# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2208396'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2022-09-20 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 N6 O3'
_chemical_formula_sum            'C15 H24 N6 O3'
_chemical_formula_weight         336.40

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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                   11.153(3)
_cell_length_b                   9.171(3)
_cell_length_c                   18.019(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1843.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3850
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      22.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.213
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            11935
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.261
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3221
_reflns_number_gt                2682
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982

_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       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         3221
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.8154(3) 0.5755(5) 0.4032(2) 0.0396(10) Uani 1 1 d . . . . .
C2 C 0.8498(5) 0.7263(6) 0.3741(3) 0.0750(17) Uani 1 1 d . . . . .
H2A H 0.902772 0.715658 0.331049 0.112 Uiso 1 1 calc R U . . .
H2B H 0.891394 0.780768 0.413146 0.112 Uiso 1 1 calc R U . . .
H2C H 0.777200 0.779155 0.359375 0.112 Uiso 1 1 calc R U . . .
C3 C 0.7561(4) 0.4828(6) 0.3447(2) 0.0599(13) Uani 1 1 d . . . . .
H3C H 0.812391 0.466023 0.303804 0.090 Uiso 1 1 calc R U . . .
H3A H 0.684775 0.533063 0.325813 0.090 Uiso 1 1 calc R U . . .
H3B H 0.732532 0.389062 0.366336 0.090 Uiso 1 1 calc R U . . .
C4 C 0.7320(3) 0.5978(4) 0.4696(2) 0.0327(9) Uani 1 1 d . . . . .
C5 C 0.7163(3) 0.6519(3) 0.6032(2) 0.0298(8) Uani 1 1 d . . . . .
C7 C 0.6881(3) 0.8138(4) 0.5978(3) 0.0442(10) Uani 1 1 d . . . . .
H7B H 0.762898 0.868987 0.593054 0.066 Uiso 1 1 calc R U . . .
H7A H 0.645546 0.845058 0.642688 0.066 Uiso 1 1 calc R U . . .
H7C H 0.637517 0.831621 0.554278 0.066 Uiso 1 1 calc R U . . .
C6 C 0.7962(3) 0.6206(4) 0.6703(2) 0.0358(9) Uani 1 1 d . . . . .
H6B H 0.814324 0.516104 0.672324 0.054 Uiso 1 1 calc R U . . .
H6A H 0.754543 0.649779 0.715794 0.054 Uiso 1 1 calc R U . . .
H6C H 0.871108 0.675827 0.665728 0.054 Uiso 1 1 calc R U . . .
C8 C 0.5985(3) 0.5642(3) 0.6115(2) 0.0245(7) Uani 1 1 d . . . . .
C9 C 0.5152(3) 0.3117(3) 0.6191(2) 0.0281(8) Uani 1 1 d . . . . .
C11 C 0.5730(3) 0.1619(4) 0.6185(3) 0.0469(11) Uani 1 1 d . . . . .
H11B H 0.611209 0.145102 0.570282 0.070 Uiso 1 1 calc R U . . .
H11A H 0.511579 0.087350 0.627036 0.070 Uiso 1 1 calc R U . . .
H11C H 0.633592 0.156448 0.657818 0.070 Uiso 1 1 calc R U . . .
C10 C 0.4556(4) 0.3391(4) 0.6944(2) 0.0410(10) Uani 1 1 d . . . . .
H10C H 0.517428 0.350489 0.732561 0.061 Uiso 1 1 calc R U . . .
H10A H 0.403946 0.256278 0.706972 0.061 Uiso 1 1 calc R U . . .
H10B H 0.407148 0.428142 0.691738 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4186(3) 0.3108(3) 0.5585(2) 0.0277(8) Uani 1 1 d . . . . .
C13 C 0.3513(4) 0.3886(5) 0.4370(3) 0.0476(11) Uani 1 1 d . . . . .
H13A H 0.291047 0.311174 0.445658 0.057 Uiso 1 1 calc R U . . .
H13B H 0.308824 0.483361 0.436267 0.057 Uiso 1 1 calc R U . . .
C14 C 0.4079(4) 0.3649(5) 0.3654(3) 0.0475(11) Uani 1 1 d . . . . .
C15 C 0.4548(5) 0.3462(5) 0.3073(3) 0.0568(13) Uani 1 1 d . . . . .
H15 H 0.492530 0.331193 0.260672 0.068 Uiso 1 1 calc R U . . .
N1 N 1.0924(4) 0.4878(6) 0.3528(3) 0.0789(14) Uani 1 1 d . . . . .
N2 N 1.0102(3) 0.4970(5) 0.3883(2) 0.0548(11) Uani 1 1 d . . . . .
N3 N 0.9255(3) 0.5004(4) 0.4322(2) 0.0486(9) Uani 1 1 d . . . . .
N4 N 0.7818(2) 0.6047(3) 0.53638(17) 0.0299(7) Uani 1 1 d . . . . .
H4 H 0.857610 0.579862 0.540979 0.036 Uiso 1 1 calc R U . . .
N5 N 0.6098(2) 0.4188(3) 0.60392(16) 0.0242(6) Uani 1 1 d . . . . .
H5 H 0.679446 0.385358 0.588597 0.029 Uiso 1 1 calc R U . . .
N6 N 0.4374(3) 0.3882(3) 0.49751(17) 0.0333(8) Uani 1 1 d . . . . .
H6 H 0.503325 0.440355 0.493575 0.040 Uiso 1 1 calc R U . . .
O1 O 0.6236(2) 0.6148(3) 0.45905(15) 0.0396(7) Uani 1 1 d . . . . .
O2 O 0.50442(19) 0.6240(2) 0.62822(14) 0.0330(6) Uani 1 1 d . . . . .
O3 O 0.3293(2) 0.2336(3) 0.56741(16) 0.0427(7) 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 N3 1.502(5) . ?
C1 C3 1.508(6) . ?
C1 C4 1.528(5) . ?
C1 C2 1.528(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 O1 1.234(4) . ?
C4 N4 1.327(5) . ?
C5 N4 1.473(4) . ?
C5 C7 1.521(5) . ?
C5 C6 1.529(5) . ?
C5 C8 1.548(4) . ?
C7 H7B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6C 0.9800 . ?
C8 O2 1.221(4) . ?
C8 N5 1.346(4) . ?
C9 N5 1.467(4) . ?
C9 C11 1.518(4) . ?
C9 C10 1.531(5) . ?
C9 C12 1.534(5) . ?
C11 H11B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C12 O3 1.233(4) . ?
C12 N6 1.325(5) . ?
C13 C14 1.452(7) . ?
C13 N6 1.453(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.183(7) . ?
C15 H15 0.9500 . ?
N1 N2 1.121(5) . ?
N2 N3 1.234(5) . ?
N4 H4 0.8800 . ?
N5 H5 0.8800 . ?
N6 H6 0.8800 . ?

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
N3 C1 C3 110.1(3) . . ?
N3 C1 C4 106.7(3) . . ?
C3 C1 C4 110.8(3) . . ?
N3 C1 C2 109.2(3) . . ?
C3 C1 C2 112.3(4) . . ?
C4 C1 C2 107.5(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
H3C C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3C C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C4 N4 122.9(3) . . ?
O1 C4 C1 119.6(3) . . ?
N4 C4 C1 117.4(3) . . ?
N4 C5 C7 109.7(3) . . ?
N4 C5 C6 107.6(3) . . ?
C7 C5 C6 110.8(3) . . ?
N4 C5 C8 110.3(3) . . ?
C7 C5 C8 109.7(3) . . ?
C6 C5 C8 108.7(3) . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
O2 C8 N5 123.4(3) . . ?
O2 C8 C5 121.3(3) . . ?
N5 C8 C5 115.2(3) . . ?
N5 C9 C11 107.4(2) . . ?
N5 C9 C10 111.6(3) . . ?
C11 C9 C10 109.9(3) . . ?
N5 C9 C12 112.1(3) . . ?
C11 C9 C12 106.7(3) . . ?
C10 C9 C12 109.0(3) . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
C9 C10 H10C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C12 N6 122.9(3) . . ?
O3 C12 C9 118.6(3) . . ?
N6 C12 C9 118.4(3) . . ?
C14 C13 N6 112.3(3) . . ?
C14 C13 H13A 109.2 . . ?
N6 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
N6 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 179.4(5) . . ?
C14 C15 H15 180.0 . . ?
N1 N2 N3 174.2(5) . . ?
N2 N3 C1 114.5(3) . . ?
C4 N4 C5 123.2(3) . . ?
C4 N4 H4 118.4 . . ?
C5 N4 H4 118.4 . . ?
C8 N5 C9 125.2(3) . . ?
C8 N5 H5 117.4 . . ?
C9 N5 H5 117.4 . . ?
C12 N6 C13 121.3(3) . . ?
C12 N6 H6 119.4 . . ?
C13 N6 H6 119.4 . . ?

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
N3 C1 C4 O1 -157.7(3) . . . . ?
C3 C1 C4 O1 -37.9(5) . . . . ?
C2 C1 C4 O1 85.2(4) . . . . ?
N3 C1 C4 N4 25.4(4) . . . . ?
C3 C1 C4 N4 145.2(4) . . . . ?
C2 C1 C4 N4 -91.7(4) . . . . ?
N4 C5 C8 O2 -136.2(3) . . . . ?
C7 C5 C8 O2 -15.3(5) . . . . ?
C6 C5 C8 O2 106.0(4) . . . . ?
N4 C5 C8 N5 48.0(4) . . . . ?
C7 C5 C8 N5 169.0(3) . . . . ?
C6 C5 C8 N5 -69.7(4) . . . . ?
N5 C9 C12 O3 -174.5(3) . . . . ?
C11 C9 C12 O3 68.1(4) . . . . ?
C10 C9 C12 O3 -50.5(4) . . . . ?
N5 C9 C12 N6 8.3(4) . . . . ?
C11 C9 C12 N6 -109.0(4) . . . . ?
C10 C9 C12 N6 132.4(3) . . . . ?
C3 C1 N3 N2 71.6(5) . . . . ?
C4 C1 N3 N2 -168.1(4) . . . . ?
C2 C1 N3 N2 -52.2(5) . . . . ?
O1 C4 N4 C5 -8.2(5) . . . . ?
C1 C4 N4 C5 168.5(3) . . . . ?
C7 C5 N4 C4 -68.9(4) . . . . ?
C6 C5 N4 C4 170.5(3) . . . . ?
C8 C5 N4 C4 52.0(4) . . . . ?
O2 C8 N5 C9 -4.3(6) . . . . ?
C5 C8 N5 C9 171.3(3) . . . . ?
C11 C9 N5 C8 -168.8(3) . . . . ?
C10 C9 N5 C8 -48.3(4) . . . . ?
C12 C9 N5 C8 74.3(4) . . . . ?
O3 C12 N6 C13 1.1(5) . . . . ?
C9 C12 N6 C13 178.1(3) . . . . ?
C14 C13 N6 C12 -131.9(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
C7 H7C O1 0.98 2.63 3.178(5) 115.5 . yes
C6 H6C O2 0.98 2.46 3.384(4) 157.6 3_565 yes
C10 H10B O2 0.98 2.39 2.923(4) 113.5 . yes
N5 H5 O3 0.88 2.03 2.895(3) 166.5 3 yes
N6 H6 O1 0.88 2.18 3.019(4) 159.5 . yes
C7 H7C O1 0.98 2.63 3.178(5) 115.5 . yes
C6 H6C O2 0.98 2.46 3.384(4) 157.6 3_565 yes
C10 H10B O2 0.98 2.39 2.923(4) 113.5 . yes
N5 H5 O3 0.88 2.03 2.895(3) 166.5 3 yes
N6 H6 O1 0.88 2.18 3.019(4) 159.5 . yes

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.043



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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2247295'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2023-03-08 deposited with the CCDC.	2023-04-14 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         'C15 H24 N6 O3'
_chemical_formula_sum            'C15 H24 N6 O3'
_chemical_formula_weight         336.40

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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                   11.2274(13)
_cell_length_b                   9.2607(12)
_cell_length_c                   18.166(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1888.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3618
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      19.63

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.183
_exptl_crystal_density_method    None
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            25529
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4680
_reflns_number_gt                2806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.999

_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       'APEX3/SAINT (Bruker 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3-2014.1(Farrugia, 1997)'
_computing_publication_material  "SHELXL-2018/3'(Sheldrick, 2018)"
_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)+(0.0771P)²+0.2198P] 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 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         4680
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

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
O2 O 0.4880(2) 0.6159(3) 0.63148(16) 0.0555(8) Uani 1 1 d . . . . .
N5 N 0.3836(3) 0.4178(3) 0.60131(19) 0.0424(7) Uani 1 1 d . . . . .
N4 N 0.2171(3) 0.6067(4) 0.5359(2) 0.0535(9) Uani 1 1 d . . . . .
H4 H 0.143306 0.582768 0.539361 0.064 Uiso 1 1 calc R U . . .
C12 C 0.5740(3) 0.3144(4) 0.5562(2) 0.0489(9) Uani 1 1 d . . . . .
N6 N 0.5601(3) 0.3978(4) 0.4987(2) 0.0613(10) Uani 1 1 d . . . . .
H6 H 0.496657 0.449463 0.495489 0.074 Uiso 1 1 calc R U . . .
O3 O 0.6617(3) 0.2362(4) 0.5644(2) 0.0808(11) Uani 1 1 d . . . . .
C8 C 0.3953(3) 0.5596(4) 0.6125(2) 0.0407(8) Uani 1 1 d . . . . .
O1 O 0.3751(3) 0.6209(4) 0.46078(19) 0.0713(9) Uani 1 1 d . . . . .
C9 C 0.4764(3) 0.3094(4) 0.6144(2) 0.0473(9) Uani 1 1 d . . . . .
C4 C 0.2676(4) 0.6035(4) 0.4700(3) 0.0571(10) Uani 1 1 d . . . . .
C5 C 0.2801(3) 0.6490(4) 0.6033(2) 0.0483(9) Uani 1 1 d . . . . .
C14 C 0.5952(6) 0.3824(7) 0.3681(3) 0.0865(18) Uani 1 1 d . . . . .
C6 C 0.3096(4) 0.8092(4) 0.6014(3) 0.0745(14) Uani 1 1 d . . . . .
H6A H 0.364610 0.827885 0.562059 0.112 Uiso 1 1 calc R U . . .
H6B H 0.344741 0.837226 0.647343 0.112 Uiso 1 1 calc R U . . .
H6C H 0.237915 0.863616 0.593426 0.112 Uiso 1 1 calc R U . . .
C7 C 0.1982(4) 0.6162(5) 0.6683(3) 0.0616(12) Uani 1 1 d . . . . .
H7A H 0.126460 0.671948 0.663822 0.092 Uiso 1 1 calc R U . . .
H7B H 0.237876 0.640861 0.713363 0.092 Uiso 1 1 calc R U . . .
H7C H 0.178790 0.515270 0.668480 0.092 Uiso 1 1 calc R U . . .
C1 C 0.1860(4) 0.5791(6) 0.4035(3) 0.0721(14) Uani 1 1 d . . . . .
C10 C 0.4189(4) 0.1609(4) 0.6081(4) 0.0830(16) Uani 1 1 d . . . . .
H10A H 0.360901 0.149332 0.646461 0.125 Uiso 1 1 calc R U . . .
H10B H 0.478942 0.087696 0.612733 0.125 Uiso 1 1 calc R U . . .
H10C H 0.380588 0.152155 0.561040 0.125 Uiso 1 1 calc R U . . .
C13 C 0.6479(5) 0.4062(8) 0.4402(3) 0.0924(18) Uani 1 1 d . . . . .
H13A H 0.709247 0.334353 0.448685 0.111 Uiso 1 1 calc R U . . .
H13B H 0.685291 0.500556 0.441150 0.111 Uiso 1 1 calc R U . . .
N3 N 0.0743(4) 0.5061(8) 0.4329(3) 0.119(2) Uani 1 1 d . . . . .
N2 N -0.0079(5) 0.5034(11) 0.3886(3) 0.134(3) Uani 1 1 d . . . . .
C15 C 0.5515(6) 0.3630(8) 0.3106(4) 0.100(2) Uani 1 1 d . . . . .
H15 H 0.516736 0.347473 0.264873 0.120 Uiso 1 1 calc R U . . .
C11 C 0.5338(5) 0.3292(6) 0.6906(3) 0.0791(15) Uani 1 1 d . . . . .
H11A H 0.584055 0.413047 0.689987 0.119 Uiso 1 1 calc R U . . .
H11B H 0.580675 0.245537 0.702267 0.119 Uiso 1 1 calc R U . . .
H11C H 0.472646 0.341241 0.726949 0.119 Uiso 1 1 calc R U . . .
C2 C 0.2417(8) 0.4735(11) 0.3526(4) 0.138(3) Uani 1 1 d . . . . .
H2A H 0.320524 0.505257 0.340063 0.207 Uiso 1 1 calc R U . . .
H2B H 0.194573 0.466082 0.308619 0.207 Uiso 1 1 calc R U . . .
H2C H 0.245970 0.380725 0.376031 0.207 Uiso 1 1 calc R U . . .
N1 N -0.0863(6) 0.4926(14) 0.3525(5) 0.197(5) Uani 1 1 d . . . . .
C3A C 0.1417(12) 0.7186(13) 0.3779(9) 0.128(5) Uani 0.7 1 d . . P A 2
H3AA H 0.089581 0.759133 0.414389 0.192 Uiso 0.7 1 calc R U P A 2
H3AB H 0.098682 0.705711 0.332697 0.192 Uiso 0.7 1 calc R U P A 2
H3AC H 0.207532 0.782789 0.369809 0.192 Uiso 0.7 1 calc R U P A 2
C3B C 0.233(3) 0.696(3) 0.3408(13) 0.118(10) Uani 0.3 1 d . . P A 1
H3BA H 0.237132 0.790573 0.362324 0.177 Uiso 0.3 1 calc R U P A 1
H3BB H 0.177874 0.697379 0.300287 0.177 Uiso 0.3 1 calc R U P A 1
H3BC H 0.310102 0.667882 0.323578 0.177 Uiso 0.3 1 calc R U P A 1
H5 H 0.321(4) 0.392(4) 0.587(2) 0.050(12) 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
O2 C8 1.214(4) . ?
N5 C8 1.336(5) . ?
N5 C9 1.466(4) . ?
N5 H5 0.79(4) . ?
N4 C4 1.326(6) . ?
N4 C5 1.467(5) . ?
N4 H4 0.8600 . ?
C12 O3 1.231(5) . ?
C12 N6 1.308(5) . ?
C12 C9 1.523(6) . ?
N6 C13 1.452(6) . ?
N6 H6 0.8600 . ?
C8 C5 1.545(5) . ?
O1 C4 1.228(5) . ?
C9 C10 1.523(5) . ?
C9 C11 1.537(6) . ?
C4 C1 1.533(6) . ?
C5 C6 1.521(6) . ?
C5 C7 1.527(6) . ?
C14 C15 1.167(9) . ?
C14 C13 1.453(9) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C1 C3A 1.461(12) . ?
C1 C2 1.485(10) . ?
C1 N3 1.521(7) . ?
C1 C3B 1.66(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N3 N2 1.225(7) . ?
N2 N1 1.102(7) . ?
C15 H15 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N5 C9 125.4(3) . . ?
C8 N5 H5 116(3) . . ?
C9 N5 H5 119(3) . . ?
C4 N4 C5 123.6(3) . . ?
C4 N4 H4 118.2 . . ?
C5 N4 H4 118.2 . . ?
O3 C12 N6 122.6(4) . . ?
O3 C12 C9 118.3(4) . . ?
N6 C12 C9 119.1(3) . . ?
C12 N6 C13 122.4(4) . . ?
C12 N6 H6 118.8 . . ?
C13 N6 H6 118.8 . . ?
O2 C8 N5 123.4(3) . . ?
O2 C8 C5 121.2(3) . . ?
N5 C8 C5 115.3(3) . . ?
N5 C9 C10 107.8(3) . . ?
N5 C9 C12 112.2(3) . . ?
C10 C9 C12 106.3(4) . . ?
N5 C9 C11 111.3(3) . . ?
C10 C9 C11 110.7(4) . . ?
C12 C9 C11 108.6(3) . . ?
O1 C4 N4 122.7(4) . . ?
O1 C4 C1 119.9(4) . . ?
N4 C4 C1 117.3(4) . . ?
N4 C5 C6 110.2(4) . . ?
N4 C5 C7 107.6(3) . . ?
C6 C5 C7 110.1(4) . . ?
N4 C5 C8 110.6(3) . . ?
C6 C5 C8 110.1(3) . . ?
C7 C5 C8 108.3(3) . . ?
C15 C14 C13 179.1(7) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3A C1 C2 121.9(9) . . ?
C3A C1 N3 102.9(7) . . ?
C2 C1 N3 105.9(6) . . ?
C3A C1 C4 108.9(6) . . ?
C2 C1 C4 109.7(5) . . ?
N3 C1 C4 106.4(4) . . ?
C2 C1 C3B 82.5(12) . . ?
N3 C1 C3B 142.4(13) . . ?
C4 C1 C3B 104.8(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C13 C14 112.1(4) . . ?
N6 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N6 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N2 N3 C1 113.5(6) . . ?
N1 N2 N3 174.0(11) . . ?
C14 C15 H15 180.0 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3A H3AA 109.5 . . ?
C1 C3A H3AB 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
C1 C3A H3AC 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C1 C3B H3BA 109.5 . . ?
C1 C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
C1 C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C12 N6 C13 -0.8(7) . . . . ?
C9 C12 N6 C13 -178.7(4) . . . . ?
C9 N5 C8 O2 4.1(6) . . . . ?
C9 N5 C8 C5 -173.1(4) . . . . ?
C8 N5 C9 C10 169.8(4) . . . . ?
C8 N5 C9 C12 -73.6(5) . . . . ?
C8 N5 C9 C11 48.3(5) . . . . ?
O3 C12 C9 N5 174.4(4) . . . . ?
N6 C12 C9 N5 -7.6(5) . . . . ?
O3 C12 C9 C10 -68.1(5) . . . . ?
N6 C12 C9 C10 109.9(4) . . . . ?
O3 C12 C9 C11 51.0(5) . . . . ?
N6 C12 C9 C11 -131.0(4) . . . . ?
C5 N4 C4 O1 7.9(6) . . . . ?
C5 N4 C4 C1 -171.1(4) . . . . ?
C4 N4 C5 C6 68.7(5) . . . . ?
C4 N4 C5 C7 -171.3(4) . . . . ?
C4 N4 C5 C8 -53.2(5) . . . . ?
O2 C8 C5 N4 136.7(4) . . . . ?
N5 C8 C5 N4 -46.1(4) . . . . ?
O2 C8 C5 C6 14.7(5) . . . . ?
N5 C8 C5 C6 -168.1(4) . . . . ?
O2 C8 C5 C7 -105.7(4) . . . . ?
N5 C8 C5 C7 71.6(4) . . . . ?
O1 C4 C1 C3A -90.9(9) . . . . ?
N4 C4 C1 C3A 88.1(8) . . . . ?
O1 C4 C1 C2 44.7(7) . . . . ?
N4 C4 C1 C2 -136.2(6) . . . . ?
O1 C4 C1 N3 158.8(5) . . . . ?
N4 C4 C1 N3 -22.2(6) . . . . ?
O1 C4 C1 C3B -42.5(13) . . . . ?
N4 C4 C1 C3B 136.6(12) . . . . ?
C12 N6 C13 C14 127.6(5) . . . . ?
C3A C1 N3 N2 53.1(10) . . . . ?
C2 C1 N3 N2 -75.8(8) . . . . ?
C4 C1 N3 N2 167.5(6) . . . . ?
C3B C1 N3 N2 22.6(19) . . . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.228
_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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2208398'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2022-09-20 deposited with the CCDC.	2023-04-14 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         'C15 H24 N6 O3, H2 O'
_chemical_formula_sum            'C15 H26 N6 O4'
_chemical_formula_weight         354.42

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      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                   17.887(3)
_cell_length_b                   8.7802(12)
_cell_length_c                   12.944(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.215(5)
_cell_angle_gamma                90
_cell_volume                     1930.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4868
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.82

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.218
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            34282
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.611
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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             3411
_reflns_number_gt                2370
_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       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+0.6916P] 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         3411
_refine_ls_number_parameters     268
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.030
_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 0.12827(14) 0.3670(3) 0.35795(18) 0.0506(6) Uani 1 1 d . . . . .
C2 C 0.04752(17) 0.3100(5) 0.2902(3) 0.0992(12) Uani 1 1 d . . . . .
H2A H 0.045631 0.201114 0.295995 0.149 Uiso 1 1 calc R U . . .
H2B H 0.038012 0.337922 0.215526 0.149 Uiso 1 1 calc R U . . .
H2C H 0.007945 0.354820 0.316467 0.149 Uiso 1 1 calc R U . . .
C3 C 0.1332(2) 0.5396(3) 0.3532(3) 0.0805(9) Uani 1 1 d . . . . .
H3A H 0.094533 0.584115 0.381462 0.121 Uiso 1 1 calc R U . . .
H3B H 0.123289 0.571178 0.279135 0.121 Uiso 1 1 calc R U . . .
H3C H 0.184713 0.572468 0.396041 0.121 Uiso 1 1 calc R U . . .
C4 C 0.19050(13) 0.3020(2) 0.31187(18) 0.0402(5) Uani 1 1 d . . . . .
C5 C 0.31329(13) 0.1598(2) 0.33918(17) 0.0393(5) Uani 1 1 d . . . . .
C6 C 0.38242(15) 0.1173(3) 0.43757(19) 0.0536(6) Uani 1 1 d . . . . .
H6A H 0.398906 0.204895 0.483400 0.080 Uiso 1 1 calc R U . . .
H6B H 0.425230 0.082073 0.413940 0.080 Uiso 1 1 calc R U . . .
H6C H 0.366843 0.037895 0.477586 0.080 Uiso 1 1 calc R U . . .
C7 C 0.28136(17) 0.0198(3) 0.2697(2) 0.0583(7) Uani 1 1 d . . . . .
H7A H 0.261336 -0.051323 0.310895 0.088 Uiso 1 1 calc R U . . .
H7B H 0.322863 -0.027182 0.248713 0.088 Uiso 1 1 calc R U . . .
H7C H 0.239781 0.049806 0.205864 0.088 Uiso 1 1 calc R U . . .
C8 C 0.34178(12) 0.2782(2) 0.27106(16) 0.0359(5) Uani 1 1 d . . . . .
C9 C 0.39392(13) 0.5422(2) 0.27423(17) 0.0410(5) Uani 1 1 d . . . . .
C10 C 0.46982(15) 0.4923(3) 0.2531(2) 0.0601(7) Uani 1 1 d . . . . .
H10A H 0.504287 0.445310 0.317338 0.090 Uiso 1 1 calc R U . . .
H10B H 0.495309 0.579621 0.234535 0.090 Uiso 1 1 calc R U . . .
H10C H 0.457475 0.420697 0.194092 0.090 Uiso 1 1 calc R U . . .
C11 C 0.41249(18) 0.6666(3) 0.3616(2) 0.0658(8) Uani 1 1 d . . . . .
H11A H 0.364966 0.696015 0.375922 0.099 Uiso 1 1 calc R U . . .
H11B H 0.434530 0.753392 0.336572 0.099 Uiso 1 1 calc R U . . .
H11C H 0.449600 0.628293 0.427203 0.099 Uiso 1 1 calc R U . . .
C12 C 0.33825(15) 0.6115(3) 0.17060(19) 0.0488(6) Uani 1 1 d . . . . .
C13 C 0.2088(4) 0.6259(11) 0.0365(6) 0.0829(19) Uani 0.774(7) 1 d . . P A 1
H13A H 0.225607 0.726046 0.021055 0.099 Uiso 0.774(7) 1 calc R U P A 1
H13B H 0.210410 0.558292 -0.022003 0.099 Uiso 0.774(7) 1 calc R U P A 1
C14 C 0.1301(4) 0.6351(8) 0.0395(5) 0.099(3) Uani 0.774(7) 1 d . . P A 1
C15 C 0.0645(5) 0.6301(10) 0.0308(5) 0.174(4) Uani 0.774(7) 1 d . . P A 1
H15 H 0.011199 0.625924 0.023784 0.209 Uiso 0.774(7) 1 calc R U P A 1
C13' C 0.2024(12) 0.6892(16) 0.0786(15) 0.064(5) Uani 0.226(7) 1 d D . P A 2
H13C H 0.169735 0.721003 0.122019 0.077 Uiso 0.226(7) 1 calc R U P A 2
H13D H 0.227795 0.777904 0.059894 0.077 Uiso 0.226(7) 1 calc R U P A 2
C14' C 0.1605(19) 0.6157(19) -0.0097(17) 0.098(9) Uani 0.226(7) 1 d D . P A 2
C15' C 0.1300(13) 0.568(2) -0.1010(18) 0.143(10) Uani 0.226(7) 1 d D . P A 2
H15' H 0.106543 0.531448 -0.171107 0.172 Uiso 0.226(7) 1 calc R U P A 2
N1 N 0.0770(2) 0.4181(4) 0.5786(2) 0.1233(14) Uani 1 1 d . . . . .
N2 N 0.10890(14) 0.3707(3) 0.52338(18) 0.0735(7) Uani 1 1 d . . . . .
N3 N 0.14745(13) 0.3122(3) 0.47227(17) 0.0672(7) Uani 1 1 d . . . . .
N4 N 0.25164(10) 0.22694(19) 0.37803(14) 0.0397(4) Uani 1 1 d . . . . .
H4 H 0.255136 0.217510 0.445515 0.048 Uiso 1 1 calc R U . . .
N5 N 0.35772(10) 0.41649(17) 0.31644(13) 0.0351(4) Uani 1 1 d . . . . .
H5 H 0.345808 0.432924 0.374904 0.042 Uiso 1 1 calc R U . . .
N6 N 0.26331(13) 0.5701(3) 0.13903(18) 0.0707(7) Uani 1 1 d D . . . .
H6 H 0.246495 0.509719 0.179200 0.085 Uiso 1 1 calc R U . A 1
O1 O 0.18322(9) 0.32425(18) 0.21543(12) 0.0500(4) Uani 1 1 d . . . . .
O2 O 0.35155(10) 0.24451(16) 0.18430(12) 0.0489(4) Uani 1 1 d . . . . .
O3 O 0.36326(12) 0.7083(2) 0.12107(15) 0.0714(6) Uani 1 1 d . . . . .
O1' O 0.33928(13) 1.0063(2) 0.02958(13) 0.0648(5) Uani 1 1 d D . . . .
H1A H 0.3467(17) 0.915(2) 0.059(2) 0.090(10) Uiso 1 1 d D . . . .
H1B H 0.3419(19) 1.069(3) 0.085(2) 0.102(11) Uiso 1 1 d 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 N3 1.491(3) . ?
C1 C3 1.520(4) . ?
C1 C2 1.521(4) . ?
C1 C4 1.528(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O1 1.230(2) . ?
C4 N4 1.334(3) . ?
C5 N4 1.471(3) . ?
C5 C6 1.518(3) . ?
C5 C7 1.524(3) . ?
C5 C8 1.549(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O2 1.226(2) . ?
C8 N5 1.340(3) . ?
C9 N5 1.469(3) . ?
C9 C12 1.525(3) . ?
C9 C10 1.530(3) . ?
C9 C11 1.533(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.230(3) . ?
C12 N6 1.324(3) . ?
C13 C14 1.421(9) . ?
C13 N6 1.465(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.144(8) . ?
C15 H15 0.9300 . ?
C13' C14' 1.322(18) . ?
C13' N6 1.536(14) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' C15' 1.211(16) . ?
C15' H15' 0.9300 . ?
N1 N2 1.124(3) . ?
N2 N3 1.209(3) . ?
N4 H4 0.8600 . ?
N5 H5 0.8600 . ?
N6 H6 0.8600 . ?
O1' H1A 0.880(17) . ?
O1' H1B 0.893(17) . ?

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
N3 C1 C3 111.3(2) . . ?
N3 C1 C2 110.4(2) . . ?
C3 C1 C2 111.2(3) . . ?
N3 C1 C4 107.28(19) . . ?
C3 C1 C4 107.4(2) . . ?
C2 C1 C4 109.2(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N4 122.4(2) . . ?
O1 C4 C1 118.5(2) . . ?
N4 C4 C1 119.03(19) . . ?
N4 C5 C6 108.23(17) . . ?
N4 C5 C7 110.00(18) . . ?
C6 C5 C7 110.68(19) . . ?
N4 C5 C8 109.92(16) . . ?
C6 C5 C8 108.42(18) . . ?
C7 C5 C8 109.56(17) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N5 123.28(19) . . ?
O2 C8 C5 121.74(18) . . ?
N5 C8 C5 114.93(17) . . ?
N5 C9 C12 112.62(18) . . ?
N5 C9 C10 111.74(17) . . ?
C12 C9 C10 109.19(19) . . ?
N5 C9 C11 106.26(16) . . ?
C12 C9 C11 107.22(19) . . ?
C10 C9 C11 109.7(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N6 121.8(2) . . ?
O3 C12 C9 119.4(2) . . ?
N6 C12 C9 118.8(2) . . ?
C14 C13 N6 112.3(4) . . ?
C14 C13 H13A 109.2 . . ?
N6 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
N6 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 171.2(11) . . ?
C14 C15 H15 180.0 . . ?
C14' C13' N6 103.2(16) . . ?
C14' C13' H13C 111.1 . . ?
N6 C13' H13C 111.1 . . ?
C14' C13' H13D 111.1 . . ?
N6 C13' H13D 111.1 . . ?
H13C C13' H13D 109.1 . . ?
C15' C14' C13' 167(3) . . ?
C14' C15' H15' 180.0 . . ?
N1 N2 N3 173.9(3) . . ?
N2 N3 C1 114.3(2) . . ?
C4 N4 C5 122.05(17) . . ?
C4 N4 H4 119.0 . . ?
C5 N4 H4 119.0 . . ?
C8 N5 C9 125.16(16) . . ?
C8 N5 H5 117.4 . . ?
C9 N5 H5 117.4 . . ?
C12 N6 C13 120.7(4) . . ?
C12 N6 C13' 117.3(8) . . ?
C12 N6 H6 119.6 . . ?
C13 N6 H6 119.6 . . ?
H1A O1' H1B 104(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
N3 C1 C4 O1 175.1(2) . . . . ?
C3 C1 C4 O1 -65.1(3) . . . . ?
C2 C1 C4 O1 55.5(3) . . . . ?
N3 C1 C4 N4 -6.6(3) . . . . ?
C3 C1 C4 N4 113.1(2) . . . . ?
C2 C1 C4 N4 -126.2(2) . . . . ?
N4 C5 C8 O2 -135.2(2) . . . . ?
C6 C5 C8 O2 106.6(2) . . . . ?
C7 C5 C8 O2 -14.3(3) . . . . ?
N4 C5 C8 N5 47.4(2) . . . . ?
C6 C5 C8 N5 -70.7(2) . . . . ?
C7 C5 C8 N5 168.38(19) . . . . ?
N5 C9 C12 O3 -173.3(2) . . . . ?
C10 C9 C12 O3 -48.6(3) . . . . ?
C11 C9 C12 O3 70.1(3) . . . . ?
N5 C9 C12 N6 9.4(3) . . . . ?
C10 C9 C12 N6 134.2(2) . . . . ?
C11 C9 C12 N6 -107.1(3) . . . . ?
N6 C13' C14' C15' -108(13) . . . . ?
C3 C1 N3 N2 53.8(3) . . . . ?
C2 C1 N3 N2 -70.2(3) . . . . ?
C4 C1 N3 N2 171.0(2) . . . . ?
O1 C4 N4 C5 -2.5(3) . . . . ?
C1 C4 N4 C5 179.30(18) . . . . ?
C6 C5 N4 C4 166.71(19) . . . . ?
C7 C5 N4 C4 -72.3(2) . . . . ?
C8 C5 N4 C4 48.5(2) . . . . ?
O2 C8 N5 C9 -4.7(3) . . . . ?
C5 C8 N5 C9 172.64(18) . . . . ?
C12 C9 N5 C8 71.8(3) . . . . ?
C10 C9 N5 C8 -51.6(3) . . . . ?
C11 C9 N5 C8 -171.1(2) . . . . ?
O3 C12 N6 C13 6.8(6) . . . . ?
C9 C12 N6 C13 -176.0(4) . . . . ?
O3 C12 N6 C13' -28.8(10) . . . . ?
C9 C12 N6 C13' 148.4(10) . . . . ?
C14 C13 N6 C12 -151.2(7) . . . . ?
C14' C13' N6 C12 129(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
C7 H7C O1 0.96 2.63 3.154(3) 114.6 . yes
C10 H10C O2 0.96 2.42 2.970(3) 116.3 . yes
N5 H5 O1' 0.86 2.11 2.958(2) 168.4 4_576 yes
N6 H6^a O1 0.86 2.12 2.928(3) 156.9 . yes
O1' H1A O3 0.880(17) 1.969(17) 2.848(2) 178(3) . yes
O1' H1B O2 0.893(17) 1.980(17) 2.857(2) 167(3) 1_565 yes
C7 H7C O1 0.96 2.63 3.154(3) 114.6 . yes
C10 H10C O2 0.96 2.42 2.970(3) 116.3 . yes
N5 H5 O1' 0.86 2.11 2.958(2) 168.4 4_576 yes
N6 H6^a O1 0.86 2.12 2.928(3) 156.9 . yes
O1' H1A O3 0.880(17) 1.969(17) 2.848(2) 178(3) . yes
O1' H1B O2 0.893(17) 1.980(17) 2.857(2) 167(3) 1_565 yes

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_NEWORTHO1
_database_code_depnum_ccdc_archive 'CCDC 2208397'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2022-09-20 deposited with the CCDC.	2023-04-14 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         ?
_chemical_formula_sum            'C15 H24 N6 O3'
_chemical_formula_weight         336.40

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.885(5)
_cell_length_b                   18.470(5)
_cell_length_c                   10.697(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3533.7(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5669
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      24.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SADABS (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39620
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_av_R_equivalents  0.1690
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3109
_reflns_number_gt                1007
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3109
_refine_ls_number_parameters     653
_refine_ls_number_restraints     2247
_refine_ls_R_factor_all          0.2678
_refine_ls_R_factor_gt           0.1183
_refine_ls_wR_factor_ref         0.4135
_refine_ls_wR_factor_gt          0.3016
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      0.903
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4423(7) 0.4208(11) 0.8043(15) 0.082(4) Uani 0.439(10) 1 d D U P A 1
C2 C 0.4762(15) 0.4974(14) 0.803(3) 0.110(8) Uani 0.439(10) 1 d D U P A 1
H2A H 0.483629 0.513697 0.887227 0.165 Uiso 0.439(10) 1 calc R U P A 1
H2B H 0.523394 0.496400 0.760087 0.165 Uiso 0.439(10) 1 calc R U P A 1
H2C H 0.442838 0.529857 0.760550 0.165 Uiso 0.439(10) 1 calc R U P A 1
C3 C 0.5051(11) 0.3718(15) 0.861(2) 0.097(6) Uani 0.439(10) 1 d D U P A 1
H3A H 0.518766 0.389673 0.942044 0.145 Uiso 0.439(10) 1 calc R U P A 1
H3B H 0.487104 0.323025 0.868342 0.145 Uiso 0.439(10) 1 calc R U P A 1
H3C H 0.548077 0.372625 0.807105 0.145 Uiso 0.439(10) 1 calc R U P A 1
C4 C 0.3727(11) 0.4154(17) 0.8833(18) 0.079(5) Uani 0.439(10) 1 d D U P A 1
C5 C 0.2458(17) 0.4660(17) 0.913(3) 0.069(5) Uani 0.439(10) 1 d D U P A 1
C6 C 0.2538(17) 0.5422(16) 0.967(3) 0.089(7) Uani 0.439(10) 1 d D U P A 1
H6A H 0.210511 0.553504 1.016831 0.134 Uiso 0.439(10) 1 calc R U P A 1
H6B H 0.297647 0.544381 1.019054 0.134 Uiso 0.439(10) 1 calc R U P A 1
H6C H 0.258242 0.576639 0.900588 0.134 Uiso 0.439(10) 1 calc R U P A 1
C7 C 0.1775(17) 0.4791(17) 0.832(4) 0.075(7) Uani 0.439(10) 1 d D U P A 1
H7A H 0.138091 0.498982 0.882476 0.113 Uiso 0.439(10) 1 calc R U P A 1
H7B H 0.189918 0.512436 0.766593 0.113 Uiso 0.439(10) 1 calc R U P A 1
H7C H 0.161318 0.434083 0.796384 0.113 Uiso 0.439(10) 1 calc R U P A 1
C8 C 0.230(3) 0.413(2) 1.020(3) 0.072(5) Uani 0.439(10) 1 d D U P A 1
C9 C 0.1807(9) 0.2882(9) 1.0645(13) 0.083(4) Uani 0.439(10) 1 d D U P A 1
C10 C 0.1559(11) 0.2284(8) 0.9748(17) 0.102(5) Uani 0.439(10) 1 d D U P A 1
H10A H 0.120848 0.247777 0.915616 0.153 Uiso 0.439(10) 1 calc R U P A 1
H10B H 0.198625 0.209690 0.931174 0.153 Uiso 0.439(10) 1 calc R U P A 1
H10C H 0.132547 0.190091 1.021319 0.153 Uiso 0.439(10) 1 calc R U P A 1
C11 C 0.1158(10) 0.3195(11) 1.1414(18) 0.090(6) Uani 0.439(10) 1 d D U P A 1
H11A H 0.079689 0.340788 1.086101 0.135 Uiso 0.439(10) 1 calc R U P A 1
H11B H 0.092615 0.281419 1.188580 0.135 Uiso 0.439(10) 1 calc R U P A 1
H11C H 0.134545 0.355777 1.197434 0.135 Uiso 0.439(10) 1 calc R U P A 1
C12 C 0.2348(8) 0.2560(11) 1.1545(18) 0.095(5) Uani 0.439(10) 1 d D U P A 1
C13 C 0.3659(8) 0.2380(8) 1.2158(15) 0.103(5) Uani 0.439(10) 1 d D U P A 1
H13A H 0.344090 0.217547 1.290855 0.124 Uiso 0.439(10) 1 calc R U P A 1
H13B H 0.406690 0.269519 1.240646 0.124 Uiso 0.439(10) 1 calc R U P A 1
C14 C 0.3965(8) 0.3233(8) 0.6332(16) 0.114(5) Uani 0.439(10) 1 d D U P A 1
C15 C 0.4023(9) 0.3280(11) 0.5016(17) 0.143(7) Uani 0.439(10) 1 d D U P A 1
H15 H 0.386506 0.292722 0.445439 0.171 Uiso 0.439(10) 1 calc R U P A 1
N1 N 0.4345(9) 0.3924(10) 0.4699(15) 0.146(6) Uani 0.439(10) 1 d D U P A 1
N2 N 0.4501(7) 0.4292(7) 0.5780(15) 0.112(5) Uani 0.439(10) 1 d D U P A 1
N3 N 0.4271(5) 0.3869(7) 0.6802(12) 0.083(4) Uani 0.439(10) 1 d D U P A 1
N4 N 0.3043(14) 0.4360(19) 0.834(3) 0.068(4) Uani 0.439(10) 1 d D U P A 1
H4 H 0.296189 0.430806 0.755489 0.082 Uiso 0.439(10) 1 calc R U P A 1
N5 N 0.2156(11) 0.3483(15) 0.9854(19) 0.075(4) Uani 0.439(10) 1 d D U P A 1
H5 H 0.226991 0.337236 0.909643 0.090 Uiso 0.439(10) 1 calc R U P A 1
N6 N 0.3089(8) 0.2808(9) 1.1489(15) 0.097(5) Uani 0.439(10) 1 d D U P A 1
H6 H 0.320540 0.319306 1.108135 0.116 Uiso 0.439(10) 1 calc R U P A 1
O1 O 0.3797(11) 0.3964(9) 0.9916(18) 0.098(6) Uani 0.439(10) 1 d D U P A 1
O2 O 0.225(2) 0.435(2) 1.127(3) 0.077(7) Uani 0.439(10) 1 d D U P A 1
O3 O 0.2157(8) 0.2050(6) 1.2215(14) 0.115(5) Uani 0.439(10) 1 d D U P A 1
C1A C 0.451(3) 0.405(2) 0.801(5) 0.091(6) Uani 0.072(4) 1 d D U P B 2
C2A C 0.455(5) 0.473(3) 0.717(8) 0.097(12) Uani 0.072(4) 1 d D U P B 2
H2A1 H 0.441529 0.514907 0.764787 0.145 Uiso 0.072(4) 1 calc R U P B 2
H2A2 H 0.504848 0.478515 0.685283 0.145 Uiso 0.072(4) 1 calc R U P B 2
H2A3 H 0.420795 0.467365 0.648441 0.145 Uiso 0.072(4) 1 calc R U P B 2
C3A C 0.515(4) 0.416(4) 0.898(6) 0.094(12) Uani 0.072(4) 1 d D U P B 2
H3A1 H 0.507207 0.460971 0.942014 0.142 Uiso 0.072(4) 1 calc R U P B 2
H3A2 H 0.514868 0.376836 0.956481 0.142 Uiso 0.072(4) 1 calc R U P B 2
H3A3 H 0.562238 0.417871 0.855566 0.142 Uiso 0.072(4) 1 calc R U P B 2
C4A C 0.377(3) 0.399(4) 0.867(6) 0.082(6) Uani 0.072(4) 1 d D U P B 2
C5A C 0.248(3) 0.448(3) 0.897(5) 0.077(6) Uani 0.072(4) 1 d D U P B 2
C6A C 0.221(5) 0.526(3) 0.916(8) 0.084(12) Uani 0.072(4) 1 d D U P B 2
H6A1 H 0.177594 0.525953 0.968435 0.126 Uiso 0.072(4) 1 calc R U P B 2
H6A2 H 0.260270 0.553149 0.955599 0.126 Uiso 0.072(4) 1 calc R U P B 2
H6A3 H 0.209435 0.546785 0.836720 0.126 Uiso 0.072(4) 1 calc R U P B 2
C7A C 0.179(4) 0.422(5) 0.827(8) 0.079(13) Uani 0.072(4) 1 d D U P B 2
H7A1 H 0.134731 0.431506 0.875782 0.119 Uiso 0.072(4) 1 calc R U P B 2
H7A2 H 0.175147 0.446612 0.748386 0.119 Uiso 0.072(4) 1 calc R U P B 2
H7A3 H 0.182390 0.370529 0.812201 0.119 Uiso 0.072(4) 1 calc R U P B 2
C8A C 0.255(6) 0.412(3) 1.024(5) 0.078(6) Uani 0.072(4) 1 d D U P B 2
C9A C 0.229(4) 0.287(3) 1.106(5) 0.087(7) Uani 0.072(4) 1 d D U P B 2
C10A C 0.250(6) 0.212(3) 1.055(8) 0.093(11) Uani 0.072(4) 1 d D U P B 2
H10D H 0.234710 0.208998 0.968830 0.139 Uiso 0.072(4) 1 calc R U P B 2
H10E H 0.303065 0.206124 1.060433 0.139 Uiso 0.072(4) 1 calc R U P B 2
H10F H 0.225285 0.175540 1.102587 0.139 Uiso 0.072(4) 1 calc R U P B 2
C11A C 0.145(3) 0.302(6) 1.113(9) 0.092(12) Uani 0.072(4) 1 d D U P B 2
H11D H 0.124210 0.302947 1.029568 0.138 Uiso 0.072(4) 1 calc R U P B 2
H11E H 0.120500 0.264915 1.160434 0.138 Uiso 0.072(4) 1 calc R U P B 2
H11F H 0.136331 0.348247 1.151831 0.138 Uiso 0.072(4) 1 calc R U P B 2
C12A C 0.255(3) 0.287(4) 1.241(5) 0.093(7) Uani 0.072(4) 1 d D U P B 2
C13A C 0.384(3) 0.272(3) 1.319(6) 0.096(10) Uani 0.072(4) 1 d D U P B 2
H13C H 0.358485 0.233027 1.360747 0.115 Uiso 0.072(4) 1 calc R U P B 2
H13D H 0.408070 0.300867 1.383397 0.115 Uiso 0.072(4) 1 calc R U P B 2
C14A C 0.448(2) 0.263(2) 0.742(4) 0.106(8) Uani 0.072(4) 1 d D U P B 2
C15A C 0.494(3) 0.225(2) 0.657(5) 0.112(10) Uani 0.072(4) 1 d D U P B 2
H15A H 0.491972 0.176179 0.637654 0.134 Uiso 0.072(4) 1 calc R U P B 2
N1A N 0.544(3) 0.274(3) 0.607(4) 0.114(11) Uani 0.072(4) 1 d D U P B 2
N2A N 0.530(2) 0.341(2) 0.657(4) 0.105(7) Uani 0.072(4) 1 d D U P B 2
N3A N 0.4706(19) 0.335(2) 0.741(3) 0.103(6) Uani 0.072(4) 1 d D U P B 2
N4A N 0.313(4) 0.432(7) 0.822(7) 0.078(6) Uani 0.072(4) 1 d D U P B 2
H4A H 0.312036 0.444364 0.743998 0.093 Uiso 0.072(4) 1 calc R U P B 2
N5A N 0.267(4) 0.344(3) 1.025(6) 0.081(6) Uani 0.072(4) 1 d D U P B 2
H5A H 0.299603 0.327783 0.973085 0.097 Uiso 0.072(4) 1 calc R U P B 2
N6A N 0.325(3) 0.319(3) 1.264(7) 0.094(8) Uani 0.072(4) 1 d D U P B 2
H6A4 H 0.333655 0.363588 1.246810 0.113 Uiso 0.072(4) 1 calc R U P B 2
O1A O 0.378(4) 0.369(5) 0.968(7) 0.088(11) Uani 0.072(4) 1 d D U P B 2
O2A O 0.261(4) 0.449(4) 1.118(6) 0.077(12) Uani 0.072(4) 1 d D U P B 2
O3A O 0.239(4) 0.231(4) 1.298(6) 0.091(12) Uani 0.072(4) 1 d D U P B 2
C1B C 0.4340(14) 0.4205(16) 0.766(3) 0.173(9) Uani 0.489(11) 1 d D U P C 3
C2B C 0.464(2) 0.4986(16) 0.755(3) 0.168(13) Uani 0.489(11) 1 d D U P C 3
H2B1 H 0.471682 0.518261 0.836583 0.252 Uiso 0.489(11) 1 calc R U P C 3
H2B2 H 0.510000 0.498460 0.709290 0.252 Uiso 0.489(11) 1 calc R U P C 3
H2B3 H 0.427762 0.527817 0.710836 0.252 Uiso 0.489(11) 1 calc R U P C 3
C3B C 0.495(2) 0.371(2) 0.816(4) 0.219(14) Uani 0.489(11) 1 d D U P C 3
H3B1 H 0.506272 0.383693 0.901138 0.328 Uiso 0.489(11) 1 calc R U P C 3
H3B2 H 0.479061 0.321643 0.812097 0.328 Uiso 0.489(11) 1 calc R U P C 3
H3B3 H 0.539741 0.376826 0.766214 0.328 Uiso 0.489(11) 1 calc R U P C 3
C4B C 0.381(2) 0.429(2) 0.876(3) 0.148(9) Uani 0.489(11) 1 d D U P C 3
C5B C 0.249(2) 0.4678(17) 0.915(5) 0.100(7) Uani 0.489(11) 1 d D U P C 3
C6B C 0.2771(16) 0.5443(13) 0.946(3) 0.114(10) Uani 0.489(11) 1 d D U P C 3
H6B1 H 0.321856 0.541232 0.995540 0.172 Uiso 0.489(11) 1 calc R U P C 3
H6B2 H 0.287419 0.569993 0.870259 0.172 Uiso 0.489(11) 1 calc R U P C 3
H6B3 H 0.239294 0.569691 0.992742 0.172 Uiso 0.489(11) 1 calc R U P C 3
C7B C 0.179(2) 0.4566(16) 0.838(4) 0.103(11) Uani 0.489(11) 1 d D U P C 3
H7B1 H 0.183298 0.483331 0.761650 0.154 Uiso 0.489(11) 1 calc R U P C 3
H7B2 H 0.173518 0.406053 0.820008 0.154 Uiso 0.489(11) 1 calc R U P C 3
H7B3 H 0.136658 0.473383 0.884536 0.154 Uiso 0.489(11) 1 calc R U P C 3
C8B C 0.233(3) 0.422(3) 1.031(4) 0.109(8) Uani 0.489(11) 1 d D U P C 3
C9B C 0.2253(14) 0.2948(12) 1.114(2) 0.132(7) Uani 0.489(11) 1 d D U P C 3
C10B C 0.2123(15) 0.2220(10) 1.047(2) 0.146(9) Uani 0.489(11) 1 d D U P C 3
H10G H 0.202521 0.185139 1.108302 0.219 Uiso 0.489(11) 1 calc R U P C 3
H10H H 0.170207 0.226213 0.991993 0.219 Uiso 0.489(11) 1 calc R U P C 3
H10I H 0.255981 0.209353 0.999953 0.219 Uiso 0.489(11) 1 calc R U P C 3
C11B C 0.1561(15) 0.3106(15) 1.190(2) 0.147(9) Uani 0.489(11) 1 d D U P C 3
H11G H 0.150116 0.274044 1.252570 0.220 Uiso 0.489(11) 1 calc R U P C 3
H11H H 0.161067 0.357123 1.228807 0.220 Uiso 0.489(11) 1 calc R U P C 3
H11I H 0.113216 0.310750 1.135721 0.220 Uiso 0.489(11) 1 calc R U P C 3
C12B C 0.2896(13) 0.2888(13) 1.204(2) 0.131(7) Uani 0.489(11) 1 d D U P C 3
C13B C 0.4102(12) 0.3299(12) 1.3005(17) 0.167(8) Uani 0.489(11) 1 d D U P C 3
H13E H 0.451559 0.356443 1.263882 0.200 Uiso 0.489(11) 1 calc R U P C 3
H13F H 0.424765 0.279269 1.300343 0.200 Uiso 0.489(11) 1 calc R U P C 3
C14B C 0.4266(18) 0.4131(12) 0.504(2) 0.253(11) Uani 0.489(11) 1 d D U P C 3
H14B H 0.439945 0.457793 0.471155 0.304 Uiso 0.489(11) 1 calc R U P C 3
C15B C 0.4064(13) 0.3528(13) 0.4371(19) 0.240(11) Uani 0.489(11) 1 d D U P C 3
N1B N 0.3911(11) 0.2964(11) 0.525(2) 0.266(10) Uani 0.489(11) 1 d D U P C 3
N2B N 0.4022(14) 0.3243(15) 0.643(2) 0.238(9) Uani 0.489(11) 1 d D U P C 3
N3B N 0.4234(11) 0.3949(14) 0.635(2) 0.195(8) Uani 0.489(11) 1 d D U P C 3
N4B N 0.317(2) 0.444(2) 0.833(4) 0.121(8) Uani 0.489(11) 1 d . U P C 3
H4B H 0.310567 0.440075 0.753896 0.145 Uiso 0.489(11) 1 calc R U P C 3
N5B N 0.2390(12) 0.3449(17) 1.020(2) 0.107(7) Uani 0.489(11) 1 d . U P C 3
H5B H 0.252043 0.328179 0.947872 0.128 Uiso 0.489(11) 1 calc R U P C 3
N6B N 0.3469(11) 0.3363(9) 1.211(2) 0.170(7) Uani 0.489(11) 1 d D U P C 3
H6B4 H 0.346813 0.372495 1.160552 0.204 Uiso 0.489(11) 1 calc R U P C 3
O1B O 0.3878(11) 0.4341(10) 0.989(3) 0.134(7) Uani 0.489(11) 1 d D U P C 3
O2B O 0.209(2) 0.450(2) 1.128(4) 0.102(10) Uani 0.489(11) 1 d D U P C 3
O3B O 0.2907(12) 0.2461(10) 1.2912(18) 0.179(7) Uani 0.489(11) 1 d D U P C 3


_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 N3 1.492(14) . ?
C1 C4 1.507(14) . ?
C1 C2 1.540(16) . ?
C1 C3 1.565(15) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O1 1.217(14) . ?
C4 N4 1.39(4) . ?
C5 N4 1.45(5) . ?
C5 C7 1.515(15) . ?
C5 C8 1.529(14) . ?
C5 C6 1.530(16) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O2 1.224(15) . ?
C8 N5 1.28(4) . ?
C9 C12 1.489(15) . ?
C9 N5 1.53(3) . ?
C9 C10 1.530(15) . ?
C9 C11 1.535(14) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.233(14) . ?
C12 N6 1.402(14) . ?
C13 N6 1.476(14) . ?
C13 C14 1.537(16) 8_566 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N3 1.390(14) . ?
C14 C15 1.414(15) . ?
C15 N1 1.366(15) . ?
C15 H15 0.9300 . ?
N1 N2 1.369(14) . ?
N2 N3 1.406(14) . ?
N4 H4 0.8600 . ?
N5 H5 0.8600 . ?
N6 H6 0.8600 . ?
C1A N3A 1.485(16) . ?
C1A C4A 1.513(17) . ?
C1A C2A 1.541(17) . ?
C1A C3A 1.553(17) . ?
C2A H2A1 0.9600 . ?
C2A H2A2 0.9600 . ?
C2A H2A3 0.9600 . ?
C3A H3A1 0.9600 . ?
C3A H3A2 0.9600 . ?
C3A H3A3 0.9600 . ?
C4A O1A 1.223(18) . ?
C4A N4A 1.38(4) . ?
C5A N4A 1.45(5) . ?
C5A C8A 1.517(17) . ?
C5A C7A 1.523(17) . ?
C5A C6A 1.529(17) . ?
C6A H6A1 0.9600 . ?
C6A H6A2 0.9600 . ?
C6A H6A3 0.9600 . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
C8A O2A 1.226(19) . ?
C8A N5A 1.28(5) . ?
C9A C12A 1.513(18) . ?
C9A N5A 1.52(4) . ?
C9A C11A 1.530(17) . ?
C9A C10A 1.530(17) . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12A O3A 1.230(18) . ?
C12A N6A 1.414(17) . ?
C13A N6A 1.479(17) . ?
C13A C14A 1.544(16) 8_566 ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C14A N3A 1.402(16) . ?
C14A C15A 1.416(16) . ?
C15A N1A 1.378(17) . ?
C15A H15A 0.9300 . ?
N1A N2A 1.369(17) . ?
N2A N3A 1.398(16) . ?
N4A H4A 0.8600 . ?
N5A H5A 0.8600 . ?
N6A H6A4 0.8600 . ?
C1B N3B 1.489(19) . ?
C1B C4B 1.516(16) . ?
C1B C3B 1.53(2) . ?
C1B C2B 1.543(19) . ?
C2B H2B1 0.9600 . ?
C2B H2B2 0.9600 . ?
C2B H2B3 0.9600 . ?
C3B H3B1 0.9600 . ?
C3B H3B2 0.9600 . ?
C3B H3B3 0.9600 . ?
C4B O1B 1.221(15) . ?
C4B N4B 1.26(5) . ?
C5B C7B 1.513(18) . ?
C5B C8B 1.526(16) . ?
C5B C6B 1.535(18) . ?
C5B N4B 1.56(6) . ?
C6B H6B1 0.9600 . ?
C6B H6B2 0.9600 . ?
C6B H6B3 0.9600 . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
C8B O2B 1.228(17) . ?
C8B N5B 1.44(6) . ?
C9B N5B 1.39(3) . ?
C9B C12B 1.508(17) . ?
C9B C11B 1.509(19) . ?
C9B C10B 1.538(18) . ?
C10B H10G 0.9600 . ?
C10B H10H 0.9600 . ?
C10B H10I 0.9600 . ?
C11B H11G 0.9600 . ?
C11B H11H 0.9600 . ?
C11B H11I 0.9600 . ?
C12B O3B 1.218(16) . ?
C12B N6B 1.351(17) . ?
C13B N6B 1.486(16) . ?
C13B C15B 1.523(15) 1_556 ?
C13B H13E 0.9700 . ?
C13B H13F 0.9700 . ?
C14B C15B 1.375(17) . ?
C14B N3B 1.439(17) . ?
C14B H14B 0.9300 . ?
C15B N1B 1.426(17) . ?
N1B N2B 1.379(17) . ?
N2B N3B 1.361(17) . ?
N4B H4B 0.8600 . ?
N5B H5B 0.8600 . ?
N6B H6B4 0.8600 . ?

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
N3 C1 C4 108.7(14) . . ?
N3 C1 C2 116.6(15) . . ?
C4 C1 C2 113.0(18) . . ?
N3 C1 C3 103.5(13) . . ?
C4 C1 C3 109.8(16) . . ?
C2 C1 C3 104.6(18) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N4 122.0(18) . . ?
O1 C4 C1 117.9(19) . . ?
N4 C4 C1 120.0(18) . . ?
N4 C5 C7 108(3) . . ?
N4 C5 C8 109(3) . . ?
C7 C5 C8 112(3) . . ?
N4 C5 C6 120(2) . . ?
C7 C5 C6 98(3) . . ?
C8 C5 C6 109(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N5 125(3) . . ?
O2 C8 C5 120(4) . . ?
N5 C8 C5 115(2) . . ?
C12 C9 N5 112.5(14) . . ?
C12 C9 C10 107.8(15) . . ?
N5 C9 C10 107.2(13) . . ?
C12 C9 C11 107.2(13) . . ?
N5 C9 C11 109.4(15) . . ?
C10 C9 C11 112.8(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N6 122.4(15) . . ?
O3 C12 C9 120.1(14) . . ?
N6 C12 C9 117.1(14) . . ?
N6 C13 C14 111.2(13) . 8_566 ?
N6 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 8_566 . ?
N6 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 8_566 . ?
H13A C13 H13B 108.0 . . ?
N3 C14 C15 106.3(9) . . ?
N3 C14 C13 123.7(14) . 8_565 ?
C15 C14 C13 130.0(15) . 8_565 ?
N1 C15 C14 109.3(11) . . ?
N1 C15 H15 125.3 . . ?
C14 C15 H15 125.3 . . ?
C15 N1 N2 108.0(11) . . ?
N1 N2 N3 108.8(10) . . ?
C14 N3 N2 107.6(10) . . ?
C14 N3 C1 138.4(13) . . ?
N2 N3 C1 114.0(12) . . ?
C4 N4 C5 121(3) . . ?
C4 N4 H4 119.3 . . ?
C5 N4 H4 119.3 . . ?
C8 N5 C9 127(2) . . ?
C8 N5 H5 116.5 . . ?
C9 N5 H5 116.5 . . ?
C12 N6 C13 117.3(14) . . ?
C12 N6 H6 121.4 . . ?
C13 N6 H6 121.4 . . ?
N3A C1A C4A 110(3) . . ?
N3A C1A C2A 116(3) . . ?
C4A C1A C2A 112(3) . . ?
N3A C1A C3A 103(3) . . ?
C4A C1A C3A 110(3) . . ?
C2A C1A C3A 105(3) . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
C1A C3A H3A1 109.5 . . ?
C1A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C1A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
O1A C4A N4A 122(3) . . ?
O1A C4A C1A 116(3) . . ?
N4A C4A C1A 122(3) . . ?
N4A C5A C8A 110(3) . . ?
N4A C5A C7A 108(4) . . ?
C8A C5A C7A 112(4) . . ?
N4A C5A C6A 121(4) . . ?
C8A C5A C6A 109(4) . . ?
C7A C5A C6A 96(3) . . ?
C5A C6A H6A1 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C5A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
C5A C7A H7A1 109.5 . . ?
C5A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C5A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
O2A C8A N5A 123(5) . . ?
O2A C8A C5A 119(4) . . ?
N5A C8A C5A 117(3) . . ?
C12A C9A N5A 114(3) . . ?
C12A C9A C11A 105(3) . . ?
N5A C9A C11A 110(3) . . ?
C12A C9A C10A 105(3) . . ?
N5A C9A C10A 108(3) . . ?
C11A C9A C10A 115(3) . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C9A C11A H11D 109.5 . . ?
C9A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C9A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
O3A C12A N6A 117(3) . . ?
O3A C12A C9A 114(3) . . ?
N6A C12A C9A 116(3) . . ?
N6A C13A H13C 106.4 . . ?
C14A C13A H13C 106.4 8_566 . ?
N6A C13A H13D 106.4 . . ?
C14A C13A H13D 106.4 8_566 . ?
H13C C13A H13D 106.5 . . ?
N3A C14A C15A 106.9(13) . . ?
N1A C15A C14A 108.4(15) . . ?
N1A C15A H15A 125.8 . . ?
C14A C15A H15A 125.8 . . ?
N2A N1A C15A 108.3(13) . . ?
N1A N2A N3A 109.3(13) . . ?
N2A N3A C14A 107.2(14) . . ?
N2A N3A C1A 113(2) . . ?
C14A N3A C1A 140(2) . . ?
C4A N4A C5A 124(4) . . ?
C4A N4A H4A 118.1 . . ?
C5A N4A H4A 118.1 . . ?
C8A N5A C9A 127(4) . . ?
C8A N5A H5A 116.3 . . ?
C9A N5A H5A 116.3 . . ?
C12A N6A C13A 118(2) . . ?
C12A N6A H6A4 121.2 . . ?
C13A N6A H6A4 121.2 . . ?
N3B C1B C4B 133(2) . . ?
N3B C1B C3B 103(2) . . ?
C4B C1B C3B 104(3) . . ?
N3B C1B C2B 105(2) . . ?
C4B C1B C2B 100(3) . . ?
C3B C1B C2B 110(3) . . ?
C1B C2B H2B1 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
C1B C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 109.5 . . ?
C1B C3B H3B1 109.5 . . ?
C1B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C1B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
O1B C4B N4B 115(4) . . ?
O1B C4B C1B 136(4) . . ?
N4B C4B C1B 108(3) . . ?
C7B C5B C8B 102(4) . . ?
C7B C5B C6B 121(3) . . ?
C8B C5B C6B 113(4) . . ?
C7B C5B N4B 107(4) . . ?
C8B C5B N4B 116(4) . . ?
C6B C5B N4B 98(3) . . ?
C5B C6B H6B1 109.5 . . ?
C5B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C5B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
C5B C7B H7B1 109.5 . . ?
C5B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C5B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
O2B C8B N5B 121(4) . . ?
O2B C8B C5B 121(5) . . ?
N5B C8B C5B 118(3) . . ?
N5B C9B C12B 112(2) . . ?
N5B C9B C11B 114(2) . . ?
C12B C9B C11B 107(2) . . ?
N5B C9B C10B 106(2) . . ?
C12B C9B C10B 110(2) . . ?
C11B C9B C10B 107(2) . . ?
C9B C10B H10G 109.5 . . ?
C9B C10B H10H 109.5 . . ?
H10G C10B H10H 109.5 . . ?
C9B C10B H10I 109.5 . . ?
H10G C10B H10I 109.5 . . ?
H10H C10B H10I 109.5 . . ?
C9B C11B H11G 109.5 . . ?
C9B C11B H11H 109.5 . . ?
H11G C11B H11H 109.5 . . ?
C9B C11B H11I 109.5 . . ?
H11G C11B H11I 109.5 . . ?
H11H C11B H11I 109.5 . . ?
O3B C12B N6B 111.6(19) . . ?
O3B C12B C9B 123(2) . . ?
N6B C12B C9B 124(2) . . ?
N6B C13B C15B 124.1(19) . 1_556 ?
N6B C13B H13E 106.3 . . ?
C15B C13B H13E 106.3 1_556 . ?
N6B C13B H13F 106.3 . . ?
C15B C13B H13F 106.3 1_556 . ?
H13E C13B H13F 106.4 . . ?
C15B C14B N3B 108.0(12) . . ?
C15B C14B H14B 126.0 . . ?
N3B C14B H14B 126.0 . . ?
C14B C15B N1B 107.4(11) . . ?
N2B N1B C15B 107.5(12) . . ?
N3B N2B N1B 110.1(12) . . ?
N2B N3B C14B 107.0(11) . . ?
N2B N3B C1B 106(2) . . ?
C14B N3B C1B 147(2) . . ?
C4B N4B C5B 124(4) . . ?
C4B N4B H4B 117.9 . . ?
C5B N4B H4B 117.9 . . ?
C9B N5B C8B 126(3) . . ?
C9B N5B H5B 117.0 . . ?
C8B N5B H5B 117.0 . . ?
C12B N6B C13B 124.1(17) . . ?
C12B N6B H6B4 118.0 . . ?
C13B N6B H6B4 118.0 . . ?

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
N3 C1 C4 O1 135(2) . . . . ?
C2 C1 C4 O1 -94(3) . . . . ?
C3 C1 C4 O1 23(3) . . . . ?
N3 C1 C4 N4 -48(3) . . . . ?
C2 C1 C4 N4 83(3) . . . . ?
C3 C1 C4 N4 -161(3) . . . . ?
N4 C5 C8 O2 133(4) . . . . ?
C7 C5 C8 O2 -108(4) . . . . ?
C6 C5 C8 O2 0(5) . . . . ?
N4 C5 C8 N5 -53(4) . . . . ?
C7 C5 C8 N5 67(5) . . . . ?
C6 C5 C8 N5 174(3) . . . . ?
N5 C9 C12 O3 -177.2(19) . . . . ?
C10 C9 C12 O3 -59(2) . . . . ?
C11 C9 C12 O3 62(2) . . . . ?
N5 C9 C12 N6 -4(2) . . . . ?
C10 C9 C12 N6 113.9(19) . . . . ?
C11 C9 C12 N6 -124.4(19) . . . . ?
N3 C14 C15 N1 -0.5(11) . . . . ?
C13 C14 C15 N1 -178.8(10) 8_565 . . . ?
C14 C15 N1 N2 0.3(9) . . . . ?
C15 N1 N2 N3 0.0(5) . . . . ?
C15 C14 N3 N2 0.5(9) . . . . ?
C13 C14 N3 N2 178.9(8) 8_565 . . . ?
C15 C14 N3 C1 -178.5(8) . . . . ?
C13 C14 N3 C1 -0.1(15) 8_565 . . . ?
N1 N2 N3 C14 -0.3(5) . . . . ?
N1 N2 N3 C1 179.0(5) . . . . ?
C4 C1 N3 C14 -48.6(18) . . . . ?
C2 C1 N3 C14 -177.7(15) . . . . ?
C3 C1 N3 C14 68.1(15) . . . . ?
C4 C1 N3 N2 132.5(15) . . . . ?
C2 C1 N3 N2 3.3(14) . . . . ?
C3 C1 N3 N2 -110.9(12) . . . . ?
O1 C4 N4 C5 27(4) . . . . ?
C1 C4 N4 C5 -149(3) . . . . ?
C7 C5 N4 C4 -177(3) . . . . ?
C8 C5 N4 C4 -55(4) . . . . ?
C6 C5 N4 C4 71(4) . . . . ?
O2 C8 N5 C9 9(6) . . . . ?
C5 C8 N5 C9 -165(2) . . . . ?
C12 C9 N5 C8 -77(4) . . . . ?
C10 C9 N5 C8 165(3) . . . . ?
C11 C9 N5 C8 42(4) . . . . ?
O3 C12 N6 C13 7(3) . . . . ?
C9 C12 N6 C13 -166.1(15) . . . . ?
C14 C13 N6 C12 86.9(19) 8_566 . . . ?
N3A C1A C4A O1A 79(8) . . . . ?
C2A C1A C4A O1A -151(8) . . . . ?
C3A C1A C4A O1A -35(8) . . . . ?
N3A C1A C4A N4A -108(8) . . . . ?
C2A C1A C4A N4A 23(9) . . . . ?
C3A C1A C4A N4A 139(8) . . . . ?
N4A C5A C8A O2A 114(9) . . . . ?
C7A C5A C8A O2A -126(8) . . . . ?
C6A C5A C8A O2A -20(10) . . . . ?
N4A C5A C8A N5A -55(8) . . . . ?
C7A C5A C8A N5A 65(8) . . . . ?
C6A C5A C8A N5A 171(7) . . . . ?
N5A C9A C12A O3A -162(6) . . . . ?
C11A C9A C12A O3A 78(6) . . . . ?
C10A C9A C12A O3A -45(6) . . . . ?
N5A C9A C12A N6A -21(5) . . . . ?
C11A C9A C12A N6A -141(5) . . . . ?
C10A C9A C12A N6A 96(5) . . . . ?
N3A C14A C15A N1A 0.0(12) . . . . ?
C13A C14A C15A N1A -179.7(10) 8_565 . . . ?
C14A C15A N1A N2A -0.1(10) . . . . ?
C15A N1A N2A N3A 0.1(5) . . . . ?
N1A N2A N3A C14A -0.1(5) . . . . ?
N1A N2A N3A C1A -179.9(5) . . . . ?
C15A C14A N3A N2A 0.0(10) . . . . ?
C13A C14A N3A N2A 179.7(10) 8_565 . . . ?
C15A C14A N3A C1A 179.8(9) . . . . ?
C13A C14A N3A C1A -0.5(18) 8_565 . . . ?
C4A C1A N3A N2A 167(3) . . . . ?
C2A C1A N3A N2A 39(4) . . . . ?
C3A C1A N3A N2A -75(3) . . . . ?
C4A C1A N3A C14A -13(3) . . . . ?
C2A C1A N3A C14A -141(4) . . . . ?
C3A C1A N3A C14A 105(3) . . . . ?
O1A C4A N4A C5A 13(15) . . . . ?
C1A C4A N4A C5A -160(6) . . . . ?
C8A C5A N4A C4A -9(11) . . . . ?
C7A C5A N4A C4A -132(10) . . . . ?
C6A C5A N4A C4A 119(10) . . . . ?
O2A C8A N5A C9A 56(12) . . . . ?
C5A C8A N5A C9A -135(6) . . . . ?
C12A C9A N5A C8A -74(7) . . . . ?
C11A C9A N5A C8A 43(8) . . . . ?
C10A C9A N5A C8A 169(7) . . . . ?
O3A C12A N6A C13A 20(8) . . . . ?
C9A C12A N6A C13A -119(6) . . . . ?
C14A C13A N6A C12A 100(6) 8_566 . . . ?
N3B C1B C4B O1B 160(4) . . . . ?
C3B C1B C4B O1B 36(6) . . . . ?
C2B C1B C4B O1B -77(5) . . . . ?
N3B C1B C4B N4B -31(6) . . . . ?
C3B C1B C4B N4B -155(3) . . . . ?
C2B C1B C4B N4B 92(4) . . . . ?
C7B C5B C8B O2B -98(5) . . . . ?
C6B C5B C8B O2B 34(7) . . . . ?
N4B C5B C8B O2B 145(5) . . . . ?
C7B C5B C8B N5B 75(5) . . . . ?
C6B C5B C8B N5B -153(4) . . . . ?
N4B C5B C8B N5B -41(6) . . . . ?
N5B C9B C12B O3B -177(2) . . . . ?
C11B C9B C12B O3B 57(3) . . . . ?
C10B C9B C12B O3B -59(4) . . . . ?
N5B C9B C12B N6B 13(4) . . . . ?
C11B C9B C12B N6B -113(3) . . . . ?
C10B C9B C12B N6B 131(3) . . . . ?
N3B C14B C15B N1B -0.5(12) . . . . ?
N3B C14B C15B C13B -167(2) . . . 1_554 ?
C14B C15B N1B N2B 0.2(10) . . . . ?
C13B C15B N1B N2B 170.1(15) 1_554 . . . ?
C15B N1B N2B N3B 0.2(5) . . . . ?
N1B N2B N3B C14B -0.5(5) . . . . ?
N1B N2B N3B C1B 180.0(5) . . . . ?
C15B C14B N3B N2B 0.6(10) . . . . ?
C15B C14B N3B C1B 179.9(10) . . . . ?
C4B C1B N3B N2B -64(4) . . . . ?
C3B C1B N3B N2B 61(2) . . . . ?
C2B C1B N3B N2B 176(2) . . . . ?
C4B C1B N3B C14B 117(4) . . . . ?
C3B C1B N3B C14B -119(3) . . . . ?
C2B C1B N3B C14B -3(2) . . . . ?
O1B C4B N4B C5B 1(6) . . . . ?
C1B C4B N4B C5B -171(3) . . . . ?
C7B C5B N4B C4B -162(4) . . . . ?
C8B C5B N4B C4B -48(5) . . . . ?
C6B C5B N4B C4B 72(5) . . . . ?
C12B C9B N5B C8B -78(4) . . . . ?
C11B C9B N5B C8B 44(4) . . . . ?
C10B C9B N5B C8B 161(4) . . . . ?
O2B C8B N5B C9B -6(7) . . . . ?
C5B C8B N5B C9B -179(3) . . . . ?
O3B C12B N6B C13B 9(4) . . . . ?
C9B C12B N6B C13B -180(2) . . . . ?
C15B C13B N6B C12B -80(3) 1_556 . . . ?

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
C7^a H7A^a N1^a 0.96 2.57 3.44(4) 151.1 2_565 yes
C7^a H7B^a O2^a 0.96 2.34 3.22(5) 152.0 2_564 yes
C11^a H11C^a O2^a 0.96 2.31 2.90(5) 119.0 . yes
N5^a H5^a O3^a 0.86 2.17 2.99(3) 159.8 8_565 yes
N6^a H6^a O1^a 0.86 2.17 3.00(2) 162.4 . yes
C6A^b H6A3^b N6A^b 0.96 2.67 3.41(9) 133.4 2_564 yes
C6A^b H6A3^b O2A^b 0.96 2.40 3.24(9) 145.8 2_564 yes
C7A^b H7A1^b N2A^b 0.96 2.54 3.05(8) 113.6 6_557 yes
C7A^b H7A2^b O2A^b 0.96 2.63 3.44(10) 141.8 2_564 yes
C7A^b H7A3^b O3A^b 0.96 2.14 3.04(11) 155.2 8_565 yes
C10A^b H10D^b O3A^b 0.96 2.14 2.95(10) 140.6 8_565 yes
C11A^b H11D^b N1A^b 0.96 2.11 3.00(8) 153.2 6_557 yes
C13A^b H13C^b O1A^b 0.97 2.23 3.06(12) 143.0 8_566 yes
N5A^b H5A^b O1A^b 0.86 1.59 2.13(10) 117.6 . yes
N5A^b H5A^b O3A^b 0.86 2.42 2.84(8) 110.1 8_565 yes
N6A^b H6A4^b O2A^b 0.86 2.47 3.10(9) 130.1 . yes
C2B^c H2B3^c O2B^c 0.96 2.64 3.51(5) 150.8 2_564 yes
C6B^c H6B1^c O1B^c 0.96 2.30 2.88(4) 117.5 . yes
C6B^c H6B2^c O2B^c 0.96 2.62 3.42(5) 140.8 2_564 yes
C10B^c H10I^c N1B^c 0.96 2.43 3.22(3) 139.7 8_566 yes
C10B^c H10I^c O3B^c 0.96 2.46 3.13(3) 127.0 8_565 yes
C11B^c H11H^c O2B^c 0.96 2.20 2.82(5) 121.2 . yes
C13B^c H13F^c N2B^c 0.97 2.58 3.31(3) 132.3 8_566 yes
N4B^c H4B^c N3B^c 0.86 2.53 2.98(5) 114.2 . yes
N4B^c H4B^c O2B^c 0.86 2.46 2.99(6) 119.8 2_564 yes
N5B^c H5B^c O3B^c 0.86 2.27 3.11(3) 163.3 8_565 yes
N6B^c H6B4^c O1B^c 0.86 2.28 3.07(3) 153.3 . yes
C7^a H7A^a N1^a 0.96 2.57 3.44(4) 151.1 2_565 yes
C7^a H7B^a O2^a 0.96 2.34 3.22(5) 152.0 2_564 yes
C11^a H11C^a O2^a 0.96 2.31 2.90(5) 119.0 . yes
N5^a H5^a O3^a 0.86 2.17 2.99(3) 159.8 8_565 yes
N6^a H6^a O1^a 0.86 2.17 3.00(2) 162.4 . yes
C6A^b H6A3^b N6A^b 0.96 2.67 3.41(9) 133.4 2_564 yes
C6A^b H6A3^b O2A^b 0.96 2.40 3.24(9) 145.8 2_564 yes
C7A^b H7A1^b N2A^b 0.96 2.54 3.05(8) 113.6 6_557 yes
C7A^b H7A2^b O2A^b 0.96 2.63 3.44(10) 141.8 2_564 yes
C7A^b H7A3^b O3A^b 0.96 2.14 3.04(11) 155.2 8_565 yes
C10A^b H10D^b O3A^b 0.96 2.14 2.95(10) 140.6 8_565 yes
C11A^b H11D^b N1A^b 0.96 2.11 3.00(8) 153.2 6_557 yes
C13A^b H13C^b O1A^b 0.97 2.23 3.06(12) 143.0 8_566 yes
N5A^b H5A^b O1A^b 0.86 1.59 2.13(10) 117.6 . yes
N5A^b H5A^b O3A^b 0.86 2.42 2.84(8) 110.1 8_565 yes
N6A^b H6A4^b O2A^b 0.86 2.47 3.10(9) 130.1 . yes
C2B^c H2B3^c O2B^c 0.96 2.64 3.51(5) 150.8 2_564 yes
C6B^c H6B1^c O1B^c 0.96 2.30 2.88(4) 117.5 . yes
C6B^c H6B2^c O2B^c 0.96 2.62 3.42(5) 140.8 2_564 yes
C10B^c H10I^c N1B^c 0.96 2.43 3.22(3) 139.7 8_566 yes
C10B^c H10I^c O3B^c 0.96 2.46 3.13(3) 127.0 8_565 yes
C11B^c H11H^c O2B^c 0.96 2.20 2.82(5) 121.2 . yes
C13B^c H13F^c N2B^c 0.97 2.58 3.31(3) 132.3 8_566 yes
N4B^c H4B^c N3B^c 0.86 2.53 2.98(5) 114.2 . yes
N4B^c H4B^c O2B^c 0.86 2.46 2.99(6) 119.8 2_564 yes
N5B^c H5B^c O3B^c 0.86 2.27 3.11(3) 163.3 8_565 yes
N6B^c H6B4^c O1B^c 0.86 2.28 3.07(3) 153.3 . yes

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.079


# start Validation Reply Form
_vrf_PLAT088_NEWORTHO1           
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.76 Note  
RESPONSE: The structure is threefold disordered which makes
the number of refinement parameters threefold and hence 
poor reflection to parameter ratio.
;
_vrf_PLAT026_NEWORTHO1           
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        32% Check 
RESPONSE: The sample was poorly diffracting. 
;
_vrf_PLAT084_NEWORTHO1           
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.41 Report
RESPONSE: The sample was poorly diffracting with a large 
percentage of reflection at higher Bragg angle very weak.
Weak reflections tend to have poor signal to noise ratio
which leads to more uncertainity of measured intensities.
;
# end Validation Reply Form

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

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2208399'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2022-09-20 deposited with the CCDC.	2023-04-14 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         'C15 H24 N6 O3'
_chemical_formula_sum            'C15 H24 N6 O3'
_chemical_formula_weight         336.40

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                   18.146(4)
_cell_length_b                   10.719(2)
_cell_length_c                   18.540(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.90(3)
_cell_angle_gamma                90
_cell_volume                     3593.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5006
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      22.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.243
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            47089
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6317
_reflns_number_gt                3734
_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       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0481P)²+1.3198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6317
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.56704(15) 0.1940(2) 0.43544(14) 0.0465(7) Uani 1 1 d . . . . .
C1B C 0.94233(15) 0.7038(2) 0.42692(14) 0.0454(6) Uani 1 1 d . . . . .
C2A C 0.62099(18) 0.1446(3) 0.49476(17) 0.0747(9) Uani 1 1 d . . . . .
H2A1 H 0.603801 0.065722 0.511210 0.112 Uiso 1 1 calc R U . . .
H2A2 H 0.668556 0.133966 0.476556 0.112 Uiso 1 1 calc R U . . .
H2A3 H 0.625040 0.202626 0.534344 0.112 Uiso 1 1 calc R U . . .
C2B C 0.8962(2) 0.6546(3) 0.48317(18) 0.0835(11) Uani 1 1 d . . . . .
H2B1 H 0.916752 0.577344 0.501790 0.125 Uiso 1 1 calc R U . . .
H2B2 H 0.895399 0.713969 0.521849 0.125 Uiso 1 1 calc R U . . .
H2B3 H 0.846690 0.640641 0.462134 0.125 Uiso 1 1 calc R U . . .
C3A C 0.49077(18) 0.2063(3) 0.46020(18) 0.0772(10) Uani 1 1 d . . . . .
H3A1 H 0.474533 0.126567 0.476386 0.116 Uiso 1 1 calc R U . . .
H3A2 H 0.491585 0.265060 0.499317 0.116 Uiso 1 1 calc R U . . .
H3A3 H 0.457385 0.234998 0.420727 0.116 Uiso 1 1 calc R U . . .
C3B C 1.02158(18) 0.7210(3) 0.4562(2) 0.0848(11) Uani 1 1 d . . . . .
H3B1 H 1.040890 0.643076 0.475076 0.127 Uiso 1 1 calc R U . . .
H3B2 H 1.050246 0.748594 0.418021 0.127 Uiso 1 1 calc R U . . .
H3B3 H 1.024186 0.782171 0.494118 0.127 Uiso 1 1 calc R U . . .
C4A C 0.56241(13) 0.1072(2) 0.37092(14) 0.0415(6) Uani 1 1 d . . . . .
C4B C 0.94106(13) 0.6155(2) 0.36352(14) 0.0407(6) Uani 1 1 d . . . . .
C5A C 0.53445(13) 0.0877(2) 0.24030(13) 0.0403(6) Uani 1 1 d . . . . .
C5B C 0.96106(13) 0.5899(2) 0.23639(14) 0.0417(6) Uani 1 1 d . . . . .
C6A C 0.45448(14) 0.0510(2) 0.24026(17) 0.0588(8) Uani 1 1 d . . . . .
H6A1 H 0.439910 0.004487 0.197150 0.088 Uiso 1 1 calc R U . . .
H6A2 H 0.447910 0.000489 0.281982 0.088 Uiso 1 1 calc R U . . .
H6A3 H 0.424543 0.124699 0.241638 0.088 Uiso 1 1 calc R U . . .
C6B C 1.04147(14) 0.5527(3) 0.24617(18) 0.0662(9) Uani 1 1 d . . . . .
H6B1 H 1.053591 0.504012 0.205349 0.099 Uiso 1 1 calc R U . . .
H6B2 H 1.071749 0.626208 0.249824 0.099 Uiso 1 1 calc R U . . .
H6B3 H 1.050224 0.504095 0.289559 0.099 Uiso 1 1 calc R U . . .
C7A C 0.54560(16) 0.1707(2) 0.17646(14) 0.0554(7) Uani 1 1 d . . . . .
H7A1 H 0.531600 0.126504 0.132382 0.083 Uiso 1 1 calc R U . . .
H7A2 H 0.515588 0.244122 0.178815 0.083 Uiso 1 1 calc R U . . .
H7A3 H 0.596708 0.194373 0.177560 0.083 Uiso 1 1 calc R U . . .
C7B C 0.94573(18) 0.6705(3) 0.16959(15) 0.0639(8) Uani 1 1 d . . . . .
H7B1 H 0.957068 0.624482 0.127526 0.096 Uiso 1 1 calc R U . . .
H7B2 H 0.894504 0.694048 0.164836 0.096 Uiso 1 1 calc R U . . .
H7B3 H 0.975932 0.744117 0.174131 0.096 Uiso 1 1 calc R U . . .
C8A C 0.58287(14) -0.0279(2) 0.23537(13) 0.0381(6) Uani 1 1 d . . . . .
C8B C 0.91232(14) 0.4738(2) 0.22789(13) 0.0408(6) Uani 1 1 d . . . . .
C9A C 0.71093(14) -0.1049(2) 0.23911(15) 0.0483(7) Uani 1 1 d . . . . .
C9B C 0.78269(13) 0.3976(2) 0.21610(14) 0.0428(6) Uani 1 1 d . . . . .
C10A C 0.78530(16) -0.0411(3) 0.2482(2) 0.0839(11) Uani 1 1 d . . . . .
H10A H 0.823639 -0.101207 0.242594 0.126 Uiso 1 1 calc R U . . .
H10B H 0.787328 0.022907 0.212224 0.126 Uiso 1 1 calc R U . . .
H10C H 0.792237 -0.004546 0.295548 0.126 Uiso 1 1 calc R U . . .
C10B C 0.70963(15) 0.4651(3) 0.20360(19) 0.0687(9) Uani 1 1 d . . . . .
H10D H 0.670549 0.405375 0.194283 0.103 Uiso 1 1 calc R U . . .
H10E H 0.700980 0.512964 0.245817 0.103 Uiso 1 1 calc R U . . .
H10F H 0.710939 0.519844 0.162748 0.103 Uiso 1 1 calc R U . . .
C11A C 0.70021(19) -0.1654(3) 0.16539(17) 0.0799(10) Uani 1 1 d . . . . .
H11A H 0.737800 -0.227394 0.161163 0.120 Uiso 1 1 calc R U . . .
H11B H 0.652379 -0.204186 0.159539 0.120 Uiso 1 1 calc R U . . .
H11C H 0.703639 -0.103175 0.128602 0.120 Uiso 1 1 calc R U . . .
C11B C 0.79398(17) 0.3195(3) 0.14984(16) 0.0653(8) Uani 1 1 d . . . . .
H11D H 0.755043 0.258952 0.142898 0.098 Uiso 1 1 calc R U . . .
H11E H 0.793267 0.372576 0.108078 0.098 Uiso 1 1 calc R U . . .
H11F H 0.840791 0.277511 0.156562 0.098 Uiso 1 1 calc R U . . .
C12A C 0.71330(15) -0.2041(2) 0.29758(16) 0.0493(7) Uani 1 1 d . . . . .
C12B C 0.77613(15) 0.3118(2) 0.27998(16) 0.0506(7) Uani 1 1 d . . . . .
C13A C 0.6776(2) -0.2647(3) 0.4146(2) 0.0819(11) Uani 1 1 d . . . . .
H13A H 0.628171 -0.288290 0.425447 0.098 Uiso 1 1 calc R U . . .
H13B H 0.704425 -0.340352 0.404814 0.098 Uiso 1 1 calc R U . . .
C13B C 0.8110(2) 0.2655(3) 0.40571(19) 0.0837(11) Uani 1 1 d . . . . .
H13C H 0.774704 0.199653 0.396520 0.100 Uiso 1 1 calc R U . . .
H13D H 0.857982 0.226685 0.421092 0.100 Uiso 1 1 calc R U . . .
C14A C 0.7141(2) -0.2028(4) 0.4757(2) 0.0879(12) Uani 1 1 d . . . . .
C14B C 0.7889(2) 0.3435(4) 0.4629(2) 0.0784(11) Uani 1 1 d . . . . .
C15A C 0.7435(3) -0.1485(5) 0.5233(3) 0.1276(19) Uani 1 1 d . . . . .
H15A H 0.767337 -0.104550 0.561786 0.153 Uiso 1 1 calc R U . . .
C15B C 0.7734(3) 0.4064(5) 0.5083(2) 0.1113(15) Uani 1 1 d . . . . .
H15B H 0.760649 0.458118 0.545518 0.134 Uiso 1 1 calc R U . . .
N1A N 0.5910(2) 0.4856(3) 0.48668(19) 0.1110(12) Uani 1 1 d . . . . .
N1B N 0.9055(2) 0.9919(3) 0.4729(2) 0.1209(13) Uani 1 1 d . . . . .
N2A N 0.59001(15) 0.4006(2) 0.45241(14) 0.0680(7) Uani 1 1 d . . . . .
N2B N 0.91023(16) 0.9074(2) 0.43879(15) 0.0727(8) Uani 1 1 d . . . . .
N3A N 0.59348(14) 0.3151(2) 0.41023(13) 0.0620(7) Uani 1 1 d . . . . .
N3B N 0.91172(16) 0.8222(2) 0.39769(13) 0.0716(8) Uani 1 1 d . . . . .
N4A N 0.55631(11) 0.15830(17) 0.30583(11) 0.0408(5) Uani 1 1 d . . . . .
H4A H 0.565630 0.236565 0.301968 0.049 Uiso 1 1 calc R U . . .
N4B N 0.94310(11) 0.66353(17) 0.29841(11) 0.0405(5) Uani 1 1 d . . . . .
H4B H 0.933438 0.741549 0.292289 0.049 Uiso 1 1 calc R U . . .
N5A N 0.65526(11) -0.01036(16) 0.24805(11) 0.0403(5) Uani 1 1 d . . . . .
H5A H 0.670200 0.062251 0.262610 0.048 Uiso 1 1 calc R U . . .
N5B N 0.83989(10) 0.49161(16) 0.22992(11) 0.0395(5) Uani 1 1 d . . . . .
H5B H 0.825655 0.565475 0.240355 0.047 Uiso 1 1 calc R U . . .
N6A N 0.67310(13) -0.1866(2) 0.35166(13) 0.0583(6) Uani 1 1 d . . . . .
H6A H 0.642442 -0.125232 0.349497 0.070 Uiso 1 1 calc R U . . .
N6B N 0.81805(14) 0.3334(2) 0.33959(13) 0.0620(7) Uani 1 1 d . . . . .
H6B H 0.851254 0.390622 0.339310 0.074 Uiso 1 1 calc R U . . .
O1A O 0.56146(10) -0.00498(15) 0.38087(10) 0.0548(5) Uani 1 1 d . . . . .
O1B O 0.94127(10) 0.50313(15) 0.37469(10) 0.0554(5) Uani 1 1 d . . . . .
O2A O 0.55566(9) -0.12746(15) 0.21764(10) 0.0532(5) Uani 1 1 d . . . . .
O2B O 0.93903(9) 0.37351(15) 0.21567(10) 0.0569(5) Uani 1 1 d . . . . .
O3A O 0.75463(11) -0.29364(17) 0.29418(12) 0.0724(6) Uani 1 1 d . . . . .
O3B O 0.73032(12) 0.22911(18) 0.27534(12) 0.0814(7) 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
C1A N3A 1.474(3) . ?
C1A C3A 1.501(4) . ?
C1A C2A 1.505(4) . ?
C1A C4A 1.512(3) . ?
C1B N3B 1.470(3) . ?
C1B C2B 1.489(4) . ?
C1B C3B 1.504(4) . ?
C1B C4B 1.508(3) . ?
C4A O1A 1.217(3) . ?
C4A N4A 1.321(3) . ?
C4B O1B 1.222(3) . ?
C4B N4B 1.316(3) . ?
C5A N4A 1.457(3) . ?
C5A C6A 1.503(3) . ?
C5A C7A 1.508(3) . ?
C5A C8A 1.526(3) . ?
C5B N4B 1.454(3) . ?
C5B C6B 1.509(3) . ?
C5B C7B 1.516(4) . ?
C5B C8B 1.527(3) . ?
C8A O2A 1.210(3) . ?
C8A N5A 1.328(3) . ?
C8B O2B 1.209(3) . ?
C8B N5B 1.332(3) . ?
C9A N5A 1.451(3) . ?
C9A C10A 1.509(4) . ?
C9A C11A 1.510(4) . ?
C9A C12A 1.516(4) . ?
C9B N5B 1.454(3) . ?
C9B C10B 1.511(3) . ?
C9B C12B 1.512(4) . ?
C9B C11B 1.515(3) . ?
C12A O3A 1.223(3) . ?
C12A N6A 1.303(3) . ?
C12B O3B 1.213(3) . ?
C12B N6B 1.308(3) . ?
C13A C14A 1.426(5) . ?
C13A N6A 1.433(4) . ?
C13B C14B 1.433(5) . ?
C13B N6B 1.441(4) . ?
C14A C15A 1.150(6) . ?
C14B C15B 1.133(5) . ?
N1A N2A 1.110(3) . ?
N1B N2B 1.113(3) . ?
N2A N3A 1.210(3) . ?
N2B N3B 1.190(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
N3A C1A C3A 110.7(2) . . ?
N3A C1A C2A 109.4(2) . . ?
C3A C1A C2A 111.5(2) . . ?
N3A C1A C4A 106.8(2) . . ?
C3A C1A C4A 107.8(2) . . ?
C2A C1A C4A 110.5(2) . . ?
N3B C1B C2B 110.3(2) . . ?
N3B C1B C3B 110.3(2) . . ?
C2B C1B C3B 111.6(3) . . ?
N3B C1B C4B 106.0(2) . . ?
C2B C1B C4B 110.5(2) . . ?
C3B C1B C4B 107.9(2) . . ?
O1A C4A N4A 123.1(2) . . ?
O1A C4A C1A 119.2(2) . . ?
N4A C4A C1A 117.6(2) . . ?
O1B C4B N4B 122.8(2) . . ?
O1B C4B C1B 119.2(2) . . ?
N4B C4B C1B 118.0(2) . . ?
N4A C5A C6A 109.3(2) . . ?
N4A C5A C7A 107.61(19) . . ?
C6A C5A C7A 110.4(2) . . ?
N4A C5A C8A 110.76(19) . . ?
C6A C5A C8A 110.4(2) . . ?
C7A C5A C8A 108.4(2) . . ?
N4B C5B C6B 109.2(2) . . ?
N4B C5B C7B 107.4(2) . . ?
C6B C5B C7B 110.9(2) . . ?
N4B C5B C8B 110.9(2) . . ?
C6B C5B C8B 110.1(2) . . ?
C7B C5B C8B 108.4(2) . . ?
O2A C8A N5A 123.2(2) . . ?
O2A C8A C5A 120.6(2) . . ?
N5A C8A C5A 116.13(19) . . ?
O2B C8B N5B 123.0(2) . . ?
O2B C8B C5B 120.4(2) . . ?
N5B C8B C5B 116.4(2) . . ?
N5A C9A C10A 107.2(2) . . ?
N5A C9A C11A 111.5(2) . . ?
C10A C9A C11A 109.9(3) . . ?
N5A C9A C12A 112.7(2) . . ?
C10A C9A C12A 105.5(2) . . ?
C11A C9A C12A 109.8(2) . . ?
N5B C9B C10B 107.40(19) . . ?
N5B C9B C12B 112.7(2) . . ?
C10B C9B C12B 106.5(2) . . ?
N5B C9B C11B 112.5(2) . . ?
C10B C9B C11B 108.5(2) . . ?
C12B C9B C11B 108.9(2) . . ?
O3A C12A N6A 122.6(3) . . ?
O3A C12A C9A 119.6(3) . . ?
N6A C12A C9A 117.7(2) . . ?
O3B C12B N6B 122.4(3) . . ?
O3B C12B C9B 119.2(3) . . ?
N6B C12B C9B 118.4(2) . . ?
C14A C13A N6A 111.4(3) . . ?
C14B C13B N6B 112.7(3) . . ?
C15A C14A C13A 177.2(5) . . ?
C15B C14B C13B 178.1(4) . . ?
N1A N2A N3A 173.0(3) . . ?
N1B N2B N3B 174.3(4) . . ?
N2A N3A C1A 115.2(2) . . ?
N2B N3B C1B 117.0(2) . . ?
C4A N4A C5A 122.82(19) . . ?
C4B N4B C5B 122.6(2) . . ?
C8A N5A C9A 124.68(19) . . ?
C8B N5B C9B 125.97(19) . . ?
C12A N6A C13A 123.0(3) . . ?
C12B N6B C13B 122.8(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
N3A C1A C4A O1A 160.3(2) . . . . ?
C3A C1A C4A O1A -80.7(3) . . . . ?
C2A C1A C4A O1A 41.4(3) . . . . ?
N3A C1A C4A N4A -22.6(3) . . . . ?
C3A C1A C4A N4A 96.4(3) . . . . ?
C2A C1A C4A N4A -141.5(2) . . . . ?
N3B C1B C4B O1B -157.4(2) . . . . ?
C2B C1B C4B O1B -37.9(3) . . . . ?
C3B C1B C4B O1B 84.5(3) . . . . ?
N3B C1B C4B N4B 25.6(3) . . . . ?
C2B C1B C4B N4B 145.1(3) . . . . ?
C3B C1B C4B N4B -92.6(3) . . . . ?
N4A C5A C8A O2A 136.1(2) . . . . ?
C6A C5A C8A O2A 14.9(3) . . . . ?
C7A C5A C8A O2A -106.0(3) . . . . ?
N4A C5A C8A N5A -47.1(3) . . . . ?
C6A C5A C8A N5A -168.2(2) . . . . ?
C7A C5A C8A N5A 70.8(3) . . . . ?
N4B C5B C8B O2B -135.1(2) . . . . ?
C6B C5B C8B O2B -14.2(3) . . . . ?
C7B C5B C8B O2B 107.3(3) . . . . ?
N4B C5B C8B N5B 49.2(3) . . . . ?
C6B C5B C8B N5B 170.1(2) . . . . ?
C7B C5B C8B N5B -68.5(3) . . . . ?
N5A C9A C12A O3A 175.6(2) . . . . ?
C10A C9A C12A O3A -67.8(3) . . . . ?
C11A C9A C12A O3A 50.6(3) . . . . ?
N5A C9A C12A N6A -7.6(3) . . . . ?
C10A C9A C12A N6A 109.0(3) . . . . ?
C11A C9A C12A N6A -132.6(3) . . . . ?
N5B C9B C12B O3B 180.0(2) . . . . ?
C10B C9B C12B O3B 62.4(3) . . . . ?
C11B C9B C12B O3B -54.5(3) . . . . ?
N5B C9B C12B N6B 3.1(3) . . . . ?
C10B C9B C12B N6B -114.4(3) . . . . ?
C11B C9B C12B N6B 128.7(3) . . . . ?
C3A C1A N3A N2A 52.5(3) . . . . ?
C2A C1A N3A N2A -70.8(3) . . . . ?
C4A C1A N3A N2A 169.6(2) . . . . ?
C2B C1B N3B N2B 63.0(4) . . . . ?
C3B C1B N3B N2B -60.7(4) . . . . ?
C4B C1B N3B N2B -177.3(3) . . . . ?
O1A C4A N4A C5A 11.5(4) . . . . ?
C1A C4A N4A C5A -165.4(2) . . . . ?
C6A C5A N4A C4A 69.2(3) . . . . ?
C7A C5A N4A C4A -170.9(2) . . . . ?
C8A C5A N4A C4A -52.6(3) . . . . ?
O1B C4B N4B C5B -13.1(4) . . . . ?
C1B C4B N4B C5B 163.9(2) . . . . ?
C6B C5B N4B C4B -68.8(3) . . . . ?
C7B C5B N4B C4B 170.9(2) . . . . ?
C8B C5B N4B C4B 52.6(3) . . . . ?
O2A C8A N5A C9A 3.1(4) . . . . ?
C5A C8A N5A C9A -173.6(2) . . . . ?
C10A C9A N5A C8A 171.6(3) . . . . ?
C11A C9A N5A C8A 51.3(3) . . . . ?
C12A C9A N5A C8A -72.8(3) . . . . ?
O2B C8B N5B C9B -1.9(4) . . . . ?
C5B C8B N5B C9B 173.7(2) . . . . ?
C10B C9B N5B C8B -164.4(3) . . . . ?
C12B C9B N5B C8B 78.6(3) . . . . ?
C11B C9B N5B C8B -45.0(3) . . . . ?
O3A C12A N6A C13A 4.9(4) . . . . ?
C9A C12A N6A C13A -171.8(3) . . . . ?
C14A C13A N6A C12A 106.9(4) . . . . ?
O3B C12B N6B C13B -3.2(4) . . . . ?
C9B C12B N6B C13B 173.5(3) . . . . ?
C14B C13B N6B C12B -116.1(3) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.043



