# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_3sepb_a
_database_code_depnum_ccdc_archive 'CCDC 2540887'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2026-03-25 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_audit_creation_date             2025-12-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N5 O2'
_chemical_formula_sum            'C10 H13 N5 O2'
_chemical_formula_weight         235.25
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1778(4)
_cell_length_b                   5.2062(2)
_cell_length_c                   21.0514(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.1250(10)
_cell_angle_gamma                90
_cell_volume                     1106.85(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8067
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1193 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9372.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16372
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_min         2.346
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2408
_reflns_number_total             2745
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+0.3197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.41824(9) 0.89524(17) 0.53793(4) 0.0242(2) Uani 1 1 d . . . . .
O1 O 0.32228(9) 0.82185(18) 0.62240(4) 0.0261(2) Uani 1 1 d . . . . .
N3 N 0.37451(9) 0.60846(19) 0.43616(4) 0.0181(2) Uani 1 1 d . . . . .
H3 H 0.423972 0.734452 0.453737 0.022 Uiso 1 1 calc R U . . .
N5 N 0.33860(10) 0.76869(19) 0.56589(4) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.10110(10) 0.2348(2) 0.53126(5) 0.0211(2) Uani 1 1 d . . . . .
N2 N 0.21622(10) 0.30093(19) 0.43965(4) 0.0198(2) Uani 1 1 d . . . . .
N4 N 0.14016(9) 0.4760(2) 0.62217(5) 0.0199(2) Uani 1 1 d . . . . .
H4 H 0.187243 0.592374 0.645218 0.024 Uiso 1 1 calc R U . . .
C3 C 0.28774(10) 0.4949(2) 0.46978(5) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.16990(10) 0.4256(2) 0.56321(5) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.26749(10) 0.5656(2) 0.53373(5) 0.0163(2) Uani 1 1 d . . . . .
C5 C 0.03516(11) 0.3494(2) 0.64961(5) 0.0200(2) Uani 1 1 d . . . . .
H5 H -0.056228 0.374125 0.626899 0.024 Uiso 1 1 calc R U . . .
C8 C 0.38899(12) 0.5296(2) 0.37193(5) 0.0205(2) Uani 1 1 d . . . . .
H8 H 0.391998 0.340278 0.364285 0.025 Uiso 1 1 calc R U . . .
C6 C 0.06200(13) 0.0982(2) 0.68311(6) 0.0256(3) Uani 1 1 d . . . . .
H6A H 0.151744 0.023766 0.684085 0.031 Uiso 1 1 calc R U . . .
H6B H -0.010803 -0.028966 0.680423 0.031 Uiso 1 1 calc R U . . .
C4 C 0.12949(12) 0.1866(2) 0.47228(5) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.04751(13) 0.3394(2) 0.72100(6) 0.0251(3) Uani 1 1 d . . . . .
H7A H -0.034170 0.360190 0.741584 0.030 Uiso 1 1 calc R U . . .
H7B H 0.128366 0.412918 0.745246 0.030 Uiso 1 1 calc R U . . .
C9 C 0.47389(13) 0.6910(3) 0.33517(6) 0.0266(3) Uani 1 1 d . . . . .
H9A H 0.528890 0.602590 0.306260 0.032 Uiso 1 1 calc R U . . .
H9B H 0.514442 0.846859 0.356258 0.032 Uiso 1 1 calc R U . . .
C10 C 0.32594(14) 0.6894(3) 0.31709(6) 0.0309(3) Uani 1 1 d . . . . .
H10A H 0.275785 0.843917 0.327240 0.037 Uiso 1 1 calc R U . . .
H10B H 0.290240 0.599521 0.277217 0.037 Uiso 1 1 calc R U . . .
H4A H 0.0785(15) 0.048(3) 0.4501(7) 0.027(4) 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 N5 1.2474(12) . ?
O1 N5 1.2524(12) . ?
N3 H3 0.8800 . ?
N3 C3 1.3362(13) . ?
N3 C8 1.4379(13) . ?
N5 C1 1.4065(14) . ?
N1 C2 1.3462(14) . ?
N1 C4 1.3331(15) . ?
N2 C3 1.3556(14) . ?
N2 C4 1.3249(14) . ?
N4 H4 0.8800 . ?
N4 C2 1.3396(14) . ?
N4 C5 1.4364(13) . ?
C3 C1 1.4349(15) . ?
C2 C1 1.4339(14) . ?
C5 H5 1.0000 . ?
C5 C6 1.4948(17) . ?
C5 C7 1.4933(16) . ?
C8 H8 1.0000 . ?
C8 C9 1.4891(15) . ?
C8 C10 1.5010(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5047(17) . ?
C4 H4A 0.974(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5067(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C3 N3 H3 119.2 . . ?
C3 N3 C8 121.56(9) . . ?
C8 N3 H3 119.2 . . ?
O2 N5 O1 120.13(9) . . ?
O2 N5 C1 119.71(9) . . ?
O1 N5 C1 120.16(9) . . ?
C4 N1 C2 116.40(10) . . ?
C4 N2 C3 116.47(10) . . ?
C2 N4 H4 118.4 . . ?
C2 N4 C5 123.20(9) . . ?
C5 N4 H4 118.4 . . ?
N3 C3 N2 115.69(10) . . ?
N3 C3 C1 124.39(10) . . ?
N2 C3 C1 119.92(10) . . ?
N1 C2 C1 120.28(10) . . ?
N4 C2 N1 116.37(10) . . ?
N4 C2 C1 123.34(10) . . ?
N5 C1 C3 121.27(9) . . ?
N5 C1 C2 121.11(9) . . ?
C2 C1 C3 117.61(9) . . ?
N4 C5 H5 116.3 . . ?
N4 C5 C6 119.31(10) . . ?
N4 C5 C7 116.53(10) . . ?
C6 C5 H5 116.3 . . ?
C7 C5 H5 116.3 . . ?
C7 C5 C6 60.47(8) . . ?
N3 C8 H8 116.2 . . ?
N3 C8 C9 117.48(10) . . ?
N3 C8 C10 118.76(11) . . ?
C9 C8 H8 116.2 . . ?
C9 C8 C10 60.52(9) . . ?
C10 C8 H8 116.2 . . ?
C5 C6 H6A 117.8 . . ?
C5 C6 H6B 117.8 . . ?
C5 C6 C7 59.71(8) . . ?
H6A C6 H6B 114.9 . . ?
C7 C6 H6A 117.8 . . ?
C7 C6 H6B 117.8 . . ?
N1 C4 H4A 115.0(9) . . ?
N2 C4 N1 129.33(11) . . ?
N2 C4 H4A 115.7(9) . . ?
C5 C7 C6 59.82(8) . . ?
C5 C7 H7A 117.8 . . ?
C5 C7 H7B 117.8 . . ?
C6 C7 H7A 117.8 . . ?
C6 C7 H7B 117.8 . . ?
H7A C7 H7B 114.9 . . ?
C8 C9 H9A 117.8 . . ?
C8 C9 H9B 117.8 . . ?
C8 C9 C10 60.13(8) . . ?
H9A C9 H9B 114.9 . . ?
C10 C9 H9A 117.8 . . ?
C10 C9 H9B 117.8 . . ?
C8 C10 C9 59.35(8) . . ?
C8 C10 H10A 117.8 . . ?
C8 C10 H10B 117.8 . . ?
C9 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
H10A C10 H10B 115.0 . . ?

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
O2 N5 C1 C3 2.05(17) . . . . ?
O2 N5 C1 C2 -176.52(10) . . . . ?
O1 N5 C1 C3 -177.78(10) . . . . ?
O1 N5 C1 C2 3.65(17) . . . . ?
N3 C3 C1 N5 1.07(18) . . . . ?
N3 C3 C1 C2 179.69(10) . . . . ?
N3 C8 C9 C10 -109.20(13) . . . . ?
N3 C8 C10 C9 107.12(12) . . . . ?
N1 C2 C1 N5 178.80(10) . . . . ?
N1 C2 C1 C3 0.18(16) . . . . ?
N2 C3 C1 N5 -178.97(10) . . . . ?
N2 C3 C1 C2 -0.35(16) . . . . ?
N4 C2 C1 N5 -0.16(18) . . . . ?
N4 C2 C1 C3 -178.78(10) . . . . ?
N4 C5 C6 C7 105.71(12) . . . . ?
N4 C5 C7 C6 -110.25(12) . . . . ?
C3 N3 C8 C9 171.50(11) . . . . ?
C3 N3 C8 C10 101.83(13) . . . . ?
C3 N2 C4 N1 0.2(2) . . . . ?
C2 N1 C4 N2 -0.4(2) . . . . ?
C2 N4 C5 C6 85.94(14) . . . . ?
C2 N4 C5 C7 155.36(11) . . . . ?
C5 N4 C2 N1 -4.15(17) . . . . ?
C5 N4 C2 C1 174.85(10) . . . . ?
C8 N3 C3 N2 0.64(16) . . . . ?
C8 N3 C3 C1 -179.40(10) . . . . ?
C4 N1 C2 N4 179.19(11) . . . . ?
C4 N1 C2 C1 0.15(17) . . . . ?
C4 N2 C3 N3 -179.86(10) . . . . ?
C4 N2 C3 C1 0.18(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_16mayc_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2540888'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2026-03-25 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_audit_creation_date             2026-01-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N5 O3'
_chemical_formula_sum            'C10 H13 N5 O3'
_chemical_formula_weight         251.25
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1034(2)
_cell_length_b                   10.0245(5)
_cell_length_c                   11.6245(5)
_cell_angle_alpha                68.3950(10)
_cell_angle_beta                 83.137(2)
_cell_angle_gamma                82.244(2)
_cell_volume                     546.28(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4489
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1164 before and 0.0607 after correction.
The Ratio of minimum to maximum transmission is 0.8604.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.761
_diffrn_reflns_theta_min         1.890
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3366
_reflns_number_total             4452
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.175
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²+0.1488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1594
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C7(H7A,H7B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N007(H007), N008(H008)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12086(16) 0.12195(9) 0.42516(8) 0.01738(18) Uani 1 1 d . . . . .
O2 O 0.24312(18) 0.29233(9) 0.25589(7) 0.01969(19) Uani 1 1 d . . . . .
O3 O 0.93685(17) 0.36425(9) 0.62300(8) 0.01967(19) Uani 1 1 d . . . . .
N004 N 0.26409(18) 0.22252(10) 0.36995(9) 0.01374(18) Uani 1 1 d . . . . .
N005 N 0.56934(19) 0.46537(10) 0.25623(8) 0.01474(19) Uani 1 1 d . . . . .
H005 H 0.475821 0.438795 0.210891 0.018 Uiso 1 1 calc R U . . .
N006 N 0.64230(18) 0.21325(10) 0.62672(8) 0.01404(18) Uani 1 1 d . . . . .
N007 N 0.34176(18) 0.06405(10) 0.63045(8) 0.01397(18) Uani 1 1 d . . . . .
H007 H 0.234157 0.034586 0.592966 0.017 Uiso 1 1 calc R U . . .
N008 N 0.75451(18) 0.40867(10) 0.44232(8) 0.01330(18) Uani 1 1 d . . . . .
H008 H 0.848411 0.482673 0.406375 0.016 Uiso 1 1 calc R U . . .
C8 C 0.6879(2) 0.59917(11) 0.19734(10) 0.0144(2) Uani 1 1 d . . . . .
H8 H 0.657506 0.668234 0.242603 0.017 Uiso 1 1 calc R U . . .
C9 C 0.9460(2) 0.60119(13) 0.12013(11) 0.0194(2) Uani 1 1 d . . . . .
H9A H 1.030159 0.508711 0.114323 0.023 Uiso 1 1 calc R U . . .
H9B H 1.071403 0.668815 0.119335 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6910(2) 0.66422(13) 0.05882(10) 0.0188(2) Uani 1 1 d . . . . .
H10A H 0.660178 0.770481 0.020367 0.023 Uiso 1 1 calc R U . . .
H10B H 0.618941 0.610401 0.015356 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5904(2) 0.37906(11) 0.37377(9) 0.01210(19) Uani 1 1 d . . . . .
C2 C 0.4757(2) 0.17716(11) 0.56504(9) 0.01192(19) Uani 1 1 d . . . . .
C4 C 0.7820(2) 0.32667(11) 0.56842(10) 0.01322(19) Uani 1 1 d . . . . .
C1 C 0.4426(2) 0.25683(11) 0.43402(9) 0.01223(19) Uani 1 1 d . . . . .
C7 C 0.1728(2) -0.11488(13) 0.83095(11) 0.0204(2) Uani 1 1 d . . . . .
H7A H 0.236529 -0.204564 0.897368 0.024 Uiso 1 1 calc R U . . .
H7B H 0.030929 -0.125439 0.784680 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3697(2) -0.01081(12) 0.76114(10) 0.0162(2) Uani 1 1 d . . . . .
H5 H 0.555204 -0.037894 0.787171 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1646(3) 0.02538(14) 0.85229(11) 0.0245(3) Uani 1 1 d . . . . .
H6A H 0.018421 0.100761 0.818770 0.029 Uiso 1 1 calc R U . . .
H6B H 0.224152 0.021585 0.931530 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N004 1.2542(11) . ?
O2 N004 1.2608(12) . ?
O3 C4 1.2428(13) . ?
N004 C1 1.3921(13) . ?
N005 H005 0.8800 . ?
N005 C8 1.4414(13) . ?
N005 C3 1.3291(13) . ?
N006 C2 1.3371(13) . ?
N006 C4 1.3404(13) . ?
N007 H007 0.8800 . ?
N007 C2 1.3346(13) . ?
N007 C5 1.4405(13) . ?
N008 H008 0.8800 . ?
N008 C3 1.3509(13) . ?
N008 C4 1.4053(13) . ?
C8 H8 1.0000 . ?
C8 C9 1.5008(16) . ?
C8 C10 1.4973(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5065(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C3 C1 1.4326(14) . ?
C2 C1 1.4544(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C5 1.4906(15) . ?
C7 C6 1.5096(18) . ?
C5 H5 1.0000 . ?
C5 C6 1.5050(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N004 O2 119.03(9) . . ?
O1 N004 C1 120.38(9) . . ?
O2 N004 C1 120.59(9) . . ?
C8 N005 H005 117.5 . . ?
C3 N005 H005 117.5 . . ?
C3 N005 C8 125.01(9) . . ?
C2 N006 C4 120.12(9) . . ?
C2 N007 H007 119.3 . . ?
C2 N007 C5 121.36(9) . . ?
C5 N007 H007 119.3 . . ?
C3 N008 H008 118.5 . . ?
C3 N008 C4 122.99(9) . . ?
C4 N008 H008 118.5 . . ?
N005 C8 H8 116.3 . . ?
N005 C8 C9 119.27(9) . . ?
N005 C8 C10 116.57(9) . . ?
C9 C8 H8 116.3 . . ?
C10 C8 H8 116.3 . . ?
C10 C8 C9 60.33(7) . . ?
C8 C9 H9A 117.8 . . ?
C8 C9 H9B 117.8 . . ?
C8 C9 C10 59.72(7) . . ?
H9A C9 H9B 114.9 . . ?
C10 C9 H9A 117.8 . . ?
C10 C9 H9B 117.8 . . ?
C8 C10 C9 59.95(7) . . ?
C8 C10 H10A 117.8 . . ?
C8 C10 H10B 117.8 . . ?
C9 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
H10A C10 H10B 114.9 . . ?
N005 C3 N008 119.02(9) . . ?
N005 C3 C1 123.56(9) . . ?
N008 C3 C1 117.41(9) . . ?
N006 C2 C1 121.79(9) . . ?
N007 C2 N006 116.24(9) . . ?
N007 C2 C1 121.97(9) . . ?
O3 C4 N006 121.93(10) . . ?
O3 C4 N008 117.68(9) . . ?
N006 C4 N008 120.39(9) . . ?
N004 C1 C3 120.46(9) . . ?
N004 C1 C2 122.16(9) . . ?
C3 C1 C2 117.28(9) . . ?
H7A C7 H7B 114.9 . . ?
C5 C7 H7A 117.7 . . ?
C5 C7 H7B 117.7 . . ?
C5 C7 C6 60.21(8) . . ?
C6 C7 H7A 117.7 . . ?
C6 C7 H7B 117.7 . . ?
N007 C5 C7 117.09(9) . . ?
N007 C5 H5 116.3 . . ?
N007 C5 C6 118.65(10) . . ?
C7 C5 H5 116.3 . . ?
C7 C5 C6 60.52(8) . . ?
C6 C5 H5 116.3 . . ?
C7 C6 H6A 117.8 . . ?
C7 C6 H6B 117.8 . . ?
C5 C6 C7 59.27(8) . . ?
C5 C6 H6A 117.8 . . ?
C5 C6 H6B 117.8 . . ?
H6A C6 H6B 115.0 . . ?

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
O1 N004 C1 C3 -174.81(9) . . . . ?
O1 N004 C1 C2 1.40(16) . . . . ?
O2 N004 C1 C3 4.89(16) . . . . ?
O2 N004 C1 C2 -178.90(9) . . . . ?
N005 C8 C9 C10 105.71(11) . . . . ?
N005 C8 C10 C9 -110.14(11) . . . . ?
N005 C3 C1 N004 -0.23(16) . . . . ?
N005 C3 C1 C2 -176.63(9) . . . . ?
N006 C2 C1 N004 -178.14(9) . . . . ?
N006 C2 C1 C3 -1.82(15) . . . . ?
N007 C2 C1 N004 1.87(16) . . . . ?
N007 C2 C1 C3 178.20(9) . . . . ?
N007 C5 C6 C7 106.69(11) . . . . ?
N008 C3 C1 N004 178.13(9) . . . . ?
N008 C3 C1 C2 1.74(14) . . . . ?
C8 N005 C3 N008 -6.80(16) . . . . ?
C8 N005 C3 C1 171.54(10) . . . . ?
C3 N005 C8 C9 97.92(13) . . . . ?
C3 N005 C8 C10 167.17(10) . . . . ?
C3 N008 C4 O3 -179.34(10) . . . . ?
C3 N008 C4 N006 -0.11(16) . . . . ?
C2 N006 C4 O3 179.30(10) . . . . ?
C2 N006 C4 N008 0.11(16) . . . . ?
C2 N007 C5 C7 167.61(10) . . . . ?
C2 N007 C5 C6 98.12(12) . . . . ?
C4 N006 C2 N007 -179.14(9) . . . . ?
C4 N006 C2 C1 0.88(16) . . . . ?
C4 N008 C3 N005 177.58(10) . . . . ?
C4 N008 C3 C1 -0.86(15) . . . . ?
C5 N007 C2 N006 2.17(15) . . . . ?
C5 N007 C2 C1 -177.85(9) . . . . ?
C6 C7 C5 N007 -109.24(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
