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

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

data_11octe_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2157221'
loop_
_audit_author_name
_audit_author_address
'Srinivas D'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-05-15 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_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         'C4 H N8 O3'
_chemical_formula_sum            'C4 H N8 O3'
_chemical_formula_weight         209.13
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   3.5936(4)
_cell_length_b                   20.287(3)
_cell_length_c                   11.0324(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.998(4)
_cell_angle_gamma                90
_cell_volume                     804.17(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8579
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1471 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8713.
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    1.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.395
_diffrn_reflns_theta_min         2.728
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1732
_reflns_number_total             2009
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.053
_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)+(0.1090P)²+1.0711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1861
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N8 N 0.6550(5) 0.11895(8) 0.60584(15) 0.0157(4) Uani 1 1 d . . . . .
N5 N 0.6196(5) 0.24377(8) 0.56776(15) 0.0134(4) Uani 1 1 d . . . . .
N3 N 0.4321(5) 0.33074(9) 0.45070(15) 0.0153(4) Uani 1 1 d . . . . .
N15 N 0.7350(4) 0.35401(8) 0.63772(14) 0.0132(4) Uani 1 1 d . . . . .
N13 N 1.0126(5) 0.43124(9) 0.80281(16) 0.0179(4) Uani 1 1 d . . . . .
N12 N 1.0400(5) 0.37105(9) 0.82746(15) 0.0171(4) Uani 1 1 d . . . . .
N2 N 0.4168(5) 0.39243(9) 0.43965(16) 0.0191(4) Uani 1 1 d . . . . .
N7 N 0.8086(5) 0.15288(8) 0.68877(16) 0.0174(4) Uani 1 1 d . . . . .
O1 O 0.5303(6) 0.08225(9) 0.54085(17) 0.0318(5) Uani 1 1 d . . . . .
O4 O 1.0102(7) 0.48651(10) 0.79563(19) 0.0421(5) Uani 1 1 d . . . . .
C6 C 0.7800(5) 0.22133(9) 0.67014(17) 0.0136(4) Uani 1 1 d . . . . .
C4 C 0.6068(5) 0.30929(10) 0.55929(17) 0.0129(4) Uani 1 1 d . . . . .
C11 C 0.8926(5) 0.32858(10) 0.73865(17) 0.0132(4) Uani 1 1 d . . . . .
O6 O 0.3819(8) 0.44559(11) 0.4163(2) 0.0473(6) Uani 1 1 d . . . . .
C10 C 0.9216(5) 0.26164(10) 0.76149(17) 0.0147(4) Uani 1 1 d . . . . .
H10 H 1.030156 0.244618 0.834115 0.018 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
N8 N7 1.264(2) . ?
N8 O1 1.121(3) . ?
N5 C6 1.339(2) . ?
N5 C4 1.333(2) . ?
N3 N2 1.259(2) . ?
N3 C4 1.412(2) . ?
N15 C4 1.330(2) . ?
N15 C11 1.344(2) . ?
N13 N12 1.254(2) . ?
N13 O4 1.124(3) . ?
N12 C11 1.402(2) . ?
N2 O6 1.115(3) . ?
N7 C6 1.407(2) . ?
C6 C10 1.388(3) . ?
C11 C10 1.385(3) . ?
C10 H10 0.9500 . ?

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 N8 N7 171.4(2) . . ?
C4 N5 C6 114.33(16) . . ?
N2 N3 C4 114.00(16) . . ?
C4 N15 C11 114.42(16) . . ?
O4 N13 N12 170.6(2) . . ?
N13 N12 C11 114.80(17) . . ?
O6 N2 N3 171.3(2) . . ?
N8 N7 C6 113.69(16) . . ?
N5 C6 N7 119.21(17) . . ?
N5 C6 C10 124.01(18) . . ?
C10 C6 N7 116.78(17) . . ?
N5 C4 N3 112.40(16) . . ?
N15 C4 N5 128.54(17) . . ?
N15 C4 N3 119.05(17) . . ?
N15 C11 N12 119.47(17) . . ?
N15 C11 C10 123.83(17) . . ?
C10 C11 N12 116.70(17) . . ?
C6 C10 H10 122.6 . . ?
C11 C10 C6 114.85(17) . . ?
C11 C10 H10 122.6 . . ?

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
N8 N7 C6 N5 -3.7(3) . . . . ?
N8 N7 C6 C10 175.99(17) . . . . ?
N5 C6 C10 C11 -1.2(3) . . . . ?
N15 C11 C10 C6 1.2(3) . . . . ?
N13 N12 C11 N15 -0.6(3) . . . . ?
N13 N12 C11 C10 179.15(17) . . . . ?
N12 C11 C10 C6 -178.60(17) . . . . ?
N2 N3 C4 N5 -179.73(17) . . . . ?
N2 N3 C4 N15 0.1(3) . . . . ?
N7 C6 C10 C11 179.10(17) . . . . ?
C6 N5 C4 N3 -179.35(16) . . . . ?
C6 N5 C4 N15 0.8(3) . . . . ?
C4 N5 C6 N7 179.99(17) . . . . ?
C4 N5 C6 C10 0.3(3) . . . . ?
C4 N15 C11 N12 179.55(17) . . . . ?
C4 N15 C11 C10 -0.2(3) . . . . ?
C11 N15 C4 N5 -0.9(3) . . . . ?
C11 N15 C4 N3 179.31(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
