2) . ?
C3 C4 1.395(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.384(2) . ?
C8 C11 1.515(2) . ?
C9 C10 1.370(2) . ?
C9 C13 1.420(2) 5_656 ?
C10 C11 1.417(2) . ?
C11 C12 1.376(2) . ?
C12 C13 1.423(2) . ?
C13 C9 1.420(2) 5_656 ?
C13 C13 1.422(3) 5_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 108.49(14) . . ?
C1 N2 C7 108.53(14) . . ?
N3 C1 N1 125.06(16) . . ?
N3 C1 N2 125.19(15) . . ?
N1 C1 N2 109.75(15) . . ?
C3 C2 N1 131.80(16) . . ?
C3 C2 C7 121.32(16) . . ?
N1 C2 C7 106.87(14) . . ?
C2 C3 C4 116.88(16) . . ?
C5 C4 C3 121.49(17) . . ?
C6 C5 C4 121.62(17) . . ?
C7 C6 C5 116.92(16) . . ?
C6 C7 N2 131.88(16) . . ?
C6 C7 C2 121.76(16) . . ?
N2 C7 C2 106.36(15) . . ?
O1 C8 O2 124.14(16) . . ?
O1 C8 C11 118.65(15) . . ?
O2 C8 C11 117.19(15) . . ?
C10 C9 C13 121.13(15) . 5_656 ?
C9 C10 C11 120.51(15) . . ?
C12 C11 C10 119.45(15) . . ?
C12 C11 C8 119.95(15) . . ?
C10 C11 C8 120.57(15) . . ?
C11 C12 C13 121.41(15) . . ?
C9 C13 C13 118.79(19) 5_656 5_656 ?
C9 C13 C12 122.50(15) 5_656 . ?
C13 C13 C12 118.71(19) 5_656 . ?

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
N1 H1 O1 0.868(5) 1.913(6) 2.7794(19) 176(3) 4_546
N2 H2 O2 0.871(5) 1.916(10) 2.7460(19) 159(2) .
N3 H3A O1 0.868(5) 2.024(6) 2.8865(19) 172(2) 7_556
N3 H3B O2 0.868(5) 2.047(10) 2.875(2) 159(2) 4_546
C6 H6 O3 0.95 2.56 3.448(2) 156.4 .
O3 H3W O2 0.865(5) 2.086(14) 2.9107(18) 159(3) .

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.098

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_d303
_database_code_depnum_ccdc_archive 'CCDC 2075481'
loop_
_audit_author_name
_audit_author_address
'Jagadese VITTAL'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N6 O5'
_chemical_formula_weight         476.49

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   17.637(2)
_cell_length_b                   10.0843(13)
_cell_length_c                   12.2714(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.452(3)
_cell_angle_gamma                90
_cell_volume                     2131.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    866
_cell_measurement_theta_min      4.12
_cell_measurement_theta_max      27.46

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7595
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7330
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.725
_diffrn_reflns_point_group_measured_fraction_full 0.747
_reflns_number_total             3538
_reflns_number_gt                3465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.454
_reflns_Friedel_fraction_max     0.453
_reflns_Friedel_fraction_full    0.496

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Initially C2/c space group was attempted.However, the anisotropic 
 thermal parameters were large and the disorder at the CCA ligand 
 due to crystallogrpahy imposed disorder could not be resolved 
 satisfactorily. Hence Cc was tried. To our surprice, the model 
 refined very well in this space group. The occupancy was refined 
 to 0.8101(9). A common isotorpic thermal parameter was refined for 
 the minor disorder to 0.012(2). Soft constraints FLAT and SAME 
 were used to restrain hexagonal geomtry for the minor disordered 
 phenyl ring of CCA ligand. The option DFIX was used for the two 
 H atoms of lattice water. The hydrogen bonding table is given 
 in the res file below. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0829P)²+2.2439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3538
_refine_ls_number_parameters     348
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.095
_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 0.43129(18) 0.8203(3) 0.5223(2) 0.0210(6) Uani 1 1 d . . . . .
O2 O 0.47680(16) 0.8660(3) 0.7023(2) 0.0182(6) Uani 1 1 d . . . . .
O3 O 0.14375(17) 0.1920(3) 0.8180(2) 0.0203(6) Uani 1 1 d . . . . .
O4 O 0.09505(16) 0.1327(3) 0.64193(19) 0.0174(5) Uani 1 1 d . . . . .
N1 N 0.51982(19) 0.5624(3) 0.2341(2) 0.0143(6) Uani 1 1 d . . . . .
H1 H 0.5452 0.5019 0.2045 0.017 Uiso 1 1 calc R U . . .
N2 N 0.4798(2) 0.6836(3) 0.3587(2) 0.0176(7) Uani 1 1 d . . . . .
H2 H 0.4749 0.7154 0.4235 0.021 Uiso 1 1 calc R U . . .
N3 N 0.5743(2) 0.5185(3) 0.4245(3) 0.0218(7) Uani 1 1 d . . . . .
H3A H 0.6039 0.4547 0.4079 0.026 Uiso 1 1 calc R U . . .
H3B H 0.5760 0.5386 0.4947 0.026 Uiso 1 1 calc R U . . .
C1 C 0.5272(2) 0.5843(4) 0.3437(3) 0.0167(8) Uani 1 1 d . . . . .
C2 C 0.4662(2) 0.6499(4) 0.1754(3) 0.0157(7) Uani 1 1 d . . . . .
C3 C 0.4379(2) 0.6700(4) 0.0627(3) 0.0183(8) Uani 1 1 d . . . . .
H3 H 0.4555 0.6179 0.0086 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3828(2) 0.7686(4) 0.0310(3) 0.0229(8) Uani 1 1 d . . . . .
H4A H 0.3625 0.7844 -0.0461 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3564(3) 0.8458(4) 0.1106(4) 0.0245(9) Uani 1 1 d . . . . .
H5A H 0.3181 0.9120 0.0866 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3856(3) 0.8266(4) 0.2240(3) 0.0214(8) Uani 1 1 d . . . . .
H6 H 0.3688 0.8796 0.2783 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4396(2) 0.7280(4) 0.2546(3) 0.0173(7) Uani 1 1 d . . . . .
C8 C 0.0483(2) 0.5894(4) 0.5054(3) 0.0190(8) Uani 1 1 d . . . . .
C9 C 0.1088(2) 0.6495(3) 0.6772(3) 0.0163(7) Uani 1 1 d . . . . .
C10 C 0.1350(2) 0.6639(4) 0.7913(3) 0.0182(8) Uani 1 1 d . . . . .
H10 H 0.1164 0.6095 0.8432 0.022 Uiso 1 1 calc R U . . .
C11 C 0.1902(2) 0.7627(4) 0.8258(3) 0.0234(8) Uani 1 1 d . . . . .
H11 H 0.2098 0.7763 0.9034 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2172(3) 0.8418(4) 0.7496(4) 0.0251(9) Uani 1 1 d . . . . .
H12 H 0.2547 0.9083 0.7767 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1911(3) 0.8268(4) 0.6355(4) 0.0252(9) Uani 1 1 d . . . . .
H13 H 0.2102 0.8807 0.5838 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1358(2) 0.7293(4) 0.6006(3) 0.0197(8) Uani 1 1 d . . . . .
N4 N 0.05437(19) 0.5624(3) 0.6143(2) 0.0165(7) Uani 1 1 d . . . . .
H4 H 0.0285 0.5005 0.6416 0.020 Uiso 1 1 calc R U . . .
N5 N 0.0981(2) 0.6880(3) 0.4944(3) 0.0200(7) Uani 1 1 d . . . . .
H5 H 0.1053 0.7205 0.4309 0.024 Uiso 1 1 calc R U . . .
N6 N 0.0025(2) 0.5254(3) 0.4223(2) 0.0226(7) Uani 1 1 d . . . . .
H6A H -0.0269 0.4599 0.4366 0.027 Uiso 1 1 calc R U . . .
H6B H 0.0014 0.5483 0.3528 0.027 Uiso 1 1 calc R U . . .
C15 C 0.4351(2) 0.7994(3) 0.6252(3) 0.0159(7) Uani 1 1 d . . . . .
C16 C 0.3856(3) 0.6895(4) 0.6511(4) 0.0111(10) Uani 0.811(9) 1 d . U P A 1
C17 C 0.3876(3) 0.6537(4) 0.7609(3) 0.0147(9) Uani 0.811(9) 1 d . U P A 1
H17 H 0.4226 0.6967 0.8199 0.018 Uiso 0.811(9) 1 calc R U P A 1
C18 C 0.3388(3) 0.5556(4) 0.7847(3) 0.0166(9) Uani 0.811(9) 1 d . U P A 1
H18 H 0.3413 0.5323 0.8604 0.020 Uiso 0.811(9) 1 calc R U P A 1
C19 C 0.2861(3) 0.4897(4) 0.7013(5) 0.0149(10) Uani 0.811(9) 1 d . U P A 1
C20 C 0.2848(3) 0.5257(5) 0.5902(5) 0.0190(10) Uani 0.811(9) 1 d . U P A 1
H20 H 0.2501 0.4826 0.5308 0.023 Uiso 0.811(9) 1 calc R U P A 1
C21 C 0.3334(3) 0.6227(5) 0.5672(5) 0.0173(9) Uani 0.811(9) 1 d . U P A 1
H21 H 0.3316 0.6454 0.4916 0.021 Uiso 0.811(9) 1 calc R U P A 1
C22 C 0.2348(3) 0.3880(4) 0.7336(5) 0.0163(10) Uani 0.811(9) 1 d . U P A 1
H22B H 0.2397 0.3761 0.8117 0.020 Uiso 0.811(9) 1 calc R U P A 1
C23 C 0.1817(4) 0.3094(6) 0.6675(4) 0.0169(11) Uani 0.811(9) 1 d . U P A 1
H23 H 0.1725 0.3207 0.5889 0.020 Uiso 0.811(9) 1 calc R U P A 1
C24 C 0.1369(2) 0.2051(3) 0.7140(3) 0.0162(7) Uani 1 1 d . U . . .
O1W O 0.2835(4) 0.9318(3) 0.4264(4) 0.0567(8) Uani 1 1 d D . . . .
H1W H 0.253(3) 0.852(4) 0.400(5) 0.068 Uiso 1 1 d D U . . .
H2W H 0.321(3) 0.901(6) 0.493(3) 0.068 Uiso 1 1 d D U . . .
C16A C 0.1918(17) 0.322(3) 0.6944(15) 0.012(2) Uiso 0.189(9) 1 d D U P A 2
C17A C 0.2382(11) 0.3773(17) 0.7863(19) 0.012(2) Uiso 0.189(9) 1 d D U P A 2
H17A H 0.2377 0.3510 0.8605 0.014 Uiso 0.189(9) 1 calc R U P A 2
C18A C 0.2871(10) 0.4778(17) 0.760(2) 0.012(2) Uiso 0.189(9) 1 d D U P A 2
H18A H 0.3215 0.5225 0.8184 0.014 Uiso 0.189(9) 1 calc R U P A 2
C19A C 0.2862(11) 0.5140(19) 0.6467(18) 0.012(2) Uiso 0.189(9) 1 d D U P A 2
C20A C 0.2341(10) 0.4459(16) 0.5569(14) 0.012(2) Uiso 0.189(9) 1 d D U P A 2
H20A H 0.2340 0.4659 0.4813 0.014 Uiso 0.189(9) 1 calc R U P A 2
C21A C 0.1830(11) 0.3482(16) 0.5844(15) 0.012(2) Uiso 0.189(9) 1 d D U P A 2
H21A H 0.1453 0.3043 0.5291 0.014 Uiso 0.189(9) 1 calc R U P A 2
C22A C 0.3358(12) 0.6178(19) 0.619(2) 0.012(2) Uiso 0.189(9) 1 d . U P A 2
H22A H 0.3320 0.6352 0.5417 0.014 Uiso 0.189(9) 1 calc R U P A 2
C23A C 0.3842(16) 0.688(2) 0.688(2) 0.012(2) Uiso 0.189(9) 1 d . U P A 2
H23A H 0.3914 0.6797 0.7666 0.014 Uiso 0.189(9) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.268(4) . ?
O2 C15 1.260(4) . ?
O3 C24 1.263(4) . ?
O4 C24 1.256(5) . ?
N1 C1 1.342(4) . ?
N1 C2 1.378(5) . ?
N2 C1 1.343(5) . ?
N2 C7 1.394(5) . ?
N3 C1 1.325(5) . ?
C2 C3 1.380(5) . ?
C2 C7 1.407(5) . ?
C3 C4 1.386(6) . ?
C4 C5 1.405(6) . ?
C5 C6 1.389(6) . ?
C6 C7 1.372(6) . ?
C8 N6 1.324(5) . ?
C8 N4 1.346(5) . ?
C8 N5 1.351(5) . ?
C9 C10 1.385(5) . ?
C9 C14 1.398(5) . ?
C9 N4 1.403(5) . ?
C10 C11 1.393(6) . ?
C11 C12 1.389(6) . ?
C12 C13 1.385(6) . ?
C13 C14 1.386(6) . ?
C14 N5 1.393(5) . ?
C15 C16 1.487(6) . ?
C15 C23A 1.72(3) . ?
C16 C17 1.388(6) . ?
C16 C21 1.397(7) . ?
C17 C18 1.382(6) . ?
C18 C19 1.394(6) . ?
C19 C20 1.406(6) . ?
C19 C22 1.478(7) . ?
C20 C21 1.369(7) . ?
C22 C23 1.355(7) . ?
C23 C24 1.499(8) . ?
C24 C16A 1.58(4) . ?
C16A C21A 1.35(2) . ?
C16A C17A 1.36(2) . ?
C17A C18A 1.41(2) . ?
C18A C19A 1.43(2) . ?
C19A C20A 1.45(2) . ?
C19A C22A 1.45(3) . ?
C20A C21A 1.42(2) . ?
C22A C23A 1.28(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.1(3) . . ?
C1 N2 C7 108.9(3) . . ?
N3 C1 N1 125.2(3) . . ?
N3 C1 N2 125.4(3) . . ?
N1 C1 N2 109.3(3) . . ?
N1 C2 C3 132.6(3) . . ?
N1 C2 C7 106.9(3) . . ?
C3 C2 C7 120.5(3) . . ?
C2 C3 C4 117.8(4) . . ?
C3 C4 C5 121.3(4) . . ?
C6 C5 C4 120.8(4) . . ?
C7 C6 C5 117.4(4) . . ?
C6 C7 N2 132.0(4) . . ?
C6 C7 C2 122.1(3) . . ?
N2 C7 C2 105.9(3) . . ?
N6 C8 N4 124.8(4) . . ?
N6 C8 N5 125.7(4) . . ?
N4 C8 N5 109.5(4) . . ?
C10 C9 C14 122.1(4) . . ?
C10 C9 N4 131.4(3) . . ?
C14 C9 N4 106.4(3) . . ?
C9 C10 C11 116.2(3) . . ?
C12 C11 C10 121.6(4) . . ?
C13 C12 C11 122.1(4) . . ?
C12 C13 C14 116.6(4) . . ?
C13 C14 N5 131.7(4) . . ?
C13 C14 C9 121.3(4) . . ?
N5 C14 C9 107.0(3) . . ?
C8 N4 C9 108.5(3) . . ?
C8 N5 C14 108.5(3) . . ?
O2 C15 O1 123.8(4) . . ?
O2 C15 C16 120.8(3) . . ?
O1 C15 C16 115.4(3) . . ?
O2 C15 C23A 106.8(9) . . ?
O1 C15 C23A 129.4(10) . . ?
C17 C16 C21 117.7(5) . . ?
C17 C16 C15 120.5(4) . . ?
C21 C16 C15 121.7(4) . . ?
C18 C17 C16 120.3(4) . . ?
C17 C18 C19 122.2(4) . . ?
C18 C19 C20 117.2(5) . . ?
C18 C19 C22 118.9(5) . . ?
C20 C19 C22 123.9(4) . . ?
C21 C20 C19 120.3(5) . . ?
C20 C21 C16 122.3(5) . . ?
C23 C22 C19 129.0(5) . . ?
C22 C23 C24 122.4(5) . . ?
O4 C24 O3 124.3(4) . . ?
O4 C24 C23 114.7(3) . . ?
O3 C24 C23 121.0(4) . . ?
O4 C24 C16A 127.9(7) . . ?
O3 C24 C16A 107.7(7) . . ?
C21A C16A C17A 132(3) . . ?
C21A C16A C24 110.8(18) . . ?
C17A C16A C24 117.2(19) . . ?
C16A C17A C18A 113(2) . . ?
C17A C18A C19A 121.9(18) . . ?
C18A C19A C20A 119.3(19) . . ?
C18A C19A C22A 122.1(16) . . ?
C20A C19A C22A 118.6(19) . . ?
C21A C20A C19A 118.6(15) . . ?
C16A C21A C20A 115(2) . . ?
C23A C22A C19A 126(2) . . ?
C22A C23A C15 114(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
N1 H1 O4 0.88 1.87 2.749(4) 177.1 4_554
N2 H2 O1 0.88 1.89 2.722(4) 156.4 .
N3 H3A O3 0.88 2.06 2.899(4) 159.8 4_554
N3 H3B O4 0.88 2.00 2.856(4) 163.0 3
C6 H6 O1W 0.95 2.65 3.531(7) 154.4 .
C13 H13 O1W 0.95 2.60 3.487(7) 156.2 .
N4 H4 O2 0.88 1.88 2.756(4) 178.0 3_445
N5 H5 O3 0.88 1.89 2.749(4) 165.6 2_564
N6 H6A O1 0.88 1.99 2.833(4) 159.5 3_445
N6 H6B O2 0.88 2.00 2.857(4) 164.5 4_464
O1W H1W O3 0.985(13) 2.02(4) 2.826(7) 137(5) 2_564
O1W H2W O1 0.985(13) 2.07(5) 2.850(7) 135(5) .

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.073

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_b441
_database_code_depnum_ccdc_archive 'CCDC 2075479'
loop_
_audit_author_name
_audit_author_address
'Jagadese VITTAL'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N4 O8'
_chemical_formula_weight         452.46

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                   7.0741(11)
_cell_length_b                   11.0582(17)
_cell_length_c                   14.289(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.460(3)
_cell_angle_gamma                90
_cell_volume                     1105.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1024
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.28

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7447
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'
_exptl_absorpt_special_details   none

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7546
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.338
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2525
_reflns_number_gt                2406
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 In P2(1)/c, Z = 2, asymmetric unit has one 4apy, half cca and two
 water molecules. Due to inversion center cca looks like nda.
 Coordinates and U(eq) of all the N-H and  
 O-H H atoms were fined.The H bond table is given in the 
 res file below.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+2.0168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2525
_refine_ls_number_parameters     209
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.1868
_refine_ls_wR_factor_gt          0.1858
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_restrained_S_all      1.248
_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 0.4990(3) 0.49331(17) 0.32092(13) 0.0235(4) Uani 1 1 d . . . . .
O2 O 0.5262(3) 0.68685(18) 0.36232(14) 0.0321(5) Uani 1 1 d . . . . .
C1 C 0.4560(4) 0.5833(2) 0.36729(18) 0.0240(6) Uani 1 1 d . . . . .
C2 C 0.3240(8) 0.5781(6) 0.4355(4) 0.0185(8) Uani 0.5 1 d . U P A -1
H2C H 0.3244 0.6398 0.4818 0.022 Uiso 0.5 1 calc R U P A -1
C3 C 0.2036(8) 0.4875(5) 0.4327(4) 0.0185(7) Uani 0.5 1 d . U P A -1
H3D H 0.2244 0.4224 0.3920 0.022 Uiso 0.5 1 calc R U P A -1
C4 C 0.0385(8) 0.4741(5) 0.4854(4) 0.0184(6) Uani 0.5 1 d . U P A -1
C5 C -0.0172(8) 0.5666(5) 0.5419(4) 0.0186(6) Uani 0.5 1 d . U P A -1
H5 H 0.0512 0.6408 0.5481 0.022 Uiso 0.5 1 calc R U P A -1
C6 C -0.1736(8) 0.5495(5) 0.5890(4) 0.0184(6) Uani 0.5 1 d . U P A -1
H6 H -0.2118 0.6125 0.6273 0.022 Uiso 0.5 1 calc R U P A -1
C7 C -0.2739(9) 0.4425(6) 0.5809(5) 0.0179(7) Uani 0.5 1 d . U P A -1
C8 C -0.2214(7) 0.3501(4) 0.5239(3) 0.0182(6) Uani 0.5 1 d . U P A -1
H3C H -0.2920 0.2768 0.5171 0.022 Uiso 0.5 1 calc R U P A -1
C9 C -0.0645(7) 0.3663(4) 0.4769(3) 0.0185(6) Uani 0.5 1 d . U P A -1
H9 H -0.0270 0.3030 0.4386 0.022 Uiso 0.5 1 calc R U P A -1
N1 N 0.7977(3) 0.5171(2) 0.22781(15) 0.0225(5) Uani 1 1 d . . . . .
H1 H 0.683(5) 0.508(3) 0.259(2) 0.026(8) Uiso 1 1 d . . . . .
C10 C 0.9131(4) 0.6131(3) 0.24562(19) 0.0242(6) Uani 1 1 d . . . . .
H10 H 0.8834 0.6729 0.2889 0.029 Uiso 1 1 calc R U . . .
C11 C 1.0719(4) 0.6266(2) 0.20312(18) 0.0226(5) Uani 1 1 d . . . . .
H11 H 1.1511 0.6957 0.2164 0.027 Uiso 1 1 calc R U . . .
C12 C 1.1189(4) 0.5378(2) 0.13917(17) 0.0205(5) Uani 1 1 d . . . . .
C13 C 0.9939(4) 0.4375(2) 0.12236(18) 0.0209(5) Uani 1 1 d . . . . .
H13 H 1.0201 0.3751 0.0804 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8359(4) 0.4306(2) 0.16652(19) 0.0232(5) Uani 1 1 d . . . . .
H14 H 0.7514 0.3639 0.1540 0.028 Uiso 1 1 calc R U . . .
N2 N 1.2728(3) 0.5495(2) 0.09591(16) 0.0237(5) Uani 1 1 d . . . . .
H2A H 1.349(6) 0.614(4) 0.114(3) 0.041(10) Uiso 1 1 d . . . . .
H2B H 1.308(5) 0.495(4) 0.060(3) 0.039(10) Uiso 1 1 d . . . . .
O3 O 0.6634(3) 0.83900(19) 0.51012(16) 0.0299(5) Uani 1 1 d . . . . .
H3A H 0.632(6) 0.810(4) 0.561(3) 0.046(11) Uiso 1 1 d . . . . .
H3B H 0.619(5) 0.790(3) 0.471(3) 0.033(10) Uiso 1 1 d . . . . .
O4 O 0.5186(3) 0.75048(19) 0.67399(14) 0.0253(4) Uani 1 1 d . . . . .
H4A H 0.532(5) 0.768(4) 0.733(3) 0.040(10) Uiso 1 1 d . . . . .
H4B H 0.515(7) 0.679(5) 0.671(3) 0.059(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.258(3) . ?
O2 C1 1.254(3) . ?
C1 C2 1.446(7) . ?
C2 C3 1.312(8) . ?
C3 C4 1.488(7) . ?
C4 C9 1.393(7) . ?
C4 C5 1.395(9) . ?
C5 C6 1.389(7) . ?
C6 C7 1.375(8) . ?
C7 C8 1.391(8) . ?
C8 C9 1.390(7) . ?
N1 C10 1.340(4) . ?
N1 C14 1.351(4) . ?
C10 C11 1.362(4) . ?
C11 C12 1.414(4) . ?
C12 N2 1.335(3) . ?
C12 C13 1.416(4) . ?
C13 C14 1.364(4) . ?

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 C1 O1 124.3(2) . . ?
O2 C1 C2 112.0(3) . . ?
O1 C1 C2 123.6(3) . . ?
C3 C2 C1 119.4(5) . . ?
C2 C3 C4 127.9(5) . . ?
C9 C4 C5 119.3(4) . . ?
C9 C4 C3 118.7(5) . . ?
C5 C4 C3 122.0(5) . . ?
C6 C5 C4 119.5(5) . . ?
C7 C6 C5 120.9(5) . . ?
C6 C7 C8 120.2(5) . . ?
C9 C8 C7 119.3(5) . . ?
C8 C9 C4 120.8(5) . . ?
C10 N1 C14 120.6(2) . . ?
N1 C10 C11 121.5(2) . . ?
C10 C11 C12 120.0(2) . . ?
N2 C12 C11 121.1(2) . . ?
N2 C12 C13 121.9(2) . . ?
C11 C12 C13 116.9(2) . . ?
C14 C13 C12 119.9(2) . . ?
N1 C14 C13 121.1(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
N1 H1 O1 0.99(3) 1.69(3) 2.671(3) 175(3) .
N2 H2A O4 0.91(4) 2.03(4) 2.931(3) 172(3) 4_675
N2 H2B O3 0.85(4) 2.02(4) 2.850(3) 164(4) 2_745
O3 H3A O4 0.85(4) 2.02(4) 2.863(3) 172(4) .
O3 H3B O2 0.81(4) 1.96(4) 2.762(3) 172(4) .
O4 H4A O2 0.86(4) 1.92(4) 2.772(3) 172(4) 4_576
O4 H4B O1 0.79(5) 1.92(5) 2.700(3) 173(5) 3_666

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.080

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_F232
_database_code_depnum_ccdc_archive 'CCDC 2075482'
loop_
_audit_author_name
_audit_author_address
'Jagadese VITTAL'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N4 O4'
_chemical_formula_weight         404.42

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                   9.1101(5)
_cell_length_b                   10.3633(6)
_cell_length_c                   11.2788(7)
_cell_angle_alpha                100.613(2)
_cell_angle_beta                 98.629(2)
_cell_angle_gamma                113.035(2)
_cell_volume                     933.68(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9465
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.26

_exptl_crystal_description       'prism frag'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.359
_exptl_crystal_size_min          0.219
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture'
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21764
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.216
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4660
_reflns_number_gt                3789
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 In triclinic P-1 with Z = 2, the asymmetric unit contains two
 half nda anions two full 2apy cations. The coordinations and 
 a commom U(eq) of all the N-H hydrogen atoms were refined.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+0.3184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4660
_refine_ls_number_parameters     290
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.40128(11) 0.31036(10) 0.43653(8) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.39485(11) 0.35131(10) 0.63715(8) 0.0176(2) Uani 1 1 d . . . . .
O3 O 0.43409(11) 0.84377(10) 0.08386(8) 0.0177(2) Uani 1 1 d . . . . .
O4 O 0.29128(11) 0.74255(10) -0.11513(8) 0.0198(2) Uani 1 1 d . . . . .
N1 N 0.62198(12) 0.20732(11) 0.47421(9) 0.0136(2) Uani 1 1 d D . . . .
H1 H 0.5501(18) 0.2521(18) 0.4674(16) 0.0340(19) Uiso 1 1 d D U . . .
C1 C 0.68634(15) 0.18084(13) 0.37651(11) 0.0164(3) Uani 1 1 d . . . . .
H1A H 0.6649 0.2145 0.3059 0.020 Uiso 1 1 calc R U . . .
C2 C 0.78117(16) 0.10681(14) 0.37791(12) 0.0202(3) Uani 1 1 d . . . . .
H2 H 0.8277 0.0898 0.3100 0.024 Uiso 1 1 calc R U . . .
C3 C 0.80816(16) 0.05630(14) 0.48273(13) 0.0210(3) Uani 1 1 d . . . . .
H3A H 0.8702 0.0010 0.4844 0.025 Uiso 1 1 calc R U . . .
C4 C 0.74635(15) 0.08562(13) 0.58249(12) 0.0170(3) Uani 1 1 d . . . . .
H4 H 0.7671 0.0526 0.6536 0.020 Uiso 1 1 calc R U . . .
C5 C 0.65122(14) 0.16562(12) 0.57879(11) 0.0135(2) Uani 1 1 d . . . . .
N2 N 0.58841(13) 0.20222(12) 0.67206(10) 0.0165(2) Uani 1 1 d D . . . .
H2A H 0.5227(19) 0.2519(17) 0.6611(15) 0.0340(19) Uiso 1 1 d D U . . .
H2B H 0.597(2) 0.1684(17) 0.7422(12) 0.0340(19) Uiso 1 1 d D U . . .
N3 N 0.63716(12) 0.72308(11) 0.04462(9) 0.0134(2) Uani 1 1 d D . . . .
H3 H 0.5649(18) 0.7670(17) 0.0527(16) 0.0340(19) Uiso 1 1 d D U . . .
C6 C 0.60828(15) 0.62151(12) -0.06161(11) 0.0131(2) Uani 1 1 d . . . . .
C7 C 0.71663(15) 0.55374(13) -0.06709(12) 0.0169(3) Uani 1 1 d . . . . .
H7 H 0.6984 0.4798 -0.1389 0.020 Uiso 1 1 calc R U . . .
C8 C 0.84681(16) 0.59536(15) 0.03128(12) 0.0202(3) Uani 1 1 d . . . . .
H8 H 0.9192 0.5499 0.0274 0.024 Uiso 1 1 calc R U . . .
C9 C 0.87604(16) 0.70439(14) 0.13857(12) 0.0188(3) Uani 1 1 d . . . . .
H9 H 0.9686 0.7353 0.2063 0.023 Uiso 1 1 calc R U . . .
C10 C 0.76728(15) 0.76398(13) 0.14213(11) 0.0161(3) Uani 1 1 d . . . . .
H10 H 0.7828 0.8359 0.2146 0.019 Uiso 1 1 calc R U . . .
N4 N 0.48017(13) 0.58945(11) -0.15378(10) 0.0156(2) Uani 1 1 d D . . . .
H4A H 0.4134(18) 0.6374(16) -0.1433(15) 0.0340(19) Uiso 1 1 d D U . . .
H4B H 0.456(2) 0.5165(15) -0.2248(12) 0.0340(19) Uiso 1 1 d D U . . .
C11 C 0.34984(14) 0.35393(12) 0.52644(11) 0.0131(2) Uani 1 1 d . . . . .
C12 C 0.22226(14) 0.41065(12) 0.49804(11) 0.0123(2) Uani 1 1 d . . . . .
C13 C 0.14383(14) 0.44146(12) 0.58656(11) 0.0128(2) Uani 1 1 d . . . . .
H13 H 0.1724 0.4293 0.6669 0.015 Uiso 1 1 calc R U . . .
C14 C 0.02085(14) 0.49120(12) 0.56041(10) 0.0119(2) Uani 1 1 d . . . . .
C15 C 0.18076(15) 0.42943(12) 0.37809(11) 0.0133(2) Uani 1 1 d . . . . .
H15 H 0.2357 0.4091 0.3170 0.016 Uiso 1 1 calc R U . . .
C16 C 0.06213(14) 0.47668(12) 0.34959(11) 0.0127(2) Uani 1 1 d . . . . .
H16 H 0.0351 0.4881 0.2687 0.015 Uiso 1 1 calc R U . . .
C17 C 0.32292(15) 0.82507(13) -0.00967(11) 0.0136(2) Uani 1 1 d . . . . .
C18 C 0.22019(14) 0.90782(12) 0.01135(11) 0.0124(2) Uani 1 1 d . . . . .
C19 C 0.26581(14) 1.01816(12) 0.12323(11) 0.0130(2) Uani 1 1 d . . . . .
H19 H 0.3643 1.0431 0.1833 0.016 Uiso 1 1 calc R U . . .
C20 C 0.16967(14) 1.08920(12) 0.14577(11) 0.0127(2) Uani 1 1 d . . . . .
H20 H 0.2016 1.1623 0.2215 0.015 Uiso 1 1 calc R U . . .
C21 C 0.07941(14) 0.87363(12) -0.07628(10) 0.0119(2) Uani 1 1 d . . . . .
H21 H 0.0497 0.8003 -0.1515 0.014 Uiso 1 1 calc R U . . .
C22 C -0.02269(14) 0.94555(12) -0.05688(10) 0.0116(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2614(14) . ?
O2 C11 1.2632(14) . ?
O3 C17 1.2754(15) . ?
O4 C17 1.2484(14) . ?
N1 C5 1.3537(15) . ?
N1 C1 1.3572(15) . ?
N1 H1 0.942(10) . ?
C1 C2 1.3617(18) . ?
C1 H1A 0.9500 . ?
C2 C3 1.4049(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3688(18) . ?
C3 H3A 0.9500 . ?
C4 C5 1.4158(17) . ?
C4 H4 0.9500 . ?
C5 N2 1.3347(15) . ?
N2 H2A 0.939(10) . ?
N2 H2B 0.928(9) . ?
N3 C6 1.3553(15) . ?
N3 C10 1.3559(16) . ?
N3 H3 0.942(10) . ?
C6 N4 1.3260(16) . ?
C6 C7 1.4200(17) . ?
C7 C8 1.3609(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.4058(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3587(18) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
N4 H4A 0.931(10) . ?
N4 H4B 0.926(9) . ?
C11 C12 1.5136(16) . ?
C12 C13 1.3728(16) . ?
C12 C15 1.4186(16) . ?
C13 C14 1.4201(16) . ?
C13 H13 0.9500 . ?
C14 C16 1.4197(16) 2_566 ?
C14 C14 1.423(2) 2_566 ?
C15 C16 1.3707(17) . ?
C15 H15 0.9500 . ?
C16 C14 1.4197(16) 2_566 ?
C16 H16 0.9500 . ?
C17 C18 1.5124(16) . ?
C18 C21 1.3719(16) . ?
C18 C19 1.4183(16) . ?
C19 C20 1.3698(16) . ?
C19 H19 0.9500 . ?
C20 C22 1.4193(16) 2_575 ?
C20 H20 0.9500 . ?
C21 C22 1.4184(16) . ?
C21 H21 0.9500 . ?
C22 C20 1.4194(16) 2_575 ?
C22 C22 1.426(2) 2_575 ?

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 N1 C1 122.43(11) . . ?
C5 N1 H1 118.8(10) . . ?
C1 N1 H1 118.7(10) . . ?
N1 C1 C2 121.11(12) . . ?
N1 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C1 C2 C3 118.00(12) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.95(12) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 119.42(12) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N2 C5 N1 118.02(11) . . ?
N2 C5 C4 123.98(11) . . ?
N1 C5 C4 118.00(11) . . ?
C5 N2 H2A 118.8(10) . . ?
C5 N2 H2B 120.6(10) . . ?
H2A N2 H2B 120.1(13) . . ?
C6 N3 C10 122.25(10) . . ?
C6 N3 H3 119.9(11) . . ?
C10 N3 H3 117.8(10) . . ?
N4 C6 N3 118.65(11) . . ?
N4 C6 C7 123.60(11) . . ?
N3 C6 C7 117.74(11) . . ?
C8 C7 C6 119.57(11) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.15(12) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 117.72(12) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
N3 C10 C9 121.50(11) . . ?
N3 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C6 N4 H4A 119.0(10) . . ?
C6 N4 H4B 119.0(10) . . ?
H4A N4 H4B 122.0(13) . . ?
O1 C11 O2 124.87(11) . . ?
O1 C11 C12 117.09(10) . . ?
O2 C11 C12 118.03(10) . . ?
C13 C12 C15 119.58(10) . . ?
C13 C12 C11 120.63(10) . . ?
C15 C12 C11 119.78(10) . . ?
C12 C13 C14 121.33(11) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C16 C14 C13 122.27(10) 2_566 . ?
C16 C14 C14 118.99(13) 2_566 2_566 ?
C13 C14 C14 118.73(13) . 2_566 ?
C16 C15 C12 120.59(11) . . ?
C16 C15 H15 119.7 . . ?
C12 C15 H15 119.7 . . ?
C15 C16 C14 120.77(11) . 2_566 ?
C15 C16 H16 119.6 . . ?
C14 C16 H16 119.6 2_566 . ?
O4 C17 O3 125.15(11) . . ?
O4 C17 C18 118.25(10) . . ?
O3 C17 C18 116.59(10) . . ?
C21 C18 C19 119.52(10) . . ?
C21 C18 C17 120.11(10) . . ?
C19 C18 C17 120.33(10) . . ?
C20 C19 C18 120.85(11) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C22 120.52(11) . 2_575 ?
C19 C20 H20 119.7 . . ?
C22 C20 H20 119.7 2_575 . ?
C18 C21 C22 121.33(10) . . ?
C18 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C20 122.22(10) . 2_575 ?
C21 C22 C22 118.70(13) . 2_575 ?
C20 C22 C22 119.07(13) 2_575 2_575 ?

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
N1 H1 O1 0.942(10) 1.702(10) 2.6371(13) 171.2(17) .
C1 H1A O4 0.95 2.34 3.2060(15) 151.9 2_665
N2 H2A O2 0.939(10) 1.854(10) 2.7927(13) 179.0(15) .
N2 H2B O3 0.928(9) 2.044(12) 2.9024(13) 153.2(14) 2_666
N3 H3 O3 0.942(10) 1.715(10) 2.6524(13) 173.5(16) .
N4 H4A O4 0.931(10) 1.859(10) 2.7885(13) 176.4(15) .
N4 H4B O2 0.926(9) 1.917(10) 2.8392(13) 174.0(16) 1_554

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_B429
_database_code_depnum_ccdc_archive 'CCDC 2075483'
loop_
_audit_author_name
_audit_author_address
'Jagadese VITTAL'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N4 O6'
_chemical_formula_weight         416.43

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                   9.7799(11)
_cell_length_b                   12.2291(15)
_cell_length_c                   18.194(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.443(3)
_cell_angle_gamma                90
_cell_volume                     2172.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1598
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      20.39

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7409
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15041
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4983
_reflns_number_gt                2773
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 In P2(1)/c,the asymmetric unit has one disordered cca, two api
 and 2 water molecules. The disordered cca anions are approxima-
 tely related by inversion center and the occupancy refined to
 0.785(5). Only a common U(eq) was refined for the minor dis-
 ordered cca. All the coordinates of N-H and O-H atoms were 
 refined with DFIX options.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0959P)²+0.4663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4983
_refine_ls_number_parameters     327
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.2220
_refine_ls_wR_factor_gt          0.1914
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.7248(2) 0.91966(19) -0.02862(12) 0.0820(7) Uani 1 1 d . . . . .
O2 O 0.5387(2) 0.93038(17) -0.10440(12) 0.0729(6) Uani 1 1 d . . . . .
O3 O 0.09437(19) 0.33793(16) 0.08391(11) 0.0654(6) Uani 1 1 d . . . . .
O4 O 0.2606(2) 0.3321(2) 0.17056(13) 0.0846(7) Uani 1 1 d . . . . .
N1 N 0.3695(2) 0.88427(19) 0.16529(12) 0.0545(6) Uani 1 1 d D . . . .
H1N H 0.395(3) 0.9464(14) 0.1436(13) 0.065 Uiso 1 1 d D U . . .
N2 N 0.1720(3) 0.8857(2) 0.09078(14) 0.0649(7) Uani 1 1 d D . . . .
H21N H 0.0940(19) 0.859(2) 0.0704(14) 0.078 Uiso 1 1 d D U . . .
H22N H 0.194(3) 0.9463(16) 0.0672(14) 0.078 Uiso 1 1 d D U . . .
N3 N 0.1629(3) 0.1528(2) 0.22513(14) 0.0739(8) Uani 1 1 d D . . . .
H3N H 0.190(3) 0.2150(16) 0.2039(17) 0.089 Uiso 1 1 d D U . . .
N4 N -0.0191(3) 0.1387(2) 0.14160(14) 0.0709(7) Uani 1 1 d D . . . .
H41N H -0.092(2) 0.108(2) 0.1182(15) 0.085 Uiso 1 1 d D U . . .
H42N H 0.009(3) 0.1965(17) 0.1171(14) 0.085 Uiso 1 1 d D U . . .
C1 C 0.6104(4) 0.8882(2) -0.05104(17) 0.0639(8) Uani 1 1 d . . . . .
C2 C 0.5600(4) 0.7912(3) -0.0112(2) 0.0589(10) Uani 0.785(5) 1 d . . P A 1
H2 H 0.6196 0.7579 0.0246 0.071 Uiso 0.785(5) 1 calc R U P A 1
C3 C 0.4398(4) 0.7507(3) -0.02291(19) 0.0522(9) Uani 0.785(5) 1 d . . P A 1
H3 H 0.3826 0.7857 -0.0590 0.063 Uiso 0.785(5) 1 calc R U P A 1
C4 C 0.3812(4) 0.6558(3) 0.01351(19) 0.0461(9) Uani 0.785(5) 1 d . . P A 1
C5 C 0.4553(4) 0.5926(3) 0.0653(2) 0.0588(10) Uani 0.785(5) 1 d . . P A 1
H5 H 0.5468 0.6111 0.0785 0.071 Uiso 0.785(5) 1 calc R U P A 1
C6 C 0.3983(3) 0.5041(3) 0.09757(18) 0.0540(10) Uani 0.785(5) 1 d . . P A 1
H6 H 0.4500 0.4635 0.1332 0.065 Uiso 0.785(5) 1 calc R U P A 1
C7 C 0.2658(4) 0.4741(3) 0.0781(2) 0.0488(9) Uani 0.785(5) 1 d . . P A 1
C8 C 0.1903(4) 0.5360(3) 0.0272(2) 0.0598(10) Uani 0.785(5) 1 d . . P A 1
H8 H 0.0993 0.5166 0.0137 0.072 Uiso 0.785(5) 1 calc R U P A 1
C9 C 0.2475(4) 0.6258(3) -0.0037(2) 0.0597(10) Uani 0.785(5) 1 d . . P A 1
H9 H 0.1940 0.6681 -0.0376 0.072 Uiso 0.785(5) 1 calc R U P A 1
C10 C 0.2022(3) 0.3720(2) 0.11425(17) 0.0565(7) Uani 1 1 d . . . . .
C8X C 0.3595(14) 0.7699(11) -0.0565(8) 0.058(2) Uiso 0.215(5) 1 d . U P A 2
H8X H 0.3154 0.8121 -0.0940 0.070 Uiso 0.215(5) 1 calc R U P A 2
C6X C 0.5473(13) 0.7359(12) 0.0293(7) 0.058(2) Uiso 0.215(5) 1 d . U P A 2
H6X H 0.6344 0.7535 0.0507 0.070 Uiso 0.215(5) 1 calc R U P A 2
C9X C 0.2876(14) 0.6810(13) -0.0292(8) 0.058(2) Uiso 0.215(5) 1 d . U P A 2
H9X H 0.2004 0.6624 -0.0499 0.070 Uiso 0.215(5) 1 calc R U P A 2
C7X C 0.491(2) 0.7996(15) -0.0321(9) 0.058(2) Uiso 0.215(5) 1 d . U P A 2
C2X C 0.289(2) 0.4538(16) 0.1008(10) 0.058(2) Uiso 0.215(5) 1 d D U P A 2
H2X H 0.3729 0.4604 0.1288 0.070 Uiso 0.215(5) 1 calc R U P A 2
C5X C 0.4724(16) 0.6465(14) 0.0579(9) 0.058(2) Uiso 0.215(5) 1 d . U P A 2
H5X H 0.5112 0.6053 0.0975 0.070 Uiso 0.215(5) 1 calc R U P A 2
C3X C 0.2571(19) 0.5229(14) 0.0493(9) 0.058(2) Uiso 0.215(5) 1 d D U P A 2
H3X H 0.1730 0.5130 0.0224 0.070 Uiso 0.215(5) 1 calc R U P A 2
C4X C 0.3469(18) 0.6212(15) 0.0285(10) 0.058(2) Uiso 0.215(5) 1 d . U P A 2
C11 C 0.2487(3) 0.8382(2) 0.14407(14) 0.0510(6) Uani 1 1 d . . . . .
C12 C 0.2108(3) 0.7429(2) 0.17998(16) 0.0631(7) Uani 1 1 d . . . . .
H12 H 0.1273 0.7083 0.1664 0.076 Uiso 1 1 calc R U . . .
C13 C 0.2957(3) 0.7006(3) 0.23472(17) 0.0729(9) Uani 1 1 d . . . . .
H13 H 0.2705 0.6364 0.2590 0.088 Uiso 1 1 calc R U . . .
C14 C 0.4209(3) 0.7520(3) 0.25532(17) 0.0763(9) Uani 1 1 d . . . . .
H14 H 0.4795 0.7233 0.2934 0.092 Uiso 1 1 calc R U . . .
C15 C 0.4547(3) 0.8425(3) 0.21953(16) 0.0658(8) Uani 1 1 d . . . . .
H15 H 0.5384 0.8775 0.2321 0.079 Uiso 1 1 calc R U . . .
C16 C 0.0504(3) 0.0998(2) 0.20011(15) 0.0546(7) Uani 1 1 d . . . . .
C17 C 0.0123(3) 0.0056(3) 0.23778(17) 0.0666(8) Uani 1 1 d . . . . .
H17 H -0.0666 -0.0335 0.2214 0.080 Uiso 1 1 calc R U . . .
C18 C 0.0886(3) -0.0289(3) 0.2974(2) 0.0881(11) Uani 1 1 d . . . . .
H18 H 0.0620 -0.0913 0.3231 0.106 Uiso 1 1 calc R U . . .
C19 C 0.2063(4) 0.0273(4) 0.3209(2) 0.1159(16) Uani 1 1 d . . . . .
H19 H 0.2614 0.0026 0.3617 0.139 Uiso 1 1 calc R U . . .
C20 C 0.2400(4) 0.1182(4) 0.2842(2) 0.1163(17) Uani 1 1 d . . . . .
H20 H 0.3186 0.1579 0.3001 0.140 Uiso 1 1 calc R U . . .
O1W O 0.9205(2) 0.7788(3) 0.04806(14) 0.0943(8) Uani 1 1 d D . . . .
H11W H 0.858(3) 0.822(2) 0.0319(18) 0.113 Uiso 1 1 d D U . . .
H12W H 0.919(4) 0.732(2) 0.0130(15) 0.113 Uiso 1 1 d D U . . .
O2W O 0.2671(3) 0.9915(3) -0.11614(15) 0.1051(9) Uani 1 1 d D . . . .
H21W H 0.250(4) 1.035(3) -0.0810(18) 0.126 Uiso 1 1 d D U . . .
H22W H 0.3527(14) 0.981(3) -0.107(2) 0.126 Uiso 1 1 d D 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 1.230(4) . ?
O2 C1 1.272(4) . ?
O3 C10 1.233(3) . ?
O4 C10 1.242(3) . ?
N1 C11 1.345(3) . ?
N1 C15 1.353(3) . ?
N2 C11 1.324(3) . ?
N3 C16 1.333(4) . ?
N3 C20 1.344(4) . ?
N4 C16 1.317(3) . ?
C1 C2 1.489(5) . ?
C1 C7X 1.65(2) . ?
C2 C3 1.281(5) . ?
C3 C4 1.471(5) . ?
C4 C9 1.376(5) . ?
C4 C5 1.389(5) . ?
C5 C6 1.366(5) . ?
C6 C7 1.372(5) . ?
C7 C8 1.376(5) . ?
C7 C10 1.558(5) . ?
C8 C9 1.368(5) . ?
C10 C2X 1.35(2) . ?
C8X C7X 1.38(2) . ?
C8X C9X 1.40(2) . ?
C6X C5X 1.43(2) . ?
C6X C7X 1.44(2) . ?
C9X C4X 1.38(2) . ?
C2X C3X 1.287(9) . ?
C5X C4X 1.35(2) . ?
C3X C4X 1.55(2) . ?
C11 C12 1.397(4) . ?
C12 C13 1.360(4) . ?
C13 C14 1.407(5) . ?
C14 C15 1.336(4) . ?
C16 C17 1.402(4) . ?
C17 C18 1.347(4) . ?
C18 C19 1.386(5) . ?
C19 C20 1.348(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C15 122.9(2) . . ?
C16 N3 C20 122.2(3) . . ?
O1 C1 O2 125.1(3) . . ?
O1 C1 C2 114.2(3) . . ?
O2 C1 C2 120.8(3) . . ?
O1 C1 C7X 141.4(7) . . ?
O2 C1 C7X 93.5(7) . . ?
C3 C2 C1 123.6(4) . . ?
C2 C3 C4 127.5(4) . . ?
C9 C4 C5 117.2(4) . . ?
C9 C4 C3 119.9(3) . . ?
C5 C4 C3 122.9(3) . . ?
C6 C5 C4 121.5(3) . . ?
C5 C6 C7 120.3(3) . . ?
C6 C7 C8 119.1(4) . . ?
C6 C7 C10 120.0(3) . . ?
C8 C7 C10 120.9(3) . . ?
C9 C8 C7 120.1(4) . . ?
C8 C9 C4 121.8(4) . . ?
O3 C10 O4 125.1(3) . . ?
O3 C10 C2X 134.7(8) . . ?
O4 C10 C2X 100.2(8) . . ?
O3 C10 C7 115.8(3) . . ?
O4 C10 C7 119.2(3) . . ?
C7X C8X C9X 124.5(15) . . ?
C5X C6X C7X 120.8(14) . . ?
C4X C9X C8X 119.0(15) . . ?
C8X C7X C6X 114.4(16) . . ?
C8X C7X C1 139.9(14) . . ?
C6X C7X C1 105.7(14) . . ?
C3X C2X C10 119.3(17) . . ?
C4X C5X C6X 120.4(16) . . ?
C2X C3X C4X 124.7(19) . . ?
C5X C4X C9X 120.9(17) . . ?
C5X C4X C3X 126.8(16) . . ?
C9X C4X C3X 112.3(16) . . ?
N2 C11 N1 118.4(3) . . ?
N2 C11 C12 123.7(3) . . ?
N1 C11 C12 118.0(2) . . ?
C13 C12 C11 119.5(3) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C14 C13 118.5(3) . . ?
C14 C15 N1 120.6(3) . . ?
N4 C16 N3 118.4(3) . . ?
N4 C16 C17 123.5(3) . . ?
N3 C16 C17 118.1(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 120.2(3) . . ?
C20 C19 C18 118.7(3) . . ?
N3 C20 C19 120.9(3) . . ?

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
N1 H1N O2 0.898(10) 1.805(11) 2.700(3) 175(3) 3_675
N2 H21N O1W 0.892(10) 1.979(11) 2.852(3) 166(2) 1_455
N2 H22N O1 0.888(10) 1.971(11) 2.846(3) 168(2) 3_675
N3 H3N O4 0.901(10) 1.717(11) 2.612(3) 172(3) .
N4 H41N O2W 0.888(10) 2.104(15) 2.915(4) 152(3) 3_565
N4 H42N O3 0.887(10) 2.030(11) 2.900(3) 167(3) .
C15 H15 O4 0.94 2.62 3.331(4) 132.4 2_655
O1W H11W O1 0.847(10) 2.040(14) 2.873(4) 168(3) .
O1W H12W O3 0.854(10) 1.958(15) 2.790(3) 164(4) 3_665
O2W H21W O1 0.858(10) 2.07(2) 2.846(3) 150(4) 3_675
O2W H22W O2 0.854(10) 1.920(12) 2.756(4) 166(4) .

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.044


_shelxl_version_number           2014/6



