# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_KB194_0m
_database_code_depnum_ccdc_archive 'CCDC 2180241'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N4 O3, C9 H9 N4 O4'
_chemical_formula_sum            'C23 H28 N8 O7'
_chemical_formula_weight         528.53

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                   7.9637(2)
_cell_length_b                   9.4953(2)
_cell_length_c                   17.6571(4)
_cell_angle_alpha                104.2296(6)
_cell_angle_beta                 95.4410(7)
_cell_angle_gamma                97.9255(7)
_cell_volume                     1270.29(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9639
_cell_measurement_theta_min      2.2445
_cell_measurement_theta_max      30.4005

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23764
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.244
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4441
_reflns_number_gt                3757
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0620P)²+0.3449P] 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         4441
_refine_ls_number_parameters     368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.5069(2) 0.51323(17) 0.38199(9) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.3629(2) 0.39482(17) 0.35843(9) 0.0353(4) Uani 1 1 d . . . . .
C3 C 0.5030(2) 0.24886(17) 0.41964(9) 0.0348(4) Uani 1 1 d . . . . .
C4 C 0.6449(2) 0.48479(17) 0.42330(9) 0.0364(4) Uani 1 1 d . . . . .
H4 H 0.741585 0.557283 0.439966 0.044 Uiso 1 1 calc R U . . .
C5 C 0.5010(2) 0.65985(17) 0.36435(9) 0.0360(4) Uani 1 1 d . . . . .
H5A H 0.576673 0.734763 0.405446 0.043 Uiso 1 1 calc R U . . .
H5B H 0.385851 0.681143 0.367728 0.043 Uiso 1 1 calc R U . . .
C6 C 0.54957(19) 0.67529(17) 0.28496(9) 0.0336(3) Uani 1 1 d . . . . .
C7 C 0.5327(2) 0.80667(18) 0.26581(10) 0.0385(4) Uani 1 1 d . . . . .
H7 H 0.485703 0.878066 0.299348 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5857(2) 0.83190(18) 0.19681(10) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.6575(2) 0.72515(19) 0.14665(10) 0.0407(4) Uani 1 1 d . . . . .
C10 C 0.6712(2) 0.59329(18) 0.16528(9) 0.0385(4) Uani 1 1 d . . . . .
C11 C 0.6178(2) 0.56812(18) 0.23459(9) 0.0369(4) Uani 1 1 d . . . . .
H11 H 0.627934 0.479652 0.246911 0.044 Uiso 1 1 calc R U . . .
C12 C 0.5186(3) 1.0745(2) 0.22528(14) 0.0631(6) Uani 1 1 d . . . . .
H12A H 0.502999 1.150628 0.199440 0.095 Uiso 1 1 calc R U . . .
H12B H 0.602840 1.113644 0.271021 0.095 Uiso 1 1 calc R U . . .
H12C H 0.412090 1.038913 0.240949 0.095 Uiso 1 1 calc R U . . .
C13 C 0.6071(3) 0.7334(4) 0.01394(13) 0.0910(9) Uani 1 1 d . . . . .
H13A H 0.666586 0.754638 -0.027803 0.137 Uiso 1 1 calc R U . . .
H13B H 0.525122 0.798296 0.025281 0.137 Uiso 1 1 calc R U . . .
H13C H 0.549041 0.633083 -0.001996 0.137 Uiso 1 1 calc R U . . .
C14 C 0.7670(3) 0.3613(2) 0.12968(12) 0.0643(6) Uani 1 1 d . . . . .
H14A H 0.658338 0.306800 0.133080 0.097 Uiso 1 1 calc R U . . .
H14B H 0.839565 0.381644 0.179015 0.097 Uiso 1 1 calc R U . . .
H14C H 0.819563 0.304436 0.088562 0.097 Uiso 1 1 calc R U . . .
O1 O 0.57435(19) 0.95716(14) 0.17280(8) 0.0596(4) Uani 1 1 d . . . . .
O2 O 0.72551(16) 0.75399(16) 0.08207(7) 0.0570(4) Uani 1 1 d . . . . .
O3 O 0.74255(17) 0.49539(15) 0.11256(7) 0.0526(3) Uani 1 1 d . . . . .
N1 N 0.36346(17) 0.26777(14) 0.37866(8) 0.0392(3) Uani 1 1 d . . . . .
N2 N 0.64602(17) 0.35330(15) 0.44111(8) 0.0370(3) Uani 1 1 d . . . . .
H2N H 0.739(3) 0.332(2) 0.4724(12) 0.060(6) Uiso 1 1 d . . . . .
N3 N 0.2213(2) 0.40564(19) 0.31560(10) 0.0499(4) Uani 1 1 d . . . . .
H3NA H 0.140(3) 0.325(3) 0.3052(13) 0.070(7) Uiso 1 1 d . . . . .
H3NB H 0.205(2) 0.488(2) 0.3001(11) 0.051(5) Uiso 1 1 d . . . . .
N4 N 0.5049(2) 0.12245(16) 0.43917(9) 0.0453(4) Uani 1 1 d . . . . .
H4NA H 0.404(3) 0.062(2) 0.4316(12) 0.055(6) Uiso 1 1 d . . . . .
H4NB H 0.594(3) 0.114(2) 0.4724(12) 0.053(5) Uiso 1 1 d . . . . .
C15 C 0.8863(2) 0.1569(2) 0.88748(10) 0.0460(4) Uani 1 1 d . . . . .
C16 C 0.91699(19) 0.26441(18) 0.77262(9) 0.0358(4) Uani 1 1 d . . . . .
C17 C 0.96507(19) 0.12848(17) 0.73552(9) 0.0329(3) Uani 1 1 d . . . . .
C18 C 0.96932(19) 0.01495(17) 0.77037(9) 0.0351(4) Uani 1 1 d . . . . .
C19 C 0.9486(4) -0.0897(3) 0.88401(13) 0.0738(7) Uani 1 1 d . . . . .
H19A H 0.923173 -0.183667 0.845703 0.111 Uiso 1 1 calc R U . . .
H19B H 0.872274 -0.087543 0.923070 0.111 Uiso 1 1 calc R U . . .
H19C H 1.064538 -0.074617 0.908922 0.111 Uiso 1 1 calc R U . . .
C20 C 0.8273(3) 0.4048(2) 0.89391(12) 0.0570(5) Uani 1 1 d . . . . .
H20A H 0.750539 0.439826 0.860252 0.085 Uiso 1 1 calc R U . . .
H20B H 0.927726 0.478161 0.913952 0.085 Uiso 1 1 calc R U . . .
H20C H 0.771553 0.385580 0.937076 0.085 Uiso 1 1 calc R U . . .
C21 C 1.0492(2) -0.05821(18) 0.65903(9) 0.0398(4) Uani 1 1 d . . . . .
H21 H 1.086589 -0.116498 0.615533 0.048 Uiso 1 1 calc R U . . .
C22 C 1.0554(2) 0.16583(19) 0.60712(9) 0.0375(4) Uani 1 1 d . . . . .
H22A H 1.132175 0.119857 0.573014 0.045 Uiso 1 1 calc R U . . .
H22B H 1.115030 0.263002 0.636270 0.045 Uiso 1 1 calc R U . . .
C23 C 0.8995(2) 0.18366(17) 0.55585(9) 0.0350(4) Uani 1 1 d . . . . .
N5 N 0.92718(18) 0.02657(16) 0.84506(8) 0.0421(3) Uani 1 1 d . . . . .
N6 N 0.87640(18) 0.26824(16) 0.84862(8) 0.0415(3) Uani 1 1 d . . . . .
N7 N 1.01945(16) 0.07908(14) 0.66305(7) 0.0343(3) Uani 1 1 d . . . . .
N8 N 1.02012(18) -0.10326(15) 0.72303(8) 0.0410(3) Uani 1 1 d . . . . .
O4 O 0.8565(2) 0.17328(18) 0.95508(8) 0.0709(4) Uani 1 1 d . . . . .
O5 O 0.90779(16) 0.36908(13) 0.74401(7) 0.0480(3) Uani 1 1 d . . . . .
O6 O 0.76588(16) 0.09423(15) 0.54810(8) 0.0593(4) Uani 1 1 d . . . . .
O7 O 0.92195(15) 0.28516(14) 0.52246(7) 0.0495(3) 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
C1 C4 1.356(2) . ?
C1 C2 1.441(2) . ?
C1 C5 1.505(2) . ?
C2 N3 1.327(2) . ?
C2 N1 1.340(2) . ?
C3 N1 1.326(2) . ?
C3 N4 1.329(2) . ?
C3 N2 1.359(2) . ?
C4 N2 1.362(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.524(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.386(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9300 . ?
C8 O1 1.3685(19) . ?
C8 C9 1.397(2) . ?
C9 O2 1.3780(19) . ?
C9 C10 1.386(2) . ?
C10 O3 1.369(2) . ?
C10 C11 1.397(2) . ?
C11 H11 0.9300 . ?
C12 O1 1.416(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.412(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O3 1.413(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 H2N 0.95(2) . ?
N3 H3NA 0.90(2) . ?
N3 H3NB 0.91(2) . ?
N4 H4NA 0.90(2) . ?
N4 H4NB 0.90(2) . ?
C15 O4 1.216(2) . ?
C15 N5 1.378(2) . ?
C15 N6 1.402(2) . ?
C16 O5 1.2281(19) . ?
C16 N6 1.403(2) . ?
C16 C17 1.418(2) . ?
C17 C18 1.369(2) . ?
C17 N7 1.382(2) . ?
C18 N8 1.360(2) . ?
C18 N5 1.373(2) . ?
C19 N5 1.458(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N6 1.471(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N8 1.332(2) . ?
C21 N7 1.343(2) . ?
C21 H21 0.9300 . ?
C22 N7 1.4574(19) . ?
C22 C23 1.520(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O6 1.240(2) . ?
C23 O7 1.2491(19) . ?

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
C4 C1 C2 115.33(14) . . ?
C4 C1 C5 122.69(14) . . ?
C2 C1 C5 121.94(13) . . ?
N3 C2 N1 116.08(15) . . ?
N3 C2 C1 121.82(15) . . ?
N1 C2 C1 122.10(14) . . ?
N1 C3 N4 119.10(15) . . ?
N1 C3 N2 122.23(14) . . ?
N4 C3 N2 118.66(14) . . ?
C1 C4 N2 121.97(15) . . ?
C1 C4 H4 119.0 . . ?
N2 C4 H4 119.0 . . ?
C1 C5 C6 117.09(13) . . ?
C1 C5 H5A 108.0 . . ?
C6 C5 H5A 108.0 . . ?
C1 C5 H5B 108.0 . . ?
C6 C5 H5B 108.0 . . ?
H5A C5 H5B 107.3 . . ?
C11 C6 C7 119.87(14) . . ?
C11 C6 C5 122.57(14) . . ?
C7 C6 C5 117.46(13) . . ?
C8 C7 C6 120.36(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O1 C8 C7 124.75(16) . . ?
O1 C8 C9 115.38(15) . . ?
C7 C8 C9 119.87(15) . . ?
O2 C9 C10 119.74(15) . . ?
O2 C9 C8 120.55(15) . . ?
C10 C9 C8 119.54(15) . . ?
O3 C10 C9 115.36(14) . . ?
O3 C10 C11 124.14(15) . . ?
C9 C10 C11 120.49(15) . . ?
C6 C11 C10 119.85(14) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 O1 C12 117.51(14) . . ?
C9 O2 C13 115.69(15) . . ?
C10 O3 C14 118.27(14) . . ?
C3 N1 C2 118.87(14) . . ?
C3 N2 C4 119.40(13) . . ?
C3 N2 H2N 116.8(13) . . ?
C4 N2 H2N 123.6(13) . . ?
C2 N3 H3NA 113.6(15) . . ?
C2 N3 H3NB 123.6(12) . . ?
H3NA N3 H3NB 122.7(19) . . ?
C3 N4 H4NA 116.3(13) . . ?
C3 N4 H4NB 118.9(13) . . ?
H4NA N4 H4NB 121.6(18) . . ?
O4 C15 N5 121.43(17) . . ?
O4 C15 N6 121.48(17) . . ?
N5 C15 N6 117.07(14) . . ?
O5 C16 N6 121.60(15) . . ?
O5 C16 C17 126.34(15) . . ?
N6 C16 C17 112.05(13) . . ?
C18 C17 N7 105.00(13) . . ?
C18 C17 C16 123.29(14) . . ?
N7 C17 C16 131.68(14) . . ?
N8 C18 C17 112.14(14) . . ?
N8 C18 N5 126.48(14) . . ?
C17 C18 N5 121.38(14) . . ?
N5 C19 H19A 109.5 . . ?
N5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C21 N7 113.84(14) . . ?
N8 C21 H21 123.1 . . ?
N7 C21 H21 123.1 . . ?
N7 C22 C23 115.25(13) . . ?
N7 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
N7 C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
O6 C23 O7 126.12(15) . . ?
O6 C23 C22 118.18(14) . . ?
O7 C23 C22 115.63(14) . . ?
C18 N5 C15 119.74(14) . . ?
C18 N5 C19 120.43(15) . . ?
C15 N5 C19 119.26(15) . . ?
C15 N6 C16 126.26(14) . . ?
C15 N6 C20 116.38(15) . . ?
C16 N6 C20 117.28(14) . . ?
C21 N7 C17 105.99(13) . . ?
C21 N7 C22 127.42(14) . . ?
C17 N7 C22 126.24(13) . . ?
C21 N8 C18 103.01(13) . . ?

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
C4 C1 C2 N3 -177.86(15) . . . . ?
C5 C1 C2 N3 4.4(2) . . . . ?
C4 C1 C2 N1 2.4(2) . . . . ?
C5 C1 C2 N1 -175.36(14) . . . . ?
C2 C1 C4 N2 -0.1(2) . . . . ?
C5 C1 C4 N2 177.68(14) . . . . ?
C4 C1 C5 C6 95.06(18) . . . . ?
C2 C1 C5 C6 -87.32(18) . . . . ?
C1 C5 C6 C11 -8.2(2) . . . . ?
C1 C5 C6 C7 175.52(14) . . . . ?
C11 C6 C7 C8 -0.7(2) . . . . ?
C5 C6 C7 C8 175.60(14) . . . . ?
C6 C7 C8 O1 179.91(15) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
O1 C8 C9 O2 5.9(2) . . . . ?
C7 C8 C9 O2 -173.76(14) . . . . ?
O1 C8 C9 C10 -178.73(14) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
O2 C9 C10 O3 -4.8(2) . . . . ?
C8 C9 C10 O3 179.81(14) . . . . ?
O2 C9 C10 C11 173.83(14) . . . . ?
C8 C9 C10 C11 -1.6(2) . . . . ?
C7 C6 C11 C10 0.8(2) . . . . ?
C5 C6 C11 C10 -175.37(14) . . . . ?
O3 C10 C11 C6 178.89(15) . . . . ?
C9 C10 C11 C6 0.4(2) . . . . ?
C7 C8 O1 C12 5.8(3) . . . . ?
C9 C8 O1 C12 -173.83(16) . . . . ?
C10 C9 O2 C13 101.5(2) . . . . ?
C8 C9 O2 C13 -83.2(2) . . . . ?
C9 C10 O3 C14 177.37(16) . . . . ?
C11 C10 O3 C14 -1.2(2) . . . . ?
N4 C3 N1 C2 -179.33(15) . . . . ?
N2 C3 N1 C2 -0.7(2) . . . . ?
N3 C2 N1 C3 178.20(15) . . . . ?
C1 C2 N1 C3 -2.1(2) . . . . ?
N1 C3 N2 C4 3.0(2) . . . . ?
N4 C3 N2 C4 -178.37(14) . . . . ?
C1 C4 N2 C3 -2.5(2) . . . . ?
O5 C16 C17 C18 -178.64(15) . . . . ?
N6 C16 C17 C18 0.5(2) . . . . ?
O5 C16 C17 N7 3.2(3) . . . . ?
N6 C16 C17 N7 -177.65(15) . . . . ?
N7 C17 C18 N8 -1.18(18) . . . . ?
C16 C17 C18 N8 -179.76(14) . . . . ?
N7 C17 C18 N5 178.25(13) . . . . ?
C16 C17 C18 N5 -0.3(2) . . . . ?
N7 C22 C23 O6 -20.1(2) . . . . ?
N7 C22 C23 O7 162.91(14) . . . . ?
N8 C18 N5 C15 176.68(15) . . . . ?
C17 C18 N5 C15 -2.7(2) . . . . ?
N8 C18 N5 C19 5.4(3) . . . . ?
C17 C18 N5 C19 -173.96(18) . . . . ?
O4 C15 N5 C18 -176.36(17) . . . . ?
N6 C15 N5 C18 5.1(2) . . . . ?
O4 C15 N5 C19 -5.0(3) . . . . ?
N6 C15 N5 C19 176.54(18) . . . . ?
O4 C15 N6 C16 176.23(17) . . . . ?
N5 C15 N6 C16 -5.3(3) . . . . ?
O4 C15 N6 C20 -0.4(3) . . . . ?
N5 C15 N6 C20 178.13(15) . . . . ?
O5 C16 N6 C15 -178.42(15) . . . . ?
C17 C16 N6 C15 2.4(2) . . . . ?
O5 C16 N6 C20 -1.8(2) . . . . ?
C17 C16 N6 C20 178.96(14) . . . . ?
N8 C21 N7 C17 -0.45(18) . . . . ?
N8 C21 N7 C22 173.07(14) . . . . ?
C18 C17 N7 C21 0.95(16) . . . . ?
C16 C17 N7 C21 179.36(16) . . . . ?
C18 C17 N7 C22 -172.67(13) . . . . ?
C16 C17 N7 C22 5.7(3) . . . . ?
C23 C22 N7 C21 106.86(18) . . . . ?
C23 C22 N7 C17 -80.87(19) . . . . ?
N7 C21 N8 C18 -0.25(18) . . . . ?
C17 C18 N8 C21 0.90(18) . . . . ?
N5 C18 N8 C21 -178.49(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
_geom_hbond_publ_flag
C13 H13B O1 0.96 2.63 3.133(3) 112.9 . yes
C14 H14C O4 0.96 2.45 3.356(2) 158.2 1_554 yes
N2 H2N O7 0.95(2) 1.80(2) 2.7497(17) 174.3(19) . yes
N3 H3NA N8 0.90(2) 2.22(3) 3.110(2) 169(2) 2_656 yes
N3 H3NB O5 0.91(2) 2.00(2) 2.8722(19) 161.1(17) 2_666 yes
N4 H4NA O6 0.90(2) 1.99(2) 2.833(2) 155.6(18) 2_656 yes
N4 H4NB O6 0.90(2) 1.88(2) 2.7823(19) 174.9(18) . yes
C21 H21 O7 0.93 2.55 3.442(2) 159.7 2_756 yes

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_KB102_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2180242'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N4 O3, C4 H2 F N2 O2'
_chemical_formula_sum            'C18 H21 F N6 O5'
_chemical_formula_weight         420.41

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'
F F 0.0171 0.0103 '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                   8.5911(2)
_cell_length_b                   8.6242(2)
_cell_length_c                   13.5809(3)
_cell_angle_alpha                105.7372(6)
_cell_angle_beta                 90.1053(6)
_cell_angle_gamma                93.1570(6)
_cell_volume                     966.89(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.4575
_cell_measurement_theta_max      30.487

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20165
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.527
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3344
_reflns_number_gt                2953
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0445P)²+0.2786P] 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         3344
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.48665(15) 0.69557(16) 0.26275(10) 0.0314(3) Uani 1 1 d . . . . .
C2 C 0.53839(16) 0.85090(16) 0.32920(10) 0.0304(3) Uani 1 1 d . . . . .
C3 C 0.65545(16) 0.73139(16) 0.44074(10) 0.0321(3) Uani 1 1 d . . . . .
C4 C 0.52268(16) 0.56736(16) 0.29551(10) 0.0336(3) Uani 1 1 d . . . . .
H4 H 0.490423 0.464499 0.256111 0.040 Uiso 1 1 calc R U . . .
C5 C 0.39667(17) 0.67558(18) 0.16473(11) 0.0371(3) Uani 1 1 d . . . . .
H5A H 0.304772 0.737753 0.180116 0.045 Uiso 1 1 calc R U . . .
H5B H 0.361238 0.562984 0.138920 0.045 Uiso 1 1 calc R U . . .
C6 C 0.48441(15) 0.72623(15) 0.07986(10) 0.0302(3) Uani 1 1 d . . . . .
C7 C 0.64377(16) 0.75951(17) 0.08499(10) 0.0346(3) Uani 1 1 d . . . . .
H7 H 0.701695 0.744960 0.139385 0.042 Uiso 1 1 calc R U . . .
C8 C 0.71791(16) 0.81487(17) 0.00878(10) 0.0340(3) Uani 1 1 d . . . . .
C9 C 0.63236(16) 0.83244(16) -0.07420(10) 0.0310(3) Uani 1 1 d . . . . .
C10 C 0.47288(16) 0.79179(15) -0.08106(10) 0.0304(3) Uani 1 1 d . . . . .
C11 C 0.39928(16) 0.74001(16) -0.00412(10) 0.0318(3) Uani 1 1 d . . . . .
H11 H 0.292465 0.714346 -0.008662 0.038 Uiso 1 1 calc R U . . .
C12 C 0.96841(18) 0.8362(2) 0.08958(14) 0.0544(4) Uani 1 1 d . . . . .
H12A H 0.968505 0.723072 0.084848 0.082 Uiso 1 1 calc R U . . .
H12B H 0.927935 0.892432 0.154510 0.082 Uiso 1 1 calc R U . . .
H12C H 1.073016 0.877255 0.083382 0.082 Uiso 1 1 calc R U . . .
C13 C 0.7972(2) 0.7915(2) -0.21680(12) 0.0511(4) Uani 1 1 d . . . . .
H13A H 0.732630 0.708120 -0.262389 0.077 Uiso 1 1 calc R U . . .
H13B H 0.866569 0.743842 -0.179382 0.077 Uiso 1 1 calc R U . . .
H13C H 0.856895 0.850889 -0.255613 0.077 Uiso 1 1 calc R U . . .
C14 C 0.23699(19) 0.7716(2) -0.17796(13) 0.0534(4) Uani 1 1 d . . . . .
H14A H 0.200379 0.790313 -0.240353 0.080 Uiso 1 1 calc R U . . .
H14B H 0.185411 0.839525 -0.121001 0.080 Uiso 1 1 calc R U . . .
H14C H 0.214683 0.660572 -0.179788 0.080 Uiso 1 1 calc R U . . .
O1 O 0.87330(12) 0.85950(15) 0.00959(8) 0.0485(3) Uani 1 1 d . . . . .
O2 O 0.70115(12) 0.89829(12) -0.14681(7) 0.0401(3) Uani 1 1 d . . . . .
O3 O 0.40044(12) 0.80787(13) -0.16719(7) 0.0411(3) Uani 1 1 d . . . . .
N1 N 0.62164(14) 0.86479(13) 0.41495(8) 0.0334(3) Uani 1 1 d . . . . .
N2 N 0.60386(14) 0.58245(13) 0.38342(9) 0.0346(3) Uani 1 1 d . . . . .
H1N H 0.624(2) 0.492(2) 0.4020(13) 0.052 Uiso 1 1 d . U . . .
N3 N 0.50599(16) 0.98765(15) 0.30833(10) 0.0401(3) Uani 1 1 d . . . . .
H2N H 0.460(2) 0.987(2) 0.2514(15) 0.051(5) Uiso 1 1 d . . . . .
H3N H 0.549(2) 1.084(2) 0.3534(15) 0.056(5) Uiso 1 1 d . . . . .
N4 N 0.74057(17) 0.74211(16) 0.52319(10) 0.0437(3) Uani 1 1 d . . . . .
H4N H 0.787(2) 0.840(3) 0.5589(15) 0.066 Uiso 1 1 d . U . . .
C15 C 0.89004(18) 0.16309(17) 0.60825(11) 0.0391(3) Uani 1 1 d . . . . .
C16 C 0.75690(16) 0.30831(16) 0.50341(10) 0.0332(3) Uani 1 1 d . . . . .
C17 C 0.93903(18) 0.44616(18) 0.62390(12) 0.0415(4) Uani 1 1 d . . . . .
H17 H 0.995093 0.542243 0.655458 0.050 Uiso 1 1 calc R U . . .
C18 C 0.96874(17) 0.31449(18) 0.65399(11) 0.0393(3) Uani 1 1 d . . . . .
O4 O 0.90799(16) 0.03580(14) 0.63095(10) 0.0614(4) Uani 1 1 d . . . . .
O5 O 0.65810(13) 0.29663(12) 0.43279(8) 0.0433(3) Uani 1 1 d . . . . .
N5 N 0.78608(15) 0.17111(14) 0.53278(9) 0.0367(3) Uani 1 1 d . . . . .
H5N H 0.733(2) 0.078(2) 0.4961(13) 0.051(5) Uiso 1 1 d . . . . .
N6 N 0.83311(15) 0.44791(14) 0.55088(10) 0.0412(3) Uani 1 1 d . . . . .
H6N H 0.774(2) 0.647(2) 0.5341(14) 0.057(5) Uiso 1 1 d . . . . .
F1 F 1.07915(12) 0.32153(12) 0.72714(8) 0.0615(3) 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
C1 C4 1.3492(19) . ?
C1 C2 1.4435(19) . ?
C1 C5 1.5021(19) . ?
C2 N3 1.3289(17) . ?
C2 N1 1.3394(17) . ?
C3 N4 1.3155(18) . ?
C3 N1 1.3363(17) . ?
C3 N2 1.3587(18) . ?
C4 N2 1.3532(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.5256(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.3810(19) . ?
C6 C11 1.3892(18) . ?
C7 C8 1.3935(19) . ?
C7 H7 0.9300 . ?
C8 O1 1.3680(17) . ?
C8 C9 1.3911(19) . ?
C9 O2 1.3832(16) . ?
C9 C10 1.3920(19) . ?
C10 O3 1.3674(16) . ?
C10 C11 1.3840(19) . ?
C11 H11 0.9300 . ?
C12 O1 1.4218(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.4297(19) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O3 1.4203(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 H1N 0.911(19) . ?
N3 H2N 0.867(19) . ?
N3 H3N 0.94(2) . ?
N4 H4N 0.92(2) . ?
N4 H6N 0.94(2) . ?
C15 O4 1.2354(17) . ?
C15 N5 1.3765(18) . ?
C15 C18 1.417(2) . ?
C16 O5 1.2593(17) . ?
C16 N6 1.3358(18) . ?
C16 N5 1.3822(17) . ?
C17 C18 1.343(2) . ?
C17 N6 1.3484(19) . ?
C17 H17 0.9300 . ?
C18 F1 1.3593(17) . ?
N5 H5N 0.920(19) . ?

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
C4 C1 C2 115.22(12) . . ?
C4 C1 C5 121.61(12) . . ?
C2 C1 C5 123.17(12) . . ?
N3 C2 N1 116.52(12) . . ?
N3 C2 C1 121.67(13) . . ?
N1 C2 C1 121.81(11) . . ?
N4 C3 N1 120.14(12) . . ?
N4 C3 N2 118.36(12) . . ?
N1 C3 N2 121.50(12) . . ?
C1 C4 N2 122.63(12) . . ?
C1 C4 H4 118.7 . . ?
N2 C4 H4 118.7 . . ?
C1 C5 C6 116.04(11) . . ?
C1 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C1 C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C11 119.84(12) . . ?
C7 C6 C5 122.00(12) . . ?
C11 C6 C5 118.16(12) . . ?
C6 C7 C8 120.10(12) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O1 C8 C9 115.22(12) . . ?
O1 C8 C7 124.63(12) . . ?
C9 C8 C7 120.13(12) . . ?
O2 C9 C8 121.14(12) . . ?
O2 C9 C10 119.37(12) . . ?
C8 C9 C10 119.38(12) . . ?
O3 C10 C11 124.88(12) . . ?
O3 C10 C9 114.88(11) . . ?
C11 C10 C9 120.24(12) . . ?
C10 C11 C6 120.23(12) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 O1 C12 117.81(11) . . ?
C9 O2 C13 114.14(11) . . ?
C10 O3 C14 117.77(11) . . ?
C3 N1 C2 119.16(11) . . ?
C4 N2 C3 119.59(11) . . ?
C4 N2 H1N 118.7(11) . . ?
C3 N2 H1N 121.7(11) . . ?
C2 N3 H2N 121.1(12) . . ?
C2 N3 H3N 116.4(11) . . ?
H2N N3 H3N 121.8(16) . . ?
C3 N4 H4N 120.0(12) . . ?
C3 N4 H6N 118.1(11) . . ?
H4N N4 H6N 119.8(17) . . ?
O4 C15 N5 121.73(14) . . ?
O4 C15 C18 126.13(14) . . ?
N5 C15 C18 112.13(12) . . ?
O5 C16 N6 122.44(12) . . ?
O5 C16 N5 118.33(12) . . ?
N6 C16 N5 119.22(13) . . ?
C18 C17 N6 124.18(14) . . ?
C18 C17 H17 117.9 . . ?
N6 C17 H17 117.9 . . ?
C17 C18 F1 120.82(13) . . ?
C17 C18 C15 121.20(14) . . ?
F1 C18 C15 117.94(13) . . ?
C15 N5 C16 125.65(13) . . ?
C15 N5 H5N 119.0(11) . . ?
C16 N5 H5N 115.3(11) . . ?
C16 N6 C17 117.57(12) . . ?

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
C4 C1 C2 N3 -177.49(13) . . . . ?
C5 C1 C2 N3 1.5(2) . . . . ?
C4 C1 C2 N1 2.59(19) . . . . ?
C5 C1 C2 N1 -178.41(12) . . . . ?
C2 C1 C4 N2 -1.11(19) . . . . ?
C5 C1 C4 N2 179.87(12) . . . . ?
C4 C1 C5 C6 -114.33(15) . . . . ?
C2 C1 C5 C6 66.73(18) . . . . ?
C1 C5 C6 C7 11.72(19) . . . . ?
C1 C5 C6 C11 -167.71(12) . . . . ?
C11 C6 C7 C8 3.3(2) . . . . ?
C5 C6 C7 C8 -176.08(13) . . . . ?
C6 C7 C8 O1 176.28(13) . . . . ?
C6 C7 C8 C9 -1.8(2) . . . . ?
O1 C8 C9 O2 -3.08(19) . . . . ?
C7 C8 C9 O2 175.19(12) . . . . ?
O1 C8 C9 C10 -179.29(12) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
O2 C9 C10 O3 5.95(18) . . . . ?
C8 C9 C10 O3 -177.76(12) . . . . ?
O2 C9 C10 C11 -173.94(12) . . . . ?
C8 C9 C10 C11 2.3(2) . . . . ?
O3 C10 C11 C6 179.28(12) . . . . ?
C9 C10 C11 C6 -0.8(2) . . . . ?
C7 C6 C11 C10 -2.0(2) . . . . ?
C5 C6 C11 C10 177.42(12) . . . . ?
C9 C8 O1 C12 -176.70(14) . . . . ?
C7 C8 O1 C12 5.1(2) . . . . ?
C8 C9 O2 C13 75.77(16) . . . . ?
C10 C9 O2 C13 -108.01(15) . . . . ?
C11 C10 O3 C14 1.2(2) . . . . ?
C9 C10 O3 C14 -178.69(13) . . . . ?
N4 C3 N1 C2 178.19(13) . . . . ?
N2 C3 N1 C2 -1.8(2) . . . . ?
N3 C2 N1 C3 178.87(12) . . . . ?
C1 C2 N1 C3 -1.2(2) . . . . ?
C1 C4 N2 C3 -1.7(2) . . . . ?
N4 C3 N2 C4 -176.73(13) . . . . ?
N1 C3 N2 C4 3.2(2) . . . . ?
N6 C17 C18 F1 178.98(14) . . . . ?
N6 C17 C18 C15 1.1(3) . . . . ?
O4 C15 C18 C17 -179.35(16) . . . . ?
N5 C15 C18 C17 0.4(2) . . . . ?
O4 C15 C18 F1 2.7(3) . . . . ?
N5 C15 C18 F1 -177.54(13) . . . . ?
O4 C15 N5 C16 179.03(15) . . . . ?
C18 C15 N5 C16 -0.7(2) . . . . ?
O5 C16 N5 C15 179.96(13) . . . . ?
N6 C16 N5 C15 -0.4(2) . . . . ?
O5 C16 N6 C17 -178.54(14) . . . . ?
N5 C16 N6 C17 1.9(2) . . . . ?
C18 C17 N6 C16 -2.3(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
_geom_hbond_publ_flag
C4 H4 O3 0.93 2.56 3.3355(17) 140.9 2_665 yes
C12 H12C O2 0.96 2.63 3.495(2) 149.8 2_775 yes
C13 H13B O1 0.96 2.49 3.0326(19) 115.9 . yes
C13 H13C O4 0.96 2.52 3.431(2) 157.6 1_564 yes
N2 H1N O5 0.911(19) 1.877(19) 2.7865(15) 176.4(17) . yes
N3 H2N O2 0.867(19) 2.411(19) 3.2086(16) 153.1(15) 2_675 yes
N3 H2N O3 0.867(19) 2.596(18) 3.0187(16) 111.1(14) 2_675 yes
N3 H3N O5 0.94(2) 2.04(2) 2.9716(17) 171.7(16) 1_565 yes
N4 H4N O4 0.92(2) 1.95(2) 2.8646(18) 173.3(18) 1_565 yes
N5 H5N N1 0.920(19) 2.05(2) 2.9703(17) 177.4(16) 1_545 yes
N4 H6N N6 0.94(2) 1.89(2) 2.8195(17) 176.6(17) . yes

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_KA111_0m
_database_code_depnum_ccdc_archive 'CCDC 2180243'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 N4 O5'
_chemical_formula_sum            'C20 H24 N4 O5'
_chemical_formula_weight         400.43

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      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                   9.0355(6)
_cell_length_b                   10.9956(7)
_cell_length_c                   11.9267(7)
_cell_angle_alpha                108.0068(18)
_cell_angle_beta                 111.5684(18)
_cell_angle_gamma                99.678(2)
_cell_volume                     993.38(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.4445
_cell_measurement_theta_max      30.0615

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32063
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.444
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6041
_reflns_number_gt                3997
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0551P)²+0.2680P] 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         6041
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.54500(16) 0.40324(12) 0.82941(12) 0.0347(3) Uani 1 1 d . . . . .
C2 C 0.72241(17) 0.44236(13) 0.89405(12) 0.0355(3) Uani 1 1 d . . . . .
C3 C 0.73629(17) 0.66279(12) 0.99032(13) 0.0355(3) Uani 1 1 d . . . . .
C4 C 0.48003(17) 0.50657(14) 0.85148(13) 0.0406(3) Uani 1 1 d . . . . .
H4 H 0.363864 0.485007 0.809851 0.049 Uiso 1 1 calc R U . . .
C5 C 0.43561(18) 0.25859(13) 0.75346(13) 0.0416(3) Uani 1 1 d . . . . .
H5A H 0.326883 0.253688 0.752406 0.050 Uiso 1 1 calc R U . . .
H5B H 0.484055 0.207498 0.802076 0.050 Uiso 1 1 calc R U . . .
C6 C 0.40642(16) 0.18795(12) 0.61239(12) 0.0353(3) Uani 1 1 d . . . . .
C7 C 0.48530(18) 0.24734(14) 0.55381(13) 0.0405(3) Uani 1 1 d . . . . .
H7 H 0.557947 0.335546 0.600542 0.049 Uiso 1 1 calc R U . . .
C8 C 0.45579(18) 0.17465(14) 0.42408(14) 0.0419(3) Uani 1 1 d . . . . .
C9 C 0.34382(19) 0.04438(14) 0.35282(13) 0.0426(3) Uani 1 1 d . . . . .
C10 C 0.26330(17) -0.01376(13) 0.41194(13) 0.0401(3) Uani 1 1 d . . . . .
C11 C 0.29556(17) 0.05634(13) 0.54138(13) 0.0390(3) Uani 1 1 d . . . . .
H11 H 0.243409 0.015737 0.580829 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6145(3) 0.3605(2) 0.4098(2) 0.0778(6) Uani 1 1 d . . . . .
H12A H 0.659374 0.378645 0.352952 0.117 Uiso 1 1 calc R U . . .
H12B H 0.704039 0.390592 0.496808 0.117 Uiso 1 1 calc R U . . .
H12C H 0.534819 0.407594 0.413191 0.117 Uiso 1 1 calc R U . . .
C13 C 0.2317(2) 0.0136(2) 0.12826(16) 0.0606(5) Uani 1 1 d . . . . .
H13A H 0.180871 -0.059505 0.042755 0.091 Uiso 1 1 calc R U . . .
H13B H 0.312058 0.085189 0.131054 0.091 Uiso 1 1 calc R U . . .
H13C H 0.146676 0.046229 0.145094 0.091 Uiso 1 1 calc R U . . .
C14 C 0.0733(3) -0.20820(18) 0.3904(2) 0.0669(5) Uani 1 1 d . . . . .
H14A H 0.008028 -0.299321 0.328288 0.100 Uiso 1 1 calc R U . . .
H14B H 0.001070 -0.161404 0.413124 0.100 Uiso 1 1 calc R U . . .
H14C H 0.156634 -0.208742 0.468330 0.100 Uiso 1 1 calc R U . . .
N1 N 0.81637(14) 0.57100(11) 0.97636(11) 0.0389(3) Uani 1 1 d . . . . .
N2 N 0.57039(15) 0.63766(11) 0.92879(12) 0.0407(3) Uani 1 1 d . . . . .
N3 N 0.80434(18) 0.35301(13) 0.87731(14) 0.0521(4) Uani 1 1 d . . . . .
H1N H 0.916(3) 0.3801(19) 0.9255(19) 0.057(5) Uiso 1 1 d . . . . .
H2N H 0.747(2) 0.267(2) 0.8267(19) 0.062(5) Uiso 1 1 d . . . . .
N4 N 0.83243(19) 0.79138(12) 1.07332(14) 0.0513(3) Uani 1 1 d . . . . .
H3N H 0.943(3) 0.8093(19) 1.1258(19) 0.060(5) Uiso 1 1 d . . . . .
H4N H 0.786(2) 0.8526(19) 1.0948(18) 0.056(5) Uiso 1 1 d . . . . .
O1 O 0.53504(17) 0.22219(12) 0.36095(12) 0.0626(3) Uani 1 1 d . . . . .
O2 O 0.31452(17) -0.03280(12) 0.22631(10) 0.0599(3) Uani 1 1 d . . . . .
O3 O 0.15339(14) -0.14199(10) 0.33334(11) 0.0549(3) Uani 1 1 d . . . . .
C15 C 0.25801(18) 0.78267(14) 0.85046(14) 0.0412(3) Uani 1 1 d . . . . .
C16 C 0.1947(2) 0.86301(15) 0.78737(15) 0.0450(3) Uani 1 1 d . . . . .
C17 C 0.0270(2) 0.82156(19) 0.70112(19) 0.0641(5) Uani 1 1 d . . . . .
H17 H -0.014856 0.875015 0.658504 0.077 Uiso 1 1 calc R U . . .
C18 C -0.0791(3) 0.7010(2) 0.6777(3) 0.0869(7) Uani 1 1 d . . . . .
H18 H -0.192205 0.672823 0.618721 0.104 Uiso 1 1 calc R U . . .
C19 C -0.0176(3) 0.6226(2) 0.7415(3) 0.0803(7) Uani 1 1 d . . . . .
H19 H -0.089583 0.542056 0.726878 0.096 Uiso 1 1 calc R U . . .
C20 C 0.1507(2) 0.66310(17) 0.82740(18) 0.0544(4) Uani 1 1 d . . . . .
H20 H 0.191799 0.609352 0.869900 0.065 Uiso 1 1 calc R U . . .
O4 O 0.42420(14) 0.83140(11) 0.93637(12) 0.0575(3) Uani 1 1 d . . . . .
H4O H 0.471(3) 0.760(2) 0.938(2) 0.082(7) Uiso 1 1 d . . . . .
O5 O 0.29666(18) 0.98442(12) 0.81252(15) 0.0635(4) Uani 1 1 d . . . . .
H5O H 0.400(4) 0.997(3) 0.873(3) 0.111(10) 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
C1 C4 1.3630(18) . ?
C1 C2 1.4154(18) . ?
C1 C5 1.4999(17) . ?
C2 N3 1.3361(17) . ?
C2 N1 1.3454(16) . ?
C3 N2 1.3373(17) . ?
C3 N1 1.3417(16) . ?
C3 N4 1.3503(17) . ?
C4 N2 1.3504(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.5168(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.384(2) . ?
C6 C11 1.3950(18) . ?
C7 C8 1.4016(19) . ?
C7 H7 0.9300 . ?
C8 O1 1.3663(19) . ?
C8 C9 1.388(2) . ?
C9 O2 1.3806(16) . ?
C9 C10 1.391(2) . ?
C10 O3 1.3713(16) . ?
C10 C11 1.3857(19) . ?
C11 H11 0.9300 . ?
C12 O1 1.395(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.429(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O3 1.417(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N3 H1N 0.90(2) . ?
N3 H2N 0.89(2) . ?
N4 H3N 0.91(2) . ?
N4 H4N 0.87(2) . ?
C15 O4 1.3604(18) . ?
C15 C20 1.377(2) . ?
C15 C16 1.392(2) . ?
C16 O5 1.363(2) . ?
C16 C17 1.376(2) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O4 H4O 0.95(2) . ?
O5 H5O 0.90(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
C4 C1 C2 114.74(12) . . ?
C4 C1 C5 122.08(13) . . ?
C2 C1 C5 122.91(12) . . ?
N3 C2 N1 116.87(12) . . ?
N3 C2 C1 121.56(12) . . ?
N1 C2 C1 121.57(11) . . ?
N2 C3 N1 125.58(12) . . ?
N2 C3 N4 117.63(12) . . ?
N1 C3 N4 116.78(12) . . ?
N2 C4 C1 125.40(13) . . ?
N2 C4 H4 117.3 . . ?
C1 C4 H4 117.3 . . ?
C1 C5 C6 118.25(12) . . ?
C1 C5 H5A 107.7 . . ?
C6 C5 H5A 107.7 . . ?
C1 C5 H5B 107.7 . . ?
C6 C5 H5B 107.7 . . ?
H5A C5 H5B 107.1 . . ?
C7 C6 C11 119.86(12) . . ?
C7 C6 C5 123.14(11) . . ?
C11 C6 C5 116.99(13) . . ?
C6 C7 C8 120.04(13) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O1 C8 C9 115.78(12) . . ?
O1 C8 C7 124.09(13) . . ?
C9 C8 C7 120.11(14) . . ?
O2 C9 C8 122.26(15) . . ?
O2 C9 C10 118.26(13) . . ?
C8 C9 C10 119.41(12) . . ?
O3 C10 C11 124.11(14) . . ?
O3 C10 C9 115.21(12) . . ?
C11 C10 C9 120.69(12) . . ?
C10 C11 C6 119.86(14) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 N1 C2 117.54(11) . . ?
C3 N2 C4 115.01(11) . . ?
C2 N3 H1N 119.0(12) . . ?
C2 N3 H2N 119.9(13) . . ?
H1N N3 H2N 120.7(18) . . ?
C3 N4 H3N 119.3(12) . . ?
C3 N4 H4N 120.2(12) . . ?
H3N N4 H4N 117.9(17) . . ?
C8 O1 C12 119.20(13) . . ?
C9 O2 C13 115.47(12) . . ?
C10 O3 C14 117.56(12) . . ?
O4 C15 C20 123.88(14) . . ?
O4 C15 C16 116.76(14) . . ?
C20 C15 C16 119.31(14) . . ?
O5 C16 C17 119.39(14) . . ?
O5 C16 C15 120.55(14) . . ?
C17 C16 C15 120.04(16) . . ?
C16 C17 C18 120.20(17) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 119.91(19) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.17(19) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.35(17) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C15 O4 H4O 111.1(14) . . ?
C16 O5 H5O 107.5(18) . . ?

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
C4 C1 C2 N3 -177.12(14) . . . . ?
C5 C1 C2 N3 8.7(2) . . . . ?
C4 C1 C2 N1 3.6(2) . . . . ?
C5 C1 C2 N1 -170.58(13) . . . . ?
C2 C1 C4 N2 -0.7(2) . . . . ?
C5 C1 C4 N2 173.53(13) . . . . ?
C4 C1 C5 C6 103.51(16) . . . . ?
C2 C1 C5 C6 -82.71(17) . . . . ?
C1 C5 C6 C7 4.8(2) . . . . ?
C1 C5 C6 C11 -175.95(12) . . . . ?
C11 C6 C7 C8 -1.0(2) . . . . ?
C5 C6 C7 C8 178.24(13) . . . . ?
C6 C7 C8 O1 -176.16(14) . . . . ?
C6 C7 C8 C9 1.8(2) . . . . ?
O1 C8 C9 O2 0.2(2) . . . . ?
C7 C8 C9 O2 -177.91(13) . . . . ?
O1 C8 C9 C10 177.25(13) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
O2 C9 C10 O3 -3.70(19) . . . . ?
C8 C9 C10 O3 179.18(12) . . . . ?
O2 C9 C10 C11 176.25(12) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
O3 C10 C11 C6 -178.32(12) . . . . ?
C9 C10 C11 C6 1.7(2) . . . . ?
C7 C6 C11 C10 -0.8(2) . . . . ?
C5 C6 C11 C10 179.94(12) . . . . ?
N2 C3 N1 C2 -0.3(2) . . . . ?
N4 C3 N1 C2 179.98(13) . . . . ?
N3 C2 N1 C3 177.54(14) . . . . ?
C1 C2 N1 C3 -3.2(2) . . . . ?
N1 C3 N2 C4 3.0(2) . . . . ?
N4 C3 N2 C4 -177.28(14) . . . . ?
C1 C4 N2 C3 -2.4(2) . . . . ?
C9 C8 O1 C12 163.56(17) . . . . ?
C7 C8 O1 C12 -18.4(2) . . . . ?
C8 C9 O2 C13 -67.4(2) . . . . ?
C10 C9 O2 C13 115.53(16) . . . . ?
C11 C10 O3 C14 -2.6(2) . . . . ?
C9 C10 O3 C14 177.35(14) . . . . ?
O4 C15 C16 O5 -0.2(2) . . . . ?
C20 C15 C16 O5 177.28(15) . . . . ?
O4 C15 C16 C17 -178.71(15) . . . . ?
C20 C15 C16 C17 -1.2(2) . . . . ?
O5 C16 C17 C18 -177.94(19) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
O4 C15 C20 C19 178.02(17) . . . . ?
C16 C15 C20 C19 0.7(3) . . . . ?
C18 C19 C20 C15 0.4(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
_geom_hbond_publ_flag
N3 H1N N1 0.90(2) 2.14(2) 3.0376(18) 174.1(17) 2_767 yes
N3 H2N O2 0.89(2) 2.36(2) 3.1843(18) 154.7(17) 2_656 yes
N3 H2N O3 0.89(2) 2.526(19) 3.0398(17) 117.6(15) 2_656 yes
N4 H3N O3 0.91(2) 2.32(2) 3.1357(19) 148.2(16) 1_666 yes
N4 H4N O5 0.87(2) 2.19(2) 3.0579(19) 169.0(17) 2_677 yes
O4 H4O N2 0.95(2) 1.74(2) 2.6844(15) 172(2) . yes
O5 H5O O4 0.90(3) 2.19(3) 2.6977(17) 115(2) . yes
O5 H5O O4 0.90(3) 2.22(3) 2.9002(19) 132(2) 2_677 yes

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_KB369_0m
_database_code_depnum_ccdc_archive 'CCDC 2180244'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N4 O3, C5 H6 N2 O2, H2 O'
_chemical_formula_sum            'C38 H52 N12 O12'
_chemical_formula_weight         868.91

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                   11.2418(11)
_cell_length_b                   16.0951(15)
_cell_length_c                   24.413(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.814(3)
_cell_angle_gamma                90
_cell_volume                     4352.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.232
_cell_measurement_theta_max      25.4565

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4276
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41449
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7648
_reflns_number_gt                5045
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1027P)²+1.1219P] 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         7648
_refine_ls_number_parameters     615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1932
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
C1A C 0.9764(2) 0.52433(15) 0.65616(10) 0.0431(6) Uani 1 1 d . . . . .
C2A C 0.8949(2) 0.48399(14) 0.68546(10) 0.0403(6) Uani 1 1 d . . . . .
C3A C 0.8131(2) 0.61011(15) 0.70257(11) 0.0466(6) Uani 1 1 d . . . . .
C4A C 0.9653(2) 0.60875(16) 0.65232(11) 0.0487(7) Uani 1 1 d . . . . .
H4A H 1.017040 0.637120 0.632919 0.058 Uiso 1 1 calc R U . . .
C5A C 1.0749(2) 0.47738(17) 0.63499(11) 0.0508(7) Uani 1 1 d . . . . .
H5A H 1.120742 0.447128 0.665936 0.061 Uiso 1 1 calc R U . . .
H5B H 1.129071 0.517550 0.622723 0.061 Uiso 1 1 calc R U . . .
C6A C 1.0367(2) 0.41638(15) 0.58793(10) 0.0451(6) Uani 1 1 d . . . . .
C7A C 1.1028(3) 0.34449(17) 0.58535(11) 0.0520(7) Uani 1 1 d . . . . .
H7A H 1.168259 0.333277 0.613178 0.062 Uiso 1 1 calc R U . . .
C8A C 1.0728(3) 0.28882(17) 0.54172(12) 0.0530(7) Uani 1 1 d . . . . .
C9A C 0.9767(3) 0.30592(17) 0.49951(11) 0.0505(7) Uani 1 1 d . . . . .
C10A C 0.9096(3) 0.37719(18) 0.50262(11) 0.0527(7) Uani 1 1 d . . . . .
C11A C 0.9395(2) 0.43249(17) 0.54660(11) 0.0508(7) Uani 1 1 d . . . . .
H11A H 0.893925 0.480390 0.548143 0.061 Uiso 1 1 calc R U . . .
C12A C 1.2251(3) 0.1935(2) 0.58216(16) 0.0845(11) Uani 1 1 d . . . . .
H12A H 1.256785 0.139791 0.575396 0.127 Uiso 1 1 calc R U . . .
H12B H 1.192440 0.192037 0.616004 0.127 Uiso 1 1 calc R U . . .
H12C H 1.288650 0.233998 0.585444 0.127 Uiso 1 1 calc R U . . .
C13A C 0.8487(4) 0.1997(3) 0.45803(17) 0.1007(14) Uani 1 1 d . . . . .
H13A H 0.782859 0.232609 0.466365 0.151 Uiso 1 1 calc R U . . .
H13B H 0.870785 0.159085 0.486767 0.151 Uiso 1 1 calc R U . . .
H13C H 0.824622 0.172066 0.423046 0.151 Uiso 1 1 calc R U . . .
N1A N 0.81274(19) 0.52713(12) 0.70835(8) 0.0433(5) Uani 1 1 d . . . . .
N2A N 0.8848(2) 0.65363(13) 0.67468(9) 0.0502(6) Uani 1 1 d . . . . .
N3A N 0.8956(3) 0.40155(14) 0.69235(11) 0.0523(6) Uani 1 1 d . . . . .
H1N H 0.952(3) 0.3675(19) 0.6811(12) 0.061(9) Uiso 1 1 d . . . . .
H2N H 0.845(3) 0.3774(19) 0.7124(12) 0.065(9) Uiso 1 1 d . . . . .
N4A N 0.7304(3) 0.65286(17) 0.72553(13) 0.0690(9) Uani 1 1 d . . . . .
H3N H 0.697(3) 0.628(2) 0.7479(14) 0.074(11) Uiso 1 1 d . . . . .
H4N H 0.743(3) 0.708(2) 0.7286(12) 0.066(9) Uiso 1 1 d . . . . .
O1A O 1.1323(2) 0.21534(13) 0.53709(10) 0.0770(7) Uani 1 1 d . . . . .
O2A O 0.94899(19) 0.25186(13) 0.45494(8) 0.0654(6) Uani 1 1 d . . . . .
O3A O 0.8158(2) 0.38857(15) 0.45947(8) 0.0798(7) Uani 1 1 d . . . . .
C14A C 0.7300(4) 0.4500(3) 0.46537(16) 0.1093(15) Uani 1 1 d . . . . .
H14A H 0.694920 0.438438 0.497744 0.164 Uiso 1 1 calc R U . . .
H14B H 0.667935 0.450184 0.433065 0.164 Uiso 1 1 calc R U . . .
H14C H 0.768674 0.503386 0.469325 0.164 Uiso 1 1 calc R U . . .
C15A C 0.4879(2) 0.39588(15) 0.65515(10) 0.0432(6) Uani 1 1 d . . . . .
C16A C 0.4924(2) 0.31301(15) 0.66106(10) 0.0462(6) Uani 1 1 d . . . . .
H16A H 0.537894 0.282864 0.639522 0.055 Uiso 1 1 calc R U . . .
C17A C 0.3669(2) 0.31057(15) 0.72974(11) 0.0441(6) Uani 1 1 d . . . . .
C18A C 0.4142(2) 0.44152(15) 0.68744(10) 0.0402(6) Uani 1 1 d . . . . .
C19A C 0.5586(3) 0.44260(18) 0.61809(11) 0.0573(7) Uani 1 1 d . . . . .
H19A H 0.601725 0.403929 0.598838 0.086 Uiso 1 1 calc R U . . .
H19B H 0.614843 0.479161 0.640217 0.086 Uiso 1 1 calc R U . . .
H19C H 0.504277 0.474558 0.591570 0.086 Uiso 1 1 calc R U . . .
N5A N 0.4339(2) 0.27046(14) 0.69700(9) 0.0465(6) Uani 1 1 d . . . . .
H5N H 0.436(2) 0.2105(19) 0.6989(11) 0.058(8) Uiso 1 1 d . . . . .
N6A N 0.3580(2) 0.39469(12) 0.72294(9) 0.0423(5) Uani 1 1 d . . . . .
H6N H 0.303(3) 0.4198(17) 0.7419(12) 0.061(9) Uiso 1 1 d . . . . .
O4A O 0.31684(19) 0.27418(11) 0.76395(9) 0.0630(6) Uani 1 1 d . . . . .
O5A O 0.39817(17) 0.51725(11) 0.68527(8) 0.0559(5) Uani 1 1 d . . . . .
C1B C 0.4803(2) -0.03485(15) 0.66354(9) 0.0396(6) Uani 1 1 d . . . . .
C2B C 0.3862(2) -0.07202(15) 0.68628(9) 0.0396(6) Uani 1 1 d . . . . .
C3B C 0.3373(2) 0.05491(15) 0.71955(10) 0.0425(6) Uani 1 1 d . . . . .
C4B C 0.4919(2) 0.04849(15) 0.67079(10) 0.0430(6) Uani 1 1 d . . . . .
H4B H 0.552537 0.074879 0.655771 0.052 Uiso 1 1 calc R U . . .
C5B C 0.5597(2) -0.08471(16) 0.63237(10) 0.0451(6) Uani 1 1 d . . . . .
H5C H 0.588480 -0.132928 0.654560 0.054 Uiso 1 1 calc R U . . .
H5D H 0.629529 -0.051300 0.628429 0.054 Uiso 1 1 calc R U . . .
C6B C 0.5009(2) -0.11414(15) 0.57527(10) 0.0409(6) Uani 1 1 d . . . . .
C7B C 0.5364(2) -0.18876(16) 0.55428(11) 0.0489(7) Uani 1 1 d . . . . .
H7B H 0.591832 -0.222650 0.576469 0.059 Uiso 1 1 calc R U . . .
C8B C 0.4893(3) -0.21286(16) 0.50042(11) 0.0510(7) Uani 1 1 d . . . . .
C9B C 0.4075(3) -0.16257(17) 0.46661(10) 0.0490(7) Uani 1 1 d . . . . .
C10B C 0.3714(2) -0.08848(16) 0.48809(10) 0.0445(6) Uani 1 1 d . . . . .
C11B C 0.4179(2) -0.06488(15) 0.54196(9) 0.0429(6) Uani 1 1 d . . . . .
H11B H 0.392860 -0.015265 0.555882 0.051 Uiso 1 1 calc R U . . .
C12B C 0.6086(4) -0.3357(2) 0.50938(19) 0.1105(15) Uani 1 1 d . . . . .
H12D H 0.623156 -0.384220 0.488622 0.166 Uiso 1 1 calc R U . . .
H12E H 0.580734 -0.352170 0.542796 0.166 Uiso 1 1 calc R U . . .
H12F H 0.682188 -0.304622 0.518794 0.166 Uiso 1 1 calc R U . . .
C13B C 0.2495(3) -0.2201(2) 0.40115(13) 0.0742(9) Uani 1 1 d . . . . .
H13D H 0.228471 -0.232896 0.362286 0.111 Uiso 1 1 calc R U . . .
H13E H 0.192202 -0.181312 0.411365 0.111 Uiso 1 1 calc R U . . .
H13F H 0.248411 -0.270117 0.422500 0.111 Uiso 1 1 calc R U . . .
C14B C 0.2451(3) 0.03071(19) 0.47460(12) 0.0642(8) Uani 1 1 d . . . . .
H14D H 0.311455 0.067248 0.487534 0.096 Uiso 1 1 calc R U . . .
H14E H 0.204968 0.016460 0.505016 0.096 Uiso 1 1 calc R U . . .
H14F H 0.189226 0.058030 0.446148 0.096 Uiso 1 1 calc R U . . .
N1B N 0.31578(19) -0.02750(12) 0.71474(8) 0.0431(5) Uani 1 1 d . . . . .
N2B N 0.4224(2) 0.09607(12) 0.69809(8) 0.0450(5) Uani 1 1 d . . . . .
N3B N 0.3617(3) -0.15328(15) 0.68026(10) 0.0562(7) Uani 1 1 d . . . . .
H7N H 0.405(2) -0.1857(16) 0.6653(11) 0.044(8) Uiso 1 1 d . . . . .
H8N H 0.299(3) -0.1749(18) 0.6972(13) 0.062(9) Uiso 1 1 d . . . . .
N4B N 0.2650(2) 0.09898(16) 0.74682(11) 0.0572(7) Uani 1 1 d . . . . .
H9N H 0.218(3) 0.0711(19) 0.7646(12) 0.063(9) Uiso 1 1 d . . . . .
H10N H 0.277(2) 0.1527(19) 0.7537(11) 0.052(8) Uiso 1 1 d . . . . .
O1B O 0.5193(2) -0.28528(13) 0.47659(9) 0.0762(7) Uani 1 1 d . . . . .
O2B O 0.36676(19) -0.18468(12) 0.41192(7) 0.0622(6) Uani 1 1 d . . . . .
O3B O 0.28892(18) -0.04259(12) 0.45259(7) 0.0604(5) Uani 1 1 d . . . . .
C15B C 0.9732(2) 0.95790(16) 0.65086(10) 0.0473(6) Uani 1 1 d . . . . .
C16B C 0.9623(3) 0.87477(17) 0.64797(11) 0.0504(7) Uani 1 1 d . . . . .
H16B H 1.003407 0.846401 0.623749 0.060 Uiso 1 1 calc R U . . .
C17B C 0.8316(2) 0.86658(14) 0.71431(10) 0.0416(6) Uani 1 1 d . . . . .
C18B C 0.9067(2) 1.00082(16) 0.68785(10) 0.0443(6) Uani 1 1 d . . . . .
C19B C 1.0463(3) 1.00836(19) 0.61738(13) 0.0680(9) Uani 1 1 d . . . . .
H19D H 1.087206 0.972038 0.595504 0.102 Uiso 1 1 calc R U . . .
H19E H 1.104723 1.040466 0.641881 0.102 Uiso 1 1 calc R U . . .
H19F H 0.994121 1.045003 0.593248 0.102 Uiso 1 1 calc R U . . .
N5B N 0.8944(2) 0.82966(14) 0.67853(9) 0.0455(5) Uani 1 1 d . . . . .
H11N H 0.891(2) 0.7734(18) 0.6763(11) 0.052(8) Uiso 1 1 d . . . . .
N6B N 0.8403(2) 0.95105(12) 0.71761(9) 0.0427(5) Uani 1 1 d . . . . .
H12N H 0.801(3) 0.9743(18) 0.7414(12) 0.063(9) Uiso 1 1 d . . . . .
O4B O 0.76906(17) 0.82714(10) 0.74245(8) 0.0525(5) Uani 1 1 d . . . . .
O5B O 0.90579(18) 1.07651(11) 0.69421(8) 0.0616(5) Uani 1 1 d . . . . .
O1W O 0.4783(3) 0.67962(16) 0.65823(15) 0.1303(12) Uani 1 1 d . . . . .
H1W H 0.557676 0.676537 0.678782 0.195 Uiso 1 1 d R U . . .
H2W H 0.441316 0.630996 0.665069 0.195 Uiso 1 1 d R U . . .
O2W O 1.0250(3) 1.23659(14) 0.69689(13) 0.1060(9) Uani 1 1 d . . . . .
H3W H 1.076965 1.235241 0.731077 0.159 Uiso 1 1 d R U . . .
H4W H 0.992618 1.184664 0.692433 0.159 Uiso 1 1 d 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
C1A C4A 1.366(3) . ?
C1A C2A 1.413(3) . ?
C1A C5A 1.503(3) . ?
C2A N3A 1.337(3) . ?
C2A N1A 1.350(3) . ?
C3A N2A 1.338(3) . ?
C3A N1A 1.343(3) . ?
C3A N4A 1.353(3) . ?
C4A N2A 1.344(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.517(3) . ?
C5A H5A 0.9700 . ?
C5A H5B 0.9700 . ?
C6A C11A 1.380(4) . ?
C6A C7A 1.382(4) . ?
C7A C8A 1.389(4) . ?
C7A H7A 0.9300 . ?
C8A O1A 1.373(3) . ?
C8A C9A 1.387(4) . ?
C9A C10A 1.382(4) . ?
C9A O2A 1.386(3) . ?
C10A O3A 1.370(3) . ?
C10A C11A 1.391(4) . ?
C11A H11A 0.9300 . ?
C12A O1A 1.425(4) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A O2A 1.418(4) . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
N3A H1N 0.91(3) . ?
N3A H2N 0.90(3) . ?
N4A H3N 0.82(3) . ?
N4A H4N 0.90(3) . ?
O3A C14A 1.406(4) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A C16A 1.342(3) . ?
C15A C18A 1.439(3) . ?
C15A C19A 1.503(4) . ?
C16A N5A 1.367(3) . ?
C16A H16A 0.9300 . ?
C17A O4A 1.231(3) . ?
C17A N5A 1.353(3) . ?
C17A N6A 1.366(3) . ?
C18A O5A 1.232(3) . ?
C18A N6A 1.380(3) . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
N5A H5N 0.97(3) . ?
N6A H6N 0.93(3) . ?
C1B C4B 1.356(3) . ?
C1B C2B 1.409(3) . ?
C1B C5B 1.500(3) . ?
C2B N3B 1.339(3) . ?
C2B N1B 1.345(3) . ?
C3B N4B 1.338(3) . ?
C3B N2B 1.342(3) . ?
C3B N1B 1.350(3) . ?
C4B N2B 1.348(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.513(3) . ?
C5B H5C 0.9700 . ?
C5B H5D 0.9700 . ?
C6B C11B 1.379(3) . ?
C6B C7B 1.390(3) . ?
C7B C8B 1.386(4) . ?
C7B H7B 0.9300 . ?
C8B O1B 1.370(3) . ?
C8B C9B 1.387(4) . ?
C9B O2B 1.382(3) . ?
C9B C10B 1.391(4) . ?
C10B O3B 1.372(3) . ?
C10B C11B 1.383(3) . ?
C11B H11B 0.9300 . ?
C12B O1B 1.426(5) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B O2B 1.419(4) . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14B O3B 1.419(3) . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
N3B H7N 0.84(3) . ?
N3B H8N 0.95(3) . ?
N4B H9N 0.86(3) . ?
N4B H10N 0.89(3) . ?
C15B C16B 1.344(4) . ?
C15B C18B 1.443(4) . ?
C15B C19B 1.495(4) . ?
C16B N5B 1.364(3) . ?
C16B H16B 0.9300 . ?
C17B O4B 1.238(3) . ?
C17B N5B 1.351(3) . ?
C17B N6B 1.364(3) . ?
C18B O5B 1.228(3) . ?
C18B N6B 1.383(3) . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
N5B H11N 0.91(3) . ?
N6B H12N 0.87(3) . ?
O1W H1W 0.9478 . ?
O1W H2W 0.9146 . ?
O2W H3W 0.9338 . ?
O2W H4W 0.9107 . ?

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
C4A C1A C2A 115.6(2) . . ?
C4A C1A C5A 122.7(2) . . ?
C2A C1A C5A 121.5(2) . . ?
N3A C2A N1A 116.6(2) . . ?
N3A C2A C1A 121.9(2) . . ?
N1A C2A C1A 121.4(2) . . ?
N2A C3A N1A 125.9(2) . . ?
N2A C3A N4A 117.4(2) . . ?
N1A C3A N4A 116.6(2) . . ?
N2A C4A C1A 124.5(2) . . ?
N2A C4A H4A 117.8 . . ?
C1A C4A H4A 117.8 . . ?
C1A C5A C6A 117.1(2) . . ?
C1A C5A H5A 108.0 . . ?
C6A C5A H5A 108.0 . . ?
C1A C5A H5B 108.0 . . ?
C6A C5A H5B 108.0 . . ?
H5A C5A H5B 107.3 . . ?
C11A C6A C7A 119.3(2) . . ?
C11A C6A C5A 121.3(2) . . ?
C7A C6A C5A 119.4(2) . . ?
C6A C7A C8A 120.8(3) . . ?
C6A C7A H7A 119.6 . . ?
C8A C7A H7A 119.6 . . ?
O1A C8A C9A 116.0(2) . . ?
O1A C8A C7A 124.1(3) . . ?
C9A C8A C7A 119.9(3) . . ?
C10A C9A O2A 120.8(3) . . ?
C10A C9A C8A 119.1(2) . . ?
O2A C9A C8A 120.0(3) . . ?
O3A C10A C9A 115.1(2) . . ?
O3A C10A C11A 124.1(3) . . ?
C9A C10A C11A 120.7(3) . . ?
C6A C11A C10A 120.1(3) . . ?
C6A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
O1A C12A H12A 109.5 . . ?
O1A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
O1A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O2A C13A H13A 109.5 . . ?
O2A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
O2A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C3A N1A C2A 117.0(2) . . ?
C3A N2A C4A 115.5(2) . . ?
C2A N3A H1N 123.2(18) . . ?
C2A N3A H2N 120.6(19) . . ?
H1N N3A H2N 116(3) . . ?
C3A N4A H3N 117(2) . . ?
C3A N4A H4N 115.3(19) . . ?
H3N N4A H4N 120(3) . . ?
C8A O1A C12A 116.9(2) . . ?
C9A O2A C13A 113.8(2) . . ?
C10A O3A C14A 117.8(3) . . ?
O3A C14A H14A 109.5 . . ?
O3A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
O3A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C16A C15A C18A 117.6(2) . . ?
C16A C15A C19A 123.2(2) . . ?
C18A C15A C19A 119.1(2) . . ?
C15A C16A N5A 123.6(2) . . ?
C15A C16A H16A 118.2 . . ?
N5A C16A H16A 118.2 . . ?
O4A C17A N5A 122.6(2) . . ?
O4A C17A N6A 121.5(2) . . ?
N5A C17A N6A 115.9(2) . . ?
O5A C18A N6A 119.2(2) . . ?
O5A C18A C15A 125.1(2) . . ?
N6A C18A C15A 115.7(2) . . ?
C15A C19A H19A 109.5 . . ?
C15A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C15A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C17A N5A C16A 121.2(2) . . ?
C17A N5A H5N 117.2(16) . . ?
C16A N5A H5N 121.6(16) . . ?
C17A N6A C18A 125.9(2) . . ?
C17A N6A H6N 114.4(17) . . ?
C18A N6A H6N 119.5(17) . . ?
C4B C1B C2B 115.5(2) . . ?
C4B C1B C5B 122.9(2) . . ?
C2B C1B C5B 121.6(2) . . ?
N3B C2B N1B 116.7(2) . . ?
N3B C2B C1B 121.7(2) . . ?
N1B C2B C1B 121.6(2) . . ?
N4B C3B N2B 117.8(2) . . ?
N4B C3B N1B 116.7(2) . . ?
N2B C3B N1B 125.5(2) . . ?
N2B C4B C1B 125.1(2) . . ?
N2B C4B H4B 117.4 . . ?
C1B C4B H4B 117.4 . . ?
C1B C5B C6B 115.5(2) . . ?
C1B C5B H5C 108.4 . . ?
C6B C5B H5C 108.4 . . ?
C1B C5B H5D 108.4 . . ?
C6B C5B H5D 108.4 . . ?
H5C C5B H5D 107.5 . . ?
C11B C6B C7B 119.1(2) . . ?
C11B C6B C5B 120.6(2) . . ?
C7B C6B C5B 120.2(2) . . ?
C8B C7B C6B 120.3(3) . . ?
C8B C7B H7B 119.9 . . ?
C6B C7B H7B 119.9 . . ?
O1B C8B C7B 124.0(3) . . ?
O1B C8B C9B 115.5(2) . . ?
C7B C8B C9B 120.5(2) . . ?
O2B C9B C8B 120.1(2) . . ?
O2B C9B C10B 121.0(3) . . ?
C8B C9B C10B 118.9(2) . . ?
O3B C10B C11B 123.9(2) . . ?
O3B C10B C9B 115.6(2) . . ?
C11B C10B C9B 120.5(2) . . ?
C6B C11B C10B 120.7(2) . . ?
C6B C11B H11B 119.6 . . ?
C10B C11B H11B 119.6 . . ?
O1B C12B H12D 109.5 . . ?
O1B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
O1B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O2B C13B H13D 109.5 . . ?
O2B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
O2B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O3B C14B H14D 109.5 . . ?
O3B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
O3B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C2B N1B C3B 117.1(2) . . ?
C3B N2B C4B 115.1(2) . . ?
C2B N3B H7N 122.3(18) . . ?
C2B N3B H8N 117.8(17) . . ?
H7N N3B H8N 120(3) . . ?
C3B N4B H9N 117(2) . . ?
C3B N4B H10N 122.0(18) . . ?
H9N N4B H10N 120(3) . . ?
C8B O1B C12B 116.5(2) . . ?
C9B O2B C13B 115.3(2) . . ?
C10B O3B C14B 116.7(2) . . ?
C16B C15B C18B 117.2(2) . . ?
C16B C15B C19B 124.5(3) . . ?
C18B C15B C19B 118.3(2) . . ?
C15B C16B N5B 123.7(2) . . ?
C15B C16B H16B 118.1 . . ?
N5B C16B H16B 118.1 . . ?
O4B C17B N5B 122.8(2) . . ?
O4B C17B N6B 121.3(2) . . ?
N5B C17B N6B 115.9(2) . . ?
O5B C18B N6B 119.4(2) . . ?
O5B C18B C15B 124.8(2) . . ?
N6B C18B C15B 115.8(2) . . ?
C15B C19B H19D 109.5 . . ?
C15B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C15B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C17B N5B C16B 121.5(2) . . ?
C17B N5B H11N 117.2(17) . . ?
C16B N5B H11N 121.3(17) . . ?
C17B N6B C18B 125.9(2) . . ?
C17B N6B H12N 115(2) . . ?
C18B N6B H12N 119(2) . . ?
H1W O1W H2W 105.9 . . ?
H3W O2W H4W 105.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A C1A C2A N3A 180.0(2) . . . . ?
C5A C1A C2A N3A -4.9(4) . . . . ?
C4A C1A C2A N1A -0.6(4) . . . . ?
C5A C1A C2A N1A 174.6(2) . . . . ?
C2A C1A C4A N2A 0.7(4) . . . . ?
C5A C1A C4A N2A -174.3(2) . . . . ?
C4A C1A C5A C6A -116.6(3) . . . . ?
C2A C1A C5A C6A 68.6(3) . . . . ?
C1A C5A C6A C11A 35.7(4) . . . . ?
C1A C5A C6A C7A -146.4(3) . . . . ?
C11A C6A C7A C8A 0.2(4) . . . . ?
C5A C6A C7A C8A -177.7(2) . . . . ?
C6A C7A C8A O1A -178.3(3) . . . . ?
C6A C7A C8A C9A 1.2(4) . . . . ?
O1A C8A C9A C10A 177.4(2) . . . . ?
C7A C8A C9A C10A -2.2(4) . . . . ?
O1A C8A C9A O2A -2.6(4) . . . . ?
C7A C8A C9A O2A 177.8(2) . . . . ?
O2A C9A C10A O3A 0.7(4) . . . . ?
C8A C9A C10A O3A -179.3(2) . . . . ?
O2A C9A C10A C11A -178.3(2) . . . . ?
C8A C9A C10A C11A 1.7(4) . . . . ?
C7A C6A C11A C10A -0.7(4) . . . . ?
C5A C6A C11A C10A 177.2(2) . . . . ?
O3A C10A C11A C6A -179.1(3) . . . . ?
C9A C10A C11A C6A -0.3(4) . . . . ?
N2A C3A N1A C2A 2.3(4) . . . . ?
N4A C3A N1A C2A 179.9(3) . . . . ?
N3A C2A N1A C3A 178.7(2) . . . . ?
C1A C2A N1A C3A -0.8(3) . . . . ?
N1A C3A N2A C4A -2.2(4) . . . . ?
N4A C3A N2A C4A -179.7(3) . . . . ?
C1A C4A N2A C3A 0.5(4) . . . . ?
C9A C8A O1A C12A -175.2(3) . . . . ?
C7A C8A O1A C12A 4.4(4) . . . . ?
C10A C9A O2A C13A -77.9(4) . . . . ?
C8A C9A O2A C13A 102.1(4) . . . . ?
C9A C10A O3A C14A 167.5(3) . . . . ?
C11A C10A O3A C14A -13.6(4) . . . . ?
C18A C15A C16A N5A -1.9(4) . . . . ?
C19A C15A C16A N5A 176.1(2) . . . . ?
C16A C15A C18A O5A -177.7(2) . . . . ?
C19A C15A C18A O5A 4.2(4) . . . . ?
C16A C15A C18A N6A 1.9(3) . . . . ?
C19A C15A C18A N6A -176.2(2) . . . . ?
O4A C17A N5A C16A -177.3(3) . . . . ?
N6A C17A N5A C16A 2.4(4) . . . . ?
C15A C16A N5A C17A -0.4(4) . . . . ?
O4A C17A N6A C18A 177.4(2) . . . . ?
N5A C17A N6A C18A -2.3(4) . . . . ?
O5A C18A N6A C17A 179.8(2) . . . . ?
C15A C18A N6A C17A 0.1(4) . . . . ?
C4B C1B C2B N3B 177.4(2) . . . . ?
C5B C1B C2B N3B -1.3(4) . . . . ?
C4B C1B C2B N1B -2.1(3) . . . . ?
C5B C1B C2B N1B 179.3(2) . . . . ?
C2B C1B C4B N2B 0.9(4) . . . . ?
C5B C1B C4B N2B 179.5(2) . . . . ?
C4B C1B C5B C6B -106.4(3) . . . . ?
C2B C1B C5B C6B 72.2(3) . . . . ?
C1B C5B C6B C11B 36.0(3) . . . . ?
C1B C5B C6B C7B -148.5(2) . . . . ?
C11B C6B C7B C8B 0.5(4) . . . . ?
C5B C6B C7B C8B -175.1(2) . . . . ?
C6B C7B C8B O1B -179.9(2) . . . . ?
C6B C7B C8B C9B 0.7(4) . . . . ?
O1B C8B C9B O2B -3.3(4) . . . . ?
C7B C8B C9B O2B 176.1(2) . . . . ?
O1B C8B C9B C10B 179.2(2) . . . . ?
C7B C8B C9B C10B -1.4(4) . . . . ?
O2B C9B C10B O3B 3.5(4) . . . . ?
C8B C9B C10B O3B -179.0(2) . . . . ?
O2B C9B C10B C11B -176.5(2) . . . . ?
C8B C9B C10B C11B 1.0(4) . . . . ?
C7B C6B C11B C10B -0.9(4) . . . . ?
C5B C6B C11B C10B 174.7(2) . . . . ?
O3B C10B C11B C6B -179.8(2) . . . . ?
C9B C10B C11B C6B 0.2(4) . . . . ?
N3B C2B N1B C3B -178.0(2) . . . . ?
C1B C2B N1B C3B 1.5(3) . . . . ?
N4B C3B N1B C2B 178.5(2) . . . . ?
N2B C3B N1B C2B 0.4(4) . . . . ?
N4B C3B N2B C4B -179.6(2) . . . . ?
N1B C3B N2B C4B -1.5(4) . . . . ?
C1B C4B N2B C3B 0.8(4) . . . . ?
C7B C8B O1B C12B -3.0(4) . . . . ?
C9B C8B O1B C12B 176.4(3) . . . . ?
C8B C9B O2B C13B 102.0(3) . . . . ?
C10B C9B O2B C13B -80.6(3) . . . . ?
C11B C10B O3B C14B -3.7(4) . . . . ?
C9B C10B O3B C14B 176.3(2) . . . . ?
C18B C15B C16B N5B -1.2(4) . . . . ?
C19B C15B C16B N5B -179.5(3) . . . . ?
C16B C15B C18B O5B -178.6(3) . . . . ?
C19B C15B C18B O5B -0.2(4) . . . . ?
C16B C15B C18B N6B 1.4(3) . . . . ?
C19B C15B C18B N6B 179.8(2) . . . . ?
O4B C17B N5B C16B 179.9(2) . . . . ?
N6B C17B N5B C16B 0.2(3) . . . . ?
C15B C16B N5B C17B 0.4(4) . . . . ?
O4B C17B N6B C18B -179.6(2) . . . . ?
N5B C17B N6B C18B 0.1(4) . . . . ?
O5B C18B N6B C17B 179.1(2) . . . . ?
C15B C18B N6B C17B -0.9(4) . . . . ?

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
_geom_hbond_publ_flag
C13A H13A O3A 0.96 2.55 3.063(5) 113.8 . yes
N3A H1N O2W 0.91(3) 2.27(3) 3.020(3) 139(2) 1_545 yes
N3A H2N O4B 0.90(3) 2.00(3) 2.898(3) 178(3) 2_646 yes
N4A H3N O5B 0.82(3) 2.14(4) 2.952(4) 173(3) 2_646 yes
N4A H4N O4B 0.90(3) 1.96(3) 2.858(3) 175(3) . yes
C16A H16A O2B 0.93 2.38 3.303(3) 169.6 3_656 yes
N5A H5N N2B 0.97(3) 1.85(3) 2.810(3) 174(2) . yes
N6A H6N N1B 0.93(3) 2.03(3) 2.952(3) 178(3) 2_556 yes
C13B H13E O3B 0.96 2.61 3.122(4) 113.8 . yes
N3B H7N O1W 0.84(3) 2.34(3) 3.079(4) 148(2) 1_545 yes
N3B H8N O4A 0.95(3) 1.92(3) 2.860(3) 174(3) 2_546 yes
N4B H9N O5A 0.86(3) 2.12(3) 2.980(3) 172(3) 2_546 yes
N4B H10N O4A 0.89(3) 2.01(3) 2.895(3) 174(3) . yes
C16B H16B O2A 0.93 2.61 3.509(3) 162.0 3_766 yes
N5B H11N N2A 0.91(3) 1.93(3) 2.836(3) 178(2) . yes
N6B H12N N1A 0.87(3) 2.10(3) 2.964(3) 173(3) 2_656 yes
O1W H1W N4A 0.95 2.11 3.055(5) 172.5 . yes
O1W H2W O5A 0.91 1.98 2.877(3) 167.4 . yes
O2W H4W O5B 0.91 2.00 2.900(3) 169.4 . yes

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.064

